HK1097607B - Polarizing devices and methods of making the same - Google Patents

Description

Polarizing device and method of manufacturing the same

Cross Reference to Related Applications

Not applicable.

Statement regarding federally sponsored research or development

Not applicable.

Reference to sequence listing

Not applicable.

Background

Polarizing ophthalmic devices, such as sunglasses, can reduce glare due to light reflected off of some surfaces (e.g., but not limited to, road surfaces, water, and snow), thus enhancing vision in glare conditions. Accordingly, there is increasing interest in using polarized ophthalmic devices in sports and other outdoor activities where reflected glare is an issue.

Conventional polarizing filters for ophthalmic devices are formed from sheets or layers of polymeric materials that have been stretched or otherwise oriented and impregnated with iodine chromophores or dichroic dyes. For example, one method of forming conventional polarizing filters 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 such that the iodine or dye molecules attach to the aligned polymer chains and adopt a particular order or alignment. Alternatively, the iodine chromophore or dichroic dye can be first impregnated into the PVA sheet, after which the sheet can be heated and stretched as described above to orient the PVA polymer chains and associated chromophore or dye.

Iodine chromophores and dichroic dyes are dichroic materials, i.e. they absorb one of the two orthogonal plane-polarizing components of transmitted radiation more strongly (than the other component). While dichroic materials are capable of preferentially absorbing one of the two orthogonal plane-polarized components of transmitted radiation, if the molecules of the dichroic material are not properly positioned or aligned, a net polarization of transmitted radiation cannot be achieved. That is, due to the random positioning of the molecules of the dichroic material, the selective absorption of the individual molecules can cancel each other out, so that a net or overall polarizing effect cannot be achieved. However, by properly positioning or aligning the molecules of the dichroic material within the oriented polymer chains of the PVA sheet, net polarization can be achieved. That is, a PVA sheet can be made to polarize transmitted radiation, or in other words, a polarizing filter can be formed. The term "polarize" as used herein means to confine the vibration of the electric vector of a light wave to one direction.

One method of forming a polarizing ophthalmic device using a polarizing polymer sheet filter is to laminate or adhere the filter to a convex outer surface of a lens substrate. Another method of forming a lens using a conventional polarizing polymer sheet filter includes lining a surface of a lens mold with a polarizing sheet and subsequently filling the mold with a matrix material such that the polarizing sheet is on the surface of the lens when removed from the mold. Yet another method includes introducing a filter optic into the lens structure itself. For example, the filter can be incorporated into the lens structure by laminating the filter between two substrates together to form a lens, or by casting a substrate material around the filter. In the latter method, the polarizing filter can be placed into a mold, which is then filled with a matrix material (typically a thermosetting plastic monomer) such that the matrix material surrounds and encapsulates the polarizing filter. Thereafter, the matrix material can be cured to form the lens.

It is also known to form a polarizing layer by forming a film layer of a linear photopolymerizable material exhibiting selective orientation on a release layer portion of a transfer foil (transfer foil). Thereafter, a liquid crystal polymer material containing a dichroic dye can be applied to the linear photopolymerizable material and to the chains of the aligned liquid crystal polymer. Since the 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 a net polarizing effect can be achieved. The polarizing layer is then transferred from the transfer foil onto a suitable substrate, for example by hot stamping.

Other methods of forming polarizing sheets or layers using liquid crystal materials are also known. For example, polarizing sheets formed from oriented thermotropic liquid crystal films containing dichroic dyes have been disclosed. Further, a polarizing sheet formed by extrusion processing of a liquid crystal polymer containing a dichroic dye covalently linked as a part of the polymer main chain has been disclosed.

SUMMARY

Various non-limiting embodiments disclosed herein provide optical elements and devices and ophthalmic elements and devices. For example, one non-limiting embodiment provides an ophthalmic element comprising an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of at least one outer surface of the ophthalmic element.

Another non-limiting embodiment provides an ophthalmic element comprising at least one orientation facility on at least a portion of at least one outer surface of the ophthalmic element, and an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of the at least one orientation facility.

Another non-limiting embodiment provides an ophthalmic element comprising at least one at least partial coating comprising an alignment medium on at least a portion of at least one outer surface of the ophthalmic element, at least one at least partial coating comprising an alignment transfer (transfer) material on at least a portion of the at least one at least partial coating comprising an alignment transfer material, and at least one at least partial coating comprising an anisotropic material and at least one dichroic material on at least a portion of the at least one at least partial coating comprising an alignment transfer material.

Yet another non-limiting embodiment provides an ophthalmic element comprising a substrate, at least one orientation facility comprising an at least partial coating comprising a photo-orientable polymer network on at least a portion of at least one outer surface of the substrate, and an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of the at least one at least partial coating comprising a photo-orientable polymer network, the at least partial coating adapted to polarize at least transmitted radiation comprising a liquid crystal polymer and at least one dichroic dye.

Yet another non-limiting embodiment provides an optical element comprising an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of at least one outer surface of the optical element, the at least partial coating comprising an at least partially ordered liquid crystal material and at least one at least partially aligned dichroic material.

Another non-limiting embodiment provides an optical device comprising at least one optical element comprising an at least partial coating comprising an alignment medium on at least a portion of at least one outer surface of the at least one optical element, and an at least partial coating comprising an anisotropic material and at least one dichroic material on at least a portion of the at least one at least partial coating comprising an alignment medium.

Other non-limiting embodiments disclosed herein provide methods of making optical elements and ophthalmic elements. For example, one non-limiting embodiment provides a method of making an ophthalmic element comprising forming an at least partial coating suitable for polarizing at least transmitted radiation on at least a portion of at least one exterior surface of the ophthalmic element.

Another non-limiting embodiment provides a method of making an ophthalmic element comprising administering at least one alignment facility comprising an at least partial coating of an alignment medium on at least a portion of at least one outer surface of the ophthalmic element, and applying at least one dichroic material to at least a portion of the at least one alignment facility, and allowing at least a portion of the at least one dichroic material to be at least partially aligned.

Another non-limiting embodiment provides a method of making an ophthalmic element comprising applying at least a portion of a coating to at least a portion of at least one outer surface of the ophthalmic element and polarizing at least transmitted radiation with at least a portion of the at least partial coating.

Yet another non-limiting embodiment provides a method of making an ophthalmic element comprising applying an at least partial coating comprising an alignment medium to at least a portion of at least one outer surface of the ophthalmic element, at least partially ordering at least a portion of the alignment medium, applying an at least partial coating comprising an anisotropic material and at least one dichroic material to at least a portion of the at least partial coating comprising the at least partially ordered alignment medium, and at least partially aligning at least a portion of the at least one dichroic material.

Another non-limiting embodiment provides a method of manufacturing a lens for ophthalmic applications, the method comprising applying an at least partial coating comprising a photo-orientable polymer network to at least a portion of at least one outer surface of the lens, causing at least a portion of the photo-orientable polymer network to become at least partially ordered with plane-polarized ultraviolet radiation, applying an at least partial coating comprising a liquid crystal material and at least one dichroic dye to at least a portion of the at least one at least partial coating comprising a photo-orientable polymer network, at least a portion of the at least partial coating comprising a liquid crystal material and at least one dichroic dye to become at least partially aligned, and at least a portion of the coating comprising a liquid crystal polymer and at least one dichroic dye to become at least partially cured.

Yet another non-limiting embodiment provides a method of making an optical element, the method comprising applying at least a portion of a coating to at least a portion of at least one outer surface of the optical element, and adjusting (adapt) at least a portion of the coating to polarize at least transmitted radiation.

Detailed Description

The articles "a," "an," and "the" as used in the specification and in the appended claims are intended to include plural referents unless expressly limited to one referent.

In addition, for the purposes of this specification, unless otherwise indicated, all numbers expressing quantities of ingredients, reaction conditions, and other properties or parameters used in the specification are to be understood as being modified in all instances by the term "about". Accordingly, unless indicated otherwise, it is to be understood that the numerical parameters set forth in the following specification and attached claims are approximations. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

Furthermore, notwithstanding that the numerical ranges and parameter settings setting forth the broad scope of the invention are approximations as discussed above, the numerical values set forth in the examples section are reported as precisely as possible. However, it should be understood that such values inherently contain certain errors resulting from the measurement device and/or measurement technique.

Elements and devices according to various non-limiting embodiments of the present invention will now be described. One non-limiting embodiment provides an optical element, and more particularly an ophthalmic element, comprising an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of at least one exterior surface of the ophthalmic element.

As discussed previously, the term "polarize" means to confine the vibration of the electric vector of a light wave to one direction. As further discussed previously, conventional polarizing ophthalmic elements, such as lenses for ophthalmic devices, are typically formed by laminating or molding a polarizing filter lens formed from a stretched PVA sheet (or layer) containing a dichroic material, such as an iodine chromophore, onto a lens substrate. However, according to various non-limiting embodiments disclosed herein, the ophthalmic element includes an at least partial coating on at least a portion of at least one outer surface of the ophthalmic element suitable for polarizing at least transmitted radiation. Thus, according to these non-limiting embodiments, the conventional laminate structure discussed above is not required. The preposition "on" as used herein means that the subject coating is attached directly to the surface of the object or indirectly via one or more other coatings or structures. Further, the term "coating" as used herein refers to a film, which may or may not be of uniform thickness, and specifically excludes prior art stretched polymer sheets.

The term "ophthalmic" as used herein refers to elements and devices relating to the eye and vision, such as, but not limited to, the lenses of eyeglasses, and eyeglasses. Thus, for example, according to various non-limiting embodiments disclosed herein, an ophthalmic element can be selected from a corrective lens, a non-corrective lens, and a magnifying lens.

Further, ophthalmic elements according to various non-limiting embodiments disclosed herein can be formed from any suitable substrate material (including, but not limited to, glass and organic materials).

For example, according to various non-limiting embodiments disclosed herein, an ophthalmic element can be formed from an organic base material. Suitable organic substrate materials for use in conjunction with the various non-limiting embodiments disclosed herein include, but are not limited to, polymers well known in the art that are useful as ophthalmic elements, for example, organic optical resins for making optically clear castings for optical applications such as ophthalmic lenses.

Specific non-limiting examples of organic substrate materials that can be used to form the ophthalmic elements disclosed herein include polymeric materials, such as homopolymers and copolymers prepared from the monomers and monomer mixtures disclosed in U.S. Pat. No. 5,962,617 and in U.S. Pat. No. 5,658,501 at column 15, line 28 through column 16, line 17, the disclosures of both of which are specifically incorporated herein by reference. For example, such polymeric materials can be thermoplastic or thermoset polymeric materials, can be transparent or optically transparent, and can have any desired refractive index. Non-limiting examples of such monomers and polymers disclosed include: polyol (allyl carbonate) monomers, for example, allyl diglycol carbonate such as diethylene glycol bis (allyl carbonate), sold under the trademark CR-39 by PPG Industries, inc; poly (urea-urethane) polymers, for example prepared by reaction of a polyurethane prepolymer and a diamine curative, one such polymer composition being sold under the trade mark TRIVEX by PPG Industries, inc; a polyol (meth) acryloyl-terminated carbonate monomer; diethylene glycol dimethacrylate monomer; ethoxylated phenolic methacrylate monomers; diisopropenyl benzene monomer; ethoxylated trimethylolpropane triacrylate monomer; ethylene glycol dimethacrylate monomer; a poly (ethylene glycol) dimethacrylate monomer; a urethane acrylate monomer; poly (ethoxylated bisphenol a dimethacrylate); poly (vinyl acetate); poly (vinyl alcohol); poly (vinyl chloride); poly (vinylidene chloride); polyethylene; polypropylene; a polyurethane; polythiourethanes, thermoplastic polycarbonates, such as carbonate-linked resins formed from bisphenol a and phosgene, one such material being sold under the trademark 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 the reaction of polyfunctional isocyanates with polythiols or polysulfide monomers, homopolymerization or co-and or ter-copolymerization with polythiols, polyisocyanates, polyisothiocyanates, and optionally ethylenically unsaturated monomers or halogenated aromatic hydrocarbon group-containing vinyl monomers. Also contemplated are copolymers of such monomers and blends of the polymers and copolymers with other polymers, for example, to form block copolymers. Although the precise nature of the organic substrate is not critical to the various non-limiting embodiments disclosed herein, in one non-limiting embodiment, the organic substrate material should be chemically compatible with at least a portion of the coating on at least a portion of at least one outer surface of the ophthalmic element that is suitable for polarizing at least transmitted radiation.

Further, according to certain non-limiting embodiments disclosed herein, the substrates forming the ophthalmic elements can have a protective coating on their outer surfaces, such as, but not limited to, an abrasion resistant coating, such as a "hard coat". For example, commercially available thermoplastic polycarbonate lens substrates are often sold with abrasion resistant coatings already applied to their outer surfaces because these surfaces tend to scratch, abrade or abrade easily. An example of such a lens substrate is GENTEX^TMPolycarbonate lenses (available from genetex Optics). Thus, the term "substrate" as used herein includes substrates having a protective coating (such as, but not limited to, an abrasion resistant coating) on one or more surfaces thereof.

Still further, ophthalmic elements and substrates used to form ophthalmic elements according to various non-limiting embodiments disclosed herein can be uncolored, colored, photochromic, or tinted-photochromic ophthalmic elements.

The term "uncolored" as used herein with respect to ophthalmic elements and substrates means substantially free of colorant additives (such as, but not limited to, conventional dyes) and having an absorption spectrum for visible radiation that does not change significantly in response to actinic radiation. The term "actinic radiation" as used herein refers to electromagnetic radiation capable of eliciting a response. Although not meant to be limiting herein, actinic radiation can include both visible and ultraviolet radiation.

The term "tinted" as used herein with respect to ophthalmic elements and substrates means to include colorant additives (such as, but not limited to, conventional dyes) and to have an absorption spectrum for visible radiation that does not change significantly in response to actinic radiation.

The term "photochromic" as used herein refers to a visible radiation absorption spectrum that changes in response to at least actinic radiation and is thermally reversible. Although not limited thereto, for example, photochromic elements, substrates, coatings, and materials used in conjunction with the various non-limiting embodiments disclosed herein can change from a transparent state to a colored state in response to radiation, or they can change from one colored state to another colored state in response to radiation. For example, in one non-limiting embodiment the photochromic ophthalmic element can change from a clear state to a colored state in response to actinic radiation and revert back to the clear state in response to thermal radiation or heat. Alternatively, the photochromic ophthalmic element can change from a first colored state to a second colored state in response to actinic radiation and revert back to the first colored state in response to thermal radiation or heat.

The term "tinted-photochromic" as used herein with respect to ophthalmic elements and substrates means containing a colorant additive and a photochromic material and having an absorption spectrum for visible radiation that changes in response to at least actinic radiation and is thermally reversible. Thus, for example, in one non-limiting embodiment, the tinted-photochromic substrate can have a first color characteristic of the colorant and a second color characteristic of the combination of the colorant and the photochromic material when exposed to actinic radiation.

As discussed above, ophthalmic elements according to various non-limiting embodiments disclosed herein include an at least partial coating on at least a portion of at least one outer surface of the ophthalmic element suitable for polarizing at least transmitted radiation. The term "transparent to radiation" as used herein refers to radiation that is transmitted through at least a portion of an element or substrate. Although not limited thereto, the transmitted radiation can be visible radiation or can be a combination of visible and ultraviolet radiation. According to various non-limiting embodiments disclosed herein, at least a portion of the coating can be utilized to polarize transmitted visible radiation, or it can be utilized to polarize a combination of transmitted visible radiation and transmitted ultraviolet radiation.

Further, at least a partial coating on at least a portion of at least one outer surface of the ophthalmic element suitable for polarizing at least transmitted radiation can comprise at least one dichroic material. The terms "dichroic material" and "dichroic dye" as used herein refer to a material that more strongly absorbs one of two orthogonal plane-polarizing components of at least transmitted radiation (as compared to the other component). One measure of how strongly a dichroic material absorbs one of two orthogonal plane-polarizing components is the "absorption ratio". The term "absorption ratio" as used herein refers to the ratio of the absorbance of radiation linearly polarized in a first plane to the absorbance of radiation of the same wavelength linearly polarized in a plane orthogonal to the first plane, where the first plane is taken as the plane with the highest absorbance. The method of determining the absorption ratio is described in detail in the examples section.

Dichroic materials that can be used in combination with the various non-limiting embodiments disclosed herein include, but are not limited to, dichroic materials having an absorption ratio of 2 to 30 (or higher, as desired). For example, according to certain non-limiting embodiments, the dichroic material can have an absorption ratio of at least 3, at least 5, at least 7, at least 10, or more. Further, combinations of dichroic materials having different absorption ratios can be used in accordance with the various non-limiting embodiments disclosed herein. For example, in one non-limiting embodiment, at least a portion of the coating utilized to polarize at least transmitted radiation can include a first type of dichroic material having a first absorption ratio and at least one second type of dichroic material having a second absorption ratio different from the first absorption ratio.

Non-limiting examples of dichroic materials suitable for use in combination with the various non-limiting embodiments described herein include azomethines, indigoids, thioindigoids, merocyanines, indanes, quinophthalone dyes, perylenes, phthalidins, triphendioxanesAzines, indoloquinoxalines, imidazotriazines, tetrazines, azo and (poly) azo dyes, benzoquinones, naphthoquinones, anthraquinones and (poly) anthraquinones, anthrapyrimidinones, iodine and iodates.

Although not meant to be limiting herein, in one non-limiting embodiment, the dichroic material is selected from azo and poly (azo) dyes. In another non-limiting embodiment, the dichroic material is anthraquinone and (poly) anthraquinone.

Further, in another non-limiting embodiment, the dichroic material can be a polymerizable dichroic material. That is, according to this non-limiting embodiment, the dichroic material can include at least one group capable of polymerizing (i.e., "polymerizable group"). For example, although not limited herein, in one non-limiting embodiment at least one dichroic material can have at least one alkoxy, polyalkoxy, alkyl, or polyalkyl substituent terminated by at least one polymerizable group.

According to one non-limiting embodiment, the at least partial coating on at least a portion of at least one outer surface of the ophthalmic element suitable for polarizing at least transmitted radiation can comprise at least one dichroic material and at least one anisotropic material. The term "anisotropic" as used herein means having at least one property that differs in value when measured in at least one different direction. Thus, an "anisotropic material" is a material that has at least one numerically different optical property when measured in at least one different direction. For example, although not limited thereto, anisotropic materials that can be used in connection with the various non-limiting embodiments disclosed herein can be optically anisotropic materials.

Non-limiting examples of anisotropic materials suitable for use in conjunction with the various non-limiting embodiments disclosed herein include liquid crystal materials selected from the group consisting of liquid crystal polymers, liquid crystal prepolymers, and liquid crystal monomers. The term "prepolymer" as used herein refers to a partially polymerized material. For example, according to one non-limiting embodiment, an at least partial coating on at least a portion of at least one outer surface of an ophthalmic element suitable for polarizing at least transmitted radiation can comprise at least one dichroic material and at least one anisotropic material selected from the group consisting of liquid crystal polymers, liquid crystal prepolymers, and liquid crystal monomers.

Liquid crystal monomers suitable for use as anisotropic materials in combination with the various non-limiting embodiments disclosed herein include monofunctional liquid crystal monomers and multifunctional liquid crystal monomers. Further, according to various non-limiting embodiments disclosed herein, the liquid crystal monomer can be a crosslinkable liquid crystal monomer, and can further be a photo-crosslinkable liquid crystal monomer. The term "photocrosslinkable" as used herein refers to a material, such as a monomer, prepolymer, or polymer, that crosslinks upon exposure to actinic radiation.

Non-limiting examples of cross-linkable liquid crystal monomers suitable for use as the anisotropic material according to the various non-limiting embodiments disclosed herein include liquid crystal monomers having functional groups selected from the group consisting of acrylate, methacrylate, allyl ether, alkyne, amino, anhydride, epoxy, hydroxyl, isocyanate, blocked isocyanate, siloxane, thiocyanate, thiol, urea, vinyl ether and combinations thereof. Non-limiting examples of photo-crosslinkable liquid crystal monomers suitable for use as the anisotropic material according to the various non-limiting embodiments disclosed herein include liquid crystal monomers having functional groups selected from acrylates, methacrylates, alkynes, epoxy groups, thiols, and combinations thereof.

Liquid crystal polymers and prepolymers suitable for use as anisotropic materials in combination with the various non-limiting embodiments disclosed herein include thermotropic liquid crystal polymers and prepolymers, and lyotropic liquid crystal polymers and prepolymers. Further, the liquid crystal polymers and prepolymers can be backbone polymers and prepolymers or side chain polymers and prepolymers. In addition, according to various non-limiting embodiments disclosed herein, the liquid crystalline polymer or prepolymer can be crosslinkable, and can further be photo-crosslinkable.

Non-limiting examples of suitable liquid crystal polymers and prepolymers suitable for use as anisotropic materials according to the various non-limiting embodiments disclosed herein include, but are not limited to, backbone and side chain polymers and prepolymers having functional groups selected from the group consisting of acrylate, methacrylate, allyl ether, alkyne, amino, anhydride, epoxy, hydroxyl, isocyanate, blocked isocyanate, siloxane, thiocyanate, thiol, urea, vinyl ether, and combinations thereof. Non-limiting examples of photo-crosslinkable liquid crystal polymers and prepolymers suitable for use as anisotropic materials according to the various non-limiting embodiments disclosed herein include those polymers and prepolymers having functional groups selected from the group consisting of acrylates, methacrylates, alkynes, epoxy groups, thiols, and combinations thereof.

Additionally, although not limited herein, at least a portion of the anisotropic material can be at least partially ordered and at least a portion of the at least one dichroic material can be at least partially aligned with at least a portion of the at least partially ordered anisotropic material, according to various non-limiting embodiments. The term "ordering" as used herein means achieving a suitable arrangement or orientation, such as by orienting the arrangement with another structure, or by some other force or action. Further, the term "aligned" as used herein means to cause proper alignment or orientation by interacting with another structure.

As discussed previously, although dichroic materials absorb one of two orthogonal plane-polarized components of transmitted radiation more strongly than the other, the molecules of the dichroic material must be suitably positioned or arranged to achieve a net polarization of the transmitted radiation. Thus, according to various non-limiting embodiments disclosed herein, at least a portion of at least one dichroic material can be suitably positioned or aligned (i.e., ordered or aligned) such that an overall polarizing effect can be achieved.

For example, in one non-limiting embodiment, the at least partial coating can comprise an at least partially ordered anisotropic material (such as, but not limited to, a liquid crystal material) and at least one at least partially aligned dichroic material, wherein the at least one at least partially aligned dichroic material is at least partially aligned with the at least partially ordered anisotropic material. Although not limiting herein, at least a portion of at least one dichroic material according to this non-limiting embodiment can be at least partially aligned such that the long axis of at least a portion of at least one dichroic material is generally parallel to the ordering direction of the anisotropic material.

In another non-limiting embodiment the at least one dichroic material is capable of bonding to or reacting with at least a portion of the anisotropic material. For example, according to this non-limiting embodiment, the at least one dichroic material is capable of polymerizing into or reacting with at least a portion of the anisotropic material. Further, although not meant to be limiting herein, the at least one dichroic material can include a composition comprising end groups and/or side groups according to this non-limiting embodimentIs selected from the group consisting of hydroxyl, carboxyl, (meth) acryloxy, 2- (methacryloxy) ethylcarbamoyl (-OC (O) NHC₂H₄OC(O)C(CH₃)＝CH₂) Epoxy groups or mixtures thereof.

In addition to the at least one dichroic material and the at least one anisotropic material, according to various non-limiting embodiments disclosed herein, the at least partial coating on at least a portion of at least one outer surface of the ophthalmic element suitable for polarizing at least transmitted radiation can further comprise at least one photochromic material. As discussed previously, the photochromic material has an absorption spectrum that changes in response to at least actinic radiation.

For example, although not meant to be limiting herein, the at least one photochromic material can be selected from pyrans,oxazines, fulgides and fulgimides, and metal dithizonates. However, according to various non-limiting embodiments, the particular photochromic materials selected are not critical, and their selection will depend on the end application and the color or shade desired for the application. In one non-limiting embodiment, the at least one photochromic material has at least one absorption maximum between 300 and 1000 nanometers when activated (i.e., exposed to actinic radiation).

Further, in some non-limiting embodiments, at least a portion of the coating can include a mixture of photochromic materials. Generally, although not limited herein, photochromic materials are often selected to complement one another when two or more photochromic materials are used in combination to produce a desired color or shade. For example, mixtures of photochromic materials can be used in accordance with certain non-limiting embodiments disclosed herein to achieve certain activated colors, such as near neutral gray or near neutral brown. See, for example, U.S. patent 5,645,767, column 12, line 66 to column 13, line 19, the disclosure of which is incorporated herein by reference, which describes parameters for determining neutral gray and brown.

Non-limiting examples of photochromic pyrans for use in conjunction with the various non-limiting embodiments disclosed herein include benzopyrans, naphthopyrans, e.g., naphtho [1, 2-b ] pyran, naphtho [2, 1-b ] pyran, spiro-9-fluoreno [1, 2-b ] pyran, phenanthropyrans, quinopyrans, and indeno-fused naphthopyrans, such as those disclosed in U.S. Pat. No. 5,645,767; spiropyrans, e.g., spiro (indoline) naphthopyrans, spiro (indoline) benzopyrans, spiro (indoline) naphthopyrans, spiro (indoline) quinopyrans and spiro (indoline) pyrans; and heterocyclic-fused naphthopyrans, such as those disclosed in U.S. Pat. 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 in US patent 5,658,501, column 11, line 57 to column 13, line 36, which is hereby expressly incorporated herein by reference.

Photochromic articles that can be used in combination with the various non-limiting embodiments disclosed hereinNon-limiting examples of oxazines include benzoOxazines and thiophenesOxazines, and spiroOxazines, e.g. spiro (indoline) thiopheneOxazine, spiro (indoline) pyridobenzoOxazine, spiro (benzindoline) pyridinesBenzo (a) and (b)Oxazines, spiro (benzindoline) thiophenesOxazine, spiro (indoline) benzoOxazines, and spiro (indoline) fluoranthenoAnd (3) an oxazine.

Non-limiting examples of photochromic fulgides and fulgimides that can be used in combination with the various non-limiting embodiments disclosed herein include 3-furyl and 3-thienyl fulgides and fulgimides, which are described in U.S. Pat. No. 4,931,220 (which is hereby expressly incorporated herein by reference) at column 20, line 5 to column 21, line 38, and mixtures of any of the foregoing photochromic materials/compounds.

Non-limiting examples of photochromic metal dithizonates that can be used in conjunction with the various non-limiting embodiments disclosed herein include mercury dithizonates, which are described, for example, in U.S. Pat. No. 3,361,706 (which is hereby specifically incorporated herein by reference).

Additionally, it is contemplated that photochromic materials such as photochromic dyes and photochromic compounds encapsulated in metal oxides can be used in accordance with the various non-limiting embodiments disclosed herein. See, for example, the materials described in U.S. Pat. Nos. 4,166,043 and 4,367,170, which are hereby specifically incorporated herein by reference. In addition, polymerizable photochromic materials, such as those disclosed in U.S. Pat. No. 6,113,814 (which is hereby specifically incorporated by reference), and compatibilized photochromic materials, such as those disclosed in U.S. Pat. No. 6,555,028 (which is hereby specifically incorporated by reference), can also be used in combination with the various non-limiting embodiments disclosed herein.

Still further, in accordance with various non-limiting embodiments disclosed herein, the at least partial coating utilized to polarize at least transmitted radiation can further include at least one additive that can facilitate one or more of processing, performance, or characteristics of the at least partial coating. Non-limiting examples of such additives include dyes, alignment promoters, kinetic enhancing additives, photoinitiators, solvents, light stabilizers (such as, but not limited to, ultraviolet light absorbers and light stabilizers, such as Hindered Amine Light Stabilizers (HALS)), heat stabilizers, mold release agents, rheology control agents, leveling agents (such as, but not limited to, surfactants), free radical scavengers, and adhesion promoters (such as hexanediol diacrylate and coupling agents). In one non-limiting embodiment, the additive is a dye.

The term "alignment promoter" as used herein means an additive that promotes at least one of the rate and uniformity of alignment of a material to which it is added. Non-limiting examples of alignment promoters that can be present in at least a portion of the coating according to various non-limiting embodiments disclosed herein include those described in US patent 6,338,808 and US patent publication No.2002/0039627, which are hereby expressly incorporated herein by reference.

Non-limiting examples of dyes that can be present in at least a portion of a coating according to various non-limiting embodiments disclosed herein include organic dyes that can impart a desired color or optical property to at least a portion of a coating.

Non-limiting examples of kinetic enhancing additives that can be present in at least a portion of the coating according to various non-limiting embodiments disclosed herein include epoxy-containing compounds, organic polyols, and/or plasticizers. More specific examples of such kinetic enhancing additives are disclosed in US patent 6,433,043 and US patent publication No.2003/0045612, which are hereby specifically incorporated herein by reference.

Can be implemented in accordance with the various non-limiting implementations disclosed hereinNon-limiting examples of photoinitiators present in at least a portion of the coating of the embodiments include cleavage-type photoinitiators and abstraction-type photoinitiators. Non-limiting examples of cleavage-type photoinitiators include acetophenone, α -aminoalkylphenones, benzoin ethers, benzoyl oximes, acylphosphine oxides and bisacylphosphine oxides or mixtures of such initiators. A commercial example of such a photoinitiator is DAROCURE, commercially available from Ciba Chemicals, Inc4265. Non-limiting examples of abstraction-type photoinitiators include benzophenone, Michler's ketone, thioxanthone, anthraquinone, camphorquinone, fluorone, ketocoumarin or mixtures of such initiators.

Another non-limiting example of a photoinitiator that can be present in at least a portion of the coating according to various non-limiting embodiments disclosed herein is a visible photoinitiator. Non-limiting examples of suitable visible light photoinitiators are set forth in U.S. patent 6,602,603, column 12, line 11 through column 13, line 21, which is hereby specifically incorporated by reference.

Non-limiting examples of solvents that can be present in at least a portion of the coating according to various non-limiting embodiments disclosed herein include those solvents that dissolve the solid components of the coating, are compatible with the coating and the ophthalmic element and substrate, and/or are capable of ensuring uniform coverage of the exterior surface of the applied coating. Possible solvents include, but are not limited to, the following: acetone, pentyl propionate, anisole, benzene, butyl acetate, cyclohexane, dialkyl ethers of ethylene glycol, e.g. diglyme and their derivatives (as CELLOSOLVE)Commercial solvent sales), diethylene glycol dibenzoate, dimethyl sulfoxide, dimethylformamide, dimethoxybenzene, ethyl acetate, isopropanol, methylcyclohexanone, cyclopentanone, methyl ethyl ketone, methyl isobutyl ketone, methyl propionate, propylene carbonate, tetrahydrofuran, toluene, xylene, 2-methoxyethyl ether, 1,3-propylene glycol monomethyl ether, and mixtures thereof.

Ophthalmic elements according to various non-limiting embodiments disclosed herein can further include one or more other coatings capable of promoting adhesion, bonding, or wetting of at least a portion of the coating on at least a portion of at least one outer surface of the ophthalmic element suitable for polarizing at least transmitted radiation. For example, an ophthalmic element according to one non-limiting embodiment can include an at least partial base (primer) coating between at least a portion of the at least partial coating adapted to polarize at least transmitted radiation and at least a portion of at least one outer surface of the ophthalmic element. Further, although not required, according to this non-limiting embodiment, the primer layer can function as a barrier coating to prevent interaction between the coating components and the ophthalmic element or substrate surface, and vice versa.

Non-limiting examples of base coats that can be used in conjunction with the various non-limiting embodiments disclosed herein include coatings that include coupling agents, at least partial hydrolysates of coupling agents, and mixtures thereof. As used herein, "coupling agent" refers to a material having at least one group capable of reacting, binding and/or associating with a group on at least one surface. In one non-limiting embodiment, the coupling agent is capable of acting as a molecular bridge at the interface of at least two surfaces (the same or different surfaces). In another non-limiting embodiment, the coupling agent can be a monomer, oligomer, and/or polymer. Such materials include, but are not limited to, metal organic compounds such as silanes, titanates, zirconates, aluminates, zirconium aluminates, their hydrolysates, and mixtures thereof. The phrase "at least partial hydrolysis product of a coupling agent" as used herein means that at least some to all of the hydrolyzable groups on the coupling agent are hydrolyzed. In addition to the coupling agent and/or the hydrolysis product of the coupling agent, the base coat can include other adhesion enhancing ingredients. For example, the primer layer can further include an adhesion-enhancing amount of an epoxy-containing material, although not limited thereto. When added to a coupling agent-containing coating composition, an adhesion-enhancing amount of an epoxy-containing material can improve the adhesion of a subsequently applied coating compared to a coupling agent-containing coating composition that is substantially free of epoxy-containing material. Other non-limiting examples of base coats suitable for use in connection with the various non-limiting embodiments disclosed herein include those described in U.S. Pat. No. 6,602,603 and U.S. Pat. No. 6,150,430, which are hereby specifically incorporated by reference.

In addition, ophthalmic elements according to various non-limiting embodiments disclosed herein can further include at least one additional at least partial coating on at least a portion of the ophthalmic element selected from the group consisting of photochromic coatings, antireflective coatings, transitional coatings, undercoats, and protective coatings. For example, although not limiting herein, the at least one additional at least partial coating can be located on at least a portion of the at least partial coating adapted to polarize at least transmitted radiation, i.e., as an overcoat. Additionally or alternatively, at least a partial coating suitable for polarizing radiation can be disposed on at least a portion of a first outer surface of the ophthalmic element, and at least one additional at least partial coating can be disposed on at least a portion of a second outer surface of the ophthalmic element, wherein the first outer surface of the ophthalmic element is opposite the second outer surface of the ophthalmic element.

Non-limiting examples of photochromic coatings include coatings comprising any of the photochromic materials discussed above. For example, although not meant to be limiting herein, the photochromic coating can be a photochromic polyurethane coating, such as those described in US patent 6,187,444; photochromic aminoplast resin coatings such as those described in U.S. Pat. nos. 4,756,973, 6,432,544B1 and 6,506,488; photochromic polysilane coatings such as those described in US patent 4,556,605; photochromic poly (meth) acrylate coatings such as those described in US patents 6,602,603, 6,150,430 and 6,025,026, and WIPO publication WO 01/02449a 2; polyanhydride photochromic coatings, such as those described in U.S. patent 6,436,525; photochromic polyacrylamide coatings such as those described in US patent 6,060,001; photochromic epoxy coatings such as those described in US patents 4,756,973 and 6,268,055B 1; and photochromic poly (urea-urethane) coatings, such as those described in US patent 6,531,076. The specifications of the above-mentioned US patents and international publications are specifically incorporated herein by reference.

The term "transitional coating" as used herein means a coating that assists in creating a property gradient between two coatings. For example, although not limited in this regard, the transitional coating can assist in creating a hardness gradient between the harder coating and the softer coating. Non-limiting examples of transitional coatings include radiation-hardened acrylate-based films.

Non-limiting examples of protective coatings include: abrasion resistant coatings comprising organosilanes, abrasion resistant coatings comprising radiation hardened acrylate-based films, abrasion resistant coatings based on inorganic materials such as silica, titania and/or zirconia, organic abrasion resistant coatings belonging to the ultraviolet light curable type, oxygen barrier coatings, UV blocking coatings, and combinations thereof. For example, according to one non-limiting embodiment, the protective coating can include a first coat of radiation-hardened acrylate-based film and a second coat comprising an organosilane. Non-limiting examples of commercial protective coating products include SILVUE commercially available from SDC Coatings, Inc. and PPG Industries, Inc. respectively124 and HI-GARDAnd (4) coating.

Another non-limiting embodiment of the present invention provides an ophthalmic element comprising at least one orientation facility on at least a portion of at least one exterior surface of the ophthalmic element and an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of at least the orientation facility. The term "orientation mechanism" as used herein means a mechanism that is capable of facilitating the positioning of one or more other structures that directly, indirectly, or both directly and indirectly contact at least a portion of the orientation mechanism. Non-limiting examples of orientation mechanisms that can be used in conjunction with this and other non-limiting embodiments include at least partial coatings comprising at least partially ordered alignment media, at least partially stretched polymeric sheets, at least partially treated surfaces, and combinations thereof.

For example, although not limiting herein, the at least one orientation facility can comprise, according to one non-limiting embodiment, at least one at least partial coating comprising an at least partially ordered alignment medium. The term "directionally aligned medium" as used herein means a material that is capable of facilitating the positioning of one or more other materials. Non-limiting methods that result in at least a portion of the ordering of the directionally aligned media are described in detail below.

Non-limiting examples of suitable alignment media that can be used in conjunction with the various non-limiting embodiments disclosed herein include photo-alignment materials, rubbing-alignment materials, and liquid crystal materials. For example, according to one non-limiting embodiment, the at least one alignment mechanism can comprise at least one at least partial coating comprising an at least partially ordered alignment medium selected from photo-alignment materials, rubbing-alignment materials, and liquid crystal materials.

Non-limiting examples of liquid crystal materials suitable for use as an alignment medium according to the various non-limiting embodiments disclosed herein include liquid crystal polymers, liquid crystal prepolymers, and liquid crystal monomers. For example, according to one non-limiting embodiment, the at least one alignment mechanism can comprise at least one at least partial coating comprising an at least partially ordered liquid crystal material selected from a liquid crystal polymer, a liquid crystal prepolymer, and a liquid crystal monomer.

Liquid crystal monomers suitable for use as alignment media according to the various non-limiting embodiments disclosed herein include monofunctional as well as multifunctional liquid crystal monomers. Further, according to various non-limiting embodiments disclosed herein, the liquid crystal monomer can be a crosslinkable liquid crystal monomer, and can in turn be a photo-crosslinkable liquid crystal monomer.

Non-limiting examples of cross-linkable liquid crystal monomers suitable for use as alignment media according to the various non-limiting embodiments disclosed herein include liquid crystal monomers having functional groups selected from the group consisting of acrylate, methacrylate, allyl ether, alkyne, amino, anhydride, epoxy, hydroxyl, isocyanate, blocked isocyanate, siloxane, thiocyanate, thiol, urea, vinyl ether and combinations thereof. Non-limiting examples of photo-crosslinkable liquid crystal monomers suitable for use as the anisotropic material according to the various non-limiting embodiments disclosed herein include liquid crystal monomers having functional groups selected from acrylates, methacrylates, alkynes, epoxy groups, thiols, and combinations thereof.

Liquid crystal polymers and prepolymers suitable for use as alignment media in combination with the various non-limiting embodiments disclosed herein include thermotropic liquid crystal polymers and prepolymers, and lyotropic liquid crystal polymers and prepolymers. Further, the liquid crystal polymers and prepolymers can be backbone polymers and prepolymers or side chain polymers and prepolymers. In addition, according to various non-limiting embodiments disclosed herein, the liquid crystalline polymer or prepolymer can be crosslinkable, and can further be photo-crosslinkable.

Non-limiting examples of liquid crystal polymers and prepolymers suitable for use as alignment media according to the various non-limiting embodiments disclosed herein include, but are not limited to, backbone and side chain polymers and prepolymers having functional groups selected from the group consisting of acrylate, methacrylate, allyl ether, alkyne, amino, anhydride, epoxy, hydroxyl, isocyanate, blocked isocyanate, siloxane, thiocyanate, thiol, urea, vinyl ether, and combinations thereof. Non-limiting examples of photo-crosslinkable liquid crystalline polymers and prepolymers suitable for use as alignment media according to the various non-limiting embodiments disclosed herein include those polymers and prepolymers having functional groups selected from the group consisting of acrylates, methacrylates, alkynes, epoxy groups, thiols, and combinations thereof.

Non-limiting examples of photo-alignment materials suitable for use as an alignment medium in conjunction with the various non-limiting embodiments disclosed include photo-aligned polymer networks. Specific, non-limiting examples of suitable photo-orientable polymer networks include azobenzene derivatives, cinnamic acid derivatives, coumarin derivatives, ferulic acid derivatives, and polyimides. For example, according to one non-limiting embodiment, the orientation means can comprise at least one at least partial coating comprising an at least partially ordered photo-orientable polymer network selected from azobenzene derivatives, cinnamic acid derivatives, coumarin derivatives, ferulic acid derivatives, and polyimides. Specific non-limiting examples of cinnamic acid derivatives that can be used as alignment media in conjunction with the various non-limiting embodiments disclosed herein include polyvinyl cinnamate and polyvinyl esters of p-methoxycinnamic acid.

The term "rubbed oriented material" as used herein means a material that is capable of being at least partially ordered by rubbing at least a portion of the surface of the material with another suitably textured material. For example, although not limited thereto, in one non-limiting embodiment, the rubbed alignment material can be rubbed with a suitably textured cloth or velvet brush. Non-limiting examples of rubbing orientation materials suitable for use as an alignment medium in conjunction with the various non-limiting embodiments disclosed herein include (poly) imides, (poly) siloxanes, (poly) acrylates, and (poly) coumarins. Thus, for example, although not limiting herein, in one non-limiting embodiment, the at least partial coating comprising an alignment medium can be an at least partial coating comprising polyimide that has been rubbed with velvet or cloth to at least partially order at least a portion of the surface of the polyimide.

As discussed above, at least one orientation mechanism according to various non-limiting embodiments disclosed herein can include an at least partially stretched polymer sheet. For example, although not limiting herein, a sheet of polyvinyl alcohol ("PVA") can be at least partially stretched, at least partially ordering PVA polymer chains, and thereafter the sheet can be bonded to at least a portion of at least one outer surface of the ophthalmic element to form an orientation mechanism.

Still further, as discussed above, the at least one orientation mechanism according to various non-limiting embodiments disclosed herein can include an at least partially treated surface. The term "treated surface" as used herein refers to a surface that has been physically altered to order the surface. Non-limiting examples of at least partially treating the surface include at least partially rubbing the surface and at least partially etching the surface. For example, according to one non-limiting embodiment, the at least one orientation mechanism comprises an at least partially treated surface selected from an at least partially rubbed surface and an at least partially etched surface.

Non-limiting examples of etched surfaces that can be used to form an orientation mechanism according to various non-limiting embodiments disclosed herein include chemically etched surfaces, plasma etched surfaces, nano-etched surfaces (e.g., surface etching using a scanning tunneling microscope or atomic force microscope), laser etched surfaces, and electron beam etched surfaces.

Further, according to various non-limiting embodiments, the at least one orientation facility can include a first ordered region having a first general direction and at least a second ordered region adjacent to the first region having a second general direction different from the first general direction. Thus, the orientation mechanism can have multiple regions, and thus have various arrangements as needed to form a desired pattern or design. Additionally, as discussed above, one or more different orientation mechanisms can be combined to form an orientation mechanism according to various non-limiting embodiments disclosed herein.

As discussed previously, the at least partial coating suitable for polarizing at least transmitted radiation can include at least one dichroic material, according to various non-limiting embodiments. Non-limiting examples of suitable dichroic materials are described in detail above. Furthermore, as discussed previously, it is generally desirable to at least partially align at least a portion of at least one dichroic material to achieve a net polarizing effect. Thus, according to various non-limiting embodiments, at least a portion of at least one dichroic material can be at least partially aligned by being in direct contact with at least a portion of an orientation mechanism or by being in indirect contact with at least a portion of an orientation mechanism (e.g., via one or more other structures or materials).

For example, in one non-limiting embodiment, at least a portion of the dichroic material can be at least partially aligned by direct contact with at least a portion of at least one alignment mechanism. Although not limiting herein, at least a portion of the at least one dichroic material according to this non-limiting embodiment can be at least partially aligned such that the long axis of at least a portion of the at least one dichroic material is generally parallel to the general direction of the at least one ordered region of the orientation means. Further, although not meant to be limiting herein, according to this non-limiting embodiment, the alignment mechanism can comprise a liquid crystal material.

In another non-limiting embodiment, the at least partial coating suitable for polarizing at least transmitted radiation can comprise an anisotropic material and at least one dichroic material. Although not limiting herein, according to this non-limiting embodiment, at least a portion of the anisotropic material can be at least partially aligned with at least one alignment mechanism and at least a portion of the at least one dichroic material can be at least partially aligned with at least one at least partially aligned anisotropic material, as discussed above. Suitable non-limiting examples of anisotropic materials are described above in detail.

Further, in addition to the at least one orientation facility and the at least partial coating adapted to polarize at least transmitted radiation, according to various non-limiting embodiments disclosed herein, an ophthalmic element can include at least one at least partial coating comprising an alignment transfer material, and further can include a plurality of at least partial coatings comprising an alignment transfer material. The term "directionally aligned transfer material" as used herein means a material that facilitates the proper alignment or positioning of materials transferred from one structure or material to another.

For example, in one non-limiting embodiment, at least one at least partial coating comprising an alignment transfer material can be between the at least one orientation mechanism and the at least a portion of the at least partial coating adapted to polarize at least transmitted radiation. According to this non-limiting embodiment, at least a portion of the alignment transfer material can be aligned with at least a portion of the alignment facility, and at least a portion of the at least one dichroic material of the at least partial coating can be aligned with at least a portion of the alignment transfer material. That is, the alignment transfer material is capable of facilitating the transfer of proper alignment or orientation from the at least one alignment facility to the at least one dichroic material. Furthermore, if the at least partial coating adapted to polarize radiation comprises an anisotropic material, at least a portion of the anisotropic material can be at least partially aligned with the alignment-transferring material and at least one dichroic material can be at least partially aligned with the at least one anisotropic material, as discussed above.

Non-limiting examples of alignment-transferring materials suitable for use in conjunction with the various non-limiting embodiments disclosed herein include liquid crystal materials selected from the group consisting of liquid crystal polymers, liquid crystal prepolymers, and liquid crystal monomers.

Liquid crystal monomers suitable for use as alignment transfer materials in combination with the various non-limiting embodiments disclosed herein include monofunctional liquid crystal monomers as well as multifunctional liquid crystal monomers. Further, according to various non-limiting embodiments disclosed herein, the liquid crystal monomer can be a crosslinkable liquid crystal monomer, and can in turn be a photo-crosslinkable liquid crystal monomer.

Non-limiting examples of cross-linkable liquid crystal monomers suitable for use as alignment transfer materials according to the various non-limiting embodiments disclosed herein include liquid crystal monomers having functional groups selected from the group consisting of acrylate, methacrylate, allyl ether, alkyne, amino, anhydride, epoxy, hydroxyl, isocyanate, blocked isocyanate, siloxane, thiocyanate, thiol, urea, vinyl ether and combinations thereof. Non-limiting examples of photo-crosslinkable liquid crystal monomers suitable for use as alignment transfer materials according to the various non-limiting embodiments disclosed herein include liquid crystal monomers having functional groups selected from acrylates, methacrylates, alkynes, epoxy groups, thiols, and combinations thereof.

Liquid crystal polymers and prepolymers suitable for use as alignment transfer materials in combination with the various non-limiting embodiments disclosed herein include, but are not limited to, thermotropic liquid crystal polymers and prepolymers, and lyotropic liquid crystal polymers and prepolymers. Further, the liquid crystal polymers and prepolymers can be backbone polymers and prepolymers or side chain polymers and prepolymers. In addition, the liquid crystal polymer or prepolymer can be crosslinkable, and further can be photo-crosslinkable, according to various non-limiting embodiments disclosed herein.

Non-limiting examples of liquid crystal polymers and prepolymers suitable for use as alignment transfer materials according to the various non-limiting embodiments disclosed herein include, but are not limited to, backbone and side chain polymers and prepolymers having functional groups selected from the group consisting of acrylate, methacrylate, allyl ether, alkyne, amino, anhydride, epoxy, hydroxyl, isocyanate, blocked isocyanate, siloxane, thiocyanate, thiol, urea, vinyl ether, and combinations thereof. Non-limiting examples of photo-crosslinkable liquid crystal polymers and prepolymers suitable for use as alignment transfer materials according to the various non-limiting embodiments disclosed herein include those polymers and prepolymers having functional groups selected from the group consisting of acrylates, methacrylates, alkynes, epoxy groups, thiols, and combinations thereof.

Ophthalmic elements according to various non-limiting embodiments disclosed herein can further comprise one or more coatings capable of promoting bonding, adhesion, or wetting of at least a portion of at least one outer surface of the ophthalmic element by at least one orientation mechanism. For example, the ophthalmic element can further comprise at least a portion of a primer layer located between the at least one orientation facility and the at least a portion of the at least one outer surface of the ophthalmic element. Non-limiting examples of primer layers suitable for use in connection with this non-limiting embodiment are described in detail below.

Yet another non-limiting embodiment provides an ophthalmic element comprising at least one at least partial coating comprising an alignment medium on at least a portion of at least one outer surface of the ophthalmic element, at least one at least partial coating comprising an alignment transfer material on at least a portion of the at least one at least partial coating comprising an alignment transfer material, and at least one at least partial coating comprising an anisotropic material and at least one dichroic material on at least a portion of the at least one at least partial coating comprising an alignment transfer material.

According to various non-limiting embodiments disclosed herein, the at least partial coating comprising the alignment medium can have a thickness that varies widely depending on the final application and/or processing device used. For example, in one non-limiting embodiment, the thickness of the at least partial coating comprising the alignment medium can be at least 2 nanometers to 10,000 nanometers. In another non-limiting embodiment, the at least partial coating comprising the alignment medium can have a thickness of from at least 5 nanometers to 1000 nanometers. In yet another non-limiting embodiment, the at least partial coating comprising the alignment medium can have a thickness of from at least 10 nanometers to 100 nanometers. In yet another non-limiting embodiment, at least a portion of the coating comprising the alignment medium can have a thickness from 50 nanometers to 100 nanometers. Additionally, according to various non-limiting embodiments, the ophthalmic element can include a plurality of at least partial coatings comprising an alignment medium. Further, each of the plurality of at least partial coatings can have a thickness that is the same as or different from another at least partial coating among the plurality.

Further, according to various non-limiting embodiments disclosed herein, at least a portion of the coating comprising the alignment transfer material can have a thickness that varies widely depending on the end use application and/or the processing device used. For example, in one non-limiting embodiment, the thickness of the at least partial coating comprising at least one alignment transfer material can be from 0.5 microns to 25 microns. In another non-limiting embodiment, the at least partial coating comprising the alignment transfer material can have a thickness of from 5 microns to 10 microns. Additionally, according to various non-limiting embodiments, the ophthalmic element can include a plurality of at least partial coatings comprising the alignment transfer material. Further, each of the plurality of at least partial coatings can have a thickness that is the same as or different from another at least partial coating among the plurality.

Still further, in accordance with various non-limiting embodiments disclosed herein, the at least partial coating comprising the anisotropic material and the at least one dichroic material can have a thickness that varies over a wide range depending on the end application and/or processing device used. In one non-limiting embodiment, the at least partial coating comprising the anisotropic material and the at least one dichroic material can have a thickness of at least 5 microns. Additionally, according to various non-limiting embodiments, the ophthalmic element can include a plurality of at least partial coatings comprising the anisotropic material and the at least one dichroic material. Further, each of the plurality of at least partial coatings can have a thickness that is the same as or different from another at least partial coating among the plurality.

As discussed previously, to achieve a net polarizing effect, at least a portion of the at least one dichroic material generally must be suitably aligned or positioned (i.e., ordered or aligned). Thus, although not limiting herein, according to various non-limiting embodiments, at least a portion of the alignment medium can be at least partially ordered in a first general direction, at least a portion of the alignment transfer material can be at least partially aligned with at least a portion of the alignment medium in a second general direction that is generally parallel to the first general direction, at least a portion of the anisotropic material can be at least partially aligned with at least a portion of the alignment transfer material in a third general direction that is generally parallel to the second general direction, and at least a portion of the at least one dichroic material can be at least partially aligned with at least a portion of the anisotropic material, as previously discussed. That is, according to this non-limiting embodiment, at least a portion of the dichroic material is capable of being at least partially aligned such that the long axis of at least a portion of the dichroic material is generally parallel to the third general direction of the anisotropic material that is at least partially aligned.

Further, according to various non-limiting embodiments disclosed herein, the at least partial coating comprising an alignment medium and/or the at least partial coating comprising an alignment transfer material can further comprise at least one dichroic material, which can be the same as or different from the at least one dichroic material of the at least partial coating comprising an anisotropic material and at least one dichroic material. Additionally, any of the at least partial coatings discussed above can further include at least one photochromic material and/or at least one additive or a combination thereof that can enhance at least one of the treatment, performance, or characteristic of the at least partial coating. Non-limiting examples of suitable photochromic materials and additives are described above.

As previously discussed, ophthalmic elements according to various non-limiting embodiments disclosed herein can further include one or more coatings capable of promoting bonding, adhesion, or wetting between the at least partial coating comprising the alignment medium and at least a portion of at least one outer surface of the ophthalmic element and/or between two different at least partial coatings. For example, according to one non-limiting embodiment, at least a portion of the primer layer can be positioned between the at least a portion of the coating comprising the alignment medium and the at least a portion of the at least one outer surface of the ophthalmic element. In another non-limiting embodiment, at least a portion of the primer layer can be between the at least a portion of the coating comprising the alignment medium and the at least a portion of the coating comprising the alignment transfer material and/or between the at least a portion of the coating comprising the alignment transfer material and the at least a portion of the coating comprising the at least one anisotropic material and the at least one dichroic material. Suitable non-limiting examples of undercoats are described in detail above.

According to another non-limiting embodiment, there is provided an ophthalmic element comprising a substrate, at least one orientation mechanism comprising an at least partial coating comprising a photo-orientable polymer network on at least a portion of at least one outer surface of the substrate, and an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of the at least one at least partial coating comprising a photo-orientable polymer network. Further, according to this non-limiting embodiment, the at least partial coating suitable for polarizing radiation comprises a liquid crystal material and at least one dichroic dye.

Additionally, according to the above non-limiting embodiments, the at least partial coating comprising a photo-orientable polymer network can further comprise at least one dichroic dye, which can be the same or different from the at least one dichroic dye of the at least partial coating comprising a liquid crystal material and at least one dichroic dye. Additionally, any of such at least partial coatings can further include at least one photochromic material and/or at least one additive that can enhance at least one of the processing, performance, or characteristics of the at least partial coating. Non-limiting examples of suitable photochromic materials and additives are described above.

Further, ophthalmic elements according to this and other non-limiting embodiments disclosed herein can include an at least partial coating comprising an alignment-transferring material between the at least partial coating comprising a photo-orientable polymer network and the at least partial coating adapted to polarize at least transmitted radiation. Non-limiting examples of suitable alignment transfer materials are described above.

Additionally, ophthalmic elements according to this non-limiting embodiment can further comprise one or more coatings capable of promoting the at least partial coating comprising the photo-orientable polymer network to bond, adhere, or wet at least a portion of at least one outer surface of the substrate. For example, according to this non-limiting embodiment, at least a portion of the primer layer can be located between the at least a portion of the coating comprising the photo-orientable polymeric network and the at least a portion of the at least one outer surface of the substrate. Non-limiting examples of base coats suitable for use in connection with the non-limiting embodiments are described above.

Further, as discussed above, ophthalmic elements according to this and other non-limiting embodiments disclosed herein can further include at least one additional at least partial coating on at least a portion of the substrate, the latter selected from photochromic coatings, antireflective coatings, transitional coatings, undercoats, and protective coatings. Non-limiting examples of suitable photochromic coatings, antireflective coatings, transitional coatings, undercoats, and protective coatings are described above.

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

Another non-limiting embodiment provides an optical device comprising at least one optical element comprising an at least partial coating comprising an alignment medium on at least a portion of at least one outer surface of the at least one optical element, and an at least partial coating comprising an anisotropic material and at least one dichroic material on at least a portion of the at least one at least partial coating comprising an alignment medium. Further, although not required, an at least partial coating comprising an alignment transfer material can be between at least a portion of the at least partial coating comprising an alignment medium and the at least partial coating comprising an anisotropic material and at least one dichroic material. Optical elements, alignment mediums, alignment transfer materials, anisotropic materials, and dichroic materials that can be used in conjunction with this one non-limiting embodiment are described in detail above.

Additionally, as previously discussed, according to the various non-limiting embodiments, the at least partial coating comprising an alignment medium and/or the at least partial coating comprising an alignment transfer material can further comprise at least one dichroic material, which can be the same as or different from the at least one dichroic material of the at least partial coating comprising an anisotropic material and at least one dichroic material. Further, any of such at least partial coatings discussed above can further include at least one photochromic material and/or at least one additive that can enhance at least one of the processing, performance, or characteristics of the at least partial coating. Non-limiting examples of suitable photochromic materials and additives are described above.

In addition, optical elements according to various non-limiting embodiments disclosed herein can further include one or more layers that can promote adhesion, bonding, or wetting between any of these coatings and at least a portion of at least one outer surface of the optical element. For example, at least a portion of the primer layer can be between the at least a portion of the coating comprising the alignment medium and the at least a portion of the at least one outer surface of the optical element or it can be between the at least a portion of the coating adapted to polarize at least transmitted radiation and the at least a portion of the outer surface of the optical element or another coating. Non-limiting examples of base coats suitable for use in connection with the non-limiting embodiments are described above.

Furthermore, as discussed above with respect to the previous non-limiting embodiments, the optical element according to this one non-limiting embodiment can further include at least one additional at least partial coating on at least a portion of the element, the latter selected from the group consisting of photochromic coatings, anti-reflective coatings, transitional coatings, undercoats, and protective coatings. Non-limiting examples of suitable photochromic coatings, antireflective coatings, transitional coatings and protective coatings are described above.

Further, although not meant to be limiting herein, according to the various non-limiting embodiments disclosed herein, the optical device can be selected from corrective and non-corrective ophthalmic lenses, magnifying ophthalmic lenses, clip-on lenses attachable to ophthalmic lenses, and contact lenses.

Various non-limiting embodiments of the fabrication of polarizing devices and elements according to the present invention will now be described. One non-limiting embodiment provides a method of making an ophthalmic element comprising forming an at least partial coating suitable for polarizing at least transmitted radiation on at least a portion of at least one exterior surface of the ophthalmic element.

Although not limiting herein, forming an at least partial coating suitable for polarizing at least transmitted radiation can include applying an at least partial coating comprising at least one dichroic material and at least one anisotropic material to at least a portion of at least one outer surface of an ophthalmic element and at least partially aligning at least a portion of the at least one dichroic material, according to this one non-limiting embodiment. As discussed previously, by having at least a portion of at least one dichroic material in a suitable orientation or arrangement, a net polarizing effect can be achieved. Non-limiting examples of dichroic and anisotropic materials suitable for use in conjunction with this and other non-limiting embodiments of the methods of manufacturing ophthalmic elements disclosed herein are described above.

Non-limiting examples of methods of applying at least partial coatings used in conjunction with methods of manufacturing ophthalmic and optical elements according to various non-limiting embodiments disclosed herein include, but are not limited to: spin coating, spray coating and spin coating, curtain coating, flow coating, dip coating, injection molding, casting, roll bonding, wire coating and processes for preparing a cover coat, such as the type described in US patent 4,873,029. In general, the application method chosen will depend on the thickness of the desired coating, the geometry of the surface to which the coating is applied, and the viscosity of the coating.

Further, according to various non-limiting embodiments disclosed herein, the process of applying the at least partial coating comprising at least one dichroic material and at least one anisotropic material can be performed before, after, or substantially simultaneously with the at least partial alignment of at least a portion of the at least one dichroic material.

For example, in one non-limiting embodiment wherein the at least partial coating comprising the at least one dichroic material and the at least one anisotropic material is applied prior to at least partially aligning at least a portion of the at least one dichroic material, the method of forming the at least partial coating can comprise spin coating the at least partial coating onto at least a portion of at least one outer surface of the ophthalmic element. Thereafter, at least a portion of the at least one anisotropic material can be at least partially ordered and at least a portion of the at least one dichroic material can be at least partially aligned with the at least partially ordered anisotropic material, such as by exposing at least a portion of the at least partial coating to at least one alignment mechanism after application of the at least partial coating.

In another non-limiting embodiment, wherein the process of applying the at least partial coating comprising the at least one dichroic material and the at least one anisotropic material is performed substantially simultaneously with the process of at least partially aligning at least a portion of the at least one dichroic material, applying the at least partial coating can comprise applying the at least partial coating to at least a portion of at least one outer surface of the ophthalmic element such that during the coating process, at least a portion of the anisotropic material is at least partially ordered and at least a portion of the at least one dichroic material is at least partially aligned with the at least partially ordered anisotropic material. For example, although not limited thereto, at least a portion of the anisotropic material can undergo at least partial ordering during the coating process due to shear forces generated by relative movement of the outer surface of the ophthalmic element with respect to the applied coating. Non-limiting coating methods according to this one non-limiting embodiment include, but are not limited to, curtain coating.

Additionally, according to various non-limiting embodiments disclosed herein, forming the at least partial coating adapted to polarize at least transmitted radiation can include forming a plurality of at least partial coatings on at least a portion of at least one outer surface of the ophthalmic element, at least one of which is adapted to polarize at least transmitted radiation. For example, although not limiting herein, a process for forming the at least partial coating suitable for polarizing at least transmitted radiation can comprise, according to one non-limiting embodiment, forming a first at least partial coating comprising an alignment medium and at least partially ordering at least a portion of the alignment medium, forming a second at least partial coating comprising an alignment transfer material and at least partially aligning at least a portion of the alignment transfer material, and forming a third at least partial coating comprising at least one anisotropic material and at least one dichroic material and then at least partially aligning at least a portion of the at least one dichroic material. Additionally, according to this one non-limiting embodiment, any of the first and second at least partial coatings can further comprise at least one dichroic material. In addition, any of the first, second, or third at least partial coatings can include at least one photochromic material and/or additive that can enhance processing, performance, and characteristics of the at least partial coating. Non-limiting examples of suitable dichroic materials, photochromic materials, and additives have been described in the discussion of various non-limiting embodiments of components and devices.

Methods of manufacturing ophthalmic elements according to various non-limiting embodiments disclosed herein can further include at least partially securing at least a portion of one or more of the at least partial coatings after forming the at least partial coating on at least a portion of the element. The term "fixed (set)" as used herein means fixed at a desired position. For example, in one non-limiting embodiment, at least a portion of the at least partial coating adapted to polarize at least transmitted radiation can be at least partially secured after the at least partial coating is formed on at least a portion of at least one outer surface of the ophthalmic element. Although not meant to be limiting herein, according to various non-limiting embodiments disclosed herein, at least partially securing at least a portion of at least a partial coating can include at least one of at least partially curing, at least partially crosslinking, or at least partially drying at least a portion of the at least partial coating.

Still further, according to various non-limiting embodiments disclosed herein, at least partially immobilizing at least a portion of the coating can include at least partially curing the at least a portion of the coating by exposing the at least a portion of the coating to infrared, ultraviolet, gamma-ray, or electron radiation to initiate polymerization or crosslinking of the polymerizable component with or without a catalyst or initiator. This is followed, if appropriate, by a heating step.

In which at least part of the coating comprises at least one photocrosslinkable material, e.g. a photocrosslinkable liquidIn one non-limiting embodiment of the crystalline material, at least partially immobilizing can include at least partially crosslinking the photocrosslinkable material by exposing the photocrosslinkable material to suitable actinic radiation. For example, although not limiting herein, at least partially securing the at least partial coating comprising the photocrosslinkable material can comprise exposing at least a portion of the photocrosslinkable material to ultraviolet radiation in a substantially inert atmosphere. The term "substantially inert atmosphere" as used herein refers to an atmosphere having limited reactivity with respect to the material being cured. For example, in one non-limiting embodiment, the substantially inert atmosphere comprises no more than 100ppm O₂A gas. Examples of suitable substantially inert atmospheres include, but are not limited to, atmospheres containing nitrogen, argon, and carbon dioxide.

Methods of manufacturing an ophthalmic element according to various non-limiting embodiments disclosed herein can further comprise applying at least a partial primer layer to at least a portion of at least one exterior surface of the ophthalmic element prior to applying the at least partial coating adapted to polarize at least transmitted radiation. Additionally, although not limited thereto, at least one additional at least partial coating selected from the group consisting of photochromic coatings, antireflective coatings, transitional coatings, undercoats, and protective coatings can be applied to at least a portion of at least one outer surface of the ophthalmic element either before or after application of the at least partial coating adapted to polarize at least transmitted radiation. Non-limiting examples of suitable primer, photochromic, antireflective, transitional, and protective coatings are described in detail above.

Additionally, if appropriate, methods according to various non-limiting embodiments disclosed herein can further comprise rinsing at least a portion of the ophthalmic element or substrate prior to applying any coating on the ophthalmic element or substrate. This is done for the purpose of cleaning and/or promoting adhesion of the coating. Effective processing techniques for plastics and glass are known to those skilled in the art.

As discussed above, according to one non-limiting embodiment, a method of manufacturing an ophthalmic element is provided that includes forming an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of at least one surface of the ophthalmic element. Additionally, in accordance with this non-limiting embodiment, the method can further comprise providing at least one orientation facility onto at least a portion of at least one outer surface of the ophthalmic element prior to forming the at least partial coating thereon suitable for polarizing at least transmitted radiation. According to this non-limiting embodiment, providing at least a portion of at least one outer surface of an ophthalmic element with at least one orientation mechanism can comprise at least one of the following processes: applying an at least partial coating comprising an alignment medium to at least a portion of at least one outer surface of an ophthalmic element and at least partially ordering the at least a portion of the alignment medium, applying an at least partially stretched polymeric sheet to at least a portion of at least one outer surface of the ophthalmic element; and at least partially treating at least a portion of at least one outer surface of the ophthalmic element, such as, but not limited to, using an etching or rubbing process.

Yet another non-limiting embodiment of a method of making an ophthalmic element comprises providing at least a portion of at least one outer surface of an ophthalmic element with at least one alignment facility comprising an at least partial coating comprising an alignment medium, applying at least one dichroic material to at least a portion of the at least one alignment facility, and at least partially aligning at least a portion of the at least one dichroic material.

According to this non-limiting embodiment, providing at least one orientation mechanism to at least a portion of at least one outer surface of an ophthalmic element can comprise applying an at least partial coating comprising an alignment medium to at least a portion of at least one outer surface of an ophthalmic element and at least partially ordering the at least a portion of the alignment medium. For example, although not limiting herein, providing at least one orientation mechanism can include applying an at least partial coating comprising an alignment medium to at least a portion of at least one outer surface of an ophthalmic element and at least partially ordering at least a portion of the alignment medium. The foregoing describes non-limiting examples of alignment media suitable for use in connection with various non-limiting embodiments of the methods disclosed herein.

Non-limiting examples of methods of at least partially ordering at least a portion of the directionally arranged medium that can be used in connection with the methods of manufacturing ophthalmic elements according to the various non-limiting embodiments disclosed herein include at least one of the following: exposing the at least a portion of the alignment medium to plane-polarized ultraviolet radiation; exposing the at least a portion of the alignment medium to infrared radiation; exposing the at least a portion of the alignment medium to a magnetic field; exposing the at least a portion of the alignment medium to an electric field; drying the at least a portion of the alignment medium; etching the at least a portion of the directionally aligned dielectric; subjecting the at least a portion of the alignment medium to a shear force; and rubbing the at least a portion of the alignment medium.

For example, while not meant to be limiting herein, according to one non-limiting embodiment wherein the alignment medium is a photo-orientable material (such as, but not limited to, a photo-orientable polymeric network), a method of making an ophthalmic element can comprise applying an at least partial coating comprising the photo-orientable material to at least a portion of at least one outer surface of the ophthalmic element and at least partially ordering the at least a portion of the photo-orientable material by exposing the at least a portion to plane-polarized ultraviolet radiation. Thereafter, at least one dichroic material can be applied over at least a portion of the at least partially ordered photo-alignment material and then at least partially aligned.

Further, if desired, providing at least one orientation mechanism can further comprise at least partially securing at least a portion of the at least one orientation mechanism. As discussed above, at least partially fixing can include at least partially curing, at least partially crosslinking, or at least partially drying at least a portion of at least one orientation mechanism. For example, although not limiting herein, a method according to one non-limiting embodiment disclosed herein can comprise providing at least one alignment mechanism to at least a portion of at least one outer surface of an ophthalmic element by applying an at least partial coating comprising an alignment medium to at least a portion of at least one outer surface of the ophthalmic element, at least partially immobilizing at least a portion of the alignment medium, and at least partially ordering at least a portion of the alignment medium prior to applying the at least one dichroic material.

Non-limiting examples of methods of applying at least one dichroic material to at least a portion of at least one alignment mechanism comprising an at least partial coating of an alignment medium according to various non-limiting embodiments disclosed herein include those methods discussed above for applying the at least partial coating. For example, although not meant to be limiting herein, methods of applying the at least one dichroic material can include spin coating, spray and spin coating, curtain coating, flow coating, dip coating, injection molding, casting, roll coating, wire coating, and methods for preparing an overcoat layer, such as the type of methods described in U.S. Pat. No. 4,873,029.

In addition, the at least one dichroic material can be applied to at least a portion of the at least one alignment mechanism comprising an at least partial coating comprising an alignment medium using an imbibition process. Suitable infiltration techniques are described, for example, in US patents 5,130,353 and 5,185,390, which are hereby specifically incorporated by reference. For example, although not limiting herein, the dichroic material can be applied to at least a portion of the at least one alignment facility by applying the dichroic material (either as a neat dichroic material, or dissolved in a polymer or other organic solvent carrier) to at least a portion of the alignment facility, and then subjecting the dichroic material and the alignment facility to heat to cause the at least one dichroic material to diffuse into at least a portion of the alignment facility.

Further, according to various non-limiting embodiments disclosed herein, applying at least one dichroic material to at least a portion of the at least one alignment facility can occur prior to aligning the at least one dichroic material, after aligning the at least one dichroic material, or substantially simultaneously with aligning the at least one dichroic material. For example, although not limiting herein, the at least one dichroic material can be applied in one non-limiting embodiment by spin coating a solution or mixture of the at least one dichroic material and the liquid crystal polymer in a carrier onto at least a portion of the alignment mechanism prior to alignment, and thereafter evaporating at least a portion of the solvent or carrier to cause at least a portion of the liquid crystal polymer and at least a portion of the at least one dichroic material to undergo alignment. In another non-limiting embodiment, the at least one dichroic material can be applied and aligned substantially simultaneously, such as by impregnating at least a portion of the orientation mechanism with the at least one dichroic material. The method of infiltration is discussed in detail above.

According to various non-limiting embodiments disclosed herein, the at least one dichroic material can be applied to the at least one orientation facility as a solution or mixture with a support, or with one or more other materials such as anisotropic materials, photochromic materials, and additives that can improve at least one property among the processability, performance, or characteristics of the applied material. Non-limiting examples of suitable anisotropic materials, photochromic materials, and additives have been set forth for the various non-limiting embodiments of the elements and devices discussed above.

Additionally, methods of manufacturing an ophthalmic element according to various non-limiting embodiments disclosed herein can further comprise applying at least a portion of a primer layer to at least a portion of at least one exterior surface of the ophthalmic element prior to providing at least a portion of the exterior surface with at least one orientation mechanism. Additionally, at least one additional at least partial coating selected from the group consisting of photochromic coatings, antireflective coatings, transitional coatings, undercoats, and protective coatings can be applied to at least a portion of at least one outer surface of the ophthalmic element and/or over at least a portion of at least one dichroic material. Non-limiting examples of suitable primer coatings, photochromic coatings, antireflective coatings, transitional coatings and protective coatings are described above.

Another non-limiting embodiment provides a method of manufacturing an ophthalmic element comprising applying an at least partial coating to at least a portion of at least one outer surface of the ophthalmic element and adjusting (adapt) at least a portion of the at least partial coating to polarize at least transmitted radiation. According to this non-limiting embodiment, the process of applying the at least partial coating to at least a portion of at least one outer surface of the ophthalmic element can be performed before, after, or substantially simultaneously with adjusting at least a portion of the at least partial coating to polarize at least transmitted radiation.

For example, while not limiting herein, the process of applying at least a portion of a coating to at least a portion of at least one outer surface of an ophthalmic element can include applying an at least partial coating comprising an anisotropic material and at least one dichroic material to at least a portion of at least one outer surface, according to one non-limiting embodiment; and adjusting at least a portion of the at least partial coating to polarize at least transmitted radiation can include at least partially aligning at least a portion of the at least one dichroic material. Further, the process of at least partially aligning at least a portion of the at least one dichroic material can include at least partially ordering at least a portion of the anisotropic material and at least partially aligning the at least one dichroic material with the at least partially ordered anisotropic material.

Suitable methods of at least partially ordering at least a portion of the anisotropic material include, but are not limited to, exposing the anisotropic material to plane-polarized ultraviolet radiation, exposing the at least a portion of the anisotropic material to infrared radiation, exposing the at least a portion of the anisotropic material to a magnetic field, exposing the at least a portion of the anisotropic material to an electric field, drying the at least a portion of the anisotropic material, etching the at least a portion of the anisotropic material, subjecting the at least a portion of the anisotropic material to a shear force, rubbing the at least a portion of the anisotropic material, and aligning the at least a portion of the anisotropic material with another structure or material (e.g., without limitation, an at least partially ordered alignment medium).

In another non-limiting embodiment, the process of applying the at least one coating to at least a portion of at least one outer surface of the ophthalmic element comprises applying an at least partial coating comprising an alignment medium to at least a portion of at least one outer surface of the ophthalmic element, and the process of adjusting the at least a portion of the at least partial coating to polarize at least transmitted radiation comprises at least partially ordering at least a portion of the alignment medium, applying at least one dichroic material to at least a portion of the at least partial coating comprising an alignment medium, and at least partially aligning at least a portion of the at least one dichroic material.

Non-limiting examples of alignment media suitable for use in connection with the various non-limiting embodiments of the methods disclosed herein include those previously described with respect to the various non-limiting embodiments discussed above. For example, according to one non-limiting embodiment, wherein applying at least a partial coating to at least a portion of at least one outer surface of the ophthalmic element comprises applying at least a partial coating comprising an alignment medium to at least a portion of at least one outer surface of the ophthalmic element, the alignment medium can be selected from the group consisting of photo-alignment materials, rubbing-alignment materials, and liquid crystal materials.

Further, according to various non-limiting embodiments, at least partially ordering at least a portion of the alignment medium can include exposing the at least a portion of the alignment medium to plane-polarized ultraviolet radiation, exposing the at least a portion of the alignment medium to infrared radiation, exposing the at least a portion of the alignment medium to a magnetic field, exposing the at least a portion of the alignment medium to an electric field, drying the at least a portion of the alignment medium, etching the at least a portion of the alignment medium, subjecting the at least a portion of the alignment medium to a shear force, and rubbing the at least a portion of the alignment medium.

For example, although not limiting herein, according to one non-limiting embodiment wherein the alignment medium is a photo-orientable material (e.g., without limitation, a photo-orientable polymer network), at least partially ordering at least a portion of the photo-orientable material can comprise exposing at least a portion of the photo-orientable material to plane-polarized ultraviolet radiation.

Further, according to certain non-limiting embodiments wherein adjusting at least a portion of the at least partial coating to polarize at least transmitted radiation comprises applying at least one dichroic material to at least a portion of the at least partial coating comprising an at least partially ordered alignment medium and at least a portion of at least one dichroic material is at least partially aligned, the process of applying the at least one dichroic material can be performed before, after, or substantially simultaneously with the at least a portion of the at least one dichroic material being at least partially aligned. A non-limiting method of applying at least one dichroic material to at least a portion of the at least partial coating comprising an alignment medium comprises: spin coating, spray and spin coating, curtain coating, flow coating, dip coating, injection molding, casting, roll coating, wire coating and processes for making overcoat layers, such as the type described in U.S. Pat. No. 4,873,029, and impregnation.

Methods of manufacturing an ophthalmic element according to various non-limiting embodiments disclosed herein can further include applying at least a portion of a primer layer to at least a portion of at least one exterior surface of the ophthalmic element prior to forming the at least partial coating and adjusting the at least partial coating to polarize at least transmitted radiation. Additionally, the method of making an ophthalmic element can further comprise applying at least one additional at least partial coating selected from the group consisting of photochromic coatings, antireflective coatings, transitional coatings, undercoats, and protective coatings to at least a portion of the ophthalmic element. For example, although not limiting herein, the at least one additional at least partial coating can be applied over at least a portion of the at least partial coating adapted to polarize at least transmitted radiation. Additionally or alternatively, the at least partial coating adapted to polarize at least transmitted radiation can be formed on at least a portion of a first outer surface of the ophthalmic element and at least one additional at least partial coating can be applied to at least a portion of a second outer surface of the ophthalmic element, wherein the first outer surface of the ophthalmic element is opposite the second outer surface of the ophthalmic element. Non-limiting examples of such coatings are described in detail above.

Another non-limiting embodiment of a method of making an ophthalmic element comprises applying an at least partial coating comprising an alignment medium to at least a portion of at least one outer surface of the ophthalmic element and at least partially ordering the at least a portion of the alignment medium. Thereafter, according to this non-limiting embodiment, an at least partial coating comprising an anisotropic material and at least one dichroic material is applied over at least a portion of the at least partial coating comprising an alignment medium and at least a portion of the at least one dichroic material is at least partially aligned. Although not required, the at least one at least partial coating comprising an alignment transfer material can be applied to at least a portion of the at least partial coating comprising an alignment medium and at least partially aligned prior to applying the at least partial coating comprising an anisotropic material and at least one dichroic material on a surface thereof.

According to this non-limiting embodiment, at least partially ordering at least a portion of the alignment medium can include exposing the at least a portion of the alignment medium to plane-polarized ultraviolet radiation, exposing the at least a portion of the alignment medium to infrared radiation, exposing the at least a portion of the alignment medium to a magnetic field, exposing the at least a portion of the alignment medium to an electric field, drying the at least a portion of the alignment medium, etching the at least a portion of the alignment medium, subjecting the at least a portion of the alignment medium to a shear force, and rubbing the at least a portion of the alignment medium.

Further, although not limited in this regard, as previously discussed, any of the at least partial coatings described above can be at least partially secured after application. For example, according to one non-limiting embodiment, at least a portion of the at least partial coating comprising alignment media can be at least partially immobilized before, during, or after at least partially ordering at least a portion of the alignment media. Further, according to this non-limiting embodiment, at least a portion of the at least partial coating comprising the alignment-transferring material and/or the at least partial coating comprising the anisotropic material and the at least one dichroic material can be at least partially immobilized by curing at least a portion of the at least partial coating. For example, at least a portion of the alignment transfer material can be exposed to ultraviolet radiation under an inert atmosphere to cure at least a portion of the alignment transfer material. Similarly, at least a portion of the at least partial coating comprising the anisotropic material and the at least one dichroic material can be cured by exposing at least a portion of the anisotropic material to ultraviolet radiation under an inert atmosphere after at least a portion of the at least one dichroic material is at least partially aligned.

Another non-limiting embodiment of the present invention provides a method of making a lens for ophthalmic applications comprising applying an at least partial coating comprising a photo-orientable polymer network to at least a portion of at least one outer surface of the lens, at least partially ordering at least a portion of the photo-orientable polymer network with plane-polarized ultraviolet radiation. Thereafter, an at least partial coating comprising a liquid crystal material and at least one dichroic dye is applied to at least a portion of the at least partial coating comprising a photo-orientable polymer network, and the at least one dichroic dye is then at least partially aligned. After aligning at least a portion of the coating comprising the liquid crystal material and the at least one dichroic dye, at least a portion of the coating comprising the liquid crystal material and the at least one dichroic dye can be at least partially immobilized, such as (but not limited to) by curing. Although not required, the at least partial coating comprising the alignment transfer material can be applied to at least a portion of the at least partial coating comprising the photo-orientable polymer network prior to applying the at least partial coating comprising the liquid crystal material and the at least one dichroic dye on a surface thereof.

Other embodiments of the present invention provide methods of making an optical element comprising applying an at least partial coating to at least a portion of at least one outer surface of an optical element and adjusting at least a portion of the at least partial coating to polarize at least transmitted radiation. Suitable methods of applying at least a portion of the coating and polarizing the radiation with at least a portion of the coating are described in detail above.

Various non-limiting embodiments of the invention are now described in the following non-limiting examples.

Examples

Step 1

Preparation of solutions of anisotropic materials

To each beaker equipped with a magnetic stir bar and placed on a magnetic stirrer was added 3 grams of the following liquid crystal monomers ("LCM") (which are available from EMD Chemicals, inc.) in the order listed and with stirring:

RM 23-reported to have C₂₃H₂₃NO₅Of the formula

RM 257-reportedly has C₃₃H₃₂O₁₀Of the formula

RM 82-reported to have C₃₉H₄₄O₁₀Of the formula

RM 105-reported to have C₂₃H₂₆O₆Of the formula

Anisole (8.0 g) was then added to the contents of the beaker and the resulting mixture was heated to 60 ℃ and stirred until the solids had dissolved as determined by visual inspection. The resulting liquid crystal monomer solution (or "LCMS") is divided into two parts, an "A-LCMS part" and a "B-LCMS part". The beaker containing the a-LCMS portion was placed open on a balance in a fume hood until the percent solids increased from the initial 60% to 62%. Part B-LCMS had a 60% solids content.

Step 2

Preparation of stock solutions of anisotropic and dichroic materials

The following 3 dichroic dyes (available from Mitsubishi Chemical) were used to prepare various dichroic dye-colored liquid crystal monomer solutions (i.e., red-, blue-, yellow-or gray-LCMS):

LSR-652 is reported to be a red dye, belonging to Lot: 01J 0315;

LSR-335 is reported to be a blue dye belonging to Lot: 01C 131; and

LSR-120 is reported to be a yellow dye belonging to Lot: 2D 231.

red-LCMS, blue-LCMS and yellow-LCMS were each prepared by adding to the a-LCMS portion (prepared in step 1) the amount of dichroic dye needed to produce a dichroic dye colored LCMS having the dichroic dyes (based on the solids of the a-LCMS portion) listed below for each. gray-LCMS was prepared by using the B-LCMS portion from step 1 and adding a combination of various dichroic dyes listed below thereto in amounts required to reach the dyes listed below (based on the solids of the B-LCMS portion).

Dye coloring LCMS	Dichroic dye	Dichroic dye%
			Red-LCMS	LSR652	2.0
blue-LCMS	LSR335	3.0
			yellow-LCMS	LSR120	2.5
Grey-LCMS	LSR652LSR335LSR120	0.81.10.6

Red-LCMS, blue-LCMS and yellow-LCMS each also contained 1.0% (solids based on the A-LCMS portion) of Irgacure 819, a photoinitiator available from Ciba-Geigy Corporation; and 0.5% (based on the solids of the A-LCMS portion) of two stabilizers in a 50: 50 weight ratio. The stabilizers are TINUVIN-292, a Ciba-Geigy light stabilizer for coatings, and SANDUVOR VSU, a Clariant-available stabilizer based on oxalanilide. The grey-LCMS contains 1.0% each (based on the solids of the B-LCMS portion) of Irgacure 819 in combination with the two stabilizers described above.

And step 3:

preparation of coating solutions comprising anisotropic and dichroic materials

A coating solution comprising an anisotropic material and a dichroic material is prepared by: the raw material dichroic dye colored LCMS from step 2 was added to the beaker in the amounts indicated in examples 1-5 below (weighed on an analytical balance) and mixed and heated to 50-60 ℃ if necessary to prevent the liquid crystal monomer from precipitating and dissolving the dye. Using the gray-LCMS prepared above in step 2, the additional coating solution of example 6 was prepared, and further mixed and heated as needed. After mixing, each solution was filtered using a syringe filter with a pore size of 1.2 microns to remove any particulate matter.

Example 1

Material	Weight of materials (g)
		Red dye solution	0.6008
Blue dye solution	1.2772
		Yellow dye solution	0.5049

Example 2

Material	Weight of materials (g)
		Red dye solution	0.5415
Blue dye solution	0.8892
		Yellow dye solution	0.3501

Example 3

Material	Weight (g)
		Red dye solution	0.5410
Blue dye solution	0.8880
		Yellow dye solution	0.3945

Example 4

Material	Weight (g)
		Red dye solution	0.3939
Blue dye solution	0.6460
		Yellow dye solution	0.3272

Example 5

Material

Weight (g))

Red dye solution	0.3758
		Blue dye solution	0.4908
Yellow dye solution	0.2832

Each of the above coating solutions is used in the procedures described below in sections a-D to produce an at least partial coating on a substrate surface suitable for polarizing at least transmitted radiation. After preparation, the absorptance of each coated substrate was measured according to the absorptance measurement test described in section E.

Part A

Substrate cleaning

A square substrate having dimensions of 2 inches by 0.25 inches (5.08cm by 0.635cm) is obtained by: CR-39Monomers or TRIVEX151 lens material, both available from PPG Industries, inc;CR-607a monolithic 70mm diameter planoscope available from PPG Industries, inc; and a photochromic lens obtained from Transitions Optical Incorporated having a refractive index of 1.50. Thereafter, each substrate was cleaned by washing in a solution of liquid soap and water, rinsing with deionized water, and then rinsing with isopropyl alcohol. After washing and rinsing, the substrate was dried and then treated with oxygen plasma at 100 watts of power for one minute at an oxygen flow rate of 100 milliliters (mL)/minute.

As shown in section D below and table 1, some substrates were further treated with a primer as described in US patent 6,150,430. More specifically, these substrates were treated by dispensing the undercoating composition onto the substrate for a period of 10 seconds while the substrate was rotating at 1500 rpm. The coated substrate was then coated on a Light-weld available from Dymax CorpIn a 5000-EC UV light source, 4 inches from the light source, cure for 10 seconds.

Part B

Preparation of orientation mechanisms using photo-orientable polymer networks

The orientation mechanism is provided to a portion of the cleaned substrate (described in section a above) as follows. As Staralign2200 CP2 or CP4 solutions (both trade designations are reported to refer to 2 wt% in cyclopentane and 4 wt% in cyclopentane, respectively) solutions of photo-orientable polymer networks obtained from Huntsman advanced materials were applied to a portion of the surface of the substrate made in part a in such a way that the Staralign solution was dispensed onto the substrate over a period of 2-3 seconds. Since the Staralign solution was dispensed onto the substrate, the substrate was spun at 600-And (3) minutes. After coating, the substrate was placed in an oven maintained at 130 ℃ for 20-30 minutes. Referring to table 1 below, Staralign2200 CP2 solution was used on samples 6a1 and 6a 2. All other samples except 6A (magnetic) were coated with Staralign2200 CP 4.

At least a portion of the photo-orientable polymer network is at least partially ordered by exposure to plane-polarized ultraviolet radiation having the use of UV Power Puck available from electronic instrumentation and Technology, Inc^TM18 milliwatts/cm as measured by an electro-optical radiometer²Peak intensity of UVA (320-390 nm). The source of the UV radiation is a BLAK-RAY Model B-100A wavelength UV lamp. Again, referring to table 1, samples 1A through 6D were exposed to plane polarized uv radiation for 2 minutes and samples 6a1 and 6a2 were exposed to plane polarized uv radiation for 3 minutes.

Moiety C

Preparation of an at least partial coating suitable for polarizing at least transmitted radiation

An at least partial coating suitable for polarizing at least transmitted radiation was then formed on each of the substrates prepared in part B by coloring the LCMS with one of the dichroic dyes described above in examples 1-6 of step 3.

The dichroic dye coloring LCMS is applied to at least a part of the alignment mechanism on the surface of the substrate by spin coating. More specifically, about 1mL of the dichroic dye coloring LCMS is dispensed onto the substrate and the excess dichroic dye coloring LCMS (if any) is drained. Thereafter, the substrate was spun at 300-400 rpm for 4 to 6 minutes. After spin coating, the substrate is placed in an oven at 45-55 ℃ for 20-40 minutes to allow at least a portion of the LCM and at least a portion of the dichroic dye to align.

Thereafter, the formed coating was tested for alignment by using two cross-polarized polarizing films (#45669) obtained from Edmund Industrial Optics. Each coated substrate is placed between cross-polarized polarizer films such that the coated substrate is parallel to at least one of the films, such that visible light transmission through the polarizer films and the coated substrate's structured structure is reduced. When one of the two polarizing films is rotated by 45 degrees in the clockwise direction or the counterclockwise direction while viewing a visible light source through this configuration, at least partial alignment is verified by observing an increase in the transmitted visible light. When two at least partial coatings of dichroic dye pigmented LCMS are applied, the above steps of part C are completed before the application of the second at least partial coating.

After verifying the at least partial alignment of the coating, the at least partial coating was further cured by covering each coated substrate with a 6-base (base) polycarbonate planoscope having a diameter of 70mm and a thickness of 2.0mm such that it was about 1mm to 2mm above the surface of the coated substrate. The resulting polycarbonate lens/coated substrate assembly was placed on a uv conveyor curing line available from Eye Ultraviolet, Inc. The UV conveyor curing line has a nitrogen atmosphere with an oxygen content below 100 ppm. The conveyor was run at three feet per minute under two ultraviolet "D-type" 400 watt/inch iron iodide doped mercury lamps of 10 inch length. One of the lamps was located 2.5 inches above the conveyor and the other lamp was located 6.5 inches above the conveyor. Peak intensities of different UV wavelengths provided by UV conveyor curing line by using the UV Power Puck described previously^TMElectro-optical radiometer measurements. The peak intensity of UVA (320 to 390nm) measured was 0.239W/cm²And the peak intensity of UVV (395 to 445nm) measured was 0.416W/cm²。

Part D

Preparation of at least partial coatings suitable for polarizing at least transmitted radiation using a magnetic field

Coated with a primer coating as described in part A and consisting of CR39The square base material resulting from the polymerization product of the monomeric lens material was used to prepare coated samples in this section D. However, as described below, the substrate was not prepared as part B prior to coating the gray-LCMS.

For samples prepared according to this section D, the base coat coated substrate (described in section a above) was coated with the gray-LCMS of example 6 (described in step 3 above) generally following the procedure of section C, except that at least a portion of the coating was at least partially ordered as follows prior to curing the coated substrate. The coated substrate was placed on a temperature controlled hot plate 8 inches below the temperature controlled infrared lamp and between the N and S poles of a 0.35 tesla magnet spaced 11 cm apart. Both temperature controllers are set to maintain a temperature of about 55 c to 60 c. The coated substrate is kept under these conditions for 40-45 minutes to at least partially order the LCM and dichroic dye. Thereafter, the ordered coating is cured and the ordering of the coating is verified according to the method described in section C (for directionally aligned coatings). The resulting sample is indicated in table 1 as 6A (magnetic).

Part E

Absorption measurement test

The absorption ratio of each coated substrate was measured as follows. CARY 4000 UV-visible spectrophotometer equipped with a polarization analyzer (Moxtek ProFlux)^TMPolarizer) self-centering sample holder. The instrument set the following parameters: scanning speed is 600 nm/min; data interval 1.0 nm; the integration time is 100 ms; absorption rate range is 0-6.5; y-mode ═ absorption; the X-mode is nm and the scan range is 400-800 nm. The setting option is 3.5 SBW (slit width) and doubles for the beam mode. The baseline option is set to zero/baseline correction. Samples of each substrate without an orientation mechanism and/or a coating suitable for polarizing at least transmitted radiation were used to set the zero/baseline correction. For samples with a substrate coated with a base coat, the zero/baseline correction was passedUsing a base coated substrate. Also, the 2.5 neutral density filter is in the reference path for all scans. Coated substrate samples were maintained at room temperature maintained by a laboratory air conditioning system (73)±5) The test was carried out in the following atmosphere.

The required orientation for the sample polarizer to be parallel and perpendicular to the analyzing polarizer is accomplished in the following manner. Cary 4000 was set to 500nm (or at the peak absorbance of the sample) and the absorbance was monitored as the sample was rotated in small increments (1-5 degrees). The rotation of the sample continues until the absorption is maximal. This position is defined as the vertical or 90 degree position. The parallel position is obtained by rotating the platform (stage) clockwise or counterclockwise.

For each sample, the absorption spectra were collected at 90 degrees and 0 degrees simultaneously. Data analysis was processed using Igor Pro software obtained from WaveMetrics. The spectrum was input into Igor Pro and the absorbance was used to calculate the absorbance at 566 nm. The calculated absorption ratios are listed in table 1.

In Table 1, the sample numbers correspond to the coating compositions applied to the substrates tested (e.g., examples 1-6). The different letters associated with the sample numbers represent different substrates as follows: "A" means CR39The polymerization product of monomers; "B" means TRIVEX151 polymerization product of lens material; "C" represents a photochromic lens obtained from Transmission optical incorporated having a refractive index of 1.50; and "D" denotes CR-607The polymerization product of the monomers. The double letter indicates that the substrate was coated twice in part C. The results for samples 6a1 and 6a2 are the arithmetic mean of the 2 results. The results for the other samples were the individual coated substrates tested.

TABLE 1

Sample number	Base coat	Absorption ratio
			1A	-	3.1
2A	-	5.7
			3A	-	2.4
4A	-	4.0
			5A	-	5.4
6A	-	2.6
			6AA	-	4.4

6B	-	3.0
			6C	-	3.1
6D	-	3.9
			6A1	+	6.2
6A2	-	7.0
			6A (magnetic)	+	5.4

As shown in table 1, at least a portion of the coating suitable for polarizing at least transmitted radiation according to the non-limiting embodiments described above exhibits an absorption ratio from 2.4 to 7.0.

It should be understood that this description is only illustrative of various aspects of the invention relevant to a clear understanding of the invention. Certain aspects of the invention that are familiar to those skilled in the art and that therefore do not facilitate an understanding of the invention have not been presented herein in order to simplify the description of the invention. While the invention has been described in connection with certain embodiments, the invention is not limited to the specific embodiments or examples disclosed, but is intended to cover all modifications that are within the spirit and scope of the invention as defined by the appended claims.

Claims (99)

1. An ophthalmic element comprising:

a substrate;

at least one orientation mechanism comprising an at least partial coating comprising a photo-orientable polymer network on at least a portion of at least one outer surface of the substrate; and

an at least partial coating adapted for polarizing at least transmitted radiation on at least a portion of the at least one at least partial coating comprising a photo-orientatable polymer network, wherein the at least partial coating adapted for polarizing at least transmitted radiation comprises at least one dichroic dye, and a liquid crystal polymer.

2. The ophthalmic element of claim 1 wherein the ophthalmic element is selected from the group consisting of a corrective lens, a non-corrective lens and a magnifying lens.

3. The ophthalmic element of claim 1 wherein the ophthalmic element is selected from the group consisting of an uncolored ophthalmic element, a colored ophthalmic element, a photochromic ophthalmic element and a colored photochromic ophthalmic element.

4. The ophthalmic element of claim 1 wherein the at least partial coating adapted to polarize at least transmitted radiation is adapted to polarize at least transmitted visible radiation.

5. The ophthalmic element of claim 1 wherein the at least partial coating adapted to polarize at least transmitted radiation is adapted to polarize transmitted visible radiation and transmitted ultraviolet radiation.

6. The ophthalmic element of claim 1 wherein the at least one dichroic dye has an absorption ratio from 2 to 30.

7. The ophthalmic element of claim 1 wherein the at least one dichroic dye has an absorption ratio of at least 3.

8. The ophthalmic element of claim 1 wherein the at least one dichroic dye has an absorption ratio of at least 5.

9. The ophthalmic element of claim 1 wherein the at least one dichroic dye has an absorption ratio of at least 7.

10. The ophthalmic element of claim 1 wherein the at least one dichroic dye has an absorption ratio of at least 10.

11. The ophthalmic element of claim 1 wherein the at least one dichroic dye is selected from the group consisting of azomethines, indigoids, thioindigoids, merocyanines, indanes, quinophthalone dyes, perylenes, phthalimides, triphenodioxazines, indoloquinoxalines, imidazotriazines, tetrazines, azo and (poly) azo dyes, benzoquinones, naphthoquinones, anthraquinones and (poly) anthraquinones, anthrapyrimidinones, iodine and iodates.

12. The ophthalmic element of claim 1 wherein the at least one dichroic dye is selected from azo and (poly) azo dyes, and anthraquinone and (poly) anthraquinone.

13. The ophthalmic element of claim 1 wherein the at least one dichroic dye is a polymerizable dichroic dye.

14. The ophthalmic element of claim 1 wherein the at least partial coating adapted to polarize at least transmitted radiation comprises a first type of dichroic dye having a first absorption ratio and at least one second type of dichroic dye having a second absorption ratio different from the first absorption ratio.

15. The ophthalmic element of claim 1 wherein the liquid crystalline polymer is a crosslinkable liquid crystalline material.

16. The ophthalmic element of claim 15 wherein the liquid crystal polymer is a photocrosslinkable liquid crystal material.

17. The ophthalmic element of claim 1 wherein the liquid crystalline polymer has at least one functional group selected from the group consisting of acrylate, methacrylate, allyl ether, alkyne, amino, anhydride, epoxy, hydroxyl, isocyanate, blocked isocyanate, siloxane, thiocyanate, thiol, urea, vinyl, and vinyl ether.

18. The ophthalmic element of claim 1 wherein at least a portion of the liquid crystal polymer is at least partially ordered in a general direction and at least a portion of the at least one dichroic dye is at least partially aligned with at least a portion of the at least partially ordered liquid crystal polymer.

19. The ophthalmic element of claim 18 wherein at least a portion of the at least one dichroic dye is at least partially aligned such that the long axis of the at least a portion of the at least one dichroic dye is generally parallel to the overall direction of the at least partially ordered liquid crystal polymer.

20. The ophthalmic element of claim 18 wherein the at least a portion of the at least one dichroic dye that is at least partially aligned is bound to a liquid crystal polymer.

21. The ophthalmic element of claim 1 wherein the at least partial coating adapted to polarize radiation further comprises at least one photochromic material.

22. The ophthalmic element of claim 21 wherein the at least one photochromic material is selected from the group consisting of pyrans, oxazines, fulgides and fulgimides, and metal dithizonates.

23. The ophthalmic element of claim 21 wherein the at least one photochromic material is a metal oxide encapsulated photochromic material.

24. The ophthalmic element of claim 1 wherein the at least partial coating adapted to polarize radiation further comprises a mixture of photochromic materials.

25. The ophthalmic element of claim 1 wherein the at least partial coating adapted to polarize at least transmitted radiation further comprises at least one additive selected from the group consisting of dyes, alignment promoters, kinetic enhancing additives, photoinitiators, solvents, light stabilizers, heat stabilizers, mold release agents, rheology control agents, leveling agents, free radical scavengers, and adhesion promoters.

26. The ophthalmic element of claim 1 further comprising at least one at least partial primer layer between at least a portion of the at least partial coating adapted to polarize at least transmitted radiation and at least a portion of the at least one outer surface of the ophthalmic element.

27. The ophthalmic element of claim 1 further comprising at least one additional at least partial coating on at least a portion of the ophthalmic element, the coating selected from the group consisting of photochromic coatings, antireflective coatings, transitional coatings, undercoats, and protective coatings.

28. The ophthalmic element of claim 27 wherein the at least one additional at least partial coating is on at least a portion of the at least partial coating adapted to polarize radiation.

29. The ophthalmic element of claim 27 wherein the at least partial coating adapted to polarize radiation is on at least a portion of a first outer surface of the ophthalmic element and the at least one additional at least partial coating is on at least a portion of a second outer surface of the ophthalmic element, wherein the first outer surface of the ophthalmic element is opposite the second outer surface of the ophthalmic element.

30. The ophthalmic element of claim 1 wherein the at least one orientation facility comprises a first ordered region having a first arrangement and at least one second ordered region adjacent to the first ordered region, the at least one second ordered region having a second arrangement different from the first arrangement.

31. The ophthalmic element of claim 1 wherein the photo-orientable polymer network is a photo-orientable polymer network selected from the group consisting of azobenzene derivatives, cinnamic acid derivatives, coumarin derivatives, ferulic acid derivatives and polyimides.

32. The ophthalmic element of claim 1 wherein the at least one alignment facility has at least one ordered area with a general direction and at least a portion of the at least one dichroic dye is at least partially aligned such that the long axis of the at least a portion of the at least one dichroic dye is generally parallel to the general direction of the at least one ordered area of the alignment facility.

33. The ophthalmic element of claim 1 further comprising at least one at least partial coating comprising an alignment transfer material between at least a portion of the orientation facility and at least a portion of the at least partial coating adapted to polarize at least transmitted radiation.

34. The ophthalmic element of claim 33 wherein the ophthalmic element comprises a plurality of at least partial coatings comprising an alignment transfer material between at least a portion of the orientation facility and at least a portion of the at least partial coatings adapted to polarize at least transmitted radiation.

35. The ophthalmic element of claim 33 wherein the alignment transfer material is a liquid crystal material selected from the group consisting of liquid crystal polymers, liquid crystal prepolymers, and liquid crystal monomers.

36. The ophthalmic element of claim 35 wherein the liquid crystal material is a cross-linkable liquid crystal material.

37. The ophthalmic element of claim 36 wherein the liquid crystal material is a photocrosslinkable liquid crystal material.

38. The ophthalmic element of claim 33 wherein the alignment transfer material is a liquid crystal material having at least one functional group selected from the group consisting of acrylate, methacrylate, allyl ether, alkyne, amino, anhydride, epoxy, hydroxyl, isocyanate, blocked isocyanate, siloxane, thiocyanate, thiol, urea, vinyl, and vinyl ether.

39. The ophthalmic element of claim 1 comprising:

at least one orientation facility comprising at least one at least partial coating comprising a photo-orientable polymer network on at least a portion of at least one outer surface of the substrate;

at least one at least partial coating comprising an alignment transfer material on at least a portion of the at least one at least partial coating; and

said at least one at least partial coating comprising a liquid crystal polymer and at least one dichroic dye on at least a portion of the at least one at least partial coating comprising an alignment transfer material.

40. The ophthalmic element of claim 39 wherein at least a portion of the photo-orientatable polymer network is at least partially ordered in a first general direction, at least a portion of the alignment transfer material is at least partially aligned in a second general direction that is generally parallel to the first general direction, at least a portion of the liquid crystal polymer is at least partially aligned in a third general direction that is generally parallel to the second general direction, and at least a portion of the at least one dichroic dye is at least partially aligned with at least a portion of the liquid crystal polymer such that a long axis of the at least a portion of the at least one dichroic dye is generally parallel to the third general direction of the at least partially aligned liquid crystal polymer.

41. The ophthalmic element of claim 39 wherein the photo-orientable polymer network is a photo-orientable polymer network selected from the group consisting of azobenzene derivatives, cinnamic acid derivatives, coumarin derivatives, ferulic acid derivatives, and polyimides.

42. The ophthalmic element of claim 39 wherein the at least one at least partial coating comprising a photo-orientable polymer network has a thickness of at least 2 nanometers to 10,000 nanometers.

43. The ophthalmic element of claim 39 wherein the at least one at least partial coating comprising a photo-orientable polymer network has a thickness of at least 5 nanometers to 1000 nanometers.

44. The ophthalmic element of claim 39 wherein the at least one at least partial coating comprising a photo-orientable polymer network has a thickness of at least 10 nanometers to 100 nanometers.

45. The ophthalmic element of claim 39 wherein the at least one at least partial coating comprising a photo-orientable polymer network has a thickness of at least 50 nanometers to 100 nanometers.

46. The ophthalmic element of claim 39 wherein the ophthalmic element comprises a plurality of at least partial coatings comprising the alignment medium.

47. The ophthalmic element of claim 39 wherein the at least one at least partial coating comprising an alignment medium further comprises at least one selected from the group consisting of dichroic dyes, photochromic materials, and additives selected from the group consisting of dyes, alignment promoters, kinetic enhancing additives, photoinitiators, solvents, light stabilizers, heat stabilizers, mold release agents, rheology control agents, leveling agents, free radical scavengers, and adhesion promoters.

48. The ophthalmic element of claim 39 wherein the alignment transfer material is a liquid crystal material selected from the group consisting of liquid crystal polymers, liquid crystal prepolymers, and liquid crystal monomers.

49. The ophthalmic element of claim 48 wherein the liquid crystal material is a cross-linkable liquid crystal material.

50. The ophthalmic element of claim 49 wherein the liquid crystal material is a photocrosslinkable liquid crystal material.

51. The ophthalmic element of claim 39 wherein the alignment transfer material is a liquid crystal material having at least one functional group selected from the group consisting of acrylate, methacrylate, allyl ether, alkyne, amino, anhydride, epoxy, hydroxyl, isocyanate, blocked isocyanate, siloxane, thiocyanate, thiol, urea, vinyl, and vinyl ether.

52. The ophthalmic element of claim 39 wherein the at least one at least partial coating comprising the alignment transfer material has an average thickness of from 0.5 microns to 25 microns.

53. The ophthalmic element of claim 39 wherein the at least one at least partial coating comprising the alignment transfer material has an average thickness of from 5 microns to 10 microns.

54. The ophthalmic element of claim 39 wherein the ophthalmic element comprises a plurality of at least partial coatings comprising the alignment transfer material.

55. The ophthalmic element of claim 39 wherein the at least one at least partial coating comprising an alignment transfer material further comprises at least one selected from the group consisting of dichroic dyes, photochromic materials, and additives selected from the group consisting of dyes, alignment promoters, kinetic enhancing additives, photoinitiators, solvents, light stabilizers, heat stabilizers, mold release agents, rheology control agents, leveling agents, free radical scavengers, and adhesion promoters.

56. The ophthalmic element of claim 39 wherein the at least one at least partial coating comprising an anisotropic material and at least one dichroic dye has an average thickness of at least 5 microns.

57. The ophthalmic element of claim 39 wherein the ophthalmic element comprises a plurality of at least partial coatings comprising the anisotropic material and the at least one dichroic dye.

58. The ophthalmic element of claim 39 wherein the at least one dichroic dye has an absorption ratio of at least 3.

59. The ophthalmic element of claim 39 wherein the at least one dichroic dye has an absorption ratio of at least 5.

60. The ophthalmic element of claim 39 wherein the at least one dichroic dye has an absorption ratio of at least 7.

61. The ophthalmic element of claim 39 wherein the at least one dichroic dye has an absorption ratio of at least 10.

62. The ophthalmic element of claim 39 wherein the at least one dichroic dye is selected from the group consisting of azomethines, indigoids, thioindigoids, merocyanines, indanes, quinophthalone dyes, perylenes, phthalimides, triphenodioxazines, indoloquinoxalines, imidazotriazines, tetrazines, azo and (poly) azo dyes, benzoquinones, naphthoquinones, anthraquinones and (poly) anthraquinones, anthrapyrimidinones, iodine and iodates.

63. The ophthalmic element of claim 39 wherein the at least one dichroic dye is a polymerizable dichroic dye.

64. The ophthalmic element of claim 39 wherein the liquid crystalline polymer has at least one functional group selected from the group consisting of acrylate, methacrylate, allyl ether, alkyne, amino, anhydride, epoxy, hydroxyl, isocyanate, blocked isocyanate, siloxane, thiocyanate, thiol, urea, vinyl, and vinyl ether.

65. The ophthalmic element of claim 39 wherein the at least one at least partial coating comprising a liquid crystal polymer and at least one dichroic dye further comprises at least one photochromic material.

66. The ophthalmic element of claim 65 wherein the at least one photochromic material is selected from the group consisting of pyrans, oxazines, fulgides and fulgimides, and metal dithizonates.

67. The ophthalmic element of claim 39 wherein the at least one at least partial coating comprising a liquid crystal polymer and at least one dichroic dye further comprises at least one additive selected from the group consisting of dyes, alignment promoters, kinetic enhancing additives, photoinitiators, solvents, light stabilizers, heat stabilizers, mold release agents, rheology control agents, leveling agents, free radical scavengers, and adhesion promoters.

68. The ophthalmic element of claim 39 further comprising at least one at least partial primer layer between at least a portion of the at least one at least partial coating comprising the alignment medium and at least a portion of the at least one outer surface of the ophthalmic element.

69. The ophthalmic element of claim 39 further comprising at least one additional at least partial coating on at least a portion of the ophthalmic element, the coating selected from the group consisting of photochromic coatings, antireflective coatings, transitional coatings, undercoats, and protective coatings.

70. The ophthalmic element of claim 1 further comprising at least one at least partial coating comprising at least one alignment transfer material between at least a portion of the at least partial coating adapted to polarize at least transmitted radiation and at least a portion of the at least partial coating comprising a photo-orientable polymer network.

71. An optical device comprising at least one optical element, the optical element comprising: an at least partial coating comprising a photo-orientatable polymeric network on at least a portion of at least one outer surface of the at least one optical element; and an at least partial coating comprising a liquid crystal polymer and at least one dichroic dye on at least a portion of the at least one at least partial coating comprising a photo-orientatable polymer network.

72. The optical device of claim 71, wherein the at least one optical element further comprises at least one at least partial coating comprising at least one alignment transfer material between at least a portion of the at least partial coating comprising a liquid crystal polymer and the at least one dichroic dye and at least a portion of the at least partial coating comprising a photo-orientatable polymer network.

73. The optical device of claim 71, wherein the optical device is an ophthalmic device selected from the group consisting of ophthalmic lenses, clip-on ophthalmic lenses, and contact lenses.

74. A method of manufacturing an ophthalmic element comprising:

providing at least one orientation mechanism comprising an at least partial coating comprising a photo-orientable polymeric network on at least a portion of at least one outer surface of an ophthalmic element;

applying an at least partial coating comprising a liquid crystalline polymer and at least one dichroic dye onto at least a portion of at least one alignment facility; and

at least a portion of the at least partial coating comprising the liquid crystal polymer and the at least one dichroic dye is at least partially aligned.

75. The method of claim 74 wherein providing the at least one orientation mechanism on the at least a portion of the at least one outer surface of the ophthalmic element comprises applying an at least partial coating comprising a photo-orientable polymer network to the at least a portion of the at least one outer surface of the ophthalmic element and at least partially ordering the at least a portion of the photo-orientable polymer network.

76. The method of claim 75 wherein the photo-orientable polymer network is a photo-orientable polymer network selected from azobenzene derivatives, cinnamic acid derivatives, coumarin derivatives, ferulic acid derivatives, and polyimides.

77. The method of claim 74 in which the process of at least partially ordering at least a portion of the photo-orientable polymer network comprises at least one of: exposing the at least a portion of the photo-orientable polymer network to plane-polarized ultraviolet radiation; and exposing the at least a portion of the photo-orientable polymer network to infrared radiation.

78. The method of claim 74, wherein providing the at least one orientation mechanism on the at least a portion of the at least one outer surface of the ophthalmic element further comprises at least partially immobilizing at least a portion of the photo-orientable polymer network by at least one of at least partially drying the at least a portion of the photo-orientable polymer network, at least partially cross-linking the at least a portion of the photo-orientable polymer network, and at least partially curing the at least a portion of the photo-orientable polymer network.

79. The method of claim 74 wherein applying the at least one dichroic dye to the at least a portion of the at least one alignment facility and at least partially aligning the at least a portion of the at least one dichroic dye are performed substantially simultaneously.

80. The method of claim 74 wherein applying the at least one dichroic dye to the at least a portion of the at least one alignment facility is performed prior to at least partially aligning the at least a portion of the at least one dichroic dye.

81. The method of claim 74 wherein applying the at least one dichroic dye onto the at least a portion of the at least one alignment facility is performed after at least partially aligning the at least a portion of the at least one dichroic dye.

82. The method of claim 74 wherein the method of applying the at least one dichroic dye to the at least a portion of the at least one alignment facility comprising a photo-orientable polymer network comprises at least one of: spin coating, spray and spin coating, curtain coating, flow coating, dip coating, injection molding, casting, roll coating, wire coating, over coating, and impregnation.

83. The method of claim 74 further comprising applying at least a portion of a primer layer to at least a portion of the at least one outer surface of the ophthalmic element prior to providing the at least one orientation mechanism to the at least a portion of the at least one outer surface of the ophthalmic element.

84. The method of claim 74, further comprising applying at least one additional at least partial coating selected from the group consisting of photochromic coatings, antireflective coatings, transitional coatings, undercoats, and protective coatings to at least a portion of the at least one ophthalmic element.

85. A method of manufacturing an ophthalmic element comprising:

applying an at least partial coating comprising a photo-orientable polymeric network to at least a portion of at least one outer surface of an ophthalmic element;

at least partially ordering at least a portion of the photo-orientable polymer network;

applying the at least partial coating comprising a liquid crystal polymer and at least one dichroic dye onto at least a portion of the at least partial coating comprising an at least partially ordered photo-orientable polymer network; and

at least a portion of the at least one dichroic dye is at least partially aligned.

86. The method of claim 85, wherein the process of at least partially ordering at least a portion of the photo-orientable polymer network comprises at least one of: exposing the at least a portion of the photo-orientable polymer network to plane-polarized ultraviolet radiation; and exposing the at least a portion of the photo-orientable polymer network to infrared radiation.

87. The method of claim 85, further comprising at least partially immobilizing at least a portion of the at least partial coating comprising a photo-orientable polymer network prior to at least partially ordering at least a portion of the photo-orientable polymer network.

88. The method of claim 85, further comprising at least partially immobilizing at least a portion of the at least partial coating comprising a photo-orientable polymer network while at least partially ordering at least a portion of the photo-orientable polymer network.

89. The method of claim 85, further comprising at least partially immobilizing at least a portion of the at least partial coating comprising the photo-orientatable polymeric network after at least partially ordering at least a portion of the photo-orientatable polymeric network.

90. The method of claim 85 wherein at least partially aligning at least a portion of the at least one dichroic dye comprises at least partially aligning at least a portion of the liquid crystal polymer such that the at least a portion of the at least one dichroic dye is at least partially aligned with the at least partially aligned liquid crystal polymer.

91. The method of claim 85 further comprising at least partially immobilizing at least a portion of the at least partial coating comprising the liquid crystal polymer and the at least one partially aligned dichroic dye.

92. The method of claim 91, wherein at least partially fixing at least a portion of the at least partial coating comprising the liquid crystal polymer and the at least one partially aligned dichroic dye comprises at least partially curing the at least a portion of the at least partial coating by exposing the at least a portion of the at least partial coating to ultraviolet radiation in a substantially inert atmosphere.

93. The method of claim 85 further comprising applying an at least partial coating comprising an alignment transfer material to at least a portion of the at least partial coating comprising an at least partially ordered photo-orientable polymer network and at least partially aligning at least a portion of the alignment transfer material prior to applying the at least partial coating comprising a liquid crystal polymer and at least one dichroic dye.

94. A method of manufacturing an ophthalmic lens comprising:

applying an at least partial coating comprising a photo-orientable polymer network to at least a portion of at least one outer surface of the lens;

at least partially ordering at least a portion of the photo-orientable polymer network with plane-polarized ultraviolet radiation;

applying an at least partial coating comprising a liquid crystal material and at least one dichroic dye onto at least a portion of the at least partial coating comprising a photo-orientable polymer network;

at least partially aligning at least a portion of the at least partial coating comprising the liquid crystal material and the at least one dichroic dye; and

at least a portion of the coating comprising the liquid crystal material and the at least one dichroic dye is at least partially immobilized.

95. The method of claim 94, further comprising at least partially immobilizing at least a portion of the photo-orientable polymer network prior to at least partially ordering the at least a portion of the photo-orientable polymer network.

96. The method of claim 94, further comprising at least partially immobilizing at least a portion of the photo-orientable polymer network while at least partially ordering the at least a portion of the photo-orientable polymer network.

97. The method of claim 94, further comprising at least partially immobilizing at least a portion of the photo-orientable polymer network after at least partially ordering the at least a portion of the photo-orientable polymer network.

98. The method of claim 94, further comprising applying at least one at least partial coating selected from a protective coating and an anti-reflective coating to at least a portion of the at least partial coating comprising the liquid crystal material and the at least one dichroic dye after at least partially fixing the at least a portion of the coating comprising the liquid crystal material and the at least one dichroic dye.

99. The method of claim 98 wherein the at least partial coating comprising a photo-orientable polymer network is applied to at least a portion of a first surface of the lens and at least a partial anti-reflective coating is applied to at least a portion of a second surface of the lens, wherein the second surface is opposite the first surface.