Compositions with high refractive index and high abbe number

Abstract

To provide an ophthalmic device comprising a composition which is produced by free radical polymerization of a reactive monomer mixture and which has both a high refractive index and a high Abbe number.SOLUTION: An ophthalmic device comprises: (a) at least one hydrophobic monomer; (b) at least one hydrophilic monomer, which is poly(ethylene glycol) methyl ether methacrylate; and (c) a cross-linking agent, which is tricyclo[5.2.1.02,6]decanedimethanol di(meth)acrylate.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] (CROSS REFERENCE TO RELATED APPLICATIONS) This application claims priority to U.S. Provisional Patent Application No. 62 / 843,054, filed May 3, 2019, the entire contents of which are incorporated herein by reference.

[0002] FIELD OF THEINVENTION The present disclosure relates to copolymers made from reactive monomer mixtures that, when polymerized, form acrylic materials with high refractive index and high Abbe number. These materials, which may have editable refractive index, are designed for use in ophthalmic devices such as intraocular implants or lenses. [Background technology]

[0003] Cataract surgery is typically performed to replace the natural eye lens, which has become opaque. The material used to replace the natural lens must be soft and have good flexibility so that once formed into a lens it can be folded and passed through an incision that is typically about 2 mm. Additionally, the material must have good transparency and little to no glitter. Having a high refractive index allows thinner lenses to be used. Materials with high Abbe numbers exhibit less dispersion. This can result in improved optical results and less light scattering. Combining a high refractive index with a high Abbe number gives the material favorable optical properties.

[0004] One of the first patents in this area, U.S. Patent No. 4,573,998 (Mazzocco), discloses a deformable intraocular lens that can be rolled to fit through a relatively small incision. The deformable lens is inserted into the eye while held in a rolled configuration and released into the eye chamber. The elasticity of the lens causes it to return to its molded shape after insertion into the eye. Mazzocco discloses suitable materials for the deformable lens, including polyurethane elastomers, silicone elastomers, hydrogel polymer compounds, organic or synthetic gel compounds, and combinations thereof.

[0005] Friction within the delivery device and by the force of the physician during delivery can damage the lens. To overcome this challenge, some delivery devices are provided with additional lubricity through coatings. For example, U.S. Patent No. 8,323,799 (Hu) discloses a soft, flexible, highly lubricious coating for polymer IOL insertion cartridges that allows the IOL to be easily inserted through a small hole cartridge suitable for use in small (less than 3 mm) incisions. While such coatings are helpful, there is a need to further reduce the frictional forces imposed on the lens during insertion. Summary of the Invention [Problem to be solved by the invention]

[0006] Thus, there is a need for materials with relatively high refractive indices and Abbe numbers that can be used to form flexible intraocular lenses that can be easily rolled or folded into a configuration that fits through a small incision. There is also a need for such materials to have internal lubricity. [Means for solving the problem]

[0007] In certain embodiments, the present disclosure provides a method for the preparation of a pharmaceutical composition comprising: (A) a composition ("Composition (A)") prepared by free radical polymerization of a reactive monomer mixture comprising: (i) at least one cycloaliphatic (meth)acrylate; (ii) at least one aromatic (meth)acrylate; (iii) at least one aliphatic (meth)acrylate; and (iv) at least one crosslinker; and exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39; or (B) a composition ("Composition (B)") prepared by free radical polymerization of a reactive monomer mixture comprising: (i) at least one cycloaliphatic (meth)acrylate; (ii) at least one aliphatic (meth)acrylate; and (iii) at least one crosslinker; and exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39; (C) (i) at least one hydrophobic monomer; and (ii) at least one acrylate monomer of formula (I):

[0008] [ka] In the formula, R 1 is selected from hydrogen and methyl; R 2 is a non-aromatic moiety having at least one carbon-carbon double bond; and (iii) at least one crosslinker; (D) a composition ("Composition (D)") prepared by free radical polymerization of a reactive monomer mixture comprising: (i) at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings; (ii) at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers, and any combination thereof; and (iii) at least one crosslinker, the composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39; or (E) (i) at least one hydrophobic monomer; (ii) at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers, and any combination thereof; and (iii) tricyclo[5.2.1.0 2,6 ] and a decanedimethanol di(meth)acrylate crosslinker, and the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39 ("Composition (E)").

[0009] In certain embodiments, the present disclosure provides composition (A), composition (B), composition (C), composition (D), or composition (E). In certain other embodiments, the device is an ophthalmic device. In certain embodiments, the ophthalmic device comprises a lens, inlay, outlay, or insert selected from an intraocular implant or lens, a contact lens, a corneal inlay, a corneal outlay, and a corneal insert. In certain embodiments, the ophthalmic device is an intraocular implant or lens. More specifically, the present disclosure also provides an intraocular implant and / or lens made at least partially or completely from composition (A), composition (B), composition (C), composition (D), or composition (E).

[0010] In yet another embodiment, the present disclosure provides a method for making an ophthalmic device, the method comprising: (a) providing any one of composition (A), composition (B), composition (C), composition (D), or composition (E); and (b) forming an ophthalmic device from any one of the compositions. In another embodiment, the presently disclosed subject matter provides a method for making an ophthalmic device, the method comprising: preparing a blank from any one of composition (A), composition (B), composition (C), composition (D), or composition (E); and (b) machining an ophthalmic device from the blank. In another embodiment, the presently disclosed subject matter provides a method for making an ophthalmic device, the method comprising molding an ophthalmic device from any one of composition (A), composition (B), composition (C), composition (D), or composition (E).

[0011] In yet other embodiments, the presently disclosed subject matter provides a method for making an ophthalmic device, the method comprising: (a) molding the ophthalmic device from any one of composition (A), composition (B), composition (C), composition (D), or composition (E); and (b) refining the molded lens surface by machining.

[0012] In certain embodiments of either method, the method further comprises extracting the ophthalmic device with a solvent. In certain embodiments, the method further comprises hydrating the extracted ophthalmic device with at least one aqueous solution. In certain embodiments, the method further comprises irradiating using a laser. In more specific embodiments, the method further comprises sterilizing the ophthalmic device. [Brief description of the drawings]

[0013] [Figure 1] 1 shows the level of micro-glossides by dark field microscopy. [Diagram 2] 1 shows the macrocrystal levels of Example 35 by dark field microscopy. [Diagram 3]1 shows the levels of macrocrystals for Examples 37-43 by dark field microscopy. [Figure 4] 1 shows the levels of macrocrystals for Examples 44-51 by dark field microscopy. [Diagram 5] 1 shows the levels of macrocrystals for Examples 45, and 52-55 by dark field microscopy. [Figure 6] 1 shows the levels of microcrystals for Examples 66 and 70 by dark field microscopy. [Figure 7] 1 shows the levels of macrocrystals for Examples 72-74 by dark field microscopy. [Figure 8] 1 shows the levels of macrocrystals for Examples 75-77 by dark field microscopy. [Figure 9] 1 shows the levels of macrocrystals for Examples 78-80 by dark field microscopy. [Figure 10] 1 shows the levels of macrocrystals for Examples 81-83 by dark field microscopy. [Figure 11] 1 shows the macrocrystal levels of Example 84 by dark field microscopy. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] It is to be understood that the present disclosure is not limited to the details of construction or process steps set forth in the following description, as the present disclosure is capable of other embodiments and of being practiced or carried out in various ways using the teachings set forth herein.

[0015] A.Definition The following definitions are provided for terms used in this disclosure.

[0016] Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which this disclosure belongs. The definition of polymer is consistent with the definition disclosed in Compendium of Polymer Terminology and Nomenclature, IUPAC Recommendations 2008, edited by: Richard G. Jones, Jaroslav Kahovec, Robert Stepto, Edward S. Wilks, Michael Hess, Tatsuki Kitayama, and W. Val Metanomski. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference.

[0017] The term "reactive monomer mixture" refers to a mixture of components (both reactive and non-reactive) that, when mixed and subjected to polymerization conditions, form the compositions and ophthalmic devices disclosed herein. The reactive mixture can include reactive components such as monomers, macromers, prepolymers, crosslinkers, initiators, diluents, and additional components including, but not limited to, wetting agents, release agents, light absorbing compounds such as dyes, ultraviolet-high energy visible light (UV / HEV) absorbers, pigments, dyes, and photochromic compounds, any of which can be reactive or non-reactive and can be retained in the resulting biomedical device, e.g., ophthalmic device, as well as active ingredients including pharmaceutical and nutraceutical compounds, and optional diluents. It will be understood that various additives may be added based on the biomedical device to be produced and its method of use. In some embodiments, the concentration of the components of the reactive mixture is given in weight % of all components in the reaction mixture, excluding the diluent. When a diluent is used, the concentration of the components is given as weight % based on the amount of all components in the reaction mixture and diluent.

[0018] "Reactive components" are components in the reactive monomer mixture that become part of the structure of the polymer network of the resulting composition through covalent or hydrogen bonding. Diluents and processing aids that do not become part of the structure of the polymer are not reactive components.

[0019] As used herein, the term "(meth)" refers to any methyl substitution. Thus, a term such as "(meth)acrylate" refers to both methacrylate and acrylate.

[0020] Wherever a chemical structure is depicted, it should be understood that the disclosed options for the substituents in the structure may be combined in any combination. * and R ** and each of these contains a list of three possible groups, then nine combinations are disclosed. The same is true for combinations of features.

[0021] General formula [ *** ] n When a subscript, such as "n" in: is used to denote the number of repeating units in a chemical formula for a polymer, the formula should be interpreted as representing the number average molecular weight of the polymer.

[0022] The term "individual" includes human and non-human vertebrates.

[0023] The term "biomedical device" refers to any article designed to be used either in or on mammalian tissue or fluid, preferably in or on human tissue or fluid. Examples of these devices include, but are not limited to, wound dressings, sealants, tissue prostheses, drug delivery systems, coatings, adhesion barriers, catheters, implants, stents, and ophthalmic devices such as intraocular implants, intraocular lenses, and contact lenses. The biomedical device can be an ophthalmic device, in particular an ophthalmic implant or ophthalmic glasses made from the reactive monomer compositions described herein.

[0024] The term "ocular surface" includes the superficial and glandular epithelium of the cornea, conjunctiva, lacrimal gland, accessory lacrimal gland, nasolacrimal duct, and meibomian gland, as well as their apical and basal matrices, puncta, and adjacent or associated structures including the eyelids, which are connected as a functional system by both the continuity of the epithelium through innervation and by the endocrine and immune systems.

[0025] The term "ophthalmic device" refers to any apparatus that resides in or on the eye or any part of the eye, including the ocular surface. These devices may provide optical correction, appearance enhancement, vision enhancement, therapeutic effects (e.g., as a dressing), or delivery of active ingredients such as pharmaceutical and nutraceutical ingredients, or any combination of the foregoing. Examples of ophthalmic devices include, but are not limited to, lenses, optics, and ocular inserts (including, but not limited to, punctal plugs). "Lens" includes soft contact lenses, hard contact lenses, hybrid contact lenses, intraocular lenses, and overlay lenses. Ophthalmic devices may include intraocular implants, intraocular lenses, or contact lenses.

[0026] The term "contact lens" refers to an ophthalmic device that can be placed on the cornea of ​​an individual's eye. A contact lens can provide corrective, cosmetic, or therapeutic benefits, including wound healing, delivery of drugs or nutritional supplements, diagnostic evaluation or monitoring, ultraviolet (UV) absorption, reduction of visible (VIS) light or glare, or any combination thereof. A contact lens can be of any suitable material known in the art and can be a soft lens, a hard lens, or a hybrid lens that contains at least two separate portions with different physical, mechanical, or optical properties, such as elastic modulus, water content, light transmission, or a combination thereof.

[0027] "Intraocular lens" means a lens that is implanted within the eye. In some embodiments, an intraocular lens is implanted in the eye to replace an existing lens (e.g., because the existing lens has become clouded due to a cataract, or as a form of refractive surgery to change the refractive power of the eye, etc.).

[0028] "Target macromolecule" refers to a macromolecule that has been synthesized from a reactive monomer mixture that includes monomers, macromers, prepolymers, crosslinkers, initiators, additives, diluents, and the like.

[0029] The term "polymerizable compound" means a compound that contains one or more polymerizable groups. This term includes, for example, monomers, macromers, oligomers, prepolymers, crosslinkers, and the like.

[0030] A "polymerizable group" is a group capable of undergoing free radical and / or ionic polymerization (e.g., cationic polymerization), e.g., chain growth polymerization, such as a carbon-carbon double bond that can polymerize when subjected to radical polymerization initiation conditions. Non-limiting examples of free radical reactive groups include (meth)acrylates, styrenes, vinyl ethers, (meth)acrylamides, N-vinyl lactams, N-vinyl amides, O-vinyl carbamates, O-vinyl carbonates, and other vinyl groups. Preferably, the free radical polymerizable group comprises (meth)acrylates, (meth)acrylamides, N-vinyl lactams, N-vinyl amides, and styryl functional groups, and mixtures of any of the foregoing. More preferably, the free radical polymerizable group comprises (meth)acrylates, (meth)acrylamides, and mixtures thereof. The polymerizable group may be unsubstituted or substituted. For example, the nitrogen atom in (meth)acrylamides may be bonded to hydrogen, or the hydrogen may be substituted with alkyl or cycloalkyl (which may themselves be further substituted).

[0031] Any type of free radical polymerization can be used, including but not limited to bulk, solution, suspension, and emulsion, as well as any of the controlled radical polymerization techniques, such as stable free radical polymerization, nitric oxide mediated living polymerization, atom transfer radical polymerization, reversible addition-fragmentation chain transfer polymerization, organotellurium mediated living radical polymerization, etc.

[0032] A "monomer" is a monofunctional molecule that can undergo chain growth polymerization, particularly free radical polymerization, thereby creating repeating units within the chemical structure of a target macromolecule. Some monomers have difunctional impurities that can act as crosslinkers. A "hydrophilic monomer" is a monomer that, when mixed with deionized water at 25°C at a concentration of 5% by weight, gives a clear, single-phase solution. A "hydrophilic component" is a monomer, macromer, prepolymer, initiator, crosslinker, additive, or polymer that, when mixed with deionized water at 25°C at a concentration of 5% by weight, gives a clear, single-phase solution. A "hydrophobic component" is a monomer, macromer, prepolymer, initiator, crosslinker, additive, or polymer that is slightly soluble or insoluble in deionized water at 25°C.

[0033] A "macromolecule" is an organic compound having a number average molecular weight greater than 1500 Daltons, and may be reactive or non-reactive.

[0034] A "macromonomer" or "macromer" is a macromolecule having one group capable of undergoing chain growth polymerization, particularly free radical polymerization, thereby creating a repeating unit within the chemical structure of a target macromolecule. Generally, the chemical structure of a macromer is different from the chemical structure of a target macromolecule, i.e., the repeating units of the pendant groups of the macromer are different from the repeating units of the target macromolecule or its backbone. The only difference between a monomer and a macromer is one of the chemical structure of the pendant groups, the molecular weight, and the molecular weight distribution. As a result, and as used herein, the patent literature sometimes defines a monomer as a polymerizable compound having a relatively low molecular weight of about 1,500 daltons or less, which essentially includes some macromers. Specifically, monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane (molecular weight = 500-1500 g / mol) (mPDMS) and mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether terminated mono-n-butyl terminated polydimethylsiloxane (molecular weight = 500-1500 g / mol) (OH-mPDMS) may be referred to as monomers or macromers. Additionally, the patent literature sometimes defines macromers as having one or more polymerizable groups, essentially expanding the general definition of macromer to include prepolymers. As a result, and as used herein, difunctional and multifunctional macromers, prepolymers, and crosslinkers may be used interchangeably.

[0035] A "polymer" is a target macromolecule made up of repeating units of the monomers used during polymerization.

[0036] A "homopolymer" is a polymer made from one monomer, a "copolymer" is a polymer made from two or more monomers, and a "terpolymer" is a polymer made from three monomers. A "block copolymer" consists of compositionally distinct blocks or segments. A diblock copolymer has two blocks. A triblock copolymer has three blocks. A "comb or graft copolymer" is made from at least one macromer.

[0037] A "repeating unit" is the smallest group within a polymer that corresponds to the polymerization of a particular monomer or macromer.

[0038] An "initiator" is a molecule that is decomposable into radicals that can subsequently react with monomers to initiate a free radical polymerization reaction. Thermal initiators decompose at a specific rate depending on the temperature, and typical examples are azo compounds such as 1,1'-azobisisobutyronitrile and 4,4'-azobis(4-cyanovaleric acid), peroxides such as benzoyl peroxide, tert-butyl peroxide, tert-butyl hydroperoxide, tert-butyl peroxybenzoate, dicumyl peroxide, and lauroyl peroxide, peracids such as peracetic acid and potassium persulfate, and various redox systems. Photoinitiators decompose by a photochemical process, and typical examples are derivatives of benzil, benzoin, acetophenone, benzophenone, camphorquinone, and mixtures thereof, as well as various monoacyl and bisacylphosphine oxides, and combinations thereof.

[0039] A "crosslinker" is a di- or polyfunctional monomer or macromer that can undergo free radical polymerization at two or more positions on the molecule, thereby creating branch points and polymer networks. Common examples are ethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, methylene bisacrylamide, triallyl cyanurate, etc.

[0040] A "prepolymer" is a reaction product of monomers that contain remaining polymerizable groups that can undergo further reaction to form a polymer. The terms "reactive mixture" and "reactive monomer mixture" refer to a mixture of components (both retained and unretained) that, when mixed and subjected to polymerization conditions, results in the formation of a polymer network and the biomedical devices, ophthalmic devices, intraocular implants, contact lenses, and intraocular lenses made therefrom. Reactive mixtures can include retained components such as monomers, macromers, prepolymers, crosslinkers, and initiators; additives such as wetting agents, polymers, light absorbing compounds such as dyes, UV / HEV absorbers, pigments, photochromic compounds, pharmaceutical compounds, and / or nutraceutical compounds, any of which can be reactive or non-reactive, but can be retained in the resulting biomedical device. Reactive mixtures can also contain unretained components, such as diluents, that are intended to be removed from the device prior to use. It will be understood that a variety of additives can be added based on the biomedical device being made and its intended use. The concentrations of the components of the reactive mixture are expressed as weight percentages of all components retained in the reactive mixture, and therefore exclude unretained components such as diluents. If diluents are used, their concentrations are expressed as weight percentages based on the amounts of all components in the reactive mixture (including the diluents).

[0041] "Retained components" are the polymerizable compounds in the reactive mixture (such as monomers, macromers, oligomers, prepolymers, and crosslinkers) and any other components in the reactive mixture that are intended to be substantially retained in the polymer network after polymerization and all purification steps (such as extraction steps) and packaging steps are complete. Retained components can be retained in the polymer network by covalent bonds, hydrogen bonds, electrostatic interactions, formation of an interpenetrating polymer network, or any other method. Components that are intended to be released from the biomedical device once used are still considered "retained components". For example, pharmaceutical and nutraceutical compounds in contact lenses that are intended to be released during wear are considered "retained components". Components that are intended to be removed from the polymer network during the manufacturing process (such as by extraction), such as diluents, are "non-retained components".

[0042] The term "multifunctional" refers to a component having two or more polymerizable groups. The term "monofunctional" refers to a component having one polymerizable group.

[0043] The terms "halogen" or "halo" refer to fluorine, chlorine, bromine, and iodine.

[0044] "Alkyl" or "aliphatic" are used interchangeably herein and refer to an optionally substituted straight or branched chain alkyl group containing the indicated number of carbon atoms. If no number is indicated, the alkyl (including any optional substituents on the alkyl) can contain any of 1-16 carbon atoms, including 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, and 16 carbon atoms. Preferably, the alkyl group contains 1-10 carbon atoms, including 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10 carbon atoms, alternatively 1-8 carbon atoms, including 1, 2, 3, 4, 5, 6, 7, and 8 carbon atoms, alternatively 1-6 carbon atoms, including 1, 2, 3, and 4 carbon atoms, or alternatively 1-4 carbon atoms, including 1, 2, 3, and 4. Examples of alkyl include methyl, ethyl, propyl, isopropyl, butyl, iso-, sec- and tert-butyl, pentyl, hexyl, heptyl, 3-ethylbutyl, and the like. Examples of substituents on alkyl include one, two, or three groups independently selected from hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, thioalkyl, carbamate, carbonate, halogen, phenyl, benzyl, and combinations thereof. "Alkylene" refers to a divalent alkyl group, such as -CH-, -CHCH-, -CHCHCH-, -CHCH(CH)CH-, and -CHCHCHCHCH-.

[0045] "Haloalkyl" refers to an alkyl group as defined above substituted with one or more halogen atoms, each halogen being independently F, Cl, Br, or I. A preferred halogen is F. Preferred haloalkyl groups contain 1 to 6 carbons, more preferably 1 to 4 carbons, and even more preferably 1 to 2 carbons. "Haloalkyl" includes perhaloalkyl groups such as -CF3- or -CF2CF3-. "Haloalkylene" refers to a divalent haloalkyl group such as -CH2CF2-.

[0046] "Hydroxy" refers to the group --OH.

[0047] "Hydroxyalkyl" refers to an alkyl group, as defined herein, substituted with at least one hydroxy group. Representative examples of hydroxyalkyl include, but are not limited to, hydroxymethyl, 2-hydroxyethyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, 2,3-dihydroxypentyl, 4-hydroxybutyl, 2-ethyl-4-hydroxyheptyl, 3,4-dihydroxybutyl, and 5-hydroxypentyl.

[0048] "Cycloalkyl" or "alicyclic" are used interchangeably herein to mean an optionally substituted cyclic hydrocarbon containing the indicated number of ring carbon atoms. If no number is indicated, the cycloalkyl can contain 3 to 20 ring carbon atoms (e.g., 3 to 12 ring carbon atoms). The alicyclic group can be monocyclic, bicyclic, tricyclic, bridged, fused, and / or spirocyclic. The alicyclic group can also have one or more double bonds, provided that the group is not fully aromatic. Preferred monocyclic alicyclic groups are preferably C3-C8 cycloalkyl groups, C3-C7 cycloalkyl, more preferably C4-C7 cycloalkyl, and even more preferably C5-C6 cycloalkyl. Examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of substituents on a cycloalkyl include one, two, or three groups independently selected from alkyl, hydroxy, amino, amido, oxa, carbonyl, alkoxy, thioalkyl, amido, carbamate, carbonate, halo, phenyl, benzyl, and combinations thereof. "Cycloalkylene" refers to a divalent cycloalkyl group, such as 1,2-cyclohexylene, 1,3-cyclohexylene, or 1,4-cyclohexylene.

[0049] "Heterocycloalkyl" refers to a cycloalkyl ring or ring system as defined above in which at least one ring carbon is replaced with a heteroatom selected from nitrogen, oxygen, and sulfur. The heterocycloalkyl ring is optionally fused or otherwise attached to other heterocycloalkyl rings and / or non-aromatic hydrocarbon rings and / or phenyl rings. Preferred heterocycloalkyl groups have 5 to 7 members. More preferred heterocycloalkyl groups have 5 or 6 members. Heterocycloalkylene refers to a divalent heterocycloalkyl group.

[0050] "Aryl" refers to an optionally substituted aromatic hydrocarbon ring system containing at least one aromatic ring. The aryl group contains the indicated number of ring carbon atoms. If no number is indicated, the aryl may contain 6 to 14 ring carbon atoms. The aromatic ring may be optionally fused or otherwise attached to other aromatic or non-aromatic hydrocarbon rings. Examples of aryl groups include phenyl, naphthyl, and biphenyl. Preferred examples of aryl groups include phenyl. Examples of substituents on an aryl include one, two, or three groups independently selected from alkyl, hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, thioalkyl, carbamate, carbonate, halo, phenyl, benzyl, and combinations thereof. "Arylene" refers to a divalent aryl group, such as 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.

[0051] "Arylalkyl" means an aryl group, as defined herein, appended to the parent molecular moiety through an alkyl group, as defined herein. Representative examples of arylalkyl include phenylmethyl (i.e., benzyl), phenylethyl, and phenylpropyl.

[0052] "Heteroaryl" refers to an aryl ring or ring system, as defined above, in which at least one ring carbon atom is replaced with a heteroatom selected from nitrogen, oxygen, and sulfur. The heteroaryl ring may be fused or otherwise bonded to one or more heteroaryl rings, aromatic or non-aromatic hydrocarbon rings, or heterocycloalkyl rings. Examples of heteroaryl groups include pyridyl, furyl, and thienyl. "Heteroarylene" refers to a divalent heteroaryl group.

[0053] "Alkoxy" refers to an alkyl group attached to the parent molecular moiety through an oxygen bridge. Examples of alkoxy groups include, for example, methoxy, ethoxy, propoxy, and isopropoxy. "Thioalkyl" refers to an alkyl group attached to the parent molecular moiety through a sulfur bridge. Examples of thioalkyl groups include, for example, methylthio, ethylthio, n-propylthio, and isopropylthio. "Aryloxy" refers to an aryl group attached to the parent molecular moiety through an oxygen bridge. An example includes phenoxy. "Arylthio" refers to an aryl group attached to the parent molecular moiety through a sulfur bridge. An example includes phenylthiol. "Cyclic alkoxy" refers to a cycloalkyl group attached to the parent moiety through an oxygen bridge.

[0054] "Alkylamine" refers to an alkyl group attached to the parent molecular moiety through an -NH bridge. Alkyleneamine refers to a divalent alkylamine group, such as -CHCHNH-.

[0055] "Siloxanyl" refers to a structure having at least one Si-O-Si bond. Thus, for example, a siloxanyl group refers to a group having at least one Si-O-Si group (i.e., a siloxane group), and a siloxanyl compound refers to a compound having at least one Si-O-Si group. "Siloxanyl" refers to monomeric (e.g., Si-O-Si) as well as oligomeric / polymeric structures (e.g., -[Si-O] n- (where n is 2 or 3 or more). Each silicon atom in the siloxanyl group is independently selected to complete their valence. A Group (where R A is replaced by (as defined in options (b) to (i) of Formula A).

[0056] Formula A. The silicone-containing component may include one or more polymerizable compounds of formula A:

[0057] [ka] During the ceremony, At least one R A is the formula R g -L group, where R g is a polymerizable group, L is a linking group, and the remaining R A are each independently aR g -L-, b. C1-C optionally substituted with one or more hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, amido, carbamate, carbonate, halo, phenyl, benzyl, or combinations thereof. 16 Alkyl, c. C3-C optionally substituted with one or more alkyl, hydroxy, amino, amido, oxa, carbonyl, alkoxy, amido, carbamate, carbonate, halo, phenyl, benzyl, or combinations thereof. 12 Cycloalkyl, d. C6-C optionally substituted with one or more alkyl, hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, amido, carbamate, carbonate, halo, phenyl, benzyl, or combinations thereof. 14 Aryl groups, e.Haro, f. alkoxy, cyclic alkoxy, or aryloxy; g. Siloxy, h. Alkyleneoxy-alkyl or alkoxy-alkyleneoxy-alkyl, such as polyethyleneoxyalkyl, polypropyleneoxyalkyl, or poly(ethyleneoxy-co-propyleneoxyalkyl); or a monovalent siloxane chain comprising 1 to 100 siloxane repeat units optionally substituted with alkyl, alkoxy, hydroxy, amino, oxa, carboxy, alkylcarboxy, alkoxy, amido, carbamate, halo, or combinations thereof; n is 0 to 500, or 0 to 200, or 0 to 100, or 0 to 20, and when n is other than 0, it is understood that n is a distribution having a mode equivalent to the indicated value. When n is 2 or more, the SiO units may be the same or different R A may carry substituents, different R A When substituents are present, the n groups may be in a random or block configuration.

[0058] In formula A, three R A may each contain a polymerizable group, alternatively two R A may each contain a polymerizable group, or alternatively one R A may contain a polymerizable group.

[0059] "Silyl" refers to a structure of formula R3Si- and "siloxy" refers to a structure of formula R3Si-O-, where each R in silyl or siloxy is independently selected from trimethylsiloxy, C1-C8 alkyl (preferably C1-C3 alkyl, more preferably ethyl or methyl), and C3-C8 cycloalkyl.

[0060] "Alkyleneoxy" refers to a group having the general formula -(alkylene-O-) p -or-(O-alkylene) p-, where alkylene is as defined above, p is 1-200, or 1-100, or 1-50, or 1-25, or 1-20, or 1-10, and each alkylene is independently optionally substituted with one or more groups independently selected from hydroxyl, halo (e.g., fluoro), amino, amido, ether, carbonyl, carboxyl, and combinations thereof. When p is greater than 1, each alkylene may be the same or different, and the alkyleneoxy may be in a block or random configuration. When the alkyleneoxy forms a terminal group in a molecule, the terminus of the alkyleneoxy may be, for example, hydroxy or alkoxy (e.g., HO-[CH2CHO] p - or CH3O-[CH2CH2O] p Examples of alkyleneoxy include polyethyleneoxy, polypropyleneoxy, polybutyleneoxy, and poly(ethyleneoxy-co-propyleneoxy).

[0061] "Oxaalkylene" refers to an alkylene group as defined above in which one or more non-adjacent CH groups are replaced with an oxygen atom, such as -CHCHOCH(CH)CH-. "Thiaalkylene" refers to an alkylene group as defined above in which one or more non-adjacent CH groups are replaced with a sulfur atom, such as -CHCHSCH(CH)CH-.

[0062] The term "linking group" refers to a moiety that connects a polymerizable group to a parent molecule. The linking group may be any moiety that is compatible with the compound of which it is a part, does not undesirably interfere with the polymerization of the compound, and is stable under the polymerization conditions as well as the conditions of processing and storage of the final product. For example, the linking group may be a bond or may include one or more alkylenes, haloalkylenes, amides, amines, alkyleneamines, carbamates, esters (-CO2-), arylenes, heteroarylenes, cycloalkylenes, heterocycloalkylenes, alkyleneoxys, oxaalkylenes, thiaalkylenes, haloalkyleneoxys (alkyleneoxys substituted with one or more halo groups, e.g., -OCF2-, -OCF2CF2-, -OCF2CH2-), siloxanyls, alkylenesiloxanyls, or combinations thereof. The linking group may be optionally substituted with one or more substituents. Suitable substituents can include those independently selected from alkyl, halo (e.g., fluoro), hydroxyl, HO-alkyleneoxy, MeO-alkyleneoxy, siloxanyl, siloxy, siloxy-alkyleneoxy-, siloxy-alkylene-alkyleneoxy- (wherein more than one alkyleneoxy group can be present, and each methylene in the alkylene and alkyleneoxy is independently optionally substituted with hydroxyl), ether, amine, carbonyl, carbamate, and combinations thereof. The linking group can also be substituted with a polymerizable group (in addition to the polymerizable group to which it is attached), such as (meth)acrylate.

[0063] Preferred linking groups include C1-C8 alkylene (preferably C2-C6 alkylene) and C1-C8 oxaalkylene (preferably C2-C6 oxaalkylene), each of which is optionally substituted with one or two groups independently selected from hydroxyl and siloxy. Preferred linking groups also include carboxylate, amide, C1-C8 alkylene-carboxylate-C1-C8 alkylene, or C1-C8 alkylene-amide C1-C8 alkylene.

[0064] When the linking group is comprised of a combination of moieties as described above (e.g., alkylene and cycloalkylene), the moieties may be present in any order. For example, in Formula A above, when L is shown to be -alkylene-cycloalkylene-, Rg-L may be either Rg-alkylene-cycloalkylene-, or Rg-cycloalkylene-alkylene-. Regardless, the order listed represents the preferred order in which the moieties appear in the compound, starting from the terminal polymerizable group (Rg or Pg) to which the linking group is attached. For example, in Formula A, when L is shown to be alkylene-cycloalkylene, Rg-L is preferably Rg-alkylene-cycloalkylene-.

[0065] The term "electron-withdrawing group" (EWG) refers to a chemical group that withdraws electron density from the atom or group of atoms to which it is bonded. Examples of EWGs include, but are not limited to, cyano, amide, ester, keto, or aldehyde. A preferred EWG is cyano (CN).

[0066] The term "light absorbing compound" refers to a chemical that absorbs light within the visible spectrum (e.g., in the 380-780 nm range). A "high energy radiation absorber", "UV / HEV absorber", "UV / HEV absorbing compound", or "high energy light absorbing compound" is a chemical that absorbs various wavelengths of ultraviolet light, high energy visible light, or both. The ability of a material to absorb light of a particular wavelength can be determined by measuring its UV / VIS transmission spectrum. A compound that exhibits no absorption at a particular wavelength exhibits substantially 100 percent transmission at that wavelength. Conversely, a compound that is completely absorbing at a particular wavelength exhibits substantially 0% transmission at that wavelength. When the transmission of a material is given as a percentage for a particular wavelength range, it is understood that the material exhibits transmission at all wavelengths within that range.

[0067] When the compounds described herein contain olefinic double bonds or other centers of geometric asymmetry, and unless otherwise specified, the compounds are intended to include the cis, trans, Z-, and E-configurations, as well as all tautomeric and salt forms.

[0068] The term "optional substituent" means that a hydrogen atom of the underlying moiety is optionally replaced by a substituent. Any substituent that is sterically practical and synthetically feasible at the substitution site may be used. Identification of suitable optional substituents is well within the ability of one of ordinary skill in the art. Examples of "optional substituents" include C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl, halo, hydroxy, amino, NR 4 R 5 , benzyl, SO3H, or SO3Na (wherein R 4 and R 5 are independently H or C1-C6 alkyl). The aforementioned substituents can be optionally substituted with any substituent (preferably not further substituted unless otherwise specified). For example, alkyl can be substituted with halo (e.g., resulting in CF3).

[0069] Unless otherwise stated, ratios, percentages, parts, etc. are by weight.

[0070] Unless otherwise stated, a numerical range such as, for example, "2 to 10" is inclusive of the numbers defining the range (eg, 2 and 10).

[0071] In some embodiments, the reactive monomer mixture comprises at least one polyamide. As used herein, the term "polyamide" refers to polymers and copolymers that comprise repeating units that contain amide groups. The polyamide may comprise cyclic amide groups, non-cyclic amide groups, and combinations thereof, and may be any polyamide known to those skilled in the art. The non-cyclic polyamide comprises pendant non-cyclic amide groups and is capable of association with hydroxyl groups. The cyclic polyamide comprises cyclic amide groups and is capable of association with hydroxyl groups. Suitable polyamides for use with the compositions and methods disclosed herein are disclosed in U.S. Patent Publication No. 20180009922 (SILICONE HYDROGELS COMPRISING HIGH LEVELS OF POLYAMIDES · Alli et al., published January 11, 2018) and U.S. Patent Publication No. 20180011222 (SILICONE HYDROGELS COMPRISING POLYAMIDES · Alli et al., published January 11, 2018), each of which is incorporated by reference in its entirety.

[0072] The "Abbe number", also known as the V number or astringency of a transparent material, is a measure of the material's dispersion, i.e., variation of refractive index versus wavelength, with a high value of V indicating low dispersion. The Abbe number of a material is defined as follows:

[0073]

number

[0074] "Refractive index" is defined as follows:

[0075]

number

[0076] B. Composition In some embodiments, the subject matter disclosed herein comprises: (A) a composition prepared by free radical polymerization of a reactive monomer mixture comprising: (i) at least one alicyclic (meth)acrylate; (ii) at least one aromatic (meth)acrylate; (iii) at least one aliphatic (meth)acrylate; and (iv) at least one crosslinker, the composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39 (hereinafter, "Composition (A)"); (B) a composition prepared by free radical polymerization of a reactive monomer mixture comprising: (i) at least one alicyclic (meth)acrylate; (ii) at least one aliphatic (meth)acrylate; and (iii) at least one crosslinker, the composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39 (hereinafter, "composition (B)"); (C) (i) at least one hydrophobic monomer; and (ii) at least one acrylate monomer of formula (I):

[0077] [ka] In the formula, R 1 is selected from hydrogen and methyl; R 2 is a non-aromatic moiety having at least one carbon-carbon double bond; and (iii) at least one crosslinker (hereinafter "Composition (C)"); (D) a composition ("Composition (D)") prepared by free radical polymerization of a reactive monomer mixture comprising: (i) at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings; (ii) at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers, and any combination thereof; and (iii) at least one crosslinker, the composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39; or (E) (i) at least one hydrophobic monomer; (ii) at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers, and any combination thereof; and (iii) tricyclo[5.2.1.0 2,6 and a decanedimethanol di(meth)acrylate crosslinker, and the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39 ("Composition (E)").

[0078] Each of the compositions will now be described in more detail.

[0079] 1. Composition (A) In some embodiments, the presently disclosed subject matter provides a composition, referred to herein as “Composition (A),” prepared by free radical polymerization of a reactive monomer mixture comprising: (a) at least one cycloaliphatic (meth)acrylate; (b) at least one aromatic (meth)acrylate; (c) at least one aliphatic (meth)acrylate; and (d) at least one crosslinker, the composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39.

[0080] In some embodiments of composition (A), the at least one alicyclic (meth)acrylate comprises an alicyclic group having 1 to 4 alicyclic rings. In some embodiments, the alicyclic group has one alicyclic ring. The alicyclic ring can be a C3-C8 cycloalkyl group, a C3-C7 cycloalkyl group, a C4-C7 cycloalkyl group, or a C5-C6 cycloalkyl group. In some embodiments, the at least one alicyclic (meth)acrylate has at least one alicyclic group that includes at least one carbon-carbon double bond. In some embodiments, the alicyclic (meth)acrylate is cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, norbornyl (meth)acrylate, norbornyl PEG (meth)acrylate derivatives, isobornyl (meth)acrylate, isobornyl derivatives, norbornyl derivatives, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-ene

[0043] The compound is selected from (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl PEG (meth)acrylate derivatives and (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate derivatives, and any combination thereof.In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexylmethyl acrylate, cyclohexylmethyl methacrylate, 2-cyclohexylethyl acrylate, 2-cyclohexylethyl methacrylate, 3-cyclohexylpropyl acrylate, ethylene glycol dicyclopentenyl ether acrylate, and any combination thereof. In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, 2-cyclohexyl ethyl acrylate, 3-cyclohexyl propyl acrylate, and any combination thereof. In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl methyl acrylate, cyclohexyl methyl methacrylate, ethylene glycol dicyclopentenyl ether acrylate, and any combination thereof. In some embodiments, the cycloaliphatic (meth)acrylate is selected from 2-cyclohexyl ethyl acrylate, 2-cyclohexyl ethyl methacrylate, ethylene glycol dicyclopentenyl ether acrylate, and any combination thereof. In some embodiments, at least one cycloaliphatic (meth)acrylate is cyclohexyl acrylate. In some embodiments, at least one cycloaliphatic (meth)acrylate is cyclohexyl methyl acrylate. In some embodiments, at least one cycloaliphatic (meth)acrylate is 2-cyclohexyl ethyl acrylate. In some embodiments, the at least one alicyclic (meth)acrylate is ethylene glycol dicyclopentenyl ether acrylate.

[0081] In some embodiments, the alicyclic (meth)acrylate does not contain any substituents (e.g., hydroxy substituents) in the alicyclic portion or anywhere else on the monomer (e.g., in a monomer such as 2-cyclohexylethyl (meth)acrylate, the monomer does not contain any substituents such as hydroxy substituents in either the cyclohexyl or ethyl portion).

[0082] In some embodiments, the reactive monomer mixture of composition (A) comprises at least one cycloaliphatic (meth)acrylate in an amount of about 20 to about 80 weight percent, including about 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, and 80 weight percent, about 40 to about 80 weight percent, including about 40, 45, 50, 55, 60, 65, 70, 75, and 80 weight percent, or about 60 to about 80 weight percent, including about 60, 65, 70, 75, and 80 weight percent. In some embodiments, the weight percent of the at least one cycloaliphatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0083] In some embodiments of composition (A), at least one aromatic (meth)acrylate is a (meth)acrylate containing at least one aryl group. In some embodiments, the aryl group is a phenyl group. In some embodiments, the aryl group can be present in the aromatic (meth)acrylate as part of an arylalkyl group (e.g., benzyl, 2-phenylethyl, 3-phenylpropyl, or 4-phenylbutyl), an aryloxyalkyl group (e.g., phenoxymethyl, 2-phenoxyethyl, or 3-phenoxypropyl), or an arylthioalkyl group (e.g., phenylthiomethyl, 2-phenylthioethyl, or 3-phenylthiopropyl). In some embodiments, the at least one aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the aromatic (meth)acrylate is a combination of 2-phenylethyl acrylate and 2-phenylethyl methacrylate. In some embodiments, the at least one aromatic (meth)acrylate is 2-phenylethyl acrylate. In some embodiments, the at least one aromatic (meth)acrylate is 2-phenylethyl methacrylate. In some embodiments, the aromatic (meth)acrylate is 3-phenylpropyl acrylate.In some embodiments, the aromatic (meth)acrylate is 4-phenylbutyl acrylate.

[0084] In some embodiments, the at least one aromatic (meth)acrylate has at least one aliphatic group containing at least one carbon-carbon double bond. In some embodiments, the at least one aromatic (meth)acrylate is cinnamyl (meth)acrylate.

[0085] In some embodiments, the reactive monomer mixture of composition (A) comprises at least one aromatic (meth)acrylate in an amount of from about 5 to about 50 weight percent, including about 5, 10, 15, 20, 25, 30, 35, and 408%, from about 10 to about 40 weight percent, including about 10, 15, 20, 25, 30, 35, and 40 weight percent, or from about 15 to about 40 weight percent, including about 15, 20, 25, 30, 35, and 40 weight percent. In some embodiments, the weight percent of the at least one aromatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0086] In some embodiments of composition (A), the alicyclic (meth)acrylate and aromatic (meth)acrylate are present in the reactive monomer mixture in a ratio of about 95:5 to about 30:70, about 90:10 to about 40:60, or about 90:10 to about 45:55. For example, in some embodiments, the alicyclic (meth)acrylate and aromatic (meth)acrylate are present in the reactive monomer mixture in a ratio of about 95:5, about 90:10, about 85:15, about 80:20, about 75:25, about 70:30, about 65:35, about 60:40, about 55:45, about 50:50, about 45:55, about 40:60, about 35:65, or about 30:70.

[0087] In some embodiments of composition (A), the at least one aliphatic (meth)acrylate is selected from the group consisting of C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C 10 , C 11 , C 12 , C 13 , C 14 , C15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , and C 25 A linear or branched alkyl group (C1-C 25 In certain embodiments, the aliphatic (meth)acrylate comprises a C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , and C 20 C1-C, including alkyl (meth)acrylates 20 In a more specific embodiment, the alkyl (meth)acrylate is a C1-C 20 The alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, isodecyl (meth)acrylate, heptadecyl (meth)acrylate, dodecyl (meth)acrylate, 2-propylheptyl (meth)acrylate, stearyl (meth)acrylate, and any combination thereof. In still more specific embodiments, the aliphatic (meth)acrylate comprises a straight chain alkyl group containing 4 to 8 carbon atoms (C4-C8 straight chain alkyl group), including 4, 5, 6, 7, and 8 carbon atoms. In some embodiments, the aliphatic (meth)acrylate is n-hexyl acrylate.

[0088] In some embodiments, the at least one aliphatic (meth)acrylate has at least one aliphatic group that includes at least one carbon-carbon double bond.

[0089] In some embodiments, the reactive monomer mixture of composition (A) comprises at least one aliphatic (meth)acrylate in an amount of 1 to 40 wt%, including about 1, 5, 10, 15, 20, 25, 30, 35, and 40 wt%, about 1 to about 20 wt%, including about 1, 5, 10, 15, and 20 wt%, or about 1 to about 10 wt%, including about 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10 wt%. In some embodiments, the weight percent of the at least one aliphatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0090] In some embodiments of composition (A), the at least one crosslinking agent is selected from the group consisting of non-alicyclic crosslinking agents, alicyclic crosslinking agents, and any combination thereof. In certain embodiments, the at least one crosslinking agent is a non-alicyclic crosslinking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl(meth)acrylate) terminated polydimethylsiloxane, and any combination thereof. In more specific embodiments, the non-alicyclic crosslinking agent is ethylene glycol dimethacrylate. In certain embodiments, the at least one crosslinking agent is an alicyclic crosslinking agent comprising an alicyclic group having 1 to 4 alicyclic rings. In an even more specific embodiment, the alicyclic crosslinker is a tricyclo[5.2.1.0 2,6 ] decanedimethanol di(meth)acrylate (e.g., tricyclo[5.2.1.0 2,6 ]decane dimethanol diacrylate).

[0091] In some embodiments, the reactive monomer mixture of composition (A) comprises an alicyclic crosslinker in an amount of from about 1 to about 20 weight percent, including from about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 weight percent, from about 3 to about 15 weight percent, including from about 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15 weight percent, or from about 3 to about 10 weight percent, including from about 3, 4, 5, 6, 7, 8, 9, and 10 weight percent. In some embodiments, the weight percent of alicyclic crosslinker present in the reactive monomer mixture is calculated excluding the diluent.

[0092] In some embodiments of composition (A), the reactive monomer mixture further comprises a polyamide. In some embodiments, the at least one polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinyl-acetamide), poly(dimethylacrylamide), and copolymers or mixtures thereof. In certain embodiments, the at least one polyamide is selected from poly(vinylpyrrolidone) and poly(N-vinyl-N-methylacetamide). In certain embodiments, the at least one polyamide is a copolymer.

[0093] In some embodiments, the reactive monomer mixture of composition (A) comprises at least one polyamide in an amount of from about 0.1 wt % to about 5 wt %, including from about 0.1, 0.5, 1, 2, 3, 4, and 5 wt %, from about 0.5 wt % to about 3 wt %, including from about 0.5, 1, 2, and 3 wt %, or from about 0.5 wt % to about 2 wt %, including from about 0.5, 1, and 2 wt %. In some embodiments, the weight percent of the at least one polyamide present in the reactive monomer mixture is calculated excluding the diluent.

[0094] In some embodiments, the reactive monomer mixture of composition (A) further comprises at least one hydroxysilicone monomer.

[0095] In some embodiments, the reactive monomer mixture of composition (A) further comprises at least one hydroxysilicone monomer. In certain embodiments, the at least one hydroxysilicone monomer comprises mono-n-butyl terminated mono-(2-hydroxy-3-methacryloxypropyloxy)-propyl terminated polydimethylsiloxane, 3-(3-(1,1,1,3,5,5,5-heptamethyltrisiloxane-3-yl)propoxy)-2-hydroxypropyl methacrylate, 3-(3-(1,5-di-tert-butyl-1,1,3,5,5-pentamethyltrisiloxane-3-yl)propoxy)-2-hydroxypropyl methacrylate, or any combination thereof.

[0096] In some embodiments, the reactive monomer mixture of composition (A) comprises the hydroxysilicone monomer in an amount of from about 1 to about 25 weight percent, including from about 1, 5, 10, 15, 20, and 25 weight percent, from about 5 to about 20 weight percent, including from about 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 weight percent, or from about 10 to about 20 weight percent, including from 10, 11, 13, 13, 14, 15, 16, 17, 18, 19, and 20 weight percent. In some embodiments, the weight percent of the hydroxysilicone monomer present in the reactive monomer mixture is calculated excluding the diluent.

[0097] In some embodiments, the reactive monomer mixture of composition (A) further comprises at least one hydroxyalkyl (meth)acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate is selected from the group consisting of C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39, C40, C41, C42, C43, C44, C45, C46, ​​C47, C48, C49, C50, C51, C52, C53, C54, C55 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24, and C 25 1 to 25 carbon atoms (C1 to C 25 In some embodiments, the hydroxyalkyl (meth)acrylate is selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, and any combination thereof. In some embodiments, the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate or 2-hydroxyethyl methacrylate. In certain embodiments, the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate is 2-hydroxyethyl methacrylate.

[0098] In some embodiments, the reactive monomer mixture of composition (A) comprises hydroxyalkyl (meth)acrylate in an amount of from about 1 to about 25 weight percent, including from about 1, 5, 10, 15, 20, and 25 weight percent, from about 5 to about 20 weight percent, including from about 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 weight percent, or from about 10 to about 20 weight percent, including from 10, 11, 13, 13, 14, 15, 16, 17, 18, 19, and 20 weight percent. In some embodiments, the weight percent of hydroxyalkyl (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0099] In some embodiments, the reactive monomer mixture of composition (A) does not include a hydroxyalkyl (meth)acrylate.

[0100] In some embodiments, the reactive monomer mixture of composition (A) further comprises at least one UV / HEV absorbing compound.

[0101] In some embodiments, the UV / HEV absorbing compound can be of the form of Formula II:

[0102] [ka] During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; X is O, S, NR, SO, or SO2; Y is a linking group; P g is a polymerizable group, R, at each occurrence, is independently H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or YP g and R 1 and R 2 is, when present, independently at each occurrence C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halo), halo, hydroxy, amino, NR 3 R 4 or benzyl, where R 3 and R 4 are independently H or C1-C6 alkyl, or two adjacent R 1 Or R 2 the groups, together with the carbon atom to which they are attached, are joined to form a cycloalkyl or aryl ring; EWG is an electron withdrawing group.

[0103] The compound of formula II preferably contains one or two YP g More preferably, the compound contains one YP group. g Contains a group.

[0104] In certain embodiments, the at least one UV / HEV absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, or any combination thereof. In certain embodiments, the at least one UV / HEV absorbing compound is 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate. In certain embodiments, the at least one UV / HEV absorbing compound is 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate.

[0105] In some embodiments, the reactive monomer mix of composition (A) comprises at least one UV / HEV absorbing compound in an amount of from about 0.1 to about 5 wt%, including about 0.1, 0.5, 1, 2, 3, 4, and 5 wt%, from about 1 to about 4 wt%, including about 1, 2, 3, and 4 wt%, or from about 1 to about 3 wt%, including about 1, 2, and 3 wt%. In some embodiments, the weight percent of the at least one UV / HEV absorbing compound present in the reactive monomer mix is ​​calculated excluding the diluent.

[0106] In some embodiments, the reactive monomer mixture of composition (A) further comprises at least one hydrophilic monomer. In some embodiments, the hydrophilic monomer is selected from vinylpyrrolidone, N-vinyl-N-methylacetamide, N-methylmethacrylamide, N-vinylacetamide, N,N-dimethylacrylamide, N-hydroxyethylacrylamide, N-(2-hydroxypropyl)acrylamide, N-(3-hydroxypropyl)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, and N-(3-hydroxypropyl)(meth)acrylamide, poly(ethylene glycol) methyl ether (meth)acrylate, poly(ethylene glycol)(meth)acrylate, and any combination thereof. In some embodiments, the hydrophilic monomer has at least one aliphatic group having at least one double bond.

[0107] In some embodiments, the reactive monomer mixture of composition (A) does not include a hydrophilic monomer.

[0108] In some embodiments, composition (A) further comprises at least one diluent in the reactive monomer mixture.

[0109] In some embodiments, composition (A) has a moisture content of about 0% to about 15%, including about 0, 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15%, or about 1% to about 10%, including about 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10%, or about 1% to about 8%, including about 1, 2, 3, 4, 5, 6, 7, and 8%, or about 0.5 to less than 5%, including 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, and 4.5%. In some embodiments, the moisture content is measured when the material is hydrated at 37° C.

[0110] In some embodiments, composition (A) has a refractive index of at least 1.45 and an Abbe number of at least 45. In other embodiments, composition (A) has a refractive index of at least 1.48 and an Abbe number of at least 50. In yet other embodiments, composition (A) has a refractive index of at least 1.50 and an Abbe number of at least 50. In some embodiments, the indicated refractive index and indicated Abbe number are measured when the material is in a dry state at 25° C.

[0111] In some embodiments of composition (A), the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator. In some embodiments, the initiator is bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.

[0112] (2) Composition (B) In some embodiments, the presently disclosed subject matter provides a composition, referred to herein as “Composition (B),” prepared by free radical polymerization of a reactive monomer mixture comprising: (a) at least one cycloaliphatic (meth)acrylate; (b) at least one aliphatic (meth)acrylate; and (c) at least one crosslinker, the composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39.

[0113] In some embodiments of composition (B), the at least one alicyclic (meth)acrylate comprises an alicyclic group having 1 to 4 alicyclic rings. In some embodiments, the alicyclic group has one alicyclic ring. The alicyclic ring can be a C3-C8 cycloalkyl group, a C3-C7 cycloalkyl group, a C4-C7 cycloalkyl group, or a C5-C6 cycloalkyl group. In some embodiments, the at least one alicyclic (meth)acrylate has at least one alicyclic group that includes at least one carbon-carbon double bond.In some embodiments, the alicyclic (meth)acrylate is cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, norbornyl (meth)acrylate, isobornyl (meth)acrylate, isobornyl derivatives, norbornyl derivatives, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl (meth)acrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, poly(ethylene)glycol dicyclopentenyl ether (meth)acrylate, 2,2-bis(cyclopent-1-en-1-yloxy)ethyl (meth)acrylate, 2-(((3aR,4 R,5S,7R,7aR)-Octahydro-1H-4,7-methanoinden-5-yl)oxy)ethyl acrylate, 2-(((3aS,4R,6S,7R,7aR)-3a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, (3aS,4S,5R,7S,7aS)-Octahydro-1H-4,7-methanoinden-5-yl acrylate, (3aS,4S,5R,7S,7aS)- 3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-yl acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl PEG (meth)acrylate derivatives and (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate derivatives, and any combination thereof. In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, and any combination thereof.In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, 2-cyclohexyl ethyl acrylate, 3-cyclohexyl propyl acrylate, and ethylene glycol dicyclopentenyl ether acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, 2-cyclohexyl ethyl acrylate, and 3-cyclohexyl propyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is cyclohexyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is cyclohexyl methyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is 2-cyclohexyl ethyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is ethylene glycol dicyclopentenyl ether acrylate.

[0114] In some embodiments, the alicyclic (meth)acrylate does not contain any substituents (e.g., hydroxy substituents) in the alicyclic portion or anywhere else on the monomer (e.g., in a monomer such as 2-cyclohexylethyl (meth)acrylate, the monomer does not contain any substituents such as hydroxy substituents in either the cyclohexyl or ethyl portion).

[0115] In some embodiments, the reactive monomer mixture of composition (B) comprises at least one cycloaliphatic (meth)acrylate in an amount of about 20 to about 80 weight percent, including about 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, and 80 weight percent, about 40 to about 80 weight percent, including about 40, 45, 50, 55, 60, 65, 70, 75, and 80 weight percent, or about 60 to about 80 weight percent, including about 60, 65, 70, 75, and 80 weight percent. In some embodiments, the weight percent of the at least one cycloaliphatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0116] In some embodiments of composition (B), the at least one aliphatic (meth)acrylate is selected from the group consisting of C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , and C 25 A linear or branched alkyl group (C1-C 25 In certain embodiments, the aliphatic (meth)acrylate comprises a C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , and C 20 C1-C, including alkyl (meth)acrylates 20 In a more specific embodiment, the alkyl (meth)acrylate is a C1-C 20The alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, isodecyl (meth)acrylate, heptadecyl (meth)acrylate, dodecyl (meth)acrylate, 2-propylheptyl (meth)acrylate, stearyl (meth)acrylate, and any combination thereof. In still more specific embodiments, the aliphatic (meth)acrylate comprises a linear or branched alkyl group containing 4 to 8 carbon atoms (C4 to C8 linear alkyl group), including 4, 5, 6, 7, and 8 carbon atoms. In some embodiments, the aliphatic (meth)acrylate is isobutyl acrylate or n-hexyl acrylate.

[0117] In some embodiments, the reactive monomer mixture of composition (B) comprises at least one aliphatic (meth)acrylate in an amount of from 1 to 40 weight percent, from about 1 to about 20 weight percent, or from about 1 to about 10 weight percent. In some embodiments, the weight percent of the at least one aliphatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0118] In some embodiments of composition (B), the at least one crosslinking agent is selected from the group consisting of non-alicyclic crosslinking agents, alicyclic crosslinking agents, and any combination thereof. In certain embodiments, the at least one crosslinking agent is a non-alicyclic crosslinking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl(meth)acrylate) terminated polydimethylsiloxane, and any combination thereof. In more specific embodiments, the non-alicyclic crosslinking agent is ethylene glycol dimethacrylate. In certain embodiments, the at least one crosslinking agent is an alicyclic crosslinking agent comprising an alicyclic group having 1 to 4 alicyclic rings. In an even more specific embodiment, the alicyclic crosslinker is a tricyclo[5.2.1.0 2,6 ] decanedimethanol di(meth)acrylate (e.g., tricyclo[5.2.1.0 2,6 ]decane dimethanol diacrylate).

[0119] In some embodiments, the reactive monomer mixture of composition (B) comprises an alicyclic crosslinker in an amount of from about 1 to about 20 weight percent, including about 1, 5, 10, 15, and 20 weight percent, from about 3 to about 15 weight percent, including 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15, or from about 3 to about 10 weight percent, including 3, 4, 5, 6, 7, 8, 9, and 10 weight percent. In some embodiments, the weight percent of alicyclic crosslinker present in the reactive monomer mixture is calculated excluding the diluent.

[0120] In some embodiments, the reactive monomer mixture of composition (B) further comprises an aromatic (meth)acrylate. In some embodiments, the aromatic (meth)acrylate comprises at least one aryl group. In some embodiments, the aryl group is a phenyl group. In some embodiments, the aryl group can be present in the aromatic (meth)acrylate as part of an arylalkyl group (e.g., benzyl, 2-phenylethyl, 3-phenylpropyl, or 4-phenylpropyl), an aryloxyalkyl group (e.g., phenoxymethyl, 2-phenoxyethyl, or 3-phenoxypropyl), or an arylthioalkyl group (e.g., phenylthiomethyl, 2-phenylthioethyl, or 3-phenylthiopropyl). In some embodiments, the aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the aromatic (meth)acrylate is 2-phenylethyl acrylate. In some embodiments, the aromatic (meth)acrylate is 2-phenylethyl methacrylate. In some embodiments, the aromatic (meth)acrylate is 3-phenylpropyl acrylate. In some embodiments, the aromatic (meth)acrylate is 4-phenylbutyl acrylate.

[0121] In some embodiments, the reactive monomer mixture of composition (B) comprises an aromatic (meth)acrylate in an amount of from about 5 to about 50 weight percent, including about 5, 10, 15, 20, 25, 30, 35, 40, 45, and 50 weight percent, from about 10 to about 40 weight percent, including about 10, 15, 20, 25, 30, 35, and 40 weight percent, or from about 15 to about 40 weight percent, including about 15, 20, 25, 30, 35, and 40 weight percent. In some embodiments, the weight percent of the at least one aromatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0122] In some embodiments, composition (B) does not include aromatic monomers, such as aromatic (meth)acrylates.

[0123] In some embodiments, the reactive monomer mixture of composition (B) further comprises at least one hydrophilic monomer. In some embodiments, the hydrophilic monomer is selected from vinylpyrrolidone, N-vinyl-N-methylacetamide, N-methylmethacrylamide, N-vinylacetamide, N,N-dimethylacrylamide, N-hydroxyethylacrylamide, N-(2-hydroxypropyl)acrylamide, N-(3-hydroxypropyl)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, N-(3-hydroxypropyl)(meth)acrylamide, poly(ethylene glycol) methyl ether(meth)acrylate, poly(ethylene glycol)(meth)acrylate, and any combination thereof. In some embodiments, the hydrophilic monomer has at least one aliphatic group having at least one double bond.

[0124] In some embodiments, the reactive monomer mixture of composition (B) does not include a hydrophilic monomer.

[0125] In some embodiments, the reactive monomer mixture of composition (B) further comprises at least one hydroxyalkyl (meth)acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate is selected from the group consisting of C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39, C40, C41, C42, C43, C44, C45, C46, ​​C47, C48, C49, C50, C51, C52, C53, C54, C55 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , and C 25 1 to 25 carbon atoms (C1 to C 25 In some embodiments, the hydroxyalkyl (meth)acrylate is selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof. In some embodiments, the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate or 2-hydroxyethyl methacrylate. In certain embodiments, the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate is 2-hydroxyethyl methacrylate.

[0126] In some embodiments, the reactive monomer mixture of composition (B) comprises hydroxyalkyl (meth)acrylate in an amount of about 1 to about 25 weight percent, including about 1, 5, 10, 15, 20, and 20 weight percent, about 5 to about 20 weight percent, including about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 weight percent, about 10% to about 20 weight percent, including about 1, 5, 10, 15, 20, and 20 weight percent. In some embodiments, the weight percent of hydroxyalkyl (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0127] In some embodiments, the reactive monomer mixture of composition (B) does not include a hydroxyalkyl (meth)acrylate.

[0128] In some embodiments, the reactive monomer mixture of composition (B) further comprises a polyamide. In some embodiments, the at least one polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl N-methylacetamide), poly(N-vinyl-acetamide), poly(dimethylacrylamide), and copolymers or mixtures thereof. In certain embodiments, the at least one polyamide is selected from poly(vinylpyrrolidone) and poly(N-vinyl N-methylacetamide). In certain embodiments, the at least one polyamide is a copolymer.

[0129] In some embodiments, the reactive monomer mixture of composition (B) comprises at least one polyamide in an amount of from about 0.1 wt % to about 5 wt %, including from about 0.1, 0.5, 1, 2, 3, 4, and 5 wt %, from about 0.5 wt % to about 3 wt %, including from about 0.5, 1, 2, and 3 wt %, or from about 0.5 wt % to about 2 wt %, including from about 0.5, 1, and 2 wt %. In some embodiments, the weight percent of the at least one polyamide present in the reactive monomer mixture is calculated excluding the diluent.

[0130] In some embodiments, the reactive monomer mixture of composition (B) further comprises at least one UV / HEV absorbing compound. In some embodiments, the UV / HEV absorbing compound can take the form of Formula II:

[0131] [ka] During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; X is O, S, NR, SO, or SO2; Y is a linking group; P g is a polymerizable group, R, at each occurrence, is independently H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or YP g and R 1 and R 2 is, when present, independently at each occurrence C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halo), halo, hydroxy, amino, NR 3 R 4 or benzyl, where R 3 and R 4 are independently H or C1-C6 alkyl, or two adjacent R 1 Or R 2 the groups, together with the carbon atom to which they are attached, are joined to form a cycloalkyl or aryl ring; EWG is an electron withdrawing group.

[0132] The compound of formula II preferably contains one or two YP g More preferably, the compound contains one YP group. g Contains a group.

[0133] In certain embodiments, the at least one UV / HEV absorbing compound is a compound of formula II and is 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, or any combination thereof. In certain embodiments, the at least one UV / HEV absorbing compound is 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate. In certain embodiments, the at least one UV / HEV absorbing compound is 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate.

[0134] In some embodiments, the reactive monomer mix of composition (E) comprises at least one UV / HEV absorbing compound in an amount of from about 0.1 to about 5 wt%, including about 0.1, 0.5, 1, 2, 3, 4, and 5 wt%, from about 1 to about 4 wt%, including about 1, 2, 3, and 4 wt%, or from about 1 to about 3 wt%, including about 1, 2, and 3 wt%. In some embodiments, the weight percent of the at least one UV / HEV absorbing compound present in the reactive monomer mix is ​​calculated excluding the diluent.

[0135] In some embodiments, the reactive monomer mixture of composition (B) further comprises at least one diluent in the reactive monomer mixture.

[0136] In some embodiments, the reactive monomer mixture of composition (B) has a water content of about 0% to about 15%, including about 0, 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15% by weight, or about 1% to about 10%, including about 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10% by weight, or about 1% to about 8%, including about 1, 2, 3, 4, 5, 6, 7, and 8% by weight, or about 0.5 to less than 5%, including 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, and 4.5% by weight. In some embodiments, the water content is measured when the material is hydrated at 37° C.

[0137] In some embodiments, the reactive monomer mixture of composition (B) has a refractive index of at least 1.45 and an Abbe number of at least 45. In another embodiment, composition (B) has a refractive index of at least 1.48 and an Abbe number of at least 50. In yet another embodiment, composition (B) has a refractive index of at least 1.50 and an Abbe number of at least 50. In some embodiments, the indicated refractive index and indicated Abbe number are measured when the material is in a dry state at 25° C.

[0138] In some embodiments of composition (B), the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator. In some embodiments, the initiator is bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.

[0139] (3) Composition (C) In some embodiments, the presently disclosed subject matter provides a polymerizable composition comprising: (a) at least one hydrophobic monomer; and (b) at least one acrylate monomer having formula (I):

[0140] [ka] In the formula, R 1 is selected from hydrogen and methyl; R 2The present invention provides a composition, referred to herein as "Composition (C)," made by free radical polymerization of a reactive monomer mixture comprising at least one acrylate monomer, where the monomer is a non-aromatic moiety having at least one carbon-carbon double bond; and (c) at least one crosslinker.

[0141] In some embodiments of composition (C), the hydrophobic monomer is a hydrophobic (meth)acrylate monomer. In some embodiments, the hydrophobic (meth)acrylate is selected from an aliphatic (meth)acrylate, an aromatic (meth)acrylate, a cycloaliphatic (meth)acrylate, and any combination thereof.

[0142] In certain embodiments, the hydrophobic (meth)acrylate is an aliphatic (meth)acrylate. In some embodiments, the aliphatic (meth)acrylate is a C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39, C40, C41, C42, C43, C44, C45, C46, ​​C47, C48, C49, C50, C51, C52, C53, C54, C55, C56, C5 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , and C 18 Linear or branched alkyl groups containing 1 to 18 carbon atoms (C1 to C2) including alkyl (meth)acrylates 18 In a more specific embodiment, C1 to C 18The alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, isodecyl (meth)acrylate, heptadecyl (meth)acrylate, dodecyl (meth)acrylate, 2-propylheptyl (meth)acrylate, stearyl (meth)acrylate, and any combination thereof. In still more specific embodiments, the aliphatic (meth)acrylate comprises a straight chain alkyl group containing 4 to 8 carbon atoms (C4 to C8 straight chain alkyl group). In some embodiments, the aliphatic (meth)acrylate is n-hexyl acrylate.

[0143] In some embodiments, the hydrophobic (meth)acrylate is an aromatic (meth)acrylate. In some embodiments, the aromatic (meth)acrylate comprises at least one aryl group. In some embodiments, the aryl group is a phenyl group. In some embodiments, the aryl group can be present in the aromatic (meth)acrylate as part of an arylalkyl group (e.g., benzyl, 2-phenylethyl, 3-phenylpropyl, or 4-phenylbutyl), an aryloxyalkyl group (e.g., phenoxymethyl, 2-phenoxyethyl, or 3-phenoxypropyl), or an arylthioalkyl group (e.g., phenylthiomethyl, 2-phenylthioethyl, or 3-phenylthiopropyl). In some embodiments, the aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the aromatic (meth)acrylate is 2-phenylethyl acrylate. In some embodiments, the aromatic (meth)acrylate is 2-phenylethyl methacrylate. In some embodiments, the aromatic (meth)acrylate is a combination of 2-phenylethyl acrylate and 2-phenylethyl methacrylate. In some embodiments, the aromatic (meth)acrylate is 3-phenylpropyl acrylate. In some embodiments, the aromatic (meth)acrylate is 4-phenylbutyl acrylate.

[0144] In some embodiments of composition (C), the hydrophobic (meth)acrylate is an alicyclic (meth)acrylate. In some embodiments, the alicyclic (meth)acrylate comprises an alicyclic group having 1 to 4 alicyclic rings. In some embodiments, the alicyclic group has one alicyclic ring. The alicyclic ring can be a C3-C8 cycloalkyl group, a C3-C7 cycloalkyl group, a C4-C7 cycloalkyl group, or a C5-C6 cycloalkyl group. In some embodiments, at least one alicyclic (meth)acrylate has at least one alicyclic group that includes at least one carbon-carbon double bond.In some embodiments, the alicyclic (meth)acrylate is cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, norbornyl (meth)acrylate, isobornyl (meth)acrylate, isobornyl derivatives, norbornyl derivatives, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl (meth)acrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, poly(ethylene)glycol dicyclopentenyl ether (meth)acrylate, 2,2-bis(cyclopent-1-en-1-yloxy)ethyl (meth)acrylate, 2-(((3aR,4 R,5S,7R,7aR)-Octahydro-1H-4,7-methanoinden-5-yl)oxy)ethyl acrylate, 2-(((3aS,4R,6S,7R,7aR)-3a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, (3aS,4S,5R,7S,7aS)-Octahydro-1H-4,7-methanoinden-5-yl acrylate, (3aS,4S,5R,7S,7aS)- 3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-yl acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl PEG (meth)acrylate derivatives and (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate derivatives, and any combination thereof. In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, and any combination thereof.In some embodiments, the cycloaliphatic (meth)acrylate is cyclohexyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is cyclohexyl methyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is 2-cyclohexyl ethyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is ethylene glycol dicyclopentenyl ether acrylate.

[0145] In some embodiments, the alicyclic (meth)acrylate does not contain any substituents (e.g., hydroxy substituents) in the alicyclic portion or anywhere else on the monomer (e.g., in a monomer such as 2-cyclohexylethyl (meth)acrylate, the monomer does not contain any substituents such as hydroxy substituents in either the cyclohexyl or ethyl portion).

[0146] The composition (C) also comprises at least one acrylate monomer of formula (I):

[0147] [ka] In the formula, R 1 is selected from hydrogen and methyl; R 2 is a non-aromatic moiety having at least one carbon-carbon double bond.

[0148] In some embodiments, R 1 is hydrogen. In some embodiments, R 2 is methyl.

[0149] In some embodiments, in at least one acrylate monomer of formula (I), R 2 comprises an alkenyl or cycloalkenyl moiety. In certain embodiments, R 2contains a cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, bicyclo[2.2.1]hept-5-en-2-yl, 3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoindenyl, styryl, cinnamyl, or allyl moiety.

[0150] In more specific embodiments, the acrylate monomer of formula (I) is selected from the group consisting of ethylene glycol dicyclopentenyl ether (meth)acrylate, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl acrylate, 2-(((3aS,4R,6S,7R,7aR)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, poly(ethylene)glycol dicyclopentenyl ether (meth)acrylate, 2,2-bis(cyclopent-1-en-1-yloxy)ethyl (meth)acrylate, (3aS,4S,5R,7S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-yl acrylate, 2-(cyclopent-1-en-1-yloxy)ethyl acrylate, The aryloxy group is selected from 2-(cyclopent-3-en-1-yloxy)ethyl acrylate, cyclopenta-2,4-dien-1-yl acrylate, cyclopent-3-en-1-yl acrylate, 2-(cyclopent-3-en-1-yloxy)ethyl acrylate, cyclohexa-2,4-dien-1-yl acrylate, 2-(cyclohexa-2,4-dien-1-yloxy)ethyl acrylate, 2-(cyclohex-3-en-1-yloxy)ethyl acrylate, cyclohex-3-en-1-yl acrylate, 2-(2-(2-(2-(cyclohex-3-en-1-yloxy)ethoxy)ethoxy)ethyl acrylate, N,N-diallylacrylamide, allyl acrylate, and 2-(allyloxy)ethyl acrylate.

[0151] In some embodiments, the reactive monomer mixture of composition (C) further comprises a hydroxyl group-containing monomer. In some embodiments, the hydroxyl group-containing monomer is a hydroxyalkyl (meth)acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate is a C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39, C40, C41, C42, C43, C44, C45, C46, ​​C47, C48, C49, C50, C51, C52, C53, C54, C55, C56, C57, C58, C59, C60, C61, C62, C63, C64, C65, C66, C67, C68, C69, C71, C72, C73, C74, C75, C76, C77, C78, ​​C79, C80, C81, C82, C83, C84, C85, C86, C87, C88, C89, C91, C92, C93, C94, C95, C96, C97, C98, C99, C99, C101, C102, C103, C104, C105, C106, C107, C108, C109, C111, C112, C123, C124, C12 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , and C 25 1 to 25 carbon atoms (C1 to C 25 In some embodiments, the hydroxyalkyl (meth)acrylate is selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof. In certain embodiments, the hydroxyalkyl (meth)acrylate is 2-hydroxyethyl methacrylate or 4-hydroxybutyl acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate is 2-hydroxyethyl methacrylate.

[0152] In some embodiments, the hydroxyl group-containing monomer is a hydroxysilicone monomer. In some embodiments, the hydroxysilicone monomer is selected from 3-(3-(1,1,1,3,5,5,5-heptamethyltrisiloxane-3-yl)propoxy)-2-hydroxypropyl methacrylate (SiMAA), mono-n-butyl terminated monomethacryloxypropyl terminated polydimethylsiloxane (mPDMS), and mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether terminated mono-n-butyl terminated polydimethylsiloxane (OH-mPDMS).

[0153] In some embodiments, the reactive monomer mixture of composition (C) further comprises at least one hydrophilic monomer. In some embodiments, the hydrophilic monomer is selected from vinylpyrrolidone, N-vinyl-N-methylacetamide, N-methylmethacrylamide, N-vinylacetamide, N,N-dimethylacrylamide, N-hydroxyethylacrylamide, N-(2-hydroxypropyl)acrylamide, N-(3-hydroxypropyl)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, N-(3-hydroxypropyl)(meth)acrylamide, poly(ethylene glycol) methyl ether(meth)acrylate, poly(ethylene glycol)(meth)acrylate, and any combination thereof. In some embodiments, the hydrophilic monomer has at least one aliphatic group having at least one double bond.

[0154] In some embodiments of composition (C), the at least one crosslinking agent is selected from the group consisting of non-alicyclic crosslinking agents, alicyclic crosslinking agents, and any combination thereof. In certain embodiments, the at least one crosslinking agent is a non-alicyclic crosslinking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl(meth)acrylate) terminated polydimethylsiloxane, and any combination thereof. In more specific embodiments, the non-alicyclic crosslinking agent is ethylene glycol dimethacrylate. In certain embodiments, the at least one crosslinking agent is an alicyclic crosslinking agent comprising an alicyclic group having 1 to 4 alicyclic rings. In an even more specific embodiment, the alicyclic crosslinker is a tricyclo[5.2.1.0 2,6 ] decanedimethanol di(meth)acrylate (e.g., tricyclo[5.2.1.0 2,6 ]decane dimethanol diacrylate).

[0155] In some embodiments, the reactive monomer mixture of composition (C) comprises the cycloaliphatic crosslinker in an amount of from about 1 to about 20 weight percent, including from about 1, 5, 10, 15, and 20 weight percent, from about 3 to about 15 weight percent, including from about 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15 weight percent, or from about 3 to about 10 weight percent, including from about 3, 4, 5, 6, 7, 8, 9, and 10 weight percent. In some embodiments, the weight percent of the cycloaliphatic crosslinker present in the reactive monomer mixture is calculated excluding the diluent.

[0156] In some embodiments, the crosslinker has the formula:

[0157] [ka] wherein n is an integer from 5 to 50, including 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, and 50. In some embodiments, n is 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25. In certain embodiments, n is 20. In some embodiments, the reactive monomer mixture comprises a crosslinker in an amount of about 15% to about 22% by weight, or about 16% to about 20% by weight. In a particular embodiment, the crosslinker is present in the reactive monomer mixture in an amount of about 18% by weight.

[0158] In some embodiments of composition (C), the reactive monomer mixture further comprises a polyamide. In some embodiments, the at least one polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinyl-acetamide), poly(dimethylacrylamide), and copolymers or mixtures thereof. In certain embodiments, the at least one polyamide is selected from poly(vinylpyrrolidone) and poly(N-vinyl-N-methylacetamide). In certain embodiments, the at least one polyamide is a copolymer.

[0159] In some embodiments, the reactive monomer mixture of composition (C) comprises at least one polyamide in an amount of from about 0.1 wt % to about 5 wt %, including from about 0.1, 0.5, 1, 2, 3, 4, and 5 wt %, from about 0.5 wt % to about 3 wt %, including from about 0.5, 1, 2, and 3 wt %, or from about 0.5 wt % to about 2 wt %, including from about 0.5, 1, and 2 wt %. In some embodiments, the weight percent of the at least one polyamide present in the reactive monomer mixture is calculated excluding the diluent.

[0160] In some embodiments, composition (C) further comprises at least one UV / HEV absorbing compound in the reactive monomer mixture. In some embodiments, the UV / HEV absorbing compound can take the form of Formula II:

[0161] [ka] During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; X is O, S, NR, SO, or SO2; Y is a linking group; P g is a polymerizable group, R, at each occurrence, is independently H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or YP g and R 1 and R 2 is, when present, independently at each occurrence C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halo), halo, hydroxy, amino, NR 3 R 4 or benzyl, where R 3 and R 4 are independently H or C1-C6 alkyl, or two adjacent R 1 Or R 2 the groups, together with the carbon atom to which they are attached, are joined to form a cycloalkyl or aryl ring; EWG is an electron withdrawing group.

[0162] The compound of formula II preferably contains one or two YP g More preferably, the compound contains one YP group. g Contains a group.

[0163] In certain embodiments, the at least one UV / HEV absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, or any combination thereof. In certain embodiments, the at least one UV / HEV absorbing compound is 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate. In certain embodiments, the at least one UV / HEV absorbing compound is 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate.

[0164] In some embodiments, the reactive monomer mix of composition (C) comprises at least one UV / HEV absorbing compound in an amount of from about 0.1 to about 5 wt%, including about 0.1, 0.5, 1, 2, 3, 4, and 5 wt%, from about 1 to about 4 wt%, including about 1, 2, 3, and 4 wt%, or from about 1 to about 3 wt%, including about 1, 2, and 3 wt%. In some embodiments, the weight percent of the at least one UV / HEV absorbing compound present in the reactive monomer mix is ​​calculated excluding the diluent.

[0165] In some embodiments, composition (C) further comprises at least one diluent in the reactive monomer mixture.

[0166] In some embodiments, composition (C) has a moisture content of about 0% to about 15%, including about 0, 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15%, or about 1% to about 10%, including about 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10%, or about 1% to about 8%, including about 1, 2, 3, 4, 5, 6, 7, and 8%, or about 0.5 to less than 5%, including 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, and 4.5%. In some embodiments, the moisture content is measured when the material is hydrated at 37° C.

[0167] In some embodiments, composition (C) has a refractive index of at least 1.45 and an Abbe number of at least 45. In other embodiments, composition (C) has a refractive index of at least 1.48 and an Abbe number of at least 50. In yet other embodiments, composition (C) has a refractive index of at least 1.50 and an Abbe number of at least 50. In some embodiments, the indicated refractive index and indicated Abbe number are measured when the material is in a dry state at 25° C.

[0168] In some embodiments of composition (C), the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator. In some embodiments, the initiator is bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.

[0169] (4) Composition (D) In some embodiments, the presently disclosed subject matter provides a composition, referred to herein as “Composition (D),” prepared by free radical polymerization of a reactive monomer mixture comprising: (i) at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings; (ii) at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers, and any combination thereof; and (iii) at least one crosslinker (“Composition (D)”), the composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39.

[0170] In some embodiments, the at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings comprises two or more individual monocyclic alicyclic rings. In some embodiments, the at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings comprises a bicyclic, tricyclic, bridged, fused, and / or spirocyclic alicyclic ring system. In some embodiments, the at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings has at least one alicyclic group that contains at least one carbon-carbon double bond. In some embodiments, the alicyclic (meth)acrylate monomer containing two or more alicyclic rings is norbornyl (meth)acrylate, isobornyl (meth)acrylate, isobornyl derivatives, norbornyl derivatives, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl (meth)acrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, poly(ethylene)glycol dicyclopentenyl ether (meth)acrylate, 2,2-bis(cyclopent-1-en-1-yloxy)ethyl (meth)acrylate, 2-(((3aR,4R,5S,7R,7aR)-octahydro-1H-4,7-methanoinden-5-yl)oxy)ethyl acrylate, 2-(((3aS,4R,6S,8R,9R)-octahydro-1H-4,7-methanoinden-5-yl)oxy)ethyl acrylate, 2-(((3aS,4R,6S,8 ... S,7R,7aR)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, (3aS,4S,5R,7S,7aS)-octahydro-1H-4,7-methanoinden-5-yl acrylate, (3aS,4S,5R,7S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden The 2-methyladamantan-5-yl acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl PEG (meth)acrylate derivatives and (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate derivatives, and any combination thereof.In some embodiments, the at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings is ethylene glycol dicyclopentenyl ether acrylate.

[0171] In some embodiments, alicyclic (meth)acrylates containing two or more alicyclic rings do not include substituents (eg, hydroxy substituents) on the alicyclic moiety or anywhere else on the monomer.

[0172] In some embodiments, the reactive monomer mixture of composition (D) comprises an alicyclic (meth)acrylate monomer containing two or more alicyclic rings in an amount of about 40 to about 90 weight percent, including about 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, and 90 weight percent, about 50 to about 80 weight percent, including about 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, and 70 weight percent. In some embodiments, the weight percent of the alicyclic (meth)acrylate monomer containing two or more alicyclic rings present in the reactive monomer mixture is calculated excluding the diluent.

[0173] In some embodiments, the reactive monomer mixture of composition (D) comprises at least one hydrophilic monomer. In some embodiments, the at least one hydrophilic monomer is selected from vinylpyrrolidone, N-vinyl-N-methylacetamide, N-methylmethacrylamide, N-vinylacetamide, N,N-dimethylacrylamide, N-hydroxyethylacrylamide, N-(2-hydroxypropyl)acrylamide, N-(3-hydroxypropyl)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, and N-(3-hydroxypropyl)(meth)acrylamide, poly(ethylene glycol) methyl ether (meth)acrylate, poly(ethylene glycol)(meth)acrylate, and any combination thereof.

[0174] In some embodiments, the hydrophilic monomer is a poly(ethylene glycol)-containing monomer. In some embodiments, the poly(ethylene glycol)-containing monomer is selected from poly(ethylene glycol) methyl ether (meth)acrylate and poly(ethylene glycol) (meth)acrylate. In some embodiments, the poly(ethylene glycol)-containing monomer is poly(ethylene glycol) methacrylate. In some embodiments, the poly(ethylene glycol)-containing monomer is poly(ethylene glycol) methyl ether methacrylate. In some embodiments, the reactive monomer mixture of composition (D) comprises a combination of poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate.

[0175] In some embodiments, the poly(ethylene glycol) containing monomer is 200 g / mol, 220 g / mol, 240 g / mol, 260 g / mol, 280 g / mol, 300 g / mol, 320 g / mol, 340 g / mol, 360 g / mol, 380 g / mol, 400 g / mol, 420 g / mol, 440 g / mol, 460 g / mol, 480 g / mol, 500 g / mol, 520 g / mol, 540 g / mol, 560 g / mol, 580 g / mol, 600 g / mol, mol, 620 g / mol, 640 g / mol, 660 g / mol, 680 g / mol, 700 g / mol, 720 g / mol, 740 g / mol, 760 g / mol, 780 g / mol, 800 g / mol, 820 g / mol, 840 g / mol, 860 g / mol, 880 g / mol, 900 g / mol, 920 g / mol, 940 g / mol, 960 g / mol, 980 g / mol, and 1000 g / mol. nIn some embodiments, the poly(ethylene glycol)-containing monomer has a number average molecular weight (M) of about 200 g / mol to about 400 g / mol, including 200 g / mol, 220 g / mol, 240 g / mol, 260 g / mol, 280 g / mol, 300 g / mol, 320 g / mol, 340 g / mol, 360 g / mol, 380 g / mol, and 400 g / mol. n ).

[0176] In some embodiments, the poly(ethylene glycol)-containing monomer has the formula:

[0177] [ka] In the formula, R a and R b are each independently selected from hydrogen and methyl, and m is an integer from 2 to 25, including 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, and 25. a may be hydrogen. In some embodiments, R a is methyl. In some embodiments, R b is hydrogen. In some embodiments, R b is methyl. In certain embodiments, R a is methyl, R b is hydrogen. In some embodiments, R a is methyl, R b In some embodiments, m is an integer from 2 to 8, including 2, 3, 4, 5, 6, 7, and 8.

[0178] In some embodiments, the reactive monomer mixture of composition (D) is from about 1 to about 40 weight percent, including about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, and 40 weight percent. At least one hydrophilic monomer (e.g., a poly(ethylene glycol)-containing monomer) is included in an amount of about 10 to about 30% by weight, including 0, 21, 22, 23, 24, 25, 26, 27, 28, 29, and 30% by weight, about 12 to about 22% by weight, including about 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, and 22% by weight, or about 14 to about 20% by weight, including about 14, 15, 16, 17, 18, 19, and 20% by weight. In some embodiments, the weight percent of at least one hydrophilic monomer (e.g., a poly(ethylene glycol)-containing monomer) present in the reactive monomer mixture is calculated excluding the diluent.

[0179] In some embodiments, the reactive monomer mixture of composition (D) comprises at least one hydroxyalkyl (meth)acrylate monomer. In some embodiments, the hydroxyalkyl (meth)acrylate is selected from the group consisting of C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39, C40, C41, C42, C43, C44, C45, C46, ​​C47, C48, C49, C50, C51, C52, C53, C54, C55, C56, C57, C58, C59, C60, C61, C62, C63, C64, C65, C66, C67, C68, C69, C70, C71, C72, C73, C74, C75, C76, C77, C78, ​​C79, C80, C81, C82, C83, C84, C85, C86, C87, C88, C89, C90, C91, C92, C93, C94, C95, C96, C97, C98, C99, C99, C101, C102, C103, C104, C105, C106, C107, C108, C109, C1109, C1111, C112, C123, C124, C12 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , and C 25 1 to 25 carbon atoms (C1 to C 25In some embodiments, the hydroxyalkyl (meth)acrylate is selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, and any combination thereof. In some embodiments, the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate or 2-hydroxyethyl methacrylate. In certain embodiments, the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate is 2-hydroxyethyl methacrylate.

[0180] In some embodiments, the reactive monomer mixture of composition (D) comprises a hydroxyalkyl (meth)acrylate in an amount of from about 1 to about 10 weight percent, including from about 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10 weight percent, from about 2 to about 8 weight percent, including from about 2, 3, 4, 5, 6, 7, and 8 weight percent, or from about 4 to about 6 weight percent, including from 4, 5, and 6 weight percent. In some embodiments, the weight percent of hydroxyalkyl (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0181] In some embodiments, the reactive monomer mix of composition (D) comprises a combination of a hydrophilic monomer and a hydroxyalkyl (meth)acrylate monomer. In some embodiments, the reactive monomer mix comprises a combination of a poly(ethylene glycol)-containing monomer and a hydroxyalkyl (meth)acrylate monomer. In some embodiments, the reactive monomer mix comprises a combination of poly(ethylene glycol) methyl ether (meth)acrylate and 2-hydroxyethyl (meth)acrylate. In some embodiments, the reactive monomer mix comprises a combination of poly(ethylene glycol) (meth)acrylate and 2-hydroxyethyl (meth)acrylate.

[0182] In some embodiments, composition (D) is prepared by free radical polymerization of a reactive monomer mixture comprising: (i) at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings, (ii) at least one poly(ethylene glycol)-containing monomer, and (iii) at least one crosslinker. In some embodiments, composition (D) is prepared by free radical polymerization of a reactive monomer mixture comprising: (i) at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings, (ii) at least one poly(ethylene glycol)-containing monomer selected from poly(ethylene glycol) (meth)acrylate and poly(ethylene glycol) methyl ether (meth)acrylate, and (iii) at least one crosslinker.

[0183] In some embodiments, composition (D) is made by free radical polymerization of a reactive monomer mixture comprising: (i) ethylene glycol dicyclopentenyl ether (meth)acrylate monomer; (ii) at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers, and any combination thereof; and (iii) at least one crosslinker.

[0184] In some embodiments, composition (D) is prepared by free radical polymerization of a reactive monomer mixture comprising (i) ethylene glycol dicyclopentenyl ether (meth)acrylate monomer, (ii) at least one poly(ethylene glycol)-containing monomer, and (iii) at least one crosslinker. In some embodiments, composition (D) is prepared by free radical polymerization of a reactive monomer mixture comprising (i) ethylene glycol dicyclopentenyl ether (meth)acrylate monomer, (ii) at least one poly(ethylene glycol)-containing monomer selected from poly(ethylene glycol) (meth)acrylate and poly(ethylene glycol) methyl ether (meth)acrylate, and (iii) at least one crosslinker.

[0185] In some embodiments, the reactive monomer mixture of composition (D) further comprises at least one alicyclic (meth)acrylate containing one alicyclic ring. In some embodiments, the at least one alicyclic (meth)acrylate containing one alicyclic ring comprises an alicyclic group having at least one carbon-carbon double bond. The alicyclic ring can be a C3-C8 cycloalkyl group, a C3-C7 cycloalkyl group, a C4-C7 cycloalkyl group, or a C5-C6 cycloalkyl group. In some embodiments, the alicyclic (meth)acrylate containing one alicyclic ring is selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, and any combination thereof. In some embodiments, the alicyclic (meth)acrylate containing one alicyclic ring is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, 2-cyclohexyl ethyl acrylate, 2-cyclohexyl ethyl methacrylate, 3-cyclohexyl propyl acrylate, and any combination thereof. In some embodiments, the alicyclic (meth)acrylate containing one alicyclic ring is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, 2-cyclohexyl ethyl acrylate, and 3-cyclohexyl propyl acrylate. In some embodiments, the alicyclic (meth)acrylate is cyclohexyl acrylate. In some embodiments, the alicyclic (meth)acrylate containing one alicyclic ring is cyclohexyl methyl acrylate. In some embodiments, the alicyclic (meth)acrylate containing one alicyclic ring is cyclohexyl methyl methacrylate. In some embodiments, the cycloaliphatic (meth)acrylate containing one cycloaliphatic ring is 2-cyclohexylethyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate containing one cycloaliphatic ring is 2-cyclohexylethyl methacrylate.In some embodiments, the combination is a combination of cyclohexylmethyl acrylate and cyclohexylmethyl methacrylate. In some embodiments, the combination is a combination of 2-cyclohexylethyl acrylate and 2-cyclohexylethyl methacrylate.

[0186] In some embodiments, the alicyclic (meth)acrylate does not contain any substituents (e.g., hydroxy substituents) in the alicyclic portion or anywhere else on the monomer (e.g., in a monomer such as 2-cyclohexylethyl (meth)acrylate, the monomer does not contain any substituents such as hydroxy substituents in either the cyclohexyl or ethyl portion).

[0187] In some embodiments, the reactive monomer mixture of composition (D) comprises at least one alicyclic (meth)acrylate containing an aliphatic ring in an amount of about 10 to about 25 wt%, including about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, and 25 wt%, about 10 to about 20 wt%, including about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 wt%, or about 12 to about 15 wt%, including about 12, 13, 14, and 15 wt%. In some embodiments, the weight percent of the at least one alicyclic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0188] In some embodiments, the reactive monomer mixture of composition (D) further comprises at least one aromatic (meth)acrylate. In some embodiments, the at least one aromatic (meth)acrylate is a (meth)acrylate containing at least one aryl group. In some embodiments, the aryl group is a phenyl group. In some embodiments, the aryl group can be present in the aromatic (meth)acrylate as part of an arylalkyl group (e.g., benzyl, 2-phenylethyl, 3-phenylpropyl, or 4-phenylbutyl), an aryloxyalkyl group (e.g., phenoxymethyl, 2-phenoxyethyl, or 3-phenoxypropyl), or an arylthioalkyl group (e.g., phenylthiomethyl, 2-phenylthioethyl, or 3-phenylthiopropyl). In some embodiments, the at least one aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the at least one aromatic (meth)acrylate is selected from 2-phenylethyl acrylate, 2-phenylethyl methacrylate, 3-phenylpropyl acrylate, and 4-phenylbutyl acrylate. In some embodiments, the at least one aromatic (meth)acrylate is 2-phenylethyl acrylate.In some embodiments, at least one aromatic (meth)acrylate is 2-phenylethyl methacrylate. In some embodiments, the aromatic (meth)acrylate is 3-phenylpropyl acrylate. In some embodiments, the aromatic (meth)acrylate is 4-phenylbutyl acrylate. In some embodiments, the combination is 2-phenylethyl acrylate and 2-phenylethyl methacrylate. In some embodiments, the combination is 2-phenylethyl acrylate and 3-phenylpropyl acrylate. In some embodiments, the combination is 2-phenylethyl methacrylate and 3-phenylpropyl acrylate.

[0189] In some embodiments, the at least one aromatic (meth)acrylate has at least one aliphatic group containing at least one carbon-carbon double bond. In some embodiments, the at least one aromatic (meth)acrylate is cinnamyl (meth)acrylate.

[0190] In some embodiments, the reactive monomer mixture of composition (D) comprises at least one aromatic (meth)acrylate in an amount of from about 7 to about 25 wt%, including from about 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, and 25 wt%, from about 10 to about 20 wt%, including from about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 wt%, or from about 12 to about 15 wt%, including from about 12, 13, 14, and 15 wt%. In some embodiments, the weight percent of the at least one aromatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0191] In some embodiments, the reactive monomer mixture of composition (D) does not include aromatic monomers, such as aromatic (meth)acrylates.

[0192] In some embodiments of composition (D), the at least one crosslinking agent is selected from the group consisting of non-alicyclic crosslinking agents, alicyclic crosslinking agents, and any combination thereof. In certain embodiments, the at least one crosslinking agent is a non-alicyclic crosslinking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl(meth)acrylate) terminated polydimethylsiloxane, and any combination thereof. In more specific embodiments, the non-alicyclic crosslinking agent is ethylene glycol dimethacrylate. In certain embodiments, the at least one crosslinking agent is an alicyclic crosslinking agent comprising an alicyclic group having 1 to 4 alicyclic rings. In an even more specific embodiment, the alicyclic crosslinker is a tricyclo[5.2.1.0 2,6 ] decanedimethanol di(meth)acrylate (e.g., tricyclo[5.2.1.0 2,6 ]decane dimethanol diacrylate).

[0193] In some embodiments, the reactive monomer mixture of composition (D) comprises a crosslinker in an amount of from about 1 to about 20 weight percent, including from about 1, 5, 10, 15, and 20 weight percent, from about 3 to about 15 weight percent, including from about 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15 weight percent, or from about 3 to about 10 weight percent, including from about 3, 4, 5, 6, 7, 8, 9, and 10 weight percent. In some embodiments, the weight percent of cycloaliphatic crosslinker present in the reactive monomer mixture is calculated excluding the diluent.

[0194] In some embodiments, the crosslinker has the formula:

[0195] [ka] wherein n is an integer from 5 to 50, including 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, and 50. In some embodiments, n is 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25. In certain embodiments, n is 20. In some embodiments, the reactive monomer mixture comprises a crosslinker in an amount of about 15% to about 22% by weight, or about 16% to about 20% by weight. In a particular embodiment, the crosslinker is present in the reactive monomer mixture in an amount of about 18% by weight.

[0196] In some embodiments of composition (D), the reactive monomer mixture further comprises a polyamide. In some embodiments, the at least one polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinyl-acetamide), poly(dimethylacrylamide), and copolymers or mixtures thereof. In certain embodiments, the at least one polyamide is selected from poly(vinylpyrrolidone) and poly(N-vinyl-N-methylacetamide). In certain embodiments, the at least one polyamide is a copolymer.

[0197] In some embodiments, the reactive monomer mixture of composition (D) comprises at least one polyamide in an amount of from about 0.1 wt % to about 5 wt %, including from about 0.1, 0.5, 1, 2, 3, 4, and 5 wt %, from about 0.5 wt % to about 3 wt %, including from about 0.5, 1, 2, and 3 wt %, or from about 0.5 wt % to about 2 wt %, including from about 0.5, 1, and 2 wt %. In some embodiments, the weight percent of the at least one polyamide present in the reactive monomer mixture is calculated excluding the diluent.

[0198] In some embodiments, composition (D) further comprises at least one UV / HEV absorbing compound in the reactive monomer mixture. In some embodiments, the UV / HEV absorbing compound can take the form of Formula II:

[0199] [ka] During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; X is O, S, NR, SO, or SO2; Y is a linking group; P g is a polymerizable group, R, at each occurrence, is independently H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or YP g and R 1 and R 2 is, when present, independently at each occurrence C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halo), halo, hydroxy, amino, NR 3 R 4 or benzyl, where R 3 and R 4 are independently H or C1-C6 alkyl, or two adjacent R 1 Or R 2 the groups, together with the carbon atom to which they are attached, are joined to form a cycloalkyl or aryl ring; EWG is an electron withdrawing group.

[0200] The compound of formula II preferably contains one or two YP g More preferably, the compound contains one YP group. g Contains a group.

[0201] In certain embodiments, the at least one UV / HEV absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, or any combination thereof. In certain embodiments, the at least one UV / HEV absorbing compound is 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate. In certain embodiments, the at least one UV / HEV absorbing compound is 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate.

[0202] In some embodiments, the reactive monomer mix of composition (D) comprises at least one UV / HEV absorbing compound in an amount of from about 0.1 to about 5 wt%, including about 0.1, 0.5, 1, 2, 3, 4, and 5 wt%, from about 1 to about 4 wt%, including about 1, 2, 3, and 4 wt%, or from about 1 to about 3 wt%, including about 1, 2, and 3 wt%. In some embodiments, the weight percent of the at least one UV / HEV absorbing compound present in the reactive monomer mix is ​​calculated excluding the diluent.

[0203] In some embodiments, composition (D) further comprises at least one diluent in the reactive monomer mixture.

[0204] In some embodiments, composition (D) has a moisture content of about 0% to about 15%, including about 0, 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15%, or about 1% to about 10%, including about 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10%, or about 1% to about 8%, including about 1, 2, 3, 4, 5, 6, 7, and 8%, or about 0.5 to less than 5%, including 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, and 4.5%. In some embodiments, the moisture content is measured when the material is hydrated at 37° C.

[0205] In some embodiments, composition (D) has a refractive index of at least 1.45 and an Abbe number of at least 45. In other embodiments, composition (D) has a refractive index of at least 1.48 and an Abbe number of at least 50. In yet other embodiments, composition (D) has a refractive index of at least 1.50 and an Abbe number of at least 50. In some embodiments, the indicated refractive index and indicated Abbe number are measured when the material is in a dry state at 25° C.

[0206] In some embodiments of composition (D), the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator. In some embodiments, the initiator is bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.

[0207] (5) Composition (E) In some embodiments, the presently disclosed subject matter comprises a polymerizable composition comprising: (i) at least one hydrophobic monomer; (ii) at least one monomer selected from a hydrophilic monomer, a hydroxyalkyl (meth)acrylate monomer, and any combination thereof; and (iii) a tricyclo[5.2.1.0 2,6] and a decanedimethanol di(meth)acrylate crosslinker, and the composition, referred to herein as "Composition (E)," is prepared by free radical polymerization of a reactive monomer mixture comprising:

[0208] In some embodiments of composition (E), the hydrophobic monomer is a hydrophobic (meth)acrylate monomer. In some embodiments, the hydrophobic (meth)acrylate is selected from cycloaliphatic (meth)acrylates, aliphatic (meth)acrylates, aromatic (meth)acrylates, and any combination thereof.

[0209] In some embodiments of composition (E), the hydrophobic (meth)acrylate is an alicyclic (meth)acrylate. In some embodiments, the alicyclic (meth)acrylate comprises an alicyclic group having 1 to 4 alicyclic rings. In some embodiments, the alicyclic group has one alicyclic ring. The alicyclic ring can be a C3-C8 cycloalkyl group, a C3-C7 cycloalkyl group, a C4-C7 cycloalkyl group, or a C5-C6 cycloalkyl group. In some embodiments, the alicyclic (meth)acrylate has at least one alicyclic group that includes at least one carbon-carbon double bond.In some embodiments, the alicyclic (meth)acrylate is cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, norbornyl (meth)acrylate, isobornyl (meth)acrylate, isobornyl derivatives, norbornyl derivatives, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl (meth)acrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, poly(ethylene)glycol dicyclopentenyl ether (meth)acrylate, 2,2-bis(cyclopent-1-en-1-yloxy)ethyl (meth)acrylate, 2-(((3aR,4 R,5S,7R,7aR)-Octahydro-1H-4,7-methanoinden-5-yl)oxy)ethyl acrylate, 2-(((3aS,4R,6S,7R,7aR)-3a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, (3aS,4S,5R,7S,7aS)-Octahydro-1H-4,7-methanoinden-5-yl acrylate, (3aS,4S,5R,7S,7aS)- 3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-yl acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl PEG (meth)acrylate derivatives and (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate derivatives, and any combination thereof. In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, and any combination thereof.In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, cyclohexyl methyl methacrylate, 2-cyclohexyl ethyl acrylate, 2-cyclohexyl ethyl methacrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the cycloaliphatic (meth)acrylate is cyclohexyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is cyclohexyl methyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is 2-cyclohexyl ethyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is ethylene glycol dicyclopentenyl ether acrylate.

[0210] In some embodiments, the alicyclic (meth)acrylate does not contain any substituents (e.g., hydroxy substituents) in the alicyclic portion or anywhere else on the monomer (e.g., in a monomer such as 2-cyclohexylethyl (meth)acrylate, the monomer does not contain any substituents such as hydroxy substituents in either the cyclohexyl or ethyl portion).

[0211] In some embodiments, the reactive monomer mixture of composition (E) comprises the cycloaliphatic (meth)acrylate monomer in an amount of from about 40 to about 90 weight percent, including about 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, and 90 weight percent, from about 50 to about 80 weight percent, including about 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, and 70 weight percent. In some embodiments, the weight percent of the cycloaliphatic (meth)acrylate monomer present in the reactive monomer mixture is calculated excluding the diluent.

[0212] In certain embodiments, the hydrophobic (meth)acrylate is an aliphatic (meth)acrylate. In some embodiments, the aliphatic (meth)acrylate is a C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39, C40, C41, C42, C43, C44, C45, C46, ​​C47, C48, C49, C50, C51, C52, C53, C54, C55, C56, C5 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , and C 18 Linear or branched alkyl groups containing 1 to 18 carbon atoms (C1 to C2) including alkyl (meth)acrylates 18 In a more specific embodiment, C1 to C 18 The alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, isodecyl (meth)acrylate, heptadecyl (meth)acrylate, dodecyl (meth)acrylate, 2-propylheptyl (meth)acrylate, stearyl (meth)acrylate, and any combination thereof. In still more specific embodiments, the aliphatic (meth)acrylate comprises a straight chain alkyl group containing 4 to 8 carbon atoms (C4 to C8 straight chain alkyl group). In some embodiments, the aliphatic (meth)acrylate is n-hexyl acrylate.

[0213] In some embodiments, the reactive monomer mix of composition (E) comprises an aliphatic (meth)acrylate in an amount of from about 1 to about 20 weight percent, including from about 1, 5, 10, 15, and 20 weight percent, or from about 1 to about 10 weight percent, including from about 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10 weight percent. In some embodiments, the weight percent of the aliphatic (meth)acrylate present in the reactive monomer mix is ​​calculated excluding the diluent.

[0214] In some embodiments, the hydrophobic (meth)acrylate is an aromatic (meth)acrylate. In some embodiments, the aromatic (meth)acrylate comprises at least one aryl group. In some embodiments, the aryl group is a phenyl group. In some embodiments, the aryl group can be present in the aromatic (meth)acrylate as part of an arylalkyl group (e.g., benzyl, 2-phenylethyl, 3-phenylpropyl, or 4-phenylbutyl), an aryloxyalkyl group (e.g., phenoxymethyl, 2-phenoxyethyl, or 3-phenoxypropyl), or an arylthioalkyl group (e.g., phenylthiomethyl, 2-phenylthioethyl, or 3-phenylthiopropyl). In some embodiments, the aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. In some embodiments, the aromatic (meth)acrylate is 2-phenylethyl acrylate. In some embodiments, the aromatic (meth)acrylate is 2-phenylethyl methacrylate. In some embodiments, the aromatic (meth)acrylate is a combination of 2-phenylethyl acrylate and 2-phenylethyl methacrylate. In some embodiments, the aromatic (meth)acrylate is 3-phenylpropyl acrylate. In some embodiments, the aromatic (meth)acrylate is 4-phenylbutyl acrylate.

[0215] In some embodiments, the reactive monomer mixture of composition (E) comprises an aromatic (meth)acrylate in an amount of from about 7 to about 25 wt%, including from about 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, and 25 wt%, from about 10 to about 20 wt%, including from about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 wt%, or from about 12 to about 15 wt%, including from about 12, 13, 14, and 15 wt%. In some embodiments, the weight percent of aromatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

[0216] The reactive monomer mixture of composition (E) comprises at least one hydrophilic monomer. In some embodiments, the reactive monomer mixture of composition (E) comprises at least one hydrophilic monomer selected from vinylpyrrolidone, N-vinyl-N-methylacetamide, N-methylmethacrylamide, N-vinylacetamide, N,N-dimethylacrylamide, N-hydroxyethylacrylamide, N-(2-hydroxypropyl)acrylamide, N-(3-hydroxypropyl)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, N-(3-hydroxypropyl)(meth)acrylamide, poly(ethylene glycol) methyl ether (meth)acrylate, poly(ethylene glycol)(meth)acrylate, and any combination thereof.

[0217] In some embodiments, the at least one hydrophilic monomer is a poly(ethylene glycol)-containing monomer. In some embodiments, the poly(ethylene glycol)-containing monomer is selected from poly(ethylene glycol) methyl ether (meth)acrylate and poly(ethylene glycol) (meth)acrylate. In some embodiments, the poly(ethylene glycol)-containing monomer is poly(ethylene glycol) methacrylate. In some embodiments, the poly(ethylene glycol)-containing monomer is poly(ethylene glycol) methyl ether methacrylate. In some embodiments, the reactive monomer mixture of composition (E) comprises a combination of poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate.

[0218] In some embodiments, the poly(ethylene glycol) containing monomer is 200 g / mol, 220 g / mol, 240 g / mol, 260 g / mol, 280 g / mol, 300 g / mol, 320 g / mol, 340 g / mol, 360 g / mol, 380 g / mol, 400 g / mol, 420 g / mol, 440 g / mol, 460 g / mol, 480 g / mol, 500 g / mol, 520 g / mol, 540 g / mol, 560 g / mol, 580 g / mol, 600 g / mol, mol, 620 g / mol, 640 g / mol, 660 g / mol, 680 g / mol, 700 g / mol, 720 g / mol, 740 g / mol, 760 g / mol, 780 g / mol, 800 g / mol, 820 g / mol, 840 g / mol, 860 g / mol, 880 g / mol, 900 g / mol, 920 g / mol, 940 g / mol, 960 g / mol, 980 g / mol, and 1000 g / mol. nIn some embodiments, the poly(ethylene glycol)-containing monomer has a number average molecular weight (M) of about 200 g / mol to about 400 g / mol, including 200 g / mol, 220 g / mol, 240 g / mol, 260 g / mol, 280 g / mol, 300 g / mol, 320 g / mol, 340 g / mol, 360 g / mol, 380 g / mol, and 400 g / mol. n ).

[0219] In some embodiments, the poly(ethylene glycol)-containing monomer has the formula:

[0220] [ka] In the formula, R a and R b are each independently selected from hydrogen and methyl, and m is an integer from 2 to 25, including 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, and 25. a may be hydrogen. In some embodiments, R a is methyl. In some embodiments, R b is hydrogen. In some embodiments, R b is methyl. In certain embodiments, R a is methyl, R b is hydrogen. In some embodiments, R a is methyl, R b In some embodiments, m is an integer from 2 to 8, including 2, 3, 4, 5, 6, 7, and 8.

[0221] In some embodiments, the hydrophilic monomer is selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 4-hydroxybutyl acrylate. In some embodiments, the hydrophilic monomer is selected from 2-hydroxyethyl methacrylate and 4-hydroxybutyl acrylate. In some embodiments, the hydrophilic monomer is 4-hydroxybutyl acrylate.

[0222] In some embodiments, the reactive monomer mixture of composition (D) comprises a combination of a poly(ethylene glycol)-containing monomer and a hydrophilic monomer selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, and 4-hydroxybutyl acrylate. In some embodiments, the reactive monomer mixture of composition (D) comprises a combination of poly(ethylene glycol) (meth)acrylate and 2-hydroxyethyl (meth)acrylate. In some embodiments, the reactive monomer mixture of composition (D) comprises a combination of poly(ethylene glycol) methacrylate and 2-hydroxyethyl methacrylate. In some embodiments, the reactive monomer mixture of composition (D) comprises a combination of poly(ethylene glycol) methyl ether methacrylate and 2-hydroxyethyl methacrylate.

[0223] In some embodiments, the reactive monomer mixture of composition (E) is from about 1 to about 40 weight percent, including about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, and 40 weight percent, from about 10 to about 30 weight percent, including about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, and 30 weight percent. about 12 to about 22 wt%, including about 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, and 22 wt%, about 14 to about 20 wt%, including about 14, 15, 16, 17, 18, 19, and 20 wt%, about 1 to about 10 wt%, including about 2, 3, 4, 5, 6, 7, 8, 9, and 10 wt%, about 2 to about 8 wt%, including about 4, 5, and 6 wt%, or about 4 to about 6 wt%, including about 4, 5, and 6 wt%. In some embodiments, the weight percent of at least one hydrophilic monomer (e.g., poly(ethylene glycol)-containing monomer) present in the reactive monomer mixture is calculated excluding the diluent.

[0224] In some embodiments, tricyclo[5.2.1.0 2,6 ]Decanedimethanol di(meth)acrylate crosslinker is tricyclo[5.2.1.0 2,6 ] decanedimethanol diacrylate.

[0225] In some embodiments, the reactive monomer mixture of composition (E) comprises from about 1 to about 20 weight percent, including about 1, 5, 10, 15, and 20 weight percent, from about 3 to about 15 weight percent, including 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15, or from about 3 to about 10 weight percent, including 3, 4, 5, 6, 7, 8, 9, and 10 weight percent, of tricyclo[5.2.1.0]. 2,6 ] decanedimethanol di(meth)acrylate crosslinkers (e.g., tricyclo[5.2.1.0 2,6]decane dimethanol diacrylate). In some embodiments, the tricyclo[5.2.1.0 2,6 ] The weight percent of decanedimethanol di(meth)acrylate crosslinker is calculated excluding the diluent.

[0226] In some embodiments, the reactive monomer mixture of composition (E) comprises: (i) ethylene glycol dicyclopentenyl ether acrylate; (ii) a hydrophilic monomer selected from the group consisting of poly(ethylene glycol) methacrylate, poly(ethylene glycol) methyl ether methacrylate, 2-hydroxyethyl methacrylate, and any combination thereof; and (iii) tricyclo[5.2.1.0 2,6 ] decanedimethanol diacrylate crosslinker, and the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

[0227] In some embodiments of composition (E), the reactive monomer mixture further comprises a polyamide. In some embodiments, the at least one polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinyl-acetamide), poly(dimethylacrylamide), and copolymers or mixtures thereof. In certain embodiments, the at least one polyamide is selected from poly(vinylpyrrolidone) and poly(N-vinyl-N-methylacetamide). In certain embodiments, the at least one polyamide is a copolymer.

[0228] In some embodiments, the reactive monomer mixture of composition (E) comprises at least one polyamide in an amount of from about 0.1 wt % to about 5 wt %, including from about 0.1, 0.5, 1, 2, 3, 4, and 5 wt %, from about 0.5 wt % to about 3 wt %, including from about 0.5, 1, 2, and 3 wt %, or from about 0.5 wt % to about 2 wt %, including from about 0.5, 1, and 2 wt %. In some embodiments, the weight percent of the at least one polyamide present in the reactive monomer mixture is calculated excluding the diluent.

[0229] In some embodiments, composition (E) further comprises at least one UV / HEV absorbing compound in the reactive monomer mixture. In some embodiments, the UV / HEV absorbing compound can take the form of Formula II:

[0230] [ka] During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; X is O, S, NR, SO, or SO2; Y is a linking group; P g is a polymerizable group, R, at each occurrence, is independently H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or YP g and R 1 and R 2 is, when present, independently at each occurrence C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halo), halo, hydroxy, amino, NR 3 R 4 or benzyl, where R 3 and R 4 are independently H or C1-C6 alkyl, or two adjacent R 1 Or R 2 the groups, together with the carbon atom to which they are attached, are joined to form a cycloalkyl or aryl ring; EWG is an electron withdrawing group.

[0231] The compound of formula II preferably contains one or two YP g More preferably, the compound contains one YP group. g Contains a group.

[0232] In certain embodiments, the at least one UV / HEV absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, or any combination thereof. In certain embodiments, the at least one UV / HEV absorbing compound is 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate. In certain embodiments, the at least one UV / HEV absorbing compound is 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate.

[0233] In some embodiments, the reactive monomer mix of composition (E) comprises at least one UV / HEV absorbing compound in an amount of from about 0.1 to about 5 wt%, including about 0.1, 0.5, 1, 2, 3, 4, and 5 wt%, from about 1 to about 4 wt%, including about 1, 2, 3, and 4 wt%, or from about 1 to about 3 wt%, including about 1, 2, and 3 wt%. In some embodiments, the weight percent of the at least one UV / HEV absorbing compound present in the reactive monomer mix is ​​calculated excluding the diluent.

[0234] In some embodiments, composition (E) further comprises at least one diluent in the reactive monomer mixture.

[0235] In some embodiments, composition (E) has a moisture content of about 0% to about 15%, including about 0, 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15%, or about 1% to about 10%, including about 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10%, or about 1% to about 8%, including about 1, 2, 3, 4, 5, 6, 7, and 8%, or about 0.5 to less than 5%, including 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, and 4.5%. In some embodiments, the moisture content is measured when the material is hydrated at 37° C.

[0236] In some embodiments, composition (E) has a refractive index of at least 1.45 and an Abbe number of at least 45. In other embodiments, composition (E) has a refractive index of at least 1.48 and an Abbe number of at least 50. In yet other embodiments, composition (E) has a refractive index of at least 1.50 and an Abbe number of at least 50. In some embodiments, the indicated refractive index and indicated Abbe number are measured when the material is in a dry state at 25° C.

[0237] In some embodiments of composition (E), the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator. In some embodiments, the initiator is bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.

[0238] C. Ophthalmic Devices In some embodiments, the presently disclosed subject matter provides a device comprising the composition (A, B, C, D, or E) described immediately above.

[0239] In certain embodiments, the ophthalmic device comprises a lens, inlay, outlay, or insert selected from an intraocular implant or lens, a contact lens, a corneal inlay, a corneal outlay, and a corneal insert.

[0240] In certain embodiments, the ocular device is an intraocular implant or lens. More specifically, the presently disclosed subject matter also provides intraocular implants and / or lenses made at least partially or completely from compositions (A-E) described herein. Such intraocular implants or lenses can include an optic portion and one or more haptic portions. Typically, the presently disclosed subject matter compositions make up part or all of the optic portion of the intraocular implant or lens. In some embodiments, the optic portion of the implant or lens has a core made from one of the compositions described herein surrounded by a different polymer or material. An implant or lens whose optic portion is made at least partially from one of the presently disclosed subject matter compositions also typically has haptic portions. The haptic portions can also be made from the polymers of the present disclosure, or can be made from a different material, such as another polymer.

[0241] In some embodiments, the intraocular implant or lens of the presently disclosed subject matter is a one-piece lens with a central, flexible, foldable visual region and an outer peripheral region (haptic region), both regions being made of the same polymer. In another embodiment, the visual and haptic regions can be made of different types of polymers or materials, if desired. Some implants or lenses can also have haptic portions made of different materials, for example, one or more haptic portions made of the same material as the visual portion and another haptic portion made of a material other than the polymer of the present disclosure. Multi-component implants or lenses can be made by embedding one material in another co-extrusion process, solidifying a hard material around a soft material, or forming an interpenetrating network of rigid components into a preformed hydrophobic core. In cases where one or more haptic portions are made of a different material than the visual portion of the lens, the haptic portions can be attached to the visual portion in any manner known in the art, for example, by drilling one or more holes in the visual portion and inserting the haptic portions.

[0242] The compositions described herein are designed to be folded so that the intraocular lens can be inserted into an individual's eye through a small incision. In some cases, the incision is less than 2.5 mm, and in some cases, the incision is less than 2 mm. The haptics of the lens provide the necessary support for the implant or lens in the eye after insertion and deployment of the lens, and tend to help stabilize the lens position after insertion and after the incision is closed. The shape of the haptics design is not particularly limited and can be any desired structure, for example, either flat or thickened spiral filament, also known as C-loop design.

[0243] The optic portion of the intraocular lens can be approximately 2-6 mm in diameter before hydration. A diameter of 2-6 mm is fairly standard in the art and is generally selected to cover the pupil in a fully dilated state under naturally occurring conditions. However, other sizes are contemplated, and the subject matter disclosed herein is not limited to intraocular lenses of any particular diameter or size. Furthermore, the optic portion of the lens does not necessarily have to be circular, but can also be oval, square, or any other shape, if desired.

[0244] The intraocular lens may further include one or more non-optical haptic components that extend away from the outermost peripheral surface of the optical portion. The haptic components may be of any desired shape, such as an increasing helical filament or a flat section, and are used to support the lens in the posterior chamber of the eye. Lenses may be manufactured having any desired design configuration. If the intraocular lens includes other components in addition to the optical and haptic portions, such other portions may be made of a polymer as in the haptic and optical portions, or of another material, if desired.

[0245] The intraocular implant lens can be inserted into the eye by any method known in the art. For example, the intraocular lens can be folded prior to insertion into the eye using an intraocular lens inserter or by small, thin, forceps of the type typically used by ophthalmic surgeons. After the implant or lens is placed in the target location, the implant or lens is released and deployed. As is known in the art, typically, the crystalline lens to be replaced is removed prior to insertion of the intraocular lens. The intraocular lenses of the presently disclosed subject matter can be made from generally physiologically inert, flexible polymeric materials that can provide a clean, clear refractive lens body even after folding and deployment. In some embodiments, the foldable intraocular lenses of the presently disclosed subject matter can be inserted into the eye by injection through a small tube, such as a tube with an inner diameter of 1 mm to 3 mm, with the mechanically flexible material folded.

[0246] E. Methods for Making Ophthalmic Devices In yet another embodiment, the subject matter disclosed herein provides a method for making an ophthalmic device, the method comprising: (a) providing any one of composition (A), composition (B), composition (C), composition (D), or composition (E); and (b) forming an ophthalmic device. In another embodiment, the subject matter disclosed herein provides a method for making an ophthalmic device, the method comprising: preparing a blank from any one of composition (A), composition (B), composition (C), composition (D), or composition (E); and (b) machining an ophthalmic device from the blank. In yet another embodiment, the subject matter disclosed herein provides a method for making an ophthalmic device, the method comprising: molding an ophthalmic device from any one of composition (A), composition (B), composition (C), composition (D), or composition (E). In yet another embodiment, the presently disclosed subject matter provides a method for making an ophthalmic device, comprising molding the ophthalmic device from any one of composition (A), composition (B), composition (C), composition (D), or composition (E), and then refining the surface by lathing. In certain embodiments of the above method, the method further comprises extracting the ophthalmic device with a solvent. In certain embodiments, the method further comprises hydrating the extracted ophthalmic device with at least one aqueous solution. In certain embodiments, the method further comprises irradiating using a laser, which in certain embodiments is a two-photon laser, and in more specific embodiments is a femtosecond two-photon laser. In more specific embodiments, the method further comprises sterilizing the ophthalmic device. The ophthalmic device can be sterilized by known methods, such as, but not limited to, autoclaving.

[0247] Some embodiments of the present disclosure will now be described in detail in the following examples. EXAMPLES

[0248] Unless otherwise noted, test samples for refractive index, Abbe number, water content, and glass transition temperature were polymer buttons extracted with acetonitrile or 2-propanol and dried. Unless otherwise noted, test samples for micro- and macro-brightness testing were lenses.

[0249] Refractive Index Test Method: Refractive index was measured using an Anton Paar Abbemat WR wavelength refractometer. The instrument was equilibrated at either 25°C or 35°C for a minimum of 1 hour prior to use. The measurement wavelength was set at 589.3 nanometers. The sample was placed on the quartz plate using a pair of tweezers. The instrument lid was closed and the refractive index was recorded after a dwell time of 60 seconds. Measurements were performed on three polymer buttons and the average was reported. In some examples, where noted, measurements were performed on both sides of three polymer buttons and the average of six measurements was reported.

[0250] Abbe number test method: Following the procedure for measuring the refractive index at 589.3 nm, the refractive index at 486.1 nm and 656.3 nm were measured. Measurements were performed on three polymer buttons, and for each polymer button, the next repetition was measured after completing the refractive index measurements at all three wavelengths. The Abbe number was calculated as follows:

[0251]

number

[0252] As noted in the examples, moisture content was determined gravimetrically by either the "dry method" or the "hydrated method."

[0253] In the "dry method", three polymer buttons (approximately 2 millimeters thick and 13 millimeters in diameter, respectively) were equilibrated at 37° C. for approximately 14 days in individual glass scintillation vials containing approximately 10 mL of PBS. Each polymer button was removed from the vial using sharp metal tweezers and briefly blotted on all sides (flat surfaces and edges) using clean blotting paper to remove superficial / excess PBS. Using dry tweezers, each button was placed into a tared weighing dish and weighed individually. The wet weight of each polymer button is defined as "(total weight of dish + wet button) - weight of weighing dish only". Dry weight was measured by placing the sample dish in a vacuum oven preheated to 60° C. for 30 minutes. Vacuum was applied until the pressure reached at least 1 inch Hg (mercury); lower pressures were possible. The vacuum valve and pump were turned off and the lenses were allowed to dry for 24 hours. The purge valve was opened to admit dry air or dry nitrogen gas. Once the oven reached atmospheric pressure, the dish was removed and weighed. After weighing the dish (containing the polymer button), the polymer button was placed in the vacuum oven and allowed to dry for an additional 24 hours before being weighed to obtain data at 48 hours of drying. This procedure was repeated to generate data at 72 hours of drying. For each experiment, the dry weight was defined as the combined weight of the weigh dish and dry button minus the weight of the weigh dish alone. The moisture content of the polymer buttons was calculated as follows: Percentage of Moisture Content (%WC) = (Wet Weight - Dry Weight) / Wet Weight x 100. The mean and standard deviation of the moisture content were calculated and the mean was reported as the percent moisture content of the buttons.

[0254] Alternatively, water content was measured gravimetrically by the "hydration method." In this method, three dry polymer buttons (previously thoroughly extracted with 2-propanol and dried) were individually weighed and transferred to individual glass scintillation vials using sharp metal tweezers. Approximately 10 mL of deionized water was transferred to each vial and the samples were incubated at 37°C for 7 days. After incubation, the polymer buttons were removed from the vials using sharp metal tweezers and briefly blotted on all sides (flat surfaces and edges) using clean blotting paper to remove superficial / excess water. Using dry tweezers, each polymer button was placed into a tared weighing dish and weighed individually. After weighing, the polymer buttons were returned to the vials and incubated at 37°C for an additional 7 days, and the water content at 14 days was measured. At each time point, the moisture content of the polymer buttons was calculated as follows: (% WC) = (wet weight - dry weight) / wet weight x 100.

[0255] Glass transition temperature test method: Due to the thickness and / or brittleness of the polymer buttons, test samples were cut from the center of the polymer buttons or lenses using a razor blade. The samples could not be punched like thin films. The test samples were analyzed (in duplicate) on a DSC Q2000 TA instrument at a heating rate of 10°C / min and a cooling rate of 5°C / min under nitrogen gas atmosphere. The glass transition temperatures were measured from the first and second heating scans (first and second scans, respectively).

[0256] Microvitreous Test Method: Prior to conditioning the lenses for darkfield optical microscopy, the lenses were extracted in acetonitrile or methanol. For extraction, the lenses were individually placed in a lens case containing 3 mL of acetonitrile or methanol and extracted overnight at ambient temperature followed by three 3 mL aliquots of acetonitrile or methanol at 4 hour intervals. After the final extraction, the lenses were allowed to dry at ambient temperature for at least 6 days. The lenses were then cleaned to remove any visible residual debris from the manufacturing and extraction process and then immersed in 0.9% saline in a fluid cell. Microvacuoles can be induced by placing these cells in an oven at 35° C. for approximately 15 hours. The lenses were removed from the oven and allowed to equilibrate at room temperature for at least 2 hours and then analyzed by darkfield optical microscopy as described in Biomedical Optics Express, 2013, Vol. 4 No. 8, which is incorporated herein by reference in its entirety. Any standard optical microscope or camera capable of darkfield imaging can be used. In a dark field setting, the intraocular lens was back-illuminated by a ring of light at an oblique angle. If there were no microvacuoles or other light scattering centers present, the image would be black. As the number of microvacuoles increases, the amount of forward scattered light increases, creating a pattern of forward scattered light arrangement in the dark field. Microvacuole density was measured from dark field microscopy photographs of small populations of microvacuoles using the Image J program (or other similar image post-processing software program). A 4 mm diameter circular area was surveyed and the microvacuole density was calculated (1 mm 2 Number of microvacuoles or microvoids per mm 2 Generally speaking, intraocular lenses with fewer microvacuoles or microluminescence provide better vision than intraocular lenses with more forward scattering and are therefore preferred. 2 The micro-vitreous density is considered to be lower than and comparable to intraocular lenses that do not involve any vitreous matter.

[0257] Macroclite Test Method: Lenses were individually placed in a lens case containing 3 mL of acetonitrile (ACN). Lenses were extracted for 4 hours at ambient temperature. Acetonitrile was removed with a disposable pipette and an additional 3 mL of acetonitrile was added. Lenses were then extracted overnight at ambient temperature. Acetonitrile was removed with a disposable pipette and an additional 3 mL of acetonitrile was added. Lenses were extracted for 4 hours at ambient temperature. Acetonitrile was removed with a disposable pipette and an additional 3 mL of acetonitrile was added. Lenses were extracted for 4 hours at ambient temperature. Acetonitrile was removed with a disposable pipette and lenses were allowed to dry at ambient temperature for at least 6 days. Air-dried lenses were individually placed in a lens case containing 3 mL of methanol and equilibrated overnight at ambient temperature. Alternatively, lenses were first extracted directly overnight with a 3 mL aliquot of methanol followed by three 3 mL aliquots of methanol at 4 hour intervals. After organic extraction by either method, the lenses were placed in DPBS solution by the following "gradient equilibration" procedure: (1) lenses were individually placed in lens cases containing 3 mL of 80% (v / v) aqueous methanol for 4 hours at ambient temperature, (2) the 80% (v / v) aqueous methanol was then exchanged with 3 mL of 60% (v / v) aqueous methanol for 4 hours at ambient temperature, and (3) the 60% (v / v) aqueous methanol lenses were then exchanged with 3 mL of 50% (v / v) methanol:DPBS overnight at ambient temperature. (4) the 50% (v / v) methanol:DPBS was then exchanged with 3 mL of 40% (v / v) methanol:DPBS at ambient temperature for 4 hours, (5) the 40% (v / v) methanol:DPBS was then exchanged with 3 mL of 20% (v / v) methanol:DPBS at ambient temperature for 4 hours, and finally (6) the 20% (v / v) methanol:DPBS was exchanged with 3 mL of DPBS at ambient temperature overnight, followed by at least two rinse steps with 3 mL of DPBS to remove the methanol, followed by equilibration in DPBS overnight.Light scattering vesicles were prepared in test lenses (prepared without extraction, prepared with acetonitrile extraction followed by drying only, or prepared after organic extraction and gradient equilibration) by individually placing them in a lens case containing 3 mL of PBS. After screwing on the cap, the case was placed in an incubator at 37°C for at least 3 days. The lenses were then evaluated by dark field microscopy using a microscope (Nikon SMZ1500) at 25X to 30X magnification. Counting can be performed when the number of macroscopic vesicles is low.

[0258] The following abbreviations are used throughout the examples and have the following meanings: TL03 Light: Phillips TLK 40W / 03 bulb LED: Light Emitting Diode RMM: reactive monomer mixture RI(25) is the refractive index measured at 25°C RI(35) is the refractive index measured at 35°C. Abbe number (25): Abbe number measured at 25°C Abbe number (35): Abbe number measured at 35°C T g : Glass transition temperature (℃) measured by differential scanning calorimetry (DSC) mm: millimeters cm: centimeters μm: micrometer nm: nanometer μL: microliter mW: milliwatt g / mol: grams per mole Da or Dalton: grams / mole kDa: kilodaltons PBS: Phosphate-buffered saline DPBS: Dulbecco's phosphate buffered saline without calcium or magnesium ions ACN: Acetonitrile CHA: Cyclohexyl acrylate [CAS 3066-71-5] (TCI or Alfa Aesar) EGDCA: Ethylene glycol dicyclopentenyl ether acrylate [CAS 65983-31-5] (Sigma-Aldrich)

[0259] [ka] BCHA: ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl acrylate or cycloacrylate or [(1S,4S)-2-bicyclo[2.2.1]hept-5-enyl]methyl prop-2-enoate [CAS 95-39-6] (Monomer-Polymer and DAJAC Labs Inc.)

[0260] [ka] CAA: Cinnamyl acrylate

[0261] [ka] NHA: n-Hexyl acrylate [CAS 2499-95-8] (Sigma-Aldrich) PEA: 2-Phenylethyl acrylate [CAS 3530-36-7] (MPD) PEMA: 2-Phenylethyl methacrylate [CAS 3683-12-3] PPA: 3-Phenylpropyl acrylate [CAS 85909-41-7] TCDA: Tricyclo[5.2.1.0 2,6 ]Decanedimethanol diacrylate or dimethyloltricyclodecane diacrylate [CAS 42594-17-2] (Sigma-Aldrich or Kyoeisha Chemical Co.)

[0262] [ka] DMA: N,N-Dimethylacrylamide [CAS 2680-03-7] (TCI or Sigma-Aldrich) NVP: N-vinylpyrrolidone-2-one HEMA: 2-hydroxyethyl methacrylate (Bimax) HBA: 4-Hydroxybutyl acrylate [CAS 2478-10-6] (TCI or BASF) mPEG300: Poly(ethylene glycol) methyl ether methacrylate (M n = 300 grams / mole) (Sigma-Aldrich)

[0263] [ka] PEG-OH200: poly(ethylene glycol) methacrylate (Polysciences; the molecular weight of the PEG block is 200 grams / mole) PEG-OH360: Poly(ethylene glycol) methacrylate (M n = 360 g / mol) (Sigma-Aldrich)

[0264] [ka] PVP K90: Poly(N-vinylpyrrolidone) [CAS 9003-39-8] (Ashland) PDMA: Polydimethylacrylamide (M n = 414kDa);M w =498kDa;Toray)

[0265] Molecular weights were determined by size-exclusion chromatography with multi-angle light scattering (SEC-MALS). The SEC-MALS setup used an aqueous acetonitrile solution as the mobile phase, consisting of 80% (v / v) 50 mM Na2SO4 and 20% (v / v) acetonitrile, at a flow rate of 0.5 mL / min at 40°C. Two Tosoh Biosciences TSK-gel columns [SuperAW4000 and SuperAW5000] were used in series, equipped with an online Agilent 1200 UV / VIS diode array detector, a Wyatt Optilab rEX interference refractometer, and a Wyatt mini-DAWN Treos multi-angle laser scattering (MALS) detector (λ=658 mm). Absolute molecular weight and polydispersity data were calculated using the Wyatt ASTRA VI SEC / LS software package. Approximately 40 milligrams of PDMA was dissolved in the packing solution in a 10-mL volumetric flask. Packing solution: 18.52 grams (300 mmol) of boric acid, 3.7 grams (9.7 mmol) of sodium borate decahydrate, and 28 grams (197 mmol) of sodium sulfate were dissolved in enough deionized water to fill a 2-liter volumetric flask. Three different solutions were prepared and tested. A monomeric serum albumin sample was also tested using a solution made from only 10 milligrams of protein in 10 mL of packing solution. All solutions were filtered through a 0.45 micrometer nylon membrane filter before being injected into the SEC-MALS system. The number average molecular weight of the three samples was 414 kDa (with a standard deviation of 12 kDa) and the weight average molecular weight of the three samples was 498 kDa (with a standard deviation of 11 kDa), resulting in a polydispersity index of 1.2. Omnirad 819: Bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide [CAS 162881-26-7] (IGM Resins) AIBN: Azobisisobutyronitrile [CAS 78-67-1] mPDMS: mono-n-butyl terminated, monomethacryloxypropyl terminated polydimethylsiloxane (M n=500~1500 Daltons) (Gelest) SiMAA: 2-Propenoic acid, 2-methyl-2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester (Toray), or 3-(3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)propoxy)-2-hydroxypropyl methacrylate HO-mPDMS: mono-n-butyl terminated mono-(2-hydroxy-3-methacryloxypropyloxy)-propyl terminated polydimethylsiloxane (M n = 1400 Daltons, n = 15) (Ortec or DSM-Polymer Technology Group)

[0266] [ka] EGDMA: Ethylene glycol dimethacrylate (Esstech) ac-PDMS: bis-3-acryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane (Tegomer V-Si 2250 from Evonik) XLMA: Bis-3-methacryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane (M n = 2000 Daltons, n = 20) (Shin Etsu)

[0267] [ka] UV-HEV or UV / HEV: Ultraviolet and / or High Energy Visible Light UVB: 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate or 2-methylacrylic acid, 3-[3-tert-butyl-5-(5-chlorobenzothiazol-2-yl)-4-hydroxyphenyl]-propyl ester (Adesis)

[0268] [ka] HEVB: 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate

[0269] [ka] Preparation of HEVB: The synthesis of 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)-ethyl methacrylate (B) is shown in Scheme 1.

[0270] [ka]

[0271] Methyl cyanoacetate (40 grams, 0.4037 moles) and 25 mL of dichloromethane were stirred in a three-necked 500 mL round bottom flask equipped with a reflux condenser under a nitrogen environment. After 2-aminoethanol (23.8 grams, 0.3897 moles, .about.0.97 equiv.) was added to the solution via an addition funnel, the temperature rose and the methylene chloride began to reflux. After the exotherm ceased, external heat was applied to continue the gentle reflux for a total of 2 hours after which no ethanolamine was observed by thin layer chromatography.

[0272] The reaction may also be carried out at room temperature and is complete within a few hours.

[0273] The mixture was cooled to room temperature and all methylene chloride was evaporated under reduced pressure. The residual oil was washed with 50 mL of ethyl acetate three times to remove unreacted starting material and non-polar impurities. The residual ethyl acetate was then removed under reduced pressure and the resulting oil was used for acylation without further purification.

[0274] The crude N-2-hydroxyethylacetamide derivative was dissolved in 150 mL of dichloromethane containing 40 grams of pyridine (~0.5 moles) in a three-neck round bottom flask equipped with a reflux condenser, an addition funnel, and a magnetic stir bar. The flask was immersed in an ice bath and cooled to about 0°C. Methacryloyl chloride (45.76 g, ~0.44 moles) was added dropwise through the addition funnel and the resulting reactive mixture was allowed to warm to room temperature while constantly stirring the system. Methanol (20 mL) was added to the flask to quench any unreacted methacryloyl chloride. The volatile components were removed by rotary evaporation under reduced pressure and the crude product was dissolved in 800 mL of dilute aqueous HCl. The resulting aqueous solution was extracted three times with 100 mL of hexane in a separatory funnel to remove any non-polar impurities. The organic layer was discarded. Sodium chloride was added to the aqueous layer, which was then extracted three times with 300 mL of ethyl acetate. Approximately 50 milligrams of BHT was added as an inhibitor to the combined organic fractions, and the ethyl acetate was removed by rotary evaporation under reduced pressure. The crude product crystallized out of solution during solvent removal. When approximately 100 mL of ethyl acetate remained in the flask, 250 mL of hexane was added, and the crude product was isolated by vacuum filtration using a fritted glass funnel. Thin layer chromatography indicated the presence of a single compound. The filter cake was washed twice with 150 mL of hexane, then dried under vacuum at 40° C. to give 53 grams (approximately 70% yield) of 2-(2-cyanoacetamido)ethyl methacrylate (A). 1 H NMR (500MHz, CDCl3) δ1.93(3H,s,CH3),3.36(2H,s,CNCH2),3.60(2H,dd,CH2NH),4.26(2H,t,CH2OC=O),5.59(1H,m,vinylic),6.11(1H,bs,vinylic),6.52(1H,bs,NH).

[0275] A mixture of 9H-thioxanthen-9-one (2.12 grams, 0.01 moles) and thionyl chloride (5 mL, 8.2 grams, .about.0.07 moles) was refluxed in a 50 mL round bottom flask under constant stirring under a nitrogen atmosphere. After 2 hours, the red solution was evaporated to dryness to ensure that all unreacted thionyl chloride was removed from the system. 2-(2-cyanoacetamido)ethyl methacrylate (A) (2.3 grams, 0.0117 moles, .about.1.17 equiv.) and 15 mL of dichloromethane were added and the resulting reactive mixture was heated to reflux under a nitrogen blanket. The reaction was monitored by thin layer chromatography. After 2 hours, no change was observed in the chromatogram so the reactive mixture was cooled to room temperature. After passing through a short silica gel column (CH2Cl2, followed by 8 wt% EtOAc in CH2Cl2), 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate (B) was isolated as yellow crystals (3.2 grams, 82% yield). 1 H NMR(500MHz,CDCl3)δ1.84(3H,s,CH3),3.47(2H,m,CH2NH),4.01(2H,t,CH2OC=O),5.55(1H,m,vinylic),5.91(1H,bs,NH),5.98(1H,bs,vin ylic),7.24(1H,t,Ar-H),7.31(1H,t,Ar-H),7.39(2H,m,Ar-H),7.49(1H,d,Ar-H),7.55(1H,m,Ar-H),7.61(1H,d,Ar-H),8.04(1H,m,Ar-H). CHMA: Cyclohexylmethyl acrylate

[0276] [ka] CHEA: 2-Cyclohexylethyl acrylate

[0277] [ka] CHPA: 3-cyclohexylpropyl acrylate

[0278] [ka]

[0279] Synthesis of cyclohexylmethyl acrylate (CHMA): Cyclohexylmethanol (25.0 g, 219.0 mmol) and triethylamine (33.46 g, 330.7 mmol) were dissolved in dichloromethane (450 mL) and cooled to about 0° C. using an ice bath. Acryloyl chloride (29.74 g, 328.5 mmol) was added over 20 minutes while maintaining a constant temperature of about 0° C. After the addition was complete, the reaction mixture was stirred at 0° C.-30° C. and then at ambient temperature overnight. Thin layer chromatography was used to monitor the progress of the reaction. When the reaction was complete, triethylammonium chloride was separated by filtration, dissolved in deionized water (200 mL) and extracted with dichloromethane (3×50 mL). The combined filtrate and organic extracts were washed with water (2×50 mL), brine (25 mL), dried over anhydrous NaSO, vacuum filtered, and concentrated by rotary evaporation. The crude product was then passed through a short plug of silica gel and eluted with 10% ethyl acetate in n-hexane to give the desired product, CHMA, as a clear oil (98% yield). 1 H-NMR(500MHz,CDCl3)δ6.39(1H,dd,J=1.0,17.0Hz),6.12(1H,dd,J=10.0,17.0Hz),5.81(1H,dd ,J=1.5,10.0Hz),3.97(2H,d,J=6.0Hz),1.76-1.62(6H,m),1.31-1.15(3H,m),0.95-1.01(2H,m).

[0280] Synthesis of 2-cyclohexylethyl acrylate (CHEA): 2-cyclohexylethyl acrylate was prepared by the same procedure except that 2-cyclohexylethanol was used instead of cyclohexyl (99% yield). 1H-NMR (500MHz, CDCl3): δ6.38(1H,dd,J=1.1,17.2Hz),6.11(1H,dd,J=10.1,17.2Hz),5.80(1H,dd,J=1.4,10.1Hz),4 .18(2H,t,J=7.0Hz),1.74-1.62(5H,m),1.58-1.54(2H,m),1.39-1.36(1H,m),1.27-1.13(3H,m),0.97-0.90(2H,m).

[0281] Synthesis of 3-cyclohexylpropyl acrylate (CHPA): 3-Cyclohexylpropyl acrylate was prepared by the same procedure except that 3-cyclohexylpropanol was used instead of cyclohexylmethanol (99% yield). 1 H-NMR (500MHz, CDCl3): δ6.40(1H,dd,J=1.0,17.1Hz),6.11(1H,dd,J=10.0,17.1Hz),5.81(1H,dd ,J=1.5,10.0Hz),4.13(2H,t,J=7.1Hz),1.71-1.64(7H,m),1.25-1.20(6H,m),0.91-0.88(2H,m).

[0282] Examples 1 to 5 Under yellow lighting, the RMMs described in Table 1 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was refilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and nitrogen gas atmospheric pressure with an internal temperature of ambient temperature. Polymer buttons (approximately 2 millimeters thick and 13 millimeters in diameter) were fabricated using a Teflon cup and a circular glass plate held in a stainless steel fixture (base and open screw cap). Approximately 350 microliters of the RMMs were dispensed into the Teflon cup and assembled with the glass plate and stainless steel fixture. The assembly was transferred to a curing box maintained at a temperature of 55°C to 60°C and irradiated with 3 to 4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2The cured assemblies were then manually removed from the mold. All samples were clear and exhibited low levels of surface tack. The refractive index and Abbe number were measured on the unextracted button for each example and are listed in Table 1.

[0283] [Table 1]

[0284] The RMM in Table 1 contains cyclohexyl acrylate, phenylethyl acrylate, n-hexyl acrylate, and a cycloaliphatic crosslinker. The amount of cyclohexyl acrylate and phenylethyl acrylate can vary, but the amount of n-hexyl acrylate, a cycloaliphatic crosslinker, is fixed. Tests show that as the concentration of cyclohexyl acrylate decreases, the Abbe number also decreases, but the RI measurement increases.

[0285] Examples 6 to 10 Under yellow lighting, the RMMs described in Table 2 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was backfilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and nitrogen gas atmospheric pressure with an internal temperature of ambient temperature. Polymer buttons were fabricated as described in Examples 1-5. Approximately 350 microliters of the RMMs were dispensed between Teflon cups and assembled with a glass plate and stainless steel fixture. The assembly was then transferred to a curing box maintained at a temperature of 55°C-60°C and 3-4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2The cured assemblies were then manually removed from the mold. All samples were clear and showed low levels of surface tackiness, which decreased with increasing amounts of TCDA. The refractive index and Abbe number were measured on the unextracted button for each example and are listed in Table 2. In some examples, these measurements were performed on the front and back of the sample. These surfaces were in contact with either a Teflon cup or a glass fixture. Small differences in refractive index and Abbe number were measured between the surfaces in contact with the Teflon and the glass.

[0286] Examples 11 and 12 Under yellow lighting, the RMMs described in Table 2 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was backfilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and atmospheric pressure of nitrogen gas with an internal temperature of ambient temperature. Approximately 350 microliters of the RMMs were dispensed into an O-ring placed between two glass plates and held together by a clamp, after which the device was transferred to a curing box maintained at a temperature of 55°C to 60°C and 3 to 4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2 The cured assemblies were then manually removed from the mold. All samples were clear and showed low levels of surface tack. Example 12 showed no tack. The refractive index and Abbe number were measured on the unextracted button for each example and are listed in Table 2.

[0287] [Table 2]

[0288] The RMMs shown in Examples 6-10 maintained approximately the same amounts of cyclohexyl acrylate and phenylethyl acrylate, but varied the n-hexyl acrylate and crosslinker. The Abbe number was generally constant across these examples, but there was a measurable increase in refractive index as the concentration of cycloaliphatic crosslinker was increased. The RMMs shown in Examples 11-12 generally show that the inclusion of the XMLA crosslinker does not materially affect the RI or Abbe measurements. However, as the amount of cyclohexyl acrylate was reduced and the amount of phenylethyl acrylate was relatively increased, the Abbe number decreased compared to Examples 6-10.

[0289] Examples 13-14 Under yellow lighting, the RMMs described in Table 3 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was backfilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and nitrogen gas atmospheric pressure with an internal temperature of ambient temperature. Polymer buttons were fabricated as described in Examples 1-5. Approximately 350 microliters of the RMMs were dispensed between Teflon cups and assembled with a glass plate and stainless steel fixture. The assembly was then transferred to a curing box maintained at a temperature of 55°C-60°C and 3-4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2 The cured assemblies were then manually removed from the mold. All samples were clear and showed no surface tack. The refractive index and Abbe number were measured on the unextracted button for each example and are listed in Table 3. These experiments show the effect on RI and Abbe as the concentrations of HBA and PVP90 are changed.

[0290] Example 15 Under yellow lighting, the RMMs described in Table 3 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was backfilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and atmospheric pressure of nitrogen gas with an internal temperature of ambient temperature. Polymer buttons were made by dispensing approximately 350 microliters of the RMMs using a Teflon Cup assembly, or alternatively, by dispensing into an O-ring placed between two glass plates and held together by a clamp, after which the device was transferred to a curing box maintained at a temperature of 55°C-60°C and 3-4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2 The cured assemblies were then manually removed from the mold. The samples were substantially transparent and showed no surface tack. The refractive index and Abbe number were measured on the unextracted button for each example and are listed in Table 3.

[0291] Example 16 Under yellow lighting, the RMMs described in Table 3 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was backfilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and atmospheric pressure of nitrogen gas with an internal temperature of ambient temperature. Approximately 350 microliters of the RMMs were dispensed into an O-ring placed between two glass plates and held together by a clamp, after which the device was transferred to a curing box maintained at a temperature of 55°C to 60°C and 3 to 4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2 The cured assemblies were then manually removed from the mold. The samples were substantially transparent and showed no surface tack. The refractive index and Abbe number were measured on the unextracted button for each example and are listed in Table 3.

[0292] Example 17 Under yellow lighting, the RMMs described in Table 3 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was backfilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and atmospheric pressure of nitrogen gas with an internal temperature of ambient temperature. Approximately 350 microliters of the RMMs were dispensed into an O-ring placed between two glass plates and held together by a clamp, after which the device was transferred to a curing box maintained at a temperature of 55°C to 60°C and 3 to 4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2 The cured assemblies were then manually removed from the mold. The samples were substantially transparent (slightly hazy) and showed no surface tack. The refractive index and Abbe number were measured on the unextracted button for each example and are listed in Table 3.

[0293] Example 18 Under yellow lighting, the RMMs listed in Table 3 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was refilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and atmospheric pressure of nitrogen gas with an internal temperature of ambient temperature. Approximately 350 microliters of the RMMs were dispensed into a Teflon cup and assembled with a glass plate and stainless steel fixture. The apparatus was then transferred to a curing box maintained at a temperature of 55°C to 60°C and irradiated with 3 to 4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2 The cured assemblies were manually removed from the mold. All samples were clear and showed slight surface tack. The refractive index and Abbe number were measured on the unextracted button for each example and are listed in Table 3. In some examples, these measurements were performed on the front and back of the sample. These surfaces were in contact with either a Teflon cup, a glass fixture, or a glass plate. Small differences in refractive index and Abbe number were measured between the surfaces in contact with the Teflon and the glass.

[0294] [Table 3]

[0295] All of the above examples exhibited desirable RI and Abbe numbers.

[0296] Examples 19 to 24 Under yellow lighting, the RMMs described in Table 4 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was backfilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and atmospheric pressure of nitrogen gas with an internal temperature of ambient temperature. Approximately 350 microliters of the RMMs were dispensed into an O-ring placed between two glass plates and held together by a clamp, after which the device was transferred to a curing box maintained at a temperature of 55°C to 60°C and 3 to 4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2 The cured assemblies were then manually removed from the mold. The samples were clear and showed no surface tack. The refractive index and Abbe number for each example were measured and are listed in Table 4.

[0297] Example 25 Under yellow lighting, the RMMs described in Table 4 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was backfilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and atmospheric pressure of nitrogen gas with an internal temperature of ambient temperature. Approximately 350 microliters of the RMMs were dispensed into an O-ring placed between two glass plates and held together by a clamp, after which the device was transferred to a curing box maintained at a temperature of approximately 40° C. and 18-20 mW / cm. 2 The cured assemblies were manually removed from the mold. The samples were clear and showed no surface tack. The refractive index and Abbe number were measured on the unextracted button for each example and are listed in Table 4.

[0298] [Table 4]

[0299] Examples 26 to 32 Under yellow lighting, the RMMs described in Table 5 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was backfilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and atmospheric pressure of nitrogen gas with an internal temperature of ambient temperature. Approximately 350 microliters of the RMMs were dispensed into an O-ring placed between two glass plates and held together by a clamp, after which the device was transferred to a curing box maintained at a temperature of 55°C to 60°C and 3 to 4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2 The cured assemblies were manually removed from the mold. The samples were clear and showed no surface tack. The refractive index and Abbe number were measured on the unextracted button for each example and are listed in Table 5.

[0300] [Table 5]

[0301] As can be seen, Examples 26-32 present data for samples made with similar components as the previous examples, but also containing a polyamide wetting agent (PVP) and additional hydroxybutyl acrylate monomer. High refractive index measurements (all above 1.5) and Abbe numbers (48-50) are recorded.

[0302] Examples 33-34 Under yellow lighting, the RMMs described in Table 6 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was backfilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and atmospheric pressure of nitrogen gas with an internal temperature of ambient temperature. Approximately 350 microliters of the RMMs were dispensed into an O-ring placed between two glass plates and held together by a clamp, after which the device was transferred to a curing box maintained at a temperature of 55°C to 60°C and 3 to 4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2 The cured assemblies were then manually removed from the mold. Example 33 was clear and did not exhibit any surface tack. Example 34 was slightly hazy and did not exhibit any surface tack. The refractive index and Abbe number were measured on the unextracted button for each example and are listed in Table 6.

[0303] [Table 6]

[0304] Examples 35 to 36 and Comparative Examples 1 to 2 Under yellow lighting, reactive monomer mixtures were prepared from the formulations listed in Table 7. All components were accurately weighed into amber glass containers and tightly closed with PTFE-lined screw caps. The containers were placed on a jar roller and rolled until a homogenous mixture was obtained. The RMM was filtered through a 0.45 μm PTFE membrane (Pall Corporation, Part#66148) using a Luer-lock glass syringe and stainless steel filter fixture, then degassed by sparging with nitrogen gas for at least 3 minutes and backfilled with nitrogen gas. The degassed RMM was placed in the RMM mold filling section of the glove box (<0.1% oxygen, room temperature). The cap was opened and the RMM was allowed to equilibrate for approximately 3 minutes before use.

[0305] In a glove box with atmospheric nitrogen gas and less than 0.1% oxygen gas (vol / vol), approximately 75-100 μL of the reactive mixture was dispensed at room temperature using an Eppendorf pipette into a polypropylene front curve mold. A base curve mold, also made of polypropylene, was then placed onto the front curve mold. The polypropylene mold was equilibrated in the glove box for a minimum of 12 hours prior to dispensing. The assembly was transferred to an adjacent glove box maintained at approximately 60-65°C, and the lenses were irradiated with the following profile: 5 mW / cm 2 (Top 2.5mW / cm 2 , and lower 2.5 mW / cm 2 ) for 20 minutes at 10mW / cm 2 (Top 5mW / cm 2 , and lower 5mW / cm 2 ) for 20 minutes at 20mW / cm 2 (Top 10mW / cm 2 , and lower 10 mW / cm 2 ) for 20 minutes and 30mW / cm 2 (Top 15mW / cm 2 , and lower 15mW / cm 2 ) for 30 minutes and 435 nm LED light on each side for a total of 90 hours, top and bottom curing.

[0306] The cured assembly was manually demolded. The base curve mold was separated from the front curve mold using tweezers and any polymer flash was removed. The front curve mold with the lens still attached was placed in a 4° C. refrigerator for at least 1 minute. The chilled mold was removed and force was applied to the reverse side of the mold to mechanically release the lens.

[0307] Example 36 was prepared following the procedure of Example 35, except that instead of light curing, the lenses were heat cured for 72 hours at 60-65° C. Both light cured and heat cured lenses were used for fluoride analysis.

[0308] Polymer buttons were prepared for refractive index, Abbe number, and glass transition temperature measurements. Approximately 350 microliters of RMM was dispensed into an O-ring placed between two glass plates and held together with a clamp. The assembly was transferred to an adjacent glove box maintained at approximately 60-65°C and cured using the light conditions described above for the corresponding lenses. The polymer buttons for Example 36 were similarly prepared, except that instead of being light cured, they were heat cured at 60-65°C for 72 hours.

[0309] For Example 35, the refractive index, Abbe number, and glass transition temperature were measured on the unextracted polymer button and are listed in Table 7. Additionally, the glass transition temperature of Example 36 was also measured. The unextracted lenses of Example 35 and Comparative Examples 1 and 2 were analyzed for micro-vacuoles or micro-brightness according to the procedure of the "Micro-brightness Test Method" above, and the dark field micrographs are shown in FIG. 1. Example 35 was also analyzed for macro-vesicles or macro-brightness according to the procedure of the "Macro-brightness Test Method" above, and the dark field micrographs are shown in FIG. 2. Three conditions were compared. In the first condition, lenses were prepared and incubated in PBS at 37° C. for 3 days without extraction. In the second condition, lenses were prepared, extracted with acetonitrile, dried according to the steps described in the "Macro-brightness Test Method" above, and then incubated in PBS at 37° C. for 3 days. In the third condition, lenses were prepared, extracted with acetonitrile, dried, passed through the gradient equilibration steps described above in the "Macrovites Test Method," and finally incubated for 3 days in PBS at 37°C.

[0310] [Table 7]

[0311] As shown in the micrograph in Figure 1, Example 35 contained less microcrystals than the comparative example. At the more severe gradient equilibration conditions, Example 35 exhibited levels of macrocrystals that were not observed in lenses made without extraction or when the lenses were dried after extraction with acetonitrile alone.

[0312] Examples 37 to 43 A series of RMMs (Examples 38-43) were prepared by first making a masterbatch formulation (Example 37) and then adding enough hydrophilic monomer to a portion of the masterbatch to make new RMMs containing the weight percentages of hydrophilic monomer listed in Table 8. These new RMMs contained approximately equal molar equivalents of hydrophilic monomer with different polymerizable moieties that would affect the incorporation kinetics compared to the other components of the RMM. Thus, the effect of the desired polymerizable functionality and the desired relative hydrophilicity can be found from the perspective of the macrobrighteners. Lenses were made from the masterbatch and the new RMMs containing hydrophilic monomer using the procedure described in Example 35. Lenses were made according to the procedure in the "Macrobrighteners Test Method" above, extracted with acetonitrile, dried, gradient equilibrated, and incubated in PBS for 3 days at 37°C. All lenses were analyzed for macrovesicles or macrobrighteners, and dark field micrographs are shown in Figure 3.

[0313] [Table 8]

[0314] As shown in Figure 3, the incorporation of hydrophilic monomers into the lens composition reduced macrobrightness compared to the masterbatch control lenses. The macrobrightness data in Figure 3 corresponds to the following order of severity: control lenses>NVP>DMA>mPEG300>HBA>HEMA>PEG-OH360. The reactivity of the hydrophilic monomers compared to other reactive components in the composition corresponds to the following order: HBA>HEMA, PEG-OH360, mPEG300>DMA>NVP, while the relative hydrophilicity of the hydrophilic monomers corresponds to the following order: DMA>NVP, PEG-OH360>mPEG300>HEMA>HBA. This suggests that the level of macrobrightness obtained is controlled by both the reactivity of the hydrophilic monomers with respect to other reactive components in the composition and the relative hydrophilicity of the hydrophilic monomers, with the former having a more pronounced effect. Although DMA and NVP are more hydrophilic, they react or polymerize much slower in their respective RMMs compared to the other reactive components, and the resulting lenses exhibit the highest levels of macro-crystals compared to the control. Although HEMA, HBA, m-PEG300, and PEG-OH360 are less hydrophilic compared to DMA and NVP, their reactivity is comparable to the other reactive components in their respective RMMs, and the resulting lenses have much less micro-crystals compared to the control lenses and lenses containing DMA and NVP. With PEG-OH360, not only is its reactivity comparable to the other reactive components in the RMMs, it is the most hydrophilic monomer in this group of (meth)acrylate monomers studied, and the resulting lenses are substantially free of macro-crystals. It is speculated that the slow monomers, DMA, and NVP, similarly create hydrophilic domains or localized regions of DMA / NVP enrichment, resulting in a non-uniform, or anisotropic, distribution of water in the hydrated crosslinked polymer. The reactivity of hydrophilic monomers (e.g., HEMA, HBA, mPEG300, PEG-OH360) in RMMs corresponding to other reactive components may create more random crosslinked polymers or networks in which the hydrophilic monomers are more uniformly distributed or delocalized, resulting in a more uniform or isotropic distribution of water in the hydrated polymer.

[0315] Examples 44 to 51 Under yellow lighting, reactive monomer mixtures were prepared from the formulations listed in Table 9. All components were accurately weighed into amber glass containers and tightly closed with PTFE-lined screw caps. The containers were placed on a jar roller and rolled until a homogenous mixture was obtained. The RMM was filtered through a 0.45 μm PTFE membrane (Pall Corporation, Part#66148) using a Luer-lock glass syringe and stainless steel filter fixture, then degassed by sparging with nitrogen gas for at least 3 minutes and backfilled with nitrogen gas. The degassed RMM was placed in the RMM mold filling section of the glove box (<0.1% oxygen, room temperature). The cap was opened and the RMM was allowed to equilibrate for approximately 3 minutes before use. Polymer buttons were made for measuring refractive index, Abbe number, glass transition temperature, and water content, and lenses were made for evaluation of macrocrystals.

[0316] Polymer buttons: In a glove box with atmospheric pressure of nitrogen gas and less than 0.1% oxygen gas (vol / vol), approximately 350 μL of the reactive mixture was dispensed at room temperature using an Eppendorf pipette into an O-ring placed between two glass plates and held together with a clamp. The apparatus was then transferred to an adjacent glove box maintained at approximately 60-65 °C and the buttons were heated with an ion source with the following profile: 5 mW / cm 2 (Top 2.5mW / cm 2 , and lower 2.5 mW / cm 2 ) for 20 minutes at 10mW / cm 2 (Top 5mW / cm 2 , and lower 5mW / cm 2 ) for 20 minutes at 20mW / cm 2 (Top 10mW / cm 2 , and lower 10 mW / cm 2 ) for 20 minutes and 30mW / cm 2 (Top 15mW / cm 2 , and lower 15mW / cm 2 ) for 30 minutes on each side using 435nm LED light for a total of 90 hours, top and bottom curing.

[0317] The hardened buttons were manually removed from the mold. The glass plates were pried open with a spatula and razor blade. The temperature was increased or decreased in some cases to facilitate removal from the mold. Any polymer flash was removed as well. The buttons were extracted with 2-propanol and dried using the following procedure: 1) The buttons were placed in individual amber glass containers (with PTFE lined screw caps), approximately 30 mL of 2-propanol was added, and placed on a bench size orbital shaker at 100 rpm overnight at room temperature. 2) The 2-propanol was completely decanted, approximately 25 mL of 2-propanol was added, and extraction was continued on a bench size orbital shaker at 100 rpm for approximately 2 hours at room temperature. 3) The 2-propanol was completely decanted, approximately 25 mL of 2-propanol was added, and extraction was continued on a bench size orbital shaker at 100 rpm for approximately 2 hours at room temperature. 4) The 2-propanol was decanted completely and the buttons were placed on a Teflon surface to dry overnight. 5) The air-dried buttons on the Teflon surface were placed in a glove box at room temperature with a nitrogen atmosphere and less than 0.1% oxygen content maintained by an active nitrogen sparge and the buttons were allowed to dry overnight. 6) The Teflon surfaced buttons were transferred to a heated glove box maintained at 60-65°C with a nitrogen atmosphere and less than 0.1% oxygen content maintained by an active nitrogen sparge and the buttons were allowed to dry for 3 days.

[0318] A dry button was used to measure the refractive index, Abbe number, glass transition temperature, and water content, which are listed in Table 10 for each example.

[0319] The dry refractive index and Abbe number on both sides of the polymer buttons were measured at 25° C. and the average was reported. The wet refractive index on both sides of the polymer buttons was measured at 25° C. after suspension in PBS for 14 days at 37° C. and the average was reported. Prior to the wet refractive index measurement, the surface of the polymer button was thoroughly wiped with clean blotting paper to remove surface / excess PBS. The refractive index difference (ΔRI) is defined as the wet refractive index minus the dry refractive index. For water content measurement, the buttons were incubated in PBS at 37° C. for 14 days and then the water content was measured using the “drying method” described above. The water content was measured after 24, 48, and 72 hours of drying. Although it did not change significantly over this period, the average values ​​were calculated and listed in Table 10.

[0320] Lenses: In a glove box with atmospheric nitrogen gas and less than 0.1% oxygen gas (vol / vol), approximately 75-100 μL of the reactive mixture was dispensed at room temperature into a polypropylene front curve mold using an Eppendorf pipette. A base curve mold, also made of polypropylene, was then placed into the front curve mold. The polypropylene mold was equilibrated in the glove box for a minimum of 12 hours prior to dispensing. The lens mold assembly was transferred to an adjacent glove box maintained at approximately 60-65°C, and the lenses were then irradiated with the following profile: 5 mW / cm 2 (Top 2.5mW / cm 2 , and lower 2.5 mW / cm 2 ) for 20 minutes at 10mW / cm 2 (Top 5mW / cm 2 , and lower 5mW / cm 2 ) for 20 minutes at 20mW / cm 2 (Top 10mW / cm 2 , and lower 10 mW / cm 2 ) for 20 minutes and 30mW / cm 2 (Top 15mW / cm 2 , and lower 15mW / cm 2) for 30 minutes on each side using 435 nm LED light for a total of 90 hours from the top and bottom. The cured assembly was manually removed from the mold. The base curve mold was separated from the front curve mold using tweezers and any polymer flash was removed. The front curve mold with the lens still attached was placed in a 4° C. refrigerator for at least 1 minute. The chilled mold was removed and force was applied to the opposite side of the mold to mechanically release the lens.

[0321] For each example, the lenses were extracted with methanol, gradient equilibrated with PBS, and analyzed for macrovesicles or macrobrightens according to the procedure in the "Macrobrightens Test Method" above, and dark field micrographs taken by dark field microscopy are shown in Figure 4. The size of the macrovesicles or macrobrightens was large enough to be counted, and the range of numbers of macrovesicles or macrobrightens per lens for the four lenses is shown in Table 10.

[0322] [Table 9]

[0323] [Table 10] 1 3 polymer buttons, double-sided measurement, average of 6 measurements 2 drying method 3 Four lenses

[0324] For the most part, Examples 44-51 exhibited an excellent balance of properties, including refractive indices greater than about 1.52 and Abbe numbers greater than about 47, without exhibiting any visible macroscopic crystals.

[0325] Examples 52 to 55 Lenses were prepared from the RMMs listed in Table 11 according to the procedures of Examples 44-51. For each example, the lenses were extracted with methanol, gradient equilibrated with PBS, and analyzed for macrovesicles or macrobrightness according to the procedures in the "Macrobrightness Test Method" above. Four lenses were analyzed, and for each example, a dark field micrograph of the lens with the greatest number of macrobrightness is shown in FIG. 5.

[0326] [Table 11]

[0327] In Examples 45 and 52-55, as the amount of PEG-OH360 was decreased and the amount of TCDA was increased, the level of macro-crystals increased as shown in FIG.

[0328] Examples 56 to 71 For polymer buttons only, the light source is 5-6mW / cm 2Polymer buttons and lenses were prepared from the RMMs listed in Table 12 following the procedure for Examples 44-51, except that the light was TL03 light with an intensity of 0.01 μm. For each example, the refractive index, Abbe number, glass transition temperature, and water content were measured and are listed in Table 13. The dry refractive index and Abbe number on both sides of the button were measured at 25° C. and the average was reported. The wet refractive index on both sides of the button was measured at 25° C. after suspension in PBS for 14 days at 37° C. and the average was reported. Prior to the wet refractive index measurement, the surface of the button was thoroughly wiped with clean blotting paper to remove surface / excess PBS. The difference in refractive index (ΔRI) is defined as the wet refractive index minus the dry refractive index. For the water content measurement, the dry buttons were weighed and incubated in deionized water at 37° C. and the water content was measured at 7 and 14 days by the "hydration method". For each example, the lenses were extracted with methanol, gradient equilibrated with PBS, and analyzed for macrovesicles or macrobrights by dark field microscopy according to the procedure in the "Macrobrights Test Method" above. The macrovesicles or macrobrights were large enough to be counted, and the range of numbers of macrovesicles or macrobrights per lens observed in four lenses is shown in Table 13. For each example, the lenses were extracted with methanol, dried, and analyzed for microbrights density according to the procedure in the "Microbrights Test Method" above. The results measured by dark field microscopy are listed in Table 13.

[0329] [Table 12]

[0330] [Table 13] 1 3 buttons, double-sided measurement, average of 6 measurements 2 hydration method 3 Four lenses were evaluated 4 Average density from 4 lenses

[0331] For the most part, Examples 56-66 exhibited an excellent balance of properties, including refractive index greater than about 1.52 and Abbe number greater than about 48, while exhibiting no visible macrocrystals and low microcrystal density. When PEA was replaced by PEMA in the formulation of Example 56, the dry RI was 1.528864 (0.000084). The wet RI at 37°C after 14 days was 1.520183 (0.000694). The ΔRI was 0.008681. The Abbe number at 25°C was 51.46 (4.99). The %WC at 37°C on days 7 and 14 was 3.45 (0.03) and 4.08 (0.04), respectively. T g (first and second scans) were 9.7°C and 6.6°C, respectively. The extent of macro-crystals per lens was less than 1.23 / mm 2 Example 66 having a microcrystal density of 13.3 / mm 2 A dark field micrograph of an individual lens from Example 70 having a micro-vitreous density of 1.0 mm is shown in FIG.

[0332] Examples 72 to 84 For polymer buttons only, the light source is 5-6mW / cm 2Polymer buttons and lenses were prepared from the RMMs listed in Table 14 following the procedure for Examples 44-51, except that the light source was TL03 light with an intensity of 0.01 μm. For each example, the refractive index, Abbe number, glass transition temperature, and water content were measured and are listed in Table 15. The dry refractive index and Abbe number on both sides of the polymer buttons were measured at 25° C. and the average was reported. The wet refractive index on both sides of the polymer buttons was measured at 25° C. after suspension in PBS for 14 days at 37° C. and the average was reported. Prior to the wet refractive index measurement, the surface of the polymer button was thoroughly wiped with clean blotting paper to remove surface / excess PBS. The difference in refractive index (ΔRI) is defined as the wet refractive index minus the dry refractive index. For the water content measurement, the dry polymer buttons were weighed and incubated in deionized water at 37° C. and the water content was measured at 7 and 14 days by the "hydration method". For each example, four lenses were extracted with methanol, gradient equilibrated with PBS, and analyzed for macrovesicles or macrobrightens according to the procedure in the "Macrobrightens Test Method" above. Dark field micrographs of the lenses with the minimum and maximum number of macrovesicles or macrobrightens for each example are shown in Figures 7-11. The lenses of Examples 72-74 were incubated at 37°C in PBS for three days, while the lenses of Examples 75-84 were incubated at 37°C in PBS for five days. The macrovesicles or macrobrightens were large enough to be counted, and the range of macrovesicle numbers observed in the four lenses is listed in Table 15.

[0333] [Table 14]

[0334] [Table 15] 1 3 polymer buttons, double-sided measurement, average of 6 measurements 2 drying method 3 Four lenses

[0335] In Examples 72-84, formulations having 14-16 wt% PEG-OH360 and 4-6 wt% HEMA exhibited low levels of macrocrystals, as shown in Figures 7-11.

[0336] Examples 85 to 88 Under yellow lighting, the RMMs described in Table 16 were degassed by sparging with nitrogen gas for at least 3 minutes, the headspace was backfilled with nitrogen gas, and then immediately transferred to a charging box with 0.1% (vol / vol) oxygen gas and atmospheric pressure of nitrogen gas with an internal temperature of ambient temperature. Approximately 350 microliters of the RMMs were dispensed into an O-ring placed between two glass plates and held together by a clamp, after which the device was transferred to a curing box maintained at a temperature of 55°C to 60°C and 3 to 4 mW / cm. 2 for 15 min using TL03 light with an intensity of 6–7 mW / cm 2 The cured assemblies were manually removed from the mold. All of the polymer buttons were clear and not tacky. All of the polymer buttons were not extractable with any solvent. The dry refractive index, wet refractive index, Abbe number, and water content for each example were measured and are listed in Table 17.

[0337] The dry refractive index and Abbe number on both sides of the polymer buttons were measured at 25° C. and the average was reported. The wet refractive index on both sides of the polymer buttons was measured at 25° C. after suspension in PBS for 7 days at 37° C. and the average was reported. Prior to the wet refractive index measurement, the surface of the polymer button was thoroughly wiped with clean blotting paper to remove surface / excess PBS. The refractive index difference (ΔRI) is defined as the wet refractive index minus the dry refractive index. For the water content measurement, the polymer buttons were incubated in PBS at 37° C. for 7 days and then the water content was measured using the "Dry Method" described above.

[0338] [Table 16]

[0339] [Table 17] 1 3 polymer buttons, double-sided measurement, average of 6 measurements 2 drying method

[0340] term For completeness reasons, various aspects of the disclosure are described in the following numbered sections.

[0341] Item 1.a. at least one hydrophobic monomer; b. at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers, and any combination thereof; c. Tricyclo[5.2.1.0 2,6 ] decanedimethanol di(meth)acrylate crosslinker; The polymer is prepared by free radical polymerization of a reactive monomer mixture comprising: A composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39.

[0342] Item 2. The composition of item 1, wherein the hydrophobic monomer is a hydrophobic (meth)acrylate monomer.

[0343] Item 3. The composition described in item 2, wherein the hydrophobic (meth)acrylate is selected from an aliphatic (meth)acrylate, an aromatic (meth)acrylate, an alicyclic (meth)acrylate, and any combination thereof.

[0344] Item 4. The composition described in item 3, wherein the hydrophobic (meth)acrylate is a cycloaliphatic (meth)acrylate.

[0345] Item 5. Alicyclic (meth)acrylates include cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, norbornyl (meth)acrylate, isobornyl (meth)acrylate, isobornyl derivatives, norbornyl derivatives, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl (meth)acrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, poly(ethylene)glycol dicyclopentenyl ether (meth)acrylate, 2-(((3aR,4R,5S,7R,7aR)-octahydro-1H-4,7-methano 2-(((3aS,4R,6S,7R,7aR)-3a,4,5,6,7,7aHexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, (3aS,4S,5R,7S,7aS)-Octahydro-1H-4,7-methanoinden-5-yl acrylate, (3aS,4S,5R,7S,7aS)-3a,4,5,6,7,7aHexahydro-1H-4,7-methanoinden-5-yl acrylate 5. The composition of claim 4, wherein the hydroxyl group is selected from H-4,7-methanoinden-5-yl acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl PEG (meth)acrylate derivatives and (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate derivatives, and any combination thereof.

[0346] Item 6. The composition described in item 5, wherein the alicyclic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, cyclohexyl methyl methacrylate, 2-cyclohexyl ethyl acrylate, 2-cyclohexyl ethyl methacrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, and any combination thereof.

[0347] Item 7. The composition described in item 6, wherein the alicyclic (meth)acrylate is ethylene glycol dicyclopentenyl ether (meth)acrylate.

[0348] Item 8. The composition according to any one of items 4 to 7, wherein the reactive monomer mixture contains an alicyclic (meth)acrylate in an amount of about 40 to about 90% by weight, about 50 to about 80% by weight, or about 50 to about 70% by weight.

[0349] Item 9. The composition described in item 3, wherein the hydrophobic (meth)acrylate is an aliphatic (meth)acrylate.

[0350] Item 10. Aliphatic (meth)acrylates are C1-C 18 10. The composition according to claim 9, which is an alkyl (meth)acrylate.

[0351] Section 11.C1~C 18 11. The composition of claim 10, wherein the alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, isodecyl (meth)acrylate, heptadecyl (meth)acrylate, dodecyl (meth)acrylate, 2-propylheptyl (meth)acrylate, stearyl (meth)acrylate, and any combination thereof.

[0352] Section 12.C1~C 18 12. The composition of claim 11, wherein the alkyl (meth)acrylate is n-hexyl acrylate.

[0353] Item 13. The composition according to any one of items 9 to 12, wherein the reactive monomer mixture contains an aliphatic (meth)acrylate in an amount of about 1 to about 20% by weight, or about 1 to about 10% by weight.

[0354] Item 14. The composition described in item 3, wherein the hydrophobic (meth)acrylate is an aromatic (meth)acrylate.

[0355] Item 15. The composition of item 14, wherein the aromatic (meth)acrylate is selected from the group consisting of 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 4-chlorophenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis-phenylthiol-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof.

[0356] Item 16. The composition of item 15, wherein the aromatic (meth)acrylate is 2-phenylethyl acrylate.

[0357] Item 17. The composition of item 15, wherein the aromatic (meth)acrylate is 2-phenylethyl methacrylate.

[0358] Item 18. The composition described in item 15, wherein the aromatic (meth)acrylate is a combination of 2-phenylethyl acrylate and 2-phenylethyl methacrylate.

[0359] Item 19. The composition described in item 15, wherein the aromatic (meth)acrylate is a combination of 2-phenylethyl methacrylate and 3-phenylpropyl acrylate.

[0360] Item 20. The composition according to any one of items 14 to 19, wherein the reactive monomer mixture comprises an aromatic (meth)acrylate in an amount of about 7 to about 25 weight percent, about 10 to about 20 weight percent, or about 12 to about 15 weight percent.

[0361] Item 21. The composition according to any one of items 1 to 20, wherein the reactive monomer mixture comprises at least one hydrophilic monomer.

[0362] Item 22. The composition of item 21, wherein the at least one hydrophilic monomer is selected from vinylpyrrolidone, N-vinyl N-methylacetamide, N-methylmethacrylamide, N-vinylacetamide, N,N-dimethylacrylamide, N-hydroxyethylacrylamide, N-(2-hydroxypropyl)acrylamide, N-(3-hydroxypropyl)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, N-(3-hydroxypropyl)(meth)acrylamide, poly(ethylene glycol) methyl ether (meth)acrylate, poly(ethylene glycol) (meth)acrylate, and any combination thereof.

[0363] Item 23. The composition of item 22, wherein at least one hydrophilic monomer is a poly(ethylene glycol)-containing monomer.

[0364] Item 24. The composition of item 23, wherein the poly(ethylene glycol)-containing monomer is selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate, and combinations thereof.

[0365] Item 25. The poly(ethylene glycol)-containing monomer has a number average molecular weight (M) of about 200 g to about 1000 g / mol, or about 200 g / mol to about 400 g / mol. n 25. The composition according to claim 23 or 24, having a structure comprising:

[0366] Item 26. A poly(ethylene glycol)-containing monomer having the formula:

[0367] [ka] In the formula, R a and R b 24. The composition according to item 23, wherein each is independently selected from hydrogen and methyl, and m is an integer from 2 to 25.

[0368] Section 27.R a is methyl and R b 27. The composition according to claim 26, wherein is hydrogen.

[0369] Item 28. The composition according to any one of items 26 and 27, wherein m is an integer from 2 to 8.

[0370] Item 29. The composition described in any one of items 1 to 28, wherein the reactive monomer mixture comprises at least one hydrophilic monomer in an amount of about 1 to about 40 weight percent, about 10 to about 30 weight percent, about 12 to about 22 weight percent, or about 14 to about 20 weight percent.

[0371] Item 30. The composition of any one of items 1 to 29, wherein the reactive monomer mixture comprises at least one hydroxyalkyl (meth)acrylate monomer.

[0372] Item 31. The composition of item 30, wherein the hydroxyalkyl (meth)acrylate monomer is selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof.

[0373] Item 32. The composition of item 31, wherein the hydroxyalkyl (meth)acrylate monomer is 2-hydroxyethyl methacrylate.

[0374] Item 33. The composition described in any one of items 1 to 32, wherein the reactive monomer mixture comprises at least one hydroxyalkyl (meth)acrylate monomer in an amount between about 1 and about 10 weight percent, about 2 to about 8 weight percent, or about 4 to about 6 weight percent.

[0375] Item 34. The composition of any one of items 1 to 33, wherein the reactive monomer mixture comprises a combination of a hydrophilic monomer and a hydroxyalkyl (meth)acrylate monomer.

[0376] Item 35. The composition of item 34, wherein the hydrophilic monomer is a poly(ethylene glycol)-containing (meth)acrylate monomer and the hydroxyalkyl (meth)acrylate monomer is 2-hydroxyethyl (meth)acrylate.

[0377] Item 36. The composition of item 35, wherein the hydrophilic monomer is selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate, and the hydroxyalkyl (meth)acrylate monomer is 2-hydroxyethyl acrylate.

[0378] Item 37. Tricyclo[5.2.1.0 2,6 ]Decanedimethanol di(meth)acrylate crosslinker is tricyclo[5.2.1.0 2,6 37. The composition according to any one of items 1 to 36, wherein the compound is decanedimethanol diacrylate.

[0379] Item 38. The reactive monomer mixture comprises about 1 to about 20 weight percent, about 3 to about 15 weight percent, or about 3 to about 10 weight percent of tricyclo[5.2.1.0 2,6 ] The composition according to any one of items 1 to 37, comprising a decanedimethanol di(meth)acrylate crosslinking agent.

[0380] Item 39. The hydrophobic monomer is ethylene glycol dicyclopentenyl ether (meth)acrylate, the hydrophilic monomer is selected from the group consisting of poly(ethylene glycol) methacrylate, poly(ethylene glycol) methyl ether methacrylate, 2-hydroxyethyl methacrylate, and any combination thereof, and the crosslinker is tricyclo[5.2.1.0 2,6 ] decanedimethanol diacrylate, Item 39. The composition according to any one of items 1 to 38.

[0381] Item 40. The composition of any one of items 1 to 39, wherein the reactive monomer mixture further comprises a polyamide.

[0382] Item 41. The composition of item 40, wherein the polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinyl-acetamide), poly(dimethylacrylamide), and copolymers or mixtures thereof.

[0383] Item 42. The composition of item 41, wherein the polyamide is poly(vinylpyrrolidone).

[0384] Item 43. The composition of item 40, wherein the polyamide is a copolymer.

[0385] Item 44. The composition described in any one of items 40 to 43, wherein the reactive monomer mixture comprises polyamide in an amount of about 0.1% by weight to about 5% by weight, about 0.5% by weight to about 3% by weight, or about 0.5% by weight to about 2% by weight.

[0386] Item 45. The composition described in any one of items 1 to 44, further comprising at least one UV / HEV absorbing compound in the reactive monomer mixture.

[0387] Item 46. The composition of item 45, wherein the UV / HEV absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, or any combination thereof.

[0388] Item 47. The composition described in item 45 or 46, wherein the reactive monomer mixture comprises a UV / HEV absorbing compound in an amount of about 0.1 to about 5 weight percent, about 1 to about 4 weight percent, or about 1 to about 3 weight percent.

[0389] Item 48. The composition described in any one of items 1 to 47, further comprising at least one diluent in the reactive monomer mixture.

[0390] Item 49. The composition described in any one of items 1 to 48, having a water content of about 0% to about 15% by weight, about 1% to about 10% by weight, or about 1% to about 8% by weight.

[0391] Item 50. The composition has a refractive index of at least 1.45 and an Abbe number of at least 45, the composition has a refractive index of at least 1.48 and an Abbe number of at least 50, or the composition has a refractive index of at least 1.50 and an Abbe number of at least 50. Item 1. The composition according to any one of items 1 to 49.

[0392] Item 51. The composition described in any one of items 1 to 50, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator.

[0393] Item 52. An ophthalmic device comprising the composition described in any one of items 1 to 51.

[0394] Clause 53. The ophthalmic device of clause 52, wherein the ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal outlay, or a corneal insert.

[0395] Item 54. The ophthalmic device of item 53, wherein the ophthalmic device comprises an intraocular lens.

[0396] Item 55. A method for making an ophthalmic device, comprising: a. providing a composition according to any one of paragraphs 1 to 51; b. forming an ophthalmic device; A method comprising:

[0397] Item 56. The method of item 55, further comprising extracting the ophthalmic device with a solvent.

[0398] Item 57. The method of item 56, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

[0399] 58. A method for making an ophthalmic device, comprising: a. preparing a blank from the composition according to any one of claims 1 to 51; b. machining an ophthalmic device from the blank; A method comprising:

[0400] Item 59. The method of item 58, further comprising extracting the ophthalmic device with a solvent.

[0401] Clause 60. The method of clause 59, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

[0402] Item 61. The method of any one of items 55 to 60, further comprising an irradiation step using a femtosecond two-photon laser.

[0403] Item 62. The method of any one of items 55 to 61, further comprising a step of sterilizing the ophthalmic device.

[0404] Clause 63. A method for making an ophthalmic device, comprising molding the device from a composition described in any one of clauses 1 to 51.

[0405] 64.a. at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings; b. at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers, and any combination thereof; c. at least one crosslinker; The present invention is prepared by free radical polymerization of a reactive monomer mixture comprising: A composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39.

[0406] Item 65. The composition described in item 64, wherein the at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings comprises two or more individual monocyclic alicyclic rings, or a bicyclic, tricyclic, bridged, fused, and / or spirocyclic alicyclic ring system.

[0407] Item 66. At least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings is selected from the group consisting of norbornyl (meth)acrylate, isobornyl (meth)acrylate, isobornyl derivatives, norbornyl derivatives, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl (meth)acrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, poly(ethylene)glycol dicyclopentenyl ether (meth)acrylate, 2,2-bis(cyclopent-1-en-1-yloxy)ethyl (meth)acrylate, 2-(((3aR,4R,5S,7R,7aR)-octahydro-1H-4,7-methanoinden-5-yl)oxy)ethyl acrylate, 2-(((3aS,4R,6S,7R,7aR) -3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, (3aS,4S,5R,7S,7aS)-octahydro-1H-4,7-methanoinden-5-yl acrylate, (3aS,4S,5R,7S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-yl acrylate, ( Item 64. The composition according to item 64 or 65, which is selected from (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl PEG (meth)acrylate derivatives and (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate derivatives, and any combination thereof.

[0408] Item 67. The composition described in any one of items 64 to 66, wherein the at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings is ethylene glycol dicyclopentenyl ether acrylate.

[0409] Item 68. The composition described in any one of items 64 to 67, wherein the reactive monomer mixture comprises at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings in an amount of about 40 to about 90 weight percent, about 50 to about 80 weight percent, or about 50 to about 70 weight percent.

[0410] Item 69. The composition described in any one of items 64 to 68, wherein the reactive monomer mixture includes at least one hydrophilic monomer.

[0411] Item 70. The composition of item 69, wherein the at least one hydrophilic monomer is selected from vinylpyrrolidone, N-vinyl N-methylacetamide, N-methylmethacrylamide, N-vinylacetamide, N,N-dimethylacrylamide, N-hydroxyethylacrylamide, N-(2-hydroxypropyl)acrylamide, N-(3-hydroxypropyl)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, N-(3-hydroxypropyl)(meth)acrylamide, poly(ethylene glycol) methyl ether (meth)acrylate, poly(ethylene glycol) (meth)acrylate, and any combination thereof.

[0412] Item 71. The composition described in item 69, wherein at least one hydrophilic monomer is a poly(ethylene glycol)-containing monomer.

[0413] Item 72. The composition of item 71, wherein the poly(ethylene glycol)-containing monomer is selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate, and combinations thereof.

[0414] Item 73. The poly(ethylene glycol)-containing monomer has a number average molecular weight (M) of about 200 g to about 1000 g / mol, or about 200 g / mol to about 400 g / mol. n 73. The composition according to claim 71 or 72, having

[0415] Item 74. A poly(ethylene glycol)-containing monomer having the formula:

[0416] [ka] In the formula, R a and R b 72. The composition according to item 71, wherein each is independently selected from hydrogen and methyl, and m is an integer from 2 to 25.

[0417] Section 75.R a is methyl and R b 75. The composition according to paragraph 74, wherein is hydrogen.

[0418] Item 76. The composition according to any one of items 74 and 75, wherein m is an integer from 2 to 8.

[0419] Item 77. The composition described in any one of items 64 to 76, wherein the reactive monomer mixture comprises at least one hydrophilic monomer in an amount of about 1 to about 40 weight percent, about 10 to about 30 weight percent, about 12 to about 22 weight percent, or about 14 to about 20 weight percent.

[0420] Item 78. The composition of any one of items 64 to 77, wherein the reactive monomer mixture comprises at least one hydroxyalkyl (meth)acrylate monomer.

[0421] Item 79. The composition of item 78, wherein the hydroxyalkyl (meth)acrylate is selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof.

[0422] Item 80. The composition of item 79, wherein the hydroxyalkyl (meth)acrylate monomer is 2-hydroxyethyl methacrylate.

[0423] Item 81. The composition described in any one of items 64 to 80, wherein the reactive monomer mixture comprises at least one hydroxyalkyl (meth)acrylate monomer in an amount between about 1 and about 10 weight percent, about 2 to about 8 weight percent, or about 4 to about 6 weight percent.

[0424] Item 82. The composition of any one of items 64 to 81, wherein the reactive monomer mixture comprises a combination of a hydrophilic monomer and a hydroxyalkyl (meth)acrylate monomer.

[0425] Item 83. The composition of item 82, wherein the hydrophilic monomer is a poly(ethylene glycol)-containing (meth)acrylate monomer and the hydroxyalkyl (meth)acrylate monomer is 2-hydroxyethyl (meth)acrylate.

[0426] Item 84. The composition of item 83, wherein the hydrophilic monomer is selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate, and the hydroxyalkyl (meth)acrylate monomer is 2-hydroxyethyl acrylate.

[0427] Item 85. The composition described in any one of items 64 to 84, wherein the at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings is ethylene glycol dicyclopentenyl ether acrylate, and the at least one hydrophilic monomer is selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate.

[0428] Item 86. The composition described in any one of items 64 to 85, wherein the reactive monomer mixture further comprises at least one alicyclic (meth)acrylate containing one alicyclic ring.

[0429] Item 87. The composition described in item 86, wherein the alicyclic (meth)acrylate containing one alicyclic ring has at least one alicyclic group that contains at least one carbon-carbon double bond.

[0430] Item 88. The composition described in item 86, wherein the alicyclic (meth)acrylate containing one alicyclic ring is selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, and any combination thereof.

[0431] Item 89. The composition described in item 88, wherein the alicyclic (meth)acrylate containing one alicyclic ring is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, 2-cyclohexyl ethyl acrylate, 2-cyclohexyl ethyl methacrylate, 3-cyclohexyl propyl acrylate, and any combination thereof.

[0432] Item 90. The method of any one of items 86 to 89, wherein the reactive monomer mixture comprises an alicyclic (meth)acrylate containing one alicyclic ring in an amount of about 10 to about 25 weight percent, about 10 to about 20 weight percent, or about 12 to about 15 weight percent.

[0433] Item 91. The composition described in any one of items 64 to 90, wherein the reactive monomer mixture further comprises at least one aromatic (meth)acrylate.

[0434] Item 92. The composition of item 91, wherein the at least one aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof.

[0435] Item 93. The composition of item 91 or 92, wherein the at least one aromatic (meth)acrylate is 2-phenylethyl acrylate.

[0436] Item 94. The composition described in any one of items 91 to 93, wherein the reactive monomer mixture contains an aromatic (meth)acrylate in an amount of about 10 to about 25 weight percent, about 10 to about 20 weight percent, or about 12 to about 15 weight percent.

[0437] Item 95. The composition described in any one of items 64 to 94, wherein the reactive monomer mixture further comprises a hydroxyalkyl (meth)acrylate.

[0438] Item 96. The composition of item 95, wherein the hydroxyalkyl (meth)acrylate comprises a straight-chain, branched-chain, or cyclic hydroxyalkyl group having 1 to 25 carbon atoms.

[0439] Item 97. The composition of item 95 or 96, wherein the hydroxyalkyl (meth)acrylate is selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof.

[0440] Item 98. The composition according to any one of items 95 to 97, wherein the hydroxyalkyl (meth)acrylate is 2-hydroxyethyl methacrylate.

[0441] Item 99. The composition described in any one of items 95 to 98, wherein the reactive monomer mixture comprises a hydroxyalkyl (meth)acrylate in an amount of about 1 to about 10 weight percent, about 2 to about 8 weight percent, or about 4 to about 6 weight percent.

[0442] Item 100. The composition according to any one of items 64 to 99, wherein the crosslinking agent is selected from the group consisting of a non-alicyclic crosslinking agent, an alicyclic crosslinking agent, and any combination thereof.

[0443] Item 101. The composition according to any one of items 64 to 100, wherein the crosslinking agent is an alicyclic crosslinking agent containing an alicyclic group having 1 to 4 alicyclic rings.

[0444] Item 102. Alicyclic crosslinking agent is tricyclo[5.2.1.0 2,6 ] decanedimethanol di(meth)acrylate, the composition according to item 101.

[0445] Item 103. The composition described in any one of items 64 to 102, wherein the reactive monomer mixture comprises a crosslinker in an amount of about 1 to about 20 weight percent, about 3 to about 15 weight percent, or about 3 to about 10 weight percent.

[0446] Item 104. The composition of any one of items 64 to 103, wherein the reactive monomer mixture further comprises a polyamide.

[0447] Item 105. The composition of item 104, wherein the polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinyl-acetamide), poly(dimethylacrylamide), and copolymers or mixtures thereof.

[0448] Item 106. The composition of item 105, wherein the polyamide is poly(vinylpyrrolidone).

[0449] Item 107. The composition of item 104, wherein the polyamide is a copolymer.

[0450] Item 108. The composition of any one of items 104 to 107, wherein the reactive monomer mixture comprises polyamide in an amount of about 0.1% to about 5% by weight, about 0.5% to about 3% by weight, or about 0.5% to about 2% by weight.

[0451] Item 109. The composition of any one of items 64 to 108, further comprising at least one UV / HEV absorbing compound in the reactive monomer mixture.

[0452] Item 110. The composition of item 109, wherein the UV / HEV absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, or any combination thereof.

[0453] Item 111. The composition of item 109 or 110, wherein the reactive monomer mixture comprises a UV / HEV absorbing compound in an amount of about 0.1 to about 5 weight percent, about 1 to about 4 weight percent, or about 1 to about 3 weight percent.

[0454] Item 112. The composition described in any one of items 64 to 111, further comprising at least one diluent in the reactive monomer mixture.

[0455] Item 113. The composition described in any one of items 64 to 112, having a water content of about 0% to about 15% by weight, about 1% to about 10% by weight, or about 1% to about 8% by weight.

[0456] Item 114. The composition has a refractive index of at least 1.45 and an Abbe number of at least 45; the composition has a refractive index of at least 1.48 and an Abbe number of at least 50; or the composition has a refractive index of at least 1.50 and an Abbe number of at least 50. Item 64. The composition according to any one of items 64 to 113.

[0457] Item 115. The composition described in any one of items 64 to 114, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator.

[0458] Item 116. An ophthalmic device comprising the composition described in any one of items 64 to 115.

[0459] Item 117. The ophthalmic device of item 116, wherein the ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal outlay, or a corneal insert.

[0460] Item 118. The ophthalmic device of item 117, wherein the ophthalmic device comprises an intraocular lens.

[0461] Item 119. A method for making an ophthalmic device, comprising: c. Providing a composition according to any one of paragraphs 64 to 115; d. forming an ophthalmic device; A method comprising:

[0462] Item 120. The method of item 119, further comprising extracting the ophthalmic device with a solvent.

[0463] Item 121. The method of item 120, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

[0464] Item 122. A method for making an ophthalmic device, comprising: c. Preparing a blank from the composition according to any one of paragraphs 64 to 115; d. Machining an ophthalmic device from the blank; The method includes:

[0465] Item 123. The method of item 122, further comprising extracting the ophthalmic device with a solvent.

[0466] Item 124. The method of item 123, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

[0467] Item 125. The method of any one of items 119 to 124, further comprising an irradiation step using a femtosecond two-photon laser.

[0468] Item 126. The method of any one of items 119 to 125, further comprising a step of sterilizing the ophthalmic device.

[0469] Clause 127. A method for making an ophthalmic device, comprising molding the device from a composition described in any one of clauses 64 to 115.

[0470] Item 128.a. at least one hydroxyalkyl (meth)acrylate; b. at least one aromatic (meth)acrylate; c. at least one aliphatic (meth)acrylate; d. at least one crosslinker; The polymer is prepared by free radical polymerization of a reactive monomer mixture comprising: A composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39.

[0471] Item 129. The composition described in item 128, wherein the alicyclic (meth)acrylate contains an alicyclic group having 1 to 4 alicyclic rings.

[0472] Item 130. The composition of item 128 or 129, wherein the cycloaliphatic (meth)acrylate has at least one cycloaliphatic group containing at least one carbon-carbon double bond.

[0473] Item 131. Cycloaliphatic (meth)acrylates include cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, norbornyl (meth)acrylate, isobornyl (meth)acrylate, isobornyl derivatives, norbornyl derivatives, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl 129. The composition of claim 128 or 129, wherein the compound is selected from the group consisting of (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl PEG (meth)acrylate derivatives and (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate derivatives, and any combination thereof.

[0474] Item 132. The composition of item 128 or 129, wherein the alicyclic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, cyclohexyl methyl methacrylate, 2-cyclohexyl ethyl acrylate, 2-cyclohexyl ethyl methacrylate, 3-cyclohexyl propyl acrylate, ethylene glycol dicyclopentenyl ether acrylate, and any combination thereof.

[0475] Item 133. The composition described in any one of items 128 to 132, wherein the reactive monomer mixture comprises an alicyclic (meth)acrylate in an amount of about 20 to about 80 weight percent, about 40 to about 80 weight percent, or about 60 to about 80 weight percent.

[0476] Item 134. The composition according to any one of items 128 to 133, wherein the aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis-phenylthiol-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof.

[0477] Item 135. The composition of item 134, wherein the aromatic (meth)acrylate is selected from 2-phenylethyl acrylate, 2-phenylethyl methacrylate, 3-phenylpropyl acrylate, and combinations thereof.

[0478] Item 136. The composition according to any one of items 128 to 133, wherein the aromatic (meth)acrylate has at least one aliphatic group containing at least one carbon-carbon double bond.

[0479] Item 137. The composition of item 136, wherein the aromatic (meth)acrylate is cinnamyl (meth)acrylate.

[0480] Item 138. The composition described in any one of items 128 to 137, wherein the reactive monomer mixture comprises an aromatic (meth)acrylate in an amount of about 5 to about 50 weight percent, about 10 to about 40 weight percent, or about 15 to about 40 weight percent.

[0481] Item 139. The composition of any one of items 128 to 138, wherein the aliphatic (meth)acrylate comprises a linear or branched alkyl group containing 1 to 25 carbon atoms.

[0482] Item 140. The composition according to any one of items 128 to 139, wherein the aliphatic (meth)acrylate has at least one aliphatic group containing at least one carbon-carbon double bond.

[0483] Item 141. The composition of any one of items 128 to 139, wherein the aliphatic (meth)acrylate comprises a linear alkyl group containing 4 to 8 carbon atoms.

[0484] Item 142. The composition of item 141, wherein the aliphatic (meth)acrylate is n-hexyl acrylate.

[0485] Item 143. The composition according to any one of items 128 to 142, wherein the reactive monomer mixture comprises an aliphatic (meth)acrylate in an amount of 1 to 40 weight percent, about 1 to about 20 weight percent, or about 1 to about 10 weight percent.

[0486] Item 141. The composition described in any one of items 128 to 143, wherein the crosslinking agent is selected from the group consisting of non-alicyclic crosslinking agents, alicyclic crosslinking agents, and any combination thereof.

[0487] Item 145. The composition of item 144, wherein the crosslinking agent is a non-alicyclic crosslinking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl(meth)acrylate) terminated polydimethylsiloxane, and any combination thereof.

[0488] Item 146. The composition described in item 145, wherein the non-alicyclic crosslinker is ethylene glycol dimethacrylate.

[0489] Item 147. The composition described in item 146, wherein the crosslinking agent is an alicyclic crosslinking agent containing an alicyclic group having 1 to 4 alicyclic rings.

[0490] Item 148. Alicyclic crosslinker is tricyclo[5.2.1.0 2,6] decanedimethanol di(meth)acrylate, and the composition according to item 147.

[0491] Item 149. The composition of item 148 or 148, wherein the reactive monomer mixture comprises an alicyclic crosslinker in an amount of about 1 to about 20 weight percent, about 3 to about 15 weight percent, or about 3 to about 10 weight percent.

[0492] Item 150. The composition of any one of items 128 to 149, wherein the reactive monomer mixture further comprises a polyamide.

[0493] Item 151. The composition of item 150, wherein the polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinyl-acetamide), poly(dimethylacrylamide), and copolymers or mixtures thereof.

[0494] Item 152. The composition of item 151, wherein the polyamide is poly(vinylpyrrolidone).

[0495] Item 153. The composition of item 150, wherein the polyamide is a copolymer.

[0496] Item 154. The composition of any one of items 150 to 153, wherein the reactive monomer mixture comprises polyamide in an amount of about 0.1% to about 5% by weight, about 0.5% to about 3% by weight, or about 0.5% to about 2% by weight.

[0497] Item 155. The composition of any one of items 128 to 154, further comprising at least one hydroxysilicone monomer.

[0498] Item 156. The composition of item 155, wherein the hydroxysilicone monomer comprises mono-n-butyl terminated mono-(2-hydroxy-3-methacryloxypropyloxy)-propyl terminated polydimethylsiloxane, 3-(3-(1,1,1,3,5,5,5-heptamethyltrisiloxane-3-yl)propoxy)-2-hydroxypropyl methacrylate, 3-(3-(1,5-di-tert-butyl-1,1,3,5,5-pentamethyltrisiloxane-3-yl)propoxy)-2-hydroxypropyl methacrylate, or any combination thereof.

[0499] Item 157. The composition described in item 155 or 156, wherein the reactive monomer mixture comprises a hydroxysilicone monomer in an amount of about 1 to about 25 weight percent, about 5 to about 20 weight percent, or about 10 to about 20 weight percent.

[0500] Item 158. The composition according to any one of items 128 to 157, further comprising at least one hydroxyalkyl (meth)acrylate.

[0501] Item 159. The composition of item 158, wherein the hydroxyalkyl (meth)acrylate comprises a straight-chain, branched-chain, or cyclic hydroxyalkyl group having 1 to 25 carbon atoms.

[0502] Item 160. The composition of item 159, wherein the hydroxyalkyl (meth)acrylate is selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof.

[0503] Item 161. The composition according to item 160, wherein the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate or 2-hydroxyethyl methacrylate.

[0504] Item 162. The composition described in any one of items 158 to 161, wherein the reactive monomer mixture comprises a hydroxyalkyl (meth)acrylate in an amount of about 1 to about 25 weight percent, about 5 to about 20 weight percent, or about 10 to about 20 weight percent.

[0505] Item 163. The composition of any one of items 128 to 162, further comprising at least one UV / HEV absorbing compound in the reactive monomer mixture.

[0506] Item 164. The composition of item 163, wherein the UV / HEV absorbing compound is a compound of formula I, 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, or any combination thereof.

[0507] Item 165. The composition of item 163 or 164, wherein the reactive monomer mixture comprises a UV / HEV absorbing compound in an amount of about 0.1 to about 5 weight percent, about 1 to about 4 weight percent, or about 1 to about 3 weight percent.

[0508] Item 166. The composition described in any one of items 128 to 165, further comprising at least one hydrophilic monomer.

[0509] Item 167. The composition described in item 166, wherein the hydrophilic monomer is selected from vinylpyrrolidone, N-vinyl-N-methylacetamide, N-methylmethacrylamide, N-vinylacetamide, N,N-dimethylacrylamide, poly(ethylene glycol) methyl ether (meth)acrylate, poly(ethylene glycol) (meth)acrylate, and any combination thereof.

[0510] Item 168. The composition described in item 166, wherein the hydrophilic monomer has at least one aliphatic group having at least one double bond.

[0511] Item 169. The composition described in any one of items 128 to 168, further comprising at least one diluent in the reactive monomer mixture.

[0512] Item 170. The composition described in any one of items 128 to 169, having a water content of about 0% to about 15% by weight, about 1% to about 10% by weight, or about 1% to about 8% by weight.

[0513] Item 171. The composition has a refractive index of at least 1.45 and an Abbe number of at least 45; the composition has a refractive index of at least 1.48 and an Abbe number of at least 50; or the composition has a refractive index of at least 1.50 and an Abbe number of at least 50. Item 128. The composition according to any one of items 128 to 170.

[0514] Item 172. The composition described in any one of items 128 to 171, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator.

[0515] Item 173. An ophthalmic device comprising a composition described in any one of items 128 to 172.

[0516] Clause 174. The ophthalmic device of clause 173, wherein the ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal outlay, or a corneal insert.

[0517] Clause 175. The ophthalmic device of clause 174, wherein the ophthalmic device comprises an intraocular lens.

[0518] 176. A method for making an ophthalmic device, comprising: a. providing a composition according to any one of paragraphs 128-172; b. forming an ophthalmic device; A method comprising:

[0519] Item 177. The method of item 176, further comprising extracting the ophthalmic device with a solvent.

[0520] Item 178. The method of item 177, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

[0521] 179. A method for making an ophthalmic device, comprising forming: a. preparing a blank from any of the compositions of paragraphs 128-172 and machining an ophthalmic device from the blank; or b. Molding a lens from the composition according to any one of paragraphs 128 to 172; or c. Molding a lens from the composition according to any one of items 128 to 172, and refining the surface by machining. 3. A method comprising the steps of:

[0522] Item 180. The method of item 179, further comprising extracting the ophthalmic device with a solvent.

[0523] Item 181. The method of item 290, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

[0524] Item 182. The method of any one of items 176 to 181, further comprising an irradiation step using a femtosecond two-photon laser.

[0525] Item 183. The method of any one of items 176 to 182, further comprising the step of sterilizing the ophthalmic device.

[0526] Clause 184. A method for making an ophthalmic device, comprising molding the device from a composition described in any one of clauses 128 to 172.

[0527] 185.a. at least one hydroxyalkyl (meth)acrylate; b. at least one aliphatic (meth)acrylate; c. at least one crosslinker; The present invention is prepared by free radical polymerization of a reactive monomer mixture comprising: A composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39.

[0528] Item 186. The composition described in item 185, wherein the alicyclic (meth)acrylate contains an alicyclic group having 1 to 4 alicyclic rings.

[0529] Item 187. Alicyclic (meth)acrylates include cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, norbornyl (meth)acrylate, isobornyl (meth)acrylate, (meth)acrylate, isobornyl derivatives, norbornyl derivatives, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl (meth)acrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, poly(ethylene)glycol dicyclopentenyl ether (meth)acrylate, 2-(((3aR,4R,5S,7R,7aR)-octahydro-1H-4,7-methanoindene -5-yl)oxy)ethyl acrylate, 2-(((3aS,4R,6S,7R,7aR)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, (3aS,4S,5R,7S,7aS)-octahydro-1H-4,7-methanoinden-5-yl acrylate, (3aS,4S,5R,7S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7- Item 185 or 186. The composition according to item 185 or 186, wherein the compound is selected from methanoinden-5-yl acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl PEG (meth)acrylate derivatives and (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate derivatives, and any combination thereof.

[0530] Item 188. The composition according to any one of items 185 to 187, wherein the alicyclic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, cyclohexyl methyl methacrylate, 2-cyclohexyl ethyl acrylate, 2-cyclohexyl ethyl methacrylate, 3-cyclohexyl propyl acrylate, ethylene glycol dicyclopentenyl ether acrylate, and any combination thereof.

[0531] Item 189. The composition described in any one of items 185 to 188, wherein the reactive monomer mixture comprises an alicyclic (meth)acrylate in an amount of about 20 to about 80 weight percent, about 40 to about 80 weight percent, or about 60 to about 80 weight percent.

[0532] Item 190. The composition of any one of items 185 to 189, wherein the aliphatic (meth)acrylate comprises a linear or branched alkyl group containing 1 to 25 carbon atoms.

[0533] Item 191. The composition of item 190, wherein the aliphatic (meth)acrylate contains a linear or branched alkyl group containing from 4 to 8 carbon atoms.

[0534] Item 192. The composition according to item 191, wherein the aliphatic (meth)acrylate is isobutyl acrylate or n-hexyl acrylate.

[0535] Item 193. The composition according to any one of items 185 to 192, wherein the reactive monomer mixture comprises an aliphatic (meth)acrylate in an amount of about 1 to about 40 weight percent, about 1 to about 20 weight percent, or about 1 to about 10 weight percent.

[0536] Item 194. The composition described in any one of items 185 to 193, wherein the crosslinking agent is selected from a non-alicyclic crosslinking agent, an alicyclic crosslinking agent, and any combination thereof.

[0537] Item 195. The composition of item 194, wherein the crosslinking agent is a non-alicyclic crosslinking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl(meth)acrylate) terminated polydimethylsiloxane, and any combination thereof.

[0538] Item 196. The composition described in item 195, wherein the non-alicyclic crosslinker is ethylene glycol dimethacrylate.

[0539] Item 197. The composition described in item 194, wherein the crosslinking agent is an alicyclic crosslinking agent containing an alicyclic group having 1 to 4 alicyclic rings.

[0540] Item 198. Alicyclic crosslinking agent is tricyclo[5.2.1.0 2,6 ] decanedimethanol di(meth)acrylate, and the composition described in item 197.

[0541] Item 199. The composition of any one of items 185 to 198, wherein the reactive monomer mixture comprises a crosslinker in an amount of about 1 to about 20 weight percent, about 1 to about 15 weight percent, or about 1 to about 5 weight percent.

[0542] Item 200. The composition according to any one of items 185 to 199, further comprising an aromatic (meth)acrylate.

[0543] Item 201. The composition of item 200, wherein the aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis-phenylthiol-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof.

[0544] Item 202. The composition of item 201, wherein the aromatic (meth)acrylate is selected from 2-phenylethyl acrylate, 2-phenylethyl methacrylate, 3-phenylpropyl acrylate, and combinations thereof.

[0545] Item 203. The composition of any one of items 200 to 202, wherein the reactive monomer mixture comprises an aromatic (meth)acrylate in an amount of about 5 to about 50 weight percent, about 10 to about 40 weight percent, or about 15 to about 40 weight percent.

[0546] Item 204. The composition according to any one of items 185 to 203, further comprising at least one hydroxyalkyl (meth)acrylate.

[0547] Item 205. The composition of item 204, wherein the hydroxyalkyl (meth)acrylate comprises a straight chain, branched chain, or cyclic hydroxyalkyl group having 1 to 25 carbon atoms.

[0548] Item 206. The composition of item 205, wherein the hydroxyalkyl (meth)acrylate is selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof.

[0549] Item 207. The composition of item 206, wherein the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate or 2-hydroxyethyl methacrylate.

[0550] Item 208. The composition of any one of items 204 to 207, wherein the reactive monomer mixture comprises a hydroxyalkyl (meth)acrylate in an amount of about 1 to about 25 weight percent, about 5 to about 20 weight percent, or about 10 to about 20 weight percent.

[0551] Item 209. The composition of any one of items 185 to 209, wherein the reactive monomer mixture further comprises at least one hydrophilic monomer.

[0552] Item 210. The composition of item 209, wherein the at least one hydrophilic monomer is selected from vinyl pyrrolidone, N-vinyl N-methyl acetamide, N-methyl methacrylamide, N-vinyl acetamide, N,N-dimethyl acrylamide, N-hydroxyethyl acrylamide, N-(2-hydroxypropyl)acrylamide, N-(3-hydroxypropyl)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, N-(3-hydroxypropyl)(meth)acrylamide, poly(ethylene glycol) methyl ether (meth)acrylate, poly(ethylene glycol) (meth)acrylate, and any combination thereof.

[0553] Item 211. The composition of any one of items 185 to 209, wherein the reactive monomer mixture further comprises a polyamide.

[0554] Item 212. The composition of item 211, wherein the polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl N-methylacetamide), poly(N-vinyl-acetamide), poly(dimethylacrylamide), and copolymers or mixtures thereof.

[0555] Item 213. The composition of item 212, wherein the polyamide is poly(vinylpyrrolidone).

[0556] Item 214. The composition of item 213, wherein the polyamide is a copolymer.

[0557] Item 215. The composition of any one of items 185 to 214, wherein the reactive monomer mixture comprises polyamide in an amount of about 0.1% to about 5% by weight, about 0.5% to about 3% by weight, or about 0.5% to about 2% by weight.

[0558] Item 216. The composition of any one of items 185 to 215, further comprising at least one UV / HEV absorbing compound in the reactive monomer mixture.

[0559] Item 217. The composition of item 216, wherein the UV / HEV absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, or any combination thereof.

[0560] Item 218. The composition of item 216 or 217, wherein the reactive monomer mixture comprises a UV / HEV absorbing compound in an amount of about 0.1 to about 5 weight percent, about 1 to about 4 weight percent, or about 1 to about 3 weight percent.

[0561] Item 219. The composition described in any one of items 185 to 218, further comprising at least one diluent in the reactive monomer mixture.

[0562] Item 220. The composition described in any one of items 185 to 219, having a moisture content of about 0% to about 15% by weight, about 1% to about 10% by weight, or about 1% to about 8% by weight.

[0563] Item 221. The composition has a refractive index of at least 1.45 and an Abbe number of at least 45; the composition has a refractive index of at least 1.48 and an Abbe number of at least 50; or the composition has a refractive index of at least 1.50 and an Abbe number of at least 50. Item 185. The composition according to any one of items 185 to 220.

[0564] Item 222. The composition described in any one of items 185 to 221, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator.

[0565] Item 223. An ophthalmic device comprising a composition described in any one of items 185 to 222.

[0566] Item 224. The ophthalmic device of item 223, wherein the ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal outlay, or a corneal insert.

[0567] Item 225. The ophthalmic device of item 224, wherein the ophthalmic device comprises an intraocular lens.

[0568] 226. A method for making an ophthalmic device, comprising: a. providing a composition according to any one of paragraphs 185-225; b. forming an ophthalmic device; A method comprising:

[0569] Item 227. The method of item 226, further comprising extracting the ophthalmic device with a solvent.

[0570] Item 228. The method of item 227, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

[0571] 229. A method for making an ophthalmic device, comprising: a. preparing a blank from the composition according to any one of paragraphs 185 to 225; b. machining an ophthalmic device from the blank; 13. A method comprising:

[0572] Item 230. The method of item 229, further comprising extracting the ophthalmic device with a solvent.

[0573] Item 231. The method of item 230, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

[0574] Item 232. The method of any one of items 226 to 231, further comprising an irradiation step using a femtosecond two-photon laser.

[0575] Item 233. The method of any one of items 226 to 232, further comprising the step of sterilizing the ophthalmic device.

[0576] Item 234. A method for making an ophthalmic device, comprising molding the device from a composition described in any one of items 185 to 225.

[0577] 235.a. at least one hydrophobic monomer; b. at least one acrylate monomer of formula (I):

[0578] [ka] In the formula, R 1 is selected from hydrogen and methyl; R 2 is a non-aromatic moiety having at least one carbon-carbon double bond; and c. at least one crosslinker; 1. A composition made by free radical polymerization of a reactive monomer mixture comprising:

[0579] Item 236. The composition of item 235, wherein the hydrophobic monomer is a hydrophobic (meth)acrylate monomer.

[0580] Item 237. The composition described in item 236, wherein the hydrophobic (meth)acrylate is selected from an aliphatic (meth)acrylate, an aromatic (meth)acrylate, a cycloaliphatic (meth)acrylate, and any combination thereof.

[0581] Item 238. The composition according to item 237, wherein the hydrophobic (meth)acrylate is an aliphatic (meth)acrylate.

[0582] Item 239. Aliphatic (meth)acrylates C1-C 18 239. The composition according to paragraph 238, which is an alkyl (meth)acrylate.

[0583] Section 240.C1~C 18 239. The composition of claim 239, wherein the alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, isodecyl (meth)acrylate, heptadecyl (meth)acrylate, dodecyl (meth)acrylate, 2-propylheptyl (meth)acrylate, stearyl (meth)acrylate, and any combination thereof.

[0584] Section 241.C1~C 18 241. The composition according to paragraph 240, wherein the alkyl (meth)acrylate is n-hexyl acrylate.

[0585] Item 242. The composition described in item 237, wherein the hydrophobic (meth)acrylate is an aromatic (meth)acrylate.

[0586] Item 243. The composition of item 242, wherein the aromatic (meth)acrylate is selected from the group consisting of 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 4-chlorophenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis-phenylthiol-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof.

[0587] Item 244. The composition of item 243, wherein the aromatic (meth)acrylate is 2-phenylethyl acrylate.

[0588] Item 245. The composition of item 243, wherein the aromatic (meth)acrylate is 2-phenylethyl methacrylate.

[0589] Item 246. The composition described in item 243, wherein the aromatic (meth)acrylate is a combination of 2-phenylethyl acrylate and 2-phenylethyl methacrylate.

[0590] Item 247: The composition described in item 243, wherein the aromatic (meth)acrylate is a combination of 2-phenylethyl methacrylate and 3-phenylpropyl acrylate.

[0591] Item 248. The composition described in item 237, wherein the hydrophobic (meth)acrylate is a cycloaliphatic (meth)acrylate.

[0592] Item 249. Alicyclic (meth)acrylates are cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, norbornyl (meth)acrylate, isobornyl (meth)acrylate, (meth)acrylate, isobornyl derivatives, norbornyl derivatives, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl (meth)acrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, poly(ethylene)glycol dicyclopentenyl ether (meth)acrylate, 2-(((3aR,4R,5S,7R,7aR)-octahydro-1H-4,7-methano 2-(((3aS,4R,6S,7R,7aR)-3a,4,5,6,7,7aHexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, (3aS,4S,5R,7S,7aS)-Octahydro-1H-4,7-methanoinden-5-yl acrylate, (3aS,4S,5R,7S,7aS)-3a,4,5,6,7,7aHexahydro-1H-4,7-methanoinden-5-yl acrylate 248. The composition according to claim 248, wherein the compound is selected from H-4,7-methanoinden-5-yl acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate, (1R,3S,5f,7r)-2-methyladamantan-2-yl PEG (meth)acrylate derivatives and (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate derivatives, and any combination thereof.

[0593] Item 250. The composition of item 249, wherein the cycloaliphatic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, cyclohexyl methyl methacrylate, 2-cyclohexyl ethyl acrylate, 2-cyclohexyl ethyl methacrylate, and any combination thereof.

[0594] Section 251.R 2 251. The composition according to any one of paragraphs 235 to 250, wherein contains an alkenyl or cycloalkenyl moiety.

[0595] Section 252.R 2 252. The composition according to paragraph 251, wherein contains a cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, bicyclo[2.2.1]hept-5-en-2-yl, hexahydro-1H-4,7-methanoindenyl, or allyl moiety.

[0596] Item 253. The acrylate monomer of formula (I) is ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl acrylate, 2-(((3aS,4R,6S,7R,7aR)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, (3aS,4S,5R,7S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-yl acrylate, 2-(cyclopenta-2,4-dien-1-yloxy)ethyl acrylate, cyclopenta-2,4-dien-1-yl acrylate, cyclopenta-3-en-1-yl acrylamide, cyclopenta-3-en-1-yl acrylate ... 251. The composition according to any one of items 235 to 250, wherein the alkyl acrylate is selected from 2-(cyclopent-3-en-1-yloxy)ethyl acrylate, cyclohexa-2,4-dien-1-yl acrylate, 2-(cyclohexa-2,4-dien-1-yloxy)ethyl acrylate, 2-(cyclohex-3-en-1-yloxy)ethyl acrylate, cyclohex-3-en-1-yl acrylate, 2-(2-(2-(2-(cyclohex-3-en-1-yloxy)ethoxy)ethoxy)ethyl acrylate, N,N-diallylacrylamide, allyl acrylate, and 2-(allyloxy)ethyl acrylate.

[0597] Item 254. The composition according to any one of items 235 to 253, wherein the composition further comprises a hydroxyl group-containing monomer.

[0598] Item 255. The composition of item 254, wherein the hydroxyl-containing monomer is a hydroxyalkyl (meth)acrylate.

[0599] Item 256. The composition of item 255, wherein the hydroxyalkyl (meth)acrylate is selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof.

[0600] Item 257. The composition of item 256, wherein the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate or 2-hydroxyethyl methacrylate.

[0601] Item 258. The composition described in item 254, wherein the hydroxyl-containing monomer is a hydroxysilicone monomer.

[0602] Item 259. The composition described in item 258, wherein the hydroxysilicone monomer is selected from 3-(3-(1,1,1,3,5,5,5-heptamethyltrisiloxane-3-yl)propoxy)-2-hydroxypropyl methacrylate (SiMAA), mono-n-butyl terminated monomethacryloxypropyl terminated polydimethylsiloxane (mPDMS), and mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether terminated mono-n-butyl terminated polydimethylsiloxane (OH-mPDMS).

[0603] Item 260. The composition of any one of items 235 to 259, wherein the reactive monomer mixture further comprises at least one hydrophilic monomer.

[0604] Item 261. The composition of item 260, wherein the at least one hydrophilic monomer is selected from vinyl pyrrolidone, N-vinyl N-methyl acetamide, N-methyl methacrylamide, N-vinyl acetamide, N,N-dimethyl acrylamide, N-hydroxyethyl acrylamide, N-(2-hydroxypropyl)acrylamide, N-(3-hydroxypropyl)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, N-(3-hydroxypropyl)(meth)acrylamide, poly(ethylene glycol) methyl ether (meth)acrylate, poly(ethylene glycol) (meth)acrylate, and any combination thereof.

[0605] Item 262. The composition described in any one of items 235 to 261, wherein the crosslinking agent is selected from the group consisting of non-alicyclic crosslinking agents, alicyclic crosslinking agents, and any combination thereof.

[0606] Item 263. The composition of item 262, wherein the crosslinking agent is a non-alicyclic crosslinking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl(meth)acrylate) terminated polydimethylsiloxane, and any combination thereof.

[0607] Item 264. The composition described in item 263, wherein the non-alicyclic crosslinker is ethylene glycol dimethacrylate.

[0608] Item 265. The composition described in item 262, wherein the crosslinking agent is an alicyclic crosslinking agent containing an alicyclic group having 1 to 4 alicyclic rings.

[0609] Item 266. Alicyclic crosslinking agent is tricyclo[5.2.1.0 2,6 ] decanedimethanol di(meth)acrylate, and the composition described in item 265.

[0610] Item 267. The composition of any one of items 235 to 266, wherein the reactive monomer mixture comprises a crosslinker in an amount of about 1 to about 20 weight percent, about 3 to about 15 weight percent, or about 3 to about 10 weight percent.

[0611] Item 268. A crosslinking agent having the formula:

[0612] [ka] 262. The composition according to any one of items 235 to 261, wherein n is an integer from 5 to 50.

[0613] Item 269. The composition described in item 268, wherein n is 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25.

[0614] Item 270. The composition described in item 269, wherein n is 20.

[0615] Item 271. The composition of any one of items 134 to 136, wherein the reactive monomer mixture comprises a crosslinker in an amount of about 15% to about 22% by weight, or about 16% to about 20% by weight.

[0616] Item 272. The composition described in item 271, wherein the crosslinking agent is present in the reactive monomer mixture in an amount of about 18% by weight.

[0617] Item 273. The composition of any one of items 235-272, wherein the reactive monomer mixture further comprises a polyamide.

[0618] Item 274. The composition of item 273, wherein the polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl N-methylacetamide), poly(N-vinyl-acetamide), poly(dimethylacrylamide), and copolymers or mixtures thereof.

[0619] Item 275. The composition of item 274, wherein the polyamide is poly(vinylpyrrolidone) or poly(N-vinyl N-methylacetamide).

[0620] Item 276. The composition of item 273, wherein the polyamide is a copolymer.

[0621] Item 277. The composition of any one of items 273 to 276, wherein the reactive monomer mixture comprises polyamide in an amount of about 0.1% to about 5% by weight, or about 0.25% to about 2% by weight.

[0622] Item 278. The composition of any one of items 235-277, further comprising at least one UV / HEV absorbing compound in the reactive monomer mixture.

[0623] Item 279. The composition of item 278, wherein the UV / HEV absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, or any combination thereof.

[0624] Item 280. The composition of item 278 or 279, wherein the reactive monomer mixture comprises a UV / HEV absorbing compound in an amount of about 0.1 to about 5 weight percent, about 1 to about 4 weight percent, or about 1 to about 3 weight percent.

[0625] Item 281. The composition described in any one of items 235 to 280, further comprising at least one diluent in the reactive monomer mixture.

[0626] Item 282. The composition described in any one of items 235 to 281, having a moisture content of about 0% to about 15% by weight, about 1% to about 10% by weight, or about 1% to about 8% by weight.

[0627] Item 283. The composition has a refractive index of at least 1.45 and an Abbe number of at least 45; the composition has a refractive index of at least 1.48 and an Abbe number of at least 50; or the composition has a refractive index of at least 1.50 and an Abbe number of at least 50. Item 235-282. The composition according to any one of items 235-282.

[0628] Item 284. The composition described in any one of items 235 to 283, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator.

[0629] Item 285. An ophthalmic device comprising a composition described in any one of items 235 to 284.

[0630] Item 286. The ophthalmic device of item 285, wherein the ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal outlay, or a corneal insert.

[0631] Item 287. The ophthalmic device of item 286, wherein the ophthalmic device comprises an intraocular lens.

[0632] 288. A method for making an ophthalmic device, comprising: a. providing a composition according to any one of paragraphs 235-284; b. forming an ophthalmic device; A method comprising:

[0633] Item 289. The method of item 288, further comprising extracting the ophthalmic device with a solvent.

[0634] Item 290. The method of item 289, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

[0635] 291. A method for making an ophthalmic device, comprising: a. preparing a blank from the composition of any one of paragraphs 235 to 284; b. machining an ophthalmic device from the blank; 13. A method comprising:

[0636] Item 292. The method of item 291, further comprising extracting the ophthalmic device with a solvent.

[0637] Item 293. The method of item 292, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

[0638] Item 294. The method of any one of items 288 to 293, further comprising an irradiation step using a femtosecond two-photon laser.

[0639] Item 295. The method of any one of items 288 to 294, further comprising the step of sterilizing the ophthalmic device.

[0640] Item 296. A method for making an ophthalmic device, comprising molding the device from a composition described in any one of items 235 to 284.

[0641] [Embodiment] (1) a. at least one hydrophobic monomer; b. at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers, and any combination thereof; c. Tricyclo[5.2.1.0 2,6 ] decanedimethanol di(meth)acrylate crosslinker; The present invention is prepared by free radical polymerization of a reactive monomer mixture comprising: A composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39. (2) The composition according to embodiment 1, wherein the hydrophobic monomer is a hydrophobic (meth)acrylate monomer selected from an aliphatic (meth)acrylate, an aromatic (meth)acrylate, an alicyclic (meth)acrylate, and any combination thereof. (3) The composition of embodiment 2, wherein the hydrophobic (meth)acrylate is a cycloaliphatic (meth)acrylate selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, cyclohexyl methyl methacrylate, 2-cyclohexyl ethyl acrylate, 2-cyclohexyl ethyl methacrylate, ethylene glycol dicyclopentenyl ether acrylate, and any combination thereof. (4) The hydrophobic (meth)acrylate is selected from the group consisting of C1 to C 18 The composition of embodiment 2, wherein the (meth)acrylate is an aliphatic (meth)acrylate selected from alkyl (meth)acrylates. (5) The composition of embodiment 2, wherein the hydrophobic (meth)acrylate is an aromatic (meth)acrylate selected from the group consisting of 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 4-chlorophenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis-phenylthiol-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof.

[0642] (6) The composition according to any one of the preceding claims, wherein the reactive monomer mixture comprises at least one hydrophilic monomer which is a poly(ethylene glycol)-containing monomer selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate. (7) The composition of any one of the preceding embodiments, wherein the reactive monomer mixture comprises at least one hydroxyalkyl (meth)acrylate monomer selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof. (8) The composition of any one of the preceding claims, wherein the reactive monomer mixture comprises a mixture of a hydrophilic monomer and a hydroxyalkyl (meth)acrylate monomer, the hydrophilic monomer being selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate, and the hydroxyalkyl (meth)acrylate monomer being 2-hydroxyethyl acrylate. (9) The tricyclo[5.2.1.0 2,6 ]Decanedimethanol di(meth)acrylate crosslinker is tricyclo[5.2.1.0 2,6 9. The composition of any one of embodiments 1 to 8, wherein the compound is decanedimethanol diacrylate. (10) a. at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings; b. at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers, and any combination thereof; c. at least one crosslinker; The present invention is prepared by free radical polymerization of a reactive monomer mixture comprising: A composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39.

[0643] (11) The composition of embodiment 10, wherein the at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings comprises two or more individual monocyclic alicyclic rings, or a bicyclic, tricyclic, bridged, fused, and / or spirocyclic alicyclic ring system. (12) The composition according to any one of the preceding claims 10 to 11, wherein the at least one alicyclic (meth)acrylate monomer containing two or more alicyclic rings is ethylene glycol dicyclopentenyl ether acrylate. (13) The composition according to any one of embodiments 10 to 12, wherein the reactive monomer mixture comprises at least one hydrophilic monomer which is a poly(ethylene glycol)-containing monomer selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate. (14) The composition of any one of embodiments 10 to 13, wherein the reactive monomer mixture comprises at least one hydroxyalkyl (meth)acrylate monomer selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof. (15) The composition according to any one of embodiments 10 to 14, wherein the reactive monomer mixture comprises a mixture of a hydrophilic monomer and a hydroxyalkyl (meth)acrylate monomer, the hydrophilic monomer being selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate, and the hydroxyalkyl (meth)acrylate monomer being 2-hydroxyethyl acrylate.

[0644] (16) The composition according to any one of embodiments 10 to 15, wherein the reactive monomer mixture further comprises at least one alicyclic (meth)acrylate containing one alicyclic ring. (17) The composition of embodiment 16, wherein the alicyclic (meth)acrylate containing one alicyclic ring is selected from cyclohexyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, and any combination thereof. (18) The composition according to any one of embodiments 10 to 17, wherein the reactive monomer mixture further comprises at least one aromatic (meth)acrylate selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. (19) The composition according to any one of embodiments 10 to 18, wherein the reactive monomer mixture further comprises a hydroxyalkyl (meth)acrylate selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof. (20) The composition according to any one of embodiments 10 to 19, wherein the crosslinking agent is an alicyclic crosslinking agent containing an alicyclic group having 1 to 4 alicyclic rings.

[0645] (21) The alicyclic crosslinking agent is tricyclo[5.2.1.0 2,6 ]Decanedimethanol di(meth)acrylate. (22) a. at least one alicyclic (meth)acrylate; b. at least one aromatic (meth)acrylate; c. at least one aliphatic (meth)acrylate; d. at least one crosslinker; The polymer is prepared by free radical polymerization of a reactive monomer mixture comprising: A composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39. (23) The composition of embodiment 22, wherein the alicyclic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, 2-cyclohexyl ethyl acrylate, 3-cyclohexyl propyl acrylate, ethylene glycol dicyclopentenyl ether acrylate, and any combination thereof. (24) The composition of any one of the preceding claims 22 to 23, wherein the aromatic (meth)acrylate is selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis-phenylthiol-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. (25) The composition according to any one of embodiments 22 to 24, wherein the aliphatic (meth)acrylate comprises a linear or branched alkyl group containing 1 to 25 carbon atoms, or 4 to 8 carbon atoms.

[0646] (26) The composition according to embodiment 25, wherein the aliphatic (meth)acrylate is n-hexyl acrylate. (27) The composition according to any one of embodiments 22 to 26, wherein the crosslinking agent is a non-alicyclic crosslinking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl(meth)acrylate)-terminated polydimethylsiloxane, and any combination thereof. (28) The composition according to any one of embodiments 22 to 26, wherein the crosslinking agent is an alicyclic crosslinking agent containing an alicyclic group having 1 to 4 alicyclic rings. (29) The alicyclic crosslinking agent is tricyclo[5.2.1.0 2,6 ] decanedimethanol di(meth)acrylate. (30) a. at least one alicyclic (meth)acrylate; b. at least one aliphatic (meth)acrylate; c. at least one crosslinker; The present invention is prepared by free radical polymerization of a reactive monomer mixture comprising: A composition exhibiting a refractive index of at least 1.45 and an Abbe number of at least 39.

[0647] (31) The composition according to embodiment 30, wherein the alicyclic (meth)acrylate comprises an alicyclic group having 1 to 4 alicyclic rings. (32) The composition according to any one of embodiments 30 to 31, wherein the alicyclic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, 2-cyclohexyl ethyl acrylate, 3-cyclohexyl propyl acrylate, ethylene glycol dicyclopentenyl ether acrylate, and any combination thereof. (33) The composition according to any one of embodiments 30 to 32, wherein the aliphatic (meth)acrylate comprises a linear or branched alkyl group containing 1 to 25 carbon atoms, or 4 to 8 carbon atoms. (34) The composition according to any one of embodiments 30 to 33, wherein the crosslinking agent is a non-alicyclic crosslinking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl(meth)acrylate)-terminated polydimethylsiloxane, and any combination thereof. (35) The composition according to any one of embodiments 30 to 34, wherein the crosslinking agent is an alicyclic crosslinking agent containing an alicyclic group having 1 to 4 alicyclic rings.

[0648] (36) The alicyclic crosslinking agent is tricyclo[5.2.1.0 2,6 ]Decanedimethanol di(meth)acrylate. (37) The composition according to any one of embodiments 30 to 36, further comprising an aromatic (meth)acrylate or a hydroxyalkyl (meth)acrylate. (38) a. at least one hydrophobic monomer; b. at least one acrylate monomer of formula (I):

[0649] [ka] In the formula, R 1 is selected from hydrogen and methyl; R 2 is a non-aromatic moiety having at least one carbon-carbon double bond; and c. at least one crosslinker; 1. A composition made by free radical polymerization of a reactive monomer mixture comprising: (39) The composition of embodiment 38, wherein the hydrophobic monomer is a hydrophobic (meth)acrylate monomer selected from an aliphatic (meth)acrylate, an aromatic (meth)acrylate, a cycloaliphatic (meth)acrylate, and any combination thereof. (40) The hydrophobic (meth)acrylate is selected from the group consisting of C1 to C 18 The composition of embodiment 39, wherein the (meth)acrylate is an aliphatic (meth)acrylate chosen from alkyl (meth)acrylates.

[0650] (41) The composition of embodiment 39, wherein the hydrophobic (meth)acrylate is an aromatic (meth)acrylate selected from the group consisting of 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 4-chlorophenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis-phenylthiol-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof. (42) The hydrophobic (meth)acrylate is selected from the group consisting of cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, norbornyl (meth)acrylate, isobornyl (meth)acrylate, isobornyl derivatives, norbornyl derivatives, ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl (meth)acrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, poly(ethylene)glycol dicyclopentene Nyl ether (meth)acrylate, 2-(((3aR,4R,5S,7R,7aR)-octahydro-1H-4,7-methanoinden-5-yl)oxy)ethyl acrylate, 2-(((3aS,4R,6S,7R,7aR)-3a,4,5,6,7,7ahexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, (3aS,4 40. The composition of embodiment 39, wherein the alicyclic (meth)acrylate is selected from (3aS,4S,5R,7S,7aS)-octahydro-1H-4,7-methanoinden-5-yl acrylate, (3aS,4S,5R,7S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-yl acrylate, and any combination thereof. (43) R 2 comprises a cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, bicyclo[2.2.1]hept-5-en-2-yl, hexahydro-1H-4,7-methanoindenyl, or allyl moiety. (44) The acrylate monomer of formula (I) is ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl acrylate, 2-(((3aS,4R,6S,7R,7aR)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl)oxy)ethyl acrylate, (3aS,4S,5R,7S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-yl acrylate, 2-(cyclopenta-2,4-dien-1-yloxy)ethyl acrylate, cyclopenta-2,4-dien-1-yl acrylate, cyclopenta-3- ... 44. The composition of any one of embodiments 38 to 43, wherein the alkyl acrylate is selected from aryl acrylate, 2-(cyclopent-3-en-1-yloxy)ethyl acrylate, cyclohexa-2,4-dien-1-yl acrylate, 2-(cyclohexa-2,4-dien-1-yloxy)ethyl acrylate, 2-(cyclohex-3-en-1-yloxy)ethyl acrylate, cyclohex-3-en-1-yl acrylate, 2-(2-(2-(cyclohex-3-en-1-yloxy)ethoxy)ethoxy)ethyl acrylate, N,N-diallylacrylamide, allyl acrylate, and 2-(allyloxy)ethyl acrylate. (45) The composition according to any one of embodiments 38 to 44, wherein the reactive monomer mixture further comprises a hydroxyalkyl (meth)acrylate.

[0651] (46) The composition according to any one of embodiments 38 to 45, wherein the crosslinking agent is a non-alicyclic crosslinking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl(meth)acrylate) terminated polydimethylsiloxane, and any combination thereof. (47) The composition according to any one of embodiments 38 to 46, wherein the crosslinking agent is an alicyclic crosslinking agent containing an alicyclic group having 1 to 4 alicyclic rings. (48) The alicyclic crosslinking agent is tricyclo[5.2.1.0 2,6 ]Decanedimethanol di(meth)acrylate. (49) The crosslinker has the formula:

[0652] [ka] The composition of any one of embodiments 38 to 45, wherein n is an integer from 5 to 50. (50) The composition of any one of the preceding embodiments, further comprising at least one UV / HEV absorbing compound in the reactive monomer mixture.

[0653] (51) The composition of embodiment 50, wherein the UV / HEV absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, or any combination thereof. (52) The composition according to any one of the preceding embodiments, further comprising at least one diluent in the reactive monomer mixture. (53) The composition according to any one of embodiments 1 to 52, having a water content of from about 0% to about 15% by weight, from about 1% to about 10% by weight, or from about 1% to about 8% by weight. (54) The composition has a refractive index of at least 1.45 and an Abbe number of at least 45, or the composition has a refractive index of at least 1.48 and an Abbe number of at least 50, or the composition has a refractive index of at least 1.50 and an Abbe number of at least 50. 54. The composition according to any one of embodiments 1 to 53. (55) The composition according to any one of the preceding embodiments, wherein the free radical polymerization is a photopolymerization using a bisacylphosphine oxide initiator.

[0654] (56) An ophthalmic device comprising the composition according to any one of embodiments 1 to 55. (57) The ophthalmic device of embodiment 56, wherein the ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal outlay, or a corneal insert. (58) A method for making an ophthalmic device, comprising: a. providing a composition according to any one of embodiments 1 to 55; b. forming an ophthalmic device; A method comprising: (59) The method of embodiment 58, further comprising extracting the ophthalmic device with a solvent. (60) The method of embodiment 59, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

[0655] (61) A method for making an ophthalmic device, comprising: a. Preparing a blank from the composition according to any one of embodiments 1 to 55; b. machining an ophthalmic device from said blank; The method includes: (62) The method of embodiment 61, further comprising extracting the ophthalmic device with a solvent. (63) The method of embodiment 62, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution. (64) The method according to any one of embodiments 58 to 63...

Claims

1. 1. An ophthalmic device comprising a composition made by free radical polymerization of a reactive monomer mixture, the reactive monomer mixture comprising: (a) at least one hydrophobic monomer; (b) at least one hydrophilic monomer which is poly(ethylene glycol) methyl ether methacrylate; (c) tricyclo[5.2.1.0 ２，６ ] decanedimethanol di(meth)acrylate crosslinker; Including, the reactive monomer mixture comprises the at least one hydrophobic monomer in an amount of 50 to 80 weight percent; the reactive monomer mixture comprises the at least one hydrophilic monomer in an amount of 12 to 22 weight percent; The reactive monomer mixture comprises 1 to 20 weight percent of the tricyclo[5.2.1.0 ２，６ ] containing a decanedimethanol di(meth)acrylate crosslinker, the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39; The ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal outlay, or a corneal insert.

2. 2. The ophthalmic device of claim 1, wherein the hydrophobic monomer is a hydrophobic (meth)acrylate monomer selected from an aliphatic (meth)acrylate, an aromatic (meth)acrylate, a cycloaliphatic (meth)acrylate, and any combination thereof.

3. 3. The ophthalmic device of claim 2, wherein the hydrophobic (meth)acrylate monomer is a cycloaliphatic (meth)acrylate selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, cyclohexyl methyl methacrylate, 2-cyclohexyl ethyl acrylate, 2-cyclohexyl ethyl methacrylate, ethylene glycol dicyclopentenyl ether acrylate, and any combination thereof.

4. The hydrophobic (meth)acrylate monomer is １ ~C １８ The ophthalmic device of claim 2 , wherein the (meth)acrylate is an aliphatic (meth)acrylate selected from alkyl (meth)acrylates.

5. 3. The ophthalmic device of claim 2, wherein the hydrophobic (meth)acrylate monomer is an aromatic (meth)acrylate selected from the group consisting of 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 4-chlorophenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis-phenylthiol-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof.

6. The tricyclo[5.2.1.0 ２，６ ] decanedimethanol di(meth)acrylate crosslinker is tricyclo[5.2.1.0 ２，６ ] decanedimethanol diacrylate.

7. further comprising at least one UV / HEV absorbing compound in said reactive monomer mixture; the UV / HEV absorbing compound is selected from 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, a compound of formula II, and any combination thereof; 【Chemistry 1】 During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; X is O, S, NR, SO, or SO ２ and Y is a linking group; P ｇ is a polymerizable group, R, in each occurrence, is independently H, C １ ~C ６ Alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or Y-P ｇ and R １ and R ２ When present, each occurrence independently represents C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Thioalkyl, C ３ ~C ７ Cycloalkyl, aryl, halo, hydroxy, amino, NR ３ R ４ or benzyl, where R ３ and R ４ are independently H or C １ ~C ６ alkyl or two adjacent R １ Or R ２ the groups, together with the carbon atom to which they are attached, are joined to form a cycloalkyl or aryl ring; The ophthalmic device of claim 1 , wherein EWG is an electron withdrawing group.

8. The ophthalmic device of claim 1 , further comprising at least one diluent in the reactive monomer mixture.

9. The ophthalmic device of claim 1 having a water content of about 0% to about 15% by weight.

10. The ophthalmic device of claim 1 , wherein the composition has a refractive index of at least 1.45 and an Abbe number of at least 45.

11. The ophthalmic device of claim 1 , wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator.

12. 13. A method for making the ophthalmic device of claim 1, comprising: (a) providing a composition made by free radical polymerization of said reactive monomer mixture; (b) forming an ophthalmic device; A method comprising:

13. The ophthalmic device of claim 3 , wherein the cycloaliphatic (meth)acrylate is ethylene glycol dicyclopentenyl ether acrylate.

14. The aliphatic (meth)acrylate is ４ ~C ８ The ophthalmic device of claim 4 comprising a straight chain alkyl group.

15. The ophthalmic device of claim 3, wherein the reactive monomer mixture comprises the at least one cycloaliphatic (meth)acrylate in an amount of 50 to 80% by weight.

Images