Benzopyran compounds
AssigneeTransitions Optical, Inc.
InventorAnil Kumar
Life of this patent
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Abstract
Described are novel reversible photochromic benzopyran compounds, examples of which are compounds having the 2,3 position of a benzofurano or benzothieno group fused to the f, g, or h side of the benzopyran, or a benzo group fused to the f side of the benzopyran, and (i) a substituted or unsubstituted phenyl and (ii) a substituted or unsubstituted benzothienyl or benzofuranyl group attached (via the 2 or 3 position of the group) at the 2 position of the pyran ring. 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 benzopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro (indoline) type compounds, are also described.
Claims22
A benzopyran compound represented by the following graphic formula:
- ##STR10## wherein (a) A is selected from the group consisting of benzothieno, benzofurano, and benzo, the 2,3 position of said benzothieno or benzofurano group being fused to the f, g, or h side of said benzopyran compound, said benzo group being fused to the f side of the benzopyran, and X is oxygen or sulfur;
- (b) each R.sub.1 is C.sub.1 -C.sub.5 alkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.5 alkyl substituted C.sub.5 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.5 alkylcarbonyl, C.sub.1 -C.sub.5 alkoxycarbonyl, halo(C.sub.1 -C.sub.5)alkylcarbonyl, C.sub.1 -C.sub.5 monoalkylaminocarbonyl, formyl, halogen, R(R')N--, or the group --O--L, wherein R is a C.sub.1 -C.sub.3 alkyl, R' is hydrogen or C.sub.1 -C.sub.3 alkyl, L is hydrogen, C.sub.1 -C.sub.5 alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.5 alkylcarbonyl, halo(C.sub.1 -C.sub.5)alkylcarbonyl, C.sub.1 -C.sub.5 monoalkylaminocarbonyl, acrylyl, methacrylyl, acetonyl, pyridyl, or substituted or unsubstituted arylcarbonyl, said aryl of the arylcarbonyl group being phenyl or naphthyl, said aryl substituents being C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, halogen, C.sub.5 -C.sub.7 cycloalkyl, or C.sub.1 -C.sub.5 alkyl substituted C.sub.5 -C.sub.7 cycloalkyl;
- and
- (c) Each R.sub.2 is C.sub.1 -C.sub.5 alkyl, C.sub.5 -C.sub.7 cycloalkyl, halogen, R(R')N--, or the group --O--L', wherein L' is hydrogen, C.sub.1 -C.sub.5 alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, acrylyl, or methacrylyl;
- each R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy;
- R.sub.4 is hydrogen or C.sub.1 -C.sub.5 alkyl;
- each R.sub.5 is C.sub.1 -C.sub.5 alkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.5 alkylcarbonyl, C.sub.1 -C.sub.5 alkoxycarbonyl, halo(C.sub.1 -C.sub.5)alkylcarbonyl, C.sub.1 -C.sub.5 monoalkylaminocarbonyl, formyl, halogen, cyano, R(R')N--, or the group --O--L, wherein R, R' and L are as defined for R.sub.1 ;
- said halogen (or halo) groups in R.sub.1, R.sub.2 and R.sub.5 being chloro, fluoro, or bromo;
- and a, b, c, and d are each the integers 0, 1, or 2, provided that when A is benzo, a and d are each 0.
A benzopyran selected from the group consisting of:
- (a) 3-phenyl-3-(benzofur-2-yl)-3H-naphtho[2,1-b]pyran;
- (b) 3-(2-fluorophenyl)-3-(benzofur-2-yl)-3H-naphtho[2,1-b]pyran;
- (c) 3-phenyl-3-(benzothiophen-2-yl)-3H-naphtho[2,1-b]pyran;
- (d) 3-phenyl-3-(benzofur-2-yl) -3H-benzo (b)furo[3,2-f]-1-benzopyran;
- (e) 3-phenyl-3-(benzothiophen-3-yl)-3H-naphtho[2,1-b]pyran;
- (f) 2-(2-methoxyphenyl)-2-(benzofur-2-yl)-2H-benzo (b)furo[2,3-g]-1-benzopyran;
- (g) 3-(2-fluorophenyl)-3-(benzofur-2-yl)-3H-benzo(b)thieno[3,2-f]-1-benzopyran
- (h) 3-phenyl-3-(benzothiophen-2-yl)-3H-benzo(b)furo[3,2-f]-1-benzopyran;
- (i) 3-phenyl-3-(benzothiophen-3-yl)-3H-benzo(b)furo[3,2-f]-1-benzopyran;
- and
- (j) 3-(2-methoxyphenyl)-3-(benzofur-2-yl)-3H-benzo(b)thieno[3,2-f]-1-benzopyra n.
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:
- ##STR12## wherein, A is selected from the group consisting of benzothieno, benzofurano, and benzo, the 2,3 position of said benzothieno or benzofurano group being fused to the f, g, or h s side of said benzopyran compound, and said benzo group being fused to the f side of the benzopyran;
- X is oxygen or sulfur;
- each R.sub.1 is C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkylcarbonyl, C.sub.1 -C.sub.5 alkoxycarbonyl, C.sub.1 -C.sub.5 monoalkylaminocarbonyl, formyl, or the group --O--L, wherein L is a C.sub.1 -C.sub.5 alkyl;
- each R.sub.2 is C.sub.1 -C.sub.5 alkyl, fluoro, or the group --O--L', wherein L' is a C.sub.1 -C.sub.5 alkyl;
- each R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy;
- R.sub.4 is hydrogen or C.sub.1 -C.sub.5 alkyl;
- each R.sub.5 is formyl, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkylcarbonyl, C.sub.1 -C.sub.5 alkoxycarbonyl, C.sub.1 -C.sub.5 monoalkylaminocarbonyl, or the group --O--L, wherein L is as defined for R.sub.1 ;
- and a, b, c, and d are each the integers 0, 1, or 2, provided that when A is benzo, a and d are each 0;
- (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, 2H-naphtho[2,1-b]pyrans, 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.
Dependencies are inferred from the claim text.