US20220098439A1 - Glycidyl ether based optical coating compositions - Google Patents
Glycidyl ether based optical coating compositions Download PDFInfo
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- US20220098439A1 US20220098439A1 US17/549,453 US202117549453A US2022098439A1 US 20220098439 A1 US20220098439 A1 US 20220098439A1 US 202117549453 A US202117549453 A US 202117549453A US 2022098439 A1 US2022098439 A1 US 2022098439A1
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- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 239000008199 coating composition Substances 0.000 title abstract description 10
- 230000003287 optical effect Effects 0.000 title description 9
- 238000000576 coating method Methods 0.000 claims abstract description 43
- 239000000758 substrate Substances 0.000 claims abstract description 35
- 239000011248 coating agent Substances 0.000 claims abstract description 32
- 229910000077 silane Inorganic materials 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims description 83
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 48
- 238000012360 testing method Methods 0.000 claims description 45
- WPYCRFCQABTEKC-UHFFFAOYSA-N Diglycidyl resorcinol ether Chemical compound C1OC1COC(C=1)=CC=CC=1OCC1CO1 WPYCRFCQABTEKC-UHFFFAOYSA-N 0.000 claims description 25
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 22
- 239000004417 polycarbonate Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000003999 initiator Substances 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- 229920000515 polycarbonate Polymers 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 7
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- FSYPIGPPWAJCJG-UHFFFAOYSA-N 2-[[4-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OCC1CO1 FSYPIGPPWAJCJG-UHFFFAOYSA-N 0.000 claims description 4
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims description 4
- KFUSXMDYOPXKKT-VIFPVBQESA-N (2s)-2-[(2-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC=C1OC[C@H]1OC1 KFUSXMDYOPXKKT-VIFPVBQESA-N 0.000 claims description 3
- KFUSXMDYOPXKKT-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC=C1OCC1OC1 KFUSXMDYOPXKKT-UHFFFAOYSA-N 0.000 claims description 3
- AVKQYWUBGXNBCW-UHFFFAOYSA-N 2-[(4-nonylphenoxy)methyl]oxirane Chemical compound C1=CC(CCCCCCCCC)=CC=C1OCC1OC1 AVKQYWUBGXNBCW-UHFFFAOYSA-N 0.000 claims description 3
- FCDHDTLCENSJSU-UHFFFAOYSA-N benzene-1,3-diol;2-(oxiran-2-ylmethoxymethyl)oxirane Chemical compound OC1=CC=CC(O)=C1.C1OC1COCC1CO1 FCDHDTLCENSJSU-UHFFFAOYSA-N 0.000 claims description 3
- 239000012952 cationic photoinitiator Substances 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 1
- -1 alkoxy silane Chemical compound 0.000 abstract description 34
- 239000004593 Epoxy Substances 0.000 abstract description 13
- 230000007062 hydrolysis Effects 0.000 abstract description 8
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 8
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005299 abrasion Methods 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 125000002091 cationic group Chemical group 0.000 description 11
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- 229910001868 water Inorganic materials 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000004615 ingredient Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 7
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical group C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 4
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 4
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 3
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 3
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- WNISWKAEAPQCJQ-UHFFFAOYSA-N 2-[(2-nonylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCC1=CC=CC=C1OCC1OC1 WNISWKAEAPQCJQ-UHFFFAOYSA-N 0.000 description 2
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NACPTFCBIGBTSJ-UHFFFAOYSA-N 2-hydroxy-2-phenyl-1-(2-propan-2-ylphenyl)ethanone Chemical compound CC(C)C1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 NACPTFCBIGBTSJ-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 2
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 2
- 229920002574 CR-39 Polymers 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229940000489 arsenate Drugs 0.000 description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 239000012949 free radical photoinitiator Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 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 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
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 1
- OAKFFVBGTSPYEG-UHFFFAOYSA-N (4-prop-2-enoyloxycyclohexyl) prop-2-enoate Chemical compound C=CC(=O)OC1CCC(OC(=O)C=C)CC1 OAKFFVBGTSPYEG-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 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
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- KFQPRNVTVMCYEH-UHFFFAOYSA-N 1-amino-3-(4-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=C(OCC(O)CN)C=C1 KFQPRNVTVMCYEH-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- ROYZOPPLNMOKCU-UHFFFAOYSA-N 2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl-tripropoxysilane Chemical compound C1C(CC[Si](OCCC)(OCCC)OCCC)CCC2OC21 ROYZOPPLNMOKCU-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-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
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- PRJQBLZFLQSJOM-UHFFFAOYSA-N 2-[[1,3-dibromo-2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C(C1CO1)OC(C(C)(C(OCC1CO1)Br)C)Br PRJQBLZFLQSJOM-UHFFFAOYSA-N 0.000 description 1
- HIGURUTWFKYJCH-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC1(COCC2OC2)CCCCC1 HIGURUTWFKYJCH-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- GGRBZHPJKWFAFZ-UHFFFAOYSA-N 3,4-bis(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(OC(=O)C(C)=C)COC(=O)C(C)=C GGRBZHPJKWFAFZ-UHFFFAOYSA-N 0.000 description 1
- HTWRFCRQSLVESJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)C(C)=C HTWRFCRQSLVESJ-UHFFFAOYSA-N 0.000 description 1
- YXYCGBBZGQNOFX-UHFFFAOYSA-N 3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl-tripropoxysilane Chemical compound C1C(CCC[Si](OCCC)(OCCC)OCCC)CCC2OC21 YXYCGBBZGQNOFX-UHFFFAOYSA-N 0.000 description 1
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 description 1
- GFLJTEHFZZNCTR-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC(=O)C=C GFLJTEHFZZNCTR-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-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
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- PTOCVXOZAZOZTJ-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl(tripropoxy)silane Chemical compound C1C(C[Si](OCCC)(OCCC)OCCC)CCC2OC21 PTOCVXOZAZOZTJ-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- CQHKDHVZYZUZMJ-UHFFFAOYSA-N [2,2-bis(hydroxymethyl)-3-prop-2-enoyloxypropyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CO)COC(=O)C=C CQHKDHVZYZUZMJ-UHFFFAOYSA-N 0.000 description 1
- ZSOXNXDUYPYGJO-UHFFFAOYSA-N [2-(chloromethyl)phenyl]-phenylmethanone Chemical class ClCC1=CC=CC=C1C(=O)C1=CC=CC=C1 ZSOXNXDUYPYGJO-UHFFFAOYSA-N 0.000 description 1
- OFIMLDVVRXOXSK-UHFFFAOYSA-N [4-(2-methylprop-2-enoyloxy)cyclohexyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCC(OC(=O)C(C)=C)CC1 OFIMLDVVRXOXSK-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000006117 anti-reflective coating Substances 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical group C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 230000036624 brainpower Effects 0.000 description 1
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- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
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- DBUFXGVMAMMWSD-UHFFFAOYSA-N trimethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OC)(OC)OC)CCC2OC21 DBUFXGVMAMMWSD-UHFFFAOYSA-N 0.000 description 1
- ZOWVSEMGATXETK-UHFFFAOYSA-N trimethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OC)(OC)OC)CCC2OC21 ZOWVSEMGATXETK-UHFFFAOYSA-N 0.000 description 1
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- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
Definitions
- the present invention relates to the field of transparent coatings for polymeric objects such as eyeglass lenses.
- U.S. Pat. No. 6,100,313 provides, inter alia, a coating composition that accepts dye well, that provides exceptional abrasion-resistance (AR), and that is substantially free of volatiles.
- the composition includes a partially hydrolyzed epoxy-functional alkoxysilane, and can also include a polymerizable ether selected from the group consisting of glycidyl ethers, allyl ethers and vinyl ethers.
- Glycidyl ethers said to be useful in the invention of the '313 patent include “triglycidyl ether, ⁇ -glycidoxypropyl trimethoxy silane, triglycidyl ether, 1,4-butanediol diglycidyl ether, Bisphenol A diglycidyl ether, the C8-C14 alkyl glycidyl ethers, butyl glycidyl ether, cresyl glycidyl ether, phenyl glycidyl ether, nonylphenyl glycidyl ether, p-tert-butylphenyl glycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, resorcinol diglycidyl ether, polyglycidyl ethers of aliphatic polyols, cyclohe
- Oxetane describes a combination comprising a coated and cured composition as a layer upon the surface of a polymeric material, that includes a partially hydrolyzed organo-functional alkoxysilane and a polymerizable aromatic oxetane, such as 1,4-Bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, which is an aromatic, difunctional oxetane available commercially as “OXT-121”).
- a polymeric material that includes a partially hydrolyzed organo-functional alkoxysilane and a polymerizable aromatic oxetane, such as 1,4-Bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, which is an aromatic, difunctional oxetane available commercially as “OXT-121”).
- optical and other industries continue to seek materials, and corresponding surface treatments or coatings, that provide improved properties, such as adhesion, tintability, abrasion resistance, and solubility.
- the present invention provides a combination comprising a substrate and cured coating formed of the hydrolysis product of an epoxy functional alkoxy silane in combination with one or more monoaromatic (mono- or di)glycidyl ethers.
- a coating of this invention preferably exhibits an optimal combination of properties that meet or exceed those provided by conventional coatings, including to provide improved adhesion resistance, preferably without the need for a primer, and as determined by crosshatch adhesion tests according to ASTM 3359 (including those involving deionized water, humidity and/or QUV testing).
- the compositions can be adapted to be tintable as well, using conventional methods and as described herein.
- the invention provides a coating composition for forming an abrasion-resistant coating upon a substrate, the composition comprising an ether selected from the group consisting of:
- the ether comprises RDGE (compound (A) above), either alone or in combination with one or more other ethers, including aliphatic or other monoaromatic ethers from within the list provided above.
- RDGE tends to provide improved solubility for use in compositions of the present invention, particularly as compared to ethers (B) through (F) listed above.
- coatings of the present invention provide a surprising and optimal combination of properties that include usefulness with a variety of substrates.
- a composition of this invention can provide comparable or improved properties selected from the group consisting of adhesion resistance, stability, tintability, and abrasion resistance, among others.
- a composition that includes RDGE can be used to provide a UV curable coating having the potential to meet each of three different adhesion tests used in the optical industry (deionized water, humidity, and QUV), which taken together are typically considered to provide the most stringent adhesion tests used in the industry.
- Prior UV cured coatings, at their closest, tend to meet only two or fewer of such tests, and particularly when used on High Index substrates, can tend to meet only one of such tests, at most.
- compositions of the present invention provide the only known UV curable, and optionally tintable, coating capable of meeting each of these tests, and in particularly the stringent QUV test.
- FIG. 1 provides a chart showing common names, IUPAC names, structures and formulas for each of the preferred glycidyl ethers of this invention.
- a UV-cured composition of the present invention can be used as a base coat to provide abrasion resistance (e.g., as determined by Bayer abrasion) that approximates that of a comparable thermally cured base coating, when used as the base coat for an antireflective coating (stack) positioned thereon.
- the present composition provides various advantages over such thermal cure coatings, including shorter processing times, while having the potential to provide tintability that is as good or better than conventional compositions.
- the composition is particularly well suited for use as the base coat, before the application of one or more additional layers.
- additional layers often include, for instance, a quartz or oxide (e.g., silicon dioxide) layer, followed by a plurality of coated layers.
- the resulting “stack” of coated layers can be applied in order to provide an improved array of properties to the overall coated material, including in particular abrasion resistance, as compared to conventional compositions.
- Applicant has discovered the manner in which particular polymerizable monomers from the group described herein as monoaromatic (mono- or di)glycidyl ethers can be used in combination with organofunctional silanes in order to provide improved compositions, and corresponding base coats having excellent adhesion to polycarbonate and other substrates.
- the compositions of this invention have comparable or even improved tintability, as compared to conventional compositions.
- an abrasion resistant coating for use on eyeglass lenses, will typically begin with the application of a composition of this invention, e.g., by spin coating and curing the composition with ultraviolet energy. Thereafter, the coated base composition can be subjected to one or more intermediate treatments, for instance, it can be tinted using conventional means, e.g., by dipping the coated lens into a tint bath.
- the lens material can be subjected to a conventional coating machine, for the application of an antireflection coating, in the form of a ‘stack’ or plurality of layers.
- an antireflection coating in the form of a ‘stack’ or plurality of layers.
- the coated lens is typically degassed (e.g., under suitable conditions of time, vacuum, and temperature), followed by the application of an intermediate layer (e.g., quartz or silicon dioxide), which itself can be compacted by e-beam or other means, and finally by the application of one or more AR coatings applied by means of vapor deposition.
- an intermediate layer e.g., quartz or silicon dioxide
- the composition can be used to provide an improved combination of properties, particularly for use in coating lenses and other transparent polymeric materials.
- lens materials include those having an array of properties (e.g., refractive index), and preferably includes both polycarbonate and high index lenses.
- the coating composition is itself substantially solvent free, and in turn, provides minimal, if any, detectable volatiles in the course of its application, curing, or use. Detectable volatiles are likely to be found, if at all, upon the elimination of methanol upon curing of certain compositions.
- compositions of this invention are particularly well suited for polymeric substrates, and particularly high refractive index substrates intended for optical applications, including thermosetting and thermoplastic polycarbonates, as well as polyurethanes.
- substrates can be used for a variety of applications, including for automotive instrumentation, aviation gauges and instruments, display and/or shielding windows, eyewear lenses, handheld meters and devices, molded display windows and panels, outdoor equipment gauges and displays, test & laboratory instrument displays, screen printing POP signage, thermoformed displays, medical displays and panels, and video and LED filters.
- a coated substrate of this invention comprises a high index material.
- high index materials of this type comprise a polyisocyanate compound and a polythiol compound, to provide are described in U.S. Pat. No. 5,652,321, the disclosure of which is incorporated herein by reference. Such materials are described as having an extremely high refractive index and excellent heat resistance, as exemplified in commercial products such as the MR8 and MR10 lines of lenses available from Mitsui Toatsu Chemicals, Inc.
- a monoaromatic glycidyl ether can be selected and used to provide desired performance, for instance, based upon the overall formulation, the substrate being coated, additional AR or other coatings to be used, and conditions of use.
- the monoaromatic (mono- or digylcidyl) ether can be present in the coating compositions of the invention at a weight concentration (solids basis) of between about 1 and about 10 weight percent, more preferably between about 2 and about 8 weight percent, and most preferably between about 4 and about 6 weight percent.
- the monoaromatic ether can be present in the coating compositions of the invention at a weight concentration (solids basis) between about 1 and about 40 weight percent, more preferably between about 10 and about 30 weight percent, and most preferably between about 15 and about 25 weight percent.
- a ‘tintable’ coating of this type is typically one that can be coated using standard conditions (e.g., dipping in BPI Black for 15 minutes at 95-1000) so as to provide between 18-22% transmission, as compared to a substantially non-tintable coating, which under comparable conditions would result in between 40-45% transmission.
- standard conditions e.g., dipping in BPI Black for 15 minutes at 95-1000
- substantially non-tintable coating which under comparable conditions would result in between 40-45% transmission.
- a composition of the present invention comprises a partially hydrolyzed organo-functional alkoxysilane in combination with a monoaromatic glycidyl ether, and optionally other ingredients.
- the organo-functional alkoxysilane can be of any suitable type, and is preferably selected from the group consisting of epoxy-, vinyl- and acryloxy-functional alkoxysilanes.
- the organo-functional alkoxysilane when present, can be used in any suitable amount, e.g., between about 10 and about 60 weight percent, and more preferably between about 20 and about 50 weight percent.
- Suitable acryloxy-functional organosilanes include, are selected from the group consisting of: 3((meth)acryloxypropyl)trimethoxy silane, 3((meth)acryloxyproply)methyl dimethoxy silane, and 3((meth)acryloxypropyl)dimethyl methoxy silane, including combinations thereof.
- Suitable vinyl-functional organosilanes include, but are selected from the group consisting of: vinyldimethyl ethoxysilane, vinylmethyl dimethoxysilane, vinylphenyl diethoxysilane, vinyltrimethoxysilane, and vinyltriethoxysilane, including combinations thereof.
- Suitable epoxy functional alkoxy silane precursors for use in preparing the at least partially hydrolyzed polymerizable ingredient, are selected from the group consisting of epoxyalkylalkoxysilanes of the following structure: Q-R 1 —Si(R 2 ) m —(OR 3 ) 3-m ,
- the epoxy functional alkoxy silane precursor of the at least partially hydrolyzed polymerizable ingredient is preferably an epoxyalkylalkoxysilane of the following structure: Q-R 1 —Si(R 2 ) m —(OR 3 ) 3-m ,
- R 1 is a C 1 -C 14 alkylene group
- R 2 and R 3 independently are C 1 -C 4 alkyl groups and Q is a glycidoxy or epoxycyclohexyl group, and m is 0 or 1.
- the alkoxy groups are at least partially hydrolyzed to form silanol groups with the release of the R 3 OH alcohol, and some condensation of the silanol groups occurs. Epoxy reactivity is preserved, however.
- epoxy-functional alkoxysilanes are suitable as hydrolysis precursors, including glycidoxymethyl-trimethoxysilane, glycidoxymethyltriethoxysilane, glycidoxymethyl-tripropoxysilane, glycidoxymethyl-tributoxysilane, b-glycidoxyethyltrimethoxysilane, b-glycidoxyethyltriethoxysilane, b-glycidoxyethyl-tripropoxysilane, b-glycidoxyethyl-tributoxysilane, b-glycidoxyethyltrimethoxysilane, a-glycidoxyethyl-triethoxysilane, a-glycidoxyethyl-tripropoxysilane, a-glycidoxyethyltributoxysilane, g-glycidoxypropyl-trimethoxysilane, g-glycidoxy
- a particularly preferred organo-functional alkoxysilane is ⁇ -glicidoxypropyl trimethoxy silane due to its wide commercial availability.
- Hydrolysis of the alkoxy-functional alkoxysilane precursor may occur in an acidic environment, and reference is made to U.S. Pat. No. 4,378,250, the teachings of which are incorporated herein by reference. Hydrolysis of the alkoxy groups liberates the associated alcohol to form silanol groups; these, in turn, are relatively unstable and tend to condense spontaneously.
- the alkoxysilane is reacted with a stoichiometricly sufficient quantity of water to hydrolyze at least 50% of the alkoxy groups and most preferably from about 60% to about 70% of the alkoxy groups.
- good results have been obtained by reacting the silane with a stoichiometricly sufficient quantity of water to hydrolyze two-thirds of the alkoxy groups.
- composition of this invention further comprises a monomeric organofunctional silane, and more preferably a monomeric (silanol free) alkoxy functional silane, which can also be referred to as an unhydrolyzed alkoxy functional alkoxy silane.
- a monomeric organofunctional silane and more preferably a monomeric (silanol free) alkoxy functional silane, which can also be referred to as an unhydrolyzed alkoxy functional alkoxy silane.
- certain preferred compositions can include both hydrolyzed and unhydrolyzed alkoxy functional alkoxy silanes, with the latter being present in an amount sufficient to reduce the viscosity of the composition itself.
- hydrolysis product of such a silane can certainly include compounds that are themselves partially hydrolyzed (depending on the mole ratio of water to alkoxy groups as described herein), whereas an unhydrolyzed silane of the sort claimed is clearly one that is prepared and used in the substantial absence of water.
- water is removed from the hydrolysis product component, prior to the addition of an unhydrolyzed component, in order to permit the latter to retain its unhydrolyzed nature.
- the composition desirably includes an effective amount up of a suitable non-hydrolyzed alkoxy functional silane, including those selected from the silanes listed above.
- a suitable non-hydrolyzed alkoxy functional silane including those selected from the silanes listed above.
- the non-hydrolyzed epoxy functional alkoxy silane desirably is present in an amount not less than about 5%, preferably at least about 20%, and most preferably from about 40% to about 50% by weight, solids basis.
- the epoxy functional alkoxy silane that is included as the non-hydrolyzed component also is of the same or similar type as that employed to make the hydrolyzed component. It should be understood that the hydrolyzed and non-hydrolyzed components may be different and each may utilize one or a blend of different epoxy functional alkoxy silanes, as desired.
- the monomeric silane is optional, and therefore used in an amount of between about 0% and about 50%, and more preferably between about 10% and about 40%, and even more preferably between about 20% and about 40% by weight of the composition, with typically more monomeric silane (e.g., about 35 to about 45%) being used in substantially non-tintable compositions, as compared to substantially tintable compositions (e.g., having about 35% to about 45% by weight).
- a composition of the present invention can further comprise one or more additional reactive ingredients, selected from the group consisting of one or more non-hydrolyzed silanes, one or more polyermizable ethers, and one or more ethylenically unsaturated monomer components, desirably an acrylic monomer component that preferably includes a monomer having an acrylic functionality of not more than two.
- an acrylic monomer though optional, is particularly preferred for use in compositions intended to coat conventional, e.g., polycarbonate, substrates, as compared to high index materials.
- ethylenically unsaturated monomers can be employed in the coating composition of the invention, and acrylic monomers and oligomers, particularly those having acrylic functionalities of not greater than two, are preferred.
- Useful acrylic compounds for improving adhesion to polycarbonate substrates include both mono and di-functional monomers, but other or additional polyfunctional acrylic monomers may also be included.
- monofunctional acrylic monomers include acrylic and methacrylic esters such as ethyl acrylate, butyl acrylate, 2-hydroxypropyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, and the like.
- polyfunctional acrylic monomers including both difunctional and tri and tetrafunctional monomers, include neopentylglycol diacrylate, pentaerythritol triacrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, tetraethylene glycol diacrylate, 1,3-butylene glycol diacrylate, trimethylolpropane trimethacrylate, 1,3-butylene glycol dimethacrylate, ethylene glycol dimethacrylate, pentaerythritol tetraacrylate, tetraethylene glycol dimethacrylate, 1,6-hexanediol dimethacrylate, ethylene glycol diacrylate, diethylene glycol diacrylate, glycerol diacrylate, glycerol triacrylate, 1,3-propanediol diacrylate, 1,3-propanediol dimethacrylate, 1,2,4-butanetriol
- the composition preferably also contains one or more cationic initiators, sufficient to polymerize the epoxy-functional components, and one or more free radical initiators sufficient to initiate polymerization of the ethylenically unsaturated coating components (e.g., acrylic-functional components).
- one or more cationic initiators sufficient to polymerize the epoxy-functional components
- one or more free radical initiators sufficient to initiate polymerization of the ethylenically unsaturated coating components (e.g., acrylic-functional components).
- Useful cationic initiators for the purposes of this invention can include thermal or photoinitators (e.g., UV initiators) and include the aromatic onium salts, including salts of Group Va elements, such as phosphonium salts, e.g., triphenyl phenacylphosphonium hexafluorophosphate, salts of Group VIa elements, such as sulfonium salts, e.g., triphenylsulfonium tetrafluoroborate, triphenylsulfonium hexafluorophosphate and triphenylsulfonium hexafluoroantimonate, and salts of Group VIIa elements, such as iodonium salts, e.g., diphenyliodonium chloride.
- Group Va elements such as phosphonium salts, e.g., triphenyl phenacylphosphonium hexafluorophosphate
- salts of Group VIa elements such as
- Preferred cationic initiators for use in the compositions of this invention are the salts of Group VIa elements and especially the sulfonium salts.
- Particular cationic catalysts include diphenyl iodonium salts of tetrafluoro borate, hexafluoro phosphate, hexafluoro arsenate, and hexafluoro antimonate; and triphenyl sulfonium salts of tetrafluoroborate, hexafluoro phosphate, hexafluoro arsenate, and hexafluoro antimonate.
- photoactivated free-radical initiator are preferred, thermally activated free radical and cationic initiators may also be used.
- Useful photoinitiators for this purpose are the haloalkylated aromatic ketones, chloromethylbenzophenones, certain benzoin ethers, certain acetophenone derivatives such as diethoxyacetophenone and 2-hydroxy-2-methyl-1-phenylpropan-1-one.
- a preferred class of free-radical photoinitiators is the benzil ketals, which produce rapid cures.
- a preferred photoinitiator is ⁇ , ⁇ -dimethoxy- ⁇ -phenyl acetophenone (IragacureTM 651, Ciba-Geigy, disclosed in U.S. Pat. Nos.
- the most preferred photoinitiator in accordance with this invention, is 2-hydroxy-2-methyl-1-phenylpropane-1-one (DarocureTM 1173, Ciba-Geigy Corporation).
- Specific examples of photoinitiators include ethyl benzoin ether, isopropyl benzoin ether, dimethoxyphenyl acetophenone, diethoxy acetophenone, and benzophenone.
- a preferred class of free-radical photoinitiators is the benzil ketals, which produce rapid cures.
- Suitable photoinitiators include .alpha.,.alpha.-dimethoxy-.alpha.-phenyl acetophenone (IragacureTM 651), and 2-hydroxy-2-methyl-1-phenylpropane-1-one (DarocureTM 1173, Ciba-Geigy Corporation).
- a preferred photoiniator is 1-hydroxycyclohexyl phenyl ketone (available as Irgacure 184).
- photoinitiators include ethyl benzoin ether, isopropyl benzoin ether, dimethoxyphenyl acetophenone, diethoxy acetophenone, and benzophenone.
- suitable initiators are diethoxy acetophenone (“DEAP”, First Chemical Corporation) and 1-benzoyl-1-hydroxycyclohexane (“Irgacure 184”, Ciba Geigy).
- compositions of the present invention can be used to coat a variety of materials, generally polymeric materials, and most preferably those used for the manufacture of optical lenses.
- materials generally polymeric materials, and most preferably those used for the manufacture of optical lenses.
- the lens material chosen for a particular use or prescription can be differentiated by various factors, including its weight, thickness, transmission of radiant energy and optical performance.
- a composition of this invention can include other ingredients as well, e.g., other materials that are reactive with the epoxy groups such as hydroxyl bearing compounds such as trimethylol propane or cyclohexane dimethanol may be used to modify the composition.
- the composition can include one or more flow control agents such as BYK 307, rheology modifiers such as cellulose acetate butyrate, metal oxides such as colloidal titanium dioxide, colloidal silica, etc.
- the following table shows the index of refraction of some available lens materials.
- a composition of the present invention can be detected by virtue of the significant concentration of aromatic groups associated with the glycidyl ethers described herein, as compared to what will typically be a considerably smaller concentration of aromatic groups, if any, that may be associated with one or more initiators described herein.
- the invention may be better understood by reference to the following non-limiting examples. Unless otherwise indicated, the concentration of ingredients in a composition is described as a percentage (solids basis) based on the weight of the overall composition. Cured coatings were subjected to several tests, outlined as follows:
- Glycidyl ethers suitable for use in a composition of this invention are described herein, the structures and suitable sources for which are shown in FIG. 1 .
- a stripped, hydrolyzed epoxy silane resin (resin A) was prepared as the reaction product of nonhydrolyzed silane (A187), together with H2O, and (10%) HCl, in the manner described in U.S. Pat. No. 6,100,313 and U.S. Ser. No. 12/987,650, the disclosures of which are incorporated herein by reference.
- Various compositions were prepared as described herein, based upon the master batch, and were coated on a variety of conventional lens materials that included a polycarbonate, a 1.6 high index material, and a 1.67 high index material. All amounts are in weight percent, unless otherwise indicated. Initial results are provided below.
- compositions were coated on conventional polycarbonate and high index lenses, cured and evaluated for both adhesion and other properties.
- composition that instead contained a trifunctional aliphatic ether (in particular, trimethylolpropane triglycidyl ether, of the type described in Applicant's prior U.S. Pat. No. 6,100,313), and
- composition that instead contained 1,4-Bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, which is an aromatic, difunctional oxetane available commercially as “OXT-121”), and
- composition that included RDGE, in combination with one or more conventional aliphatic glycidyl ethers.
- adhesion is preferably determined by means of ASTM 3359, using test methods conventional in the optical (e.g., eyeglass) lens coating industry, though with the notable exception that the lenses are provided in ground, polished form (as routinely done in commercial applications), as compared to first being chemically etched. Briefly, this industry standard test involves scoring the cured coating with a blade assembly in a cross-hatched fashion to leave diamond-shaped patches. This is followed by an attempt to lift the diamond-shaped patches from the substrate through the use of a pressure sensitive adhesive tape that is applied to the cross hatched surface and then pulled away.
- ASTM 3359 ASTM 3359
- composition (a) having an ether of this invention was compared with one (b) having an ether exemplified in the “oxetane” application described above.
- Table 1 it was found that the composition containing RDGE passed each of the crosshatch adhesion tests (deionized water, humidity, QUV), as compared to the oxetane composition, which passed only the deionized water test, but failed the humidity and QUV tests.
- all ingredients are indicated as weight percentages, based on the weight of the compositions themselves.
- composition (a)—RDGE compositions having an ether of this invention
- composition (b) having Heloxy 5048 compositions having Heloxy 5048
- composition (c) compositions having both ethers
- Tintability was adjusted in the manner commonly accepted in the optical industry, in order to render the transmission of each comparable, and less than 23.
- Table 2 it can be seen that both compositions with RDGE performed surprisingly better than the composition b, having conventional ether. Specific amounts of ingredients were determined in order to approximate the same tintability and adhesion in each.
- Adhesion test 1 Adhesion Adhesion (deionized test 2 test 3 Adhesion test 1 water) (humidity) (QUV) RDGE on PC Pass Pass Pass Heloxy 5048 on PC Pass Fail Fail Oxetane on PC Pass Pass Fail RDGE on MR8 (1.60) Pass Pass Pass Heloxy 5048 on MR8 (1.60) Fail Fail Fail Oxetane on MR8(1.60) Pass Pass Fail RDGE on MR10 (1.67) Pass Pass Pass Heloxy 5048 on MR10 (1.67) Fail Fail Fail Oxetane on MR10 (1.67) Pass Pass Fail
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Abstract
Description
- This application is a continuation of U.S. patent application Ser. No. 14/624,036, filed Feb. 17, 2015, the entire contents of which are incorporated herein by reference.
- The present invention relates to the field of transparent coatings for polymeric objects such as eyeglass lenses.
- There is an ongoing need and desire to provide coating compositions that are capable of providing lenses and other such surfaces with improved combinations of properties. For instance, Applicant's U.S. Pat. No. 6,100,313 provides, inter alia, a coating composition that accepts dye well, that provides exceptional abrasion-resistance (AR), and that is substantially free of volatiles. The composition includes a partially hydrolyzed epoxy-functional alkoxysilane, and can also include a polymerizable ether selected from the group consisting of glycidyl ethers, allyl ethers and vinyl ethers.
- Glycidyl ethers said to be useful in the invention of the '313 patent include “triglycidyl ether, γ-glycidoxypropyl trimethoxy silane, triglycidyl ether, 1,4-butanediol diglycidyl ether, Bisphenol A diglycidyl ether, the C8-C14 alkyl glycidyl ethers, butyl glycidyl ether, cresyl glycidyl ether, phenyl glycidyl ether, nonylphenyl glycidyl ether, p-tert-butylphenyl glycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, resorcinol diglycidyl ether, polyglycidyl ethers of aliphatic polyols, cyclohexane dimethanol diglycidyl ether, 2-ethylhexyl glycidyl ether, polyglycol diepoxide, polyglycidyl ether of castor oil, trimethylolethane triglycidyl ether, trimethylolpropane triglycidyl ether, dibromoneopentyl glycol diglycidyl ether, and 3,4-epoxycyclohexyl methyl-3,4-epoxycyclohexane carboxylate. Glycidyl ethers, if used alone as the polymerizable ether, are present preferably in a weight concentration (solids basis) of from about 10% to about 50%.”
- Also, Applicant's US patent application Serial No. U.S. Ser. No. 13/789,998 (“Oxetane”) describes a combination comprising a coated and cured composition as a layer upon the surface of a polymeric material, that includes a partially hydrolyzed organo-functional alkoxysilane and a polymerizable aromatic oxetane, such as 1,4-Bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, which is an aromatic, difunctional oxetane available commercially as “OXT-121”).
- The optical and other industries continue to seek materials, and corresponding surface treatments or coatings, that provide improved properties, such as adhesion, tintability, abrasion resistance, and solubility.
- In one embodiment, the present invention provides a combination comprising a substrate and cured coating formed of the hydrolysis product of an epoxy functional alkoxy silane in combination with one or more monoaromatic (mono- or di)glycidyl ethers. A coating of this invention preferably exhibits an optimal combination of properties that meet or exceed those provided by conventional coatings, including to provide improved adhesion resistance, preferably without the need for a primer, and as determined by crosshatch adhesion tests according to ASTM 3359 (including those involving deionized water, humidity and/or QUV testing). The compositions can be adapted to be tintable as well, using conventional methods and as described herein.
- In one embodiment, the invention provides a coating composition for forming an abrasion-resistant coating upon a substrate, the composition comprising an ether selected from the group consisting of:
-
- a. resorcinol diglycidyl ether (also referred to as 1,3-benzenediol-2,2′-[oxybis(methylene)]dioxirane (1:1) (“RDGE”),
- b. cresyl glycidyl ether (also referred to as epoxidized ortho cresol, o-cresyl glycidyl ether; 2-[(2-methylphenoxy)methyl]oxirane, Tradename GE10),
- c. p-tert-butylphenyl glycidyl ether (also referred to as p-tert-butylphenyl-1-(2,3-epoxy)propyl ether; IUPAC Name: 2-[(4-tert-butylphenoxy)methyl]oxirane, Tradename GE11),
- d. phenyl glicidyl ether (also referred to as epoxidized phenol, 2-(phenoxymethyl)oxirane, an aromatic monofunctional compound (monoepoxide), Tradename GE13),
- e. nonylphenyl glycidyl ether (also referred to as 2-[(4-nonylphenoxy)methyl]oxirane), and
- f. hydroquinone diglycidyl ether (also referred to as 1,4-bis(glycidyloxy) benzene).
- In a particularly preferred embodiment, the ether comprises RDGE (compound (A) above), either alone or in combination with one or more other ethers, including aliphatic or other monoaromatic ethers from within the list provided above. In addition to improved adhesion, RDGE tends to provide improved solubility for use in compositions of the present invention, particularly as compared to ethers (B) through (F) listed above.
- Though each of monoaromatic ethers (A) through (E) (though not (F)) as described herein can be found within the listing of ethers described in the '313 patent, coatings of the present invention provide a surprising and optimal combination of properties that include usefulness with a variety of substrates. In turn, a composition of this invention can provide comparable or improved properties selected from the group consisting of adhesion resistance, stability, tintability, and abrasion resistance, among others. In a particularly preferred embodiment, a composition that includes RDGE can be used to provide a UV curable coating having the potential to meet each of three different adhesion tests used in the optical industry (deionized water, humidity, and QUV), which taken together are typically considered to provide the most stringent adhesion tests used in the industry. Prior UV cured coatings, at their closest, tend to meet only two or fewer of such tests, and particularly when used on High Index substrates, can tend to meet only one of such tests, at most.
- To the best of applicant's awareness, compositions of the present invention provide the only known UV curable, and optionally tintable, coating capable of meeting each of these tests, and in particularly the stringent QUV test.
- In the Drawing,
FIG. 1 provides a chart showing common names, IUPAC names, structures and formulas for each of the preferred glycidyl ethers of this invention. - A UV-cured composition of the present invention can be used as a base coat to provide abrasion resistance (e.g., as determined by Bayer abrasion) that approximates that of a comparable thermally cured base coating, when used as the base coat for an antireflective coating (stack) positioned thereon. The present composition, however, provides various advantages over such thermal cure coatings, including shorter processing times, while having the potential to provide tintability that is as good or better than conventional compositions.
- In turn, the composition is particularly well suited for use as the base coat, before the application of one or more additional layers. Such additional layers often include, for instance, a quartz or oxide (e.g., silicon dioxide) layer, followed by a plurality of coated layers. The resulting “stack” of coated layers can be applied in order to provide an improved array of properties to the overall coated material, including in particular abrasion resistance, as compared to conventional compositions. Applicant has discovered the manner in which particular polymerizable monomers from the group described herein as monoaromatic (mono- or di)glycidyl ethers can be used in combination with organofunctional silanes in order to provide improved compositions, and corresponding base coats having excellent adhesion to polycarbonate and other substrates. More preferably, and desirably, the compositions of this invention have comparable or even improved tintability, as compared to conventional compositions.
- The formation of an abrasion resistant coating, for use on eyeglass lenses, will typically begin with the application of a composition of this invention, e.g., by spin coating and curing the composition with ultraviolet energy. Thereafter, the coated base composition can be subjected to one or more intermediate treatments, for instance, it can be tinted using conventional means, e.g., by dipping the coated lens into a tint bath.
- Once the base composition has been applied, cured, and tinted, the lens material can be subjected to a conventional coating machine, for the application of an antireflection coating, in the form of a ‘stack’ or plurality of layers. Once coated with the composition of this invention, in the form of an initial base coat, the coated lens is typically degassed (e.g., under suitable conditions of time, vacuum, and temperature), followed by the application of an intermediate layer (e.g., quartz or silicon dioxide), which itself can be compacted by e-beam or other means, and finally by the application of one or more AR coatings applied by means of vapor deposition.
- The composition can be used to provide an improved combination of properties, particularly for use in coating lenses and other transparent polymeric materials. Such lens materials include those having an array of properties (e.g., refractive index), and preferably includes both polycarbonate and high index lenses. The coating composition is itself substantially solvent free, and in turn, provides minimal, if any, detectable volatiles in the course of its application, curing, or use. Detectable volatiles are likely to be found, if at all, upon the elimination of methanol upon curing of certain compositions.
- Compositions of this invention are particularly well suited for polymeric substrates, and particularly high refractive index substrates intended for optical applications, including thermosetting and thermoplastic polycarbonates, as well as polyurethanes. Such substrates can be used for a variety of applications, including for automotive instrumentation, aviation gauges and instruments, display and/or shielding windows, eyewear lenses, handheld meters and devices, molded display windows and panels, outdoor equipment gauges and displays, test & laboratory instrument displays, screen printing POP signage, thermoformed displays, medical displays and panels, and video and LED filters.
- In a further preferred embodiment, a coated substrate of this invention comprises a high index material. Particularly preferred high index materials of this type comprise a polyisocyanate compound and a polythiol compound, to provide are described in U.S. Pat. No. 5,652,321, the disclosure of which is incorporated herein by reference. Such materials are described as having an extremely high refractive index and excellent heat resistance, as exemplified in commercial products such as the MR8 and MR10 lines of lenses available from Mitsui Toatsu Chemicals, Inc.
- Given the present description, those skilled in the art will appreciate the manner in which a monoaromatic glycidyl ether can be selected and used to provide desired performance, for instance, based upon the overall formulation, the substrate being coated, additional AR or other coatings to be used, and conditions of use.
- When used in a composition adapted to provide a substantially non-tintable coating, the monoaromatic (mono- or digylcidyl) ether can be present in the coating compositions of the invention at a weight concentration (solids basis) of between about 1 and about 10 weight percent, more preferably between about 2 and about 8 weight percent, and most preferably between about 4 and about 6 weight percent. When used in a composition adapted to provide a substantially tintable coating (e.g., for use in crafting sunglasses), the monoaromatic ether can be present in the coating compositions of the invention at a weight concentration (solids basis) between about 1 and about 40 weight percent, more preferably between about 10 and about 30 weight percent, and most preferably between about 15 and about 25 weight percent. Increasing amounts within these ranges tend to correspond with improved properties, such as improved adhesion. Those skilled in the art, given the present description, will understand the manner in which a ‘tintable’ coating of this type is typically one that can be coated using standard conditions (e.g., dipping in BPI Black for 15 minutes at 95-1000) so as to provide between 18-22% transmission, as compared to a substantially non-tintable coating, which under comparable conditions would result in between 40-45% transmission. The word “substantially”, as used with respect to the present invention, will typically refer to an amount or level sufficient for its intended use.
- In a preferred embodiment, a composition of the present invention comprises a partially hydrolyzed organo-functional alkoxysilane in combination with a monoaromatic glycidyl ether, and optionally other ingredients. The organo-functional alkoxysilane can be of any suitable type, and is preferably selected from the group consisting of epoxy-, vinyl- and acryloxy-functional alkoxysilanes. The organo-functional alkoxysilane, when present, can be used in any suitable amount, e.g., between about 10 and about 60 weight percent, and more preferably between about 20 and about 50 weight percent.
- Suitable acryloxy-functional organosilanes include, are selected from the group consisting of: 3((meth)acryloxypropyl)trimethoxy silane, 3((meth)acryloxyproply)methyl dimethoxy silane, and 3((meth)acryloxypropyl)dimethyl methoxy silane, including combinations thereof.
- Suitable vinyl-functional organosilanes include, but are selected from the group consisting of: vinyldimethyl ethoxysilane, vinylmethyl dimethoxysilane, vinylphenyl diethoxysilane, vinyltrimethoxysilane, and vinyltriethoxysilane, including combinations thereof.
- Suitable epoxy functional alkoxy silane precursors, for use in preparing the at least partially hydrolyzed polymerizable ingredient, are selected from the group consisting of epoxyalkylalkoxysilanes of the following structure: Q-R1—Si(R2)m—(OR3)3-m,
- The epoxy functional alkoxy silane precursor of the at least partially hydrolyzed polymerizable ingredient is preferably an epoxyalkylalkoxysilane of the following structure: Q-R1—Si(R2)m—(OR3)3-m,
- wherein R1 is a C1-C14 alkylene group, R2 and R3 independently are C1-C4 alkyl groups and Q is a glycidoxy or epoxycyclohexyl group, and m is 0 or 1. The alkoxy groups are at least partially hydrolyzed to form silanol groups with the release of the R3OH alcohol, and some condensation of the silanol groups occurs. Epoxy reactivity is preserved, however. Many epoxy-functional alkoxysilanes are suitable as hydrolysis precursors, including glycidoxymethyl-trimethoxysilane, glycidoxymethyltriethoxysilane, glycidoxymethyl-tripropoxysilane, glycidoxymethyl-tributoxysilane, b-glycidoxyethyltrimethoxysilane, b-glycidoxyethyltriethoxysilane, b-glycidoxyethyl-tripropoxysilane, b-glycidoxyethyl-tributoxysilane, b-glycidoxyethyltrimethoxysilane, a-glycidoxyethyl-triethoxysilane, a-glycidoxyethyl-tripropoxysilane, a-glycidoxyethyltributoxysilane, g-glycidoxypropyl-trimethoxysilane, g-glycidoxypropyl-triethoxysilane, g-glycidoxypropyl-tripropoxysilane, g-glycidoxypropyltributoxysilane, b-glycidoxypropyl-trimethoxysilane, b-glycidoxypropyl-triethoxysilane, b-glycidoxypropyl-tripropoxysilane, b-glycidoxypropyltributoxysilane, a-glycidoxypropyl-trimethoxysilane, a-glycidoxypropyl-triethoxysilane, a-glycidoxypropyl-tripropoxysilane, a-glycidoxypropyltributoxysilane, g-glycidoxybutyl-trimethoxysilane, d-glycidoxybutyl-triethoxysilane, d-glycidoxybutyl-tripropoxysilane, d-glycidoxybutyl-tributoxysilane, d-glycidoxybutyl-trimethoxysilane, g-glycidoxybutyl-triethoxysilane, g-glycidoxybutyl-tripropoxysilane, g-propoxybutyl-tributoxysilane, d-glycidoxybutyl-trimethoxysilane, d-glycidoxybutyl-triethoxysilane, d-glycidoxybutyl-tripropoxysilane, a-glycidoxybutyl-trimethoxysilane, a-glycidoxybutyl-triethoxysilane, a-glycidoxybutyl-tripropoxysilane, a-glycidoxybutyl-tributoxysilane, (3,4-epoxycyclohexyl)-methyl-trimethoxysilane, (3,4-epoxycyclohexyl)methyl-triethoxysilane, (3,4-epoxycyclohexyl)methyl-tripropoxysilane, (3,4-epoxycyclohexyl)-methyl-tributoxysilane, (3,4-epoxycyclohexyl)ethyl-triethoxysilane, (3,4-epoxycyclohexyl)ethyl-triethoxysilane, (3,4-epoxycyclohexyl)ethyl-tripropoxysilane, (3,4-epoxycyclohexyl)-ethyl-tributoxysilane, (3,4-epoxycyclohexyl)propyl-trimethoxysilane, (3,4-epoxycyclohexyl)propyl-triethoxysilane, (3,4-epoxycyclohexyl)propyl-tripropoxysilane, (3,4-epoxycyclohexyl)propyl-tributoxysilane, (3,4-epoxycyclohexyl)butyl-trimethoxysilane, (3,4-epoxycyclohexy)butyl-triethoxysilane, (3,4-epoxycyclohexyl)-butyl-tripropoxysilane, and (3,4-epoxycyclohexyl)butyl-tributoxysilane.
- A particularly preferred organo-functional alkoxysilane is γ-glicidoxypropyl trimethoxy silane due to its wide commercial availability.
- Hydrolysis of the alkoxy-functional alkoxysilane precursor may occur in an acidic environment, and reference is made to U.S. Pat. No. 4,378,250, the teachings of which are incorporated herein by reference. Hydrolysis of the alkoxy groups liberates the associated alcohol to form silanol groups; these, in turn, are relatively unstable and tend to condense spontaneously. Preferably, the alkoxysilane is reacted with a stoichiometricly sufficient quantity of water to hydrolyze at least 50% of the alkoxy groups and most preferably from about 60% to about 70% of the alkoxy groups. For the hydrolysis of an epoxy-functional trialkoxy silane, good results have been obtained by reacting the silane with a stoichiometricly sufficient quantity of water to hydrolyze two-thirds of the alkoxy groups.
- The composition of this invention further comprises a monomeric organofunctional silane, and more preferably a monomeric (silanol free) alkoxy functional silane, which can also be referred to as an unhydrolyzed alkoxy functional alkoxy silane. In turn, certain preferred compositions can include both hydrolyzed and unhydrolyzed alkoxy functional alkoxy silanes, with the latter being present in an amount sufficient to reduce the viscosity of the composition itself. It is noted that, while the “hydrolysis product” of such a silane can certainly include compounds that are themselves partially hydrolyzed (depending on the mole ratio of water to alkoxy groups as described herein), whereas an unhydrolyzed silane of the sort claimed is clearly one that is prepared and used in the substantial absence of water. As described herein, water is removed from the hydrolysis product component, prior to the addition of an unhydrolyzed component, in order to permit the latter to retain its unhydrolyzed nature. Hence, when and to the extent “partially hydrolyzed” silanes might be discussed in the art, these compounds tend to be different than, and not at all suggestive of the use of both hydrolyzed and unhydrolyzed silane components as presently described.
- In turn, the composition desirably includes an effective amount up of a suitable non-hydrolyzed alkoxy functional silane, including those selected from the silanes listed above. When used in combination with an organofunctional polysiloxane, the non-hydrolyzed epoxy functional alkoxy silane desirably is present in an amount not less than about 5%, preferably at least about 20%, and most preferably from about 40% to about 50% by weight, solids basis. Preferably, the epoxy functional alkoxy silane that is included as the non-hydrolyzed component also is of the same or similar type as that employed to make the hydrolyzed component. It should be understood that the hydrolyzed and non-hydrolyzed components may be different and each may utilize one or a blend of different epoxy functional alkoxy silanes, as desired.
- The monomeric silane is optional, and therefore used in an amount of between about 0% and about 50%, and more preferably between about 10% and about 40%, and even more preferably between about 20% and about 40% by weight of the composition, with typically more monomeric silane (e.g., about 35 to about 45%) being used in substantially non-tintable compositions, as compared to substantially tintable compositions (e.g., having about 35% to about 45% by weight).
- A composition of the present invention can further comprise one or more additional reactive ingredients, selected from the group consisting of one or more non-hydrolyzed silanes, one or more polyermizable ethers, and one or more ethylenically unsaturated monomer components, desirably an acrylic monomer component that preferably includes a monomer having an acrylic functionality of not more than two. The use of an acrylic monomer, though optional, is particularly preferred for use in compositions intended to coat conventional, e.g., polycarbonate, substrates, as compared to high index materials.
- A wide variety of ethylenically unsaturated monomers (including oligomers) can be employed in the coating composition of the invention, and acrylic monomers and oligomers, particularly those having acrylic functionalities of not greater than two, are preferred. Useful acrylic compounds for improving adhesion to polycarbonate substrates include both mono and di-functional monomers, but other or additional polyfunctional acrylic monomers may also be included.
- Examples of monofunctional acrylic monomers include acrylic and methacrylic esters such as ethyl acrylate, butyl acrylate, 2-hydroxypropyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, and the like. Examples of polyfunctional acrylic monomers, including both difunctional and tri and tetrafunctional monomers, include neopentylglycol diacrylate, pentaerythritol triacrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, tetraethylene glycol diacrylate, 1,3-butylene glycol diacrylate, trimethylolpropane trimethacrylate, 1,3-butylene glycol dimethacrylate, ethylene glycol dimethacrylate, pentaerythritol tetraacrylate, tetraethylene glycol dimethacrylate, 1,6-hexanediol dimethacrylate, ethylene glycol diacrylate, diethylene glycol diacrylate, glycerol diacrylate, glycerol triacrylate, 1,3-propanediol diacrylate, 1,3-propanediol dimethacrylate, 1,2,4-butanetriol trimethacrylate, 1,4-cyclohexanediol diacrylate, 1,4-cyclohexanediol dimethacrylate, pentaerythritol diacrylate, 1,5-pentanediol dimethacrylate, and the like. The acrylic-functional monomers and oligomers desirably are employed at a weight concentration of at least about 10% by weight, preferably from about 10% to about 50%, and most preferably from about 10% to about 25%, all on a solids basis.
- The composition preferably also contains one or more cationic initiators, sufficient to polymerize the epoxy-functional components, and one or more free radical initiators sufficient to initiate polymerization of the ethylenically unsaturated coating components (e.g., acrylic-functional components).
- Useful cationic initiators for the purposes of this invention can include thermal or photoinitators (e.g., UV initiators) and include the aromatic onium salts, including salts of Group Va elements, such as phosphonium salts, e.g., triphenyl phenacylphosphonium hexafluorophosphate, salts of Group VIa elements, such as sulfonium salts, e.g., triphenylsulfonium tetrafluoroborate, triphenylsulfonium hexafluorophosphate and triphenylsulfonium hexafluoroantimonate, and salts of Group VIIa elements, such as iodonium salts, e.g., diphenyliodonium chloride. The aromatic onium salts and their use as cationic initiators in the polymerization of epoxy compounds are described in detail in U.S. Pat. No. 4,058,401, “Photocurable Compositions Containing Group VIA Aromatic Onium Salts,” by J. V. Crivello issued Nov. 15, 1977; U.S. Pat. No. 4,069,055, “Photocurable Epoxy Compositions Containing Group VA Onium Salts,” by J. V. Crivello issued Jan. 17, 1978; U.S. Pat. No. 4,101,513, “Catalyst For Condensation Of Hydrolyzable Silanes And Storage Stable Compositions Thereof,” by F. J. Fox et al. issued Jul. 18, 1978; and U.S. Pat. No. 4,161,478, “Photoinitiators,” by J. V. Crivello issued Jul. 17, 1979, the disclosures of which are incorporated herein by reference. Other cationic initiators can also be used in addition to those referred to above; for example, the phenyldiazonium hexafluorophosphates containing alkoxy or benzyloxy radicals as substituents on the phenyl radical as described in U.S. Pat. No. 4,000,115, “Photopolymerization Of Epoxides,” by Sanford S. Jacobs issued Dec. 28, 1976, the disclosure of which is incorporated herein by reference. Preferred cationic initiators for use in the compositions of this invention are the salts of Group VIa elements and especially the sulfonium salts. Particular cationic catalysts include diphenyl iodonium salts of tetrafluoro borate, hexafluoro phosphate, hexafluoro arsenate, and hexafluoro antimonate; and triphenyl sulfonium salts of tetrafluoroborate, hexafluoro phosphate, hexafluoro arsenate, and hexafluoro antimonate.
- Although photoactivated free-radical initiator are preferred, thermally activated free radical and cationic initiators may also be used. Useful photoinitiators for this purpose are the haloalkylated aromatic ketones, chloromethylbenzophenones, certain benzoin ethers, certain acetophenone derivatives such as diethoxyacetophenone and 2-hydroxy-2-methyl-1-phenylpropan-1-one. A preferred class of free-radical photoinitiators is the benzil ketals, which produce rapid cures. A preferred photoinitiator is α,α-dimethoxy-α-phenyl acetophenone (Iragacure™ 651, Ciba-Geigy, disclosed in U.S. Pat. Nos. 3,715,293 and 3,801,329). The most preferred photoinitiator, in accordance with this invention, is 2-hydroxy-2-methyl-1-phenylpropane-1-one (Darocure™ 1173, Ciba-Geigy Corporation). Specific examples of photoinitiators include ethyl benzoin ether, isopropyl benzoin ether, dimethoxyphenyl acetophenone, diethoxy acetophenone, and benzophenone.
- A preferred class of free-radical photoinitiators is the benzil ketals, which produce rapid cures. Suitable photoinitiators include .alpha.,.alpha.-dimethoxy-.alpha.-phenyl acetophenone (Iragacure™ 651), and 2-hydroxy-2-methyl-1-phenylpropane-1-one (Darocure™ 1173, Ciba-Geigy Corporation). A preferred photoiniator is 1-hydroxycyclohexyl phenyl ketone (available as Irgacure 184). Specific examples of photoinitiators include ethyl benzoin ether, isopropyl benzoin ether, dimethoxyphenyl acetophenone, diethoxy acetophenone, and benzophenone. Other examples of suitable initiators are diethoxy acetophenone (“DEAP”, First Chemical Corporation) and 1-benzoyl-1-hydroxycyclohexane (“Irgacure 184”, Ciba Geigy).
- Compositions of the present invention can be used to coat a variety of materials, generally polymeric materials, and most preferably those used for the manufacture of optical lenses. Those skilled in the corresponding art will appreciate the manner in which the lens material chosen for a particular use or prescription can be differentiated by various factors, including its weight, thickness, transmission of radiant energy and optical performance.
- A composition of this invention can include other ingredients as well, e.g., other materials that are reactive with the epoxy groups such as hydroxyl bearing compounds such as trimethylol propane or cyclohexane dimethanol may be used to modify the composition. In addition, the composition can include one or more flow control agents such as BYK 307, rheology modifiers such as cellulose acetate butyrate, metal oxides such as colloidal titanium dioxide, colloidal silica, etc.
- The following table shows the index of refraction of some available lens materials.
-
Lens Material Index of Refraction allyl diglycol carbonate (e.g., “CR-39”) 1.498 Crown Glass 1.523 Polycarbonate 1.586 MR8 1.6 MR10 1.67 - With certain preferred embodiments as described herein, a composition of the present invention can be detected by virtue of the significant concentration of aromatic groups associated with the glycidyl ethers described herein, as compared to what will typically be a considerably smaller concentration of aromatic groups, if any, that may be associated with one or more initiators described herein.
- The invention may be better understood by reference to the following non-limiting examples. Unless otherwise indicated, the concentration of ingredients in a composition is described as a percentage (solids basis) based on the weight of the overall composition. Cured coatings were subjected to several tests, outlined as follows:
- Materials and Methods
- Glycidyl ethers suitable for use in a composition of this invention are described herein, the structures and suitable sources for which are shown in
FIG. 1 . - A187 Glycidoxy propyl trimethoxy silane (GE Silicones)
- A 1630 Methyl trimethoxy silane (Crompton Corp)
SR 9209 alkoxylated aliphatic diacrylate (Sartomer, Inc.)
SR 444 pentaerythritol triacrylate (Sartomer, Inc.)
SR-351 trimethylolpropane triacrylate (TMPTA, Sartomer, Inc.)
SR-238 1,6 hexanediol diacrylate (HDODA, Sartomer, Inc.)
DEAP 2,2-diethoxy acetophenone, free radical initiator (First Chemical Corporation)
CPI 6976 Cationic initiator (Aceto Corp.)
CPI 6972 Cationic initiator (Aceto Corp.)
Irgacure 184 Free radical photoiniator (Ciba Geigy)
Irgacure 250 Cationic photoiniator (Ciba Geigy)
Uvacure 1502 Cycloaliphatic epoxy resin (UCB Chemicals Corp)
OXT-121 (1,4-Bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, CAS No. 142627-97-2 (Toagosei Co.)
BYK 307 Silicone type flow control agent (BYK-Chemie)
HELOXY™ 107 diglycidyl ether of cyclohexane dimethanol (Momentive, Inc.)
HELOXY™ 48 low viscosity aliphatic triglycidyl ether (Momentive, Inc.) - Preparation—a stripped, hydrolyzed epoxy silane resin (resin A) was prepared as the reaction product of nonhydrolyzed silane (A187), together with H2O, and (10%) HCl, in the manner described in U.S. Pat. No. 6,100,313 and U.S. Ser. No. 12/987,650, the disclosures of which are incorporated herein by reference. Various compositions were prepared as described herein, based upon the master batch, and were coated on a variety of conventional lens materials that included a polycarbonate, a 1.6 high index material, and a 1.67 high index material. All amounts are in weight percent, unless otherwise indicated. Initial results are provided below.
- The various compositions were coated on conventional polycarbonate and high index lenses, cured and evaluated for both adhesion and other properties.
- Experiments were also performed to determine the effect of various compositions in coating high index lenses, and in particular, those lenses prepared from polymers sold under the brandnames MR8 and MR10. All samples were coated on 1.6 RI lenses made from monomer blend MR8 at 4-5 microns thickness and UV cured using high pressure mercury lamp. The same results were obtained when coated on 1.67 RI lenses made from MR10 monomer blend. The samples were evaluated for adhesion as per ASTM D 3359 as described herein.
- Experiments were performed in order to compare a silane composition containing RDGE, a preferred ether of the present invention, in combination with various other compositions, including:
- i) a composition that instead contained a trifunctional aliphatic ether (in particular, trimethylolpropane triglycidyl ether, of the type described in Applicant's prior U.S. Pat. No. 6,100,313), and
- ii) a composition that instead contained 1,4-Bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, which is an aromatic, difunctional oxetane available commercially as “OXT-121”), and
- iii) a composition that included RDGE, in combination with one or more conventional aliphatic glycidyl ethers.
- For purposes of the present specification, adhesion is preferably determined by means of ASTM 3359, using test methods conventional in the optical (e.g., eyeglass) lens coating industry, though with the notable exception that the lenses are provided in ground, polished form (as routinely done in commercial applications), as compared to first being chemically etched. Briefly, this industry standard test involves scoring the cured coating with a blade assembly in a cross-hatched fashion to leave diamond-shaped patches. This is followed by an attempt to lift the diamond-shaped patches from the substrate through the use of a pressure sensitive adhesive tape that is applied to the cross hatched surface and then pulled away. The degree to which the cross-hatched portions of the coating remain adhered to the substrate provides a measure of adhesion to that substrate, and is reported as the percentage of diamond-shapes that remain adhered to the substrate. Crosshatch adhesion tests were run under three conditions, in the manner described in Colts Laboratories catalog of standard services available at www.colts-laboratories.com, which include:
(1) boiling water (deionized water). This involves a standard crosshatch adhesion test in which a series of fine cuts are first made across and into the surface of the coated test lens, which is then subjected to boiling water for a period of time, before tape is placed firmly on the crosshatched area and quickly pulled off.
(2) Cycle humidity oven (CHOCA). This involves a 3 day adhesion test in which coated lenses are submitted to both a crosshatch test and a cycle humidity test. The crosshatch cuts are completed prior to the start of the humidity portion, thereby attempting to replicate what might occur under actual conditions. In this test the oven cycles to 95% RH three times at 65 C, and the test lenses are inspected following each 8 hour cycle.
(3) Cycle humidity QUV/crosshatch, which mimics the most aggressive components of accelerated weathering. This involves a 3 day adhesion test in which coated lenses are submitted to both a crosshatch test and the cycle humidity test. The crosshatch cuts are completed prior to the start of the humidity portion, thereby attempting to replicate what may occur under actual conditions. The QUV equipment alternates between UVA and condensation cycles. - Results were scored according to standard acceptable proceedures (as provided, for instance, by Colts Laboratories). Standard protocols and operating procedures were followed to determine crosshatch adhesion results under the following three categories:
-
- 5B—the edges of the cuts are completely smooth, none of the squares of the crosshatched area are detached.
- 4B—small flakes of the coating are detached at the intersections of the squares, less than 5% of the total area is affected.
- 3B—small flakes of the coating are detached along the edges and at intersections of cuts. The area affected is 5-15% of the total area.
- 2B—the coating has flaked along the edges and on parts of the squares. The area affected is 15-35% of the total area.
- 1B—the coating has flaked along edges of the cuts in large ribbons and whole squares are detached. The area affected is 35-655 of the total area.
- 0B—flaking and detachment worse than Classification 1 (greater than 65%).
Tintability—A coated and cured sample is immersed in BPI Black Dye (Brain Power Inc.) at 98-102° C. for 15 minutes and then rinsed with water and dried. Transmissivity is measured spectrophotometrically, and tintability is reported as percentage transmissivity.
Bayer abrasion (scratch resistance) testing—is performed by suitable modification of the oscillating sand method (ASTM-F735-94 Standard Test Method for Abrasion Resistance of Transparent Plastics and coatings), modified slightly to allow for use in the optical field. The test consists of a small pan that is shaken back and forth a distance of 4 inches, at 150 cycles for 4 minutes, using abrasion media the material known as Aluminum Oxide from Black Lab corp. Designation AO-14 Brown. Holes have been placed through the center section of the pan to allow the lenses to protrude up through the center of each hole, allowing the abrasion to take place without the loss of media.
- A composition (a) having an ether of this invention (RDGE-H) was compared with one (b) having an ether exemplified in the “oxetane” application described above. Surprisingly, as shown in Table 1, it was found that the composition containing RDGE passed each of the crosshatch adhesion tests (deionized water, humidity, QUV), as compared to the oxetane composition, which passed only the deionized water test, but failed the humidity and QUV tests. Unless otherwise indicated, all ingredients are indicated as weight percentages, based on the weight of the compositions themselves.
-
TABLE 1 (b) Oxetane (a) RDGE (OXT121) A18790 42.5 47.5 (Resin A, hydrolyzed epoxy silane) A187 (glycidoxypropyl trimethoxy 37.4 31.7 silane) BDDA (butane diol diacrylate) 10.7 7.9 Glycidyl ether RDGE 5.3 0 Oxetane OXT 121 0 7.9 IRG184 (free radical initiator) 0.29 0.4 CPI 6976 (cationic initator) 4.37 4.35 BYK307 (flow control agent) 0.25 0.25 TOTAL 100 100 PROPERTIES/TEST RESULTS Tint BPI black (% transmission) — — Bayer abrasion 2.2 2.3 Boiling DI water - PC 5B 5B Boiling DI MR8 (1.60) 5B 5B Boiling DI MR10 (1.67) 5B 5B Humidity PC 5B 5B Humidity 1.60 MR8 (1.60) 5B 5B Humidity 1.67 MR10 (1.67) 5B 5B QUV PC 5B 5B (for the first of 3 cycles) (0B second cycle) QUV MR8 (1.60) 5B 0B QUV MR10 (1.67) 5B 0B - Experiments were also performed to compare compositions having an ether of this invention (composition (a)—RDGE) with one exemplified in Applicant's above-captioned '313 patent and currently used in corresponding commercial products such as UV-87 available from Walman Ultra-Optics (composition (b) having Heloxy 5048), as well as the combination of both ethers (composition (c)). Tintability was adjusted in the manner commonly accepted in the optical industry, in order to render the transmission of each comparable, and less than 23. In Table 2, it can be seen that both compositions with RDGE performed surprisingly better than the composition b, having conventional ether. Specific amounts of ingredients were determined in order to approximate the same tintability and adhesion in each.
-
TABLE 2 (c) Both RDGE and (b) Heloxy Heloxy (a) RDGE 5048 5048 A18790 30.0 31.6 30.15 (Resin A, hydrolyzed epoxy silane) A187 (glycidoxypropyl trimethoxy 30.35 20.0 16.0 silane) BDDA (butane diol diacrylate) 20.0 18.75 25.1 Glycidyl ether RDGE 15.0 0 10.05 Heloxy 5048 polymerizable 0 25.0 15.08 ether trimethylolypropane IRG184 (free radical initiator) 0.6 0.56 0.75 CPI 6976 (cationic initator) 3.8 3.85 3.52 BYK307 (flow control) 0.25 0.25 0.25 TOTAL 100 100 100 PROPERTIES/TEST RESULTS Tint BPI black (% transmission) 20.0 22.2 22.0 Boiling DI water/PC 5B 5B 5B Boiling DI water MR8 (1.60) 5B 0B 5B Boiling DI water MR10 (1.67) 5B 0B 5B Humidity PC 5B 0B 5B Humidity MR8 (1.60) 5B 0B 5B Humidity MR10 (1.67) 5B 0B 5B QUV PC 5B 0B 5B QUV MR8 (1.60) 5B 0B 5B QUV MR10 (1.67) 5B 0B 5B -
TABLE 3 Adhesion test 1 Adhesion Adhesion (deionized test 2test 3Adhesion test 1 water) (humidity) (QUV) RDGE on PC Pass Pass Pass Heloxy 5048 on PC Pass Fail Fail Oxetane on PC Pass Pass Fail RDGE on MR8 (1.60) Pass Pass Pass Heloxy 5048 on MR8 (1.60) Fail Fail Fail Oxetane on MR8(1.60) Pass Pass Fail RDGE on MR10 (1.67) Pass Pass Pass Heloxy 5048 on MR10 (1.67) Fail Fail Fail Oxetane on MR10 (1.67) Pass Pass Fail - Results are summarized in Table 3 above. It can be seen, that under the conditions of the current experiments, the composition based upon the use of RDGE surprisingly passed each of adhesion tests 1-3, as compared to compositions previously known and described, which failed one or more tests, most notably the QUV adhesion test.
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