Photochromic naphthopyrans

Claim 2

A naphthopyran represented by the following graphic formula: ##STR15## wherein R 5 and R 9 are each selected from the group consisting of hydrogen, C 1 -C 4 alkoxy and C 1 -C 4 alkyl, R 8 is selected from the group consisting of halogen, C 1 -C 5 acyloxy, benzoyloxy, methoxybenzoyloxy, di(C 1 -C 5 )alkylamino, and LO-, wherein L is a C 1 -C 12 alkyl, C 6 -C 9 aryl(C 1 -C 3 )alkyl, C 5 -C 7 cycloalkyl, or C 1 -C 4 alkyl substituted C 5 -C 7 cycloalkyl, and B and B' are each selected from the group consisting of the unsubstituted or substituted aryl groups phenyl and naphthyl, said aryl group substituents each being selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl, di(C 1 -C 5 )alkylamino, and halogen, said halogen and halo substituents being selected from the group consisting of fluorine, chlorine and bromine, provided that at least one of B and B' is a substituted or unsubstituted phenyl.

Claim 3

A naphthopyran represented by the following graphic formula: ##STR16## wherein R 5 and R 9 are each selected from the group consisting of hydrogen, C 1 -C 4 alkoxy and C 1 -C 4 alkyl, R 8 is selected from the group consisting of halogen, C 1 -C 5 acyloxy, benzoyloxy, methoxybenzoyloxy, di(C 1 -C 5 )alkylamino, and LO-, wherein L is a C 1 -C 12 alkyl, C 6 -C 9 aryl(C 1 -C 3 )alkyl, C 5 -C 7 cycloalkyl, or C 1 -C 4 alkyl substituted C 5 -C 7 cycloalkyl, and B and B' are the phenyl groups represented respectively by the following graphic formulae: ##STR17## wherein Y 1 is selected from the group consisting of C 1 -C 5 alkyl, C 1 -C 5 alkoxy, fluoro and chloro, Z 1 is selected from the group consisting of hydrogen and Y 1 , each Y 2 and Z 2 are selected from the group consisting of C 1 -C 5 alkyl, C 1 -C 5 alkoxy, cyano, hydroxy, halogen, acrylyl, methacrylyl, acryloxy (C 1 -C 4 ) alkyl and methacryloxy (C 1 -C 4 ) alkyl, and a and b are each integers of from 0 to 2.

Claim 4

A naphthopyran represented by the following graphic formula: ##STR16## wherein R 5 and R 9 are each selected from the group consisting of hydrogen, C 1 -C 4 alkoxy and C 1 -C 4 alkyl, R 8 is selected from the group consisting of halogen, C 1 -C 5 acyloxy, benzoyloxy, methoxybenzoyloxy, di(C 1 -C 5 )alkylamino, and LO-, wherein L is a C 1 -C 12 alkyl, C 6 -C 9 aryl(C 1 -C 3 )alkyl, C 5 -C 7 cycloalkyl, or C 1 -C 4 alkyl substituted C 5 -C 7 cycloalkyl, and B and B' are the phenyl groups represented respectively by the following graphic formulae: ##STR17## wherein Y 1 is selected from the group consisting of C 1 -C 5 alkyl, C 1 -C 5 alkoxy, fluoro and chloro, Z 1 is selected from the group consisting of hydrogen and Y 1 , each Y 2 and Z 2 are selected from the group consisting of C 1 -C 5 alkyl, C 1 -C 5 alkoxy, cyano, hydroxy, halogen, acrylyl, methacrylyl, acryloxy (C 1 -C 4 ) alkyl and methacryloxy (C 1 -C 4 ) alkyl, and a and b are each integers of from 0 to 2.

Claim 5

The naphthopyran of claim 2 wherein L is C 1 -C 4 alkyl, C 6 -C 7 aryl(C 1 -C 2 ) alkyl, C 5 -C 6 cycloalkyl, and C 1 -C 2 alkyl substituted C 5 -C 6 cycloalkyl.

Claim 6

The naphthopyran of claim 2 wherein R 8 is methoxy, chloro or bromo.

Claim 7

The naphthopyran of claim 4 wherein Y 1 is C 1 -C 3 alkyl, C 1 -C 3 alkoxy or fluoro; Z 1 is hydrogen; each Y 2 and Z 2 is selected from the group consisting of C 1 -C 3 alkyl and C 1 -C 3 alkoxy; a is 0 or 1; and b is an integer from 0 to 2.

Claim 8

The naphthopyrans of claim 5 wherein the position of each Y 2 and Z 2 is meta or para to the carbon atom attached to the pyran ring when a and b are 1.

Claim 9

A naphthopyran selected from the group consisting of: (a) 8-methoxy-3,3,-diphenyl-3H-naphtho[2,1-b]pyran, (b) 8-methoxy-3-(2-fluorophenyl)-3-(4-methoxyphenyl)-3H-naphtho[2,1-b]pyran, (c) 8-methoxy-3-phenyl-3-(4-methylphenyl)-3H-naphtho[2,1-b]pyran, (d) 8-methoxy-3-phenyl-3-(4-trifluoromethyl)-3H-naphtho[2,1-b]pyran, (e) 8-methoxy-3-(2-fluorophenyl)-3-(4-methylphenyl)-3H-naphtho[2,1-b]pyran, (f) 8-methoxy-3-(4-dimethylaminophenyl)-3-(phenyl)-3H-naphtho[2,1-b]pyran, and (g) 8-acetoxy-3,3-diphenyl-3H-naphtho[2,1-b]pyran.

Claim 10

A naphthopyran selected from the group consisting of: (a) 8-methoxy-3,3,-diphenyl-3H-naphtho[2,1-b]pyran, (b) 8-methoxy-3-(2-fluorophenyl)-3-(4-methoxyphenyl)-3H-naphtho[2,1-b]pyran, (c) 8-methoxy-3-phenyl-3-(4-methylphenyl)-3H-naphtho[2,1-b]pyran, (d) 8-methoxy-3-phenyl-3-(4-trifluoromethyl)-3H-naphtho[2,1-b]pyran, (e) 8-methoxy-3-(2-fluorophenyl)-3-(4-methylphenyl)-3H-naphtho[2,1-b]pyran, (f) 8-methoxy-3-(4-dimethylaminophenyl)-3-(phenyl)-3H-naphtho[2,1-b]pyran, and (g) 8-acetoxy-3,3-diphenyl-3H-naphtho[2,1-b]pyran.

Claim 11

A photochromic article comprising a polymerized organic host material and a photochromic amount of a naphthopyran compound represented by the following graphic formula: ##STR18## wherein R 5 and R 9 are each selected from the group consisting of hydrogen, C 1 -C 4 alkoxy and C 1 -C 4 alkyl, R 8 is selected from the group consisting of halogen, C 1 -C 5 acyloxy, benzoyloxy, methoxybenzoyloxy, di(C 1 -C 5 )alkylamino, and LO-, wherein L is a C 1 -C 12 alkyl, C 6 -C 9 aryl(C 1 -C 3 )alkyl, C 5 -C 7 cycloalkyl, or C 1 -C 4 alkyl substituted C 5 -C 7 cycloalkyl, and B and B' are each selected from the group consisting of the unsubstituted or substituted aryl groups phenyl and naphthyl, said aryl group substituents each being selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl, di(C 1 -C 5 )alkylamino, and halogen, said halogen and halo substituents being selected from the group consisting of fluorine, chlorine and bromine, provided that at least one of B and B' is a substituted or unsubstituted phenyl.

Claim 12

A photochromic article comprising a polymerized organic host material and a photochromic amount of a naphthopyran compound represented by the following graphic formula: ##STR18## wherein R 5 and R 9 are each selected from the group consisting of hydrogen, C 1 -C 4 alkoxy and C 1 -C 4 alkyl, R 8 is selected from the group consisting of halogen, C 1 -C 5 acyloxy, benzoyloxy, methoxybenzoyloxy, di(C 1 -C 5 )alkylamino, and LO-, wherein L is a C 1 -C 12 alkyl, C 6 -C 9 aryl(C 1 -C 3 )alkyl, C 5 -C 7 cycloalkyl, or C 1 -C 4 alkyl substituted C 5 -C 7 cycloalkyl, and B and B' are each selected from the group consisting of the unsubstituted or substituted aryl groups phenyl and naphthyl, said aryl group substituents each being selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl, di(C 1 -C 5 )alkylamino, and halogen, said halogen and halo substituents being selected from the group consisting of fluorine, chlorine and bromine, provided that at least one of B and B' is a substituted or unsubstituted phenyl.

Claim 13

The photochromic article of claim 8 wherein the organic host material is selected from the group consisting of polymers of polyol(allyl carbonate) monomer, polyacrylates, poly(alkylacrylates), polymers of polyfunctional acrylate monomers, cellulose, acetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, poly(vinyl acetate), poly(vinyl alcohol), poly(vinyl chloride), poly(vinylidene chloride), polycarbonates, polyurethanes, poly(ethylene terephthalate), polystyrene, copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile), polyvinylbutyral, and polymers of diallylidene pentaerythritol.

Claim 14

A photochromic article comprising a polymerized organic host material and a photochromic amount of a naphthopyran represented by the following graphic formula: ##STR19## wherein R 5 and R 9 are each selected from the group consisting of hydrogen, C 1 -C 4 alkoxy and C 1 -C 4 alkyl, R 8 is selected from the group consisting of halogen, C 1 -C 5 acyloxy, benzoyloxy, methoxybenzoyloxy, di(C 1 -C 5 )alkylamino, and LO-, wherein L is a C 1 -C 12 alkyl, C 6 -C 9 aryl(C 1 -C 3 )alkyl, C 5 -C 7 cycloalkyl, or C 1 -C 4 alkyl substituted C 5 -C 7 cycloalkyl, and B and B' are the phenyl groups represented respectively by the following graphic formulae: ##STR20## wherein Y 1 is selected from the group consisting of C 1 -C 5 alkyl, C 1 -C 5 alkoxy, fluoro and chloro, Z 1 is selected from the group consisting of hydrogen and Y 1 , each Y 2 and Z 2 are selected from the group consisting of C 1 -C 5 alkyl, C 1 -C 5 alkoxy, cyano, hydroxy, halogen, acrylyl, methacrylyl, acryloxy (C 1 -C 4 ) alkyl and methacryloxy (C 1 -C 4 ) alkyl, and a and b are each integers of from 0 to 2.

Claim 15

A photochromic article comprising a polymerized organic host material and a photochromic amount of a naphthopyran represented by the following graphic formula: ##STR19## wherein R 5 and R 9 are each selected from the group consisting of hydrogen, C 1 -C 4 alkoxy and C 1 -C 4 alkyl, R 8 is selected from the group consisting of halogen, C 1 -C 5 acyloxy, benzoyloxy, methoxybenzoyloxy, di(C 1 -C 5 )alkylamino, and LO-, wherein L is a C 1 -C 12 alkyl, C 6 -C 9 aryl(C 1 -C 3 )alkyl, C 5 -C 7 cycloalkyl, or C 1 -C 4 alkyl substituted C 5 -C 7 cycloalkyl, and B and B' are the phenyl groups represented respectively by the following graphic formulae: ##STR20## wherein Y 1 is selected from the group consisting of C 1 -C 5 alkyl, C 1 -C 5 alkoxy, fluoro and chloro, Z 1 is selected from the group consisting of hydrogen and Y 1 , each Y 2 and Z 2 are selected from the group consisting of C 1 -C 5 alkyl, C 1 -C 5 alkoxy, cyano, hydroxy, halogen, acrylyl, methacrylyl, acryloxy (C 1 -C 4 ) alkyl and methacryloxy (C 1 -C 4 ) alkyl, and a and b are each integers of from 0 to 2.

Claim 16

The photochromic article of claim 10 wherein R 8 is C 1 -C 4 alkoxy, chloro or bromo.

Claim 17

The photochromic article of claim 11 wherein R 8 is methoxy.

Claim 18

The photochromic article of claim 11 wherein Y 1 is C 1 -C 3 alkyl, C 1 -C 3 alkoxy and fluoro; Z 1 is hydrogen; each Y 2 and Z 2 is selected from the group consisting of C 1 -C 3 alkyl and C 1 -C 3 alkoxy; a is 0 or 1; and b is an integer from 0 to 2.

Claim 19

The photochromic article of claim 13 wherein the position of each Y 2 and Z 2 is meta or para to the carbon atom attached to the pyran ring when a and b are 1.

Claim 20

The photochromic article of claim 13 wherein the organic host material is a solid transparent homopolymer or copolymer of diethylene glycol bis(allyl carbonate), the carbonate-linked resin derived from a bisphenol and phosgene, polymethylmethacrylate, a polyacrylate or polyvinylbutyral.

Claim 21

The photochromic article of claim 15 wherein the photochromic compound is present in an amount of from about 0.01 to 20 weight percent.

Claim 22

The photochromic article of claim 16 wherein the article is a lens.

Claim 23

The photochromic article of claim 13 wherein there is present in addition a photochromic amount of a further photochromic substance selected from the group consisting of spiro(indolino) naphthoxazines, spiro(indolino)pyrido benzoxazines, spiro(indolino) benzoxazines, 3,3-diaryl substituted naphthopyrans free of substitution at the number 8 carbon atom on the naphtho portion of the naphthopyran, and mixtures of such photochromic substances.

Claim 24

The photochromic article of claim 18 wherein the mole ratio of the naphthopyran compound to the further photochromic substance is from about 1:3 to 3:1.

Claim 25

The photochromic article of claim 18 wherein the further photochromic substance is a spiro(indolino) pyrido benzoxazine, spiro(indolino) benzoxazine, 3,3-diaryl substituted naphthopyran free of substitution at the number 8 carbon atom on the naphtho portion of the naphthopyran, and mixtures of such photochromic substances.

Claim 26

The photochromic article of claim 20 wherein the article is a lens.

Claim 27

The photochromic article of claim 21 wherein each photochromic substance is present in amounts of from about 0.05 to about 10 weight percent.