WO2001057106A1 - Photochromic coated articles - Google Patents
Photochromic coated articles Download PDFInfo
- Publication number
- WO2001057106A1 WO2001057106A1 PCT/US2001/002380 US0102380W WO0157106A1 WO 2001057106 A1 WO2001057106 A1 WO 2001057106A1 US 0102380 W US0102380 W US 0102380W WO 0157106 A1 WO0157106 A1 WO 0157106A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- photochromic
- article
- coating
- polyol
- poly
- Prior art date
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- 238000000576 coating method Methods 0.000 claims abstract description 86
- 239000011248 coating agent Substances 0.000 claims abstract description 60
- -1 poly(urea-urethane) Polymers 0.000 claims abstract description 44
- 229920005862 polyol Polymers 0.000 claims abstract description 44
- 150000003077 polyols Chemical class 0.000 claims abstract description 42
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 229920000768 polyamine Polymers 0.000 claims abstract description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 30
- 125000003277 amino group Chemical group 0.000 claims abstract description 14
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 10
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 5
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 5
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 3
- 150000002009 diols Chemical class 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 52
- 229920001228 polyisocyanate Polymers 0.000 claims description 33
- 239000005056 polyisocyanate Substances 0.000 claims description 33
- 239000000758 substrate Substances 0.000 claims description 31
- OYQYHJRSHHYEIG-UHFFFAOYSA-N ethyl carbamate;urea Chemical compound NC(N)=O.CCOC(N)=O OYQYHJRSHHYEIG-UHFFFAOYSA-N 0.000 claims description 24
- 230000003287 optical effect Effects 0.000 claims description 18
- 239000000376 reactant Substances 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 14
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 13
- 229920000647 polyepoxide Polymers 0.000 claims description 13
- 229920000570 polyether Polymers 0.000 claims description 13
- 229920000728 polyester Polymers 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000004985 diamines Chemical class 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 239000003822 epoxy resin Substances 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 229920003180 amino resin Polymers 0.000 claims description 6
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical group C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 150000004880 oxines Chemical class 0.000 claims description 6
- 239000004814 polyurethane Substances 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 6
- 238000005299 abrasion Methods 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 229920002732 Polyanhydride Polymers 0.000 claims description 4
- 230000003667 anti-reflective effect Effects 0.000 claims description 4
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 229920000193 polymethacrylate Polymers 0.000 claims description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 4
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 3
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 claims description 3
- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000004893 oxazines Chemical class 0.000 claims description 3
- 229920002401 polyacrylamide Polymers 0.000 claims description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims 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 claims description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 2
- VDHWOHDSOHPGPC-UHFFFAOYSA-N 3,3-dihydroxyoxepan-2-one Chemical compound OC1(O)CCCCOC1=O VDHWOHDSOHPGPC-UHFFFAOYSA-N 0.000 claims description 2
- MOGCNGHSEICQCE-UHFFFAOYSA-N 3,4-bis(4-hydroxyphenyl)hexane-3,4-diol Chemical compound C=1C=C(O)C=CC=1C(O)(CC)C(O)(CC)C1=CC=C(O)C=C1 MOGCNGHSEICQCE-UHFFFAOYSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 239000004386 Erythritol Substances 0.000 claims description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 150000001562 benzopyrans Chemical class 0.000 claims description 2
- FSDSKERRNURGGO-UHFFFAOYSA-N cyclohexane-1,3,5-triol Chemical compound OC1CC(O)CC(O)C1 FSDSKERRNURGGO-UHFFFAOYSA-N 0.000 claims description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 2
- 235000019414 erythritol Nutrition 0.000 claims description 2
- 229940009714 erythritol Drugs 0.000 claims description 2
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- HOVAGTYPODGVJG-ZFYZTMLRSA-N methyl alpha-D-glucopyranoside Chemical compound CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-ZFYZTMLRSA-N 0.000 claims description 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims description 2
- 229960001553 phloroglucinol Drugs 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 12
- 239000011253 protective coating Substances 0.000 abstract description 12
- 229920003023 plastic Polymers 0.000 abstract description 7
- 239000004033 plastic Substances 0.000 abstract description 7
- 230000001464 adherent effect Effects 0.000 abstract description 3
- 239000002987 primer (paints) Substances 0.000 abstract description 2
- 239000008199 coating composition Substances 0.000 description 38
- 238000000034 method Methods 0.000 description 26
- 239000000463 material Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000178 monomer Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000523 sample Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000008859 change Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920000058 polyacrylate Polymers 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 238000004381 surface treatment Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000002537 cosmetic Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
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- 230000007246 mechanism Effects 0.000 description 5
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- 238000010992 reflux Methods 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
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- 238000002834 transmittance Methods 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000007766 curtain coating Methods 0.000 description 3
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- 238000003618 dip coating Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
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- 229920001223 polyethylene glycol Polymers 0.000 description 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 2
- AGJCSCSSMFRMFQ-UHFFFAOYSA-N 1,4-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=C(C(C)(C)N=C=O)C=C1 AGJCSCSSMFRMFQ-UHFFFAOYSA-N 0.000 description 2
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 2
- RQBUVIFBALZGPC-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanatophenyl)benzene Chemical group C1=CC(N=C=O)=CC=C1C1=CC=C(N=C=O)C=C1 RQBUVIFBALZGPC-UHFFFAOYSA-N 0.000 description 2
- GFSXWQUSLTVUBW-UHFFFAOYSA-N 10bh-benzo[h]chromene Chemical compound C1=CC=C2C3OC=CC=C3C=CC2=C1 GFSXWQUSLTVUBW-UHFFFAOYSA-N 0.000 description 2
- ZVDSMYGTJDFNHN-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3-diamine Chemical compound CC1=CC(C)=C(N)C(C)=C1N ZVDSMYGTJDFNHN-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
- VIOMIGLBMQVNLY-UHFFFAOYSA-N 4-[(4-amino-2-chloro-3,5-diethylphenyl)methyl]-3-chloro-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C(=C(CC)C(N)=C(CC)C=2)Cl)=C1Cl VIOMIGLBMQVNLY-UHFFFAOYSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
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- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 2
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- 150000002170 ethers Chemical class 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 229940100892 mercury compound Drugs 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical class C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 1
- WPWHDQYZWPRQFO-UHFFFAOYSA-N n-(1,1-diethoxybutan-2-yl)-2-methylprop-2-enamide Chemical compound CCOC(OCC)C(CC)NC(=O)C(C)=C WPWHDQYZWPRQFO-UHFFFAOYSA-N 0.000 description 1
- MHXFVFMTJDZGGN-UHFFFAOYSA-N n-(1,1-diethoxybutan-2-yl)prop-2-enamide Chemical compound CCOC(OCC)C(CC)NC(=O)C=C MHXFVFMTJDZGGN-UHFFFAOYSA-N 0.000 description 1
- IJXACZWYAHYTJN-UHFFFAOYSA-N n-(1-oxobutan-2-yl)prop-2-enamide Chemical compound CCC(C=O)NC(=O)C=C IJXACZWYAHYTJN-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 229910001453 nickel ion Inorganic materials 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 239000013047 polymeric layer Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010107 reaction injection moulding Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000007984 tetrahydrofuranes Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 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
- 239000013638 trimer Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
- C08G18/8077—Oximes
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- 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
-
- 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]
- Y10T428/31511—Of epoxy ether
-
- 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]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31554—Next to second layer of polyamidoester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31562—Next to polyamide [nylon, 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]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31573—Next to addition polymer of ethylenically unsaturated monomer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31573—Next to addition polymer of ethylenically unsaturated monomer
- Y10T428/31576—Ester monomer type [polyvinylacetate, 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]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31594—Next to aldehyde or ketone condensation product [phenol-aldehyde, 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]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31598—Next to silicon-containing [silicone, cement, etc.] layer
Definitions
- the present invention relates to certain photochromic impact resistant polymerizates . More particularly, this invention relates to certain poly (urea-urethane) articles comprising the reaction product of at least one polyol, e.g., diol, at least one polyisocyanate and at least one polyamine curing agent, which articles are provided with a photochromic polymeric coating.
- the present invention also relates to such poly (urea-urethane) impact articles having applied directly thereto a photochromic polymeric coating without previously treating the surface or applying a primer or protective coating to the surface to obtain adhesion of the coating.
- Photochromic compounds exhibit a reversible change in color when exposed to light radiation involving ultraviolet rays, such as the ultraviolet radiation in sunlight or the light of a mercury lamp.
- Various classes of photochromic compounds have been synthesized and suggested for use in applications in which a sunlight-induced reversible color change or darkening is desired.
- the most widely described classes of photochromic compounds are oxazines, pyrans and fulgides .
- the colored form of fulgide photochromic compounds is produced by an electrocyclic mechanism involving the transformation of a colorless open ring form into a colored closed ring form.
- the photochromic compounds require an environment in which they can reversibly transform.
- the rates at which the photochromic processes of activation, i.e., formation of color or darkening, and fading, i.e., the return to the original or colorless state, occur are believed to be dependent on the free volume in the polymer matrix.
- the free volume of the polymer matrix is dependent upon the flexibility of the chain segments of the polymer environment surrounding the photochromic compound, i.e., the local mobility or local viscosity of the chain segments comprising the matrix.
- the free volume of the polymer matrix is dependent upon the flexibility of the chain segments of the polymer environment surrounding the photochromic compound, i.e., the local mobility or local viscosity of the chain segments comprising the matrix.
- Claus D. Eisenbach "New Aspects of Photochromism in Bulk Polymers", Photographic Science and Engineering, 1979, pp. 183-190.
- One of the main obstacles reported by Claus D. Eisenbach, for the larger commercial application of photochromic systems is the slow rate of photochromic activation and fade in a solid polymer matrix.
- the use of photochromic compounds in polymeric coatings is known. Polyurethane coatings containing photochromic compounds are disclosed in European Patent Applications 0 146 136, U.S. Patent 4,889,413, Japanese Patent Applications 3- 269507 and
- impact resistant photochromic articles can be produced by the direct application of polymeric coatings containing photochromic compounds to poly (urea-urethane) substrates produced from a composition comprising the reaction product of (a) at least one polyol, e.g., diol; (b) at least one polyisocyanate having at least two isocyanato groups; (c) at least one polyamine having at least two amino groups, and optionally (d) at least one polyol having at least three hydroxyl groups.
- the number of isocyanato groups of the polyisocyanate reactant is greater than the number of hydroxyl groups of the polyol reactants .
- photochromic articles particularly photochromic plastic materials for optical applications
- photochromic ophthalmic plastic lenses have been investigated because of the weight advantage they offer, vis-a-vis, glass lenses.
- photochromic transparencies for vehicles such as cars, boats and airplanes
- Polymers that are typically used to prepare impact resistant articles include polymers based on bisphenol-A- polycarbonates and acrylic polymers. Thermoplastic polycarbonates are considered superior to acrylics in impact resistance but have limited wearability since resistance to abrasion and chemicals is poor.
- the performance of photochromic compounds in such polycarbonates is also poor because the polycarbonate does not have sufficient internal free volume for photochromic compounds to function properly, i.e., to achieve an acceptable activated intensity and acceptable rates of activation and fade .
- photochromic coatings enables the preparation of photochromic plastic articles without the need to incorporate the photochromic compound (s) into the plastic substrate, which is advantageous for plastics such as thermoplastic polycarbonates.
- the coating composition of the present invention enables preparation of photochromic articles without the development of special optical resins for use with photochromic compounds. Further, use of photochromic coatings results in more efficient utilization of photochromic compounds by avoiding the losses associated with more conventional transfer methods, e.g., imbibition or permeation, to produce photochromic articles .
- the exact nature of the polymer-forming coating is not critical other than it be organic and photochromic in nature. Any photochromic organic coating can be used since the essence of the present invention relates to the impact resistant substrate described herein which has a surface containing reactive amino and/or isocyanato groups. The presence of the surface reactive groups on the substrate allows good adhesion of the coating to the substrate without having to pretreat the surface prior to coating.
- the polymer-forming coating composition used to produce the photochromic coated articles of the present invention includes compositions resulting in thermoplastic or thermosetting coatings that are described in the Kirk-Othmer Encyclopedia of Chemical Technology, Fourth Edition, Volume 6, pages 669 to 760, which description is incorporated herein by reference. Such coatings may be transparent, translucent or opaque; but preferably are transparent. Specifically contemplated is a coating that upon curing forms a polymeric layer selected from the group consisting of polyurethanes, aminoplast resins, pol (meth) acrylates, e.g., polyacrylates and polymethacrylates, polyanhydrides, polyacrylamides, and epoxy resins.
- a photochromic polyurethane may be used to prepare the photochromic coated articles of the present invention.
- Such polyurethanes are those produced by the catalyzed or uncatalyzed reaction of an organic polyol component and an isocyanate component in the presence of photochromic compound(s).
- Materials and methods for the preparation of polyurethanes are described in Ullmann's Encyclopedia of Industrial Chemistry, Fifth Edition, 1992, Vol. A21, pages 665 to 716, which description is herein incorporated by reference.
- Examples of organic polyols, isocyanates and other components that may be used to prepare the polyurethane coating are disclosed in International Patent Application WO 98/37115, which disclosure is incorporated herein by reference.
- a photochromic aminoplast resin coating composition that can be used to produce the photochromic coated articles of the present invention may be prepared by combining a photochromic component with the reaction product of hydroxyl-functional component (s) having at least two functional groups or different functional component (s) having at least two different functional groups selected from hydroxyl, carbamate, urea or mixtures of such functional groups and an aminoplast resin, i.e., crosslinking agent.
- hydroxyl-functional component having at least two functional groups or different functional component (s) having at least two different functional groups selected from hydroxyl, carbamate, urea or mixtures of such functional groups and an aminoplast resin, i.e., crosslinking agent.
- aminoplast resin i.e., crosslinking agent
- Photochromic poly(meth) acrylate coating compositions contemplated for use in preparing the photochromic coated articles of the present invention may be prepared by combining photochromic compound (s) with monomer (s) selected from the group consisting of pentaerythritol di-, tri- and tetra-acrylates, pentaerythritol di-, tri- and tetra-methacrylates , butanediol di (meth) acrylate, hexanediol di (meth) acrylate, nonanediol di (meth) acrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, poly(oxyalkylene dimethacrylates) , e.g., polyethylene glycol (600) dimethacrylate, ethoxylated bisphenol A dimethacrylate monomers, ethylene glycol bismethacrylate monomers, poly (ethylene glycol) bis methacrylate monomers, poly
- Patent 5,373,033 polyfunctional, e.g., mono-, di- or multi-functional, acrylate and/or methacrylate monomers, C]_-C-
- polyol [ (meth) acryloyl terminated carbonate] monomer e.g., 2 , 5, 8, 10, 13-pentaoxahexadec
- a polyanhydride photochromic coating composition that can be used to prepare the photochromic coated articles of the present invention may be prepared by the reaction of hydroxyl - functional component (s) having at least two hydroxyl groups and polymeric anhydride-functional component (s) having at least two cyclic carboxylic acid anhydride groups in a composition including at least one organic photochromic component.
- hydroxyl -functional components, anhydride -functional component (s) and other components that may be used to prepare the polyanhydride photochromic coatings are disclosed in U.S. Patents 4,798,745, 4,798,746 and 5,239,012, which disclosures are incorporated herein by reference .
- Photochromic polyacrylamide coating compositions contemplated for use in preparing the photochromic coated articles of the present invention may be prepared by combining a photochromic component with the free radical initiated reaction product of a polymerizable ethylenically unsaturated composition comprising: a) from 25 to 80% by weight of an N- alkoxymethyl (meth) acrylamide; and b) from 20 to 75% by weight of at least one other copoly erizable ethylenically unsaturated monomer, said weight percentages being based on the total weight of the polymerizable ethylenically unsaturated monomers.
- Methods for preparing N-alkoxymethyl (meth) acrylamide functional polymer are described in U.S.
- N-alkoxymethyl (meth) acrylamide means either N-alkoxymethylacrylamide or N- alkoxymethylmethacrylamide .
- the copolymerizable ethylenically unsaturated monomers substantially free of alkoxyacrylamide functionality used in the polymerizable composition include vinyl aromatic monomers such as styrene, alpha-methyl styrene, and tertiary butyl styrene; (meth) acrylamidobutyraldehyde dialkyl acetal monomers such as acrylamidobutyraldehyde diethyl acetal (ABDA) , methacrylamidobutyraldehyde diethyl acetal (MABDA) , and the like; vinyl aliphatic monomers such as ethylene, propylene, and 1,3- butadiene; pol (alkyleneglycol) (meth) acrylate,
- Photochromic epoxy resin coating compositions that can be used to prepare the photochromic coated articles of the present invention may be prepared by combining photochromic compound(s), epoxy resins or polyepoxides and curing agents as disclosed in International Patent Application WO 99/29791, which disclosure is incorporated herein by reference.
- the polyepoxides which can be used are epoxy-containing acrylic polymers, epoxy condensation polymers such as polyglycidyl ethers of alcohols and phenols and polyglycidyl esters of polycarboxylic acids, certain polyepoxide monomers and oligomers and mixtures of such polyepoxides . Examples of these materials are described in U.S. Patent 5,256,452 column 3, line 28 to column 4, line 46, which disclosure is incorporated herein by reference.
- the preferred polyepoxide is the epoxy-containing acrylic polymer.
- Curing agents for the photochromic epoxy resin coating composition of the present invention are polyacid curing agent having a high average acid functionality.
- the polyacid curing agents which may be used are carboxylic acid group- containing polymers such as acrylic polymers, polyesters, and polyurethanes; oligomers such as ester group-containing oligomers and monomers . Examples of such curing agents and other epoxy resin coating composition components are disclosed in U.S. Patents 4,764,430 and 5,196,485, which disclosures are incorporated herein by reference.
- photochromic polymer-forming coating compositions used to prepare the photochromic coated articles of the present invention, may further comprise additional conventional ingredients that impart desired physical characteristics to the coating composition or the resultant cured layer; that are required for the process used to apply and cure the coating composition to the substrate; and/or that enhance the cured coating layer made therefrom.
- Such additional ingredients include solvents, rheology control agents, plasticizers, leveling agents, e.g., surfactants, catalysts, e.g., polymerization initiators, e.g., thermal and photopolymerization initiators, cure-inhibiting agents, free radical scavengers and adhesion promoting agents, such as trialkoxysilanes, e.g., ⁇ -glycidoxypropyltrimethoxysilane.
- leveling agents e.g., surfactants
- catalysts e.g., polymerization initiators, e.g., thermal and photopolymerization initiators
- cure-inhibiting agents e.g., free radical scavengers
- adhesion promoting agents such as trialkoxysilanes, e.g., ⁇ -glycidoxypropyltrimethoxysilane.
- Organic photochromic compounds contemplated for use in the polymer-forming coating compositions of the present invention are organic photochromic compounds having at least one activated absorption maxima within the range of between about 400 and 700 nanometers, or substances containing the same.
- the photochromic compounds may each be used alone or in combination with one or more other organic photochromic materials.
- the organic photochromic materials may include substituted and unsubstituted naphthopyrans , indenonaphthopyrans , oxazines, 2H-phenanthro [4, 3-b]pyrans, 3H-phenanthro [1, 2-b]pyrans, benzopyrans and mixtures of such photochromic compounds.
- Such photochromic compounds are described in U.S.
- Spiro (indoline) pyrans are also described in the text, Techniques in
- the organic photochromic materials may also include polymerizable photochromic compounds, such as those disclosed in U.S. Patents 4,719,296; 5,166,345; 5,236,958; 5,252,742; 5,359,035; and 5,488,119.
- organo- metal dithiozonates i.e., (arylazo) -thioformic arylhydrazidates , e.g., mercury dithizonates which are described in, for example, U.S. Patent 3,361,706; and fulgides and fulgimides, e.g., the 3- furyl and 3-thienyl fulgides and fulgimides, which are described in U.S. Patent 4,931,220 at column 20, line 5 through column 21, line 38.
- organo- metal dithiozonates i.e., (arylazo) -thioformic arylhydrazidates
- mercury dithizonates e.g., mercury dithizonates
- fulgides and fulgimides e.g., the 3- furyl and 3-thienyl fulgides and fulgimides, which are described in U.S. Patent 4,931,220 at column 20, line 5 through column 21, line 38.
- organic photochromic substance resistant to the effects of a polymerization initiator may also be added to the coating composition.
- organic photochromic substances include photochromic pigments and photochromic compounds encapsulated in metal oxides, the latter of which are described in United States Patents 4,166,043 and 4,367,170.
- the disclosures relating to such photochromic compounds in the aforedescribed patents are incorporated herein, in toto, by reference.
- the photochromic articles of the present invention may contain one photochromic compound or a mixture of photochromic compounds, as desired. Mixtures of photochromic compounds may be used to attain certain activated colors such as a near neutral gray or brown or a fashionable color, e.g., pink. Further discussion of neutral colors and ways to describe colors may be found in United States Patent 5,645,767, column 12, line 66 to column 13, line 19.
- the organic photochromic compounds may be incorporated into the polymer-forming coating composition by various methods described in the art. Such methods include adding the photochromic compounds to one or more of the materials used to form the coating composition. In such methods, the photochromic compounds may be dissolved and/or dispersed in an aqueous or organic solvent prior to being incorporated into one or more of the components of the coating composition. Alternatively, the photochromic compounds may be incorporated into the cured coating by imbibition, permeation or other transfer methods as known by those skilled in the art.
- the amount of the photochromic substances described herein to be used in the coatings of the present invention is an amount sufficient to produce a photochromic effect discernible to the naked eye upon activation. Generally such amount can be described as a photochromic amount .
- the photochromic compounds are used in photochromic amounts and in a ratio (when mixtures are used) such that a coating composition to which the compound (s) is applied or in which it is incorporated exhibits a desired resultant color when activated with unfiltered sunlight.
- the amount of photochromic material incorporated into the coating composition ranges from 0.1 to 40 weight percent based on the weight of the liquid coating composition.
- the concentration of photochromic material ranges from 1.0 to 30 weight percent, more preferably, from 3 to 20 weight percent, and most preferably, from 5 to 15 weight percent, e.g., from 7 to 14 weight percent, based on the weight of the liquid coating composition.
- the amount of photochromic substance in the coating may range between any combination of these values, inclusive of the recited range.
- Compatible (chemically and color-wise) tints, i.e., dyes may be added to the coating composition, applied to the coated article or applied to the substrate prior to coating to achieve a more aesthetic result, for medical reasons, or for reasons of fashion.
- the dye selected will vary and depend on the aforesaid need and result to be achieved.
- the dye may be selected to complement the color resulting from the activated photochromic substances, e.g., to achieve a more neutral color or absorb a particular wavelength of incident light.
- the dye may be selected to provide a desired hue to the substrate and/or coated article when the photochromic substances is in an unactivated state.
- Adjuvant materials may also be incorporated into the coating composition with the photochromic material used, prior to, simultaneously with or subsequent to application or incorporation of the photochromic material in the coating composition or cured coating.
- ultraviolet light absorbers may be admixed with photochromic substances before their addition to the coating composition or such absorbers may be superposed, e.g., superimposed, as a layer between the photochromic coating and the incident light.
- stabilizers may be admixed with the photochromic substances prior to their addition to the coating composition to improve the light fatigue resistance of the photochromic substances.
- Stabilizers such as hindered amine light stabilizers (HALS) , asymmetric diaryloxalamide (oxanilide) compounds and singlet oxygen quenchers, e.g., a nickel ion complex with an organic ligand, or mixtures of stabilizers are contemplated. They may be used alone or in combination. Such stabilizers are described in U.S. Patents 4,720,356 and 5,391,327, respectively.
- the aforedescribed coating compositions are applied to substrates prepared from poly (urea-urethane) resin compositions described herein.
- the amount of the coating composition applied to the substrate is an amount necessary to incorporate a sufficient quantity of the organic photochromic substance (s) to produce a coating that exhibits a photochromic response.
- the applied coating may have a thickness of at least 5 microns, preferably, at least 10 microns, more preferably at least 20 microns, e.g., 25 microns.
- the applied coating will also usually have a thickness of not more than 200 microns, preferably, not more than 100 microns, and more preferably not more than 50 microns, e.g., 40 microns.
- the thickness of the coating may range between any combination of these values, inclusive of the recited values.
- the coating composition of the present invention may be applied by any of the methods used in coating technology such as, for example, spray coating, spin coating, spread coating, curtain coating, dip coating, casting or roll-coating.
- the coating composition is applied by spin coating, curtain coating, dip coating, spray coating methods, or by methods used in preparing overlays.
- Such methods for producing overlays are disclosed in U.S. Patent 4,873,027, which patent is incorporated herein by reference.
- the coating is cured.
- the coating may be cured at temperatures ranging from 22°C to 200°C. If heating is required to obtain a cured coating, temperatures of between 80°C and a temperature above which the substrate is damaged due to heating, e.g., 80°C to 200°C, are typically used. While a range of temperatures has been described for curing the coated substrate, it will be recognized by persons skilled in the art that temperatures other than those disclosed herein may be used. Additional methods for curing the photochromic coating composition include irradiating the coating with infrared, ultraviolet, visible, microwave, or electron radiation. This may be followed by a heating step.
- the resulting cured coating meets commercially acceptable "cosmetic" standards for optical coatings.
- cosmetic defects of coated lens include an orange peel-like appearance, pits, spots, inclusions, cracks and crazing of the coating.
- the coatings prepared using the photochromic coating composition of the present invention are substantially free of cosmetic defects.
- the substrate for the photochromic coatings is an impact-resistant non-elastomeric poly (urea-urethane) polymerizate.
- the poly (urea-urethane) comprises the reaction product of reactants comprising (a) at least one polyol, e.g., diol; (b) at least one polyisocyanate having at least two isocyanato groups; (c) at least one polyamine having at least two amino groups, each amino group being independently selected from primary amino and secondary amino; and optionally, (d) at least one polyol having at least three hydroxyl groups ; wherein the number of isocyanato groups of the isocyanate reactants is greater than the number of hydroxyl groups of the polyol reactants .
- One polyol e.g., diol, or more than one diol may be employed in forming the poly (urea-urethane) .
- the polyols which can be used are numerous and widely varied. They are preferably substantially free from ethylenic or acetylenic unsaturation.
- the polyols which are used are most often aliphatic, alicyclic, aromatic, aliphatic-alicyclic, aliphatic-aromatic, alicyclic-aromatic, or aliphatic-alicyclic-aromatic in nature.
- the polyols are usually simple diols, e.g., diols having a molecular weight less than 500 grams per mole, ester diols, polyester diols, ether diols, polyether diols, or mixtures of such diols. Although other kinds of diols can be employed as desired.
- the aliphatic groups of the diols can be straight or branched. Examples of such polyols are disclosed in U.S. Patent 5,684,083, which disclosure is incorporated herein by reference.
- the diols which are employed usually have a weight average molecular weight ranging from at least 62 , preferably from 100, more preferably from 200, and most preferably from at least 300.
- the weight average molecular weight of the diol is usually not more than 20,000, preferably not more than 10,000, more preferably, not more than 8,000, and most preferably, not more than 2,000.
- the weight average molecular weight of the diol may range from 400 to 1,500.
- the weight average molecular weight of the diol may range between any combination of these values, inclusive of the recited values.
- suitable diols include: 1, 2-ethanediol, 1, 2-propanediol , 1, 3-propanediol, 1, 3-butanediol , 1, 4-butanediol , 1, 5-pentanediol , 2 , 2-dimethylpropane-l, 3-diol, 2-butyl-2-ethylpropane-l, 3-diol , 1, 5-hexanediol , 1, 6-hexanediol, 1, 8-octanediol, 1, 10-decanediol, 1, 12-dodecanediol, 2,2,4, 4-tetramethylcyclobutane-l, 3-diol, 1, 3-cyclopentanediol , 1, 2-cyclohexanediol, 1 , 3-cyclohexanediol, 1, 4-cyclohexanediol , 1, 2-cyclo
- polyalkylene glycols such as: diethylene glycol, triethylene glycol, tetraethylene glycol, higher poly (ethylene glycol), such as those having number average molecular weights of from 220 to 2000, dipropylene glycol, tripropylene glycol, and higher poly (propylene glycol) such as those having number average molecular weights of from 234 to 2000.
- suitable diols include
- Polyester diols constitute yet another class of diols which can be used.
- the polyester diols which are employed usually have a weight average molecular weight in the range of from 500 to 1200. Often the polyester diols have a weight average molecular weight in the range of from 500 to 1000. A weight average molecular weight in the range of from 600 to 900 is preferred.
- One type of polyester diol that can be used is that prepared by the reaction of a diol and a dicarboxylic acid.
- dicarboxylic acids include: malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, isophthalic acid, and terephthalic acid.
- Anhydrides, where they exist can be used in lieu of the corresponding dicarboxylic acids.
- polyester diol Another type of polyester diol that can be used is poly (caprolactone diol) , which is the reaction product of one or more diols and ⁇ - caprolactone . While any of the diols described above can be used in that reaction, the simpler diols such as 1, 2-ethanediol , 1, 4-butanediol, 2 , 2-dimethylpropane-l, 3-diol ,
- Polyether diols are commonly made by polymerizing one or more cyclic ethers such as epoxides (e.g., ethylene oxide, propylene oxide), oxetanes, oxolanes (e.g., tetrahydrofuran) , or the like, in the presence of water or a diol starter.
- the polyether diols are made using any suitable catalyst, including, for example, potassium hydroxide, boron trifluoride, or a double metal cyanide. Double metal cyanide catalysts are preferred because they easily give polyether diols with exceptionally low unsaturation or monol content.
- the diols can be homopolymers (e.g., poly (oxypropylene) diols), random copolymers of two or more cyclic ethers (e.g., a random copolymer of propylene oxide and ethylene oxide), block copolymers (e.g., a poly (oxypropylene) core with poly (oxyethylene) caps, "tipped” copolymers (e.g., a poly (oxypropylene-co-oxyethylene core having one oxypropylene to oxyethylene ratio, which core is tipped with poly (oxypropylene- co-oxyethylene) having a different oxypropylene to oxyethylene ratio.
- homopolymers e.g., poly (oxypropylene) diols
- random copolymers of two or more cyclic ethers e.g., a random copolymer of propylene oxide and ethylene oxide
- block copolymers e.g., a poly (oxypropylene
- the polyether diol has a weight average molecular weight in the range of from 1500 to 20,000. Often the weight average molecular weight is in the range of from 2000 to 10,000. Preferably the weight average molecular weight is in the range of from 2000 to 8000.
- polyether diols usually varies and often depends on the nature of the catalyst used to make the polyether diol. While a polyether diol made by conventional KOH catalysis typically has an actual hydroxyl functionality of only about 1.6 or 1.7, one made using double metal cyanide catalyst may have an actual hydroxyl functionality very close to 2.
- Preferred polyether diols for use in the present invention have low unsaturations .
- preferred polyether diols have unsaturations less than 0.02 meq/g.
- the unsaturation is less than 0.01 meq/g.
- the unsaturation is less than 0.007 meq/g.
- polyether diols can be made by various known methods, including use of double metal cyanide catalysts, as described in United States Patents No. 5,158,922; 5,470,813; and 5,482,908, the disclosures of which are, in their entireties, incorporated herein by reference.
- One polyisocyanate having at least two isocyanato groups or a mixture of more than one such polyisocyanate may be used in forming the poly (urea-urethane) .
- the polyisocyanate has two isocyanato groups.
- the mixture usually (but not necessarily) contains one or more polyisocyanates having two isocyanato groups.
- the average isocyanato functionality is in the range of from 2 to 4 isocyanato groups per molecule.
- the average isocyanato functionality is in the range of from 2 to 3 isocyanato groups per molecule.
- the average isocyanato functionality is in the range of from 2 to 2.5 isocyanato groups per molecule.
- the average isocyanato functionality is 2 isocyanato groups per molecule.
- polyisocyanates which can be used, are numerous and widely varied. Examples of types and classes of polyisocyanates include aliphatic polyisocyanates, alicyclic polyisocyanates where one or more isocyanato groups are attached directly to the ring, alicyclic polyisocyanates where one or more isocyanato groups are not attached directly to the ring, aromatic polyisocyanates where one or more isocyanato groups are attached directly to the ring, aromatic polyisocyanates where one or more isocyanato groups are not attached directly to the ring, hybrids of any of the foregoing and mixtures of such polyisocyanates .
- suitable polyisocyanates include, but are not limited to:
- An example is an adduct (approximately 3:1, molar) of l-isocyanatomethyl-5-isocyanato- 1, 3 , 3-trimethylcyclohexane and 2 -ethyl-2- (hydroxymethyl) -1, 3-propanediol .
- the preferred polyisocyanate is bis (4-isocyanatocyclohexyl) methane.
- the trans-trans isomer, the cis-trans isomer or the cis-cis isomer may be used either alone or in combination with either or both of the other isomers; however, the trans-trans isomer is preferred.
- the trans-trans isomer constitutes from 20 to 100 percent of the bis (4 -isocyanatocyclohexyl) methane. It is especially preferred that the bis (4-isocyanatocyclohexyl) - methane contain at least about 50 percent of the trans-trans isomer and no more than 20 percent of the cis-cis isomer.
- the polyamine has at least two amino groups, each amino group being independently selected from primary amino (-NH 2 ) or secondary amino (-NH-) . Preferably all of the amino groups are primary amino.
- the polyamine reactant may be selected from aliphatic polyamines, cycloaliphatic polyamines, aromatic polyamines and polyamines of mixed aliphatic, cycloaliphatic, and/or aromatic types, or mixtures thereof. Preferably the polyamine reactant has at least two primary amino groups .
- the polyamines which can be used are numerous and widely varied.
- suitable diamines include, but are not limited to: 1, 2-ethanediamine, 1, 3-propanediamine, 1 , 4-butanediamine, 1, 5-pentanediamine, 1, 6-hexanediamine, 1, 7-heptanediamine, 1, 8-octanediamine, 1, 9-nonanediamine, 1, 10-decanediamine, 1, 2-benzenediamine, 1, 3-benzenediamine, 1, 4-benzenediamine, 1, 5-naphthalenediamine, 1 , 8-naphthalenediamine , 2,4-toluenediamine , 2 , 5-toluenediamine, 3,3' -dimethyl-4 , 4 ' -biphenyldiamine, 4, 4 ' -methylenebis [aniline] , 4, 4 ' -methylenebis [2-chloroaniline] , 4,4' -oxybis [aniline] , [1,1' -biphenyl] -4,
- a preferred embodiment is an isomeric mixture containing mostly 3 , 5-diethyl-2 , 4 -toluenediamine and 3 , 5-diethyl-2 , 6 -toluenediamine .
- the polyamine reactant can be selected from one or more diamines represented by Formula (I) :
- R 3 and R 4 are each independently C1 . -C 3 alkyl, and R 5 is selected from hydrogen and halogen, e.g., chlorine and bromine.
- the diamine represented by Formula (I) can be described generally as a 4, 4 ' -methylene-bis (dialkylaniline) .
- diamines represented by Formula (I) include, but are not limited to: 4, 4 ' -methylenebis [2 , 6 -dimethylaniline] , 4,4' -methylenebis [2 , 6-diethylaniline] , 4,4' -methylenebis [2-ethyl-6-methylaniline] , 4,4' -methylenebis [2 , 6-diisopropylaniline] , 4 , 4 ' -methylenebis [2-isopropyl-6 -methylaniline] , and 4,4' -methylenebis [2 , 6-diethyl-3-chloroaniline] .
- a preferred diamine represented by Formula (I) is 4,4' -methylenebis [2 , 6-diethyl-3-chloroaniline] .
- the polyamine may contain more than two amino groups . Examples include: diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, 2 -amino-1- ethylpiperazine, and N,N' -bis (3-aminopropylene)piperazine .
- One or more polyols having at least three hydroxyl groups may optionally be used in forming the poly (urea-urethane) . Such polyols include the triols, tetrols, or higher functional polyols. These polyols are numerous and widely varied. Examples include, but are not limited to: glycerol, 1, 1, 1-trimethylolethane, 1, 1 , 1-trimethylolpropane,
- the polyol having at least three hydroxyl groups has an average hydroxyl functionality of three hydroxyl groups per molecule.
- a polyol having at least three hydroxyl groups is employed, it is used in minor amount.
- the diol and the polyol having at least three hydroxyl groups will be collectively referred to herein as "total polyol".
- the ratio of the hydroxyl equivalents of polyol having at least three hydroxyl groups to the hydroxyl equivalents of diol present in the total polyol is in the range of from 0 to 0.25:1. Often the ratio is in the range of from 0 to 0.2:1. Preferably the ratio is in the range of from 0.1:1 to 0.2:1. A ratio of 0.15:0.85 is especially preferred.
- the average isocyanato functionality of the polyisocyanate having at least two isocyanato groups used in preparing the poly (urea-urethane) is in the range of from 2 to 3 isocyanato groups per molecule.
- the polyisocyanate has an average isocyanato functionality of 2 isocyanato groups per molecule.
- the average amino functionality of the polyamine having at least two amino groups used in preparing the poly (urea-urethane) is in the range of from 2 to 4 amino groups per molecule.
- the polyamine has an average amino functionality of 2 amino groups per molecule.
- an aromatic polyamine that has relatively low yellowness.
- a low-yellowness polyamine will tend to give low yellowness poly (urea-urethanes) .
- Low-yellowness polyamines (especially low-yellowness diamines) are available commercially.
- the yellowness of aromatic polyamines with higher yellowness can be reduced by conventional means (e.g., distillation, carbon treatment, addition of reducing agents, and the like.)
- the polymeric substrates of this invention can be prepared by the one shot, quasi -prepolymer, or full prepolymer methods, all of which are well known in the art. Of these, the full prepolymer method is preferred.
- a prepolymer is first made by reacting the polyisocyanate and the total polyol at an NCO/OH equivalent ratio in the range of from 1.3:1 to 4.5:1.
- the NCO/OH equivalent ratio is in the range of from 2.4:1 to 4:1.
- the reaction may conveniently be conducted at temperatures in the range of from 40 °C to 145 °C under a blanket of unreactive gas such as nitrogen or helium.
- the temperature is in the range of from 70°C to 135°C. Frequently the temperature is in the range of from 90°C to 130°C. Either or both of the reactants may be fed to the reaction mixture during the reaction, but it is more usual to simply admix the reactants and then heat the mixture to reaction temperature under a blanket of unreactive gas and maintain the reaction mixture at the reaction temperature for a period in the range of from 10 to 60 minutes. In general, higher reaction temperatures favor shorter reaction periods .
- a catalyst is preferably an organometallic catalyst, such as, for example, an organometallic tin, lead, iron, bismuth, or mercury compound. Organotin compounds such as dibutyltin dilaurate are preferred. Delayed-action catalysts can also be used. Other suitable catalysts are described in Unites States Patent No. 5,646,230, the entire disclosure of which is incorporated herein by reference. When a catalyst is used, it is ordinarily used in an amount in the range of from 25 to 1000 parts per million of total reactants, by weight. Inasmuch as the polyisocyanate is used in excess, the product is an isocyanate- terminated prepolymer.
- organometallic catalyst such as, for example, an organometallic tin, lead, iron, bismuth, or mercury compound. Organotin compounds such as dibutyltin dilaurate are preferred. Delayed-action catalysts can also be used. Other suitable catalysts are described in Unites States Patent No.
- Small additional amounts of polyisocyanate may optionally be added to the prepolymer when it is desired to increase the isocyanato content.
- the polyamine, photochromic compound (s) and the prepolymer are admixed to form a reaction mixture which is poured into a preheated mold and cured to form a photochromic poly (urea-urethane) article.
- the mold is a lens mold and the poly (urea-urethane) article is a photochromic ophthalmic lens.
- the polyamine and the prepolymer are admixed at an amine/NCO equivalent ratio in the range of from 0.85:1 to 1.2:1. Often the amine/NCO equivalent ratio is in the range of from 0.9:1 to 1.1:1.
- the amine/NCO equivalent ratio is in the range of from 0.9:1 to 1.05:1.
- the amine/NCO equivalent ratio is in the range of from 0.92:1 to 1:1.
- the poly (urea-urethane) may be prepared by a quasi-prepolymer method of reacting the polyisocyanate with 0.3 to 0.8 equivalents of the total polyol to form a prepolymer, and then the remaining 0.2 to 0.7 equivalents of the total polyol are added with the diamine curing agent .
- the curing reaction may conveniently be conducted at temperatures in the range of from 40°C to 135°C . Often the temperature is in the range of from 45°C to 110°C. Frequently the temperature is in the range of from 50°C to 100°C.
- the curing period is usually in the range of from 3 minutes to 24 hours, depending upon the rate of reaction between the amino groups of the polyamine and the isocyanato groups of the prepolymer.
- the poly (urea-urethane) may be removed from the mold and post-cured by heating it in an oven for several hours (usually overnight) .
- the potlife of the reaction mixture (that is, the maximum time the formulator has to fill the mold with the reaction mixture after admixing the polyamine, photochromic compounds and the prepolymer) is at least 20 seconds, and more preferably at least 30 seconds.
- additives may be incorporated into the reaction mixture which is polymerized in accordance with the invention.
- additives may include light stabilizers, heat stabilizers, antioxidants, ultraviolet light absorbers, mold release agents, static (non-photochromic) dyes, pigments, and flexibilizing additives, e.g., alkoxylated phenol benzoates and poly(alkylene glycol) dibenzoates .
- Antiyellowing additives e.g., 3-methyl-2-butenol , organo pyrocarbonates and triphenyl phosphite, may also be added to enhance resistance to yellowing.
- Such additives are typically present in amounts totaling less than 10 % by weight, preferably less than 5 % by weight, and more preferably less than 3 % by weight, based on the total weight of the combined polyamine and prepolymer. While such conventional additives may be added to either the prepolymer or the polyamine, they are preferably incorporated into the polyamine.
- the preparation of poly (urea-urethane) is described in United States Patents No. 3,866,242; 5,811,506; 5,962,617; and 5,962,619, the disclosures of which are, in their entireties, incorporated herein by reference.
- Specifically contemplated is the use of the combination of the photochromic coating compositions with optically clear poly (urea-urethane) polymerizates, i.e., materials suitable for optical applications, such as optical elements, e.g., piano and vision correcting ophthalmic lenses, windows, clear polymeric films, automotive transparencies, e.g., windshields, aircraft transparencies, plastic sheeting, etc. More specifically contemplated, is the use of the combination of the photochromic coating compositions with optical elements to produce photochromic optical articles.
- optically clear poly (urea-urethane) polymerizates i.e., materials suitable for optical applications, such as optical elements, e.g., piano and vision correcting ophthalmic lenses, windows, clear polymeric films, automotive transparencies, e.g., windshields, aircraft transparencies, plastic sheeting, etc.
- optical elements e.g., piano and vision correcting ophthalmic lenses, windows, clear polymeric films, automotive transparencies, e.
- Such articles are prepared by sequentially applying to at least one surface of the optical element the photochromic coating composition and optionally appropriate protective coating(s), e.g., abrasion resistant coatings, and/or surface treatments, e.g., antireflective coatings and hydrophobic coatings.
- the poly (urea-urethane) substrate can be coated/treated sequentially with a photochromic polymeric coating, an abrasion resistant coating and an antireflective surface as the outermost surface treatment.
- the resulting cured coating preferably meets commercially acceptable "cosmetic" standards for optical coatings, and most preferably, is substantially free of cosmetic defects .
- the photochromic poly (urea-urethane) article prepared in accordance with the present invention is a non-elastomeric, optically clear solid (which exhibits low yellowness) having an adherent photochromic polymeric coating.
- the photochromic coated articles of the present invention may be further coated with a protective coating of silica, titania, and/or zirconia-based hard coating material.
- a protective coating of silica, titania, and/or zirconia-based hard coating material may be applied so as to form a hard surface layer, whereby the surface hardness is enhanced.
- Application of such coatings may be by any of the methods used in coating technology such as, for example, spray coating, spin coating, spread coating, curtain coating, dip coating or roll-coating.
- a tintable coating, antireflective surface, etc. may also be applied to the photochromic articles of the present invention.
- An antireflective coating e.g., a monolayer or multilayer of metal oxides, metal fluorides, or other such materials, may be deposited onto the photochromic articles, e.g., lenses, of the present invention through vacuum evaporation, sputtering, or some other method.
- the presence of isocyanato and/or amino groups on the surface of the poly (urea-urethane) substrate allows good adhesion of the photochromic polymeric coating to the substrate. Therefore, the photochromic polymeric coating may be applied directly to the substrate without an intermediate layer, coating or surface treatment to improve adhesion. Since the photochromic polymeric coating can be selected from a wide variety of organic polymeric coatings, there may be occasions when there is a need to improve the adhesion of the coating.
- Effective treatment techniques for cleaning the surface and promoting adhesion of the photochromic polymeric coating include ultrasonic cleaning; washing with an aqueous mixture of organic solvent, e.g., a 50:50 mixture of isopropanol; water or ethanol; water; UV treatment; activated gas treatment, e.g., treatment with low temperature plasma or corona discharge; or chemical treatment such as hydroxylation, i.e., etching of the surface with an aqueous solution of alkali, e.g., sodium hydroxide or potassium hydroxide, that may also contain a fluorosurfactant. See U.S. Patent 3,971,892, column 3, lines 13 to 25; U.S. Patent 4,904,525, column 6, lines 10 to 48; and U.S. Patent 5,104,692, column 13, lines 10 to 59, which describe surface treatments of polymeric organic materials.
- an aqueous mixture of organic solvent e.g., a 50:50 mixture of isopropanol
- water or ethanol water
- Composition A The following materials were added in the order and manner described to a suitable reaction vessel equipped with an agitator, a reflux column, an addition funnel, nitrogen inlet, an internal temperature probe connected to an external electronic controller and a heating mantle:
- Example 1 Part A The following materials were added in the order and the manner described to a suitable reaction vessel equipped with an agitator, a thermometer, nitrogen inlet and heat/cooling capabilities. After addition of the materials, nitrogen was introduced into the vessel to provide a nitrogen blanket and the agitator was turned on. Heat was applied until the prepolymer reaction mixture reached a temperature of 250°F (121°C) . Further heating was discontinued. The resulting exothermic reaction usually caused an increase in the temperature of the reaction mixture to about 280°F (138°C) . If the temperature continued to rise above 280°F (138°C) , cooling was applied. After the reaction temperature reached about 220°F (104°C) , the prepolymer product was filtered through a 400 mesh filter. The resulting filtrate was cooled and transferred to a suitable container.
- Polycaprolactone diol having an equivalent weight of about 400 ( 2 ) Polycaprolactone diol having an equivalent weight of about 200.
- reaction injection molding (RIM) machine such as the Max Mixer available from Max Machines:
- Charge-1 was added to the container.
- Charge-2 was added and the contents were rapidly mixed in the Max Mixer.
- Part C The product of Part B was poured into molds measuring 60-80 mm that were treated with an external mold release agent, preheated to 150°C and placed in an oven at 150°C for 16 hours. Afterwards, the polymerizates were removed from the molds.
- a naphtho [1, 2 -b]pyran that exhibits a blue color when irradiated with ultraviolet light.
- a naphtho [1, 2-b]pyran that exhibits a red-orange color when irradiated with ultraviolet light.
- Charge- 1 was added to the vessel, the agitator was turned on and the contents were mixed until the solids were dissolved.
- Charges 2, 3, and 4 were separately added and after each addition, the solution was mixed.
- the resulting solution was filtered through a 10 micron filter and degassed under vacuum for about 20 minutes.
- Example 2 The procedure of Example 1 was followed except that the following formulation was used in Part A to prepare the prepolymer.
- Example 3 Prior to application of the photochromic polymeric solution described in Part D of Example 1, some of the lenses of Example 1 and all of the lenses of Example 2 were treated with oxygen plasma in a PLASMAtech/PLASMAfinish microwave gas plasma system (unit) .
- the following treatment conditions were used: power was set to 100 Watts; gas pressure was 42 pascals; a gas flowrate of lOOmL/minute was used; and the processing time was 60 seconds .
- Half of the plasma treated lenses of Examples 1 and 2 were additionally coated with Hi-Gard® 1080 protective coating.
- the lenses having the substrate protective coating were designaged 1C and 2C in Table 1. After application of the protective coating, the lenses were cured in a convection oven at 60°C for 20 minutes followed by further curing at 120°C for 3 hours. The thickness of the dried coating was approximately 2 microns .
- the photochromic polymeric solution described in Part D of Example 1 was applied via a spincoating method to the plasma-treated lenses of Examples 1 and 2 . Approximately 800 milligrams of solution was dispensed onto each lens that was spinning at 2000 rpm, which resulted in a wet film weight of approximately 200 milligrams per lens.
- the coated lenses were initially exposed to infrared light for a time sufficient to reduce the sticky nature of the coated lenses and then were cured for 40 minutes in a convection oven maintained at 140°C. The final thickness of the dried coatings was approximately 20 microns . All of the lenses were additionally coated with an organosilane-containing protective coating and cured following the same conditions used to cure the Hi-Gard® 1080 protective coating.
- Part B The photochromic coated test samples prepared in Part
- the photochromic test samples Prior to testing on the optical bench, the photochromic test samples were exposed to 365 nanometer ultraviolet light for about 20 minutes to activate the photochromic compounds and then placed in a 75 °C oven for about 20 minutes to bleach (inactivate) the photochromic compounds.
- the coated test samples were then cooled to room temperature, exposed to fluorescent room lighting for at least 3 hours and then kept covered for at least 1 hour prior to testing on an optical bench.
- the bench was fitted with a 300 watt Xenon arc lamp, a remote controlled shutter, a Schott 3 mm KG-2 band-pass filter, which removes short wavelength radiation, neutral density filter(s), a quartz cell sample holder for maintaining sample temperature in which the test sample to be tested was inserted.
- the power output of the optical bench i.e., the dosage of light that the test sample would be exposed to, was adjusted to 0.67 milliwatts per square centimeter (mW/cm 2 ) using a GRASEBY Optronics Model S-371 portable photometer (Serial #21536) with a TJV-A detector (Serial # 22411) .
- the UV-A detector was placed into the sample holder and the light output was measured.
- Adjustments to the power output were made by increasing or decreasing the lamp wattage or by adding or removing neutral density filters in the light path.
- a monitoring, collimated beam of light from a tungsten lamp was passed through the sample at 30° normal to the surface of the lens. After passing through the lens, the light from the tungsten lamp was directed through a photopic filter attached to a detector. The output signals from the detector were processed by a radiometer. The control of the test conditions and acquisition of data was handled by the Labtech Notebook Pro software and the recommended I/O board.
- the ⁇ OD was measured after the first thirty (30) seconds of UV exposure and then after fifteen (15) minutes with the optical bench maintained at a temperature of 72°F (22°C) .
- the Bleach Rate (T 1/2) is the time interval in seconds for the ⁇ OD of the activated form of the photochromic compound in the coated test samples to reach one half the highest ⁇ OD at (72°F, 22 °C) after removal of the source of activating light. Results for the photochromic coated test samples for each Example are listed in Table 1.
- Part C The lenses of Example 1 that were not treated with oxygen plasma were cleaned with a tissue soaked with isopropyl alcohol. After drying, the lenses were coated with the photochromic polymeric solution of Part D of Example 1 via the spincoating and curing procedure described in Part A herein. The final thickness of the cured coating was approximately 20 microns.
- Adhesion of the coatings on the test lenses was measured using ASTM D-3359-93 Standard Test Method for Measuring Adhesion by Tape Test-Method B. Testing was performed prior to immersing the lenses in boiling deionized water and after 60 minutes of immersion in the boiling water. Immersion in boiling water simulated chemical attack. The adhesion test results revealed no loss of the coating before or after immersion in the boiling water for the lenses of Example 1 that were not treated with oxygen plasma.
Abstract
Description
Claims
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AU2001231128A AU2001231128A1 (en) | 2000-02-04 | 2001-01-25 | Photochromic coated articles |
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US49905400A | 2000-02-04 | 2000-02-04 | |
US09/499,054 | 2000-02-04 |
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PCT/US2001/002380 WO2001057106A1 (en) | 2000-02-04 | 2001-01-25 | Photochromic coated articles |
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US (1) | US6733887B2 (en) |
AU (1) | AU2001231128A1 (en) |
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US6733887B2 (en) | 2004-05-11 |
US20030044620A1 (en) | 2003-03-06 |
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