Photochromic article comprising photochromic layer and UV absorbing layer

Abstract

The present invention relates to a photochromic article comprising: (a) a substrate; (b) a photochromic layer comprising a photochromic compound on the substrate; and (c) a UV absorbing layer comprising a UV absorber on the photochromic layer. The photochromic layer has an unactivated state absorbance greater than 0 over at least a portion of a wavelength of 250 nm to 450 nm. An end minimum absorbance wavelength value of the UV absorbing layer is at least 45 nm less than a first unactivated end minimum absorbance wavelength value of the photochromic layer. The invention also relates to ophthalmic articles, such as corrective lenses.

Description

Technical Field

[0001] The present invention relates to a photochromic article, which includes: a substrate; a photochromic layer containing a photochromic compound on the substrate; and an ultraviolet (UV) absorbing layer containing a UV absorber on the photochromic layer, wherein the UV absorbing layer has a terminal minimum absorbance wavelength value that is at least 45 nm less than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer. Background Art

[0002] Photochromic compounds and materials can be used in compositions to form, for example, layers, such as films, such as photochromic coatings, which are photochromic. In some cases, the photochromic composition is curable and a cured photochromic layer, such as a cured photochromic coating, can be formed therefrom. Exposing the photochromic layer to actinic radiation (such as sunlight including ultraviolet (UV) light / radiation) typically and ideally results in the photochromic material of the photochromic layer being converted from an unactivated (or whitish, e.g., substantially colorless) state to an activated (or colored) state. Without exposure to actinic radiation, such photochromic compounds and materials can reversibly convert from an activated (or colored) state back to an unactivated (or whitish) state.

[0003] After prolonged and repeated exposure to actinic radiation, the photochromic material of the photochromic layer may become undesirably unstable or fatigued. Instability and fatigue of the photochromic material can result in, for example, a reduction in the efficiency and amplitude of the color change of the photochromic material, a color shift of the activated photochromic material, and the development of discoloration such as yellowing of the matrix of the photochromic layer. Typically, the reduction in the efficiency of the color change of the photochromic material is proportional to the half-life (T 1 / 2 A decrease in the magnitude of the color change of a photochromic material is typically associated with a decrease in the optical density change (ΔOD) value.

[0004] To improve the stability and fatigue resistance of the photochromic layer, one or more UV absorbers may be included in the photochromic layer and / or in a separate layer thereon. The presence of UV absorbers in and / or on the photochromic layer generally has associated therewith undesirable effects, such as undesirable attenuation of the photochromic material thereof. Attenuation of the photochromic material is typically evidenced by a reduction in the level or amplitude of the coloration of the photochromic material when fully activated.

[0005] It would be desirable to develop photochromic articles whose photochromic materials have improved stability and fatigue resistance. It would also be desirable for such newly developed photochromic articles to have minimal attenuation of the photochromic materials. Summary of the invention

[0006] According to the present invention, a photochromic article is provided, which comprises: (a) a substrate; (b) a photochromic layer comprising a photochromic material, wherein the photochromic layer is stacked on the substrate, and the photochromic layer has an unactivated state absorbance greater than 0 over at least a portion of the wavelength from 250 nm to 450 nm and a first unactivated state terminal minimum absorbance wavelength value; and (c) a UV absorbing layer comprising a UV absorber, the UV absorbing layer is stacked on the photochromic layer, and the UV absorbing layer has a terminal minimum absorbance wavelength value. The terminal minimum absorbance wavelength value of the UV absorbing layer is at least 45 nm smaller than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer.

[0007] The features that characterize the present invention are specifically pointed out in the claims, which are attached to and form a part of this disclosure. These and other features of the present invention, its operating advantages and specific objects obtained by its use will be more fully understood from the following detailed description, in which non-limiting embodiments of the present invention are illustrated and described. BRIEF DESCRIPTION OF THE DRAWINGS

[0008] Figure 1 is a representative side cross-sectional view of a photochromic article according to the present invention; and

[0009] Figure 2 is a graphical representation of absorbance versus wavelength obtained from photochromic layer test samples (Examples 1 and 2) and UV absorbing layer test samples (Examples BH) as described in further detail in the Examples herein.

[0010] Unless otherwise stated, Figure 1 and 2 1 and 2. In the present disclosure, like reference numerals may refer to like parts and / or elements as appropriate. DETAILED DESCRIPTION

[0011] As used herein, the articles "a," "an," and "the" include plural referents unless expressly and unequivocally limited to the one referent.

[0012] Unless otherwise indicated, all ranges or ratios disclosed herein should be understood to include any and all values ​​and subranges or subratios contained therein. For example, the range or ratio of "1 to 10" should be deemed to include: any and all values ​​therebetween, including the end values ​​(such as 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10); and the subranges between the minimum value 1 and the maximum value 10 (and including the end values), that is, all subranges or subratios starting with a minimum value of 1 or greater and ending with a maximum value of 10 or less, such as but not limited to 1 to 6.1, 3.5 to 7.8, and 5.5 to 10.

[0013] As used herein, unless otherwise indicated, a left-to-right representation of a linking group, such as a divalent linking group, includes other suitable orientations, such as but not limited to a right-to-left orientation. For non-limiting illustration purposes, a divalent linking group or equivalently, the left-to-right representation of -C(O)O- includes its right-to-left representation or equivalently -O(O)C- or -OC(O)-.

[0014] Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients, reaction conditions, and so forth used in the specification and claims are to be understood as modified in all instances by the term "about".

[0015] As used herein, the term "polymer" means homopolymers (eg, prepared from a single monomer species), copolymers (eg, prepared from at least two monomer species), and grafted polymers.

[0016] As used herein, the term "(meth)acrylate" and similar terms (such as "(meth)acrylic acid ester") means methacrylate and / or acrylate. As used herein, the term "(meth)acrylic acid" means methacrylic acid and / or acrylic acid.

[0017] As used herein, the term "photochromic" and similar terms (such as "photochromic compound") means having an absorption spectrum for at least visible radiation that changes in response to the absorption of at least actinic radiation. Further, as used herein, the term "photochromic material" means any substance suitable for displaying photochromic properties (such as suitable for having an absorption spectrum for at least visible radiation that changes in response to the absorption of at least actinic radiation) and containing at least one photochromic compound.

[0018] As used herein, the term "actinic radiation" means electromagnetic radiation capable of inducing a material response, such as, but not limited to, transforming a photochromic material from one form or state to another, as discussed in further detail herein.

[0019] As used herein, the term "photochromic material" includes thermally reversible photochromic materials and compounds and non-thermally reversible photochromic materials and compounds. As used herein, the term "thermally reversible photochromic compound / material" means a compound / material that can be converted from a first state (e.g., a "transparent state") to a second state (e.g., a "colored state") in response to actinic radiation and can return to the first state in response to thermal energy. As used herein, the term "non-thermally reversible photochromic compound / material" means a compound / material that can be converted from a first state (e.g., a "transparent state") to a second state (e.g., a "colored state") in response to actinic radiation and can return to the first state in response to one or more wavelengths of actinic radiation that are substantially the same as one or more absorptions of the colored state.

[0020] As used herein, the terms "first" and "second" are not intended to refer to any particular order or timing, but rather to two different conditions or properties, for purposes of non-limiting illustration. For purposes of non-limiting illustration, the first state and the second state of the photochromic compound may differ in at least one optical property, such as, but not limited to, the absorption of visible radiation and / or UV radiation. Thus, according to various non-limiting embodiments disclosed herein, the photochromic compounds of the present invention may have different absorption spectra in each of the first and second states. For example, although not limited herein, the photochromic compounds of the present invention may be transparent in the first state and colored in the second state. Alternatively, the photochromic compounds of the composition of the present invention may have a first color in the first state and a second color in the second state.

[0021] The first state (e.g., transparent state or first color) of a photochromic compound / material (whether thermally reversible or non-thermally reversible) is also referred to herein as the "unactivated state" of the photochromic compound / material. The second state (e.g., colored state or second color) of a photochromic compound / material (whether thermally reversible or non-thermally reversible) is also referred to herein as the "activated state" of the photochromic compound / material.

[0022] As used herein, the term "optical" means relating to or associated with light and / or vision. For example, according to various non-limiting embodiments disclosed herein, the optical article or element or device can be selected from ophthalmic articles, elements and devices, display articles, elements and devices, windows, mirrors, and active and passive liquid crystal cell articles, elements and devices.

[0023] As used herein, the term "ophthalmic" means pertaining to or relating to the eye and vision. Non-limiting examples of ophthalmic articles or components include corrective and non-corrective lenses (including single-vision or multi-vision lenses, which may be segmented or non-segmented multi-vision lenses (such as, but not limited to, bifocal lenses, trifocal lenses, and progressive lenses)), and other components used to correct, protect, or enhance (cosmetic or other) vision (including, but not limited to, contact lenses, intraocular lenses, magnifying lenses, and protective lenses or goggles).

[0024] As used herein, the term "display" means a visible or machine-readable representation of information in the form of words, numbers, symbols, designs, or diagrams. Non-limiting examples of display elements include screens, monitors, and security elements, such as security markings.

[0025] As used herein, the term "window" means an aperture adapted to allow radiation to be transmitted therethrough. Non-limiting examples of windows include automotive and aircraft transparencies, windshields, filters, shutters, and optical switches.

[0026] As used herein, the term "mirror" means a surface that specularly reflects a significant portion of incident light.

[0027] As used herein, the term "liquid crystal cell" refers to a structure containing liquid crystal material that is capable of being ordered. A non-limiting example of a liquid crystal cell element is a liquid crystal display.

[0028] As used herein, the term "unactivated state" with respect to the photochromic layer of a photochromic article means that the photochromic layer is in a "first state" as previously described herein (eg, in a transparent state or having a first color).

[0029] As used herein, the term "first unactivated state terminal minimum absorbance wavelength value" means the wavelength at which the photochromic layer (which contains the photochromic material) in the unactivated state has an end (or upper limit) minimum absorbance. For some embodiments, the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer corresponds to a wavelength above which the absorbance is no greater than 0.05 AU. This can be determined using a Varian Cary 300 UV / VIS spectrophotometer with a range of 550-250 nm (average time 0.100 s, data interval 1.100, and scan rate 600 nm / min) to determine the absorbance as a function of wavelength within a specified wavelength range, and evaluating the raw data to identify the lowest wavelength at which the absorbance reaches 0.05 or less.

[0030] As used herein, and with respect to the UV absorbing layer, the term "terminal minimum absorbance wavelength value" means the wavelength value at which the UV absorbing layer (which contains the UV absorber) has an end (or upper limit) minimum absorbance. For some embodiments, the end minimum absorbance wavelength value of the UV absorbing layer corresponds to a wavelength above which the absorbance is no greater than 0.05 AU. This can be determined using the same method discussed above for the first unactivated state end minimum absorbance wavelength value.

[0031] As used herein, and unless otherwise indicated, "percent transmittance" is measured by a spectrophotometer, such as a Varian Cary 300 UV / VIS spectrophotometer or Determined by MCS 601 spectrophotometer.

[0032] As used herein, spatial or directional terms, such as "left", "right", "inner", "outer", "above", "below", etc., relate to various orientations of the invention as may be further described herein, such as articles and multilayer articles of the invention. However, it should be understood that the invention may assume various alternative orientations to those described herein, and therefore, such terms should not be considered limiting.

[0033] As used herein, the terms "formed over", "deposited over", "provided over", "applied over", "residing over", or "positioned over" mean formed, deposited, provided, applied, applied, present, or positioned on an underlying element, or on a surface of an underlying element, but not necessarily in direct (or adjacent) contact therewith. For example, a layer "positioned on a substrate" does not exclude the presence of one or more other layers, coatings, or films of the same or different composition located between the positioned or formed layer and the substrate.

[0034] As used herein, "at least one of" is synonymous with "one or more of," whether the elements are listed in conjunction or separately. For example, the phrases "at least one of A, B, and C" and "at least one of A, B, or C" each mean any one of A, B, or C, or any combination of any two or more of A, B, or C. For example, A alone; or B alone; or C alone; or A and B; or A and C; or B and C; or all of A, B, and C.

[0035] As used herein, "selected from" is synonymous with "chosen from", regardless of whether the elements are listed in combination or separately. Further, the phrases "selected from A, B, and C" and "selected from A, B, or C" each mean any one of A, B, or C, or any combination of any two or more of A, B, or C. For example, A alone; or B alone; or C alone; or A and B; or A and C; or B and C; or all of A, B, and C.

[0036] All documents (such as, but not limited to, issued patents and patent applications) mentioned herein and unless otherwise indicated are deemed to be "incorporated by reference" in their entirety.

[0037] As used herein, the term "aliphatic group" and similar terms (such as "aliphatic substituent") means a straight or branched aliphatic group and / or alicyclic group that is not aromatic and that optionally contains at least one carbon-carbon unsaturated bond, such as at least one olefinic bond (-C=C-) and / or at least one acetylenic bond (-C≡C-). For some embodiments, the straight or branched aliphatic group herein contains 1 to 10 carbon atoms, and the alicyclic group contains 3 to 10 carbon atoms.

[0038] As used herein, the description of a "straight or branched" group (such as a straight or branched alkyl group) is understood herein to include: methylene or methyl; straight chain groups, such as a straight chain C2-C 10 Alkyl; and appropriately branched groups, such as branched C3-C 10 alkyl.

[0039] As used herein, the term "alkyl" refers to a linear or branched, cyclic or non-cyclic C1-C 10 Alkyl. A straight chain or branched chain alkyl may include C1-C 15 Alkyl, such as C1-C 10 Alkyl groups such as C1-C5 alkyl groups, such as C2-C5 alkyl groups, such as C2-C4 alkyl groups. Examples of alkyl groups from which the various alkyl groups of the present invention can be selected include, but are not limited to, those further listed herein. Alkyl groups may include "cycloalkyl groups". As used herein, the term "cycloalkyl group" means a suitable cyclic group, such as, but not limited to, a C3-C 10 Cycloalkyl (including but not limited to cyclic C3-C8 alkyl, or cyclic C5-C7 alkyl).

[0040] Representative alkyl includes but is not limited to methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, and decyl. Representative cycloalkyl includes but is not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl.

[0041] As used herein, the term "aromatic group" and similar terms (such as "aromatic substituent" or "aryl" or "aryl substituent") refer to a group that is aromatic and can contain one ring, or two or more condensed rings. Each aromatic group can be unsubstituted or substituted with one or more substituents. Examples of substituents of substituted aromatic groups include, but are not limited to, aliphatic groups, aliphatic ether groups, and aliphatic carboxylate groups. Examples of aromatic groups include, but are not limited to, phenyl, naphthyl, anthracenyl, and phenanthrenyl.

[0042] As used herein, the recitation of a "substituted" group is intended to refer to groups including, but not limited to, alkyl, cycloalkyl, and / or aryl groups in which at least one hydrogen has been replaced or substituted with a group or "substituent" other than hydrogen, such as, but not limited to, alkoxy; halide (e.g., F, Cl, I, and Br); hydroxy; thiol; alkylthio; arylthio; ketone; aldehyde; carboxylic ester; carboxylic acid; phosphoric acid; phosphate; sulfonic acid; sulfonate; nitro; cyano; alkyl; alkenyl; alkynyl; haloalkyl; perhaloalkyl; heterocycloalkyl; aryl (including alkaryl, including hydroxy-substituted aryl, such as phenol, and including polycondensed ring aryl); aralkyl; heteroaryl (including polycondensed ring heteroaryl); amino, such as -N(R 11’ )(R 12’ ), where R 11’ and R 12’ Each is independently selected from, for example, hydrogen, alkyl, or aryl groups; carboxylate groups; siloxane groups; alkoxysilane groups; polysiloxane groups; amide groups; carbamate groups; carbonate groups; urea groups; trialkylsilyl groups; nitrogen-containing heterocyclic compounds; or combinations thereof.

[0043] refer to Figure 1, and for non-limiting illustrative purposes, a photochromic article 2 according to the present invention is depicted. The photochromic article 2 includes a substrate 11 having a first surface 14 and a second surface 17, wherein the first surface 14 and the second surface 17 are opposite to each other. The first surface 14 of the substrate 11 faces the incident actinic radiation depicted by arrow 20. The photochromic article 2 further includes a photochromic layer 23 on (e.g., adjacent to) the substrate 11 and particularly on (e.g., adjacent to) the first surface 14 of the substrate 11. The photochromic article 2 further includes a UV absorbing layer 26 on (e.g., adjacent to) the photochromic layer 23. For some embodiments, the photochromic article 2 optionally includes one or more additional layers, as will be further described herein.

[0044] According to the present invention, the terminal minimum absorbance wavelength value of the UV absorbing layer is at least 45 nm smaller than the terminal minimum absorbance wavelength value of the first unactivated state of the photochromic layer.

[0045] For some embodiments of the present invention, the terminal minimum absorbance wavelength value of the UV absorbing layer is at least 50 nm less than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer.

[0046] For some additional embodiments of the present invention, the terminal minimum absorbance wavelength value of the UV absorbing layer is at least 55 nm less than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer.

[0047] According to some further embodiments, the terminal minimum absorbance wavelength value of the UV absorbing layer is 45 nm to 80 nm, or 50 nm to 80 nm, or 55 nm to 80 nm less than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer.

[0048] refer to Figure 2 , and for non-limiting purposes, the photochromic layer of Example 1 has a first unactivated state end minimum absorbance wavelength value of 422 nm. Further reference Figure 2 , the UV absorbing layer of Example B has a terminal minimum absorbance wavelength value 32 of 350 nm. Accordingly, the terminal minimum absorbance wavelength value 32 of the UV absorbing layer of Example B is 72 nm smaller than the first unactivated terminal minimum absorbance wavelength value 29 of the photochromic layer of Example 1.

[0049] The photochromic layer has an unactivated state absorbance greater than 0 over at least a portion of the wavelengths from 250 nm to 450 nm. The absorption spectrum can be measured using a UV / VIS spectrophotometer as previously described herein.

[0050] For some embodiments, the minimum absorbance wavelength value of the first unactivated state end of the photochromic layer is greater than 390nm. For some other embodiments, the minimum absorbance wavelength value of the first unactivated state end of the photochromic layer is greater than 410nm. According to some embodiments, the minimum absorbance wavelength value of the first unactivated state end of the photochromic layer is less than 450nm. For some other embodiments, the minimum absorbance wavelength value of the first unactivated state end of the photochromic layer is greater than 410nm and less than 450nm.

[0051] The photochromic material or compound of the photochromic layer can be selected from one or more photochromic materials or compounds recognized in the art. For some embodiments, the photochromic material of the photochromic layer is selected from at least one of the following: naphthopyran, benzopyran, phenanthropyran, indenonaphthopyran, spiro(indoline)phenoxazine, spiro(indoline)pyridobenzoxazine, spiro(benzidindoline)pyridobenzoxazine, spiro(benzidindoline)phenoxazine, spiro(indoline)-benzoxazine, fulgide, diarylethene, and / or fulgimide. For some other embodiments, the photochromic material of the photochromic layer includes one or more indeno-naphthopyrans, such as one or more indeno[2',3':3,4]naphtho[1,2-b]pyrans, wherein hydrogen and / or various substituents are at positions 3 and 5-13 thereof.

[0052] Additional examples of other photochromic materials and compounds that can be used in the photochromic layer of the present invention include, but are not limited to, those disclosed in US Pat. No. 9,028,728 B2, column 34, line 20 to column 35, line 13, the disclosure of which is specifically incorporated herein by reference.

[0053] The photochromic material may be present in the photochromic layer in any suitable amount, provided that the photochromic article has a desired level of photochromic properties, such as a photochromic effective amount. For some embodiments, the photochromic material is present in the photochromic layer in an amount of 0.001 weight percent to 40 weight percent, or 0.001 weight percent to 10 weight percent, or 0.01 weight percent to 5 weight percent, or 0.1 weight percent to 2.5 weight percent, wherein the weight percentages are in each case based on the total solid weight of the photochromic layer. The photochromic material may be introduced into the photochromic layer according to methods recognized in the art, including but not limited to imbibition of components used to prepare the photochromic layer and / or mixing with components used to prepare the photochromic layer.

[0054] For some embodiments, the end minimum absorbance wavelength value of the UV absorbing layer is greater than 330 nm and less than 380 nm, or greater than 340 nm and less than 370 nm.

[0055] The UV absorbing layer may include any suitable UV absorber or combination of UV absorbers, provided that: the terminal minimum absorbance wavelength value of the UV absorbing layer is at least 45 nm less than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer. For some embodiments, the UV absorber is present in the UV absorbing layer in an amount of 0.25 weight percent to 7 weight percent, or 0.50 weight percent to 6 weight percent, or 1 weight percent to 5 weight percent, the weight percent being in each case based on the total solid weight of the UV absorbing layer.

[0056] For some embodiments, the UV absorbing layer comprises at least one of an unsubstituted oxalanilide, a substituted oxalanilide, a cinnamate, a salicylate, and / or a cyanoacrylate.

[0057] As used herein, the term "unsubstituted oxalyl anilide" means N,N'-diphenyl oxalamide. As used herein, the term "substituted oxalyl anilide" means N,N'-diphenyl oxalamide, wherein one or both of its phenyl rings have one or more substituents covalently bonded thereto, including one or more of those substituents previously listed herein. For some embodiments, each substituent of the substituted oxalyl anilide is independently selected from: an aliphatic group, such as a linear or branched C1-C 12 Alkyl; cycloalkyl, such as C3-C7 cycloalkyl; and / or aliphatic ether group, such as linear or branched C1-C 12 alkyl.

[0058] As used herein, the term "cinnamate" means an ester of cinnamic acid. For some embodiments, each cinnamate is independently selected from: aliphatic esters of cinnamic acid, such as straight or branched C1-C1 esters of cinnamic acid. 12 and aromatic esters of cinnamic acid, such as unsubstituted phenyl esters of cinnamic acid and substituted phenyl esters of cinnamic acid. For some embodiments, each substituent of the substituted phenyl ester of cinnamic acid is independently selected from those substituents previously listed herein.

[0059] As used herein, the term "salicylate" means an ester of salicylic acid (or 2-hydroxybenzoic acid). For some embodiments, each salicylate is independently selected from: aliphatic esters of salicylic acid, such as straight or branched C1-C 12 and aromatic esters of salicylic acid, such as unsubstituted phenyl esters of salicylic acid and substituted phenyl esters of salicylic acid. For some embodiments, each substituent of the substituted phenyl ester of salicylic acid is independently selected from those substituents previously listed herein.

[0060] As used herein, the term "cyanoacrylate" means an ester of cyanoacrylic acid. For some embodiments, each cyanoacrylate is independently selected from: an aliphatic ester of cyanoacrylic acid, such as a linear or branched C1-C1 12 Alkyl esters; and aromatic esters of cyanoacrylate, such as unsubstituted phenyl esters of cyanoacrylate and substituted phenyl esters of cyanoacrylate. For some embodiments, each substituent of the substituted phenyl ester of cyanoacrylate is independently selected from those substituents previously listed herein. For some embodiments, the 3,3-substituents of the cyanoacrylate are each independently selected from: hydrogen (-H); aliphatic groups, such as linear or branched alkyl groups and optionally substituted cycloalkyl groups; and optionally substituted aryl groups, such as optionally substituted phenyl (wherein each substituent of the substituted cycloalkyl group and the substituted aryl group is independently selected from those substituents previously listed herein). According to some embodiments, a non-limiting example of a cyanoacrylate is 2-cyano-3,3-diphenylacrylate 2-ethylhexyl ester (also known as octocrylene).

[0061] According to some embodiments, the UV absorbing layer comprises one or more substituted oxalylanilides. According to some other embodiments, the UV absorbing layer comprises at least one of N-(2-ethoxyphenyl)-N'-(4-(10-methylundecyl)phenyl)oxalamide and / or N-(2-ethoxyphenyl)-N'-(4-ethylphenyl)oxalamide.

[0062] For some embodiments, the photochromic article of the present invention may optionally include one or more additional layers, such as but not limited to: one or more primer layers; one or more top coating layers; one or more anti-reflective layers; one or more hard coating layers; one or more polarizing layers; and one or more orientation layers. The types and examples of such additional optional layers are described in US8,828,284 B2, column 20, line 30 to column 21, line 38, the disclosure of which is incorporated herein by reference.

[0063] For some embodiments of the present invention, the photochromic layer, UV absorber layer and one or more additional optional layers of the photochromic article may each optionally and independently contain at least one additive, provided that the terminal minimum absorbance wavelength value of the UV absorber layer is at least 45 nm less than the terminal minimum absorbance wavelength value of the first unactivated state of the photochromic layer. For some embodiments, each additive is independently selected from static dyes, orientation promoters, dynamic enhancement additives, photoinitiators, thermal initiators, inhibitors, solvents, light stabilizers, thermal stabilizers, mold release agents, rheology control agents, leveling agents, free radical scavengers, adhesion promoters, blue light blockers, or a combination of two or more thereof. Types and examples of blue light blocking (or filtering) agents include, but are not limited to, those described in US 9,683,102B2 and US2015 / 0234208 A1, the relevant parts of which are incorporated herein by reference.

[0064] For some embodiments, the photochromic layer, UV absorbing layer, and any additional optional layers provided on the substrate of the photochromic article of the present invention each independently comprise an organic matrix, such as an organic polymer matrix, which may be a cured (or cross-linked) organic matrix, a thermoplastic organic matrix, or a combination thereof. Accordingly, each layer of the photochromic article of the present invention (including the photochromic layer and the UV absorbing layer) may each independently be selected from a cured (or cross-linked) layer and a thermoplastic layer. The organic matrix of each layer of the photochromic article of the present invention may each independently comprise a bond, such as, but not limited to: an ether bond; a carboxylate bond; a urethane bond; an amide bond; a urea bond; a carbonate bond; a bond formed by free radical polymerization of a free radical polymerizable ethylenically unsaturated group (such as, but not limited to, a vinyl group, an allyl group, and / or a (meth)acrylate group); and a combination of two or more thereof.

[0065] Each layer of the photochromic article of the present invention (including the photochromic layer and the UV absorbing layer) can be formed by methods recognized in the art, such as but not limited to lamination methods and coating methods. Coating methods include, but are not limited to: spray coating methods; spin coating methods; curtain coating methods; dip coating methods; micro-spray coating methods (such as inkjet coating methods); in-mold coating methods; and combinations thereof. Lamination methods include, but are not limited to: extrusion lamination methods (such as directly on the substrate); in-mold lamination methods (wherein the laminate is placed in a mold and the substrate is formed against it in the mold); thermal lamination methods (wherein the laminate is thermally fused on the substrate); adhesive lamination methods (wherein the laminate is adhered to the substrate by an adhesive layer placed in between); and combinations thereof.

[0066] For some embodiments, the substrate of the photochromic article can be composed of one or more suitable materials, including but not limited to: organic materials, such as organic polymer materials (such as cross-linked organic polymer materials and / or thermoplastic organic polymer materials), such as but not limited to thermoplastic polycarbonates, cross-linked polycarbonates, poly (meth) acrylates, and combinations thereof; glass, such as silica-based glass; metal; ceramic materials; and combinations of two or more thereof. Examples of substrates that can be included in the photochromic articles of the present invention include, but are not limited to, those described in US 8,628,685 B2, column 35, line 5 to column 36, line 57, the disclosure of which is incorporated herein by reference.

[0067] For some embodiments, the photochromic article is selected from the group consisting of an ophthalmic article, a display article, a window, a mirror, an active liquid crystal cell article, and a passive liquid crystal cell article.

[0068] For some further embodiments, the photochromic article is selected from ophthalmic articles, and the ophthalmic article is selected from corrective lenses, non-corrective lenses, contact lenses, intraocular lenses, magnifying lenses, protective lenses, and goggles.

[0069] For some additional embodiments, the photochromic article is selected from a display article, and the display article is selected from a screen, a monitor, and a security element.

[0070] The present invention may be further characterized by one or more of the following non-limiting clauses.

[0071] Item 1: A photochromic article comprising:

[0072] (a) substrate;

[0073] (b) a photochromic layer comprising a photochromic material, the photochromic layer being superimposed on the substrate, the photochromic layer having an unactivated state absorbance greater than 0 (or for some embodiments, greater than 0.05) over at least a portion of the wavelength range from 250 nm to 450 nm and a first unactivated state terminal minimum absorbance wavelength value; and

[0074] (c) a UV absorbing layer comprising a UV absorber, the UV absorbing layer being superposed on the photochromic layer, the UV absorbing layer having a terminal minimum absorbance wavelength value,

[0075] The terminal minimum absorbance wavelength value of the UV absorbing layer is at least 45 nm smaller than the first unactivated terminal minimum absorbance wavelength value of the photochromic layer.

[0076] Item 2: The photochromic article of Item 1, wherein the terminal minimum absorbance wavelength value of the UV absorbing layer is at least 50 nm less than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer.

[0077] Item 3: The photochromic article of Item 1 or Item 2, wherein the terminal minimum absorbance wavelength value of the UV absorbing layer is at least 55 nm less than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer.

[0078] Item 4: The photochromic article of any one of Items 1 to 3, wherein the terminal minimum absorbance wavelength value of the UV absorbing layer is at least 60 nm less than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer.

[0079] Item 5: A photochromic article as described in any of Items 1 to 4, wherein the terminal minimum absorbance wavelength value of the UV absorbing layer is 45nm to 80nm, or 45nm to 75nm, or 45nm to 70nm, or 45nm to 65nm, or 45nm to 60nm, or 45nm to 55nm, or 45nm to 50nm smaller than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer.

[0080] Item 6: The photochromic article according to any one of Items 1 to 5, wherein the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer is greater than 410 nm and less than or equal to 450 nm.

[0081] Item 7: The photochromic article of any one of Items 1 to 6, wherein the terminal minimum absorbance wavelength value of the UV absorbing layer is greater than 330 nm and less than 380 nm.

[0082] Item 8: The photochromic article of any one of Items 1 to 7, wherein the UV absorbing layer comprises at least one of an unsubstituted oxalanilide, a substituted oxalanilide, a cinnamate, a salicylate, or a cyanoacrylate.

[0083] Item 9: A photochromic article as described in any of Items 1 to 8, wherein the UV absorbing layer comprises at least one substituted oxalic acid anilide, and each substituted oxalic acid anilide is independently selected from N-(2-ethoxyphenyl)-N'-(4-(10-methylundecyl)phenyl)oxalamide and N-(2-ethoxyphenyl)-N'-(4-ethylphenyl)oxalamide.

[0084] Item 10: A photochromic article as described in any of Items 1 to 9, wherein the photochromic material of the photochromic layer comprises at least one of the following: naphthopyran, benzopyran, phenanthropyran, indenonaphthopyran, spiro(indoline)phenoxazine, spiro(indoline)pyridobenzoxazine, spiro(benzindoline)pyridobenzoxazine, spiro(benzindoline)phenoxazine, spiro(indoline)-benzoxazine, fulgide, diarylethene, and / or fulgimide.

[0085] Clause 11: The photochromic article of any of Clauses 1 to 10, wherein the photochromic article is selected from the group consisting of an ophthalmic article, a display article, a window, a mirror, an active liquid crystal cell article, and a passive liquid crystal cell article.

[0086] Clause 12: The photochromic article of any of Clauses 1 to 11, wherein the photochromic article is selected from ophthalmic articles, and the ophthalmic article is selected from the group consisting of corrective lenses, non-corrective lenses, contact lenses, intraocular lenses, magnifying lenses, protective lenses, and goggles.

[0087] Clause 13: The photochromic article of any of Clauses 1 to 12, wherein the photochromic article is selected from a display article, and the display article is selected from the group consisting of a screen, a monitor, and a security element.

[0088] The present invention is more particularly described in the following examples, which are intended to be illustrative only, since numerous modifications and variations therein will be apparent to those skilled in the art. Unless otherwise indicated, all parts and all percentages are by weight.

[0089] Examples

[0090] In Section 1 of the following Examples, the preparation of a curable photochromic composition is described. In Section 2, the preparation of a composition for preparing a UV absorber layer is described. In Section 3, a method for determining the terminal minimum absorbance wavelength value is described. In Section 4, the preparation of a photochromic article test sample is described. In Section 5, a procedure for testing a photochromic article test sample is described. In Section 6, a procedure for determining photochromic fatigue is described.

[0091] Part 1 - Preparation of curable photochromic compositions

[0092] The curable photochromic composition was prepared according to the procedure described in Example 8 of US 10,954,397 B2.

[0093] Example 1 includes a mixture of five indeno-fused naphthopyran dyes formulated to provide a grey color upon activation.

[0094] Example 2 includes a mixture of two indeno-fused naphthopyran dyes formulated to provide a grey color upon activation.

[0095] Part 2 - Preparation of UV absorbing layer

[0096] The UV absorbing layer was prepared as described below.

[0097] In a first step, a stock solution (Control Solution A) was prepared by combining the ingredients listed in Table 1 in a suitable amber glass bottle equipped with a magnetic stir bar. The solution was stirred at 25°C for 2 hours.

[0098] Table 1

[0099] Control solution A

[0100]

[0102] (1) Blocked aliphatic polyisocyanates available from Covestro AG

[0103] (2) Photoinitiators available from IGM Resins

[0104] (3) Type I photoinitiators available from IGM Resins

[0105] In each case, a 5.0 g portion of control solution A was introduced into seven separate 20 mL amber glass vials equipped with a stirring bar. The UV absorber was then added to each vial according to the amount (in grams) listed in Table 2 and allowed to stir well.

[0106] Table 2

[0107] Solutions with various UV absorbers

[0108]

[0110] (4) Oxalanilide-based UV absorbers from Clariant.

[0111] (5) Benzotriazole-based UV absorbers from BASF.

[0112] (6) Benzophenone based UV absorbers from Solvay.

[0113] Part 3 - Determine the wavelength value of minimum absorbance at the end.

[0114] Substrate preparation:

[0115] The following procedure was used to prepare the pre-treated substrate. A CR-39 poly(allyl diglycol carbonate) substrate (processed without UV absorber) of 2×2 inch (5.1×5.1 cm) size was obtained from Piedmont Plastics. Each substrate was cleaned by wiping with a paper towel soaked with isopropyl alcohol, dried with a stream of air, and then corona treated on a conveyor belt in a Tantec EST Systems Serial No. 020270 PowerGenerator HV 2000 series corona treatment unit with a high voltage transformer. The substrate was exposed to a corona generated at 70.00 KV and 1000 watts while traveling on a conveyor belt speed of 3 ft / min (0.91 m / min) on a conveyor.

[0116] The photochromic coating compositions of Example 1 and Example 2 were applied separately to the pretreated substrates by dispensing approximately 1.5 mL of the photochromic coating composition onto the surface of each pretreated substrate, followed by spinning the substrates at 1050 revolutions per minute (rpm) for 8 seconds. The photochromic coated substrates were placed in a forced air oven maintained at 125° C. for 60 minutes, which resulted in the formation of a photochromic layer test sample.

[0117] In each case, the UV absorbing compositions of Control Solution A and Examples AH were individually spin coated onto the pretreated substrate at 700 revolutions per minute (rpm) for 2 seconds, followed by 1900 rpm for 2 seconds. The UV absorber coated substrates were cured in a UV curing oven designed and built by Belcan Engineering in a nitrogen atmosphere under 4 UV lamps while running on a conveyor belt at 6 ft / min with a peak intensity of 1.50 W / cm 2 UVA and UV dose is 4.5-5.0J / cm 2 The UV absorber coated test sample was then placed in a forced air oven at 105°C for 3 hours, which resulted in the formation of a control solution A test sample and a UV absorbing layer test sample.

[0118] The photochromic layer test samples, the control solution A test samples and the UV absorbing layer test samples were analyzed in each case using a Varian Cary 300 UV / VIS spectrophotometer with a range of 550-250 nm (averaging time 0.100 s, data interval 1.100, and scan rate 600 nm / min). The photochromic layer test samples were scanned and analyzed directly. After generating a baseline scan of the test samples prepared with control solution A alone (without any UV absorber added thereto) and then zeroing each sample, a scan of each UV absorbing layer test sample was run. Figure 1 The raw data of the absorbance relative wavelength graph shown in is also used to determine the terminal minimum absorbance wavelength value (TMAW value) of each layer. The shortest (lowest) wavelength with an absorbance (AU) less than 0.0500 is identified as the terminal minimum absorbance wavelength value of the corresponding layer, and each is reported in Table 3.

[0119] Table 3

[0120] Minimum absorbance wavelength at the end of a single layer

[0121]

[0123] *Not activated.

[0124] Part 4 - Procedures for preparing photochromic articles.

[0125] Substrate preparation.

[0126] Polycarbonate plano lenses (6 base; 76 mm diameter) were obtained from Gentex Optical. Each substrate was cleaned by wiping with a paper towel soaked with isopropyl alcohol, dried with a stream of air and then corona treated under the conditions described in Section 3 above, which resulted in a pre-treated lens.

[0127] Each curable photochromic coating composition of Example 1 and Example 2 was applied to the pretreated lenses (in duplicate for the examples shown in Table 4) by dispensing approximately 1.5 mL of the curable photochromic coating composition onto the surface of each pretreated lens, followed by spinning at 1050 revolutions per minute (rpm) for 8 seconds. The photochromic coated pretreated lenses were placed in a forced air oven maintained at 125°C for 60 minutes. Once the photochromic coated lenses cooled to room temperature, solutions of the UV absorber coating compositions of Control Solution A and Example BH were spin coated on the cured photochromic coatings formed from Examples 1 and 2 at a rate of 700 revolutions per minute (rpm) for 2 seconds, followed by 1900 revolutions for 2 seconds. The coated substrates were cured in a UV curing oven designed and built by Belken Engineering in a nitrogen atmosphere under 4 UV lamps while running on a conveyor belt at a speed of 6 ft / min, with a peak intensity of 1.50 W / cm 2 UVA and UV dose is 4.5-5.0J / cm 2 The coated samples were then placed in a forced air oven at 105°C for 3 hours, which resulted in the formation of a photochromic article test sample.

[0128] Table 4

[0129] Photochromic product test samples

[0130]

[0131] Part 5 - Test procedures for properties of test specimens of photochromic articles.

[0132] The photochromic performance of the photochromic article test samples and their corresponding replicas as summarized in Table 4 were evaluated using the Photochromic Performance Test conducted on an Advanced Platform for Measuring Photochromism ("A-BMP") optical bench. For each sample, the optical bench was maintained at a constant temperature of 23°C.

[0133] Prior to testing on the optical table, each of the photochromic article test samples was exposed to 365 nanometer ultraviolet light at a distance of about 14 centimeters for about 10 minutes to activate the photochromic material. The UVA (315 to 380 nm) irradiance at the photochromic article test sample was measured with a Goosch & Housego OL 756 spectroradiometer with an OL 86-T cosine receptor and found to be 22.2 watts per square meter. The photochromic article test sample was then placed under a 500-watt high-intensity halogen lamp for about 10 minutes at a distance of about 36 centimeters to bleach (deactivate) the photochromic material. The illuminance at the photochromic article test sample was measured with an OL 756 spectroradiometer and found to be 21.9 Klux. The photochromic article test sample was then kept in a dark environment at room temperature (21° C. to 24° C.) for at least 1 hour prior to testing on the optical table. Prior to the optical bench measurement, the UV absorbance of the photochromic article test sample was measured at 390 nm.

[0134] The A-BMP optical bench is equipped with two 150-watt Model #66057 Xenon Arc Lamp. The light path from lamp 1 was directed through a 3 mm SCHOTT KG-2 bandpass filter and appropriate neutral density filters, which facilitated the desired UV and partial visible light irradiance levels. The light path from lamp 2 was directed through a 3 mm SCHOTT KG-2 bandpass filter, a SCHOTT GG400 short waveband cutoff filter, and appropriate neutral density filters to provide supplemental visible light illumination. A 2 inch x 2 inch (5.1 cm x 5.1 cm) 50% polka dot beam splitter at 45° to each lamp was used to mix the two beams. The intensity of the irradiance was adjusted using a combination of neutral density filters and xenon arc lamp voltage control. Proprietary software (i.e., PTSoft version 6.7) was used on the A-BMP to control timing, irradiance, gas chamber and sample temperature, shutters, filter selection, and response measurements. A 100 mm x 200 mm optical fiber cable was used to transmit light through the lens. Model MCS 601 spectrophotometer performed response and color measurements. Photopic response measurements were collected for each photochromic article test sample.

[0135] The power output of the optical bench (i.e., the dose of light to which the photochromic article test sample is exposed) was adjusted to 6.7 W / m 2) UVA, integrated from 315-380nm, and 50Klux illumination, integrated from 380-780nm. The measurement of this power set point is performed using an irradiance probe and a calibrated Zeiss spectrophotometer. The lens sample pool is equipped with a quartz window and an automatic centering sample holder. The temperature in the sample pool is controlled by software with an AirJet XE custom-connected to a bubbling water bath to deliver 50% RH air maintained at a desired temperature. The measurement of the dynamic photochromic response of the photochromic product test sample and the color measurement are performed using the same Zeiss spectrophotometer, which has a fiber optic cable for transmitting light from a halogen tungsten lamp and passing through the test sample. The collimated monitoring beam from the fiber optic cable is kept perpendicular to the test sample while passing through the photochromic product test sample and being guided to the receiving fiber optic cable assembly attached to the spectrophotometer. The exact placement point of the photochromic article test sample in the sample cell is where the activation xenon arc beam and the monitoring beam intersect to form two concentric circles of light. The incident angle of the xenon arc beam at the sample placement point is 30° relative to the vertical line.

[0136] The response measurement, expressed as the change in optical density (ΔOD) from the unactivated or blanched state to the activated or colored state, is determined by establishing an initial unactivated transmittance, opening the shutter of the xenon lamp and measuring the transmittance through activation at selected time intervals. The change in optical density is determined according to the following formula: ΔOD = log (10) (% Tb / % Ta), where % Tb is the percent transmittance in the blanched state and % Ta is the percent transmittance in the activated state. Delta optical density measurements are based on photopic optical density.

[0137] The saturation ΔOD was recorded after activation at 23°C for 15 minutes. The fading half-life (“T 1 / 2 ”) value is the time interval (in seconds) for the ΔOD of the activated form of the photochromic material in the coating to reach half of the ΔOD recorded after activation at 23°C for 15 minutes as described above after removal of the activating light source. Subsequent T1 / 2 fading time intervals (in seconds) are calculated using the same method as above using ΔOD, such as 3 / 4 ΔOD (2nd T1 / 2), 7 / 8 ΔOD (3rd T1 / 2) and 15 / 16 ΔOD (4th T1 / 2) to determine the time interval (in seconds) for fading of the photochromic article test sample to the corresponding ΔOD after activation at 23°C for 15 minutes as described above after removal of the activating light source. The time to reach 70% T (in minutes) is determined by recording the fading of the photochromic article test sample to 70% photopic % T after removal of the activating light source at the end of 15 minutes of activation at 23°C.

[0138] The performance data of the photochromic article test samples containing the photochromic layer formed from the curable photochromic composition of Example 1 are shown in Table 5. The performance data of the photochromic article test samples containing the photochromic layer formed from the curable photochromic composition of Example 2 are shown in Table 6.

[0139] Table 5

[0140] Photochromic Articles Having a Photochromic Layer Formed from Example 1 The samples were tested for photochromic properties.

[0141]

[0142] Table 6

[0143] Photochromic Articles Having Photochromic Layers Formed from Example 2 The samples were tested for photochromic properties.

[0144]

[0145]

[0146] Part 6 - Test procedure for determining photochromic fatigue

[0147] The photochromic article test samples and their corresponding replicas used for the performance tests in Section 5 above were evaluated for fatigue according to the following procedure (the data for each sample group were averaged).

[0148] Simulated solar radiation accelerated aging (i.e., fatigue) was performed using an Atlas Ci5000 weathering tester. The photochromic article test sample was exposed to a one-hour dark cycle and then a 65-hour light cycle using a boron / borosilicate filtered xenon arc lamp (with an output of 0.25 watts / square meter at 340 nm). The temperature in the Atlas Ci4000 weathering tester was maintained at 45°C during the light cycle, and the relative humidity was controlled at 70% humidity. The temperature of the black panel with a thermometer connected to it and representing the test sample was maintained at 55°C. This accelerated aging procedure was then performed a second time on the photochromic article test sample.

[0149] After the photochromic article test samples were subjected to this second UV exposure fatigue cycle, they were preconditioned and measured on an optical bench to obtain the final photopic response (ΔOD) under the same conditions as described for the initial testing. 最终 Percent fatigue is determined by measuring the difference between the ΔOD of a photochromic article test sample before and after accelerated aging according to the following formula: % fatigue = (ΔOD 初始 -ΔOD 最终 ) / ΔOD 初始× 100. The Δb* value was also determined. The Δb* value is the b* measured on a Hunter UltraScan Pro device before exposure in an Atlas Ci4000 weathering tester. 初始 Subtract the b* measured for the lens in the whitened state after the 65 hour UV exposure fatigue cycle. 最终 The Δb* value indicates the amount of yellowing that occurs to the lens during fatigue.

[0150] Fatigue data for test samples of photochromic articles containing photochromic layers formed from the curable composition of Example 1 are summarized in Table 7. Fatigue data for test samples of photochromic articles containing photochromic layers formed from the curable composition of Example 2 are summarized in Table 8.

[0151] Table 7

[0152] Fatigue Data of Examples and Comparative Examples 1A-H

[0153]

[0154] Table 8 Fatigue data of Examples and Comparative Examples 2A-H

[0155]

[0156] Referring to the data summarized in Tables 5 and 6, Examples BD in which the difference in the terminal minimum absorbance wavelength value between the photochromic layer and the overlying UV absorbing layer is 45 nm or more have an activated optical density ΔOD value equal to or greater than that of Control Examples 1-A or 2-A (without a UV absorber layer). It was observed that the comparative examples with a terminal minimum absorbance wavelength value difference of less than 45 nm (relative to the photochromic layer) demonstrated attenuation (reduction) of optical density in the activated state. In addition, it was demonstrated that the presence of a UV absorber layer with a terminal minimum absorbance wavelength value difference of 45 nm or more (relative to the photochromic layer) maintained or improved late fading (most obvious in the 4th T1 / 2 measurement); while a UV absorber layer with a terminal minimum absorbance wavelength value difference of less than 45 nm (relative to the photochromic layer) demonstrated a slower fading rate. In addition, Tables 7 and 8 show that when compared to the control (without a UV absorber layer), each UV absorbing layer provides equal or improved fatigue as compared to the control, as demonstrated by less yellowing after exposure and equal or lower optical density loss. Thus, the presence of a UV absorbing layer having a terminal minimum absorbance wavelength value difference (relative to the photochromic layer) of at least 45 nm provides stability without sacrificing darkness or fading speed.

[0157] The invention has been described with reference to specific details of particular embodiments of the invention. It is not intended that such details be considered limitations on the scope of the invention unless and to the extent they are included in the appended claims.

Claims

1. A photochromic article comprising: (a) substrate; (b) a photochromic layer comprising a photochromic material, the photochromic layer being stacked on the substrate, the photochromic layer having an unactivated state absorbance greater than 0 over at least a portion of the wavelength range from 250 nm to 450 nm and a first unactivated state terminal minimum absorbance wavelength value; as well as (c) a UV absorbing layer comprising a UV absorber, the UV absorbing layer being stacked on the photochromic layer, the UV absorbing layer having a terminal minimum absorbance wavelength value, The terminal minimum absorbance wavelength value of the UV absorbing layer is at least 45 nm smaller than the first unactivated terminal minimum absorbance wavelength value of the photochromic layer.

2. The photochromic article according to claim 1, wherein: The terminal minimum absorbance wavelength value of the UV absorbing layer is at least 50 nm smaller than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer.

3. The photochromic article according to claim 1, wherein: The terminal minimum absorbance wavelength value of the UV absorbing layer is at least 55 nm smaller than the first unactivated state terminal minimum absorbance wavelength value of the photochromic layer.

4. The photochromic article according to claim 1, wherein: The minimum absorbance wavelength value of the photochromic layer at the end of the first unactivated state is greater than 410 nm.

5. The photochromic article according to claim 4, wherein: The terminal minimum absorbance wavelength value of the UV absorption layer is greater than 330 nm and less than 380 nm.

6. The photochromic article according to claim 1, wherein: The UV absorbing layer comprises at least one of unsubstituted oxalic acid anilide, substituted oxalic acid anilide, cinnamate, salicylate, or cyanoacrylate.

7. The photochromic article according to claim 6, wherein: The substituted oxalic acid anilide comprises at least one of N-(2-ethoxyphenyl)-N′-(4-(10-methylundecyl)phenyl)oxalamide or N-(2-ethoxyphenyl)-N′-(4-ethylphenyl)oxalamide.

8. The photochromic article according to claim 1, wherein: The photochromic material of the photochromic layer includes at least one of the following: naphthopyran, benzopyran, phenanthropyran, indenonaphthopyran, spiro(indoline)phenoxazine, spiro(indoline)pyridobenzoxazine, spiro(benzoindoline)pyridobenzoxazine, spiro(benzoindoline)phenoxazine, spiro(indoline)-benzoxazine, fulgide, diarylethene, or fulgimide.

9. The photochromic article according to claim 1, wherein: The photochromic article is selected from the group consisting of an ophthalmic article, a display article, a window, a mirror, an active liquid crystal cell article, and a passive liquid crystal cell article.

10. The photochromic article according to claim 9, wherein: The photochromic article is selected from ophthalmic articles, and the ophthalmic article is selected from the group consisting of corrective lenses, non-corrective lenses, contact lenses, intraocular lenses, magnifying lenses, protective lenses, and goggles.

11. The photochromic article according to claim 9, wherein: The photochromic article is selected from display articles, and the display article is selected from the group consisting of: a screen, a monitor, and a security element.

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