DE69905739T2 - Naphthopyrane die in c5-c6 anneliert sind, ihre herstellung sowie sie enthaltende zubereitungen und (co)polymermatrizen - Google Patents
Naphthopyrane die in c5-c6 anneliert sind, ihre herstellung sowie sie enthaltende zubereitungen und (co)polymermatrizenInfo
- Publication number
- DE69905739T2 DE69905739T2 DE69905739T DE69905739T DE69905739T2 DE 69905739 T2 DE69905739 T2 DE 69905739T2 DE 69905739 T DE69905739 T DE 69905739T DE 69905739 T DE69905739 T DE 69905739T DE 69905739 T2 DE69905739 T2 DE 69905739T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- carbon atoms
- formula
- linear
- aryl
- 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.)
- Expired - Lifetime
Links
- 229920001577 copolymer Polymers 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 119
- 125000004432 carbon atom Chemical group C* 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- -1 naphthoxy group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Chemical group 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 239000011159 matrix material Substances 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000001301 oxygen Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 239000005864 Sulphur Substances 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- VCMLCMCXCRBSQO-UHFFFAOYSA-N 3h-benzo[f]chromene Chemical group C1=CC=CC2=C(C=CCO3)C3=CC=C21 VCMLCMCXCRBSQO-UHFFFAOYSA-N 0.000 claims description 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003086 colorant Substances 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 238000004132 cross linking Methods 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 4
- 229920000515 polycarbonate Polymers 0.000 claims description 4
- 239000004417 polycarbonate Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical class OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229920008347 Cellulose acetate propionate Polymers 0.000 claims description 2
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229920002396 Polyurea Polymers 0.000 claims description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 229920002301 cellulose acetate Polymers 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 238000007255 decyanation reaction Methods 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920002578 polythiourethane polymer Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- RFNDMLXNYMQMGN-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol Chemical compound C1=CC(OC)=CC=C1C(O)(C#C)C1=CC=C(OC)C=C1 RFNDMLXNYMQMGN-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000002576 ketones Chemical group 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- SNWQUNCRDLUDEX-UHFFFAOYSA-N inden-1-one Chemical group C1=CC=C2C(=O)C=CC2=C1 SNWQUNCRDLUDEX-UHFFFAOYSA-N 0.000 description 3
- 150000004780 naphthols Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- ZDIUWPRARMWVMG-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-1-phenylprop-2-yn-1-ol Chemical compound C1=CC(N(C)C)=CC=C1C(O)(C#C)C1=CC=CC=C1 ZDIUWPRARMWVMG-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- AETOCTWURFLYKR-UHFFFAOYSA-N 2-naphthalen-1-ylcyclohexan-1-one Chemical class O=C1CCCCC1C1=CC=CC2=CC=CC=C12 AETOCTWURFLYKR-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- MFMVRILBADIIJO-UHFFFAOYSA-N benzo[e][1]benzofuran Chemical group C1=CC=C2C(C=CO3)=C3C=CC2=C1 MFMVRILBADIIJO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QYFQIRGYFJJVNQ-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)-1-phenylprop-2-yn-1-ol Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(C#C)(O)C1=CC=CC=C1 QYFQIRGYFJJVNQ-UHFFFAOYSA-N 0.000 description 1
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
- QKXUIBZLBWCUNU-UHFFFAOYSA-N 1-hydroxynaphthalene-2-carbonitrile Chemical compound C1=CC=C2C(O)=C(C#N)C=CC2=C1 QKXUIBZLBWCUNU-UHFFFAOYSA-N 0.000 description 1
- GTBXZWADMKOZQJ-UHFFFAOYSA-N 1-phenanthrol Chemical compound C1=CC2=CC=CC=C2C2=C1C(O)=CC=C2 GTBXZWADMKOZQJ-UHFFFAOYSA-N 0.000 description 1
- UFRXMQMDSOZSQC-UHFFFAOYSA-N 1-phenyl-1-thiophen-2-ylprop-2-yn-1-ol Chemical compound C=1C=CC=CC=1C(C#C)(O)C1=CC=CS1 UFRXMQMDSOZSQC-UHFFFAOYSA-N 0.000 description 1
- PTRLOLYOFGOMOM-UHFFFAOYSA-N 1-phenyl-3,4-dihydro-1h-naphthalen-2-one Chemical compound O=C1CCC2=CC=CC=C2C1C1=CC=CC=C1 PTRLOLYOFGOMOM-UHFFFAOYSA-N 0.000 description 1
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
- AQMADBTVRPWMEG-UHFFFAOYSA-N 2-naphthalen-1-ylcyclopentan-1-one Chemical compound O=C1CCCC1C1=CC=CC2=CC=CC=C12 AQMADBTVRPWMEG-UHFFFAOYSA-N 0.000 description 1
- BIXBNZDQRGVVJE-UHFFFAOYSA-N 2h-naphtho[2,1-f]chromene Chemical group C1=CC=C2C3=CC=C4OCC=CC4=C3C=CC2=C1 BIXBNZDQRGVVJE-UHFFFAOYSA-N 0.000 description 1
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical group C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 1
- VOSRGDRDAOZSQU-UHFFFAOYSA-N 7-methoxy-4-(4-methoxyphenyl)-1,2-dihydronaphthalene Chemical class C1=CC(OC)=CC=C1C1=CCCC2=CC(OC)=CC=C12 VOSRGDRDAOZSQU-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- XUHWJLMOAFPKEV-UHFFFAOYSA-N Sepiol Natural products OC1=C(O)C(OC)=CC=C1C1=CC2=CC=C(O)C=C2OC1 XUHWJLMOAFPKEV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- JMSRBKPMLUGHCR-UHFFFAOYSA-N bromohydrin Chemical compound BrC[C]1CO1 JMSRBKPMLUGHCR-UHFFFAOYSA-N 0.000 description 1
- 150000008371 chromenes Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000003137 locomotive effect Effects 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- VGKONPUVOVVNSU-UHFFFAOYSA-N naphthalen-1-yl acetate Chemical compound C1=CC=C2C(OC(=O)C)=CC=CC2=C1 VGKONPUVOVVNSU-UHFFFAOYSA-N 0.000 description 1
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
- C07D311/94—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 condensed with rings other than six-membered or with ring systems containing such rings
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/02—Coumarine dyes
-
- 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
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/146—Laser beam
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Eyeglasses (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Optical Filters (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9811519A FR2783248A1 (fr) | 1998-09-11 | 1998-09-11 | Naphtopyranes anneles en c5-c6, leur preparation, et les compositions et matrices (co)polymeres les renfermant |
| FR9900162A FR2783249B1 (fr) | 1998-09-11 | 1999-01-06 | Naphtopyranes anneles en c5-c6, leur preparation et les compositions et matrices (co)polymeres les renfermant |
| PCT/US1999/020471 WO2000015628A1 (en) | 1998-09-11 | 1999-09-07 | Naphthopyrans annelated in c5-c6, their preparation and compositions and (co) polymer matrices containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69905739D1 DE69905739D1 (de) | 2003-04-10 |
| DE69905739T2 true DE69905739T2 (de) | 2003-12-24 |
Family
ID=26234545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69905739T Expired - Lifetime DE69905739T2 (de) | 1998-09-11 | 1999-09-07 | Naphthopyrane die in c5-c6 anneliert sind, ihre herstellung sowie sie enthaltende zubereitungen und (co)polymermatrizen |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6506538B1 (https=) |
| EP (1) | EP1119560B1 (https=) |
| JP (2) | JP4737830B2 (https=) |
| CN (1) | CN1315948A (https=) |
| AR (1) | AR021799A1 (https=) |
| AT (1) | ATE233749T1 (https=) |
| AU (1) | AU747191B2 (https=) |
| BR (1) | BR9912649A (https=) |
| CA (1) | CA2342338A1 (https=) |
| DE (1) | DE69905739T2 (https=) |
| ES (1) | ES2195659T3 (https=) |
| FR (1) | FR2783249B1 (https=) |
| WO (1) | WO2000015628A1 (https=) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2783249B1 (fr) * | 1998-09-11 | 2001-06-22 | Flamel Tech Sa | Naphtopyranes anneles en c5-c6, leur preparation et les compositions et matrices (co)polymeres les renfermant |
| US6686468B2 (en) * | 2000-09-14 | 2004-02-03 | Optische Werke G. Rodenstock | H-annellated benzo[f]chromenes |
| FR2815034B1 (fr) * | 2000-10-11 | 2003-02-07 | Corning Sa | Naphtopyranes anneles en c5-c6 par un carbocycle de type dihydrobenzocycloheptatriene et les compositions et matrices les refermant |
| US6736998B2 (en) * | 2000-12-29 | 2004-05-18 | Transitions Optical, Inc. | Indeno-fused photochromic naphthopyrans |
| US7048876B2 (en) * | 2001-05-02 | 2006-05-23 | Tokuyama Corporation | Chromene compound |
| US6608215B2 (en) | 2001-09-20 | 2003-08-19 | Vision-Ease Lens, Inc. | Oxygen-containing heterocyclic fused naphthopyrans |
| TW200302828A (en) * | 2001-11-16 | 2003-08-16 | Tokuyama Corp | Chromene compound |
| AU2003286709B8 (en) * | 2002-10-28 | 2009-11-19 | Insight Equity A.P.X., Lp | Oxygen-containing heterocyclic fused naphthopyrans |
| FR2854631B1 (fr) * | 2003-05-05 | 2007-12-21 | Corning Inc | Benzo-, naphto- et phenantrochromenes substitues en position 2 par un groupe arylamine et les compositions les renfermant |
| JP2007505842A (ja) | 2003-09-18 | 2007-03-15 | ローデンストック．ゲゼルシャフト．ミット．ベシュレンクテル．ハフツング | 置換されたフェナントロピラン |
| ES2326215T3 (es) * | 2003-11-05 | 2009-10-05 | Corning Incorporated | Piranos condensados fotocromicos sustituidos con fenilo que porta un grupo carbamilo o urea. |
| WO2005047277A1 (en) * | 2003-11-05 | 2005-05-26 | Corning Incorporated | Photochromic fused pyrans substituted with phenyl carrying a carbamyl or urea group |
| TW200530373A (en) * | 2003-12-12 | 2005-09-16 | Sumitomo Chemical Co | Polymer and light-emitting element using said polymer |
| EP1945625B1 (de) * | 2005-11-10 | 2010-03-03 | Rodenstock GmbH | Photochrome spirodihydrophenanthropyrane |
| KR20080091349A (ko) | 2006-01-25 | 2008-10-10 | 가부시끼가이샤 도꾸야마 | 크로멘 화합물 |
| JP2008074832A (ja) | 2006-08-24 | 2008-04-03 | Tokuyama Corp | クロメン化合物 |
| JP2009014689A (ja) * | 2007-07-09 | 2009-01-22 | Saitama Univ | フォトクロミック化合物を利用した紫外線強度測定装置 |
| US20090122261A1 (en) * | 2007-11-09 | 2009-05-14 | Insight Equity A.P.X., L.P. | Reflective Polarized Lenses With High Transmission |
| WO2009068247A1 (de) * | 2007-11-26 | 2009-06-04 | Rodenstock Gmbh | Photochrome benzopyrane |
| DE102008060096A1 (de) | 2007-12-20 | 2009-06-25 | Rodenstock Gmbh | Photochrome Spirobenzopyranobenzopyrane |
| WO2009132842A1 (de) | 2008-04-30 | 2009-11-05 | Rodenstock Gmbh | Photochrome naphthopyrane mit doppelt verbrückter terphenyl-untereinheit |
| US8217188B2 (en) * | 2008-08-27 | 2012-07-10 | Corning Incorporated | 2H-chromenes annelated at C5-C6 and methods of making and using thereof |
| DE102009058906A1 (de) | 2008-12-18 | 2010-06-24 | Rodenstock Gmbh | Photochrome Naphthopyrane mit Verbrückung zweier aromatischer Teilsysteme |
| US7829745B1 (en) | 2009-08-18 | 2010-11-09 | Corning Incorporated | Methods for selectively synthesizing 1-aryl-2-tetralones |
| US8188181B2 (en) * | 2009-09-22 | 2012-05-29 | Corning Incorporated | Photochromic compositions, resins and articles obtained therefrom |
| WO2013045086A1 (de) | 2011-09-26 | 2013-04-04 | Rodenstock Gmbh | Photochrome zweifach-annellierte naphthopyrane |
| ES2563502T3 (es) | 2011-12-09 | 2016-03-15 | Rodenstock Gmbh | Naftopiranos fotocromáticos doblemente indenoanillados |
| KR101610574B1 (ko) | 2012-06-26 | 2016-04-07 | 미쓰이 가가쿠 가부시키가이샤 | 광학재료용 중합성 조성물, 해당 조성물로부터 얻어지는 광학재료 및 플라스틱렌즈 |
| ES2578007T3 (es) | 2012-07-12 | 2016-07-20 | Rodenstock Gmbh | Fluorenopiranos fotocrómicos con anillación Dibenzo[b,d]-pirano |
| CN102976911A (zh) * | 2012-07-16 | 2013-03-20 | 上海甘田光学材料有限公司 | 萘酚酮衍生物及其制备方法和应用 |
| US9529118B2 (en) | 2012-11-30 | 2016-12-27 | Mitsui Chemicals, Inc. | Composition for optical material and use of same |
| JP6328751B2 (ja) * | 2013-06-17 | 2018-05-23 | ローデンシュトック ゲーエムベーハー | Ｕｖ硬化適合性フォトクロミック縮合ナフトピラン |
| KR101776540B1 (ko) | 2013-08-02 | 2017-09-07 | 미쯔이가가꾸가부시끼가이샤 | 포토크로믹 광학 재료의 제조 방법 |
| KR101821078B1 (ko) | 2014-02-03 | 2018-01-22 | 미쯔이가가꾸가부시끼가이샤 | 광학 재료용 중합성 조성물, 당해 조성물로부터 얻어지는 광학 재료 및 플라스틱 렌즈 |
| WO2017047745A1 (ja) | 2015-09-16 | 2017-03-23 | 三井化学株式会社 | 光学材料用重合性組成物、該組成物から得られる光学材料およびプラスチックレンズ |
| EP3351573B1 (en) * | 2015-09-16 | 2020-06-17 | Mitsui Chemicals, Inc. | Molded body and polymerizable composition for optical materials |
| US10921489B2 (en) | 2015-09-16 | 2021-02-16 | Mitsui Chemicals, Inc. | Polymerizable composition for optical material, optical material obtained from the composition, and plastic lens |
| JP6949946B2 (ja) | 2016-09-26 | 2021-10-13 | ローデンシュトック ゲーエムベーハー | 可視波長帯に向けて遠くから伸びる超長波長吸収を有する、フォトクロミック多環縮合ナフトピラン |
| MX2019003634A (es) | 2016-09-30 | 2019-06-17 | Mitsui Chemicals Inc | Composicion polimerizable para material optico y producto moldeado. |
| EP3650480A4 (en) | 2017-07-03 | 2021-03-24 | Mitsui Chemicals, Inc. | POLYMERIZABLE COMPOSITION FOR OPTICAL MATERIALS AND SHAPED BODIES |
| JP7123082B2 (ja) | 2018-02-09 | 2022-08-22 | 三井化学株式会社 | レンズおよびレンズの製造方法 |
| DE102018004790A1 (de) | 2018-06-14 | 2019-12-19 | Rodenstock Gmbh | Photochrome annellierte Naphthopyran-Systeme mit speziellen Substituenten zur Realisierung sehr schneller Aufhellgeschwindigkeiten |
| CN113135883B (zh) * | 2021-04-16 | 2023-04-07 | 天津孚信阳光科技有限公司 | 䓛并[1,2,f]吡喃光致变色化合物及其制备方法和应用 |
| EP4240797B1 (de) * | 2022-01-17 | 2024-08-28 | Rodenstock GmbH | Kombination spezifischer annellierter naphthopyran-isomere |
| DE102023109737A1 (de) | 2023-04-18 | 2024-10-24 | Rodenstock Gmbh | Höhermolekulare photochrome Farbstoffe mit mindestens einer und höchstens vier Naphthopyran-Untereinheiten sowie mehreren Polyether-Ketten |
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| US5066818A (en) * | 1990-03-07 | 1991-11-19 | Ppg Industries, Inc. | Photochromic naphthopyran compounds |
| US5384077A (en) * | 1993-06-21 | 1995-01-24 | Transitions Optical, Inc. | Photochromic naphthopyran compounds |
| US5451344A (en) | 1994-04-08 | 1995-09-19 | Transitions Optical, Inc. | Photochromic naphthopyran compounds |
| US5514817A (en) | 1994-08-04 | 1996-05-07 | Ppg Industries, Inc. | Substituted phenanthropyrans |
| IL115803A (en) * | 1994-11-03 | 2000-02-17 | Ppg Industries Inc | Indeno-naphthopyran derivatives useful for photochromic articles |
| US5645767A (en) | 1994-11-03 | 1997-07-08 | Transitions Optical, Inc. | Photochromic indeno-fused naphthopyrans |
| US5723072A (en) * | 1996-06-17 | 1998-03-03 | Ppg Industries, Inc. | Photochromic heterocyclic fused indenonaphthopyrans |
| US5955520A (en) | 1996-06-17 | 1999-09-21 | Ppg Industries, Inc. | Photochromic indeno-fused naphthopyrans |
| US5698141A (en) * | 1996-06-17 | 1997-12-16 | Ppg Industries, Inc. | Photochromic heterocyclic fused indenonaphthopyrans |
| CN1220734A (zh) * | 1996-07-25 | 1999-06-23 | 康宁股份有限公司 | 萘并吡喃、包含萘并吡喃的组合物和制品 |
| DE19741705A1 (de) | 1997-09-22 | 1999-04-01 | Rodenstock Optik G | Naphtopyrane |
| WO1999015518A1 (de) | 1997-09-22 | 1999-04-01 | Optische Werke G. Rodenstock | Photochrome naphthopyran-farbstoffe, verfahren zu ihrer herstellung, ihre verwendung sowie ein photochromer gegenstand |
| US5783116A (en) * | 1997-10-16 | 1998-07-21 | Ppg Industries, Inc. | Derivatives of carbocyclic fused naphthopyrans |
| US5869658A (en) | 1997-12-15 | 1999-02-09 | Ppg Industries, Inc. | Photochromic indeno-fused naptho 2,1-b!pyrans |
| WO1999067234A1 (de) * | 1998-06-19 | 1999-12-29 | Optische Werke G. Rodenstock | Photochrome naphthopyrane |
| US6022497A (en) | 1998-07-10 | 2000-02-08 | Ppg Industries Ohio, Inc. | Photochromic six-membered heterocyclic-fused naphthopyrans |
| US6022495A (en) | 1998-07-10 | 2000-02-08 | Transitions Optical, Inc. | Photochromic benzopyrano-fused naphthopyrans |
| FR2783249B1 (fr) * | 1998-09-11 | 2001-06-22 | Flamel Tech Sa | Naphtopyranes anneles en c5-c6, leur preparation et les compositions et matrices (co)polymeres les renfermant |
| US5961892A (en) | 1998-09-11 | 1999-10-05 | Ppg Industries Ohio, Inc. | Polyalkoxylated naphthopyrans |
| FR2789680B1 (fr) * | 1999-02-17 | 2002-05-17 | Corning Sa | Naphtopyranes et phenanthropyranes anneles en c5-c6 avec un groupe bicyclique et les compositions et matrices (co)polymeres les renfermant |
| US6296785B1 (en) * | 1999-09-17 | 2001-10-02 | Ppg Industries Ohio, Inc. | Indeno-fused photochromic naphthopyrans |
| FR2800739B1 (fr) * | 1999-11-04 | 2002-10-11 | Corning Sa | Naphtopyranes avec un heterocycle en position 5,6, preparation et compositions et matrices (co) polymeres les renfermant |
| FR2801052B1 (fr) * | 1999-11-17 | 2004-04-02 | Corning Sa | Naphtopyranes anneles en c5-c6 par un carbocycle de type indene ou dihydronaphtalene et les compositions et matrices (co) polymeres les renfermant |
| FR2815034B1 (fr) * | 2000-10-11 | 2003-02-07 | Corning Sa | Naphtopyranes anneles en c5-c6 par un carbocycle de type dihydrobenzocycloheptatriene et les compositions et matrices les refermant |
| ES2326215T3 (es) * | 2003-11-05 | 2009-10-05 | Corning Incorporated | Piranos condensados fotocromicos sustituidos con fenilo que porta un grupo carbamilo o urea. |
-
1999
- 1999-01-06 FR FR9900162A patent/FR2783249B1/fr not_active Expired - Fee Related
- 1999-09-07 CN CN99810262.8A patent/CN1315948A/zh active Pending
- 1999-09-07 BR BR9912649-4A patent/BR9912649A/pt not_active IP Right Cessation
- 1999-09-07 AT AT99969091T patent/ATE233749T1/de not_active IP Right Cessation
- 1999-09-07 WO PCT/US1999/020471 patent/WO2000015628A1/en not_active Ceased
- 1999-09-07 JP JP2000570167A patent/JP4737830B2/ja not_active Expired - Lifetime
- 1999-09-07 DE DE69905739T patent/DE69905739T2/de not_active Expired - Lifetime
- 1999-09-07 CA CA002342338A patent/CA2342338A1/en not_active Abandoned
- 1999-09-07 AU AU60284/99A patent/AU747191B2/en not_active Ceased
- 1999-09-07 ES ES99969091T patent/ES2195659T3/es not_active Expired - Lifetime
- 1999-09-07 EP EP99969091A patent/EP1119560B1/en not_active Expired - Lifetime
- 1999-09-09 US US09/393,213 patent/US6506538B1/en not_active Expired - Lifetime
- 1999-09-10 AR ARP990104548A patent/AR021799A1/es unknown
-
2002
- 2002-07-16 US US10/196,114 patent/US7332260B2/en not_active Expired - Lifetime
-
2011
- 2011-02-14 JP JP2011028893A patent/JP5325243B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20020197562A1 (en) | 2002-12-26 |
| JP2004500319A (ja) | 2004-01-08 |
| BR9912649A (pt) | 2001-11-27 |
| DE69905739D1 (de) | 2003-04-10 |
| JP5325243B2 (ja) | 2013-10-23 |
| AU747191B2 (en) | 2002-05-09 |
| JP4737830B2 (ja) | 2011-08-03 |
| AU6028499A (en) | 2000-04-03 |
| ATE233749T1 (de) | 2003-03-15 |
| ES2195659T3 (es) | 2003-12-01 |
| FR2783249B1 (fr) | 2001-06-22 |
| CN1315948A (zh) | 2001-10-03 |
| US6506538B1 (en) | 2003-01-14 |
| CA2342338A1 (en) | 2000-03-23 |
| US7332260B2 (en) | 2008-02-19 |
| EP1119560A1 (en) | 2001-08-01 |
| EP1119560B1 (en) | 2003-03-05 |
| AR021799A1 (es) | 2002-08-07 |
| FR2783249A1 (fr) | 2000-03-17 |
| WO2000015628A1 (en) | 2000-03-23 |
| JP2011144181A (ja) | 2011-07-28 |
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