AU2004311372B8 - Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles - Google Patents
Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles Download PDFInfo
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- AU2004311372B8 AU2004311372B8 AU2004311372A AU2004311372A AU2004311372B8 AU 2004311372 B8 AU2004311372 B8 AU 2004311372B8 AU 2004311372 A AU2004311372 A AU 2004311372A AU 2004311372 A AU2004311372 A AU 2004311372A AU 2004311372 B8 AU2004311372 B8 AU 2004311372B8
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- Prior art keywords
- alkyl
- chosen
- mono
- alkoxy
- phenyl
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- 150000004780 naphthols Chemical class 0.000 title description 9
- -1 dibenzofuranyl Chemical group 0.000 claims description 197
- 239000000463 material Substances 0.000 claims description 185
- 125000000217 alkyl group Chemical group 0.000 claims description 138
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 130
- 239000001257 hydrogen Substances 0.000 claims description 97
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- 125000003545 alkoxy group Chemical group 0.000 claims description 81
- 238000000576 coating method Methods 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 59
- 239000011248 coating agent Substances 0.000 claims description 56
- 150000002431 hydrogen Chemical class 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 46
- 125000001624 naphthyl group Chemical group 0.000 claims description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 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 40
- 239000000178 monomer Substances 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
- 125000001153 fluoro group Chemical group F* 0.000 claims description 36
- 239000000758 substrate Substances 0.000 claims description 31
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 27
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 230000003287 optical effect Effects 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 19
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 14
- 239000008199 coating composition Substances 0.000 claims description 14
- 150000002430 hydrocarbons Chemical group 0.000 claims description 14
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 238000005299 abrasion Methods 0.000 claims description 12
- 150000002829 nitrogen Chemical class 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 229920001577 copolymer Chemical compound 0.000 claims description 11
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 11
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 10
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
- 229920001169 thermoplastic Polymers 0.000 claims description 10
- 229920001187 thermosetting polymer Polymers 0.000 claims description 10
- 239000004416 thermosoftening plastic Substances 0.000 claims description 10
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims description 8
- 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004197 benzothien-3-yl group Chemical group [H]C1=C(*)C2=C([H])C([H])=C([H])C([H])=C2S1 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 239000004814 polyurethane Substances 0.000 claims description 7
- 229920002635 polyurethane Polymers 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 5
- 239000006117 anti-reflective coating Substances 0.000 claims description 5
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- 229920000193 polymethacrylate Polymers 0.000 claims description 5
- 239000012815 thermoplastic material Substances 0.000 claims description 5
- 229920002732 Polyanhydride Polymers 0.000 claims description 4
- 229920003180 amino resin Polymers 0.000 claims description 4
- 125000004986 diarylamino group Chemical group 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000011368 organic material Substances 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 4
- 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 4
- 229920000548 poly(silane) polymer Polymers 0.000 claims description 4
- 229920000515 polycarbonate Polymers 0.000 claims description 4
- 239000004417 polycarbonate Substances 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 3
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 150000008371 chromenes Chemical class 0.000 claims description 3
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 3
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 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 3
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 3
- 150000004893 oxazines Chemical class 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 3
- 229920002401 polyacrylamide Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 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 claims description 2
- GFSXWQUSLTVUBW-UHFFFAOYSA-N 10bh-benzo[h]chromene Chemical compound C1=CC=C2C3OC=CC=C3C=CC2=C1 GFSXWQUSLTVUBW-UHFFFAOYSA-N 0.000 claims description 2
- KJLKDWJTPOQDFG-UHFFFAOYSA-N 21-ethyl-5,5-bis(4-methoxyphenyl)-18-morpholin-4-yl-6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15(20),16,18-nonaen-21-ol Chemical compound CCC1(O)C2=CC(N3CCOCC3)=CC=C2C(C2=CC=CC=C2C=2O3)=C1C=2C=CC3(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 KJLKDWJTPOQDFG-UHFFFAOYSA-N 0.000 claims description 2
- OOXMQACSWCZQLX-UHFFFAOYSA-N 3,9-bis(ethenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane Chemical compound C1OC(C=C)OCC21COC(C=C)OC2 OOXMQACSWCZQLX-UHFFFAOYSA-N 0.000 claims description 2
- XKIRPBOJRMZGBN-UHFFFAOYSA-N 4-[17-methoxy-5,5-bis(4-methoxyphenyl)-21,21-dimethyl-6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaen-18-yl]morpholine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=CC(OC)=CC=2)C=CC(C=2C(C3=CC(=C(OC)C=C3C=2C=2C3=CC=CC=2)N2CCOCC2)(C)C)=C3O1 XKIRPBOJRMZGBN-UHFFFAOYSA-N 0.000 claims description 2
- OQMBARZIVWRVCB-UHFFFAOYSA-N 4-[4-[5-(4-methoxyphenyl)-21,21-dimethyl-18-morpholin-4-yl-6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15(20),16,18-nonaen-5-yl]phenyl]morpholine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=CC(=CC=2)N2CCOCC2)C=CC(C=2C(C3=CC(=CC=C3C=2C=2C3=CC=CC=2)N2CCOCC2)(C)C)=C3O1 OQMBARZIVWRVCB-UHFFFAOYSA-N 0.000 claims description 2
- FZXRKTFOEFOVBD-UHFFFAOYSA-N 4-[5-(3,4-dimethoxyphenyl)-5-(4-methoxyphenyl)-21,21-dimethyl-6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15(20),16,18-nonaen-18-yl]morpholine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(OC)C(OC)=CC=2)C=CC(C=2C(C3=CC(=CC=C3C=2C=2C3=CC=CC=2)N2CCOCC2)(C)C)=C3O1 FZXRKTFOEFOVBD-UHFFFAOYSA-N 0.000 claims description 2
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 claims description 2
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- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 2
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- 125000004076 pyridyl group Chemical group 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 11
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 5
- 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 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- SKESERDUDQOXKM-UHFFFAOYSA-N 2-methylprop-2-enoic acid;phenol Chemical class CC(=C)C(O)=O.CC(=C)C(O)=O.OC1=CC=CC=C1 SKESERDUDQOXKM-UHFFFAOYSA-N 0.000 claims 1
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- 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 claims 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims 1
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- 125000005702 oxyalkylene group Chemical group 0.000 claims 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- 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]
-
- 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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/259—Coating or impregnation provides protection from radiation [e.g., U.V., visible light, I.R., micscheme-change-itemave, high energy particle, etc.] or heat retention thru radiation absorption
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2007202187A AU2007202187B2 (en) | 2003-03-20 | 2007-05-16 | Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/393,177 US7262295B2 (en) | 2003-03-20 | 2003-03-20 | Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles |
| US10/393,177 | 2003-03-20 | ||
| PCT/US2004/008156 WO2005090327A1 (en) | 2003-03-20 | 2004-03-16 | Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007202187A Division AU2007202187B2 (en) | 2003-03-20 | 2007-05-16 | Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| AU2004311372A1 AU2004311372A1 (en) | 2005-09-15 |
| AU2004311372B2 AU2004311372B2 (en) | 2007-08-02 |
| AU2004311372B8 true AU2004311372B8 (en) | 2009-03-05 |
| AU2004311372A8 AU2004311372A8 (en) | 2009-03-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004311372A Expired AU2004311372B8 (en) | 2003-03-20 | 2004-03-16 | Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles |
Country Status (13)
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| 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 |
| US8545984B2 (en) | 2003-07-01 | 2013-10-01 | Transitions Optical, Inc. | Photochromic compounds and compositions |
| US8518546B2 (en) | 2003-07-01 | 2013-08-27 | Transitions Optical, Inc. | Photochromic compounds and compositions |
| US20110140056A1 (en) | 2003-07-01 | 2011-06-16 | Transitions Optical, Inc. | Indeno-fused ring compounds |
| US8211338B2 (en) * | 2003-07-01 | 2012-07-03 | Transitions Optical, Inc | Photochromic compounds |
| US8698117B2 (en) | 2003-07-01 | 2014-04-15 | Transitions Optical, Inc. | Indeno-fused ring compounds |
| US7632540B2 (en) | 2003-07-01 | 2009-12-15 | Transitions Optical, Inc. | Alignment facilities for optical dyes |
| WO2005059060A1 (en) * | 2003-12-15 | 2005-06-30 | Worcester Polytechnic Institute | Films with photoresponsive wettability |
| US7556750B2 (en) * | 2005-04-08 | 2009-07-07 | Transitions Optical, Inc. | Photochromic materials with reactive substituents |
| US8647538B2 (en) | 2005-04-08 | 2014-02-11 | Transitions Optical, Inc. | Photochromic compounds having at least two photochromic moieties |
| US20060226402A1 (en) * | 2005-04-08 | 2006-10-12 | Beon-Kyu Kim | Ophthalmic devices comprising photochromic materials having extended PI-conjugated systems |
| US9028728B2 (en) | 2005-04-08 | 2015-05-12 | Transitions Optical, Inc. | Photochromic materials that include indeno-fused naphthopyrans |
| 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 |
| 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 |
| 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 |
| US20060227287A1 (en) * | 2005-04-08 | 2006-10-12 | Frank Molock | Photochromic ophthalmic devices made with dual initiator system |
| US9139552B2 (en) | 2005-04-08 | 2015-09-22 | Transitions Optical, Inc. | Indeno-fused naphthopyrans having ethylenically unsaturated groups |
| US9052438B2 (en) * | 2005-04-08 | 2015-06-09 | Johnson & Johnson Vision Care, Inc. | Ophthalmic devices comprising photochromic materials with reactive substituents |
| US9034457B2 (en) * | 2006-09-11 | 2015-05-19 | Alphamicron Incorporated | Photochromic devices and methods for making the same |
| WO2008049755A2 (en) * | 2006-10-26 | 2008-05-02 | Ciba Holding Inc. | Light absorbing layer for photo-chromic systems |
| US8748634B2 (en) * | 2006-10-30 | 2014-06-10 | Transitions Optical, Inc. | Photochromic materials demonstrating improved fade rates |
| US7667285B2 (en) * | 2006-12-14 | 2010-02-23 | Motorola, Inc. | Printed electronic substrate havine photochromic barrier layer |
| JP5320722B2 (ja) * | 2007-11-06 | 2013-10-23 | 東ソー株式会社 | ベンゾフルオレノン誘導体及びその製造方法 |
| US20090326186A1 (en) * | 2008-06-27 | 2009-12-31 | Transitions Optical, Inc. | Mesogen containing compounds |
| US20100014010A1 (en) * | 2008-06-27 | 2010-01-21 | Transitions Optical, Inc. | Formulations comprising mesogen containing compounds |
| US8623238B2 (en) | 2008-06-27 | 2014-01-07 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US8628685B2 (en) | 2008-06-27 | 2014-01-14 | Transitions Optical, Inc | Mesogen-containing compounds |
| US7910019B2 (en) | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Mesogen containing compounds |
| US8349210B2 (en) | 2008-06-27 | 2013-01-08 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US8431039B2 (en) | 2008-06-27 | 2013-04-30 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US7910020B2 (en) * | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Liquid crystal compositions comprising mesogen containing compounds |
| US8613868B2 (en) | 2008-06-27 | 2013-12-24 | Transitions Optical, Inc | Mesogenic stabilizers |
| US8217188B2 (en) * | 2008-08-27 | 2012-07-10 | Corning Incorporated | 2H-chromenes annelated at C5-C6 and methods of making and using thereof |
| CN101503484B (zh) * | 2009-03-04 | 2010-11-17 | 东北师范大学 | 含萘酚吡喃基团光致变色交联聚合物的合成方法 |
| US8518305B2 (en) | 2009-10-28 | 2013-08-27 | Transitions Optical, Inc. | Photochromic materials |
| WO2011078030A1 (ja) * | 2009-12-22 | 2011-06-30 | 株式会社トクヤマ | クロメン化合物 |
| US9139571B2 (en) | 2010-12-16 | 2015-09-22 | Transitions Optical, Inc. | Methods of making fused ring compounds |
| US9034219B2 (en) | 2010-12-16 | 2015-05-19 | Transitions Optical, Inc. | Photochromic compounds and compositions |
| US8920928B2 (en) | 2010-12-16 | 2014-12-30 | Transitions Optical, Inc. | Photochromic compounds and compositions |
| US8859097B2 (en) * | 2010-12-16 | 2014-10-14 | Transitions Optical, Inc. | Photochromic compounds, compositions and articles |
| HUE025467T2 (en) | 2011-01-28 | 2016-02-29 | Tokuyama Corp | Chromene compound |
| WO2014136804A1 (ja) * | 2013-03-04 | 2014-09-12 | 株式会社トクヤマ | フォトクロミック硬化性組成物、その硬化体及びその硬化体を含む積層体 |
| US9029565B1 (en) | 2013-11-20 | 2015-05-12 | Transitions Optical, Inc. | Fused ring indeno compounds for preparation of photochromic compounds |
| US9206151B2 (en) | 2013-11-20 | 2015-12-08 | Transitions Optical, Inc. | Method of preparing fused ring indeno compounds |
| US9051332B1 (en) | 2013-11-20 | 2015-06-09 | Transitions Optical, Inc. | Photochromic indeno-fused ring pyran compounds |
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| WO2020126029A1 (en) | 2018-12-21 | 2020-06-25 | Transitions Optical, Ltd. | Articles comprising indolenaphthopyrans |
| AU2018454273A1 (en) | 2018-12-21 | 2021-07-15 | Transitions Optical, Ltd. | Indolenaphthopyrans and photochromic compositions comprising them |
| AU2018454681B2 (en) | 2018-12-21 | 2023-11-23 | Transitions Optical, Ltd. | Indolonaphthopyrans |
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| JP2022151089A (ja) * | 2021-03-26 | 2022-10-07 | ホヤ レンズ タイランド リミテッド | インデノ縮合ナフトピラン化合物の粒子、重合性組成物の製造方法及びフォトクロミック物品の製造方法 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19741705A1 (de) * | 1997-09-22 | 1999-04-01 | Rodenstock Optik G | Naphtopyrane |
| WO2001019813A1 (en) * | 1999-09-17 | 2001-03-22 | Transitions Optical, Inc. | Novel indeno-fused photochromic naphthopyrans |
| US6340765B1 (en) * | 1999-05-20 | 2002-01-22 | Tokuyama Corporation | Chromene compound |
Family Cites Families (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3361706A (en) | 1964-03-06 | 1968-01-02 | American Cyanamid Co | Control of the photochromic return rate of (arylazo) thioformic arylhydrazidates |
| US4166043A (en) | 1974-12-23 | 1979-08-28 | American Optical Corporation | Stabilized photochromic materials |
| US4367170A (en) | 1975-01-24 | 1983-01-04 | American Optical Corporation | Stabilized photochromic materials |
| US4360653A (en) | 1981-10-23 | 1982-11-23 | Ppg Industries, Inc. | Polymerizate of (allyl carbonate) and aliphatic polyurethane having acrylic unsaturation |
| US4720356A (en) | 1982-03-22 | 1988-01-19 | American Optical Corporation | Photochromic composition resistant to fatigue |
| US4556605A (en) | 1982-09-09 | 1985-12-03 | Kabushiki Kaisha Suwa Seikosha | Photochromic coating composition and photochromic synthetic resin ophthalmic lens |
| AU564689B2 (en) | 1985-07-09 | 1987-08-20 | Kureha Kagaku Kogyo K.K. | Photochromic lens |
| CA1340939C (en) | 1987-02-02 | 2000-03-28 | Ryojiro Akashi | Photochromic compound |
| GB8712210D0 (en) | 1987-05-22 | 1987-06-24 | Pilkington Brothers Plc | Photochromic articles |
| US4798746A (en) | 1987-08-24 | 1989-01-17 | Ppg Industries, Inc. | Basecoat/clearcoat method of coating utilizing an anhydride additive in the thermoplastic polymer-containing basecoat for improved repairability |
| US4798745A (en) | 1987-08-24 | 1989-01-17 | Ppg Industries, Inc. | Non-yellowing coating composition based on a hydroxy component and an anhydride component and utilization in a process of coating |
| US4873029A (en) | 1987-10-30 | 1989-10-10 | Blum Ronald D | Method for manufacturing lenses |
| US4931220A (en) | 1987-11-24 | 1990-06-05 | Ppg Industries, Inc. | Organic photochromic pigment particulates |
| US5252742A (en) | 1989-02-28 | 1993-10-12 | Otsuka Kagaku Kabushiki Kaisha | Spiropyran compounds |
| US4994208A (en) | 1989-04-18 | 1991-02-19 | Ppg Industries, Inc. | Photochromic polymeric article |
| EP0420397B1 (en) | 1989-07-28 | 1995-11-29 | Wako Pure Chemical Industries Ltd | Fulgimide derivatives |
| WO1991013072A1 (fr) | 1990-02-23 | 1991-09-05 | Otsuka Kagaku Kabushiki Kaisha | Benzoselenazoline-spiro-vinylpyrane et polymere contenant un tel compose |
| US5373033A (en) | 1990-04-20 | 1994-12-13 | Sola International Holdings Limited | Casting composition |
| US5239012A (en) | 1991-02-21 | 1993-08-24 | Ppg Industries, Inc. | Ambient temperature curing compositions containing a hydroxy component and an anhydride component and an onium salt |
| US5200483A (en) | 1991-11-07 | 1993-04-06 | Ppg Industries, Inc. | Polyol(allyl carbonate) composiitons and articles prepared there from |
| BR9307220A (pt) | 1992-09-25 | 1999-05-25 | Ppg Industries Inc | Artigo ótico fotocrómico |
| US5274132A (en) | 1992-09-30 | 1993-12-28 | Transitions Optical, Inc. | Photochromic naphthopyran compounds |
| DE59304881D1 (de) | 1992-10-15 | 1997-02-06 | Ciba Geigy Ag | Polymerisierbare photochrome Napthacendione, Polymere dieser Monomeren, Verfahren zu deren Herstellung, und deren Verwendung |
| AU665480B2 (en) | 1993-01-29 | 1996-01-04 | Tokuyama Corporation | Polymerizable composition, polymer, organic glass and ophthalmic lens |
| US5618586A (en) | 1994-03-29 | 1997-04-08 | Ppg Industries, Inc. | N-alkoxymethyl (meth)acrylamide functional polymers and their use in self-crosslinkable coating compositions |
| FR2723218A1 (fr) | 1994-07-29 | 1996-02-02 | Essilor Internal Cie Gle Optique | Composes photochromiques de structure spiro (indoline-(2,3')-benzoxazine) a groupement cyano en 6', et leur utilisation dans le domaine de l'optique ophtalmique |
| US5760100B1 (en) | 1994-09-06 | 2000-11-14 | Ciba Vision Corp | Extended wear ophthalmic lens |
| US5645767A (en) | 1994-11-03 | 1997-07-08 | Transitions Optical, Inc. | Photochromic indeno-fused naphthopyrans |
| IL115803A (en) | 1994-11-03 | 2000-02-17 | Ppg Industries Inc | Indeno-naphthopyran derivatives useful for photochromic articles |
| US5658501A (en) | 1995-06-14 | 1997-08-19 | Transitions Optical, Inc. | Substituted naphthopyrans |
| AUPN443695A0 (en) | 1995-07-28 | 1995-08-17 | Sola International Holdings Ltd | Photochromic polymer |
| US5753146A (en) | 1996-03-29 | 1998-05-19 | Transitions Optical, Inc. | Photochromic naphthopyran compositions of neutral color |
| US5770115A (en) | 1996-04-19 | 1998-06-23 | Ppg Industries, Inc. | Photochromic naphthopyran compositions of improved fatigue resistance |
| US5723072A (en) | 1996-06-17 | 1998-03-03 | Ppg Industries, Inc. | Photochromic heterocyclic fused indenonaphthopyrans |
| SG54538A1 (en) | 1996-08-05 | 1998-11-16 | Hoya Corp | Soft contact lens with high moisture content and method for producing the same |
| US5821287A (en) | 1996-08-08 | 1998-10-13 | National Science Council | Photochromic pigment |
| AU718471B2 (en) | 1997-02-21 | 2000-04-13 | Ppg Industries Ohio, Inc. | Photochromic polyurethane coating and articles having such a coating |
| US6025026A (en) | 1997-06-30 | 2000-02-15 | Transitions Optical, Inc. | Process for producing an adherent polymeric layer on polymeric substrates and articles produced thereby |
| US5961631A (en) * | 1997-07-16 | 1999-10-05 | Arm Limited | Data processing apparatus and method for pre-fetching an instruction in to an instruction cache |
| US6146554A (en) | 1997-09-22 | 2000-11-14 | Optische Werke G. Rodenstock | Photochromic naphtopyrane colorants, method for the production and use thereof, photochromic object |
| US6268055B1 (en) | 1997-12-08 | 2001-07-31 | Ppg Industries Ohio, Inc. | Photochromic epoxy resin coating composition and articles having such a coating |
| US5869658A (en) * | 1997-12-15 | 1999-02-09 | Ppg Industries, Inc. | Photochromic indeno-fused naptho 2,1-b!pyrans |
| EP0987260B1 (de) | 1998-05-29 | 2004-03-03 | Rodenstock GmbH | Photochrome Spirofluorenopyrane |
| DE69903042T2 (de) | 1998-07-10 | 2003-08-07 | Transitions Optical Inc | Photochrome sechsgliedrige heterocyclisch kondensierte naphthopyrane |
| BR9913869A (pt) | 1998-09-11 | 2004-12-28 | Ppg Ind Ohio Inc | Composto naftopiranos e artigos fotocrÈnico |
| US5961892A (en) | 1998-09-11 | 1999-10-05 | Ppg Industries Ohio, Inc. | Polyalkoxylated naphthopyrans |
| US6555028B2 (en) | 1998-09-11 | 2003-04-29 | Transitions Optical, Inc. | Polymeric matrix compatibilized naphthopyrans |
| US6060001A (en) | 1998-12-14 | 2000-05-09 | Ppg Industries Ohio, Inc. | Alkoxyacrylamide photochromic coatings compositions and photochromic articles |
| US6432544B1 (en) | 1998-12-18 | 2002-08-13 | Ppg Industries Ohio, Inc. | Aminoplast resin photochromic coating composition and photochromic articles |
| US6506488B1 (en) | 1998-12-18 | 2003-01-14 | Ppg Industries Ohio, Inc. | Aminoplast resin photochromic coating composition and photochromic articles |
| US6432522B1 (en) * | 1999-02-20 | 2002-08-13 | Saint-Gobain Vitrage | Transparent acoustical and mechanical barrier |
| ES2174816T3 (es) | 1999-07-02 | 2002-11-16 | Rodenstock Optik G | Espirofluorenpiranos. |
| JP4567932B2 (ja) | 1999-07-02 | 2010-10-27 | ピーピージー・インダストリーズ・オハイオ・インコーポレイテッド | フォトクロミックポリ（メタ）アクリルコーティングを含む物品 |
| US6150430A (en) | 1999-07-06 | 2000-11-21 | Transitions Optical, Inc. | Process for adhering a photochromic coating to a polymeric substrate |
| US6348604B1 (en) | 1999-09-17 | 2002-02-19 | Ppg Industries Ohio, Inc. | Photochromic naphthopyrans |
| FR2800738B1 (fr) * | 1999-11-04 | 2002-02-08 | Corning Sa | Naphtopyranes ayant un substituant perfluoroalkyle en position 5, preparation et compositions et matrices (co)polymeres les renfermant |
| DE50009644D1 (de) * | 1999-11-10 | 2005-04-07 | Rodenstock Gmbh | Heterocyclisch annellierte indenochromenderivate |
| US6353102B1 (en) | 1999-12-17 | 2002-03-05 | Ppg Industries Ohio, Inc. | Photochromic naphthopyrans |
| JP4157245B2 (ja) | 2000-02-21 | 2008-10-01 | 株式会社トクヤマ | クロメン化合物 |
| WO2001094336A1 (de) * | 2000-06-07 | 2001-12-13 | Optische Werke G. Rodenstock | Photochrome pyranderivate |
| CN1152108C (zh) * | 2000-06-12 | 2004-06-02 | 中国科学院感光化学研究所 | 芳杂环取代的萘并吡喃类光致变色化合物及其制法和用途 |
| US20040186241A1 (en) * | 2003-03-20 | 2004-09-23 | Gemert Barry Van | Photochromic ocular devices |
| US7166357B2 (en) * | 2003-03-20 | 2007-01-23 | Transitions Optical, Inc. | Photochromic articles that activate behind ultraviolet radiation blocking transparencies and methods for preparation |
-
2003
- 2003-03-20 US US10/393,177 patent/US7262295B2/en active Active
-
2004
- 2004-03-16 JP JP2005518823A patent/JP4160980B2/ja not_active Expired - Lifetime
- 2004-03-16 CA CA 2512605 patent/CA2512605C/en not_active Expired - Lifetime
- 2004-03-16 EP EP20110001285 patent/EP2345648B1/en not_active Expired - Lifetime
- 2004-03-16 EP EP04749405.9A patent/EP1606274B9/en not_active Expired - Lifetime
- 2004-03-16 WO PCT/US2004/008156 patent/WO2005090327A1/en active IP Right Grant
- 2004-03-16 KR KR1020057017368A patent/KR100752834B1/ko active IP Right Grant
- 2004-03-16 EP EP20110001284 patent/EP2345647A3/en not_active Withdrawn
- 2004-03-16 AU AU2004311372A patent/AU2004311372B8/en not_active Expired
- 2004-03-16 BR BRPI0408540-0B1A patent/BRPI0408540B1/pt active IP Right Grant
- 2004-03-16 MX MXPA05009631A patent/MXPA05009631A/es active IP Right Grant
- 2004-03-16 ES ES11001285T patent/ES2394446T3/es not_active Expired - Lifetime
- 2004-03-16 CN CN2004800075708A patent/CN1761660B/zh not_active Expired - Lifetime
- 2004-03-16 CN CN201110376517.7A patent/CN102532088B/zh not_active Expired - Lifetime
- 2004-03-16 ES ES04749405.9T patent/ES2688272T3/es not_active Expired - Lifetime
-
2005
- 2005-10-10 ZA ZA200508177A patent/ZA200508177B/en unknown
-
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- 2006-08-25 HK HK06109470A patent/HK1089161A1/xx not_active IP Right Cessation
-
2007
- 2007-03-01 US US11/712,657 patent/US7517982B2/en not_active Expired - Lifetime
-
2008
- 2008-11-11 US US12/268,653 patent/US7557208B2/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19741705A1 (de) * | 1997-09-22 | 1999-04-01 | Rodenstock Optik G | Naphtopyrane |
| US6340765B1 (en) * | 1999-05-20 | 2002-01-22 | Tokuyama Corporation | Chromene compound |
| WO2001019813A1 (en) * | 1999-09-17 | 2001-03-22 | Transitions Optical, Inc. | Novel indeno-fused photochromic naphthopyrans |
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