CA2512605A1 - Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles - Google Patents

Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles Download PDF

Info

Publication number
CA2512605A1
CA2512605A1 CA 2512605 CA2512605A CA2512605A1 CA 2512605 A1 CA2512605 A1 CA 2512605A1 CA 2512605 CA2512605 CA 2512605 CA 2512605 A CA2512605 A CA 2512605A CA 2512605 A1 CA2512605 A1 CA 2512605A1
Authority
CA
Canada
Prior art keywords
alkyl
chosen
mono
alkoxy
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA 2512605
Other languages
French (fr)
Other versions
CA2512605C (en
Inventor
Robert W. Walters
Anil Kumar
Clara E. Nelson
Anu Chopra
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Transitions Optical Inc
Original Assignee
Transitions Optical, Inc.
Robert W. Walters
Anil Kumar
Clara E. Nelson
Anu Chopra
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Transitions Optical, Inc., Robert W. Walters, Anil Kumar, Clara E. Nelson, Anu Chopra filed Critical Transitions Optical, Inc.
Publication of CA2512605A1 publication Critical patent/CA2512605A1/en
Application granted granted Critical
Publication of CA2512605C publication Critical patent/CA2512605C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02—Organic tenebrescent materials
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/259—Coating or impregnation provides protection from radiation [e.g., U.V., visible light, I.R., micscheme-change-itemave, high energy particle, etc.] or heat retention thru radiation absorption

Abstract

Described are photochromic materials of indeno[2', 3':3,4]naphtho[1,2-b]pyran structure of formula I.

(see formula I) They have a nitrogen or sulfur containing substituent at the 11-position ring atom, are substantially free of spiro-substituents at the 13-position and have been adapted to provide an increase in the sensitivity, visible lambda max or a combination thereof as measured in the Indenonaphthopyran Photochromic Performance Test.
Optional substituents can be present at the other positions of the indeno[2', 3':3,4]naphtho[1,2-b]pyran structure. Also described are naphthols used to produce the photochromic materials and photochromic articles that contain or that have coatings containing at least one of the novel photochromic materials or combinations thereof with other photochromic materials.

Claims (56)

1. A photochromic material of indeno
[2',3':3,4]naphtho[1,2-b]pyran structure, characterized in that it comprises a nitrogen or sulfur containing substituent at the 11-position ring atom, said ring atoms being numbered according to the International Union of Pure and Applied Chemistry rules of nomenclature starting with the 1-position ring atom being the carbon atom para to the oxygen atom of the pyran ring and numbering clockwise therefrom, said photochromic material being substantially free of spiro-substituents at the 13-position, and said photochromic material being adapted to provide an increase in the sensitivity, visible lambda max or a combination thereof as measured in the Indenonaphthopyran Photochromic Performance Test.

2. The photochromic material of claim 1 wherein the sulfur containing substituent at the 11-position ring atom is the group, -SR7, R7 being chosen from C1-C6 alkyl, aryl, mono- or di-substituted aryl, said aryl group being phenyl or naphthyl and each of said aryl substitutents being chosen independently from C1-C6 alkyl, C1-C6 alkoxy or halogen.
3. The photochromic material of claim 2 wherein R7 is chosen from C1-C6 alkyl or phenyl.
4. The photochromic material of claim 1 wherein the nitrogen containing substituent at the 11-position ring atom is represented by:

(i) -N(R15)R16, R15 and R16 each being independently chosen from hydrogen, C1-C8 alkyl, aryl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, benzopyridyl, fluorenyl, C1-C8 alkylaryl, C3-C20 cycloalkyl, C4-C20 bicycloalkyl, C5-C20 tricycloalkyl or C1-C20 alkoxyalkyl and said aryl group being phenyl or naphthyl:

(ii) a nitrogen containing ring represented by the following graphic formula:

wherein each Y being independently chosen for each occurrence from -CH2-, -CH(R17)-, -C(R17)(R17)-, -CH(aryl)-, -C(aryl)2-or -C(R17)(aryl)-; X being -Y-, -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(R17)- or -N(aryl)-: R17 being C1-C6 alkyl; said aryl group being phenyl or naphthyl, m being chosen from the integer 1, 2 or 3 and p being chosen from the integer 0, 1, 2 or 3; provided that when p is 0, X is Y;
(iii) a group represented by one of the following graphic formulae:

wherein each R19, R20 and R21 being chosen independently for each occurrence in each formula from hydrogen, C1-C5 alkyl, phenyl or naphthyl; or the groups R19 and R20 together form a ring of 5 to 8 carbon atoms; R18 being chosen independently for each occurrence from C1-C6 alkyl, C1-6 alkoxy, fluoro or chloro and n being chosen from the integer 0, 1 or 2;
(iv) unsubstituted, mono- or di- substituted C4-C18 spirobicyclic amine: or (v) unsubstituted, mono- or di- substituted C4-Cl8 spirotricyclic amine; said substituents for (iv) and (v) being independently chosen for each occurrence from aryl, C1-C6 alkyl, C1-6 alkoxy or phenyl(C1-C6)alkyl.
5. The photochromic material of claim 4 wherein the nitrogen containing substituent at the 11-position ring atom is represented by:
(i) -N(R15)R16, R15 and R16 each being independently chosen from C1-C6 alkyl or phenyl;
(ii) a nitrogen containing ring represented by the following graphic formula:

wherein each Y being -CH2- and X being independently chosen from -Y-, -0-, -S-, -N(R17)- and -N(phenyl)-, R17 being C1-C6 alkyl, m being chosen from the integer 1, 2 or 3, and p being chosen from the integer 0, 1, 2 or 3;
(iii) a group represented by one of the following graphic formulae:

wherein R19, R20 and R21 each being independently chosen from hydrogen or C1-C5 alkyl, R18 being independently chosen from hydrogen, C1-C4 alkyl, C1-4 alkoxy, fluoro or chloro and n being chosen from the integer 0 or 1;
(iv) unsubstituted or mono-substituted C5-C18 spirobicyclic amines; or (v) unsubstituted or mono-substituted C5-C18 spirotricyclic amine; said substituents for (iv) and (v) being independently chosen for each occurrence from phenyl, C1-C3 alkyl, C1-C3 alkoxy or phenyl(C1-C3)alkyl.
6. The photochromic material of claim 5 wherein the nitrogen containing substituent at the 11-position ring atom is represented by:

(i) -N(R15)R16, R15 and R16 each being C1-C3;
(ii) a nitrogen containing ring represented by the following graphic formula:

wherein each Y being -CH2- and X being independently chosen from -Y-, -O-, and -N(R17)-, R17 being C1-C4 alkyl, m being chosen from the integer 1 or 2, and p being chosen from the integer 0, 1 or 2; or (iii) a group represented by the following graphic formulae:

wherein R19, R20, and R21 each being hydrogen and n is 0.
7. The photochromic material of claim 1 wherein said photochromic material is chosen from:
(a) a single photochromic compound;
(b) a mixture of photochromic compounds;
(c) a material comprising at least one photochromic compound;

(d) a material to which at least one photochromic compound is chemically bonded;
(e) material (c) or (d) further comprising a coating to substantially prevent contact of the at least one photochromic compound with external materials;
(f) a photochromic polymer; or (g) mixtures thereof.
8. A photochromic article comprising an at least partially cured polymer and at least a photochromic amount of at least one photochromic material of indeno [2',3':3,4]-naphtho[1,2-b]pyran structure characterized in that it comprises a nitrogen or sulfur containing substituent at the 11-position ring atom, said ring atoms being numbered according to the International Union of Pure and Applied Chemistry rules of nomenclature starting with the 1-position ring atom being the carbon atom para to the oxygen atom of the pyran ring and numbering clockwise therefrom, said photochromic material being substantially free of spiro-substituents at the 13-position, and said photochromic material being adapted to provide an increase in the sensitivity, visible lambda max or a combination thereof as measured in the Indenonaphthopyran Photochromic Performance Test.
9. The photochromic article of claim 8 further comprising at least one other photochromic material comprising at least one activated absorption maxima within the range of from 400 to 700 nanometers.
10. The photochromic article of claim 8 wherein the at least partially cured polymer is chosen from thermosetting or thermoplastic organic polymeric materials.
11. The photochromic article of claim 8 further comprising a superstrate connected to at least a portion of the at least partially cured polymer, said superstrate comprising at least one organic polymeric material.
12. The photochromic article of claim 11 wherein the superstrate is an organic polymeric material and is chosen from thermosetting or thermoplastic materials.
13. The photochromic article of claim 11 further comprising an at least partially abrasion resistant film superposed on at least a portion of the superstrate.
14. The photochromic article of claim 13 wherein the at least partially abrasion resistant film is an organic polymeric material chosen from thermoplastic and thermosetting materials.
15. A photochromic article comprising a substrate and an at least partial coating of a photochromic polymeric coating comprising a film forming polymer and at least a photochromic amount of at least one photochromic material of indeno [2',3':3,4]naphtho[1,2-b]pyran structure characterized in that it comprises a nitrogen or sulfur containing substituent at the 11-position ring atom, said ring atoms being numbered according to the International Union of Pure and Applied Chemistry rules of nomenclature starting with the 1-position ring atom being the carbon atom para to the oxygen atom of the pyran ring and numbering clockwise therefrom, said photochromic material being substantially free of spiro-substituents at the 13-position, and said photochromic material being adapted to provide an increase in the sensitivity, visible lambda max or a combination thereof as measured in the Indenonaphthopyran Photochromic Performance Test.
16. The photochromic article of claim 15 wherein the substrate is paper, glass, ceramic, wood, masonry, textile, metal or polymeric organic material.
17. The photochromic article of claim 16 wherein the substrate is a polymeric organic material and is chosen from thermosetting or thermoplastic organic polymeric materials.
18. The photochromic article of claim 15 wherein the film-forming polymer is chosen from thermosetting or thermoplastic organic polymeric materials.
19. The photochromic article of claim 18 wherein the film forming polymer is thermosetting and is chosen from polyurethanes, aminoplast resins, polysilanes, polyanhydrides, polyacrylamides or epoxy resins.
20. The photochromic article of claim 15 wherein the photochromic polymeric coating further comprises at least one other photochromic material comprising at least one activated absorption maxima within the range of from 400 to 700 nanometers.
21. The photochromic article of claim 15 wherein the substrate is an optical element.
22. A naphthopyran represented by the following graphic formula:

wherein, (a) R1 is represented by:
(i) -SR7, R7 being chosen from C1-C6 alkyl, aryl, mono- or di-substituted aryl, said aryl group being phenyl or naphthyl and each of said aryl substitutents being chosen independently from C1-C6 alkyl, C1-C6 alkoxy or halogen;
(ii) -N(R15)R16, R15 and R16 each being independently chosen from hydrogen, C1-C8 alkyl, aryl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, benzopyridyl, fluorenyl, C1-C8 alkylaryl, C3-C20 cycloalkyl, C4-C20 bicycloalkyl, C5-C20 tricycloalkyl or C1-C20 alkoxyalkyl and said aryl group being phenyl or naphthyl;
(iii) a nitrogen containing ring represented by the following graphic formula:

wherein each Y being independently chosen for each occurrence from -CH2-, -CH(R17)-, -C(R17)(R17)-, -CH(aryl)-, -C(aryl)2-or -C(R17)(aryl)-: X being -Y-, -0-, -S-, -S(0)-, -S(02)-, -NH-, -N(R17)- or -N(aryl)-; R17 being Cl-C6 alkyl; said aryl group being phenyl or naphthyl, m being chosen from the integer 1, 2 or 3 and p being chosen from the integer 0, 1, 2 or 3; provided that when p is 0, X is Y;
(iv) a group represented by one of the following graphic formulae:

wherein each R19, R20 and R21 being chosen independently for each occurrence in each formula from hydrogen, Cl-C5 alkyl, phenyl or naphthyl; or the groups Rl9 and R20 together form a ring of 5 to 8 carbon atoms; Rl8 being chosen independently for each occurrence from Cl-C6 alkyl, Cl-C6 alkoxy, fluoro or chloro and n being chosen from the integer 0, 1 or 2;
(v) unsubstituted, mono- or di- substituted C4-C18 spirobicyclic amine; or (vi) unsubstituted, mono- or di- substituted C4-Cl8 spirotricyclic amine; said substituents for (v) and (vi) being independently chosen for each occurrence from aryl, Cl-C6 alkyl, Cl-6 alkoxy or phenyl(C1-C6)alkyl;
(b) Rl is independently chosen for each occurrence from Cl-C6 alkyl or Cl-C6 alkoxy and n being chosen from the integer 0, 1 or 2;
(c) R2 and R3 are each independently chosen from:
(i) hydrogen, hydroxy, amino, mono- or di-substituted amino, Cl-C12 alkyl, C3-C12 alkylidene, C2-C12 alkylidyne, vinyl, C3-C7 cycloalkyl, Cl-C6 aloalkyl, allyl, benzyl, mono-substituted benzyl, chloro, fluoro or -C(0)W, wherein W being hydroxy, Cl-C6 alkyl, C1-C6 alkoxy, phenyl, mono-substituted phenyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, morpholino, piperidino or pyrrolidyl;
said amino substituents being C1-C6 alkyl, phenyl, benzyl or naphthyl; each of said benzyl and phenyl substituents being C1-C6 alkyl or C1-C6 alkoxy;
(ii) an unsubstituted, mono- di- or tri-substituted group chosen from phenyl, naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl or indolyl; each of said group substituents in (c)(ii) being chosen independently for each occurrence from chloro, fluoro, C1-C6 alkyl or C1-C6 alkoxy;
(iii) a monosubstituted phenyl, said phenyl having a substituent located at the para position being -(CH2)t- or -0-(CH2)t-, connected to an aryl group which is a member of another photochromic material, and t being chosen from the integer 1, 2, 3, 4, 5 or 6;
(iv) -OR8, R8 being chosen from C1-C6 alkyl, C1-C6 aryl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, allyl, tri(C1-C6)alkylsilyl, tri(C1-C6)alkoxysilyl, di(C1-C6)alkyl (C1-C6)alkoxysilyl, di(C1-C6)alkoxy(C1-C6)alkylsilyl, benzoyl, mono-substituted benzoyl, naphthoyl or mono-substituted naphthoyl; each of said benzoyl and naphthoyl substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
or R8 being -CH(R9)Q, wherein R9 being chosen from hydrogen or C1-C3 alkyl and Q being chosen from -CN, -CF3, or -COOR10 and R10 being chosen from hydrogen or C1-C3 alkyl; or R8 being -C(O)V, wherein V being chosen from hydrogen, C1-C6 alkoxy, phenoxy, mono- or di-(C1-C6)alkyl substituted phenoxy, mono-or di-(C1-C6)alkoxy substituted phenoxy, an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono-or di-(C1-C6)alkyl substituted phenylamino, or mono- or di-(C1-C6)alkoxy substituted phenylamino: each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(v) -CH(Q')2, Q' being chosen from -CN or -COOR11 and R11 being chosen from hydrogen, C1-C6 alkyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl; each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(vi) -CH(R12)G, R12 being chosen from hydrogen, C1-C6 alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, and G being chosen from -COOR11, -COR13 or -CH2OR14, wherein R13 being chosen from hydrogen, C1-C6 alkyl, an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono- or di-(C1-C6)alkyl substituted phenylamino, mono- or di-(C1-C6)alkoxy substituted phenylamino, diphenylamino, mono- or di(C1-C6)alkyl substituted diphenylamino, mono- or di(C1-C6)alkoxy substituted diphenylamino, morpholino or piperidino R14 being chosen from hydrogen, -C(O)R11, C1-C6 alkyl, C1-C3 alkoxy(C1-C6)alkyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(vii) the group T represented by the formula:
-Z[(OC2H4)x (OC3H6)y (OC4H8)z]Z' -[(OC2H4)x (OC3H6) y (OC9He)z]Z' wherein -Z being chosen from -C(O)- or -CH2-, Z' being chosen from C1-C3 alkoxy or a polymerizable group, x, y and z each being independently chosen from a number between 0 and 50, and the sum of x, y and z being between 2 and 50; or (viii) R2 and R3 together form an oxo group;
(d) R4 is chosen from hydrogen, C1-C6 alkyl or the group R a chosen from:
(i) -OR8', R8' being chosen from phenyl(C1-C3)alkyl, C1-C6 alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, allyl or -CH(R9)Q, R9 being chosen from hydrogen or C1-C3 alkyl; or (ii) a group chosen from:
(1) -N(R15)R16 wherein R15 and R16 being the same as described hereinbefore in (a)(ii);
(2) a nitrogen containing ring represented by the following graphic formula:

wherein Y, X, m and p being the same as described hereinbefore in (a) (iii) ; or (3) a group represented by the following graphic formulae:

wherein R18, R19, R20, R21 and n being the same as described hereinbefore in (a)(iv);
(e) R5 is chosen from hydrogen, C1-C6 alkyl or R a, said R a being the same as described hereinbefore in (d);
(f) R6 is chosen from hydrogen, C1-C6 alkyl or R a, said R a being the same as described hereinbefore in (d): or (g) R5 and R6 together form one of the following graphic formulae:

wherein J and K being independently chosen for each occurrence in each formula from oxygen or -N(R15)-, R15 being the same as described hereinbefore in (a)(ii), R19 and R20 each being the same as described hereinbefore in (a)(iv);
(h) B and B' are each independently chosen from:
(i) mono-T-substituted phenyl;
(ii) an unsubstituted, mono-, di-, or tri-substituted aryl group, phenyl or naphthyl;
(iii) 9-julolidinyl or the unsubstituted, mono-or di-substituted heteroaromatic group chosen from pyridyl furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl or fluorenyl, each of said aryl and heteroaromatic substituents in (h) (ii) and (iii) being independently chosen from hydroxy, -C(O)W, described hereinbefore in (c)(i), aryl, mono(C1-C6)alkoxyaryl, di(C1-C6)alkoxyaryl, mono(C1-C6)alkylaryl, di(C1-C6)alkylaryl, chloroaryl, fluoroaryl, C3-C7 cycloalkylaryl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C3-C7 cycloalkyloxy(C1-C6)alkyl, C3-C7 cycloalkyloxy(C1-C6)alkoxy, aryl(C1-C6)alkyl, aryl(C1-C6)alkoxy, aryloxy, aryloxy(C1-C6)alkyl, aryloxy(C1-C6)alkoxy, mono- or di-(C1-C6)alkylaryl(C1-C6)alkyl, mono- or di-(C1-C6)alkoxyaryl(C1-C6)alkyl, mono- or di-(C1-C6)alkylaryl(C1-C6)alkoxy, mono- or di-(C1-C6)alkoxyaryl(C1-C6)alkoxy, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, diarylamino, piperazino, N-(Cl-C6)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, C1-C6 alkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy, mono(C1-C6)alkoxy(C1-C4)alkyl, acryloxy, methacryloxy, bromo, chloro or fluoro, said aryl being chosen from phenyl or naphthyl;
(iv) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolinyl, phenothiazinyl, phenoxazinyl, phenazinyl or acridinyl, each of said substituents being independently chosen from C1-C6 alkyl, C1-C6 alkoxy, phenyl, fluoro, chloro or bromo;
(v) mono-substituted phenyl, said phenyl having a substituent located at the para position as described hereinbefore in (c)(iii);
(vi) a group represented by one of the following graphic formulae:

wherein A being independently chosen in each formula from methylene or oxygen and D being independently chosen in each formula from oxygen or substituted nitrogen, provided that when D is substituted nitrogen, A is methylene; said nitrogen substituents being chosen from hydrogen, C1-C6 alkyl, or C2-C6 acyl; each R24 being independently chosen for each occurrence in each formula from C1-C6 alkyl, C1-C6 alkoxy, hydroxy, chloro or fluoro; R22 and R23 each being independently chosen in each formula from hydrogen or C1-C6 alkyl; and q being chosen from the integer 0, 1 or 2;
(vii) C1-C6 alkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy(C1-C4)alkyl, C3-C6 cycloalkyl, mono(C1-C6)alkoxy(C3-C6)cycloalkyl, mono(C1-C6)alkyl(C3-C6)-cycloalkyl, chloro(C3-C6)cycloalkyl, fluoro(C3-C6)cyclo-alkyl or C4-C12 bicycloalkyl;
(viii)a group represented by the following graphic formula:

wherein L being chosen from hydrogen or C1-C4 alkyl and M
being chosen from an unsubstituted, mono-, or di-substituted group chosen from naphthyl, phenyl, furanyl, or thienyl; each of said group substituents being independently chosen from C1-C4 alkyl, C1-C4 alkoxy, fluoro, or chloro; or (i) B and B' taken together form fluoren-9-ylidene, mono-, or di-substituted fluoren-9-ylidene or a group being independently chosen from saturated C3-C12 spiro-monocyclic hydrocarbon rings, saturated C7-C12 spiro-bicyclic hydrocarbon rings or saturated C7-C12 spiro-tricyclic hydrocarbon rings; each of said fluoren-9-ylidene substituents being independently chosen from C1-C4 alkyl, C1-C4 alkoxy, fluoro or chloro.
23. The naphthopyran of claim 22 wherein:
(a) R1 is represented by:
(i) -SR7, R7 being chosen from C1-C6 alkyl or aryl, said aryl group being phenyl;
(ii) -N(R15)R16, R15 and R16 each being independently chosen from hydrogen, C1-C6 alkyl, phenyl or C3-C20 cycloalkyl;
(iii) a nitrogen containing ring represented by the following graphic formula:

wherein each Y being -CH2- and X being independently chosen from -Y-, -O-, -S-, -N(R17)- or -N(phenyl)-, R17 being C1-C6 alkyl, m being chosen from the integer 1, 2 or 3, and p being chosen from the integer 0, 1, 2 or 3;
(iv) a group represented by one of the following graphic formulae:

wherein R19, R20 and R21 each being independently chosen from hydrogen, C1-C5 alkyl or phenyl, R18 being independently chosen from hydrogen, C1-C4 alkyl, C1-4 alkoxy, fluoro or chloro and n being chosen from the integer 0 or 1:
(vii) unsubstituted or mono-substituted C5-C18 spirobicyclic amine; or (viii)unsubstituted or mono-substituted C5-C18 spirotricyclic amine:
(b) R1' being independently chosen from C1- C4 alkyl or C1- C4 alkoxy and n being chosen from the integer 0 or 1;
(c) R2 and R3 each being independently chosen from:
(i) hydrogen, hydroxy, C3-C7 cycloalkyl, allyl, benzyl or the group, -C(O)W, wherein W being C1-C6 alkyl or C1-C6 alkoxy:
(ii) an unsubstituted or mono-substituted phenyl, said substituent being chosen from chloro, fluoro, C1-C4 alkyl or C1-C4 alkoxy;
(iii)a mono-substituted phenyl, having a substituent located at the para position that is -(CH2)t- or -O-(CH2)t-, wherein t being chosen from the integer 2 or 3, connected to an aryl group which is a member of another photochromic naphthopyran;
(iv) -OR8, R8 being chosen from C1-C6 alkyl, C1-C6 acyl or phenyl(C1-C3)alkyl: or R8 being the group -CH(R9)Q, wherein R8 being hydrogen and Q being -COOR10, R10 being C1-C3 alkyl, or R8 being the group, -C(O)V, wherein V
being C1-C6 alkoxy;
(v) -CH(Q')2, Q' being -COOR11, wherein R11 being C1-C6 alkyl;

(vi) -CH(R12)G, R12 being hydrogen or C1-C6 alkyls G being -COOR11 or -CH2OR14, wherein R14 being hydrogen, C1-C6 alkyl, or C1-C3 alkoxy(C1-C6)alkyl;
(vii) the group T represented by the formula:
-Z[(OC2H4)x (OC3H6)y (OC4H8)z]Z' wherein -Z being -CH2-, Z' being C1-C3 alkoxy or a polymerizable group, x, y and z each being independently chosen from a number between 0 and 30, and the sum of x, y and z being between 2 and 30; or (viii) R2 and R3 together form an oxo group;
(d) R4 being hydrogen, C1-C6 alkyl or R a, said R a being chosen from:
(i) -OR8', R8' being phenyl(C1-C3)alkyl or C1-C6 alkyl;
(ii) -N(R15)R16, R15 and R16 each being the same as described hereinbefore in (a)(ii);
(iii) a nitrogen containing ring represented by the following graphic formula:

wherein each Y being -CH2-, and X being independently chosen from -Y-, -O-, -S-, -NH-, -N(R17)- or -N(aryl)-, wherein R17 is C1-C6 alkyl, said aryl being chosen from phenyl or naphthyl, m being chosen from the integer 1, 2 or 3, and p being chosen from the integer 0, 1, 2 or 3 provided that when p is 0, X is Y; or (iv) a group represented by one of the following graphic formulae:

wherein R19, R20 and R21 each being independently chosen from hydrogen, C1-C5 alkyl or phenyl;
(e) R5 being chosen from hydrogen, C1-C4 alkyl or R a, said R a being described hereinbefore in (d);
(f) R6 being chosen from hydrogen, C1-C4 alkyl or R a, said R a being described hereinbefore in (d); or (g) R5 and R6 together form one of the following graphic formula:

wherein J and K each being oxygen; and R19 and R20 being the same as described hereinbefore in (d)(iv);
(h) B and B' each being independently chosen from:
(i) mono-T-substituted phenyl;
(ii) an unsubstituted, mono-, di-, or tri substituted aryl group, said aryl being phenyl or naphthyl;
(iii) 9-julolidinyl or the unsubstituted, mono or di-substituted heteroaromatic group chosen from pyridyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, or carbazoyl, each of said aryl and heteroaromatic substituents in (h) (ii) and (iii) being independently chosen from hydroxy, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, aryl(C1-C6)alkyl, aryloxy, aryloxy(C1-C6)alkoxy, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, diarylamino, piperazino, N-arylpiperazino, indolino, piperidino, morpholino, thiomorpholino, pyrrolidyl, C1-C6 alkyl, C1-C6 alkoxy or fluoro;
(iv) an unsubstituted or mono-substituted group chosen from phenothiazinyl or phenoxazinyl, each of said substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(v) a monosubstituted phenyl, said phenyl having a substituent at the para position as described hereinbefore in (c)(iii);
(vi) a group represented by one of the following graphic formulae:

wherein A being independently chosen in each formula from methylene or oxygen and D being independently chosen in each formula from oxygen or substituted nitrogen, provided that when D is substituted nitrogen, A is methylene, said nitrogen substituents being chosen from hydrogen or C1-C4 alkyl; each R24 being C1-C4 alkyl; R22 and R23 each being hydrogen; and q being the integer 0, 1 or 2;
(vii) C1-C6 alkyl, C3-C6 cycloalkyl or C4-C12 bicycloalkyl;
(viii)a group represented by the following graphic formula:

wherein L being chosen from hydrogen or C1-C4 alkyl and M
being chosen from an unsubstituted, mono-, or di-substituted phenyl; each of said phenyl substituents being independently chosen from C1-C4 alkyl or C1-C4 alkoxy; or (i) B and B' taken together form fluoren-9-ylidene or mono-substituted fluoren-9-ylidene or a group being independently chosen from saturated C3-C12 spiro-monocyclic hydrocarbon rings, saturated C3-C12 spiro-bicyclic hydrocarbon rings or saturated C7-C12 spiro-tricyclic hydrocarbon rings;
said fluoren-9-ylidene substituent being chosen from C1-C4 alkyl or C1-C4 alkoxy.
24. The naphthopyran of claim 23 wherein:
(a) R1 is represented by:
(i) -N(R15)R16, R15 and R16 each being independently chosen from C1-C4 alkyl or phenyl:
(ii) a nitrogen containing ring represented by the following graphic formula:

wherein each Y for each occurrence being -CH2- and X being independently chosen from -Y-, -O-, or -N(R17)-, R17 being C1-C4 alkyl, m being chosen from the integer 1 or 2, and p being chosen from the integer 0, 1 or 2; or (iii) a group represented by the following graphic formulae:

wherein R19, R20, and R21 each being hydrogen and n is 0;
(b) R1' being C1-C2 alkyl or C1-C3 alkoxy;
(c) R2 and R3 each being independently chosen from:
(i) hydrogen, hydroxy or C3-C7 cycloalkyl;
(ii) phenyl or mono-(C1-C4 alkoxy) substituted phenyl;
(iii) a mono-substituted phenyl, having a substituent located at the para position being -O-(CH2)t-, t being chosen from the integer 2 or 3, connected to an aryl group being a member of another photochromic naphthopyran;
(iv) -OR8, R8 being C1-C6 alkyl or -CH(R9)Q, R9 being hydrogen, Q being -COOR10, and R10 being C1-C3 alkyl:
(v) -CH(R12)G, R12 being hydrogen; G being -COOR11, wherein R10 being C1-C6 alkyl or C1-C3 alkoxy(C1-C6)alkyl; or (vi) the group T represented by the formula:
-Z[(OC2H4)x (OC3H6)y (OC4H8)z]Z' wherein -Z being -CH2-, Z' being C1-C3 alkoxy, x, y and z each being independently chosen from a number between 0 and 20, and the sum of x, y and z being between 2 and 20;
(d) R4 being hydrogen, C1-C6 alkyl or R a, said R a being chosen from:
(i) -OR8', R8' being C1-C4 alkyl;
(ii) -N(R15)R16, R15 and R16 each being the same as described hereinbefore in (a)(i); or (iii) a nitrogen containing ring represented by the following graphic formula:

wherein each Y being -CH2-, and X being independently chosen from -Y-, -O-, -S-, or -N(R17)-, R17 being C1-C4 alkyl, m being chosen form the integer 1, 2 or 3, and p being chosen form the integer 0, 1, 2 or 3:
(e) R5 being hydrogen or C1-C4 alkyl;
(f) R6 being hydrogen:
(g) B and B' each being independently chosen from:
(i) mono-, di-, and tri-substituted phenyl;
(ii) an unsubstituted, mono- or di-substituted heteroaromatic group chosen from benzofuran-2-yl or dibenzofuranyl, each of said aryl and heteroaromatic substituents in (g) (i) and (ii) being independently chosen from C3-C7 cycloalkyl, aryloxy, aryloxy(C1-C6)alkoxy, di(C1-C6)alkylamino, piperazino, indolino, piperidino, morpholino, pyrrolidyl, C1-C6 alkyl, C1-C6 alkoxy or fluoro;
(iii) a monosubstituted phenyl, said phenyl having a substituent at the para position as described hereinbefore in (c)(iii);
(iv) a group represented by one of the following graphic formulae:

wherein A being methylene and D being independently chosen in each formula from oxygen or substituted nitrogen, said nitrogen substituents being C1-C3 alkyl; each R24 being C1-C3 alkyl; R22 and R23 each being hydrogen; and q being chosen from the integer 0, 1 or 2;
(v) C1-C4 alkyl or C3-C5 cycloalkyl;
(vi) the group represented by the following graphic formula:

wherein L being hydrogen and M being chosen from an unsubstituted, mono-, or di-substituted phenyl, each of said phenyl substituents being C1-C4 alkoxy; or (i) B and B' taken together form fluoren-9-ylidene, mono-substituted fluoren-9-ylidene or a saturated C7-C12 spiro-bicyclic hydrocarbon ring, each of said fluoren-9-ylidene substituents being C1-C4 alkoxy.
25. The naphthopyran of claim 22 wherein said naphthopyran is chosen from:
(a) 3,3-di(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(b) 3-phenyl-3-(4-morpholino-phenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho-[1,2-b]pyran;
(c) 3,3-di(4-(2-methoxyethoxyphenyl))-11-morpholino-13,13 dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(d) 3,3-di(4-methoxyphenyl)-11-morpholino-13-hydroxy-13-ethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(e) 3,3-di(4-methoxyphenyl)-10-methoxy-11-morpholino-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(f) 3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-10-methoxy-11-morpholino-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(g) 3-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)- 11-morpholino -13,13- dimethyl-3H,13H-indeno [2',3':3,4]naphtho[1,2-b]pyran;
(h) 3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-11-morpholino -13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran; or (i) mixtures thereof.
26. The photochromic material of claim 22 wherein said photochromic material is chosen from:
(a) a single photochromic compound (b) a mixture of photochromic compounds;
(c) a material comprising at least one photochromic compound;
(d) a material to which at least one photochromic compound is chemically bonded;
(e) material (c) or (d) further comprising a coating to substantially prevent contact of the at least one photochromic compound with external materials;
(f) a photochromic polymer; or (g) mixtures thereof.
27. A photochromic article comprising an at least partially cured polymer and a photochromic amount of at least one naphthopyran represented by the following graphic formula:

wherein, (a) R1 is represented by:
(i) -SR7, R7 being chosen from C1-C6 alkyl, aryl, mono- or di-substituted aryl, said aryl group being phenyl or naphthyl and each of said aryl substitutents being chosen independently from C1-C6 alkyl, C1-C6 alkoxy or halogen;

(ii) -N(R15)R16, R15 and R16 each being independently chosen from hydrogen, C1-C8 alkyl, aryl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, benzopyridyl, fluorenyl, C1-C8 alkylaryl, C3-C20 cycloalkyl, C4-C20 bicycloalkyl, C5-C20 tricycloalkyl or C1-C20 alkoxyalkyl and said aryl group being phenyl or naphthyl;
(iii) a nitrogen containing ring represented by the following graphic formula:

wherein each Y being independently chosen for each occurrence from -CH2-, -CH(R17)-, -C(R17)(R17)-, -CH(aryl)-, -C(aryl)2-or -C(R17)(aryl)-; X being -Y-, -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(R17)- or -N(aryl)-; R17 being C1-C6 alkyl; said aryl group being phenyl or naphthyl, m being chosen from the integer 1, 2 or 3 and p being chosen from the integer 0, 1, 2 or 3; provided that when p is 0, X is Y;
(iv) a group represented by one of the following graphic formulae:

wherein each R19, R20 and R21 being chosen independently for each occurrence in each formula from hydrogen, C1-C5 alkyl, phenyl or naphthyl; or the groups R19 and R20 together form a ring of 5 to 8 carbon atoms; R18 being chosen independently for each occurrence from C1-C6 alkyl, C1-6 alkoxy, fluoro or chloro and n being chosen from the integer 0, 1 or 2;
(v) unsubstituted, mono- or di- substituted C4-C18 spirobicyclic amine; or (vi) unsubstituted, mono- or di- substituted C4-C18 spirotricyclic amine; said substituents for (v) and (vi) being independently chosen for each occurrence from aryl, C1-C6 alkyl, C1-6 alkoxy or phenyl (C1-C6) alkyl;
(b) R1' is independently chosen for each occurrence from C1-C6 alkyl or C1-C6 alkoxy and n being chosen from the integer 0, 1 or 2;
(c) R2 and R3 are each independently chosen from:
(i) hydrogen, hydroxy, amino, mono- or di-substituted amino, C1-C12 alkyl, C3-C12 alkylidene, C2-C12 alkylidyne, vinyl, C3-C7 cycloalkyl, allyl, C1-C6 haloalkyl, benzyl, mono-substituted benzyl, chloro, fluoro or -C(O)W, wherein W being hydroxy, C1-C6 alkyl, C1-C6 alkoxy, phenyl, mono-substituted phenyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, morpholino, piperidino or pyrrolidyl;
said amino substituents being C1-C6 alkyl, phenyl, benzyl or naphthyl; each of said benzyl and phenyl substituents being C1-C6 alkyl or C1-C6 alkoxy;
(ii) an unsubstituted, mono- di- or tri-substituted group chosen from phenyl, naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl or indolyl; each of said group substituents in (c)(ii) being chosen independently for each occurrence from chloro, fluoro, C1-C6 alkyl or C1-C6 alkoxy;
(iii) a mono-substituted phenyl, said phenyl having a substituent located at the para position being -(CH2)t- or -O-(CH2)t-, connected to an aryl group which is a member of another photochromic material, and t being chosen from the integer 1, 2, 3, 4, 5 or 6;
(iv) -OR8, R8 being chosen from C1-C6 alkyl, C1-C6 acyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, allyl, tri(C1-C6)alkylsilyl, tri(C1-C6)alkoxysilyl, di(C1-C6)alkyl (C1-C6)alkoxysilyl, di(C1-C6)alkoxy(C1-C6)alkylsilyl, benzoyl, mono-substituted benzoyl, naphthoyl or mono-substituted naphthoyl; each of said benzoyl and naphthoyl substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy; or R8 being -CH(R9)Q, wherein R9 being chosen from hydrogen or C1-C3 alkyl and Q being chosen from -CN, -CF3, or -COOR10 and R10 being chosen from hydrogen or C1-C3 alkyl; or R8 being -C(O)V, wherein V being chosen from hydrogen, C1-C6 alkoxy, phenoxy, mono- or di-(C1-C6)alkyl substituted phenoxy, mono- or di-(C1-C6)alkoxy substituted phenoxy, an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono- or di-(C1-C6)alkyl substituted phenylamino, or mono- or di-(C1-C6)alkoxy substituted phenylamino; each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(v) -CH(Q')2, Q' being chosen from -CN or -COOR11 and R11 being chosen from hydrogen, C1-C6 alkyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl; each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(vi) -CH(R12)G, R12 being chosen from hydrogen, C1-C6 alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, and G being chosen from -COOR11, -COR13 or -CH2OR14, wherein R13 being chosen from hydrogen, C1-C6 alkyl, an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono- or di-(C1-C6)alkyl substituted phenylamino, mono- or di-(C1-C6)alkoxy substituted phenylamino, diphenylamino, mono- or di(C1-C6)alkyl substituted diphenylamino, mono- or di(C1-C6)alkoxy substituted diphenylamino, morpholino or piperidino R14 being chosen from hydrogen, -C(O)R11, C1-C6 alkyl, C1-C3 alkoxy(C1-C6)alkyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(vii) the group T represented by the formula:
-Z[(OC2H4)x (OC3H6)y (OC4H8)z]Z' or -[(OC2H9)x (OC3H6)y (OC4H8)Z]Z, wherein -Z being chosen from -C(O)- or -CH2-, Z' being chosen from C1-C3 alkoxy or a polymerizable group, x, y and z each being independently chosen from a number between 0 and 50, and the sum of x, y and z being between 2 and 50; or (viii) R2 and R3 together form an oxo group;
(d) R4 is chosen from hydrogen, C1-C6 alkyl or the group R a chosen from:

(i) -OR8', R8' being chosen from phenyl(C1-C3)alkyl, C1-C6 alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C3-C4 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, allyl or -CH(R9)Q, R9 being chosen from hydrogen or C1-C3 alkyl; or (ii) a group chosen from:
(1) -N(R15)R16 wherein R15 and R16 being the same as described hereinbefore in (a)(ii);
(2) a nitrogen containing ring represented by the following graphic formula:

wherein Y, X, m and p being the same as described hereinbefore in (a)(iii); or (3) a group represented by the following graphic formulae:

wherein R18, R19, R20, R21 and n being the same as described hereinbefore in (a)(iv);
(e) R5 is chosen from hydrogen, C1-C6 alkyl or R a, said R a being the same as described hereinbefore in (d);
(f) R6 is chosen from hydrogen, C1-C6 alkyl or R a, said R a being the same as described hereinbefore in (d); or (g) R5 and R6 together form one of the following graphic formulae:

wherein J and K being independently chosen for each occurrence in each formula from oxygen or -N(R15)-, R19 and R20 each being the same as described herein before;
(h) B and B' are each independently chosen from:
(i) mono-T-substituted phenyl;
(ii) an unsubstituted, mono-, di-, or tri-substituted aryl group, phenyl or naphthyl;
(iii) 9-julolidinyl or the unsubstituted, mono-or di-substituted heteroaromatic group chosen from pyridyl furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl or fluorenyl, each of said aryl and heteroaromatic substituents in (h) (ii) and (iii) being independently chosen from hydroxy, the group, -C(O)W, defined hereinbefore, aryl, mono(C1-C6)alkoxyaryl, di(C1-C6)alkoxyaryl, mono(C1-C6)alkylaryl, di(C1-C6)alkylaryl, chloroaryl, fluoroaryl, C3-C7 cycloalkylaryl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C3-C7 cycloalkyloxy(C1-C6)alkyl, C3-C7 cycloalkyloxy(C1-C6)alkoxy, aryl(C1-C6)alkyl, aryl(C1-C6)alkoxy, aryloxy, aryloxy(C1-C6)alkyl, aryloxy(C1-C6)alkoxy, mono- or di-(C1-C6)alkylaryl(C1-C6)alkyl, mono- or di-(C1-C6)alkoxyaryl(C1-C6)alkyl, mono- or di-(C1-C6)alkylaryl(C1-C6)alkoxy, mono- or di-(C1-C6)alkoxyaryl(C1-C6)alkoxy, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, diarylamino, piperazino, N-(C1-C6)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, C1-C6 alkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy, mono(C1-C6)alkoxy(C1-C4)alkyl, acryloxy, methacryloxy, bromo, chloro or fluoro, said aryl being chosen from phenyl or naphthyl;
(iv) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolinyl, phenothiazinyl, phenoxazinyl, phenazinyl or acridinyl, each of said substituents being independently chosen from C1-C6 alkyl, C1-C6 alkoxy, phenyl, fluoro, chloro or bromo;
(v) monosubstituted phenyl, said phenyl having a substituent at the para position as described hereinbefore in (c)(iii);
(vi) a group represented by one of the following graphic formulae:

wherein A being independently chosen in each formula from methylene or oxygen and D being independently chosen in each formula from oxygen or substituted nitrogen, provided that when D is substituted nitrogen, A is methylene; said nitrogen substituents being chosen from hydrogen, C1-C6 alkyl, or C2-C6 acyl; each R24 being independently chosen for each occurrence in each formula from C1-C6 alkyl, C1-C6 alkoxy, hydroxy, chloro or fluoro; R22 and R23 each being independently chosen in each formula from hydrogen or C1-C6 alkyl; and q being chosen from the integer 0, 1 or 2;
(vii) C1-C6 alkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy(C1-C4)alkyl, C3-C6 cycloalkyl, mono(C1-C6)alkoxy(C3-C6)cycloalkyl, mono(C1-C6)alkyl(C3-C6)-cycloalkyl, chloro(C3-C6)cycloalkyl, fluoro(C3-C6)cyclo-alkyl or C4-C12 bicycloalkyl;
(viii)a group represented by the following graphic formula:

wherein L being chosen from hydrogen or C1-C4 alkyl and M
being chosen from an unsubstituted, mono-, or di-substituted group chosen from naphthyl, phenyl, furanyl, or thienyl; each of said group substituents being independently chosen from C1-C4 alkyl, C1-C4 alkoxy, fluoro, or chloro; or (i) B and B' taken together form fluoren-9-ylidene, mono-, or di-substituted fluoren-9-ylidene or a group being independently chosen from saturated C3-C12 spiro-monocyclic hydrocarbon rings, saturated C7-C12 spiro-bicyclic hydrocarbon rings or saturated C7-C12 spiro-tricyclic hydrocarbon rings; each of said fluoren-9-ylidene substituents being independently chosen from C1-C4 alkyl, C1-C4 alkoxy, fluoro or chloro.
28. The photochromic article of claim 27 further comprising at least one other photochromic material comprising at least one activated absorption maxima within the range of from 400 to 700 nanometers.
29. The photochromic article of claim 28 wherein the at least one other photochromic material is chosen from chromenes, spiropyrans, oxazines, organo-metal dithiozonates, fulgides, fulgimides or a mixture thereof.
30. The photochromic article of claim 27 wherein the at least partially cured polymer is chosen from thermosetting or thermoplastic organic polymeric materials.
31. The photochromic article of claim 30 wherein the at least partially cured polymer is a thermosetting or thermoplastic organic polymeric material which is chosen from poly(C1-C12 alkyl methacrylates), poly(oxyalkylene dimethacrylates), poly(alkoxylated phenol methacrylates), cellulose acetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, poly(vinyl acetate), poly(vinyl alcohol), poly(vinyl chloride), poly(vinylidene chloride), thermoplastic polycarbonates, polyesters, polyurethanes, polythiourethanes, poly(urea-urethane), poly(ethylene terephthalate), polystyrene, poly(alpha methylstyrene), copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile), polyvinylbutyral or is polymerized from monomers chosen from bis(allyl carbonate) monomers, polyfunctional acrylate monomers, polyfunctional methacrylate monomers, diethylene glycol dimethacrylate monomers, diisopropenyl benzene monomers, ethoxylated bisphenol A dimethacrylate monomers, ethylene glycol bismethacrylate monomers, poly(ethylene glycol) bismethacrylate monomers, ethoxylated phenol bis methacrylate monomers, alkoxylated polyhydric alcohol polyacrylate monomers, styrene monomers, urethane acrylate monomers, glycidyl acrylate monomers, glycidyl methacrylate monomers, diallylidene pentaerythritol monomers or mixtures thereof.
32. The photochromic article of claim 27 wherein the at least partially cured polymer is an optical element.
33. The photochromic article of claim 32 wherein the at least partially cured polymer is an optical element and said optical element is an ophthalmic lens.
34. The photochromic article of claim 27 further comprising a superstrate connected to at least a portion of the at least partially cured polymer, said superstrate comprising at least one organic polymeric material.
35. The photochromic article of claim 34 wherein the superstrate is adheringly bonded to at least a portion of the at least partially cured polymer.
36. The photochromic article of claim 34 wherein the superstrate is an organic polymeric material chosen from thermosetting or thermoplastic materials.
37. The photochromic article of claim 36 wherein the superstrate is a thermoplastic material and is polyurethane.
38. The photochromic article of claim 30 further comprising an at least partially abrasion resistant film superposed on at least a portion of the superstrate.
39. The photochromic article of claim 38 wherein the at least partially abrasion resistant film is an organic polymeric material chosen from thermoplastic or thermosetting materials.
40. The photochromic article of claim 39 wherein the at least partially abrasion resistant film is a thermoplastic material and is polycarbonate.
41. The photochromic article of claim 38 further comprising an at least partial coating of an at least partially antireflective coating applied to the at least partially abrasion resistant film superposed on at least a portion of the superstrate.
42. A photochromic article comprising a substrate and an at least partial coating of a photochromic polymeric coating composition comprising a film forming polymer and at least a photochromic amount of at least one naphthopyran represented by the following graphic formula:

wherein, (a) R1 is represented by:
(i) -SR7, R7 being chosen from C1-C6 alkyl, aryl, mono- or di-substituted aryl, said aryl group being phenyl or naphthyl and each of said aryl substitutents being chosen independently from C1-C6 alkyl, C1-C6 alkoxy or halogen;
(ii) -N(R15)R16, R15 and R16 each being independently chosen from hydrogen, C1-C8 alkyl, aryl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, benzopyridyl, fluorenyl, C1-C8 alkylaryl, C3-C20 cycloalkyl, C4-C20 bicycloalkyl, C5-C20 tricycloalkyl or C1-C20 alkoxyalkyl and said aryl group being phenyl or naphthyl;
(iii) a nitrogen containing ring represented by the following graphic formula:

wherein each Y being independently chosen for each occurrence from -CH2-, -CH(R17)-, -C(R17)(R17)-, -CH(aryl)-, -C(aryl)2-or -C(R17)(aryl)-; X being -Y-, -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(R17)- or -N(aryl)-; R17 being C1-C6 alkyl; said aryl group being phenyl or naphthyl, m being chosen from the integer 1, 2 or 3 and p being chosen from the integer 0, 1, 2 or 3; provided that when p is 0, X is Y;
(iv) a group represented by one of the following graphic formulae:

wherein each R19, R20 and R21 being chosen independently for each occurrence in each formula from hydrogen, C1-C5 alkyl, phenyl or naphthyl; or the groups R19 and R20 together form a ring of 5 to 8 carbon atoms; R18 being chosen independently for each occurrence from C1-C6 alkyl, C1-6 alkoxy, fluoro or chloro and n being chosen from the integer 0, 1 or 2;
(v) unsubstituted, mono- or di- substituted C4-C18 spirobicyclic amine; or (vi) unsubstituted, mono- or di- substituted C4-C18 spirotricyclic amine said substituents for (v) and (vi) are independently chosen for each occurrence from aryl, C1-C6 alkyl, C1-6 alkoxy or phenyl (C1-C6) alkyl;
(b) R1' is independently chosen for each occurrence from C1-C6 alkyl or C1-C6 alkoxy and n being chosen from the integer 0, 1 or 2;
(c) R2 and R3 are each independently chosen from:
(i) hydrogen, hydroxy, amino, mono- or di-substituted amino, C1-C12 alkyl, C3-C12 alkylidene, C2-C12 alkylidyne, vinyl, C3-C7 cycloalkyl, allyl, C1-C6 haloalkyl, benzyl, mono-substituted benzyl, chloro, fluoro or -C(O)W, wherein W being hydroxy, C1-C6 alkyl, C1-C6 alkoxy, phenyl, mono-substituted phenyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, morpholino, piperidino or pyrrolidyl;
said amino substituents being C1-C6 alkyl, phenyl, benzyl or naphthyl; each of said benzyl and phenyl substituents being C1-C6 alkyl or C1-C6 alkoxy;
(ii) an unsubstituted, mono- di- or tri-substituted group chosen from phenyl, naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl or indolyl; each of said group substituents in (c)(ii) being chosen independently for each occurrence from chloro, fluoro, C1-C6 alkyl or C1-C6 alkoxy;
(iii) a mono-substituted phenyl, said phenyl having a substituent located at the para position being -(CH2)t- or -O-(CH2)t-, connected to an aryl group which is a member of another photochromic material, and t being chosen from the integer 1, 2, 3, 4, 5 or 6;
(iv) -OR8, R8 being chosen from C1-C6 alkyl, C1-C6 acyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, allyl, tri-C1-C6 alkylsilyl, tri-C1-C6 alkoxysilyl, di-C1-C6 alkyl (C1-C6)alkoxy) silyl, di-C1-C6 alkoxy(C1-C6)alkyl) silyl, benzoyl, mono-substituted benzoyl, naphthoyl or mono-substituted naphthoyl; each of said benzoyl and naphthoyl substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy; or R8 being -CH(R9)Q, wherein R9 being chosen from hydrogen or C1-C3 alkyl and Q being chosen from -CN, -CF3, or -COOR10 and R10 being chosen from hydrogen or C1-C3 alkyl; or R8 being -C(O)V, wherein V being chosen from hydrogen, C1-C6 alkoxy, phenoxy, mono- or di-(C1-C6)alkyl substituted phenoxy, mono- or di-(C1-C6)alkoxy substituted phenoxy, an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono- or di-(C1-C6)alkyl substituted phenylamino, or mono- or di-(C1-C6)alkoxy substituted phenylamino; each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(v) -CH(Q')2, Q' being chosen from -CN or -COOR11 and R11 being chosen from hydrogen, C1-C6 alkyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl; each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(vi) -CH(R12)G, R12 being chosen from hydrogen, C1-C6 alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, and G being chosen from -COOR11, -COR13 or -CH2OR14, wherein R13 being chosen from hydrogen, C1-C6 alkyl, an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono- or di-(C1-C6)alkyl substituted phenylamino, mono- or di-(C1-C6)alkoxy substituted phenylamino, diphenylamino, mono- or di(C1-C6)alkyl substituted diphenylamino, mono- or di(C1-C6)alkoxy substituted diphenylamino, morpholino or piperidino R14 being chosen from hydrogen, -C(O)R11, C1-C6 alkyl, C1-C3 alkoxy(C1-C6)alkyl, phenyl(C1-C6)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(vii) the group T represented by the formula:
-Z[(OC2H4)x (OC3H6)y (OC4H8)z]Z' or -[(C2H4)x (OC3H6)y (OC4H8)z]Z' wherein -Z being chosen from -C(O)- or -CH2-, Z' being chosen from C1-C3 alkoxy or a polymerizable group, x, y and z each being independently chosen from a number between 0 and 50, and the sum of x, y and z being between 2 and 50; or (viii) R2 and R3 together form an oxo group;
(d) R4 is chosen from hydrogen, C1-C6 alkyl or the group R a chosen from:
(i) -OR8', R8' being chosen from phenyl(C1-C3)alkyl, C1-C6 alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, allyl or -CH(R9)Q, R9 being chosen from hydrogen or C1-C3 alkyl; or (ii) a group chosen from:

(1) -N(R15)R16 wherein R15 and R16 being the same as described hereinbefore in (a)(ii);
(2) a nitrogen containing ring represented by the following graphic formula:

wherein Y, X, m and p being the same as described hereinbefore in (a)(iii); or (3) a group represented by the following graphic formulae:

wherein R18, R19, R20, R21 and n being the same as described hereinbefore in (a)(iv);
(e) R5 is chosen from hydrogen, C1-C6 alkyl or R a, said R a being the same as described hereinbefore in (d);
(f) R6 is chosen from hydrogen, C1-C6 alkyl or R a, said R a being the same as described hereinbefore in (d); or (g) R5 and R6 together form one of the following graphic formulae:

wherein J and K being independently chosen for each occurrence in each formula from oxygen or -N(R15)-, R19 and R20 each being the same as described herein before;
(h) B and B' are each independently chosen from:

(i) mono-T-substituted phenyl;
(ii) an unsubstituted, mono-, di-, or tri-substituted aryl group, phenyl or naphthyl;
(iii) 9-julolidinyl or the unsubstituted, mono-or di-substituted heteroaromatic group chosen from pyridyl furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl or fluorenyl, each of said aryl and heteroaromatic substituents in (h) (ii) and (iii) being independently chosen from hydroxy, the group, -C(O)W, defined hereinbefore, aryl, mono(C1-C6)alkoxyaryl, di(C1-C6)alkoxyaryl, mono(C1-C6)alkylaryl, di(C1-C6)alkylaryl, chloroaryl, fluoroaryl, C3-C7 cycloalkylaryl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C3-C7 cycloalkyloxy(C1-C6)alkyl, C3-C7 cycloalkyloxy(C1-C6)alkoxy, aryl(C1-C6)alkyl, aryl(C1-C6)alkoxy, aryloxy, aryloxy(C1-C6)alkyl, aryloxy(C1-C6)alkoxy, mono- or di-(C1-C6)alkylaryl(C1-C6)alkyl, mono- or di-(C1-C6)alkoxyaryl(C1-C6)alkyl, mono- or di-(C1-C6)alkylaryl(C1-C6)alkoxy, mono- or di-(C1-C6)alkoxyaryl(C1-C6)alkoxy, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, diarylamino, piperazino, N-(C1-C6)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, C1-C6 alkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy, mono(C1-C6)alkoxy(C1-C4)alkyl, acryloxy, methacryloxy, bromo, chloro or fluoro, said aryl being chosen from phenyl or naphthyl;
(iv) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolinyl, phenothiazinyl, phenoxazinyl, phenazinyl or acridinyl, each of said substituents being independently chosen from C1-C6 alkyl, C1-C6 alkoxy, phenyl, fluoro, chloro or bromo;
(v) monosubstituted phenyl, said phenyl having a substituent at the para position as described hereinbefore in (c)(iii);
(vi) a group represented by one of the following graphic formulae:

wherein A being independently chosen in each formula from methylene or oxygen and D being independently chosen in each formula from oxygen or substituted nitrogen, provided that when D is substituted nitrogen, A is methylene; said nitrogen substituents being chosen from hydrogen, C1-C6 alkyl, or C2-C6 acyl; each R24 being independently chosen for each occurrence in each formula from C1-C6 alkyl, C1-C6 alkoxy, hydroxy, chloro or fluoro; R22 and R23 each being independently chosen in each formula from hydrogen or C1-C6 alkyl; and q being chosen from the integer 0, 1 or 2;
(vii) C1-C6 alkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy(C1-C4)alkyl, C3-C6 cycloalkyl, mono(C1-C6)alkoxy(C3-C6)cycloalkyl, mono(C1-C6)alkyl(C3-C6)-cycloalkyl, chloro(C3-C6)cycloalkyl, fluoro(C3-C6)cyclo-alkyl or C4-C12 bicycloalkyl;
(viii)a group represented by the following graphic formula:

wherein L being chosen from hydrogen or C1-C4 alkyl and M
being chosen from an unsubstituted, mono-, or di-substituted group chosen from naphthyl, phenyl, furanyl, or thienyl; each of said group substituents being independently chosen from C1-C4 alkyl, C1-C4 alkoxy, fluoro, or chloro.
43. The photochromic article of claim 42 wherein the photochromic polymeric coating composition further comprises at least one other photochromic material comprising at least one activated absorption maxima within the range of from 400 to 700 nanometers.
44. The photochromic article of claim 43 wherein the at least one other photochromic material is chosen from chromenes, spiropyrans, oxazines, organo-metal dithiozonates, fulgides, fulgimides or a mixture thereof.
45. The photochromic article of claim 43 wherein the substrate is paper, glass, ceramic, wood, masonry, textile, metal or polymeric organic material.
46. The photochromic article of claim 45 wherein the substrate is polymeric organic material which is a solid transparent polymer chosen from thermosetting or thermoplastic organic polymeric materials.
47. The photochromic article of claim 46 wherein the substrate is a solid transparent polymer which is an optical element.
48. The photochromic article of claim 47 wherein the substrate is an optical element which is an ophthalmic lens.
49. The photochromic article of claim 42 wherein the film-forming polymer is chosen from thermosetting or thermoplastic organic polymeric materials.
50. The photochromic article of claim 49 wherein the film forming polymer is thermosetting and is chosen from polyurethanes, poly(meth)acrylates, aminoplast resins, polysilanes, polyanhydrides, polyacrylamides or epoxy resins.
51. The photochromic article of claim 42 further comprising a primer at least partially interposed between the substrate and the at least partial coating of a photochromic polymeric coating composition.
52. The photochromic article of claim 51 further comprising an at least partially abrasion resistant coating applied to at least a portion of the surface of the at least partial coating of a photochromic polymeric coating composition.
53. The photochromic article of claim 52 further comprising an at least partial coating of an at least partially antireflective coating applied to the at least partially abrasion resistant coating applied to at least a portion of the surface of the at least partial coating of a photochromic polymeric coating composition.
54. A naphthol represented by one of the following graphic formulae:

wherein, Leaving Group is chosen from halogen, tosyl, brosyl, mesyl or trifyl;
(a) R1 is represented by:
(i) -SR7, R7 being chosen from C1-C6 alkyl, aryl, mono- or di-substituted aryl, said aryl group being phenyl or naphthyl and each of said aryl substitutents being chosen independently from C1-C6 alkyl, C1-C6 alkoxy or halogen;
(ii) -N(R15)R16, R15 and R16 each being independently chosen from hydrogen, C1-C8 alkyl, aryl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, benzopyridyl, fluorenyl, C1-C8 alkylaryl, C3-C20 cycloalkyl, C3-C20 bicycloalkyl, C5-C20 tricycloalkyl or C1-C20 alkoxyalkyl and said aryl group being phenyl or naphthyl;
(iii) a nitrogen containing ring represented by the following graphic formula:

wherein each Y being independently chosen for each occurrence from -CH2-, -CH(R17)-, -C(R17)(R17)-, -CH(aryl)-, -C(aryl)2-or -C(R17)(aryl)-; X being -Y-, -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(R17)- or -N(aryl)-; R17 being C1-C6 alkyls said aryl group being phenyl or naphthyl, m being chosen from the integer 1, 2 or 3 and p being chosen from the integer 0, 1, 2 or 3; provided that when p is 0, X is Y;
(iv) a group represented by one of the following graphic formulae:

wherein each R19, R20 and R21 being chosen independently for each occurrence in each formula from hydrogen, C1-C5 alkyl, phenyl or naphthyl; or the groups R19 and R20 together form a ring of 5 to 8 carbon atoms; R18 being chosen independently for each occurrence from C1-C6 alkyl, C1-C6 alkoxy, fluoro or chloro and n being chosen from the integer 0, 1 or 2:
(v) unsubstituted, mono- or di- substituted C4-C18 spirobicyclic amine; or (vi) unsubstituted, mono- or di- substituted C4-C18 spirotricyclic amine; said substituents for (v) and (vi) being independently chosen for each occurrence from aryl, C1-C6 alkyl or C1-C6 alkoxy or phenyl (C1-C6) alkyl;
(b) R1' is independently chosen for each occurrence from C1-C6 alkyl or C1-C6 alkoxy and n being chosen from the integer 0, 1 or 2:
(c) each R2 or each R3 is independently chosen for each occurrence from:
(i) hydrogen, hydroxy, amino, mono- or di-substituted amino, C1-C12 alkyl, C3-C12 alkylidene, C2-C12 alkylidyne, vinyl, C3-C7 cycloalkyl, C1-C6 aloalkyl, allyl, benzyl, mono-substituted benzyl, chloro, fluoro or -C(O)W, wherein W being hydroxy, C1-C6 alkyl, C1-C6 alkoxy, phenyl, mono-substituted phenyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, morpholino, piperidino or pyrrolidyl;
said amino substituents being C1-C6 alkyl, phenyl, benzyl or naphthyl; each of said benzyl and phenyl substituents being C1-C6 alkyl or C1-C6 alkoxy;
(ii) an unsubstituted, mono- di- or tri-substituted group chosen from phenyl, naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl or indolyl; each of said group substituents in (c)(ii) being chosen independently for each occurrence from chloro, fluoro, C1-C6 alkyl or C1-C6 alkoxy;
(iii) a monosubstituted phenyl, said phenyl having a substituent located at the para position being -(CH2)t- or -O-(CH2)t-, connected to an aryl group which is a member of another photochromic material, and t being chosen from the integer 1, 2, 3, 4, 5 or 6;
(iv) -OR8, R8 being chosen from C1-C6 alkyl, C1-C6 acyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, allyl, tri(C1-C6)alkylsilyl, tri(C1-C6)alkoxysilyl, di(C1-C6)alkyl (C1-C6)alkoxysilyl, di(C1-C6)alkoxy(C1-C6)alkylsilyl, benzoyl, mono-substituted benzoyl, naphthoyl or mono-substituted naphthoyl; each of said benzoyl and naphthoyl substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
or R8 being -CH(R9)Q, wherein R9 being chosen from hydrogen or C1-C3 alkyl and Q being chosen from -CN, -CF3, or -COOR10 and R10 being chosen from hydrogen or C1-C3 alkyl; or R8 being -C(O)V, wherein V being chosen from hydrogen, C1-C6 alkoxy, phenoxy, mono- or di-(C1-C6)alkyl substituted phenoxy, mono-or di-(C1-C6)alkoxy substituted phenoxy, an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono-or di-(C1-C6)alkyl substituted phenylamino, or mono- or di-(C1-C6)alkoxy substituted phenylamino; each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(v) -CH(Q')2, Q' being chosen from -CN or -COOR11 and R11 being chosen from hydrogen, C1-C6 alkyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl; each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(vi) -CH(R12)G, R12 being chosen from hydrogen, C1-C6 alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, and G being chosen from -COOR11, -COR13 or -CH2OR14, wherein R13 being chosen from hydrogen, C1-C6 alkyl, an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono- or di-(C1-C6)alkyl substituted phenylamino, mono- or di-(C1-C6)alkoxy substituted phenylamino, diphenylamino, mono- or di(C1-C6)alkyl substituted diphenylamino, mono- or di(C1-C6)alkoxy substituted diphenylamino, morpholino or piperidino R14 being chosen from hydrogen, -C(O)R11, C1-C6 alkyl, C1-C3 alkoxy(C1-C6)alkyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl or an unsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl, each of said aryl group substituents being independently chosen from C1-C6 alkyl or C1-C6 alkoxy;
(vii) the group T represented by the formula:
-Z[(OC2H4)x (OC3H6)y (OC4H8)z]Z' -[(OC2H4)x (OC3H6)y (OC4H8)z]Z' wherein -Z being chosen from -C(O)- or -CH2-, Z' being chosen from C1-C3 alkoxy or a polymerizable group, x, y and z each being independently chosen from a number between 0 and 50, and the sum of x, y and z being between 2 and 50; or (viii) R2 and R2 or R3 and R3 together form an oxo group:
(d) R4 is chosen from hydrogen, C1-C6 alkyl or the group R a chosen from:
(i) -OR8', R8' being chosen from phenyl(C1-C3)alkyl, C1-C6 alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, allyl or -CH(R9)Q, R9 being chosen from hydrogen or C1-C3 alkyl; or (ii) a group chosen from:
(1) -N(R15)R16 wherein R15 and R16 being the same as described hereinbefore in (a)(ii);
(2) a nitrogen containing ring represented by the following graphic formula:

wherein Y, X, m and p being the same as described hereinbefore in (a)(iii); or (3) a group represented by the following graphic formulae:

wherein R18, R19, R20, R21 and n being the same as described herein before;
(e) R5 is chosen from hydrogen, C1-C6 alkyl or R a, said R a being the same as described hereinbefore in (d);
(f) R6 is chosen from hydrogen, C1-C6 alkyl or R a, said R a being the same as described hereinbefore in (d); or (g) R5 and R6 together form one of the following graphic formulae:

wherein J and K being independently chosen for each occurrence in each formula from oxygen or -N(R15)-, R15 being the same as described hereinbefore in (a)(ii), R19 and R20 each being the same as described hereinbefore in (a)(iv).
55. The naphthol of claim 54 wherein said naphthol is represented by one of the following graphic formulae:

56. The naphthol of claim 54 wherein said naphthol is chosen from:
(a) 7,7-dimethyl-5-hydroxy-9-fluoro-7H-benzo[C]fluorene;
(b) 7-dimethyl-7-methoxy-5-hydroxy-9-fluoro-7H-benzo[C]fluorene;
(c) 7,7-dimethyl-5-hydroxy-9-morpholino-7H-benzo[C]fluorene;
(d) 7,7-dimethyl-5-hydroxy-10-methoxy-9-morpholino-7H-benzo[C]fluorene;
(e) 7-dimethyl-7-methoxy-5-hydroxy-9-dimethylamino-7H-benzo[C]fluorene;
(f) 7-ethyl-7-methoxy-5-hydroxy-9-piperidino-7H-benzo[C]fluorene;

(g) 7,7-dimethyl-5-hydroxy-9-piperidino-7H-benzo[C]fluorene;
(h) 7,7-dimethyl-3-methoxy-5-hydroxy-9-morpholino-7H-benzo[C]fluorene;
(i) 7,7-dimethyl-3,4-dimethoxy-5-hydroxy-9-morpholino-7H-benzo[C]fluorene;
(j) 7,7-dimethyl-3-methoxy-4-methyl-5-hydroxy-9-morpholino-7H-benzo[C]fluorene;
(k) 7,7-dimethyl-5-hydroxy-9-phenylthio-7H-benzo[C]fluorene;
(l) 7-phenyl-7-hydroxy-3-methoxy-4-methyl-5-hydroxy-9-morpholino-7H-benzo[C]fluorene;
(m) 7-ethyl-7-methoxy-5-hydroxy-9-phenylthio-7H-benzo[C]fluorene; or (n) mixtures thereof.
CA 2512605 2003-03-20 2004-03-16 Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles Expired - Lifetime CA2512605C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/393,177 US7262295B2 (en) 2003-03-20 2003-03-20 Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles
US10/393,177 2003-03-20
PCT/US2004/008156 WO2005090327A1 (en) 2003-03-20 2004-03-16 Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles

Publications (2)

Publication Number Publication Date
CA2512605A1 true CA2512605A1 (en) 2004-09-20
CA2512605C CA2512605C (en) 2012-05-29

Family

ID=32988076

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2512605 Expired - Lifetime CA2512605C (en) 2003-03-20 2004-03-16 Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles

Country Status (13)

Country Link
US (3) US7262295B2 (en)
EP (3) EP1606274B9 (en)
JP (1) JP4160980B2 (en)
KR (1) KR100752834B1 (en)
CN (2) CN1761660B (en)
AU (1) AU2004311372B8 (en)
BR (1) BRPI0408540B1 (en)
CA (1) CA2512605C (en)
ES (2) ES2394446T3 (en)
HK (1) HK1089161A1 (en)
MX (1) MXPA05009631A (en)
WO (1) WO2005090327A1 (en)
ZA (1) ZA200508177B (en)

Families Citing this family (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050258408A1 (en) * 2001-12-20 2005-11-24 Molock Frank F Photochromic contact lenses and methods for their production
US20110140056A1 (en) * 2003-07-01 2011-06-16 Transitions Optical, Inc. Indeno-fused ring compounds
US8698117B2 (en) 2003-07-01 2014-04-15 Transitions Optical, Inc. Indeno-fused ring compounds
US8211338B2 (en) 2003-07-01 2012-07-03 Transitions Optical, Inc Photochromic compounds
US7632540B2 (en) 2003-07-01 2009-12-15 Transitions Optical, Inc. Alignment facilities for optical dyes
US8545984B2 (en) 2003-07-01 2013-10-01 Transitions Optical, Inc. Photochromic compounds and compositions
US8518546B2 (en) 2003-07-01 2013-08-27 Transitions Optical, Inc. Photochromic compounds and compositions
WO2005059060A1 (en) * 2003-12-15 2005-06-30 Worcester Polytechnic Institute Films with photoresponsive wettability
US8147725B2 (en) 2005-04-08 2012-04-03 Transitions Optical, Inc Photochromic materials having extended pi-conjugated systems and compositions and articles including the same
US20060227287A1 (en) * 2005-04-08 2006-10-12 Frank Molock Photochromic ophthalmic devices made with dual initiator system
US9028728B2 (en) 2005-04-08 2015-05-12 Transitions Optical, Inc. Photochromic materials that include indeno-fused naphthopyrans
US9139552B2 (en) 2005-04-08 2015-09-22 Transitions Optical, Inc. Indeno-fused naphthopyrans having ethylenically unsaturated groups
US20060226402A1 (en) * 2005-04-08 2006-10-12 Beon-Kyu Kim Ophthalmic devices comprising photochromic materials having extended PI-conjugated systems
US7556750B2 (en) * 2005-04-08 2009-07-07 Transitions Optical, Inc. Photochromic materials with reactive substituents
US8158037B2 (en) 2005-04-08 2012-04-17 Johnson & Johnson Vision Care, Inc. Photochromic materials having extended pi-conjugated systems and compositions and articles including the same
US9052438B2 (en) * 2005-04-08 2015-06-09 Johnson & Johnson Vision Care, Inc. Ophthalmic devices comprising photochromic materials with reactive substituents
US8647538B2 (en) 2005-04-08 2014-02-11 Transitions Optical, Inc. Photochromic compounds having at least two photochromic moieties
US20060228557A1 (en) * 2005-04-08 2006-10-12 Beon-Kyu Kim Photochromic materials having extended pi-conjugated systems and compositions and articles including the same
US9034457B2 (en) * 2006-09-11 2015-05-19 Alphamicron Incorporated Photochromic devices and methods for making the same
EP2076767A2 (en) * 2006-10-26 2009-07-08 Ciba Holding Inc. Light absorbing layer for photo-chromic systems
US8748634B2 (en) * 2006-10-30 2014-06-10 Transitions Optical, Inc. Photochromic materials demonstrating improved fade rates
US7667285B2 (en) * 2006-12-14 2010-02-23 Motorola, Inc. Printed electronic substrate havine photochromic barrier layer
JP5320722B2 (en) * 2007-11-06 2013-10-23 東ソー株式会社 Benzofluorenone derivative and method for producing the same
US20100014010A1 (en) * 2008-06-27 2010-01-21 Transitions Optical, Inc. Formulations comprising mesogen containing compounds
US20090326186A1 (en) * 2008-06-27 2009-12-31 Transitions Optical, Inc. Mesogen containing compounds
US8628685B2 (en) 2008-06-27 2014-01-14 Transitions Optical, Inc Mesogen-containing compounds
US8431039B2 (en) 2008-06-27 2013-04-30 Transitions Optical, Inc. Mesogenic stabilizers
US8623238B2 (en) 2008-06-27 2014-01-07 Transitions Optical, Inc. Mesogenic stabilizers
US8613868B2 (en) 2008-06-27 2013-12-24 Transitions Optical, Inc Mesogenic stabilizers
US7910020B2 (en) * 2008-06-27 2011-03-22 Transitions Optical, Inc. Liquid crystal compositions comprising mesogen containing compounds
US7910019B2 (en) 2008-06-27 2011-03-22 Transitions Optical, Inc. Mesogen containing compounds
US8349210B2 (en) 2008-06-27 2013-01-08 Transitions Optical, Inc. Mesogenic stabilizers
US8217188B2 (en) * 2008-08-27 2012-07-10 Corning Incorporated 2H-chromenes annelated at C5-C6 and methods of making and using thereof
CN101503484B (en) * 2009-03-04 2010-11-17 东北师范大学 Method for synthesizing photochromic cross-linked polymer containing naphthyl hydroxide pyran group
US8518305B2 (en) 2009-10-28 2013-08-27 Transitions Optical, Inc. Photochromic materials
JPWO2011078030A1 (en) * 2009-12-22 2013-05-02 株式会社トクヤマ Chromene compounds
US9139571B2 (en) 2010-12-16 2015-09-22 Transitions Optical, Inc. Methods of making fused ring compounds
US8859097B2 (en) * 2010-12-16 2014-10-14 Transitions Optical, Inc. Photochromic compounds, compositions and articles
US8920928B2 (en) 2010-12-16 2014-12-30 Transitions Optical, Inc. Photochromic compounds and compositions
US9034219B2 (en) * 2010-12-16 2015-05-19 Transitions Optical, Inc. Photochromic compounds and compositions
ES2545336T3 (en) 2011-01-28 2015-09-10 Tokuyama Corporation Chromene compound
JP6355209B2 (en) * 2013-03-04 2018-07-11 株式会社トクヤマ Photochromic curable composition, cured product thereof, and laminate comprising the cured product
US9029565B1 (en) 2013-11-20 2015-05-12 Transitions Optical, Inc. Fused ring indeno compounds for preparation of photochromic compounds
US9206151B2 (en) 2013-11-20 2015-12-08 Transitions Optical, Inc. Method of preparing fused ring indeno compounds
US9051332B1 (en) 2013-11-20 2015-06-09 Transitions Optical, Inc. Photochromic indeno-fused ring pyran compounds
US20190048122A1 (en) * 2015-09-16 2019-02-14 Mitsui Chemicals, Inc. Polymerizable composition for optical material, optical material obtained from the composition, and plastic lens
CN106218172A (en) * 2016-08-30 2016-12-14 常州山由帝杉防护材料制造有限公司 Photochromic fenestrated membrane
CN108047008A (en) * 2017-12-18 2018-05-18 蚌埠学院 A kind of preparation method of 3,4- dimethoxy-benzophenones
CN112105676B (en) * 2018-05-17 2023-08-29 株式会社德山 Low water content polyrotaxane monomer and curable composition containing the same
CN113227053A (en) 2018-12-21 2021-08-06 光学转变有限公司 Process for preparing indole naphthopyrans
BR112021011870A2 (en) 2018-12-21 2021-08-31 Transitions Optical, Ltd. ARTICLES INCLUDING INDOLNAPHTOPIRANS
CN113227098A (en) 2018-12-21 2021-08-06 光学转变有限公司 Indol naphthopyrans
AU2018454273A1 (en) 2018-12-21 2021-07-15 Transitions Optical, Ltd. Indolenaphthopyrans and photochromic compositions comprising them
JP2022151089A (en) * 2021-03-26 2022-10-07 ホヤ レンズ タイランド リミテッド Indeno-fused naphthopyran compound particles, method for producing polymerizable composition, and method for producing photochromic article
CN113735694A (en) * 2021-09-14 2021-12-03 西安瑞联新材料股份有限公司 Method for synthesizing 9-halogen-7H-benzo [ c ] fluorene-7-ketone

Family Cites Families (66)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3361706A (en) 1964-03-06 1968-01-02 American Cyanamid Co Control of the photochromic return rate of (arylazo) thioformic arylhydrazidates
US4166043A (en) 1974-12-23 1979-08-28 American Optical Corporation Stabilized photochromic materials
US4367170A (en) 1975-01-24 1983-01-04 American Optical Corporation Stabilized photochromic materials
US4360653A (en) 1981-10-23 1982-11-23 Ppg Industries, Inc. Polymerizate of (allyl carbonate) and aliphatic polyurethane having acrylic unsaturation
US4720356A (en) 1982-03-22 1988-01-19 American Optical Corporation Photochromic composition resistant to fatigue
US4556605A (en) 1982-09-09 1985-12-03 Kabushiki Kaisha Suwa Seikosha Photochromic coating composition and photochromic synthetic resin ophthalmic lens
AU564689B2 (en) 1985-07-09 1987-08-20 Kureha Kagaku Kogyo K.K. Photochromic lens
CA1340939C (en) 1987-02-02 2000-03-28 Ryojiro Akashi Photochromic compound
GB8712210D0 (en) 1987-05-22 1987-06-24 Pilkington Brothers Plc Photochromic articles
US4798745A (en) 1987-08-24 1989-01-17 Ppg Industries, Inc. Non-yellowing coating composition based on a hydroxy component and an anhydride component and utilization in a process of coating
US4798746A (en) 1987-08-24 1989-01-17 Ppg Industries, Inc. Basecoat/clearcoat method of coating utilizing an anhydride additive in the thermoplastic polymer-containing basecoat for improved repairability
US4873029A (en) 1987-10-30 1989-10-10 Blum Ronald D Method for manufacturing lenses
US4931220A (en) 1987-11-24 1990-06-05 Ppg Industries, Inc. Organic photochromic pigment particulates
US5252742A (en) 1989-02-28 1993-10-12 Otsuka Kagaku Kabushiki Kaisha Spiropyran compounds
US4994208A (en) 1989-04-18 1991-02-19 Ppg Industries, Inc. Photochromic polymeric article
ATE130850T1 (en) 1989-07-28 1995-12-15 Wako Pure Chem Ind Ltd FULGIMIDE DERIVATIVES.
DE69119507T2 (en) 1990-02-23 1996-10-02 Otsuka Kagaku Kk BENZOSELENAZOLINE SPIRO VINYL PYRANE DERIVATIVE AND POLYMER BASED ON IT
US5373033A (en) 1990-04-20 1994-12-13 Sola International Holdings Limited Casting composition
US5239012A (en) 1991-02-21 1993-08-24 Ppg Industries, Inc. Ambient temperature curing compositions containing a hydroxy component and an anhydride component and an onium salt
US5200483A (en) 1991-11-07 1993-04-06 Ppg Industries, Inc. Polyol(allyl carbonate) composiitons and articles prepared there from
CA2144084C (en) 1992-09-25 1999-01-12 John S. Ligas Photochromic compositions of improved fatigue resistance
US5274132A (en) 1992-09-30 1993-12-28 Transitions Optical, Inc. Photochromic naphthopyran compounds
EP0593397B1 (en) 1992-10-15 1996-12-27 Ciba-Geigy Ag Polymerisable photochromic naphthacendiones, polymers of these monomers, their process of preparation and their use
AU665480B2 (en) 1993-01-29 1996-01-04 Tokuyama Corporation Polymerizable composition, polymer, organic glass and ophthalmic lens
US5618586A (en) 1994-03-29 1997-04-08 Ppg Industries, Inc. N-alkoxymethyl (meth)acrylamide functional polymers and their use in self-crosslinkable coating compositions
FR2723218A1 (en) 1994-07-29 1996-02-02 Essilor Internal Cie Gle Optique PHOTOCHROMIC COMPOUNDS WITH A SPIRO STRUCTURE (INDOLINE- (2,3 ') - BENZOXAZINE) WITH A CYANO GROUP IN 6', AND THEIR USE IN THE FIELD OF OPHTHALMIC OPTICS
US5760100B1 (en) 1994-09-06 2000-11-14 Ciba Vision Corp Extended wear ophthalmic lens
US5645767A (en) 1994-11-03 1997-07-08 Transitions Optical, Inc. Photochromic indeno-fused naphthopyrans
IL115803A (en) 1994-11-03 2000-02-17 Ppg Industries Inc Indeno-naphthopyran derivatives useful for photochromic articles
US5658501A (en) 1995-06-14 1997-08-19 Transitions Optical, Inc. Substituted naphthopyrans
AUPN443695A0 (en) 1995-07-28 1995-08-17 Sola International Holdings Ltd Photochromic polymer
US5753146A (en) 1996-03-29 1998-05-19 Transitions Optical, Inc. Photochromic naphthopyran compositions of neutral color
US5770115A (en) 1996-04-19 1998-06-23 Ppg Industries, Inc. Photochromic naphthopyran compositions of improved fatigue resistance
US5723072A (en) 1996-06-17 1998-03-03 Ppg Industries, Inc. Photochromic heterocyclic fused indenonaphthopyrans
SG54538A1 (en) 1996-08-05 1998-11-16 Hoya Corp Soft contact lens with high moisture content and method for producing the same
US5821287A (en) 1996-08-08 1998-10-13 National Science Council Photochromic pigment
AU718471B2 (en) 1997-02-21 2000-04-13 Ppg Industries Ohio, Inc. Photochromic polyurethane coating and articles having such a coating
US6025026A (en) 1997-06-30 2000-02-15 Transitions Optical, Inc. Process for producing an adherent polymeric layer on polymeric substrates and articles produced thereby
US5961631A (en) * 1997-07-16 1999-10-05 Arm Limited Data processing apparatus and method for pre-fetching an instruction in to an instruction cache
DE19741705A1 (en) 1997-09-22 1999-04-01 Rodenstock Optik G Photochromic indeno(2,1-f)naphtho(1,2-b)pyran compounds useful e.g. in photochromic spectacle lenses
WO1999015518A1 (en) 1997-09-22 1999-04-01 Optische Werke G. Rodenstock Photochromic naphtopyrane colorants, method for the production and use thereof, photochromic object
US6268055B1 (en) 1997-12-08 2001-07-31 Ppg Industries Ohio, Inc. Photochromic epoxy resin coating composition and articles having such a coating
US5869658A (en) * 1997-12-15 1999-02-09 Ppg Industries, Inc. Photochromic indeno-fused naptho 2,1-b!pyrans
EP0987260B1 (en) 1998-05-29 2004-03-03 Rodenstock GmbH Photochromic spirofluorenopyrans
DE69903042T2 (en) 1998-07-10 2003-08-07 Transitions Optical Inc PHOTOCHROME SIX-LINKED HETEROCYCLIC-CONDENSED NAPHTHOPYRANE
US5961892A (en) 1998-09-11 1999-10-05 Ppg Industries Ohio, Inc. Polyalkoxylated naphthopyrans
BR9913869A (en) 1998-09-11 2004-12-28 Ppg Ind Ohio Inc Naphthoopyran Compound and Photochromic Articles
US6555028B2 (en) 1998-09-11 2003-04-29 Transitions Optical, Inc. Polymeric matrix compatibilized naphthopyrans
US6060001A (en) 1998-12-14 2000-05-09 Ppg Industries Ohio, Inc. Alkoxyacrylamide photochromic coatings compositions and photochromic articles
US6432544B1 (en) 1998-12-18 2002-08-13 Ppg Industries Ohio, Inc. Aminoplast resin photochromic coating composition and photochromic articles
US6506488B1 (en) 1998-12-18 2003-01-14 Ppg Industries Ohio, Inc. Aminoplast resin photochromic coating composition and photochromic articles
US6432522B1 (en) * 1999-02-20 2002-08-13 Saint-Gobain Vitrage Transparent acoustical and mechanical barrier
US6340765B1 (en) * 1999-05-20 2002-01-22 Tokuyama Corporation Chromene compound
WO2001002449A2 (en) 1999-07-02 2001-01-11 Ppg Industries Ohio, Inc. Poly(meth)acrylic photochromic coating
DE50000137D1 (en) 1999-07-02 2002-05-16 Rodenstock Optik G Spirofluorenopyrane
US6150430A (en) 1999-07-06 2000-11-21 Transitions Optical, Inc. Process for adhering a photochromic coating to a polymeric substrate
US6348604B1 (en) 1999-09-17 2002-02-19 Ppg Industries Ohio, Inc. Photochromic naphthopyrans
US6296785B1 (en) 1999-09-17 2001-10-02 Ppg Industries Ohio, Inc. Indeno-fused photochromic naphthopyrans
FR2800738B1 (en) * 1999-11-04 2002-02-08 Corning Sa NAPHTOPYRANS HAVING A PERFLUOROALKYL SUBSTITUTE IN POSITION 5, PREPARATION AND COMPOSITIONS AND (CO) POLYMERIC MATRICES CONTAINING THEM
CA2359046C (en) * 1999-11-10 2006-10-10 Optische Werke G. Rodenstock Heterocyclically anellated indenochromene derivatives
US6353102B1 (en) 1999-12-17 2002-03-05 Ppg Industries Ohio, Inc. Photochromic naphthopyrans
JP4157245B2 (en) 2000-02-21 2008-10-01 株式会社トクヤマ Chromene compounds
WO2001094336A1 (en) 2000-06-07 2001-12-13 Optische Werke G. Rodenstock Photochromic pyran derivatives
CN1152108C (en) * 2000-06-12 2004-06-02 中国科学院感光化学研究所 Arylheterocycle substituted naphthopyran-type photochromic compound and its preparing process and usage
US7166357B2 (en) * 2003-03-20 2007-01-23 Transitions Optical, Inc. Photochromic articles that activate behind ultraviolet radiation blocking transparencies and methods for preparation
US20040186241A1 (en) * 2003-03-20 2004-09-23 Gemert Barry Van Photochromic ocular devices

Also Published As

Publication number Publication date
US20070155964A1 (en) 2007-07-05
CN102532088B (en) 2016-10-12
JP4160980B2 (en) 2008-10-08
US7557208B2 (en) 2009-07-07
CA2512605C (en) 2012-05-29
JP2006525378A (en) 2006-11-09
EP2345648B1 (en) 2012-10-24
MXPA05009631A (en) 2006-08-25
ZA200508177B (en) 2007-01-31
CN1761660B (en) 2012-01-11
EP1606274A1 (en) 2005-12-21
CN1761660A (en) 2006-04-19
BRPI0408540B1 (en) 2014-09-02
ES2688272T3 (en) 2018-10-31
WO2005090327A1 (en) 2005-09-29
US7262295B2 (en) 2007-08-28
US20090062533A1 (en) 2009-03-05
AU2004311372A8 (en) 2009-03-05
KR100752834B1 (en) 2007-08-29
EP1606274B1 (en) 2018-08-08
EP2345647A2 (en) 2011-07-20
HK1089161A1 (en) 2006-11-24
US20040185255A1 (en) 2004-09-23
AU2004311372B8 (en) 2009-03-05
EP1606274B9 (en) 2019-01-16
AU2004311372A1 (en) 2005-09-15
CN102532088A (en) 2012-07-04
EP2345647A3 (en) 2011-11-23
EP2345648A1 (en) 2011-07-20
KR20060061289A (en) 2006-06-07
US7517982B2 (en) 2009-04-14
ES2394446T3 (en) 2013-01-31
BRPI0408540A (en) 2006-03-07
AU2004311372B2 (en) 2007-08-02

Similar Documents

Publication Publication Date Title
CA2512605A1 (en) Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles
CA2385725A1 (en) Novel indeno-fused photochromic naphthopyrans
JP2003509418A5 (en)
EP1866699B1 (en) Photochromic materials with reactive substituents
AU709675B2 (en) Novel photochromic heterocyclic fused indenonaphthopyrans
CA2603706A1 (en) Photochromic indeno-fused naphthopyrans having extended pi-conjugated systems, compositions and articles including the same
CO5410192A1 (en) NEW PHOTOCROMIC NAFTOPIRANS
JP2007526223A5 (en)
JP2002524559A5 (en)
KR970707453A (en) A novel photochromic indeno-fused naphthopyran (NOVEL PHOTOCHROMIC INDENO-FUSED NAPHTHOPYRANS)
JPH06500100A (en) Photochromic chromene compound
WO2000015629B1 (en) Polymerizable polyalkoxylated naphthopyrans
US8535577B2 (en) Photochromic materials that include 6-amino substituted indeno-fused naphthopyrans
JP2013545803A5 (en)
AU2007202187B2 (en) Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles
DE29522188U1 (en) New photochromic indeno-fused naphthopyrans

Legal Events

Date Code Title Description
EEER Examination request