Ophthalmic devices with high refractive index and Abbe number

Abstract

An ophthalmic device that is a polymerization product of a monomer mixture includes (a) about 30 to about 75 weight percent of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture; (b) greater than about 25 weight percent of one or more hydrophilic monomers, based on the total weight of the monomer mixture; and (c) one or more crosslinkers, wherein the ophthalmic device has a refractive index of about 1.48 to about 1.52 and an Abbe number of 50 or greater.

Description

[Background technology]

[0001] Priority claims This application claims priority to U.S. Provisional Patent Application No. 63 / 440,790, filed January 24, 2023, entitled "Ophthalmic Devices with High Refractive Index and Abbe Number," the contents of which are incorporated herein by reference in their entirety.

[0002] One of the more common human eye disorders is the progressive clouding of the matrix of the natural lens, a condition known as a cataract. Cataracts are now commonly treated by surgically removing the cloudy natural lens and replacing it with an artificial intraocular lens (IOL) in a procedure known as cataract extraction. In extracapsular extraction, the natural lens is removed from its capsule, while leaving the posterior portion of the capsule, and preferably at least a portion of the anterior portion, in place within the eye. In this case, the capsule remains anchored to the ciliary body of the eye via the zonular fibers. The capsule continues to provide a natural barrier between the aqueous humor at the front of the eye and the vitreous humor at the back of the eye. Summary of the Invention

[0003] In one exemplary embodiment, the ophthalmic device is a polymerization product of a monomer mixture comprising: (a) about 15 to about 75 weight percent of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture; (b) greater than 25 weight percent of one or more hydrophilic monomers, based on the total weight of the monomer mixture; and (c) one or more crosslinkers, wherein the ophthalmic device has a refractive index of about 1.48 to about 1.52 and an Abbe number of 50 or greater.

[0004] According to another exemplary embodiment, a method of making an ophthalmic device includes: (a) providing a monomer mixture including: (i) about 15 to about 75 wt. % of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture; (ii) greater than 25 wt. % of one or more hydrophilic monomers, based on the total weight of the monomer mixture; and (iii) one or more crosslinkers; and (b) subjecting the monomer mixture to polymerization conditions to provide an ophthalmic device having a refractive index of about 1.48 to about 1.52 and an Abbe number of 50 or greater. DETAILED DESCRIPTION OF THE INVENTION

[0005] Various exemplary embodiments described herein relate to ophthalmic devices, such as intraocular lenses, having high refractive indices and Abbe numbers. As noted above, one of the most common human eye diseases is the progressive clouding of the matrix of the natural lens, forming a condition known as a cataract. To treat cataracts, it is now common to surgically remove the cataract-affected human lens and implant an artificial intraocular lens in place of the natural lens.

[0006] Hydrogel materials generally have a relatively low refractive index, requiring a thicker lens optic to achieve a given refractive power, making them less desirable than other materials. Silicone materials generally have a higher refractive index than hydrogels, but they tend to unfold explosively after being placed in the eye in a folded state. This explosive unfolding can damage the corneal endothelium and rupture the natural lens capsule. Acrylic materials are desirable because they typically have a higher refractive index than silicone materials and unfold more slowly or in a more controlled manner than silicone materials.

[0007] Materials used to replace the natural crystalline lens must be soft and highly flexible so that, once formed into a lens, they can be folded and passed through an incision, typically about 2 millimeters (mm). Additionally, materials must have excellent transparency and little to no sheen. A high refractive index allows for the use of thinner lenses. Materials with a high Abbe number have less dispersion, which allows for improved optical results and reduced light scattering. Therefore, a high refractive index must be combined with a high Abbe number to give the material the desired optical properties.

[0008] Thus, the ophthalmic devices described herein overcome the above problems and advantageously provide ophthalmic devices with high refractive index and Abbe number.

[0009] definition

[0010] The following definitions are provided to more clearly define the terms used herein. Unless otherwise noted, the following definitions apply to this disclosure. When a term is used in this disclosure but not specifically defined herein, the definition from the IUPAC Chemical Glossary can be applied, unless that definition conflicts with other disclosures or definitions applicable herein or would obscure or invalidate the claim to which that definition applies. To the extent that a definition or usage provided by any document incorporated by reference herein conflicts with the definition or usage provided herein, the definition or usage provided herein controls.

[0011] Although compositions and methods are described in terms "comprising" various components or steps, unless otherwise indicated, the compositions and methods can also "consist essentially of" or "consist of" the various components or steps.

[0012] The terms "a," "an," and "the" are intended to include plural alternatives (e.g., at least one). The terms "including," "with," and "having," as used herein, are defined as "comprising" (i.e., open language) unless otherwise specified.

[0013] Various numerical ranges are disclosed herein. When applicant discloses or claims any type of range, applicant's intent, unless otherwise specified, is to separately disclose or claim each numerical value that such range can reasonably encompass, including the endpoints of the ranges and any subranges and combinations of subranges encompassed therein. For example, all numerical endpoints of ranges disclosed herein are approximations unless excluded by disclaimer.

[0014] Values ​​or ranges may be expressed herein as "about" from one particular value and / or to another particular value. When such values ​​or ranges are expressed, other disclosed embodiments include the recited specific values ​​from the one particular value and / or to the other particular value. Similarly, when values ​​are expressed as approximations, it will be understood that by using the antecedent "about," the particular value forms another embodiment. It will be understood that there are several values ​​disclosed therein, and that each value is also herein disclosed as "about" that particular value in addition to the value itself. In other aspects, the use of the term "about" can mean ±20% of the stated value, ±15% of the stated value, ±10% of the stated value, ±5% of the stated value, ±3% of the stated value, or ±1% of the stated value.

[0015] Applicant reserves the right to disclaim or exclude any individual member of any such group of values ​​or ranges (including any subranges or combinations of subranges within a group) that may be claimed according to ranges or in any similar manner if, for any reason, Applicant elects to claim only a portion rather than the entire scope of the disclosure, for example, to take into account references that Applicant may not be aware of at the time of filing. Applicant further reserves the right to disclaim or exclude any member of a claimed group.

[0016] In non-limiting exemplary embodiments, the ophthalmic devices described herein are the polymerization product of a monomer mixture comprising: (a) about 30 to about 75 wt. % of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture; (b) greater than about 25 wt. % of one or more hydrophilic monomers, based on the total weight of the monomer mixture; and (c) one or more crosslinkers.

[0017] According to non-limiting exemplary embodiments, the ophthalmic devices described herein have a refractive index of about 1.48 to about 1.52 and an Abbe number of 50 or greater. In another exemplary embodiment, the ophthalmic devices described herein have a refractive index of about 1.49 to about 1.52 and an Abbe number of 50 or greater. In another exemplary embodiment, the ophthalmic devices described herein have a refractive index of about 1.49 to about 1.51 and an Abbe number of 50 or greater. In another exemplary embodiment, the ophthalmic devices described herein have a refractive index of about 1.49 to about 1.50 and an Abbe number of 50 or greater. In an exemplary embodiment, the ophthalmic devices described herein have a refractive index of about 1.50 to about 1.51 and an Abbe number of 50 or greater. In the aforementioned exemplary embodiments, the upper limit of the Abbe number can be 60 or less.

[0018] The refractive index and Abbe number are measured using an Abbe refractometer and material samples equilibrated in a balanced salt solution at 35°C before measurement.

[0019] The refractive index is defined as follows:

number

[0020] The "Abbe number", also known as the V number or convergence of a transparent material, is a measure of a material's dispersion, or the change in refractive index with wavelength, with higher V values ​​indicating lower dispersion. D ) is calculated using the following formula:

number

[0021] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the glass transition temperature (“Tg”) affecting the folding and unfolding characteristics of the ophthalmic devices described herein has an upper limit of less than about 25°C, or about 20°C or less, or about 15°C or less, or about 10°C or less, or about 5°C or less, and a lower limit of about 10°C, or about 5°C, or about 0°C, or about −5°C, or about −10°C, where any of the lower limits may be combined with any of the upper limits.

[0022] The Tg is measured by differential scanning calorimetry at 5°C / min and determined as the half height of the heat capacity increase.

[0023] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the ophthalmic devices described herein may have an equilibrium water content (EWC) that is greater than 2% and less than or equal to 9%. In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the ophthalmic devices described herein may have an equilibrium water content (EWC) that is greater than 2% and less than or equal to 6%.

[0024] In a non-limiting exemplary embodiment, component (a) of the monomer mixture comprises about 15 to about 75 weight percent of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture. In a non-limiting exemplary embodiment, component (a) of the monomer mixture comprises about 30 to about 75 weight percent of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture. In a non-limiting exemplary embodiment, component (a) of the monomer mixture comprises about 60 to about 75 weight percent of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture. In a non-limiting exemplary embodiment, component (a) of the monomer mixture comprises about 60 to about 71 weight percent of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture.

[0025] As used herein, the term "(meth)" refers to an optional methyl substituent. Thus, for example, a term such as "(meth)acrylic" refers to either methacryl or acrylic, "(meth)acrylate" refers to either methacrylate or acrylate, and "(meth)acrylamide" refers to either methacrylamide or acrylamide.

[0026] The terms "cycloalkyl" and "cycloaliphatic" are used interchangeably herein and refer to an optionally substituted cyclic hydrocarbon containing the designated number of ring carbon atoms. If no numerical value is specified, the cycloalkyl may contain 3 to 12 ring carbon atoms. In exemplary embodiments, if no numerical value is specified, the cycloalkyl may contain 3 to 10 ring carbon atoms. In exemplary embodiments, if no numerical value is specified, the cycloalkyl may contain 3 to 8 ring carbon atoms. In exemplary embodiments, if no numerical value is specified, the cycloalkyl may contain 5 to 7 ring carbon atoms. Alicyclic groups can be monocyclic, bicyclic, tricyclic, bridged, fused, and / or spirocyclic. Alicyclic groups can also have one or more double bonds if they are not fully aromatic. Suitable monocyclic alicyclic groups include, for example, C3-C8 cycloalkyl groups, C3-C7 cycloalkyl, C4-C7 cycloalkyl, and C5-C6 cycloalkyl. Representative examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc. Representative examples of substituents on cycloalkyl include one, two, or three groups independently selected from alkyl, hydroxy, amino, amido, oxa, carbonyl, alkoxy, thioalkyl, amido, carbamate, carbonate, halo, phenyl, benzyl, and combinations thereof.

[0027] Representative examples of cycloalkylalkyl groups for use herein include, by way of example, the aforementioned substituted or unsubstituted cyclic ring-containing radicals, e.g., cyclopropylmethyl, cyclobutylethyl, cyclopentylethyl, and the like, which are directly bonded to an alkyl group and then attached to the main structure of the monomer at any carbon from the alkyl group to create a stable structure, and the cyclic ring can optionally contain one or more heteroatoms, such as O and N.

[0028] The terms "alkyl" and "aliphatic" are used interchangeably herein and refer to an optionally substituted straight-chain or branched alkyl group containing the indicated number of carbon atoms. When no number is specified, the alkyl (including any substituents thereon) can contain any of 1 to 16 carbon atoms, including 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, and 16 carbon atoms. In one exemplary embodiment, the alkyl group can contain 1 to 10 carbon atoms, including 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10 carbon atoms, or 1 to 8 carbon atoms, including 1, 2, 3, 4, 5, 6, 7, and 8 carbon atoms, or 1 to 6 carbon atoms, including 1, 2, 3, and 4 carbon atoms, or 1 to 4 carbon atoms, including 1, 2, 3, and 4 carbon atoms. Representative examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, 3-ethylbutyl, etc. Representative examples of substituents on alkyl include one, two, or three groups independently selected from hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, thioalkyl, carbamate, carbonate, halogen, phenyl, benzyl, and combinations thereof.

[0029] The term "alkylene" refers to a divalent alkyl group such as, for example, -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH(CH3)CH2-, and -CH2CH2CH2CH2-.

[0030] In non-limiting exemplary embodiments, the one or more cycloaliphatic (meth)acrylic monomers include a monocyclic cycloaliphatic group and a (meth)acrylic group. In some embodiments, the monocyclic cycloaliphatic group is a C3-C8 cycloalkyl group. In non-limiting exemplary embodiments, the one or more cycloaliphatic (meth)acrylic monomers can be represented by the structure of Formula I: [ka]

[0031] In the formula, x is an integer from 0 to 17, or 1 to 9, or 1 to 5, or 1 to 4; y is an integer from 0 to 3 or 1 to 3; B is O, NR, or S; R is H, CH3, CH2CH3, or CH(CH3)2; D is O, S, or a bond; A is H or CH3; and z is 0 to 4, with the proviso that when D is a bond, at least one of y and z is 0.

[0032] In an exemplary embodiment, the one or more alicyclic (meth)acrylic monomers are represented by the structure of Formula I, where x is an integer from 1 to 4, y is 0, D is O, z is an integer from 1 to 4, B is O, and A is H or CH3.

[0033] In an exemplary embodiment, the one or more alicyclic (meth)acrylic monomers are represented by the structure of Formula I, where x is an integer from 1 to 4, y is 0, D is O, z is an integer from 2 to 3, B is O, and A is H or CH3.

[0034] In an exemplary embodiment, the one or more alicyclic (meth)acrylic monomers are represented by the structure of Formula I, where x is an integer from 1 to 4, y is an integer from 1 to 4, D is a bond, z is 0, B is O, and A is H or CH3.

[0035] In an exemplary embodiment, the one or more alicyclic (meth)acrylic monomers are represented by the structure of Formula I, where x is an integer from 1 to 4, y is 0, D is a bond, z is 0, B is O, and A is H or CH3.

[0036] In an exemplary embodiment, the (meth)acrylic group of the one or more cycloaliphatic (meth)acrylic monomers is a (meth)acrylate-containing reactive end group. Suitable (meth)acrylate-containing reactive end groups can be represented by the following structure: [ka] where R is hydrogen or methyl, and L is O, NR 1 , or S and R 1 is H, CH3, CH2CH3, or CH(CH3)2, m is an integer from 0 to 4, and R* is a linking group or a bond. Suitable linking groups include, for example, an independent, linear or branched, substituted or unsubstituted C1 to C6 alkyl group, or -OR 2 group (where R 2 is an alkyl group having 1 to 6 carbon atoms).

[0037] Suitable cycloaliphatic (meth)acrylic monomers include, for example, 2-cyclohexylethyl acrylate, 2-cyclopentylethyl acrylate, 3-cyclohexylpropyl acrylate, 3-cyclopentylpropyl acrylate, and 2-(cyclohexyloxy)ethyl acrylate. In one exemplary embodiment, the cycloaliphatic (meth)acrylic monomer used in the present invention is cyclohexylmethyl acrylate, cyclohexylethyl acrylate, or both.

[0038] The alicyclic (meth)acrylic monomers used in the present invention can be prepared by methods known in the art and are described in the examples. Also see, for example, WO2022 / 090857, the contents of which are incorporated herein by reference.

[0039] In a non-limiting exemplary embodiment that can be combined with one or more of the preceding paragraphs, component (b) of the monomer mix includes greater than about 25% by weight of one or more hydrophilic monomers, based on the total weight of the monomer mix. In a non-limiting exemplary embodiment that can be combined with one or more of the preceding paragraphs, component (b) of the monomer mix includes greater than about 25% to about 40% by weight of one or more hydrophilic monomers, based on the total weight of the monomer mix. In a non-limiting exemplary embodiment that can be combined with one or more of the preceding paragraphs, component (b) of the monomer mix includes greater than about 25% to about 35% by weight of one or more hydrophilic monomers, based on the total weight of the monomer mix.

[0040] Suitable hydrophilic monomers include, for example, unsaturated carboxylic acids, acrylamides, vinyl lactams, hydroxyl-containing (meth)acrylates, hydrophilic vinyl carbonates, hydrophilic vinyl carbamates, hydrophilic oxazolones, and poly(alkene glycols) functionalized with polymerizable groups, as well as mixtures thereof. Representative examples of unsaturated carboxylic acids include methacrylic acid, acrylic acid, and mixtures thereof. Representative examples of amides include alkylamides, such as N,N-dimethylacrylamide and N,N-dimethylmethacrylamide, as well as mixtures thereof. Representative examples of cyclic lactams include N-vinyl-2-pyrrolidone, N-vinylcaprolactam, N-vinyl-2-piperidone, and mixtures thereof. Representative examples of hydroxyl-containing (meth)acrylates include 2-hydroxyethyl methacrylate (HEMA), glycerol methacrylate, and mixtures thereof. Further examples are the hydrophilic vinyl carbonate or vinyl carbamate monomers disclosed in U.S. Patent No. 5,070,215 and the hydrophilic oxazolone monomers disclosed in U.S. Patent No. 4,910,277. Other suitable hydrophilic monomers will be apparent to those skilled in the art. Mixtures of the aforementioned hydrophilic monomers can also be used in the monomer mixtures herein.

[0041] In an exemplary embodiment, the hydrophilic monomer is one or more of an acrylamide and a hydroxyl-containing (meth)acrylate, as defined above.

[0042] In a non-limiting exemplary embodiment, the hydrophilic monomers used in the present invention can be hydrophilic monomers or homopolymers with a high glass transition temperature (Tg). A "high glass transition temperature hydrophilic monomer or homopolymer" is a hydrophilic monomer or homopolymer that, when incorporated into a polymer with one or more other monomers and a crosslinker, increases the glass transition temperature of the resulting polymer compared to a polymer formed without the high glass transition temperature hydrophilic monomer or homopolymer. In an exemplary embodiment, the hydrophilic monomers and / or their corresponding homopolymers can have a Tg value greater than 50°C, e.g., a Tg value between about 60°C and about 100°C. For example, a hydrophilic monomer such as HEMA does not have a Tg value, but when polymerized into its corresponding homopolymer (polyHEMA), the corresponding homopolymer can have a Tg value of about 60°C. Increasing the Tg value has the added benefit of reducing surface tack, which is advantageous for producing IOLs with minimal particulates and other cosmetic defects.

[0043] Thus, to achieve the desired Tg value (less than 25°C) for the ophthalmic devices described herein, a sufficient amount of one or more alicyclic (meth)acrylic monomers described above having a relatively low Tg value and a sufficient amount of a hydrophilic monomer described above having a relatively high Tg value are used in the monomer mixture.

[0044] In a non-limiting exemplary embodiment, component (c) of the monomer mixture includes one or more crosslinkers, which can be combined with one or more of the preceding paragraphs. Suitable crosslinkers for use herein are known to those skilled in the art. For example, in a non-limiting exemplary embodiment, suitable one or more crosslinkers include one or more crosslinkers comprising at least two ethylenically unsaturated reactive end groups. In one embodiment, the ethylenically unsaturated reactive end groups are (meth)acrylate-containing reactive end groups. In another embodiment, the ethylenically unsaturated reactive end groups are non-(meth)acrylate reactive end groups. In one embodiment, the ethylenically unsaturated reactive end groups are a combination of one or more (meth)acrylate-containing reactive end groups and one or more non-(meth)acrylate reactive end groups.

[0045] In an exemplary embodiment, suitable one or more crosslinkers comprising at least two ethylenically unsaturated reactive end groups include, for example, one or more di-, tri-, or tetra(meth)acrylate-containing crosslinkers. In exemplary embodiments, useful one or more di-, tri-, or tetra(meth)acrylate-containing crosslinkers include, for example, alkane polyol di-, tri-, or tetra(meth)acrylate-containing crosslinkers, such as one or more alkylene glycol di(meth)acrylate crosslinkers, one or more alkylene glycol tri(meth)acrylate crosslinkers, one or more alkylene glycol tetra(meth)acrylate crosslinkers, one or more alkane diol di(meth)acrylate crosslinkers, alkane diol tri(meth)acrylate crosslinkers, alkane diol tetra(meth)acrylate crosslinkers, agents, one or more alkane triol di(meth)acrylate crosslinkers, alkane triol tri(meth)acrylate crosslinkers, alkane triol tetra(meth)acrylate crosslinkers, agents, one or more alkane tetraol di(meth)acrylate crosslinkers, alkane tetraol tri(meth)acrylate crosslinkers, and alkane tetraol tetra(meth)acrylate crosslinkers, and mixtures thereof.

[0046] In exemplary embodiments, the one or more alkylene glycol di(meth)acrylate crosslinkers include tetraethylene glycol dimethacrylate, ethylene glycol di(meth)acrylate having up to about 10 ethylene glycol repeating units, butylene glycol di(meth)acrylate, and the like. In one embodiment, the one or more alkanediol di(meth)acrylate crosslinkers include butanediol di(meth)acrylate crosslinkers, hexanediol di(meth)acrylate, and the like. In one embodiment, the one or more alkanetriol tri(meth)acrylate crosslinkers are trimethylolpropane trimethacrylate crosslinkers. In one embodiment, the one or more alkanetetraol tetra(meth)acrylate crosslinkers are pentaerythritol tetramethacrylate crosslinkers.

[0047] In non-limiting exemplary embodiments, suitable crosslinkers include, for example, ethylene glycol diacrylate, diethylene glycol diacrylate, allyl acrylate, 1,3-propanediol diacrylate, 2,3-propanediol diacrylate, 1,6-hexanediol diacrylate, 1,4-butanediol diacrylate, triethylene glycol diacrylate, cyclohexane-1,1-diyldimethanol diacrylate, 1,4-cyclohexanediol diacrylate, 1,3-adamantanediol diacrylate, 1,3-adamantanedimethyl diacrylate, 2,2-diethyl-1,3-propanediol diacrylate, 2,2-diisobutyl-1,3-propanediol diacrylate, 1,3-cyclohexanedimethyl diacrylate, 1,4-cyclohexanedimethyl diacrylate, neopentyl glycol diacrylate, tetraethylene glycol diacrylate, polyethylene glycol diacrylate, and the corresponding methacrylates.

[0048] In non-limiting exemplary embodiments, suitable crosslinkers include, for example, 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, 1,3-propanediol diacrylate, 1,3-propanediol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, poly(ethylene glycol) diacrylate (Mn=700 Daltons), poly(ethylene glycol) dimethacrylate (Mn=700 Daltons), and poly(ethylene glycol) dimethacrylate (Mn=1000 Daltons).

[0049] In a non-limiting exemplary embodiment, which can be combined with one or more of the preceding paragraphs, the one or more crosslinking agents are present in the monomer mixture in an amount that forms an ophthalmic device. In a non-limiting exemplary embodiment, which can be combined with one or more of the preceding paragraphs, the one or more crosslinking agents are present in the monomer mixture in an amount of about 1 to about 10 wt %, based on the total weight of the monomer mixture. In a non-limiting exemplary embodiment, which can be combined with one or more of the preceding paragraphs, the one or more crosslinking agents are present in the monomer mixture in an amount of about 3 to about 5 wt %, based on the total weight of the monomer mixture.

[0050] In a non-limiting exemplary embodiment, which can be combined with one or more of the preceding paragraphs, the monomer mixture comprises one or more C3-C 12 It may further contain an aliphatic (meth)acrylate monomer. Suitable C3-C 12Aliphatic (meth)acrylate monomers include, for example, n-propyl acrylate, n-butyl acrylate, isobutyl acrylate, sec-butyl acrylate, n-hexyl acrylate, 2-ethylhexyl acrylate, n-hexyl methacrylate, and 2-ethylhexyl methacrylate. In a non-limiting exemplary embodiment, one or more C3-C6 alkyl acrylates, which may be combined with one or more of the preceding paragraphs, 12 The aliphatic (meth)acrylate monomer is present in the monomer mixture in an amount of about 15 to about 40 weight percent, based on the total weight of the monomer mixture.

[0051] In a non-limiting exemplary embodiment, which can be combined with one or more of the preceding paragraphs, the monomer mixture can further include a reactive (polymerizable) ultraviolet (UV) absorber and / or a reactive blue light absorber. Suitable reactive UV absorbers can be any known reactive UV absorber. In a non-limiting exemplary embodiment, suitable reactive UV absorbers include, for example, 2-(2'-hydroxy-3'-methallyl-5'-methylphenyl)benzotriazole (commercially available as o-methallyl Tinuvin P ("oMTP") from Polysciences, Inc., Warrington, Pennsylvania), 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenylethyl methacrylate, and 2-(3-(tert-butyl)-4-hydroxy-5-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenoxy)ethyl methacrylate.

[0052] In one exemplary embodiment, suitable UV blocking agents include, for example, one or more compounds of the following formula: [ka] [ka] (2-propenoic acid, 2-methyl, 2-(4-benzoyl-3-hydroxyphenoxy)-1-[(4-benzoyl 3-hydroxyphenoxy)methyl ester), [ka] [ka] [ka] [ka] These compounds are merely exemplary and are not intended to be limiting. Any known or later developed UV blocking agent is contemplated for use herein.

[0053] In an exemplary embodiment, the UV absorber can be present in the monomer mix in an amount ranging from about 0.1 to about 5 weight percent, based on the total weight of the monomer mix. In another exemplary embodiment, the UV absorber can be present in the monomer mix in an amount ranging from about 1.5 to about 2.5 weight percent, based on the total weight of the monomer mix. In other non-limiting exemplary embodiments, the UV absorber can be present in the monomer mix in an amount ranging from about 1.5 to about 2 weight percent, based on the total weight of the monomer mix.

[0054] Many reactive blue-light-absorbing compounds are known. Preferred reactive blue-light-absorbing compounds are disclosed in U.S. Patent Nos. 5,470,932, 8,207,244, and 8,329,775, the contents of which are incorporated herein by reference. In one embodiment, the blue-light-absorbing dye is N-2-[3-(2'-methylphenylazo)-4-hydroxyphenyl]ethyl methacrylamide. In an exemplary embodiment, the blue-light absorber can be present in the monomer mixture in an amount ranging from about 0.005 to about 1 wt %, based on the total weight of the monomer mixture. In another exemplary embodiment, the blue-light absorber can be present in the monomer mixture in an amount ranging from about 0.01 to about 1 wt %, based on the total weight of the monomer mixture.

[0055] The ophthalmic devices, e.g., intraocular lenses, of the exemplary embodiments described herein can be made by polymerizing the aforementioned monomer mixture to form a product that can then be formed into the appropriate shape by, for example, lathing, injection molding, compression molding, cutting, etc. For example, the ophthalmic devices described herein can be made by combining one or more alicyclic (meth)acrylic monomers, one or more hydrophilic monomers, and one or more crosslinkers and polymerizing the resulting mixture.

[0056] The polymerization can be accelerated by exposing the mixture to heat and / or radiation such as ultraviolet light, visible light, or high-energy radiation. A polymerization initiator can be included in the mixture to accelerate the polymerization process. Suitable polymerization initiators include thermal initiators and photoinitiators. Representative examples of free-radical thermal polymerization initiators include organic peroxides such as acetyl peroxide, lauroyl peroxide, decanoyl peroxide, stearoyl peroxide, benzoyl peroxide, peroxypivalate, and peroxydicarbonate. Suitable free radical thermal polymerization initiators include, for example, 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) (VAZO33), 2,2'-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride (VAZO44), 2,2'-azobis(2-amidinopropane) dihydrochloride (VAZO50), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO52), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO53), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO54), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO55), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO56), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO57), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO58), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO59), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO60), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO61), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO62), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO63), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO64), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO65), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO66), 2,2'-azobis(2,4- Also included are 2'-azobis(isobutyronitrile) (VAZO64 or AIBN), 2,2'-azobis-2-methylbutyronitrile (VAZO67), 1,1-azobis(1-cyclohexanecarbonitrile) (VAZO88), 2,2'-azobis(2-cyclopropylpropionitrile), 2,2'-azobis(methylisobutyric acid), 4,4'-azobis(4-cyanovaleric acid), and combinations thereof. In one embodiment, the thermal initiator is 2,2'-azobis(isobutyronitrile) (VAZO64 or AIBN).

[0057] Representative UV initiators are known in the art and include benzoin methyl ether, benzoin ethyl ether, Darocure® 1173, 1164, 2273, 1116, 2959, 3331 (EM Industries), and Irgacure® 184, 651 and 819 (Ciba-Geigy).

[0058] In an exemplary embodiment, the initiator is used in the monomer mixture in an amount ranging from about 0.01 to about 5 weight percent, based on the total weight of the monomer mixture. In another exemplary embodiment, the initiator is used in the monomer mixture in an amount ranging from about 0.01 to about 3 weight percent, based on the total weight of the monomer mixture. In another exemplary embodiment, the initiator is used in the monomer mixture in an amount ranging from about 0.01 to about 1.5 weight percent, based on the total weight of the monomer mixture.

[0059] Generally, polymerization can be carried out for about 15 minutes to about 72 hours under an inert atmosphere, such as nitrogen or argon. When using thermoplastic molds made from various types of polymer resins, the molds can be treated with an inert gas, such as nitrogen or argon, before use. The resulting crude polymerization product can be extracted using an organic solvent, such as acetone or isopropyl alcohol, to remove unreacted components or by-products typically formed during free-radical polymerization. If desired, the resulting polymerization product can be dried under vacuum, for example, for about 5 to about 72 hours, to remove residual solvent. The final product can be packaged as a dry lens or left in aqueous solution in its final packaging configuration.

[0060] If desired, it may be desirable to remove residual diluent from the lens prior to the edge finishing operation, which can be accomplished by evaporation at or near ambient pressure or under vacuum. High temperatures can be used to reduce the time required to evaporate the diluent. The time, temperature, and pressure conditions for the solvent removal step will vary depending on factors such as the volatility of the diluent and the particular monomer component, but can be readily determined by one skilled in the art. If desired, the mixture used to make the hydrogel lens may further include crosslinkers and wetting agents known in the prior art for making hydrogel materials.

[0061] The ophthalmic devices, such as intraocular lenses, obtained herein may be subjected to optional machining operations. For example, other optional machining steps may include buffing or polishing the lens edges and / or surfaces. Generally, such machining processes may be performed before or after the product is released from the mold parts; for example, the lens is dry-released from the mold by lifting the lens from the mold with vacuum tweezers, after which the lens is transferred by mechanical tweezers to a second set of vacuum tweezers and placed against a rotating surface to smooth the surface or edges. The lens may then be flipped over to machine the other side of the lens.

[0062] The lenses may then be transferred to individual lens packages containing a buffered saline solution. The saline may be added to the package either before or after the lenses are transferred. Suitable package designs and materials are known in the art. The plastic package is peelably sealed with a film. Suitable sealing films are known in the art and include foils, polymer films, and mixtures thereof. The sealed package containing the lenses is then sterilized to ensure a sterile product. Suitable sterilization means and conditions are known in the art and include, for example, autoclaving.

[0063] As one skilled in the art would readily appreciate, other steps can be included in the above-described molding and packaging process, including, for example, coating the formed lenses, surface treating the lenses during formation (e.g., via mold transfer), inspecting the lenses, discarding defective lenses, cleaning mold halves, and recycling mold halves, as well as combinations thereof.

[0064] The ophthalmic devices described herein are intended to be in direct contact with body tissues or fluids. As used herein, the term "ophthalmic device" refers to devices that reside in and on the eye. These devices may provide optical correction, wound treatment, drug delivery, diagnostic functionality, or cosmetic enhancement or effect, or a combination of these properties.

[0065] In an exemplary embodiment, the ophthalmic device includes a lens, inlay, outlay, or insert selected from an intraocular implant or lens, a contact lens, a corneal inlay, a corneal outlay, and a corneal insert.

[0066] In a non-limiting exemplary embodiment, which can be combined with one or more of the preceding paragraphs, the ophthalmic device described herein is an intraocular implant or lens. Specifically, the ophthalmic device described herein includes an intraocular implant and / or lens made at least partially or completely from the polymerized monomer mixture described herein. Such an intraocular implant or lens can include an optic and one or more haptics. For example, the polymerized monomer mixture described herein can constitute part or all of the optic of the intraocular implant or intraocular lens. In some embodiments, the optic of the implant or lens has a core made from one of the polymerized monomer mixtures described herein, surrounded by a different polymer or material. An implant or lens whose optic is made at least partially from one of the polymerized monomer mixtures described herein typically also has haptics. The haptics can be made from the polymerized monomer mixture described herein or from a different material, such as another polymer.

[0067] In some embodiments, the intraocular implant or intraocular lens is a monolithic lens having a soft, foldable central optic region and a peripheral region (haptics), both made from the same polymer. In other embodiments, the optic and haptics regions can be formed from different types of polymers or materials, if desired. Some implants or lenses can have haptics composed of different materials, e.g., one or more haptics made from the same material as the optic, while other haptics are made from a material other than the polymerized monomer mixture described herein. Multi-component implants or lenses can be made by embedding one material within another, by co-extrusion, solidifying a hard material around a soft material, or by forming an interpenetrating network of hard components around a pre-formed hydrophobic core. If one or more haptics are made from a different material than the optic of the lens, the haptics can be attached to the optic by any method known in the art, such as drilling one or more holes in the optic and inserting the haptics.

[0068] The polymerized monomer mixture described herein is designed to be foldable so that the resulting intraocular lens can be inserted into an individual's eye through a small incision. In an exemplary embodiment, the incision will be less than 2.5 mm, and in another exemplary embodiment, the incision will be less than 2 mm. The haptics of the lens tend to provide the necessary support for the implant or lens within the eye after insertion and deployment of the lens, and to help stabilize the position of the lens after insertion and incision closure. The design of the haptics is not particularly limited and can be any desired configuration, such as, for example, a plate-type or a spiral filament with graduated thickness (also known as a C-loop design).

[0069] The optic of an intraocular lens is approximately 2-6 mm in diameter before hydration. This 2-6 mm diameter is standard in the art and is typically selected to cover the pupil in its fully dilated state under natural circumstances. However, this size is not limited to any particular diameter or size of intraocular lens; other sizes are also contemplated. Furthermore, the lens optic does not have to be circular; it can be oval, square, or other shapes as desired.

[0070] The intraocular lens can further include one or more non-optical haptics extending away from the outermost surface of the optic. The haptics can be of any desired shape, such as stepped spiral filaments or flat plates, and are used to support the lens in the posterior chamber of the eye. Lenses can be fabricated with any desired design configuration. If the intraocular lens includes other components in addition to the optic and haptics, such other components can be fabricated from the same polymer as the haptics and optic, or can be fabricated from other materials as needed.

[0071] The intraocular implant or lens can be inserted into the eye by any method known in the art. For example, in one embodiment, the intraocular lens can be folded before insertion into the eye using an intraocular lens inserter or small, thin forceps of the type commonly used by ophthalmologists. After the implant or lens is positioned at the target location, it is released and unfolded. As is known in the art, a replacement lens is typically removed before inserting the intraocular lens. The intraocular lenses described herein can be made from soft, generally physiologically inert polymeric materials that provide a clear, transparent refractive lens body even after folding and unfolding. In some embodiments, the foldable intraocular lens can be inserted into any eye by injection, in which a mechanically flexible material is folded and forced through a small tube, such as a tube with an inner diameter of 1 mm to 3 mm.

[0072] The following examples are provided to enable one skilled in the art to practice the invention and are illustrative only and should not be read as limiting the scope of the invention, which is defined by the claims.

[0073] As discussed below, various polymerization products were formed and characterized by standard test procedures as follows.

[0074] Water %: Two sets of six hydrated lenses or films are blotted dry on filter paper to remove excess water and the samples are weighed (wet weight). The samples are then placed in a jar containing desiccant and heated in a microwave oven for 10 minutes. The samples are then allowed to stand for 30 minutes to equilibrate to room temperature and reweighed (dry weight). The moisture content is calculated from the wet and dry weights.

[0075] Refractive Index Test Method: Refractive index was measured using an Anton Paar Abbemat WR wavelength refractometer. The instrument was equilibrated at 25°C or 35°C for a minimum of 1 hour before use. The measurement wavelength was set to 589.3 nanometers. Using tweezers, the sample was placed on a quartz plate. The instrument lid was closed and held for 60 seconds before the refractive index was recorded. Measurements were performed on three polymer buttons and the average value reported. In cases where noted, measurements were taken on both sides of the three polymer buttons, and the average value of six measurements was reported.

[0076] Abbe Number Test Method: The refractive index at 486.1 nm and 656.3 nm was measured according to the refractive index measurement procedure at 589.3 nm. Measurements were performed on three polymer buttons, and for each polymer button, refractive index measurements at all three wavelengths were completed before the next repeat measurement was taken. The Abbe number was calculated as follows:

number

[0077] Glass transition temperature test method: Due to the thickness and / or fragility of the polymer buttons, test samples were cut from the center of the polymer buttons or lenses using a razor blade. Samples could not be punched out like thin films. Test samples were analyzed (in duplicate) under nitrogen gas atmosphere using a DSCQ2000TA instrument at a heating rate of 10°C / min and a cooling rate of 5°C / min.

[0078] The glass transition temperature was measured before and after extraction.

[0079] In the examples, the following abbreviations are used:

[0080] CHEA: 2-cyclohexylethyl acrylate

[0081] CHPA: 3-cyclohexylethyl acrylate

[0082] CHOPA: 3-(cyclohexyloxy)propyl acrylate

[0083] CyA: cyclohexyl acrylate

[0084] HEMA: 2-hydroxyethyl methacrylate

[0085] BDDA: 1,4-butanediol diacrylate

[0086] EGDMA: Ethylene glycol dimethacrylate

[0087] TEGDA: Tetraethylene glycol diacrylate

[0088] 2-EHA: 2-ethylhexyl acrylate

[0089] PEG-MA: Poly(ethylene glycol) dimethacrylate (average Mn = 750 Daltons)

[0090] NPGDA: Neopentyl glycol diacrylate

[0091] oMTP: Ortho-Methallyl Tinuvin P (2-(2H-benzo[d][1,2,3]triazol-2-yl)-4-methyl-6-(2-methylallyl)phenol)

[0092] UV416: 4-(2-acryloxyethoxy)-2-hydroxybenzophenone

[0093] AIBN: Azobisisobutyronitrile for thermosetting polymerization.

[0094] Irg819: Irgacure® 819, a photoinitiator for free radical light-cure polymerization available from SigmaAldrich.

[0095] Example 1 The synthesis of CHEA was carried out according to the following scheme. [ka]

[0096] Acrylic acid (8.43 g, 0.1170 mol, 1.5 equiv.) was dissolved in dichloromethane (150 mL) in a 500 mL round-bottom flask equipped with a magnetic stir bar. The entire system was cooled to approximately 0 °C in an ice bath, and then 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (37.38 g, 0.1950 mol, 2.5 equiv.), 2-cyclohexylethyl alcohol (10.00 g, 0.0780 mol, 1 equiv.), and 4-dimethylaminopyridine (0.95 g, 0.0078 mol, 0.1 equiv.) were added sequentially with stirring at approximately 0 °C. After the addition was complete, the flask was covered with a rubber septum and allowed to warm slowly to room temperature. The reaction mixture was stirred at room temperature for 48 h. Thin-layer chromatography was used to monitor the progress of the reaction. Upon completion of the reaction, an additional 150 mL of dichloromethane was added to the system. The mixture was washed with 1 M hydrochloric acid (3 × 300 mL), saturated sodium bicarbonate (3 × 300 mL), water (3 × 300 mL), and finally brine (2 × 300 mL). The final product was dried over anhydrous magnesium sulfate, filtered, and concentrated on a rotary evaporator. Finally, the crude product was purified by Biotage flash chromatography using a gradient elution of 1%-8% ethyl acetate in n-hexane to give the desired product, CHEA, as a clear, pale yellow oil (10.10 g, 0.0554 mol, 71% yield). 1 HNMR (400MHz, CDCl3): δppm, 6.38 (1H, dd, J=1.38, 17.4Hz), 6.11 (1H, m), 5.80 (1H, dd, J=1.35, 10.4Hz), 4.18 (2 H, t, J=6.9Hz), 1.76-1.60(5H, m), 1.59-1.52(2H, m), 1.44-1.31(1H, m), 1.30-1.08(3H, m), 1.00-0.86(2H, m).

[0097] Example 2 The synthesis of CHPA was carried out according to the following scheme. [ka]

[0098] Acrylic acid (7.60 g, 0.1055 mol, 1.5 equiv.) was dissolved in dichloromethane (150 mL) in a 500 mL round-bottom flask equipped with a magnetic stir bar. The entire system was cooled to approximately 0 °C in an ice bath, and then 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (33.69 g, 0.1758 mol, 2.5 equiv.), 3-cyclohexyl-1-propanol (10.00 g, 0.0703 mol, 1 equiv.), and 4-dimethylaminopyridine (0.86 g, 0.0070 mol, 0.1 equiv.) were added sequentially with stirring at approximately 0 °C. After the addition was complete, the flask was covered with a rubber septum and allowed to warm slowly to room temperature. The reaction mixture was stirred at room temperature for 48 h. Thin-layer chromatography was used to monitor the progress of the reaction. Upon completion of the reaction, an additional 150 mL of dichloromethane was added to the system. The mixture was washed with 1 M hydrochloric acid (3 × 300 mL), saturated sodium bicarbonate (3 × 300 mL), water (3 × 300 mL), and finally brine (2 × 300 mL). The final product was dried over anhydrous magnesium sulfate, filtered, and concentrated on a rotary evaporator. Finally, the crude product was purified by Biotage flash chromatography using a gradient elution of 1%-8% ethyl acetate in n-hexane to give the desired product, CHPA, as a clear, pale yellow oil (9.74 g, 0.0496 mol, 71% yield). 1 HNMR (400MHz, CDCl3): δppm, 6.39 (1H, dd, J=1.24, 17.33Hz), 6.11 (1H, m), 5.80 (1H, dd, J=1.2 8, 10.44Hz), 4.12 (2H, t, J=6.81Hz), 1.76-1.59 (7H, m), 1.29-1.05 (6H, m), 0.94-0.81 (2H, m).

[0099] Example 3 CHOPA was synthesized according to the following scheme. [ka]

[0100] 3-(Cyclohexyloxy)propan-1-ol (4.85 g, 30.7 mmol, 1 equiv.) was dissolved in anhydrous THF (200 mL) in a 500 mL round-bottom flask equipped with a magnetic stirrer. Acrylic anhydride (5.11 g, 40.6 mmol, 1.3 eq.), triethylamine (8.07 g, 79.7 mmol, 2.6 eq.), and 4-methoxyphenol (MEHQ, 0.100 g, 0.810 mmol) were added, and the reaction mixture was heated at 55 °C for 20 h. The solvent was removed under reduced pressure, and dichloromethane (300 mL) was added. The reaction mixture was washed with saturated sodium bicarbonate (300 mL x 3), 1 M hydrochloric acid (300 mL x 3), and water (300 mL x 3). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated on a rotary evaporator. The crude product (6.34 g, 94.5% yield) was finally purified using a Biotage flash chromatography purification system with a gradient elution of 1% to 12% ethyl acetate in n-hexane to give the desired product CHOPA as a clear, pale yellow oil. 1 The purity was confirmed to be 97.9% by HNMR (400 MHz, CDCl3).

[0101] Examples 4 to 11 A monomer mixture was made by mixing the following components listed in Table 1 in amounts per weight percent based on the total weight of the mixture. [Table 1]

[0102] The monomer mixture was molded into intraocular contact lenses (+21.0D or +34.0D) and flat disks (approximately 1 cm diameter, 0.5–1.0 mm thick). The formulation components were combined in a 20 mL scintillation vial, vortexed for 1–3 minutes, and then filtered through 1.0 μm and 0.2 μm AcroDisc PTFE syringe filters, respectively. Approximately 80–120 μL of the monomer mixture was dispensed and pressed into two polypropylene mold halves that had been stored under nitrogen for at least 20 hours before use. Thermal cure cycle: The mold assembly was placed in a preheated oven at 110°C. Samples were heated at 110°C for 20 minutes and at 100°C for 3 hours. Light-curing cycle: Samples were cast in a yellow lab with appropriate light filters and placed inside a nitrogen-filled glove box equipped with a fluorescent light fixture (UVP Ultraviolet Transilluminator, Type T-8, 15 watts, medium bi-pin) and a lamp (F15T8 / BL / 421 nm, LDC M2-7S-05Hg). The sample was placed on a borosilicate glass plate, which was placed directly on top of the lamp assembly. The instrument was turned on and the sample was allowed to cure for 2-4 hours.

[0103] Lenses and discs were removed from the molds, extracted in acetone at room temperature for 20 hours, air-dried for a minimum of 5 hours, and then vacuum-dried (1-5 mm Hg) at 60-90°C for at least 20 hours. Samples were further hydrated in deionized water for an additional 20 hours, and the equilibrium water content (EWC) was calculated: EWC = 100 × (hydrated mass - solvent-extracted dry mass) / hydrated mass. Refractive index and Abbe values ​​were measured at 20°C using a Schmidt-Hensch ATR critical angle refractometer. Refractive index (RI) measurements at 589 nm were verified using an Atago DR-M2 multi-wavelength Abbe refractometer.

[0104] Examples 12 to 19 A monomer mixture was made by mixing the following components listed in Table 2 in amounts per weight percent based on the total weight of the mixture. [Table 2]

[0105] The monomer mixture was molded into intraocular contact lenses (+21.0D or +34.0D) and flat disks (approximately 1 cm diameter, 0.5–1.0 mm thick). The formulation components were combined in a 20 mL scintillation vial, vortexed for 1–3 minutes, and then filtered through 1.0 μm and 0.2 μm AcroDisc PTFE syringe filters, respectively. Approximately 80–120 μL of the monomer mixture was dispensed and pressed into two polypropylene mold halves that had been stored under nitrogen for at least 20 hours before use. Thermal cure cycle: The mold assembly was placed in a preheated oven at 110°C. Samples were heated at 110°C for 20 minutes and at 100°C for 3 hours. Light-curing cycle: Samples were cast in a yellow lab with appropriate light filters and placed inside a nitrogen-filled glove box equipped with a fluorescent light fixture (UVP Ultraviolet Transilluminator, Type T-8, 15 watts, medium bi-pin) and a lamp (F15T8 / BL / 421 nm, LDC M2-7S-05Hg). The sample was placed on a borosilicate glass plate, which was placed directly on top of the lamp assembly. The instrument was turned on and the sample was allowed to cure for 2-4 hours.

[0106] Lenses and discs were removed from the molds, extracted in acetone at room temperature for 20 hours, air-dried for a minimum of 5 hours, and then vacuum-dried (1-5 mm Hg) at 60-90°C for at least 20 hours. Samples were further hydrated in deionized water for an additional 20 hours, and the equilibrium water content (EWC) was calculated: EWC = 100 × (hydrated mass - solvent-extracted dry mass) / hydrated mass. Refractive index and Abbe values ​​were measured at 20°C using a Schmidt-Hensch ATR critical angle refractometer. Refractive index (RI) measurements at 589 nm were verified using an Atago DR-M2 multi-wavelength Abbe refractometer.

[0107] Examples 20 to 25 A monomer mixture was made by mixing the following components listed in Table 3 in amounts per weight percent based on the total weight of the mixture. [Table 3]

[0108] The monomer mixture was molded into intraocular contact lenses (+21.0D or +34.0D) and flat disks (approximately 1 cm diameter, 0.5–1.0 mm thick). The formulation components were combined in a 20 mL scintillation vial, vortexed for 1–3 minutes, and then filtered through 1.0 μm and 0.2 μm AcroDisc PTFE syringe filters, respectively. Approximately 80–120 μL of the monomer mixture was dispensed and pressed into two polypropylene mold halves that had been stored under nitrogen for at least 20 hours before use. Thermal cure cycle: The mold assembly was placed in a preheated oven at 110°C. Samples were heated at 110°C for 20 minutes and at 100°C for 3 hours. Light-curing cycle: Samples were cast in a yellow lab with appropriate light filters and placed inside a nitrogen-filled glove box equipped with a fluorescent light fixture (UVP Ultraviolet Transilluminator, Type T-8, 15 watts, medium bi-pin) and a lamp (F15T8 / BL / 421 nm, LDC M2-7S-05Hg). The sample was placed on a borosilicate glass plate, which was placed directly on top of the lamp assembly. The instrument was turned on and the sample was allowed to cure for 2-4 hours.

[0109] Lenses and discs were removed from the molds, extracted in acetone at room temperature for 20 hours, air-dried for a minimum of 5 hours, and then vacuum-dried (1-5 mm Hg) at 60-90°C for at least 20 hours. Samples were further hydrated in deionized water for an additional 20 hours, and the equilibrium water content (EWC) was calculated: EWC = 100 × (hydrated mass - solvent-extracted dry mass) / hydrated mass. Refractive index and Abbe values ​​were measured at 20°C using a Schmidt-Hensch ATR critical angle refractometer. Refractive index (RI) measurements at 589 nm were verified using an Atago DR-M2 multi-wavelength Abbe refractometer.

[0110] Examples 26 to 28 A monomer mixture was made by mixing the following components listed in Table 4 in amounts per weight percent based on the total weight of the mixture. [Table 4]

[0111] The monomer mixture was molded into intraocular contact lenses (+21.0D or +34.0D) and flat disks (approximately 1 cm diameter, 0.5–1.0 mm thick). The formulation components were combined in a 20 mL scintillation vial, vortexed for 1–3 minutes, and then filtered through 1.0 μm and 0.2 μm AcroDisc PTFE syringe filters, respectively. Approximately 80–120 μL of the monomer mixture was dispensed and pressed into two polypropylene mold halves that had been stored under nitrogen for at least 20 hours before use. Thermal cure cycle: The mold assembly was placed in a preheated oven at 110°C. Samples were heated at 110°C for 20 minutes and at 100°C for 3 hours. Light-curing cycle: Samples were cast in a yellow lab with appropriate light filters and placed inside a nitrogen-filled glove box equipped with a fluorescent light fixture (UVP Ultraviolet Transilluminator, Type T-8, 15 watts, medium bi-pin) and a lamp (F15T8 / BL / 421 nm, LDC M2-7S-05Hg). The sample was placed on a borosilicate glass plate, which was placed directly on top of the lamp assembly. The instrument was turned on and the sample was allowed to cure for 2-4 hours.

[0112] Lenses and discs were removed from the molds, extracted in acetone at room temperature for 20 hours, air-dried for a minimum of 5 hours, and then vacuum-dried (1-5 mm Hg) at 60-90°C for at least 20 hours. Samples were further hydrated in deionized water for an additional 20 hours, and the equilibrium water content (EWC) was calculated: EWC = 100 × (hydrated mass - solvent-extracted dry mass) / hydrated mass. Refractive index and Abbe values ​​were measured at 20°C using a Schmidt-Hensch ATR critical angle refractometer. Refractive index (RI) measurements at 589 nm were verified using an Atago DR-M2 multi-wavelength Abbe refractometer.

[0113] Examples 29 to 31 A monomer mixture was made by mixing the following components listed in Table 5 in amounts per weight percent based on the total weight of the mixture. [Table 5]

[0114] The monomer mixture was molded into intraocular contact lenses (+21.0D or +34.0D) and flat disks (approximately 1 cm diameter, 0.5–1.0 mm thick). The formulation components were combined in a 20 mL scintillation vial, vortexed for 1–3 minutes, and then filtered through 1.0 μm and 0.2 μm AcroDisc PTFE syringe filters, respectively. Approximately 80–120 μL of the monomer mixture was dispensed and pressed into two polypropylene mold halves that had been stored under nitrogen for at least 20 hours before use. Thermal cure cycle: The mold assembly was placed in a preheated oven at 110°C. Samples were heated at 110°C for 20 minutes and at 100°C for 3 hours. Light-curing cycle: Samples were cast in a yellow lab with appropriate light filters and placed inside a nitrogen-filled glove box equipped with a fluorescent light fixture (UVP Ultraviolet Transilluminator, Type T-8, 15 watts, medium bi-pin) and a lamp (F15T8 / BL / 421 nm, LDC M2-7S-05Hg). The sample was placed on a borosilicate glass plate, which was placed directly on top of the lamp assembly. The instrument was turned on and the sample was allowed to cure for 2-4 hours.

[0115] Lenses and discs were removed from the molds, extracted in acetone at room temperature for 20 hours, air-dried for a minimum of 5 hours, and then vacuum-dried (1-5 mm Hg) at 60-90°C for at least 20 hours. Samples were further hydrated in deionized water for an additional 20 hours, and the equilibrium water content (EWC) was calculated: EWC = 100 × (hydrated mass - solvent-extracted dry mass) / hydrated mass. Refractive index and Abbe values ​​were measured at 20°C using a Schmidt-Hensch ATR critical angle refractometer. Refractive index (RI) measurements at 589 nm were verified using an Atago DR-M2 multi-wavelength Abbe refractometer.

[0116] Examples 32-33 A monomer mixture was made by mixing the following components listed in Table 6 in amounts per weight percent based on the total weight of the mixture. [Table 6]

[0117] The monomer mixture was molded into intraocular contact lenses (+21.0D or +34.0D) and flat disks (approximately 1 cm diameter, 0.5–1.0 mm thick). The formulation components were combined in a 20 mL scintillation vial, vortexed for 1–3 minutes, and then filtered through 1.0 μm and 0.2 μm AcroDisc PTFE syringe filters, respectively. Approximately 80–120 μL of the monomer mixture was dispensed and pressed into two polypropylene mold halves that had been stored under nitrogen for at least 20 hours before use. Thermal cure cycle: The mold assembly was placed in a preheated oven at 110°C. Samples were heated at 110°C for 20 minutes and at 100°C for 3 hours. Light-curing cycle: Samples were cast in a yellow lab with appropriate light filters and placed inside a nitrogen-filled glove box equipped with a fluorescent light fixture (UVP Ultraviolet Transilluminator, Type T-8, 15 watts, medium bi-pin) and a lamp (F15T8 / BL / 421 nm, LDC M2-7S-05Hg). The sample was placed on a borosilicate glass plate, which was placed directly on top of the lamp assembly. The instrument was turned on and the sample was allowed to cure for 2-4 hours.

[0118] Lenses and discs were removed from the molds, extracted in acetone at room temperature for 20 hours, air-dried for a minimum of 5 hours, and then vacuum-dried (1-5 mm Hg) at 60-90°C for at least 20 hours. Samples were further hydrated in deionized water for an additional 20 hours, and the equilibrium water content (EWC) was calculated: EWC = 100 × (hydrated mass - solvent-extracted dry mass) / hydrated mass. Refractive index and Abbe values ​​were measured at 20°C using a Schmidt-Hensch ATR critical angle refractometer. Refractive index (RI) measurements at 589 nm were verified using an Atago DR-M2 multi-wavelength Abbe refractometer.

[0119] According to one aspect of the present invention, the ophthalmic device is a polymerization product of a monomer mixture, the ophthalmic device comprising:

[0120] (a) about 15 to about 75 weight percent of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture;

[0121] (b) greater than 25 wt. % of one or more hydrophilic monomers, based on the total weight of the monomer mixture;

[0122] (c) one or more cross-linking agents;

[0123] Here, the ophthalmic device has a refractive index of about 1.48 to about 1.52 and an Abbe number of 50 or greater.

[0124] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more alicyclic (meth)acrylic monomers include one or more monocyclic alicyclic (meth)acrylic monomers.

[0125] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more alicyclic (meth)acrylic monomers comprise a C3-C8 cycloalkyl group and a (meth)acrylic group.

[0126] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the (meth)acrylic comprises a (meth)acrylate-containing reactive end group.

[0127] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the (meth)acrylate-containing reactive end group is represented by the structure: [ka]

[0128] wherein R is hydrogen or methyl, and L is O, NR 1 , or S and R 1is H, CH3, CH2CH3, or CH(CH3)2, m is an integer from 0 to 4, and R* is a linking group or a bond.

[0129] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, R* is selected from the group consisting of a linear or branched, substituted or unsubstituted C1-C6 alkyl group, and -OR 2 groups, and R 2 is an alkyl group having 1 to 6 carbon atoms.

[0130] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, L is O, m is 1-4, and R* is a bond.

[0131] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more cycloaliphatic (meth)acrylic monomers are represented by the structure of Formula I: [ka]

[0132] In the formula, x is an integer from 0 to 9, y is an integer from 0 to 3, B is O, NR, or S, R is H, CH3, CH2CH3, or CH(CH3)2, D is O, S, or a bond, A is H or CH3, and z is 0 to 4, with the proviso that when D is a bond, at least one of y and z is 0.

[0133] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, x is an integer from 1 to 4, y is 0, D is O, z is an integer from 1 to 4, B is O, and A is H or CH3.

[0134] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, x is an integer from 1 to 4, y is an integer from 1 to 4, D is a bond, z is 0, B is O, and A is H or CH3.

[0135] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more hydrophilic monomers are selected from the group consisting of unsaturated carboxylic acids, acrylamides, vinyl lactams, hydroxyl-containing (meth)acrylates, hydrophilic vinyl carbonates, hydrophilic vinyl carbamate monomers, hydrophilic oxazolone monomers, and mixtures thereof.

[0136] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more hydrophilic monomers are one or more of 2-hydroxyethyl methacrylate and N,N-dimethylacrylamide.

[0137] In one or more additional non-limiting exemplary embodiments, which can be combined with one or more of the preceding paragraphs, the one or more hydrophilic monomers comprise greater than 25% to about 40% by weight, based on the total weight of the monomer mixture.

[0138] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more crosslinkers are selected from the group consisting of 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, ethylene glycol dimethacrylate, (diethylene glycol) diacrylate, (diethylene glycol) dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, 1,3-propanediol diacrylate, 1,3-propanediol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, and poly(ethylene glycol) dimethacrylate.

[0139] In one or more additional non-limiting exemplary embodiments, which can be combined with one or more of the preceding paragraphs, the one or more crosslinking agents comprise from about 1% to about 10% by weight, based on the total weight of the monomer mixture.

[0140] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more crosslinkers comprise about 3% to about 5% by weight of ethylene glycol dimethacrylate, based on the total weight of the monomer mixture.

[0141] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the monomer mixture comprises:

[0142] (a) about 30 to about 75 weight percent of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture;

[0143] (b) greater than 25 wt. % to about 40 wt. % of one or more hydrophilic monomers, based on the total weight of the monomer mixture;

[0144] (c) about 1 to about 10 wt % of one or more crosslinking agents, based on the total weight of the monomer mixture.

[0145] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the ophthalmic device further comprises one or more of a reactive ultraviolet absorber and a reactive blue light absorber.

[0146] In one or more additional non-limiting exemplary embodiments, which can be combined with one or more of the preceding paragraphs, the monomer mixture comprises from about 0.1 to about 5 wt. % of a reactive UV absorber, based on the total weight of the monomer mixture.

[0147] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the monomer mixture may comprise one or more C3-C 12 It further comprises an aliphatic (meth)acrylate monomer.

[0148] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the ophthalmic device has a Tg of less than 25°C.

[0149] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the ophthalmic device has an equilibrium water content (EWC) that is greater than 2% and less than or equal to 9%.

[0150] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the ophthalmic device is a thermoset polymerization product.

[0151] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the ophthalmic device is an intraocular lens.

[0152] According to another aspect of the present invention, a method of making an ophthalmic device includes:

[0153] (a)

[0154] (i) about 15 to about 75 weight percent of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture;

[0155] (ii) greater than 25 wt. % of one or more hydrophilic monomers, based on the total weight of the monomer mixture;

[0156] (iii) providing a monomer mixture comprising one or more crosslinkers;

[0157] (b) subjecting the monomer mixture to polymerization conditions to obtain an ophthalmic device having a refractive index of about 1.48 to about 1.52 and an Abbe number of 50 or greater.

[0158] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more alicyclic (meth)acrylic monomers include one or more monocyclic alicyclic (meth)acrylic monomers.

[0159] In one or more additional non-limiting exemplary embodiments, which can be combined with one or more of the preceding paragraphs, the one or more alicyclic (meth)acrylic monomers comprise a C3-C8 cycloalkyl group and a (meth)acrylic group.

[0160] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the (meth)acrylic group comprises a (meth)acrylate-containing reactive end group.

[0161] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the (meth)acrylate-containing reactive end group is represented by the structure: [ka]

[0162] where R is hydrogen or methyl, and L is O, NR 1 , or S and R 1 is H, CH3, CH2CH3, or CH(CH3)2, m is an integer from 0 to 4, and R* is a linking group or a bond.

[0163] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, R* is selected from the group consisting of a linear or branched, substituted or unsubstituted C1-C6 alkyl group, and -OR 2 groups, and R 2 is an alkyl group from 1 to 6 carbon atoms.

[0164] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, L is O, m is 1-4, and R* is a bond.

[0165] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more cycloaliphatic (meth)acrylic monomers are represented by the structure of Formula I: [ka]

[0166] In the formula, x is an integer from 0 to 9, y is an integer from 0 to 3, B is O, NR, or S, R is H, CH3, CH2CH3, or CH(CH3)2, D is O, S, or a bond, A is H or CH3, and z is 0 to 4, with the proviso that when D is a bond, at least one of y and z is 0.

[0167] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, x is an integer from 1 to 4, y is 0, D is O, z is an integer from 1 to 4, B is O, and A is H or CH3.

[0168] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, x is an integer from 1 to 4, y is an integer from 1 to 4, D is a bond, z is 0, B is O, and A is H or CH3.

[0169] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more hydrophilic monomers are selected from the group consisting of unsaturated carboxylic acids, acrylamides, vinyl lactams, hydroxyl-containing (meth)acrylates, hydrophilic vinyl carbonates, hydrophilic vinyl carbamate monomers, hydrophilic oxazolone monomers, and mixtures thereof.

[0170] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more hydrophilic monomers are one or more of 2-hydroxyethyl methacrylate and N,N-dimethylacrylamide.

[0171] In one or more additional non-limiting exemplary embodiments, which can be combined with one or more of the preceding paragraphs, the one or more hydrophilic monomers comprise greater than 25% to about 40% by weight, based on the total weight of the monomer mixture.

[0172] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more crosslinkers are selected from the group consisting of 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, ethylene glycol dimethacrylate, (diethylene glycol) diacrylate, (diethylene glycol) dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, 1,3-propanediol diacrylate, 1,3-propanediol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, and poly(ethylene glycol) dimethacrylate.

[0173] In one or more additional non-limiting exemplary embodiments, which can be combined with one or more of the preceding paragraphs, the one or more crosslinking agents comprise from about 1% to about 10% by weight, based on the total weight of the monomer mixture.

[0174] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the one or more crosslinkers comprise about 3% to about 5% by weight of ethylene glycol dimethacrylate, based on the total weight of the monomer mixture.

[0175] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the monomer mixture comprises:

[0176] (i) about 30 to about 75 weight percent of one or more alicyclic (meth)acrylic monomers, based on the total weight of the monomer mixture;

[0177] (ii) greater than 25 wt. % to about 40 wt. % of one or more hydrophilic monomers, based on the total weight of the monomer mixture;

[0178] (iii) about 1 to about 10 weight percent of one or more crosslinking agents, based on the total weight of the monomer mixture.

[0179] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the monomer mixture further includes one or more of a reactive ultraviolet absorber and a reactive blue light absorber.

[0180] In one or more additional non-limiting exemplary embodiments, which can be combined with one or more of the preceding paragraphs, the monomer mixture comprises from about 0.1 to about 5 wt. % of a reactive UV absorber, based on the total weight of the monomer mixture.

[0181] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the monomer mixture may comprise one or more C3-C 12 It further comprises an aliphatic (meth)acrylate monomer.

[0182] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the ophthalmic device has a Tg of less than 25°C.

[0183] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the ophthalmic device has an equilibrium water content (EWC) that is greater than 2% and less than or equal to 9%.

[0184] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, subjecting the monomer mixture to polymerization conditions includes subjecting the monomer mixture to thermosetting polymerization conditions.

[0185] In one or more additional non-limiting exemplary embodiments, which may be combined with one or more of the preceding paragraphs, the ophthalmic device is an intraocular lens.

[0186] For brevity, various features disclosed herein are described in the context of a single embodiment, but may also be provided separately or in any suitable subcombination. All combinations of embodiments are specifically embraced by the exemplary embodiments disclosed herein, just as if each and every combination were individually and expressly disclosed. In addition, all subcombinations listed in the embodiments describing such variables are also specifically embraced by the compositions of the present invention, and are disclosed herein, just as if each and every such subcombination were individually and expressly disclosed herein.

[0187] It is understood that various modifications may be made to the embodiments disclosed herein. Therefore, the above description should not be construed as limiting, but merely as exemplifications of preferred embodiments. For example, the functions described above and implemented as the best mode for operating the invention are for illustrative purposes only. Other arrangements and methods may be implemented by those skilled in the art without departing from the scope and spirit of the invention. Moreover, those skilled in the art will envision other modifications within the scope and spirit of the additional features and advantages described herein.

Claims

1. 1. An ophthalmic device that is the polymerization product of a monomer mixture, the monomer mixture comprising: (a) from about 15 to about 75 weight percent of one or more cycloaliphatic (meth)acrylic monomers, based on the total weight of the monomer mixture; (b) greater than 25 wt. % of one or more hydrophilic monomers, based on the total weight of the monomer mixture; (c) one or more cross-linking agents; An ophthalmic device, wherein said ophthalmic device has a refractive index of about 1.48 to about 1.52 and an Abbe number of 50 or greater.

2. The ophthalmic device of claim 1 , wherein the one or more alicyclic (meth)acrylic monomers comprise one or more monocyclic alicyclic (meth)acrylic monomers.

3. The one or more monocyclic alicyclic monomers are ３ ~C ８ The ophthalmic device of claim 2 comprising a cycloalkyl group and a (meth)acrylic group.

4. The ophthalmic device of any one of claims 1 to 3, wherein the (meth)acrylic group of the one or more cycloaliphatic (meth)acrylic monomers is a (meth)acrylate-containing reactive end group.

5. The one or more alicyclic (meth)acrylic monomers are represented by the structure of Formula I: [Chemical Formula I] In the formula, x is an integer from 0 to 9, y is an integer from 0 to 3, B is O, NR, or S, and R is H, CH ３ , C.H. ２ CH ３ , or CH(CH ３ ) ２ where D is O, S, or a bond, and A is H or CH ３ and z is 0 to 4, with the proviso that when D is a bond, at least one of y and z is 0.

6. x is an integer from 1 to 4, y is 0, D is O, z is an integer from 1 to 4, B is O, and A is H or CH ３ 6. The ophthalmic device of claim 5, wherein:

7. x is an integer from 1 to 4, y is an integer from 1 to 4, D is a bond, z is 0, B is O, and A is H or CH ３ 6. The ophthalmic device of claim 5, wherein:

8. 8. The ophthalmic device of any one of claims 1 to 7, wherein the one or more hydrophilic monomers are selected from the group consisting of unsaturated carboxylic acids, acrylamides, vinyl lactams, hydroxyl-containing (meth)acrylates, hydrophilic vinyl carbonates, hydrophilic vinyl carbamate monomers, hydrophilic oxazolone monomers, and mixtures thereof.

9. The ophthalmic device of any one of claims 1 to 7, wherein the one or more hydrophilic monomers are one or more of 2-hydroxyethyl methacrylate and N,N-dimethylacrylamide.

10. The ophthalmic device of any one of claims 1 to 9, wherein the one or more hydrophilic monomers comprise greater than 25% to about 40% by weight, based on the total weight of the monomer mixture.

11. 11. The ophthalmic device of any one of claims 1 to 10, wherein the one or more crosslinkers are selected from the group consisting of 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, 1,3-propanediol diacrylate, 1,3-propanediol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, and poly(ethylene glycol) dimethacrylate.

12. The ophthalmic device of any one of claims 1 to 11, wherein the one or more crosslinking agents comprise from about 1% to about 10% by weight, based on the total weight of the monomer mixture.

13. The ophthalmic device of any one of claims 1 to 11, wherein the one or more crosslinkers comprise about 3% to about 5% by weight ethylene glycol dimethacrylate, based on the total weight of the monomer mixture.

14. the monomer mixture (a) about 30 to about 75 weight percent of one or more cycloaliphatic (meth)acrylic monomers, based on the total weight of the monomer mixture; (b) greater than 25% by weight to about 40% by weight of one or more hydrophilic monomers, based on the total weight of the monomer mixture; and (c) about 1 to about 10 wt % of one or more crosslinkers, based on the total weight of the monomer mixture.

15. The ophthalmic device of any one of claims 1 to 14, further comprising one or more of a reactive ultraviolet absorber and a reactive blue light absorber.

16. The monomer mixture may comprise one or more C ３ ~C １２ The ophthalmic device of any one of claims 1 to 15, further comprising an aliphatic (meth)acrylate monomer.

17. The ophthalmic device of any one of claims 1 to 16, wherein the ophthalmic device has a Tg of less than 25°C.

18. The ophthalmic device of any one of claims 1 to 17, wherein the ophthalmic device has an equilibrium water content (EWC) that is greater than 2% and less than or equal to 9%.

19. The ophthalmic device of any one of claims 1 to 18, wherein the ophthalmic device is a thermoset polymerization product.

20. The ophthalmic device according to any one of claims 1 to 19, wherein the ophthalmic device is an intraocular lens.

21. 1. A method for making an ophthalmic device, comprising: (a) (i) about 15 to about 75 weight percent of one or more cycloaliphatic (meth)acrylic monomers, based on the total weight of the monomer mixture; (ii) greater than 25 wt. % of one or more hydrophilic monomers, based on the total weight of the monomer mixture; (iii) providing a monomer mixture comprising one or more crosslinking agents; (b) subjecting the monomer mixture to polymerization conditions to obtain an ophthalmic device having a refractive index of about 1.48 to about 1.52 and an Abbe number of 50 or greater.

22. 22. The method of claim 21, wherein the one or more alicyclic (meth)acrylic monomers comprise one or more monocyclic alicyclic (meth)acrylic monomers.

23. The monocyclic alicyclic group is C ３ -C ８ 23. The method of claim 22, comprising a cycloalkyl group.

24. The one or more alicyclic (meth)acrylic monomers are represented by the structure of Formula I: [Chemical Formula I] In the formula, x is an integer from 0 to 9, y is an integer from 0 to 3, B is O, NR, or S, and R is H, CH ３ , C.H. ２ CH ３ , or CH(CH ３ ) ２ where D is O, S, or a bond, and A is H or CH ３ and z is 0 to 4, with the proviso that when D is a bond, at least one of y and z is 0.

25. x is an integer from 1 to 4, y is 0, D is O, z is an integer from 1 to 4, B is O, and A is H or CH ３ 25. The ophthalmic device of claim 24, wherein:

26. x is an integer from 1 to 4, y is an integer from 1 to 4, D is a bond, z is 0, B is O, and A is H or CH ３ 25. The ophthalmic device of claim 24, wherein:

27. 27. The method of any one of claims 21 to 26, wherein the one or more hydrophilic monomers are selected from the group consisting of unsaturated carboxylic acids, acrylamides, vinyl lactams, hydroxyl-containing (meth)acrylates, hydrophilic vinyl carbonates, hydrophilic vinyl carbamate monomers, hydrophilic oxazolone monomers, and mixtures thereof.

28. 27. The method of any one of claims 21 to 26, wherein the one or more hydrophilic monomers are one or more of 2-hydroxyethyl methacrylate and N,N-dimethylacrylamide.

29. 29. The method of any one of claims 21 to 28, wherein the one or more hydrophilic monomers comprise from greater than 25% to about 40% by weight, based on the total weight of the monomer mixture.

30. the monomer mixture (i) about 30 to about 75 weight percent of one or more cycloaliphatic (meth)acrylic monomers, based on the total weight of the monomer mixture; (ii) greater than 25 wt. % to about 40 wt. % of one or more hydrophilic monomers, based on the total weight of the monomer mixture; (iii) about 1 to about 10 weight percent of one or more crosslinking agents, based on the total weight of the monomer mixture.

31. The method of any one of claims 21 to 30, further comprising one or more of a reactive ultraviolet absorber and a reactive blue light absorber.

32. The monomer mixture comprises one or more C ３ ~C １２ The method of any one of claims 21 to 31, further comprising an aliphatic (meth)acrylate monomer.

33. The method of any one of claims 21 to 32, wherein the ophthalmic device has a Tg of less than 25°C.

34. 34. The method of any one of claims 21 to 33, wherein the ophthalmic device has an equilibrium water content (EWC) that is greater than 2% and less than or equal to 9%.

35. 35. The method of any one of claims 21 to 34, wherein subjecting the monomer mixture to polymerization conditions comprises subjecting the monomer mixture to heat-curing polymerization conditions.

36. The method of any one of claims 21 to 35, wherein the ophthalmic device is an intraocular lens.

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