Optical elements comprising compatiblizing coatings and methods of making the same

(54) Title: OPTICAL ELEMENT, METHOD TO MANUFACTURE AN OPTICAL ELEMENT, COMPATIBILIZER COATING COMPOSITION, METHOD TO FORM AN OPHTHALMIC ELEMENT AND OPHTHALMIC ELEMENT (30) Unionist Priority: 26/01/2007 us 11 / 627,688 (73) Owner (es) ): transitions optical, inc.

(72) Inventor (s): Kevin W. Seybert (74) Attorney (s): Antonio Maurício Pedras Arnaud (86) International Order: pct us2008050384 of 07/01/2008 (57) Summary: optical element, method to manufacture UM OPTICAL ELEMENT, COMPATIBILIZER COATING COMPOSITION, METHOD TO FORM AN OPHTHALMIC ELEMENT AND OPHTHALMIC ELEMENT. The present invention relates to optical elements, such as ophthalmic elements, including a substrate, a compatibilizer coating that optionally includes a dendritic polymer on at least a portion of the substrate surface and a functional organic coating, such as, but not limited to, a alignment coating, photochromic coating, or lined liquid crystal coating, in contact with at least a portion of the compatibilizer coating opposite from the substrate. The present invention also relates to compositions of dendritic polymer compatibilizer coatings that can be used to form compatibilizer coatings on the surface of an optical element, and to methods for making optical elements using the compatibilizer coatings.

(87) International Publication: wo 2008 / 094722of 07/08/2008

<img file="BRPI0806374A2_D0001.tif" />

10'

<img file="BRPI0806374A2_D0002.tif" />

ΡΙ0806374 -5

OPTICAL ELEMENT, METHOD FOR MANUFACTURING AN OPTICAL ELEMENT, COMPATIBILIZER COATING COMPOSITION, METHOD FOR FORMING AN OPHTHALMIC ELEMENT AND OPHTHALMIC ELEMENT.

Historic

In general, the present invention relates to optical elements, such as ophthalmic elements, comprising a substrate, a compatible coating and a functional organic coating on at least a portion of a substrate surface. The present invention also relates to compositions of compatibilizer coatings that can 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, can be adapted for use in certain applications by placing one or more functional organic coatings on the element. For example, it is possible to adapt an optical element, such as an ophthalmic element, for use in photochromic applications for ocular use, 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 user with an appropriate level of transmitted radiation depending on environmental conditions.

In addition, 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 polarizing lenses for ocular 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 photochromatic and dichroic properties under certain conditions by forming a coating comprising an aligned liquid crystal material and a photochromatic / dichroic dye on the element's surface. Optical elements with photochromic / dichroic coatings can 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 can return to the first state in absence of actinic radiation and in response to thermal energy. For example, ophthalmic elements with photochromic / dichroic coatings, such as lenses for eye applications, can transition between a clear non-polarized state and a colored polarized state to provide the user with both an appropriate level of transmitted radiation and a reduced brightness of reflected light depending on environmental conditions.

However, if the interaction between the functional organic coating and the surface on which it is applied is insufficient, the functional organic coating (or portions thereof) may not properly adhere to the surface. For example, if a liquid crystal coating (such as those discussed above) and the substrate surface lacks sufficient compatibility, the coating may not adhere properly to the surface and can be easily removed from the surface, for example, by exfoliating. In the context of lenses for ophthalmic applications, exfoliation of the polarizing coating from the lens surface will degrade the overall performance of the lens by allowing non-polarized light to pass through those portions of the lens that have had the coating removed.

It is possible to apply a compatibilizer coating to the surface of a substrate to improve compatibility between the substrate and a photochromic coating applied to it. However, the compatibilizer coating that is used over 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 matching coatings.

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

Brief summary of disclosure

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

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

In addition, the present invention provides a compatibilizer coating composition. The compatibilizer 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, an coupling, a hydrolyzate at least partial thereof, or a mixture thereof, and an initiator, the compatibilizing coating composition being free of photochromic materials.

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

There are also provided methods for an ophthalmic element comprising creating a compatibilizer coating on at least a portion of a substrate surface 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.

The present invention provides an ophthalmic element comprising an ophthalmic substrate, a compatibilizer 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 a coating containing a material-resistant coating. abrasion, in contact with at least a portion of the opposing compatibilizer coating of the ophthalmic substrate. The compatibilizer coating is formed by a compatibilizer composition comprising an isocyanate including at least two reactive functional groups, a material containing (meth) acrylate including at least two reactive functional groups, at least one of which is a (meth) acrylate group, a resin aminoplastic comprising at least two reactive groups, a coupling agent, a hydrolyzate at least partial thereof, or a mixture thereof, and at least one initiator and a catalyst.

Methods for making ophthalmic elements are also disclosed. The methods comprise forming a compatibilizer coating that is essentially free of photochromic materials on at least a portion of an ophthalmic substrate surface, at least partially fixing a portion of the compatibilizer coating by exposing at least one portion to at least one of UV radiation, electronic beam radiation, and thermal radiation, and form a functional organic coating other than a hard coating, over at least a portion of the compatibilizer 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 together with the figures. Figures 1-3 are schematic cross-sectional drawings of optical elements according to the present invention. Description of various non-limiting embodiments It is understood that although the present invention is described herein in relation to certain embodiments and examples, the present invention is not limited by particular embodiments and examples, but is intended to cover modifications that are within the spirit and the scope of the invention, 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. Consequently, certain aspects of the invention that would be obvious to those of ordinary skill in the art and that would therefore not facilitate a better understanding of the invention have not been presented in order to simplify the present description. When used in this report and in the appended claims, articles one, one, and the include the plural of them, unless expressly and unambiguously limited to a referent. Additionally, for the purposes of this report, unless otherwise stated, all numbers expressing quantities, such as percentages by weight 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 approximately. Consequently, unless otherwise indicated, it should be understood that the numerical parameters presented in the following report and in the attached claims are approximations. At a minimum, and not as an attempt to limit the application of the doctrine of equivalents within the scope of the claims, the numerical parameters should be read in the light of the number of significant figures reported and the application of the usual rounding techniques.

In addition, although the numerical parameters and 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 must be understood that such numerical values ​​inherently contain certain errors resulting, for example, from the equipment and / or the measurement technique. In addition, when numerical ranges are reported here, these ranges include their extreme points.

In addition, it should be understood that where relationships of possible substituting groups are provided using titles and subtitles, such as, for example: (a), (b). . . ; (1), (2) ...; (I), (II) ..., etc., these titles and subtitles are provided for convenience of reading only and are not intended to limit the choice of substituting groups. As discussed above, the present invention relates to optical elements, and in particular, optical elements comprising a substrate, a compatible coating on at least a portion of a substrate and functional surface other than an abrasion, in contact with at least a portion of the compatibilizer coating in front of the substrate.

an organic coating resistant coating

That is, compatibilizer coating is between the substrate and the functional organic coating.

When used here, the term optical means to relate 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 here, ophthalmic means to relate 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 can be segmented or non-segmented vision lenses (such as, limited to, bifocal lenses, progressive trifocal lenses), as well as as other elements used to correct, protect or improve (cosmetically or differently) vision, including without limitation, contact lenses, intraocular lenses and protective lenses or visors.

When used here, the term display means the or machine-readable but not multiple and lenses representing visible information in words, numbers, symbols, plans or drawings. Examples screens, monitors and safety signs.

Display elements include security elements, such as When used herein, the term window means an opening adapted to allow radiation to be transmitted through it. Non-limiting examples of windows include aircraft and automotive transparencies, filters, shutters and optical switches. When used here, the term mirror means a surface that speculatively reflects a large fraction of incident light. When used herein, the term liquid crystal cell refers to a structure containing a liquid crystal material that is capable of being ordered. In a typical liquid crystal cell, a liquid crystal material is contained between two substrates that are sealed together to form 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 ordered state. A non-limiting example of a liquid crystal cell element is a liquid crystal display. Substrates that are suitable for use in conjunction with various embodiments of the present invention disclosed herein include, but are not limited to, substrates formed from organic materials, inorganic materials or combinations thereof, for example, composite materials. In addition, the substrates disclosed herein may have any appropriate shape, including but not limited to, flat, cylindrical, spherical, plane-concave (ie flat on one side and concave on the other) and plane-convex (ie flat on one side) side and convex on the other). For example, the substrate may be a plano-convex or planoconcheal ophthalmic lens having a flat surface and a curved surface (convex or concave) that has a curvature corresponding to any of several basic curves for ophthalmic lenses. Specific non-limiting examples of materials that can form substrates are described in more detail below.

Non-limiting examples of organic materials that can be used to form the substrates disclosed herein include polymeric materials, for example, homopolymers and copolymers prepared from monomers and mixtures of monomers disclosed in US Patent No. 5,962,617, column 2, row 9 to column 7 to row 46, and in US Patent No. 5,658,501 to column 15, row 28 to column 16 to row 17, the disclosures of which are hereby specifically incorporated by reference. Such organic materials can be thermoplastic or thermoset polymeric materials, can be transparent or optically clear, and can have any required refractive index. For example, although non-limiting here, the refractive index of optically clear or transparent 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 can be used to form the substrates of optical elements disclosed herein include: polyol monomers (allyl carbonate), such as whose monomer is sold under the trade name CR-39 ™ by PPG Industries, Inc Pittsburgh, Pennsylvania; polyurea / polyurethane polymers (polyurea / urethane), for example, diglycol diethylene glycol allyl carbonates (allyl carbonate), are prepared, for example, by the reaction of a polyurethane prepolymer and a composition for such curing agent polymer being trade name TRIVEX ™ by PPG Industries Ohio, Inc., Cleveland, Ohio; functional acrylic monomers, such as, but not limited to, polyol (meth) acryloyl terminated carbonate monomer, diamine monomers, one sold under diethylene glycol dimethacrylate, ethoxylated phenol methacrylate monomers, trimethylol triacrylate monomers ethoxylated, poly (ethylene glycol) bis methacrylate monomers, urethane acrylate monomers, and poly (ethoxylated bisphenol A dimethacrylate) monomers; diisopropenyl benzene monomers; poly (vinyl acetate); poly (vinyl alcohol); polyvinyl chloride); poly (vinylidene chloride); polyethylene; polypropylene; polyurethanes; polythiourethanes, which include but are not limited to materials such as the optical resins designated by MR-6, MR-7, and MR-8 by Mitsui Toatsu Chemicals, Inc .; thermoplastic polycarbonates, such as bisphenol A carbonate and phosgene bonded resin, such material being sold under the trade name LEXAN®; polyesters, such as material sold under the trade name MYLAR®; poly (ethylene terephthalate); (poly vinyl butyral); norbornene homopolymers and copolymers, such as those materials sold under the trade name ARTON® by JSR Corp., Saitama, Japan; poly (methyl methacrylate), such as the material sold under the trade name PLEXIGLAS®, and polymers prepared by reacting polyfunctional isocyanates with polythiols or polysulfide monomers, copolymerized / copolymerized / polypolymerized with polythiols, polyisocyanates, polyisomycoses and polyisomycosides, polyisomycosis and polyisomycoses. ethylenically unsaturated monomers. also copolymers of such monomers and halogenated or Mixtures of the polymers and copolymers described with other polymers are considered, for example, to form block copolymers or interpenetrating network products.

the substrate can be one used here, the term

As mentioned earlier, ophthalmic substrate. When ophthalmic substrate refers to lenses, partially molded lenses, and lens generators. Non-limiting examples of organic materials from which ophthalmic substrates according to the various non-limiting embodiments disclosed herein can be formed include, but are not limited to, polymers recognized in the art that are useful for forming optically clear or transparent blocks for optical applications.

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 forming substrates that can be used in conjunction with various non-limiting embodiments disclosed herein include glasses based on inorganic oxides, minerals, ceramics, and metals. For example, the substrate may comprise glass based on inorganic oxide. Likewise, the substrate can comprise a ceramic, metallic or mineral substrate, which, optionally, can be polished to form a reflective surface. Where it is desired to have a substrate reflecting surface, a reflective coating or coating may be deposited or applied differently to a surface of an inorganic or organic substrate to make it reflective or improve its reflectivity.

In addition, the substrates can be colorless, colored and / or photochromatic. When used herein, the term colorless substrates means substrates essentially free of agent additions (such as, but not limited to, conventional dyes).

When used here, the term actinic radiation means electromagnetic radiation, such as, but not limited to, visible and ultraviolet radiation, which is capable of causing a response. In addition, the term colored substrates means substrates that have an addition of coloring agent (such as, but not limited to, conventional dyes), in which the coloring agent has one that is colored by the absorption spectrum for visible radiation that does not vary significantly in response to actinic radiation. When used here, the term photochromatic substrates means substrates that have the addition of photochromatic material. In addition, substrates according to various non-limiting embodiments disclosed herein can be colored as well as photochromic, that is, the substrates can comprise both a conventional dye coloring agent (which has an absorption spectrum for visible radiation that does not vary significantly in response to actinic radiation) as a photochromatic material.

Furthermore, optical substrates 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 its 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 tend to be quickly scratched, rubbed or scraped. An example of such a polycarbonate lens substrate is sold under the trade name GENTEX® (by Gentex Optics, Inc., Dudley, Massachusetts). When used herein, the term protective coating refers to a coating, such as transient coatings, abrasion resistant coatings (or hard 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 thin films based on radiation cured acrylate, abrasion resistant coatings based on inorganic materials such as silica, titania, and / or zirconia, and combinations of these substrates worn by the coatings. For example, the protective coating may comprise a first thin film coating based on radiation cured acrylate and a second coating comprising a silane. Non-limiting examples of commercial protective coatings products include SILVUE® 124 and HI-GARD® coatings, obtainable from SDC Coatings, Inc. and PPG Industries, Inc., respectively.

Although non-limiting here, 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., liquid crystal coatings ), may have less than desired adhesion to organic substrate surfaces, and in particular, to organic substrate surfaces having abrasion resistant coatings on them. It has also been found that the compatibilizer coatings of the present invention can be useful for improving and / or enhancing the adhesion 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 can comprise a substrate including an abrasion resistant coating in contact with at least a portion of its surface, and the compatibilizer coating can be in contact with at least a portion of the abrasion resistant coating on the substrate surface to improve or enhance the adhesion between the abrasion resistant coating on the substrate and the functional organic coating applied on it.

As discussed earlier, the present invention relates to optical elements comprising a substrate, a compatible coating on 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 compatibilizing coating in front of the substrate.

When used herein, the term coating means a structure comprising one or more complete or partial layers derived from compositions capable of flowing, and which may have uniform cross-section thickness and / or composition. When used herein, the term compatibilizer coating refers to a coating that improves compatibility between a surface and another coating applied to it and / or facilitates the formation or application of other coatings on the surface. For example, a compatibilizer coating can be applied to a surface, for example on the surface of a substrate or on the surface of another coating, to improve one or more of wetting, chemical compatibility, and adhesion of another coating to the surface.

Furthermore, when used here in the context of a coating being on a surface or object, the term about 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 here, the term connected to means associated, directly or indirectly, with another material or structure. Thus, for example, a coating that is on a surface can be applied directly on the surface or it can be applied on one or more other coatings, at least one of which is applied directly on the surface.

compatibilizer coating that is on at least a portion of the substrate surface comprises a dendritic polymer. When used herein, the term dendritic polymer refers to a three-dimensional macromolecular material comprising a polyvalent core that is covalently attached to a plurality of dendrites (or tree-like structures). The term dendrite means a tree-like structure having multiple layers of branching (or generations) emanating from a focal point, such as a multi-purpose 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 reactive terminal sites (or terminal functional groups) from which the successor generation (if any) can extend, or in the case of the last generation, which can provide a terminal functional group in the dendritic polymer. Dendritic polymers generally have a large number of terminal functional groups, have no hitches, and have a low hydrodynamic volume. In addition, when used herein, the term dendritic polymers includes both dendrimers and hyperbranched polymers. When used herein, the term dendrimer refers to a dendritic polymer having a symmetrical globular architecture that results from a controlled process giving an essentially monodispersed molecular weight distribution. When used herein, the term hyperbranched polymer refers to a dendritic polymer having a certain degree of asymmetry and a polydispersed molecular weight distribution.

Although non-limiting here, dendritic polymers can be formed, for example, by forming dendrites in stages in a multi-purpose nucleus. For example, although non-limiting here, a polyester-like dendritic polymer can 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 nucleus with several dendrites comprising a first branching (or generation) layer connected thereto. Each of the dendrites will comprise a number of terminal functional groups (for example, in the present example, hydroxyl terminal groups), which are located on the periphery of the first branching layer. These terminal functional groups can react with yet another first chain extender to produce a second branching layer in the core. The continuous reproduction of branching layers by reacting the terminal functional groups on the periphery of the last branching layer formed with additional first chain extenders will form the dendrites and will normally produce an increase in the number of terminal functional groups (for example, in the present example, terminal groups hydroxyl) in the dendritic polymer. After adding the final branching layer to the dendritic polymer, any remaining terminal functional groups (for example, in the present example any remaining terminal hydroxyl groups) in the final branching layer of the dendritic polymer can form the terminal functional groups of the dendritic polymer; they can also extend the chain, for example by alkoxylation; they can terminate, for example by reaction with a chain switch; or they can be functionalized by reaction with another material to provide a different terminal functional group in the dendritic polymer. When used herein, the term chain switch includes chain extenders lacking appropriate functional groups to react with a subsequent chain extender group.

A non-limiting example of a step method for forming a polyester-like dendritic polymer in a polyvalent core is described in US patent No. 5,418,301 in column 6, lines 1 through 60. The US patent No. 5,418,301 also provides several examples of polyvalent cores suitable for use in forming polyester-type dendritic polymers in column 2, row 45 through column 3, row 68; several examples of chain extenders suitable for use in forming polyester-type dendritic polymers in column 4, lines 1 through 55, and several examples of chain switches suitable for use in forming polyester-type dendritic polymers in column 4, line 56 through column 5, line 68. The aforementioned portions of US patent disclosure No. 5,418,301 are incorporated herein specifically by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein. In addition, during the step process described above, after the formation of any branching layer (i.e., the first branching layer, the second branching layer, etc.), an intermediate substituent (which can also be referred to as separation chain) that is different from the first chain extender (for example, although non-limiting here, a different polyfunctional carboxylic acid or different anhydride, containing reactive end functionality), can react with the hydroxyl end groups of the last branching layer formed. Thereafter, terminal functional groups of the intermediate substituent can react with a second chain extender, which may be different 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 presented in the US patent No. 6,569,956 in column 3, line 33 to column 4, line 42, whose disclosure is incorporated herein specifically by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein.

Alternatively, dendritic polymers can be formed by pre-producing dendrites and subsequently linking the dendrites to a polyvalent core. For example, a polyester-like dendritic polymer can be formed by condensing one or more hydroxyls of carboxylic acids at normal esterification temperatures, allowing mono-, di-, tri- or polyfunctional acids to form ester bonds with mono-, di-, tri- or polyfunctional or epoxides, or by similar procedures resulting in ester bonds, ether bonds or other chemical bonds, to form dendrites. The raw materials used to produce the dendrites can be chosen to provide each dendrite with a functional group at its focal point, and this functional focal point group can react with a polyvalent nucleus to link the dendrite to the nucleus, and a plurality of groups functional terminals on the periphery of the dendrite. A non-limiting example of such a method for forming a polyester-like dendritic polymer is shown in the US patent. No. 5,663,247 in column 7, lines 23 to 51, and in column 8, lines 1 to 38, which is incorporated herein 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 can be produced from ester or polyester units, optionally in combination with ether or polyester units. For example, the dendritic polymer of the compatibilizer coating may be a polyester-type dendritic polymer comprising a monomeric or polymeric core having at least one reactive epoxide, hydroxyl, carboxyl or anhydride group, to which 1 to 100 may be added, and most commonly of 1 to 20, for example 2 to 8, branching layers. The branching layers can 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 earlier, polyester-like dendritic polymers can optionally also contain at least one separation chain extender, which can 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 earlier, the polyester-type 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 if partially or completely terminated by at least one monomeric or polymeric chain switch and / or functionalized with a different functional group.

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

The dendritic polymer of the compatibilizer coating may be a polyester-type dendritic polymer that is at least one of a hyper-branched polyester oligomer and a hyper-branched polyester acrylate oligomer. Non-limiting examples of commercially obtainable polyester-type dendritic polymers that can be used can include polyester-type dendritic polymers supplied by Perstop Specialty Chemicals, Perstop, Sweden under the trade name BOLTORN® and designated as dendritic macromolecules H20, H30, and H40, which comprise hydroxy terminal groups. According to the manufacturer, these materials generally have a weight average molecular weight in the range of 1,000 to 4000 atomic mass units and materials H20, H30 and H40 have an average of 16, 32 and 64 hydroxy terminal 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 as 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 trade name BOLTORN® and designated as P500.

Other non-limiting examples of dendritic polymers that can be used in compatibilizer coatings can include mixed polyester / polyether dendritic polymers, epoxide / mine dendritic polymers, carbosilane-based dendritic polymers, starch / amine dendritic polymers, polysulfide dendritic polymers, polysiloxane dendritic polymers, polyaminesulfide dendritic polymers, polyether dendritic polymers, polythether dendritic polymers, polyester dendritic polymers, amide polyester dendritic polymers, poly (ketone ether) dendritic polymers, and the like. In addition, as discussed above, such materials can be functionalized, for example, by reaction with acrylating agents to provide terminal acrylic groups or terminated using an appropriate chain switch.

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

The dendritic polymer of the compatibilizer coating may be an epoxide / amine dendritic polymer. The dendritic polymer of epoxide / amine can be prepared by a repetitive reaction sequence (a) from the conversion of plots that are suitable for generation of primary amino groups; (b) a ring-opening addition reaction of the primary amino portions generated in (a) and the epoxide of the branching molecules having an epoxide portion and having at least one portion that is suitable for generating at least one primary amino group ; and (c) a termination reaction that is characterized by the reaction of adding 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 US patent no.

5,760,142. The description found in column 1, line 65 through column 3, line 56 of US Patent No. 5,760,142 herein is incorporated by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein.

The dendritic polymer of the compatibilizer coating can also be a carbosilane-based dendritic polymer. Carbensilane-based dendritic polymers can 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 dendritic carbosilane polymers are described in US Patent No. 5,276,110, particularly in column 1, line 58 through column 5, line 5, the description of which is incorporated herein by reference to the extent that the disclosure is incorporated. do not conflict with the terms and definitions provided herein.

In addition, the dendritic polymer of the compatibilizer coating can be a dendritic polymer that is prepared by the polycondensation of cyclic anhydrides with diisopropanolamine. Non-limiting examples of such dendritic polymers are commercially obtainable under the trade name HYBRANE ™ from DSM NV, and are prepared with acrylate and methacrylate functional groups. A specific non-limiting example of such a dendritic polymer is the commercially obtainable HYBRANE ™ H1500 (unmodified) polymer.

The dendritic polymer of the compatibilizer coating can also be a polysiloxane dendritic polymer, which can be prepared, for example and without limitation, by repeated silane hydroxylation and displacement of chloride on the silicon atom. The preparation of dendritic polymers of specific polysiloxanes is described by Uchida et al., J. Am. Chem. Soc., 1990, 112, 70777079, the description 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 earlier, the terminal functional groups of the last branching layer formed of a dendritic polymer can optionally be functionalized, that is, it can react to provide the dendritic polymer with different terminal functional groups. For example, polyester-like dendritic polymers comprising hydroxyl end groups can be acrylated to provide an acrylate functional group on the periphery of the dendritic polymer. For example, although not limiting here, the acrylation of polyester-like dendritic polymers, and the recovery and purification of the acrylated dendritic polymer, can be performed using methods well known in the literature, such as the methods described in the article Acrylic Ester Polymers, which found in 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 (βmethacrylic acid), condensation with an isocyanate (meth) acrylate , or a direct reaction with an anhydride and / or acyl halide corresponding to acrylic acid, methacrylic acid, or crotonic acid, usually in a molar ratio of hydroxyl groups to said acid, anhydride and / or acyl 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 acrylates and methacrylates with epoxide or anhydride functionality, such as glycidyl methacrylate. Those skilled in the art will understand that, typically, the acrylating agent is used in a stoichiometric molar excess.

The percentage of terminal functional groups in the dendritic polymer that can be functionalized, for example, by acrylation to provide acrylate terminal groups, can vary. For example, according to various non-limiting embodiments disclosed herein, from about 1 to 100% of the terminal functional groups of the dendritic polymer of the compatibilizer coating can be functionalized. The percentage of acrylate end groups in an acrylated (ie functionalized) polyester dendritic polymer can vary from 1 to 100%, for example, from 20 to 100%, or from 40 to 100%, such as from 45 to 100%, and it can also vary between any combination of these percentages, including the percentages mentioned.

The dendritic polymers of the compatibilizer coating can be polyester-type dendritic polymers comprising hydroxyl end groups (such as those described above), or one or more of the hydroxyl end groups can be functionalized to provide the dendritic polymer with one or more different end functional groups. For example, as discussed above, the hydroxyl groups of a polyester-like dendritic polymer can be functionalized to provide one or more acrylate end groups.

The compatibilizer coating comprising the dendritic polymer can be formed by a compatibilizer coating composition comprising a dendritic polymer including a terminal functional group, with a terminal functional group being at least one among hydroxyl, acrylate, methacrylate, acid, isocyanate, thiol, amine , epoxy, silane, and glycidyl. Non-limiting examples of dendritic polymer comprising a terminal functional group and methods for preparing the same are discussed above.

In addition to the dendritic polymers discussed above, the compatibilizer coating compositions from which the compatibilizer coatings can be derived may further comprise: (a) an epoxy-containing material comprising at least two reactive functional groups of which at least one is an epoxy group; (b) an isocyanate-containing material comprising at least two reactive functional groups of which at least one is an isocyanate group; (c) a material containing (meth) acrylate 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. In addition, the compatibilizer coating compositions from which the compatibilizer coatings can 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 that can 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 compatibilizer coating composition can be an epoxy-containing material comprising at least two epoxy groups. Non-limiting examples of epoxy-containing materials comprising at least two epoxy groups can be represented by the following structural formulas I, II, or a mixture thereof:

\ / I o

(I)

R

<img file="BRPI0806374A2_D0003.tif" />

II (II) in which: (a) R¹ can represent a group, such as hydrogen or C 1 -C alkyl₃; (b) m can represent an integer ranging from 2 to 4; (c) A can represent a group, such as, (I) C alkylene₂-Ç₂₀, substituted C alkylene₂-Ç₂o, C cycloalkylene₃-Ç₂o, C-substituted cycloalkylene₃-Ç₂₀, a substituted or unsubstituted arylene group, such as phenylene or naphthylene, C 1 -C 3 aryl alkylene, C 1 aryl alkylene_xÇ₃ substituted, each of the alkylene and cycloalkylene substituents independently being carboxy, hydroxy, or C alkoxy_x-Ç₃, or C alkyl_x-Ç₃; (II) the group —C (= 0) R²(0 =) C-, where R² represents a group, such as arylene or C2-C20 alkylene; (III) the -R group³(OR³-) n or - (0R³) n-, in which R³ represents a group, such as C2-C alkylene₄ en represents an integer from 1 to 20; (IV) phtaioyl, isoftaioia, terephthaloyl, hydroxyl substituted phthaloyl, hydroxyl substituted isoftaioi, hydroxyl substituted terephthaloyl; or (V) a group represented by the following structural formula:

<img file="BRPI0806374A2_D0004.tif" />

in which each R⁴ and R⁵ independently represents a group, such as C alkyl_x-Ç₄, chlorine or bromine, each pq independently represents an integer ranging from 0 to 4; each independently represents a group, such as a divalent benzene group or a divalent cyclohexane group, and, when

<img file="BRPI0806374A2_D0005.tif" />

is a divalent benzene group, G will represent a group, such as, -O-, -S-, -S (O₂) -, -C (= 0) -, -CH₂-, -CH = CH-, C (CH₃)₂-, -C (CH₃) (Ç₆H₅)-, -(Ç₆H₄) -, or

<img file="BRPI0806374A2_D0006.tif" />

or when

<img file="BRPI0806374A2_D0007.tif" />

is a bivalent cyclohexane group, G will represent a group, such as -O-, -S-, -CH₂- or -C (CH₃)₂-; (d) B represents a group, such as C alkyl₂-Ç₂o, substituted C alkyl₂-Ç₂o, C cycloalkyl₃-Ç₂or substituted cycloalkyl of C₃-Ç₂o, aryl groups substituted or unsubstituted, phenyl and naphthyl, aryl alkyl of Ci ~ C₃, aryl Ci ~ C alkyl₃ substituted, each of said alkyl and cycloalkyl substituents being, independently, carboxy, hydroxy, C1- C alkoxy₃, or Ci-C alkyl₃.

The epoxy-containing material of the compatibilizer coating composition can also be represented by structural formulas I, II or a mixture thereof in which: R¹ it is hydrogen; A represents a group, such as, (R⁵),

<img file="BRPI0806374A2_D0008.tif" />

in which R⁴, R⁵, E and G can represent groups such as those discussed above, and p and q are defined above;

C alkylene₂-Ci₀, phenylene; -R³- (OR³) n^- or - (0R³) n^-/ which R³ and en are the same as defined above or phthaloyl; and B represents a group, such as C2-C10 alkyl, phenyl or C1-C3 phenyl alkyl.

Specific non-limiting examples of epoxy-containing material comprising at least two epoxy groups that can be used in the compatibilizer coating compositions may include glycerol polyglycidyl ether, diglycerol polyglycidyl ether, glycerol propoxylate triglycidyl ether, trimethylol propane triglycidyl ether, sorbitol polyglycidyl ether, polyglycidyl ether, polyglycidyl ether diglycidyl ether, diglycidyl poly (propylene glycol), diglycidyl ether, neopentyl glycol, N, N-diglycidyl-4-glycidyloxy-aniline, N, N'diglycidyl toluidine, 1,6-hexanediol diglycidyl ether, 1,2-cyclohexane diglycidyl carboxylate, diglycidyl bisphenol A (eg diglycidyl bisphenol A ether ), a polymer of diglycidyl bisphenol A, capped glycidyl poly (bisphenol A-co-epichlorohydrin), diglycidyl of a hydrogenated propylene oxide bisphenol A adduct, diglycidyl ester of terephthalic acid, 1,2,3,6-tetrahydrophthalate diglycidyl, spiro glycol diglycidyl ether, diglycidyl ether hydroquinone, and mixtures thereof.

Non-limiting examples of isocyanate-containing materials that can be used in the compatibilizer coating compositions of the present invention can include isocyanate-containing materials comprising at least one isocyanate group and at least one among a hydroxyl group, an acrylate group, an acid group, an acid group additional isocyanate, a thiol group, an amine group, an epoxy group, a silane group, a vinyl group, an allyl group, and a glycidyl group. When used herein, the term isocyanate-containing material includes materials containing at least one isocyanate group, which can 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 that can be used, may include: m-isopropenylα, α-dimethyl benzyl isocyanate; a product of the reaction of an acrylic functional monomer and isocyanic acid; a reaction product of an unsaturated monomer 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 above. Such isocyanate-containing materials and methods for preparing them are described in detail in US Patent No. 6,025,026 in column 6, line 37 through column 8, line 65, the disclosure of which is hereby specifically incorporated by reference.

For example, isocyanate-containing material can be selected from one or more polyisocyanates such as diisocyanates and triisocyanates including biurets and isocyanurates. Biurets of any suitable diisocyanate including 1,4-tetramethylene diisocyanate and 1,6-hexamethylene diisocyanate can be used as the isocyanate-containing material in the preparation of the reaction product of the present disclosure. Also, biurets of cycloaliphatic diisocyanates such as isophorone diisocyanate and 4,4-methylene-bis- (cyclohexyl isocyanate) can be used. Examples of suitable aralkyl diisocyanates from which biurets can be prepared are meta-xylylene diisocyanate and a, ct, α ', a'-tetramethyl-meta-xylylene diisocyanate. The diisocyanates themselves can be used as the isocyanate-containing material in the preparation of the reaction product of the present disclosure.

Trifunctional isocyanates can 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, an adduct cyclobutane diisocyanate;

trimethylol and tetramethyl xylene diisocyanate sold under the trade name CYTHANE 3160 by CYTEC Industries, and DESMODUR N 3300, which is the hexamethylene diisocyanate isocyanurate, obtainable from Bayer Corporation. In addition, polyisocyanates can include cyclic isocyanates, such as, for example, diisocyanate isocyanurates such as hexamethylene diisocyanate and isophorone diisocyanate.

polyisocyanate that can be used as the isocyanate-containing material can 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.

The isocyanate-containing material of the compatibilizer coating composition can 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, paraphenylene diisocyanate, 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 fumarate (ethyl isocyanate); isophorone diisocyanate, obtainable under the trade name DESMODUR PL 340 from Bayer Materialscience, Pittsburgh, PA; ethylene diisocyanate, 1.12 dodecane,

Cyclohexane 1,3-diisocyanate, cyclohexyl; Hexahydro toluene 2,4-diisocyanate; 1,3 hexahydro phenylene diisocyanate; Hexahydro phenylene 1,4-diisocyanate, perhydrodiphenyl methane 2,4'-diisocyanate, perhydrodiphenyl methane 4,4'-diisocyanate, naphthylene 1,5diisocyanate; and mixtures thereof.

Cyclohexane 1,3-diisocyanate, methyl 1,4 diisocyanate

When used here, the terms (meth) acrylic, (meth) acrylic or (meth) acrylate are intended to cover both the acrylic / acrylic / acrylate forms and the methacryl / methacrylic / methacrylate forms of the material indicated. Non-limiting examples of materials containing (meth) acrylate that can be used in compatibilizer coating compositions may include: acrylate and methacrylate monomers, including polyfunctional acrylates and methacrylates, for example, di, tri, tetra and pentafunctional acrylates and methacrylates.

The compatibilizer coating can be prepared using acrylic and methacrylic monomers or a mixture of acrylic and / or methacrylic monomers. The mixture of (meth) acrylic monomers can 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 that can be used in the compatibilizer coating compositions according to the present invention can be represented by the following general formula VI:

R⁸- (OC (= O) C (R⁹) = CH₂)_s (VI) in which R⁸ represents a group, such as an aliphatic or aromatic group containing from 2 to 20 carbon atoms and optionally from 1 to 20 alkyleneoxy bonds; R⁹ represents a group, such as hydrogen or an alkyl group containing 1 to 4 carbon atoms, es represents an integer ranging from 1 to 5. When s is greater than 1, R⁸ it will be a linking group that joins the acrylic functional groups. Typically, R⁹ is hydrogen or methyl, es 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:

ίο

H, C C-Ç — O — R¹¹—Oc — C =

CH, (VII) in which R¹⁰ and R¹² they can be the same or different and each one of them 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:

\ /'

R¹³

I (OCH₂CH)_Vch₃^λ'(VIII) in which 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; eu and v are numbers ranging from 0 to 20, for example, from 1 to 15, or from

<img file="BRPI0806374A2_D0009.tif" />

to 10. The values ​​of eu when calculated can be a fractional number.

The (meth) acrylates having a v are average numbers and an integer or an epoxy group can be represented by the following general formula IX:

H, C^:

-Co

- (R¹⁶O) w- (R^I7O) X — ch₂c — ch₂ (ix) in which R¹* and R^1Q they can be the same or different and each one independently represents a group, such as hydrogen or alkyl groups of 1 to 4 carbon atoms, for example, methyl; R¹⁶ and R¹⁷ may be alkylene groups containing 2 to 3 carbon atoms, for example, ethylene and propylene, ewex 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 o another will be 1, the group R¹⁶ or R¹⁷remainder can be an aromatic group having the following Formula X:

<img file="BRPI0806374A2_D0010.tif" />

for example, a group derived from the 2,2-diphenylene propane radical, whose phenyl groups can be substituted with C 1 to C alkyl groups₄ or with halogens, for example, methyl and / or chlorine.

The compatibilizer coating compositions may further comprise an aminoplastic resin. Aminoplastic resins include condensation products of amines or amides with aldehydes and have at least two reactive groups. Suitable aminoplastics can be prepared by reacting materials having NH groups, such as urea, melamine, benzoguanamine, glycouryl, and cyclic ureas, with carbonyl compounds 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 from other amines and amines can also be used, for example, aldehyde condensates from triazines, diazines, triazoles, guanadines, guanamines and melamines substituted with alkyl and aryl. Aminoplastic resins are commercially available from Cytec Industries, Inc., under the trade names CYMEL and RESIMENE. Non-limiting examples of such products include CYMEL® 345, 350 and / or 370 resins and RESIMENE® 717, 730 and / or resins

735. Suitable reactive functional groups on the aminoplastic resin include any of the reactive groups disclosed herein, for example, hydroxyl, acrylate, methacrylate, acid, isocyanate, thiol, amine, epoxy, silane, and glycidyl.

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

<td colspan="4">zirconates.</td>

<td>For example, 0</td><td>agent of</td><td>coupling can</td><td>be an agent</td>

<td>coupling</td><td>silane</td><td>having the formula</td><td>structural V</td>

<td>Following:</td><td>(R¹⁸O)_y-</td><td>Si- (R¹⁹)_Z (V)</td><td></td>

<td colspan="2">in which for each</td><td>/ * · 1 fi occurrence: R</td><td>represents,</td>

independently, 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, mercapto, halogen, ureido, or alkoxy; R¹⁹ independently represents 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 carbon atoms that are unsubstituted or substituted with epoxy, glycidoxy, amino, vinyl, benzine, styryl, (meth) acryloxy, mercapto, halogen, ureido, or alkoxy, or two R groups¹⁹ they can combine to form a C4-C7 cycloalkyl group or heterocyclic group in which the heteroatom is at least one among 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 compatibilizer coating composition does not comprise a coupling agent, the dendritic polymer of the compatibilizer coating composition may optionally comprise, in addition to one or more hydroxyl end groups, (meth) acrylate, carboxylic acid, isocyan, thiol, amine, epoxy, or glycidyl, at least one terminal silane group. Additionally or alternatively, at least one of the functional groups of the epoxy-containing material, the isocyanate-containing material, the (meth) acrylate-containing material, or the aminoplastic resin material of the compatibilizing coating composition may be a silane group.

As indicated above, the compatibilizer coating compositions that can be used to form the compatibilizer coatings can optionally comprise at least one of an initiator and a catalyst. In addition, when used here, the term catalyst refers to a substance that increases the rate of a chemical reaction without 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 that can facilitate attachment of the epoxy-containing material generating an acid by 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 Brönsted acid. In addition, if the compatibilizer coating composition comprises a silane coupling agent or at least partial hydrolyzate thereof (as discussed above), the acid generated by the initiator may also facilitate the condensation of the silane coupling agent by lowering the pH of the composition. When used herein with reference to coatings, coating compositions, or components thereof, the terms fixing, fixing, etc., are intended to include processes such as, but not limited to, curing, polymerization, crosslinking, and drying.

Although non-limiting here, it is considered that if, in addition to at least one epoxy-containing material, the compatibilizer coating composition comprises a dendritic polymer that includes (meth) acrylate end groups (e.g., an acrylated 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 fixation (for example, cross-linking) of the dendritic polymer, in addition to facilitating the fixation of material containing epoxy. A combination of an initiator that is capable of generating an acid and an initiator that is capable of generating a free radical can also be used.

The initiator can be a photoinitiator that adapts to generate an acid upon exposure to actinic radiation. Non-limiting examples of appropriate photoinitiators that can adapt to generate an acid upon exposure to actinic radiation include onium salts and iodosyl salts, aromatic diazonium salts, metallocene salts, o-nitro-benzaldehyde, sulfonate esters or aromatic alcohols containing a carbonyl group in 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 that can be used in conjunction with various non-limiting embodiments disclosed herein include diaryl iodonium salts and triaryl sulfonium salts. Other appropriate 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 is incorporated herein by reference. Non-limiting examples of triaryl sulfonium salts include triaryl sulfonium hexafluorophosphate salts and hexafluoroantimonate salts of triaryl sulfonium. Non-limiting examples of diaryl iodonium salts include: 4,4'-dimethyl diphenyl iodonium tetrafluoroborate salts, phenyl-4-octyloxyphenyl phenyl iodonium hexafluoroantimonate salts, hexodluorohydronate dodecyl diphenyl iodonium hexafluoroantimonate salts [(2tetradecanol) oxy] phenyl] phenyl iodonium, and mixing any of them.

Furthermore, where the compatibilizer composition comprises at least isocyanate-containing, the compatibilizer composition will generally comprise a catalyst, which can be a photo-catalyst, which can facilitate the fixation of the isocyanate-containing material. Non-limiting examples of catalysts coating an appropriate tin coating material and may include organic catalysts organic bismuth catalysts. Furthermore, if in addition to the isocyanate-containing material, the compatibilizer coating composition comprises an epoxy-containing material, a silane or hydrolyzate coupling agent at least partial thereof, and / or a dendritic polymer that includes acrylate end groups, the composition of compatibilizer coating may also comprise a primer that adapts to generate an acid, and that, optionally, can also generate a free radical, to facilitate the fixing of these materials. Non-limiting examples of suitable primers are presented above.

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

The compatibilizer coating compositions of the present invention can further comprise one or more additives that can assist in the processing and / or performance of the composition or a coating or an 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 control agents, leveling agents (such as, but not limited to, surfactants), free radical scavengers, and combinations and mixtures of any of them.

The compatibilizer coating comprising the dendritic polymer that is on at least a portion of the substrate surface can 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 an epoxy group; (c) an aminoplastic resin comprising at least two reactive functional groups; (d) a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and, optionally, (e) an initiator. For example, the dendritic polymer can be a dendritic polymer comprising at least one acrylate end group; the epoxy-containing material can be an epoxy-containing material comprising at least two epoxy groups; the aminoplastic resin can 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 hydrolyzate by the partial thereof, or a mixture thereof; and the initiator can be a photoinitiator adapted to generate an acid upon exposure to actinic radiation. Suitable non-limiting examples of dendritic polymers comprising at least one acrylate end 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 an acid by exposure to actinic radiation are shown in detail above.

In addition, the compatibilizer coating comprising the dendritic polymer that is on at least a portion of the substrate surface can be derived from a compatibilizer coating composition comprising: (a) a dendritic polymer comprising an acrylate end group; (b) an isocyanate-containing material comprising at least two isocyanate groups; (c) an aminoplastic resin comprising at least two reactive functional groups; (d) a silane coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and, optionally, (e) at least one of a catalyst and an initiator. For example, the dendritic polymer can be a dendritic polymer comprising at least one acrylate end 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 can 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 hydrolyzate by the partial thereof, or a mixture thereof; and the initiator can be a photoinitiator; and the catalyst can 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 end group, of isocyanate-containing materials comprising at least two isocyanate groups (which may be blocked or unblocked), of aminoplastic resins comprising at least two reactive functional groups, silane coupling, photoinitiators, and catalysts that can be used in conjunction with these non-limiting embodiments are shown in detail above.

In addition, the compatibilizer coating comprising the dendritic polymer that is on at least a portion of the substrate surface can be derived from a compatibilizer coating composition comprising: (a) a dendritic polymer comprising a (meth) acrylate end group; (b) a material containing (meth) acrylate 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 a partial hydrolyzate thereof, or a mixture thereof; and, optionally, (e) a primer, which can be, for example, a photoinitiator. Suitable non-limiting examples of dendritic polymers comprising a terminal (meth) acrylate group, of materials containing (meth) acrylate comprising at least two (meth) acrylate groups, of aminoplastic resins comprising at least two reactive functional groups, of coupling agents of silane, initiators, and more particularly photoinitiators, which can be used in conjunction with these non-limiting embodiments are shown in detail above.

The compatibilizer coating compositions disclosed herein may comprise, for example, at least 20 percent by weight of a dendritic polymer based on total solids, such as 20 to 80 percent by weight of the compatibilizer coating composition based on total solids, or 30 to 70 weight percent of the compatibilizer coating composition based on total solids.

Based on total solids, the compatibilizer coating composition can 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, of a material containing isocyanate, a material containing (meth) acrylate, the aminoplastic resin, or a mixture of any of them.

Based on total solids, the compatibilizer coating composition can 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 hydrolyzate at least partial, or mixing.

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

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 compatibilizer coatings can comprise a dendritic polymer or an aminoplastic resin.

material containing (meth) acrylate from the compatibilizer coating can be

For example, the composition of a dendritic polymer (such as those dendritic polymers functionalized with (meth) acrylate described above), or the compatibilizer coating composition may comprise a dendritic polymer comprising a functional group other than 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 an ophthalmic substrate surface, the compatibilizer coating being formed by a compatibilizer coating composition comprising: (I) an isocyanate-containing material comprising at least two groups isocyanate; (II) a material containing (meth) acrylate 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 a 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 compatibilizing coating opposite to the ophthalmic substrate.

For example, according to these unblocked incorporations43); a material (that is, applied.

limiting, the isocyanate-containing material of the compatibilizer coating composition may be an isocyanate-containing material comprising at least two isocyanate groups (which may or may not be blocked the material containing (meth) acrylate may be containing (meth) acrylate comprising at least two groups ( met) acrylate: the aminoplastic resin can be an aminoplastic resin comprising at least two reactive functional groups; the coupling agent, at least partially hydrolyzed therefrom, or a mixture thereof, may be a silane coupling agent; the initiator can be a photoinitiator; and the catalyst can be at least one of an organic tin catalyst or an organic bismuth catalyst. Non-limiting examples of these, as well as other materials containing isocyanate, materials containing (meth) acrylate, aminoplastic resins, coupling agents, initiators, and appropriate catalysts that may be present in the compatibilizer coating compositions according to these non-limiting incorporations are presented above.

Although non-limiting here, the compatibilizer coating that is on at least a portion of a substrate surface can also be an alignment coating for a functional organic coating comprising a liquid crystal material (a liquid crystal coating) when used herein. , the term alignment coating refers to a coating comprising at least partially ordered alignment means that can be used to confer an appropriate position or arrangement for another material or coating. When used here, the term ordering (and other forms thereof, for example, ordering, wages, etc.) means causing an appropriate position or arrangement, such as aligning with another structure or material, by some other force or effect. Therefore, when used here, ordering includes both contact methods for ordering a material, such as aligning the material with another structure or material, as well as non-contact methods for ordering a material, such as exposing the material to an external force or effect. (for example, polarized radiation, an electric or magnetic field, a shear force, etc.). The order may also include combinations of contact and non-contact methods. In addition, when used here, the term align (and other forms thereof, for example, alignment, aligned, etc.) means to cause an appropriate position or arrangement by interacting with another material, compound or structure. For example, although non-limiting here, liquid crystal coatings (i.e., coatings comprising a liquid crystal material) can be aligned at least partially by contact with the surface of an alignment coating. When 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 mesogens.

More specifically, since liquid crystal materials contain mesogens having structures such as disks or rods, a long rigid axis, and strong dipoles, liquid crystal materials are generally able to be ordered or aligned in order to acquire direction general. Therefore, a liquid crystal material can be ordered or aligned by interaction with an external force or with another structure (such as an alignment liner) such that the long axes of the material's mesogens (or some portion of the material) acquire general direction that it is usually parallel to a common axis. When used here, 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 can have a general direction even if there is some variation within the arrangement of the material or structure, as long as the material or structure, or some portion thereof, has at least one predominant arrangement. Non-limiting examples of liquid crystal materials that can be used to form liquid crystal coatings disclosed herein are presented 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 can be rubbed using, for example, a textured cloth, a velvet brush, or the like, or the surface can be textured. example, by cauterization, to desired for the compatibilizing surface. In addition, where the compatibilizer coating also serves as an alignment coating, the compatibilizer coating can be fixed at least partially before rubbing or texturing the coating.

The compatibilizer coatings or compatibilizer coating compositions from which they can be derived can be essentially free of photochromic materials. When used herein with respect to the various coatings described herein, the term essentially free (s) of photochromic materials means that the coating contains less than photochromatic of such materials or photochromatic. When used here, the term photochromatic means to have an absorption spectrum for at least visible radiation that varies in response to at least actinic radiation. When used here, the term photochromatic material means any substance that adapts to exhibit photochromatic properties, that is, that adapts to have an absorption spectrum for at least visible radiation that varies in response to at least actinic radiation. In addition, when used herein, the term photochromatic quantity means a quantity differently, as an amount of the photochromic material is not sufficiently sufficient to confer visibly discernible photochromic properties to a coating or other article in which the photochromic material is incorporated. Therefore, compatibilizer coatings and / or the compatibilizer coating compositions from which they can be derived that are essentially free of photochromatic materials may comprise less than a photochromatic amount of photochromatic materials or may be free of photochromatic materials, that is, they do not contain any materials photochromatic.

As discussed above, the present invention also provides optical elements comprising a substrate, such as, but not limited to those described above, a compatibilizer coating comprising a dendritic polymer on at least a portion of a substrate surface, which can be derived from the coating compositions compatibilizer, as discussed above, and a functional organic coating, other than an abrasion resistant coating, in contact with at least a portion of the compatibilizer coating in front of the substrate. When used herein, the term functional organic coating which gives a desired characteristic to an article to which it connects and comprises, predominantly, by weight percentage, an organic material (i.e., an organic or hydrocarbon compound). The functional organic coatings of the present invention can be derived from compositions comprising organic material, and which, comprise inorganic materials or other carbon compounds, such as, for example, other additives. Other additives suitable for use in the organic coating, for example, light stabilizing inhibitors (such as property one or predominantly one optionally, may functional may include, polymerization, solvents, such as, but not limited to, ultraviolet light absorbers and light stabilizers, such as hindered amine light stabilizers (HALS), thermal stabilizers, release agents, rheology control agents, leveling agents (such as, but not limited to, surfactants), free radical scavengers, and combinations and mixtures of any of them. The functional organic coating can be at least one of a photochromatic coating, an alignment coating and a liquid crystal coating. Non-limiting examples of such functional organic coatings are shown in detail below.

The functional organic coating that is in contact with at least a portion of the compatibilizer coating may be a photochromic coating. When used herein, the term photochromatic coating refers to a coating comprising a photochromatic amount of at least one photochromatic material. As discussed earlier, photochromic coatings can impart photochromatic 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 photochromatic material contained in the photochromic coating in its fundamental state form, and a second colored state that corresponds to the color of the photochromatic material contained in the photochromic coating in its basic form. activated state (that is, when exposed to actinic radiation). For example, if an optical element is an ophthalmic lens comprising the photochromic coating, the lens may change from a colorless state to a colored state when the user is exposed to UV radiation, for example, from sunlight, and may return to the state colorless when the user is not exposed to UV radiation.

Non-limiting examples of photochromic coating compositions that can be used to prepare photochromic coatings according to the non-limiting embodiments disclosed herein are described below. Such photochromic coating compositions are known and can be prepared with components according to methods well known and understood by those skilled in the art. For example, compositions of photochromic polyurethane coatings that can be used to prepare photochromic coatings according to the present invention can be produced by the catalyzed or non-catalyzed reaction of an organic polyol component and an isocyanate component in the presence of photochromatic materials. Materials and methods for the preparation of 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 can used to prepare the polyurethane coating are disclosed in US patents No. 4,889,413 (in column 2, row 42 to column 12, row 21) and 6,187,444 (in column 2, row 52 to column 12, row 15). Other isocyanate-containing coating compositions, such as mono-isocyanate coating compositions that 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 ( non-limiting examples of which are presented in the 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 shown in US patent No. 6,916,537 in column 7, line 38 through 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 shown in the US patent No. 6,916,537 in column 8, line 50 to column 9, line 44), which optionally comprises a copolymerizable monomer by addition (non-limiting examples of which are shown in US patent No. 6,916,537 in column 11, line 47 through column 20, line 43). The aforementioned disclosures herein are specifically incorporated by reference. Non-limiting examples of photochromatic aminoplastic resin coating composition that can be used to produce photochromatic coatings according to the present invention can be prepared by combining a photochromatic material with the functional component reaction product having at least two functional groups chosen from hydroxyl , carbamate, urea, or a mixture of any of them and an aminoplastic resin, for example, crosslinking agent described in US Patent No. 4,756,973, in column 4, row to column 7, row 3; in US Patent No. 6,506,488, in column 2, line 43 to column 12, line 23; and in US patent No. 6,432,544, in column 2, line 32 to column 14, line 5. The above-mentioned disclosures herein are specifically incorporated by reference.

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

Non-limiting examples of photochromatic poly (meth) acrylate coating composition considered for use in the preparation of photochromatic coatings of the present invention can be prepared by combining photochromatic materials 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; in 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 above-mentioned disclosures herein are specifically incorporated by reference.

Non-limiting examples of composition of photochromatic polyanhydride coatings that can be used in the preparation of photochromic coatings of the present invention can be prepared by reacting a component with hydroxyl functionality and a polymer component with anhydride functionality in a composition including at least one organic photochromatic material as described in US patent No. 6,432,544, in column 2, row 32 through column 14, row 5. Non-limiting examples of components with hydroxyl functionality, component with anhydride functionality, and other components that can be used to prepare photochromic polyanhydride coatings are disclosed in US Patent Nos. 4,798,745 (in column 2, line 67 through column 8, line 65), 4,798,746 (in column 2, row 32 to column 11, row 45), and 5,239,012 (in column 3, row 17 to column 6, row 52). Other suitable polyanhydride coating compositions are described in US Patent No. 6,436,525, in column 2, line 15 through column 11, line 60. The above-mentioned disclosures are incorporated specifically by reference.

Non-limiting examples of photochromatic poly (meth) acrylamide coatings compositions considered for use in the preparation of photochromatic coatings can be prepared by combining a photochromatic material with the reaction product initiated via free radicals of a polymerizable ethylenically unsaturated composition comprising N-alkoxymethyl ( met) acrylamide and at least one other copolymerizable ethylenically unsaturated monomer, as described in US patent no.

6,060,001, in column 2, row 6 to column 5, row 39. Methods for preparing polymers with Nalcoxymethyl (meth) acrylamide functionality are described in US Patent No. 5,618,586, in column 1, row 65 to column 7 , line 2. The aforementioned disclosures are incorporated specifically by reference.

Non-limiting examples of epoxy resin photochromic coating compositions that can be used to prepare photochromic coating of the present invention can be prepared by combining photochromic compounds with epoxy resin or with polyepoxides and curing agents as described in US Patent Nos. 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 aforementioned disclosures herein are specifically incorporated by reference.

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

Non-limiting examples of suitable photochromatic materials may include benzopyrans, naphthopyranes (for example, those disclosed in column 1, line 64 through column 13, line 36 of US Patent No. 5,658,501), melted indene naphthyranes (e.g. those disclosed in column 1, row 10 through column 12, row 57 of the US patent No. 5.6456767); spiropyranes (e.g., spiro (benzindoline) naphthyranes, spiro (indoline) benzopyranes, spiro (indoline) naphthyranes, spiro (indoline) quinopyranes, and spiro (indoline) pirans); oxazines; fulgides and fulgimides (for example, those disclosed in column 20, line 5 through column 21, line 38 of US patent No. 4,931,220); and metallic dithiozonates (for example, those disclosed coatings coatings in US Patent No. 3,361,706). The previous disclosures here are incorporated specifically by reference. Additional non-limiting examples of photochromatic compounds, polymerizable photochromatic compounds, and complementary photochromatic compounds that can be used in the present invention are described in US patents. 5,166,345 (in column 3, line 36 to column 14, line 3); 5,236,958 (in column 1, row 45 through column 6, row 65); 5,252,742 (in column 1, row 45 through column 6, row 65); 5,359,085 (in column 5, line 25 to column 19, line 55); 5,821,287 (in column 3, row 5 through column 11, row 39); 6,113,814 (in column 2, line 23 to column 23, line 28); 6,153,126 (in column 2, line 18 through column 8, line 60); 6,296,785 (in column 2, line 47 to column 31, line 5); 6,348,604 (in column 3, line 26 to column 17, line 15); and 6,353,102 (in column 1, row 62 through column 11, row 64). The aforementioned disclosures herein are specifically incorporated by reference.

The functional organic coating that may be in contact with at least a portion of the compatibilizer coating may be an alignment coating. As discussed earlier, the term alignment coating refers to a coating comprising an at least partially ordered alignment means that can be used to confer an appropriate position or arrangement for another material or coating. Non-limiting examples of alignment coatings include scrub-oriented alignment, photo-oriented alignment, and ordered liquid crystal alignment coatings. When used herein, the terms rub-guided alignment liner and rubbed alignment liner refer to a liner that is at least partially ordered by rubbing, or texturing differently, at least a portion of the liner surface. When used herein, the term photo-oriented alignment coating refers to a coating that is ordered at least partially by exposure to polarized actinic radiation. The ordered 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 non-limiting here, alignment coatings can impart desirable orientation properties to the optical elements to which they are attached.

For example, the functional organic coating that is in contact with at least a portion of the compatibilizer coating may be an alignment coating, and more specifically, it may be a scrub-oriented coating comprising a polyimide that is capable of being ordered at least partially by rubbing. . Also, the alignment coating can be a photo-oriented coating comprising a photo-orientation material that is capable of being at least partially oriented by exposure to polarized actinic radiation. When used herein, the term photoorientation material means a material that is able to be oriented at least partially by exposure to polarized actinic radiation. Non-limiting examples of photo-orientation materials include cinnamate derivatives, azobenzene derivatives, coumarin derivatives, and ferulic acid derivatives. For example, the photo-orientation material can be a cinnamate derivative, such as a poly (vinyl cinnamate), a poly (vinyl ester) of para-methoxy-cinnamic acid, or a poly (acrylic ester) of acid para-methoxy-cinnamic. Other non-limiting examples of appropriate photo-orientation materials and methods for forming photo-oriented alignment coatings are disclosed in US Patent No. 5,389,698, in column 1, line 35 to column 4, line 19, reference; Effects in Applications whose disclosure is incorporated by and in Kozenkov et al., Photoanisotropic

Poly (Vinyl-Cinnamate) Derivatives and Their, Mol. Cryst. Liq. Cryst., Volume 409 (2004) on pages 215-259 and 265, whose disclosure is incorporated herein by reference. In addition, the alignment coating may be 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.

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 compatibilizer coating is an alignment coating, the optical element may further comprise a liquid crystal coating comprising a liquid crystal material aligned at least partially that 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 can 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 to a material (such as, but not limited to, a monomer, oligomer, or polymer) that comprises liquid crystal mesogens. Non-limiting examples of liquid crystal materials that can be used to form liquid crystal coatings can include monomers, oligomers, and liquid crystal polymers, both lyotropic and thermotropic.

In a particular embodiment, the liquid crystal coating may comprise a thermotropic liquid crystal material.

Specific non-limiting examples of liquid crystal materials that can be used in conjunction with various non-limiting embodiments disclosed herein include monofunctional as well as polyfunctional liquid crystal monomers. In addition, the liquid crystal monomer can be a crosslinkable liquid crystal monomer, and it can also be a photo-crosslinkable liquid crystal monomer. When used herein, the term photo-crosslinkable means a material, such as a monomer, oligomer, or polymer that can be cross-linked by exposure to actinic radiation. For example, photo-crosslinkable liquid crystal monomers include those liquid crystal monomers that are crosslinkable by 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 the 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, ureas, vinyl groups, vinyl ethers, and mixtures of any of them. Non-limiting examples of photo-crosslinkable liquid crystal monomers suitable for use in at least partial coatings of the alignment features of the present invention can include liquid crystal monomers having functional groups chosen from acrylates, methacrylates, alkalis, epoxides, thiols, and mixtures any of them.

Liquid crystal oligomers and polymers are suitable for use in the present invention can include both main chain liquid crystal oligomers and polymers and side chain liquid crystal oligomers and polymers. Typically, although non-limiting here, in main chain liquid crystal oligomers and polymers, liquid crystal mesogens as disks or rods are located mainly in the main chain of the oligomer or polymer. Furthermore, although non-limiting here, in side chain liquid crystal oligomers and polymers, liquid crystal mesogens as disks or rods are located mainly in the side chains of the oligomer or polymer. In addition, liquid crystal oligomers and polymers can be crosslinkable, and can also be photo-crosslinkable. 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 and side chain oligomers and polymers having functional groups chosen from acrylates, methacrylates, groups allyl, allyl ethers, alkynes, amino groups, anhydrides, epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, ureas, vinyl groups, vinyl ethers, and mixtures of any of them. Non-limiting examples of photo-crosslinkable liquid crystal oligomers and polymers that are suitable for use according to the various embodiments disclosed herein include those oligomers and polymers having functional groups chosen from acrylates, methacrylates, alkalis, epoxides, thiols, and mixtures of any of the same . Further description of appropriate non-limiting examples of monomers, oligomers and liquid crystal polymers can be found in US Patent No. 7,044,599 B2, in column 8, row 4 to column 9, row 3, the disclosure of which is specifically incorporated herein by reference.

Liquid crystal mesogens that are suitable for use in the present invention can include thermotropic liquid crystal mesogens and lyotropic liquid crystal mesogens. Non-limiting examples of suitable thermotropic liquid crystal mesogens may include calamitic liquid crystal mesogens (either as a rod or rod), discotic crystal mesogens (or as a disc) and cholesteric liquid crystal mesogens.

Alternatively, as discussed earlier, the compatibilizer coating itself can be a scrub-oriented alignment coating. In addition, the functional organic coating that is in contact with the compatibilizer coating can be another alignment coating, for example, an ordered liquid crystal alignment coating or a photo-ordered alignment coating, or it can be a liquid crystal coating comprising a liquid crystal material which may be partially aligned with at least partially ordered compatibilizer coating. Although non-limiting here, lined liquid crystal coatings can confer certain desirable optical properties, such as, for example, varying the refractive index for the optical elements to which they are attached. In addition, as discussed in more detail below, the aligned liquid crystal coatings themselves can be used to align other materials or coatings to provide, for example and without limitation, polarizing coatings, photochromic and polarizing coatings, and photochromatic / dichroic coatings. Non-limiting examples of liquid crystal materials that can be used to form the aligned liquid crystal coatings are discussed in detail above. The lined liquid crystal coating may comprise a material adapted to exhibit dichroism, and at least a portion of the material adapted to exhibit dichroism can be at least partially aligned with at least a portion of the liquid crystal material at least partially aligned. When used herein, the term material adapted to exhibit dichroism means a material that is adapted to absorb one of two polarized components in the orthogonal plane of at least one radiation transmitted more strongly than the other. Non-limiting examples of materials that are adapted to exhibit dichroism can include dichroic dyes and photochromatic / dichroic dyes. When used herein, the term dichroic dye means a dye that has a generally constant absorption spectrum and is adapted to absorb one of two polarized components in the orthogonal plane of at least one radiation transmitted more strongly than the other. When used herein, the term photochromatic / dichroic dye means a dye that has an absorption spectrum for at least visible radiation that varies in response to at least actinic radiation and that absorbs one of two polarized components in the orthogonal plane of at least one transmitted radiation more strongly than the other in response to at least actinic radiation.

Non-limiting examples of dichroic dyes that can be used can include those disclosed in US Patent No. 7,044,599, in column 7, lines 18-56, which is incorporated herein specifically by reference.

Non-limiting examples of photochromatic / dichroic dyes that can be used may include those materials presented and described in US patent application publications No. 2005/0004361, from paragraph 27 to paragraph 158, and 2005/0012998 Al, from paragraph 89 to paragraph 251, which are hereby specifically incorporated by reference.

Although non-limiting here, the functional organic coating may be a polarizing coating comprising an aligned liquid crystal coating and an aligned dichroic dye. When used herein, the term polarizing coating refers to a coating that is adapted to confine the vibrations of the electromagnetic vector of light waves in one direction or plane. Generally, although not required, polarizing coatings comprising conventional dichroic dyes may have a 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 the US patent application publication No. 2005/0151926, from paragraph 10 to paragraph 159, which is specifically incorporated herein by reference.

The polarizing coating may further comprise a photochromic material. Where the photochromic material is present, the coating can be either a polarizing coating or a photochromatic coating, i.e., one that exhibits both conventional polarizing properties as well as conventional photochromatic 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 tint of the dichroic dye, and a second colored polarized state when exposed to actinic radiation due to the combined effect of the dichroic dye 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 colored polarized state when the user is not exposed to UV or actinic sunlight, to a second colored polarized state. when the user is exposed to UV or actinic radiation from sunlight. In addition, the functional organic coating may be a photochromatic / dichroic coating comprising an aligned liquid crystal coating including an aligned photochromatic / dichroic dye. When used herein, the term photochromatic / dichroic coating refers to a coating that is adapted to exhibit both photochromatic and polarizing properties in response to at least actinic radiation. For example, according to various non-limiting embodiments disclosed herein, the functional organic coating may be a photochromic / dichroic coating that is adapted to change reversibly from a first non-polarized, optically colorless state to a second colored polarized state in response to at least the actinic radiation. For example, if the optical element is an ophthalmic lens comprising the photochromic / dichroic coating, the lens may reversibly change from a non-polarized, optically colorless state when the user is not exposed to UV or actinic radiation, for example, sunlight , to a polarized colored state when the user is exposed to UV or actinic radiation, for example, from sunlight. Non-limiting examples of such coatings are described in US patent application publication No. 2005/0012998, from paragraph 11 to paragraph 442, which is hereby specifically incorporated by reference.

Other types of functional organic coatings that can be used in accordance with the present invention may include: paints, for example, a pigmented paste or liquid used for decorating, protecting, and / or identifying a substrate; and printing inks, for example, paste or pigmented liquid used to write and print on substrates, such as in the production of check marks on security documents, for example, documents such as bank notes, passports, driver's licenses, for which you may want authentication or authenticity verification.

compatibilizer. By functional in contact

In addition, the optical element may comprise at least one functional organic coating that is in contact with 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 example coating, the organic coating with at least a portion of the matching 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 that is in contact and aligned with at least a portion of the alignment coating. In addition, as discussed above, the lined liquid crystal coating may comprise a material adapted to exhibit dichroism, and at least a portion of the material adapted to exhibit dichroism can be at least partially aligned with at least a portion of the aligned liquid crystal material. at least partially.

In addition to the compatibilizer coatings and the functional organic coatings described above, at least one of a protective coating previously), and a transition coat, one of those discussed anti-reflection may portion of the coating element (such as coating being connected to at least one optical. When used here, the term transition coating refers to a coating that helps to create a gradient in properties between two coatings. For example, although non-limiting here, a transition coating can help create a gradient in hardness between a relatively relatively hard coating and a soft coating. Non-limiting examples of transition (which may also be bonding layers) include cured acrylate-based thin films, for example, such as those presented in US patent application publications nos 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 hereby specifically incorporated by reference.

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

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, can be on at least a portion of the abrasion resistant coating 12, and a functional organic coating 30, for example, a photochromic coating, a coating of alignment, or a liquid crystal coating, described herein, can be on at least a portion of the compatibilizer coating 20. In addition, as shown in Figure 1, a transition coating 40 can be on at least a portion of the functional organic coating 20.

In addition, as shown in Figure 1, a transition coating 40 can be on at least a portion of the functional organic coating 30, and a protective coating 50 can be on at least a portion of the transition coating 40. Still further, although not shown in Figure 1, an anti-reflection coating can be positioned on the protective coating 50 and / or on a surface of the substrate 10 opposite the surface 11.

Also, as shown in Figure 2, the optical element may comprise a substrate 210 resistant coating a portion of an additionally, as shown in the compatibilizer coating 220 dendritic polymer, described herein, may be on at least a portion of the abrasion resistant coating 212 and a functional organic coating 230, for example, a photo-oriented alignment coating, described herein, may be on at least a portion of the compatibilizer coating 220. In addition, as shown in Figure 2, a second functional organic coating 232, for example, an aligned liquid crystal coating, described herein, may be on at least a portion of the coating functional organic 230, and a protective coating 250, described herein, can be on at least one functional organic portion 232.

As shown in Figure 3, it will 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, can be on at least a portion of the coating comprising an abrasion 212 on at least surface 211 thereof.

Figure 2, one comprising one of the second coating the optical element can compatibilizer 320. Furthermore, as shown in Figure 3, a protective coating 350 can be on at least a portion of the functional organic coating 330. As discussed earlier, the present invention considers still 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 substrate surface, and forming a functional organic coating, other than a resistant coating to abrasion, on 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.

Also, methods are provided for forming an ophthalmic element comprising: forming a compatibilizer coating that is substantially free of photochromic materials on at least a portion of a surface of an ophthalmic substrate, the compatibilizer coating being derived from a compatibilizer coating composition comprising : (I) an isocyanate-containing material comprising at least two isocyanate groups; (II) a material containing (meth) acrylate 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 a partial hydrolyzate thereof, or a mixture thereof; and (V) at least one of an initiator and a catalyst; at least partially fixing at least a portion of the compatibilizer coating exposing the portion to at least one of UV and thermal radiation; and forming a functional organic coating, other than a duct coating, on at least a portion of the compatibilizer coating opposite the substrate.

As discussed earlier, 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.

The formation of the compatibilizer coating on at least a portion of the substrate surface may comprise applying a compatibilizer composition on at least one example, by coating one portion of the one or more of the substrate, by rotation coating, spray coating.

coating by coating by coating a portion of the coating by rotating and spraying, laminating, curtain coating, and dipping. Alternatively, the compatibilizer formation on at least the substrate surface may comprise mold casting or overmoulding.

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

Where the compatibilizer coating is formed by casting in a mold, one or more layers of a compatibilizer coating composition can be applied in an aqueous but 5,104,692 polymeric treatments.

mold, at least partially, and after that, a substrate can be poured over the coating. For example, according to a non-limiting embodiment, an optical resin that is used to form the substrate can be poured into the mold, onto the compatibilizer coating, and subsequently fixed at least partially to form the substrate.

Before forming the compatibilizer coating on at least a portion of the substrate surface, the surface can be cleaned and / or treated to provide a clean surface and a surface that can improve the adhesion of the compatibilizer coating on the substrate. Effective treatments and cleaning commonly used include, but are not limited to, ultrasonic washing with 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, for example, treatment with low temperature crown or plasma discharge; and chemical treatment that results in hydroxylation of the substrate surface, for example, by cauterizing the surface with an aqueous solution of alkali metal hydroxide, 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 12 weight percent, hydroxide alkali metal. See, for example, US Patent Nos. 3,971,872 (column 3, lines 13 to 25), 4,904,525 (column 6, lines 10 to 48), (column 13, lines 10 to 59) which describe the surface of organic materials These disclosures are hereby specifically incorporated by reference.

The substrate surface treatment can be a low temperature plasma treatment. Although not limited here, this method allows surface treatment to improve adhesion of a coating formed on it, and can be a clean and efficient way to change the physical surface, for example, wrinkling or chemically altering the surface without affecting the rest of the article . Inert gases, such as argon, and reactive gases, such as oxygen, have been used as the plasma gas. Inert gases can wrinkle the surface, while reactive gases (such as oxygen) can 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 limited here, it is considered that oxygen may provide a small but effective physical wrinkle of the surface along with a small but effective chemical modification of the surface. Those skilled in the art will understand that the extent of the wrinkling and / or chemical modification of the surface will be a function of the plasma gas and the operating conditions of the plasma unit (including the duration of treatment).

The surface of the substrate subjected to plasma treatment may be at room temperature or may be slightly preheated before or during plasma treatment. Although not limited here, according to several non-limiting embodiments, the temperature of the surface to be subjected to plasma treatment can be maintained at a temperature below a temperature at which the surface can be adversely affected (other than the intended increase in the surface area by wrinkling and minor chemical modification) by the plasma. Those skilled in the art can quickly select the operating conditions of the plasma unit, relative to the treated plastic substrate, to achieve an improvement in the adhesion of a film / coating superimposed on the plasma treated surface.

After forming the compatibilizer coating and before forming the functional organic coating, at least a portion of the compatibilizer coating can be fixed at least partially. For example, the at least partial attachment of 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. In addition, fixing of the compatibilizer coating can be performed using a double curing process, that is, using a two-step process involving a UV curing step and a thermal curing step. The curing steps in the double curing process can be performed in series, that is, one directly after the other, such that the matching coating is completely fixed (cured) before further processing, or alternatively, the curing steps can be carried out such that the compatibilizer coating is partially cured using the first curing step (either thermal or UV) before forming additional coatings on it. After that, the entire structure is subjected to a second curing step to complete the curing of the compatibilizing coating and to cure the additional coatings simultaneously. Such double curing processes are well known in the art and are described in more detail below.

When the compatibilizer coating composition comprises a dendritic 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 a partial hydrolyzate thereof, or a mixture thereof; and a photoinitiator adapted to generate an acid upon exposure to actinic radiation, the at least partial cure of at least a portion of the compatibilizer coating may comprise exposing the portion to UV radiation or electronic beam radiation (i.e., ionizing radiation), and may further understand exposing the portion to thermal radiation.

Also, when the compatibilizer 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 a partial hydrolyzate thereof, or a mixture thereof; a catalyst; and a photoinitiator, the at least partial cure of at least a portion of the compatibilizer coating may comprise exposing the portion to UV radiation and subsequently exposing the portion to thermal radiation. In addition, where the compatibilizer coating comprises an isocyanate-containing material and a (meth) acrylate-containing material (as discussed above), before forming the functional coating on the compatibilizer coating, the compatibilizer coating may be cured at least partially using a double cure in which the coating is first exposed to UV or electronic beam radiation and subsequently it is exposed to thermal radiation. Those skilled in the art will understand that UV curing requires the presence of at least one photoinitiator. The light curing process and examples of photoinitiators are disclosed in US Patent No. 6,602,603, column 12, lines 11 to 37 and line 41 through column 13, line 36, the disclosures of which are hereby incorporated by reference. Curing by electronic beam techniques does not require the presence of a photoinitiator. For example, the coating can be exposed to UV or electronic beam radiation to, at one stage, cure at least partially the materials containing (meth) acrylate of the composition, and subsequently expose to thermal radiation to, at another stage, cure at least partially the isocyanate-containing materials in the composition. These curing steps can be performed, for example, in series before forming the functional organic coating on it. Alternatively, one of the curing steps can be performed before forming the functional organic coating on the compatibilizer coating, and one of the curing steps can be performed after forming the functional organic compatible coating. For example, non-limiting incorporation, on the coating according to a compatibilizing coating can be exposed to UV radiation or electronic beam radiation before forming the functional organic coating on it, and after that, both coatings can be exposed to thermal radiation.

The functional organic coating that forms on at least a portion of the compatibilizer coating can be at least one of a photochromic coating, an alignment coating, and a liquid crystal coating.

Where the functional organic coating can be a photochromatic coating, the formation of the photochromatic coating may comprise applying a coating composition comprising a photochromatic amount of a photochromatic material to at least a portion of the substrate, for example, by one or more of the coating by rotation , spray coating, spin and spray coating, laminate coating, curtain coating, and dip coating.

Alternatively, the photochromic coating can be formed on the substrate by overmoulding. For example, a coating composition comprising a photochromatic amount of a photochromatic material can be applied to a mold and after that, a substrate can 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 can be placed in the mold such that there is a gap between the mold and a surface of the substrate and after that,

Additionally, at least one portion inject the photochromic coating composition into the slit to form the coating.

Additionally, a coating composition with less than a photochromatic amount of a photochromatic material, or without any photochromatic material, can be formed on the substrate surface, for example, by any of the previous methods, and thereafter, a photochromatic material. or an additional amount of a photochromic material can be absorbed by the coating to form the photochromic coating. Where the functional organic coating comprises an alignment coating, the formation of the alignment coating may comprise applying a coating composition comprising an alignment means to at least a portion of the compatible coating, ordering at least partially at least a portion of the alignment means , and at least partially curing at least a portion of the alignment means.

at least partial ordering of hair from the alignment means may occur before, during, or after at least partial curing of at least a portion of the alignment means.

For example, the formation of the alignment coating 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 for applying coating compositions described herein, and simultaneously ordering at least partially and curing at least partially at least a portion of the photo-orientation material by exposing the photo-orientation material to polarized plane UV radiation. For example, according to this non-limiting embodiment, the photoorientation material can be a material formed from a photo-orientable polymeric network (or PPN), such as those described in the US patent.

5,389,698, in column 2, row 1 to column 4, row 10; and in Kozenkov et al

Photoanisotropic Effects in Poly (Vinyl-Cinnamate) Derivatives and Their Applications, Mol. Cryst. Liq. Cryst., Volume 409 (2004) on pages 251-267, whose disclosures are hereby incorporated by reference.

Where the alignment coating comprises a photo-oriented alignment coating, forming the alignment coating 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 for applying coating compositions described herein, and ordering at least partially at least a portion of the photo-orientation material by exposing the photo-orientation material to polarized plane UV radiation, and subsequently curing at least partially the ordered portion of the photo-orientation material. For example, although non-limiting here, according to this non-limiting embodiment, the photo-orientation material can be an azobenzene derivative, as described in US patent No. 4,974,941 in the column whose disclosure comprises one by one. rotation, partially coated

2, line 28 to column 9, line 63, is incorporated by reference.

Where the alignment coating 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, on at least a portion of the compatibilizer coating, for example , by any of the methods for applying compositions described herein, cure at least a portion of the rotation-oriented alignment material, and subsequently, ordering at least a portion of the rotation-oriented alignment material by rubbing the portion with an appropriate textured cloth.

Where the alignment coating comprises a liquid crystal alignment coating, forming 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 of the methods for applying coating compositions described herein; ordering at least partially 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 partial curing of 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 the at least partial ordering of the liquid crystal material.

In addition, as discussed earlier, 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, on at least a portion of the alignment coating and aligning with the 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 can 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 an elevated temperature.

In addition, at least a portion of the liquid crystal material can be cured at least partially during or after alignment. For example, where the liquid crystal material comprises a photo-crosslinkable liquid crystal monomer, at least partial curing of 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.

As discussed earlier, the liquid crystal coating aligned in accordance with various non-limiting embodiments disclosed herein may further comprise a material adapted to exhibit dichroism. Material adapted to exhibit dichroism can be mixed and / or bonded with at least a portion of the liquid crystal material before applying the liquid crystal material to the substrate, and at least partially aligned with at least a portion of the liquid crystal material for form a functional organic coating, such as, for example, a polarizing coating or a photochromatic / dichroic coating. Additionally or alternatively, the material adapted to exhibit dichroism can be applied to the liquid crystal coating before or after alignment of the liquid crystal coating. For example, material adapted to exhibit dichroism can 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 liquids to form a functional organic coating, such as, for example, a polarizing coating or a photochromatic / dichroic coating. Non-limiting examples of materials adapted to exhibit dichroism are discussed in detail above.

In addition, 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 photochromatic material (i.e., to form a polarizing and photochromatic coating) . For example, the photochromic material can 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 photochromatic material can be absorbed by the liquid crystal coating or before or after aligning it with the alignment liner.

Additionally, as discussed earlier, at least compatibilizer coating may be less partially to form alignment before a portion of the ordered by the coating an

one forms less functional organic coating over at least the portion of the compatibilizer coating. For example, at least a portion of the compatibilizer coating may be ordered at least partially by rubbing or cauterizing a portion of the compatibilizer coating, typically after at least partially curing the portion of the compatibilizer coating composition. 0 functional organic coating that forms on at least a portion of compatibilizing coating ordered at least partially may be a coating of liquid crystals aligned at least partially, which may optionally include at least one material adapted to exhibit dichroism and / or a material Methods non-limiting aligned liquid crystals, which may include materials adapted to exhibit dichroism and / or photochromatic materials, are described above.

In addition, a liquid crystal coating can be applied to the compatibilizer coating without ordering the photochromic.

coatings partially to form at least 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 can be ordered at least partially, for example, by exposing the liquid crystal coating to at least one among one magnetic field, an electric field, or a shear force. As discussed above, such ordered liquid crystal coatings can be used as alignment coatings for another coating, such as, for example, another liquid crystal coating. In addition, such ordered liquid crystal coatings can be used without further modification, for example, to impart certain desired optical properties to the optical element (for example, a desired refractive index), or the ordered liquid crystal coating can 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 can be used to align a dichroic dye or a photochromatic / dichroic dye to produce a polarizing coating or a photochromatic / dichroic coating. In addition, although not required, one or more coatings, such as a transition coating, a protective coating, and / or an anti-reflective coating, can also be formed on the optical elements. For example, as described above with respect to Figure 1, a transition coating can be formed on at least a portion of the functional organic coating and a protective coating can be formed on at least a portion of the transition coating. Although non-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.

Various non-limiting embodiments of the present invention, or aspects of it, are more particularly described in the following non-limiting 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 presented in the claims, they will become obvious to those skilled in the art.

Examples

In Part 1 of the following examples, the materials and methods used to prepare coated lenses with and without primer are described. In Part 2, the methods used to test adherence are described, as well as the results reported in Table 1.

Part 1 - Lens Preparation

Seven pairs of lens substrates were used, each with a diameter measuring 74 mm and having the base curvature listed in Table 1. The lenses treated with a corona discharge from a Tantec corona unit operating at 60 Hz and 1, 3 kVA. The test lenses were then washed in an automatic process that rubbed the surface with soapy water, rinsed with deionized water, and air dried. Composition A spin-coated one of each pair of lenses to obtain a wet film weight of approximately 0.025 g.

Composition A was prepared by mixing in the following order in the quantities listed as a percentage by weight based on the total weight of the composition: 4 5.9 percent by weight of CN2302 reported as a polyester acrylate oligomer obtained from Sartomer Corporation, Exton, Pennsylvania ; 13.8 weight percent of test EPON® epoxy resin was for 15 seconds

828, reported as diglycidyl bisphenol A ether, obtained from Miller-Stephenson, Danbury, Connecticut; 32.1 weight percent SILQUEST A-187® reported as gamma-glycidoxy propyl trimethoxysilane, obtained from GE Silicones, Wilton Connecticut; and 8.3 percent by weight of triaryl sulfonium hexafluorophosphate salts mixed in 50 percent by weight of propylene carbonate obtained from Sigma Aldrich, St. Louis, Missouri.

Composition A coated lenses were placed approximately 20.32 cm (8 inches) from lens to lamp, under a 400 watt / inch type D iron iodide mercury bulb having a length of 15.24 cm (6 inches) for 30 seconds until cured.

These samples as well as the uncoated lenses were then coated with a solution of a photo-orientable polymeric mesh 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 rotation 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 (CO) oven 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.

After applying the photo-orientable polymeric net to each of the test lenses, at least partially, at least a portion of the photo-orientable polymeric net was exposed for 35 seconds to linearly polarized ultraviolet light from the same type D bulb mentioned previously, which was filtered with fused silica polarizer having a transmission 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 polymeric network, the lenses were cooled to room temperature.

Composition B was applied to the lenses by rotating 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 maintained at 65 ° C; 4.4 weight percent dichroic dyes formulated to produce a gray color were added; and mixed for 60 min. A liquid crystal monomer, 27.3 weight percent of liquid crystal monomer RM 105 was reported as having the molecular formula C₂₃H₂6C&gt; 6, which was obtained from EMD Chemicals, Inc., Gibbstown, New Jersey, and the composition was mixed for 30 min. Then, 27.2 weight percent liquid crystal monomer RM 257 reported as having the molecular formula C33H32O10, which was also obtained from EMD Chemicals, Inc., Gibbstown, New Jersey, was added and the composition was mixed for 30 min. Next, 1.1 weight percent bis- (2,6-dimethoxy benzoyl) phenyl phosphine oxide was added and the composition was mixed for 30 min.

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

The carrier UV curing line had a nitrogen atmosphere in which the oxygen level was less than 100 ppm. The carrier traveled at 7.2 mm / s under ultraviolet light from a 400 watt / inch (157.5 J / s / inch) type D 25.4 cm (10 inch) iron iodide mercury 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 15.24 cm x 5.08 cm (6 inches x 2 inches) area to expose the lens. A 300 nm filter was placed under the funnel to block UV wavelengths above 300 nm for the lenses. 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

The adherence of the coating formed by Composition B on the 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 uncoated with Composition A. In the primary test or dry test, a cutting tool made up of eleven Xacto® utility knife blades spaced 1 mm apart (end to end) and 0.65 mm thick was used to perform a first long cut, for example, from the center of the lens 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 hatch zones. A piece of Scotch® 250 tape (3M, St. Paul, Minnesota) 2.54 cm (1 inch) wide and 5 to 6.3 cm (2 to 2.5 inches) long was applied in the direction from the first cut that was pressed to smooth and avoid any bubbles. Before testing, the tape was stored at 23 ° C +/- 5 ° C with a relative humidity below 60%. The tape then hurts from the surface with a strong, fast 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 areas produced by the second and third cuts in a 90 ° direction with respect to the direction of the first tape. The tape was pulled in the same way as before. The resulting lenses were inspected using a point light source and a magnifying glass / magnifying glass. The average percentage of coating remaining from these 2 sites was determined and reported in Table 1 as results of the Primary adhesion test. After removing, drying and cooling the samples to room temperature, the above procedure was repeated. The average results of this test were reported in Table 1 as Secondary adherence test results.

Table 1

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

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

<td>1B^(1&gt;</td><td> 2,25</td><td> 100</td><td> 100</td>

<td>2A^(2&gt;</td><td> 6,00</td><td> 0</td><td> 0</td>

<td>2B^&lt;2&gt;</td><td> 6, 00</td><td> 100</td><td> 100</td>

<td>3Ã ^</td><td> 6,25</td><td> 100</td><td> 0</td>

<td>3b ^</td><td> 6, 25</td><td> 100</td><td> 100</td>

<td>4A &lt;⁴’</td><td> 6, 75</td><td> 98</td><td> 0</td>

<td>4B^&lt;4)</td><td> 6, 75</td><td> 100</td><td> 100</td>

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

<td>5B^&lt;5)</td><td> 4,00</td><td> 95</td><td> 95</td>

<td>6A^&lt;6)</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>7A⁽⁷⁾</td><td> 3,50</td><td> 0</td><td> 0</td>

<td>7B⁽⁷⁾</td><td> 3,50</td><td> 100</td><td> 100</td>

(1) Uncoated lenses made from CR-607 monomer sold by PPG Industries, Inc., Pittsburgh, Pennsylvania.

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

(3) Hard-coated lenses, prepared by Younger Optics (Torrance, California) made of polycarbonate monomer.

(4) Hard coated lenses, prepared by Gentex Optics, Inc., Dudley, Massachusetts, made of polycarbonate and designated as Poly GLC.

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

(6) Lenses prepared by Seiko Optical Products, Mahwah, New Jersey, and designated as uncoated MR10.

(7) Lenses prepared by Seiko Optical Products, Mahwah, New Jersey, and designated as hard coated MR10. As previously discussed, although the present invention is described here together with certain embodiments and examples, the present invention is not limited to the particular embodiments and examples disclosed, but intends to cover modifications that are within the spirit and scope of the invention, defined by the appended claims. . In addition, it should be understood that the present description illustrates aspects of the invention relevant to a clear understanding of the invention. Consequently, certain aspects of the invention that would be obvious to those skilled in the art and that, therefore, would not facilitate a better understanding of the invention were not presented in order to simplify the present description.