Optical elements comprising compatiblizing coatings and methods of making the same

“COMPOSITION OF COMPATIBILIZER COATING, OPTICAL ELEMENT AND METHOD FOR MANUFACTURING AN OPTICAL ELEMENT

Background In general, the present invention relates to optical elements, such as ophthalmic elements, comprising a substrate, a compatibilizer coating and a functional organic coating on at least a portion of a substrate surface. The present invention also relates to compatibilizer coating compositions which may be used to form compatibilizer coatings on the surface of an optical element, and to methods for producing optical elements comprising compatibilizer coatings.

Optical elements such as, for example, ophthalmic elements, may be adapted for use in certain applications by placing one or more functional organic coatings on the element. For example, an optical element, such as an ophthalmic element, can be adapted for use in photochromic eye applications by placing a photochromic coating on the surface of the element. Ophthalmic elements with photochromic coatings, such as photochromic lenses for eye use applications, can provide the wearer with an appropriate level of transmitted radiation depending on environmental conditions.

Further, it is possible to adapt an optical element, such as an ophthalmic element, for use in polarization applications by forming a polarizing coating comprising an aligned liquid crystal material and a dichroic dye on the surface of the element. Ophthalmic elements with polarizing coatings such as lenses

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2/95 polarizing devices for eye use applications can provide the user with reduced brightness of reflected light by linearly polarizing some percentage of the radiation transmitted through the element.

It is also possible to adapt an optical element to exhibit photochromic and dichroic properties under certain conditions by forming a coating comprising an aligned liquid crystal material and a photochromic / dichroic dye on the surface of the element. Optical elements with photochromic / dichroic coatings may change from a first state, for example a clear non-polarized state, to a second state, for example a colored polarized state, in response to actinic radiation, and may return to the first state in the art. absence of actinic radiation and in response to thermal energy. For example, photochromic / dichroic coated ophthalmic elements, such as eyepiece lenses, can transition between a clear unpolarized state and a colored polarized state to provide the wearer with both an appropriate level of transmitted radiation and reduced light brightness. reflected depending on environmental conditions.

However, if the interaction between the functional organic coating and the surface to which it is applied is insufficient, the functional organic coating (or portions thereof) may not adhere properly to the surface. For example, if a liquid crystal coating (such as those discussed above) and the substrate surface lack sufficient compatibility, the coating may not adhere properly to the surface and may be

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3/95 easily removed from the surface, eg exfoliating. In the context of lenses for ophthalmic applications, exfoliating the lens surface polarizing coating will degrade overall lens performance by allowing unpolarized light to pass through those portions of the lens that have had the coating removed.

It is possible to apply a compatibilizer coating on the surface of a substrate to improve compatibility between the substrate and a photochromic coating applied on it. However, compatibilizer coating that is used on a coating / surface combination cannot provide adequate compatibility between the same surface and a different coating. Thus, different coating / surface combinations may require the use of different compatibilizing coatings.

However, the need to use different compatibilizing coatings over different coating / surface combinations can lead, among other things, to manufacturing inefficiencies and increased costs. Accordingly, it would be advantageous to develop compatibilizing coatings that could be used to enhance the compatibility of a variety of surface / coating combinations to provide satisfactory compatibility between coatings and surfaces.

Brief Summary of the Disclosure Various non-limiting embodiments of the present invention provide optical elements and methods for forming optical elements. For example, the present invention provides an optical element comprising a substrate, a compatibilizer coating comprising a dendritic polymer on

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At least a portion of a substrate surface, and a functional organic coating other than an abrasion resistant coating, in contact with at least a portion of the opposite compatibilizing coating of the substrate.

The present invention also provides a method for manufacturing an optical element. The method comprises forming a compatibilizer coating comprising a dendritic polymer on at least a portion of a surface of a substrate and forming a functional organic coating other than an abrasion resistant coating on at least a portion of the compatibilizing coating such that the functional organic coating be in contact with at least a portion of the compatibilizer coating in front of the substrate surface.

In addition, the present invention provides a compatibilizing coating composition. The compatibilizing coating composition comprises a dendritic polymer including a terminal functional group, an epoxy containing material comprising at least two reactive functional groups, at least one of which is an epoxy group, an aminoplastic resin comprising at least two reactive groups, a coupling, at least partial hydrolysate thereof, or a mixture thereof, and an initiator, wherein the compatibilizing coating composition is free of photochromic materials.

[011] The present invention also relates to an optical element comprising a substrate, a compatibilizer coating on at least a portion of a substrate surface and a functional organic coating on at least a portion of the compatibilizer coating.

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5/95

The compatibilizer coating is derived from a compatibilizer coating composition described herein.

Also provided are methods for an ophthalmic element comprising creating a compatibilizer coating on at least a portion of a surface of a substrate and forming a functional organic coating on at least a portion of the compatibilizer coating. The compatibilizer coating is derived from a compatibilizer coating composition described herein.

[013] The present invention provides an ophthalmic element comprising an ophthalmic substrate, a compatibilizing coating that is essentially free of photochromic materials on at least a portion of an ophthalmic substrate surface, and a functional organic coating other than an abrasion resistant coating, in contact with at least a portion of the opposite compatibilizer coating of the ophthalmic substrate. The compatibilizer coating is formed of a compatibilizer coating composition comprising an isocyanate-containing material including at least two reactive functional groups, a (meth) acrylate-containing material including at least two reactive functional groups, at least one of which is a (meth) group. acrylate, an aminoplastic resin comprising at least two reactive groups, a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof, and at least one initiator and a catalyst.

[014] Also disclosed are methods for making ophthalmic elements. The methods comprise forming a

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Compatibilizer coating which is essentially free of photochromic materials on at least a portion of a surface of an ophthalmic substrate, at least partially fixing a portion of the compatibilizer coating by exposing at least a portion to at least one of UV radiation, electron beam, and thermal radiation, form a functional organic coating other than a hard coating over at least a portion of the compatibilizing coating. The compatibilizer coating is derived from a compatibilizer coating composition described herein.

Brief Description of the Various Views of the Drawings Aspects of the present invention will be better understood when read in conjunction with the figures. Figures 1-3 are schematic cross-sectional drawings of optical elements according to the present invention.

DESCRIPTION OF VARIOUS NON-LIMITATIVE EMBODIMENTS It is understood that while the present invention is described herein with respect to certain embodiments and examples, the present invention is not limited by the embodiments and particular examples, but is intended to cover modifications that are within the scope within the spirit and scope of the invention as defined by the appended claims. Furthermore, it is understood that the present description illustrates relevant aspects of the invention for a clear understanding of the invention. Accordingly, certain aspects of the invention that would be obvious to those of ordinary skill in the art and thus would not facilitate a better understanding of the invention were not presented in order to simplify the present disclosure.

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When used in this report and in the appended claims, articles one ”,“ one ”, and o include the plural of them, unless expressly and unambiguously limited to a referent. In addition, for the purposes of this report, unless otherwise indicated, all numbers expressing quantities, such as weight percentages and processing parameters, and other properties or parameters used in the report will be understood to be modified in all cases by the term about. of or about. Accordingly, unless otherwise indicated, it is to be understood that the numerical parameters set forth in the following report and the appended claims are approximations. At a minimum, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, numerical parameters should be read in light of the number of significant digits reported and the application of usual rounding techniques.

Furthermore, although the parameters and numerical ranges showing the broad scope of the invention are approximations as discussed above, the numerical values ​​presented in the Examples section are reported as precisely as possible. However, it should be understood that such numerical values ​​inherently contain certain errors resulting, for example, from equipment and / or measurement technique. In addition, when numeric ranges are reported here, these ranges include their extreme points.

In addition, it should be understood that where relationships of possible substituent groups are provided using titles and

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8/95 subtitles such as, for example: (a), (b) ...; (1), (2) ...; (I), (II) ..., etc., these titles and subtitles are provided for readability only and are not intended to limit the choice of substituent groups.

As discussed above, the present invention relates to optical elements, and in particular optical elements comprising a substrate, a compatibilizer coating on at least a portion of a substrate surface and a functional organic coating other than a coating. abrasion resistant, in contact with at least a portion of the compatibilizer coating in front of the substrate. That is, the compatibilizer coating is between the substrate and the functional organic coating.

[021] When used herein, the term "optical" means to relate to or be associated with light and / or vision. Non-limiting examples of optical elements include ophthalmic elements, display elements, windows, mirrors, and active and passive liquid crystal cells. When used herein, "ophthalmic" means to relate to or be associated with eye and / or vision. Non-limiting examples of ophthalmic elements include corrective and non-corrective lenses, including single vision or multiple vision lenses, which may be segmented or non-segmented multiple vision lenses (such as, but not limited to, bifocal lenses, trifocal lenses and progressive lenses), as well as other elements used to correct, protect or improve (cosmetically or otherwise) vision, including without limitation contact lenses, intraocular lenses and protective lenses or visors.

[022] When used herein, the term “display” means the

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9/95 machine-visible or machine-readable representation in words, numbers, symbols, plans or drawings. Examples of display elements include displays, monitors, and security elements such as security signals. When used herein, the term "window" means an aperture adapted to permit radiation transmission therethrough. Non-limiting examples of windows include aircraft and automotive transparencies, filters, shutters, and optical switches. When used herein, the term "mirror" means a surface that specularly reflects a large fraction of incident light. As used herein, the term "liquid crystal cell" refers to a structure containing a liquid crystal material that is capable of ordering. In a typical liquid crystal cell, a liquid crystal material is contained between two substrates which are sealed together forming a chamber. Active liquid crystal cells are cells in which a liquid crystal material is capable of exchanging between ordered and disordered states or between two ordered states by the application of an external force, such as an electric or magnetic field. Passive liquid crystal cells are cells in which a liquid crystal material maintains an orderly state. A non-limiting example of a liquid crystal cell element is a liquid crystal display.

Substrates which are suitable for use in conjunction with various embodiments of the present invention disclosed herein include, but are not limited to substrates formed of organic materials, inorganic materials or combinations thereof, for example composite materials. In addition, the substrates disclosed herein may have any shape

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Suitable, including, but not limited to, flat, cylindrical, spherical, flat-concave (i.e. flat on one side and concave on the other) and flat-convex (i.e. flat on one side and convex on the other). For example, the substrate may be a flat-convex or flat-concave ophthalmic lens having a flat surface and a curved (convex or concave) surface that has a curvature corresponding to any of several basic ophthalmic lens curves. Specific non-limiting examples of substrate forming materials are described in more detail below.

Non-limiting examples of organic materials that may be used to form the substrates disclosed herein include polymeric materials, for example, homopolymers and copolymers prepared from monomers and monomer mixtures disclosed in U.S. Pat.² No. 5,962,617, from column 2, line 9 to column 7 to line 46, and in US patent no.²No. 5,658,501 to column 15, row 28 to column 16 to row 17, the disclosures of which are specifically incorporated herein by reference. Such organic materials may be thermoplastic or thermoset polymeric materials, may be optically transparent or clear, and may have any required refractive index. For example, although not limitless herein, the refractive index of optically clear or optically clear organic polymeric materials from which ophthalmic lenses can be formed typically ranges from 1.48 to 1.74.

Specific non-limiting examples of monomers and polymers that may be used to form the optical element substrates disclosed herein include: polyol (allyl carbonate) monomers, for example diglycol carbonates

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11/95 allyl such as diethylene glycol bis (allyl carbonate), whose monomer is sold under the tradename CR-39 ™ by PPG Industries, Inc., Pittsburgh, Pennsylvania; polyurea / polyurethane polymers (polyurea / urethane), which are prepared, for example, by the reaction of a polyurethane prepolymer and a diamine curing agent, a composition for such polymer being sold under the tradename TRIVEX ™ by PPG Industries Ohio, Inc., Cleveland, Ohio; acrylic functional monomers such as, but not limited to, polyol (meth) acryloyl terminated carbonate monomer, diethylene glycol dimethacrylate monomers, ethoxylated phenol methacrylate monomers, ethoxylated propyl trimethylol triacrylate monomers, poly (ethylene glycol) monomers ) bis methacrylate, urethane acrylate monomers, and ethoxylated poly (bisphenol A dimethacrylate) monomers; diisopropenyl benzene monomers; poly (vinyl acetate); polyvinyl alcohol; polyvinyl chloride); polyvinylidene chloride; polyethylene; polypropylene; polyurethanes; polythiourethanes, including but not limited to materials such as optical resins designated as MR-6, MR-7, and MR8 from Mitsui Toatsu Chemicals, Inc .; thermoplastic polycarbonates, such as bisphenol A carbonate bonded resin and phosgene, such material being sold under the tradename LEXAN®; polyesters, such as material sold under the tradename MYLAR®; poly (ethylene terephthalate); (polyvinyl butyral); norbornene homopolymers and copolymers, such as those materials sold under the tradename ARTON® of JSR Corp., Saitama, Japan; polymethyl methacrylate, such as material sold under the tradename PLEXIGLAS®, and

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Polymers prepared by reacting polyfunctional isocyanates with polythiols or polypisulfide monomers, copolymerized or copolymerized / terpolymerized with polythiols, polyisocyanates, polyisothiocyanates, and optionally halogenated aromatic-containing vinyl monomers or ethylenically unsaturated monomers. Copolymers of such monomers and mixtures of the polymers and copolymers described with other polymers are also considered, for example, to form block copolymers or interpenetrating lattice products.

As mentioned above, the substrate may be an ophthalmic substrate. As used herein, the term "ophthalmic substrate" refers to lenses, partially molded lenses, and lens generators. Nonlimiting examples of organic materials from which ophthalmic substrates according to various nonlimiting embodiments disclosed herein may be formed include, but are not limited to, art-recognized polymers that are useful for forming optically clear or transparent blocks for applications. optical.

Other non-limiting examples of organic materials suitable for use in forming the substrates disclosed herein may include natural and synthetic organic materials, including without limitation: opaque or translucent polymeric materials, natural and synthetic textiles, and cellulosic materials. Non-limiting examples of inorganic materials suitable for use in substrate formation which may be used in conjunction with various non-limiting embodiments disclosed herein include glasses based on inorganic oxides, minerals, ceramics, and metals. For example, the

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The substrate may comprise an inorganic oxide based glass. Also, the substrate may comprise a ceramic, metallic or mineral substrate, which optionally may be polished to form a reflective surface. Where a reflective substrate surface is desired, a reflective layer or coating may be deposited or applied differently to a surface of an inorganic or organic substrate to make it reflective or to enhance its reflectivity.

[028] In addition, substrates may be colorless, colored and / or photochromic. As used herein, the term "colorless substrates" means substrates that are essentially free of colorant additions (such as, but not limited to, conventional dyes). As used herein, the term "actinic radiation" means electromagnetic radiation, such as, but not limited to, visible and ultraviolet radiation that is capable of causing a response. In addition, the term colored substrates means substrates having a coloring agent addition (such as, but not limited to conventional dyes), wherein the coloring agent has a visible radiation absorption spectrum that does not vary significantly in response to actinic radiation. As used herein, the term "photochromic substrates means substrates having the addition of photochromic material. In addition, substrates according to various non-limiting embodiments disclosed herein may be tinted as well as photochromic, that is, the substrates may comprise both a conventional dye coloring agent (which has an absorption spectrum for visible radiation that does not vary

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14/95 significantly in response to actinic radiation) as a photochromic material.

Furthermore, the substrates of the optical elements may have a protective coating such as, but not limited to, an abrasion resistant coating (also referred to as a "hard coating") on one or more of their surfaces. For example, commercially obtainable thermoplastic polycarbonate ophthalmic lens substrates are often sold with an abrasion-resistant coating applied to their surfaces because the surfaces of these substrates tend to be quickly scratched, chafed or scraped. An example of such a polycarbonate lens substrate is sold under the tradename GENTEX® (by Gentex Optics, Inc., Dudley, Massachusetts).

[030] When used herein, the term "protective coating" refers to a coating such as transitional coatings, abrasion resistant (or hard coatings) coatings, oxygen barrier coatings, and UV protection coatings. Non-limiting examples of abrasion-resistant coatings include, abrasion-resistant coatings comprising silanes, abrasion-resistant coatings comprising radiation-cured acrylate-based thin films, abrasion-resistant coatings based on inorganic materials such as silica, titania, and / or zirconia. , and combinations of these coatings. For example, the protective coating may comprise a first radiation-cured acrylate-based thin film coating and a second coating comprising a silane. Non-Limiting Product Examples

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15/95 commercial protective coatings include SILVUE® 124 and HI-GARD® coatings, obtainable from SDC Coatings, Inc. and PPG Industries, Inc., respectively.

Although not limiting herein, the inventors have observed that some functional organic coatings, for example, alignment coatings comprising photo-orientation materials (such as polyvinyl cinnamates) and coatings comprising liquid crystal materials (i.e. crystals) may have less than desired adhesion to organic substrate surfaces, and in particular to organic substrate surfaces having abrasion resistant coatings thereon. It has also been found that compatibilizing coatings of the present invention may be useful for improving and / or enhancing the adherence of functional coatings, such as, for example, alignment coatings and liquid crystal coatings on ophthalmic substrates, and in particular on substrates. ophthalmic having hard coated surfaces. Thus, the optical elements of the present invention may comprise a substrate including an abrasion resistant coating in contact with at least a portion of the surface thereof, and the compatibilizing coating may be in contact with at least a portion of the abrasion resistant coating on the surface. substrate surface to improve or enhance the adhesion between the abrasion-resistant coating on the substrate and the functional organic coating applied thereon.

As discussed above, the present invention relates to optical elements comprising a substrate, a compatibilizer coating on at least a portion of

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A substrate surface and a functional organic coating, other than an abrasion resistant coating, contact at least a portion of the compatibilizing coating in front of the substrate. As used herein, the term "coating" means a structure comprising one or more complete or partial layers derived from flowable compositions. and which may have uniform cross-sectional thickness and / or composition. As used herein, the term "compatibilizer coating" refers to a coating that improves compatibility between a surface and another coating applied thereon and / or facilitates the formation or application of other coatings on the surface. For example, a compatibilizer coating may be applied to a surface, for example, the surface of a substrate or the surface of another coating, to improve one or more of wetting, chemical compatibility, and adherence of another coating to the surface.

In addition, when used herein in the context of a coating being "on" a surface or object, the term "over" means that the subject coating is connected to the surface or object such that the subject coating is supported or carried by the surface. or object. In addition, when used herein, the term "connected to" means associated, directly or indirectly, with another material or structure. Thus, for example, a coating that is "on" a surface may be applied directly to the surface or it may be applied to one or more other coatings, at least one of which is applied directly to the surface.

[034] The compatibilizing coating that is on at least

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At least a portion of the substrate surface comprises a dendritic polymer. As used herein, the term "dendritic polymer" refers to a three-dimensional macromolecular material comprising a polyvalent core that is covalently bonded to a plurality of dendrites (or tree-like structures). The term "dendrite" means a tree-like structure having multiple branching layers (or "generations) emanating from a focal point, such as a multipurpose nucleus. Each branching layer or successor generation of a dendrite extends from the previous generation, and each branching layer or generation in the dendrite has one or more terminal reactive sites (or "terminal functional groups) from which the successor generation (if any) it may extend, or in the case of the last generation, which may provide a terminal functional group in the dendritic polymer. Dendritic polymers generally have a large number of terminal functional groups, are non-embarrassing, and have a low hydrodynamic volume. Further, when used herein, the term "dendritic polymers" includes both "dendrimers and" hyperbranched polymers. As used herein, the term "dendrimer" refers to a dendritic polymer having a symmetrical globular architecture that results from a controlled process giving an essentially monodisperse molecular weight distribution. As used herein, the term "hyperbranched polymer" refers to a dendritic polymer having a certain degree of asymmetry and a polydisperse molecular weight distribution.

Although not limiting herein, dendritic polymers may be formed, for example, by the stepwise formation of dendrites in a polyvalent core. For example,

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Although not limiting herein, a polyester-like dendritic polymer may be formed by reacting a polyol core with a first chain extender, such as, but not limited to, a carboxylic acid comprising two or more hydroxyl groups under typical conditions. of esterification to form a multi-dendrite core comprising a first branch (or generation) layer attached thereto. Each of the dendrites will comprise a number of terminal functional groups (e.g., in the present example, hydroxyl terminal groups) which lie on the periphery of the first branch layer. These terminal functional groups may be reacted with yet another first chain extender to produce a second branch layer at the core. The reproduction

<td>continuous</td><td>layers</td><td>in</td><td>reacting branch</td><td>the</td><td>groups</td>

<td>functional</td><td>terminals</td><td>at</td><td>periphery of the last</td><td colspan="2">layer of</td>

<td>branch</td><td>formed</td><td>with</td><td>first extenders</td><td>in</td><td>jail</td>

The additional dendrites will form and usually produce an increase in the number of terminal functional groups (e.g., in the present example, hydroxyl terminal groups) in the dendritic polymer. After the final branching layer is added to the dendritic polymer, any remaining terminal functional groups (e.g., in the present example any remaining terminal hydroxyl groups) on the final branching layer of the dendritic polymer may form the terminal functional groups of the dendritic polymer; they may further extend chain, for example by alkoxylation; may terminate, for example by reaction with a chain switch; or may be functionalized by reaction with another material to provide a different terminal functional group on the dendritic polymer. When used herein, the term “switch

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Chain strands include chain extenders devoid of appropriate functional groups to react with a subsequent chain extender group.

A non-limiting example of a stepwise method for forming a polyester-like dendritic polymer in a polyvalent core is described in US Pat.² 5,418,301 in column 6, lines 1 to 60. US patent no.² No. 5,418,301 also provides several examples of polyvalent cores suitable for use in forming polyester dendritic polymers in column 2, line 45 to column 3, line 68; several examples of chain extenders suitable for use in forming polyester dendritic polymers in column 4, lines 1 to 55, and several examples of chain switches suitable for use in forming polyester dendritic polymers in column 4, line 56 to column 5, line 68. The foregoing portions of US patent disclosure No. 5,418,301 herein are specifically incorporated by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein.

In addition, during the stepwise process described above, upon formation of any branching layer (i.e. the first branching layer, the second branching layer, etc.), an intermediate substituent (which may also be referred to as such as a "splitter chain extender" which is different from the first chain extender (for example, although not limiting herein, a different polyfunctional carboxylic acid or anhydride, containing reactive terminal functionality), may react with the hydroxyl end groups of the last formed branch layer. Thereafter, terminal functional groups of the substituent

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The intermediate may react with a second chain extender, which may differ from both the first chain extender and the separation chain extender, to provide a dendritic polymer having the desired structure and functionality. A non-limiting example of such a method is disclosed in U.S. Pat.² 6,569,956 in column 3, line 33 through column 4, line 42, the disclosure of which is specifically incorporated herein by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein.

Alternatively, dendritic polymers may be formed by pre-producing dendrites and subsequently binding the dendrites to a polyvalent nucleus. For example, a polyester-like dendritic polymer may be formed by condensing one or more carboxylic acid hydroxyls at normal esterification temperatures, allowing mono-, di-, tri- or polyfunctional acids to form ester bonds with mono-, di-, or polyfunctional or epoxide, or similar procedures resulting in ester bonds, ether bonds or other chemical bonds to form dendrites. The raw materials used to produce the dendrites may be chosen to provide each dendrite with a functional group at its focal point, and this focal point functional group may react with a polyvalent core to connect the dendrite to the nucleus, and a plurality of groups. functional endpoints on the periphery of the dendrite. A non-limiting example of such a method for forming a polyester-like dendritic polymer is disclosed in US Pat.² 5,663,247 in column 7, lines 23 to 51, and in column 8, lines 1 to 38, which is incorporated herein

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21/95 specifically by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein.

As indicated above, polyester-type dendritic polymers may be produced from ester or polyester units, optionally in combination with ether or polyester units. For example, the compatibilizer coating dendritic polymer may be a polyester-like dendritic polymer comprising a monomeric or polymeric core having at least one epoxide, hydroxyl, carboxyl or anhydride reactive group to which it may be added from 1 to 100, and more commonly from 1 to 100. 1 to 20, e.g. 2 to 8, branch layers. Branch layers may be formed from monomeric or polymeric branch chain extenders having at least three reactive groups, of which at least one is a hydroxyl group and at least one is a carboxyl, anhydride or epoxide group. As discussed above, polyester-like dendritic polymers may optionally also contain at least one splitting chain extender, which may be a compound having two reactive groups. For example, the separation chain extender may comprise a hydroxyl group, and a carboxyl group or anhydride group, or an internal ester, such as a lactone, of such a compound. In addition, as discussed above, the polyester-like dendritic polymer may also contain a terminal functional group such as, for example, hydroxyl, carboxyl or anhydride groups, and / or the dendritic polymer may optionally be partially or completely terminated by at least a monomeric or polymeric chain switch and / or functionalized with a

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22/95 different functional group.

As discussed above, US patent no.² No. 5,418,301 provides several examples of polyvalent cores suitable for use in forming polyester-like dendritic polymers in column 2, line 45 to column 3, line 68; several examples of extenders suitable for use in forming polyester dendritic polymers in column 4, lines 1 to 55, and several examples of chain switches suitable for use in forming polyester dendritic polymers in column 4, line 56 to column 5 , line 68. Additional non-limiting examples of polyvalent cores that may be used in the formation of polyester-like dendritic polymers are disclosed in US Pat.² No. 5,663,247 in column 3, line 22 to column 4, line 45. Additional non-limiting examples of chain extenders that may be used in forming polyester dendritic polymers are disclosed in US Patent No. 5,663,247 in column 4 , line 45 to column 5, line 7. Additional non-limiting examples of chain switches that can be used in forming polyester dendritic polymers are disclosed in US patent No. 5,663,247 in column 5, line 33 to column 6, line 60. Additional non-limiting examples of strand separation extenders that may be used in the formation of polyester dendritic polymers are disclosed in US Patent No. 5,663. 247 in column 5, lines 7 to 32. The above-mentioned portions of US patents Nos. 5,663,247 and 5,418,301 are specifically incorporated herein by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein.

[041] The dendritic coating polymer

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Compatible acrylate polymers can be a polyester-like dendritic polymer that is at least one of a hyperbranched polyester oligomer and a hyperbranched polyester oligomer. Non-limiting examples of commercially obtainable polyester dendritics that may be used may include polyester dendritic polymers provided by Perstop Specialty Chemicals, Perstop, Sweden under the tradename BOLTORN® and designated as dendritic macromolecules H20, H30, and H40, which comprise groups. hydroxy terminals. According to the manufacturer, these materials generally have a weight average molecular weight in the range of 1,000 to 4,000 atomic mass units and materials H20, H30 and H40 average 16, 32 and 64 hydroxy end groups, respectively. Another non-limiting example of a polyester-like dendritic polymer is a polyester acrylate oligomer obtainable from Sartomer Company of Exton, Pennsylvania, designated CN2302 and comprising acrylate end groups. Another non-limiting example of a useful dendritic polymer is a polyester / polyether blend dendritic polymer such as those obtainable from Perstop Specialty Chemicals, Perstop, Sweden under the tradename BOLTORN® and designated as P500.

Other nonlimiting examples of dendritic polymers that may be used in compatibilizing coatings may include mixed polyester / polyether dendritic polymers, epoxide / mine dendritic polymers, dendritic polymers based on starch / amine dendritic polymers polysulfide, polysiloxane dendritic polymers,

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Polyaminesulfide dendritic polymers, polyether dendritic polymers, polythio dendritic polymers, polyester dendritic polymers, polyester amide dendritic polymers, poly (ketone ether) dendritic polymers, and the like. In addition, as discussed above, such materials may be functionalized, for example, by reaction with acrylating agents to provide acrylic end groups or terminated using an appropriate chain switch.

Additionally, the dendritic polymer of the compatibilizer coating may be an amine dendritic starch polymer, which may also be referred to as a dense polyamidoamine star polymer. See, for example, US patent no.² 4,558,120. Dendritic amine starch polymers can be represented by the formula mentioned in column 7, lines 10-15 of US patent no.² 4,558,120. A description of dendritic amine starch polymers and their preparation can be found in column 2, line 39 to column 9, line 18 of US Patent No. 4,558,120, the disclosure of which is incorporated herein by reference to the extent that the disclosure incorporated does not conflict with the terms and definitions provided herein.

The compatibilizer coating dendritic polymer may be an epoxide / amine dendritic polymer. The epoxide / amine dendritic polymer may be prepared by repeating reaction sequence (a) from the conversion of portions that are suitable for generation of primary amino groups; (b) a ring-opening addition reaction of the primary amino moieties generated in (a) and the epoxide of the branching molecules having an epoxide moiety and having

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At least a portion that is suitable for generation of at least one primary amino group; and (c) a termination reaction characterized by the addition reaction of at least one substituted or unsubstituted acrylate in the amino functions of the dendritic polymer. The termination reaction can be performed using 2,3-epoxy propyl (meth) acrylate. Non-limiting examples of epoxide / amine dendritic polymers are described in U.S. Pat.² 5,760,142. The description found in column 1, line 65 to column 3, line 56 of US patent no.² 5,760,142 herein incorporated by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein.

The compatibilizing coating dendritic polymer may also be a carbosilane based dendritic polymer. Carbosilane-based dendritic polymers may comprise a carbosilane core having (a) a central silane core; (b) multiple dendrites comprising carbosilane branching layers extending externally from the central silane core, with the peripheral branching layer having silane end groups; and (c) polymeric addition chain arms emanating from core peripheral silane endpoints. Non-limiting examples of carbosilane dendritic polymers are described in US Patent No. 5,276,110, particularly in column 1, line 58 to column 5, line 5, the disclosure of which is incorporated herein by reference to the extent that the incorporated disclosure do not conflict with the terms and definitions provided herein.

Additionally, the dendritic polymer of the compatibilizer coating may be a dendritic polymer.

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26/95 which is prepared by polycondensation of cyclic anhydrides with diisopropanolamine. Non-limiting examples of such dendritic polymers are commercially available under the trademark HYBRANE ™ of DSM NV, and are prepared with acrylate and methacrylate ester functional groups. A specific non-limiting example of such a dendritic polymer is the commercially available HYBRANE ™ H1500 (unmodified) dendritic polymer.

The dendritic polymer of the compatibilizer coating may also be a polysiloxane dendritic polymer, which may be prepared, for example, and without limitation, by repeated silane hydroxylation and displacement of chloride at the silicon atom. The preparation of specific polysiloxane dendritic polymers is described by Uchida et al., J. Am. Chem. Soc., 1990, 112, 7077-7079, the disclosure of which is incorporated herein by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein. See also column 5, line 60 to column 6, line 13 of US Patent No. 6,889,735, the disclosure of which is incorporated herein by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein.

As discussed above, the terminal functional groups of the last formed branch layer of a dendritic polymer may optionally be functionalized, that is, it may react to provide the dendritic polymer with different terminal functional groups. For example, polyester-like dendritic polymers comprising hydroxyl end groups may be acrylated to provide an acrylate functional group on the periphery of the dendritic polymer. Per

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For example, while not limiting here, the acrylation of the polyester dendritic polymers, and the recovery and purification of the acrylic dendritic polymer can be performed using methods well known in the literature, such as the methods described in the article "Acrylic Ester". Polymers, found at Kirk-Othmer Encyclopedia of Chemical Technology (1980, volume 1, pages 386-413). Those skilled in the art will understand that acrylation is generally a direct reaction, such as esterification, of the molecule to be acrylated with, for example, acrylic acid, methacrylic acid, or crotonic acid (β-methacrylic acid), condensation with a (met) isocyanate acrylate, or a direct reaction with an acyl anhydride and / or halide corresponding to acrylic acid, methacrylic acid, or crotonic acid, usually in a molar ratio of hydroxyl groups to said acid, acyl anhydride and / or halide generally between 1: 0.1 and 1: 5, more usually between 1: 0.5 and 1: 1.5. Other non-limiting examples of acrylating agents include epoxide or anhydride functional acrylates and methacrylates, such as glycidyl methacrylate. Those skilled in the art will understand that typically the acrylating agent is used in a stoichiometric molar excess.

[049] The percentage of terminal functional groups in the dendritic polymer that can be functionalized, for example by acrylation to provide acrylate terminal groups, may vary. For example, according to various non-limiting embodiments disclosed herein, from 1 to 100% of the terminal functional groups of the dendritic polymer of the compatibilizer coating may be functionalized. The percentage of acrylate end groups in a dendritic polymer type

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Acrylic (i.e. functionalized) polyester may range from 1 to 100%, e.g. from 20 to 100%, or from 40 to 100%, such as from 45 to 100%, and may even vary between any combination. percentages, including the percentages mentioned. The dendritic polymers of the compatibilizer coating may be polyester-like dendritic polymers comprising hydroxyl end groups (such as those described above), or one or more of the hydroxyl end groups may be functionalized to provide the dendritic polymer with one or more terminal functional groups. many different. For example, as discussed above, the hydroxyl groups of a polyester-like dendritic polymer may be functionalized to provide one or more acrylate end groups.

The compatibilizer coating comprising the dendritic polymer may be formed of a compatibilizer coating composition comprising a dendritic polymer including a terminal functional group, wherein a terminal functional group is at least one of hydroxyl, acrylate, methacrylate, acid, isocyanate, thiol, amine, epoxy, silane, and glycidyl. Nonlimiting examples of dendritic polymer comprising a terminal functional group and methods for preparing it are discussed above.

In addition to the dendritic polymers discussed above, compatibilizer coating compositions from which compatibilizer coatings may be derived may further comprise: (a) an epoxy containing material comprising at least two reactive functional groups of which at least one is one. epoxy group; (b) an isocyanate-containing material comprising at least two groups

Petition 870180160193, of 07/12/2018, p. 34/109

Reactive functional of which at least one is an isocyanate group; (c) a (meth) acrylate-containing material comprising at least two reactive functional groups of which at least one is a (meth) acrylate group; and / or (d) an aminoplastic resin comprising at least two reactive functional groups. Additionally, compatibilizer coating compositions from which compatibilizer coatings may be derived may optionally comprise a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and at least one of an initiator and a catalyst. Non-limiting examples of epoxy containing materials which may be used include epoxy containing materials comprising at least one epoxy group and at least one of an acrylate group, an isocyanate group, a thiol group, an additional epoxy group, a silane group , and a glycidyl group.

The epoxy containing material of the compatibilizing coating composition may be an epoxy containing material comprising at least two epoxy groups. Non-limiting examples of epoxy containing materials comprising at least two epoxy groups may be represented by the following structural formulas I, II, or a mixture thereof:

R¹

A - (OCH2C CHj)

HI)

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30/95

Β — Ν - (- CH₂C-CH₂) \ \/ '2

II (II) where: (a) R¹ may represent a group such as hydrogen or C1-C3 alkyl; (b) m may represent an integer ranging from 2 to 4; (c) A may represent a group such as (I) C 2 -C 20 alkylene substituted C 2 -C 20 alkylene C 3 -C 20 cycloalkylene substituted C 3 -C 20 cycloalkylene a substituted or unsubstituted arylene group, such as phenylene or naphthylene, C1-C3 aryl alkylene, substituted C1-C3 aryl alkylene, each of which cycloalkylene alkylene substituents are independently C1-C3 carboxy, hydroxy or alkoxy or C1-alkyl -C3; (II) the group -C (= 0) R² (0 =) C-, where R²represents a group such as C 2 -C 20 arylene or alkylene; (III) the -R group³- (OR³-) n or - (0R³) n-, where R³ represents a group such as C 2 -C 4 alkylene and n represents an integer from 1 to 20; (IV) phthaloyl, isophthaloyl, terephthalyl, hydroxyl substituted phthaloyl, hydroxyl substituted isophthaloyl, hydroxyl substituted terephthaloyl; or (V) a group represented by the following structural formula:

<img file="BRPI0806374B1_D0001.tif" />

where each R⁴ and R⁵ independently represents a group, such as C1 -C4 alkyl, chlorine or bromine, each small independently represents an integer ranging from 0 to 4; each independently represents a group such as a group

Petition 870180160193, of 07/12/2018, p. 36/109

Divalent benzene or a divalent cyclohexane group, and where

<img file="BRPI0806374B1_D0002.tif" />

is a divalent benzene group, G will represent a group such as -0-, -S-, -S (0₂) -, -C (= 0) -, -CH₂-, -CH = CH-, -C (CH₃)₂-,

-C (CH₃) (W₆H₅)-, -(W₆H₄) -, or

<img file="BRPI0806374B1_D0003.tif" />

or when

V?

is a divalent cyclohexane group, G will represent a group such as -0-, -S-, -CH₂- or -C (CH₃)₂-; (d) B represents a group such as C1 -C4 alkyl₂-W₂O, C-substituted alkyl₂-W₂o, C cycloalkyl₃-W₂o, substituted C cycloalkyl₃W₂o, substituted or unsubstituted aryl groups, phenyl and naphthyl, C aryl alkyl₂-W₃aryl C alkyl₂-W₃wherein each of said alkyl and cycloalkyl substituents is independently carboxy, hydroxy, C1-4 alkoxy.₂-W₃, or C1 -C6 alkyl₃.

The epoxy containing material of the compatibilizing coating composition may also be represented by structural formula I, II or a mixture thereof wherein: R¹ is hydrogen; A represents a group such as

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32/95 (r \

<img file="BRPI0806374B1_D0004.tif" />

where R⁴, R⁵, E and G may represent groups such as those discussed above, and eq are defined above;

<td>alkylene</td><td>in</td><td>C2^_Cio,</td><td>phenylene; -R³- (OR³)_no-</td><td>or - (OR³)_no-,</td><td>in the</td>

<td>which R³</td><td>and</td><td>n are</td><td>the same as defined</td><td>previously</td><td>or</td>

<td>phthaloyl;</td><td>and B</td><td colspan="3">represents a group such as alkyl of</td><td>W₂-</td>

diglycidyl adduct

C10 -C10 phenyl, phenyl or phenyl alkyl.

Specific non-limiting examples of epoxy containing material comprising at least two epoxy groups which may be used in compatibilizing coating compositions may include glycerol polyglycidyl ether, diglycerol polyglycidyl ether, glycerol propoxylate triglycidyl ether, trimethylol propane triglycidyl ether, sorbitol polyglycidyl ether poly (ethylene glycol) diglycidyl ether, poly (propylene glycol) diglycidyl ether, neopentyl glycol diglycidyl ether, N, N-diglycidyl-4-glycidyloxy aniline, N, N-diglycidyl toluidine, 1,6-hexanediol diglycidyl ether, diglycidyl 1,2-cyclohexane carboxylate, diglycidyl bisphenol A (e.g., bisphenol ether diglycidyl ether A), a diglycidyl bisphenol A polymer, poly (bisphenol A-co-epichlorohydrin) capped glycidyl, a hydrogenated propylene oxide bisphenol A diglycidyl, diglycidyl tetrahydrophthalate acid ester, spiro glycol diglycidyl ether, hydroquinone diglycidyl ether , and mixtures thereof.

terephthalic,

1,2,3,6Petition 870180160193, of 07/12/2018, p. 38/109

Non-limiting examples of isocyanate-containing materials that may be used in the compatibilizing coating compositions of the present invention may include isocyanate-containing materials comprising at least one isocyanate group and at least one of a hydroxyl group, an acrylate group, an acid group, an additional isocyanate group, a thiol group, an amino group, an epoxy group, a silane group, a vinyl group, an allyl group, and a glycidyl group. As used herein, the term "isocyanate-containing material" includes materials containing at least one isocyanate group, which may be a blocked isocyanate group or an unblocked isocyanate group.

Non-limiting examples of isocyanate-containing materials comprising at least two reactive functional groups at least one of which is an isocyanate group which may be used may include: m-isopropenyl isocyanate, α-dimethyl benzyl; a reaction product of a monomer of acrylic functionality and isocyanic acid; an unsaturated monomer reaction product having a functional group chosen from amino, hydroxy, thio and a combination thereof with isocyanate-containing compounds having at least two isocyanate functional groups; and mixing any of the foregoing. Such isocyanate-containing materials and methods for preparing them are described in detail in US Pat.² 6,025,026 in column 6, line 37 to column 8, line 65, the disclosure of which is specifically incorporated herein by reference.

For example, the isocyanate-containing material may be selected from one or more polyisocyanates such as diisocyanates and triisocyanates including biurets and

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34/95 isocyanurates. Biurides of any suitable diisocyanate including 1,4-tetramethylene diisocyanate and 1,6-hexamethylene diisocyanate may be used as the isocyanate-containing material in the preparation of the reaction product of the present disclosure. Also, cycloaliphatic diisocyanate biurets such as isophorone diisocyanate and 4,4-methylene bis (cyclohexyl isocyanate) may be employed. Examples of suitable aralkyl diisocyanates from which biurides can be prepared are metaxylene diisocyanate and a, a, a ', a^,tetramethyl metaxylene. The diisocyanates themselves may be used as the isocyanate-containing material in the preparation of the reaction product of the present disclosure.

Trifunctional isocyanates may also be used as the isocyanate-containing material, for example isophorone diisocyanate trimers, nonane triisocyanate, triphenyl methane triisocyanate, 1,3,5benzene triisocyanate, 2,4,6-toluene triisocyanate , a trimethylol and tetramethyl xylene diisocyanate adduct sold under the tradename CYTHANE 3160 by CYTEC Industries, and DESMODUR N 3300, which is hexamethylene diisocyanate isocyanurate, obtainable from Bayer Corporation. In addition, polyisocyanates may include cyclic isocyanates, such as, for example, diisocyanate isocyanurates such as hexamethylene diisocyanate and isophorone diisocyanate.

The polyisocyanate which may be used as the isocyanate-containing material may also be one of those disclosed above with extended chain with one or more polyamines and / or polyols using appropriate materials and techniques known to those skilled in the art.

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The isocyanate-containing material of the compatibilizing coating composition may be an isocyanate-containing material comprising at least two isocyanate groups. Non-limiting examples of isocyanate-containing materials comprising at least two isocyanate groups include: toluene 2,4-diisocyanate, toluene 2,6-diisocyanate, diphenyl methane 4,4'-diisocyanate, diphenyl methane 2,4'-diisocyanate, diisocyanate paraphenylene, biphenyl diisocyanate, 3,3'-dimethyl-4,4'-diphenylene diisocyanate, tetramethylene 1,4-diisocyanate; Hexamethylene 1,6-diisocyanate, 2,2,4-trimethyl hexane 1,6-diisocyanate, lysine methyl ester diisocyanate; bis (ethyl isocyanate) fumarate; isophorone diisocyanate, obtainable under the tradename DESMODUR PL 340 from Bayer Materialscience, Pittsburgh, PA; ethylene diisocyanate, dodecane 1,12-diisocyanate, cyclobutane 1,3-diisocyanate; Cyclohexane 1,3 diisocyanate, cyclohexane 1,4 diisocyanate, methyl cyclohexyl diisocyanate; Hexahydro toluene 2,4-diisocyanate; Phenylene hexahydro 1,3 diisocyanate; Phenylene hexahydro 1,4-diisocyanate, perhydrodiphenyl methane 2,4'-diisocyanate, perhydrodiphenyl methane 4,4'-diisocyanate, naphthylene 1,5 diisocyanate; and mixtures thereof.

[063] When used herein, the terms (meth) acryl, (meth) acrylic or (meth) acrylate are intended to cover both the acryl / acrylic / acrylate forms and the methacryl / methacrylic / methacrylate forms of the indicated material. Non-limiting examples of (meth) acrylate-containing materials which may be used in compatibilizing coating compositions may include: acrylate monomers and

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Methacrylates, including polyfunctional acrylates and methacrylates, for example di, tri, tetra and pentafunctional acrylates and methacrylates.

The compatibilizer coating may be prepared using acrylic and methacrylic monomers or a mixture of acrylic and / or methacrylic monomers. The (meth) acrylic monomer mixture may include mono, di, tri, tetra and penta-acrylic functional monomers.

Non-limiting examples of (meth) acrylate monomers include polyfunctional (meth) acrylates, for example di, tri, tetra and pentafunctional (meth) acrylates. Non-limiting examples of (meth) acrylates which may be used in the compatibilizing coating compositions according to the present invention may be represented by the following general formula VI:

R⁸- (OC (= O) C (R⁹) = CH2) s (VI) ₈ wherein R represents a group such as an aliphatic or aromatic group containing from 2 to 20 carbon atoms and optionally from 1 to 20 alkylenoxy bonds; R⁹ represents a group such as hydrogen or an alkyl group containing from 1 to 4 carbon atoms and s represents a number ₈ integer ranging from 1 to 5. When s is greater than 1, R will be a linking group that joins the acrylic functional groups. Typically R⁹ is hydrogen or methyl, and s is an integer ranging from 1 to 3. More specifically, di (meth) acrylates (when s is 2) can be represented by the general formula VII:

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37/95

R¹⁰_r12 H₂c = c-c-o-R¹ oc — c = ch₂

OO (VII) where R¹⁰ and R¹² they may be the same or different and each represents groups such as hydrogen or alkyl groups containing from 1 to 4 carbon atoms, preferably hydrogen or methyl, and R¹¹ represents a hydrocarbon linking group, for example from 1 to 20 carbon atoms, for example an alkylene group, one or more oxyalkylene groups (or mixture of different oxyalkylene groups); or group of the following general formula VIII:

<img file="BRPI0806374B1_D0005.tif" />

where each R¹³ independently represents a group such as hydrogen or an alkyl group of 1 to 4 carbon atoms, for example methyl; each J independently represents a halogen atom, for example chlorine; each t independently represents an integer ranging from 0 to 4, px, from 0 to 1; euev are numbers ranging from 0 to 20, for example from 1 to 15, or from 2 to 10. The values ​​of u and u are average numbers and when calculated can be an integer or a fractional number.

(Meth) acrylates having an epoxy group may be represented by the following general formula IX:

Petition 870180160193, of 07/12/2018, p. 43/109

38/95

H₂CC-Ç- (R¹⁶0) w- (R¹⁷O) jt-CH2CÇ /^CH2

OO (IX) where R¹⁴ and R¹⁵ they may be the same or different and each independently represents a group such as hydrogen or alkyl groups of 1 to 4 carbon atoms, for example methyl; R¹⁶ and R¹⁷ they may be alkylene groups containing from 2 to 3 carbon atoms, for example ethylene and propylene, and wex are numbers from 0 to 20, for example from 0 or 1 to 25 or from 2 to 10. When one of wex is 0 another will be 1, the group R¹⁶ or R¹⁷ The remainder may be an aromatic group having the following Formula X:

<img file="BRPI0806374B1_D0006.tif" />

for example, a group derived from the 2,2-diphenylene propane radical, whose phenyl groups may be substituted with C1 to C alkyl groups₄ or with halogens, for example methyl and / or chlorine.

The compatibilizing coating compositions may further comprise an aminoplastic resin. Aminoplastic resins include amine or amide condensation products with aldehydes and have at least two reactive groups. Appropriate aminoplastics may be prepared by reaction of materials having NH groups such as urea, melamine, benzoguanamine, glycouryl, and cyclic urea with compounds.

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Carbonyls such as formaldehyde or higher aldehydes and ketones, and alcohols such as methanol, ethanol, butanol, propanol, and hexanol. Condensation products obtained from the reaction of alcohols and formaldehyde with melamine, urea or benzoguanamine are very common. However, condensation products of other amines and amines may also be used, for example, triazine aldehyde condensates, diazines, triazoles, guanadines, guanamines and alkyl and aryl substituted melamines. Aminoplastic resins are commercially obtainable from Cytec Industries, Inc., under the tradename CYMEL and RESIMENE. Non-limiting examples of such products include CYMEL® 345, 350 and / or 370 resins and RESIMENE® 717, 730 and / or 735 resins. Suitable reactive functional groups in the aminoplastic resin include any of the reactive groups disclosed herein, for example. for example hydroxyl, acrylate, methacrylate, acid, isocyanate, thiol, amine, epoxy, silane, and glycidyl.

As discussed above, compatibilizer coating compositions which may be used to form compatibilizer coatings according to the present invention may optionally comprise a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof. . When used herein, the phrase "at least partially hydrolyzed from a coupling agent" refers to a coupling agent that is at least partially or completely hydrolyzed. Non-limiting examples of coupling agents that may be used may include silanes, titanates and / or zirconates.

For example, the coupling agent may be a silane coupling agent having the structural formula V

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40/95 as follows:

(R¹⁸O) y-Si- (R¹⁹)_z (V) mercapto, represents the

wherein for each occurrence: R independently represents a group such as a hydrocarbon substituent having no more than 20 carbon atoms that is unsubstituted or substituted with epoxy, glycidoxy, amino, vinyl, benzine, styryl, (meth) acryloxy, ₁ halogen, ureido, or alkoxy; R is independently a group such as epoxy, glycidoxy, amino, vinyl, benzine, styryl, (meth) acryloxy, mercapto, halogen, ureido, alkoxy, or an aliphatic, cycloaliphatic or aromatic hydrocarbon substituent having no more than 20 atoms carbon which is unsubstituted or substituted with epoxy, glycidoxy, amino, vinyl, benzine, styryl, (meth) acryloxy, mercapto, halogen, ureido, or alkoxy, or two R groups may combine to form a cycloalkyl group of W₄-W₇ or heterocyclic group in which the heteroatom is at least one of oxygen or nitrogen; y represents an integer ranging from 1 to 4; ez represents an integer ranging from 0 to 3 as long as the sum y + z is 4.

Where the compatibilizing coating composition does not comprise a coupling agent, the dendritic polymer of the compatibilizing coating composition may optionally comprise, in addition to one or more hydroxyl end groups, (meth) acrylate, carboxylic acid, isocyanate, thiol. , amine, epoxy, or glycidyl, at least one silane terminal group. Additionally or alternatively, at least one of the functional groups of the epoxy containing material, the isocyanate containing material, the

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41/95 (meth) acrylate, or the aminoplastic resin material of the compatibilizing coating composition may be a silane group.

As indicated above, compatibilizer coating compositions which may be used to form compatibilizer coatings may optionally comprise at least one of an initiator and a catalyst. Further, when used herein, the term "catalyst" refers to a substance that increases the rate of a chemical reaction without itself undergoing any permanent chemical change.

Where the compatibilizer coating composition comprises at least one epoxy containing material (as discussed above), the compatibilizer coating composition will generally comprise at least one initiator, for example a thermal initiator and / or a photoinitiator which may facilitate fixing the epoxy containing material by generating an acid upon exposure to heat and / or actinic radiation. For example, and without limitation here, the acid generated by the initiator may be a Lewis acid or a Bronsted acid. In addition, if the compatibilizing coating composition comprises a silane coupling agent or at least a partial hydrolyzate thereof (as discussed above), the acid generated by the initiator may also facilitate condensation of the silane coupling agent by lowering the pH of the silane coupling agent. composition. When used herein with reference to coatings, coating compositions, or components thereof, the terms "fix", "fixation", etc. are intended to include processes such as, but not limited to, curing, polymerization, crosslinking, and drying.

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Although not limiting herein, it is considered that if, in addition to at least one epoxy-containing material, the compatibilizing coating composition comprises a dendritic polymer that includes (meth) acrylate end groups (for example, a polymer polyester-like dendritic polymer, examples of which are discussed above), the use of primers that are capable of generating both an acid and a free radical may facilitate the attachment (e.g. crosslinking) of the dendritic polymer, as well as facilitating the attachment of epoxy containing material. A combination of an initiator capable of generating an acid and a primer capable of generating a free radical may also be used. The primer may be a photoinitiator that adapts to generate an acid upon exposure to actinic radiation. Nonlimiting examples of suitable photoinitiators that may be adapted to generate an acid upon exposure to actinic radiation include onium salts and iodosyl salts, aromatic diazonium salts, metallocene salts, o-nitrobenzaldehyde, sulfonate esters or aromatic alcohols containing a carbonyl group at an alpha or beta position for the sulfonate ester group, N-sulfonyloxy derivatives of an aromatic amide or imide, aromatic oxime sulfonates, quinone diazides, and resins containing benzoin groups in the chain.

Specific non-limiting examples of onium salts which may be used in conjunction with various non-limiting embodiments disclosed herein include diaryl iodonium salts and triaryl sulfonium salts. Other suitable onium salts are described in US Patent No. 5,639,802, in column 8, line 59 to column 10, line 46, the disclosure of which

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43/95 is incorporated herein by reference. Non-limiting examples of triaryl sulfonium salts include triaryl sulfonium hexafluorophosphate salts and triaryl sulfonium hexafluoroantimonate salts. Non-limiting examples of diaryl iodonium salts include: 4,4'-dimethyl diphenyl iodonium tetrafluoroborate salts, phenyl-4octyloxyphenyl phenyl iodonium hexafluoroantimonate salts, dodecyl diphenyl iodonium hexafluoroantimonate salts, hexafluoro [4] (2-tetradecanol) oxy] phenyl] phenyl iodonium, and a mixture of any thereof.

In addition, where the compatibilizing coating composition comprises at least one isocyanate-containing material, the compatibilizing coating composition will generally comprise a catalyst, which may be a photocatalyst, which may facilitate the attachment of the isocyanate-containing material. Nonlimiting examples of suitable catalysts may include organic tin catalysts and organic bismuth catalysts. In addition, if in addition to the isocyanate-containing material, the compatibilizing coating composition comprises an epoxy-containing material, at least partially hydrolysed or silane coupling agent, and / or a dendritic polymer including acrylate end groups, the compatibilizer coating may also comprise an initiator which is adapted to generate an acid, and which optionally may also generate a free radical, to facilitate the fixation of these materials. Non-limiting examples of suitable primers are given above.

Where the compatibilizing coating composition

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Comprising a photoinitiator and / or a photo catalyst, optionally, a photosensitive dye may be added to the compatibilizer coating composition to adjust the actinic radiation wavelength for that need to activate the photoinitiator and / or photocatalyst. Non-limiting examples of photosensitive dyes may include acridine cationic dyes, benzoflavin cationic dyes, benzophenone basic dyes, perylene dyes, fluorine dyes, and mixtures and combinations thereof.

The compatibilizing coating compositions of the present invention may further comprise one or more additives which may aid in the processing and / or performance of the composition or a coating or article derived therefrom. Non-limiting examples of such additives may include, for example, polymerization inhibitors, solvents, light stabilizers (such as, but not limited to, ultraviolet light absorbers and light stabilizers, such as hindered amine light stabilizers (HALS). )), thermal stabilizers, release agents, rheology controlling agents, leveling agents (such as, but not limited to surfactants), free radical scavengers, and combinations and mixtures thereof. The compatibilizer coating comprising the dendritic polymer which is on at least a portion of the substrate surface may be derived from a compatibilizer coating composition comprising: (a) a dendritic polymer comprising a terminal functional group; (b) an epoxy containing material comprising at least two reactive functional groups, at least one of which is a

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45/95 epoxy; (c) an aminoplastic resin comprising at least two reactive functional groups; (d) a coupling agent, at least partial hydrolyzate thereof, or a mixture thereof; and optionally (e) an initiator. For example, the dendritic polymer may be a dendritic polymer comprising at least one acrylate terminal group; the epoxy containing material may be an epoxy containing material comprising at least two epoxy groups; the aminoplastic resin may be an aminoplastic resin comprising at least two reactive functional groups; the coupling agent, hydrolyzed by the partial thereof, or a mixture thereof, may be a silane coupling agent, a hydrolyzed by the partial thereof, or a mixture thereof; and the initiator may be a photoinitiator adapted to generate an acid upon exposure to actinic radiation. Suitable nonlimiting examples of dendritic polymers comprising at least one acrylate terminal group of epoxy containing materials comprising at least two epoxy groups of aminoplastic resins comprising at least two reactive functional groups of silane coupling agents and photoinitiators adapted to generate acid by exposure to actinic radiation are shown in detail above.

Additionally, the compatibilizer coating comprising the dendritic polymer which is on at least a portion of the substrate surface may be derived from a compatibilizer coating composition comprising: (a) a dendritic polymer comprising an acrylate terminal group; (b) an isocyanate-containing material comprising at least two isocyanate groups; (c) a resin

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46/95 same; and, aminoplastic catalyst comprising at least two reactive functional groups; (d) a silane coupling agent, a hydrolysate at least partially thereof, or a mixture of them optionally, (e) at least one of one and an initiator. For example, the dendritic polymer may be a dendritic polymer comprising at least one acrylate terminal group; the isocyanate-containing material may be an isocyanate-containing material comprising at least two isocyanate groups (which may be blocked or unblocked); the aminoplastic resin may be an aminoplastic resin comprising at least two reactive functional groups; the coupling agent, hydrolyzed by the partial thereof, or a mixture thereof, may be a silane coupling agent, a hydrolyzed by the partial thereof, or a mixture thereof; and the initiator may be a photoinitiator; and the catalyst may be at least one of an organic tin catalyst and an organic bismuth catalyst. Suitable non-limiting examples of dendritic polymers comprising at least one acrylate terminal group, isocyanate-containing materials comprising at least two isocyanate groups (which may be blocked or unblocked), aminoplastic resins comprising at least two reactive functional groups, silane coupling, photoinitiators, and catalysts that may be used in conjunction with these non-limiting embodiments are shown in detail above.

In addition, the compatibilizing coating comprising the dendritic polymer which is on at least a portion of the substrate surface may be derived from a

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Compatibilizing coating composition comprising: (a) a dendritic polymer comprising a (meth) acrylate terminal group; (b) a (meth) acrylate containing material comprising at least two (meth) acrylate groups; (c) an aminoplastic resin comprising at least two reactive functional groups; (d) a silane coupling agent, at least partial hydrolyzate thereof, or a mixture thereof; and optionally (e) an initiator, which may be, for example, a photoinitiator. Suitable non-limiting examples of dendritic polymers comprising a (meth) acrylate terminal group of (meth) acrylate-containing materials comprising at least two (meth) acrylate groups of aminoplastic resins comprising at least two reactive functional groups of coupling agents. silane, primers, and more particularly photoinitiators, which may be used in conjunction with these nonlimiting embodiments are shown in detail above.

The compatibilizer coating compositions disclosed herein may comprise, for example, at least 20 percent by weight of a total solids-based dendritic polymer, such as from 20 to 80 percent by weight of the solids-based compatibilizer coating composition or 30 to 70 weight percent of the total solids compatibilizer coating composition. Based on the total solids, the compatibilizing coating composition may comprise from 5 to 50 weight percent, such as from 10 to 40 weight percent or from 15 to 30 weight percent of an epoxy-containing material. isocyanate-containing material, (meth) acrylate-containing material, aminoplast resin, or a mixture of

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48/95 any of them.

Based on the total solids, the compatibilizer coating composition may comprise from 5 to 50 weight percent, such as from 10 to 40 weight percent or from 15 to 30 weight percent of a coupling agent of at least partially hydrolysed, or a mixture thereof.

The amount of initiators and / or catalysts present in the compatibilizing coating composition may be any amount sufficient to provide the coating with the desired attachment characteristics. To the extent the precise amount of initiators and / or catalysts employed in the compatibilizer coating compositions disclosed herein will depend on a number of factors, such as, but not limited to, curing conditions, desired curing time, etc., those skilled in the art. will be able to quickly determine the types and amounts of initiators and / or catalysts required to achieve the desired attachment characteristics. For example, initiators and / or catalysts may be present in compatibilizing coating compositions in an amount ranging from 0.1 to 10 weight percent based on total solids.

[086] The present invention also relates to compatibilizer coatings which are essentially free of photochromic materials and which are derived from a compatibilizer coating composition comprising an isocyanate containing material and a (meth) acrylate containing material. Optionally, such compatibilizing coatings may comprise a dendritic polymer

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49/95 or an aminoplastic resin. For example, the (meth) acrylate-containing material of the compatibilizer coating composition may be a dendritic polymer (such as those (meth) acrylate functionalized dendritic polymers described above), or the compatibilizing coating composition may comprise a dendritic polymer comprising a group. different from a (meth) acrylate group.

For example, the present invention provides an ophthalmic element comprising: (a) an ophthalmic substrate; (b) a compatibilizer coating that is essentially free of photochromic materials on at least a portion of a surface of the ophthalmic substrate, the compatibilizer coating being formed of a compatibilizer coating composition comprising: (I) an isocyanate-containing material comprising at least two groups isocyanate; (II) a (meth) acrylate-containing material comprising at least two reactive functional groups of which at least one is a (meth) acrylate group; (III) an aminoplastic resin comprising at least two reactive functional groups; (IV) a coupling agent, at least partial hydrolyzate thereof, or a mixture thereof; (V) at least one of an initiator and a catalyst; and (c) a functional organic coating, other than an abrasion resistant coating, in contact with at least a portion of the opposing compatibilizing coating of the ophthalmic substrate.

For example, according to these non-limiting embodiments, the isocyanate-containing material of the compatibilizing coating composition may be an isocyanate-containing material comprising at least two isocyanate groups.

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50/95 (which may be blocked or unblocked); the (meth) acrylate containing material may be a (meth) acrylate containing material comprising at least two (meth) acrylate groups; the aminoplastic resin may be an aminoplastic resin comprising at least two reactive functional groups; the at least partially hydrolyzed coupling agent or mixture thereof may be a silane coupling agent; the initiator may be a photoinitiator; and the catalyst may be at least one of an organic tin catalyst or an organic bismuth catalyst. Non-limiting examples of these as well as other isocyanate-containing materials, (meth) acrylate-containing materials, aminoplastic resins, coupling agents, initiators, and suitable catalysts which may be present in compatibilizing coating compositions according to these non-limiting embodiments are presented above. Although not limiting herein, the compatibilizing coating that is on at least a portion of a substrate surface may also be an alignment coating for a functional organic coating comprising a liquid crystal material (i.e. a crystal coating liquids) applied to it. As used herein, the term "alignment coating" refers to a coating comprising an at least partially ordered alignment means that may be used to impart an appropriate position or arrangement to another material or coating. When used herein, the term "sorting (and other forms thereof, for example sorting, sorting, etc.) means causing appropriate position or arrangement, such as aligning with another structure or material, by some other

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51/95 force or effect. Therefore, when used herein, "sorting" includes both contact methods for sorting a material, such as aligning the material with another structure or material, as well as non-contact methods for sorting a material, such as exposing the material to a force or external effect (eg polarized radiation, an electric or magnetic field, a shear force, etc.). Ordering can also include combinations of contact and non-contact methods. In addition, when used herein, the term "aligning" (and other forms thereof, eg alignment, alignment, etc.) means causing proper position or arrangement by interaction with another material, compound or structure. For example, although not limiting herein, liquid crystal coatings (i.e. coatings comprising a liquid crystal material) may be aligned at least partially by contacting the surface of an alignment coating. As used herein, the term "liquid crystal material" refers to a liquid crystal material or mesogen (such as, but not limited to monomer, oligomer, or polymer) that comprises liquid crystal mesogen.

More specifically, since liquid crystal materials contain mesogens having structures such as discs or rods, a rigid long axis, and strong dipoles, liquid crystal materials are generally capable of being ordered or aligned in order acquire a general direction. Therefore, a liquid crystal material may be ordered or aligned by interaction with an external force or other structure (such as an alignment coating) such that the long axes of the mesogen of the

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The material (or some portion of the material) acquires general direction which is generally parallel to a common axis. As used herein, the term "general direction" refers to the predominant orientation or arrangement of a material or structure. However, it should be understood that a material or structure may have a general direction even if there is some variation within the arrangement of the material or structure, provided that the material or structure, or some portion thereof, has at least one predominant arrangement. Non-limiting examples of liquid crystal materials that may be used to form liquid crystal coatings disclosed herein are set forth in detail below.

For example, where the compatibilizer coating also serves as an alignment coating, at least a portion of the surface of the compatibilizer coating may be scrubbed using, for example, a textured cloth, a velvet brush, or the like, or the surface. may be differently textured, for example by cauterization, to impart a desired order to the surface of the compatibilizer coating. In addition, where the compatibilizer coating also serves as an alignment coating, the compatibilizer coating may be fixed at least partially before rubbing or texturing the coating.

Compatibilizing coatings or compatibilizing coating compositions from which they may essentially be derived may be photochromic free coatings.

As used herein with respect to the various described herein, essentially free term (s) of photochromic materials means that

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The coating contains less than a photochromic amount of such materials or no photochromic material. As used herein, the term "photochromic" means to have an absorption spectrum for at least visible radiation that varies in response to at least actinic radiation. As used herein, the term "photochromic material" means any substance that is adapted to exhibit photochromic properties, that is, that is adapted to have an absorption spectrum for at least visible radiation that varies in response to at least actinic radiation. Additionally, as used herein, the term "photochromic amount" means an amount of photochromic material sufficient to impart visibly discernible photochromic properties to a coating or other article in which the photochromic material is incorporated. Therefore, compatibilizer coatings and / or compatibilizer coating compositions from which they may be derived that are essentially free of photochromic materials may comprise less than a photochromic amount of photochromic materials or may be free of photochromic materials, that is, they do not contain any materials. photochromic.

As discussed above, the present invention also provides optical elements comprising a substrate, such as, but not limited to those described above, a compatibilizing coating comprising a dendritic polymer on at least a portion of a substrate surface, which may be derived from the substrate. compatibilizing coating compositions, as discussed above, and a functional organic coating, other than an abrasion resistant coating, in contact with at least a portion of the coating

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54/95 compatibilizer in front of substrate. As used herein, the term "functional organic coating" refers to a coating that confers a desired property or characteristic to an article to which it connects and predominantly comprises, on a weight percent basis, an organic material (ie, an organic compound or hydrocarbon). The functional organic coatings of the present invention may be derived from compositions comprising predominantly an organic material, and which optionally may comprise inorganic materials or other carbon compounds, such as, for example, other additives. Other additives suitable for use in functional organic coating may include, for example, polymerization inhibitors, solvents, light stabilizers (such as, but not limited to, ultraviolet light absorbers and light stabilizers, such as hindered amine light stabilizers. (HALS)), thermal stabilizers, release agents, rheology controlling agents, leveling agents (such as, but not limited to surfactants), free radical scavengers, and combinations and mixtures thereof. The functional organic coating may be at least one of a photochromic coating, an alignment coating and a liquid crystal coating. Non-limiting examples of such functional organic coatings are shown in detail below.

[094] The functional organic coating that is in contact with at least a portion of the compatibilizing coating may be a photochromic coating. When used herein, the term "photochromic coating" refers to a coating comprising an amount of

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55/95 of at least one photochromic material. As discussed earlier, photochromic coatings can impart photochromic properties to optical elements, such as ophthalmic elements, to which they attach. In general, a photochromic coating has a first colorless state that corresponds to the color of the photochromic material contained in the photochromic coating in its ground state form, and a second colored state that corresponds to the color of the photochromic material contained in the photochromic coating in its ground state form. activated state (ie when exposed to actinic radiation). For example, if an optical element is an ophthalmic lens comprising the photochromic coating, the lens may turn from a colorless state to a colored state when the user is exposed to UV radiation, such as sunlight, and

<td>may</td><td>turn back</td><td>to colorless state</td><td>When</td><td>the user</td><td>not</td>

<td>is</td><td>exposed to</td><td>UV radiation.</td><td></td><td></td><td></td>

<td> [095]</td><td>Examples</td><td>non-limiting</td><td>in</td><td>compositions</td><td>in</td>

photochromic coatings which may be used to prepare photochromic coatings according to non-limiting embodiments disclosed herein are described below. Such photochromic coating compositions are known and may be prepared with components according to methods well known and understood from those skilled in the art. For example, photochromic polyurethane coating compositions which may be used to prepare photochromic coatings according to the present invention may be produced by catalyzed or uncatalyzed reaction of an organic polyol component and an isocyanate component in the presence of materials.

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56/95 photochromes. Materials and methods for preparing polyurethanes are described in Ullmann's Encyclopedia of Industrial Chemistry, Fifth Edition, 1992, Volume A21, pages 665 to 716. Non-limiting examples of methods and materials, for example, organic polyols, isocyanates and other components which may be used to prepare the polyurethane coating are disclosed in US patents. Nos. 4,889,413 (in column 2, line 42 to column 12, line 21) and 6,187,444 (in column 2, line 52 to column 12, line 15). Other isocyanate-containing coating compositions, such as monoisocyanate coating compositions which are disclosed in US Patent No. 6,916,537, in column 3, lines 1 to 12, comprise (in addition to a photochromic material) a reaction product (examples not shown). which are disclosed in US patent No. 6,916,537 in column 7, line 4-37) of a polyol comprising at least one carbonate group (non-limiting examples of which are set forth in US Patent No. 6,916,537 in column 7, line 38 to column 8 , line 49) and an isocyanate comprising at least one reactive isocyanate group and at least one polymerizable double bond (non-limiting examples of which are set forth in US patent No. 6,916,537 in column 8, row 50 to column 9, row 44), and optionally comprising an addition copolymerizable monomer (non-limiting examples of which are set forth in US Patent No. 6,916,537 in column 11, line 47 to column 20, line 43).

reference are incorporated herein.

[096] Non-limiting examples herein

The above disclosures specifically by composition of

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Photochromic aminoplastic resin coating that can be used to produce photochromic coatings according to the present invention can be prepared by combining a photochromic material with the functional component reaction product having at least two functional groups chosen from hydroxyl, carbamate, urea , or a mixture thereof and an aminoplastic resin, for example, cross-linking agent described in US Patent No.² 4,756,973, in column 4, row 59 to column

<td> 7,</td><td>line 3;</td><td>at</td><td>patent</td><td>US n²</td><td colspan="2"> 6.506.488,</td><td>at</td><td>column 2, row</td>

<td> 43</td><td colspan="4">to column 12, line 23; and</td><td>at</td><td>patent</td><td>U.</td><td>S. No. 6,432,544,</td>

<td>at</td><td>column</td><td> 2,</td><td>line</td><td>32 to</td><td>The</td><td>column</td><td> 14</td><td>, line 5. The</td>

<td colspan="2">disclosures</td><td></td><td>above</td><td colspan="2">mentioned</td><td>on here</td><td></td><td>incorporate</td>

specifically by reference.

Non-limiting examples of photochromic polysilane coating composition considered for use in the preparation of photochromic coatings may be prepared by hydrolyzing at least one silane monomer, such as glycidoxy propyl trimethoxysilane, vinyl trimethoxysilane, methacryloxy propyl trimethoxysilane, tetramethoxysilane, and / or methyl trimethoxysilane, and by combining the hydrolyzate with at least one photochromic material as described in US patent no.² No. 4,556,605, in column 4, line 6 to column 17, line 40, the disclosure of which is specifically incorporated herein by reference.

Non-limiting examples of photochromic poly (meth) acrylate coating composition considered for use in the preparation of photochromic coatings of the present invention may be prepared by combining materials

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58/95 photochromes with mono, di, or multifunctional (meth) acrylates as described in US Patent No. 6,025,026, in column 6, line 5 to column 11, line 28; US Patent No. 6,150,430 in column 2, line 51 to column 8, line 58; and in US Patent No. 6,602,603, in column 2, line 60 to column 7, line 50. The aforementioned disclosures are specifically incorporated herein by reference.

Non-limiting examples of the composition of photochromic polyanhydride coatings that may be used in the preparation of photochromic coatings of the present invention may be prepared by reacting a hydroxyl functional component and an anhydride functional polymeric component in a composition comprising at least one. organic photochromic material as described in US Patent No. 6,432,544, in column 2, line 32 to column 14, line 5. Non-limiting examples of hydroxyl functional components, anhydride functional components, and other components that may be used to prepare photochromic polyanhydride coatings are disclosed in US patents.

4,798,745 (in column 2, line 67 to column 8, line 65),

4,798,746 (in column 2, line 32 to column 11, line 45), and 5,239,012 (in column 3, line 17 to column 6, line 52). Other suitable polyanhydride coating compositions are described in US Patent No. 6,436,525, column 2, line 15 to column 11, line 60. The aforementioned disclosures are specifically incorporated herein by reference.

[100] Non-limiting examples of compositions of

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Considered photochromic coatings of poly (meth) acrylamides for use in the preparation of photochromic coatings may be prepared by combining a photochromic material with the free radical initiated reaction product of a polymerizable ethylenically unsaturated composition comprising N-alkoxymethyl (meth) acrylamide and at least one other ethylenically copolymerizable unsaturated monomer as described in US patent No. 6,060,001, column 2, line 6 to column 5, line 39. Methods for preparing Nalcoxymethyl (meth) acrylamide-functional polymers are described in US Patent No. 5,618,586, column 1, line 65 to column 7, line 2. The above disclosures herein are specifically incorporated by reference.

[101] Non-limiting examples of epoxy resin photochromic coating compositions that can be used to prepare photochromic coating of the present invention may be prepared by combining epoxy resin or polyepoxide photochromic compounds and curing agents as described in US Pat. s 4,756,973 (in column 3, line 50 to column 7, line 3), and 6,268,055 (in column 2, line 63 to column 17, line 3). The above-mentioned disclosures herein are specifically incorporated by reference.

[102] Other non-limiting examples of photochromic coating compositions that may be used to form photochromic coatings disclosed herein may include the poly (urea / urethane) compositions disclosed in US Patent No. 6,531,076, column 3, row 4 to column 10, line 49, the disclosure of which is specifically incorporated herein by

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60/95 reference.

[103] Non-limiting examples of suitable photochromic materials may include benzopyran, naphthopyran (for example those disclosed in column 1, line 64 to column 13, line 36 of US Patent No. 5,658,501), fused indene naphthopyran ( for example those disclosed in column 1, line 10 through column 12, line 57 of US patent No. 5,6456767); spiropyran (e.g., spiro (benzindoline) naphthopyran, spiro (indoline) benzopyran, spiro (indoline) naphthopyran, spiro (indoline) quinopyran, and spiro (indoline) pyran); oxazines; fused and fulgimized (e.g., those disclosed in column 20, line 5 through column 21, line 38 of US Patent No. 4,931,220); and metal dithiozonates (e.g., those disclosed in US Patent No. 3,361,706). The foregoing disclosures are specifically incorporated herein by reference.

[104] Additional non-limiting examples of photochromic compounds, polymerizable photochromic compounds, and complementary photochromic compounds that may be used in the present invention are described in US Pat.

<td> 5.166.345</td><td>(at</td><td>column</td><td> 3,</td><td>line</td><td> 36</td><td>up until</td><td>The</td><td>column</td><td> 14,</td><td>line 3);</td>

<td> 5.236.958</td><td>(at</td><td>column</td><td> 1,</td><td>line</td><td> 45</td><td>up until</td><td>The</td><td>column</td><td> 6,</td><td>line 65);</td>

<td> 5.252.742</td><td>(at</td><td>column</td><td> 1,</td><td>line</td><td> 45</td><td>up until</td><td>The</td><td>column</td><td> 6,</td><td>line 65);</td>

<td> 5.359.085</td><td>(at</td><td>column</td><td> 5,</td><td>line</td><td> 25</td><td>up until</td><td>The</td><td>column</td><td> 19,</td><td>line 55);</td>

<td> 5.821.287</td><td>(at</td><td>column</td><td> 3,</td><td>line</td><td> 5</td><td>up until</td><td>The</td><td>column</td><td> 11,</td><td>line 39);</td>

<td> 6.113.814</td><td>(at</td><td>column</td><td> 2,</td><td>line</td><td> 23</td><td>up until</td><td>The</td><td>column</td><td> 23,</td><td>line 28);</td>

<td> 6.153.126</td><td>(at</td><td>column</td><td> 2,</td><td>line</td><td> 18</td><td>up until</td><td>The</td><td>column</td><td> 8,</td><td>line 60);</td>

<td> 6.296.785</td><td>(at</td><td>column</td><td> 2</td><td colspan="2">, line</td><td colspan="2">47 to</td><td colspan="2">the column</td><td>31, line</td>

<td> 5);6.348.</td><td> 604</td><td colspan="2">(in column</td><td colspan="2">3, line</td><td> 26</td><td colspan="3">to the column</td><td>17, line</td>

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61/95

15); and 6,353,102 (in column 1, line 62 to column 11, line 64). The above-mentioned disclosures herein are specifically incorporated by reference.

[105] The functional organic coating that may be in contact with at least a portion of the compatibilizing coating may be an alignment coating.

As discussed above, the term alignment coating refers to a coating comprising an at least partially ordered alignment means that can be used to impart an appropriate position or arrangement to another material or coating. Non-limiting examples of alignment coatings include scrub-oriented alignment coatings, photo-oriented alignment coatings, and ordered liquid crystal alignment coatings. As used herein, the terms "scrub-oriented alignment coating" and "scrubbed alignment coating" refer to a coating that is at least partially ordered by rubbing or otherwise texturing at least a portion of the surface of the coating. As used herein, the term "photoriented alignment coating" refers to a coating that is ordered at least partially by exposure to polarized actinic radiation. Orderly liquid crystal alignment coatings may include liquid crystal coatings that have been ordered at least partially by exposure to an external force, such as, for example, a magnetic field, an electric field, or a shear force. Although not limiting here, alignment coatings may impart desirable orientation properties to

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62/95 optical elements to which they are connected.

[106] For example, the functional organic coating that is in contact with at least a portion of the compatibilizing coating may be an alignment coating, and more specifically, may be a scrub-oriented coating comprising a polyimide that is capable of being ordered by less partially rubbing. Also, the alignment coating may be a photo-oriented coating comprising a photo-orientation material that is capable of being oriented at least partially by exposure to polarized actinic radiation. As used herein, the term "photo-orientation material" means a material that is capable of being oriented at least partially by exposure to polarized actinic radiation. Nonlimiting examples of photo orientation materials include cinnamate derivatives, azobenzene derivatives, coumarin derivatives, and ferulic acid derivatives. For example, the photo-orientation material may be a cinnamate derivative, such as a polyvinyl cinnamate, a para-methoxycinnamic acid polyvinyl ester, or a para-methoxy acid poly (acrylic ester). methoxycinnamic. Other non-limiting examples of suitable photo-orientation materials and methods for forming photo-oriented alignment coatings are disclosed in US Pat.² 5,389,698, in column 1, line 35 to column 4, line 19, the disclosure of which is incorporated herein by reference; and in Kozenkov et al., "Photoanisotropic Effects in Poly (Vinyl-Cinnamate) Derivatives and Their Applications, Mol. Cryst. Liq. Cryst., Volume 409 (2004) at pages 215259 and 265, the disclosure of which is incorporated herein by reference. Additionally, the alignment liner may be a

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An ordered liquid crystal alignment coating comprising a liquid crystal material that has been ordered at least partially by exposure to an external force, such as, for example, a magnetic field, an electric field, or a shear force.

[107] As discussed earlier, alignment coatings can be used, for example, to align liquid crystal coatings that are in contact with them. Therefore, when the functional organic coating in contact with at least a portion of the compatibilizing coating is an alignment coating, the optical element may further comprise a liquid crystal coating comprising at least partially aligned liquid crystal material which is connected, and may still be in direct contact, with at least a portion of the alignment coating such that at least a portion of the liquid crystal material may align with at least a portion of the alignment coating. As discussed above, when used herein, the term "liquid crystal coating" refers to a coating comprising a liquid crystal material; and the term "liquid crystal material" refers to a liquid crystal mesogen, or a material (such as, but not limited to, a monomer, oligomer, or polymer) comprising liquid crystal mesogen. Non-limiting examples of liquid crystal materials that can be used to form liquid crystal coatings may include both lyotropic and thermotropic liquid crystal monomers, oligomers, and polymers. In a particular embodiment, the coating of liquid crystals

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64/95 may comprise a material of thermotropic liquid crystals.

[108] Specific nonlimiting examples of liquid crystal materials that may be used in conjunction with various nonlimiting embodiments disclosed herein include monofunctional as well as polyfunctional liquid crystal monomers. Additionally, the liquid crystal monomer may be a liquid crystal monomer.

<td>crosslinkable,</td><td>and can</td><td>to be</td><td>still one</td><td>i monomer</td><td>in</td><td>crystals</td>

<td>photo liquids ·</td><td colspan="2">-recriculable.</td><td colspan="2">When used herein, the</td><td colspan="2">term “photo-</td>

<td>crosslinkable</td><td>means</td><td>one</td><td>material,</td><td>such as</td><td>one</td><td>monomer,</td>

<td>oligomer, or</td><td>polymer</td><td>what</td><td>Can be</td><td>lattice</td><td>per</td><td>exhibition</td>

<td colspan="2">to actinic radiation.</td><td>Per</td><td>example,</td><td>monomers</td><td>in</td><td>crystals</td>

<td colspan="3">photo crosslinkable liquids</td><td>include</td><td>those</td><td colspan="2">monomers of</td>

liquid crystals that are crosslinkable upon exposure to ultraviolet radiation and / or visible radiation, with or without the use of polymerization initiators and / or catalysts. Non-limiting examples of crosslinkable liquid crystal monomers suitable for use in accordance with various non-limiting embodiments disclosed herein include liquid crystal monomers having functional groups chosen from acrylates, methacrylates, allyl groups, allyl ethers, alkynes, amino groups, anhydrides , epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl groups, vinyl ethers, and mixtures thereof. Non-limiting examples of photo-crosslinkable liquid crystal monomers suitable for use in the at least partial coatings of the alignment features of the present invention may include liquid crystal monomers having groups.

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65/95 functional compounds chosen from acrylates, methacrylates, alkynes, epoxides, thiols, and mixtures thereof.

[109] Liquid crystal oligomers and polymers suitable for use in the present invention may include both main chain liquid crystal oligomers and polymers as well as side chain liquid crystal oligomers and polymers. Typically, although not limiting herein, in main chain liquid crystal oligomers and polymers, the liquid crystal mesogens as disks or as rods are located primarily in the main chain of the oligomer or polymer. In addition, although not limiting herein, in side chain liquid crystal oligomers and polymers, the liquid crystal mesogens such as disks or rods are located primarily lateral to the oligomer or polymer. oligomers and polymers of liquid crystals may be crosslinkable, and may still be photoreticulable.

[110] Non-limiting examples of liquid crystal oligomers and polymers that are suitable for use in accordance with the present invention include, but are not limited to, main chain and side chain oligomers and polymers having functional groups chosen from acrylates, methacrylates, allyl groups, allyl ethers, alkynes, amino groups, anhydrides, epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, ureas, vinyl groups, vinyl ethers, and mixtures thereof. Non-limiting examples of photo-crosslinkable liquid crystal oligomers and polymers which are suitable for use in accordance with various embodiments herein in the chains. In addition,

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Disclosed disclosures include those oligomers and polymers having functional groups chosen from acrylates, methacrylates, alkynes, epoxides, thiols, and mixtures thereof. Further description of suitable non-limiting examples of liquid crystal monomers, oligomers and polymers can be found in US Patent No. 7,044,599 B2, column 8, line 4 to column 9, line 3, the disclosure of which is specifically incorporated herein. by reference.

[111] Liquid crystal mesogens which are suitable for use in the present invention may include thermotropic liquid crystal mesogens and liotropic liquid crystal mesogens. Nonlimiting examples of suitable thermotropic liquid crystal mesogens may include calamitic liquid crystal mesogen (or as a rod or rod), discotic crystal mesogen (or disk) and cholesteric liquid crystal mesogen.

[112] Alternatively, as discussed above, the compatibilizer coating itself may be a scrub-oriented alignment coating. Additionally, the functional organic coating that is in contact with the compatibilizing coating may be another alignment coating, for example, an ordered liquid crystal alignment coating or a photo-ordered alignment coating, or it may be a liquid crystal coating. comprising a liquid crystal material that may be aligned with the partially at least partially ordered compatibilizer coating. Although not limiting herein, aligned liquid crystal coatings may impart certain desirable optical properties, such as, for example,

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67/95 refractive index variation for the optical elements to which they are connected. In addition, as discussed in more detail below, the aligned liquid crystal coatings themselves may be used to align other materials or coatings to provide, for example and without limitation, polarizing coatings, photochromic and polarizing coatings, and photochromic / dichroic coatings. Non-limiting examples of liquid crystal materials that can be used to form aligned liquid crystal coatings are discussed in detail above.

[113] The aligned liquid crystal coating may comprise a material adapted to exhibit dichroism, and at least a portion of the material adapted to exhibit dichroism may be at least partially aligned with at least a portion of the at least partially aligned liquid crystal material. As used herein, the term "material adapted to exhibit dichroism means a material that is adapted to absorb one of two orthogonal plane polarized components of at least one radiation transmitted more strongly than the other. Nonlimiting examples of materials that are adapted to exhibit dichroism may include dichroic dyes and photochromic / dichroic dyes. As used herein, the term "dichroic dye means a dye having a generally constant absorption spectrum and which is adapted to absorb one of two orthogonal plane polarized components of at least one radiation transmitted more strongly than the other. When used herein, the term photochromic / dichroic dye means a dye that has an absorption spectrum for

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At least visible radiation varying in response to at least actinic radiation and absorbing one of two orthogonal plane polarized components of at least one radiation transmitted more strongly than the other in response to at least actinic radiation.

[114] Non-limiting examples of dichroic dyes that may be used may include those disclosed in U.S. Pat.² 7,044,599, in column 7, lines 18-56, which is specifically incorporated herein by reference.

[115] Non-limiting examples of photochromic / dichroic dyes that may be used may include those materials disclosed and described in U.S. Patent Publication Nos.²2005/0004361, from paragraph 27 to paragraph 158, and 2005/0012998 A1, from paragraph 89 to paragraph 251, which are specifically incorporated herein by reference.

[116] Although not limiting herein, the functional organic coating may be a polarizing coating comprising an aligned liquid crystal coating and an aligned dichroic dye. As used herein, the term "polarizing coating" refers to a coating that is adapted to confine the vibrations of the electromagnetic light wave vector in one direction or plane. Generally, although not required, polarizing coatings comprising conventional dichroic dyes may have constant (or "fixed") color or hue due to the presence of the dichroic dye. For example, the polarizing coating may have a brown or bluish color or hue. Non-limiting examples of suitable polarizing coatings comprising aligned liquid crystal materials and dichroic dyes are described in

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69/95 US Patent Application Publication No.² 2005/0151926, from paragraph 10 to paragraph 159, which is specifically incorporated herein by reference.

[117] The polarizing coating may further comprise a photochromic material. Where the photochromic material is present, the coating may be either a polarizing coating or a photochromic coating, i.e. one which exhibits both conventional polarizing as well as conventional photochromic properties. For example, the polarizing and photochromic coating may have a first colored polarized state when not exposed to actinic radiation due mainly to the dichroic dye hue, and a second colored polarized state when exposed to actinic radiation due to the combined effect of dichroic dye hue and the color of the photochromic material when exposed to actinic radiation. For example, if the optical element is an ophthalmic lens comprising the polarizing and photochromic coating, the lens may reversibly change from a first color polarized state when the user is not exposed to UV or actinic sunlight radiation to a second color polarized state. when the user is exposed to UV or actinic radiation from sunlight.

[118] Additionally, the functional organic coating may be a photochromic / dichroic coating comprising an aligned liquid crystal coating including an aligned photochromic / dichroic dye. As used herein, the term "photochromic / dichroic coating" refers to a coating that is adapted to exhibit both photochromic and polarizing properties in response to

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70/95 at least to actinic radiation. For example, according to

2005/0012998, incorporated herein by several non-limiting embodiments disclosed herein, the functional organic coating may be a photochromic / dichroic coating that is adapted to shift reversibly from a first non-polarized, optically colorless state to a second colored polarized state in response at least to actinic radiation. For example, if the optical element is an ophthalmic lens comprising the photochromic / dichroic coating, the lens may reversibly change from an unpolarized, optically colorless state when the user is not exposed to UV or actinic radiation, for example sunlight. , for a colored polarized state when the user is exposed to UV or actinic radiation, such as sunlight. Non-limiting examples of such coatings are described in US patent publication

paragraph 11 to paragraph 442, which specifically by reference.

[119] Other types of functional organic coatings that may be used in accordance with the present invention may include: inks, for example a pigmented paste or liquid used for the decoration, protection, and / or identification of a substrate; and printing inks, for example, pigmented paste or liquid used for writing and printing on substrates, such as producing check marks on security documents, for example, documents such as banknotes, passports, driver's licenses, for which authentication or authenticity checking may be desired.

[120] In addition, the optical element may comprise at least one functional organic coating which is in

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Contacting at least a portion of the compatibilizer coating and one or more functional organic coatings that are connected to at least a portion of the functional organic coating that is in contact with at least a portion of the compatibilizer coating. For example, the functional organic coating in contact with at least a portion of the compatibilizing coating may be an alignment coating, and the optical element may further comprise a liquid crystal coating including at least partially aligned liquid crystal material. and aligned with at least a portion of the alignment liner. Additionally, as discussed above, the aligned liquid crystal coating may comprise a material adapted to exhibit dichroism, and at least a portion of the material adapted to exhibit dichroism may be at least partially aligned with at least a portion of the liquid crystal material aligned with the dichroism. least partially.

[121] In addition to the compatibilizing coatings and functional organic coatings described above, at least one of a transition coat, a protective coat (such as those discussed above), and an anti-reflection coating may be attached to at least a portion of the optical element. As used herein, the term "transition coat" refers to a coat that helps create a gradient in properties between two coatings. For example, although not limiting here, a transition coating can help create a hardness gradient between a relatively hard coating and a relatively soft coating. Non-limiting examples of

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Transition coatings (which may also be termed "bonding layers" or "bonding coatings") include cured acrylate-based thin films, for example, such as those disclosed in US patent application publications. 2003/0165686 (from paragraphs 79 to 173), 2004/0207809 (from paragraphs 108 to 204), 2005/0196616 (from paragraphs 107 to 158), 2005/196617 (from paragraphs 24 to 129), 2005/196618 (from paragraphs 28 to 291), 2005/0196626 (from paragraphs 164 to 217), and 2005/196696 (from paragraphs 24 to 141), the disclosures of which are specifically incorporated herein by reference.

[122] When used herein, the term "anti-deflection coating" refers to a coating that enhances light transmittance through a substrate by reducing the amount of light that is reflected by the substrate. Non-limiting examples of anti-reflective coatings include, for example, a layer or multilayer of metal oxides, metal fluorides, or other such materials. Non-limiting examples of suitable anti-reflective coatings can be found in US patent. No. 5,580,819 in column 2, line 50 to column 11, line 44, the disclosure of which is specifically incorporated herein by reference.

[123] For example, as shown in Figure 1, the optical element may comprise a substrate 10 comprising an abrasion resistant coating 12 on at least a portion of a surface 11 thereof. Additionally, as shown in Figure 1, a compatibilizer coating 20 comprising a dendritic polymer described herein may be over at least a portion of the abrasion resistant coating 12, and a functional organic coating 30, for example.

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For example, a photochromic coating, an alignment coating, or a liquid crystal coating described herein may be over at least a portion of the compatibilizer coating 20. In addition, as shown in Figure 1, a transition coating 40 it may be over at least a portion of the functional organic coating 20. Additionally, as shown in Figure 1, a transition coating 40 may be over at least a portion of functional organic coating 30, and a protective coating 50 may be over at least a portion of transition coating 40. Still further, although not shown In Figure 1, an anti-reflective coating may be positioned on the protective coating 50 and / or on a surface of the substrate 10 opposite surface 11.

Also, as shown in Figure 2, the optical element may comprise a substrate 210 comprising an abrasion resistant coating 212 on at least a portion of a surface 211 thereof. Additionally, as shown in Figure 2, a compatibilizer coating 220 comprising a dendritic polymer described herein may be over at least a portion of the abrasion resistant coating 212, and a functional organic coating 230, for example, a photo-aligned coating. oriented, described herein, may be over at least a portion of the compatibilizer liner 220. Furthermore, as shown in Figure 2, a second functional organic coating 232, for example an aligned liquid crystal coating described herein, may be over at least a portion of the functional organic coating 230, and a protective coating 250 described herein. , may be over at least one

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74/95 portion of the second functional organic coating 232.

[125] As shown in Figure 3, the optical element may also comprise a substrate 310 comprising a compatibilizer coating 320 comprising a dendritic polymer described herein on at least a portion of a surface 311 thereof. A functional organic coating 330, for example a photochromic coating, an alignment coating or a liquid crystal coating described herein may be over at least a portion of the compatibilizer coating 320. In addition, as shown in Figure 3, a coating protector 350 may be over at least a portion of the functional organic coating 330.

[126] As discussed above, the present invention further contemplates methods for making the optical elements described above. For example, the present invention relates to methods for making an optical element comprising forming a compatibilizer coating comprising a dendritic polymer on at least a portion of a surface of a substrate, and forming a functional organic coating, other than a coating resistant to abrasion, over at least a portion of the compatibilizer coating such that the functional organic coating is in contact with at least a portion of the compatibilizer coating opposite the substrate.

[127] Also provided are methods for forming an ophthalmic element comprising: forming a compatibilizing coating that is substantially free of photochromic materials on at least a portion of a surface of an ophthalmic substrate, wherein the

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Compatibilizer coating is derived from a compatibilizer coating composition comprising: (I) an isocyanate-containing material comprising at least two isocyanate groups; (II) a (meth) acrylate-containing material comprising at least two reactive functional groups of which at least one is a (meth) acrylate group; (III) an aminoplastic resin comprising at least two reactive functional groups; (IV) a coupling agent, at least partial hydrolyzate thereof, or a mixture thereof; and (V) at least one of an initiator and a catalyst; at least partially securing at least a portion of the compatibilizing coating by exposing the portion to at least one of UV radiation and thermal radiation; and forming a functional organic coating, other than a duct coating, over at least a portion of the compatibilizing coating opposite the substrate.

[128] As discussed above, the substrate on which the compatibilizer coating is formed may comprise an abrasion resistant coating on at least a portion of its surface and the compatibilizer coating may be in contact with at least a portion of the abrasion resistant coating. . Non-limiting examples of abrasion resistant substrates and coatings are described above.

[129] Formation of the compatibilizer coating on at least a portion of the substrate surface may comprise applying a compatibilizer coating composition on at least a portion of the substrate, for example by one or more of spin coating, spray coating, coating. by rotation and

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76/95 spraying, lamination coating, curtain coating, and dip coating. Alternatively, the formation of the compatibilizer coating on at least a portion of the substrate surface may comprise mold casting or overmolding.

[130] For example, where the compatibilizer coating is formed by overmolding, a compatibilizer coating composition may be applied to a mold and thereafter a substrate may be placed in the mold such that the compatibilizer coating composition is forced to spread between the mold and the mold. the substrate surface to form a coating on at least a portion of the substrate surface. Alternatively, the substrate may be placed in the mold such that there is a gap between the mold and the substrate surface and thereafter the compatibilizing coating composition may be injected into the slot to form a coating on at least a portion of the substrate surface.

[131] Where the compatibilizer coating is formed by mold casting, one or more layers of a compatibilizer coating composition may be applied to a mold at least partially and thereafter a substrate may be poured onto the coating. For example, according to a non-limiting embodiment, an optical resin used to form the substrate may be cast into the mold onto the compatibilizer coating and subsequently fixed at least partially to form the substrate.

[132] Prior to forming the compatibilizing coating on at least a portion of the substrate surface, the surface may be cleaned and / or treated to provide a

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A clean surface is a surface that can improve the adhesion of the compatibilizer coating to the substrate. Commonly used effective treatments and cleanings include, but are not limited to, ultrasonic washing with aqueous soap / detergent solution; cleaning with an aqueous solvent mixture, for example a 50:50 mixture of isopropanol: water or ethanol: water; UV treatment, activated gas treatment, eg low temperature plasma or crown discharge treatment; and chemical treatment which results in hydroxylation of the substrate surface, for example by cauterizing the surface with an aqueous alkali metal hydroxide solution, for example sodium or potassium hydroxide, the solution of which contains a fluorinated surfactant. Generally, the alkali metal hydroxide solution is a dilute aqueous solution, for example from 5 to 40 weight percent, more typically from 10 to 15 weight percent, such as weight percent metal hydroxide. alkali. See, for example, U.S. Patent Nos. 3,971,872 (column 3, lines 25), 4,904,525 (column 6, lines 10 to 48), and 5,104,692 (column 13, lines 10 to 59) which describe surface treatments of polymeric organic materials. These disclosures are specifically incorporated herein by reference.

[133] Substrate surface treatment may be low temperature plasma treatment. Although not limiting here, this method allows surface treatment to improve the adhesion of a coating formed thereon, and can be a clean and efficient means of altering the physical surface, for example by wrinkling or chemically altering the surface without affecting the rest of the article. . Gases

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Inert gases such as argon and reactive gases such as oxygen have been used as plasma gas. Inert gases may wrinkle the surface, while reactive gases (such as oxygen) may wrinkle and chemically alter the surface exposed to plasma, for example, producing hydroxyl or carboxyl units on the surface. Oxygen can be used as the plasma gas. Although not limiting herein, it is considered that oxygen can provide a small but effective physical surface wrinkling along with a small but effective chemical modification of the surface. Those skilled in the art will understand that the extent of wrinkling and / or chemical surface modification will be a function of plasma gas and plasma unit operating conditions (including duration of treatment).

[134] The surface of the plasma treated substrate may be at room temperature or may be slightly preheated before or during plasma treatment. Although not limited herein, according to various non-limiting embodiments, the surface temperature to be subjected to plasma treatment may be maintained at a temperature below a temperature at which the surface may be adversely affected (other than the intended increase. surface area by wrinkling and slight chemical modification) by plasma. One skilled in the art can readily select the operating conditions of the plasma unit with respect to the treated plastic substrate to achieve improved adhesion of a film / coating overlaid on the plasma treated surface.

[135] After forming the compatibilizer coating and before

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In order to form the functional organic coating, at least a portion of the compatibilizing coating may be at least partially attached. For example, at least partially fixing at least a portion of the compatibilizer coating may comprise exposing the compatibilizer coating to at least one of actinic radiation, such as UV radiation, and thermal radiation. Further, the fixing of the compatibilizer coating can be performed using a double cure process, that is, using a two step process involving a UV curing step and a thermal curing step. The curing steps in the dual curing process may be performed in series, that is, one directly after the other, such that the compatibilizer coating is completely fixed (cured) prior to further processing, or alternatively the curing steps may be such that the compatibilizer coating is partially cured using the first (or thermal or UV) curing step before forming additional coatings thereon. Thereafter, the entire structure is subjected to a second curing step to complete curing of the compatibilizer coating and to cure the additional coatings simultaneously. Such double cure processes are well known in the art and are described in more detail below.

dendritic coating [136] When the compatibilizer composition comprises a polymer comprising at least one terminal (meth) acrylate group; an epoxy containing material comprising at least two epoxy groups; a silane coupling agent, at least partial hydrolyzate thereof, or a mixture thereof; it is a

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80/95 photoinitiator adapted to generate an acid upon exposure to actinic radiation, at least partially curing at least a portion of the compatibilizer coating may comprise exposing the portion to UV radiation or electron beam radiation (i.e. ionizing radiation), and It may further comprise exposing the portion to thermal radiation.

[137] Also, when the compatibilizing coating composition comprises a dendritic polymer comprising at least one terminal acrylate group; an isocyanate-containing material comprising at least two isocyanate groups; a silane coupling agent, at least partial hydrolyzate thereof, or a mixture thereof; a catalyst; and a photoinitiator, at least partially curing at least a portion of the compatibilizer coating may comprise exposing the portion to UV radiation and subsequently exposing the portion to thermal radiation.

[138] In addition, where the compatibilizer coating comprises an isocyanate-containing material and a (meth) acrylate-containing material (as discussed above), prior to forming the functional coating on the compatibilizer coating, the compatibilizer coating may be cured at least partially using a double cure process in which the coating is first exposed to UV or electron beam radiation and subsequently exposed to thermal radiation. Those skilled in the art will understand that UV curing requires the presence of at least one photoinitiator. The photopolymerization process and examples of photoinitiators are disclosed in US Patent No. 6,602,603, column 12, lines 11 to 37 and line 41 to column 13, line 36, the disclosures of which

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81/95 are incorporated herein by reference. Curing by electronic beam techniques does not require the presence of a photoinitiator. For example, the coating may be exposed to UV or electron beam radiation to at least partially cure the (meth) acrylate-containing materials of the composition and subsequently to thermal radiation to at least partially cure at another stage. the isocyanate-containing materials of the composition. These curing steps may be performed, for example, in series before forming the functional organic coating thereon. Alternatively, one of the curing steps may be performed prior to forming the functional organic coating on the compatibilizing coating, and one of the curing steps may be performed after forming the functional organic coating on the compatibilizing coating. For example, according to a non-limiting embodiment, the compatibilizer coating may be exposed to UV radiation or electron beam radiation before forming the functional organic coating thereon, and thereafter both coatings may be exposed to radiation. thermal

[139] The functional organic coating forming on at least a portion of the compatibilizing coating may be at least one of a photochromic coating, an alignment coating, and a liquid crystal coating.

[140] Where the functional organic coating may be a photochromic coating, the formation of the photochromic coating may comprise applying a coating composition comprising a photochromic amount of a photochromic material to at least a portion of the substrate,

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For example, by one or more of spin coating, spray coating, spin coating and spray coating, lamination coating, curtain coating, and dip coating.

[141] Alternatively, the photochromic coating may be formed on the substrate by overmolding. For example, a coating composition comprising a photochromic amount of a photochromic material may be applied to a mold and thereafter, a substrate may be placed in the mold such that the photochromic coating composition is forced to spread between the mold and at least a portion of a substrate surface. Alternatively, the substrate may be placed in the mold such that there is a gap between the mold and a surface of the substrate and thereafter the photochromic coating composition may be injected into the slot to form the coating.

[142] Additionally, a coating composition with less than a photochromic amount of a photochromic material, or without any photochromic material, may be formed on the surface of the substrate, for example by any of the above methods, and thereafter. a photochromic material or an additional amount of a photochromic material may be absorbed by the coating to form the photochromic coating.

[143] Where the functional organic coating comprises an alignment coating, forming the alignment coating may comprise applying a coating composition comprising an alignment means to at least a compatibilizing coated portion, at least partially ordering at least a portion of the coating. middle of

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At least partially curing at least a portion of the alignment means. Additionally, at least partial ordering of at least a portion of the alignment means may occur before, during, or after at least partial curing of at least a portion of the alignment means.

[144] For example, alignment coating formation may comprise applying a coating composition comprising a photo orientation material to at least a portion of the compatibilizer coating, for example by any of the methods of applying coating compositions described herein. , and simultaneously at least partially ordering and at least partially curing at least a portion of the photo orientation material by exposing the photo orientation material to polarized plane UV radiation. For example, in accordance with this non-limiting embodiment, the photo orientation material may be a material formed from photo orientable polymeric mesh (or PPN) such as those described in US patent No. 5,389,698, in column 2, line 1 to column 4, line 10; and in Kozenkov et al., "Photoanisotropic Effects in Poly (VinylCinnamate) Derivatives and Their Applications, Mol. Cryst. Liq. Cryst., Volume 409 (2004) on pages 251-267, the disclosures of which are incorporated herein by reference.

[145] Where the alignment coating comprises a photo oriented alignment coating, the formation of the alignment coating may comprise applying a coating composition comprising a photoorienting material to at least a portion of the compatibilizer coating, for example by any one. of the methods

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84/95 for applying coating compositions described herein, and at least partially ordering at least a portion of the photo orientation material by exposing the photoorientation material to polarized plane UV radiation, and subsequently curing at least partially the ordered portion of the photorientation material. Photo orientation. For example, although not limiting herein, according to this non-limiting embodiment, the photo-orientation material may be an azobenzene derivative as described in US Patent No. 4,974,941 in column 2, row 28 through column 9 , line 63, the disclosure of which is incorporated herein by reference.

[146] Where the alignment coating comprises a rotation oriented alignment coating, forming the alignment coating may comprise applying coating composition comprising a rotation oriented alignment material, for example, but not limited to a polyimide, at least at least a portion of the compatibilizer coating, for example by any of the methods for applying coating compositions described herein, at least partially curing a portion of the rotation oriented alignment material, and subsequently arranging at least a portion of the rotation oriented alignment material by rubbing the portion with a suitable textured cloth.

[147] Where the alignment coating comprises a liquid crystal alignment coating, the formation of the alignment coating may comprise applying a coating composition comprising a liquid crystal material to at least a portion of the compatibilizer coating, for example by any one. one of the methods

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85/95 for applying coating compositions described herein; at least partially ordering at least a portion of the liquid crystal material by exposing liquid crystal material to a magnetic field, an electric field, or a shear force; and at least partially curing at least a portion of the liquid crystal material. For example, at least partially curing at least a portion of the liquid crystal material may comprise exposing at least a portion of the liquid crystal material to UV radiation during or after at least partial ordering of the liquid crystal material.

[148] Additionally, as discussed above, where the optical element comprises an alignment coating, the optical element may further comprise a liquid crystal coating comprising a liquid crystal material aligned at least partially on at least a portion of the alignment coating. In this case the formation of the liquid crystal coating may comprise, for example, applying a liquid crystal material, for example, by any of the methods for applying coating compositions described herein, over at least a portion of the alignment coating and aligning with at least one portion. at least partially, at least a portion of the liquid crystal material with at least a portion of the alignment coating. For example, the alignment of the liquid crystal material may be achieved by allowing the liquid crystals to be in contact with the alignment coating for a period of time sufficient to achieve the desired level and alignment, either at room temperature or at elevated temperature.

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Additionally, at least a portion of the liquid crystal material may be cured at least partially during or after alignment. For example, where the liquid crystal material comprises a photocrosslinkable liquid crystal monomer, at least partially curing at least a portion of the liquid crystal material may comprise exposing at least a portion of the liquid crystal material to UV radiation during or after at least partial alignment of the liquid crystal material.

[150] As discussed above, the coating of aligned liquid crystals according to various non-limiting embodiments disclosed herein may further comprise a material adapted to exhibit dichroism. Material adapted to exhibit dichroism may be mixed and / or bonded with at least a portion of the liquid crystal material prior to applying the liquid crystal material to the substrate, and at least partially aligned with at least a portion of the liquid crystal material to form a functional organic coating such as, for example, a polarizing coating or a photochromic / dichroic coating. Additionally or alternatively, the material adapted to exhibit dichroism may be applied to the liquid crystal coating before or after alignment of the liquid crystal coating. For example, material adapted to exhibit dichroism may be absorbed by at least a portion of the liquid crystal coating, or before or after aligning the portion of the liquid crystal coating, and at least partially aligned with at least a portion of the crystal material. to form a functional organic coating such as, for example, a

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87/95 polarizing coating or a photochromic / dichroic coating. Nonlimiting examples of materials adapted to exhibit dichroism are discussed in detail above.

[151] Additionally, where the functional organic coating is an aligned liquid crystal coating comprising an aligned dichroic dye, the liquid crystal coating may be a polarizing coating and may further comprise a conventional photochromic material (i.e. to form a polarizing coating). and photochromic). For example, the photochromic material may be mixed and / or bonded with at least a portion of a liquid crystal material before applying it to a portion of the substrate, and / or the photochromic material may be absorbed by or prior to coating the liquid crystal. or after alignment thereof with the alignment liner.

[152] Additionally, as discussed above, at least a portion of the compatibilizer coating may be ordered at least partially to form an alignment coating before forming the functional organic coating on at least a portion of the compatibilizer coating. For example, at least a portion of the compatibilizer coating may be ordered at least partially by rubbing or compatibilizing coating by etching a portion of the typically after at least partially curing the portion of the compatibilizer coating composition. The functional organic coating forming on at least a portion of at least partially ordered compatibilizer coating may be a coating of at least aligned liquid crystals

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Partially, which may optionally include at least one material adapted to exhibit dichroism and / or a photochromic material. Non-limiting methods for forming at least partially aligned liquid crystal coatings, which may include materials adapted to exhibit dichroism and / or photochromic materials, are described above.

[153] Additionally, a liquid crystal coating may be applied to the compatibilizer coating without arranging at least a portion of the compatibilizer coating. Optionally, according to these non-limiting embodiments, during or after applying the liquid crystal coating, at least a portion of the liquid crystal coating may be arranged at least partially, for example by exposing the liquid crystal coating to at least one portion. between a magnetic field, an electric field, or a shear force. As discussed above, such ordered liquid crystal coatings may be used as alignment coatings for another coating, such as, for example, another liquid crystal coating. In addition, such ordered liquid crystal coatings may be used without further modification, for example, to impart certain desired optical properties to the optical element (e.g., a desired refractive index), or the ordered liquid crystal coating may be used to align a material that is adapted to exhibit dichroism. For example, as discussed above, liquid crystal coatings comprising an ordered liquid crystal material may be used to align

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89/95 a dichroic dye or a photochromic / dichroic dye to produce a polarizing coating or a photochromic / dichroic coating.

[154] Additionally, although not required, one or more coatings, such as a transition coating, a protective coating, and / or an anti-reflection coating, may also be formed on the optical elements. For example, as described above with respect to Figure 1, a transition coating may be formed over at least a portion of the functional organic coating and a protective coating may be formed over at least a portion of the transition coating. Although not limiting here, where the functional organic coating is a photochromic coating and the protective coating is an abrasion resistant hard coating, the transition coating may provide a gradient in hardness between the relatively soft photochromic coating and the relatively hard protective coating.

[155] Various nonlimiting embodiments of the present invention, or aspects thereof, are more particularly described in the following nonlimiting examples. It should be understood that the following examples are merely illustrative examples, with modifications and variations thereof being within the spirit and scope of the present invention set forth in the claims, will become apparent to those skilled in the art.

Examples [156] In Part 1 of the following examples, the materials and methods used to prepare primer coated and uncoated lenses are described. Part 2 describes the methods used

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90/95 to test adherence as well as the results reported in Table 1.

Part 1 - Lens Preparation [157] Seven pairs of lens substrates each having a diameter measuring 74 mm and having the base curvature listed in Table 1 were used. Test lenses were treated with a corona discharge by 15 seconds from a Tantec crown unit operating at 60 Hz and 1.3 kVA. The test lenses were then washed in an automated process which rubbed the surface with soapy water, rinsed with deionized water, and air dried. Composition A rotated coated each pair of lenses to obtain a wet film weight of approximately 0.025 g.

[158] Composition A was prepared by mixing in the following order in the amounts listed as a percentage by weight based on the total weight of the composition: 45.9 weight percent CN2302 reported to be a polyester acrylate oligomer obtained from Sartomer Corporation, Exton , Pennsylvania; 13.8 weight percent EPON® 828 epoxy resin reported to be a bisphenol A diglycidyl ether obtained from Miller-Stephenson, Danbury, Connecticut; 32.1 weight percent of SILQUEST A-187® reported to be gamma-glycidoxy propyl trimethoxysilane, obtained from GE Silicones, Wilton Connecticut; and 8.3 weight percent triaryl sulfonium hexafluorophosphate salts mixed in 50 weight percent propylene carbonate obtained from Sigma Aldrich, St. Louis, Missouri.

[159] Composition A coated lenses were placed approximately 20.32 cm (8 inches) from the lens to the lamp under an iron iodide doped mercury bulb

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400 watt / inch Type D 91/95 having a length of 15.24 cm (6 inches) for 30 seconds until cured.

[160] These samples as well as the uncoated lenses were then coated with a photo-orientable polymer mesh solution obtainable as ROLIC® ROP-108 / CO obtained from Rolic Technologies, Ltd., Allschwil, Switzerland. The designation CP is reported to mean cyclopentanone. The coating solution was applied during the first spin speed of 612 rpm for 2 seconds. After coating application, the rotation speed of each coated lens increased to 1528 rpm for 12 seconds and then to 1933 rpm for 2 seconds. The coated lenses were dried in an infrared / convection oven combination on a conveyor belt traveling for 11 minutes through 5 zones having the following temperatures provided by the IR oven and / or convection oven (CO) as indicated: Zone 1 175 ° C (IR); Zone 2 - 175 ° C (IR); Zone 3 - 155 ° C (IR) and 150 ° C (CO); Zone 4 - 150 ° C (CO); and Zone 5 - 150 ° C (CO); and cooled to room temperature.

[161] After applying the photoorientable polymeric mesh to each of the test lenses, at least partially, at least a portion of the photoorientable polymeric mesh was ordered by exposure for 35 seconds to the linearly polarized ultraviolet light of the same type D bulb. mentioned above, which was filtered with fused silica polarizer having a drive shaft parallel to the long side of the rectangular filter. The lamp to lens distance was approximately 15.24 cm (6 inches). After ordering at least a portion of the photo-orientable polymer mesh, the lenses were cooled to room temperature.

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92/95 [162] Composition B was applied to the lenses by rotary coating under conditions to obtain a wet film weight of approximately 0.10 g. Composition B was prepared by mixing the materials in the following order: 39.9 weight percent anisole mixed with 0.1 weight percent BYK® UV3530 surfactant obtained from BYK Chemie, USA, Wallingford, Connecticut; heated and kept at 65 ° C; 4.4 weight percent of dichroic dyes formulated to produce a gray color were added; and mixed for 60 min. A liquid crystal monomer, 27.3 weight percent of RM 105 liquid crystal monomer reported as having the molecular formula C23H26O6, which was obtained from EMD Chemicals, Inc., Gibbstown, New Jersey, was added and mixed. the composition for 30 min. Then, 27.2 weight percent of RM 257 liquid crystal monomer reported as having the molecular formula C33H32O10, which was also obtained from EMD Chemicals, Inc., Gibbstown, New Jersey, was added and the composition mixed. for 30 min. Next, 1.1 percent by weight of bis (2,6-dimethoxy benzoyl) phenyl phosphine oxide was added and the composition was mixed for 30 min.

[163] The coated lenses were placed on a heated conveyor belt using an infrared heating system having five temperature zones as follows: 100 ° C, 90 ° C, 60 ° C, 55 ° C, and 55 ° C. Coated lenses traveled through the five zones in 5 minutes. The samples were cooled to room temperature before entering a carrier UV curing line.

[164] The carrier UV curing line had a nitrogen atmosphere in which the oxygen level was lower.

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93/95 which 100 ppm. The carrier traveled at 7.2 mm / s under ultraviolet light from a 400 watt / inch (157.5 J / s / inch) D-type iron iodide mercury doped lamp In length, the lamp power was adjusted to 94% and the lamp was positioned 20.3 cm (8.0 inches) above the conveyor. A converging funnel was placed under the lamp to direct light flow in the area of ​​15.24 cm x 5.08 cm (6 inches x 2 inches) to expose the lens. A 300 nm filter was placed under the funnel to block UV wavelengths above 300 nm for the lens. Each lens was exposed for 20 seconds under the UV lamp. The samples were then placed in a convection oven at 105 ° C (221 ° F) for 3 hours and 15 minutes.

Part 2 - Adherence Test [165] The adhesion of the Composition B coating on test lenses with and without Composition A was determined by the crosshatch tape adhesion test known to those skilled in the art and described below. . For each example test lens, lens A was uncoated with Composition A and lens B was coated with Composition A. In the primary test or dry test, a cutting tool composed of eleven X-acto® utility knife blades spaced 1 mm (end to end) and 0.65 mm thick was used to perform a first cut long, for example, from the lens center to 3 mm from the edge of a 65 mm diameter lens, in the sample followed by second and third cuts, which were made at 90 ° and through the first cut. The second and third cuts were separated from each other to provide separate hatched zones. Scotch® tape was applied

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94/95

250 (3M, St. Paul, Minnesota) 2.54 cm (1 inch) wide and 5 to 6.3 cm (2 to 2.5 inch) long toward the first cut that was pressed to smooth and prevent any bubbles. Prior to testing, the tape was stored at 23 ° C +/- 5 ° C with relative humidity below 60%. The tape then hurts from the surface with a strong, rapid and continuous movement. This procedure was repeated with a new piece of tape. A smaller piece of 3.8 cm (1.5 inch) tape was applied to each of the hatched zones produced by the second and third cuts in a 90 ° direction relative to the direction of the first tape. The tape has been torn off in the same manner as before. The resulting lenses were inspected using a point light source and magnifier / magnifying glass. The average remaining coating percentages from these two sites were determined and reported in Table 1 as the results of the “Primary. After removing, drying and cooling to room temperature, the above procedure was repeated. The average results of this test were reported in Table 1 as “Secondary.

Table 1

<td>Lens substrate</td><td>Curvature- base</td><td>% of primary adherence</td><td>% secondary adhesion</td>

<td>1A⁽¹⁾</td><td> 2, 25</td><td> 100</td><td> 99</td>

<td>ÍB¹¹</td><td> 2, 25</td><td> 100</td><td> 100</td>

<td>2A⁽²⁾</td><td> 6, 00</td><td> 0</td><td> 0</td>

<td>2B⁽²⁾</td><td> 6, 00</td><td> 100</td><td> 100</td>

<td>3A⁽³⁾</td><td> 6, 25</td><td> 100</td><td> 0</td>

<td>3B⁽³⁾</td><td> 6, 25</td><td> 100</td><td> 100</td>

<td>4A⁽⁴⁾</td><td> 6, 75</td><td> 98</td><td> 0</td>

<td>4B⁽⁴⁾</td><td> 6, 75</td><td> 100</td><td> 100</td>

<td>5A⁵</td><td> 4, 00</td><td> 0</td><td> 0</td>

<td>5B⁷⁵</td><td> 4, 00</td><td> 95</td><td> 95</td>

<td>AND THE⁶</td><td> 3,50</td><td> 0</td><td> 0</td>

<td>6B⁽⁶⁾</td><td> 3,50</td><td> 50</td><td> 50</td>

<td>OK¹⁷</td><td> 3,50</td><td> 0</td><td> 0</td>

<td>7B^TT</td><td> 3,50</td><td> 100</td><td> 100</td>

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95/95

Uncoated lenses made of CR-607 monomer sold by PPG Industries, Inc., Pittsburgh, Pennsylvania.

Uncoated lenses prepared by Younger Optics (Torrance, California) made of TRIVEX® monomer sold by PPG Industries, Inc., Pittsburgh, Pennsylvania.

Hardcoating lenses prepared by Younger Optics (Torrance, California) made of polycarbonate monomer. Hardcoating lenses prepared by Gentex Optics, Inc., Dudley, Massachusetts, made of polycarbonate and designated as Poly GLC.

Uncoated lenses prepared by Essilor of America, Dallas, Texas and designated as MR8.

Lenses prepared by Seiko Optical Products, Mahwah, New

Jersey, and designated as uncoated MR10.

Lenses prepared by Seiko Optical Products, Mahwah, New

Jersey, and designated as hard coated MR10.

[166] As discussed above, while the present invention is described herein along with certain embodiments and examples, the present invention is not limited to the particular embodiments and examples disclosed, but is intended to cover modifications that are within the spirit and scope of the invention as defined. by the attached claims. Furthermore, it is to be understood that the present description illustrates aspects of the invention relevant to a clear understanding of the invention. Accordingly, certain aspects of the invention that would be obvious to those skilled in the art and thus would not facilitate a better understanding of the invention were not presented in order to simplify the present disclosure.