# US 10,501,446 B2 · Photochromic compounds

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- Number: US 10,501,446 B2
- Document ID: US10501446B2
- Status: Granted
- Kind: B2
- Application number: 16/007,067
- Filed: 2018-06-13
- Published: 2018-10-11
- Granted: 2019-12-10
- Earliest claimed: 2003-07-01
- Assignees: Transitions Optical, Inc.
- Applicants: Transitions Optical, Inc.
- Inventors: Meng He; Darrin R. Dabideen; Terry A. Kellar, II; Anil Kumar
- Web page: https://patentgrep.com/patent/US10501446B2

## CPC

- C07D 405/10: linked by a carbon chain containing aromatic rings
- C07D 311/92: Naphthopyrans; Hydrogenated naphthopyrans
- C07D 311/94: condensed with rings other than six-membered or with ring systems containing such rings
- C09B 11/26: Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic {(phthaleins C09B11/24)}
- C09B 57/00: Other synthetic dyes of known constitution
- C09K 9/02: Organic tenebrescent materials
- G02B 1/04: made of organic materials, e.g. plastics (G02B1/08 takes precedence)
- G02B 5/223: {containing organic substances, e.g. dyes, inks or pigments}
- G02B 5/23: Photochromic filters
- G02B 5/3016: {involving passive liquid crystal elements (optical properties of liquid crystals G02F1/0063; polarising elements associated with active liquid crystal devices G02F1/133528)}
- G02C 7/102: {Photochromic filters}
- G03C 1/685: Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
- G03C 1/73: containing organic compounds
- C09K 2211/1011: Condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1033: with oxygen
- C09K 2211/1088: containing oxygen as the only heteroatom
- Y10T 428/31507: Of polycarbonate
- Y10T 428/31551: Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T 428/31663: As siloxane, silicone or silane
- Y10T 428/31786: Of polyester [e.g., alkyd, etc.]
- Y10T 428/31938: Polymer of monoethylenically unsaturated hydrocarbon
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02C: SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES (trial frames for testing the eyes A61B3/04; goggles or eyeshields not having the same features as spectacles A61F9/00)
- G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

A photochromic compound is provided, which may be a pyran, an oxazine, or a fulgide. The photochromic compound has at least one substituent Q attached thereto, each Q independently being —N3, —CN, —COOR′, —CCR′, —C(R′)C(R′)R′, —OCOR′, —OCOOR′, —SR′, —OSO2R′″, and/or —CON(R′)R′, wherein each R′ is hydrogen, an unsubstituted or substituted alkyl group having from 1 to 18 carbon atoms; an unsubstituted or substituted aryl group, an unsubstituted or substituted alkene or alkyne group having from 2 to 18 carbon atoms, wherein the substituents are halo or hydroxyl and R″′ is —CF3 or a perfluorinated alkyl group having from 2 to 18 carbon atoms The number, locations and nature of the constituents Q are dependent upon the structure of the photochromic compound.

## Claims

### Claim 1

A photochromic material represented by the following graphic formula:
wherein:
(A) substituent Q comprises —N3, —CN, —COOR′, —CCR′, —C(R′)C(R′)R′, —OCOR′, —OCOOR′, —SR′, —OSO2R″′, and/or —CONHR′, wherein R′ independently comprises hydrogen, an unsubstituted or substituted alkyl group having from 1 to 18 carbon atoms, an unsubstituted or substituted aryl group, an unsubstituted or substituted alkene or alkyne group having from 2 to 18 carbon atoms, wherein said substituents are chosen from halo and hydroxyl and R″′ comprises —CF3 or a perfluorinated alkyl group having from 2 to 18 carbon atoms;
(B) i is an integer chosen from 0 to the total number of available positions and each R is independently chosen for each occurrence from:
(a) a group represented by B described hereinafter;
(b) —C(O)X24, wherein X24 is chosen from a lengthening agent L, hydroxy, C1-C18 alkyl, C1-C18 alkoxy, phenyl that is unsubstituted or mono-substituted with C1-C18 alkyl or C1-C18 alkoxy, amino that is unsubstituted, mono- or di-substituted with at least one of C1-C18 alkyl, phenyl, benzyl, and naphthyl;
(c) —OX7 and —N(X7)2 ; wherein X7 is chosen from:
(i) a lengthening agent L, hydrogen, C1-C18 alkyl, C1-C18 acyl, phenyl(C1-C18)alkyl, mono(C1-C18)alkyl substituted phenyl(C1-C18)alkyl, mono(C1-C18)alkoxy substituted phenyl(C1-C18)alkyl; C1-C18 alkoxy(C1-C18)alkyl; C3-C10 cycloalkyl; mono(C1-C18)alkyl substituted C3-C10 cycloalkyl, C1-C18 haloalkyl, allyl, benzoyl, mono-subsituted benzoyl, naphthoyl or mono-substituted naphthoyl, wherein each of said benzoyl and naphthoyl substituents are independently chosen from C1-C18 alkyl, and C1-C18 alkoxy;
(ii) —CH(X8)X9, wherein X8 is chosen from a lengthening agent L, hydrogen or C1-C18 alkyl; and X9 is chosen from a lengthening agent L, —CN, —CF3, or —COOX10, wherein X10 is chosen from a lengthening agent L, hydrogen or C1-C18 alkyl;
(iii) —C(O)X6, wherein X6 is chosen from at least one of: a lengthening agent L, hydrogen, C1-C18 alkoxy, phenoxy that is unsubstituted, mono- or di- substituted with C1-C18 alkyl or C1-C18 alkoxy, an aryl group that is unsubstituted, mono- or di-substituted with C1-C18 alkyl or C1-C18 alkoxy, an amino group that is unsubstituted, mono- or di-substituted with C1-C18 alkyl, and a phenylamino group that is unsubstituted, mono- or di-substituted with C1-C18 alkyl or C1-C18 alkoxy;or
(iv) tri(C1-C18)alkylsilyl, tri(C1-C18)alkylsilyloxy, tri(C1-C18)alkoxysilyl, tri(C1-C 18)alkoxysilyloxy, di(C1-C18)alkyl(C1-C18 alkoxy)silyl, di(C1-C18)alkyl(C1-C18 alkoxy)silyloxy, di(C1-C18)alkoxy(C1-C18 alkyl)silyl or di(C1-C18)alkoxy(C1-C18 alkyl)silyloxy;
(d) —SX11; wherein X11 is chosen from a lengthening agent L, hydrogen, C1-C18 alkyl, C1-C18 haloalkyl, an aryl group that is unsubstituted, or mono- or di- substituted with C1-C18 alkyl, C1-C18 alkoxy, or halogen;
(e) a nitrogen containing ring represented by Formula i:
wherein
(i) n is an integer chosen from 0, 1, 2, and 3, and each U is independently chosen for each occurrence from —CH2—, —CH(X12)—, —C(X12)2—, —CH(X13)—, —C(X13)2—, and —C(X12)(X13)—, wherein X12 is chosen from a lengthening agent L and C1-C12 alkyl, and X13 is chosen from a lengthening agent L, phenyl and naphthyl, and
(ii) U′ is chosen from U, —O—, —S—, —S(O)—, —NH—, —N(X12)— or —N(X13)—, and m is an integer chosen from 1, 2, and 3;
(f) the group represented by Formula ii or iii;
wherein X14, X15, and X16 are independently chosen for each occurrence from a lengthening agent L, hydrogen, C1-C18 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 8 carbon atoms; p is an integer chosen from 0, 1, or 2, and X17 is independently chosen for each occurrence from a lengthening agent L, C1-C18 alkyl, C1-C18 alkoxy, or halogen;
(g) immediately adjacent R groups together form a group represented by Formula vii, viii, or ix:
wherein
(i) W and W′ are independently chosen for each occurrence from —O—, —N(X7)—, —C(X14)—, and —C(X17)—;
(ii) X14, X15 and X17, wherein X14, and X15 are independently chosen for each occurrence from a lengthening agent L, hydrogen, C1-C18 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 8 carbon atoms; and X17 is independently chosen for each occurrence from a lengthening agent L, C1-C18 alkyl, C1-C18 alkoxy, or halogen; and
(iii) q is an integer chosen from 0, 1, 2, 3, and 4; and
(h) a lengthening agent L represented by:
—[S1]c-[Q1-[S2]d]d′-[Q2-[S3]e]e′-[Q3-[S4]f]f′—S5—P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, liquid crystal mesogens, halogen, poly(C1-C 18 alkoxy), C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkoxycarbonyloxy, aryloxycarbonyloxy, perfluoro(C1-C18)alkoxy, perfluoro (C1-C18)alkoxycarbonyl, perfluoro(C1-C18)alkylcarbonyl, perfluoro(C1-C18)alkylamino, di-(perfluoro(C1-C18)alkyl)amino, perfluoro(C1-C18)alkylthio, C1-C18 alkylthio, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1)and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from 0 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(1) —(CH2)g—, —(CF2)h—, —Si(CH2)g—, —(Si[(CH3)2]O)h—, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(2) —N(Z)—, —C(Z)═C(Z)—, —C(Z)═N—, —C(Z′)—C(Z′)— or a single bond, wherein Z is independently chosen for each occurrence from hydrogen, C1-C18 alkyl, C3-C10 cycloalkyl and aryl, and Z′ is independently chosen for each occurrence from C1-C18 alkyl, C3-C10 cycloalkyl and aryl; and
(3) —O—, —C(O)—, —C≡C—, —N═N—, —S—, —S(O)—, —S(O)(O)—, —(O)S(O)—, —(O)S(O)O—, —O(O)S(O)O—, or straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo; provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: hydroxy, amino, C2-C18 alkenyl, C2-C18 alkynyl, azido, silyl, siloxy, silylhydride, (tetrahydro-2H-pyran-2-yl)oxy, thio, isocyanato, thioisocyanato, acryloyloxy, methacryloyloxy, 2-(acryloyloxy)ethylcarbamyl, 2-(methacryloyloxy)ethylcarbamyl, aziridinyl, allyloxycarbonyloxy, epoxy, carboxylic acid, carboxylic ester, acryloylamino, methacryloylamino, aminocarbonyl, C1-C18 alkyl aminocarbonyl, amino carbonyl(C1 -C18)alkyl, C1-C18 alkyloxycarbonyloxy, halocarbonyl, hydrogen, aryl, hydroxy(C1-C 18)alkyl, C1-C18 alkyl, C1-C18 alkoxy, amino(C1-C18)alkyl, C1-C18 alkylamino, di-(C1 -C18)alkylamino, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxy(C1-C18)alkoxy, nitro, poly(C1-C18)alkyl ether, (C1-C18)alkyl(C1-C18)alkoxy(C1-C 18)alkyl, polyethyleneoxy, polypropyleneoxy, ethyl enyl, acryloyl, acryloyloxy(C1-C18)alkyl, methacryloyl, methacryloyloxy(C1-C18)alkyl, 2-chloroacryloyl, 2-phenylacryloyl, acryloyloxyphenyl, 2-chloroacryloylamino, 2-phenylacryloylaminocarbonyl, oxetanyl, glycidyl, cyano, isocyanato(C1-C18)alkyl, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, main-chain and side-chain liquid crystal polymers, siloxane derivatives, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, or substituted or unsubstituted chiral or non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from C1-C18 alkyl, C1-C18 alkoxy, amino, C3-C10 cycloalkyl, C1-C18 alkyl(C1-C18)alkoxy, fluoro(C1-C18)alkyl, cyano, cyano(C1-C18)alkyl, cyano(C1-C18)alkoxy or mixtures thereof, or P is a structure having from 2 to 4 reactive groups or P is an unsubstituted or substituted ring opening metathesis polymerization precursor; and
(iv) d′, e′ and f′ are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d′ +e′ +f′ is at least 1;
(C) each B is independently chosen from:
(i) hydrogen, C1-C18 alkyl, C2-C18 alkylidene, C2-C18 alkylidyne, vinyl, C3-C10 cycloalkyl, C1-C18 haloalkyl, allyl, halogen, and benzyl that is unsubstituted or mono-substituted with at least one of C1-C18 alkyl and C1-C18 alkoxy;
(ii) phenyl that is mono-substituted at the para position with at least one substituent chosen from: C1-C18 alkoxy, linear or branched chain C1-C20 alkylene, linear or branched chain C1-C4 polyoxyalkylene, cyclic C3-C20 alkylene, phenylene, naphthylene, C1-C18 alkyl substituted phenylene, mono- or poly-urethane(C1-C20)alkylene, mono- or poly-ester(C1-C20)alkylene, mono-or poly-carbonate(C1-C20)alkylene, polysilanylene, polysiloxanylene and mixtures thereof wherein the at least one substituent is connected to an aryl group of a photochromic material;
(iii) —CH(CN)2 and —CH(COOX1)2, wherein X1 is chosen from at least one of a lengthening agent L, hydrogen, C1-C18 alkyl that is unsubstituted or mono-substituted with phenyl, phenyl(C1-C 18)alkyl that is mono-substituted with C1-C18 alkyl, C1-C18 haloalkyl or C1-C18 alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C18 alkyl and C1-C18 alkoxy; and lengthening agent L;
(iv) —CH(X2)(X3), wherein:
(I) X2 is chosen from at least one of a lengthening agent L, hydrogen, C1-C18 alkyl, and an aryl group that is unsubstituted, mono-or di-substituted, wherein each aryl substituent is independently chosen from C1 -C18 alkyl and C1 -C18 alkoxy; and
(2) X3 is chosen from at least one of —COOX1, —COX1, —COX4, and —CH2OX5, wherein: X4 is chosen from at least one of morpholino, piperidino, amino that is unsubstituted, mono- or di- substituted with C1-C18 alkyl, and an unsubstituted, mono or di- substituted group chosen from phenylamino and diphenylamino, wherein each substituent is independently chosen from C1-C18 alkyl or C1-C18 alkoxy;
and X5 is chosen from a lengthening agent L, hydrogen, —C(O)X2, C1-C18 alkyl that is unsubstituted or mono-substituted with (C1-C18)alkoxy or phenyl, phenyl(C1-C18)alkyl that is mono-substituted with (C1-C18)alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C18 alkyl and C1-C18 alkoxy;
(v) an unsubstituted, mono-, di-, or tri- substituted aryl group; 9-julolidinyl; or an 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; wherein each aryl and heteroaromatic group substituent is independently chosen for each occurrence from:
(1) a lengthening agent L;
(2) —COOX1 or —C(O)X6;
(3) aryl, haloaryl, C3-C10 cycloalkylaryl, and an aryl group that is mono- or di-substituted with C1-C18 alkyl or C1-C18 alkoxy;
(4) C1-C18 alkyl, C3-C10 cycloalkyl, C3-C10 cycloalkyloxy(C1-C18)alkyl, aryl(C1-C18)alkyl, aryloxy(C1-C18)alkyl, mono- or di- (C1-C18)alkylaryl(C1-C18)alkyl, mono- or di- (C1-C18)alkoxyaryl(C1-C18)alkyl, C1-C18 haloalkyl, and mono(C1-C18)alkoxy(C1-C18)alkyl;
(5) C1-C18 alkoxy, C3-C10 cycloalkoxy, cycloalkyloxy(C1-C18)alkoxy, aryl(C1-C18)alkoxy, aryloxy(C1-C18)alkoxy, mono- or di- (C1-C18)alkylaryl(C1-C18)alkoxy, and mono- or di- (C1-C18)alkoxyaryl(C1-C18)alkoxy;
(6) aminocarbonyl, aminocarbonyl(C1-C18)alkylene, amino, mono- or di-alkylamino, diarylamino, piperazino, N-(C1-C18)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, hydroxy, acryloxy, methacryloxy, and halogen;
(7) —OXO or —N(X7)2;
(8) —SX11;
(9) a nitrogen containing ring represented by Formula i;
(10) a group represented by Formula ii or iii;
(11) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolidinyl, phenothiazinyl, phenoxazinyl, phenazinyl, or acridinyl, wherein each substituent is independently chosen from a lengthening agent L, C1-C18 alkyl, C1-C18 alkoxy, phenyl, hydroxy, amino or halogen;
(12) a group represented by Formula iv or v:
wherein:
(I) V′ is independently chosen in each formula from —O—, —CH—, C1- C6 alkylene, and C3-C10 cycloalkylene,
(II) V is independently chosen in each formula from —O— or —N(X21)—, wherein X21 is a lengthening agent L, hydrogen, C1-C18 alkyl, and C2-C18 acyl, provided that if V is —N(X21)—, V′ is —CH2—,
(III) X18 and X19 are each independently chosen from a lengthening agent L, hydrogen and C1-C18 alkyl, and
(IV) k is chosen from 0, 1, and 2, and each X20 is independently chosen for each occurrence from a lengthening agent L, C1-C18 alkyl, C1-C18 alkoxy, hydroxy and halogen; or
(13) a group represented by Formula vi:
wherein
(I) X22 is chosen from a lengthening agent L, hydrogen and C1-C18 alkyl, and
(II) X23 is chosen from a lengthening agent L and an unsubstituted, mono-, or di-substituted group chosen from naphthyl, phenyl, furanyl and thienyl, wherein each substituent is independently chosen for each occurrence from C1-C18 alkyl, C1-C18 alkoxy, and halogen;
(D) provided that when said photochromic material is represented by graphic formula VI, Q comprises: —N3, —CN, —CCR′, or —OSO2R″′; E is —O— or —N(Q)-; and D is represented by the following graphic formula:
wherein: T is —S—, —O— or —N(R)—, J is a spiro-alicyclic ring and Q is the same as described hereinbefore.

### Claim 2 (depends on 1)

A photochromic composition comprising the photochromic material of claim 1 incorporated into at least a portion of an organic material, said organic material being a polymeric material, an oligomeric material, a monomeric material or a mixture or combination thereof.

### Claim 3 (depends on 2)

The photochromic composition of claim 2, wherein said polymeric material comprises self-assembling materials, polycarbonate, polyamide, polyimide, poly(meth)acrylate, polycyclic alkene, polyurethane, poly(urea)urethane, polythiourethane, polythio(urea)urethane, polyol(allyl carbonate), cellulose acetate, cellulose diacetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, polyalkene, polyalkylene-vinyl acetate, poly(vinylacetate), poly(vinyl alcohol), poly(vinyl chloride), poly(vinylformal), poly(vinylacetal), poly(vinylidene chloride), poly(ethylene terephthalate), polyester, polysulfone, polyolefin, copolymers thereof, and/or mixtures thereof.

### Claim 4 (depends on 2)

The photochromic composition of claim 2, wherein the photochromic composition further comprises at least one additive chosen from dyes, alignment promoters, kinetic enhancing additives, photoinitiators, thermal initiators, polymerization inhibitors, solvents, light stabilizers, heat stabilizers, mold release agents, rheology control agents, leveling agents, free radical scavengers, gelators and adhesion promoters.

### Claim 5 (depends on 2)

The photochromic composition of claim 2, comprising a coating composition chosen from self-assembling materials and film forming materials.

### Claim 6 (depends on 1)

A photochromic article comprising a substrate and a photochromic material according to claim 1 connected to at least a portion of a substrate.

### Claim 7 (depends on 6)

The photochromic article of claim 6, comprising an optical element, said optical element being at least one of an ophthalmic element, a display element, a window, a mirror, packaging material and an active or passive liquid crystal cell element.

### Claim 8 (depends on 7)

The photochromic article of claim 7, wherein the ophthalmic element comprises corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses, or visors.

### Claim 9 (depends on 7)

The photochromic article of claim 7, wherein the display element comprises screens, monitors and security elements.

### Claim 10 (depends on 6)

The photochromic article of claim 6, wherein the substrate comprises a polymeric material and the photochromic material is incorporated into at least a portion of the polymeric material.

### Claim 11 (depends on 10)

The photochromic article of claim 10, wherein the photochromic material is blended with at least a portion of the polymeric material, bonded to at least a portion of the polymeric material, and/or imbibed into at least a portion of the polymeric material.

### Claim 12 (depends on 6)

The photochromic article of claim 6, wherein the photochromic article comprises a coating or film connected to at least a portion of the substrate, said coating or film comprising the photochromic material.

### Claim 13 (depends on 12)

The photochromic article of claim 12, wherein said substrate is formed from organic materials, inorganic materials, or combinations thereof.

### Claim 14 (depends on 11)

The photochromic article of claim 11, further comprising at least one additional at least partial coating chosen from photochromic coatings, anti-reflective coatings, linearly polarizing coatings, transitional coatings, alignment layers, primer coatings, adhesive coatings, mirrored coatings and protective coatings including antifogging coatings, oxygen barrier coatings and ultraviolet light absorbing coatings.