JPH0611601A - Antireflection plastic lens - Google Patents
Antireflection plastic lensInfo
- Publication number
- JPH0611601A JPH0611601A JP4169282A JP16928292A JPH0611601A JP H0611601 A JPH0611601 A JP H0611601A JP 4169282 A JP4169282 A JP 4169282A JP 16928292 A JP16928292 A JP 16928292A JP H0611601 A JPH0611601 A JP H0611601A
- Authority
- JP
- Japan
- Prior art keywords
- sol
- oxide
- hard coating
- coating film
- film
- 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
- 229920003023 plastic Polymers 0.000 title claims abstract description 33
- 239000004033 plastic Substances 0.000 title claims abstract description 33
- 238000000576 coating method Methods 0.000 claims abstract description 66
- 239000011248 coating agent Substances 0.000 claims abstract description 65
- 239000008199 coating composition Substances 0.000 claims abstract description 25
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910001887 tin oxide Inorganic materials 0.000 claims abstract description 23
- 229920005862 polyol Polymers 0.000 claims abstract description 9
- 150000003077 polyols Chemical class 0.000 claims abstract description 9
- 229920006295 polythiol Polymers 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000010419 fine particle Substances 0.000 claims abstract description 7
- 239000010936 titanium Substances 0.000 claims abstract description 7
- 125000000524 functional group Chemical group 0.000 claims abstract description 6
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 6
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 6
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 5
- 229910001928 zirconium oxide Inorganic materials 0.000 claims abstract description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910000410 antimony oxide Inorganic materials 0.000 claims abstract description 4
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 4
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 4
- 239000010703 silicon Substances 0.000 claims abstract description 3
- 239000002131 composite material Substances 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 17
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 16
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
- 239000004814 polyurethane Substances 0.000 claims description 12
- 229920002635 polyurethane Polymers 0.000 claims description 12
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 10
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 6
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 5
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 5
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 claims description 4
- 229910001936 tantalum oxide Inorganic materials 0.000 claims description 4
- 150000008282 halocarbons Chemical group 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 10
- 239000010408 film Substances 0.000 abstract 6
- 239000010409 thin film Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 33
- -1 lysine ester Chemical class 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000002245 particle Substances 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 13
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 238000007740 vapor deposition Methods 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229920002574 CR-39 Polymers 0.000 description 5
- 229910010413 TiO 2 Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 2
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- YSMYVNWBCFJUIO-UHFFFAOYSA-N oxotin oxotungsten Chemical compound [W]=O.[Sn]=O YSMYVNWBCFJUIO-UHFFFAOYSA-N 0.000 description 2
- MMKQUGHLEMYQSG-UHFFFAOYSA-N oxygen(2-);praseodymium(3+) Chemical compound [O-2].[O-2].[O-2].[Pr+3].[Pr+3] MMKQUGHLEMYQSG-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229910003447 praseodymium oxide Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 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
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- ADVORQMAWLEPOI-XHTSQIMGSA-N (e)-4-hydroxypent-3-en-2-one;oxotitanium Chemical compound [Ti]=O.C\C(O)=C/C(C)=O.C\C(O)=C/C(C)=O ADVORQMAWLEPOI-XHTSQIMGSA-N 0.000 description 1
- HYZQBNDRDQEWAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese(3+) Chemical compound [Mn+3].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O HYZQBNDRDQEWAN-LNTINUHCSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- JQDNVFWOUUGUKA-UHFFFAOYSA-N 1-sulfanylbutane-2,2-diol Chemical compound SCC(CC)(O)O JQDNVFWOUUGUKA-UHFFFAOYSA-N 0.000 description 1
- GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- JVXHQHGWBAHSSF-UHFFFAOYSA-L 2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;hydron;iron(2+) Chemical compound [H+].[H+].[Fe+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O JVXHQHGWBAHSSF-UHFFFAOYSA-L 0.000 description 1
- JUVSRZCUMWZBFK-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-4-methylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1 JUVSRZCUMWZBFK-UHFFFAOYSA-N 0.000 description 1
- GJNHMDMCAAKXHV-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)propyl-(2,2,2-trimethoxyethoxy)silane Chemical compound COC(OC)(OC)CO[SiH2]CCCOCC1CO1 GJNHMDMCAAKXHV-UHFFFAOYSA-N 0.000 description 1
- GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical compound FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- NNWNNQTUZYVQRK-UHFFFAOYSA-N 5-bromo-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound BrC1=NC=C2NC(C(=O)O)=CC2=C1 NNWNNQTUZYVQRK-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- ASZFCDOTGITCJI-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hex-2-ene Chemical compound C1C=CC2OC12 ASZFCDOTGITCJI-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- NVTRPRFAWJGJAJ-UHFFFAOYSA-L EDTA monocalcium salt Chemical compound [Ca+2].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O NVTRPRFAWJGJAJ-UHFFFAOYSA-L 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
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- 150000003377 silicon compounds Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940079864 sodium stannate Drugs 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- BAWFMRPQYKKOLX-UHFFFAOYSA-B tetraaluminum;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Al+3].[Al+3].[Al+3].[Al+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O.[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O.[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O BAWFMRPQYKKOLX-UHFFFAOYSA-B 0.000 description 1
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- PGAPATLGJSQQBU-UHFFFAOYSA-M thallium(i) bromide Chemical compound [Tl]Br PGAPATLGJSQQBU-UHFFFAOYSA-M 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- YTSDVWYUJXKXCC-UHFFFAOYSA-L zinc;2-[2-[carboxylatomethyl(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate Chemical compound [Zn+2].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O YTSDVWYUJXKXCC-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Paints Or Removers (AREA)
- Surface Treatment Of Optical Elements (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、薄型軽量で優れた透明
性、耐擦傷性、密着性、反射防止性を有するプラスチッ
クレンズに関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a plastic lens which is thin and lightweight and has excellent transparency, scratch resistance, adhesion and antireflection property.
【０００２】[0002]
【従来の技術】近年、レンズ材料として従来のガラスに
代わってプラスチックが使用されるようになってきた。
特に眼鏡用レンズ材料としてその傾向は顕著なものがあ
る。プラスチックレンズ成形物は、軽量、易加工性、耐
衝撃性などの長所がある反面、硬度が不十分で傷がつき
易い、溶媒に侵されやすい、帯電し易くほこりを吸着す
る、耐熱性が不十分、などの欠点がある。ところで、従
来、プラスチック製眼鏡用レンズは、大半が、ＣＲ−39
という商品名で市販されているアリルジグリコールカー
ボネート（以下ＡＤＣと略す）というモノマーを注型重
合することにより製造されていた。このレンズは、屈折
率が約１．５０であり、ガラスレンズの屈折率約１．５
２〜１．８０に比べ低いことから、近視用レンズの場
合、縁の厚さが厚くなり、老視用レンズでは中心部が厚
くなるという欠点があり、装用者から嫌われる主因とな
っていた。2. Description of the Related Art In recent years, plastic has come to be used as a lens material instead of conventional glass.
In particular, there is a remarkable tendency as a lens material for spectacles. Plastic lens moldings have the advantages of light weight, easy processability, impact resistance, etc., but on the other hand, they have insufficient hardness and are easily scratched, easily attacked by solvents, easily charged and adsorb dust, and have poor heat resistance. There are drawbacks such as sufficient. By the way, in the past, most plastic spectacle lenses are CR-39.
It was produced by casting polymerization of a monomer called allyl diglycol carbonate (hereinafter abbreviated as ADC), which is commercially available under the trade name of. This lens has a refractive index of about 1.50, and the glass lens has a refractive index of about 1.5.
Since it is lower than 2 to 1.80, the lens for myopia has a thick edge and the lens for presbyopia has a defect that the central portion is thick, which is a main cause disliked by the wearer. .
【０００３】そこで、ＡＤＣの屈折率より高い屈折率を
有するモノマーの開発が進められ、例えば、特開昭５５
−１３７４７号、特開昭５６−１６６２１４号、特開昭
５７−２３６１１号、特開昭５７−５４９０１号などが
提案された。特開昭６０−１９９０１６号公報で提案さ
れているポリイソシアネートとポリオールおよび／また
はポリチオール化合物によるポリウレタン系プラスチッ
クレンズもその一つである。ポリウレタン系プラスチッ
クレンズは、屈折率が高く（例えば１．６０、１．６
６）、優れた透明性、染色性、耐衝撃性を有しており、
眼鏡用プラスチックレンズとして実用化されている。Therefore, the development of a monomer having a refractive index higher than that of ADC has been promoted, and, for example, JP-A-55 is used.
No. 13747, JP-A-56-166214, JP-A-57-23611 and JP-A-57-54901 have been proposed. One of them is a polyurethane plastic lens made of a polyisocyanate, a polyol and / or a polythiol compound, which is proposed in JP-A-60-199016. Polyurethane plastic lenses have a high refractive index (eg 1.60, 1.6
6), has excellent transparency, dyeability and impact resistance,
It has been put to practical use as a plastic lens for eyeglasses.
【０００４】しかし、ポリウレタン系プラスチックレン
ズは他のプラスチックレンズに比べて比較的柔らかく耐
擦傷性が不充分である。他のプラスチックレンズにおい
ては耐擦傷性を改善するために、「有機ケイ素化合物又
はその加水分解物を主成分（樹脂成分又は塗膜形成成
分）とするコーティング組成物」（例えば、特開昭５２
−１１２６１号参照）等の提案、あるいは、「有機ケイ
素化合物又はその加水分解物」にコロイド状に分散した
シリカゾルを添加したものが提案され（例えば、特開昭
５３−１１１３３６号参照）、眼鏡レンズ用として実用
化されている。However, polyurethane plastic lenses are relatively soft and have insufficient scratch resistance as compared with other plastic lenses. In other plastic lenses, in order to improve scratch resistance, "a coating composition containing an organic silicon compound or a hydrolyzate thereof as a main component (resin component or coating film forming component)" (for example, JP-A-52)
No. 11261)), or the addition of a colloidally dispersed silica sol to an “organosilicon compound or its hydrolyzate” (see, for example, JP-A-53-1113336), spectacle lenses It has been put to practical use for business.
【０００５】また、プラスチックレンズにおける多層膜
反射防止コートとしては、ＳｉＯ 2とＡｌ2 Ｏ3 に加え
てＺｒＯ2 あるいはＴｉＯ2 を用いる多層膜コーティン
グの提案（特開昭５２−１５６６４３号）、Ｔａ2 Ｏ5
とＺｒＯ2 を高屈折率成分として含む提案（特開昭５５
−２２７０４号）、ＳｉＯ2 ないしはＳｉＯに加えてＴ
ａ2 Ｏ5 を用いる提案（特開昭６０−２２５１０１号）
等がなされている。As a multilayer antireflection coating for plastic lenses, a multilayer coating using ZrO 2 or TiO 2 in addition to SiO 2 and Al 2 O 3 has been proposed (Japanese Patent Laid-Open No. 52-156643), Ta 2 O 5
And ZrO 2 as a high refractive index component (JP-A-55)
22704), SiO 2 or T in addition to SiO
Proposal using a 2 O 5 (Japanese Patent Laid-Open No. 60-225101)
And so on.
【０００６】[0006]
【発明が解決しようとする課題】ポリウレタン系プラス
チックレンズは従来のＡＤＣ樹脂のレンズ比べてに屈折
率が高いために前述の有機ケイ素化合物あるいは有機ケ
イ素化合物にシリカゾルを加えたコーティングでは、硬
質塗膜に干渉縞が見え、レンズの見栄えが悪いという第
１の問題点があった。Polyurethane-based plastic lenses have a higher refractive index than conventional ADC resin lenses. Therefore, the coating of organosilicon compound or organosilicon compound with silica sol gives a hard coating film. The first problem is that interference fringes are visible and the appearance of the lens is poor.
【０００７】また、その硬質塗膜上に形成する無機酸化
物よりなる多層膜反射防止コートにも影響を与え、反射
防止コートが設計通りの性能を発揮できなかったり、バ
ラツキを生じるという第２の問題点があった。また、第
２の問題点のために反射防止コートには反射率の低い高
性能なコーティングを施しにくいという第３の問題点が
あった。In addition, it also affects the multi-layer anti-reflection coating made of an inorganic oxide formed on the hard coating film, and the anti-reflection coating may not exhibit the performance as designed or may have variations. There was a problem. Further, due to the second problem, there is a third problem that it is difficult to apply a high-performance coating having a low reflectance to the antireflection coat.
【０００８】したがって、本発明の第１の目的は、薄
く、軽量な眼鏡用レンズを提供できる高屈折率のポリウ
レタン系プラスチックレンズに対し、硬質塗膜に干渉縞
が見えず、かつ反射色にムラやバラツキがなく、反射率
の低い高性能な反射防止性能を与えることにある。ま
た、本発明の第２の目的は、透明性、耐擦傷性、表面硬
度、耐磨耗性、可撓性、帯電防止性、耐熱性、耐水性、
耐薬品性、などに優れたプラスチックレンズを提供する
ことにある。Therefore, a first object of the present invention is to provide a thin and lightweight spectacle lens with a high refractive index polyurethane-based plastic lens, in which interference fringes are not visible on the hard coating and the reflection color is uneven. It is to provide high-performance antireflection performance with low reflectance and no variation. A second object of the present invention is transparency, scratch resistance, surface hardness, abrasion resistance, flexibility, antistatic property, heat resistance, water resistance,
It is to provide a plastic lens having excellent chemical resistance.
【０００９】[0009]
【課題を解決するための手段】本発明者らは、前述の問
題点を解決するために鋭意研究した結果、ポリイソシア
ネートとポリオールおよび／又はポリチオールとを重合
させて得られるポリウレタン系プラスチックレンズ基材
と、前記プラスチックレンズ基材の表面に設けられ、 一般式：Ｒ1 a Ｒ2 b Ｓｉ（ＯＲ3)4-(a+b) …（式I ） （但し、式中、Ｒ1 は、官能基又は不飽和２重結合を有
する炭素数４〜１４の有機基であり、Ｒ2 は、炭素数１
〜６の炭化水素基又はハロゲン化炭化水素基であり、Ｒ
3 は、炭素数１〜４のアルキル基、アルコキシアルキル
基又はアシル基であり、ａ及びｂは、それぞれ０又は１
であり、かつａ＋ｂは、１又は２である。）で表される
有機ケイ素化合物又はその加水分解物中に、酸化アンチ
モンゾル、酸化ジルコニウムゾル、酸化チタンゾル、酸
化スズゾル、酸化タンタルゾル、酸化タングステンゾ
ル、酸化アルミニウムゾル、酸化チタンと酸化セリウム
の複合ゾル、酸化チタンと鉄の複合ゾル、酸化スズと酸
化タングステンの複合ゾルで酸化スズゾルを被覆したゾ
ルから選ばれる少なくとも１種の無機微粒子を含有して
なる有機ケイ素系コーティング組成物からなる硬質塗膜
と、前記硬質塗膜上に設けられた、チタン、ケイ素の酸
化物を含む多層反射防止膜とからなることを特徴とする
反射防止性プラスチックレンズを提供する。DISCLOSURE OF THE INVENTION As a result of intensive studies to solve the above-mentioned problems, the present inventors have made a polyurethane-based plastic lens substrate obtained by polymerizing polyisocyanate and polyol and / or polythiol. And provided on the surface of the plastic lens substrate, having the general formula: R 1 a R 2 b Si (OR 3 ) 4- (a + b) (Formula I) (wherein R 1 is a functional group). A group or an organic group having an unsaturated double bond and having 4 to 14 carbon atoms, and R 2 has 1 carbon atom.
~ 6 hydrocarbon groups or halogenated hydrocarbon groups, R
3 is an alkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group or an acyl group, and a and b are 0 or 1 respectively.
And a + b is 1 or 2. ) In the organosilicon compound or a hydrolyzate thereof, antimony oxide sol, zirconium oxide sol, titanium oxide sol, tin oxide sol, tantalum oxide sol, tungsten oxide sol, aluminum oxide sol, a composite sol of titanium oxide and cerium oxide, A hard coating film comprising an organosilicon coating composition containing at least one kind of inorganic fine particles selected from a sol obtained by coating a tin oxide sol with a composite sol of titanium oxide and iron, a composite sol of tin oxide and tungsten oxide, There is provided an antireflection plastic lens comprising a multilayer antireflection film containing an oxide of titanium or silicon provided on the hard coating film.
【００１０】[0010]
（１）プラスチックレンズ基材の説明：本発明におい
て、プラスチックレンズ基材を製造するために使用する
イソシアネート系モノマー成分には特に限定はないが、
ポリイソシアネートとしては、トリレンジイソシアネー
ト、キシレンジイソシアネート、ジフェニルメタンジイ
ソシアネート、ポリメリック型ジフェニルメタンジイソ
シアネート、ナフチレンジイソシアネート、ヘキサメチ
レンジイソシアネート、水添ジフェニルメタンジイソシ
アネート、リジンジイソシアネート、トリフェニルメタ
ンジイソシアネート、トリス（イソシアネートフェニ
ル）チオフォスフェート、トランス−シクロヘキサレン
１，４−ジイソシアネート、Ｐ−フェニレンジイソシア
ネート、１，８−ジイソシアネート−４−イソシアネー
トメチルオクタン、リジンエステルトリイソシアネー
ト、１，３，６−ヘキサメチレントリイソシアネート、
ビシクロヘキサントリイソシアネート、イソホロンジイ
ソシアネート等の化合物及びそれらの化合物の、アロフ
ァネート変成体、ビュレット変成体、イソシアヌレート
変成体、ポリオール変成体又は、ポリチオールとのアダ
クト変成体等がある。また、上記化合物を単独又は混合
物として用いてもよい。上記の他には２以上の官能基を
有するイソシアネート化合物も用いることができる。さ
らに、芳香族イソシアネート化合物にハロゲン（Ｃｌな
いしはＢｒ）を導入してもよい。(1) Description of plastic lens substrate: In the present invention, the isocyanate-based monomer component used for producing the plastic lens substrate is not particularly limited,
As the polyisocyanate, tolylene diisocyanate, xylene diisocyanate, diphenylmethane diisocyanate, polymeric diphenylmethane diisocyanate, naphthylene diisocyanate, hexamethylene diisocyanate, hydrogenated diphenylmethane diisocyanate, lysine diisocyanate, triphenylmethane diisocyanate, tris (isocyanatophenyl) thiophosphate, trans -Cyclohexalene 1,4-diisocyanate, P-phenylene diisocyanate, 1,8-diisocyanate-4-isocyanate methyl octane, lysine ester triisocyanate, 1,3,6-hexamethylene triisocyanate,
There are compounds such as bicyclohexane triisocyanate and isophorone diisocyanate, and allophanate-modified compounds, buret-modified compounds, isocyanurate-modified compounds, polyol-modified compounds, and adduct-modified compounds thereof with polythiols. Moreover, you may use the said compound individually or as a mixture. In addition to the above, an isocyanate compound having two or more functional groups can also be used. Further, halogen (Cl or Br) may be introduced into the aromatic isocyanate compound.
【００１１】特に好ましいイソシアネート化合物として
は、キシレンジイソシアネート、イソホロンジイソシア
ネート、ヘキサメチレンジイソシアネート等の無黄変型
イソシアネート化合物である。ポリオールおよびまたは
ポリチオール化合物についても特に限定はない。ポリオ
ールの例として挙げられる化合物は、エチレングリコー
ル、ジエチレングリコール、プロピレングリコール、グ
リセリンブタンジオール、グリセロール、ペンタンジオ
ール、ヘキサントリオール、シクロヘキサンジオール、
シクロヘキサントリオール、モノチオグリセロール、１
−メルカプトメチル１，１−ジヒドロキシプロパン、ま
たポリチオールの例としては、エタンジチオール、ジメ
ルカプトプロパノール、４−ジメルカプト−２，３−ヒ
ドロキシブタン、プロパンジチオール、ペンタンジチオ
ール、ブタンジチオール、ヘプタンジチオール、オクタ
ンジチオール、シクロヘキサンジチオール、シクロヘプ
タンジチオール、２，５−ジクロロベンゼン−１，３−
ジチオール、ペンタエリスリトールテトラキス−３−メ
ルカプトプロピオネート、ペンタエリスリトールテトラ
キスチオグリコレート等が挙げられる。Particularly preferred isocyanate compounds are non-yellowing type isocyanate compounds such as xylene diisocyanate, isophorone diisocyanate and hexamethylene diisocyanate. The polyol and / or polythiol compound is also not particularly limited. Examples of the compound of the polyol include ethylene glycol, diethylene glycol, propylene glycol, glycerin butanediol, glycerol, pentanediol, hexanetriol, cyclohexanediol,
Cyclohexanetriol, monothioglycerol, 1
Examples of mercaptomethyl 1,1-dihydroxypropane and polythiol include ethanedithiol, dimercaptopropanol, 4-dimercapto-2,3-hydroxybutane, propanedithiol, pentanedithiol, butanedithiol, heptanedithiol, octanedithiol, Cyclohexanedithiol, cycloheptanedithiol, 2,5-dichlorobenzene-1,3-
Examples include dithiol, pentaerythritol tetrakis-3-mercaptopropionate, pentaerythritol tetrakisthioglycolate, and the like.
【００１２】特に好ましいのはメルカプト基を分子内に
２個以上有するチオールの誘導体である。なお、これら
のポリオールおよびまたはポリチオールは１種で用いて
もよいし、２種以上で用いることもできる。本発明にお
いては、上記のような、ポリイソシアネートと、ポリオ
ール及びまたはポリチオールとを、−ＮＣＯ基／−ＯＨ
基及びまたは−ＳＨ基の和＝０．５〜１．５の比率、好
ましくは１．０の比率となるように混合重合する。この
範囲を外れると、屈折率や加工性等、レンズとして望ま
しい物性が悪化する。Particularly preferred are thiol derivatives having two or more mercapto groups in the molecule. These polyols and / or polythiols may be used alone or in combination of two or more. In the present invention, the polyisocyanate and the polyol and / or the polythiol as described above are combined with -NCO group / -OH.
The mixture polymerization is carried out so that the sum of the groups and / or --SH groups = 0.5 to 1.5, preferably 1.0. Outside of this range, physical properties desirable as a lens, such as refractive index and workability, deteriorate.
【００１３】上記成分の重合は、重合開始剤の存在で行
うのが一般的である。開始剤としては、例えばジブチル
錫ジアセテート、ジブチル錫ジ−２−エチルヘキソエー
ト、ジブチル錫ジマレエート、ジブチル錫ジラウレー
ト、ジブチル錫ジクロライド等の有機錫化合物、メチル
アミン、エチルアミン、ｔ−ブチルアミン、メチルエチ
ルアミン、Ｎ，Ｎ−ジエタノール−ｐ−トルイジン、ジ
メチル−ｐ−トルイジン、ジフェニルアミン、ｏ−ニト
ロアミン、ｐ−ブロモアニリン、２，４，６−トリブロ
モアニリン等のアミン化合物等を使用することができ
る。開始剤の使用量は、用いるモノマーの種類や他の状
況にも左右されるが、一般にはモノマー混合物中に０．
０３〜０．３重量％、好ましくは０．０５〜０．１５重
量％とする。The above components are generally polymerized in the presence of a polymerization initiator. Examples of the initiator include organic tin compounds such as dibutyltin diacetate, dibutyltin di-2-ethylhexoate, dibutyltin dimaleate, dibutyltin dilaurate and dibutyltin dichloride, methylamine, ethylamine, t-butylamine, methylethylamine. , N, N-diethanol-p-toluidine, dimethyl-p-toluidine, diphenylamine, o-nitroamine, p-bromoaniline, 2,4,6-tribromoaniline and other amine compounds can be used. The amount of initiator used will depend on the type of monomers used and other circumstances, but is generally 0.
The amount is 03 to 0.3% by weight, preferably 0.05 to 0.15% by weight.
【００１４】本発明においては、更に離型剤をモノマー
混合物に添加してもよい。使用しうる離型剤は、鉱油系
離型剤、リン酸エステル系離型剤、脂肪酸アルキルエス
テル系離型剤、有機酸のグリセリドと合成樹脂とを複合
させた縮合体型離型剤等のうちいずれか１種である。こ
の離型剤の使用量は、モノマー混合物中に通常１０〜５
０００ｐｐｍ、好ましくは５００〜２０００ｐｐｍの濃
度とする。In the present invention, a releasing agent may be added to the monomer mixture. Among the release agents that can be used are mineral oil-based release agents, phosphate ester-based release agents, fatty acid alkyl ester-based release agents, and condensate-based release agents in which glycerides of organic acids and synthetic resins are combined. Any one. The amount of the release agent used is usually 10 to 5 in the monomer mixture.
The concentration is 000 ppm, preferably 500 to 2000 ppm.
【００１５】上記のような成分の他、原料混合物に紫外
線吸収剤、酸化防止剤等を添加してもよい。重合方法と
しては、通常注型重合方法が用いられ、上記のような各
種成分を均一に混合し、脱気した後、ガラス製または金
属製の鋳型中に注入し、重合反応を適切な温度で行う。
重合は低温で行うこともできる。重合温度は、使用する
モノマーの組み合わせや他の状況によって変動するが、
通常−１０℃〜１５０℃で行うのが好ましい。殊に、中
心厚の厚いレンズを製造する場合には、厚い部分におけ
る熱の発散が悪く、歪の原因となるので、このような場
合には、冷却しながら重合を行うのが好ましい。In addition to the above components, an ultraviolet absorber, an antioxidant, etc. may be added to the raw material mixture. As the polymerization method, usually a cast polymerization method is used, after uniformly mixing the various components as described above, after degassing, poured into a glass or metal mold, the polymerization reaction at an appropriate temperature. To do.
The polymerization can also be carried out at low temperatures. The polymerization temperature will vary depending on the combination of monomers used and other circumstances,
Usually, it is preferably carried out at -10 ° C to 150 ° C. In particular, when producing a lens having a thick center thickness, heat is not well radiated in a thick portion and causes distortion. Therefore, in such a case, it is preferable to carry out polymerization while cooling.
【００１６】反応時間は、使用するモノマーや開始剤、
重合温度等によって一義的には決定できないが、通常５
〜５０時間、好ましくは１０〜２５時間である。このよ
うにして得られるポリウレタン系プラスチックレンズ基
材は、高屈折率を有し、しかも重合歪あるいは成形歪を
有しない。 （２）有機ケイ素系コーティング組成物からなる硬質塗
膜の説明：有機ケイ素系コーティング組成物のビヒクル
成分として用いられる一般式(I)の化合物のうち、Ｒ1
が官能基としてエポキシ基を有するものについて言う
と、例えば、次のものが使用される。The reaction time depends on the monomers and initiators used,
Although it cannot be uniquely determined by the polymerization temperature, it is usually 5
~ 50 hours, preferably 10-25 hours. The polyurethane plastic lens substrate thus obtained has a high refractive index and has no polymerization strain or molding strain. (2) Description of hard coating film composed of organosilicon coating composition: R 1 of the compounds of general formula (I) used as a vehicle component of the organosilicon coating composition
As for those having an epoxy group as a functional group, for example, the following are used.
【００１７】(1) 一般式（II）：(1) General formula (II):
【００１８】[0018]
【化１】 [Chemical 1]
【００１９】（但し、式中、Ｒ4 は、炭素数１〜４のア
ルキル基又はアルコキシアルキル基又はアシル基、 Ｒ5
は、炭素数１〜６の炭化水素基又はハロゲン化炭素化水
素基、Ｒ6 は、水素またはメチル基、ｍは２又は３、ｐ
は１〜６、ｑは０〜２である。）で表わされる化合物。(In the formula, R 4 is an alkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group, an acyl group, R 5
Is a hydrocarbon group having 1 to 6 carbon atoms or a halohydrocarbon group, R 6 is hydrogen or a methyl group, m is 2 or 3, p
Is 1 to 6, and q is 0 to 2. ) The compound represented by.
【００２０】(2) 一般式（III ）：(2) General formula (III):
【００２１】[0021]
【化２】 [Chemical 2]
【００２２】（但し、Ｒ7 は、炭素数１〜４のアルキル
基又はアルコキシアルキル基又はアシル基、Ｒ8 は、炭
素数１〜４の炭化水素基又はハロゲン化炭素化水素基、
１は２又は３、ｒは１〜４である。）で表わされる化合
物。上記一般式で表される化合物は、いずれもエポキシ
基を有するので、エポキシシランとも呼ばれる。(Wherein R 7 is an alkyl group or an alkoxyalkyl group having 1 to 4 carbon atoms or an acyl group, R 8 is a hydrocarbon group having 1 to 4 carbon atoms or a halogenated hydrocarbon group,
1 is 2 or 3, and r is 1-4. ) The compound represented by. The compounds represented by the above general formula all have an epoxy group, and are therefore called epoxysilanes.
【００２３】エポキシシランの具体例としては、例え
ば、γ−グリシドキシプロピルトリメトキシシラン、γ
−グリシドキシプロピルトリエトキシシラン、γ−グリ
シドキシプロピルトリメトキシエトキシシラン、γ−グ
リシドキシプロピルトリアセトキシシラン、γ−グリシ
ドキシプロピルメチルジメトキシシラン、γ−グリシド
キシプロピルメチルジエトキシシラン、β−（３，４−
エポキシシクロヘキシル）エチルトリエトキシシランな
どが挙げられる。Specific examples of the epoxysilane include, for example, γ-glycidoxypropyltrimethoxysilane, γ
-Glycidoxypropyltriethoxysilane, γ-glycidoxypropyltrimethoxyethoxysilane, γ-glycidoxypropyltriacetoxysilane, γ-glycidoxypropylmethyldimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane , Β- (3,4-
Epoxycyclohexyl) ethyltriethoxysilane and the like.
【００２４】また、一般式(I) の化合物のうち、Ｒ1 が
官能基としてエポキシ基を有するもの以外（ａ＝０のも
のを含む）の例としては、例えば、次の化合物が挙げら
れる。メチルトリメトキシシラン、メチルトリエトキシ
シラン、ビニルトリメトキシシラン、ビニルトリエトキ
シシラン、ビニルトリアセトキシシラン、ビニルトリメ
トキシエトキシシラン、γ−メタクリロキシプロピルト
リメトキシシラン、アミノメチルトリメトキシシラン、
３−アミノプロピルトリメトキシシラン、３−アミノプ
ロピルトリエトキシシラン、フエニルトリメトキシシラ
ン、フエニルトリエトキシシラン、γ−クロロプロピル
トリメトキシシラン、γ−メルカプトプロピルトリエト
キシシラン、３，３，３−トリフルオロプロピルトリメ
トキシシランなどの各種トリアルコキシシラン、トリア
シロキシシランあるいはトリアルコキシアルコキシシラ
ン化合物。Examples of compounds of the general formula (I) other than those having an epoxy group as a functional group for R 1 (including those having a = 0) include the following compounds. Methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriacetoxysilane, vinyltrimethoxyethoxysilane, γ-methacryloxypropyltrimethoxysilane, aminomethyltrimethoxysilane,
3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, γ-chloropropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, 3,3,3- Various trialkoxysilanes such as trifluoropropyltrimethoxysilane, triacyloxysilane or trialkoxyalkoxysilane compounds.
【００２５】以上例示した一般式(I) の化合物は、いず
れもＳｉ原子に結合するＯＲ3 基が３個ある（ａ＋ｂ＝
１）３官能の例であるが、ＯＲ3 基が２個ある（ａ＋ｂ
＝２）２官能の相当する化合物ももちろん使用すること
ができる。２官能の相当する化合物の例としては、ジメ
チルジメトキシシラン、ジフエニルジメトキシシラン、
メチルフエニルジメトキシシラン、メチルビニルジメト
キシシラン、ジメチルジエトキシシランなどがある。The compounds of the general formula (I) exemplified above all have three OR 3 groups bonded to the Si atom (a + b =
1) This is an example of trifunctionality, but there are two OR 3 groups (a + b
= 2) The corresponding difunctional compounds can of course also be used. Examples of difunctional corresponding compounds include dimethyldimethoxysilane, diphenyldimethoxysilane,
Examples include methylphenyldimethoxysilane, methylvinyldimethoxysilane, and dimethyldiethoxysilane.
【００２６】一般式(I) の化合物は、１種で使用しても
よいが、目的に応じて２種以上を混合して使用してもよ
い。特に、２官能の化合物を使用するときには、３官能
の化合物と併用することが好ましい。併用した場合に
は、平均で２＞ａ＋ｂ＞１となる。更に、ａ＋ｂ＝０の
４官能の相当する化合物を併用することも可能である。
４官能の相当する化合物の例としては、メチルシリケー
ト、エチルシリケート、イソプロピルシリケート、ｎ−
プロピルシリケート、ｎ−ブチルシリケート、ｔ−ブチ
ルシリケート、ｓｅｃ−ブチルシリケートなどが挙げら
れる。The compound of the general formula (I) may be used alone, or two or more kinds may be mixed and used depending on the purpose. Particularly, when a bifunctional compound is used, it is preferably used in combination with a trifunctional compound. When used together, 2> a + b> 1 on average. Further, it is also possible to use a compound corresponding to a tetrafunctional compound of a + b = 0.
Examples of corresponding tetrafunctional compounds are methyl silicate, ethyl silicate, isopropyl silicate, n-
Propyl silicate, n-butyl silicate, t-butyl silicate, sec-butyl silicate and the like can be mentioned.
【００２７】一般式(I) の化合物は、そのまま使用して
もよいが、反応速度を増し、硬化温度を下げる目的で加
水分解物として使用することが望ましい。２〜４官能の
化合物の中で同一官能数の化合物を２種以上を併用する
場合、或いは異なる官能数の化合物を２種以上併用する
場合、加水分解後に併用してもよいし、加水分解前に併
用して共加水分解を行なってもよい。加水分解によりＨ
ＯＲ3 なるアルコールが遊離され、一般式(I) の化合物
は、相当するシラノール：The compound of the general formula (I) may be used as it is, but it is preferably used as a hydrolyzate for the purpose of increasing the reaction rate and lowering the curing temperature. When two or more compounds having the same functional number are used in combination among two to four functional compounds, or when two or more compounds having different functional numbers are used in combination, they may be used in combination after hydrolysis or before hydrolysis. May be used in combination for co-hydrolysis. H by hydrolysis
The alcohol OR 3 is liberated and the compound of general formula (I) has the corresponding silanol:
【００２８】[0028]
【化３】 [Chemical 3]
【００２９】になる。シラノールは、速やかに脱水縮合
が進み、オリゴマーになる。したがって、この反応が十
分に進むように、加水分解後、１〜２４時間放置（養
生）させてもよい。無機微粒子成分として用いられるも
のはコロイド状に分散した五酸化あるいは三酸化アンチ
モンゾル、酸化ジルコニウムゾル、酸化チタンゾル、酸
化スズゾル、酸化タンタルゾル、酸化タングステンゾ
ル、酸化アルミニウムゾル、酸化チタンと酸化セリウム
の複合ゾル、酸化チタンと鉄の複合ゾル、酸化スズと酸
化タングステンの複合ゾルで酸化スズゾルを被覆したゾ
ル（変性ゾル）から選ばれる少なくとも１種のゾルであ
る。It becomes Silanol rapidly undergoes dehydration condensation to become an oligomer. Therefore, it may be left (cured) for 1 to 24 hours after hydrolysis so that the reaction proceeds sufficiently. As the inorganic fine particle component, colloidally dispersed antimony pentoxide or antimony trioxide sol, zirconium oxide sol, titanium oxide sol, tin oxide sol, tantalum oxide sol, tungsten oxide sol, aluminum oxide sol, composite sol of titanium oxide and cerium oxide are used. At least one kind of sol selected from a composite sol of titanium oxide and iron, a sol obtained by coating a tin oxide sol with a composite sol of tin oxide and tungsten oxide (modified sol).
【００３０】ゾルの粒子径は１〜２００ｍμ、特に５〜
１００ｍμのものが好ましい。これより小さいと製造が
困難であり、ゾル自身の安定性も悪く、かつ効果も小さ
い。これより大きいと、コーティング組成物の安定性、
硬質塗膜の透明性、平滑性などが低下する。これらのゾ
ルは各々公知であり、一部市販品として入手可能であ
る。The particle size of the sol is 1 to 200 mμ, and especially 5 to
It is preferably 100 mμ. If it is smaller than this, the production is difficult, the stability of the sol itself is poor, and the effect is small. Above this, the stability of the coating composition,
The transparency and smoothness of the hard coating film are reduced. These sols are publicly known, and some of them are commercially available.
【００３１】上記ゾルのうち、酸化スズゾルの微粒子を
酸化タングステンと酸化スズの複合ゾルで被覆した変性
ゾルが好ましく、これは、以下のようなものである。こ
の変性ゾルは、「酸化スズ（ゾル）のコロイド粒子を
核に、その周囲を酸化スズ−酸化タングステン複合体
（ゾル）のコロイド粒子が完全に又は不完全に取り囲
んだ、二重構造を持つコロイド粒子」が分散媒中にコロ
イド状に分散したものである。核となる酸化スズのコロ
イド粒子の粒径は一般に４〜50nmである。周囲を取り
囲む複合体のコロイド粒子の粒径は、一般に２〜７nm
である。核となる酸化スズ粒子は、正に帯電してい
る。そのため、これをそのまま成分（ａ）に混合する
と、成分（ａ）の分子は−SiＯ- Ｈ+ に由来して、負の
電荷を持つので、凝集（ゲル化）する。それに対して、
複合体粒子は負に帯電している。そのため、これを成
分（ａ）と混合しても凝集しない。Among the above-mentioned sol, a modified sol in which fine particles of tin oxide sol are coated with a composite sol of tungsten oxide and tin oxide is preferable, which is as follows. This modified sol is a colloid having a double structure in which colloidal particles of tin oxide (sol) are the core and colloidal particles of tin oxide-tungsten oxide composite (sol) surround it completely or incompletely. "Particles" are dispersed in a dispersion medium in a colloidal form. The core tin oxide colloidal particles generally have a particle size of 4 to 50 nm. The particle size of the surrounding colloidal particles is generally 2 to 7 nm.
Is. The tin oxide particles serving as the core are positively charged. Therefore, if this is mixed with the component (a) as it is, the molecule of the component (a) originates in -SiO - H + and has a negative charge, and thus aggregates (gels). On the other hand,
The composite particles are negatively charged. Therefore, even if this is mixed with the component (a), it does not aggregate.
【００３２】酸化スズ−酸化タングステン複合体ゾル
は、一般には、タングステン酸ナトリウム水溶液をイオ
ン交換して製造したタングステン酸水溶液に、スズ酸ナ
トリウム水溶液を室温にて強撹拌下に加えることによっ
て、製造される。複合体ゾルのＷＯ3 ／SnＯ2 の重量比
は一般に0.5 〜100 である。0.5 より小さくても100 よ
り大きくとも、本発明の構成要件であるコーティング組
成物を調製して硬質塗膜を形成したとき、性能の劣った
硬質塗膜しか得られない。The tin oxide-tungsten oxide composite sol is generally produced by adding an aqueous sodium stannate solution at room temperature with vigorous stirring to an aqueous tungstic acid solution produced by ion exchange of an aqueous sodium tungstate solution. It The WO 3 / SnO 2 weight ratio of the composite sol is generally 0.5-100. When it is less than 0.5 or more than 100, when a coating composition, which is a constituent of the present invention, is prepared to form a hard coating, only a hard coating having poor performance can be obtained.
【００３３】変性ゾルは、酸化スズの水性ゾルの“Sn
Ｏ2 換算で100 重量部”に対して、複合体の水性ゾル
を“ＷＯ3 とSnＯ2 の合計重量換算で２〜100 重量部”
を、室温にて強撹拌下に加えることによって、製造され
る。この場合も、２重量部より少なくとも100 重量部よ
り多くとも、本発明のコーティング組成物を調製して硬
質塗膜を形成したとき、性能の劣った硬質塗膜しか得ら
れない。変性ゾルの二重構造コロイド粒子の粒径は、一
般に4.5 〜60nmである。酸化スズの水性ゾルに複合体
の水性ゾルを混合すると、酸化スズの粒子と複合体
の粒子とは、化学的に結合するものと推定される。そ
のため、製造された変性ゾルは安定に存在するものと推
定される。このような変性ゾル自身は特開平３−217230
号に詳細に記載されているように公知である。The modified sol is "Sn" which is an aqueous sol of tin oxide.
" 2 to 100 parts by weight in terms of the total weight of WO 3 and SnO 2 " of the aqueous sol of the composite with respect to 100 parts by weight in terms of O 2.
Is added at room temperature with vigorous stirring. Also in this case, when the coating composition of the present invention is prepared to form a hard coating film, even if it is more than 2 parts by weight and at least 100 parts by weight, only a hard coating film having poor performance can be obtained. The particle size of the double-structured colloidal particles of the modified sol is generally 4.5 to 60 nm. When an aqueous sol of a composite is mixed with an aqueous sol of tin oxide, it is presumed that the particles of tin oxide and the particles of the composite are chemically bonded. Therefore, it is presumed that the produced modified sol is stable. Such modified sol itself is disclosed in JP-A-3-217230.
Are well known in the art.
【００３４】ゾルは水又は有機溶媒又は両者の混合溶媒
に分散させたコロイド溶液であり、適当なアルカリ、特
に有機アミンを添加して安定化させたり、各種有機酸を
用いて安定化させたり、あるいは界面活性剤によって安
定化させたものを用いることができる。上述した酸化ア
ンチモンゾル、酸化ジルコニアゾル、酸化チタンゾル、
酸化スズゾル、酸化タンタルゾル、酸化タングステンゾ
ル、酸化チタンと酸化セリウムの複合ゾル、酸化チタン
と鉄の複合ゾル並びに酸化スズと酸化タングステンの複
合ゾルで酸化スズゾルを被覆したゾル（変性ゾル）は屈
折率が高く好ましい。これらのゾルは単独で用いてもあ
るいは２種類以上の混合物として用いてもよい。The sol is a colloidal solution dispersed in water or an organic solvent or a mixed solvent of both, and is stabilized by adding an appropriate alkali, particularly an organic amine, or by using various organic acids, Alternatively, those stabilized with a surfactant can be used. The above-mentioned antimony oxide sol, zirconia oxide sol, titanium oxide sol,
Tin oxide sol, tantalum oxide sol, tungsten oxide sol, composite sol of titanium oxide and cerium oxide, composite sol of titanium oxide and iron, and sol obtained by coating tin oxide sol with composite sol of tin oxide and tungsten oxide (modified sol) have a refractive index Highly preferred. These sols may be used alone or as a mixture of two or more kinds.
【００３５】コーティング組成物には、ビヒクル成分を
重合させて３次元網目構造の硬質塗膜を形成させる上で
時間を短縮させるために、必要に応じ、硬化触媒を使用
することができる。但し、コーティング組成物の安定性
を損なうものは好ましくなく、好ましくは、例えば次の
ようなものが使用される。A curing catalyst can be used in the coating composition, if necessary, in order to shorten the time required for polymerizing the vehicle component to form a hard coating film having a three-dimensional network structure. However, those that impair the stability of the coating composition are not preferable, and the following are preferably used.
【００３６】１．アミン類：モノエタノールアミン、ジ
エタノールアミン、イソプロパノールアミン、エチレン
ジアミン、イソプロピルアミン、ジイソプロピルアミ
ン、モルホリン、トリエタノールアミン、ジアミノプロ
パン、アミノエチルエタノールアミン、ジシアンジアミ
ド、トリエチレンジアミン、２−エチル−４−メチルイ
ミダゾール。1. Amines: monoethanolamine, diethanolamine, isopropanolamine, ethylenediamine, isopropylamine, diisopropylamine, morpholine, triethanolamine, diaminopropane, aminoethylethanolamine, dicyandiamide, triethylenediamine, 2-ethyl-4-methylimidazole.
【００３７】２．各種金属錯化合物：一般式：ＡｌＸn
Ｙ3-n （但し、式中、ＸはＯＬ（Ｌは低級アルキル
基）、Ｙは一般式Ｍ1 ＣＯＣＨ2 ＣＯ2 Ｍ2 （Ｍ1 、Ｍ
2 は低級アルキル基）及びＭ1 ＣＯＣＨ2 ＣＯＯＭ2 に
由来する配位子から選ばれる少くとも１つで、ｎは０又
は１又は２である）で示されるアルミニウムキレート化
合物。2. Various metal complex compounds: General formula: AlX n
Y 3-n (wherein, X is OL (L is a lower alkyl group), Y is a general formula M 1 COCH 2 CO 2 M 2 (M 1 , M
2 is a lower alkyl group) and at least one selected from ligands derived from M 1 COCH 2 COOM 2 , and n is 0 or 1 or 2).
【００３８】特に有用なキレート化合物としては、溶解
性、安定性、触媒効果の観点から、アルミニウムアセチ
ルアセトネート、アルミニウムビスエチルアセトアセテ
ートモノアセチルアセトネート、アルミニウム−ジ−ｎ
−ブトキシド−モノエチルアセトアセテート、アルミニ
ウム−ジ−ｉｓｏ−プロポキシドーモノメチルアセトア
セテートなどである。Particularly useful chelate compounds are aluminum acetylacetonate, aluminum bisethylacetoacetate monoacetylacetonate and aluminum-di-n from the viewpoint of solubility, stability and catalytic effect.
-Butoxide-monoethyl acetoacetate, aluminum-di-iso-propoxide monomethyl acetoacetate and the like.
【００３９】その他、クロムアセチルアセトネート、チ
タニルアセチルアセトネート、コバルトアセチルアセト
ネート、鉄（３）アセチルアセトネート、マンガンアセ
チルアセトネート、ニッケルアセチルアセトネート。そ
の他の金属錯化合物としては、 一般式：Ｍ（ＣＨ2 Ｎ（ＣＨ2 ＣＯＯ）2 ）2 Ｎａ
X （x ＝１〜３）で示されるエチレンジアミン四酢酸金
属塩化合物。In addition, chromium acetylacetonate, titanyl acetylacetonate, cobalt acetylacetonate, iron (3) acetylacetonate, manganese acetylacetonate, nickel acetylacetonate. Other metal complex compounds include those represented by the general formula: M (CH 2 N (CH 2 COO) 2 ) 2 Na
An ethylenediaminetetraacetic acid metal salt compound represented by X (x = 1 to 3).
【００４０】特に有用な化合物は、エチレンジアミン四
酢酸カルシウム、エチレンジアミン四酢酸マグマネシウ
ム、エチレンジアミン四酢酸アルミニウム、エチレンジ
アミン四酢酸マンガン、エチレンジアミン四酢酸銅、エ
チレンジアミン四酢酸亜鉛、エチレンジアミン四酢酸
鉄、エチレンジアミン四酢酸コバルト、エチレンジアミ
ン四酢酸ビスマスである。Particularly useful compounds are calcium ethylenediamine tetraacetate, magnesium magnesium ethylenediaminetetraacetate, aluminum ethylenediaminetetraacetate, manganese ethylenediaminetetraacetate, copper ethylenediaminetetraacetate, zinc ethylenediaminetetraacetate, iron ethylenediaminetetraacetate, cobalt ethylenediaminetetraacetate. It is ethylenediamine tetraacetate bismuth.
【００４１】３．金属アルコキシド：アルミニウムトリ
エトキシド、アルミニウムトリｎ−プロポキシド、アル
ミニウムトリｎ−ブトキシド、テトラエトキシチタン、
テトラｎ−ブトキシチタン、テトラｉ−プロポキシチタ
ン。 ４．有機金属塩：酢酸ナトリウム、ナフテン酸亜鉛、ナ
フテン酸コバルト、オクチル酸亜鉛、オクチル酸スズ。3. Metal alkoxides: aluminum triethoxide, aluminum tri n-propoxide, aluminum tri n-butoxide, tetraethoxy titanium,
Tetra n-butoxy titanium, tetra i-propoxy titanium. 4. Organic metal salts: sodium acetate, zinc naphthenate, cobalt naphthenate, zinc octylate, tin octylate.
【００４２】５．過塩素酸塩：過塩素酸マグネシウム、
過塩素酸アンモニウム。 ６．有機酸又はその無水物：マロン酸、コハク酸、酒石
酸、アジピン酸、アゼライン酸、マレイン酸、Ｏ−フタ
ル酸、テレフタル酸、フマル酸、イタコン酸、オキザロ
酢酸、無水コハク酸、無水マレイン酸、無水イタコン
酸、１，２−ジメチルマレイン酸無水物、無水フタル
酸、ヘキサヒドロフタル酸無水物、無水ナフタル酸。5. Perchlorate: magnesium perchlorate,
Ammonium perchlorate. 6. Organic acids or their anhydrides: malonic acid, succinic acid, tartaric acid, adipic acid, azelaic acid, maleic acid, O-phthalic acid, terephthalic acid, fumaric acid, itaconic acid, oxaloacetic acid, succinic anhydride, maleic anhydride, anhydrous Itaconic acid, 1,2-dimethylmaleic anhydride, phthalic anhydride, hexahydrophthalic anhydride, naphthalic anhydride.
【００４３】７．ルイス酸：塩化第二鉄、塩化アルミニ
ウム。 ８．ハロゲン化金属：塩化第一スズ、塩化第二スズ、臭
化スズ、塩化亜鉛、臭化亜鉛、四塩化チタン、臭化チタ
ン、臭化タリウム、塩化ゲルマニウム、塩化ハフニウ
ム、塩化鉛、臭化鉛。7. Lewis acid: ferric chloride, aluminum chloride. 8. Metal halides: stannous chloride, stannic chloride, tin bromide, zinc chloride, zinc bromide, titanium tetrachloride, titanium bromide, thallium bromide, germanium chloride, hafnium chloride, lead chloride, lead bromide.
【００４４】以上の触媒は、単独で使用することなく２
種以上混合して使用してもよい。特にビヒクル成分がエ
ポキシ基を持つときには、エポキシ基の開環重合触媒を
兼ねるものを使用してもよい。コーティング組成物の粘
度を低くするために、必要に応じて溶媒を使用すること
ができ、例えば、水、低級アルコール、アセトン、エー
テル、ケトン、エステルなどが使用される。The above catalysts can be used without being used alone.
You may use it in mixture of 2 or more types. In particular, when the vehicle component has an epoxy group, one that also serves as a ring-opening polymerization catalyst for the epoxy group may be used. If necessary, a solvent may be used to reduce the viscosity of the coating composition, and for example, water, lower alcohol, acetone, ether, ketone, ester and the like are used.
【００４５】本発明の構成要件であるコーティング組成
物においては、ビヒクル成分の１００重量部（固形分）
当たり、無機微粒子成分を１０〜４００重量部（固形
分）好ましくは５０〜２５０重量部（固形分）使用し、
ビヒクル成分と無機微粒子成分の合計１００重量部（固
形分）当たり、硬化触媒を０．００００１〜２０重量部
使用することが適当である。In the coating composition which is a constituent feature of the present invention, 100 parts by weight of the vehicle component (solid content)
Therefore, the inorganic fine particle component is used in an amount of 10 to 400 parts by weight (solid content), preferably 50 to 250 parts by weight (solid content),
It is appropriate to use 0.00001 to 20 parts by weight of the curing catalyst per 100 parts by weight (solid content) of the vehicle component and the inorganic fine particle component in total.
【００４６】溶媒は、組成物の粘度に応じて適当量使用
される。以上の成分の外に、更に必要に応じて、例え
ば、塗布される側の基材（成形物）との接着性改良、耐
候性向上などを目的として、或いはコーティング組成物
の安定性を向上させる目的で各種添加剤を併用してもよ
い。添加剤の例としてはｐＨ調節剤、粘度調節剤、レベ
リング剤、つや消し剤、染料、顔料、安定剤、紫外線吸
収剤、酸化防止剤、帯電防止剤などがある。The solvent is used in an appropriate amount depending on the viscosity of the composition. In addition to the above components, if necessary, for example, for the purpose of improving the adhesiveness with the substrate (molded product) on the side to be coated, improving the weather resistance, or improving the stability of the coating composition. Various additives may be used together for the purpose. Examples of additives include pH adjusters, viscosity adjusters, leveling agents, matting agents, dyes, pigments, stabilizers, UV absorbers, antioxidants, antistatic agents, and the like.
【００４７】その他、硬質塗膜の可撓性を向上させる目
的でエポキシ樹脂その他の有機ポリマーを併用してもよ
い。エポキシ樹脂としては、塗料、注形用に汎用されて
いる、ポリオレフィン系エポキシ、シクロペンタジエン
オキシドや、シクロヘキセンオキシド、あるいは、ポリ
グリシジルエステルなどの脂環式エポキシ樹脂、ポリグ
リシジルエーテル、エポキシ化植物油、ノボラック型フ
ェノール樹脂とエピクロルヒドリンから成る、エポキシ
ノホラック、更にはグリシジルメタクリレートとメチル
メタクリレートの共重合体などがある。In addition, an epoxy resin or other organic polymer may be used in combination for the purpose of improving the flexibility of the hard coating film. Epoxy resin, which is widely used for paints and casting, is a polyolefin-based epoxy, cyclopentadiene oxide, cyclohexene oxide, or alicyclic epoxy resin such as polyglycidyl ester, polyglycidyl ether, epoxidized vegetable oil, novolak. Epoxynoholaks consisting of phenolic resins and epichlorohydrin as well as copolymers of glycidyl methacrylate and methyl methacrylate.
【００４８】その他の有機ポリマーとしては、例えば、
ポリオール、繊維素系樹脂、メラミン樹脂などがある。
塗布時におけるフローを向上させ、硬質塗膜の平滑性を
向上させて硬質塗膜表面の摩擦係数を低下させる目的
で、各種の界面活性剤をコーティング組成物に併用する
ことも可能であり、とくにジメチルシロキサンとアルキ
レンオキシドとのブロックまたはグラフト共重合体、さ
らにはフッ素系界面活性剤などが有効である。Other organic polymers include, for example,
Examples include polyols, fibrin-based resins, and melamine resins.
For the purpose of improving the flow at the time of coating, improving the smoothness of the hard coating film and lowering the friction coefficient of the surface of the hard coating film, it is possible to use various surfactants in combination with the coating composition, in particular, Block or graft copolymers of dimethyl siloxane and alkylene oxide, and fluorine-based surfactants are effective.
【００４９】コーティング組成物を塗布し硬化させて得
られる硬質塗膜は、特にポリウレタン系プラスチックレ
ンズ基材の傷付き防止膜として有用である。塗布手段
は、刷毛塗り、浸漬、ロール塗り、スプレー塗装、流し
塗りなど通常の塗装法を用いることができる。更に、こ
のコーティング組成物を鋳型に塗布後、基材成形物とな
る原料注形重合してプラスチック成形物を成形したり、
コーティング組成物を成形物に塗布した後、未だ硬化し
ていない硬質塗膜表面を鋳型と密着させ、その上で硬質
塗膜を硬化させることもできる。The hard coating film obtained by applying and curing the coating composition is particularly useful as a scratch-preventing film for a polyurethane plastic lens substrate. As a coating means, a usual coating method such as brush coating, dipping, roll coating, spray coating and flow coating can be used. Furthermore, after applying this coating composition to a mold, casting polymerization of a raw material to be a base material molded product to mold a plastic molded product,
After applying the coating composition to the molded article, the surface of the hard coating which has not yet been cured can be brought into close contact with the mold, and then the hard coating can be cured.
【００５０】このコーティング組成物は、塗布した後、
多くの場合、加熱処理することにより硬化させて硬質塗
膜を得る。加熱温度は約５０〜２００℃好ましくは８０
〜１４０℃で十分な効果が得られる。硬質塗膜の厚さ
は、一般に乾燥後で３〜３０μ好ましくは５〜１０μも
あれば十分である。This coating composition, after being applied,
In many cases, it is cured by heat treatment to obtain a hard coating film. The heating temperature is about 50 to 200 ° C., preferably 80.
A sufficient effect can be obtained at a temperature of 140 ° C. The thickness of the hard coating is generally 3 to 30 μ, preferably 5 to 10 μ after drying.
【００５１】硬質塗膜は、透明で硬度特に耐スクラッチ
性に優れ、プラスチックレンズの問題点であった引っか
き傷による外観の低下を起こすことがなく、商品価値の
著しく高いレンズを提供できる。 （３）多層反射防止膜の説明：本発明における反射防止
膜は、低屈折率膜と高屈折率膜を交互に積層させ、この
時の高屈折率層として酸化チタン（ＴｉＯ2 ）、低屈折
率層として二酸化珪素（ＳｉＯ2 ）を用いたものが好ま
しい。基本的な膜構成としては、中屈折層と高屈折層と
低屈折層の膜厚（屈折率を考慮）が、それぞれλ／４、
λ／２、λ／４であるものや、高屈折層と低屈折層の膜
厚が、それぞれλ／２、λ／４であるものが好ましく、
前者の構成の場合は、基材側から数えて第１層目の膜は
ＴｉＯ2とＳｉＯ2 を用いた３層等価膜あるいは２層の
コンポジット膜としてもよい。また、第１層目には酸化
ジルコニウム（ＺｒＯ2 ）と酸化アルミニウム（Ａｌ2
Ｏ 3 ）の混合物質、または酸化プラセオジウム（Ｐｒ6
Ｏ11）とＡｌ2 Ｏ3 の混合物も用いることができる。The hard coating film is transparent and hardness, especially scratch resistant.
Excellent scratch resistance, which was a problem with plastic lenses
It does not deteriorate the appearance due to scratches,
A significantly higher lens can be provided. (3) Description of multilayer antireflection film: Antireflection in the present invention
The film is made by alternately laminating low refractive index films and high refractive index films.
Titanium oxide (TiO2) as a high refractive index layer2), Low refraction
Dioxide (SiO 2)2) Is preferred
Good As a basic film structure, a medium refraction layer and a high refraction layer
The thickness of the low refraction layer (considering the refractive index) is λ / 4,
λ / 2, λ / 4, high refractive index layer and low refractive index layer
It is preferable that the thicknesses are λ / 2 and λ / 4, respectively,
In the case of the former configuration, the first layer film counting from the substrate side is
TiO2And SiO2Of 3 layer equivalent film or 2 layer using
It may be a composite film. Also, the first layer is oxidized
Zirconium (ZrO2) And aluminum oxide (Al2
O 3) Or praseodymium oxide (Pr)6
O11) And Al2O3Mixtures of can also be used.
【００５２】ＴｉＯ2 を真空蒸着法により成膜する場
合、ＴｉＯ2 自身を蒸着源として用いることができる
が、一般にＴｉＯ2 はガス放出が多く、成膜時の安定性
に欠ける場合がある。この場合、蒸着源としてチタンの
低級酸化物、好ましくはＴｉＯX（１≦Ｘ＜２）を用
い、蒸着槽内にＯ2 ガスを導入する反応性蒸着法を用い
ることができる。この方法によると、極めて安定してＴ
ｉＯ2 膜を成膜することができる。When a film of TiO 2 is formed by the vacuum evaporation method, TiO 2 itself can be used as an evaporation source, but in general, TiO 2 releases a large amount of gas and may lack stability during film formation. In this case, a lower oxide of titanium, preferably TiO x (1 ≦ X <2) is used as the vapor deposition source, and a reactive vapor deposition method in which O 2 gas is introduced into the vapor deposition tank can be used. According to this method, T is extremely stable.
An iO 2 film can be formed.
【００５３】ＴｉＯ2 膜はプラスチックレンズ基材上に
使用した場合でも十分な耐久性があり、さらに２．２５
程度の高い屈折率を有するため、反射防止膜の設計上も
有利である。すなわち、反射率が低く、反射防止効果を
持つ波長域を広げることができ、上記の効果を得るため
の層数を減らすことができる。上記の反射防止膜を製膜
するに当たっては一般に真空蒸着法を用いることができ
るほか、上記の物質の焼結体を用いたスパッタリング法
や、イオンプレ−ティング法等の方法も用いることがで
きる。The TiO 2 film has sufficient durability even when used on a plastic lens base material.
Since it has a moderately high refractive index, it is advantageous in the design of the antireflection film. That is, it is possible to widen a wavelength range having a low reflectance and an antireflection effect, and it is possible to reduce the number of layers for obtaining the above effect. In forming the antireflection film, a vacuum deposition method can be generally used, and a sputtering method using a sintered body of the above substance, an ion plating method, or the like can also be used.
【００５４】以上のようにしてポリウレタン系プラスチ
ックレンズ基材上に有機ケイ素系コーティング組成物か
らなる硬質塗膜を形成し、その上に多層反射防止膜を形
成したレンズは、薄型軽量で、優れた透明性、耐擦傷
性、密着性、反射防止性を有する。以下、実施例により
本発明をより具体的に説明するが、本発明はこれに限ら
れるものではない。As described above, a lens in which a hard coating film made of an organosilicon coating composition is formed on a polyurethane plastic lens substrate, and a multilayer antireflection film is formed on the hard coating film is thin, lightweight and excellent. Has transparency, scratch resistance, adhesion, and antireflection. Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.
【００５５】[0055]
〔実施例１〕 （ポリウレタン系プラスチックレンズ基材の作成）ｍ−
キシレンジイソシアネート１００重量部と、ペンタエリ
スリトールテトラキス−３−メルカプトプロピオネート
１３０重量部と、離型剤としてリン酸ジ−ｎ−ブチル１
重量部と、重合開始剤としてジブチル錫ジクロライド
０．０２重量部と、紫外線吸収剤として２−（２’−ヒ
ドロキシ−５’−ｔ−オクチルフェニル）ベンゾトリア
ゾール０．２重量部とを混合し、１×１０-1Ｔｏｒｒの
真空下で冷却しながら３０分間脱気を行った。[Example 1] (Preparation of polyurethane plastic lens substrate) m-
100 parts by weight of xylene diisocyanate, 130 parts by weight of pentaerythritol tetrakis-3-mercaptopropionate, and di-n-butyl phosphate 1 as a release agent.
Parts by weight, 0.02 parts by weight of dibutyltin dichloride as a polymerization initiator, and 0.2 parts by weight of 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole as an ultraviolet absorber, Degassing was performed for 30 minutes while cooling under a vacuum of 1 × 10 −1 Torr.
【００５６】次に、ガラス製のレンズ成形用型と合成樹
脂製ガスケットを組み合わせて成形用鋳型を作成し、前
述の混合物を注入した。室温から１２０℃まで１５時間
かけて連続的に昇温し、１２０℃で２時間保持して重合
を行った。重合終了後ガスケットを外し、レンズ成形用
型から成形物取り外し、ポリウレタン系プラスチックレ
ンズ基材を得た。Next, a glass lens molding die and a synthetic resin gasket were combined to form a molding die, and the above-mentioned mixture was injected. Polymerization was carried out by continuously raising the temperature from room temperature to 120 ° C. over 15 hours and maintaining it at 120 ° C. for 2 hours. After completion of the polymerization, the gasket was removed and the molded product was removed from the lens molding die to obtain a polyurethane plastic lens substrate.
【００５７】得られたレンズ基材は無色透明で屈折率が
１．５９７と高く、アッベ数が３４と良好な光学特性を
持ち、歪がなく、耐衝撃性、切削性及び研磨性も優れて
いた。 （有機ケイ素系コーティング組成物からなる硬質塗膜の
作成） １．予備組成物Ａの調整：回転子を備えた反応容器中に
γ−グリシドキシプロピルメチルジエトキシシラン２４
８重量部を仕込み、マグネチックスターラーを用いて激
しく撹拌しながら、０．０５規定塩酸水溶液３６重量部
を一度に添加した。The obtained lens substrate was colorless and transparent, had a high refractive index of 1.597, had good Abbe's number of 34 and had good optical characteristics, was free of distortion, and was excellent in impact resistance, machinability and polishability. It was (Preparation of hard coating film made of organosilicon coating composition) 1. Preparation of Precomposition A: γ-glycidoxypropylmethyldiethoxysilane 24 in a reaction vessel equipped with a rotor.
8 parts by weight were charged, and 36 parts by weight of 0.05 N hydrochloric acid aqueous solution was added at once with vigorous stirring using a magnetic stirrer.
【００５８】添加直後は不均一溶液であったが、数分で
発熱しながら均一で無色透明な溶液になった。更に１時
間撹拌を続け、ビヒクル成分に相当する加水分解物を得
た。得られた加水分解物に、溶媒としてエタノール５
６．６重量部及びエチレングリコール５３．４重量部を
添加した後、硬化触媒としてアルミニウムアセチルアセ
トネート４．７重量部を加え、十分に混合溶解させて、
予備組成物Ａを調整した。 ２．予備組成物Ｂの調製：回転子を備えた反応容器中に
γ−グリシドキシプロピルトリメトキシシラン２１２．
４重量部を仕込み、容器内の温度を１０℃に保ち、マグ
ネチックスターラーを用いて激しく撹拌しながら、０．
０１規定塩酸水溶液４８．６重量部を徐々に滴下した。
滴下終了後は直ちに冷却を止めると、均一で無色透明な
溶液状のビヒクル成分に相当する加水分解物を得た。Immediately after the addition, the solution was a heterogeneous solution, but it became a uniform, colorless and transparent solution with heat generation in a few minutes. The stirring was continued for another hour to obtain a hydrolyzate corresponding to the vehicle component. The resulting hydrolyzate contains ethanol 5 as a solvent.
After adding 6.6 parts by weight and 53.4 parts by weight of ethylene glycol, 4.7 parts by weight of aluminum acetylacetonate as a curing catalyst was added and sufficiently mixed and dissolved,
Preparative composition A was prepared. 2. Preparation of Preliminary Composition B: γ-glycidoxypropyltrimethoxysilane 212. in a reaction vessel equipped with a rotor.
4 parts by weight were charged, the temperature in the container was kept at 10 ° C., and the mixture was stirred vigorously with a magnetic stirrer while stirring at 0.
48.6 parts by weight of a 01N aqueous hydrochloric acid solution was gradually added dropwise.
When the cooling was stopped immediately after completion of the dropping, a uniform, colorless and transparent solution-like hydrolyzate of the vehicle component was obtained.
【００５９】得られた加水分解物に、溶媒としてエタノ
ール７７．１重量部及びエチレングリコール３７．７重
量部を添加した後、硬化触媒としてアルミニウムアセチ
ルアセトネート７．６５重量部を加え、十分に混合溶解
させて、予備組成物Ｂを調整した。 ３．コーティング組成物の調製：ガラス容器に、前述の
１、２で調整した予備組成物Ａを２０重量部、Ｂを８０
重量部（固形分割合ではない）を秤量して注ぎいれ、そ
こへ市販の五酸化アンチモンゾルゾルを１５０重量部
（固形分ではない）、シリコーン系界面活性剤を０．４
５重量部添加し、十分に撹拌混合することにより、均一
で無色透明な溶液状のコーティング組成物を調製した。 ４．塗布：前述のレンズ基材上に浸漬法（引上げ速度１
０ｃｍ／分）で上記コーティング組成物を塗布し、１０
０℃で２時間加熱処理して、硬質塗膜を硬化させた。こ
うして硬質塗膜が形成された。 （多層反射防止膜の作成）市販の真空蒸着装置を使用し
て真空蒸着法により多層膜反射防止コートを形成した。
低屈折率膜の蒸着原料としてＳｉＯ2 を用い、高屈折率
膜の蒸着原料としてＴｉ3 Ｏ5 を用いた。To the resulting hydrolyzate, 77.1 parts by weight of ethanol and 37.7 parts by weight of ethylene glycol as a solvent were added, and then 7.65 parts by weight of aluminum acetylacetonate as a curing catalyst were added and mixed sufficiently. A preliminary composition B was prepared by dissolving. 3. Preparation of coating composition: In a glass container, 20 parts by weight of the preliminary composition A prepared in the above 1 and 2 and 80 parts of B were prepared.
Weight parts (not the solid content ratio) are weighed and poured, and 150 parts by weight of the commercially available antimony pentoxide sol sol (not the solid content) and 0.4 parts of the silicone-based surfactant are added.
By adding 5 parts by weight and thoroughly stirring and mixing, a uniform, colorless and transparent solution-like coating composition was prepared. 4. Application: Dipping method on the above-mentioned lens substrate (pulling speed 1
0 cm / min) and apply the above coating composition at 10
The hard coating film was cured by heat treatment at 0 ° C. for 2 hours. Thus, a hard coating film was formed. (Preparation of Multilayer Antireflection Film) A multilayer antireflection coating was formed by a vacuum vapor deposition method using a commercially available vacuum vapor deposition apparatus.
SiO 2 was used as a deposition material for the low refractive index film, and Ti 3 O 5 was used as a deposition material for the high refractive index film.
【００６０】前述の硬質塗膜を施したレンズ基材を真空
装置内に入れ、約８０℃に加熱しながら排気を行い、１
×１０-5Ｔｏｒｒまで排気した。電子ビーム加熱法によ
り上記蒸着原料を蒸着させた。Ｔｉ3 Ｏ5 の蒸着時は１
×１０-4Ｔｏｒｒになるように酸素ガスを導入して蒸着
を行った。反射防止膜の構成を表１に示す。The lens base material coated with the above-mentioned hard coating is placed in a vacuum apparatus, and is evacuated while being heated to about 80 ° C.
It was evacuated to × 10 -5 Torr. The above vapor deposition material was vapor-deposited by an electron beam heating method. 1 when depositing Ti 3 O 5
Deposition was carried out by introducing oxygen gas so that the pressure was × 10 -4 Torr. Table 1 shows the structure of the antireflection film.
【００６１】[0061]
【表１】 [Table 1]
【００６２】（評価）以上のようにして作製したレンズ
を次の試験に供し、性能を評価した。 １．外観 通常の白色蛍光灯を光源にした照度１０００ルックスの
照明装置を用いて目視判定により次の項目の評価を行っ
た。 （１）透明性……着色あるいは白濁等がないこと （２）レンズ内部の均一性……レンズ内部に脈理等の不
均一がないこと （３）反射防止膜の均一性……反射色が均一であること 評価は下記のように行った。(Evaluation) The lens manufactured as described above was subjected to the following test to evaluate the performance. 1. Appearance The following items were evaluated by visual judgment using an illuminating device having an illuminance of 1000 lux with a normal white fluorescent lamp as a light source. (1) Transparency: No coloring or cloudiness (2) Uniformity within the lens: No nonuniformity of striae inside the lens (3) Uniformity of antireflection film: Reflection color Uniformity was evaluated as follows.
【００６３】○……問題がない △……やや問題がある ×……問題がある ２．反射特性 ３５０ｎｍ〜８００ｎｍの分光反射率を、株式会社日立
製作所製３３０型分光光度計により測定した。 ３．視感透過率の測定 旭分光株式会社製モデル３０４型視感度透過率計を用い
て視感度透過率を測定した。 ４．密着性 作成したレンズを９０℃の熱水に２時間浸漬後、硬質塗
膜と反射防止膜とを施したレンズ表面にナイフで１ｍｍ
おきに縦方向横方向にカット線を入れることにより１０
０個のゴバンの目を作り、その後、セロハン粘着テープ
（商品名“セロテープ”ニチバン株式会社製）を強く張
り付けた。テープの一端を手に持って９０度方向に急速
にはがし、レンズ表面のゴバンの目が何個剥がれるかを
調べた。剥がれたゴバンの目の数Ｘを分子にしてＸ／１
００で表す。Ｘが小さいほど密着性がよい。 ５．耐摩傷性試験 スチールウール＃００００でレンズ表面を摩擦し傷付き
難さを調べた。尚、評価は次のように行なった。○: No problem △: Some problem ×: Problem 2. Reflection characteristics Spectral reflectance of 350 nm to 800 nm was measured by Hitachi Ltd. model 330 spectrophotometer. 3. Measurement of luminous transmittance The luminous transmittance was measured using a model 304 type luminous transmittance meter manufactured by Asahi Spectroscopy Co., Ltd. 4. Adhesion The prepared lens was dipped in hot water at 90 ° C for 2 hours, and then 1 mm with a knife on the surface of the lens coated with hard coating and antireflection coating.
10 every time by putting a cutting line in the vertical and horizontal directions
Zero Gobang eyes were made, and then cellophane adhesive tape (trade name "Cellotape" manufactured by Nichiban Co., Ltd.) was strongly attached. By holding one end of the tape in the hand and rapidly peeling it in the direction of 90 degrees, it was examined how many Gobang eyes on the lens surface were peeled off. The number X of peeled Gobang is used as the numerator, X / 1
Represented by 00. The smaller X is, the better the adhesion is. 5. Scratch resistance test The lens surface was rubbed with steel wool # 0000 to examine the scratch resistance. The evaluation was performed as follows.
【００６４】◎……強く摩擦しても傷がつかない。 ○……かなり強く摩擦すると少し傷がつく。 ×……弱い摩擦でも傷がつく。 ちなみに硬質塗膜なしのレンズの評価は×であった。以
上の評価結果を図１及び表２に示す。⊚ · No scratches even when rubbed strongly. ○ …… Slightly scratched when rubbed considerably. × …… Scratches even with weak friction. Incidentally, the evaluation of the lens without a hard coating was x. The above evaluation results are shown in FIG. 1 and Table 2.
【００６５】[0065]
【表２】 [Table 2]
【００６６】〔実施例２〕実施例１において、五酸化ア
ンチモンゾルに代えて、酸化チタンと酸化セリウムの複
合ゾルを使用した外は実施例１と全く同様にして硬質塗
膜を形成した。そして、硬質塗膜上に実施例１と同じ真
空蒸着法によって表３に示す構成の多層反射防止膜を作
成した。Example 2 A hard coating film was formed in the same manner as in Example 1 except that a composite sol of titanium oxide and cerium oxide was used instead of the antimony pentoxide sol in Example 1. Then, a multilayer antireflection film having the structure shown in Table 3 was formed on the hard coating film by the same vacuum vapor deposition method as in Example 1.
【００６７】[0067]
【表３】 [Table 3]
【００６８】評価結果を図２及び表２に示す。 〔実施例３〕実施例１において、五酸化アンチモンゾル
に代えて、酸化チタンと鉄の複合ゾルを用いた外は実施
例１と全く同様にして硬質塗膜を形成した。The evaluation results are shown in FIG. 2 and Table 2. [Example 3] A hard coating film was formed in the same manner as in Example 1 except that a composite sol of titanium oxide and iron was used in place of the antimony pentoxide sol in Example 1.
【００６９】そして、硬質塗膜上に実施例１と同じ真空
蒸着法によって表４に示す構成の多層反射防止膜を作成
した。Then, a multilayer antireflection film having the constitution shown in Table 4 was formed on the hard coating film by the same vacuum vapor deposition method as in Example 1.
【００７０】[0070]
【表４】 [Table 4]
【００７１】ここで、Ｚ＋Ａは酸化ジルコニウムと酸化
アルミニウムの混合物質を示し、Ｐ＋Ａは酸化プラセオ
ジウムと酸化アルミニウムの混合物質を示す。評価結果
を図３及び表２に示す。 〔実施例４〕実施例１において、五酸化アンチモンゾル
に代えて、酸化スズと酸化タングステンの複合ゾルで酸
化スズゾルを被覆したゾル（変性ゾル）を用いた外は、
実施例１と全く同様にして硬質塗膜を形成した。Here, Z + A represents a mixed substance of zirconium oxide and aluminum oxide, and P + A represents a mixed substance of praseodymium oxide and aluminum oxide. The evaluation results are shown in FIG. 3 and Table 2. [Example 4] In Example 1, except that a sol obtained by coating a tin oxide sol with a composite sol of tin oxide and tungsten oxide (modified sol) was used instead of the antimony pentoxide sol,
A hard coating film was formed in exactly the same manner as in Example 1.
【００７２】そして、硬質塗膜上に実施例１と同じ真空
蒸着法により、表５に示す構成の多層反射防止膜を作成
した。Then, a multilayer antireflection film having the constitution shown in Table 5 was formed on the hard coating film by the same vacuum vapor deposition method as in Example 1.
【００７３】[0073]
【表５】 [Table 5]
【００７４】評価結果を図４及び表２に示す。 〔比較例１〕実施例１において、五酸化アンチモンゾル
に代えて、二酸化ケイ素ゾルを用いてコーティング組成
物を用いた外は、実施例１と全く同様にして硬質塗膜を
作成した。The evaluation results are shown in FIG. 4 and Table 2. [Comparative Example 1] A hard coating film was prepared in exactly the same manner as in Example 1, except that the silicon dioxide sol was used in place of the antimony pentoxide sol in Example 1 and the coating composition was used.
【００７５】そして、硬質塗膜上に実施例１と同じ真空
蒸着法により、表６の構成の多層反射防止膜を作成し
た。Then, a multilayer antireflection film having the constitution shown in Table 6 was formed on the hard coating film by the same vacuum vapor deposition method as in Example 1.
【００７６】[0076]
【表６】 [Table 6]
【００７７】反射特性を図５に示す。反射特性に細かい
凸凹があり、反射色にムラが著しかった。また、透過率
もやや劣るものであった。 〔比較例２〕実施例１において、レンズ基材としてポリ
カーボネート系射出成形レンズ基材を用いた外は、実施
例１と全く同様に硬質塗膜及び多層反射防止膜を作成し
た。The reflection characteristics are shown in FIG. There were fine irregularities in the reflection characteristics, and the reflection color was notably uneven. In addition, the transmittance was slightly inferior. [Comparative Example 2] A hard coating film and a multilayer antireflection film were prepared in the same manner as in Example 1 except that a polycarbonate-based injection molded lens substrate was used as the lens substrate.
【００７８】反射特性は図１とほぼ同じであったが、透
明性、内部の均一性、密着性、耐擦傷性に劣るものであ
った。比較例１、２の評価結果は表２に示す。比較例２
の密着性において、８／１００とあるのは、ゴバン目に
おいて、硬質塗膜と多層反射防止膜とを施したレンズか
ら、８枚のゴバン目が硬質塗膜ごと剥がれたことを意味
している。The reflection characteristics were almost the same as those in FIG. 1, but they were inferior in transparency, internal uniformity, adhesion and scratch resistance. The evaluation results of Comparative Examples 1 and 2 are shown in Table 2. Comparative example 2
The adhesiveness of 8/100 means that, in the goggles, the eight gobangs were peeled off together with the hard paint from the lens provided with the hard paint and the multilayer antireflection film. .
【００７９】[0079]
【発明の効果】以上の通り、本発明によれば、反射防止
性プラスチックレンズに関して次のような効果が得られ
る。 （１）透明性、内部の均一性に優れ、薄型軽量である。 （２）反射防止性に優れ、表面のギラツキが少なくメガ
ネレンズに使用した場合目元がすっきりと見える。 （３）透過率が良く、メガネレンズに使用した場合すっ
きりとした視界を得ることができる。 （４）反射防止膜の反射色にムラがない。 （５）反射率の低い高性能な反射防止膜が少ない層数で
形成できる。 （６）耐擦傷性、表面硬度、耐摩耗性に優れ、硬質塗膜
および反射防止膜の密着性も優れる 。 （７）可撓性、耐熱性、耐温水性、耐薬品性に優れる。 （８）帯電防止性が優れ、汚れが比較的付きにくい。As described above, according to the present invention, the following effects can be obtained regarding the antireflection plastic lens. (1) It has excellent transparency and internal uniformity, and is thin and lightweight. (2) It has excellent anti-reflection properties, has less glare on the surface, and when used in spectacle lenses, the eyes can be seen clearly. (3) The transmittance is good, and a clear field of view can be obtained when used for a spectacle lens. (4) The reflection color of the antireflection film is uniform. (5) A high-performance antireflection film having a low reflectance can be formed with a small number of layers. (6) It has excellent scratch resistance, surface hardness, and abrasion resistance, and also has excellent adhesion between the hard coating film and the antireflection film. (7) Excellent in flexibility, heat resistance, warm water resistance, and chemical resistance. (8) The antistatic property is excellent, and dirt is relatively hard to attach.
【図１】本発明の実施例１におけるレンズの反射特性を
表したグラフである。FIG. 1 is a graph showing a reflection characteristic of a lens in Example 1 of the present invention.
【図２】本発明の実施例２におけるレンズの反射特性を
表したグラフである。FIG. 2 is a graph showing a reflection characteristic of a lens in Example 2 of the present invention.
【図３】本発明の実施例３におけるレンズの反射特性を
表したグラフである。FIG. 3 is a graph showing a reflection characteristic of a lens in Example 3 of the present invention.
【図４】本発明の実施例４におけるレンズの反射特性を
表したグラフである。FIG. 4 is a graph showing a reflection characteristic of a lens in Example 4 of the present invention.
【図５】比較例１におけるレンズの反射特性を表したグ
ラフである。5 is a graph showing the reflection characteristics of the lens in Comparative Example 1. FIG.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０９Ｄ 183/04 ＰＭＴ 8319−4Ｊ (72)発明者 吉田 好徳 東京都品川区西大井１丁目６番３号 株式 会社ニコン大井製作所内 (72)発明者 斉藤 誠治 東京都品川区西大井１丁目６番３号 株式 会社ニコン大井製作所内 (72)発明者 瀧 和也 東京都品川区西大井１丁目６番３号 株式 会社ニコン大井製作所内 (72)発明者 成澤 孝司 東京都品川区西大井１丁目６番３号 株式 会社ニコン大井製作所内─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification number Office reference number FI technical display location C09D 183/04 PMT 8319-4J (72) Inventor Yoshinori Yoshida 1-6-3 Nishioi, Shinagawa-ku, Tokyo No. Ltd. Nikon Oi Works (72) Inventor Seiji Saito 1-6-3 Nishioi, Shinagawa-ku, Tokyo Inside Nikon Oi Works (72) Inventor Kazuya Taki 1-3-6 Nishioi, Shinagawa-ku, Tokyo Nikon Oi Manufacturing Co., Ltd. (72) Inventor Koji Narizawa 1-3-6 Nishioi, Shinagawa-ku, Tokyo Inside Nikon Oi Manufacturing Co., Ltd.
Claims (1)
び／又はポリチオールとを重合させて得られるポリウレ
タン系プラスチックレンズ基材と、前記プラスチックレ
ンズ基材の表面に設けられ、 一般式：Ｒ1 a Ｒ2 b Ｓｉ（ＯＲ3)4-(a+b) …（式I ） （但し、式中、Ｒ1 は、官能基又は不飽和２重結合を有
する炭素数４〜１４の有機基であり、Ｒ2 は、炭素数１
〜６の炭化水素基又はハロゲン化炭化水素基であり、Ｒ
3 は、炭素数１〜４のアルキル基、アルコキシアルキル
基又はアシル基であり、ａ及びｂは、それぞれ０又は１
であり、かつａ＋ｂは、１又は２である。）で表される
有機ケイ素化合物又はその加水分解物中に、酸化アンチ
モンゾル、酸化ジルコニウムゾル、酸化チタンゾル、酸
化スズゾル、酸化タンタルゾル、酸化タングステンゾ
ル、酸化アルミニウムゾル、酸化チタンと酸化セリウム
の複合ゾル、酸化チタンと鉄の複合ゾル、酸化スズと酸
化タングステンの複合ゾルで酸化スズゾルを被覆したゾ
ルから選ばれる少なくとも１種の無機微粒子を含有して
なる有機ケイ素系コーティング組成物からなる硬質塗膜
と、前記硬質塗膜上に設けられた、チタン、ケイ素の酸
化物を含む多層反射防止膜とからなることを特徴とする
反射防止性プラスチックレンズ。1. A polyurethane plastic lens substrate obtained by polymerizing polyisocyanate with a polyol and / or a polythiol, and a surface of the plastic lens substrate having the general formula: R 1 a R 2 b Si ( OR 3 ) 4- (a + b) (Formula I) (In the formula, R 1 is a functional group or an organic group having an unsaturated double bond and having 4 to 14 carbon atoms, and R 2 is Carbon number 1
~ 6 hydrocarbon groups or halogenated hydrocarbon groups, R
3 is an alkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group or an acyl group, and a and b are 0 or 1 respectively.
And a + b is 1 or 2. ) In the organosilicon compound or a hydrolyzate thereof, antimony oxide sol, zirconium oxide sol, titanium oxide sol, tin oxide sol, tantalum oxide sol, tungsten oxide sol, aluminum oxide sol, a composite sol of titanium oxide and cerium oxide, A hard coating film comprising an organosilicon coating composition containing at least one kind of inorganic fine particles selected from a sol obtained by coating a tin oxide sol with a composite sol of titanium oxide and iron, a composite sol of tin oxide and tungsten oxide, An antireflection plastic lens comprising a multilayer antireflection film containing an oxide of titanium or silicon provided on the hard coating film.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16928292A JP3491164B2 (en) | 1992-06-26 | 1992-06-26 | Anti-reflective plastic lens |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16928292A JP3491164B2 (en) | 1992-06-26 | 1992-06-26 | Anti-reflective plastic lens |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0611601A true JPH0611601A (en) | 1994-01-21 |
| JP3491164B2 JP3491164B2 (en) | 2004-01-26 |
Family
ID=15883630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16928292A Expired - Lifetime JP3491164B2 (en) | 1992-06-26 | 1992-06-26 | Anti-reflective plastic lens |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3491164B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001123115A (en) * | 1999-08-16 | 2001-05-08 | Nissan Chem Ind Ltd | Coating composition and optical member |
| WO2001088048A1 (en) * | 2000-05-18 | 2001-11-22 | Itoh Optical Industrial Co.,Ltd. | Optical element |
| US7229686B2 (en) | 2002-09-25 | 2007-06-12 | Shin-Etsu Chemical Co., Ltd. | Antireflection film and making method |
| JP2009155541A (en) * | 2007-12-27 | 2009-07-16 | Ito Kogaku Kogyo Kk | Hard coat composition |
| KR101349355B1 (en) * | 2012-03-14 | 2014-01-16 | 한국전기연구원 | High refractive thin films using tin-oxide sol and their manufacturing method |
| EP2660260A4 (en) * | 2010-12-27 | 2014-06-11 | Mitsubishi Gas Chemical Co | COMPOSITION FOR OPTICAL EQUIPMENT |
-
1992
- 1992-06-26 JP JP16928292A patent/JP3491164B2/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001123115A (en) * | 1999-08-16 | 2001-05-08 | Nissan Chem Ind Ltd | Coating composition and optical member |
| JP4654492B2 (en) * | 1999-08-16 | 2011-03-23 | 日産化学工業株式会社 | Coating composition and optical member |
| WO2001088048A1 (en) * | 2000-05-18 | 2001-11-22 | Itoh Optical Industrial Co.,Ltd. | Optical element |
| US6773465B1 (en) | 2000-05-18 | 2004-08-10 | Itoh Optical Industrial Co., Ltd. | Optical element |
| US7229686B2 (en) | 2002-09-25 | 2007-06-12 | Shin-Etsu Chemical Co., Ltd. | Antireflection film and making method |
| JP2009155541A (en) * | 2007-12-27 | 2009-07-16 | Ito Kogaku Kogyo Kk | Hard coat composition |
| EP2660260A4 (en) * | 2010-12-27 | 2014-06-11 | Mitsubishi Gas Chemical Co | COMPOSITION FOR OPTICAL EQUIPMENT |
| KR101349355B1 (en) * | 2012-03-14 | 2014-01-16 | 한국전기연구원 | High refractive thin films using tin-oxide sol and their manufacturing method |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3491164B2 (en) | 2004-01-26 |
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