DE69806367T2 - Rot färbende hyperchromische 3h-naphto(2,1-b)pyranen - Google Patents
Rot färbende hyperchromische 3h-naphto(2,1-b)pyranenInfo
- Publication number
- DE69806367T2 DE69806367T2 DE69806367T DE69806367T DE69806367T2 DE 69806367 T2 DE69806367 T2 DE 69806367T2 DE 69806367 T DE69806367 T DE 69806367T DE 69806367 T DE69806367 T DE 69806367T DE 69806367 T2 DE69806367 T2 DE 69806367T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- naphtho
- pyran
- substituent
- morpholino
- 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
- 150000004880 oxines Chemical class 0.000 title description 16
- 230000000215 hyperchromic effect Effects 0.000 title description 2
- -1 naphthopyran compound Chemical class 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- WIFWCSTVYGGLAE-UHFFFAOYSA-N 4ah-benzo[f]chromene Chemical compound C1=CC=C2C3=CC=COC3C=CC2=C1 WIFWCSTVYGGLAE-UHFFFAOYSA-N 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 238000004040 coloring Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- ATLCBJKMZQTSQT-UHFFFAOYSA-N 4-[4-(6-morpholin-4-yl-3-phenylbenzo[f]chromen-3-yl)phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2(C=CC3=C4C=CC=CC4=C(N4CCOCC4)C=C3O2)C=2C=CC=CC=2)C=C1 ATLCBJKMZQTSQT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- RYAYXLSKRVENJL-UHFFFAOYSA-N 4-[3-phenyl-3-(4-piperidin-1-ylphenyl)benzo[f]chromen-6-yl]morpholine Chemical compound C1CCCCN1C1=CC=C(C2(C=CC3=C4C=CC=CC4=C(N4CCOCC4)C=C3O2)C=2C=CC=CC=2)C=C1 RYAYXLSKRVENJL-UHFFFAOYSA-N 0.000 claims description 2
- UJNPGNLVOVBKKM-UHFFFAOYSA-N 4-[3-phenyl-3-(4-pyrrolidin-1-ylphenyl)benzo[f]chromen-6-yl]morpholine Chemical compound C1CCCN1C1=CC=C(C2(C=CC3=C4C=CC=CC4=C(N4CCOCC4)C=C3O2)C=2C=CC=CC=2)C=C1 UJNPGNLVOVBKKM-UHFFFAOYSA-N 0.000 claims description 2
- UQLRXKPUGYIEDG-UHFFFAOYSA-N 4-[4-(3-phenylbenzo[f]chromen-3-yl)phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2(C=CC3=C4C=CC=CC4=CC=C3O2)C=2C=CC=CC=2)C=C1 UQLRXKPUGYIEDG-UHFFFAOYSA-N 0.000 claims description 2
- 229920008347 Cellulose acetate propionate Polymers 0.000 claims description 2
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 2
- 239000004793 Polystyrene Substances 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
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 229920002301 cellulose acetate Polymers 0.000 claims description 2
- 229920006217 cellulose acetate butyrate Polymers 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 2
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 2
- 239000011118 polyvinyl acetate Substances 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- VMLLJHJOSUOYCU-UHFFFAOYSA-N 4-[3-(4-morpholin-4-ylphenyl)-3-[4-(trifluoromethyl)phenyl]benzo[f]chromen-6-yl]morpholine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(C=2C=CC(=CC=2)N2CCOCC2)C=CC2=C3C=CC=CC3=C(N3CCOCC3)C=C2O1 VMLLJHJOSUOYCU-UHFFFAOYSA-N 0.000 claims 1
- FXXHWDQPGSXESH-UHFFFAOYSA-N 4-[3-(4-morpholin-4-ylphenyl)-3-thiophen-2-ylbenzo[f]chromen-6-yl]morpholine Chemical compound C1COCCN1C1=CC=C(C2(C=CC3=C4C=CC=CC4=C(N4CCOCC4)C=C3O2)C=2SC=CC=2)C=C1 FXXHWDQPGSXESH-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 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 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- VCMLCMCXCRBSQO-UHFFFAOYSA-N 3h-benzo[f]chromene Chemical compound C1=CC=CC2=C(C=CCO3)C3=CC=C21 VCMLCMCXCRBSQO-UHFFFAOYSA-N 0.000 description 5
- IPHLOJFBRZIUGM-UHFFFAOYSA-N 4-morpholin-4-ylnaphthalen-2-ol Chemical compound C=12C=CC=CC2=CC(O)=CC=1N1CCOCC1 IPHLOJFBRZIUGM-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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 1
- SMCLTAARQYTXLW-UHFFFAOYSA-N 1,1-diphenylprop-2-yn-1-ol Chemical compound C=1C=CC=CC=1C(C#C)(O)C1=CC=CC=C1 SMCLTAARQYTXLW-UHFFFAOYSA-N 0.000 description 1
- PEANAJOQMCAPBH-UHFFFAOYSA-N 1-(4-methoxyphenyl)-1-(4-piperidin-1-ylphenyl)prop-2-yn-1-ol Chemical compound C1=CC(OC)=CC=C1C(O)(C#C)C1=CC=C(N2CCCCC2)C=C1 PEANAJOQMCAPBH-UHFFFAOYSA-N 0.000 description 1
- AIBIEAJBGHJQJF-UHFFFAOYSA-N 1-phenyl-1-(4-piperidin-1-ylphenyl)prop-2-yn-1-ol Chemical compound C=1C=C(N2CCCCC2)C=CC=1C(C#C)(O)C1=CC=CC=C1 AIBIEAJBGHJQJF-UHFFFAOYSA-N 0.000 description 1
- YTQSPEFEDIMSGT-UHFFFAOYSA-N 1-phenyl-1-(4-pyrrolidin-1-ylphenyl)prop-2-yn-1-ol Chemical compound C=1C=C(N2CCCC2)C=CC=1C(C#C)(O)C1=CC=CC=C1 YTQSPEFEDIMSGT-UHFFFAOYSA-N 0.000 description 1
- 150000004786 2-naphthols Chemical class 0.000 description 1
- UBNNJVRNPJVYBU-UHFFFAOYSA-N 3,3-diphenylbenzo[f]chromene Chemical compound O1C2=CC=C3C=CC=CC3=C2C=CC1(C=1C=CC=CC=1)C1=CC=CC=C1 UBNNJVRNPJVYBU-UHFFFAOYSA-N 0.000 description 1
- JPUIWORCIIRWJP-UHFFFAOYSA-N 4-[3,3-bis(4-methoxyphenyl)benzo[f]chromen-6-yl]morpholine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=CC(OC)=CC=2)C=CC2=C3C=CC=CC3=C(N3CCOCC3)C=C2O1 JPUIWORCIIRWJP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000005001 aminoaryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07D405/10—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 linked by a carbon chain containing aromatic 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9706939.7A GB9706939D0 (en) | 1997-04-04 | 1997-04-04 | Red colouring hyperchromic 3H-naptho[2,1-6]pyrans |
| PCT/GB1998/000995 WO1998045281A1 (en) | 1997-04-04 | 1998-04-03 | RED COLOURING HYPERCHROMIC 3H-NAPHTHO[2,1-b]PYRANS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69806367D1 DE69806367D1 (de) | 2002-08-08 |
| DE69806367T2 true DE69806367T2 (de) | 2003-04-03 |
Family
ID=10810343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69806367T Expired - Lifetime DE69806367T2 (de) | 1997-04-04 | 1998-04-03 | Rot färbende hyperchromische 3h-naphto(2,1-b)pyranen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6294112B1 (https=) |
| EP (1) | EP0973761B1 (https=) |
| JP (1) | JP4324661B2 (https=) |
| DE (1) | DE69806367T2 (https=) |
| DK (1) | DK0973761T3 (https=) |
| ES (1) | ES2179480T3 (https=) |
| GB (2) | GB9706939D0 (https=) |
| WO (1) | WO1998045281A1 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9726361D0 (en) * | 1997-12-12 | 1998-02-11 | James Robinson Ltd | Photochromic dyes |
| EP0945451B1 (de) * | 1998-03-25 | 2002-12-18 | Optische Werke G. Rodenstock | Photochrome Diaryl-Naphthopyrane mit zumindest einem aminosubstituierten Arylrest |
| US6478988B1 (en) | 1998-12-31 | 2002-11-12 | Bmc Vision-Ease Lens, Inc. | Photochromic substituted naphthopyran compounds |
| DE60021345T2 (de) * | 1999-06-03 | 2006-04-27 | Tokuyama Corp., Shunan | Chromenverbindungen |
| US6719926B2 (en) * | 1999-06-03 | 2004-04-13 | Tokuyama Corporation | Chromene compound |
| FR2796077B1 (fr) * | 1999-07-08 | 2001-10-05 | Essilor Int | Composes photochromiques naphto (2,1-b) pyranes a substitutions bi ou terthienyle, leur procede de fabrication, materiaux et articles photochromiques obtenus |
| GB9918951D0 (en) * | 1999-08-11 | 1999-10-13 | James Robinson Ltd | Rapid fading photo-responsive materials |
| US6340766B1 (en) * | 2000-01-12 | 2002-01-22 | Transition Optical, Inc. | Substituted napthopyrans |
| AU2002361203A1 (en) | 2002-01-03 | 2003-07-15 | Rodenstock Gmbh | 3h-naphtho(2,1-b)-pyrane derivatives and the use of the same |
| JP4325939B2 (ja) | 2002-05-22 | 2009-09-02 | 株式会社トクヤマ | フォトクロミック性組成物 |
| US20040228818A1 (en) * | 2002-10-18 | 2004-11-18 | L'oreal | Cosmetic composition combining at least two dyes including at least one photochromic dye |
| US20040228817A1 (en) * | 2002-10-18 | 2004-11-18 | L'oreal | Makeup combining at least one photochromic dye and at least one goniochromatic agent |
| US20050276767A1 (en) * | 2002-10-18 | 2005-12-15 | L'oreal | Composition containing an oily phase and a naphthopyran dye, cosmetic treatment processes |
| ES2280711T3 (es) * | 2002-10-18 | 2007-09-16 | L'oreal | Producto de maquillaje que asocia dos composiciones a base respectivamente de una materia colorante fotocromatica y de un agente goniocromatico. |
| EP1410786B1 (fr) * | 2002-10-18 | 2008-01-02 | L'oreal | Composition cosmétique associant au moins deux matières colorantes dont au moins une matière colorante photochrome |
| DE60311622T2 (de) * | 2002-10-18 | 2007-10-25 | L'oreal | Kosmetische Zusammensetzung enthaltend eine Ölphase und einen Farbstoff aus der Gruppe der Naphthopyrane sowie Methode |
| US8698117B2 (en) | 2003-07-01 | 2014-04-15 | Transitions Optical, Inc. | Indeno-fused ring compounds |
| US8518546B2 (en) | 2003-07-01 | 2013-08-27 | Transitions Optical, Inc. | Photochromic compounds and compositions |
| US8545984B2 (en) | 2003-07-01 | 2013-10-01 | Transitions Optical, Inc. | Photochromic compounds and compositions |
| US8211338B2 (en) | 2003-07-01 | 2012-07-03 | Transitions Optical, Inc | Photochromic compounds |
| WO2005035529A1 (de) | 2003-09-18 | 2005-04-21 | Rodenstock Gmbh | Substituierte phenanthropyrane |
| KR100649959B1 (ko) | 2005-08-30 | 2006-11-27 | 한국화학연구원 | 나프토피란계 광변색 염료의 제조방법 |
| JP2007091595A (ja) * | 2005-09-27 | 2007-04-12 | Tokuyama Corp | ナフトピラン化合物の製造方法 |
| EP2481771B1 (de) | 2011-01-26 | 2017-05-03 | THÜRINGISCHES INSTITUT FÜR TEXTIL- UND KUNSTSTOFF-FORSCHUNG e.V. | Polymerzusammensetzung und Verfahren zur Herstellung von Produkten mit variabler biologischer Abbaubarkeit |
| US12577454B2 (en) | 2021-11-24 | 2026-03-17 | Nano And Advanced Materials Institute Limited | Photochromic compositions |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8614680D0 (en) | 1986-06-17 | 1986-07-23 | Plessey Co Plc | Photoreactive lenses |
| GB9306587D0 (en) * | 1993-03-30 | 1993-05-26 | Pilkington Plc | Photochromic compounds |
| US5384077A (en) | 1993-06-21 | 1995-01-24 | Transitions Optical, Inc. | Photochromic naphthopyran compounds |
| US5466398A (en) * | 1993-06-21 | 1995-11-14 | Transitions Optical, Inc. | Photochromic substituted naphthopyran compounds |
| US5552090A (en) * | 1993-06-21 | 1996-09-03 | Ppg Industries, Inc. | Photochromic naphthopyran compounds |
| JPH09124645A (ja) * | 1995-11-02 | 1997-05-13 | Tokuyama Corp | クロメン化合物 |
| AU710875B2 (en) * | 1995-12-06 | 1999-09-30 | Tokuyama Corporation | Chromene compounds and photochromic materials |
| JP3982770B2 (ja) * | 1997-04-30 | 2007-09-26 | 株式会社トクヤマ | クロメン化合物 |
| US5879592A (en) * | 1997-12-10 | 1999-03-09 | Ppg Industries, Inc. | Water soluble photochromic compounds, compositions and optical elements comprising the compounds |
| GB9726361D0 (en) * | 1997-12-12 | 1998-02-11 | James Robinson Ltd | Photochromic dyes |
| EP0945451B1 (de) * | 1998-03-25 | 2002-12-18 | Optische Werke G. Rodenstock | Photochrome Diaryl-Naphthopyrane mit zumindest einem aminosubstituierten Arylrest |
-
1997
- 1997-04-04 GB GBGB9706939.7A patent/GB9706939D0/en active Pending
-
1998
- 1998-04-03 DE DE69806367T patent/DE69806367T2/de not_active Expired - Lifetime
- 1998-04-03 JP JP54249498A patent/JP4324661B2/ja not_active Expired - Fee Related
- 1998-04-03 GB GB9922328A patent/GB2338233B/en not_active Expired - Lifetime
- 1998-04-03 EP EP98914972A patent/EP0973761B1/en not_active Expired - Lifetime
- 1998-04-03 US US09/402,355 patent/US6294112B1/en not_active Expired - Fee Related
- 1998-04-03 DK DK98914972T patent/DK0973761T3/da active
- 1998-04-03 ES ES98914972T patent/ES2179480T3/es not_active Expired - Lifetime
- 1998-04-03 WO PCT/GB1998/000995 patent/WO1998045281A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001518893A (ja) | 2001-10-16 |
| EP0973761B1 (en) | 2002-07-03 |
| DE69806367D1 (de) | 2002-08-08 |
| US6294112B1 (en) | 2001-09-25 |
| DK0973761T3 (da) | 2002-07-22 |
| WO1998045281A1 (en) | 1998-10-15 |
| GB9922328D0 (en) | 1999-11-17 |
| GB9706939D0 (en) | 1997-05-21 |
| GB2338233A (en) | 1999-12-15 |
| EP0973761A1 (en) | 2000-01-26 |
| GB2338233B (en) | 2001-09-05 |
| ES2179480T3 (es) | 2003-01-16 |
| JP4324661B2 (ja) | 2009-09-02 |
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