Photochromic naphthopyran compounds
AssigneeTransitions Optical, Inc.
InventorDavid B. Knowles
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Abstract
Described are novel reversible photochromic naphthopyran compounds, examples of which are compounds substituted at the 3 position of the pyran ring with (i) an aryl substituent and (ii) a phenyl substituent having a 5- or 6-member heterocyclic ring fused at the number 3 and 4 carbon atoms of the phenyl substituent. 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.
Claims19
A naphthopyran compound represented by the following graphic formula:
- ##STR7## wherein, (a) R.sub.1 and R.sub.2 are each C.sub.1 -C10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, halogen, R(R')N--, or the group, --O--L, wherein R and R' are each hydrogen or C.sub.1 -C.sub.3 alkyl, L is C.sub.1 -C.sub.12 alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.3 alkylphenyl, C.sub.1 -C.sub.5 alkylcarbonyl, halo(C.sub.1 -C.sub.4)alkylcarbonyl, C.sub.1 -C.sub.4 monoalkylaminocarbonyl, acetonyl, pyridyl, substituted or unsubstituted arylcarbonyl, said aryl group being phenyl or naphthyl, said aryl substituents being C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.5 -C.sub.7 cycloalkyl, or C.sub.1 -C.sub.4 alkyl substituted C.sub.5 -C.sub.7 cycloalkyl, said halogen (or halo) groups being chloro, fluoro, or bromo;
- and a and b are each the integers 0, 1, or 2, provided that the sum of a and b is not more than 2.
- (b) B is the substituted or unsubstituted aryl group, naphthyl or phenyl, said aryl substituents being C.sub.1 -C.sub.5 alkyl, halo(C.sub.1 -C.sub.5)alkyl, hydroxy, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.4)alkyl, halogen, or R(R')N--, wherein R and R' are each hydrogen or C.sub.5 -C.sub.7 alkyl, and said halogen (or halo) groups being fluorine, chlorine, or bromine;
- and
- (c) B' is selected from the groups represented by the following graphic formulae:
- ##STR8## wherein X is oxygen and Y is carbon or oxygen;
- R.sub.4 and R.sub.5 are each hydrogen or C.sub.1 -C.sub.5 alkyl;
- each R.sub.3 is a C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, hydroxy, or halogen, said halogen being chloro, fluoro, or bromo, and c is an integer from 0 to 3.
A naphthopyran compound selected from the group consisting of:
- (a) 3-(2,3-dihydrobenzofuran-5-yl )-3-phenyl-3H-naphtho-[2,1-b]pyran;
- (b) 3-(2,3-dihydrobenzofuran-5-yl )-3-(2-fluorophenyl)-3H-naphtho[2,1-b]pyran;
- (c) 3-(2,3-dihydrobenzofuran-5-yl )-3-(2-methoxyphenyl)-3H-naphtho[2,1-b]pyran;
- (d) 3-(2-methyldihydrobenzofuran-5-yl)-3-(2-fluoro-phenyl)-3H-naphtho[2,1-b]py ran;
- (e) 8-methoxy-3-(2,3-dihydrobenzofuran-5-yl)-3-(2-fluorophenyl)-3H-naphtho[2,1 -b]pyran;
- (f) 3-(4-methoxyphenyl)-3-(2,4,7-trimethyl-2,3-dihydrobenzofuran-5-yl )-3H-naphtho[2,1-b]pyran;
- and
- (g) 3-(1,3-benzodioxole-5-yl )-3-phenyl-3H-naphtho-(2,1-b)pyran.
A photochromic article comprising an organic host material and a photochromic amount of a naphthopyran compound represented by the following graphic formula:
- ##STR11## wherein, (a) R.sub.1 and R.sub.2 are each C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, halogen, R(R')N--, or the group, --O--L, wherein R and R' are each hydrogen or C.sub.1 -C.sub.3 alkyl, L is C.sub.1 -C.sub.12 alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.3 alkylphenyl, C.sub.1 -C.sub.5 alkylcarbonyl, halo(C.sub.1 -C4)alkylcarbonyl, C.sub.1 -C.sub.4 monoalkylaminocarbonyl, acetonyl, pyridyl, substituted or unsubstituted arylcarbonyl, said aryl group being phenyl or naphthyl, said aryl substituents being C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.5 -C.sub.7 cycloalkyl, or C.sub.1 -C.sub.4 alkyl substituted C.sub.5 -C.sub.7 cycloalkyl, said halogen (or halo) groups being chloro, fluoro, or bromo;
- and a and b are each the integers 0, 1, or 2, provided that the sum of a and b is not more than 2;
- (b) B is the substituted or unsubstituted aryl group, naphthyl or phenyl, said aryl substituents being C.sub.1 -C.sub.5 alkyl, halo(C.sub.1 -C.sub.5)alkyl, hydroxy, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.4)alkyl, halogen, or R(R')N--, wherein R and R' are each hydrogen or C.sub.1 -C.sub.3 alkyl, and said halogen (or halo) groups being fluorine, chlorine, or bromine;
- and
- (c) B' is selected from the groups represented by the following graphic formulae:
- ##STR12## wherein X is oxygen and Y is carbon or oxygen;
- R.sub.4 and R.sub.5 are each hydrogen or C.sub.1 -C.sub.5 alkyl;
- each R.sub.3 is a C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, hydroxy, or halogen, said halogen being chloro, fluoro, or bromo, and c is an integer from 0 to 3.
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, and spiro(indoline) benzoxazines, and benzopyrans or naphthopyrans having a nitrogen-containing substituent in the 2-position of the pyran ring, and (b) a second photochromic substance selected from naphthopyran compounds represented by the following graphic formula:
- ##STR15## wherein, (a) R.sub.1 and R.sub.2 are each C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, halogen, R(R')N--, or the group, --O--L, wherein R and R' are each hydrogen or C.sub.1 -C.sub.3 alkyl, L is C.sub.1 -C.sub.12 alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.3 alkylphenyl, C.sub.1 -C.sub.5 alkylcarbonyl, halo(C.sub.1 -C.sub.4)alkylcarbonyl, C.sub.1 -C.sub.4 monoalkylaminocarbonyl, acetonyl, pyridyl, substituted or unsubstituted arylcarbonyl, said aryl group being phenyl or naphthyl, said aryl substituents being C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.5 -C.sub.7 cycloalkyl, or C.sub.1 -C.sub.4 alkyl substituted C.sub.5 -C.sub.7 cycloalkyl, said halogen (or halo) groups being chloro, fluoro, or bromo;
- and a and b are each the integers 0, 1, or 2, provided that the sum of a and b is not more than 2;
- (b) B is the substituted or unsubstituted aryl group, naphthyl or phenyl, said aryl substituents being C.sub.1 -C.sub.5 alkyl, halo(C.sub.1 -C.sub.5)alkyl, hydroxy, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.4)alkyl, halogen, or R(R')N--, wherein R and R' are each hydrogen or C.sub.1 -C.sub.3 alkyl, and said halogen (or halo) groups being fluorine, chlorine, or bromine;
- and
- (c) B' is selected from the groups represented by the following graphic formulae:
- ##STR16## wherein X is oxygen and Y is carbon or oxygen provided;
- R.sub.4 and R.sub.5 are each hydrogen or C.sub.1 -C.sub.5 alkyl;
- each R.sub.3 is a C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, hydroxy or halogen, said halogen being chloro, fluoro, or bromo, and c is an integer from 0 to 3.
Dependencies are inferred from the claim text.