Polarizing devices and methods of making the same

1/98

OPHTHALMIC ELEMENT, AND METHODS FOR MANUFACTURING AN OPHTHALMIC ELEMENT

background

[0001] The polarization of ophthalmic devices, such as the polarization of sunglasses, can reduce glare due to light reflected by surfaces, such as, but not limited to, pavement, water and snow, increasing thus vision under dazzling conditions. Consequently, polarization of ophthalmic devices has become of increasing interest for use in sports and other outdoor activities where reflected glare can be problematic.

[0002] Conventional polarizing filters for ophthalmic devices are formed from sheets or layers of a polymeric material that has been stretched or otherwise oriented and impregnated with an iodine chromophore or dichroic dye. For example, one method of forming a conventional polarizing filter for ophthalmic devices is to heat a sheet or layer of polyvinyl alcohol (PVA) to soften the PVA and then stretch the sheet to orient the PVA polymer chains. Thereafter, an iodine chromophore or dichroic dye is impregnated into the sheet in such a way that the iodine molecules or dye aggregate to the aligned polymer chains and assume a particular order or alignment.

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2/98

Alternatively, the iodine chromophore or dichroic dye may first be impregnated into the PVC sheet, and thereafter the sheet may be heated and stretched as described above to orient the PVA polymer chains and associated chromophore or dye.

[0003] Iodine chromophores and dichroic dyes are dichroic materials, that is, they absorb one of two components of transmitted radiation polarized in the orthogonal plane more strongly than the other. Even though dichroic materials will preferentially absorb one of two components of transmitted radiation polarized in the orthogonal plane, if the molecules of the dichroic material are not properly positioned or arranged, no effective polarization of the transmitted radiation will be achieved. That is, due to the random placement of molecules in the dichroic material, selective absorption by the individual molecules will neutralize each other in such a way that no effective or global polarizing effect will be achieved. However, by proper positioning or ordering of the molecules of the dichroic material within the oriented polymer chains of the PVA sheet, effective polarization can be achieved. That is, the PVA sheet can be prepared to polarize transmitted radiation, or in other words, a polarizing filter can be formed. As used in this context, the term polarize means to confine the vibrations of the electrical vector of

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3/98 light waves.

[0004] One method of forming an ophthalmic polarizing device using such polarizing polymer sheet filters is to laminate or glue the filter to the convex outer surface of a lens substrate. Another method for forming lenses using conventional polarizing polymer sheet filters involves coating the surface of a lens mold with the polarizing sheet and subsequently filling the mold with the substrate material in such a way as the sheet. of polarization stay on the surface of the lens when removed from the mold. Still other methods involve incorporating the filter into the lens structure itself. For example, the filter can be incorporated into the lens structure by laminating the filter between two substrates that form the lens together, or by casting a substrate material around the filter. In the latter method, the bias filter can be placed in a mold and the mold filled with the substrate material, typically a thermoset plastic monomer, in such a way that the substrate material surrounds and surrounds the bias filter. Thereafter, the substrate material can be cured to form the lens.

[0005] It is also known to form a polarizing layer by forming a film of a linear photopolymerizable material that exhibits selective orientation in a layer component of

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4/98 release of a transfer tinsel. Thereafter, a polymeric liquid crystal material containing a dichroic dye can be applied to the linear photopolymerizable material and the chains of the liquid crystal polymer aligned. Since a dichroic dye is contained within the liquid crystal polymer, when the liquid crystal polymer chains are aligned, the dichroic dye molecules are also aligned and an effective polarizing effect can then be achieved. The polarizing layer can then be transferred from the transfer tinsel to a suitable substrate by means of, for example, hot stamping.

[0006] Other methods of forming sheets or polarizing layers using liquid crystal materials are also known. For example, polarization sheets formed from oriented thermotropic liquid crystal films containing dichroic dyes have been exposed. Furthermore, polarization sheets formed by extrusion of liquid crystalline polymers containing covalently bonded dichroic dyes as part of the main polymer chains have been exposed.

summary

[0007] Several non-limiting embodiments set out in this context provide optical elements and devices and ophthalmic elements and devices. For example, an embodiment does not limit

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5/98 provides an ophthalmic element which comprises a partial coating which is adapted to polarize transmitted radiation on a portion of an outer surface of the ophthalmic element.

[0008] Another non-limiting embodiment provides an ophthalmic element which comprises a guidance feature on a part of an outer surface of the ophthalmic element, and a partial coating that is adapted to polarize transmitted radiation in a part of a guidance feature.

[0009] Another non-limiting embodiment provides an ophthalmic element comprising a partial coating comprising an alignment means on a part of an outer surface of the ophthalmic element, a partial coating comprising an alignment transfer material on a part of a coating partial that comprises the means of alignment, and a partial coating comprising an anisotropic material and a dichroic material on a portion of a partial coating comprising the alignment transfer material.

[00010] Yet another non-limiting embodiment provides an ophthalmic element comprising a substrate, an orientation feature comprising a partial coating comprising a photo-orientable polymeric network on a portion of an outer surface of the substrate, and an even coating.

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6/98 adapted to polarize transmitted radiation in a part of a partial coating comprising the photo-orientable polymeric network, the partial coating adapted to polarize transmitted radiation comprising a liquid crystal polymer and a dichroic dye.

[00011] Yet another non-limiting embodiment provides an optical element comprising a partial coating adapted to polarize transmitted radiation on a part of an outer surface of the optical element, the partial coating comprising a partially ordered liquid crystal material and a partially dichroic material lined up.

[00012] Another non-limiting embodiment provides an optical device comprising an optical element comprising a partial coating comprising an alignment means on a part of an outer surface of an optical element, and the partial coating comprising an anisotropic material and a dichroic material in a part of a partial coating comprising the alignment means.

[00013] Other non-limiting embodiments discussed in this context provide methods for manufacturing optical elements and ophthalmic elements. For example, a non-limiting embodiment provides a method for manufacturing an element of

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7/98 which comprises forming a partial coating adapted to polarize transmitted radiation on a part of an outer surface of the ophthalmic element.

[00014] Another non-limiting embodiment provides a method for manufacturing an ophthalmic element comprising imparting a guidance feature comprising a partial coating comprising an alignment means on a part of an outer surface of the ophthalmic element, applying a dichroic material to a part of an orientation feature, and partially align a part of a dichroic material.

[00015] Another non-limiting embodiment provides a method for manufacturing an ophthalmic element comprising applying a partial coating to a part of an outer surface of the ophthalmic element, and adapting a part of the partial coating to polarize transmitted radiation.

[00016] Yet another non-limiting embodiment provides a method for manufacturing an ophthalmic element comprising applying a partial coating comprising an alignment means to a part of an outer surface of the ophthalmic element, partially ordering a part of the alignment means, applying a partial coating comprising an anisotropic material and a dichroic material to a part of the partial coating comprising

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8/98 the partially ordered alignment means, and partially align a part of a dichroic material.

[00017] Another non-limiting embodiment provides a method for manufacturing a lens for ophthalmic applications comprising applying a partial coating comprising a photo-orientable polymeric network to a portion of an outer surface of a lens, partially ordering a portion of the polymeric network photo-orientable with plane-polarized ultraviolet radiation, applying a partial coating comprising a liquid crystal material and a dichroic dye to a portion of a partial coating comprising the photoorientable polymeric network, partially aligning a portion of the partial coating comprising the liquid crystal material and a dichroic dye, and fixing partially a part of the coating comprising the liquid crystal polymer and a dichroic dye.

[00018] Yet another non-limiting embodiment provides a method for manufacturing an optical element comprising applying a partial coating to a portion of an outer surface of the optical element, and adapting a portion of the partial coating to polarize transmitted radiation.

Detailed Description

[00019] As used in this report and the appended claims, articles a, one, and o, include several references to no.

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9/98 unless expressly and unambiguously limited to a reference.

[00020] In addition, for the purposes of this report, unless otherwise indicated, all numbers expressing amounts of ingredients, reaction conditions, and other properties or parameters used in the report are intended to be understood to be modified in all cases by the term “about”. Consequently, unless otherwise indicated, it should be understood that the numerical parameters set out in the following report and in the appended claims are approximations. Lastly, and not in an attempt to limit the application of the equivalents doctrine to the scope of the claims, numerical parameters should be read in light of the number of significant digits reported and the application of conventional rounding techniques.

[00021] Furthermore, even though the numerical ranges and parameters which establish the broad scope of the invention are approximations as discussed above, the numerical values ​​set out in the Examples section are reported as accurately as possible. It should be understood, however, that these numerical values ​​inherently contain certain errors resulting from the measurement equipment and/or measurement technique.

[00022] Elements and devices according to various non-limiting embodiments of the

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10/98 of the present invention will be described below. A non-limiting embodiment provides an optical element, and more specifically provides an ophthalmic element comprising a partial coating adapted to polarize transmitted radiation on a portion of an outer surface of the ophthalmic element.

[00023] As discussed earlier, polarizing means confining the vibrations of the electrical vector of light waves to one direction. As discussed above, conventional polarizing ophthalmic elements, such as lenses for ophthalmic devices, are typically formed by laminating or molding a polarizing filter formed from a stretched PVA sheet (or layer) that contains a dichroic material, such as like iodine chromophore, to a lens substrate. However, in accordance with various non-limiting embodiments set out in this context, the ophthalmic element comprises a partial coating adapted to polarize transmitted radiation on a portion of an outer surface of the ophthalmic element. Thus, according to these non-limiting embodiments, the conventional laminate structure discussed above is not required. As discussed in this context, the preposition em means that the coating in question is connected directly to the object surface or indirectly connected to the object surface through one or more other coatings or structures. Furthermore,

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11/98 as used in this context, the term coating means a film which may or may not have a uniform thickness, and specifically excludes the stretched polymeric sheets of the prior art.

[00024] As used in this context, the term ophthalmic refers to the elements and devices that are associated with the eye and vision, such as, but not limited to, lenses for ocular use, and articles eyepieces. Thus, for example, in accordance with various non-limiting embodiments set out in this context, the ophthalmic element may be selected from corrective lenses, non-corrective lenses, and magnifying lenses.

[00025] Furthermore, ophthalmic elements according to various non-limiting embodiments set out in this context may be formed from any substrate material that is suitable, including, but not limited to, glass and organic materials.

[00026] For example, according to various non-limiting embodiments set out in this context, the ophthalmic element can be formed from an organic substrate material. Organic substrate materials that are suitable for use in conjunction with the various non-limiting embodiments set forth herein include, but are not limited to, art-recognized polymers that are useful as ophthalmic elements, by

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12/98 example, organic optical resins which are used to prepare optically clear castings for optical applications such as ophthalmic lenses.

[00027] Specific non-limiting examples of organic substrate materials that can be used to form the ophthalmic elements disclosed in this context include polymeric materials, for example, homopolymer and copolymers, prepared from monomers and monomer mixtures disclosed in US patent No. 5,962,617 and in US Patent No. 5,658,501 from column 15, line 28 to column 16, line 17; US patent exhibitions those that are specifically incorporated in this context by reference. For example, such polymeric materials can be thermoplastic or thermosetting polymeric materials, can be transparent or optically pure, and can have any required index of refraction. Non-limiting examples of such exposed monomers and polymers include: polyol(allyl carbonate) monomers, for example, allyl diglycol carbonates such as diethylene glycol bis(allyl carbonate), which monomer is sold under the trade mark CR-39 by PPG Industries, Inc.; Polyurea-polyurethane (polyurea-urethane) polymers, which are prepared, for example, by the reaction of a polyurethane prepolymer and a diamine curing agent, a composition for one of these polymers being sold under the trade name TRIVEX by PPG Industries, Inc.; poly carbonate monomer

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13/98 finished ol(meth)acryloyl; diethylene glycol dimethacrylate monomers; ethoxylated phenol methacrylate monomers; diisopropenyl benzene monomers; ethoxylated trimethylol propane triacrylate monomers; ethylene glycol bismethacrylate monomers; poly(ethylene glycol) bismethacrylate monomers; urethane acrylate monomers; poly(ethoxylated) bisphenol A dimethacrylate; poly(vinyl acetate); poly(vinyl) alcohol; poly(vinyl chloride); poly(vinylidene) chloride; polyethylene; polypropylene; polyurethanes; polythiourethanes; thermoplastic polycarbonates, such as the carbonate resin derivative bonded from bisphenol A and phosgene, one such material being sold under the trade name LEXAN; polyesters, such as the material sold under the trademark MYLAR; poly(ethylene terephthalate); polyvinyl butyral; poly(methyl methacrylate), such as the material sold under the trademark PLEXIGLAS, and polymers prepared by reacting polyfunctional isocyanates with polythiols or polyepisulphide monomers, either homopolymerized or co-and/or terpolymerized with polythiols, polyisocyanates, polyisothiocyanates and optionally monomers ethylenically unsaturated or vinyl monomers containing halogenated aromatics. Also considered are copolymers of these monomers and mixtures of the described polymers and copolymers with other polymers, for example, to form block copolymers or interpenetration network products. Even though the exact nature of the ma

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14/98 organic substrate material is not of major importance for the various non-limiting embodiments set out in this context, according to a non-limiting embodiment, the organic substrate material should be chemically compatible with partial coatings adapted to polarize transmitted radiation in a part of the outer surface of the ophthalmic element.

[00028] Furthermore, according to certain non-limiting embodiments set out in this context, the substrates that form the ophthalmic elements may have a protective coating, such as, but not limited to, an abrasion resistant coating, such as as a "hard coating" on their outer surfaces. For example, commercially available thermoplastic polycarbonate lens substrates are often sold with an abrasion resistant coating already applied to their exterior surfaces because these surfaces tend to be easily scratched, scraped, or rubbed. An example of such a lens substrate is the GENTEX™ polycarbonate lens (available from Gentex Optics). Consequently, as used in this context, the term "substrate" includes a substrate provided with a protective coating, such as, but not limited to, an abrasion resistant coating, on its(s) surface(s).

[00029] On the other hand, the elements

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15/98 and ophthalmic substrates used to form the ophthalmic elements in accordance with the various non-limiting embodiments discussed in this context may be uncolored, colored, photochromic, or color-photochromic ophthalmic elements.

[00030] As used in this context, the term "uncolored" with respect to ophthalmic elements and substrates means essentially free from additions of coloring agents (such as, but not limited to, conventional dyes) and having an absorption spectrum for visible radiation that does not vary significantly in response to actinic radiation. As used in this context, “actinic radiation” means electromagnetic radiation that is capable of eliciting a response. Although not limiting in this context, actinic radiation can include both visible and ultraviolet radiation.

[00031] As used in this context, the term "colored" with respect to ophthalmic elements and substrates means that it contains a coloring adding agent (such as, but not limited to, conventional dyes) and that it has an absorption spectrum for visible radiation that does not vary significantly in response to actinic radiation.

[00032] As used in this context, the term "photochromic" means that it has

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16/98 an absorption spectrum for visible radiation which varies in response to actinic radiation and which is thermally reversible. Although not limiting in this context, for example, photochromic elements, substrates, coatings and materials that can be used in conjunction with various non-limiting embodiments set out in this context can change from a transparent state to a colored state in response to radiation, or they can change from one colored state to the other colored state in response to radiation. For example, according to a non-limiting embodiment the photochromic ophthalmic element may change from a transparent state to a colored state in response to actinic radiation and return to a transparent state in response to thermal radiation or heat. Alternatively, the photochromic ophthalmic element may change from a first colored state to a second colored state in response to actinic radiation and return to the first colored state in response to thermal radiation or heat.

[00033] As used in this context, the term color-photochromic with respect to ophthalmic elements and substrates means containing an addition of coloring agent and a photochromic material, and having an absorption spectrum for visible radiation that varies in response to radiation actinic and is thermally reversible. Thus, for example, in a non-limiting embodiment, the color-photochromic substrate may have a first characteristic color.

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17/98 shows the coloring agent and a second color characteristic of the combination of the coloring agent and the photochromic material when exposed to actinic radiation.

[00034] As discussed above, ophthalmic elements according to the various non-limiting embodiments that are set out in this context comprise a partial coating adapted to polarize radiation transmitted on a part of an outer surface of the ophthalmic elements. As used in this context, the term "transmitted radiation" refers to radiation that is caused to pass through a part of an element or substrate. Although not limiting in this regard, transmitted radiation could be visible radiation or could be a combination of visible radiation and ultraviolet radiation. In accordance with various non-limiting embodiments set out in this context, the partial coating may be adapted to polarize transmitted visible radiation, or it may be adapted to polarize a combination of transmitted visible and transmitted ultraviolet radiation.

[00035] Furthermore, the partial coating adapted to polarize radiation transmitted on a part of an outer surface of the ophthalmic element may comprise a dichroic material. As used herein, the terms “dichroic material and “dichroic dye” refer to a material that absorbs one of two plane-polarized components.

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18/98 orthogonal radiation transmitted more strongly than the other. A measure of how strongly the dichroic material absorbs one of two orthogonal planopolarized components comprises the “absorption ratio. As used in this context, the term "absorption ratio refers to the ratio of the absorbance of radiation polarized linearly in a foreground to the absorbance of radiation of the same wavelength linearly polarized in a plane orthogonal to the foreground, in that the foreground is taken as the plane with the highest absorbance. Methods for determining absorption ratios are described in detail below in the Examples section.

[00036] Dichroic materials that can be used in conjunction with various non-limiting embodiments set forth in this context include, but are not limited to, dichroic materials having absorptive ratios ranging from 2 to 30 (or higher as required) . For example, in accordance with certain non-limiting embodiments, the dichroic material may be provided with an absorption ratio of 3, 5, 7, 10 or greater. Furthermore, combinations of dichroic materials endowed with different absorption ratios can be used in accordance with various non-limiting embodiments set out in this context. For example, in a non-limiting embodiment, the partial coating adapted to polarize

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19/98 a transmitted radiation may comprise a first dichroic material having a first absorption ratio and a second dichroic material having a second absorption ratio which is different from the first absorption ratio.

[00037] Non-limiting examples of dichroic materials that are suitable for use in conjunction with the various non-limiting embodiments described herein include azomethines, indigoids, thioindigoids, merocyanines, indans, quinophthalonic dyes, perylenes, phthaloperines, triphenodioxazines, indoloquinoxalines, im , tetrazines, azo and (poly)azo dyes, benzoquinones, naphthoquinones, anthraquinone and (poil)anthraquinones, anthrapyrimidinones, iodine, as well as iodates.

[00038] Although not limiting in this context, in a non-limiting embodiment, the dichroic material is selected from azo and (poly)azo dyes. In another non-limiting embodiment, the dichroic material comprises anthraquinones and (poly)anthraquinones.

[00039] Furthermore, in another non-limiting embodiment, the dichroic material may be a polymerizable dichroic material. That is, in accordance with this one non-limiting embodiment, the dichroic material may comprise a group that is capable of being polymerized (i.e., a "polymerizable group"). For example, although not limiting in this context

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20/98 to, in a non-limiting embodiment the a dichroic material may have an alkoxy, polyalkoxy, alkyl, or polyalkyl substituent terminated with a polymerizable group.

[00040] According to a non-limiting embodiment, the partial coating adapted to polarize radiation transmitted on a part of an outer surface of the ophthalmic element may comprise a dichroic material and an anisotropic material. As used in this context, the term anisotropic means to have a property that differs in value when measured in a different direction. Thus, anisotropic materials are materials that have a property that differs in value when measured in a different direction. For example, although not limiting in this context, anisotropic materials can be used in conjunction with the various non-limiting embodiments set out in this context can be optically anisotropic materials.

[00041] Non-limiting examples of anisotropic materials that are suitable for use in conjunction with various non-limiting embodiments set forth herein include liquid crystal materials selected from liquid crystal polymers, liquid crystal prepolymers, and crystal monomers liquid. As used in this context, the term prepolymer means partially polymerized materials. For example, according to

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21/98 a non-limiting embodiment, the partial coating adapted to polarize transmitted radiation on a part of an outer surface of the ophthalmic element may comprise a dichroic material and an anisotropic material selected from liquid crystal polymers, liquid crystal prepolymers , and liquid crystal monomers.

[00042] Liquid crystal monomers that are suitable for use as anisotropic materials in conjunction with various non-limiting embodiments set out in this context include mono-functional as well as multi-functional liquid crystal monomers. Furthermore, according to various non-limiting embodiments set out in this context, the liquid crystal monomer can be a liquid crystal monomer capable of being cross-linked, and it can further be a liquid crystal monomer capable of being photo-crosslinkable. As used in this context, the term photo-crosslinkable means a material, such as a monomer, a prepolymer, or a polymer, that can be crosslinked by exposure to actinic radiation.

[00043] Non-limiting examples of photo-crosslinkable liquid crystal monomers that are suitable for use as anisotropic materials according to various non-limiting embodiments set out in this context include liquid crystal monomers that have functional groups selected from

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22/98 acrylates, methacrylates, allyl, allyl ethers, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, vinyl ethers and mixtures thereof. Non-limiting examples of photo-crosslinkable liquid crystal monomers suitable for use as anisotropic materials in accordance with various non-limiting embodiments set forth herein include liquid crystal monomers which are endowed with functional groups selected from acrylates, methacrylates, alkynes, epoxides , thiols and their mixtures.

[00044] Liquid crystal polymers and prepolymers that are suitable for use as anisotropic materials in conjunction with various non-limiting embodiments set forth herein include thermotropic liquid crystal polymers and prepolymers, and liquid crystal polymers and prepolymers lyotropic drugs. Furthermore, the liquid crystal polymers and prepolymers can be main chain polymers and prepolymers or side chain polymers and prepolymers. Additionally, in accordance with various non-limiting embodiments set out in this context, the liquid crystal polymer or prepolymer may be capable of being cross-linked, and may further be susceptible of being photo-cross-linked.

[00045] Non-limiting examples of suitable liquid crystal polymers and prepolymers that are suitable for use as anisotropic materials.

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23/98 cos according to various non-limiting embodiments set out in this context include, but are not limited to, main and side chain polymers and prepolymers which are endowed with functional groups selected from acrylates, methacrylates , allyl, allyl ethers, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, vinyl ethers, as well as mixtures thereof. Non-limiting examples of photocrosslinkable liquid crystal polymers and prepolymers that are suitable for use as anisotropic materials in accordance with various non-limiting embodiments set out in this context include those polymers and prepolymers that have functional groups selected from acrylates, methacrylates, alkynes, epoxides, thiols and mixtures thereof.

[00046] Additionally, although not limiting in this context, according to various non-limiting embodiments, a part of the anisotropic material can be partially ordered and a part of the dichroic material can be partially aligned with a part of the partially ordered anisotropic material. As used in this context, the term ordered means to be brought into a suitable position or arrangement, such as by alignment with another structure or by some other force or effect. Furthermore, the way it is used

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24/98 in this context, the term aligned means to be brought into a suitable position or disposition by interaction with another structure.

[00047] As discussed above, even though dichroic materials absorb one of two orthogonal plane-polarized components of transmitted radiation more strongly than the other, the dichroic material molecules must be properly positioned or arranged to achieve an effective polarization of the transmitted radiation. In this way, according to various non-limiting embodiments set out in this context, a part of a dichroic material may be brought into a suitable position or arrangement (i.e. ordered or aligned) in such a way that an overall polarization effect can be achieved. .

[00048] For example, according to a non-limiting embodiment, the partial coating may comprise a partially ordered anisotropic material (such as, but not limited to, a liquid crystal material) and a partially aligned dichroic material, wherein the a partially aligned dichroic material is partially aligned with the partially aligned anisotropic material. Although not limiting in this context, according to this non-limiting embodiment, a part of a dichroic material may be partially aligned in such a way that the long axis of a part of the one.

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25/98 dichroic material is generally parallel to the direction of order of the anisotropic material.

[00049] According to another non-limiting embodiment, the a dichroic material can be bonded or caused to react with a part of the anisotropic material. For example, according to this non-limiting embodiment, a dichroic material can be polymerized in one part or caused to react with a part of the anisotropic material. Furthermore, although not limiting in this regard, in accordance with this non-limiting embodiment, a dichroic material may comprise a substituent containing terminal and/or pendant groups selected from hydroxyl, carboxyl, (meth)acryloxy, 2(methacryloxy ) ethylcarbamil (OC(O)NHC₂H₄OC(O)C(CH3)=CH₂), epoxide or a mixture thereof.

[00050] In addition to a dichroic material and an anisotropic material, the partial coating adapted to polarize transmitted radiation on a part of an outer surface of the ophthalmic element according to various non-limiting embodiments set out in this context may further comprise a photochromic material. As discussed above, photochromic materials are endowed with an absorption spectrum that varies in response to actinic radiation.

[00051] For example, although not

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26/98 limiting in this context, a photochromic material may be selected from pyrans, oxazines, fulgiides and fulgimides, and metallic dithiozonates. Nevertheless, according to several non-limiting embodiments, the selected photochromic material is not of the greatest importance, and its selection will depend on the definitive application and the desired color or hue for that application. According to a non-limiting embodiment, a photochromic material is endowed with a maximum absorption between 300 and 1000 nanometers when activated (i.e., exposed to actinic radiation).

[00052] Furthermore, in some non-limiting embodiments, the partial coating may comprise a mixture of photochromic materials. Generally speaking, although not limiting in this context, when two or more photochromic materials are used in combination, the photochromic materials are often selected to complement each other to produce a desired color or hue. For example, mixtures of photochromic materials can be used in accordance with certain non-limiting embodiments set out in this context to achieve certain activated colors, such as an approximately neutral gray or an approximately neutral brown. See, for example, US Patent No. 5,645,767, column 12, line 66 through column 13, line 19, the disclosure of which is specifically incorporated herein by reference, which describes parameters defining colors

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27/98 gray and neutral brown.

[00053] Non-limiting examples of photochromic pyrans that can be used in conjunction with various non-limiting embodiments set forth in this context include benzopyrans, naphthopyrans, e.g. naphtho[1,2-b]pyrans, naphtho[2.1-b]pyrans , fused-in naphthopyrans, such as those set forth in the US patent No. 5,645,767; spiropyrans, for example, spiro(benzindoline)naphthopyrans, spiro(indoline)benzopyrans, spiro(indoline)naphthopyrans, spiro(indoline)quinopyrans and spiro(indoline)pyrans; and heterocyclic-fused naphthopyrans, such as those set forth in US Patent Nos. 5,723,072, 5,698,141, 6,153,126, and 6,022,497, which are incorporated herein by reference. More specific examples of naphthopyrans and complementary organic photochromic substances are described from column 11, line 57, through column 13, line 36, in US Patent No. 5,658,501, which is specifically incorporated herein by reference.

[00054] Non-limiting examples of photochromic oxazines that can be used in conjunction with various non-limiting embodiments set forth in this context include benzoxazines, naphthoxazines, and spiro-oxazines, e.g., spiro(indoline)naphtoxazines, spiro(indoline)pyridobenzoxazines,

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28/98 spiro (benzindoline)pyridobenzoxazines, spiro(benzindoline) naphthoxazines, spiro(indoline)benzoxazines, and spiro(in-doline)fluoranthenoxazine.

[00055] Non-limiting examples of photochromic etchings and effulmides that can be used in conjunction with various non-limiting embodiments set forth in this context include the 3-furyl and 3-thienyl etchings and effulmides, which are set forth in column 20, line 5 through to column 21, line 38, of the US patent. No. 4,931,220 (which is hereby specifically incorporated herein by reference) and mixtures of any of the aforementioned photochromic materials/compounds.

[00056] Non-limiting examples of photochromic metallic dithizonates that can be used in conjunction with various non-limiting embodiments disclosed herein include mercury dithizonates, which are described, for example, in US Patent No. 3,361,706, which is hereby incorporated. specifically incorporated herein by reference.

[00057] Furthermore, it is considered that photochromic materials such as photochromic dyes and photochromic compounds encapsulated in metal oxides can be used according to several non-limiting embodiments set out in this context. See, for example, the materials described in US Patent Nos. 4,166,043 and 4,367,170, which are specific

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29/98 are incorporated in this context by reference. Additionally, polymerizable photochromic materials, such as those set forth in US Patent No. 6,113,814, which is specifically incorporated herein by reference, and compatibilized photochromic materials, such as those set forth in US Patent No. 6,555,028, which is specifically incorporated herein by reference, may also be used in conjunction with various non-limiting embodiments set forth in this context.

[00058] On the other hand, according to various non-limiting embodiments set out in this context, the partial coating adapted to polarize transmitted radiation may further comprise an additive that can facilitate one or more of the processing properties, or the performance of the partial coating. Non-limiting examples of such additives include dyes, alignment enhancers, kinetic enhancement additives, photoinitiators, solvents, light stabilizers (such as, but not limited to, ultraviolet light absorbers and light stabilizers) such as stabilizers Amino Light Delayed (HALS), heat stabilizers, mold release agents, rheology control agents, leveling agents (such as, but not limited to, surface active agents), free radical scavengers, and adhesion promoters (such as hexanediol diacrylate and agents

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30/98 coupling). In a non-limiting embodiment, the additive is a colorant.

[00059] As used in this context, the term “alignment promoter” means an additive that can facilitate one of the rate and uniformity of alignment of a material to which it is added. Non-limiting examples of alignment enhancers that may be present in the partial coating in accordance with various non-limiting embodiments set forth herein include those described in US Patent No. 6,338,808 and in US Patent Publication No. 2002/0039627, which are specifically incorporated by reference in this context.

[00060] Non-limiting examples of dyes that may be present in the partial coating according to the various non-limiting embodiments set out in this context include organic dyes that are capable of imparting a desired color or optical properties to the partial coating.

[00061] Non-limiting examples of kinetic enhancement additives that may be present in the partial coating according to various non-limiting embodiments set out in this context include compounds containing epoxide, organic polyols, and/or plasticizers. More specific examples of such kinetic enhancement additives are disclosed in US Patent No. 6,433,043 and in the publication

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31/98 of US Patent No. 2003/0045612, which are specifically incorporated by reference in this context.

[00062] Non-limiting examples of photoinitiators that may be present in the partial coating according to various non-limiting embodiments set out in this context include cleavage type photoinitiators and abstraction type photoinitiators. Non-limiting examples of cleavage type photoinitiators include acetophenones, α-aminoalkylphenones, benzoin ethers, benzoyl oximes, acylphosphine oxides and bisacylphosphine oxides or mixtures of such initiators. A commercial example of such photoinitiators is DAROCURE® 4265, which can be found available from Ciba Chemicals, Inc. Non-limiting examples of abstraction type photoinitiators include benzophenone, Michler's ketone, thioxanthone, anthraquinone, camphorquinone, fluorone, ketocoumarin or mixtures of these initiators.

[00063] Another non-limiting example of a photoinitiator that may be present in the partial coating according to various non-limiting embodiments set out in this context is a visible light photoinitiator. Non-limiting examples of suitable visible light photoinitiators are set forth in column 12, line 11 through column 13, line 21 of US Patent No. 6,602,603, which is specifically incorporated by reference herein.

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32/98

[00064] Non-limiting examples of solvents that may be present in the partial coating according to various non-limiting embodiments set out in this context include those that will dissolve the solid components of the coating, which are compatible with the coating and the elements and substrates, and/or can ensure uniform coverage of the outer surface(s) to which the coating is applied. Potential solvents include, but are not limited to, the following: acetone, amyl propionate, anisole, benzene, butyl acetate, cyclohexane, ethylene glycol dialkyl ethers, e.g., diethylene glycol dimethyl ether and its derivatives (sold as CELLOSOLVE® industrial solvents), diethylene glycol dibenzoate, dimethyl sulfoxide, dimethyl formamide, dimethoxybenzene, ethyl acetate, isopropyl alcohol, methyl cyclohexanone, cyclopentanone, methyl ethyl ketone, methyl isobutyl ketone, methyl propionate, propylene carbonate, tetrahydrofuran, toluene, xylene, 2-methoxyethyl ether, 3-propylene glycol methyl ether, as well as mixtures thereof.

[00065] Ophthalmic elements according to various non-limiting embodiments set out in this context may further comprise one or more other coatings that can facilitate binding, adhesion, or wettability of the partial coating adapted to polarize radiation transmitted in a part of an outer surface of the elements ophthal

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33/98 tamarins. For example, ophthalmic elements according to a non-limiting embodiment may comprise a partial preparative coating between a part of the partial coating adapted to polarize transmitted radiation and a part of an outer surface of the ophthalmic elements. Furthermore, although not required, in accordance with this non-limiting embodiment, the primer coating can serve as a barrier coating to prevent the interaction of the coating ingredients with the ophthalmic element or substrate surface and vice versa.

[00066] Non-limiting examples of primer coatings that can be used in conjunction with various non-limiting embodiments set out in this context include coatings comprising coupling agents, hydrolysates of partial coupling agents, and mixtures thereof. As used in this context, coupling agent means a material that has a group capable of reacting, agglutinating and/or associating with a group on a surface. According to a non-limiting embodiment, a coupling agent can serve as a molecular bond at the interface of two surfaces that can be similar or different surfaces. Coupling agents, in another non-limiting embodiment, can be monomers, oligomers, prepolymers and/or polymers. These materials include, but are not limited to, organo

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34/98 metals such as silanes, titanates, zirconates, aluminates, zirconium aluminates, their hydrolysates and their mixtures. As used in this context, the phrase "partly hydrolysates of coupling agents means that some to all groups capable of being hydrolyzed in the coupling agent are hydrolyzed. In addition to coupling agents and/or coupling agent hydrolysates, the preparative coatings may comprise other adhesion enhancing ingredients. For example, although not limiting in this regard, the primer coating may further comprise an enhancing amount of an epoxide-containing material. Adhesion enhancing amounts of epoxy-containing materials when added to the coupling agent-containing coating composition can improve the adhesion of a subsequently applied coating compared to a coupling agent-containing coating composition that is essentially free of the material that contains epoxide. Other non-limiting examples of primer coatings that are suitable for use in conjunction with the various non-limiting embodiments set forth herein include those described in US Patent No. 6,602,603 ​​and US Patent No. 6,150,430, which are specifically incorporated herein. by reference.

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35/98

[00067] In addition, ophthalmic elements according to various non-limiting embodiments set out in this context may, furthermore, comprise an additional partial coating selected from photochromic coatings, anti-reflective coatings, transition coatings, preparative coatings and coatings. protection in of the ophthalmic element. For example, although not limiting in this context, an additional partial coating may be on a part of the partial coating adapted to polarize transmitted radiation, i.e. as an overlay. Additionally or alternatively, the partial coating adapted to polarize radiation may be used on a part of a first outer surface of the ophthalmic element, and the partial additional coating may be formed on a part of a second outer surface of preferably the ophthalmic element, in that the first outer surface on the ophthalmic element is opposite the second outer surface of the ophthalmic element.

[00068] Non-limiting examples of conventional photochromic coatings include coatings comprising any of the photochromic materials discussed below. For example, although not limiting in this regard, photochromic coatings may be polyurethane photochromic coatings, such as those described in US Patent No. 6,187,444; photochromic coatings

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36/98 aminoplast resin cos, such as those described in US Patent Nos. 4,756,973, 6,432,544B1 and 6,506,488; polysilane photochromic coatings, such as those described in US Patent No. 4,556,605; photochromic poly(meth)acrylate coatings, such as those described in US Patent Nos. 6,602,603, 6,150,430 and 6,025,026, and WIPO publication WO 01/02449 A2; photochromic polyanhydride coatings, such as those described in the US patent No. 6,436,525; photochromic polyacrylamide coatings such as those described in US Patent No. 6,060,001; epoxy resin photochromic coatings, such as those described in US Patent Nos. 4,756,973 and 6,268,055; and poly(urea-urethane) photochromic coatings, such as those described in US Patent No. 6,531,076. US patent reports and the aforementioned international publications are hereby specifically incorporated in this context.

[00069] As used in this context, the term “transition coating” means a coating that helps to create a gradient in properties between two coatings. For example, although not limiting in this regard, a transition coating can help to create a gradient in hardness between a relatively hard coating and a relatively soft coating. Examples I haven't read

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37/98 transition coatings mitotic include radiation cured acrylate-based thin films.

[00070] Non-limiting examples of protective coatings include abrasion resistant coatings comprising organosilanes, abrasion resistant coatings comprising radiation cured acrylate-based thin films, abrasion resistant coatings based on inorganic materials such as silica, titania and/or zirconia, abrasion resistant organic coatings of the type that are curable by ultraviolet light, oxygen barrier coatings, UV shielding coatings, and combinations thereof. For example, according to a non-limiting embodiment, the protective coating may comprise a first coating of a radiation-cured acrylate-based thin film and a second coating comprising an organosilane. Non-limiting examples of commercial protective coating products include SILVUE® 124 and HI-GARD® coatings, available from SDC Revestimentos, Inc. and PPG Industries, Inc., respectively.

[00071] Another non-limiting embodiment of the present invention provides an ophthalmic element comprising a guiding feature on a part of an outer surface of the ophthalmic element, and a partial coating adapted to polarize transmitted radiation in a part of the ophthalmic feature.

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38/98 guidance. As used in this context, the term orientation feature means a mechanism that can facilitate the positioning of one or more other structures that are exposed to a part of the feature, either directly or indirectly from a combination of the same. Non-limiting examples of guide features that can be used in conjunction with this and other non-limiting embodiments set forth herein include partial coatings comprising a partially ordered alignment means, partially stretched polymeric sheets, partially treated surfaces, and combinations thereof.

[00072] For example, although not limiting in this context, according to a non-limiting embodiment, an orientation feature may comprise a partial coating comprising a partially ordered alignment means. As used in this context, the term aligning means means a material that can facilitate the positioning of one or more other materials. Non-limiting methods of ordering a part of the alignment medium are described in detail below.

[00073] Non-limiting examples of suitable alignment means that can be used in conjunction with various non-limiting embodiments set forth in this context set out in this context include photo-orientation materials, frictional orientation materials, and liquid crystal materials. for example

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39/98 plo, according to a non-limiting embodiment, the an orientation feature may comprise a partially ordered alignment means which is selected from photo-orientation materials, friction orientation materials, and liquid crystal materials .

[00074] Non-limiting examples of liquid crystal materials that are suitable for use as an alignment means in accordance with various non-limiting embodiments set forth herein include liquid crystal polymers, liquid crystal prepolymers, and liquid crystal monomers . For example, according to a non-limiting embodiment, the an orientation feature may comprise a partial coating comprising a partially ordered liquid crystal material selected from liquid crystal polymers, liquid crystal prepolymers, and crystal monomers liquid.

[00075] Liquid crystal monomers that are suitable for use as an alignment means in conjunction with various non-limiting embodiments set out in this context include monofunctional as well as multifunctional liquid crystal monomers. Furthermore, in accordance with various non-limiting embodiments set out in this context, the liquid crystal monomer may be a liquid crystal monomer capable of being cross-linked and may further be a liquid crystal monomer capable of being photo-crosslinked.

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40/98

[00076] Non-limiting examples of crosslinkable liquid crystal monomers that are suitable for use as an alignment means in accordance with various non-limiting embodiments set out in this context include liquid crystal monomers that are endowed with functional groups selected from of acrylates, methacrylates, allyl, allyl ethers, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, vinyl ethers, and their blends. Non-limiting examples of cross-linkable liquid crystal monomers suitable for use as an anisotropic material in accordance with various non-limiting embodiments set out herein include liquid crystal monomers having functional groups selected from acrylates, methacrylates, alkynes, epoxides , thiols, and mixtures thereof.

[00077] Liquid crystal polymers and prepolymers that are suitable for use as an alignment means in conjunction with in accordance with various non-limiting embodiments set forth herein include thermotropic liquid crystal polymers and prepolymers, and polymers and prepolymers. -lyotropic liquid crystal polymers. Furthermore, the liquid crystal polymers and prepolymers can be main chain polymers and prepolymers or side chain polymers and prepolymers. Additionally, according to

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41/98 with various non-limiting embodiments set out in this context, the liquid crystal polymer or prepolymer may be cross-linkable, and it may further be photo-crosslinkable.

[00078] Non-limiting examples of liquid crystal polymers and pre-polymers that are suitable for use as an alignment means in accordance with various non-limiting embodiments set forth herein include, but are not limited to, polymers and pre- - main chain and side chain polymers that are endowed with functional groups selected from acrylates, methacrylates, allyl, allyl ethers, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, vinyl ethers, as well as their mixtures. Non-limiting examples of liquid crystal polymers and prepolymers capable of being crosslinked suitable for use as an alignment means in accordance with various non-limiting embodiments set forth herein include those polymers and prepolymers which are provided with selected functional groups a from acrylates, methacrylates, alkynes, epoxides, thiols, and mixtures thereof.

[00079] Non-limiting examples of photo-orientation materials that are suitable for use as a means of alignment in conjunction with in accordance with various non-limiting embodiments expos.

Petition 870180025102, dated 03/28/2018, p. 47/114

42/98 tas include azobenzene derivatives, cinnamic acid derivatives, coumarin derivatives, ferulic acid derivatives, and polyimides. For example, according to a non-limiting embodiment, the orientation feature may comprise a partial coating comprising a partially ordered photo-orientable polymer network selected from azobenzene derivatives, cinnamic acid derivatives, coumarin derivatives, derivatives of ferulic acid and polyimides. Specific non-limiting examples of cinnamic acid derivatives that can be used as a means of alignment in conjunction with various non-limiting embodiments set forth herein include polyvinyl cinnamate and polyvinyl esters of paramethoxycinnamic acid.

[00080] As used in this context, the term "friction-oriented material" means a material that can be partially ordered by friction on a portion of a surface of the material with another suitably textured material. For example, although without limitation in this context, according to a non-limiting embodiment, the friction-oriented material may be rubbed with a suitably textured cloth or velvet. Non-limiting examples of friction-oriented materials that are suitable for use as an alignment means in conjunction with various non-limiting embodiments set forth herein include (poly)imides, (poly)siloxanes, (poly)acrylates, and (poly)coumarins . of

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43/98 so, for example, although without limitation in this context, the partial coating comprising the aligning means may be a partial coating comprising a polyimide that has been rubbed with velvet or a cloth in order to partially sort out, a part of the surface of the polyimide.

[00081] As discussed above, the an orientation feature in accordance with certain non-limiting embodiments set forth in this context may comprise a partially ordered polymer sheet. For example, although without limitation in this context, a sheet of polyvinyl alcohol (PVA) may be partially stretched to partially arrange the PVA polymer chain, and thereafter the sheet may be bonded to a portion of an outer surface of the ophthalmic element to form the guidance feature.

[00082] Furthermore, as discussed above, an orientation feature according to various non-limiting embodiments set out in this context may comprise a partially treated surface. As used in this context, the term treated surface refers to a portion of a surface that has been physically altered to create an ordered region on a portion of the surface. Non-limiting examples of partially treated surfaces include partially rubbed surfaces and partially etched surfaces.

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44/98

For example, according to a non-limiting embodiment, the an orientation feature comprises a partially treated surface selected from partially rubbed surfaces and partially etched surface.

[00083] Non-limiting examples of etched surfaces that are of use in forming guidance features according to various non-limiting embodiments set forth in this context include chemically etched surfaces, plasma etched surfaces, nanocausticized surfaces (such as surfaces etched using a scanning tunneling microscope, surfaces etched using a microscope or an atomic force microscope), laser etched surfaces, and electron beam etched surfaces.

[00084] further, according to various non-limiting embodiments, the an orientation feature may comprise a first ordered region having a first general direction and a second ordered region adjacent to the first region having a second general direction that is different from first general direction. In this way, the orientation feature can have a plurality of regions that have various arrangements required to form a desired pattern or design. Additionally, as discussed above, one or more different guidance features can be combined to form the guidance feature.

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45/98 tion in accordance with various non-limiting embodiments set out in this context.

[00085] As discussed above, according to various non-limiting embodiments, the partial coating adapted to polarize transmitted radiation may comprise a dichroic material. Non-limiting examples of suitable dichroic materials are set out in detail above. Furthermore, as discussed above, it is generally necessary to partially align a portion of a dichroic material to achieve an effective polarizing effect. In this way, according to various non-limiting embodiments, a part of a dichroic material may be partially aligned by direct contact with a part of the orientation resource or by indirect contact with a part of the orientation resource, e.g. plus other structures or materials.

[00086] For example, in a non-limiting embodiment, a part of dichroic material may be partially aligned with a part of an orientation feature. although not limiting in this context, according to this a non-limiting embodiment a part of a dichroic material may be partially aligned such that the longitudinal axis of a part of a dichroic material is generally parallel to a general direction of an ordered region of the guidance feature. Beyond

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46/98 further, although not limiting in this context, according to this non-limiting embodiment, the guidance resource may comprise a liquid crystal material.

[00087] According to another non-limiting embodiment, the partial coating adapted to polarize transmitted radiation may comprise an anisotropic material and a dichroic material. Although not limiting in this context, in accordance with this non-limiting embodiment, a part of the anisotropic material may be partially aligned with a guide feature and a portion of a dichroic material may be partially aligned with a partially aligned anisotropic material such as discussed previously. Suitable non-limiting examples of anisotropic material are set out in detail above.

[00088] Furthermore, in addition to an orientation feature and the partial coating adapted to polarize transmitted radiation, according to various non-limiting embodiments set out in this context, the ophthalmic elements may comprise a partial coating comprising an alignment transfer material, and further may comprise a plurality of partial coatings comprising an alignment transfer material. As used in this context, the term "alignment transfer material signiPetition 870180025102 of 03/28/2018, p. 52/114

47/98 is a material that can facilitate the propagation of a suitable arrangement or position from one structure or material to another.

[00089] For example, in a non-limiting embodiment, a partial coating comprising an alignment transfer material may be between an orientation feature and a part of the partial coating adapted to polarize transmitted radiation. According to this non-limiting embodiment, a part of the alignment transfer material can be aligned with a part of the orientation feature, and a part of the partial coating dichroic material can be aligned with a part of the alignment transfer material . That is, the alignment transfer material can facilitate the propagation of a suitable arrangement or position from an orientation feature to a dichroic material. Furthermore, if the partial coating adapted to polarize radiation comprises an anisotropic material, a portion of the anisotropic material may be partially aligned with the alignment transfer material and a dichroic material may be partially aligned with the anisotropic material, as discussed previously.

[00090] Non-limiting examples of alignment transfer materials that are suitable for use in conjunction with various non-limiting embodiments set forth in this context include material.

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48/98 liquid crystal products selected from liquid crystal polymers, liquid crystal prepolymers, and liquid crystal monomers.

[00091] Liquid crystal monomers that are suitable for use as an alignment transfer material in conjunction with various non-limiting embodiments set out in this context include mono-functional as well as multi-functional liquid crystal monomers. Furthermore, in accordance with various non-limiting embodiments set out in this context, the liquid crystal monomer can be a liquid crystal monomer capable of being cross-linked, and it can further be a liquid crystal monomer capable of being photo-crosslinked.

[00092] Non-limiting examples of crosslinkable liquid crystal monomers that are suitable for use as an alignment transfer material in accordance with various non-limiting embodiments set out in this context include liquid crystal monomers that are provided with selected functional groups from acrylates, methacrylates, allyl, allyl ethers, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, vinyl ethers, as well as mixtures thereof. Non-limiting examples of liquid crystal monomers capable of being photo-crosslinked, suitable for use as an aliquot transfer material.

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49/98 according to various non-limiting embodiments set out in this context include liquid crystal monomers having functional groups selected from acrylates, methacrylates, alkynes, epoxides, thiols, as well as mixtures thereof.

[00093] Liquid crystal polymers and prepolymers that are suitable for use as an alignment transfer material in conjunction with various non-limiting embodiments set forth herein include, but are not limited to, polymers and prepolymers of thermotropic liquid crystals, and lyotropic liquid crystal polymers and prepolymers. Furthermore, the liquid crystal polymers and prepolymers can be main chain polymers and prepolymers or side chain polymers and prepolymers. Additionally, in accordance with various non-limiting embodiments set out in this context, the liquid crystal polymer or prepolymer may be cross-linkable, and may further be photo-cross-linkable.

[00094] Non-limiting examples of liquid crystal polymers and prepolymers that are suitable for use in accordance with various non-limiting embodiments set forth herein include, but are not limited to, main chain polymers and prepolymers and side chain which are endowed with functional groups selected from acrylates, methacrylates, allyl, ethers.

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50/98 allyl, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, vinyl ethers, as well as mixtures thereof. Non-limiting examples of photocrosslinkable liquid crystal polymers and prepolymers that are suitable for use in the alignment transfer materials in accordance with various non-limiting embodiments set forth herein include those polymers and prepolymers that are provided with selected functional groups a from acrylates, methacrylates, alkynes, epoxides, thiols, as well as their mixtures.

[00095] Furthermore, the ophthalmic element according to various non-limiting embodiments set out in this context may comprise one or more coatings that can facilitate agglutination, adhesion, or wetting of a part of an outer surface of the ophthalmic element by an orientation feature. For example, the ophthalmic element may further comprise a partial primer coating positioned between a guide feature and a portion of an outer surface of the ophthalmic element. Non-limiting examples of preparative coatings which may be suitable for use in conjunction with this non-limiting embodiment are set out in detail above.

[00096] Yet another non-limiting embodiment provides an ophthalmic element that

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51/98 comprises a partial coating comprising an alignment means on a part of an outer surface of the ophthalmic element, a partial coating comprising an alignment transfer material on a part of a partial coating comprising the alignment means, and the a partial coating comprising an anisotropic material and a dichroic material on a portion of a partial coating comprising the alignment transfer material.

[00097] According to various non-limiting embodiments set out in this context, the partial coating comprising the alignment means may have a thickness that varies widely, depending on the final application and/or the processing equipment employed. For example, in a non-limiting embodiment, the thickness of the partial coating comprising the alignment means can range from 2 nanometers to 10,000 nanometers. In another non-limiting embodiment, the partial coating comprising the aligning means may have a variable thickness from 5 nanometers to 1000 nanometers. In yet another non-limiting embodiment, the partial coating comprising the alignment means may have a variable thickness from 10 nanometers to 100 nanometers. According to yet another non-limiting embodiment, the partial coating comprising the alignment means may have a thickness

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52/98 variable from 50 nanometers to 100 nanometers. Additionally, in accordance with various non-limiting embodiments, the ophthalmic element may comprise a plurality of partial coatings comprising an alignment arrangement. In addition, each of the plurality of subcoats may have the same or a different thickness as the other subcoats in the plurality.

[00098] Furthermore, according to various non-limiting embodiments set out in this context, the partial coating comprising the alignment transfer material can have a thickness that varies widely, depending on the final application and/or the processing equipment employed. For example, in a non-limiting embodiment, the thickness of the partial coating comprising the partially ordered alignment transfer material may range from 0.5 micrometer to 25 micrometer. In another non-limiting embodiment, the partial coating comprising the partially ordered alignment transfer material may have a thickness ranging from 5 to 10 micrometers. Additionally, in accordance with various non-limiting embodiments, the ophthalmic element may comprise a plurality of partial coatings comprising an alignment transfer material. Furthermore, each of the plurality of partial coatings may be provided with the same or a thickness

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53/98 different from the others in the partial coverings of the plurality.

[00099] Furthermore, according to various non-limiting embodiments set out in this context, the partial coating comprising the anisotropic material and the a dichroic material may have a thickness that varies widely, depending on the final application and/or processing equipment employee. According to a non-limiting embodiment, the partial coating comprising the anisotropic material and the dichroic material may have a thickness of 5 micrometers. Additionally, in accordance with various non-limiting embodiments, the ophthalmic element may comprise a plurality of partial coatings comprising an anisotropic material and a dichroic material. Furthermore, each of the plurality of subcoats may be of the same thickness or a different thickness relative to the other subcoats in the plurality.

[000100] As discussed above, in order to achieve an effective polarization effect, a portion of a dichroic material in general must be brought into a suitable arrangement or position (ie, ordered or aligned). Thus, although not limiting in this context, according to various non-limiting embodiments, a part of the alignment means can be partially ordered

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54/98 in a first general direction, a part of the alignment transfer material may be aligned with a part of the alignment means in a second general direction which is generally parallel to the first general direction, a part of the anisotropic material may be partially aligned with a portion of the transfer material aligning in a third general direction that is generally parallel to the second general direction, and a part of the dichroic material may be partially aligned with a part of the anisotropic material as discussed above. That is, according to this non-limiting embodiment a part of the dichroic material can be partially aligned such that the longitudinal axis of the part of the dichroic material is generally parallel to the third direction of the partially aligned anisotropic material.

[000101] Furthermore, according to various non-limiting embodiments set out in this context, the partial coating comprising the alignment means and/or the partial coating comprising the alignment transfer material may further comprise a dichroic material, the which may be the same or different from a dichroic material of the partial coating comprising the anisotropic material and the dichroic material. Additionally, any of the partial coatings discussed above may further comprise a soft material.

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55/98 tochromic and/or an additive that may enhance one of the processing properties, or the performance of the partial coating, or combinations thereof. Non-limiting examples of suitable photochromic materials and additives are given above.

[000102] As discussed above, the ophthalmic element according to the various non-limiting embodiments set out in this context may further comprise one or more coatings that can facilitate the agglutination, adhesion, or wetting of the partial coating comprising the surface alignment means exterior or a part thereof, of the ophthalmic element and/or between two different partial coatings. For example, according to a non-limiting embodiment, a partial preparative coating may be between the partial coating comprising the alignment means and a part of an outer surface of the ophthalmic element. In another non-limiting embodiment, a partial primer coating may be between the partial coating comprising the alignment means and the partial coating comprising the alignment transfer material and/or between the partial coating comprising the alignment transfer material and the partial coating comprising both an anisotropic material and a dichroic material. Non-limiting examples of suitable coatings

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56/98 preparers are discussed in detail above.

[000103] According to another non-limiting embodiment there is provided an ophthalmic element comprising a substrate, an orientation feature comprising a partial coating comprising a network of photo-orientable polymers on a part of an outer surface of the substrate, and a partial coating adapted to polarize transmitted radiation on a part of a partial coating comprising the network of photoorientable polymers. Furthermore, according to this non-limiting embodiment, the partial coating adapted to polarize radiation comprises a liquid crystal material and a dichroic dye.

[000104] Additionally, according to the non-limiting embodiment mentioned above, the partial coating comprising the network of photo-orientable polymers may further comprise a dichroic dye, which may be the same or different from a dichroic dye of the partial coating which comprises liquid crystal material and a dichroic dye. Furthermore, any of the partial coatings may further comprise a photochromic material and/or an additive that may enhance one of the processing properties, or the performance of the partial coating. Non-limiting examples of ma

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57/98 photochromic materials and suitable additives are discussed above.

[000105] In addition, the ophthalmic element according to this and other non-limiting embodiments set out in this context may comprise a partial coating comprising an alignment transfer material between the partial coating comprising the network of photoorientable polymers and the adapted partial coating to polarize transmitted radiation. Non-limiting examples of alignment transfer materials that are suitable are set out above.

[000106] Additionally, the ophthalmic element according to this non-limiting embodiment may further comprise one or more layers that may facilitate the partial coating comprising the network of photo-orientable polymers to agglutinate, adhere or moisten to a part of an outer surface of the substrate. For example, in accordance with this non-limiting embodiment, a partial primer coating may be disposed between the partial coating comprising the network of photoorientable polymers and a portion of an outer surface of the substrate. Non-limiting examples of preparative coatings which are suitable for use in conjunction with according to this non-limiting embodiment are set out above.

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[000107] In addition, as discussed above, the ophthalmic element according to this and others according to this non-limiting embodiments set out in this context may further comprise an additional partial coating selected from photochromic coatings, anti-reflective coatings, coatings transition coatings, primer coatings, and protective coatings on a part of the substrate. Non-limiting examples of suitable photochromic coatings, anti-reflective coatings, transition coatings, primer coatings, and protective coatings are discussed above.

[000108] As discussed above, embodiments of the present invention consider optical elements and devices. For example, a non-limiting embodiment provides an optical element comprising a partial coating adapted to polarize radiation transmitted on a portion of an outer surface of the optical element, the partial coating comprising a partially ordered liquid crystal material and a partially aligned dichroic material.

[000109] Another non-limiting embodiment provides an optical device comprising an optical element comprising a partial coating comprising an alignment means on a part of an outer surface of an element

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59/98 optical, and a partial coating comprising an anisotropic material and a dichroic material on a part of the partial coating comprising the alignment means. Furthermore, although not required, a partial coating comprising an alignment transfer material may be disposed between a portion of the partial coating comprising the alignment means and the partial coating comprising the anisotropic material and the dichroic material. Optical elements, alignment means, alignment transfer materials, anisotropic materials, and dichroic materials that can be used in conjunction with this non-limiting embodiment are discussed in detail above.

[000110] Additionally, as discussed above, according to various non-limiting embodiments, the partial coating comprising the alignment means and/or the partial coating comprising the alignment transfer material may further comprise a dichroic material, which may be the same or different from a partial coating dichroic material comprising a partial coating dichroic material comprising the anisotropic material and the dichroic material. In addition, any of the partial coatings discussed above may further comprise a photochromic material and/or an additive.

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60/98 vo which may intensify one of the processing properties, or the performance of the partial coating. Non-limiting examples of suitable photochromic materials and additives are set out above.

[000111] In addition, optical elements according to various non-limiting embodiments set out in this context may further comprise one or more layers that may facilitate the agglutination, adhesion, or wetting of any of the coatings to a part of an outer surface of the element optical. For example, a partial preparative coating may be provided between the partial coating comprising the alignment means and a part of an outer surface of the optical element or it may be between the partial coating adapted to polarize transmitted radiation and a part of the outer surface. of the optical element or another coating. Non-limiting examples of preparative coatings which are suitable for use in conjunction with this non-limiting embodiment are set out below.

[000112] Additionally, as discussed above with respect to the foregoing non-limiting embodiments, optical elements according to this non-limiting embodiment may further comprise an additional partial coating selected from selected from optical coatings.

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61/98 tochromics, anti-reflective coatings, transition coatings, preparatory coatings, and protective coatings on a part of the substrate. Non-limiting examples of suitable photochromic coatings, anti-reflective coatings, transition coatings, primer coatings, and protective coatings are discussed above.

[000113] Furthermore, although not limiting in this context, according to various non-limiting embodiments set out in this context, the optical device may be selected from corrective and non-corrective ocular articles, magnifying ocular articles, attachable snap lenses to eyewear, and contact lenses.

[000114] Several non-limiting embodiments of methods for manufacturing devices and polarization elements according to the present invention will be described below. A non-limiting embodiment provides a method for manufacturing an ophthalmic element which comprises forming a partial coating adapted to polarize transmitted radiation on a portion of an outer surface of the ophthalmic element.

[000115] although not limiting in this context, according to this non-limiting embodiment, forming the partial coating adapted to polarize transmitted radiation may comprise

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62/98 apply a partial coating comprising a dichroic material and an anisotropic material to a portion of an outer surface of the ophthalmic element and partially align a portion of the dichroic material. As discussed above, by bringing a part of a dichroic material into the proper position or arrangement, an effective polarizing effect can be achieved. Non-limiting examples of suitable dichroic and anisotropic materials for use in conjunction with this and other non-limiting embodiments of the methods for manufacturing ophthalmic elements set forth in this context are set forth above.

[000116] Non-limiting examples of application of partial coatings that can be used in conjunction with methods for manipulating ophthalmic and optical elements according to various non-limiting embodiments set forth in this context include, but are not limited to: spin coating, spray coating, spray and spin coating, curtain coating, flow coating, dip coating, injection molding, casting, roll coating, wire coating, and methods used in the overlay preparation, such as the method of the type described in US Patent No. 4,873,029. Generally speaking, the application method selected will depend on, among other things, the desired coating thickness, surface geometry.

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63/98 cie to which the coating is applied, and the viscosity of the coating.

[000117] Furthermore, according to various non-limiting embodiments set out in this context, the application of the partial coating comprising a dichroic material and an anisotropic material may occur before, after, or essentially at the same time as the partial alignment occurs of a part of a dichroic material.

[000118] For example, in a non-limiting embodiment where the application of the partial coating comprising a dichroic material and an anisotropic material occurs before partially aligning a part of a dichroic material, the method of forming the partial coating may comprise by rotation coating the partial coating on a portion of an outer surface of the ophthalmic element. Thereafter, a part of an anisotropic material can be partially ordered and a part of a dichroic material can be partially aligned with the partially aligned anisotropic material, for example, by exposing, , a part of the partial coating to a feature orientation after partial coating application.

[000119] According to another non-limiting embodiment, according to which to apply the partial coating comprising a dichroic material and an anisotropic material, occurs

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64/98 essentially while partially aligning a portion of a dichroic material, applying the partial coating may comprise coating the partial coating on a portion of an outer surface of the ophthalmic element such that, during coating, a portion of the anisotropic material is partially ordered and a portion of a dichroic material is partially aligned with the partially ordered anisotropic material. For example, although not limiting in this context, a portion of the anisotropic material may be partially ordered during coating due to shear forces created by the relative movement of the outer surface of the ophthalmic element relative to the coating being applied. Non-limiting coating methods in accordance with this non-limiting embodiment include, but are not limited to, curtain coating.

[000120] Additionally, according to various non-limiting embodiments set out in this context, forming the partial coating adapted to polarize transmitted radiation may comprise forming a plurality of partial coatings on a part of an outer surface of the ophthalmic element, one of which is adapted to polarize transmitted radiation. For example, although it is not limiting in this context, according to a non-limiting embodiment, the partial coating is formed.

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65/98 able to polarize transmitted radiation may comprise forming a first partial coating comprising an alignment means and partially arranging a portion of the aligning means, forming a second partial coating comprising an alignment transfer material and align part of the alignment transfer material, and forming a third partial coating comprising an anisotropic material and a dichroic material and partially aligning a portion of the dichroic material. Additionally, in accordance with this non-limiting embodiment, any one of the first and second partial coatings may further comprise a dichroic material. In addition, any one of the first, second or third partial coatings may comprise a photochromic material and/or an additive which may enhance the processing, properties or performance of the partial coating. Non-limiting examples of suitable dichroic materials, photochromic materials and additives are set forth above in the discussion of the various non-limiting embodiments of elements and devices.

[000121] The method for manufacturing ophthalmic elements according to various non-limiting embodiments set out in this context may further comprise partially fixing a part of one or more of the partial coatings after formation of the partial coating on one part of the element.

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66/98

As used in this context, the term fix means to fix in a desired position. For example, in a non-limiting embodiment, a part of the partial coating adapted to polarize transmitted radiation may be attached after formation of the partial coating on a part of an outer surface of the ophthalmic element. Although not limiting in this regard, in accordance with various non-limiting embodiments set out in this context, partially curing a part of a partial coating may comprise one of partially curing, partially crosslinking, or partially drying a part of the partial coating.

[000122] Furthermore, according to various non-limiting embodiments set out in this context, partially fixing a part of a partial coating may comprise curing partially to a part by exposing a part of the partial coating to infrared, ultraviolet, gamma radiation. or electronics in such a way as to initiate the polymerization reaction of the polymerizable components or crosslinking with or without a catalyst or initiator. This can be followed by a warm-up step if appropriate.

[000123] According to a non-limiting embodiment in which the partial coating comprises a material that is capable of being photocrosslinked, such as a liquid crystal material ca.

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67/98 In addition to being photo-crosslinked, partially curing may include partially crosslinking material capable of being photo-crosslinked by exposing that material to appropriate actinic radiation. For example, although not limiting in this regard, partially curing a partial coating comprising a material capable of being photo-crosslinked may comprise exposing a portion of the material capable of being photo-crosslinked to ultraviolet radiation in an essentially inert atmosphere. As used in this context, the term “essentially inert atmosphere” means an atmosphere that is endowed with limited reactivity in the material being cured. For example, in a non-limiting embodiment, the essentially inert atmosphere comprises no more than 100 ppm of O gas.₂. Examples of essentially inert atmospheres that are suitable include, but are not limited to, an atmosphere that contains nitrogen, argon, and carbon dioxide.

[000124] Methods for manufacturing ophthalmic elements in accordance with various non-limiting embodiments set forth in this context may further comprise applying a partial primer coating to a portion of an outer surface of the ophthalmic element prior to application of the partial coating adapted to polarize radiation transmitted. Furthermore, although not limiting in this context, an additional partial coating selected from

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68/98 of photochromic coatings, anti-reflective coatings, transition coatings, preparatory coatings, and protective coatings may be applied to a portion of an outer surface of the ophthalmic element either before or after application of the partial coating adapted to polarize transmitted radiation. Non-limiting examples of suitable preparative coatings, photochromic coatings, anti-reflective coatings, transition coatings, and protective coatings are described in detail above.

[000125] Additionally, if appropriate, the methods according to the various non-limiting embodiments set out in this context may further comprise cleaning a part of the ophthalmic element or substrate before applying any coating thereto. This can be done for the purpose of cleaning and/or promoting adhesion of the coating. Treatment techniques that are effective for plastic and glass are known to those skilled in the art.

[000126] As discussed above, according to a non-limiting embodiment there is provided a method for manufacturing an ophthalmic element comprising forming a partial coating adapted to polarize radiation transmitted on a part of a surface of the ophthalmic element. Additionally, according to this embodiment no

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69/98 limiting, the method may further comprise imparting an orientation feature to a portion of an outer surface of the ophthalmic element before forming the partial coating adapted to polarize transmitted radiation. According to this non-limiting embodiment, imparting an orientation feature to a part of an outer surface of the ophthalmic element may comprise applying a partial coating comprising an alignment means to a part of an outer surface of the ophthalmic element and ordering partially a portion of the alignment means, applying a partially stretched polymer sheet to a portion of an outer surface of the ophthalmic element, and partially treating a portion of an outer surface of the ophthalmic element, for example, but not limited thereto, by causticizing or rubbing.

[000127] Yet another non-limiting embodiment of a suitable method for manufacturing an ophthalmic element comprises imparting a guidance feature which comprises a partial coating comprising a means of alignment to a part of an outer surface of the ophthalmic element; apply a dichroic material to a portion of an orientation feature, and partially align a portion of a dichroic material.

[000128] In accordance with this non-limiting embodiment, transmitting an original resource

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70/98 Engaging a portion of an outer surface of the ophthalmic element may comprise applying a partial coating comprising an alignment means to a portion of an outer surface of the ophthalmic element and partially ordering a portion of the alignment means. For example, although not limiting in this context, imparting an orientation feature may comprise applying a partial coating comprising an alignment means to a portion of an outer surface of the ophthalmic element and partially arranging a portion of the alignment means. Non-limiting examples of alignment means which are suitable for use in conjunction with the various non-limiting embodiments of the methods which are presented in this context are set out above.

[000129] Non-limiting examples of suitable methods for partially ordering a part of the alignment means that can be used in conjunction with methods of manufacturing ophthalmic elements according to various non-limiting embodiments set out in this context include one of exposing a part of the plane-polarized ultraviolet radiation alignment means; exposing a part of the alignment medium to infrared radiation; exposing a portion of the alignment medium to a magnetic field; expose a part of the alignment medium to an electric field; dry to a part of the alignment medium; scorch a part of the middle of the alignment; expose to a part of

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71/98 means of alignment to a shear force; and rub the middle part of alignment.

[000130] For example, although not limiting in this context, according to a non-limiting example in which the alignment means is a photo-orientation material (such as, but not limited to, a polymeric network that is able to be photo-oriented), the method of manufacturing an ophthalmic element may comprise applying a partial coating comprising a photo-orientation material to a part of an outer surface of the ophthalmic element and partially arranging a part of the photo-orientation material by exposing the part to plane-polarization ultraviolet radiation. Thereafter, a dichroic material can be applied to a part of the partially ordered and partially aligned photoorientation material.

[000131] In addition, if required, transmitting a guidance resource may further comprise partially fixing a part of a guidance resource. As discussed above, partially fixing may include partially curing, partially cross-linking, or partially drying a portion of an orientation feature. For example, although not limiting in this context, the method according to a non-limiting embodiment set out in this context may comprise transmitting an orientation feature to a part of a surface.

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72/98 of the exterior of an ophthalmic element by applying a partial coating comprising an alignment means to a portion of an outer surface of the ophthalmic element, partially affixing a portion of the alignment means, and partially arranging a portion of the alignment means before applying a dichroic material.

[000132] Non-limiting examples for methods of applying a dichroic material to a part of an orientation feature comprising the partial coating comprising the alignment means according to the various non-limiting embodiments set out in this context, include those methods which discussed above for application of partial coatings. For example, although not limiting in this regard, methods of applying a dichroic material may include spin coating, spray coating, spray and spin coating, curtain coating, flow coating, dip coating, injection molding, casting , roll coating, wire coating, and methods used in preparing overlay, such as the method of the type described in US Patent No. 4,873,029.

[000133] Additionally, the a dichroic material can be applied to a part of the an orientation feature comprising the partial coating comprising the impregnating alignment means

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73/98 tion. Suitable impregnation techniques are described, for example, in US Patent Nos. 5,130,353 and 5,185,390, which are specifically incorporated by reference herein. For example, although not limiting in this context, dichroic material may be applied to a part of an orientation resource by applying a dichroic material to a part of the orientation resource, either as pure dichroic material or dissolved in a polymeric carrier or other organic solvent, and then subjecting the dichroic material and the orientation feature to heat to cause the dichroic material to spread on a portion of the orientation feature.

[000134] Furthermore, according to various non-limiting embodiments set out in this context, the application of a dichroic material to a part of an orientation feature can occur before the alignment of a dichroic material, after the alignment of a dichroic material, or essentially at the same time as the alignment of a dichroic material. For example, although not limiting in this context, in a non-limiting embodiment, a dichroic material may be applied prior to alignment by spin coating on a solution or mixture of a dichroic material and a liquid crystal polymer in a carrier over a part of the orientation feature and thereafter evaporating a part of the solvent or carrier to align a part of the powder.

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74/98 liquid crystal polymer and a part of a dichroic material. According to another non-limiting embodiment, a dichroic material can be applied and aligned at essentially the same time, for example, by instilling a part of the orientation feature with a dichroic material. Instillation methods are described in detail above.

[000135] According to various non-limiting embodiments set out in this context, a dichroic material can be applied to an orientation feature as a solution or mixture with a carrier, or in conjunction with one or more other materials, such as anisotropic materials, photochromic materials, and additives that can improve one's processing, properties, or performance of the applied material. Non-limiting examples of anisotropic materials, photochromic materials, and additives that are suitable are set forth in connection with various non-limiting embodiments of elements and devices discussed above.

[000136] Additionally, methods for manufacturing ophthalmic elements in accordance with various non-limiting embodiments set forth in this context may further comprise applying a partial primer coating to a portion of an outer surface of the ophthalmic element prior to imparting a guidance feature to the a part of the outer surface. Also, a partial coating

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Additional 75/98 selected from photochromic coatings, anti-reflective coatings, transition coatings, preparatory coatings, and protective coatings can be applied to a portion of an outer surface of the ophthalmic element and/or over a portion of a dichroic material. Non-limiting examples of suitable preparative coatings, photochromic coatings, anti-reflective coatings, transition coatings, preparatory coatings, and protective coatings are all described above.

[000137] Another non-limiting embodiment provides a method for manufacturing an ophthalmic element comprising applying a partial coating to a part of an outer surface of the ophthalmic element and adapting a part of the partial coating to polarize transmitted radiation. In accordance with this non-limiting embodiment, applying the partial coating to a portion of an outer surface of the ophthalmic element may occur before, after, or essentially at the same time as adapting a portion of the partial coating to polarize transmitted radiation.

[000138] For example, although not limiting in this context, according to a non-limiting embodiment applying the partial coating to a part of an outer surface of the ophthalmic element may comprise applying a coating

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partial 76/98 comprising an anisotropic material and a dichroic material to a part of an outer surface; and adapting a portion of the partial coating to polarize transmitted radiation may comprise partially aligning a portion of a dichroic material. Furthermore, partially aligning a portion of a dichroic material may comprise partially arranging a portion of the anisotropic material and partially aligning the dichroic material with a portion of the partially ordered anisotropic material.

[000139] Suitable methods of partially ordering a portion of the anisotropic material include, but are not limited to, exposing the anisotropic material to plane-polarized ultraviolet radiation, exposing a portion of the anisotropic material to infrared radiation, exposing the a part of the anisotropic material to a magnetic field, exposing a part of the anisotropic material to an electric field, drying a part of the anisotropic material, causticizing a part of the anisotropic material, exposing a part of the anisotropic material to a shear force, rubbing a part of the anisotropic material, and aligning a part of the anisotropic material with another structure or material, such as, if not is limited thereto, a partially ordered means of alignment.

[000140] In another non-limiting embodiment, apply the partial coating to the

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77/98 a part of an outer surface of the ophthalmic element comprises applying a partial coating comprising an alignment means to a part of an outer surface of the ophthalmic element, and adapting a part of the partial coating to polarize transmitted radiation comprises partially ordering a part of the alignment means, apply a dichroic material to a part of the partial coating comprising the alignment means, and partially aligning a portion of mm with a dichroic material.

[000141] Non-limiting examples of alignment means that are suitable for use in conjunction with various non-limiting embodiments of methods set forth in this context include those alignment means described above with respect to the various non-limiting embodiments discussed above. For example, according to a non-limiting embodiment, wherein applying the partial coating to a portion of an outer surface of the ophthalmic element comprises applying a partial coating comprising an alignment means to a portion of an outer surface of the ophthalmic element, the alignment medium can be selected from photo-orientation materials, friction-orientation materials, and liquid crystal materials.

[000142] Still according to various non-limiting embodiments, partially ordering a part of the alignment means may comprise a

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78/98 exposure of the alignment medium to plane-polarized ultraviolet radiation, exposure of a portion of the alignment medium to infrared radiation, exposure of a portion of the alignment medium to a magnetic field, exposure of a portion of the alignment medium to a electric field, drying of one part alignment medium, causticizing one part alignment medium, exposing one part alignment medium to a shear force, and rub the middle part of alignment.

[000143] For example, although not limiting in this context, according to a non-limiting embodiment in which the alignment means is a photo-orientation material (such as, but not limited to, a network of polymers orientable material), partially arranging a portion of the photoorientation material may comprise exposing a portion of the photoorientation material to plane-polarized ultraviolet radiation.

[000144] Furthermore, according to some non-limiting embodiments in which adapting a part of the partial coating to polarize transmitted radiation comprises applying a dichroic material to a part of the partial coating comprising a partially ordered alignment means and partially aligning a part of the a dichroic material, applying a dichroic material may occur before, after, or substantially at the same time in

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79/98 which partially aligns a part of a dichroic material. Non-limiting methods of applying a dichroic material to a part of the partial coating comprising the alignment means include spin coating, spray coating, spin and spray coating, curtain coating, flow coating, dip coating, molding by injection, casting, roll coating, wire coating, and methods used in preparing overlay, such as the method of the type described in the US patent No. 4,873,029 and instillation.

[000145] Methods for manufacturing ophthalmic elements in accordance with various non-limiting embodiments set forth in this context may further comprise applying a partial primer coating to a portion of an outer surface of the ophthalmic element prior to forming and adapting the partial coating to polarize transmitted radiation . Additionally, the methods used to manufacture ophthalmic elements may further comprise applying an additional partial coating, selected from photochromic coatings, anti-reflective coatings, transition coatings, primer coatings and protective coatings to a portion of the ophthalmic elements. For example, although not limiting in this context, an additional partial coating can be applied over a part of the partial coating that is adapted to

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80/98 polarize transmitted radiation. Alternatively, or additionally, the partial coating adapted to polarize transmitted radiation may be formed on a part of a first outer surface of the ophthalmic element, and the partial additional coating may be on a part of a second outer surface, preferably the ophthalmic element, in that the first outer surface on the ophthalmic element is opposite the second outer surface of the ophthalmic element. Non-limiting examples of such coatings are described in detail above.

[000146] Another non-limiting embodiment of a method for manufacturing an ophthalmic element comprises applying a partial coating comprising an alignment means to a part of an outer surface of the ophthalmic element and partially ordering a part of the alignment means. Thereafter, according to this non-limiting embodiment, a partial coating comprising an anisotropic material and a dichroic material is applied to a part of the partial coating comprising the alignment means and a part of a dichroic material is partially aligned. Although not required, a partial coating comprising an alignment transfer material may be applied to a portion of the partial coating comprising the alignment means, and partially align prior to application.

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81/98 the partial coating comprising the anisotropic material and a dichroic material thereto.

[000147] Still according to this non-limiting embodiment, partially ordering a part of the alignment means may comprise exposing a part of the alignment means to plane-polarized ultraviolet radiation, exposing a part of the alignment means to infrared radiation , exposing a part of the alignment medium to a magnetic field, exposing a part of the alignment medium to an electric field, drying a part of the alignment medium, etching a part of the alignment medium, exposing a part of the alignment medium to a shear force, and rubbing a part of the alignment medium.

[000148] Furthermore, although not limiting in this context, as discussed above, any of the partial coatings described above may be partially fixed after being applied. For example, according to a non-limiting embodiment, a part of the partial coating comprising the alignment means may be partially attached before, during or after being partially ordered to a part of the alignment means. Furthermore, according to this non-limiting embodiment, a part of the partial coating comprising the alignment transfer material and/or the partial coating comprising

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82/98 anisotropic material and a dichroic material may be partially fixed by curing a part of the partial coating. For example, a portion of the alignment transfer material may be exposed to ultraviolet radiation under an inert atmosphere to cure a portion of the alignment transfer material. Similarly, a portion of the partial coating comprising the anisotropic material and the dichroic material may be cured by exposing a portion of the anisotropic material to ultraviolet radiation under an inert atmosphere after partially aligning a portion of the dichroic material.

[000149] Another non-limiting embodiment of the invention provides a method for manufacturing a lens for ophthalmic applications comprising applying a partial coating comprising a network of photo-orientable polymers to a portion of an outer surface of the lens, partially ordering a portion of the network of photo-orientable polymers with plane-polarized ultraviolet radiation. Thereafter, a partial coating comprising a liquid crystal material and a dichroic dye is applied to a part of the partial coating comprising the network of photo-orientable polymers and the one dichroic dye is partially aligned. After alignment of a part of the coating comprising the liquid crystal material and a dichroic dye, a part

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83/98 of the coating comprising the liquid crystal material and a dichroic dye can be partially fixed, for example, although not limiting in this regard, by means of curing. Although not required, a partial coating comprising alignment transfer material may be applied to a portion of the partial coating comprising the network of photo-orientable polymers prior to application of the partial coating comprising the liquid crystal material and a colorant dichroic to it.

[000150] Other embodiments of the invention provide methods for manufacturing an optical element comprising applying a partial coating to a portion of an outer surface of the optical element, and adapting a portion of the partial coating to polarize radiation. Suitable methods for applying a partial coating and adapting a portion of the partial coating to polarize radiation are discussed in detail above.

[000151] Several non-limiting embodiments of the present invention will be illustrated in the non-limiting examples set out below.

EXAMPLES

Step 1

Preparation of Anisotropic Materials Solutions [000152] To a wide-mouth beaker containing a magnetic stir bar and positioned on a magnetic stirrer, 3 grams of each were added.

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84/98 one of the following liquid crystal monomers (LCM), which were found available from EMD Chemicals, Inc., in the order listed, with agitation:

RM 23 — reported as having the molecular formula of C₂₃H₂₃AT THE₅

RM 257 - reported as having the molecular formula of C33H32O10

RM 82 - reported as having the molecular formula of C39H44O10

RM 105 - reported as having the molecular formula of C₂₃H₂₆O₆

[000153] Anisole (8.0 grams) was added to the contents in the beaker and the resulting mixture was heated to 60°C and stirred until the solids dissolved as determined by visual observation. The resulting liquid crystal monomer (or LCMS) solutions were divided into two parts, “Part A-LCMS” and “Part B-LCMS. A wide-mouth cup containing Part A-LCMS was placed uncovered in a smoke hood on a scale until the solids percentage increased from the initial 60 percent to 62 percent. Part B-LCMS was 60 percent solids.

Step 2

Preparation of Stock Solutions for Anisotropic and Dichroic Materials

[000154] The following three dichroic dyes, which are available from

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85/98

Mitsubishi Chemical, were used to prepare colored liquid crystal monomer solutions by dichroic dye (i.e., Red-, Blue-, Yellow- or Gray-LCMS):

LSR-652, reported to be a red dye from Batch: 01J0315;

LSR-335, reported to be a blue dye from Lot: 01C131; and

LSR-120, reported to be a yellow dye from Lot: 2D231.

[000155] Each of the Red LCMS,

LCMS Blue, and LCMS Yellow were prepared by adding to Part A-LCMS (prepared in Step 1) the amount of dichroic dye needed to produce a color-dichroic dye LCMS having the percent dichroic dye, based on the solids of Part A-LCMS , listed for each later. The Gray LCMS was prepared using Part B-LCMS from Step 1 and adding the combination of dichroic dyes listed below in the amounts needed to give the dye percentage, based on the Part B-LCMS solids, listed below.

<td>Dye-Color LCMS</td><td>Dichroic dye</td><td>Percentage of Dichroic Dye</td>

<td>LCMS-Red</td><td>LSR652</td><td> 2,0</td>

<td>LCMS-Blue</td><td>LSR335</td><td> 3,0</td>

<td>LCMS-Yellow</td><td>LSR120</td><td> 2,5</td>

<td>LCMS-Grey</td><td>LSR652</td><td> 0,8</td>

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86/98

<td></td><td>LSR335 LSR120</td><td> 1,1 0, 6</td>

[000156] The LCMS-Red, LCMS-Blue and

Individual LCMS-Yellow also contained 1.0 percent, based on Part A-LCM solids, of Irgacure 819, a photoinitiator that is available from Ciba-Geigy Corporation; and 0.5 percent, based on Part A-LCMS solids, of a combination of stabilizers in a 50:50 weight ratio. The stabilizers were TINUVIN-292, a light stabilizer for coatings sourced from Ciba-Geigy, and SANDUVOR VSU, a light stabilizer based on oxalanilide chemistry available from Clariant. The LCMS-Grey contained 1.0 percent, based on Part B-LCMS solids, each of Irgacure 819 and the aforementioned combination of stabilizers.

Step 3:

Preparation of Coating Solutions Comprising Anisotropic and Dichroic Materials

[000157] Coating solutions comprising anisotropic materials and dichroic materials were prepared by adding the colored LCMS-stock dichroic dye from Step 2, in the indicated amounts, when weighed on an analytical balance, in Examples 1-5 below, to a wide-mouth glass and mixing with heating at 50-60°C, if ne

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87/98 necessary, to prevent the liquid crystal monomer from precipitating and to dissolve the dye. An additional coating solution, Example 6, used the LCMS-Grey prepared above in Step 2, and was also heated with mixing when required. After mixing, each solution was filtered using a syringe filter having a pore size of 1.2 micrometers to remove any particulate matter.

Example 1

<td>Material</td><td>Material Weight (grams)</td>

<td>Red Dye Solution</td><td> 0,6008</td>

<td>Blue Dye Solution</td><td> 1,2772</td>

<td>Yellow Dye Solution</td><td> 0,5049</td>

Example 2

<td>Material</td><td>Material Weight (grams)</td>

<td>Red Dye Solution</td><td> 0,5415</td>

<td>Blue Dye Solution</td><td> 0,8892</td>

<td>Yellow Dye Solution</td><td> 0,3501</td>

Example 3

<td>Material</td><td>Weight (grams)</td>

<td>Red Dye Solution</td><td> 0,5410</td>

<td>Blue Dye Solution</td><td> 0,8880</td>

<td>Yellow Dye Solution</td><td> 0,3945</td>

Example 4

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88/98

<td>Material</td><td>Weight (grams)</td>

<td>Red Dye Solution</td><td> 0,3939</td>

<td>Blue Dye Solution</td><td> 0,6460</td>

<td>Yellow Dye Solution</td><td> 0,3272</td>

Example 5

<td>Material</td><td>Weight (grams)</td>

<td>Red Dye Solution</td><td> 0,3758</td>

<td>Blue Dye Solution</td><td> 0,4908</td>

<td>Yellow Dye Solution</td><td> 0,2832</td>

[000158] Each of the aforementioned coating solutions was used in the procedure described later in Parts AD, to prepare partial coatings adapted to polarize radiation transmitted on the surface of a substrate. After preparation, the absorption ratio of each of the coated substrates was measured in the Absorption Ratio Measurement Test described in Part E. Part A Substrate Cleaning [000159] Square substrates measuring 5.08 cm x 5.08 cm x 0.635 cm (2" x 2" x 0.25") were obtained from the following material: CR-39® monomer lens material or TRIVEX®, both of which are available from PPG Industries, Inc.; 70 mm diameter flat lens of CR-607® monomer, which is available from PPG Industries, Inc.; and fo lenses

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89/98 tochromics from Transitions Optical Incorporated, with a refractive index of 1.50. Thereafter, each substrate was cleaned by washing in a liquid soap and water solution, rinsing with deionized water, and rinsing with isopropyl alcohol. After washing and rinsing, the substrates were dried and treated with oxygen plasma at a flow rate of 100 milliliters (ml) per minute and oxygen at 100 watts of power for one minute.

[000160] As indicated in Part D and Table 1 below, some of the substrates were further treated with a primer coating described in US Patent No. 6,150,430. More specifically, these substrates were treated by delivering the preparation coating composition for 10 seconds to the substrate while the substrate was rotated at 1500 rpm. The coated substrates were then cured with a Light-Welder® 5000-EC UV light source from Dymax Corp. placed at a distance of 10.16 cm (4 inches) from the light source for 10 seconds.

Part B

Orientation Resource Preparation Using a Photo-Orientable Polymer Network

[000161] An orientation feature was conveyed to a part of the cleaned substrates (described in Part A retro) as follows. A solution of a network of photo-orientable polymers available as

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90/98 Staralign® 2200 CP2 or CP4 solution, designations which are reported to mean 2 percent by weight of cyclopentane, and 4 percent by weight of cyclopentane, respectively, from Huntsman Advanced Materials, was applied to a part of the surface of the substrate prepared in Part A by dispensing the Staralign solution for 2 to 3 seconds on the substrate. When the Staralign solution was distributed on the substrate, the substrate was rotated at 600 to 800 revolutions per minute for about 2 to 3 minutes. After rotation, the substrates were placed in an oven maintained at 130°C for 20 to 30 minutes. Referring to Table 1 below, Staralign 2200 CP2 solution was used in Samples 6A1 and 6A2. All other samples, except for 6A(magnetic), were coated with Staralign 2200 CP4.

[000162] a part of the network of photo-orientable polymers was partially ordered by exposure to plane-polarized ultraviolet radiation, under a peak intensity of 18 milliWatts/cm² of UVA (320-390 nm) when measured using an electro-optical UV Power Puck™ radiometer, from Electronic Instrumentation and Technology, Inc. The ultraviolet radiation source was a BLAK-RAY Model B-100A Longwave UV Lamp. Again, referring to Table 1, Samples 1A through 6D, were exposed to plane-polarized ultraviolet radiation for 2 minutes, the Samples

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6A1 and 6A2 were exposed to planopolarized ultraviolet radiation for 3 minutes.

Part C

Preparation of Adapted Partial Coatings to Polarize Transmitted Radiation

[000163] Partial coatings adapted to polarize transmitted radiation were then formed on each of the substrates prepared in Part B using one of the dichroic dye-colloid LCMS described above in Examples 1-6 of Step 3.

[000164] Dichroic dye-color LCMS was applied to a portion of the orientation feature on the substrate surface by spin coating. More specifically, approximately 1 ml of the dichroic dye-color LCMS was distributed onto the substrate and excess dichroic dye-color LCMS, when it occurred, was drained off. Thereafter, the substrate was rotated at 300 to 400 revolutions per minute for 4 to 6 minutes. After this rotation, the substrate was placed in an oven at 45°C to 55°C for 20 to 40 minutes, to allow a part of the LCMS and a part of the dichroic dye to be aligned.

[000165] Thereafter, the resulting coatings were tested for alignment using two transversely polarized polarizing films (#45669) from Edmund Indus

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92/98 Trial Optics. Each coated substrate was positioned between the transversely polarized polarizing films such that the coated substrate was parallel to one of the films such that visible light transmitted through the configuration of the polarizing films and the coated substrate was reduced. Partial alignment was found by observing an increase in transmitted visible light when one of the polarizing films was rotated 45 degrees clockwise or counterclockwise while observing a visible light source through of the configuration. When two partial coats of the color-dichroic LCMS dye were applied, the aforementioned steps of this Part C were completed prior to the application of the second partial coat.

[000166] After checking the partial alignment of the coatings, the partial coatings were further cured by covering each of the coated substrates with a base 6 polycarbonate lens plane, having a diameter of 70 mm and a thickness of 2.0 mm, so that it was about 1 mm to 2 mm above the surface of the coated substrate. The resulting coated substrate/polycarbonate lens assembly was placed on an ultraviolet carrier cure line obtained from Eye Ultraviolet, Inc. The ultraviolet carrier cure line had a nitrogen atmosphere in which the

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93/98 oxygen level was less than 100ppm. The conveyor traveled 0.91 m (three feet) per minute under two 25.4 cm long, 400 watts/inch D-type ultraviolet iron iodide-inducted mercury lamps. One of the lamps was placed 6.35 cm (2.5 inches) above the conveyor and the other lamp was placed 13.97 cm (6.5 inches) above the conveyor. The peak intensity of the different ultraviolet wavelengths provided by the ultraviolet carrier curing line was measured using an electro-optical UV Power Puck™ radiometer, described above. The measured UVA peak intensity (320 to 390 nm) was 0.239 Watts/cm² and the UVV (395 to 445 nm) measured was 0.416 Watts/cm².

Part D

Preparation of Adapted Partial Coatings to Polarize Transmitted Radiation Using a Magnetic Field

The polymerized square substrates of CR39® monomer lens material coated with the preparation coatings as described in Part A were used to prepare samples coated in this Part D. However, as described below, the substrates did not were prepared in accordance with Part B prior to coating with LCMSCinza.

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94/98

[000168] For samples prepared in accordance with this Part D, the procedure of Part C was generally followed to coat the primer coated substrates (described above in Part A) with the LCMS-Grey of Example 6 (described above in Step 3), except that before curing the coated substrate, a part of the coating was partially ordered as follows. The coated substrate was placed on a 20.32 cm (8 inch) temperature controlled hot plate under a temperature controlled infrared lamp and between the north and south poles of a 0.35 Tesla magnet that were separated by a distance of 11 centimeters. The two temperature controllers have been adjusted to maintain a temperature of approximately 55°C to 60°C. The coated substrate was held under these conditions for 40 to 45 minutes to partially sort the LCM and dichroic dye. Thereafter, the ordered coating was cured and the ordering of the coating was checked as described in Part C (with respect to inline coatings). The resulting sample is identified as 6A(Magnetic) in Table 1.

part E

Absorption Ratio Measurement Tests [000169] The absorption ratios for each of the coated substrates were determined as follows. A CARY 4000 UV-Visible Spectrometer

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95/98 was equipped with a self-centering sample holder equipped with a polarizing analyzer (Moxtek ProFlux™ polarizer). The instrument was adjusted with the following parameters: Scanning speed = 600 nm/min; Data range = 1.0 nm; Integration time = 100 nm; Absorption range = 0-6.5; mode Y = absorbance; Mode X = nanometers and the scanning range was 400 to 800 nm. The options have been set to 3.5 SBW (vertical range bandwidth), and dual for beam mode. Baseline options have been adjusted to Zero/Baseline correction. A sample of each substrate material without the guidance feature and/or the coating adapted to polarize transmitted radiation was used to establish the Zero/Baseline correction. For samples where the substrate was coated with a primer coating, the Zero/Baseline correction was established using the primer-coated substrate. Also, 2.5 Neutral Density filters were placed in the reference path for all farms. Coated substrate samples were tested in air at an ambient temperature of 22.7°C ± 5°C (73°F ± 5°F) maintained by the laboratory air conditioning system.

[000170] The orientation of the sample polarizer to be parallel and perpendicular to the analyzer polarizer was performed as explained below. The Cary 4000 was set to 500 nm (or under

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96/98 a peak absorbance of the sample), and the absorbance was monitored when the sample was rotated in small increments (1 to 5 degrees). Rotation of the sample was continued until the absorbance was maximized. This position was defined as the perpendicular or 90 degree position. Parallel position was obtained by rotating the stage 90 degrees clockwise or counterclockwise.

[000171] The absorption spectrum was collected at 90 and 0 degrees for each sample. Data analysis was handled with the Igor Pro software, available from WaveMetrics. The spectra were loaded into Igor Pro and the absorbances were used to calculate the absorption ratios at 566 nm. The calculated absorption ratios are listed in Table 1.

[000172] In Table 1, the sample numbers correspond to the coating composition (eg Examples 1-6) that was applied to the substrate tested. Different alphabetical letters associated with the sample number indicate different substrates, as follows: A indicates a polymerizate of CR39® monomer; B indicates a polymerizate of TRIVEX® 151 lens material; C indicates the photochromic lens from Transition Optical Incorporated which has a refractive index of 1.50; and D indicates a polymerizate of CR-607® monomer. Double letters indicate that the substrate has been coated twice in Part C. The results pa

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97/98 ra Samples 6A1 and 6A2 were arithmetic means of 2 results. The results for the other samples were from plain coated substrates tested.

Table 1

<td>Sample Number</td><td>Coating Present preparer</td><td>Absorption Ratio</td>

<td>1A</td><td> ^-</td><td> 3,1</td>

<td>2A</td><td> ^-</td><td> 5,7</td>

<td>3A</td><td> ^-</td><td> 2,4</td>

<td>4A</td><td> ^-</td><td> 4,0</td>

<td>5A</td><td> ^-</td><td> 5,4</td>

<td>6A</td><td> ^-</td><td> 2,6</td>

<td>6AA</td><td> ^-</td><td> 4,4</td>

<td>6B</td><td> ^-</td><td> 3,0</td>

<td>6C</td><td> ^-</td><td> 3,1</td>

<td>6D</td><td> ^-</td><td> 3,9</td>

<td>6A1</td><td> +</td><td> 6,2</td>

<td>6A2</td><td> ^-</td><td> 7,0</td>

<td></td><td></td><td></td>

<td>6A (Magnetic)</td><td> +</td><td> 5,4</td>

[000173] As indicated in the Table

1, the partial coatings adapted to polarize transmitted radiation for the non-limiting examples described above exhibited variable absorption ratios from 2.4 to 7.0.

[000174] It should be understood that the present description illustrates aspects of the relevant invention.

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98/98 forwards for a clear understanding of the invention. Some aspects of the invention which will be evident to those skilled in the art and which, consequently, will not facilitate a better understanding of the invention have not been presented in order to simplify the present description. Although the present invention has been described in connection with certain embodiments, the present invention is not limited to the particular embodiments set forth, but is intended to cover modifications that are within the spirit and scope of the invention as defined by the appended claims.

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