Photochromic naphthopyran compounds

Claim 2

A naphthopyran compound represented by the following graphic formula: ##STR15## 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 ; Y 2 and Z 2 are each 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; a and b are each integers selected from the group consisting of 0, 1 and 2; and R 5 -R 10 are each selected from the group consisting of hydrogen, C 1 -C 10 alkyl, C 5 -C 7 cycloalkyl, phenyl, mono- or di- substituted phenyl, C 1 -C 4 alkoxy, halogen, acrylyl, methacrylyl, acryloxy (C 1 -C 4 ) alkyl, methacryloxy (C 1 -C 4 ) alkyl, furyl and thienyl, said phenyl substituents being selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, chloro and bromo.

Claim 3

A naphthopyran compound according to claim 1 wherein Y 1 is selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy and fluoro; Z 1 is selected from the group consisting of hydrogen and Y 1 ; Y 2 and Z 2 are each selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy and fluoro; a and b are each integers selected from the group consisting of 0, 1 and 2; and R 5 -R 10 are each selected from the group consisting of hydrogen, C 1 -C 5 alkyl, C 5 -C 6 cycloalkyl, C 1 -C 3 alkoxy, chloro, bromo, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, phenyl, ortho-, meta- or para- substituted phenyl, said phenyl substituents being selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, chloro and bromo.

Claim 4

A naphthopyran compound according to claim 2 wherein the R 5 -R 10 substituted phenyl substituent is a para-substituted phenyl.

Claim 5

A naphthopyran compound according to claim 2 wherein R 5 -R 10 are each selected from the group consisting of hydrogen C 1 -C 3 alkyl, C 1 -C 3 alkoxy, chloro, bromo, phenyl and C 1 -C 3 alkoxyphenyl.

Claim 6

A naphthopyran compound according to claim 4 wherein the C 1 -C 3 alkoxyphenyl is a para C 1 -C 3 alkoxyphenyl.

Claim 7

A naphthopyran compound according to claim 2 wherein R 5 -R 10 are each hydrogen.

Claim 8

A naphthopyran compound according to claim 2 wherein R 5 -R 9 are each hydrogen, R 5 -R 8 are each hydrogen, or R 5 and R 7 -R 9 are each hydrogen.

Claim 9

A naphthopyran compound according to claim 2 wherein Y 1 is selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy and fluoro; Z 1 is hydrogen; Y 2 is C 1 -C 3 alkoxy; Z 2 is selected from the group consisting of C 1 -C 3 alkyl and C 1 -C 3 alkoxy; R 5 -R 10 are each hydrogen, a is the integer 0 or 1 and b is the integer 0, 1 or 2.

Claim 10

A naphthopyran compound according to claim 8 wherein when a or b are the integer 1, the Y 2 and Z 2 substituents are located at the 3, 4 or 5 carbon atom position.

Claim 11

A naphthopyran compound according to claim 9 wherein the Y 2 and Z 2 substituents are located at the 3 or 4 carbon atom position.

Claim 12

A naphthopyran compound according to claim 8 wherein when b is 2, the Z 2 substituents are located at the 3 and 4, 3 and 5 or 4 and 5 carbon atom positions.

Claim 13

3(2-fluorophenyl)-3(4-methoxyphenyl)-3H-naphtho[2,1-b]pyran.

Claim 14

3(2-fluorophenyl)-3(4-methoxyphenyl)-3H-naphtho[2,1-b]pyran.

Claim 15

3(2-fluorophenyl)-3(3,4-dimethoxyphenyl)-3H-naphtho[2,1-b]-pyran.

Claim 16

3(2-fluorophenyl)-3(3,4-dimethoxyphenyl)-3H-naphtho[2,1-b]-pyran.

Claim 17

3(2-methyl-4-methoxyphenyl)-3(4-methoxyphenyl)-3H-naphtho [2,1-b]pyran.

Claim 18

3(2-methyl-4-methoxyphenyl)-3(4-methoxyphenyl)-3H-naphtho [2,1-b]pyran.

Claim 19

3(2-methylphenyl)-3(4-methyloxyphenyl)-3H-naphtho[2,1-b]pyran.

Claim 20

3(2-methylphenyl)-3(4-methyloxyphenyl)-3H-naphtho[2,1-b]pyran.

Claim 21

3-phenyl-3(2,4-dimethoxyphenyl)-3H-naphtho[2,1-b]pyran. 17. A photochromic article comprising a polymerized organic host material and a photochromic amount of a naphthopyran compound represented by the following graphic formula: ##STR16## wherein Y 1 is selected from the group consisting of C 1 -C 5 alkyl, C 1 -C 5 oxy, fluoro and chloro; Z 1 is selected from the group consisting of hydrogen and Y 1 ; Y 2 and Z 2 are each 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; a and b are each integers selected from the group consisting of 0, 1 and 2; and R 5 -R 10 are each selected from the group consisting of hydrogen, C 1 -C 10 alkyl, C 5 -C 7 cycloalkyl, phenyl, mono- or di- substituted phenyl, C 1 -C 4 alkoxy, halogen, acrylyl, methacrylyl, acryloxy (C 1 -C 4 ) alkyl, methacryloxy (C 1 -C 4 ) alkyl, furyl and thienyl, said phenyl substituents being selected from the group consisting of C 1 -C 4 alkyl, C 1 -

Claim 22

3-phenyl-3(2,4-dimethoxyphenyl)-3H-naphtho[2,1-b]pyran. 17. A photochromic article comprising a polymerized organic host material and a photochromic amount of a naphthopyran compound represented by the following graphic formula: ##STR16## wherein Y 1 is selected from the group consisting of C 1 -C 5 alkyl, C 1 -C 5 oxy, fluoro and chloro; Z 1 is selected from the group consisting of hydrogen and Y 1 ; Y 2 and Z 2 are each 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; a and b are each integers selected from the group consisting of 0, 1 and 2; and R 5 -R 10 are each selected from the group consisting of hydrogen, C 1 -C 10 alkyl, C 5 -C 7 cycloalkyl, phenyl, mono- or di- substituted phenyl, C 1 -C 4 alkoxy, halogen, acrylyl, methacrylyl, acryloxy (C 1 -C 4 ) alkyl, methacryloxy (C 1 -C 4 ) alkyl, furyl and thienyl, said phenyl substituents being selected from the group consisting of C 1 -C 4 alkyl, C 1 -

Claim 23

C 4 alkoxy, chloro and bromo. 18. The photochromic article of claim 17 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), polycarbonate, polyurethanes, poly(ethylene terephthalate), polystyrene, copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile),

Claim 24

polyvinylbutyral, and polymers of diallylidene pentaerythritol. 19. The photochromic article of claim 18 wherein Y 1 is selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy and fluoro; Z 1 is selected from the group consisting of hydrogen Y 2 and Z 2 are each selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy and fluoro; a and b are each integers selected from the group consisting of 0, 1 and 2; and R 5 -R 10 are each selected from the group consisting of hydrogen, C 1 -C 5 alkyl, C 5 -C 6 cycloalkyl, C 1 -C 3 alkoxy, chloro, bromo, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, phenyl, and ortho-, meta- or para- substituted phenyl, said phenyl substituents being selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4

Claim 25

alkoxy, chloro and bromo. 20. The photochromic article of claim 19 wherein Y 1 is selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy and fluoro; Z 1 is hydrogen; Y 2 is C 1 -C 3 alkoxy; Z 2 is selected from the group consisting of C 1 -C 3 alkyl and C 1 -C 3 alkoxy; R 5 -R 10 are each hydrogen, a is the integer 0 or 1 and b is the integer 0, 1 or 2.

Claim 26

The photochromic article of claim 20 wherein the organic host material is a solid transparent homopolymer or copolymer of diethylene glycol bis(allyl carbonate), poly(4,4'-dioxydiphenol-2,2-propane),

Claim 27

polymethylmethacrylate, or polyvinylbutyral. 22. The photochromic article of claim 21 wherein the photochromic compound is present in an amount of

Claim 28

from about 0.01 to 20 weight percent. 23. The photochromic article of

Claim 29

from about 0.01 to 20 weight percent. 23. The photochromic article of

Claim 30

claim 22 wherein the article is a lens. 24. 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(indolino) naphthoxazines, spiro(indolino) pyrido benzoxazines, and spiro(indolino) benzoxazines, and (b) a naphthopyran compound represented by the following graphic formula: ##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 ; Y 2 and Z 2 are each 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; a and b are each integers selected from the group consisting of 0, 1 and 2; and R 5 -R 10 are each selected from the group consisting of hydrogen, C 1 -C 10 alkyl, C 5 -C 7 cycloalkyl, phenyl, mono- or di- substituted phenyl, C 1 -C 4 alkoxy, halogen, acrylyl, methacrylyl, acryloxy (C 1 -C 4 ) alkyl, methacryloxy (C 1 -C 4 ) alkyl, furyl and thienyl, said phenyl substituents being selected from the group consisting of C 1 -C 4 alkyl,

Claim 31

C 1 - C 4 alkoxy, chloro and bromo. 25. The photochromic article of claim 24 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), polycarbonate, polyurethanes, poly(ethylene terephthalate), polystyrene, copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile),

Claim 32

polyvinylbutyral, and polymers of diallylidene pentaerythritol. 26. The photochromic article of claim 25 wherein Y 1 is selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy and fluoro; Z 1 is selected from the group consisting of hydrogen and Y 1 ; Y 2 and Z 2 are each selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy and fluoro; a and b are each integers selected from the group consisting of 0, 1 and 2; and R 5 -R 10 are each selected from the group consisting of hydrogen, C 1 -C 5 alkyl, C 5 -C 6 cycloalkyl, C 1 -C 3 alkoxy, chloro, bromo, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, phenyl, and ortho-, meta- or para- substituted phenyl, said phenyl substituents being selected from the group consisting of C 1 -C 4 alkyl, C 1

Claim 33

-C 4 alkoxy, chloro and bromo. 27. The photochromic article of claim 26 wherein Y 1 is selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy and fluoro; Z 1 is hydrogen; Y 2 is C 1 -C 3 alkoxy; Z 2 is selected from the group consisting of C 1 -C 3 alkyl and C 1 -C 3 alkoxy; R 5 -R 10 are each hydrogen, a is the integer 0 or 1 and b is the integer

Claim 34

0, 1 or 2. 28. The photochromic article of claim 27 wherein the organic host material is a solid transparent homopolymer or copolymer of diethylene glycol bis(allyl carbonate), poly(4,4'-dioxydiphenol-2,2-propane), polymethylmethacrylate, or

Claim 35

polyvinylbutyral. 29. The photochromic article of claim 27 wherein the first photochromic substance is a spiro(indolino) pyrido benzoxazine or

Claim 36

spiro(indolino) naphthoxazine. 30. The photochromic article of claim 27 wherein the first photochromic substance is a spiro(indolino) benzoxazine.

Claim 37

The photochromic article of claim 26 wherein the first photochromic substance and photochromic naphthopyran compound are each present in

Claim 38

amounts of from about 0.05 to about 10 weight percent. 32. The photochromic article of claim 31 wherein the weight ratio of the first photochromic substance to the naphthopyran compound varies from about 1:3

Claim 39

to about 3:1. 33. The photochromic article of claim 32 wherein the article is an ophthalmic lens.