Abstract: Various non-limiting embodiments of the present invention relate to photochromic materials which include a haloalkyl group. More particularly, various non-limiting embodiments disclosed herein provide photochromic materials including an indeno-fused naphthopyran, such as, an indeno[2?,3?:3,4]naphtho[1,2-b] pyran, and a haloalkyl group bonded at the 13-position thereof, wherein the haloalkyl group is a perhalogenated group or a group represented by —O(CH2)a(CX2)bCT3, wherein T is a halogen, each X is independently hydrogen or halogen, a is an integer ranging from 1 to 10, and b is an integer ranging from 1 to 10. Other non-limiting embodiments disclosed herein provide photochromic composition and photochromic articles, such as, but not limited to ophthalmic lens, which include the disclosed photochromic materials and methods of making the same.

Abstract: Provided is a method of preparing a photochromic polymeric article including: (a) providing a fluid polymerizable composition of: at least one monomer; a first initiator for inducing polymerization of the monomer at a first temperature; and a second initiator for inducing further polymerization at a second temperature higher than the first temperature; (b) heating the polymerizable composition to at least the first temperature whereby the first initiator induces polymerization of the monomer at the first temperature to produce a polymerizate; (c) heating the polymerizate of (b) to at least the second temperature to further polymerize the polymerizate; and (d) contacting the polymerizate with an organic photochromic substance to incorporate the organic photochromic substance into the polymerizate. Photochromic articles prepared by the method are also provided.

Abstract: Provided is an optical element including a substrate; a first at least partial coating of an at least partially ordered alignment medium connected to at least a portion of at least one surface of the substrate; a second at least partial coating of an alignment transfer material that is connected to and at least partially aligned with at least a portion of the at least partially ordered alignment medium; and a third at least partial coating connected to at least a portion of the alignment transfer material, the third coating including at least one anisotropic material that is at least partially aligned with at least a portion of the at least partially aligned alignment transfer material and at least one photochromic-dichroic compound that is at least partially aligned with at least a portion of the at least partially aligned anisotropic material.

Abstract: Describes a photochromic article, e.g., an ophthalmic photochromic plastic article, such as a lens, in which the article includes (1) a rigid substrate, e.g., a transparent substrate such as a glass or organic polymeric substrate, as for example, a thermoset or thermoplastic substrate, (2) a photochromic polymeric coating appended to at least a portion of at least one surface of the substrate, the photochromic polymeric coating containing a photochromic amount of at least one organic photochromic material, e.g., spirooxazine, naphthopyran, diarylethene and/or fulgide, and (3) a thermally cured transparent thermoset polymeric coating superposed on, e.g., coherently appended to, the photochromic coating, the thermally cured polymeric coating being harder than the photochromic polymeric coating. Describes also the aforedescribed photochromic article having an abrasion-resistant coating affixed to the thermally cured polymer coating, e.g.

Abstract: Described are photochromic materials of indeno [2?,3?:3,4]naphtho[1,2-b]pyran structure, characterized in that 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.

Abstract: Describes a multifocal optical article, e.g., an ophthalmic article such as a lens, in which the article includes (1) a rigid optical substrate, e.g., a transparent polymeric substrate, such as a thermoset or thermoplastic substrate, adapted to possess at least one light influencing property on at least a portion of at least one surface of the substrate, e.g., a photochromic and/or polarizing layer, and (2) a multifocal layer of an optical quality material on said substrate having the light influencing property. Describes also the aforedescribed optical article having an abrasion-resistant coating on the multifocal layer, e.g., an abrasion-resistant coating comprising an organo silane. A method for preparing the multifocal optical article comprising curing optical quality material between a multifocal mold and a preform comprising an optical substrate possessing the light influencing property is also described.

Abstract: Various embodiments disclosed herein relate to optical elements comprising an at least partial coating having a first state and a second state connected to at least a portion of a substrate, the at least partial coating being adapted to switch from the first state to the second state in response to at least actinic radiation, to revert back to the first state in response to thermal energy, and to linearly polarize at least transmitted radiation in at least one of the first state and the second state. Other embodiments relate to optical elements comprising a substrate and at least one at least partially aligned photochromic-dichroic compound connected to at least a portion of the substrate and having an average absorption ratio greater than 2.3 in the activated state as determined according to CELL METHOD. Still other embodiments relate to security devices, liquid crystal cells and methods of making the same.

Abstract: Described are optical elements made of a substrate having connected thereto an at least partial film of photochromic adhesive and an at least partial film of a polymeric organic material. Also described are optical elements made of a substrate having connected thereto an at least partial superstrate of a sealed photochromic composite of a film of a first polymeric organic material and a film of a second polymeric organic material having an at least partial film of a photochromic adhesive placed between the films of first and second polymeric organic materials. Methods to prepare the optical elements are also described.

Abstract: Describes a photochromic plastic article, e.g., an ophthalmic photochromic article, such as a lens, in which the article includes (1) a rigid substrate, e.g., polymeric substrate, such as a thermoset or thermoplastic substrate, (2) a photochromic polymeric coating appended to at least one surface of the substrate, the photochromic polymeric coating containing a photochromic amount of at least one photochromic material, e.g., spirooxazine, naphthopyran and/or fulgide, and (3) a dendritic polyester acrylate film coherently appended to the photochromic coating. Describes also the aforedescribed photochromic article having an abrasion-resistant coating affixed to the dendritic polyester acrylate film, e.g., an abrasion-resistant coating comprising an organo silane; and a photochromic article having an antireflective coating affixed to the abrasion-resistant coating.

Abstract: Described are photochromic articles that include a substrate and a photochromic amount of at least one organic photochromic material (b) represented by graphic formula XIII adapted to change from an unactivated state to an activated state by exposure to radiation substantially in a wavelength range from 380 to 410 nanometers (nm) when measured over a wavelength range of from 380 to 700 nm. The photochromic articles demonstrate a photochromic response when activated behind an ultraviolet blocking transparency such as an automotive windshield. For example, the photochromic articles retain at least 12 percent of the activation measured as change in optical density or delta OD under outdoor simulating conditions in the Outdoor Test when tested under conditions simulating an eyeglass wearer behind an automotive windshield in the Behind the Windshield Test. Methods for producing the aforedescribed photochromic articles are also described.

Abstract: Described are imbibition compositions that incorporate kinetic enhancing additive(s) into photochromic polymeric host material. Kinetic enhancing additives include organic polyol(s), epoxy-containing compound(s) or a mixture thereof that improves the performance of organic photochromic compounds in the polymeric host as determined in the Photochromic Performance Test. Also described is a process for incorporating kinetic enhancing additives into polymeric substrates prior to, after and/or with organic photochromic compounds and the resulting photochromic articles produced by such a process.

Abstract: Certain, non-limiting embodiments of the disclosure provide ophthalmic elements and devices comprising an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of at least one exterior surface of an ophthalmic element or substrate. Further, according to certain non-limiting embodiments, the at least partial coating adapted to polarize at least transmitted radiation comprises at least one at least partially aligned dichroic material. Other non-limiting embodiments of the disclosure provide methods of making ophthalmic elements and devices comprising forming an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of at least one exterior surface of the ophthalmic element or substrate. Optical elements and devices and method of making the same are also disclosed.

Abstract: Certain, non-limiting embodiments of the disclosure provide ophthalmic elements and devices comprising an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of at least one exterior surface of an ophthalmic element or substrate. Further, according to certain non-limiting embodiments, the at least partial coating adapted to polarize at least transmitted radiation comprises at least one at least partially aligned dichroic material. Other non-limiting embodiments of the disclosure provide methods of making ophthalmic elements and devices comprising forming an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of at least one exterior surface of the ophthalmic element or substrate. Optical elements and devices and method of making the same are also disclosed.

Abstract: Described are compositions of at least one material represented by a pyrano[3,2-c]quinoline structure, a pyrano[3,2-c]quinolinone structure or mixtures thereof. The pyrano[3,2-c]quinoline structure is characterized by having a nitrogen atom at the 6-position ring atom and an oxy-substituent at the 5-position ring atom. The pyrano[3,2-c]quinolinone structure is characterized by having a substituted nitrogen atom at the 6-position ring atom and an oxo-substituent at the 5-position ring atom, the nitrogen atom substituents being hydrogen, aliphatic substituents, cycloaliphatic substituents, aromatic substituents, heteroaromatic substituents or a combination thereof. Both of the pyrano[3,2-c]quinoline and pyrano[3,2-c]quinolinone structures are characterized by having two substituents at the 2-position ring atom. Also described are photochromic articles that contain or that have coatings or films containing at least one of the novel compositions or combinations thereof with other photochromic materials.

Abstract: Described is a polymerizable composition of a photochromic amount of at least one photochromic compound, at least one material having at least one carbonate group and at least one hydroxyl group, and at least one monoisocyanate containing material having at least one unsaturated group. The polymerizable composition optionally contains copolymerizable monomers. Also described are photochromic polymerizates, e.g., photochromic optical elements such as ophthalmic lenses, prepared from the polymerizable composition of the present invention.

Abstract: Described is a coating composition adapted to enhance the adhesion of a polymeric coating or film applied to a substrate. The coating composition is interposed between the substrate and the polymeric coating and comprises (a) at least one coupling agent, partial hydrolysates thereof or mixtures thereof in a concentration greater than 25 weight percent, based on the weight of the total composition, and (b) an adhesion enhancing amount of an epoxy-containing material having at least two epoxy groups. The coating composition is substantially free of photochromic materials and colloidal particles chosen from silica, alumina or mixtures thereof. Also described is a process for using the coating composition and articles coated with the composition and additional coatings and films which can be photochromic.

Abstract: Described is a photochromic article that includes a substrate and at least a partial coating of an at least partially cured polymerizable composition of a photochromic amount of at least one photochromic compound, at least one material having at least one carbonate group and at least one hydroxyl group, and at least one monoisocyanate containing material having at least one unsaturated group. Also described are photochromic optical elements such as ophthalmic lenses, prepared from an optical element substrate coated with the photochromic polymerizable composition.

Abstract: Described are novel reversible photochromic indenonaphthopyran compounds, examples of which are 2H-naphtho[1,2-b]pyrans characterized by having a substituted or unsubstituted indeno group fused at the 2,3 positions of the group to the 1 side of the 2H-naphthopyran. The compounds also have substituents at the 3 position of the pyran ring. Substituents may also be present at the number 5, 6, 7, 8, 9, 10, 11, 12, or 13 carbon atoms of the compounds. These compounds may be represented by the following graphic formulae: Also described are various substrates, e.g., paper, glass, organic polymeric materials, etc., that contain or that are coated with such compounds. Optically clear articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel indenonaphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., indenonaphthopyrans, naphthopyrans, benzopyrans, oxazine-type compounds, etc., are also described.

Abstract: Described are imbibition compositions that incorporate kinetic enhancing additive(s) into photochromic polymeric host material. Kinetic enhancing additives include organic polyol(s), epoxy-containing compound(s) or a mixture thereof that improves the performance of organic photochromic compounds in the polymeric host as determined in the Photochromic Performance Test. Also described is a process for incorporating kinetic enhancing additives into polymeric substrates prior to, after and/or with organic photochromic compounds and the resulting photochromic articles produced by such a process.

Abstract: Described are novel photochromic 6-aryl substituted 3H-naphtho[2,1-b]pyran compounds, examples of which are naphthopyran compounds having a substituted aryl group at the number 6 carbon atom and certain substituents at the 3-position of the pyran ring. Certain substituents may also be present at the number 7, 8, 9 or 10 carbon atoms of the compounds. These compounds may be represented by the following graphic formula: Also described are polymeric organic host materials that contain one or more of such compounds or combinations of such compounds) with complementary photochromic compounds, e.g., other naphthopyrans, benzopyrans and spiro(oxazine)type compounds.