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US 5,458,814 AGranted
Substituted naphthopyrans
AssigneeTransitions Optical, Inc.
InventorsAnil Kumar, Barry Van Gemert, David B. Knowles
Life of this patent
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Abstract
Described are novel reversible photochromic naphthopyran compounds, examples of which are compounds having certain substituents at the number 5 and 6 carbon atoms of the naphtho portion of the naphthopyran and at the 2-position of the pyran ring. Certain substituents may also be present at the number 7, 8, 9 or 10 carbon atoms of the naphtho portion of the naphthopyran. 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(indoline) type compounds, are also described.
Claims24
A naphthopyran compound represented by the following graphic formula:
- ##STR9## wherein, (a) R.sub.1 is 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, mono(C.sub.1 -C.sub.6)alkyl substituted phenyl, mono(C.sub.1 -C.sub.6)alkoxy substituted phenyl, phenyl(C.sub.1 -C.sub.3 )alkyl, mono(C.sub.1 -C.sub.6)alkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkoxy 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 haloalkyl 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, mono-substituted phenyl and di-substituted phenyl, said phenyl substituents being C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy, and said halo substituents being chloro or fluoro;
- (b) R.sub.2 and R.sub.3 are hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, substituted or unsubstituted phenyl, the group --OR.sub.7, wherein R.sub.7 is hydrogen, (C.sub.1 -C.sub.6)alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkoxy 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.3 -C.sub.7 cycloalkyl, mono(C.sub.1 -C.sub.4)alkyl substituted C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, allyl, the group, --CH(R.sub.8)X, wherein X is CN, CF.sub.3, halogen, or --C(O)W and R.sub.8 is hydrogen or C.sub.1 -C.sub.6 alkyl, or R.sub.7 is the group, --C(O)Y, wherein Y is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, the substituted or unsubstituted aryl groups phenyl or naphthyl, phenoxy, C.sub.1 -C.sub.6 mono- or di-alkyl substituted phenoxy, C.sub.1 -C.sub.6 mono- or di-alkoxy substituted phenoxy, C.sub.1 -C.sub.6 alkylamino, phenylamino, C.sub.1 -C.sub.6 mono- or di-alkyl substituted phenylamino, or C.sub. 1 -C.sub.6 mono- or di-alkoxy substituted phenylamino, said aryl substituents being selected from C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy, said halogen or halo substituents being chloro or fluoro and n is selected from the integers 0, 1, 2, or 3;
- and
- (c) B and B' are each 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.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.4)alkyl, acryloxy, methacryloxy and halogen, said halogen or (halo) groups being fluoro or chloro.
1 more element
A naphthopyran compound selected from the group consisting of:
- (a) 2,2-Bis(4-methoxyphenyl)-5-methoxycarbonyl-6-hydroxy-[2H]-naphtho[1,2-b]py ran;
- (b) 2,2-Bis(4-methoxyphenyl)-5-methoxycarbonyl-6-methoxy-[2H]-naphtho[1,2-b]py ran;
- (c) 2,2-Bis(4-methoxyphenyl)-5-methoxycarbonyl-6-(ethoxycarbonyl)methoxy-[2H]- naphtho[1,2-b]pyran;
- (d) 2-(4-Methoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-(cyanomethoxy)-[2H]-napht ho[1,2-b]pyran;
- (e) 2,2-Bis(4-methylphenyl)-5-methoxycarbonyl-6-(methoxycarbonyloxy)-[2H]-naph tho-[1,2-b]pyran;
- (f) 2,2-Diphenyl-5-methoxycarbonyl-6-acetoxy-[2H]-naphtho[1,2-b]pyran;
- (g) 2,2-Bis(4-methoxyphenyl)-5-methoxycarbonyl-6-methyl-[2H]-naphtho[1,2-b]pyr an;
- (h) 2,2-Bis(4-methoxyphenyl)-5-methoxycarbonyl-6-methyl-9-methoxy-[2H]-naphtho [1,2-b]pyran;
- (i) 2,2-Diphenyl-5-methoxycarbonyl-6-propionyloxy-[2H]-naphtho[1,2-b]pyran;
- and
- (j) 2,2-Bis(3-trifluoromethylphenyl)-5-methoxycarbonyl-6-acetoxy-[2H]-naphtho[ 1,2-b]pyran;
8 more elements
A photochromic article comprising, in combination, a solid transparent polymerized organic host material and a photochromic amount of
- (a) at least one organic photochromic compound represented by the graphic formula:
- ##STR10## wherein R.sub.1 is the group --C(O)W, and wherein W is the group --OR.sub.4, R.sub.4 being a C.sub.1 -C.sub.3 alkyl;
- R.sub.2 and each R.sub.3 are selected from hydrogen, C.sub.1 -C.sub.3 alkyl, or the group --OR.sub.7, wherein R.sub.7 is hydrogen, C.sub.1 -C.sub.3 alkyl, the group --CH(R.sub.8)X, wherein X is --C(O)W and R.sub.8 is hydrogen or methyl, or R.sub.7 is the group --C(O)Y wherein Y is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, and n is the integer 0 or 1;
- and B and B' are each selected from substituted or unsubstituted phenyl, wherein the phenyl substituents are C.sub.1 -C.sub.3 alkyl and C.sub.1 -C.sub.3 alkoxy;
- and
- (b) at least one organic photochromic compound selected from the group consisting of spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(indoline)benzoxazines, spiro(indoline) benzopyrans, spiro(indoline)naphthopyrans and 3H-naphtho[2,1-b]pyrans, the weight ratio of the photochromic compounds (a):(b) being from about 1:3 to about 3:1.
3 more elements
Dependencies are inferred from the claim text.