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US 5,466,398 AGranted
Photochromic substituted naphthopyran compounds
AssigneeTransitions Optical, Inc.
InventorsBarry Van Gemert, Anil Kumar
Life of this patent
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Abstract
Described are novel reversible photochromic 3H-naphtho[2,1-b]pyran compounds, of the following graphic formula: ##STR1## wherein R.sub.1 is hydrogen or alkyl, R.sub.2 is hydrogen or preferably a carboalkoxy group and R.sub.3 is hydrogen or preferably an alkyl group, provided that either R.sub.1 or R.sub.2 is hydrogen, and B and B' are the aryl groups phenyl or naphthyl, a heterocyclic aromatic group or together form a spiro adamantylene group. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(oxazine) type compounds, are also described.
Claims22
A naphthopyran compound represented by the following graphic formula:
- ##STR10## wherein:
- (a) R1 is hydrogen or a C.sub.1 -C.sub.6 alkyl;
- R.sub.2 is hydrogen or the group, -C(O)W, W being -OR.sub.4 or -N(R.sub.5)R.sub.6, wherein R.sub.4 is hydrogen, allyl, C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 monoalkyl substituted phenyl, C.sub.1 -C.sub.6 monoalkoxy substituted phenyl, phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkoxy substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.2 -C.sub.4)alkyl, or C.sub.1 -C.sub.6 monohaloalkyl, and wherein R.sub.5 and R.sub.6 are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl and mono- or di-substituted phenyl, or R.sub.5 and R.sub.6 together with the nitrogen form a mono- or di-substituted or unsubstituted heterocyclic group selected from the group consisting of indolinyl, morpholino, piperidino, 1-pyrrolidyl, 1-pyrrolinyl, 1-imidazolidyl, 2-imidazolin-1-yl, 2-pyrazolidyl, and 1-piperazinyl, said phenyl and heterocyclic ring substituents being selected from C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy and said halo substituent being chloro or fluoro;
- R.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkoxy substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.2 -C.sub.4)alkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.4 monoalkyl substituted C.sub.5 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 monohaloalkyl, allyl or the group, -C(O)X, wherein X is a C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 mono-or C.sub.1 -C.sub.6 di-alkyl substituted phenyl, C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkoxy substituted phenyl, C.sub.1 -C.sub.6 alkoxy, phenoxy, C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkyl substituted phenoxy, C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkoxy substituted phenoxy, C.sub.1 -C.sub.6 alkylamino, phenylamino, C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkyl substituted phenylamino, or C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkoxy substituted phenylamino, and said halo substituent being chloro, fluoro or bromo, provided that one of R.sub.1 and R.sub.2 is hydrogen;
- and
- (b) B and B' are each selected from the group consisting of the substituted or unsubstituted aryl groups phenyl and naphthyl, said aryl substituents being selected from the group consisting of hydroxy, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 haloalkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkoxy(C.sub.1 -C.sub.4)alkyl, C.sub.1 -C.sub.5 dialkylamino, acryloxy, methacryloxy, and halogen, said halogen or (halo) groups being fluoros chloro, or bromo, provided that at least one of B and B' is a substituted or unsubstituted phenyl.
3 more elements
A naphthopyran compound selected from the group consisting of:
- (a) 3,3-diphenyl-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;
- (b) 3,3-diphenyl-8-methoxy-9-carbophenoxy-3H-naphtho[2,1-b]pyran;
- (c) 3(2-fluorophenyl)-3-(4-methoxyphenyl)-8-methoxy-9-carbopropoxy-3H-naphtho[ 2,1-b]pyran;
- (d) 3(2-fluorophenyl)-3-(4-methoxyphenyl)-8-methoxy-9-carbomethoxy-3H-naphtho[ 2,1-b]pyran;
- (e) 3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-8-acetoxy-9-carbomethoxy-3H-na phtho[2,1-b]pyran;
- and
- (f) 3,3-diphenyl-7-methyl-8-methoxy-3H-naphtho[2,1-b]pyran.
4 more elements
A photochromic article comprising an organic host material and a photochromic amount of a naphthopyran compound represented by the following graphic formula:
- ##STR12## wherein:
- (a) R.sub.1 is hydrogen or a C.sub.1 -C.sub.6 alkyl;
- R.sub.2 is hydrogen or the group, -C(O)W, W being -OR.sub.4 or -N(R.sub.5)R.sub.6, wherein R.sub.4 is hydrogen, allyl, C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 monoalkyl substituted phenyl, C.sub.1 -C.sub.6 monoalkoxy substituted phenyl, phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkoxy substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.2 -C.sub.4)alkyl, or C.sub.1 -C.sub.6 monohaloalkyl, and wherein R.sub.5 and R.sub.6 are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl and mono- or di-substituted phenyl, or R.sub.5 and R.sub.6 together with the nitrogen form a mono- or di-substituted or unsubstituted heterocyclic group selected from the group consisting of indolinyl, morpholino, piperidino, 1-pyrrolidyl, 1-pyrrolinyl, 1-imidazolidyl, 2-imidazolin-1-yl, 2-pyrazolidyl, and 1-piperazinyl, said phenyl and heterocyclic ring substituents being selected from C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy and said halo substituent being chloro or fluoro;
- R.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkoxy substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.2 -C.sub.4)alkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.4 monoalkyl substituted C.sub.5 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 monohaloalkyl, allyl or the group, -C(O)X, wherein X is a C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 mono-or C.sub.1 -C.sub.6 di-alkyl substituted phenyl, C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkoxy substituted phenyl, C.sub.1 -C.sub.6 alkoxy, phenoxy, C.sub.1 -C.sub.6 mono- or C.sub.1 - C.sub.6 di-alkyl substituted phenoxy, C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkoxy substituted phenoxy, C.sub.1 -C.sub.6 alkylamino, phenylamino, C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkyl substituted phenylamino, or C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkoxy substituted phenylamino, and said halo substituent being chloro, fluoro or bromo, provided that one of R.sub.1 and R.sub.2 is hydrogen;
- and
- (b) B and B' are each selected from the group consisting of the substituted or unsubstituted aryl groups phenyl and naphthyl, said aryl substituents being selected from the group consisting of hydroxy, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 haloalkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkoxy(C.sub.1 -C.sub.4)alkyl, C.sub.1 -C.sub.5 dialkylamino, acryloxy, methacryloxy, and halogen, said halogen or (halo) groups being fluoro, chloro, or bromo, provided that at least one of B and B' is a substituted or unsubstituted phenyl.
3 more elements
A photochromic article comprising a solid transparent polymerized organic host material and a photochromic amount of each of (a) a first photochromic substance selected from the group consisting of spiro(indoline) naphthoxazines, spiro(indoline) pyridobenzoxazines, spiro(indoline) benzoxazines, and benzopyrans or naphthopyrans other than the photochromic substance of (b) having a nitrogen-containing substituent on the carbon atom adjacent to the oxygen of the pyran ring, and (b) a second photochromic substance selected from naphthopyran compounds represented by the following graphic formula:
- ##STR14## wherein:
- (a) R.sub.1 is hydrogen or a C.sub.1 -C.sub.6 alkyl;
- R.sub.2 is hydrogen or the group, -C(O)W, W being -OR.sub.4 or -N(R.sub.5)R.sub.6, wherein R.sub.4 is hydrogen, allyl, C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 monoalkyl substituted phenyl, C.sub.1 -C.sub.6 monoalkoxy substituted phenyl, phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkoxy substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.2 -C.sub.4)alkyl, or C.sub.1 -C.sub.6 monohaloalkyl, and wherein R.sub.5 and R.sub.6 are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl and mono- or di-substituted phenyl, or R.sub.5 and R.sub.6 together with the nitrogen form a mono- or di-substituted or unsubstituted heterocyclic group selected from the group consisting of indolinyl, morpholino, piperidino, 1-pyrrolidyl, 1-pyrrolinyl, 1-imidazolidyl, 2-imidazolin-1-yl, 2-pyrazolidyl, and 1-piperazinyl, said phenyl and heterocyclic ring substituents being selected from C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy and said halo substituent being chloro or fluoro;
- R.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 monoalkoxy substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.2 -C.sub.4)alkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.4 monoalkyl substituted C.sub.5 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 monohaloalkyl, allyl or the group, -C(O)X, wherein X is a C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 mono-or C.sub.1 -C.sub.6 di-alkyl substituted phenyl, C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkoxy substituted phenyl, C.sub.1 -C.sub.6 alkoxy, phenoxy, C.sub.1 -C.sub.6 mono- or C.sub.1 - C.sub.6 di-alkyl substituted phenoxy, C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkoxy substituted phenoxy, C.sub.1 -C.sub.6 alkylamino, phenylamino, C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkyl substituted phenylamino, or C.sub.1 -C.sub.6 mono- or C.sub.1 -C.sub.6 di-alkoxy substituted phenylamino and said halo substituent being chloro, fluoro or bromo, provided that one of R.sub.1 and R.sub.2 is hydrogen;
- and
- (b) B and B' are each selected from the group consisting of the substituted or unsubstituted aryl groups phenyl and naphthyl, said aryl substituents being selected from the group consisting of hydroxy, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 haloalkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkoxy(C.sub.1 -C.sub.4)alkyl, C.sub.1 -C.sub.5 dialkylamino, acryloxy, methacryloxy, and halogen, said halogen or (halo) groups being fluoro, chloro, or bromo, provided that at least one of B and B' is a substituted or unsubstituted phenyl.
3 more elements
Dependencies are inferred from the claim text.