RU2835913C2 - Compositions with high reaction index and high abbe number - Google Patents

Abstract

FIELD: medicine.

SUBSTANCE: invention relates to an ophthalmic device containing a composition with a high refraction index and can be used as implanted ophthalmic devices. Ophthalmic device contains a composition obtained by free-radical polymerisation of a reaction mixture of monomers containing: a) at least one hydrophobic monomer; b) at least one hydrophilic monomer, which is a poly(ethylene glycol)-containing monomer selected from poly(ethylene glycol)methacrylate and poly(ethylene glycol)methyl ester of methacrylate; and c) a tricyclo[5.2.1.02,6]decanedimethanol di(meth)acrylate cross-linking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39; and wherein the ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal patch or a corneal insert. Invention also relates to an ophthalmic device containing a composition obtained by free-radical polymerisation of a reaction mixture of monomers containing: a) at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring; b) at least one hydrophilic monomer, which is a poly(ethylene glycol)-containing monomer selected from poly(ethylene glycol)methacrylate and poly(ethylene glycol)methyl ester of methacrylate; and c) at least one cross-linking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39; and wherein the ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal patch or a corneal insert. Additionally, the invention relates to a composition for use in ophthalmic devices, to an ophthalmic device containing a composition for use in ophthalmic devices, and to a method for making an ophthalmic device.

EFFECT: providing material with relatively high refraction index and Abbe number, which is characterized by flexibility and can be used in optical devices, in flexible intraocular lenses.

63 cl, 11 dwg, 17 tbl, 88 ex

Description

Cross-references to related applications

This application claims priority to U.S. Provisional Patent Application No. 62/843,054, filed May 3, 2019, the contents of which are incorporated herein by reference in their entirety.

Field of technology

The present disclosure relates to copolymers prepared from reactive monomer mixtures that, upon polymerization, form acrylic materials having high refractive indices and large Abbe numbers. These materials, which may have a variable refractive index, are intended for use in ophthalmic devices such as intraocular implants or lenses (IOLs).

Prerequisites for the creation of an invention

Cataract surgery is usually performed to replace the natural lens of the eye that has become opaque. The materials used to replace the natural lens must be soft and have excellent flexibility so that after the lens is molded, it can be folded and passed through an incision, usually about 2 mm in size. In addition, the material must have excellent transparency and low or no glare. Having a high refractive index allows for a thinner lens to be used. A material with a high Abbe number exhibits less dispersion. This in turn provides improved optical results and less scattering of light. The combination of a high refractive index and a high Abbe number provides the preferred optical characteristics for the material.

One of the first patents in the field, U.S. Patent No. 4,573,998 to Mazzocco, describes a deformable intraocular lens that can be folded for insertion through a relatively small incision. The deformable lens is inserted into the eye while being held in a folded position and then unfolded within the eye chamber. The elastic properties of the lens allow it to recover its molded shape after insertion into the eye. Mazzocco's patent describes polyurethane elastomers, silicone elastomers, polymeric hydrogel compounds, organic or synthetic gel compounds, and combinations thereof as suitable materials for the deformable lens.

Friction from the inside of the delivery device and the force applied by the physician during delivery can damage the lens. To address this issue, some delivery devices are coated to provide additional smoothness. For example, U.S. Patent No. 8,323,799 to Hu describes soft and flexible, highly smooth coatings for polymeric IOL delivery cassettes that allow easy delivery of IOLs through small-diameter cartridges suitable for use with small (less than 3 mm) incisions. While such coatings are useful, there is a need to further reduce the frictional forces applied to the lens during placement.

Accordingly, there is a need for a material with a relatively high refractive index and Abbe number that can be used to form a flexible intraocular lens that can be easily rolled or folded into a shape that will fit through a small incision. In addition, there is a need for such a material to be internally smooth.

Statement of the essence of the invention

In certain embodiments, the present invention relates to a composition obtained by free radical polymerization of a reactive monomer mixture comprising:

(A) (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 crosslinking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39 ("composition (A)"); or

(B) (i) at least one cycloaliphatic (meth)acrylate; (ii) at least one aliphatic (meth)acrylate; and (iii) at least one crosslinking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39 (“composition (B)”);

(C) (i) at least one hydrophobic monomer; (ii) at least one acrylate monomer of the following formula (I):

(I),

wherein R ¹ is selected from hydrogen and methyl, and R ² is a non-aromatic functional group having at least one carbon-carbon double bond; and (iii) at least one cross-linking agent (“composition (C)”);

(D) (i) at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring; (ii) at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers and any combinations thereof; and (iii) at least one crosslinking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39 ("composition (D)"); or

(E) (i) at least one hydrophobic monomer; (ii) at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers and any combinations thereof; and (iii) a crosslinking agent tricyclo[5.2.1.0 ^2,6 ]decanedimethanol di(meth)acrylate; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39 (“composition (E)”).

In certain embodiments, the present disclosure provides a device comprising composition (A), composition (B), composition (C), composition (D), or composition (E). In certain other embodiments, the device is an ophthalmological device. In particular embodiments, the ophthalmological device comprises a lens, an implantable lens, an overlay lens, or an insert selected from an intraocular implant or lens, a contact lens, a corneal implantable lens, a corneal overlay lens, and a corneal insert. In particular embodiments, the ophthalmological device is an intraocular implant or lens. More specifically, the present disclosure also provides intraocular implants and/or lenses made at least partially or completely from composition (A), composition (B), composition (C), composition (D), or composition (E).

In yet other embodiments, provided herein is a method of producing an ophthalmic device, 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 said compositions. In other embodiments, the subject matter disclosed herein is a method of making an ophthalmic device, comprising: (a) providing a preform from any one of composition (A), composition (B), composition (C), composition (D), or composition (E); and (b) machining an ophthalmic device from the preform. In other embodiments, the subject matter described herein is a method of making an ophthalmic device, comprising the step of molding an ophthalmic device from any one of composition (A), composition (B), composition (C), composition (D), or composition (E).

In other embodiments, the subject matter disclosed herein provides a method of manufacturing an ophthalmic device comprising: (a) molding an ophthalmic device from any one of composition (A), composition (B), composition (C), composition (D), or composition (E), and (b) finishing the surface of the molded lens by machining.

In certain embodiments of any method, the method further comprises the step of extracting the ophthalmic device with a solvent. In certain embodiments, the method further comprises the step of hydrating the extracted ophthalmic device with at least one aqueous solution. In particular embodiments, the method further comprises the step of irradiating using a laser. In more particular embodiments, the method further comprises the step of sterilizing the ophthalmic device.

Brief description of graphic materials

FIG. 1 shows microgloss levels as measured by dark field microscopy.

FIG. 2 shows the macrogloss level of Example 35 as determined by dark field microscopy.

FIG. 3 shows the level of macrogloss in Examples 37-43 as determined by dark field microscopy.

FIG. 4 shows the level of macrogloss in Examples 44-51 as determined by dark field microscopy.

FIG. 5 shows the level of macrogloss in Examples 45 and 52-55 as determined by dark field microscopy.

FIG. 6 shows the microgloss levels for Examples 66 and 70 as determined by dark field microscopy.

FIG. 7 shows the level of macrogloss in Examples 72-74 as determined by dark field microscopy.

FIG. 8 shows the level of macrogloss in Examples 75-77 as determined by dark field microscopy.

FIG. 9 shows the macrogloss level of Examples 78-80 as determined by dark field microscopy.

FIG. 10 shows the level of macrogloss in Examples 81-83 as determined by dark field microscopy.

FIG. 11 shows the macrogloss level of Example 84 as determined by dark field microscopy.

Detailed description of the invention

It should be understood that the invention is not limited to the design characteristics or method steps presented in the following description. The invention also has other embodiments and can be implemented in practice or carried out in various ways using the ideas presented herein.

A. Definitions

With respect to the terms used in this description, the following definitions are provided.

Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the invention pertains. Definitions for polymers are consistent with those described 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 by reference.

The term "reactive monomer mixture" refers to a mixture of components (both reactive and non-reactive) that are mixed together and that, under polymerization conditions, form the presently disclosed compositions and ophthalmic devices. The reactive mixture may comprise reactive components such as monomers, macromers, prepolymers, crosslinkers, initiators, diluents, as well as additional components including, but not limited to, wetting agents, release agents, colorants, light absorbing compounds such as ultraviolet/high energy visible (UV/HEV) absorbers, pigments, dyes, and photochromic compounds, any of which may be reactive or non-reactive but still retained within the resulting biomedical device, such as an ophthalmic device, including active components, including pharmaceutical and nutraceutical compounds, as well as any diluents. It should be understood that a wide range of additives may be used based on the type of biomedical device being manufactured and its intended purpose. In some embodiments, the concentrations of the components of the reaction mixture are given in wt. % of the content of all components in the reaction mixture, with the exception of the diluent. When using diluents, their concentrations are given in wt. % of the content of all components of the reaction mixture and the diluent.

"Reactive components" are those components in the reactive monomer mixture that become part of the polymer network structure of the resulting composition by forming covalent or hydrogen bonds. Solvents and process substances that do not become part of the polymer structure are not reactive components.

As used herein, the term "(meth)" denotes the possible presence of an optional methyl substituent. Thus, the term "(meth)acrylates" refers to both methacrylates and acrylates.

It should be noted that wherever chemical structures are given, the variants represented as substituents in the structure can be combined in any combination. Thus, if the structure contains substituents R* and R**, each of which has three lists of potential groups, 9 combinations are possible. The same applies to the combination of properties.

When a subscript such as n in the standard formula [***] _n is used to indicate the number of repeating units in a polymer chemical formula, such formula should be understood to represent the number average molecular weight of the macromolecule.

As used in this document, the term "subject" includes humans and non-human vertebrates.

The term "biomedical device" means any article capable of being used in or on the surface of mammalian tissues or fluids, and preferably in or on the surface of human tissue or fluids. Examples of such devices include, but are not limited to, wound dressings, bioadhesives, tissue fillers, drug delivery systems, coatings, adhesion barriers, catheters, implants, stents, and ophthalmic devices such as intraocular implants, intraocular lenses, and contact lenses. Biomedical devices may be ophthalmic devices, in particular ophthalmic implants or ophthalmic lenses, made from the reactive monomer compositions described herein.

The term "ocular surface" includes the superficial and glandular epithelium of the cornea, conjunctiva, lacrimal glands, accessory lacrimal glands, nasolacrimal duct, and meibomian glands and their apical and basal matrices, puncta, and adjacent or associated structures, including the eyelids, related as a functional system by epithelial continuity, innervation, and the endocrine and immune systems.

The term "ophthalmic device" refers to any device that is placed in or on the eye or any part of the eye, including the ocular surface. Such devices may provide optical correction, cosmetic enhancement, vision enhancement, therapeutic effect (e.g. as a dressing), or delivery of active ingredients such as pharmaceutical and nutraceutical ingredients, or any combination thereof. Examples of ophthalmic devices include, but are not limited to, lenses and optical and ocular inserts, including, but not limited to, punctal occluders, etc. The term "lenses" includes soft contact lenses, rigid contact lenses, hybrid contact lenses, intraocular lenses, and masking lenses. An ophthalmic device may comprise an intraocular implant, an intraocular lens, or a contact lens.

The term "contact lens" refers to an ophthalmic device that can be placed on the cornea of the eye of a subject. A contact lens can provide a corrective, cosmetic, or therapeutic effect, including wound healing, drug or nutraceutical delivery, diagnostic assessment or monitoring, ultraviolet light absorption, visible or glare reduction, or any combination thereof. A contact lens can be made of any suitable material known in the art and can be a soft lens, a rigid lens, or a hybrid lens comprising at least two separate parts with different physical, mechanical, or optical properties, such as elastic modulus, water content, light transmittance, or combinations thereof.

The term "intraocular lens" refers to a lens implanted in 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 cloudy due to a cataract, or as refractive surgery to change the optical power of the eye).

The term "target macromolecule" means a macromolecule synthesized from a reactive monomer mixture containing monomers, macromers, prepolymers, cross-linking agents, initiators, additives, diluents, etc.

The term "polymerizable compound" means a compound containing one or more polymerizable groups. The term covers, for example, monomers, macromers, oligomers, prepolymers, cross-linking agents, etc.

"Polymerizable groups" are groups that can undergo chain growth polymerization, such as free radical and/or ionic polymerization (e.g., cationic polymerization), for example, a carbon-carbon double bond that can polymerize when exposed to radical initiating conditions. Non-limiting examples of free radical polymerizable 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. Free radical polymerizable groups preferably comprise (meth)acrylate, (meth)acrylamide, N-vinyl lactam, N-vinyl amide, and styryl functional groups, and mixtures of any of the foregoing. Free radical polymerizable groups more preferably comprise (meth)acrylates, (meth)acrylamides, and mixtures thereof. The polymerizable group may be substituted or unsubstituted. For example, the nitrogen atom in (meth)acrylamide may be bonded to hydrogen, or the hydrogen may be substituted by alkyl or cycloalkyl (which may themselves be further substituted).

Any type of free radical polymerization may be used, including, but not limited to, bulk, solution, suspension, and emulsion, as well as any controlled radical polymerization methods such as stable free radical-initiated polymerization, nitroxide-mediated living polymerization, atom transfer radical polymerization, reversible addition and fragmentation polymerization, organotellurium compound-mediated living radical polymerization, etc.

The term "monomer" is a monofunctional molecule that can undergo chain growth polymerization and in particular free radical polymerization, thereby creating a repeating unit in the chemical structure of the target macromolecule. Some monomers have bifunctional impurities that can act as cross-linking agents. A "hydrophilic monomer" is a monomer that yields a clear, single-phase solution when mixed with deionized water at 25 °C at a concentration of 5 wt%. A "hydrophilic component" is a monomer, macromer, prepolymer, initiator, cross-linking agent, additive, or polymer that yields a clear, single-phase solution when mixed with deionized water at 25 °C at a concentration of 5 wt%. A "hydrophobic component" is a monomer, macromer, prepolymer, initiator, cross-linking agent, additive, or polymer that is slightly soluble or insoluble in deionized water at 25 °C.

A "macromolecule" is an organic compound having a number-average molecular weight greater than 1500 daltons and may be reactive or nonreactive.

The term "macromonomer" or "macromer" is a macromolecule containing a single group that can undergo chain growth polymerization, and in particular free radical polymerization, thereby creating a repeating unit in the chemical structure of the target macromolecule. Typically, the chemical structure of a macromer is different from the chemical structure of the target macromolecule, i.e., the repeating unit of the side group of the macromer is different from the repeating unit of the target macromolecule or its main chain. The difference between a monomer and a macromer is only in the chemical structure, molecular weight, and molecular weight distribution of the side group. As a result, and in the context of this document, monomers are sometimes defined in the patent literature as polymerizable compounds having a relatively low molecular weight of about 1500 daltons or less, which obviously includes some macromers. In particular, monomers or macromers may include monomethacryloxypropyl and mono-n-butyl terminated polydimethylsiloxane (molecular weight = 500-1500 g/mol) (mPDMS) and mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether and mono-n-butyl terminated polydimethylsiloxane (molecular weight = 500-1500 g/mol) (OH-mPDMS). In addition, in the patent literature, macromers are sometimes defined as having one or more polymerizable groups, which essentially expands the general definition of macromer to include prepolymers. As a result, and when used herein, bifunctional and multifunctional macromers, prepolymers, and crosslinkers may be used interchangeably.

"Polymer" is a target macromolecule composed of repeating units of monomers used during polymerization.

A "homopolymer" is a polymer prepared from a single monomer; a "copolymer" is a polymer prepared from two or more monomers; and a "terpolymer" is a polymer prepared from three monomers. A "block copolymer" is composed of blocks or segments of different compositions. Diblock copolymers have two blocks. Triblock copolymers have three blocks. "Comb copolymers" or "graft copolymers" are composed of at least one macromer.

A "repeating unit" is the smallest group of atoms in a polymer that corresponds to the polymerization of a particular monomer or macromer.

An "initiator" is a molecule that can decompose into radicals that can subsequently react with a monomer to initiate a free-radical polymerization reaction. A thermal initiator decomposes at a specific rate depending on the temperature; typical examples are azo compounds such as 1,1'-azobisisobutyronitrile and 4,4'-azobis(4-cyanovaleric acid), peroxides such as benzoyl peroxide, t-butyl peroxide, t-butyl hydroperoxide, t-butyl peroxybenzoate, dicumyl peroxide, and lauroyl peroxide, peroxy acids such as peracetic acid and potassium persulfate, and a variety of redox systems. A photoinitiator decomposes by a photochemical process; Typical examples are derivatives of benzyl, benzoin, acetophenone, benzophenone, camphorquinone and mixtures thereof, as well as various monoacyl and bisacylphosphine oxides and combinations thereof.

A "crosslinker" is a difunctional or multifunctional monomer or macromer that can undergo free radical polymerization at two or more sites on the molecule, thereby creating branching points and forming a polymer network. Common examples include ethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, methylene bisacrylamide, triallyl cyanurate, etc.

"Prepolymer" is a reaction product of monomers that contains remaining polymerizable groups capable of undergoing 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 are mixed together and, under polymerization conditions, result in the formation of a polymer network and biomedical devices, ophthalmic devices, intraocular implants, contact lenses, and intraocular lenses made therefrom. The reactive monomer mixture may comprise reactive components such as monomers, macromers, prepolymers, crosslinkers and initiators, additives such as wetting agents, polymers, dyes, light absorbing compounds such as UV/HEV absorbers, pigments, photochromic compounds, pharmaceutical compounds and/or nutraceutical compounds, any of which may be reactive or non-reactive but are retained within the resulting biomedical device. The reaction mixture may also comprise other non-retained components such as diluents that are intended to be removed from the device prior to use. It should be understood that a wide range of additives may be used based on the type of biomedical device being manufactured and its intended purpose. The concentrations of the components of the reaction mixture are expressed as weight percentages of all retained components in the reaction mixture, excluding, therefore, non-retained components such as diluent. When diluents are used, their concentrations are expressed as weight percentages based on the amount of all components in the reaction mixture (including the diluent).

"Retained components" are polymerizable compounds (such as monomers, macromers, oligomers, prepolymers, and crosslinkers) in the reaction mixture, as well as any other components in the reaction mixture that are intended to substantially remain in the polymer network after polymerization and completion of all processing steps (such as extraction steps) and packaging steps. Retained components may be retained in the polymer network by covalent bonds, hydrogen bonds, electrostatic interactions, the formation of interpenetrating polymer networks, or any other means. Components intended to be released from the biomedical device after use are still considered "retained components." For example, pharmaceutical or nutraceutical components in a contact lens 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 (e.g. by extraction), such as diluents, are not “non-retained components”.

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

The terms "halogen" or "halo-" refer to fluorine, chlorine, bromine, and iodine.

"Alkyl" or "aliphatic" are used interchangeably herein and refer to an optionally substituted linear or branched alkyl group containing the stated number of carbon atoms. If no number is stated, the alkyl (including any optional substituents on the alkyl) may contain any number of carbon atoms from 1 to 16, 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 the alkyl group include 1, 2 or 3 groups independently selected from hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, thioalkyl, carbamate, carbonate, halogen, phenyl, _{benzyl ,} and _combinations thereof. “Alkylene” means a divalent alkyl group such as _-CH2- , _-CH2CH2- , _-CH2CH2CH2- , _{-CH2CH ( CH3 ) CH2- ,} and _{-CH2CH2CH2CH2-} .

The term "haloalkyl" refers to an alkyl group as defined above that is substituted by one or more halogen atoms, each halogen independently being F, Cl, Br or I. A preferred halogen is F. Preferred haloalkyl groups contain 1-6 carbon atoms, more preferably 1-4 carbon atoms and even more preferably _1-2 carbon atoms. The term "haloalkyl" includes perhaloalkyl groups such as _-CF3- or _-CF2CF3- . The term "haloalkylene" means a _divalent haloalkyl group such as _-CH2CF2- .

The term "hydroxy" refers to the -OH group.

As used herein, the term "hydroxyalkyl" refers to an alkyl group substituted with at least one hydroxyl 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.

"Cycloalkyl" or "cycloaliphatic" are used interchangeably herein and refer to an optionally substituted cyclic hydrocarbon having the stated number of ring carbon atoms. If no number is stated, the cycloalkyl may have from 3 to 20 ring carbon atoms (e.g., from 3 to 12 ring carbon atoms). Cycloaliphatic groups may be monocyclic, bicyclic, tricyclic, bridged, fused, and/or spirocyclic. Cycloaliphatic groups may also have one or more double bonds, provided that the group is not fully aromatic. Preferred monocyclic cycloaliphatic groups are _C3 - _C8 cycloalkyl groups, C3 _{- C7} cycloalkyl, more preferably _C4 - _C7 cycloalkyl, and even more preferably _C5 - _C6 cycloalkyl. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of substituents on a cycloalkyl group include 1, 2, or 3 groups independently selected from alkyl, hydroxy, amino, amido, oxa, carbonyl, alkoxy, thioalkyl, amido, carbamate, carbonate, halogen, phenyl, benzyl, and combinations thereof. The term "cycloalkylene" means a divalent cycloalkyl group such as 1,2-cyclohexylene, 1,3-cyclohexylene, or 1,4-cyclohexylene.

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

The term "aryl" refers to an optionally substituted aromatic hydrocarbon ring system containing at least one aromatic ring. An aryl group contains the specified number of carbon atoms in the ring. If no number is specified, aryl may contain from 6 to 14 carbon atoms in the ring. The aromatic ring may optionally be fused or otherwise attached to other aromatic hydrocarbon rings 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 group include 1, 2 or 3 groups independently selected from alkyl, hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, thioalkyl, carbamate, carbonate, halogen, phenyl, benzyl and combinations thereof. The term "arylene" means a divalent aryl group, such as 1,2-phenylene, 1,3-phenylene or 1,4-phenylene.

The term "arylalkyl" refers to an aryl group, as defined herein, appended to the parent molecular functional group through an alkyl group, as defined herein. Representative examples of arylalkyl include phenylmethyl (i.e., benzyl), phenylethyl, and phenylpropyl.

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

The term "alkoxy" means 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" means an alkyl group attached to the parent molecular moiety through a sulfur-containing bridge. Examples of thioalkyl groups include, for example, methylthio, ethylthio, n-propylthio, and isopropylthio. The term "aryloxy" means an aryl group attached to the parent molecular moiety through an oxygen bridge. Examples include phenoxy. The term "arylthio" means an aryl group attached to the parent molecular moiety through a sulfur bridge. Examples include phenylthiol. The term "cyclic alkoxy" means a cycloalkyl group attached to the parent molecular moiety through an oxygen bridge.

The term "alkylamine" refers to an alkyl group attached to the parent molecular moiety through an -NH bridge. The term "alkyleneamine" refers to a divalent alkylamine group such as -CH ₂ CH ₂ NH-.

The term "siloxanyl" refers to a structure having at least one Si-O-Si bond. Thus, for example, a siloxanyl group means a group having at least one Si-O-Si group (i.e., a siloxane group), and a siloxanyl compound means a compound having at least one Si-O-Si group. The term "siloxanyl" encompasses monomeric (e.g., Si-O-Si) as well as oligomeric/polymeric structures (e.g., -[Si-O] _n- , where n is 2 or more). Each silicon atom in a siloxanyl group is substituted with independently selected R ^A groups (where R ^A is defined as specified in (b)-(i) of formula A) to fill a valence.

Formula A. The silicone-containing component may contain one or more polymerizable compounds of formula A:

,

Where:

at least one R ^A is a group of the formula R _g -L-, where R _g is a polymerizable group and L is a linking group, and each of the remaining R ^A is independently:

a. R _g -L-,

b. C ₁ -C ₁₆ alkyl optionally substituted with one or more of hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, amido, carbamate, carbonate, halogen, phenyl, benzyl, or combinations thereof,

c. _C3 - _C12 cycloalkyl optionally substituted with one or more of alkyl, hydroxy, amino, amido, oxa, carbonyl, alkoxy, amido, carbamate, carbonate, halogen, phenyl, benzyl, or combinations thereof,

d. _C6 - _C14 aryl optionally substituted with one or more of alkyl, hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, amido, carbamate, carbonate, halogen, phenyl, benzyl, or combinations thereof,

e. halogen,

f. alkoxy, cyclic alkoxy or aryloxy,

g. siloxy,

h. alkyleneoxyalkyl or alkoxyalkyleneoxyalkyl, such as polyethyleneoxyalkyl, polypropyleneoxyalkyl or poly(ethyleneoxysopropyleneoxyalkyl), or

a monovalent siloxane chain containing from 1 to 100 siloxane repeating units optionally substituted with alkyl, alkoxy, hydroxy, amino, oxa, carboxy, alkylcarboxy, alkoxy, amido, carbamate, halogen, or combinations thereof; and

n is from 0 to 500, or from 0 to 200, or from 0 to 100, or from 0 to 20, and it is assumed that if n is different from 0, then n is a distribution having a mode equal to the stated value. If n is 2 or more, the SiO units may contain the same or different substituents R ^A , and if different substituents R ^A are present, then the n groups may have a random or block configuration.

In formula A, each of the three R ^A may contain a polymerizable group, alternatively each of the two R ^A may contain a polymerizable group, or alternatively one R ^A may contain a polymerizable group.

The term "silyl" refers to a structure of formula R ₃ Si-, and "siloxy" refers to a structure of formula R ₃ Si-O-, wherein each R in silyl or siloxy is independently selected from trimethylsiloxy, C ₁ -C ₈ alkyl (preferably C ₁ -C ₃ alkyl, more preferably alkyl or methyl) and C ₃ -C ₈ cycloalkyl.

The term "alkyleneoxy" refers to groups of the general formula -(alkylene-O) _p- or -(O-alkylene) _p- , wherein alkylene is defined as above and p is from 1 to 200, or from 1 to 100, or from 1 to 50, or from 1 to 25, or from 1 to 20, or from 1 to 10, wherein each alkylene is independently optionally substituted with one or more groups independently selected from hydroxyl, halogen (e.g., fluorine), amino, amido, ether, carbonyl, carboxyl, and combinations thereof. If p is greater than 1, then all alkylenes may be the same or different, and the alkyleneoxy may have a block or random configuration. _When alkyleneoxy forms a terminal group in a molecule, the alkyleneoxy end may, for example, be hydroxy or alkoxy (e.g., _HO- [ _CH2CH2O ] _p- or _CH3O- [ _CH2CH2O ] _p- ). Examples of alkyleneoxy include polyethyleneoxy, polypropyleneoxy, polybutyleneoxy, and poly(ethyleneoxy-co-propyleneoxy).

The term "oxaalkylene" refers to an alkylene group as defined above in which one or more non _- adjacent _CH2 groups are replaced by an oxygen atom, for example _-CH2CH2OCH ( _CH3 ) _CH2- . The term "thiaalkylene" refers to an alkylene group as defined above in which one or more non-adjacent _CH2 groups are replaced by a sulfur atom, _for example _-CH2CH2SCH ( _CH3 ) _CH2- .

The term "linking group" refers to a functional group that links a polymerizable group to a parent molecule. The linking group may be any functional group that is compatible with the compound of which it is a part, that does not adversely affect the polymerization of the compound, and that is stable under the conditions of polymerization and under the conditions of processing and storage of the finished product. For example, the linking group can be a bond or can be one or more of alkylene, haloalkylene, amide, amine, alkyleneamine, carbamate, ester ( _-CO2- ), arylene, heteroarylene, cycloalkylene, heterocycloalkylene, alkyleneoxy, oxaalkylene, thiaalkylene, haloalkyleneoxy (alkyleneoxy substituted with one or more halogen groups, such as _-OCF2- , _-OCF2CF2- , _{-OCF2CH2- )} , siloxanyl, alkylenesiloxanyl, or combinations thereof. _The linking group can optionally be substituted with 1 or more substituents. Suitable substituents may include groups independently selected from alkyl, halogen (e.g., fluorine), hydroxyl, HO-alkyleneoxy, MeO-alkyleneoxy, siloxanyl, siloxy, siloxy-alkyleneoxy-, siloxy-alkylene-alkyleneoxy- (in which more than one alkyleneoxy group may be present and in which each methylene in the alkylene or alkyleneoxy is independently optionally substituted with hydroxyl), ether, amine, carbonyl, carbamate, and combinations thereof. The linking group may also be substituted with a polymerizable group such as (meth)acrylate (in addition to the polymerizable group to which the linking group is bonded).

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 1 or 2 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.

If the linking group consists of combinations of the functional groups described above (e.g., alkylene and cycloalkylene), then these functional groups can be present in any order. For example, if in formula A above, L is designated as -alkylene-cycloalkylene-, then Rg-L can be either Rg-alkylene-cycloalkylene- or Rg-cycloalkylene-alkylene-. The order of listing is the preferred order in which the functional groups appear in the compound, starting with the terminal polymerizable group (Rg or Pg) to which the linking group is attached. For example, if in formula A, L is designated as alkylene-cycloalkylene, then Rg-L is preferably Rg-alkylene-cycloalkylene-.

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

The term "light-absorbing compound" refers to a chemical material that absorbs light in the visible spectrum (e.g., in the range from 380 nm to 780 nm). The terms "high-energy radiation absorber," "UV/HEV absorber," or "ultraviolet/high-energy visible light absorbing compound" refer to a chemical material that absorbs various wavelengths of radiation in the ultraviolet spectrum, high-energy radiation in the visible spectrum, or both. The ability of a material to absorb light of specific wavelengths can be determined by measuring its UV/VIS transmittance spectrum. Compounds that show no absorption at a specific wavelength will show substantially 100% transmittance at that wavelength. Conversely, compounds that completely absorb radiation at a specific wavelength will show substantially 0% transmittance at that wavelength. When the transmittance of a material is stated as a percentage for a particular wavelength range, it should be understood that the material exhibits a transmittance percentage at all wavelengths within that range.

Where compounds described herein contain olefinic double bonds or other centers of geometric asymmetry, and unless otherwise stated, said compounds are intended to include cis, trans, Z, and E configurations. Likewise, all tautomeric forms and salt forms are intended to include.

The term "optional substituent" means that a hydrogen atom in a substituent group is optionally substituted with a substituent. Any substituent that is sterically advantageous and synthetically achievable can be used at the site of substitution. The definition of a suitable optional substituent is well known to one skilled in the art. Examples of an "optional substituent" include, but are not limited to, _C1 - _C6 alkyl, _C1 - _C6 alkoxy, _C1 - _C6 thioalkyl, _C3 - _C7 cycloalkyl, aryl, halogen, ^hydroxy , amino, ^NR4R5 , benzyl, _SO3H , or _SO3Na , where ^R4 and ^R5 are independently H or _C1 - _C6 alkyl. The above substituents may be optionally substituted with an optional substituent (which, unless otherwise specified, is preferably not further substituted). For example, alkyl can be substituted with halogen (giving, for example, CF ₃ ).

Unless otherwise stated, ratios, percentages, shares, etc. are given by weight.

Unless otherwise stated, numeric ranges, such as in "2 to 10," include the numbers that define the range (such as 2 and 10).

In some embodiments, the reactive monomer mixture includes at least one polyamide. As used herein, the term "polyamide" refers to polymers and copolymers containing repeating units that include amide groups. The polyamide may contain cyclic amide groups, acyclic amide groups, and combinations thereof, and may be any polyamide known to those skilled in the art. Acyclic polyamides contain pendant amide groups and are capable of associating with hydroxyl groups. Cyclic polyamides contain cyclic amide groups and are capable of associating with hydroxyl groups. Polyamides suitable for use with the compositions and methods described herein are described in U.S. Patent Application Publication No. 20180009922 SILICONE HYDROGELS COMPRISING HIGH LEVELS OF POLYAMIDES, Alli et al., published January 11, 2018 and U.S. Patent Application Publication No. 20180011222 SILICONE HYDROGELS COMPRISING POLYAMIDES, Alli et al., published January 11, 2018, each of which is incorporated herein by reference in its entirety.

The Abbe number, also known as the V number or the reciprocal of the relative dispersion of a transparent material, is a measure of the dispersion of the material, i.e. the variation of the refractive index with wavelength, with high V values indicating low dispersion. The Abbe number of a material is defined as:

;

where n _D , n _F and n _C are the refractive indices of the material at the wavelengths of the Fraunhofer spectral lines D-, F- and C- (589.3 nm, 486.1 nm and 656.3 nm, respectively).

"Refractive index" is defined as:

;

where c is the speed of light in vacuum, and v is the phase velocity of light in the medium.

B. Compositions

In some embodiments, the subject matter disclosed herein provides a composition obtained by free radical polymerization of a reactive monomer mixture comprising:

(A) (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 crosslinking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39 (hereinafter referred to as "composition (A)");

(B) (i) at least one cycloaliphatic (meth)acrylate; (ii) at least one aliphatic (meth)acrylate; and (iii) at least one crosslinking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39 (hereinafter referred to as "composition (B)");

(C) (i) at least one hydrophobic monomer; (ii) at least one acrylate monomer of the following formula (I):

(I),

wherein R ¹ is selected from hydrogen and methyl, and R ² is a non-aromatic functional group having at least one carbon-carbon double bond; and (iii) at least one cross-linking agent (hereinafter referred to as “composition (C)”);

(D) (i) at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring; (ii) at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers and any combinations thereof, and (iii) at least one crosslinking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39 ("composition (D)"); or

(E) (i) at least one hydrophobic monomer; (ii) at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers and any combinations thereof; and (iii) a crosslinking agent tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39 (“composition (E)”).

Below is a more detailed description of each composition.

1. Composition (A)

In some embodiments, the subject matter disclosed herein provides a composition, referred to herein as "composition (A)", made 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 crosslinking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

In some embodiments of composition (A), at least one cycloaliphatic (meth)acrylate comprises a cycloaliphatic group having from one to four cycloaliphatic rings. In some embodiments, the cycloaliphatic group has one cycloaliphatic ring. The cycloaliphatic 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 cycloaliphatic (meth)acrylate has at least one cycloaliphatic group containing at least one carbon-carbon double bond. In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexyl methyl (meth)acrylate, 2-cyclohexyl ethyl (meth)acrylate, 3-cyclohexyl propyl (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-en-2-yl)methyl (meth)acrylate, ethylene glycol dicyclopentenyl ether (meth)acrylate, dicyclopentenyl ether (meth)acrylate poly(ethylene glycol), 2,2-bis(cyclopent-1-en-1-yloxy)ethyl (meth)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, cyclohexyl methyl (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, 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. 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, the at least one cycloaliphatic (meth)acrylate is cyclohexyl acrylate. In some embodiments, the at least one cycloaliphatic (meth)acrylate is cyclohexyl methyl acrylate. In some embodiments, the at least one cycloaliphatic (meth)acrylate is 2-cyclohexyl ethyl acrylate. In some embodiments, the at least one cycloaliphatic (meth)acrylate is ethylene glycol dicyclopentenyl ether acrylate.

In some embodiments, the cycloaliphatic (meth)acrylate does not include a substituent (e.g., a hydroxy substituent) on the cycloaliphatic functional group or anywhere else on the monomer (e.g., in a monomer such as 2-cyclohexylethyl (meth)acrylate, the monomer does not include a substituent such as a hydroxy substituent on either the cyclohexyl functional group or the ethyl functional group).

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

In some embodiments of composition (A), the at least one aromatic (meth)acrylate is a (meth)acrylate comprising at least one aryl group. In some embodiments, the aryl group is a phenyl group. In some embodiments, the aryl group may 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.

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.

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% by weight, including about 5, 10, 15, 20, 25, 30, 35, and 40% by weight, from about 10 to about 40% by weight, including about 10, 15, 20, 25, 30, 35, and 40% by weight, or from about 15 to about 40% by weight, including about 15, 20, 25, 30, 35, and 40% by weight. In some embodiments, the weight percentage of the at least one aromatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

In some embodiments of composition (A), the cycloaliphatic (meth)acrylate(s) and the aromatic (meth)acrylate(s) 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 cycloaliphatic (meth)acrylate(s) and the aromatic (meth)acrylate(s) 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.

In some embodiments of composition (A), at least one aliphatic (meth)acrylate comprises a linear or branched alkyl group containing from 1 to 25 carbon atoms ( _C1 - _C25 alkyl group), including _C1 , C2, _C3 , C4, _C5 , _C6 , _C7 , _C8 , C9, _C10 , _C11 , _{C12, C13, C14 , C15 , C16} , _C17 , _C18 , _C19 , _C20 , _{C21 , C22 , C23} , _{C24 and C25} . In particular embodiments, the aliphatic (meth)acrylate is a _C1 - _C20 alkyl (meth)acrylate, including _C1 , C2, _C3 , _C4 , C5, _C6 , _C7 , _C8 , _C9 , _C10 , _C11 , _C12 , _C13 , _C14 , _C15 , _C16 , _C17 , _C18 , _{C19 , and C20} alkyl (meth)acrylate. In more specific embodiments, the C ₁ -C ₂₀ alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-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 other more specific embodiments, the aliphatic (meth)acrylate comprises a linear alkyl group containing from 4 to 8 carbon atoms (a C ₄ -C ₈ linear alkyl group), including 4, 5, 6, 7, and 8 carbon atoms. In some embodiments, the aliphatic (meth)acrylate is n-hexyl acrylate.

In some embodiments, at least one aliphatic (meth)acrylate has at least one aliphatic group containing at least one carbon-carbon double bond.

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

In some embodiments of composition (A), the at least one crosslinking agent is selected from the group consisting of a non-cycloaliphatic crosslinking agent, a cycloaliphatic crosslinking agent, and any combination thereof. In some embodiments, the at least one crosslinking agent is a non-cycloaliphatic 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-hydroxypropyl(meth)acrylate)-terminated polydimethylsiloxanes, and any combination thereof. In more specific embodiments, the non-cycloaliphatic crosslinking agent is ethylene glycol dimethacrylate. In specific embodiments, the at least one crosslinking agent is a cycloaliphatic crosslinking agent comprising a cycloaliphatic group having one to four cycloaliphatic rings. In yet other more specific embodiments, the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate (e.g., tricyclo[5.2.1.0 ^2,6 ]decane dimethanol diacrylate).

In some embodiments, the reactive monomer mixture of composition (A) comprises a cycloaliphatic crosslinking agent in an amount of from about 1 to about 20 weight percent, including 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 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 about 3, 4, 5, 6, 7, 8, 9, and 10 weight percent. In some embodiments, the weight percentage of cycloaliphatic crosslinking agent present in the reactive monomer mixture is calculated excluding the diluent.

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

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

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

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-(2-hydroxy-3-methacryloxypropyloxy)-propyl and mono-n-butyl 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.

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

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 comprises a linear, branched, or cyclic hydroxyalkyl group having from 1 to 25 carbon atoms (C ₁ -C ₂₅ alkyl group), including C ₁ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , 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 . 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 particular embodiments, the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate is 2-hydroxyethyl methacrylate.

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

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

In some embodiments, the reactive monomer mixture of composition (A) further comprises at least one ultraviolet/high energy visible light absorbing compound.

In some embodiments, the ultraviolet/high energy visible light absorbing compound may take the form of Formula II:

Formula II,

Where:

m and n independently represent 0, 1, 2, 3, or 4;

T represents a bond, O or NR;

X is O, S, NR, SO, or SO ₂ ;

Y represents 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 YP _g ;

R ¹ and R ² , if present, are at each occurrence independently C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ thioalkyl, C ₃ -C ₇ cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halogen), halogen, hydroxy, amino, NR ³ R ⁴ or benzyl, wherein R ³ and R ⁴ are independently H or C ₁ -C ₆ alkyl, or two adjacent R ¹ or R ² groups, together with the carbon atoms to which they are attached, combine to form a cycloalkyl or aryl ring; and

EWG is an electron withdrawing group.

The compounds of formula II preferably contain one or two YP _g groups. More preferably, the compounds contain one YP _g group.

In some embodiments, the at least one ultraviolet/high energy visible light absorbing compound is a compound of Formula II, 2-(2'-hydroxy-5-methacryloxyethylphenyl)-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 ultraviolet/high-energy visible light absorbing compound is 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate. In certain embodiments, the at least one ultraviolet/high-energy visible light absorbing compound is 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate.

In some embodiments, the reactive monomer mixture of composition (A) comprises at least one ultraviolet/high-energy visible light 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 percentage of the at least one ultraviolet/high-energy visible light absorbing compound present in the reactive monomer mixture is calculated excluding the diluent.

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 and 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.

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

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

In some embodiments, the water content of composition (A) is from about 0% by weight to about 15% by weight, 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, from about 1% by weight to about 10% by weight, including about 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10% by weight, or from about 1% by weight. and up to about 8 wt.%, including about 1, 2, 3, 4, 5, 6, 7 and 8 wt.%, or from about 0.5 to less than 5 wt.%, including 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0 and 4.5 wt.%. In some embodiments, the water content is measured by hydrating the material at a temperature of 37 °C.

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 still other embodiments, composition (A) has a refractive index of at least 1.50 and an Abbe number of at least 50. In some embodiments, said refractive index and said Abbe number are measured when the material is in a dry state at a temperature of 25 °C.

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

(2) Composition (B)

In some embodiments, the subject matter described herein provides a composition, referred to herein as "composition (B)", that is made 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 crosslinking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

In some embodiments of composition (B), at least one cycloaliphatic (meth)acrylate comprises a cycloaliphatic group having from one to four cycloaliphatic rings. In some embodiments, the cycloaliphatic group has one cycloaliphatic ring. The cycloaliphatic 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 cycloaliphatic (meth)acrylate has at least one cycloaliphatic group containing at least one carbon-carbon double bond. In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexyl methyl (meth)acrylate, 2-cyclohexyl ethyl (meth)acrylate, 3-cyclohexyl propyl (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,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, (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.

In some embodiments, the cycloaliphatic (meth)acrylate does not include a substituent (e.g., a hydroxy substituent) on the cycloaliphatic functional group or anywhere else on the monomer (e.g., in a monomer such as 2-cyclohexylethyl (meth)acrylate, the monomer does not include a substituent such as a hydroxy substituent on either the cyclohexyl functional group or the ethyl functional group).

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

In some embodiments of composition (B), at least one aliphatic (meth)acrylate comprises a linear or branched alkyl group containing from 1 to 25 carbon atoms ( _C1 - _C25 alkyl group), including _C1 , C2, _C3 , C4, _C5 , _C6 , _C7 , _C8 , C9, _C10 , _C11 , _{C12, C13, C14 , C15 , C16} , _C17 , _C18 , _C19 , _C20 , _{C21 , C22 , C23} , _{C24 and C25} . In particular embodiments, the aliphatic (meth)acrylate is a _C1 - _C20 alkyl (meth)acrylate, including _C1 , C2, _C3 , _C4 , C5, _C6 , _C7 , _C8 , _C9 , _C10 , _C11 , _C12 , _C13 , _C14 , _C15 , _C16 , _C17 , _C18 , _{C19 , and C20} alkyl (meth)acrylate. In more specific embodiments, the C ₁ -C ₂₀ alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-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 other more specific embodiments, the aliphatic (meth)acrylate comprises a linear or branched alkyl group containing from 4 to 8 carbon atoms (C ₄ -C ₈ 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.

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 wt.%, from about 1 to about 20 wt.%, or from about 1 to about 10 wt.% In some embodiments, the weight percentage of the at least one aliphatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

In some embodiments of composition (B), the at least one crosslinking agent is selected from the group consisting of a non-cycloaliphatic crosslinking agent, a cycloaliphatic crosslinking agent, and any combination thereof. In some embodiments, the at least one crosslinking agent is a non-cycloaliphatic 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-hydroxypropyl(meth)acrylate)-terminated polydimethylsiloxanes, and any combination thereof. In more specific embodiments, the non-cycloaliphatic crosslinking agent is ethylene glycol dimethacrylate. In specific embodiments, the at least one crosslinking agent is a cycloaliphatic crosslinking agent comprising a cycloaliphatic group having one to four cycloaliphatic rings. In yet other more specific embodiments, the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate (e.g., tricyclo[5.2.1.0 ^2,6 ]decane dimethanol diacrylate).

In some embodiments, the reactive monomer mixture of composition (B) comprises a cycloaliphatic crosslinking agent in an amount of from about 1 to about 20 wt. %, including about 1, 5, 10, 15 and 20 wt. %, from about 3 to about 15 wt. %, including 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 and 15, or from about 3 to about 10 wt. %, including 3, 4, 5, 6, 7, 8, 9 and 10 wt. In some embodiments, the weight percentage of the cycloaliphatic crosslinking agent present in the reactive monomer mixture is calculated excluding the diluent.

In some embodiments, the reactive monomer mixture of composition (B) further comprises an aromatic (meth)acrylate. In some embodiments, the aromatic (meth)acrylate is a (meth)acrylate comprising at least one aryl group. In some embodiments, the aryl group is a phenyl group. In some embodiments, the aryl group may 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.

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% by weight, including about 5, 10, 15, 20, 25, 30, 35, 40, 45 and 50% by weight, from about 10 to about 40% by weight, including about 10, 15, 20, 25, 30, 35 and 40% by weight, or from about 15 to about 40% by weight, including about 15, 20, 25, 30, 35 and 40% by weight. In some embodiments, the weight percentage of at least one aromatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

In some embodiments, composition (B) does not include an aromatic monomer, such as an aromatic (meth)acrylate.

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 and 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.

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

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 comprises a linear, branched, or cyclic hydroxyalkyl group having from 1 to 25 carbon atoms (C ₁ -C ₂₅ alkyl group), including C ₁ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , 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 . 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 particular embodiments, the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate is 2-hydroxyethyl methacrylate.

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

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

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

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

In some embodiments, the reactive monomer mixture of composition (B) further comprises at least one ultraviolet/high-energy visible light absorbing compound. In some embodiments, the ultraviolet/high-energy visible light absorbing compound may take the form according to formula II:

Formula II,

Where:

m and n independently represent 0, 1, 2, 3, or 4;

T represents a bond, O or NR;

X is O, S, NR, SO, or SO ₂ ;

Y represents 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 YP _g ;

R ¹ and R ² , if present, are at each occurrence independently C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ thioalkyl, C ₃ -C ₇ cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halogen), halogen, hydroxy, amino, NR ³ R ⁴ or benzyl, wherein R ³ and R ⁴ are independently H or C ₁ -C ₆ alkyl, or two adjacent R ¹ or R ² groups, together with the carbon atoms to which they are attached, combine to form a cycloalkyl or aryl ring; and

EWG is an electron withdrawing group.

The compounds of formula II preferably contain one or two YP _g groups. More preferably, the compounds contain one YP _g group.

In some embodiments, the at least one ultraviolet/high energy visible light absorbing compound is a compound of Formula II - 2-(2'-hydroxy-5-methacryloxyethylphenyl)-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 ultraviolet/high-energy visible light absorbing compound is 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate. In certain embodiments, the at least one ultraviolet/high-energy visible light absorbing compound is 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate.

In some embodiments, the reactive monomer mixture of composition (B) comprises at least one ultraviolet/high-energy visible light 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 percentage of the at least one ultraviolet/high-energy visible light absorbing compound present in the reactive monomer mixture is calculated excluding the diluent.

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

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

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 other embodiments, composition (B) has a refractive index of at least 1.48 and an Abbe number of at least 50. In other embodiments, composition (B) has a refractive index of at least 1.50 and an Abbe number of at least 50. In some embodiments, said refractive index and said Abbe number are measured when the material is in a dry state at a temperature of 25 °C.

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

(3) Composition (C)

In some embodiments, the subject matter described herein provides a composition, referred to herein as "composition (C)", which is made by free radical polymerization of a reactive monomer mixture comprising: (a) at least one hydrophobic monomer; (b) at least one acrylate monomer of the following formula (I):

(I),

wherein R ¹ is selected from hydrogen and methyl, and R ² is a non-aromatic functional group having at least one carbon-carbon double bond; and (c) at least one cross-linking agent.

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.

In particular embodiments, the hydrophobic (meth)acrylate is an aliphatic (meth)acrylate. In some embodiments, the aliphatic (meth)acrylate comprises a linear or branched alkyl group containing from 1 to 18 carbon atoms _{( C1} - _C18 alkyl group), including _C1 , _C2 , _C3 , _C4 , C5, _C6 , _C7 , _C8 , _C9 , _C10 , _C11 , _C12 , _C13 , _C14 , _C15 , _C16 , _C17 , and _C18 alkyl (meth)acrylate. In more specific embodiments, the C ₁ -C ₁₈ alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-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 other more specific embodiments, the aliphatic (meth)acrylate comprises a linear alkyl group containing from 4 to 8 carbon atoms (linear C ₄ -C ₈ alkyl group). In some embodiments, the aliphatic (meth)acrylate is n-hexyl acrylate.

In some embodiments, the hydrophobic (meth)acrylate is an aromatic (meth)acrylate. In some embodiments, the aromatic (meth)acrylate is a (meth)acrylate comprising 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.

In some embodiments of composition (C), the hydrophobic (meth)acrylate is a cycloaliphatic (meth)acrylate. In some embodiments, the cycloaliphatic (meth)acrylate comprises a cycloaliphatic group having from one to four cycloaliphatic rings. In some embodiments, the cycloaliphatic group has one cycloaliphatic ring. The cycloaliphatic 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 cycloaliphatic (meth)acrylate has at least one cycloaliphatic group containing at least one carbon-carbon double bond. In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexyl methyl (meth)acrylate, 2-cyclohexyl ethyl (meth)acrylate, 3-cyclohexyl propyl (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,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, (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, cyclohexyl methyl (meth)acrylate, 2-cyclohexyl ethyl (meth)acrylate, 3-cyclohexyl propyl (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-cyclohexylethyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate is ethylene glycol dicyclopentenyl ether acrylate.

In some embodiments, the cycloaliphatic (meth)acrylate does not include a substituent (e.g., a hydroxy substituent) on the cycloaliphatic functional group or anywhere else on the monomer (e.g., in a monomer such as 2-cyclohexylethyl (meth)acrylate, the monomer does not include a substituent such as a hydroxy substituent on either the cyclohexyl functional group or the ethyl functional group).

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

(I),

where R ¹ is selected from the group consisting of hydrogen and methyl, and R ² is a non-aromatic functional group having at least one carbon-carbon double bond.

In some embodiments, R ¹ is hydrogen. In some embodiments, R ² is methyl.

In some embodiments, at least one acrylate monomer of formula (I) R²contains an alkenyl or cycloalkenyl functional group. In particular embodiments, R²contains 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 functional group.

In more specific embodiments, the acrylate monomer of formula (I) is selected from 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-(cyclopenta-2,4-dien-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-(cyclohex-3-en-1-yloxy)ethoxy)ethoxy) ethyl acrylate, N,N-diallyl acrylamide, allyl acrylate and 2-(allyloxy) ethyl acrylate.

In some embodiments, the reactive monomer mixture of composition (C) further comprises a hydroxyl-containing monomer. In some embodiments, the hydroxyl-containing monomer is a hydroxyalkyl (meth)acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate comprises a linear, branched, or cyclic hydroxyalkyl group having from ₁ to 25 carbon atoms (C1- _C25 alkyl group), including _C1 , C2, _C3 , _C4 , _C5 , _C6 , _C7 , C8, _C9 , _C10 , _C11 , _C12 , _C13 , _C14 , _C15 , _C16 , _C17 , _C18 , _C19 , _C20 , _C21 , _C22 , _{C23 , C24 ,} and _{C25 .} 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 particular embodiments, the hydroxyalkyl (meth)acrylate is 2-hydroxyethyl methacrylate or 4-hydroxybutyl acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate is 2-hydroxyethyl methacrylate.

In some embodiments, the hydroxyl-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-n-butyl-terminated mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether-terminated polydimethylsiloxane (OH-mPDMS).

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 and 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.

In some embodiments of composition (C), the at least one crosslinking agent is selected from the group consisting of a non-cycloaliphatic crosslinking agent, a cycloaliphatic crosslinking agent, and any combination thereof. In some embodiments, the at least one crosslinking agent is a non-cycloaliphatic 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-hydroxypropyl(meth)acrylate)-terminated polydimethylsiloxanes, and any combination thereof. In more specific embodiments, the non-cycloaliphatic crosslinking agent is ethylene glycol dimethacrylate. In specific embodiments, the at least one crosslinking agent is a cycloaliphatic crosslinking agent comprising a cycloaliphatic group having one to four cycloaliphatic rings. In yet other more specific embodiments, the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate (e.g., tricyclo[5.2.1.0 ^2,6 ]decane dimethanol diacrylate).

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

In some embodiments, the crosslinking agent has the formula:

where 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 some embodiments, n is 20. In some embodiments, the reactive monomer mixture comprises a crosslinking agent in an amount of from about 15 wt. % to about 22 wt. %, or from about 16 wt. % to about 20 wt. %, In particular embodiments, the crosslinking agent is present in the reactive monomer mixture in an amount of about 18 wt.

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

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

In some embodiments, the composition (C) further comprises at least one ultraviolet/high-energy visible light absorbing compound in the reactive monomer mixture. In some embodiments, the ultraviolet/high-energy visible light absorbing compound may take the form according to formula II:

Formula II,

Where:

m and n independently represent 0, 1, 2, 3, or 4;

T represents a bond, O or NR;

X is O, S, NR, SO, or SO ₂ ;

Y represents 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 YP _g ;

R ¹ and R ² , when present, are at each occurrence independently C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ thioalkyl, C ₃ -C ₇ cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halogen), halogen, hydroxy, amino, NR ³ R ⁴ or benzyl, wherein R ³ and R ⁴ are independently H or C ₁ -C ₆ alkyl, or two adjacent R ¹ or R ² groups, together with the carbon atoms to which they are attached, combine to form a cycloalkyl or aryl ring; and

EWG is an electron withdrawing group.

The compounds of formula II preferably contain one or two YP _g groups. More preferably, the compounds contain one YP _g group.

In some embodiments, the at least one ultraviolet/high energy visible light absorbing compound is a compound of Formula II, 2-(2'-hydroxy-5-methacryloxyethylphenyl)-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 ultraviolet/high-energy visible light absorbing compound is 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate. In certain embodiments, the at least one ultraviolet/high-energy visible light absorbing compound is 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate.

In some embodiments, the reactive monomer mixture of composition (C) comprises at least one ultraviolet/high-energy visible light 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 percentage of the at least one ultraviolet/high-energy visible light absorbing compound present in the reactive monomer mixture is calculated excluding the diluent.

In some embodiments, composition (C) further comprises at least one diluent in the monomer reaction mixture.

In some embodiments, the water content of composition (C) is from about 0% by weight to about 15% by weight, 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, from about 1% by weight to about 10% by weight, including about 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10% by weight, or from about 1% by weight. and up to about 8 wt.%, including about 1, 2, 3, 4, 5, 6, 7 and 8 wt.%, or from about 0.5 to less than 5 wt.%, including 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0 and 4.5 wt.%. In some embodiments, the water content is measured by hydrating the material at a temperature of 37 °C.

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 still other embodiments, composition (C) has a refractive index of at least 1.50 and an Abbe number of at least 50. In some embodiments, said refractive index and said Abbe number are measured when the material is in a dry state at a temperature of 25 °C.

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

(4) Composition (D)

In some embodiments, the subject matter described herein provides a composition, referred to herein as "composition (D)", which is made by free radical polymerization of a reactive monomer mixture comprising: (i) at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring; (ii) at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers and any combinations thereof; and (iii) at least one crosslinking agent ("composition (D)"); wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

In some embodiments, the at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring comprises two or more separate monocyclic cycloaliphatic rings. In some embodiments, the at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring comprises one bicyclic, tricyclic, bridged, fused, and/or spirocyclic cycloaliphatic ring system. In some embodiments, the at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring has at least one cycloaliphatic group containing at least one carbon-carbon double bond. In some embodiments, the cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring is selected from 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)-3 a,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, and any combination thereof. In some embodiments, at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring is ethylene glycol dicyclopentenyl ether acrylate.

In some embodiments, a cycloaliphatic (meth)acrylate containing more than one cycloaliphatic ring does not include a substituent (e.g., a hydroxyl substituent) on the cycloaliphatic functional group or anywhere else on the monomer.

In some embodiments, the reactive monomer mixture of composition (D) comprises a cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring in an amount of from about 40 to about 90 wt. %, including about 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, and 90 wt. %, from about 50 to about 80 wt. %, including about 50, 55, 60, 65, 70, 75, and 80 wt. %, or from about 50 to about 70 wt. %, including about 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69 and 70% by weight. In some embodiments, the weight percentage of cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring present in the reactive monomer mixture is calculated excluding the diluent.

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.

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.

In some embodiments, the number average molecular weight (M _n ) of the poly(ethylene glycol)-containing monomer is from about 200 g/mol to about 1000 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, 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, 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. In some embodiments, the number average molecular weight ( _Mn ) of the poly(ethylene glycol)-containing monomer is from 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.

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

,

wherein 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. In some embodiments, R ^a is hydrogen. In some embodiments, R ^a is methyl. In some embodiments, R ^b is hydrogen. In some embodiments, R ^b is methyl. In particular embodiments, R ^a is methyl and R ^b is hydrogen. In some embodiments, R ^a is methyl and R ^b is methyl. In some embodiments, m is an integer from 2 to 8, including 2, 3, 4, 5, 6, 7, and 8.

In some embodiments, the reactive monomer mixture of composition (D) comprises at least one hydrophilic monomer (e.g., a poly(ethylene glycol)-containing monomer) in an amount of 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 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 and 30 wt. %, from about 12 to about 22 wt. %, including about 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 and 22 wt. %, or from about 14 to about 20 wt. %, including about 14, 15, 16, 17, 18, 19 and 20 wt. % In some embodiments, the weight percentage of at least one hydrophilic monomer (e.g., a poly(ethylene glycol)-containing monomer) in the monomer reaction mixture is calculated excluding the diluent.

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 comprises a linear, branched, or cyclic hydroxyalkyl group having from 1 to 25 carbon atoms (C ₁ -C ₂₅ alkyl group), including C ₁ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , 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 . 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 particular embodiments, the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate. In some embodiments, the hydroxyalkyl (meth)acrylate is 2-hydroxyethyl methacrylate.

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

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

In some embodiments, composition (D) is obtained by free radical polymerization of a reactive monomer mixture comprising: (i) at least one cycloaliphatic (meth)acrylate monomer comprising more than one cycloaliphatic ring; (ii) at least one poly(ethylene glycol)-containing monomer; and (iii) at least one crosslinking agent. In some embodiments, composition (D) is obtained by free radical polymerization of a reactive monomer mixture comprising: (i) at least one cycloaliphatic (meth)acrylate monomer comprising more than one cycloaliphatic ring; (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 crosslinking agent.

In some embodiments, composition (D) is obtained 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 combinations thereof; and (iii) at least one crosslinking agent.

In some embodiments, composition (D) is obtained 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 crosslinking agent. In some embodiments, composition (D) is obtained 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 crosslinking agent.

In some embodiments, the reactive monomer mixture of composition (D) further comprises at least one cycloaliphatic (meth)acrylate comprising one cycloaliphatic ring. In some embodiments, the at least one cycloaliphatic (meth)acrylate comprising one cycloaliphatic ring comprises a cycloaliphatic group having at least one carbon-carbon double bond. The cycloaliphatic 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 cycloaliphatic (meth)acrylate containing one cycloaliphatic ring is selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexyl methyl (meth)acrylate, 2-cyclohexyl ethyl (meth)acrylate, 3-cyclohexyl propyl (meth)acrylate, and any combination thereof. In some embodiments, the cycloaliphatic (meth)acrylate containing one cycloaliphatic 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 cycloaliphatic (meth)acrylate containing one cycloaliphatic ring 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 containing one cycloaliphatic ring is cyclohexyl methyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate containing one cycloaliphatic ring is cyclohexyl methyl methacrylate. In some embodiments, the cycloaliphatic (meth)acrylate containing one cycloaliphatic ring is 2-cyclohexyl ethyl acrylate. In some embodiments, the cycloaliphatic (meth)acrylate containing one cycloaliphatic ring is 2-cyclohexyl ethyl methacrylate. In some embodiments, the combination thereof is a combination of cyclohexyl methyl acrylate and cyclohexyl methyl methacrylate. In some embodiments, the combination thereof is a combination of 2-cyclohexyl ethyl acrylate and 2-cyclohexyl ethyl methacrylate.

In some embodiments, the cycloaliphatic (meth)acrylate does not include a substituent (e.g., a hydroxy substituent) on the cycloaliphatic functional group or anywhere else on the monomer (e.g., in a monomer such as 2-cyclohexylethyl (meth)acrylate, the monomer does not include a substituent such as a hydroxy substituent on either the cyclohexyl functional group or the ethyl functional group).

In some embodiments, the reactive monomer mixture of composition (D) comprises at least one cycloaliphatic (meth)acrylate containing one aliphatic ring in an amount of from 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.%, from about 10 to about 20 wt.%, including about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 and 20 wt.%, or from about 12 to about 15 wt.%, including about 12, 13, 14 and 15 wt.%. In some embodiments, the weight percentage of at least one cycloaliphatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

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 comprising at least one aryl group. In some embodiments, the aryl group is a phenyl group. In some embodiments, the aryl group may 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-phenyl ethyl acrylate, 2-phenyl ethyl methacrylate, 3-phenyl propyl acrylate and 4-phenyl butyl acrylate. In some embodiments, the at least one aromatic (meth)acrylate is 2-phenyl ethyl acrylate. In some embodiments, the at least one aromatic (meth)acrylate is 2-phenyl ethyl methacrylate. In some embodiments, the aromatic (meth)acrylate is 3-phenyl propyl acrylate. In some embodiments, the aromatic (meth)acrylate is 4-phenyl butyl acrylate. In some embodiments, the combination thereof is a combination of 2-phenyl ethyl acrylate and 2-phenyl ethyl methacrylate. In some embodiments, the combination thereof is a combination of 2-phenyl ethyl acrylate and 3-phenyl propyl acrylate. In some embodiments, the combination thereof is a combination of 2-phenyl ethyl methacrylate and 3-phenyl propyl acrylate.

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.

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 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 about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 and 20 wt. %, or from about 12 to about 15 wt. %, including about 12, 13, 14 and 15 wt. In some embodiments, the weight percentage of at least one aromatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

In some embodiments, the reactive monomer mixture of composition (D) does not include an aromatic monomer, such as an aromatic (meth)acrylate.

In some embodiments of composition (D), the at least one crosslinking agent is selected from the group consisting of a non-cycloaliphatic crosslinking agent, a cycloaliphatic crosslinking agent, and any combination thereof. In some embodiments, the at least one crosslinking agent is a non-cycloaliphatic 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-hydroxypropyl(meth)acrylate)-terminated polydimethylsiloxanes, and any combination thereof. In more specific embodiments, the non-cycloaliphatic crosslinking agent is ethylene glycol dimethacrylate. In specific embodiments, the at least one crosslinking agent is a cycloaliphatic crosslinking agent comprising a cycloaliphatic group having one to four cycloaliphatic rings. In yet other more specific embodiments, the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate (e.g., tricyclo[5.2.1.0 ^2,6 ]decane dimethanol diacrylate).

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

In some embodiments, the crosslinking agent has the formula:

where 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 some embodiments, n is 20. In some embodiments, the reactive monomer mixture comprises a crosslinking agent in an amount of from about 15 wt. % to about 22 wt. %, or from about 16 wt. % to about 20 wt. %, In particular embodiments, the crosslinking agent is present in the reactive monomer mixture in an amount of about 18 wt.

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

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

In some embodiments, composition (D) further comprises at least one ultraviolet/high-energy visible light absorbing compound in the reactive monomer mixture. In some embodiments, the ultraviolet/high-energy visible light absorbing compound may take the form of formula II:

Formula II,

Where:

m and n independently represent 0, 1, 2, 3, or 4;

T represents a bond, O or NR;

X is O, S, NR, SO, or SO ₂ ;

Y represents 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 YP _g ;

R ¹ and R ² , if present, are at each occurrence independently C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ thioalkyl, C ₃ -C ₇ cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halogen), halogen, hydroxy, amino, NR ³ R ⁴ or benzyl, wherein R ³ and R ⁴ are independently H or C ₁ -C ₆ alkyl, or two adjacent R ¹ or R ² groups, together with the carbon atoms to which they are attached, combine to form a cycloalkyl or aryl ring; and

EWG is an electron withdrawing group.

The compounds of formula II preferably contain one or two YP _g groups. More preferably, the compounds contain one YP _g group.

In some embodiments, the at least one ultraviolet/high energy visible light absorbing compound is a compound of Formula II, 2-(2'-hydroxy-5-methacryloxyethylphenyl)-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 ultraviolet/high-energy visible light absorbing compound is 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate. In certain embodiments, the at least one ultraviolet/high-energy visible light absorbing compound is 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate.

In some embodiments, the reactive monomer mixture of composition (D) comprises at least one ultraviolet/high-energy visible light 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 percentage of the at least one ultraviolet/high-energy visible light absorbing compound present in the reactive monomer mixture is calculated excluding the diluent.

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

In some embodiments, composition (D) has a water content of from about 0% by weight to about 15% by weight, 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, from about 1% by weight to about 10% by weight, including about 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10% by weight, or from about 1% by weight. up to about 8 wt.%, including about 1, 2, 3, 4, 5, 6, 7 and 8 wt.%, or from about 0.5 to less than 5 wt.%, including 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0 and 4.5 wt.%. In some embodiments, the water content is measured by hydrating the material at a temperature of 37 °C.

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 other embodiments, composition (D) has a refractive index of at least 1.50 and an Abbe number of at least 50. In some embodiments, said refractive index and said Abbe number are measured when the material is in a dry state at a temperature of 25 °C.

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

(5) Composition (E)

In some embodiments, the subject matter described herein provides a composition, referred to herein as "composition (E)", prepared by free radical polymerization of a reactive monomer mixture comprising: (i) at least one hydrophobic monomer; (ii) at least one monomer selected from hydrophilic monomers, hydroxyalkyl (meth)acrylate monomers, and any combinations thereof; and (iii) a tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate crosslinker; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

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 a cycloaliphatic (meth)acrylate, an aliphatic (meth)acrylate, an aromatic (meth)acrylate, and any combination thereof.

In some embodiments of composition (E), the hydrophobic (meth)acrylate is a cycloaliphatic (meth)acrylate. In some embodiments, the cycloaliphatic (meth)acrylate comprises a cycloaliphatic group having from one to four cycloaliphatic rings. In some embodiments, the cycloaliphatic group has one cycloaliphatic ring. The cycloaliphatic 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 cycloaliphatic (meth)acrylate has at least one cycloaliphatic group containing at least one carbon-carbon double bond. In some embodiments, the cycloaliphatic (meth)acrylate is selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexyl methyl (meth)acrylate, 2-cyclohexyl ethyl (meth)acrylate, 3-cyclohexyl propyl (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,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, (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.

In some embodiments, the cycloaliphatic (meth)acrylate does not include a substituent (e.g., a hydroxy substituent) on the cycloaliphatic functional group or anywhere else on the monomer (e.g., in a monomer such as 2-cyclohexylethyl (meth)acrylate, the monomer does not include a substituent such as a hydroxy substituent on either the cyclohexyl functional group or the ethyl functional group).

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

In particular embodiments, the hydrophobic (meth)acrylate is an aliphatic (meth)acrylate. In some embodiments, the aliphatic (meth)acrylate comprises a linear or branched alkyl group containing from 1 to 18 carbon atoms _{( C1} - _C18 alkyl group), including _C1 , _C2 , _C3 , _C4 , C5, _C6 , _C7 , _C8 , _C9 , _C10 , _C11 , _C12 , _C13 , _C14 , _C15 , _C16 , _C17 , and _C18 alkyl (meth)acrylate. In more specific embodiments, the C ₁ -C ₁₈ alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-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 other more specific embodiments, the aliphatic (meth)acrylate comprises a linear alkyl group containing from 4 to 8 carbon atoms (linear C ₄ -C ₈ alkyl group). In some embodiments, the aliphatic (meth)acrylate is n-hexyl acrylate.

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

In some embodiments, the hydrophobic (meth)acrylate is an aromatic (meth)acrylate. In some embodiments, the aromatic (meth)acrylate is a (meth)acrylate comprising 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.

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 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 about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 wt. %, or from about 12 to about 15 wt. %, including about 12, 13, 14, and 15 wt. In some embodiments, the weight percentage of aromatic (meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

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(ethyleneglycol) methyl ether (meth)acrylate, poly(ethyleneglycol) (meth)acrylate, and any combination thereof.

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.

In some embodiments, the number average molecular weight (M _n ) of the poly(ethylene glycol)-containing monomer is from about 200 g/mol to about 1000 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, 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, 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. In some embodiments, the number average molecular weight ( _Mn ) of the poly(ethylene glycol)-containing monomer is from 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.

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

,

where R^aand R^beach 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. In some embodiments, R^ais hydrogen. In some embodiments, Ra is methyl. In some embodiments, R^bis hydrogen. In some embodiments, Rb is methyl. In particular embodiments, Ra is methyl and Rb is hydrogen. In some embodiments, Ra is methyl and Rb is methyl. In some embodiments, m is an integer from 2 to 8, including 2, 3, 4, 5, 6, 7, and 8.

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.

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, 4-hydroxybutyl acrylate. In some embodiments, the reactive monomer mixture of composition (D) comprises a combination of a poly(ethylene glycol) (meth)acrylate monomer 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.

In some embodiments, the reactive monomer mixture of composition (E) comprises at least one hydrophilic monomer (e.g., a poly(ethylene glycol)-containing monomer) in an amount of from about 1 to about 40 wt. %, 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 wt. %, about 10 to about 30 wt. %, including about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 and 30 wt.%, from about 12 to about 22 wt.%, including about 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 and 22 wt.%, from about 14 to about 20 wt.%, including about 14, 15, 16, 17, 18, 19 and 20 wt.%, from about 1 to about 10 wt.%, including about 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10 wt.%, from about 2 to about 8 wt.%, including about 2, 3, 4, 5, 6, 7 and 8 wt.%, or from about 4 to about 6 wt.%, including about 4, 5 and 6 wt.% In some embodiments, the weight percentage of at least one hydrophilic monomer (e.g., a poly(ethylene glycol)-containing monomer) in the monomer reaction mixture is calculated excluding the diluent.

In some embodiments, the tricyclo[5.2.1.0 ^2,6 ]decanedimethanol di(meth)acrylate crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decanedimethanol diacrylate.

In some embodiments, the reactive monomer mixture of composition (E) comprises a tricyclo[5.2.1.0 ^2,6 ]decanedimethanol di(meth)acrylate crosslinker (e.g., tricyclo[5.2.1.0 ^2,6 ]decanedimethanol diacrylate) in an amount of from about 1 to about 20 wt. %, including about 1, 5, 10, 15, and 20 wt. %, from about 3 to about 15 wt. %, including 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15, or from about 3 to about 10 wt. %, including 3, 4, 5, 6, 7, 8, 9, and 10 wt. %. In some embodiments, the weight percentage of the crosslinking agent tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate present in the reactive monomer mixture is calculated excluding the diluent.

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) a tricyclo[5.2.1.0 ^2,6 ]decane dimethanol diacrylate crosslinker; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

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

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

In some embodiments, the composition (E) further comprises at least one ultraviolet/high energy visible light absorbing compound in the reactive monomer mixture. In some embodiments, the ultraviolet/high energy visible light absorbing compound may take the form of formula II:

Formula II,

Where:

m and n independently represent 0, 1, 2, 3, or 4;

T represents a bond, O or NR;

X is O, S, NR, SO, or SO ₂ ;

Y represents 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 YP _g ;

R ¹ and R ² , when present, are at each occurrence independently C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ thioalkyl, C ₃ -C ₇ cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halogen), halogen, hydroxy, amino, NR ³ R ⁴ or benzyl, wherein R ³ and R ⁴ are independently H or C ₁ -C ₆ alkyl, or two adjacent R ¹ or R ² groups, together with the carbon atoms to which they are attached, combine to form a cycloalkyl or aryl ring; and

EWG is an electron withdrawing group.

The compounds of formula II preferably contain one or two YP _g groups. More preferably, the compounds contain one YP _g group.

In some embodiments, the at least one ultraviolet/high energy visible light absorbing compound is a compound of Formula II, 2-(2'-hydroxy-5-methacryloxyethylphenyl)-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 ultraviolet/high-energy visible light absorbing compound is 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate. In certain embodiments, the at least one ultraviolet/high-energy visible light absorbing compound is 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate.

In some embodiments, the reactive monomer mixture of composition (E) comprises at least one ultraviolet/high-energy visible light 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 percentage of the at least one ultraviolet/high-energy visible light absorbing compound present in the reactive monomer mixture is calculated excluding the diluent.

In some embodiments, composition (E) further comprises at least one diluent in the monomer reaction mixture.

In some embodiments, composition (E) has a water content of from about 0% by weight to about 15% by weight, 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, from about 1% by weight to about 10% by weight, including about 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10% by weight, or from about 1% by weight to about 8% by weight, including about 1, 2, 3, 4, 5, 6, 7 and 8% by weight. or from about 0.5 to less than 5% by weight, 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 by hydrating the material at a temperature of 37 °C.

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 other embodiments, composition (E) has a refractive index of at least 1.50 and an Abbe number of at least 50. In some embodiments, said refractive index and said Abbe number are measured when the material is in a dry state at a temperature of 25 °C.

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

C. Ophthalmic devices

In some embodiments, the subject matter disclosed herein provides a device comprising a composition (A, B, C, D, or E) as directly described herein above.

In specific embodiments, the ophthalmic device comprises a lens, an implantable lens, an overlay lens, or an insert selected from an intraocular implant or lens, a contact lens, a corneal implantable lens, a corneal overlay lens, and a corneal insert.

In particular embodiments, the ophthalmic device is an intraocular implant or lens. More particularly, the subject matter described herein also provides intraocular implants and/or lenses made at least in part or in whole from the compositions (A-E) described herein. Such intraocular implants or lenses may include an optic and one or more haptic portions. Typically, the compositions of the subject matter described herein comprise part or all of the optic of the intraocular implant or lens. In some embodiments, the optic of the implant or lens will have a core made from one of the compositions described herein surrounded by a different polymer or material. Implants or lenses in which the optic consists at least in part of one of the compositions of the subject matter described herein typically also have a haptic portion. The haptic portion may also be made from the polymer of the present disclosure or may be made from another material, such as another polymer.

In some embodiments, the intraocular implant or lens of the subject matter described herein is a single-piece lens having a soft, foldable central optic region and an outer peripheral region (haptic region), both regions being made of the same polymer. In other embodiments, the optic and haptic regions may be formed from different types of polymers or materials, if desired. Some implants or lenses may also have haptic portions made from different materials, such as when one or more haptic portions are made from the same material as the optic portion and the other haptic portions are made from materials other than the polymer described herein. Multi-component implants or lenses may be made by embedding one material within another, by parallel extrusion processes, by curing a hard material around a soft material, or by forming an interpenetrating network of a hard component in a preformed hydrophobic core. In cases where one or more haptic portions are made of a material different from the material of the optical portion of the lens, the haptic portion may be attached to the optical portion by any method known in the art, such as by drilling a hole or holes in the optical portion and inserting the haptic portion.

The compositions described herein have been designed to be foldable so that the intraocular lens can be inserted into the patient's eye through a small incision. In some cases, the incision will be less than 2.5 mm; in some cases, the incision will be less than 2 mm. The haptic portion of the lens provides the necessary support for the implant or lens in the eye after insertion and unfolding of the lens and tends to stabilize the position of the lens after insertion and closure of the incision. The shape of the haptic portion is not particularly limited and can have any desired configuration, such as a plate or graduated spiral thread, also known as a C-shaped configuration.

The optic portion of the intraocular lens may have a diameter of about 2-6 mm before hydration. The diameter of 2-6 mm is fairly standard in the art and is generally selected to cover the pupil in its fully dilated state under natural conditions. However, other sizes are also contemplated and the subject matter of the invention described herein is not limited to any particular diameter or size of the intraocular lens. Moreover, it is not necessary for the optic portion of the lens to have a round shape, and it may also be oval, square or any other shape if desired.

The intraocular lens may further include one or more non-optical haptic components extending from the outer peripheral surface of the optic portion. The haptic components may have any desired shape, such as graduated spiral strands or flat plate sections, and may be used to retain the lens within 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 optic and haptic portions, such other portions may be made of a polymer, as are the haptic and optic portions, or, if necessary, of another material.

The intraocular implant lenses can be inserted into the eye by any method known in the art. For example, the intraocular lens can be folded before insertion into the eye using an intraocular lens insertion device or using small, thin tweezers commonly used by ophthalmic surgeons. Once the implant or lens is in the intended location, it is released and unfolded. As is well known to those skilled in the art, the replacement lens is typically removed before insertion of the intraocular lens. The intraocular lens of the subject matter described herein can be made of a substantially physiologically inert soft polymeric material that is capable of providing a transparent refractive body of the lens even after being folded and unfolded. In some embodiments, the foldable intraocular lens of the subject matter described herein can be inserted into either eye by injection, wherein the mechanically pliable material is folded and pushed through a small tube, such as a tube with an internal diameter of 1 mm to 3 mm.

E. Method of manufacturing an ophthalmic device

In other embodiments, the subject matter disclosed herein is a method of making an ophthalmic device, comprising: (a) providing any one of composition (A), composition (B), composition (C), composition (D), or composition (E); and (b) forming the ophthalmic device. In other embodiments, the subject matter disclosed herein is a method of making an ophthalmic device, comprising: (a) preparing a preform from any one of composition (A), composition (B), composition (C), composition (D), or composition (E); and (b) milling the ophthalmic device from the preform. In other embodiments, the subject matter disclosed herein is a method of making an ophthalmic device, comprising forming the ophthalmic device from any one of composition (A), composition (B), composition (C), composition (D), or composition (E). In other embodiments, the subject matter disclosed herein relates to a method of manufacturing an ophthalmic device, comprising forming an ophthalmic device from any of composition (A), composition (B), composition (C), composition (D), or composition (E), and then cleaning the surface by grinding. In some embodiments of the above-described methods, the method further comprises the step of extracting the ophthalmic device with a solvent. In certain embodiments, the method further comprises the step of hydrating the extracted ophthalmic device with at least one aqueous solution. In particular embodiments, the method further comprises the step of irradiating using a laser, which in certain embodiments is a two-photon laser, which in other embodiments is a femtosecond two-photon laser. In more particular embodiments, the method further comprises the step of sterilizing the ophthalmic device. The ophthalmic device can be sterilized by known methods, such as, but not limited to, autoclaving.

Some embodiments of the invention will be described in detail in the examples presented below.

EXAMPLES

Unless otherwise specified, polymer capsules were used as test specimens for determining refractive index, Abbe number, water content and glass transition temperature, they were extracted with acetonitrile or 2-propanol and dried. Unless otherwise specified, the test specimens for microglitter and macroglitter were lenses.

Refractive Index Test Method: The refractive index was measured using an Anton Paar Abbemat WR-wavelength refractometer. Before use, the instrument was equilibrated at 25 °C or 35 °C for at least 1 hour. The measurement wavelength was set to 589.3 nanometers. Using tweezers, the sample was placed on a quartz plate. The lid of the instrument was closed and the refractive index was recorded after 60 seconds of standing. The measurements were performed on three polymer capsules and the average value was reported. In some examples, where noted, the measurements were performed on both sides of the three polymer capsules and the average value of the six measurements was reported.

Method for testing the Abbe number According to the instructions for measuring the refractive index at 589.3 nm, the refractive indices at 486.1 and 656.3 nm were determined. The measurements were performed on three polymer capsules, and for each polymer capsule, the refractive index measurements were performed at all three wavelengths before measuring the next sample. The Abbe number was calculated as follows:

;

where n _D , n _F and n _C are the refractive indices of the material at the wavelengths of the Fraunhofer D-, F- and C- spectral lines (589.3 nm, 486.1 nm and 656.3 nm, respectively). The average value of three measurements was recorded. In some examples, where noted, measurements were made on both sides of three polymer capsules and the average value of six measurements was reported.

As indicated in the examples, water content was measured gravimetrically either by the "drying method" or the "hydration method".

In the "drying method", three polymer capsules (each approximately 2 mm thick and 13 mm in diameter) were equilibrated in individual glass scintillation vials containing approximately 10 mL of PBS for approximately 14 days at 37 °C. Each polymer capsule was removed from the vial using fine-tipped metal tweezers and briefly blotted on all sides (flat surfaces and edges) with lint-free blotting paper to remove surface/excess PBS. Using dry tweezers, each capsule was placed on a tared balance pan and weighed individually. The wet weight of each polymer capsule was determined as the combined weight of the pan and the wet capsule minus the weight of one balance pan. Dry weight was measured by placing the sample pans in a vacuum oven that had been preheated to 140°F (60°C) for 30 minutes. The vacuum was applied until the pressure reached at least 1 in. Hg; lower pressures were acceptable. The vacuum valve and pump were turned off and the lenses were allowed to dry for 24 hours. The purge valve was opened to allow dry air or dry nitrogen to enter. When the oven pressure reached atmospheric pressure, the pans were removed and weighed. After the pans (with polymer capsules) were weighed, the polymer capsules were placed in a vacuum oven and dried for an additional 24 hours and then weighed to obtain the 48-hour drying data. This procedure was repeated to obtain the 72-hour drying data. At each time point, the dry weight was determined as the combined weight of the balance pan and dry capsules minus the weight of the balance pan alone. The water content of the polymer capsule was calculated as follows: percent water content (% WC) = (wet weight - dry weight)/wet weight X 100. The mean and standard deviation of the water content were calculated and the mean value was reported as the percent water content of the capsule.

In an alternative embodiment, the water content was determined gravimetrically by the "hydration method". In this method, three dry polymer capsules (previously extracted with 2-propanol and dried) were weighed individually and transferred to separate glass scintillation vials using fine-tipped metal tweezers. About 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 capsules were removed from the vials using fine-tipped metal tweezers and briefly blotted on all sides (flat surfaces and edge) with lint-free blotting paper to remove surface/excess water. Using dry tweezers, each polymer capsule was placed in a tared weighing pan and weighed individually. After weighing, the polymer capsules were transferred back to the vials and incubated at 37°C for an additional 7 days to determine the water content after 14 days. At each time point, the water content of the polymer capsule was calculated as follows: % water content (%WC) = (wet weight - dry weight) / wet weight × 100.

Method for testing the glass transition temperature Due to the thickness and/or fragility of the polymer capsules, the test specimens were cut from the center of the polymer capsules or lenses using a razor blade. The specimens could not be perforated as in the case of thin film. The test specimens were analyzed (both copies) 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. The glass transition temperatures were determined from the first and second heating scans (1st scan and 2nd scan, respectively).

Microshine Test Method: Prior to conditioning lenses for dark-field light microscopy, the lenses were extracted with acetonitrile or methanol. For extraction, the lenses were individually placed in a lens container containing 3 mL of acetonitrile or methanol and extracted overnight at ambient temperature, followed by 3 changes of 3 mL aliquots of acetonitrile or methanol for 4 hours. Following the final extraction, the lenses were air-dried at ambient temperature for at least six days. The lenses were then cleaned to remove all noticeable residual debris from the lens manufacturing and extraction processes and then immersed in 0.9% saline in fluidized wells. Microvacuoles can be induced by placing these wells in an oven at 35 °C for approximately 15 hours. The lenses were removed from the oven and equilibrated at room temperature for at least 2 hours and then analyzed by dark-field light microscopy as described in Biomedical Optics Express, 2013, Vol. 4 No. 8, incorporated herein by reference in its entirety. Any standard light microscope or camera capable of dark-field imaging can be used. Under dark-field conditions, the intraocular lens is illuminated with retro-light via an inclined light ring. If microvacuoles or other light-scattering centers are absent, the image appears black. As the number of microvacuoles increases, the amount of forward scattered light increases, creating a constellation pattern of forward scattered light against a dark background. Image J (or other similar post-processing software) was used to determine the density of microvacuoles obtained by dark-field microscopy for small groups of microvacuoles. A circular area of 4 mm in diameter was examined and the microvacuole density (number of microvacuoles or microglitters per millimeter ² (no./mm ² )) was calculated. In general, intraocular lenses with fewer microvacuoles or microglitters provide better vision than lenses with higher forward scatter and are therefore preferred. A microglitter density of about 4/mm ² is considered low and comparable to glare-free intraocular lenses.

Macrogloss Test Method Lenses were individually placed in a lens case containing 3 mL of acetonitrile (ACN). The lenses were extracted at ambient temperature for four hours. The acetonitrile was removed with a disposable pipette and an additional 3 mL of acetonitrile was added. The lenses were then extracted overnight at ambient temperature. The acetonitrile was removed with a disposable pipette and an additional 3 mL of acetonitrile was added. The lenses were extracted at ambient temperature for four hours. The acetonitrile was removed with a disposable pipette and an additional 3 mL of acetonitrile was added. The lenses were extracted at ambient temperature for four hours. The acetonitrile was removed with a disposable pipette and the lenses were air dried at ambient temperature for at least six days. The air-dried lenses were individually placed in lens cases containing 3 mL of methanol and kept at ambient temperature overnight. In an alternative embodiment, the lenses were initially directly extracted with 3 mL aliquots of methanol overnight, followed by 3 changes of 3 mL aliquots of methanol at 4 hour intervals. Following organic extraction by either method, the lenses were then gradually immersed in DPBS solution using the following “gradient equilibration” method: (1) the lenses were individually placed in lens cases containing 3 mL of 80% (v/v) aqueous methanol solution at ambient temperature for four hours, (2) the 80% (v/v) aqueous methanol solution was replaced with 3 mL of 60% (v/v) aqueous methanol solution at ambient temperature for four hours, (3) the 60% (v/v) aqueous methanol solution of the lenses was then replaced with 3 mL of 50% (v/v) methanol: Dulbecco's phosphate-buffered saline at ambient temperature overnight, (4) the 50% (v/v) methanol: Dulbecco's phosphate-buffered saline was then replaced with 3 mL of 40% (v/v) methanol:Dulbecco's phosphate-buffered saline at ambient temperature for four hours, (5) 40% (v/v) methanol:Dulbecco's phosphate-buffered saline was replaced with 3 ml 20% (v/v) methanol:Dulbecco's phosphate-buffered saline at ambient temperature for four hours, and finally (6) 20% (v/v) methanol:Dulbecco's phosphate-buffered saline was replaced with 3 ml Dulbecco's phosphate-buffered saline at ambient temperature overnight after at least two wash steps with 3 ml Dulbecco's phosphate-buffered saline to remove methanol and subsequent equilibration in Dulbecco's phosphate-buffered saline overnight. Light scattering vacuoles (prepared without extraction, after acetonitrile extraction followed by drying, or after organic extraction and gradient equilibration) were created in the test lenses by placing the test lenses individually in lens containers containing 3 ml of PBS. After screwing on the caps, the containers were placed in an incubator at 37 °C for at least three days. The lenses were then evaluated by darkfield microscopy using a microscope (Nikon SMZ1500) at 25x-30X magnification. If the amount of macroflares is small, they can be counted.

The following abbreviations will be used in the examples, the meanings of which are given below.

TL03 light sources: Phillips TLK 40W/03 lamps

LED: Light Emitting Diode

RMM: reactive monomer mixture(s)

RI (25): refractive index measured at 25 °C

RI (35): 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 (°C) as measured using differential scanning calorimetry (DSC)

mm: millimeter(s)

cm: centimeter(s)

µm: micrometer(s)

nm: nanometer(s)

µl: microliter(s)

mW: milliwatt(s)

g/mol: grams/mol

Yes or dalton(s): gram(s)/mol

kDa: kilodalton(s)

PBS: phosphate buffered saline

DPBS: Dulbecco's phosphate-buffered saline, which does not contain 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)

BCH ((1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-yl)methyl acrylate or cyclol acrylate or [(1S,4S)-2-bicyclo[2.2.1]hept-5-enyl]methylprop-2-enoate [CAS 95-39-6] (monomeric polymer and DAJAC Labs Inc.)

CAA: Cinnamyl Acrylate

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 dimethylol tricyclodecane diacrylate [CAS 42594-17-2] (Sigma-Aldrich or Kyoeisha Chemical Co.)

DMA: N,N-dimethylacrylamide [CAS 2680-03-7] (TCI or Sigma-Aldrich);

NVP: N-vinylpyrrolidin-2-one

HEMA: 2-hydroxyethyl methacrylate (Bimax)

HBA: 4-hydroxybutyl acrylate [CAS 2478-10-6] (TCI or BASF)

mPEG 300: poly(ethylene glycol) methyl ether methacrylate (M _{n =} 300 grams/mol) (Sigma-Aldrich)

PEGOH 200: poly(ethylene glycol) methacrylate (Polysciences; the molecular weight of the PEG block is 200 grams/mol)

PEG-OH 360: poly(ethylene glycol) methacrylate (M _{n =} 360 grams/mol) (Sigma-Aldrich)

PVP K90: poly(N-vinylpyrrolidone) [CAS 9003-39-8] (Ashland)

PDMA: polydimethylacrylamide (M _n = 414 kDa; M _{w =} 498 kDa. Toray)

Molecular weight was determined by size exclusion chromatography with multi-angle scattering (SEC-MALS). In the SEC-MALS setup, an aqueous acetonitrile solution consisting of 80% (v/v) 50 mM _Na2SO4 and 20% (v/v) acetonitrile was used as the mobile phase at a flow rate of 0.5 mL/min at 40 °C. Two Tosoh Biosciences TSK-gel columns [SuperAW4000 and SuperAW5000] with an integrated Agilent 1200 UV/VIS diode array detector, a Wyatt Optilab rEX interferometric refractometer, and a Wyatt mini-DAWN Treos multi-angle laser scattering (MALS) detector (λ=658 nm) were used in series. 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 packing solution in a 10-mL volumetric flask. Packing solution: 18.52 grams (300 mmol) boric acid, 3.7 grams (9.7 mmol) sodium borate decahydrate, and 28 grams (197 mmol) sodium sulfate were dissolved in enough deionized water to fill a 2-L volumetric flask. Three different solutions were prepared and tested. Monomeric serum albumin samples were also tested using solutions prepared with only 10 milligrams of protein in 10 mL of packing solution. All solutions were filtered through a 0.45-μm nylon membrane filter prior to injection into the SEC-MALS system. The number average molecular weight of the three samples was 414 kDa (standard deviation 12 kDa); the weight average molecular weight of the three samples was 498 kDa (standard deviation 11 kDa); the obtained polydispersity coefficient was 1.2.

Omnirad 819: bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide [CAS 162881-26-7] (IGM Resins)

AIBN: Azobisisobutyronitrile [CAS 78-67-1]

mPDMS: polydimethylsiloxane with mono-n-butyl and monomethacryloxypropyl end groups (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: polydimethylsiloxane with mono-n-butyl and mono-(2-hydroxy-3-methacryloxypropyloxy)-propyl end groups (M _n = 1400 Dalton, n = 15) (Ortec or DSM-Polymer Technology Group)

EGDMA: Ethylene glycol dimethacrylate (Esstech)

ac-PDMS: bis-3-acryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane (Tegomer V-Si 2250 from Evonik)

XLMA: bis-3-methacryloxy-2-hydroxypropyloxypropylpolydimethylsiloxane (M _n =2000 daltons, n=20) (Shin Etsu)

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-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propyl ether (Adesis)

HEVB: 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate

Preparation of HEVB Synthesis of 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate (B) as shown in Scheme 1

Scheme 1

Methyl cyanoacetate (40 g, 0.4037 mol) and 25 mL of dichloromethane were stirred in a 500 mL 3-neck round bottom flask with a reflux condenser under nitrogen. 2-Aminoethanol (23.8 grams, 0.3897 mol, ~0.97 equiv) was added to the solution via the addition funnel, after which the temperature rose and methylene chloride began to flow out. After the exotherm ceased, external heating was applied to continue the smooth reflux for a total of two hours, after which no ethanolamine was detected by thin layer chromatography.

The reaction can also be carried out at room temperature and carried out for several hours.

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

The crude N-2-hydroxyethylacetamide derivative was dissolved in 150 mL of dichloromethane containing 40 g of pyridine (~0.5 mol) in a three-necked round-bottomed flask equipped with a reflux condenser, an addition funnel, and a magnetic stirrer. The flask was immersed in an ice bath and allowed to cool to about 0 °C. Methacryloyl chloride (45.76 g, ~0.44 mol) was added dropwise from the addition funnel and the resulting reaction mixture was allowed to warm to room temperature with constant stirring of the system. Methanol (20 mL) was added to the flask to quench the reaction of any unreacted methacryloyl chloride. The volatiles were removed by evaporation on a rotary evaporator 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 layers were discarded. Sodium chloride was added to the aqueous layer, which was then extracted three times with 300 mL of ethyl acetate. About 50 milligrams of BHT was added to the combined organic fractions as an inhibitor, and the ethyl acetate was removed by evaporation on a rotary evaporator under reduced pressure. The resulting crude product crystallized from the solution during removal of the solvent. When about 100 mL of ethyl acetate remained in the flask, 250 mL of hexane was added and the crude product was isolated by vacuum filtration through a fritted glass funnel. Thin layer chromatography analysis revealed one compound. The filter cake was washed twice with 150 mL of hexane and then dried in vacuo at 40 °C to yield 53 grams (yield about 70%) of 2-(2-cyanoacetamido)ethyl methacrylate (A). ¹ P-NMR (500 MHz, CDCl ₃ ) δ 1.93 (3H, s, CH ₃ ), 3.36 (2H, s, CNCH ₂ ), 3.60 (2H, dd, CH ₂ NH), 4.26 (2H, t, CH ₂ OC=O), 5.59 (1H, m, vinylic), 6.11 (1H, bs, vinylic), 6.52 (1H, bs, NH).

A mixture of 9 H -thioxanthene-9-one (2.12 grams, 0.01 mol) and thionyl chloride (5 ml, 8.2 grams, ~0.07 mol) was heated under reflux in a 50 ml round-bottomed flask under nitrogen atmosphere with constant stirring. After two hours, the red solution was evaporated to dryness, ensuring the removal of all unreacted thionyl chloride from the system. 2-(2-cyanoacetamido)ethyl methacrylate (A) (2.3 grams, 0.0117 mol, ~1.17 equiv.) and 15 ml of dichloromethane were added, the resulting reaction mixture was heated under reflux under nitrogen. The reaction was monitored by thin layer chromatography. After two hours, no changes were observed in the chromatogram, so the reaction mixture was allowed to cool to room temperature. 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate (B) was isolated as yellow crystals (3.2 grams, 82% yield) after passage through a short silica gel column (CH ₂ Cl ₂ , then 8 wt% EtOAc in CH ₂ Cl ₂ ). ¹ P-NMR (500 MHz, CDCl ₃ ) δ 1.84 (3H, s, CH ₃ ), 3.47 (2H, m, CH ₂ NH), 4.01 (2H, t, CH ₂ OC=O), 5.55 (1H, m, vinyl), 5.91 (1H, bs, NH), 5.98 (1H, bs, vinyl), 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: cyclohexyl methyl acrylate

CHEA: 2-cyclohexyl ethyl acrylate

CHPA: 3-cyclohexylpropyl acrylate

Synthesis of cyclohexyl methyl acrylate (CHMA) Cyclohexylmethanol (25.0 g, 219.0 mmol) and triethylamine (33.46 g, 330.7 mmol) were dissolved in dichloromethane (450 mL) and the mixture was cooled to about 0^°C in an ice bath. Acryloyl chloride (29.74 g, 328.5 mmol) was added over 20 min while maintaining a constant temperature at about 0 °C. After complete addition, the reaction mixture was stirred at 0 °C for 30 min followed by stirring at ambient temperature overnight. Thin layer chromatography was used to monitor the reaction progress. After completion of the reaction, triethylammonium chloride was filtered, dissolved in deionized water (200 mL), and extracted with dichloromethane (3 x 50 mL). The combined filtrate and organic extracts were washed with water (2 x 50 mL), brine (25 mL), dried over anhydrous Na₂SO₄, filtered under vacuum and concentrated on a rotary evaporator. The crude product was then passed through a short plug of silica gel using 10% ethyl acetate inn-hexanes, to obtain the desired CHMA product in the form of a transparent oil (yield 98%).¹P-NMR (500 MHz, CDCl₃):δ6.39 (1H, dd,J=1.0, 17.0 Hz), 6.12 (1H, dd, J=10.0, 17.0 Hz), 5.81 (1H, dd, J=1.5, 10.0 Hz), 3.97 (2H, d, J=6.0 Hz), 1.76-1.62 (6H, m), 1.31-1.15 (3H, m), 0.95-1.01 (2H, m).

Synthesis of 2-cyclohexyl ethyl acrylate (CHEA) 2-Cyclohexyl ethyl acrylate was prepared according to the same general procedure except that 2-cyclohexylethanol was used instead of cyclohexylmethanol (yield 99%). ¹ P-NMR (500 MHz, CDCl ₃ ): δ 6.38 (1H, dd, J =1.1, 17.2 Hz), 6.11 (1H, dd, J =10.1, 17.2 Hz), 5.80 (1H, dd, J =1.4, 10.1 Hz), 4.18 (2H, t, J =7.0 Hz), 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).

Synthesis of 3-cyclohexylpropyl acrylate (CHPA) 3-Cyclohexylpropyl acrylate was prepared according to the same general procedure except that 3-cyclohexylpropanol was used instead of cyclohexylmethanol (yield 99%). ¹ P NMR (500 MHz, CDCl ₃ ): δ 6.40 (1H, dd, J = 1.0, 17.1 Hz), 6.11 (1H, dd, J = 10.0, 17.1 Hz), 5.81 (1H, dd, J = 1.5, 10.0 Hz), 4.13 (2H, t, J = 7.1 Hz), 1.71-1.64 (7H, m), 1.25-1.20 (6H, m), 0.91-0.88 (2H, m).

Examples 1-5

Under yellow light illumination, the RMM listed in Table 1 were degassed by bubbling with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a filling chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. Polymer capsules (approximately 2 millimeters thick and 13 millimeters in diameter) were made using a Teflon cup and a round glass plate secured together in a stainless steel fixture (base and open screw cap). Approximately 350 microliters of RMM were placed in the Teflon cup and assembled on the glass plate and stainless steel fixture. The assembly was transferred to a curing chamber maintained at 55°C to 60°C and then cured using TL03 lamps at 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were manually demolded. All specimens were clear and exhibited low levels of surface tack. For each specimen, refractive index and Abbe index values were determined using the unremoved capsules. These values are listed in Table 1.

Table 1

Components (% wt.) Ex. 1 Ex. 2 Ex. 3 Ex. 4 Ex. 5 CHA 62 57 52 47 36 PEA 10 15 20 25 36 NHA 24.85 24.85 24.85 24.85 24.85 TCDA 3 3 3 3 3 Omnirad 819 0.15 0.15 0.15 0.15 0.15 Properties Ex. 1 Ex. 2 Ex. 3 Ex. 4 Ex. 5 RI (25) 1.497947 (0.000278) 1.500535 (0.000081) 1.503177 (0.000029) 1.505821 (0.000198) 1.511641 (0.000049) RI (35) 1.494831 (0.000258) 1.497222 (0.000196) 1.499826 (0.000068) 1.502526 (0.000178) 1.508389 (0.000080) Abbe number (25) 52 (0) 51 (0) 50 (0) 48 (0) 46 (0)

The RMM in Table 1 contains cyclohexyl acrylate, phenyl ethyl acrylate, n-hexyl acrylate and cycloaliphatic crosslinker. The amounts of cyclohexyl acrylate and phenyl ethyl acrylate can vary, but the amounts of n-hexyl acrylate, cycloaliphatic crosslinker are fixed. Tests show that as the concentration of cyclohexyl acrylate decreases, the Abbe number also decreases, while the RI measurement increases.

Examples 6-10

Under yellow light illumination, the RMMs listed in Table 2 were degassed by sparging with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a casting chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. The polymer capsules were made as described in Examples 1-5. About 350 microliters of RMM were placed in a Teflon cup and assembled on a glass plate and a stainless steel fixture, then the assembly was transferred to a curing chamber maintained at a temperature of 55 °C to 60 °C and then cured using TL03 lamps at an intensity of 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at an intensity of 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were manually demolded. All samples were clear and exhibited low levels of surface tack that decreased with increasing TCDA levels. For each example, refractive index and Abbe number values were determined using the unremoved capsules. These values are listed in Table 2. In some examples, these measurements were made on the front and back surfaces of the sample. These surfaces were in contact with either the Teflon cup or the glass fixture. Small differences in refractive index and Abbe number between the Teflon and glass contact surfaces were measured.

Examples 11 and 12

Under yellow light illumination, the RMMs listed in Table 2 were degassed by bubbling with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a casting chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. About 350 microliters of RMM were dispensed into a ring that was placed between two glass plates and held in place with clamps, the device was then transferred to a curing chamber maintained at 55°C to 60°C, and then cured using TL03 lamps at 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were demolded manually. All samples were clear and exhibited low levels of surface tack; sample 12 exhibited no tack. For each sample, refractive index and Abbe number values were determined using the unextracted capsules. These values are listed in Table 2.

Table 2

Components (% wt.) Ex. 6 Ex. 7 Ex. 8 Ex. 9 Ex. 10 Ex. 11 Ex. 12 CHA 52 52 52 52 50 36 36 PEA 20 20 20 20 22 36 36 NHA 24.85 21.85 19.85 18.85 18.85 24.85 6.85 TCDA 3 6 8 9 9 3 3 XLMA 0 0 0 0 0 0 18 Omnirad 819 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Properties Ex. 6 Ex. 7 Ex. 8 Ex. 9 Ex. 10 Ex. 11 Ex. 12 RI (25) 1.503177 (0.000029) 1.506088 (0.000700) 1.508474 (0.000223) Teflon 1.509408 (0.000411)
Glass
1.508175 (0.000114) Teflon
1.509240 (0.000584)
Glass
1.508129 (0.000585) 1.511641 (0.000049) 1.503541 (0.000025) Abbe number (25) 50 (0) 50 (1) 50 (0) Teflon
50 (1)
Glass
50 (0) Teflon
49 (0)
Glass
50 (0) 46 (0) 46 (0)

RMM, as shown in Ex. 6-10, maintained essentially similar amounts of cyclohexyl acrylate and phenylethyl acrylate, but allowed the n-hexyl acrylate and crosslinker to vary. The Abbe number was essentially stable in these examples, but as the concentration of cycloaliphatic crosslinker was increased, an increase in refractive index was measured. RMM, as shown in Ex. 11-12, essentially demonstrated that the inclusion of the XMLA crosslinker did not significantly affect the RI or Abbe number measurements. However, at lower amounts of cyclohexyl acrylate and relatively higher amounts of phenyl acrylate, the Abbe number was reduced compared to Ex. 6-10.

Examples 13-14

Under yellow light illumination, the RMMs listed in Table 3 were degassed by sparging with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a casting chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. The polymer capsules were made as described in Examples 1-5. About 350 microliters of RMM were placed in a Teflon cup and assembled on a glass plate and a stainless steel fixture, then the assembly was transferred to a curing chamber maintained at a temperature of 55 °C to 60 °C and then cured using TL03 lamps at an intensity of 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at an intensity of 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were manually demolded. All samples were clear and showed no surface stickiness. For each sample, the refractive index and Abbe number were determined using the un-demolished capsules. These values are listed in Table 3. These experiments demonstrate the effect of varying the concentration of HBA and PVP 90 on the RI and Abbe number.

Example 15

Under yellow light illumination, the RMM listed in Table 3 was degassed by bubbling with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a filling chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. The polymer capsules were made by dispensing approximately 350 microliters of RMM using a Teflon cup assembly or alternatively by dispensing into a ring which was placed between two glass plates and held together with clamps, the device was then transferred to a curing chamber maintained at a temperature of 55°C to 60°C and then cured using TL03 lamps at an intensity of 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at an intensity of 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were demolded manually. The samples were essentially clear and showed no surface tackiness. For each example, the refractive index and Abbe number values were determined using the unremoved capsules. These values are listed in Table 3.

Example 16

Under yellow light, the RMM listed in Table 3 was degassed by bubbling with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a casting chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. About 350 microliters of RMM was dispensed into a ring that was placed between two glass plates and held in place with clamps, then the device was transferred to a curing chamber maintained at 55°C to 60°C and then cured using TL03 lamps at 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were demolded manually. The samples were essentially transparent and did not exhibit surface stickiness. For each sample, refractive index and Abbe number values were determined using the unextracted capsules. These values are listed in Table 3.

Example 17

Under yellow light, the RMM listed in Table 3 was degassed by bubbling with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a casting chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. About 350 microliters of RMM was dispensed into a ring that was placed between two glass plates and held in place with clamps, then the device was transferred to a curing chamber maintained at 55°C to 60°C and then cured using TL03 lamps at 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were demolded manually. The samples were essentially clear (slightly turbid) and did not exhibit surface stickiness. For each sample, refractive index and Abbe number values were determined using the unextracted capsules. These values are listed in Table 3.

Example 18

Under yellow light illumination, the RMM listed in Table 3 was degassed by bubbling with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a casting chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. About 350 microliters of RMM were placed in a Teflon cup and assembled on a glass plate and a stainless steel fixture, the apparatus was then transferred to a curing chamber maintained at 55 °C to 60 °C and then cured using TL03 lamps at 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were demolded manually. All samples were clear and showed slight surface tackiness. For each example, refractive index and Abbe number values were determined using the unextracted capsules. These values are listed in Table 3. In some examples, these measurements were made on the front and back surfaces of the sample. These surfaces were in contact with either the Teflon cup, the glass fixture, or the glass plates. Small differences in refractive index and Abbe number between the surfaces in contact with the Teflon and the glass were measured.

Table 3

Components (% wt.) Ex. 13 Ex. 14 Ex. 15 Ex. 16 Ex. 17 Ex. 18 CHA 52 52 52 52 52 26 EGDCA 0 0 0 0 0 26 PEA 20 20 20 20 20 20 NHA 9.36 9.36 12.36 0 0 18.86 HBA 10 9.5 7 7 7 0 PVP 90 0.5 1 0.5 0.5 0.5 0 TCDA 8 8 8 8 8 9 XLMA 0 0 0 12.36 0 0 OH-mPDMS 0 0 0 0 12.36 0 Omnirad 819 0.14 0.14 0.14 0.14 0.14 0.14 Properties Ex. 13 Ex. 14 Ex. 15 Ex. 16 Ex. 17 Ex. 18 RI (25) Teflon
1.510254 (0.000130)
Glass
1.509821 (0.000522) Teflon
1.509830 (0.000484)
Glass
1.510733 (0.000256) Teflon
1.508553 (0.001295)
Glass
1.507788 (0.001383)
Glass plates
1,509428 Glass plates
1,503340
(0.000267) Glass plates
1,502686 Teflon
1.509830 (0.000484)
Glass
1.510733 (0.000256) Abbe number (25) Teflon
51 (1)
Glass
52 (3) Teflon
54 (2)
Glass
50 (0) Teflon
51 (1)
Glass
52 (4)
Glass plates
50 (0) Glass plates
51 (0) Glass plates
51 (0) Teflon
54 (2)
Glass
50 (0)

All the above examples demonstrated the desired values of RI and Abbe number.

Examples 19-24

Under yellow light illumination, the RMMs listed in Table 4 were degassed by bubbling with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a casting chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. About 350 microliters of RMM were dispensed into a ring that was placed between two glass plates and held in place with clamps, the device was then transferred to a curing chamber maintained at 55°C to 60°C, and then cured using TL03 lamps at 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were demolded manually. The samples were transparent and did not exhibit surface stickiness. The refractive index and Abbe numbers were determined for each sample and are listed in Table 4.

Example 25

Under yellow light illumination, the RMM listed in Table 4 was degassed by bubbling with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a casting chamber containing a nitrogen gas atmosphere with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. About 350 microliters of RMM was dispensed into a ring that was placed between two glass plates and held in place with clamps, and the device was then transferred to a curing chamber maintained at about 40 °C and then cured using 430 nm LED lamps with an intensity of 18-20 mW/cm ² for about 60 minutes. The cured assemblies were manually demolded. The specimens were clear and showed no surface tack. For each specimen, the refractive index and Abbe number values were determined using the unremoved capsules. These values are listed in Table 4.

Table 4

Components (% wt.) Ex. 19 Ex. 20 Ex. 21 Ex. 22 Ex. 23 Ex. 24 Ex. 25 CHA 51.25 52 52.75 51.25 49.25 52.75 52.75 PEA 20 19 17.5 20 22 17.5 14 NHA 17.91 18,16 18.91 16.91 16.91 17.91 18.91 DMA 2 2 2 2 2 2 2 TCDA 8 8 8 9 9 9 8 UVB 0.7 0.7 0.7 0.7 0.7 0.7 0.7 HEVB 0 0 0 0 0 0 3.5 Omnirad 819 0.14 0.14 0.14 0.14 0.14 0.14 0.14 Properties Ex. 19 Ex. 20 Ex. 21 Ex. 22 Ex. 23 Ex. 24 Ex. 25 RI (25) 1.508904 (0.000018) 1.508730 (0.000045) 1.507245 (0.000290) 1.510277 (0.000040) 1.511075 (0.000443) 1.506641 (0.000394) 1.510551 (0.001891) RI (35) - - - - - 1.504755 (0.000382) - Abbe number 48.82 (0.04) 48.92 (0.09) 50.31 (1.24) 48.62 (0.20) 48.50 (0.16) 49.04 (0.27) 46.09 (0.52)

Examples 26-32

Under yellow light illumination, the RMMs listed in Table 5 were degassed by bubbling with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a casting chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. About 350 microliters of RMM were dispensed into a ring that was placed between two glass plates and held in place with clamps, the device was then transferred to a curing chamber maintained at 55°C to 60°C, and then cured using TL03 lamps at 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were demolded manually. The samples were transparent and did not exhibit surface stickiness. For each sample, the refractive index and Abbe number values were determined using the unextracted capsules. These values are listed in Table 5.

Table 5

Components
(% mass) Ex. 26 Ex. 27 Ex. 28 Ex. 29 Ex. 30 Ex. 31 Ex. 32 CHA 51.5 52 52.5 52 53 53 53 PEA 20 19 18 20 17.5 17.5 17.5 NHA 9.16 9.66 10.16 9.36 10.16 13.16 10.16 HBA 9.5 9.5 9.5 9.5 9.5 7 9.5 TCDA 8 8 8 8 8 8 8 UVB 0.7 0.7 0.7 0 0.7 0.7 0.7 PVP K90 1 1 1 1 1 0.5 0 PDMA 0 0 0 0 0 0 1 Omnirad 819 0.14 0.14 0.14 0.14 0.14 0.14 0.14 Properties Ex. 26 Ex. 27 Ex. 28 Ex. 29 Ave. 30 Ex. 31 Ex. 32 RI (25) 1.511588 (0.000146) 1.510858 (0.000032) 1.509719 (0.000539) 1.510733 (0.000256) 1.508937 (0.0001520) 1.507781 (0.000115) 1.508248 (0.000226) RI (35) - - 1.507042 (0.000272) - 1.506843 (0.000466) 1.504578 (0.000155) 1.505985 (0.000098) Abbe number (25) 48.86
(0.20) 49.35
(0.03) 49.82
(0.41) 50,00
(0.04) 49.37
(0.26) 49.95
(0.55) 49.64
(0.31) Abbe number (35) - - 49.66
(0.33) - 49.72
(0.10) 49.57
(0.05) 49.64
(0.31)

As can be seen, in Ex. 26-32 data are shown for samples prepared with components similar to the previous examples, but also using a polyamide wetting agent (PVP) and an additional hydroxybutyl acrylate monomer. Measurements with high refractive index (all over 1.5) and Abbe numbers (48-50) were noted.

Examples 33-34

Under yellow light illumination, the RMMs listed in Table 6 were degassed by bubbling with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a casting chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. About 350 microliters of RMM were dispensed into a ring that was placed between two glass plates and held in place with clamps, the device was then transferred to a curing chamber maintained at 55°C to 60°C, and then cured using TL03 lamps at 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were demolded manually. Example 33 was clear and did not exhibit surface stickiness. Example 34 was slightly cloudy and did not exhibit surface stickiness. For each example, the refractive index and Abbe number values were determined using the unextracted capsules. These values are listed in Table 6.

Table 6

Components
(% mass) Ex. 16 Ex. 33 Ex. 34 CHA 52 52.75 53 PEA 20 17.5 17.5 NHA 0 9.91 0 HBA 7 0 9.5 DMA 0 2 0 PVP 90 0.5 0 1 TCDA 8 7 8 XLMA 12.36 10 10.16 UVB 0 0.7 0 Omnirad 819 0.14 0.14 0.14 Properties Ex. 16 Ex. 33 Ex. 34 RI (25) 1,503340
(0.000267) 1.501516 (0.000131) 1.505650 (0.000164) RI (35) - 1.498512 (0.000365) 1.502645 (0.000137) Abbe number (25) 51 (0) 49.85 (1.07) 49.73 (0.23) Abbe number (35) - 49.98 (0.52) 49.57 (0.12)

Examples 35-36 and comparative examples 1-2

Reactive monomer mixtures were prepared from the formulations listed in Table 7 under yellow light. All components were accurately weighed into an amber glass bottle and tightly capped with a PTFE screw cap. The container was placed on a vibratory mill and vortexed until a homogeneous mixture was obtained. The RMM was filtered through a 0.45 µm PTFE membrane (Pall Corporation, catalog #66148) using a glass luer lock syringe and a stainless steel filter attachment and then degassed by sparging with nitrogen gas for at least 3 minutes and refilling with nitrogen gas. The degassed RMM was placed in the RMM mold space of a glove box (< 0.1% oxygen, room temperature); the cap was unscrewed; and the RMM was equilibrated for about 3 minutes before use.

Then, in a glove box under a nitrogen atmosphere with an oxygen content of less than 0.1 percent (v/v) at room temperature, using an Eppendorf pipette, 75-100 μl of the reaction mixture was applied to a mold with a frontal curvature made of polypropylene. Then, a mold with a base curvature, also made of polypropylene, was placed on the mold with a frontal curvature. Before application, the polypropylene matrices were kept in a glove box for at least twelve hours. The assembly was transferred to an adjacent glove box maintained at approximately 60-65 °C, and the lenses were polymerized top and bottom for a total of ninety minutes using 435 nm LED lamps on both sides with the following intensity profile: 20 minutes at 5 mW/ ^cm2 (top 2.5 mW/ ^cm2 and bottom 2.5 mW/ ^cm2 ), 20 minutes at 10 mW/ ^cm2 (top 5 mW/ ^cm2 and bottom 5 mW/ ^cm2 ), 20 minutes at 20 mW/ ^cm2 (top 10 mW/ ^cm2 and bottom 10 mW/ ^cm2 ), and 30 minutes at 30 mW/ ^cm2 (top 15 mW/ ^cm2 and bottom 15 mW/ ^cm2 ).

The cured assemblies were demolded manually. The base-curve molds were separated from the front-curve molds using tweezers and all flash resin was removed. The front-curve molds with lenses still attached were placed in a refrigerator at 4°C for at least one minute; the cold molds were then removed and the lenses were mechanically ejected by applying force to the back of the mold.

Example 36 was prepared according to the procedure described in Example 35, except that instead of photocuring, it was thermally cured at 60-65 °C for 72 hours. Both photocurable and thermally curable lenses were used for gloss analysis.

Polymer capsules were prepared to measure the refractive index, Abbe number, and glass transition temperature. About 350 microliters of RMM were placed inside a ring, which was placed between two glass plates and held together with clamps. The assembled assemblies were transferred to an adjacent glove box maintained at about 60-65 °C and polymerized under the photopolymerization conditions described above for the corresponding lenses. The polymer capsules for Example 36 were prepared in a similar manner, except that instead of photocuring, they were thermally cured at 60-65 °C for 72 hours.

For Example 35, the refractive index, Abbe number, and glass transition temperature were determined using the unextracted polymer capsules. These values are listed in Table 7. In addition, the glass transition temperature of Example 36 was also determined. The unextracted lenses of Example 35 and Comparative Examples 1 and 2 were analyzed for the presence of microvacuoles or the presence of microglitter according to the procedure described in the Microglitter Test Method section above, and the dark field micrographs are shown in FIG. 1. Example 35 was also analyzed for the presence of macrovacuoles or the presence of macroglitter according to the procedure described in the Macroglitter Test Method section above, and the dark field micrographs are shown in FIG. 2. Three conditions were compared. In the first condition, lenses were prepared without extraction and incubated for 3 days in PBS at 37 °C. In the second condition, lenses were prepared, extracted with acetonitrile, and dried according to the steps described above in the Macrogloss Test Method section, and then incubated for 3 days in PBS at 37°C. In the third condition, lenses were prepared, extracted with acetonitrile, dried, subjected to the gradient equilibration steps described previously in the Macrogloss Test Method section, and finally incubated for 3 days in PBS at 37°C.

Table 7

Components
(% mass) Ex. 35 Ex. 36 Comparative Ave. 1 Comparative pr. 2 EGDCA 53.14 53.10 0 0 NHA 18 17.93 0 0 PEA 0 0 36.68 51.68 PEMA 16.27 16.37 60 45 DMA 2 1.99 0 0 TCDA 8 7.97 0 0 EGDMA 0 0 3 3 HEVB 2.25 2.24 0 0 Omnirad 819 0.34 0 0.34 0.34 AIBN 0 0.40 0 0 Properties RI (25) 1,527 - - - Abbe number (25) 50 - - - T _g
(1st scan) 14.4 9.6 - - T _g
(2nd scan) 13 8.8 - -

As shown in the micrographs in FIG. 1, Example 35 contained less microglitter than the comparative examples. Under stronger gradient equilibration conditions, Example 35 exhibited a level of macroglitter not observed in a lens made without extraction or only after acetonitrile extraction and subsequent drying of the lens.

Examples 37-43

A series of RMMs (Examples 38-43) were first prepared to yield the masterbatch composition (Example 37) and then sufficient hydrophilic monomer was added to a portion of the masterbatch to yield a new RMM with the weight percentages of hydrophilic monomers shown in Table 8. These new RMMs contained approximately the same molar equivalents of hydrophilic monomers having different polymerizable functional groups that could affect their incorporation kinetics compared to other components in the RMM. Thus, from a macrogloss standpoint, it is possible to investigate the desired polymerizable functional group as well as the desired relative hydrophilicity. Following the procedure described in Example 35, lenses were prepared from the masterbatch as well as from the new RMM containing hydrophilic monomers. According to the procedure described above in the Macroglitter Test Method section, lenses were prepared, extracted with acetonitrile and dried, gradient equilibrated, and incubated for 3 days in PBS at 37°C. All lenses were analyzed for the presence of macrovacuoles or macroglitter, and darkfield micrographs are shown in FIG. 3.

Table 8

Components
(% mass) Ex. 37 Ex. 38 Ex. 39 Ex. 40 Ex. 41 Ex. 42 Ex. 43 EGDCA 89.41 TCDA 8 HEVB 2.25 Omnirad 819 0.34 The following hydrophilic monomers were dissolved in RMM pr. 37 in parts to obtain a new RMM with the listed weight percentages of hydrophilic monomers. NVP 0 16.8 0 0 0 0 0 DMA 0 0 15 0 0 0 0 HEMA 0 0 0 19.7 0 0 0 HBA 0 0 0 0 21.8 0 0 mPEG 300 0 0 0 0 0 21.8 0 PEG-OH 360 0 0 0 0 0 0 21.8

As shown in FIG. 3, when hydrophilic monomers were included in the lens formulation, the macro shine was reduced compared to the control lens from the masterbatch. The macro shine parameters in FIG. 3 are aligned with the following order in terms of severity: Control lens > NVP > DMA > mPEG 300 > HBA > HEMA > PEG-OH 360. While the reactivity of the hydrophilic monomer relative to the other reactive components in the formulation is in the following order: HBA > HEMA, PEG-OH 360, mPEG 300 > DMA > NVP, the relative hydrophilicity of the hydrophilic monomers is in the following order: DMA > NVP, PEG-OH 360 > mPEG 300 > HEMA > HBA. This indicates that the level of macroshine obtained is determined by both the reactivity of the hydrophilic monomer relative to the other reactive components in the formulation and the relative hydrophilicity of the hydrophilic monomer, the former having a more pronounced effect. DMA and NVP are more hydrophilic but react or polymerize much more slowly compared to the other reactive components in the corresponding RMM, and the resulting lenses showed the highest level of macroshine compared to the control. While HEMA, HBA, m-PEG 300 and PEG-OH 360 are less hydrophilic compared to DMA and NVP, their reactivity is comparable to the other reactive components in their corresponding RMM, and the resulting lenses showed much less macroshine compared to the control lenses and the lenses containing DMA and NVP. In the case of PEG-OH 360, the reactivity is not only comparable to that of the other reactive components in RMM, but also to the most hydrophilic monomer in this group of (meth)acrylate monomers studied, and macroglitter was virtually absent in the fabricated lenses. It was noted that the slower monomers, DMA and NVP, likely allowed for the formation of hydrophilic domains or localized regions of DMA/NVP enrichment, resulting in a non-uniform or anisotropic distribution of water in the hydrated crosslinked polymer. In an RMM in which the reactivity of the hydrophilic monomer (e.g., HEMA, HBA, mPEG 300, PEG-OH 360) is comparable to the other reactive components, there is the potential to produce a more random crosslinked polymer or network in which the hydrophilic monomer is more uniformly distributed or delocalized, resulting in a more uniform or isotropic distribution of water in the hydrated polymer.

Examples 44-51

Reactive monomer mixtures were prepared from the formulations listed in Table 9 under yellow light. All components were accurately weighed into an amber glass bottle and tightly capped with a PTFE screw cap. The container was placed on a vibratory mill and vortexed until a homogeneous mixture was obtained. The RMM was filtered through a 0.45 µm PTFE membrane (Pall Corporation, catalog #66148) using a glass luer lock syringe and a stainless steel filter attachment and then degassed by sparging with nitrogen gas for at least 3 minutes and refilling with nitrogen gas. The degassed RMM was placed in the RMM mold space of a glove box (< 0.1% oxygen, room temperature); the cap was unscrewed; and the RMM was equilibrated for about 3 minutes before use. Polymer capsules were fabricated to determine the refractive index, Abbe number, glass transition temperature and water content, and lenses were manufactured to evaluate macrogloss.

Polymer capsules In a glove box under nitrogen atmosphere with an oxygen content of less than 0.1 percent (v/v) at room temperature, using an Eppendorf pipette, about 350 μL of the reaction mixture was applied inside the ring, which was placed between two glass plates and held together with clamps, and then the device was transferred to an adjacent glove box, which was maintained at about 60-65 °C, and the capsules were cured from the top and bottom for ninety minutes using 435 nm LED lamps on both sides with the following intensity profile: 20 minutes at 5 mW/cm ² (top 2.5 mW/cm ² and bottom 2.5 mW/cm ² ), 20 minutes at 10 mW/cm ² (top 5 mW/cm ² and bottom 5 mW/cm ² ), 20 minutes at 20 mW/ ^cm2 (top 10 mW/ ^cm2 and bottom 10 mW/ ^cm2 ) and 30 minutes at 30 mW/ ^cm2 (top 15 mW/ ^cm2 and bottom 15 mW/ ^cm2 ).

The cured capsules were removed from the mold by hand. The glass plates were opened with a spatula and a razor blade. In some cases, the temperature was increased or decreased to facilitate removal from the mold. Any instant polymer was also removed. The capsules were extracted with 2-propanol and dried using the following procedure: 1) the capsules were placed in individual amber glass containers (with PTFE screw caps), about 30 mL of 2-propanol was added and placed on a tabletop orbital shaker at 100 rpm overnight at room temperature, 2) the 2-propanol was decanted completely, about 25 mL of 2-propanol was added and extraction was continued on a tabletop orbital shaker at 100 rpm for about 2 hours at room temperature, 3) the 2-propanol was decanted completely, about 25 mL of 2-propanol was added and extraction was continued on a tabletop orbital shaker at 100 rpm for about 2 hours at room temperature. 4) 2-propanol was completely decanted, the capsules were placed on a Teflon surface and left overnight to air dry, 5) the air-dried capsules on the Teflon surface were placed in a glove box at room temperature under a nitrogen atmosphere and less than 0.1 percent oxygen, which was maintained by bubbling active nitrogen, and the capsules were dried overnight, 6) the capsules on the Teflon surface were transferred to a heated glove box, which was maintained at a temperature of 60-65 °C, under a nitrogen atmosphere and less than 0.1 percent oxygen, which was maintained by actively purging nitrogen, and the capsules were dried for 3 days.

Dry capsules were used to measure refractive index, Abbe number, glass transition temperature and water content, which are listed in Table 10 for each example.

The dry refractive index and Abbe number were measured on both surfaces of the polymer capsules at 25 °C and the average value was reported. The wet refractive index on both surfaces of the polymer capsules was measured at 25 °C after suspension in PBS for 14 days at 37 °C and the average value was reported. Prior to the wet refractive index measurements, the surfaces of the polymer capsules were thoroughly blotted using lint-free blotting paper to remove surface/excess PBS. The refractive index difference (∆RI) is defined as the difference between the wet refractive index and the dry refractive index. For water content measurements, the capsules were incubated in PBS at 37 °C for 14 days and then the water content was determined using the “drying method” described previously. The water content was determined after 24, 48 and 72 hours of drying and did not change significantly over this time period, but an average value was calculated and is given in Table 10.

Lenses Then, in a glove box under a nitrogen atmosphere with an oxygen content of less than 0.1 percent (v/v) at room temperature, using an Eppendorf pipette, 75-100 μl of the reaction mixture was applied to a mold with a frontal curvature made of polypropylene. Then, a mold with a base curvature, also made of polypropylene, was placed on the mold with a frontal curvature. Before application, the polypropylene matrices were kept in a glove box for at least twelve hours. The mold assemblies were transferred to an adjacent glove box maintained at about 60-65 °C, and the lenses were polymerized from top to bottom for a total of ninety minutes using 435 nm LED lamps on both sides with the following intensity profile: 20 minutes at 5 mW/ ^cm2 (top 2.5 mW/ ^cm2 and bottom 2.5 mW/ ^cm2 ), 20 minutes at 10 mW/ ^cm2 (top 5 mW/ ^cm2 and bottom 5 mW/ ^cm2 ), 20 minutes at 20 mW/ ^cm2 (top 10 mW/ ^cm2 and bottom 10 mW/ ^cm2 ), and 30 minutes at 30 mW/ ^cm2 (top 15 mW/ ^cm2 and bottom 15 mW/cm ² ). The cured assemblies were demolded manually. The base-curve molds were separated from the front-curve molds using tweezers and all flash resin was removed. The front-curve molds with lenses still attached were placed in a refrigerator at 4°C for at least one minute; the cold molds were then removed and the lenses were mechanically ejected by applying force to the back of the mold.

In each example, the lenses were extracted with methanol, the gradient was equilibrated with PBS, and analyzed for the presence of macrovacuoles or the presence of macroglitter following the procedure described above in the Macroglitter Test Method section, and the dark field micrographs are shown in FIG. 4. The size of the macrovacuoles or macroglitter index was large enough to be counted, and the range of the number of macrovacuoles or microglitter index per lens was 4 lenses, as shown in Table 10.

Table 9

Components
(% mass) Ex. 44 Ex. 45 Ex. 46 Ex. 47 Ex. 48 Ex. 49 Ex. 50 Ex. 51 EGDCA 57.14 57.14 57.14 57.14 57.14 57.14 57.14 50.14 TCDA 6 8 6 8 8 8 8 8 EGDMA 0 0 2 0 0 0 0 0 HEVB 2.25 2.25 2.25 2.25 2.25 2.25 2.25 2.25 Omnirad 819 0.34 0.34 0.34 0.34 0.34 0.34 0.34 0.34 PEG-OH 360 22 20 20 20 20 20 20 20 PEA 12.27 12.27 12.27 0 0 0 0 0 PPA 0 0 0 12.27 0 0 0 0 CHMA 0 0 0 0 12.27 0 0 0 CHEA 0 0 0 0 0 12.27 0 0 CHPA 0 0 0 0 0 0 12.27 19.27

Table 10

Dry RI ¹ Wet RI ¹
Day 14 ∆RI Abbe number (25) ¹ T _g
(1st, 2nd scan) %WC ² Range in amount of macro glare per lens ³ Ex. 44 1.530530 (0.000059) 1.517558 (0.000194) 0,0130 47.67 (0.32) -0.7, -1.9 7.3 0 Ex. 45 1.531944 (0.000072) 1.521391 (0.000142) 0,0106 47.30 (0.09) 3.8, 4.3 6.8 0 Ex. 46 1.531600 (0.000056) 1.521489 (0.000198) 0,0101 47.05 (0.77) 4.0, 2.2 6.4 10-15 Ex. 47 1.530734 (0.000052) 1.520962 (0.000202) 0.0098 48.36 (0.48) 5.2, 3.3 6.8 0 Ex. 48 1.524031 (0.000054) 1.513001 (0.000170) 0,0110 52.68 (3.26) 3.8, 2.0 7.3 0 Ex. 49 1.523725 (0.000154) 1.513350 (0.000314) 0,0104 51.15 (0.85) -0.5, -2.1 6.9 0 Ex. 50 1.523122 (0.000041) 1.512792 (0.000320) 0,0103 52.03 (1.19) 3.0, 2.9 7.4 0 Ex. 51 1.520114 (0.000089) 1.509648 (0.000106) 0.0105 51.55 (0.21) 0.7, -0.5 7.1 0

¹ Three polymer capsules, both surfaces measured, average of six measurements

² Drying method

³ Four lenses

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, with virtually no macroglitter.

Examples 52-55

Lenses were prepared from the RMM shown in Table 11 following the procedure for Examples 44-51. In each example, the lenses were extracted with methanol, the gradient was equilibrated with PBS, and analyzed for the presence of macrovacuoles or the presence of macroglitter following the procedure described in the Macroglitter Test Method section above. Four lenses were analyzed, and FIG. 5 shows the darkfield micrographs of the highest amount of macroglitter for each example.

Table 11

Components
(% mass) Ex. 45 Ex. 52 Ex. 53 Ex. 54 Ex. 55 EGDCA 57.14 58.14 59.14 60.14 61.14 TCDA 8 9 10 11 12 HEVB 2.25 2.25 2.25 2.25 2.25 Omnirad 819 0.34 0.34 0.34 0.34 0.34 PEG-OH 360 20 18 16 14 12 PEA 12.27 12.27 12.27 12.27 12.27

In Examples 45 and 52-55, as the amount of PEG-OH 360 was decreased and the amount of TCDA was increased, the level of macrogloss increased, as shown in FIG. 5.

Examples 56-71

The polymer capsules and lenses were prepared from the RMM shown in Table 12 according to the procedure for Examples 44-51, except that for the polymer capsules only, the light source was TL03 lamps having an intensity of 5-6 mW/ ^cm2 . The refractive index, Abbe number, glass transition temperature and water content were determined for each example. These values are shown in Table 13. The dry refractive index and Abbe number were measured on both surfaces of the capsules at 25 °C and the average value was reported. The wet refractive index on both surfaces of the capsules was measured at 25 °C after suspension in PBS for 14 days at 37 °C, after which the average value was reported. Prior to the wet refractive index measurements, the capsule surfaces were thoroughly blotted with lint-free blotting paper to remove surface/excess PBS. The difference in refractive index (∆RI) is defined as the difference in the wet refractive index minus the dry refractive index. For water content measurements, dry capsules were weighed and incubated in deionized water at 37°C, and water content was determined by the “hydration method” after 7 days and 14 days. In each example, lenses were extracted with methanol, the gradient equilibrated with PBS, and analyzed for the presence of macrovacuoles or the presence of macroglitter using darkfield micrographs following the procedure described in the “Macroglitter test method” section above. The macrovacuoles or microglitter were large enough to be counted, and the range of observed macrovacuole counts or microglitter index was 4 lenses, as shown in Table 13. In each example, the lenses were extracted with methanol, dried, and analyzed for microglitter density following the procedure described in the Microglitter Test Method section above. The results, measured using dark-field micrographs, are shown in Table 13.

Table 12

Components
(% mass) Ex. 56 Ex. 57 Ex. 58 Ex. 59 Ave. 60 Ex. 61 Ex. 62 Ex. 63 PEG-OH 360 20 20 19.5 19.0 20 19.65 20 18 EGDCA 58.4 58 58 58 57 57 58.4 59.4 TCDA 8.25 8.65 9.15 9.65 9.65 10 8.25 9.25 PEA 12.5 12.5 12.5 12.5 12.5 12.5 12.5 12.5 UVB 0.70 0.70 0.70 0.70 0.70 0.70 0.70 0.70 Omnirad 819 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Components
(% mass) Ex. 64 Ex. 65 Ex. 66 Ex. 67 Ex. 68 Ex. 69 Ave. 70 Ex. 71 PEG-OH 360 17.5 17.0 16 14 12 8 4 0 EGDCA 59.65 59.9 60.4 63.15 65.15 69.15 73.15 77.15 TCDA 9.5 9.75 10.25 9.5 9.5 9.5 9.5 9.5 PEA 12.5 12.5 12.5 12.5 12.5 12.5 12.5 12.5 UVB 0.70 0.70 0.70 0.70 0.70 0.70 0.70 0.70 Omnirad 819 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15

Table 13

Dry RI ¹ Wet RI ¹
Day 14 at 37° ∆RI Abbe number (25) ¹ T _g
(1st, 2nd scan) %WC ²
Day 7, day 14,
37 °C Range in amount of macro glare per lens ³ Microgloss density
(pcs/ ^mm2 ) ⁴ Ex. 56 1.528565 (0.000305) 1.518041 (0.000632) 0.010524 48.87 (0.28) 1.6, 0.5 4.17 (0.03), 4.91 (0.03) 0 2.2 (0.8) Ex. 57 1.528501 (0.000189) 1.518271 (0.000317) 0.010230 48.84 (0.90) 4.1, 3.0 4.27 (0.04), 4.99 (0.13) 0 4.5 (1.7) Ex. 58 1.528883 (0.000145) 1.518999 (0.000423) 0.009884 49.24 (0.56) 3.4, 1.6 4.16 (0.02), 4.88 (0.02) 0 6.6 (6.2) Ex. 59 1.529389 (0.000198) 1.521356 (0.003561) 0,008032 50.01 (1.51) 4.9, 2.6 3.86 (0.15), 4.50 (0.17) 0 2.2 (1.5) Ave. 60 1.528920 (0.000263) 1.518796 (0.000581) 0.010124 48.63 (1.51) 3.5, 2.5 4.24 (0.04), 4.90 (0.03) 0 4.9 (1.2) Ex. 61 1.529030 (0.000054) 1.520164 (0.000425) 0,008866 48.34 (0.87) 3.5, 2.0 4.05 (0.04), 4.69 (0.01) 0 6.6 (4.7) Ex. 62 1.528757 (0.000068) 1.519120 (0.000365) 0,009637 49.00 (0.31) 3.3, 1.1 4.05 (0.04), 4.70 (0.02) 0 1.4 (1.0) Ex. 63 1.529983 (0.000042) 1.521921 (0.000311) 0,008062 49.16 (0.18) 7.8, 5.7 3.41 (0.06), 3.93 (0.03) ≤ 1 1.6 (0.8) Ex. 64 1.529939 (0.000053) 1.521807 (0.000417) 0,008131 49.02 (0.44) 8.1, 6.0 3.48 (0.02), 4.00 (0.02) 0 0.7 (0.3) Ex. 65 1.530455 (0.000060) 1.522924 (0.000249) 0.007531 49.19 (0.21) 8.9, 7.9 3.25 (0.03), 3.76 (0.05) ≤ 1 2.1 ((3.0) Ex. 66 1.531176 (0.000033) 1.524325 (0.000117) 0.006852 49.05 (0.56) 9.7, 8.6 2.94 (0.01), 3.41 (0.04) ≤ 3 1.9 (1.4) Ex. 67 1.532052 (0.000052) 1.526254 (0.000425) 0.005799 49.26 (0.94) 10.0, 8.5 2.53 (0.01), 2.92 (0.02) 10-20 4.0 (4.3) Ex. 68 1.532988 (0.000180) 1.532955 (0.000190) 0.000033 48.97 (1.01) 11.0, 9.5 2.14 (0.01), 2.51 (0.07) 10-15 1.3 (0.9) Ex. 69 1.535000 (0.000058) 1.534790 (0.000106) 0.000210 49.10 (0.40) 16.0, 14.7 1.46 (0.03), 1.67 (0.02) 30-50 1.5 (2.0) Ex. 70 1.536779 (0.000185) 1.536767 (0.000167) 0.000011 48.02 (1.14) 18.4, 17.2 0.89 (0.01), 1.03 (0.05) > 50 12.6 (2.6) Ex. 71 1.538655 (0.000181) 1.538398 (0.000243) 0.000257 48.01 (0.29) 21.9, 21.2 0.42 (0.02), 0.45 (0.03) > 50 2.3 (1.4)

¹ Three capsules, both surfaces, average of six measurements

² Method of hydration

³ Evaluation of four lenses completed

⁴ Average density of four lenses

For the most part, Examples 56-66 exhibited an excellent balance of properties, including refractive indices greater than about 1.52 and Abbe numbers greater than about 48, while exhibiting virtually no macrosheen and low microsheen density. When PEA was replaced by PEMA in Example 56, the dry RI was 1.528864 (0.000084); the wet RI after 14 days at 37°C was 1.520183 (0.000694); ∆ RI was 0.008681; the Abbe number at 25°C was 51.46 (4.99); the % WC on day 7 and day 14 at 37°C were 3.45 (0.03) and 4.08 (0.04), respectively; _Tg (first and second scans) were 9.7°C and 6.6°C, respectively; and the macro glitter range per lens was less than unity. FIG. 6 shows darkfield micrographs of individual lenses of Example 66 having a micro glitter density of 2.3/ ^mm2 and Example 70 having a micro glitter density of 13.3/ ^mm2 .

Examples 72-84

The polymer capsules and lenses were prepared from the RMM shown in Table 14 according to the procedure for Examples 44-51, except that for the polymer capsules only, the light source was TL03 lamps having an intensity of 5-6 mW/ ^cm2 . The refractive index, Abbe number, glass transition temperature and water content were determined for each example. These values are shown in Table 15. The dry refractive index and Abbe number were measured on both surfaces of the polymer capsules at 25 °C and the average value was reported. The wet refractive index on both surfaces of the polymer capsules was measured at 25 °C after suspension in PBS for 14 days at 37 °C, after which the average value was reported. Prior to the wet refractive index measurements, the surfaces of the polymer capsules were thoroughly blotted with lint-free blotting paper to remove surface/excess PBS. The difference in refractive index (∆RI) is defined as the difference in the wet refractive index and the dry refractive index. To measure water content, dry polymer capsules were weighed and incubated in deionized water at 37°C, and the water content was determined by the "hydration method" after 7 days and 14 days. For each example, four lenses were extracted with methanol, gradient equilibrated with PBS, and analyzed for macrovacuoles or macroshine according to the procedure described in the Macroshine Test Method section above. FIGS. 7-11 show dark field photomicrographs of the lenses with the fewest and most macrovacuoles or macroshine for each example. The lenses of Examples 72-74 were incubated for 3 days in PBS at 37°C, and the lenses of Examples 75-84 were incubated for 5 days in PBS at 37°C. Macrovacuoles or macroshine were large enough to be counted, and the range of macrovacuole counts observed for the 4 lenses is given in Table 15.

Table 14

Components
(% mass) Ex. 72 Ex. 73 Ex. 74 Ex. 75 Ex. 76 Ex. 77 Ex. 78 Ex. 79 Ave. 80 PEG-OH 360 14 15 16 14 14 15 15 15 0 PEG-OH 200 0 0 0 0 0 0 0 0 15 HEMA 4 4 4 5 6 5 6 6 6 EGDCA 62.4 61.4 61.4 61.4 60.4 60.4 59.4 59.4 59.4 TCDA 6.25 6.25 6.25 6.25 6.25 6.25 6.25 6.25 6.25 PPA 12.5 12.5 12.5 12.5 12.5 12.5 12.5 0 0 PEA 0 0 0 0 0 0 0 12.5 12.5 UVB 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0.7 Omnirad 819 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Components
(% mass) Ex. 81 Ex. 82 Ex. 83 Ex. 84 PEG-OH 360 15 15 15 0 PEG-OH 200 0 0 0 15 HEMA 6 6 6 6 EGDCA 59.4 59.4 59.4 59.4 TCDA 6.25 6.25 6.25 6.25 CHA 12.5 0 0 0 CHMA 0 12.5 0 0 CHEA 0 0 12.5 12.5 UVB 0.7 0.7 0.7 0.7 Omnirad 819 0.15 0.15 0.15 0.15

Table 15

Dry RI ¹ Wet RI ¹
Day 14 ∆RI Abbe number (25) ¹ T _g
(1st, 2nd scan) %WC ²
Day 7
Day 14
At 37°C Range in amount of macro glare per lens ³ Ex. 72 1.529262 (0.000129) 1.523412 (0.001836) 0,005850 49.55
(0.67) 1.9, 0.7 3.26 (0.09), 3.65 (0.09) 12-18 Ex. 73 1.528845 (0.000027) 1.521992 (0.001574) 0.006853 49.32
(0.54) 2.6, 1.1 3.56 (0.05), 4.08 (0.09) 2-5 Ex. 74 1.528999 (0.000085) 1.521973 (0.001536) 0,007026 49.45
(0.65) 2.7, 1.2 3.76 (0.15), 4.13 (0.15) 4-10 Ex. 75 1.529274 (0.000119) 1.522272 (0.001469) 0,007002 49.91
(1,00) 2.1, 0.5 3.21 (0.07), 3.81 (0.19) > 50 Ex. 76 1.529212 (0.000112) 1.521902 (0.001299) 0,007310 49.36
(0.33) 1.9, 0.4 3.68 (0.05), 4.12 (0.07) 30, 40 Ex. 77 1.528887 (0.000112) 1.521444 (0.001569) 0,007443 48.96
(0.80) 4.5, 3.1 3.85 (0.03), 4.36 (0.02) 2-5 Ex. 78 1.528457 (0.000349) 1.520182 (0.001691) 0.008275 50.34
(1.74) 3,4, 2,3 4.12 (0.02), 4.66 (0.01) 3-5 Ex. 79 1.529505 (0.000101) 1.521734 (0.001973) 0,007771 49.22
(0.81) 6.5, 4.8 4.27 (0.01), 4.74 (0.05) 10-17 Ave. 80 1.528683 (0.000174) 1.521098 (0.002100) 0.007586 50.26
(0.88) 1.9, 0.4 4.13 (0.01), 4.61 (0.01) 4-5 Ex. 81 1.522395 (0.000760) 1.514011 (0.001387) 0,008383 52.02
(1.50) 8.2, 5.8 4.29 (0.04), 4.79 (0.02) 6-15 Ex. 82 1.523441 (0.000095) 1.513080 (0.002679) 0.010360 51.96
(0.83) 0.7, -0.4 4.61 (0.04), 5.02 (0.02) 12-15 Ex. 83 1.522907 (0.000181) 1.514065 (0.001707) 0,008842 53.10
(1,14) 2.3, 1.0 4.40 (0.01), 4.84 (0.04) 5-10 Ex. 84 1.522877 (0.000109) 1.511672 (0.000190) 0.011205 51.72
(1.02) -4.0, -4.8 4.19 (0.05), 4.56 (0.06) 5-10

¹ Three polymer capsules, both surfaces measured, average of six measurements

² Drying method

³ Four lenses

In Examples 72-84, formulations containing 14-16 wt% PEG-OH 360 to 4-6 wt% HEMA exhibited low levels of macrogloss, as shown in FIGS. 7-11.

Examples 85-88

Under yellow light, the RMMs listed in Table 16 were degassed by bubbling with nitrogen gas for at least 3 minutes, refilling the headspace with nitrogen gas, and then immediately transferred to a casting chamber containing an atmosphere of nitrogen gas with less than 0.1% (v/v) oxygen gas and an internal ambient temperature. About 350 microliters of RMM were dispensed into a ring that was placed between two glass plates and held in place with clamps, the device was then transferred to a curing chamber maintained at 55°C to 60°C, and then cured using TL03 lamps at 3-4 mW/ ^cm2 for 15 minutes, followed by TL03 lamps at 6-7 mW/ ^cm2 for an additional 15 minutes. The cured assemblies were demolded manually. All polymer capsules were transparent and non-sticky. All polymer capsules were not solvent extracted. Dry refractive index, wet refractive index, Abbe number and water content were determined for each sample and are listed in Table 17.

The dry refractive index and Abbe number were measured on both surfaces of the polymer capsules at 25 °C and the average value was reported. The wet refractive index on both surfaces of the polymer capsules was measured at 25 °C after suspension in PBS for 7 days at 37 °C and the average value was reported. Before the wet refractive index measurements, the surfaces of the polymer capsules were thoroughly blotted using lint-free blotting paper to remove surface/excess PBS. The refractive index difference (∆RI) is defined as the difference between the wet refractive index and the dry refractive index. For water content measurements, the polymer capsules were incubated in PBS at 37 °C for 7 days and then the water content was determined using the “drying method” described previously.

Table 16

Components
(% mass) Ex. 85 Ex. 86 Ex. 87 Ex. 88 EGDCA 57.35 54.48 51,62 47.60 PEG-OH 360 22 25.90 29.80 35.26 PEMA 12.5 11.88 11.25 10.38 TCDA 8 7.60 7.20 6.64 Omnirad 819 0.15 0.14 0.14 0.12

Table 17

Dry RI ¹ Wet RI ¹
Day 7, 37° ∆RI Abbe number (25) ¹ %WC ² Ex. 85 1.526492 (0.010028) 1.516464 (0.002089) 0.010028 49.88 (0.68) 5.09 (0.06) Ex. 86 1.524288 (0.012844) 1.511445 (0.001745) 0.012844 51.00 (1.13) 7.07 (0.03) Ex. 77 1.522042 (0.000070) 1.505598 (0.000576) 0,016444 52.09 (1.86) 9.57 (0.17) Ex. 88 1.518925 (0.000275) 1.498656 (0.000496) 0.020269 51.45 (2.81) 12.34 (0.99)

¹ Three polymer capsules, both surfaces measured, average of six measurements

² Drying method

Points

For reasons of completeness, the various aspects of the description are presented in the following numbered paragraphs.

Item 1. A composition obtained by free-radical polymerization of a reactive monomer mixture containing:

a. at least one hydrophobic monomer;

b. at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers and any combinations thereof; and

c. cross-linking agent tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate;

wherein the composition has a refractive index of at least 1.45 and an Abbe number of at least 39.

Item 2. The composition according to item 1, wherein the hydrophobic monomer is a hydrophobic (meth)acrylate monomer.

Item 3. The composition according to item 2, wherein the hydrophobic (meth)acrylate is selected from an aliphatic (meth)acrylate, an aromatic (meth)acrylate, a cycloaliphatic (meth)acrylate, and any combination thereof.

Item 4. The composition according to item 3, wherein the hydrophobic (meth)acrylate is a cycloaliphatic (meth)acrylate.

Item 5. The composition of item 4, wherein the cycloaliphatic (meth) acrylate is selected from cyclohexyl (meth) acrylate, cyclohexyl PEG (meth) acrylate derivatives, cyclohexyl (meth) acrylate derivatives, cyclopentyl (meth) acrylate, cyclohexyl methyl (meth) acrylate, 2-cyclohexyl ethyl (meth) acrylate, 3-cyclohexyl propyl (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 derivatives, ethylene glycol dicyclopentenyl ether (meth) acrylate, poly(ethylene glycol) dicyclopentenyl 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,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, as well as any combination thereof.

Item 6. The composition according to item 5, wherein the cycloaliphatic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexyl methyl acrylate, cyclohexyl methyl methacrylate, 2-cyclohexyl ethyl acrylate, 2-cyclohexyl ethyl methacrylate, dicyclopentenyl ether ethylene glycol (meth)acrylate and any combination thereof.

Item 7. The composition according to item 6, wherein the cycloaliphatic (meth)acrylate is ethylene glycol dicyclopentenyl ether (meth)acrylate.

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

Item 9. The composition according to item 3, wherein the hydrophobic (meth)acrylate is an aliphatic (meth)acrylate.

Item 10. The composition of item 9, wherein the aliphatic (meth)acrylate is a C ₁ -C ₁₈ alkyl (meth)acrylate.

Item 11. The composition of item 10, wherein the C ₁ -C ₁₈ alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-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.

Item 12. The composition according to item 11, wherein the C ₁ -C ₁₈ alkyl (meth) acrylate is n-hexyl acrylate.

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

Item 14. The composition of item 3, wherein the hydrophobic (meth)acrylate is an aromatic (meth)acrylate.

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.

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

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

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

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

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

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

Item 22. The composition of item 21, wherein 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.

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

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.

Item 25. The composition according to item 23 or item 24, wherein the poly(ethylene glycol)-containing monomer has a number average molecular weight (M _n ) from about 200 g/mol to about 1000 g/mol or from about 200 g/mol to about 400 g/mol.

Item 26. The composition according to item 23, wherein the poly(ethylene glycol)-containing monomer has the formula:

,

where R ^a and R ^b are each independently selected from hydrogen and methyl, and m is an integer from 2 to 25.

Item 27. The composition of item 26, wherein R ^a is methyl and R ^b is hydrogen.

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

Item 29. The composition of any one of items 1-28, wherein the reactive monomer mixture comprises at least one hydrophilic monomer in an amount of from about 1 to about 40 wt.%, from about 10 to about 30 wt.%, from about 12 to about 22 wt.%, or from about 14 to about 20 wt.%.

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

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.

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

Item 33. The composition of any one of items 1-32, wherein the reactive monomer mixture comprises at least one hydroxyalkyl (meth)acrylate monomer in an amount of from about 1 to about 10 wt.%, from about 2 to about 8 wt.%, or from about 4 to about 6 wt.%.

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

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.

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.

Item 37. The composition according to any one of items 1-36, wherein the crosslinking agent tricyclo[5.2.1.0 ^2,6 ]decanedimethanol di(meth)acrylate is tricyclo[5.2.1.0 ^2,6 ]decanedimethanol diacrylate.

Item 38. The composition according to any one of items 1-37, in which the reactive monomer mixture comprises the cross-linking agent tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate in an amount of from about 1 to about 20% by weight, from about 3 to about 15% by weight, or from about 3 to about 10% by weight.

Item 39. The composition of any one of items 1-38, wherein 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 crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol diacrylate.

Item 40. The composition according to any one of items 1-39, wherein the reactive monomer mixture additionally comprises a polyamide.

Item 41. The composition according to item 40, wherein the polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinylacetamide), poly(dimethylacrylamide) and a copolymer or mixture thereof.

Item 42. The composition according to item 41, wherein the polyamide is poly(vinylpyrrolidone).

Item 43. The composition according to item 40, wherein the polyamide is a copolymer.

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

Item 45. The composition according to any one of items 1-44, further comprising at least one ultraviolet/high energy visible light absorbing compound in the reactive monomer mixture.

Item 46. The composition of item 45, wherein the ultraviolet/high energy visible light absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacryloxyethylphenyl)-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.

Item 47. The composition of item 45 or item 46, wherein the reactive monomer mixture comprises a UV/HEV light absorbing compound in an amount of from about 0.1 to about 5 wt.%, from about 1 to about 4 wt.%, or from about 1 to about 3 wt.%.

Item 48. The composition according to any one of items 1-47, further comprising at least one diluent in the reactive monomer mixture.

Item 49. The composition of any one of items 1-48, having a water content of from about 0% by weight to about 15% by weight, from about 1% by weight to about 10% by weight, or from about 1% by weight to about 8% by weight.

Item 50. A composition according to any one of items 1-49, which has a refractive index of at least 1.45 and an Abbe number of at least 45; wherein the composition has a refractive index of at least 1.48 and an Abbe number of at least 50; or wherein the composition has a refractive index of at least 1.50 and an Abbe number of at least 50.

Item 51. The composition according to any one of items 1-50, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator.

Item 52. An ophthalmic device comprising a composition according to any one of items 1-51.

Item 53. An ophthalmic device according to item 52, which comprises an intraocular lens, a contact lens, a corneal inlay, a corneal onlay, or a corneal insert.

Item 54. An ophthalmic device according to item 53, which comprises an intraocular lens.

Item 55. A method for manufacturing an ophthalmological device, comprising:

a. providing a composition according to any one of paragraphs 1-51; and

b. formation of an ophthalmic device.

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

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

Item 58. A method for manufacturing an ophthalmological device, comprising:

a. obtaining a blank from a composition according to any one of paragraphs 1-51;

b. turning an ophthalmic device from a blank.

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

Item 60. The method of item 59, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

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

Item 62. The method according to any one of items 55-61, further comprising the step of sterilizing the ophthalmic device.

Item 63. A method for manufacturing an ophthalmological device, comprising forming the device from a composition according to any one of items 1-51.

Item 64. A composition obtained by free radical polymerization of a reactive monomer mixture containing:

a. at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring;

b. at least one monomer selected from hydrophilic monomers, hydroxyalkyl (meth)acrylate monomers, and any combination thereof;

c. at least one cross-linking agent;

wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

Item 65. The composition of item 64, wherein at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring contains two or more separate monocyclic cycloaliphatic rings or one bicyclic, tricyclic, bridged, fused and/or spirocyclic cycloaliphatic ring system.

Item 66. The composition of item 64 or item 65, wherein at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring is selected from 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, (1R,3S,5f,7r)-2-methyladamantan-2-yl(meth)acrylate, derivatives (1R,3S,5f,7r)-2-methyladamantan-2-yl PEG (meth)acrylate and derivatives of (1R,3S,5f,7r)-2-methyladamantan-2-yl (meth)acrylate and any combination thereof.

Item 67. The composition according to any one of items 64-66, wherein at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring is ethylene glycol dicyclopentenyl ether acrylate.

Item 68. The composition of any one of items 64-67, wherein the reactive monomer mixture comprises at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring in an amount of from about 40 to about 90% by weight, from about 50 to about 80% by weight, or from about 50 to about 70% by weight.

Item 69. The composition according to any one of items 64-68, wherein the reactive monomer mixture comprises at least one hydrophilic monomer.

Item 70. The composition of item 69, wherein 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.

Item 71. The composition of item 69, wherein at least one hydrophilic monomer is a poly(ethylene glycol)-containing monomer.

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.

Item 73. The composition according to item 71 or item 72, wherein the poly(ethylene glycol)-containing monomer has a number average molecular weight (M _n ) from about 200 g/mol to about 1000 g/mol or from about 200 g/mol to about 400 g/mol.

Item 74. The composition of item 71, wherein the poly(ethylene glycol)-containing monomer has the formula:

,

where R ^a and R ^b are each independently selected from hydrogen and methyl, and m is an integer from 2 to 25.

Item 75. The composition of item 74, wherein R ^a is methyl and R ^b is hydrogen.

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

Item 77, The composition of any one of items 64-76, wherein the reactive monomer mixture comprises at least one hydrophilic monomer in an amount of from about 1 to about 40 wt.%, from about 10 to about 30 wt.%, from about 12 to about 22 wt.%, or from about 14 to about 20 wt.%.

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

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.

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

Item 81. The composition of any one of items 64-80, wherein the reactive monomer mixture comprises at least one hydroxyalkyl (meth)acrylate monomer in an amount of from about 1 to about 10 wt.%, from about 2 to about 8 wt.%, or from about 4 to about 6 wt.%.

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

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

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.

Item 85. The composition according to any one of items 64-84, wherein at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring is ethylene glycol dicyclopentenyl ether acrylate, and at least one hydrophilic monomer is selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate.

Item 86. The composition according to any one of items 64-85, wherein the reactive monomer mixture further comprises at least one cycloaliphatic (meth)acrylate containing one cycloaliphatic ring.

Item 87. The composition of item 86, wherein the cycloaliphatic (meth)acrylate containing one cycloaliphatic ring has at least one cycloaliphatic group containing at least one carbon-carbon double bond.

Item 88. The composition of item 86, wherein the cycloaliphatic (meth)acrylate containing one cycloaliphatic ring is selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexyl methyl (meth)acrylate, 2-cyclohexyl ethyl (meth)acrylate, 3-cyclohexyl propyl (meth)acrylate, and any combination thereof.

Item 89. The composition of item 88, wherein the cycloaliphatic (meth)acrylate containing one cycloaliphatic 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.

Item 90. The composition of any one of items 86-89, wherein the reactive monomer mixture comprises a cycloaliphatic (meth)acrylate containing one cycloaliphatic ring in an amount of from about 10 to about 25% by weight, from about 10 to about 20% by weight, or from about 12 to about 15% by weight.

Item 91. The composition according to any one of items 64-90, wherein the reactive monomer mixture further comprises at least one aromatic (meth)acrylate.

Item 92. The composition of item 91, wherein 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.

Item 93. The composition according to item 91 or item 92, wherein at least one aromatic (meth)acrylate is 2-phenylethyl acrylate.

Item 94. The composition according to any one of items 91-93, wherein the reactive monomer mixture comprises aromatic (meth)acrylate in an amount of from about 10 to about 25% by weight, from about 10 to about 20% by weight, or from about 12 to about 15% by weight.

Item 95. The composition according to any one of items 64-94, wherein the reactive monomer mixture further comprises a hydroxyalkyl (meth)acrylate.

Item 96. The composition of item 95, wherein the hydroxyalkyl (meth)acrylate comprises a linear, branched or cyclic hydroxyalkyl group having from 1 to 25 carbon atoms.

Item 97. The composition of item 95 or item 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.

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

Item 99. The composition of any one of items 95-98, wherein the reactive monomer mixture comprises hydroxyalkyl (meth)acrylate in an amount of from about 1 to about 10 wt.%, from about 2 to about 8 wt.%, or from about 4 to about 6 wt.%.

Item 100. The composition of any one of items 64-99, wherein the crosslinking agent is selected from the group consisting of a non-cycloaliphatic crosslinking agent, a cycloaliphatic crosslinking agent, and any combination thereof.

Item 101. The composition of any one of items 64-100, wherein the crosslinking agent is a cycloaliphatic crosslinking agent comprising a cycloaliphatic group having from one to four cycloaliphatic rings.

Item 102. The composition of item 101, wherein the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate.

Item 103. The composition of any one of items 64-102, wherein the reactive monomer mixture comprises a crosslinking agent in an amount of from about 1 to about 20% by weight, from about 3 to about 15% by weight, or from about 3 to about 10% by weight.

Item 104. The composition according to any one of items 64-103, wherein the reactive monomer mixture additionally comprises a polyamide.

Item 105. The composition according to item 104, wherein the polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinylacetamide), poly(dimethylacrylamide) and a copolymer or mixture thereof.

Item 106. The composition according to item 105, wherein the polyamide is poly(vinylpyrrolidone).

Item 107. The composition according to item 104, wherein the polyamide is a copolymer.

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

Item 109. The composition of any one of items 64-108, further comprising at least one ultraviolet/high energy visible light absorbing compound in the reactive monomer mixture.

Item 110. The composition of item 109, wherein the ultraviolet/high energy visible light absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacryloyloxyethylphenyl)-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.

Item 111. The composition of item 109 or item 110, wherein the reactive monomer mixture comprises a UV/HEV light absorbing compound in an amount of from about 0.1 to about 5 wt.%, from about 1 to about 4 wt.%, or from about 1 to about 3 wt.%.

Item 112. The composition according to any one of items 64-111, further comprising at least one diluent in the reactive monomer mixture.

Item 113. The composition of any one of items 64-112, having a water content of from about 0% by weight to about 15% by weight, from about 1% by weight to about 10% by weight, or from about 1% by weight to about 8% by weight.

Item 114. A composition according to any one of items 64-113, which has a refractive index of at least 1.45 and an Abbe number of at least 45; wherein the composition has a refractive index of at least 1.48 and an Abbe number of at least 50; or wherein the composition has a refractive index of at least 1.50 and an Abbe number of at least 50.

Item 115. The composition according to any one of items 64-114, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator.

Item 116. An ophthalmic device comprising a composition according to any one of items 64-115.

Item 117. An ophthalmic device according to item 116, which comprises an intraocular lens, a contact lens, a corneal inlay, a corneal onlay, or a corneal insert.

Item 118. An ophthalmic device according to item 117, which comprises an intraocular lens.

Item 119. A method for manufacturing an ophthalmological device, comprising:

c. providing a composition according to any one of paragraphs 64-115; and

d. formation of an ophthalmological device.

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

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

Item 122. A method for manufacturing an ophthalmological device, comprising:

c. obtaining a blank from a composition according to any of paragraphs 64-115;

d. turning an ophthalmic device from a blank.

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

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

Item 125. The method according to any one of items 119-124, further comprising the step of irradiating using a femtosecond two-photon laser.

Item 126. The method according to any one of items 119-125, further comprising the step of sterilizing the ophthalmic device.

Item 127. A method of manufacturing an ophthalmological device comprising forming the device from a composition according to any one of items 64-115.

Item 128. A composition obtained by free radical polymerization of a reactive monomer mixture containing:

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 cross-linking agent;

wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

Item 129. The composition of item 128, wherein the cycloaliphatic (meth)acrylate comprises a cycloaliphatic group having from one to four cycloaliphatic rings.

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

Item 131. The composition of item 128 or item 129, wherein the cycloaliphatic (meth)acrylate is selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexyl methyl (meth)acrylate, 2-cyclohexyl ethyl (meth)acrylate, 3-cyclohexyl propyl (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, dicyclopentenyl ether of ethylene glycol (meth)acrylate, dicyclopentenyl ether poly(ethylene)glycol (meth)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.

Item 132. The composition according to item 128 or item 129, wherein the cycloaliphatic (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.

Item 133. The composition of any one of items 128-132, wherein the reactive monomer mixture comprises a cycloaliphatic (meth)acrylate in an amount of from about 20 to about 80% by weight, from about 40 to about 80% by weight, or from about 60 to about 80% by weight.

Item 134. The composition of any one of items 128-133, 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.

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

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

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

Item 138. The composition of any one of items 128-137, wherein the reactive monomer mixture comprises aromatic (meth)acrylate in an amount of from about 5 to about 50% by weight, from about 10 to about 40% by weight, or from about 15 to about 40% by weight.

Item 139. A composition according to any one of items 128-138, wherein the aliphatic (meth)acrylate comprises a linear or branched alkyl group containing from 1 to 25 carbon atoms.

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

Item 141. A composition according to any one of items 128-139, wherein the aliphatic (meth)acrylate comprises a linear alkyl group containing from 4 to 8 carbon atoms.

Item 142. The composition according to item 141, wherein the aliphatic (meth)acrylate is n-hexyl acrylate.

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

Item 141. The composition of any one of items 128-143, wherein the crosslinking agent is selected from the group consisting of a non-cycloaliphatic crosslinking agent, a cycloaliphatic crosslinking agent, and any combination thereof.

Item 145. The composition of item 144, wherein the crosslinking agent is a non-cycloaliphatic 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-hydroxypropyl(meth)acrylate)-terminated polydimethylsiloxanes, and any combination thereof.

Item 146. The composition of item 145, wherein the non-cycloaliphatic crosslinking agent is ethylene glycol dimethacrylate.

Item 147. The composition of item 146, wherein the crosslinking agent is a cycloaliphatic crosslinking agent comprising a cycloaliphatic group having from one to four cycloaliphatic rings.

Item 148. The composition of item 147, wherein the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate.

Item 149. The composition of item 148 or item 148, wherein the reactive monomer mixture comprises a cycloaliphatic crosslinking agent in an amount of from about 1 to about 20 wt.%, from about 3 to about 15 wt.%, or from about 3 to about 10 wt.%.

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

Item 151. The composition according to item 150, wherein the polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinylacetamide), poly(dimethylacrylamide) and a copolymer or mixture thereof.

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

Item 153. The composition according to item 150, wherein the polyamide is a copolymer.

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

Item 155. The composition according to any one of items 128-154, further comprising at least one hydroxysilicone monomer.

Item 156. The composition of item 155, wherein the hydroxysilicone monomer comprises polydimethylsiloxane with mono-n-butyl and mono-(2-hydroxy-3-methacryloxypropyloxy)propyl terminals, 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.

Item 157. The composition of item 155 or item 156, wherein the reactive monomer mixture comprises a hydroxysilicone monomer in an amount of from about 1 to about 25 wt.%, from about 5 to about 20 wt.%, or from about 10 to about 20 wt.%.

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

Item 159. The composition of item 158, wherein the hydroxyalkyl (meth)acrylate comprises a linear, branched or cyclic hydroxyalkyl group having from 1 to 25 carbon atoms.

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.

Item 161. The composition of item 160, wherein the hydroxyalkyl (meth)acrylate is 4-hydroxybutyl acrylate or 2-hydroxyethyl methacrylate.

Item 162. The composition of any one of items 158-161, wherein the reactive monomer mixture comprises hydroxyalkyl (meth)acrylate in an amount of from about 1 to about 25 wt.%, from about 5 to about 20 wt.%, or from about 10 to about 20 wt.%.

Item 163. The composition of any one of items 128-162, further comprising at least one ultraviolet/high energy visible light absorbing compound in the reactive monomer mixture.

Item 164. The composition of item 163, wherein the ultraviolet/high energy visible light absorbing compound is a compound of formula I, 2-(2'-hydroxy-5-methacryloyloxyethylphenyl)-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.

Item 165. The composition of item 163 or item 164, wherein the reactive monomer mixture comprises a UV/HEV light absorbing compound in an amount of from about 0.1 to about 5 wt.%, from about 1 to about 4 wt.%, or from about 1 to about 3 wt.%.

Item 166. The composition according to any one of items 128-165, further comprising at least one hydrophilic monomer.

Item 167. The composition of item 166, wherein the hydrophilic monomer is selected from vinylpyrrolidone, N-vinyl-N-methylacetamide, N-methylmethacrylamide, N-vinylacetamide, N,N-dimethylacrylamide, poly(ethyleneglycol) methyl ether (meth)acrylate, (meth)acrylate, poly(ethyleneglycol) (meth)acrylate, and any combination thereof.

Item 168. The composition of item 166, wherein the hydrophilic monomer has at least one aliphatic group containing at least one double bond.

Item 169. The composition according to any one of items 128-168, further comprising at least one diluent in the reactive monomer mixture.

Item 170. The composition of any one of items 128-169, having a water content of from about 0% by weight to about 15% by weight, from about 1% by weight to about 10% by weight, or from about 1% by weight to about 8% by weight.

Item 171. A composition according to any one of items 128-170, which has a refractive index of at least 1.45 and an Abbe number of at least 45; wherein the composition has a refractive index of at least 1.48 and an Abbe number of at least 50; or wherein the composition has a refractive index of at least 1.50 and an Abbe number of at least 50.

Item 172. The composition according to any one of items 128-171, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator.

Item 173. An ophthalmic device comprising a composition according to any one of items 128-172.

Item 174. An ophthalmic device according to item 173, which comprises an intraocular lens, a contact lens, a corneal inlay, a corneal onlay, or a corneal insert.

Item 175. An ophthalmic device according to item 174, which comprises an intraocular lens.

Item 176. A method for manufacturing an ophthalmological device, comprising:

a. providing a composition according to any one of paragraphs 128-172; and

b. formation of an ophthalmic device.

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

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

Item 179. A method for producing an ophthalmological device in which the formation is carried out in one of the following ways:

a. obtaining a blank from the composition according to any one of paragraphs 128-172 and turning an ophthalmic device from the blank; or

b. forming a lens from the composition of any one of paragraphs 128-172; or

c. forming a lens from the composition according to any one of paragraphs 128-172 and finishing the surface by mechanical treatment.

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

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

Item 182. The method according to any one of items 176-181, further comprising the step of irradiating using a femtosecond two-photon laser.

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

Item 184. A method of manufacturing an ophthalmological device comprising forming the device from a composition according to any one of items 128-172.

Item 185. A composition obtained by free radical polymerization of a reactive monomer mixture containing:

a. at least one cycloaliphatic (meth)acrylate;

b. at least one aliphatic (meth)acrylate; and

c. at least one cross-linking agent;

wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

Item 186. The composition of item 185, wherein the cycloaliphatic (meth)acrylate comprises a cycloaliphatic group having from one to four cycloaliphatic rings.

Item 187. The composition of item 185 or item 186, wherein the cycloaliphatic (meth)acrylate is selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexyl methyl (meth)acrylate, 2-cyclohexyl ethyl (meth)acrylate, 3-cyclohexyl propyl (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, dicyclopentenyl ether of ethylene glycol (meth)acrylate, dicyclopentenyl ether poly(ethylene)glycol (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, (1R,3S,5f, 7r)-2-methyladamantan-2-yl (meth) acrylate, derivatives of (1R, 3S, 5f, 7r)-2-methyladamantan-2-yl PEG (meth) acrylate and derivatives of (1R, 3S, 5f, 7r)-2-methyladamantan-2-yl (meth) acrylate and any combination thereof.

Item 188. The composition according to any one of items 185-187, wherein the cycloaliphatic (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.

Item 189. The composition of any one of items 185-188, wherein the reactive monomer mixture comprises a cycloaliphatic (meth)acrylate in an amount of from about 20 to about 80% by weight, from about 40 to about 80% by weight, or from about 60 to about 80% by weight.

Item 190. A composition according to any one of items 185-189, wherein the aliphatic (meth)acrylate comprises a linear or branched alkyl group containing from 1 to 25 carbon atoms.

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

Item 192. The composition of item 191, wherein the aliphatic (meth)acrylate is isobutyl acrylate or n-hexyl acrylate.

Item 193. The composition of any one of items 185-192, wherein the reactive monomer mixture comprises an aliphatic (meth)acrylate in an amount of from about 1 to about 40 wt.%, from about 1 to about 20 wt.%, or from about 1 to about 10 wt.%.

Item 194. The composition of any one of items 185-193, wherein the crosslinking agent is selected from a non-cycloaliphatic crosslinking agent, a cycloaliphatic crosslinking agent, and any combination thereof.

Item 195. The composition of item 194, wherein the crosslinking agent is a non-cycloaliphatic 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-hydroxypropyl(meth)acrylate)-terminated polydimethylsiloxanes, and any combination thereof.

Item 196. The composition of item 195, wherein the non-cycloaliphatic crosslinking agent is ethylene glycol dimethacrylate.

Item 197. The composition of item 194, wherein the crosslinking agent is a cycloaliphatic crosslinking agent comprising a cycloaliphatic group having from one to four cycloaliphatic rings.

Item 198. The composition of item 197, wherein the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate.

Item 199. The composition of any one of items 185-198, wherein the reactive monomer mixture comprises a crosslinking agent in an amount of from about 1 to about 20% by weight, from about 1 to about 15% by weight, or from about 1 to about 5% by weight.

Item 200. A composition according to any one of items 185-199, further comprising an aromatic (meth)acrylate.

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.

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.

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

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

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

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.

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

Item 208. The composition of any one of items 204-207, wherein the reactive monomer mixture comprises hydroxyalkyl (meth)acrylate in an amount of from about 1 to about 25 wt.%, from about 5 to about 20 wt.%, or from about 10 to about 20 wt.%.

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

Item 210. The composition of item 209, wherein 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(ethyleneglycol) methyl ether (meth)acrylate, poly(ethyleneglycol) (meth)acrylate, and any combination thereof.

Item 211. The composition according to any one of items 185-209, wherein the reactive monomer mixture additionally comprises a polyamide.

Item 212. The composition according to item 211, wherein the polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinylacetamide), poly(dimethylacrylamide) and a copolymer or mixture thereof.

Item 213. The composition according to item 212, wherein the polyamide is poly(vinylpyrrolidone).

Item 214. The composition according to item 213, wherein the polyamide is a copolymer.

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

Item 216. The composition of any one of items 185-215, further comprising at least one ultraviolet/high energy visible light absorbing compound in the reactive monomer mixture.

Item 217. The composition of item 216, wherein the ultraviolet/high energy visible light absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacryloyloxyethylphenyl)-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.

Item 218. The composition of item 216 or item 217, wherein the reactive monomer mixture comprises a UV/HEV light absorbing compound in an amount of from about 0.1 to about 5 wt.%, from about 1 to about 4 wt.%, or from about 1 to about 3 wt.%.

Item 219. The composition according to any one of items 185-218, further comprising at least one diluent in the reactive monomer mixture.

Item 220. The composition of any one of items 185-219, having a water content of from about 0% by weight to about 15% by weight, from about 1% by weight to about 10% by weight, or from about 1% by weight to about 8% by weight.

Item 221. A composition according to any one of items 185-220, which has a refractive index of at least 1.45 and an Abbe number of at least 45; wherein the composition has a refractive index of at least 1.48 and an Abbe number of at least 50; or wherein the composition has a refractive index of at least 1.50 and an Abbe number of at least 50.

Item 222. The composition according to any one of items 185-221, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator.

Item 223. An ophthalmic device comprising a composition according to any one of items 185-222.

Item 224. An ophthalmic device according to item 223, which comprises an intraocular lens, a contact lens, a corneal inlay, a corneal onlay, or a corneal insert.

Item 225. An ophthalmic device according to item 224, which comprises an intraocular lens.

Item 226. A method for manufacturing an ophthalmological device, comprising:

a. providing a composition according to any one of paragraphs 185-225; and

b. formation of an ophthalmic device.

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

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

Item 229. A method for manufacturing an ophthalmic device, comprising any of the steps of:

a. obtaining a blank from a composition according to any of paragraphs 185-225 and

b. turning the ophthalmic device from the blank.

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

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

Item 232. The method according to any one of items 226-231, further comprising the step of irradiating using a femtosecond two-photon laser.

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

Item 234. A method of manufacturing an ophthalmological device comprising forming the device from a composition according to any one of items 185-225.

Item 235. A composition obtained by free-radical polymerization of a reactive monomer mixture containing:

a. at least one hydrophobic monomer;

b. at least one acrylate monomer of the following formula (I):

(I),

where R ¹ is selected from hydrogen and methyl, and R ² is a non-aromatic functional group having at least one carbon-carbon double bond; and

c. at least one cross-linking agent.

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

Item 237. The composition of 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.

Item 238. The composition of item 237, wherein the hydrophobic (meth)acrylate is an aliphatic (meth)acrylate.

Item 239. The composition of item 238, wherein the aliphatic (meth)acrylate is a C ₁ -C ₁₈ alkyl (meth)acrylate.

Item 240. The composition of item 239, wherein the C ₁ -C ₁₈ alkyl (meth)acrylate is selected from the group consisting of ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-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.

Item 241. The composition of item 240, wherein the C ₁ -C ₁₈ alkyl (meth) acrylate is n-hexyl acrylate.

Item 242. The composition of item 237, wherein the hydrophobic (meth)acrylate is an aromatic (meth)acrylate.

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.

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

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

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

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

Item 248. The composition of item 237, wherein the hydrophobic (meth)acrylate is a cycloaliphatic (meth)acrylate.

Item 249. The composition of item 248, wherein the cycloaliphatic (meth)acrylate is selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexyl methyl (meth)acrylate, 2-cyclohexyl ethyl (meth)acrylate, 3-cyclohexyl propyl (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-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, derivatives of (1R, 3S, 5f, 7r)-2-methyladamantan-2-yl PEG (meth) acrylate and derivatives of (1R, 3S, 5f, 7r)-2-methyladamantan-2-yl (meth) acrylate and any combination thereof.

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.

Item 251. A composition according to any one of items 235-250, wherein R ² comprises an alkenyl or cycloalkenyl functional group.

Item 252. The composition of item 251, wherein R ² comprises a cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, bicyclo[2.2.1]hept-5-en-2-yl, hexahydro-1H-4,7-methanoindenyl or allyl functional group.

Item 253. A composition according to any one of items 235-250, wherein the acrylate monomer of formula (I) is selected from ((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 acrylate, 2-(cyclopenta-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-diallyl acrylamide, allyl acrylate and 2-(allyloxy)ethyl acrylate.

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

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

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.

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

Item 258. The composition of item 254, wherein the hydroxyl-containing monomer is a hydroxysilicone monomer.

Item 259. The composition of 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), polydimethylsiloxane (mPDMS) with terminal mono-n-butyl and monomethacryloxypropyl groups, and polydimethylsiloxane (OH-mPDMS) with terminal mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether and mono-n-butyl groups.

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

Item 261. The composition of item 260, wherein 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(ethyleneglycol) methyl ether (meth)acrylate, poly(ethyleneglycol) (meth)acrylate, and any combination thereof.

Item 262. The composition of any one of items 235-261, wherein the crosslinking agent is selected from the group consisting of a non-cycloaliphatic crosslinking agent, a cycloaliphatic crosslinking agent, and any combination thereof.

Item 263. The composition of item 262, wherein the crosslinking agent is a non-cycloaliphatic 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-hydroxypropyl(meth)acrylate)-terminated polydimethylsiloxanes, and any combination thereof.

Item 264. The composition of item 263, wherein the non-cycloaliphatic crosslinking agent is ethylene glycol dimethacrylate.

Item 265. The composition of item 262, wherein the crosslinking agent is a cycloaliphatic crosslinking agent comprising a cycloaliphatic group having from one to four cycloaliphatic rings.

Item 266. The composition of item 265, wherein the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate.

Item 267. The composition of any one of items 235-266, wherein the reactive monomer mixture comprises a crosslinking agent in an amount of from about 1 to about 20% by weight, from about 3 to about 15% by weight, or from about 3 to about 10% by weight.

Item 268. A composition according to any one of items 235-261, wherein the crosslinking agent has the formula:

where n is an integer between 5 and 50.

Item 269. The composition of item 268, wherein n is 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25.

Item 270. The composition according to item 269, wherein n is 20.

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

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

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

Item 274. The composition according to item 273, wherein the polyamide is selected from poly(vinylpyrrolidone), poly(N-vinyl-N-methylacetamide), poly(N-vinylacetamide), poly(dimethylacrylamide) and a copolymer or mixture thereof.

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

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

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

Item 278. The composition of any one of items 235-277, further comprising at least one ultraviolet/high energy visible light absorbing compound in the reactive monomer mixture.

Item 279. The composition of item 278, wherein the ultraviolet/high energy visible light absorbing compound is a compound of formula II, 2-(2'-hydroxy-5-methacryloxyethylphenyl)-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.

Item 280. The composition of item 278 or item 279, wherein the reactive monomer mixture comprises a UV/HEV light absorbing compound in an amount of from about 0.1 to about 5 wt.%, from about 1 to about 4 wt.%, or from about 1 to about 3 wt.%.

Item 281. The composition according to any one of items 235-280, further comprising at least one diluent in the reactive monomer mixture.

Item 282. The composition of any one of items 235-281, having a water content of from about 0% by weight to about 15% by weight, from about 1% by weight to about 10% by weight, or from about 1% by weight to about 8% by weight.

Item 283. A composition according to any one of items 235-282, which has a refractive index of at least 1.45 and an Abbe number of at least 45; wherein the composition has a refractive index of at least 1.48 and an Abbe number of at least 50; or wherein the composition has a refractive index of at least 1.50 and an Abbe number of at least 50.

Item 284. The composition according to any one of items 235-283, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator.

Item 285. An ophthalmic device comprising a composition according to any one of items 235-284.

Item 286. An ophthalmic device according to item 285, which comprises an intraocular lens, a contact lens, a corneal inlay, a corneal onlay, or a corneal insert.

Item 287. An ophthalmic device according to item 286, which comprises an intraocular lens.

Item 288. A method for manufacturing an ophthalmological device, comprising:

a. providing a composition according to any one of paragraphs 235-284; and

b. formation of an ophthalmic device.

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

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

Item 291. A method for manufacturing an ophthalmic device, comprising any of the steps of:

a. obtaining a blank from a composition according to any one of paragraphs 235-284; and

b. turning the ophthalmic device from the blank.

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

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

Item 294. The method according to any one of items 288-293, further comprising the step of irradiating using a femtosecond two-photon laser.

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

Item 296. A method of manufacturing an ophthalmological device comprising forming the device from a composition according to any one of items 235-284.

Claims (100)

1. An ophthalmic device comprising a composition obtained by free radical polymerization of a reaction mixture of monomers containing: a) at least one hydrophobic monomer; b) 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; and c) cross-linking agent tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39; and wherein the ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal onlay, or a corneal insert. 2. The device of claim 1, wherein the hydrophobic monomer is a hydrophobic (meth)acrylate monomer selected from aliphatic (meth)acrylate, aromatic (meth)acrylate, cycloaliphatic (meth)acrylate, and any combination thereof. 3. The device of claim 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 device of claim 2, wherein the hydrophobic (meth)acrylate is an aliphatic (meth)acrylate selected from C ₁ -C ₁₈ alkyl (meth)acrylates. 5. The device of claim 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. 6. The device according to any one of claims 1 to 5, wherein the crosslinking agent tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol diacrylate. 7. An ophthalmic device comprising a composition obtained by free radical polymerization of a reaction mixture of monomers containing: a) at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring; b) 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; and c) at least one crosslinking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39; and wherein the ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal onlay, or a corneal insert. 8. The device of claim 7, wherein at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring contains two or more separate monocyclic cycloaliphatic rings or one bicyclic, tricyclic, bridged, fused and/or spirocyclic cycloaliphatic ring system. 9. The device according to claim 7 or 8, wherein at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring is ethylene glycol dicyclopentenyl ether acrylate. 10. The device according to any one of claims 7 to 9, wherein the reaction mixture of monomers additionally contains at least one cycloaliphatic (meth)acrylate containing one cycloaliphatic ring. 11. The device of claim 10, wherein the cycloaliphatic (meth)acrylate containing one cycloaliphatic 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. 12. The device according to any one of claims 7 to 11, wherein the reactive mixture of monomers 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. 13. The device according to any one of claims 7-12, wherein the reactive mixture of monomers 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. 14. The device of any one of claims 7 to 13, wherein the crosslinking agent is a cycloaliphatic crosslinking agent containing a cycloaliphatic group having from one to four cycloaliphatic rings. 15. The device of claim 14, wherein the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate. 16. The device according to any one of paragraphs. 1-15, further comprising at least one diluent in the reaction monomer mixture. 17. The device of any one of claims 1-16, wherein the composition has a water content of from about 0 wt.% to about 15 wt.%, from about 1 wt.% to about 10 wt.%, or from about 1 wt.% to about 8 wt.%. 18. The device of any one of claims 1 to 17, wherein 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. 19. The device according to any one of claims 1-18, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator. 20. A composition for use in ophthalmological devices obtained by free radical polymerization of a reaction mixture of monomers containing: 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 cross-linking agent. 21. The composition according to claim 20, wherein the cycloaliphatic (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. 22. The composition of claim 20, 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. 23. The composition according to claim 20, wherein the aliphatic (meth)acrylate contains a linear or branched alkyl group containing from 1 to 25 carbon atoms or from 4 to 8 carbon atoms. 24. The composition according to claim 23, wherein the aliphatic (meth)acrylate is n-hexyl acrylate. 25. The composition of any one of claims 20 to 24, wherein the crosslinking agent is a non-cycloaliphatic 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-hydroxypropyl(meth)acrylate)-terminated polydimethylsiloxanes, and any combination thereof. 26. The composition according to any one of claims 20 to 24, wherein the crosslinking agent is a cycloaliphatic crosslinking agent containing a cycloaliphatic group having from one to four cycloaliphatic rings. 27. The composition of claim 26, wherein the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate. 28. A composition for use in ophthalmological devices obtained by free radical polymerization of a reactive monomer mixture of monomers containing: a) at least one cycloaliphatic (meth)acrylate; b) at least one aliphatic (meth)acrylate; and c) at least one cross-linking agent. 29. The composition according to claim 28, wherein the cycloaliphatic (meth)acrylate contains a cycloaliphatic group having from one to four cycloaliphatic rings. 30. The composition according to any one of claims 28, 29, wherein the cycloaliphatic (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. 31. The composition according to claim 28, wherein the aliphatic (meth)acrylate contains a linear or branched alkyl group containing from 1 to 25 carbon atoms or from 4 to 8 carbon atoms. 32. The composition of any one of claims 28 to 31, wherein the crosslinking agent is a non-cycloaliphatic 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-hydroxypropyl(meth)acrylate)-terminated polydimethylsiloxanes, and any combination thereof. 33. The composition according to any one of claims 28 to 32, wherein the crosslinking agent is a cycloaliphatic crosslinking agent containing a cycloaliphatic group having from one to four cycloaliphatic rings. 34. The composition of claim 33, wherein the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate. 35. The composition according to any one of paragraphs 28-34, further comprising an aromatic (meth)acrylate or a hydroxyalkyl (meth)acrylate. 36. A composition for use in ophthalmological devices obtained by free radical polymerization of a reaction mixture of monomers containing: a) at least one hydrophobic monomer; b) at least one acrylate monomer of the following formula (I): where R ¹ is selected from hydrogen and methyl, and R ² is a non-aromatic functional group having at least one carbon-carbon double bond containing an alkenyl or cycloalkenyl functional group; and c) at least one cross-linking agent. 37. The composition of claim 36, 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. 38. The composition according to claim 37, wherein the hydrophobic (meth)acrylate is an aliphatic (meth)acrylate selected from C ₁ -C ₁₈ alkyl (meth)acrylates. 39. The composition of claim 37, 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. 40. The composition of claim 37, wherein the hydrophobic (meth)acrylate is a cycloaliphatic (meth)acrylate selected from cyclohexyl (meth)acrylate, cyclohexyl PEG (meth)acrylate derivatives, cyclohexyl (meth)acrylate derivatives, cyclopentyl (meth)acrylate, cyclohexyl methyl (meth)acrylate, 2-cyclohexyl ethyl (meth)acrylate, 3-cyclohexyl propyl (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-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, and any combination thereof. 41. The composition of claim 36, wherein R ² comprises a cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, bicyclo[2.2.1]hept-5-en-2-yl, hexahydro-1H-4,7-methanoindenyl or allyl functional group. 42. The composition according to claim 36, wherein the acrylate monomer of formula (I) is selected from ((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, 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-(cyclohex-3-en-1-yloxy)ethoxy)ethoxy)ethyl acrylate, N,N-diallyl acrylamide, allyl acrylate and 2-(allyloxy)ethyl acrylate. 43. The composition according to any one of paragraphs. 36-42, in which the reactive mixture of monomers additionally contains hydroxyalkyl (meth)acrylate. 44. The composition of any one of claims 36 to 43, wherein the crosslinking agent is a non-cycloaliphatic 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-hydroxypropyl(meth)acrylate)-terminated polydimethylsiloxanes, and any combination thereof. 45. The composition according to any one of claims 36 to 44, wherein the crosslinking agent is a cycloaliphatic crosslinking agent containing a cycloaliphatic group having from one to four cycloaliphatic rings. 46. The composition of claim 45, wherein the cycloaliphatic crosslinking agent is tricyclo[5.2.1.0 ^2,6 ]decane dimethanol di(meth)acrylate. 47. The composition according to any one of claims 36 to 43, wherein the cross-linking agent has the formula where n is an integer between 5 and 50. 48. The composition according to any one of claims 20 to 47, further comprising at least one ultraviolet/high energy visible light absorbing compound in the reactive monomer mixture. 49. The composition of claim 48, wherein the ultraviolet/high-energy visible light absorbing compound is a compound of formula II where m and n independently represent 0, 1, 2, 3, or 4; T represents a bond, O or NR; X is O, S, NR, SO, or SO ₂ ; Y represents 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 YP _g ; R ¹ and R ² , when present, are at each occurrence independently C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ thioalkyl, C ₃ -C ₇ cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halogen), halogen, hydroxy, amino, NR ³ R ⁴ or benzyl, wherein R ³ and R ⁴ are independently H or C ₁ -C ₆ alkyl, or two adjacent R ¹ or R ² groups, together with the carbon atoms to which they are attached, combine to form a cycloalkyl or aryl ring; and EWG is an electron withdrawing group, wherein the compound of formula II is: 2-(2'-hydroxy-5-methacryloxyethylphenyl)-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. 50. The composition according to any one of claims 20-49, further comprising at least one diluent in the reactive monomer mixture. 51. The composition according to any one of claims 20-50, having a water content of from about 0 wt.% to about 15 wt.%, from about 1 wt.% to about 10 wt.%, or from about 1 wt.% to about 8 wt.%. 52. The composition of any one of claims 20 to 51, wherein 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. 53. The composition according to any one of claims 20-52, wherein the free radical polymerization is photopolymerization using a bisacylphosphine oxide initiator. 54. An ophthalmic device comprising a composition according to any one of claims 20-53, wherein the ophthalmic device comprises an intraocular lens, a contact lens, a corneal inlay, a corneal onlay, or a corneal insert. 55. A method for manufacturing an ophthalmological device, comprising: a) providing a composition as defined in any of paragraphs 20 to 53; and b) formation of an ophthalmological device. 56. The method of claim 55, further comprising the step of extracting the ophthalmic device with a solvent. 57. The method of claim 56, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution. 58. A method for manufacturing an ophthalmological device, comprising: a) obtaining a preform from a composition as defined in any of paragraphs 20-53; b) turning the ophthalmic device from the blank. 59. The method of claim 58, further comprising the step of extracting the ophthalmic device with a solvent. 60. The method of claim 59, further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution. 61. The method according to any one of paragraphs 55-58, further comprising the step of irradiating using a femtosecond two-photon laser. 62. The method according to any one of paragraphs 55-61, further comprising the step of sterilizing the ophthalmic device. 63. A method of manufacturing an ophthalmic device comprising forming the device from a composition as defined in any one of paragraphs 20-53.

Images