WO2007070975A1 - Primer layer coating compositions - Google Patents
Primer layer coating compositions Download PDFInfo
- Publication number
- WO2007070975A1 WO2007070975A1 PCT/AU2006/001985 AU2006001985W WO2007070975A1 WO 2007070975 A1 WO2007070975 A1 WO 2007070975A1 AU 2006001985 W AU2006001985 W AU 2006001985W WO 2007070975 A1 WO2007070975 A1 WO 2007070975A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- optical element
- element according
- ether
- preparing
- coating
- Prior art date
Links
- 239000008199 coating composition Substances 0.000 title claims abstract description 44
- 230000003287 optical effect Effects 0.000 claims abstract description 143
- 239000000178 monomer Substances 0.000 claims abstract description 109
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000004593 Epoxy Substances 0.000 claims abstract description 43
- 239000000758 substrate Substances 0.000 claims abstract description 26
- 125000002091 cationic group Chemical group 0.000 claims abstract description 14
- 238000000576 coating method Methods 0.000 claims description 106
- 239000011248 coating agent Substances 0.000 claims description 88
- 229960000834 vinyl ether Drugs 0.000 claims description 64
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 48
- 238000005299 abrasion Methods 0.000 claims description 33
- -1 alkyl vinyl ethers Chemical class 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 30
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 11
- 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 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 8
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 6
- 238000005266 casting Methods 0.000 claims description 6
- 239000012952 cationic photoinitiator Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- 229920001289 polyvinyl ether Polymers 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 6
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 6
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 6
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 229940052303 ethers for general anesthesia Drugs 0.000 claims description 5
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical group CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims description 4
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 claims description 4
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 claims description 4
- RQZUWSJHFBOFPI-UHFFFAOYSA-N 2-[1-[1-(oxiran-2-ylmethoxy)propan-2-yloxy]propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COC(C)COCC1CO1 RQZUWSJHFBOFPI-UHFFFAOYSA-N 0.000 claims description 4
- FVCHRIQAIOHAIC-UHFFFAOYSA-N 2-[1-[1-[1-(oxiran-2-ylmethoxy)propan-2-yloxy]propan-2-yloxy]propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COC(C)COC(C)COCC1CO1 FVCHRIQAIOHAIC-UHFFFAOYSA-N 0.000 claims description 4
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 claims description 4
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 claims description 4
- OZRVXYJWUUMVOW-UHFFFAOYSA-N 2-[[4-[4-(oxiran-2-ylmethoxy)phenyl]phenoxy]methyl]oxirane Chemical group C1OC1COC(C=C1)=CC=C1C(C=C1)=CC=C1OCC1CO1 OZRVXYJWUUMVOW-UHFFFAOYSA-N 0.000 claims description 4
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 4
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical group OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 229960000250 adipic acid Drugs 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- KZYBDOUJLUPBEH-UHFFFAOYSA-N bis(4-ethenoxybutyl) benzene-1,3-dicarboxylate Chemical group C=COCCCCOC(=O)C1=CC=CC(C(=O)OCCCCOC=C)=C1 KZYBDOUJLUPBEH-UHFFFAOYSA-N 0.000 claims description 3
- 229960005137 succinic acid Drugs 0.000 claims description 3
- SDNBHBGJJPWRJG-UHFFFAOYSA-N bis[[4-(ethenoxymethyl)cyclohexyl]methyl] pentanedioate Chemical compound C1CC(COC=C)CCC1COC(=O)CCCC(=O)OCC1CCC(COC=C)CC1 SDNBHBGJJPWRJG-UHFFFAOYSA-N 0.000 claims 2
- 230000003213 activating effect Effects 0.000 claims 1
- 229920001296 polysiloxane Polymers 0.000 claims 1
- 239000010410 layer Substances 0.000 description 99
- 239000002987 primer (paints) Substances 0.000 description 90
- 239000000463 material Substances 0.000 description 30
- 239000011247 coating layer Substances 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 14
- 239000003999 initiator Substances 0.000 description 13
- 229920003023 plastic Polymers 0.000 description 12
- 239000004033 plastic Substances 0.000 description 12
- 238000009863 impact test Methods 0.000 description 10
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920002578 polythiourethane polymer Polymers 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- 150000003553 thiiranes Chemical class 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 2
- 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
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000012949 free radical photoinitiator Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- SPNAQSNLZHHUIJ-UHFFFAOYSA-N s-[4-[4-(2-methylprop-2-enoylsulfanyl)phenyl]sulfanylphenyl] 2-methylprop-2-enethioate Chemical compound C1=CC(SC(=O)C(=C)C)=CC=C1SC1=CC=C(SC(=O)C(C)=C)C=C1 SPNAQSNLZHHUIJ-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- 150000007970 thio esters Chemical class 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (1R)-1,3-butanediol Natural products CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- PCLLJCFJFOBGDE-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)methanamine Chemical compound NCC1=CC(Br)=CC=C1Cl PCLLJCFJFOBGDE-UHFFFAOYSA-N 0.000 description 1
- KILURZWTCGSYRE-LNTINUHCSA-K (z)-4-bis[[(z)-4-oxopent-2-en-2-yl]oxy]alumanyloxypent-3-en-2-one Chemical compound CC(=O)\C=C(\C)O[Al](O\C(C)=C/C(C)=O)O\C(C)=C/C(C)=O KILURZWTCGSYRE-LNTINUHCSA-K 0.000 description 1
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-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
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- FYBFGAFWCBMEDG-UHFFFAOYSA-N 1-[3,5-di(prop-2-enoyl)-1,3,5-triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CN(C(=O)C=C)CN(C(=O)C=C)C1 FYBFGAFWCBMEDG-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- CCTFAOUOYLVUFG-UHFFFAOYSA-N 2-(1-amino-1-imino-2-methylpropan-2-yl)azo-2-methylpropanimidamide Chemical compound NC(=N)C(C)(C)N=NC(C)(C)C(N)=N CCTFAOUOYLVUFG-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 description 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical class CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-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
- OPPHXULEHGYZRW-UHFFFAOYSA-N 4-methoxy-2,4-dimethyl-2-phenyldiazenylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC1=CC=CC=C1 OPPHXULEHGYZRW-UHFFFAOYSA-N 0.000 description 1
- FKAJZOZTZXQGTJ-UHFFFAOYSA-N 5,5-dimethyl-1,3-diazabicyclo[2.2.0]hex-3-ene Chemical compound C1N2C(C1(C)C)=NC2 FKAJZOZTZXQGTJ-UHFFFAOYSA-N 0.000 description 1
- PGFZYOCLSPEKSN-UHFFFAOYSA-N 5,5-dimethyl-1,3-diazabicyclo[2.2.0]hex-3-ene dihydrochloride Chemical compound Cl.Cl.CC1(C)CN2CN=C12 PGFZYOCLSPEKSN-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
- KSXJRXNHRYSLLC-UHFFFAOYSA-N 9H-fluorene prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.C1=CC=C2CC3=CC=CC=C3C2=C1 KSXJRXNHRYSLLC-UHFFFAOYSA-N 0.000 description 1
- KKRDAKIXWNNYNV-UHFFFAOYSA-N 9h-fluorene;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.C1=CC=C2CC3=CC=CC=C3C2=C1 KKRDAKIXWNNYNV-UHFFFAOYSA-N 0.000 description 1
- JKZSFALEYCUXGP-UHFFFAOYSA-N 9h-fluorene;prop-2-enoic acid Chemical class OC(=O)C=C.C1=CC=C2CC3=CC=CC=C3C2=C1 JKZSFALEYCUXGP-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- KNVWLKLAXCYRND-UHFFFAOYSA-L C(C=C)(=O)[O-].C(C=C)(=O)[O-].[Li+].[Li+] Chemical compound C(C=C)(=O)[O-].C(C=C)(=O)[O-].[Li+].[Li+] KNVWLKLAXCYRND-UHFFFAOYSA-L 0.000 description 1
- 229920002574 CR-39 Polymers 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 description 1
- NKIDFMYWMSBSRA-UHFFFAOYSA-N [4-(2-methylprop-2-enoyloxymethyl)cyclohexyl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CCC(COC(=O)C(C)=C)CC1 NKIDFMYWMSBSRA-UHFFFAOYSA-N 0.000 description 1
- VVTSZOCINPYFDP-UHFFFAOYSA-N [O].[Ar] Chemical compound [O].[Ar] VVTSZOCINPYFDP-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000006117 anti-reflective coating Substances 0.000 description 1
- 230000003667 anti-reflective effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- WPKWPKDNOPEODE-UHFFFAOYSA-N bis(2,4,4-trimethylpentan-2-yl)diazene Chemical compound CC(C)(C)CC(C)(C)N=NC(C)(C)CC(C)(C)C WPKWPKDNOPEODE-UHFFFAOYSA-N 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- TXTCTCUXLQYGLA-UHFFFAOYSA-L calcium;prop-2-enoate Chemical compound [Ca+2].[O-]C(=O)C=C.[O-]C(=O)C=C TXTCTCUXLQYGLA-UHFFFAOYSA-L 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical class [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 125000005520 diaryliodonium group Chemical group 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229940113120 dipropylene glycol Drugs 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- VWPOBUVSGMLNCM-UHFFFAOYSA-L disodium prop-2-enoate Chemical compound [Na+].C(C=C)(=O)[O-].[Na+].C(C=C)(=O)[O-] VWPOBUVSGMLNCM-UHFFFAOYSA-L 0.000 description 1
- GKCPCPKXFGQXGS-UHFFFAOYSA-N ditert-butyldiazene Chemical compound CC(C)(C)N=NC(C)(C)C GKCPCPKXFGQXGS-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 1
- JZMPIUODFXBXSC-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.CCOC(N)=O JZMPIUODFXBXSC-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229940047889 isobutyramide Drugs 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- DWLAVVBOGOXHNH-UHFFFAOYSA-L magnesium;prop-2-enoate Chemical compound [Mg+2].[O-]C(=O)C=C.[O-]C(=O)C=C DWLAVVBOGOXHNH-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- VXRNYQMFDGOGSI-UHFFFAOYSA-N n-(1,3-dihydroxy-2-methylpropan-2-yl)-2-[[1-[(1,3-dihydroxy-2-methylpropan-2-yl)amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(C)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(C)(CO)CO VXRNYQMFDGOGSI-UHFFFAOYSA-N 0.000 description 1
- WVFLGSMUPMVNTQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCO WVFLGSMUPMVNTQ-UHFFFAOYSA-N 0.000 description 1
- BUGISVZCMXHOHO-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-[[1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(CO)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(CO)(CO)CO BUGISVZCMXHOHO-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 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
- 239000012815 thermoplastic material Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00865—Applying coatings; tinting; colouring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
-
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D163/10—Epoxy resins modified by unsaturated compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31938—Polymer of monoethylenically unsaturated hydrocarbon
Definitions
- the present invention relates to a coating composition that can be used to form a primer layer on coated optical elements, such as ophthalmic lenses.
- the primer layer confers impact resistance on optical elements having an anti-reflection coating and also assists with adhesion of adjacent coating layers.
- the invention also relates to optical elements, especially ophthalmic lenses, containing the primer layer, and to methods for forming impact resistant AR coated optical elements.
- Plastic materials are widely used as substitutes for glass in many applications, and particularly for optical elements such as ophthalmic lenses. Plastic materials have a number of advantages over glass, such as lighter weight, ease of handling and ease of formation of articles. However, plastic materials rarely have all of the physical and/or optical properties required for a particular application. Most notably, plastic materials are soft and scratch quite readily in comparison to glass.
- plastic optical elements such as ophthalmic lenses are generally coated with abrasion resistant "hard coats” to reduce abrasion on the surface of the element.
- optical elements such as ophthalmic lenses often include an anti-reflection ("AR") coating to improve transmittance of visible light.
- AR anti-reflection
- coatings such as hard coats and AR coats
- problems can be problems with adhesion of hard coating layers to an optical element, or to other coating layers, and AR coatings are brittle and they crack relatively easily. These problems can reduce the product life of optical elements containing these coatings.
- lenses having a centre thickness of about 1 mm are sought after.
- the prior art contains a number of suggestions for providing primer layers for improving the impact resistance of optical elements and the adhesion of coating layers on the optical element.
- United States patent 6,051 ,310 to Cano et al. describes an ophthalmic lens having an abrasion resistant coating, a layer of impact resistant primer, and an inorganic AR coating.
- the primer layer which is inserted between the abrasion resistant coating and the AR coating, is formed using an epoxysilane based polymer.
- United States patent 6,551 ,710 to the present applicants also describes a primer composition that can be used to form impact resistant primer layers on ophthalmic lenses having hard coats and AR coats.
- the primer layer is formed using a thiolene based polymer.
- Published United States patent application 2003/0118833 to Essilor describes the formation of a primer layer from a non-hydrophilic acrylate monomer and an epoxy monomer.
- the present invention provides a coated optical element including an optical substrate and a primer layer, the primer layer being formed by cationic polymerisation of a coating composition containing an effective amount of: an epoxy monomer; and a vinyl ether monomer.
- the present invention also provides a method of preparing an optical element having a primer layer, the method including:
- a coating composition containing an effective amount of: i. an epoxy monomer; and ii. a vinyl ether monomer;
- the present invention provides a method of preparing an optical element having a primer layer, the method including:
- the present invention also provides a coating composition including an epoxy monomer and a vinyl ether monomer in amounts effective to form a primer layer on a surface of an optical element after cationic polymerisation of the coating composition.
- a “primer layer” is a coating or layer that improves the impact resistance of an optical element and/or assists with adhesion of adjacent coating layers or optical substrate materials.
- the primer layer may improve the impact resistance of optical elements having an anti-reflection coating.
- the primer layer may increase adhesion between an abrasion resistant coating and an optical element substrate.
- Primer layers of the type described herein are sometimes referred to as “impact resistant primer layers” or simply “impact resistant layers”.
- the optical element preferably has one or more further coating layers over the primer layer.
- the further coating layer is an AR coating.
- the further coating layer is an abrasion resistant coating.
- the optical element has an abrasion resistant coating as well as an AR coating.
- the abrasion resistant coating may be coated onto the primer layer, with the AR coating over the abrasion resistant coating, although variations to that arrangement are also contemplated.
- the further coating layer may also be a photochromic layer, being a layer of polymer containing one or more photochromic dyes.
- the coating composition contains 2 to 8% by weight of the epoxy monomer, and 8 to 16% by weight of the vinyl ether monomer. In another embodiment the coating composition contains 4 to 6% by weight of the epoxy monomer, and 10 to 14% by weight of the vinyl ether monomer.
- the vinyl ether monomer may be an alkyl vinyl ether, an alkoxyalkyl vinyl ether, a hydroxyalkyl vinyl ether, a vinyl ether resin, or a mixture of two or more of the aforementioned.
- the vinyl ether monomer is an aliphatic urethane divinyl ether such as the one sold under the trade name Vectomer 2020 by Morflex.
- the epoxy monomer may be selected from the group consisting of ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1 ,6 hexanediol diglycidyl ether, glycerine diglycidyl ether, trimethylol propane triglycidyl ether (such as Epolight 100MF), bisphenol-A diglycidyl ether (BPADGE), bisphenol-F diglycidyl ether, and their extended chain analogs, 1 ,4-butanediol diglycidyl ether, diglycidyl ethers of tetrabromo-bisphenol-A
- the coating composition may also contain a cationic photoinitiator and a solvent.
- the photoinitiator may be a UV photoinitiator.
- the photoinitiator may be present in the composition in an amount of 0.5 to 4% by weight, or an amount of 1 to 3% by weight.
- the coating composition also contains a supplementary polymerisable monomer (in addition to the epoxy monomer and the vinyl ether monomer).
- the supplementary polymerisable monomer may be any monomer having a polymerisable double bond.
- the supplementary polymerisable monomer is a (meth)acrylate monomer.
- (meth)acrylate is used to denote either an acrylate or a methacrylate group.
- the supplementary polymerisable monomer may be cationically polymerisable, or radically polymerisable. In the latter case, the composition may also contain a free radical photoinitiator.
- the primer layer may be coated directly onto a surface of the optical element.
- An abrasion resistant coating may then be applied prior to the deposition of an anti- reflection (AR) coating.
- the optical element may be a multilayer optical element having a primer layer as described herein, an abrasion resistant coating, and an AR coating.
- the optical element may be any optically transparent material.
- materials or substrates that may benefit from use of the present invention include lenses such as ophthalmic lenses, camera lenses, and instrument lenses.
- Other products such as domestic, commercial or residential window sheets or windows, motor vehicle windscreens or windows, transparent display panels and the like could also benefit from the present invention.
- the optical element is an ophthalmic lens.
- the optical element may be formed from any one of a variety of plastic substrates.
- the optical element may be formed from a plastic selected from the group including CR-39TM, multi-functional acrylates, polythiourethanes, thioesters, episulfide polymers, polycarbonate and the like.
- the optical element is formed from a thermoset material, such as CR-39TM, episulfide-based polymers, multi-functional acrylates, or polythiourethanes.
- the primer layer of the present invention may be used on thermoplastic substrates to enhance adhesion between the substrate and an adjacent coating layer, or between adjacent coating layers. .
- the primer layer is formed by cationic polymerisation of a coating composition containing an effective amount of: i. an epoxy monomer; and ii. a vinyl ether monomer;
- the present invention provides a coated optical element. It will be evident from the embodiments described herein that in one form of the invention the optical element is a lens, such as an ophthalmic lens. However, it will be appreciated that the methods and compositions described could also be applied to other plastic optically transparent substrates.
- the primer layer of the present invention improves adhesion and also impact resistance. Therefore, the primer layer will have a benefit when it is used between materials to increase adhesion between the materials. For example, the primer layer will improve adhesion between a substrate and a siloxane- or a (meth)acrylate-based abrasion resistant coating.
- the primer layer of the present invention is also of benefit when it is used on lenses having an anti-reflection (AR) coating. This is because AR coatings tend to be glassy and brittle and any lack of impact resistance of a lens is particularly noticeable in lenses of this type.
- the primer layer of the present invention provides a degree of impact resistance to AR coated lenses.
- the thickness of the lens also affects the impact resistance of a lens. For aesthetic reasons, there has been a trend toward making lenses as thin as possible, and lenses with a centre thickness of about 1.0 mm are now readily available. However, thinner lenses also have a lower impact resistance.
- the primer layer is formed by cationic polymerisation of a coating composition containing an effective amount of an epoxy monomer and a vinyl ether monomer.
- the epoxy monomer and the vinyl ether monomer are present in the composition in amounts effective to form a primer layer on an optical element after cationic polymerisation of the coating composition.
- reference to formation of the primer layer "on an optical element” means that the primer layer is either formed directly on a surface of the optical element, or that the primer layer is formed on a coating that is on a surface of the optical element.
- An example of the latter case is an optical element having a first abrasion resistant coating on the optical element, the primer layer on the first abrasion resistant coating, and a second abrasion resistant coating on the primer layer.
- an AR coating can then be formed on the second abrasion resistant coating.
- the coating composition may contain: 2 to 8%, and more preferably 4 to 6%, of the epoxy monomer; 8 to 16%, and more preferably 10 to 14% of the vinyl ether monomer. Unless otherwise specified, the percentages stated herein are weight percent based on the total weight of the composition.
- the vinyl ether monomer may be an alkyl vinyl ether, an alkoxyalkyl vinyl ether, a hydroxyalkyl vinyl ether, a vinyl ether resin, or a mixture of two or more of the aforementioned.
- Vinyl ethers having two or more double bonds may be referred to as polyvinyl ethers.
- the polyvinyl ether could be 1 ,3-benzenedicarboxylic acid, bis [4- (ethenyloxy)butyl]ester; pentanedioic acid, bis[[4-
- the epoxy monomer preferably has an average of two or more epoxy groups per molecule Therefore, the epoxy monomer is preferably a polymerisable monomer having two or more epoxy groups.
- the term epoxy group refers to a group of formula
- the epoxy monomer may fall into one or more of the following classes: internal, terminal, mono-functional, di-functional, tri-functional, tetra-functional, aliphatic, aromatic, cyclic, esters, ethers, and amines.
- Epoxy monomers that can be used include, but are not limited to, difunctional, trifunctional and other multi-functional epoxy monomers.
- polymerisable epoxy monomers include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1 ,6 hexanediol diglycidyl ether, glycerine diglycidyl ether, trimethylol propane triglycidyl ether, bisphenol-A diglycidyl ether (BPADGE), bisphenol-F diglycidyl ether, and their extended chain analogs, 1 ,4-butanediol diglycidyl ether, diglycidyl ethers of tetrabromo-bisphenol-A, epoxy based ethers of 4,4'
- the coating composition also contains a cationic photoinitiator, which is required for polymerisation of epoxy monomers. Any of the many compounds known to initiate polymerization by a cationic mechanism may be used.
- the cationic photoinitiator is preferably a UV activated initiator.
- Compounds known to initiate polymerisation by a cationic mechanism include, for example, diaryliodonium salts, triarylsulfonium salts, diaryliodosonium salts, dialkylphenylsulfonium salts, dialkyl(hydroxydialkylphenyl)sulfonium salts and ferrocenium salts. Such salts may be modified by the attachment of alkyl, alkoxy, siloxy and the like groups.
- Particularly useful initiators include (4-n-decyloxyphenyl) phenyliodonium hexafluoroantimonate (IOC10), (4-n-decyloxyphenyl)diphenylsulfonium hexafluoroantimonate (SOC10) and S-methyl-S-n-dodecylphenacylsulfonium hexafluoroantimonate (DPS-C 1 C 12 ).
- IOC10 phenyliodonium hexafluoroantimonate
- SOC10 (4-n-decyloxyphenyl)diphenylsulfonium hexafluoroantimonate
- DPS-C 1 C 12 S-methyl-S-n-dodecylphenacylsulfonium hexafluoroantimonate
- the amount of polymerisation initiator used and the conditions of polymerisation will be readily determined by those skilled in the art, or can easily be determined empirically.
- the polymerisation initiator is employed in concentrations ranging from 0.5 to 4% by weight based on the total weight of the coating composition.
- the polymerisation initiator is employed in concentrations of 1 to 3% by weight based on the total weight of the coating composition.
- the composition also includes a solvent.
- a thermoplastic material for example a polycarbonate polymer of bisphenol A
- the composition contains a mixture of a ketone solvent, such as methyl isobutyl ketone, and a lower alcohol solvent, such as isopropyl alcohol.
- ketone solvents affect the polymer network of an adjoining polymer layer or substrate, whilst the substrate tends to be inert to lower alcohol solvents. Therefore, by using an appropriate mixture of ketone and lower alcohol solvent it is possible to promote adhesion of the primer layer to a thermoplastic substrate, such as polycarbonate.
- thermoset material In the case of a thermoset material, the choice of solvent is not critical. Whilst not wishing to be bound by theory, we think that adhesion of the primer layer onto thermoset materials is assisted by epoxy groups of the primer layer reacting with the hydroxyl groups or other reactive functional groups on the surface of the substrate. Any of the thermoset polymers that are used in the art may be coated using the methods described herein. Common thermoset polymers include a polymer of diethylene glycol bis(allyl carbonate) (e.g. CR-39TM, a trade mark of PPG Industries, Inc), a polyacrylate copolymer (e.g. SpectraliteTM, a trade mark of Sola International Inc.), a thiolene polymer (e.g.
- the coating composition may contain a supplementary polymerisable monomer in addition to the epoxy monomer and the vinyl ether monomer.
- the supplementary polymerisable monomer may be any monomer having a polymerisable double bond. (Meth)acrylate monomers have been found to be particularly suitable as they provide some flexibility in the forumulation.
- the supplementary polymerisable monomer may be used to improve tint rate, hardness, abrasion resistance, adhesion, solvent resistance, and the like of the primer layer.
- the supplementary polymerisable monomer may be a compound having greater than one acrylate moiety per molecule.
- Examples include, but are not limited to, di-, tri ⁇ , tetra- and higher acrylates or methacrylates, urethane monomers having 2 to 6 terminal acrylic or methacrylic groups, fluorene acrylates or methacrylates, and thioacrylate or thiomethacrylate monomers, and high rigidity, high Abbe number acrylic or methacrylic monomers.
- Suitable thiodiacrylate or dimethacrylate monomers may be selected from bis(4- methacryloylthioethyl)sulfide (BMTES) and bis(4-methacryloylthiophenyl)sulfide (BMTS).
- Suitable fluorene diacrylate or dimethacrylate monomers may be selected from a bisphenol fluorene dihydroxy acrylate (BFHA) or a bisphenol fluorene dimethacrylate (BFMA) or mixtures thereof.
- the (meth)acrylate supplementary polymerisable monomer may be a polyoxy alkylene glycol diacrylate or dimethacrylate which includes ethylene oxide or propylene oxide repeating units in its backbone.
- Suitable materials include dimethylacrylates where the number of repeating ethylene oxide groups is between 4 and 14. Suitable materials include those sold under the trade names NK Ester 4G, 6G, 9G or 16G. Suitable high rigidity, High Abbe number acrylic or methacrylic monomers may be selected from acrylates or methacrylate derivatives of a cycloolefin, for example a tricyclodecane dimethanol diacrylate or methacrylate.
- a highly rigid acrylic or methacrylic monomer may be selected from highly rigid, high Abbe Number polyfu notional acrylates or methacrylates, such as pentaerythritol tetracrylate (PTA).
- PTA pentaerythritol tetracrylate
- suitable (meth)acrylate monomers include 1 ,4-butanediol diglycidylether di(meth)acrylate, bisphenol-A diglycidylether dimethacrylate, neopentylglycol diglycidylether di(meth)acrylate, N,N-bis(2- hydroxyethyl)(meth)acrylamide, methylenebis((meth)acrylamide), 1 ,6- hexamethylenebis((meth)acrylamide), diethylenetriamine tris((meth)acrylamide), bis(gamma-((meth)acrylamide)propoxy) ethane, beta-((meth)acrylamide) ethylacrylate, ethylene glycol di((meth)acrylate)), diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylateglycerol di(meth)acrylate, glycerol tri(meth)acrylate, 1 ,4-butan
- any of the following monomers may also be used: 1 ,4-butanediol di(meth)acrylate, 1 ,4-butanediol dimethacrylate, 1 ,3- butanediol glycol diacrylate, 1 ,3-butylene glycol dimethacrylate, cyclohexane dimethanol diacrylate, cyclohexane dimethanol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, dipropylene glycol diacrylate, ethylene glycol dimethacrylate, 1 ,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, and the like
- Suitable urethane acrylate monomers include urethane (meth)acrylates, such as CN962, CN964, CN965, CN980, CN9782 and other urethane acrylates sold by Sartomer Company.
- Suitable acrylate monomers may further include Epoxy Acrylate CN 120 AC16, Polybutadiene Urethane Diacrylate CN 302, Polybutadiene Dimethacrylate CN 303, (Meth)Acrylate Functional Monomer P-Cure 300, and (Meth)Acrylate Functional Monomer P-Cure 301; functional acrylic oligomers, such as the functional acrylic oligomers sold by Sartomer Company under the tradename SARCRYL ® as SARCRYL ® Functional AcrylicSarcryl CN816, SARCRYL ® Functional AcrylicSarcryl CN817, SARCRYL ® Functional AcrylicSarcryl CN818, Amine Modified Polyether Acrylate CN 501 , Amine Modified Polyether Acrylate CN 502, Amine Modified Polyether Acrylate CN 550, Amine Modified Polyether Acrylate CN 551 , Alkoxylated Trifunctional Acrylate Ester such as SR 9008 sold by Sartomer Co., Metallic Diacrylate
- the supplementary polymerisable monomer may be cationically polymerisable, or radically polymerisable. In the latter case, the composition may also contain a free radical photoinitiator.
- the free radical initiator may be a heat- or UV- activated initiator.
- Suitable free radical initiators include any one or more of: azodiisobutyronitrile (AIBN); 2,2'-azobis(N,N'-dimethyleneisobutyramidine)dihydrochloride; 2,2'-azobis(2- amidinopropane)dihydrochloride; 2,2'-azobis(N,N'-dimethyleneisobutyramidine); 4,4'- azobis(4-cyanopentanoic acid); 2,2'-azobis ⁇ 2-methyl-N-[1 ,1-bis(hydroxymethyl)-2- hydroxyethyl]propionamide ⁇ ; 2,2'-azobis ⁇ 2-methyl-N-[1 ,1- bis(hydroxymethyl)ethyl]propionamide ⁇ ; 2,2'-azobis[2-methyl-N-(2- hydroxyethyl)propionamide]; 2,2'-azobis(isobutyramide)dihydrate; 2,2'-azobis(4- methoxy-2,4-dimethylvaler
- the present invention also provides a coating composition including:
- any of the techniques that are used for that purpose in the art can be used to coat the optical element, including dip coating, spin coating, flow coating, spray coating and in- mould coating.
- the primer layer needs to be coated onto any surface that will contain an AR coating.
- an ophthalmic lens having a concave back surface and a convex front surface one or both surfaces may be coated with the primer layer.
- the primer layer is most effective for impact resistance when it is coated onto the back surface of an AR coated lens.
- the primer layer of the present invention will be deposited so that it is between the lens and the abrasion resistant coating.
- this primer-hard coat-AR coat sequence of coatings could be applied to the front and back surfaces of a lens.
- the primer layer coating composition is cured using a photoinitiated cationic curing step.
- the composition is cured by UV initiated cationic polymerisation. Ionic polymerisation enables epoxy groups of the epoxy monomer to react with free hydroxyl or other functional groups on the surface of a thermoset material.
- the primer layer will have a thickness in the range of 100 to 3,000 nm, and more preferably in the range of 500 to 2000 nm.
- the optical element of the present invention is a multilayer optical element having an impact resistant primer layer as described herein, an abrasion resistant coating, and an anti-reflection (AR) coating.
- the material of the abrasion resistant coating may include siloxane based systems together with organic coatings including heat curable epoxies and polyurethane resins and ultra violet light curable acrylic resins.
- the abrasion resistant coating will have a thickness in the range of 500 to 10,000 nm, more preferably in the range of 1000 to 5000 nm, although most preferably in the range of 1500 to 3000 nm.
- the AR coating is a substantially transparent multilayer inorganic film that is applied to substantially eliminate reflection over a relatively wide portion of the visible spectrum.
- Known anti-reflection coatings include multilayer films including alternating high and low refractive index materials (e.g., metal oxides). AR coating of this type are described in United States patent 3,432,225, United States patent 3,565,509, United States patent 4,022,947, and United States patent 5,332,618.
- AR coatings can also employ one or more electrically conductive high and/or electrically conductive low refractive index layers.
- the thickness of the AR coating will depend on the thickness of each individual layer in the multilayer film and the total number of layers in the multilayer film. Preferably, the AR coating is about 100 to about 750 nm thick.
- the AR coating is preferably about 220 to about 500 nm thick.
- Inorganic anti-reflective coatings can be single-layer systems, but more generally are multi-layer anti-reflective stacks deposited by vacuum evaporation, deposition, sputtering, ion plating, and/or ion bean assisted methods.
- the AR coating method may include the evaporation of a source material in a gas phase, such as the evaporation of an indium oxide/tin oxide material in an argon-oxygen gas mixture.
- a source material in a gas phase
- suitable source materials, gaseous atmospheres and ion assistance may be utilised as necessary.
- another suitable source material is envisaged to be a doped zinc oxide where the dopant may be aluminium, boron, phosphor or indium.
- Another method for coating a substrate with an AR coating involves the use of sputtering techniques.
- a reactant gas forms a compound with the material that is sputtered from the target.
- the reactive gas is oxygen
- silicon oxides usually in the form of SiO 2
- Another sputtering technique is to first form a sputtered metal layer on a substrate and thereafter expose this layer to a reactive gas (such as oxygen) to form a metal oxide.
- the optical element may be any optically transparent material.
- materials or substrates that may benefit from use of the present invention include lenses such as ophthalmic lenses, camera lenses, and instrument lenses.
- Other products such as a domestic, commercial or residential window sheets or windows, motor vehicle windscreens or windows, transparent display panels and the like could also benefit from the present invention.
- the optical element is an ophthalmic lens.
- the optical element may be formed from any one of a variety of plastic substrates, but is preferably formed from a plastic selected from the group consisting of CR-39TM, multi-functional acrylates, polythiourethanes, thioesters, polycarbonate and the like. Most preferably, the optical element is formed from a thermoset material, such as CR- 39TM, episulfide polymers, multi-functional acrylates, or polythiourethanes.
- the primer layer is formed by cationic polymerisation of a coating composition containing an effective amount of: an epoxy monomer; and a vinyl ether monomer;
- the optical element could include more coating layers than the three coating layers of the primer layer-hard coat layer-AR coat system.
- the optical element could include two hard coat layers and the primer layer of the present invention could be between the two hard coat layers.
- a first hard coat layer could be deposited on a surface of the optical element
- the primer layer could then be deposited on the first hard coat layer
- a second hard coat layer could then be deposited on the primer layer.
- the optical element could then be coated with an anti reflection stack.
- Further top coat layers, such as slippery coats could also be added to the multilayer coated optical element.
- the optical element could include a photochromic layer.
- Methods for preparing photochromic layers are known in the art and generally involve forming a polymeric film (such as a film formed from a blend of polyoxyalkylene glycol dimethacrylate with urethane methacrylate) and introducing a photochromic material into the film.
- the photochromic layer may be between the primer coating and a hard coating, in which case the added adhesion provided by the primer layer may be beneficial.
- the present invention also provides a method of preparing an optical element having a primer layer, the method including:
- the present invention also includes within its scope the production of coated optical elements using in-mould coating processes.
- In mould coating processes are known in the art - for example see published International patent application WO 01/21375, which is incorporated herein by reference solely for the purpose of exemplifying in-mould coating processes.
- An in-mould coating process involves applying an abrasion resistant coating composition to a surface of a mould section. The composition is then partially cured. The primer layer coating composition is then applied over the partially polymerised abrasion resistant coating and it is partially polymerised by UV initiated cationic polymerisation. Mould pieces are then fitted together to form a mould cavity that is coated with the abrasion resistant coating composition and the impact resistant primer layer in a partially polymerised form. Cross-linkable polymeric casting composition is then poured into the mould and the plastic is cured so as to form the optical element with the impact resistant coating on the surface. The moulded article is finally removed from the mould to provide the coated article. The AR coating is then applied as described previously. This then provides an in-mould coating process for forming an optical element that has a good level of impact resistance and good adhesion between the optical element substrate and the abrasion resistant coating.
- the lens samples used in this impact test were all -2.00 Stock lenses with centre thickness about 1 mm.
- the lenses can be cast or surfaced to the right through power and centre thickness.
- CR-39TM is an allyl diglycol carbonate resin marketed by PPG Industries.
- SpectraliteTM which is a polymeric casting composition that is commercially available from Sola International Inc, is a combination of a polyoxyalkylene glycol diacrylate or dimethacrylate monomer; a monomer including a recurring unit derived from at least one radical-polymerisable bisphenol monomer capable of forming a homopolymer having a high refractive index of more than 1.55; and a urethane monomer having 2 to 6 terminal groups selected from a group including acrylic and methacrylic groups.
- FinaliteTM is a high index resin that is commercially available from Sola International.
- MR7TM and MR10TM are that form thiourethane polymers after polymerisation.
- MR7TM and MR10TM are commercially available from Mitsui Chemicals.
- the above primer coating was spun coated onto the back surface of the lenses.
- the spin speed was 600 rpm and the spin time was 30 seconds.
- the coated lenses were then cured using a "Fusion" UV lamp, "D” lamp.
- the lenses were coated with hard coating solutions by the dipping method.
- the hard coating was then cured in an oven for three hours at 120 0 C.
- An AR coating was then applied using a traditional vacuum multilayer deposition method.
- the finished lenses were conditioned for 24 hours at room temperature before testing.
- the lens samples used in this impact test were all -2.00 Stock lenses with centre thickness about 1 mm.
- the lenses can be cast or surfaced to the right through power and centre thickness.
- Lenses from different materials were used in this example. These materials were CR- 39TM, SpectraliteTM, FinaliteTM, MR7TM and MR10TM.
- the above primer coating composition was spun onto the back surface of the lenses. The spin speed was 600 rpm and the spin time was 30 seconds.
- the coated lenses were then cured using a "Fusion" UV lamp, "D” lamp.
- the lenses were coated with hard coating solutions by the dipping method.
- the hard coating was cured in an oven for three hours at 120 0 C.
- An AR coating was then applied using traditional vacuum multilayer deposition method.
- the finished lenses were then conditioned for 24 hours at room temperature before testing.
- the lens samples used in this impact test are all -2.00 Stock lenses with centre thickness about 1 mm.
- the lenses can be cast or surfaced to the right through power and centre thickness.
- Lenses from different materials were used in this example. These materials are CR- 39TM, SpectraliteTM, FinaliteTM, MR7TM and MR10TM.
- the above primer coating was spun on the back surface of the lenses only, the spin speed was 600 rpm, the spin time was 30 seconds.
- the coated lenses were cured through a "Fusion” UV lamp, "D” lamp. After the curing of the primer, the lenses were coated with hard coating solutions by dipping method. The hard coating was cured in an oven for three hours at 120 0 C.
- the AR coating was applied by traditional vacuum multilayer deposition method.
- the finished lenses are conditioned for 24 hours at room temperature before testing. Twenty lenses are needed for each group in the test.
- the impact test results of lenses with primer coating layer (Table 5) are compared with the results of lenses without a primer coating layer (Table 6). In this test, the drop ball weight was 16.36 grams, the dropping height was 50 inches, the impact energy was 0.20 J. Table 5. Impact test results
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mechanical Engineering (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- Manufacturing & Machinery (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Paints Or Removers (AREA)
- Eyeglasses (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/158,476 US9975302B2 (en) | 2005-12-21 | 2006-12-21 | Primer layer coating compositions |
AU2006326863A AU2006326863A1 (en) | 2005-12-21 | 2006-12-21 | Primer layer coating compositions |
EP06840396.3A EP1963889B1 (en) | 2005-12-21 | 2006-12-21 | Primer layer coating compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2005907159A AU2005907159A0 (en) | 2005-12-21 | Primer layer coating compositions | |
AU2005907159 | 2005-12-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2007070975A1 true WO2007070975A1 (en) | 2007-06-28 |
Family
ID=38188183
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/AU2006/001985 WO2007070975A1 (en) | 2005-12-21 | 2006-12-21 | Primer layer coating compositions |
Country Status (4)
Country | Link |
---|---|
US (1) | US9975302B2 (en) |
EP (1) | EP1963889B1 (en) |
AU (1) | AU2006326863A1 (en) |
WO (1) | WO2007070975A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITIS20090001A1 (en) * | 2009-04-16 | 2010-10-17 | Giancarlo Marinelli | METHOD FOR THE PRODUCTION OF OPTICAL PHOTOCROMATIC ELEMENTS AND PHOTOCHROMIC OPTICAL ELEMENTS |
KR101620615B1 (en) * | 2014-08-18 | 2016-05-23 | 금광기업 주식회사 | Method of contructing waterproof sheet with excellent properties |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2869039B1 (en) * | 2004-04-16 | 2007-11-30 | Essilor Int | PIGMENT COLORED LATEX AND PROCESS FOR TREATING A TRANSPARENT SUBSTRATE USING THE COLOR LATEX. |
BRPI1011596B1 (en) * | 2009-03-16 | 2019-12-17 | Carl Zeiss Vision Australia Holdings Ltd | molding composition, process for the manufacture of a photochromic optical element, and, optical element |
JP6478981B2 (en) * | 2013-05-30 | 2019-03-06 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | Primer composition for injection molding |
CN113337240B (en) * | 2021-06-25 | 2022-08-05 | 宁波长阳科技股份有限公司 | UV (ultraviolet) light curing glue, screen protective film and preparation method and application thereof |
CN114350428B (en) * | 2022-01-11 | 2022-09-30 | 温州市海格阀门有限公司 | Antirust butterfly valve casting and machining method thereof |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5978304A (en) * | 1982-10-28 | 1984-05-07 | Seiko Epson Corp | Synthetic resin lens |
WO2000075241A2 (en) * | 1999-06-02 | 2000-12-14 | Sartomer Company, Inc. | Oil soluble radiation curable metal-containing compounds and compositions |
WO2001021375A1 (en) | 1999-09-21 | 2001-03-29 | Sola International Holdings Ltd | Method of forming a coated optical element |
EP0763581B1 (en) * | 1995-09-18 | 2001-12-05 | Nikon Corporation | Primer composition and optical material |
EP0699926B1 (en) * | 1994-03-18 | 2002-12-04 | Nikon Corporation | Plastic lens with primer layer |
WO2002096628A2 (en) * | 2001-05-29 | 2002-12-05 | Essilor International Compagnie Generale D'optique | Method for forming on-site a coated optical article |
WO2002096627A1 (en) * | 2001-05-29 | 2002-12-05 | Essilor International Compagnie Generale D'optique | Method for transferring from a mold a hydrophobic top coat onto an optical substrate. |
US6551710B1 (en) * | 1998-01-29 | 2003-04-22 | Sola International Holdings, Ltd. | Coating composition |
US20030118833A1 (en) * | 2001-05-29 | 2003-06-26 | Essilor International Compagnie Generale D'optique | Epoxy/acrylate based primer coating compositions and their use in the optical field |
JP2005194485A (en) * | 2004-01-09 | 2005-07-21 | Sekisui Chem Co Ltd | Hard coat composition and hard coat layer-forming method |
US20050165141A1 (en) * | 2004-01-27 | 2005-07-28 | Jean-Pierre Wolf | Thermally stable cationic photocurable compositions |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3432225A (en) | 1964-05-04 | 1969-03-11 | Optical Coating Laboratory Inc | Antireflection coating and assembly having synthesized layer of index of refraction |
US3565509A (en) | 1969-03-27 | 1971-02-23 | Bausch & Lomb | Four layered antireflection coatings |
US4022947A (en) | 1975-11-06 | 1977-05-10 | Airco, Inc. | Transparent panel having high reflectivity for solar radiation and a method for preparing same |
US5332618A (en) | 1992-02-07 | 1994-07-26 | Tru Vue, Inc. | Antireflection layer system with integral UV blocking properties |
FR2721720B1 (en) | 1994-06-27 | 1996-09-06 | Essilor Int | Ophthalmic lens made of organic glass with shock-absorbing interlayer and its manufacturing process. |
US6284162B1 (en) * | 1999-03-25 | 2001-09-04 | Sola International, Inc. | Molding method for manufacturing thin thermoplastic lenses |
JP2002006445A (en) | 2000-06-27 | 2002-01-09 | Konica Corp | Heat developable photosensitive material |
US20030205317A1 (en) * | 2002-05-01 | 2003-11-06 | Ha Chau Thi Minh | Method for sealing flat panel displays and bonding optical component parts |
-
2006
- 2006-12-21 AU AU2006326863A patent/AU2006326863A1/en not_active Abandoned
- 2006-12-21 EP EP06840396.3A patent/EP1963889B1/en active Active
- 2006-12-21 US US12/158,476 patent/US9975302B2/en active Active
- 2006-12-21 WO PCT/AU2006/001985 patent/WO2007070975A1/en active Application Filing
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5978304A (en) * | 1982-10-28 | 1984-05-07 | Seiko Epson Corp | Synthetic resin lens |
EP0699926B1 (en) * | 1994-03-18 | 2002-12-04 | Nikon Corporation | Plastic lens with primer layer |
EP0763581B1 (en) * | 1995-09-18 | 2001-12-05 | Nikon Corporation | Primer composition and optical material |
US6551710B1 (en) * | 1998-01-29 | 2003-04-22 | Sola International Holdings, Ltd. | Coating composition |
WO2000075241A2 (en) * | 1999-06-02 | 2000-12-14 | Sartomer Company, Inc. | Oil soluble radiation curable metal-containing compounds and compositions |
WO2001021375A1 (en) | 1999-09-21 | 2001-03-29 | Sola International Holdings Ltd | Method of forming a coated optical element |
WO2002096628A2 (en) * | 2001-05-29 | 2002-12-05 | Essilor International Compagnie Generale D'optique | Method for forming on-site a coated optical article |
WO2002096627A1 (en) * | 2001-05-29 | 2002-12-05 | Essilor International Compagnie Generale D'optique | Method for transferring from a mold a hydrophobic top coat onto an optical substrate. |
US20030118833A1 (en) * | 2001-05-29 | 2003-06-26 | Essilor International Compagnie Generale D'optique | Epoxy/acrylate based primer coating compositions and their use in the optical field |
JP2005194485A (en) * | 2004-01-09 | 2005-07-21 | Sekisui Chem Co Ltd | Hard coat composition and hard coat layer-forming method |
US20050165141A1 (en) * | 2004-01-27 | 2005-07-28 | Jean-Pierre Wolf | Thermally stable cationic photocurable compositions |
Non-Patent Citations (2)
Title |
---|
DATABASE WPI Week 198424, Derwent World Patents Index; Class P81, AN 1984-149236, XP003015133 * |
DATABASE WPI Week 200557, Derwent World Patents Index; Class A89, AN 2005-557886, XP003015132 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITIS20090001A1 (en) * | 2009-04-16 | 2010-10-17 | Giancarlo Marinelli | METHOD FOR THE PRODUCTION OF OPTICAL PHOTOCROMATIC ELEMENTS AND PHOTOCHROMIC OPTICAL ELEMENTS |
WO2010119477A1 (en) * | 2009-04-16 | 2010-10-21 | Giancarlo Marinelli | Method for producing photochromatic optical elements, and photochromatic optical elements |
US8922865B2 (en) | 2009-04-16 | 2014-12-30 | Giancarlo Marinelli | Method for producing photochromatic optical elements, and photochromatic optical elements |
KR101620615B1 (en) * | 2014-08-18 | 2016-05-23 | 금광기업 주식회사 | Method of contructing waterproof sheet with excellent properties |
Also Published As
Publication number | Publication date |
---|---|
AU2006326863A1 (en) | 2007-06-28 |
US9975302B2 (en) | 2018-05-22 |
EP1963889A1 (en) | 2008-09-03 |
EP1963889B1 (en) | 2019-12-04 |
US20080311287A1 (en) | 2008-12-18 |
EP1963889A4 (en) | 2010-11-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US9975302B2 (en) | Primer layer coating compositions | |
US6551710B1 (en) | Coating composition | |
EP2021423B1 (en) | Process for obtaining a hard coated article having anti-fouling properties | |
KR102066759B1 (en) | Hard coating composition and composition for forming high refractive index anti-blocking layer | |
US9890324B2 (en) | Photochromic curable composition, cured product thereof and laminate including the cured product | |
WO2008001578A1 (en) | Photochromic film, photochromic lens having the same, and process for producing photochromic lens | |
CN109021478A (en) | (methyl) acrylic resin composition and (methyl) acrylic resin film for using the composition | |
EP0590573A2 (en) | Resin for plastic lens | |
JP2017177480A (en) | Anti-glare anti-reflection film for insert molding and resin molded product produced using the same | |
WO2012133749A1 (en) | Photochromic lens | |
JP6409422B2 (en) | Anti-glare film for insert molding and resin molded product using the same | |
US20220289878A1 (en) | Polymerizable composition for optical article and optical article | |
CN107111004B (en) | UV-curable coating composition for obtaining improved abrasion resistance | |
JP6694685B2 (en) | Acrylic polymer and method for producing the same | |
US9873819B2 (en) | Curable composition and photochromic composition | |
JP2009102539A (en) | Polymerizable resin composition and optical element using it | |
AU2013200778B2 (en) | Primer layer coating compositions | |
JP2009271094A (en) | Plastic lens | |
JP2008033223A (en) | Photochromic film and photochromic lens therewith | |
US20220220240A1 (en) | Polymerizable composition for forming protective layer on photochromic article, photochromic article and eyeglasses | |
JP2021107909A (en) | Polymerizable composition for forming protective layer of photochromic article, photochromic article and spectacles | |
JP2002156503A (en) | Method for producing plastic lens and plastic lens | |
JP6016397B2 (en) | Manufacturing method of photochromic lens | |
CN113614622B (en) | Spectacle lens and spectacles | |
JP2011215240A (en) | Photochromic lens |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2006840396 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2006326863 Country of ref document: AU |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 2006326863 Country of ref document: AU Date of ref document: 20061221 Kind code of ref document: A |
|
WWP | Wipo information: published in national office |
Ref document number: 2006326863 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 12158476 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 2006840396 Country of ref document: EP |