CA2459866A1 - Photochromic bis-naphthopyran compounds and methods for their manufacture - Google Patents
Photochromic bis-naphthopyran compounds and methods for their manufacture Download PDFInfo
- Publication number
- CA2459866A1 CA2459866A1 CA002459866A CA2459866A CA2459866A1 CA 2459866 A1 CA2459866 A1 CA 2459866A1 CA 002459866 A CA002459866 A CA 002459866A CA 2459866 A CA2459866 A CA 2459866A CA 2459866 A1 CA2459866 A1 CA 2459866A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkoxy
- phenyl
- cycloalkyl
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- IJJMQFOFFIWMNN-UHFFFAOYSA-N 12-oxapentacyclo[12.8.0.02,11.03,8.015,20]docosa-1(14),2(11),3,5,7,9,15,17,19,21-decaene Chemical class C1=CC=CC2=C3COC4=CC=C(C=CC=C5)C5=C4C3=CC=C21 IJJMQFOFFIWMNN-UHFFFAOYSA-N 0.000 title abstract description 13
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- -1 phenylacetylenyl Chemical group 0.000 claims description 104
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- VCMLCMCXCRBSQO-UHFFFAOYSA-N 3h-benzo[f]chromene Chemical compound C1=CC=CC2=C(C=CCO3)C3=CC=C21 VCMLCMCXCRBSQO-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Chemical group 0.000 claims description 9
- 239000001301 oxygen Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- YEQJONKQJLKCHR-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-[5-[5-[3-(4-methoxyphenyl)benzo[f]chromen-3-yl]thiophen-2-yl]thiophen-2-yl]benzo[f]chromene Chemical compound C1=CC(OC)=CC=C1C1(C=2SC(=CC=2)C=2SC(=CC=2)C2(C=CC3=C4C=CC=CC4=CC=C3O2)C=2C=CC(OC)=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 YEQJONKQJLKCHR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 3
- KVBYJSOLTLFGAS-UHFFFAOYSA-N 3-(4-fluorophenyl)-3-[5-[5-[3-(4-fluorophenyl)benzo[f]chromen-3-yl]thiophen-2-yl]thiophen-2-yl]benzo[f]chromene Chemical compound C1=CC(F)=CC=C1C1(C=2SC(=CC=2)C=2SC(=CC=2)C2(C=CC3=C4C=CC=CC4=CC=C3O2)C=2C=CC(F)=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 KVBYJSOLTLFGAS-UHFFFAOYSA-N 0.000 claims description 3
- NYUMKEXJTPXMJR-UHFFFAOYSA-N 3-(4-methylphenyl)-3-[5-[5-[3-(4-methylphenyl)benzo[f]chromen-3-yl]thiophen-2-yl]thiophen-2-yl]benzo[f]chromene Chemical compound C1=CC(C)=CC=C1C1(C=2SC(=CC=2)C=2SC(=CC=2)C2(C=CC3=C4C=CC=CC4=CC=C3O2)C=2C=CC(C)=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 NYUMKEXJTPXMJR-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 125000004986 diarylamino group Chemical group 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 10
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 8
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims 8
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 4
- 125000004643 (C1-C12) haloalkoxy group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 2
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 2
- IFBNDCRGSQAVKS-UHFFFAOYSA-N 3-(2-fluorophenyl)-3-[5-[5-[3-(2-fluorophenyl)benzo[f]chromen-3-yl]thiophen-2-yl]thiophen-2-yl]benzo[f]chromene Chemical compound FC1=CC=CC=C1C1(C=2SC(=CC=2)C=2SC(=CC=2)C2(C=CC3=C4C=CC=CC4=CC=C3O2)C=2C(=CC=CC=2)F)C=CC2=C3C=CC=CC3=CC=C2O1 IFBNDCRGSQAVKS-UHFFFAOYSA-N 0.000 claims 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 2
- 230000004913 activation Effects 0.000 abstract description 4
- 230000004044 response Effects 0.000 abstract description 4
- 230000008859 change Effects 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 125000000217 alkyl group Chemical group 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 23
- 229940073584 methylene chloride Drugs 0.000 description 20
- 239000000203 mixture Substances 0.000 description 15
- 230000008569 process Effects 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 101100272976 Panax ginseng CYP716A53v2 gene Proteins 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 5
- 238000005562 fading Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VXMHYFQHZLBFFE-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-thiophen-2-ylbenzo[f]chromene Chemical compound C1=CC(OC)=CC=C1C1(C=2SC=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 VXMHYFQHZLBFFE-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- KLTRLSNGWVFQNG-UHFFFAOYSA-N 1-(4-methoxyphenyl)-1-thiophen-2-ylprop-2-yn-1-ol Chemical compound C1=CC(OC)=CC=C1C(O)(C#C)C1=CC=CS1 KLTRLSNGWVFQNG-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-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
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- LUIQNLIEDINBMR-UHFFFAOYSA-N 3-(4-fluorophenyl)-3-thiophen-2-ylbenzo[f]chromene Chemical compound C1=CC(F)=CC=C1C1(C=2SC=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 LUIQNLIEDINBMR-UHFFFAOYSA-N 0.000 description 2
- NRSHWKZBFDZELB-UHFFFAOYSA-N 3-(4-methylphenyl)-3-thiophen-2-ylbenzo[f]chromene Chemical compound C1=CC(C)=CC=C1C1(C=2SC=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 NRSHWKZBFDZELB-UHFFFAOYSA-N 0.000 description 2
- JORUZGFDZMBHDR-UHFFFAOYSA-N 3-naphthalen-2-yl-3-(5-thiophen-2-ylthiophen-2-yl)benzo[f]chromene Chemical compound O1C2=CC=C3C=CC=CC3=C2C=CC1(C=1C=C2C=CC=CC2=CC=1)C(S1)=CC=C1C1=CC=CS1 JORUZGFDZMBHDR-UHFFFAOYSA-N 0.000 description 2
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229940081735 acetylcellulose Drugs 0.000 description 2
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 2
- 150000008365 aromatic ketones Chemical class 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- IMTDPCTYUISKDT-UHFFFAOYSA-N bis[3-(4-methoxyphenyl)thiophen-2-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)C2=C(C=CS2)C=2C=CC(OC)=CC=2)SC=C1 IMTDPCTYUISKDT-UHFFFAOYSA-N 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- PDJFCIWHCYABGA-UHFFFAOYSA-N naphthalen-2-yl-(5-thiophen-2-ylthiophen-2-yl)methanone Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)C(S1)=CC=C1C1=CC=CS1 PDJFCIWHCYABGA-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- TWKDIVDAGCWHES-UHFFFAOYSA-N 2-(4-methoxyphenyl)thiophene Chemical compound C1=CC(OC)=CC=C1C1=CC=CS1 TWKDIVDAGCWHES-UHFFFAOYSA-N 0.000 description 1
- CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical compound CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 description 1
- NPWBWRGEKRCJKH-UHFFFAOYSA-N 3-(2-fluorophenyl)-3-thiophen-2-ylbenzo[f]chromene Chemical compound FC1=CC=CC=C1C1(C=2SC=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 NPWBWRGEKRCJKH-UHFFFAOYSA-N 0.000 description 1
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical class OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 description 1
- SANFZVXZFRQJOL-UHFFFAOYSA-N 6-ethoxy-1h-benzimidazole Chemical compound CCOC1=CC=C2N=CNC2=C1 SANFZVXZFRQJOL-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical class COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002225 anti-radical effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000005325 aryloxy aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- IUOBPBSTMKHCNS-UHFFFAOYSA-N bis[4-methoxy-2-(5-thiophen-2-ylthiophen-2-yl)phenyl]methanone Chemical compound C=1C=C(C=2SC=CC=2)SC=1C1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1C(S1)=CC=C1C1=CC=CS1 IUOBPBSTMKHCNS-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 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
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940032007 methylethyl ketone Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002578 polythiourethane polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Eyeglasses (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/945,897 | 2001-09-04 | ||
| US09/945,897 US6747145B2 (en) | 2001-09-04 | 2001-09-04 | Photochromic bis-naphthopyran compounds and methods for their manufacture |
| PCT/US2002/025669 WO2003020718A1 (en) | 2001-09-04 | 2002-08-13 | Photochromic bis-naphthopyran compounds and methods for their manufacture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2459866A1 true CA2459866A1 (en) | 2003-03-13 |
Family
ID=25483666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002459866A Abandoned CA2459866A1 (en) | 2001-09-04 | 2002-08-13 | Photochromic bis-naphthopyran compounds and methods for their manufacture |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6747145B2 (enExample) |
| EP (1) | EP1423387B1 (enExample) |
| JP (1) | JP4368679B2 (enExample) |
| KR (1) | KR100906205B1 (enExample) |
| CN (1) | CN1296371C (enExample) |
| AU (1) | AU2002332520B2 (enExample) |
| BR (1) | BR0212551A (enExample) |
| CA (1) | CA2459866A1 (enExample) |
| DE (1) | DE60235706D1 (enExample) |
| TW (1) | TW591021B (enExample) |
| WO (1) | WO2003020718A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050258408A1 (en) * | 2001-12-20 | 2005-11-24 | Molock Frank F | Photochromic contact lenses and methods for their production |
| JP4506953B2 (ja) * | 2004-05-28 | 2010-07-21 | 日本電気株式会社 | 共重合高分子膜およびその作製方法 |
| US20060227287A1 (en) * | 2005-04-08 | 2006-10-12 | Frank Molock | Photochromic ophthalmic devices made with dual initiator system |
| US9052438B2 (en) | 2005-04-08 | 2015-06-09 | Johnson & Johnson Vision Care, Inc. | Ophthalmic devices comprising photochromic materials with reactive substituents |
| US9139552B2 (en) | 2005-04-08 | 2015-09-22 | Transitions Optical, Inc. | Indeno-fused naphthopyrans having ethylenically unsaturated groups |
| US8147725B2 (en) | 2005-04-08 | 2012-04-03 | Transitions Optical, Inc | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
| US8647538B2 (en) | 2005-04-08 | 2014-02-11 | Transitions Optical, Inc. | Photochromic compounds having at least two photochromic moieties |
| US8158037B2 (en) | 2005-04-08 | 2012-04-17 | Johnson & Johnson Vision Care, Inc. | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
| US7556750B2 (en) * | 2005-04-08 | 2009-07-07 | Transitions Optical, Inc. | Photochromic materials with reactive substituents |
| US20060228557A1 (en) * | 2005-04-08 | 2006-10-12 | Beon-Kyu Kim | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
| US9028728B2 (en) | 2005-04-08 | 2015-05-12 | Transitions Optical, Inc. | Photochromic materials that include indeno-fused naphthopyrans |
| US20060226402A1 (en) * | 2005-04-08 | 2006-10-12 | Beon-Kyu Kim | Ophthalmic devices comprising photochromic materials having extended PI-conjugated systems |
| DE502006001441D1 (de) * | 2006-01-27 | 2008-10-09 | Ems Chemie Ag | Photochrome Formmassen und daraus hergestellte Gegenstände |
| US20090244479A1 (en) * | 2008-03-31 | 2009-10-01 | Diana Zanini | Tinted silicone ophthalmic devices, processes and polymers used in the preparation of same |
| US8595218B2 (en) * | 2008-06-12 | 2013-11-26 | Intellectual Ventures Holding 67 Llc | Interactive display management systems and methods |
| US10381134B2 (en) * | 2015-12-29 | 2019-08-13 | Xerox Corporation | Strain gauge polymer comprising photochromic colorant |
| CN110152728A (zh) * | 2019-05-31 | 2019-08-23 | 上海纳米技术及应用国家工程研究中心有限公司 | 具备光致变色性能的复合材料的制备方法及产品和应用 |
| US20230242808A1 (en) * | 2019-10-17 | 2023-08-03 | Tokuyama Corporation | Photochromic compound and curable composition containing the photochromic compound |
| US12326443B2 (en) * | 2020-09-21 | 2025-06-10 | B/E Aerospace Inc. | Detecting antimicrobial surfaces |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3567605A (en) | 1966-03-30 | 1971-03-02 | Ralph S Becker | Photochemical process |
| US5066818A (en) | 1990-03-07 | 1991-11-19 | Ppg Industries, Inc. | Photochromic naphthopyran compounds |
| JPH0689962A (ja) | 1992-02-28 | 1994-03-29 | Mega Chips:Kk | 半導体装置 |
| US5384077A (en) * | 1993-06-21 | 1995-01-24 | Transitions Optical, Inc. | Photochromic naphthopyran compounds |
| ATE184905T1 (de) | 1994-07-11 | 1999-10-15 | Rodenstock Optik G | Diaryl-2h-naphthopyrane |
| US5645767A (en) | 1994-11-03 | 1997-07-08 | Transitions Optical, Inc. | Photochromic indeno-fused naphthopyrans |
| US6281366B1 (en) | 2000-02-29 | 2001-08-28 | Essilor International Compagnie Generale D'optique | Photochromic [3H]naphtho[2,1-b]pyran compounds containing an acetylenic substituent, process for their manufacture, and photochromic materials and articles obtained |
-
2001
- 2001-09-04 US US09/945,897 patent/US6747145B2/en not_active Expired - Fee Related
-
2002
- 2002-08-13 JP JP2003524988A patent/JP4368679B2/ja not_active Expired - Fee Related
- 2002-08-13 EP EP02797735A patent/EP1423387B1/en not_active Expired - Lifetime
- 2002-08-13 CA CA002459866A patent/CA2459866A1/en not_active Abandoned
- 2002-08-13 DE DE60235706T patent/DE60235706D1/de not_active Expired - Lifetime
- 2002-08-13 WO PCT/US2002/025669 patent/WO2003020718A1/en not_active Ceased
- 2002-08-13 KR KR1020047003278A patent/KR100906205B1/ko not_active Expired - Fee Related
- 2002-08-13 AU AU2002332520A patent/AU2002332520B2/en not_active Ceased
- 2002-08-13 BR BR0212551-0A patent/BR0212551A/pt not_active IP Right Cessation
- 2002-08-13 CN CNB028216644A patent/CN1296371C/zh not_active Expired - Fee Related
- 2002-09-03 TW TW091119985A patent/TW591021B/zh not_active IP Right Cessation
-
2003
- 2003-10-28 US US10/695,062 patent/US6939007B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR0212551A (pt) | 2004-10-19 |
| AU2002332520B2 (en) | 2007-04-26 |
| TW591021B (en) | 2004-06-11 |
| EP1423387B1 (en) | 2010-03-17 |
| WO2003020718A1 (en) | 2003-03-13 |
| JP2005508897A (ja) | 2005-04-07 |
| KR20040041601A (ko) | 2004-05-17 |
| US20040084660A1 (en) | 2004-05-06 |
| JP4368679B2 (ja) | 2009-11-18 |
| CN1671699A (zh) | 2005-09-21 |
| US6939007B2 (en) | 2005-09-06 |
| KR100906205B1 (ko) | 2009-07-07 |
| CN1296371C (zh) | 2007-01-24 |
| US20030078441A1 (en) | 2003-04-24 |
| US6747145B2 (en) | 2004-06-08 |
| EP1423387A1 (en) | 2004-06-02 |
| DE60235706D1 (de) | 2010-04-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6747145B2 (en) | Photochromic bis-naphthopyran compounds and methods for their manufacture | |
| AU2002332520A1 (en) | Photochromic bis-naphthopyran compounds and methods for their manufacture | |
| US5552091A (en) | Benzopyran compounds | |
| US6096246A (en) | Photochromic naphthopyrans, compositions and articles containing them | |
| AU758378B2 (en) | Polyalkoxylated naphthopyrans | |
| US5429774A (en) | Benzopyran compounds | |
| AU719894B2 (en) | Novel homoazaadamantane spirooxazines and their use in the field of ophthalmic optics | |
| JP2019203144A (ja) | フォトクロミック化合物 | |
| JP2008537762A (ja) | π共役系が延長されたフォトクロミック材料を含む眼用装置 | |
| US6294112B1 (en) | Red coloring hyperchromic 3H-naphtho[2,1-B]pyrans | |
| KR101602588B1 (ko) | 6-아미노 치환된 인데노-융합된 나프토피란을 포함하는 광변색성 물질 | |
| AU1079799A (en) | 7-methylidene-5-oxo-furo fused naphthopyrans | |
| JP2003513098A (ja) | ５、６位に複素環を持つナフトピラン、その調製並びにそれらを含有する組成物およびマトリクス | |
| MXPA01011798A (es) | Benzopiranos anillados en c7-c8 con un heterociclo aromatico y composiciones y matrices de (co)polimeros que los contienen. | |
| US6608215B2 (en) | Oxygen-containing heterocyclic fused naphthopyrans | |
| EP1558603B1 (en) | Oxyge-containing heterocyclic fused naphthopyrans | |
| WO2007073463A1 (en) | Photochromic 2h-naphthopyrans | |
| US6478989B1 (en) | Aromatic substituted naphthopyrans | |
| JP2774830B2 (ja) | スピロオキサジン化合物及びその製造方法 | |
| JP2003502333A (ja) | ラクタム型ｃ６環とｃ５−ｃ６で環化されたナフトピラン並びにそれらを含有する組成物および（コ）ポリマー | |
| MXPA01008319A (en) | Naphthopyrans and phenanthropyrans annelated in c5-c6 with a bicyclic group, and compositions and (co)polymer matrices containing them | |
| MXPA01002555A (en) | Polyalkoxylated naphthopyrans |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |