Ophthalmic Devices

Abstract

An ophthalmic device for slowing, inhibiting, or preventing the progression of myopia, which is the polymerization product of a monomer mixture comprising: (a) greater than 50 weight percent of one or more non-silicone containing hydrophilic monomers, based on the total weight of the monomer mixture; (b) one or more crosslinkers; and (c) one or more red light blocking compounds that block greater than 5% to about 25% of red light transmission through the ophthalmic device at wavelengths of about 550 nm to about 800 nm, wherein the one or more red light blocking compounds have one or more ethylenically unsaturated reactive end groups.

Description

[Technical field]

[0001] Claiming priority This application claims priority to U.S. Provisional Patent Application No. 63 / 239,343, entitled "Ophthalmic Devices," filed August 31, 2021, the contents of which are incorporated by reference herein in their entirety. [Background technology]

[0002] FIELD OF THE DISCLOSURE The present disclosure relates generally to ophthalmic devices, such as contact lenses, for slowing, inhibiting, or preventing the progression of myopia.

[0003] Ophthalmic devices such as contact lenses are made from a variety of polymeric materials, including rigid gas permeable materials, soft elastomeric materials, and soft hydrogel materials. Many of the contact lenses sold today are made from soft hydrogel materials. Hydrogels are crosslinked polymer systems that absorb and retain water, typically 10 to 80 percent by weight. Hydrogel lenses are commonly prepared by polymerizing a lens-forming monomer mixture. In the case of silicone hydrogel lenses, silicone-containing monomers are copolymerized with hydrophilic monomers.

[0004] In the field of ophthalmic devices, various physical and chemical properties such as oxygen permeability, wettability, material strength, and stability are just some of the factors that must be carefully balanced to provide a usable contact lens. For example, oxygen permeability is an important feature for certain contact lens materials, since the cornea receives its oxygen supply from contact with the atmosphere. Wettability is also important in that if the lens is not sufficiently wetted, it will not remain lubricated and therefore will not be comfortable to wear on the eye. Therefore, an optimal contact lens will have at least both excellent oxygen permeability and excellent tear wettability. Summary of the Invention

[0005] According to an exemplary embodiment, an ophthalmic device for slowing, inhibiting, or preventing the progression of myopia is the polymerization product of a monomer mixture comprising: (a) greater than 50% by weight, based on the total weight of the monomer mixture, of one or more non-silicone-containing hydrophilic monomers; (b) one or more crosslinkers; and (c) one or more red light blocking compounds that block greater than about 5% to about 25% of red light transmission through the ophthalmic device at wavelengths from about 550 nanometers (nm) to about 800 nm, wherein the one or more red light blocking compounds have one or more ethylenically unsaturated reactive end groups.

[0006] According to another exemplary embodiment, a method for making an ophthalmic device for slowing, inhibiting, or preventing the progression of myopia comprises: (a) providing a monomer mixture comprising: (i) greater than 50% by weight, based on the total weight of the monomer mixture, of one or more non-silicone-containing hydrophilic monomers; (ii) one or more crosslinkers; and (iii) one or more red light blocking compounds that block greater than about 5% to about 25% of red light transmission through the ophthalmic device at wavelengths of about 550 nm to about 800 nm, wherein the one or more red light blocking compounds have one or more ethylenically unsaturated reactive end groups; (b) subjecting the monomer mixture to polymerization conditions to provide a polymerized ophthalmic device; and (c) hydrating the polymerized ophthalmic device.

[0007] According to yet another exemplary embodiment, a method for slowing, inhibiting, or preventing the progression of myopia in a subject in need thereof comprising: (a) providing an ophthalmic device that is a polymerization product of a monomer mix comprising: (i) greater than 50% by weight, based on the total weight of the monomer mix, of one or more non-silicone-containing hydrophilic monomers; (ii) one or more crosslinkers; and (iii) one or more red light blocking compounds that block greater than about 5% to about 25% of red light transmission through the ophthalmic device at wavelengths from about 550 nm to about 800 nm, wherein the one or more red light blocking compounds have one or more ethylenically unsaturated reactive end groups; and (b) inserting the ophthalmic device into the subject's eye.

[0008] Exemplary embodiments of the present disclosure are described in more detail below with reference to the accompanying drawings. [Brief description of the drawings]

[0009] [Figure 1] 1 is a graph showing the transmittance of red light passing through the lens of Example 1. [Diagram 2] 13 is a graph showing the transmittance of red light passing through the lens of Example 2. [Diagram 3] 13 is a graph showing the transmittance of red light passing through the lens of Example 3. [Figure 4] 11 is a graph showing the transmittance of red light passing through the lens of Example 4. [Diagram 5] 13 is a graph showing the transmittance of red light passing through the lens of Example 5. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] Various exemplary embodiments described herein are directed to ophthalmic devices derived from one or more red light blocking compounds in subjects (e.g., humans) in need of such devices to slow, inhibit, or prevent the progression of myopia. Generally, natural light is composed of different monochromatic lights having different wavelengths, which may not be focused on the same plane on the retina. Monochromatic lights of longer wavelengths may be focused on a plane behind the retina, while monochromatic lights of shorter wavelengths may be focused on a plane in front of the retina. The different focuses of light may contribute to a posterior displacement of the retina towards the image plane of the eye, which results in elongation of the eye. This may result in various pathologies, including myopia.

[0011] Myopia ("nearsightedness") is a vision condition in which objects close to the viewer are seen clearly, but objects farther away from the viewer become gradually blurred. Myopia can be caused by multiple reasons. One contributing factor in many cases of myopia is the long axial length of the eye. Myopia occurs when the focus of converging light forms in front of the retina. In other words, the focus of light rays entering the eye is in front of the retina. Thus, a myopic eye focuses light in front of the retinal plane. Myopia typically develops when the axial length of the eye becomes longer than the focal length of the eye's optics, i.e., the eye is too long.

[0012] It is believed that excessive stimulation of the L-cone in the human eye (especially in children) can result in suboptimal ocular elongation and myopia. Spectral filtering of red light using an ophthalmic device containing one or more red light blocking compounds can further reduce the wearer's myopia. However, current dyes (or colorants) of such red light blocking compounds typically used to manufacture dyed soft contact lenses often leach out, causing the lenses to lose their original color when subjected to sterilization conditions or during long-term storage. Thus, there is a need for improved ophthalmic devices that can filter and / or block red light, thereby inhibiting or preventing myopia in the wearer of the ophthalmic device.

[0013] Thus, the ophthalmic devices described herein overcome the aforementioned problems and advantageously provide at least one of slowing, inhibiting, or preventing the progression of myopia by blocking greater than about 5% and up to about 25% of red light transmission through the ophthalmic device at wavelengths of about 550 nanometers (nm) to about 800 nm. In a non-limiting exemplary embodiment, the ophthalmic devices described herein advantageously slow, inhibit, or prevent the progression of myopia in a subject by adding one or more red light blocking compounds that block greater than 5% to about 25% of red light transmission through the ophthalmic device at wavelengths of about 550 nm to about 800 nm, the one or more red light blocking compounds having one or more ethylenically unsaturated reactive end groups to a monomer mixture comprising (a) greater than 50% by weight, based on the total weight of the monomer mixture, of one or more non-silicone-containing hydrophilic monomers, and (b) one or more crosslinkers, the monomer mixture being polymerized to form the ophthalmic device.

[0014] The ophthalmic devices disclosed 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 lenses can provide optical correction, wound treatment, drug delivery, diagnostic functions, or cosmetic enhancements or effects, or a combination of these properties. Useful ophthalmic devices include, but are not limited to, ophthalmic lenses, such as soft contact lenses, e.g., soft hydrogel soft lenses, soft non-hydrogel soft lenses, hard contact lenses, e.g., hard gas permeable hard lens materials, intraocular lenses, overlay lenses, intraocular inserts, optical inserts, etc. As will be understood by those skilled in the art, a lens is considered to be "soft" if it can fold back on itself without breaking.

[0015] In an exemplary, non-limiting embodiment, the ophthalmic device described herein is a polymerization product of a monomer mixture comprising: (a) greater than 50% by weight, based on the total weight of the monomer mixture, of one or more non-silicone-containing hydrophilic monomers; (b) one or more crosslinking agents; and (c) one or more red light blocking compounds that block greater than 5% to about 25% of red light transmission through the ophthalmic device at wavelengths of about 550 nm to about 800 nm, wherein the one or more red light blocking compounds have one or more ethylenically unsaturated reactive end groups.

[0016] In an exemplary embodiment, the monomer mix comprises greater than 50% up to 90% by weight of one or more non-silicone containing hydrophilic monomers, based on the total weight of the monomer mix. In an exemplary embodiment, the monomer mix comprises greater than 50% up to 85% by weight of one or more non-silicone containing hydrophilic monomers, based on the total weight of the monomer mix. In an exemplary embodiment, the monomer mix comprises greater than 50% up to 80% by weight of one or more non-silicone containing hydrophilic monomers, based on the total weight of the monomer mix.

[0017] As used herein, the term "(meth)" refers to an optional methyl substituent. Thus, for example, a term such as "(meth)acrylate" refers to either methacrylate or acrylate, and "(meth)acrylamide" refers to either methacrylamide or acrylamide.

[0018] Suitable non-silicone-containing hydrophilic monomers include, for example, unsaturated carboxylic acids, acrylamides, vinyl lactams, poly(alkyleneoxy)(meth)acrylates, hydroxyl-containing (meth)acrylates, hydrophilic vinyl carbonates, hydrophilic vinyl carbamates, hydrophilic oxazolones, and poly(alkene glycols) functionalized with polymerizable groups, and 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, N,N-dimethylmethacrylamide, and 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, glycerol methacrylate, and mixtures thereof. Representative examples of useful functionalized poly(alkene glycols) include poly(diethylene glycols) of various chain lengths containing monomethacrylate or dimethacrylate end caps. In one embodiment, the poly(alkene glycol) polymer contains at least two alkene glycol monomer units. Further examples are the hydrophilic vinyl carbonate or vinyl carbamate monomers disclosed in U.S. Pat. No. 5,070,215 and the hydrophilic oxazolone monomers disclosed in U.S. Pat. No. 4,910,277. Other suitable hydrophilic monomers will be apparent to those skilled in the art. Mixtures of the aforementioned non-silicone-containing hydrophilic monomers can also be used in the monomer mixture herein.

[0019] In one exemplary embodiment, the monomer mixture includes one or more non-silicone-containing hydrophilic monomers that are one or more cyclic lactams. In another exemplary embodiment, the monomer mixture includes one or more non-silicone-containing hydrophilic monomers that are N-vinyl caprolactams.

[0020] The monomer mixture further comprises one or more crosslinking agents. Suitable crosslinking agents for use herein are known to those skilled in the art. Useful crosslinking agents can have at least two polymerizable functional groups. For example, in an exemplary non-limiting embodiment, suitable one or more crosslinking agents include one or more crosslinking agents containing at least two ethylenically unsaturated reactive end groups, where the ethylenically unsaturated reactive end groups are (meth)acrylate-containing reactive end groups, one or more crosslinking agents containing at least two ethylenically unsaturated reactive end groups, where at least one of the ethylenically unsaturated reactive end groups is a non-(meth)acrylate reactive end group, and mixtures thereof.

[0021] In an exemplary embodiment, useful one or more crosslinkers comprising at least two ethylenically unsaturated reactive end groups, where the ethylenically unsaturated reactive end groups are (meth)acrylate-containing reactive end groups, include one or more di-, tri-, or tetra-(meth)acrylate-containing crosslinkers.

[0022] In an exemplary embodiment, useful one or more di-, tri-, or tetra(meth)acrylate-containing crosslinkers include 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.

[0023] In an exemplary embodiment, the one or more alkylene glycol di(meth)acrylate crosslinkers include tetraethylene glycol dimethacrylate, and ethylene glycol di(meth)acrylate having up to about 10 ethylene glycol repeat units. In one embodiment, the one or more alkanediol di(meth)acrylate crosslinkers include butanediol di(meth)acrylate crosslinkers, and hexanediol di(meth)acrylate. 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.

[0024] In exemplary embodiments, useful one or more crosslinkers containing at least two ethylenically unsaturated reactive end groups, at least one of which is a non-(meth)acrylate reactive end group, include one or more di-, tri-, or tetracarbamate-containing crosslinkers, one or more di-, tri-, or tetracarbonate-containing crosslinkers, one or more isocyanurate-containing crosslinkers, and the like, as well as mixtures thereof.

[0025] Representative examples of the one or more di-, tri-, or tetra-carbamate-containing crosslinkers include one or more di(N-vinyl carbamate)-containing crosslinkers, one or more di(N-allyl carbamate)-containing crosslinkers, one or more di(O-vinyl carbamate)-containing crosslinkers, one or more di(O-allyl carbamate)-containing crosslinkers, one or more tri(N-vinyl carbamate)-containing crosslinkers, one or more tri(N-allyl carbamate)-containing crosslinkers, one or more tri(O-vinyl carbamate)-containing crosslinkers, one or more tri(O-allyl carbamate)-containing crosslinkers, one or more tetra(N-vinyl carbamate)-containing crosslinkers, one or more tetra(N-allyl carbamate)-containing crosslinkers, one or more tetra(O-vinyl carbamate)-containing crosslinkers, and one or more tetra(O-allyl carbamate)-containing crosslinkers, and the like, as well as mixtures thereof.

[0026] Representative examples of one or more di-, tri-, or tetracarbonate-containing crosslinkers include di(O-vinyl carbonate)-containing crosslinkers, di(O-allyl carbonate)-containing crosslinkers, tri(O-vinyl carbonate)-containing crosslinkers, tri(O-allyl carbonate)-containing crosslinkers, tetra(O-vinyl carbonate)-containing crosslinkers, and tetra(O-allyl carbonate)-containing crosslinkers, and the like, and mixtures thereof.

[0027] Representative examples of the one or more isocyanurate-containing crosslinkers include one or more of diallyl isocyanurate, triallyl isocyanurate, divinyl isocyanurate, trivinyl isocyanurate, and the like, and mixtures thereof.

[0028] In embodiments, the one or more dicarbamate-containing crosslinkers have the following structure: [ka] (wherein x is 0 to 10).

[0029] In embodiments, the one or more dicarbamate-containing crosslinkers have the following structure: [ka] (wherein x is 0 to 10).

[0030] In embodiments, the one or more di-carbamate-containing crosslinkers include diethylene glycol bis(N-vinyl carbamate), diethylene glycol bis(O-allyl carbamate), and the like, and mixtures thereof.

[0031] In embodiments, the one or more second crosslinkers are selected from the group consisting of diethylene glycol bis(N-vinyl carbamate), diethylene glycol bis(N-allyl carbamate), diethylene glycol bis(O-vinyl carbamate), diethylene glycol bis(O-allyl carbamate), and mixtures thereof, 1,4-butanediol bis(N-vinyl carbamate), ethylene glycol bis(O-vinyl carbonate), diethylene glycol bis(O-vinyl carbonate), 1,4-butanediol bis(O-vinyl carbonate), and mixtures thereof.

[0032] In an embodiment, the one or more crosslinkers containing at least two ethylenically unsaturated reactive end groups include at least one allyl-containing reactive end group and at least one (meth)acrylate-containing reactive end group. In one embodiment, the one or more second crosslinkers comprises allyl methacrylate.

[0033] In embodiments, suitable crosslinkers include divinylbenzene, allyl methacrylate, ethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, vinyl carbonate derivatives of glycol dimethacrylate, and methacryloxyethyl vinyl carbonate.

[0034] Generally, one or more crosslinking agents are present in the monomer mixture in an ophthalmic device-forming amount. In embodiments, one or more crosslinking agents are present in the monomer mixture in an amount of about 0.1 to about 2.0 weight percent, based on the total weight of the monomer mixture.

[0035] The monomer mixture further comprises one or more red light blocking compounds that block greater than about 5% to about 25% of red light transmission through the ophthalmic device at wavelengths between about 550 nm and about 800 nm, the one or more red light blocking compounds having one or more ethylenically unsaturated reactive end groups. In an exemplary embodiment, the one or more red light blocking compounds comprise one or more red light blocking compounds that block greater than about 5% to about 25% of red light transmission through the ophthalmic device at wavelengths between about 550 nm and about 700 nm, the one or more red light blocking compounds having one or more ethylenically unsaturated reactive end groups. In an exemplary embodiment, the one or more red light blocking compounds comprise one or more red light blocking compounds that block greater than about 5% to about 25% of red light transmission through the ophthalmic device at wavelengths between about 650 nm and about 680 nm, the one or more red light blocking compounds having one or more ethylenically unsaturated reactive end groups.

[0036] In another exemplary embodiment, the one or more red light blocking compounds include one or more red light blocking compounds that block about 10% to about 15% of the red light transmission through the ophthalmic device at wavelengths between about 550 nm and about 800 nm, and the one or more red light blocking compounds have one or more ethylenically unsaturated reactive end groups. In an exemplary embodiment, the one or more red light blocking compounds include one or more red light blocking compounds that block about 10% to about 15% of the red light transmission through the ophthalmic device at wavelengths between about 550 nm and about 700 nm, and the one or more red light blocking compounds have one or more ethylenically unsaturated reactive end groups. In an exemplary embodiment, the one or more red light blocking compounds include one or more red light blocking compounds that block more than about 10% to about 15% of the red light transmission through the ophthalmic device at wavelengths between about 650 nm and about 680 nm, and the one or more red light blocking compounds have one or more ethylenically unsaturated reactive end groups.

[0037] In an exemplary embodiment, the one or more red light blocking compounds include one or more red light blocking compounds that block greater than 5% to about 25% of red light transmission through the ophthalmic device at wavelengths between about 550 nm and about 800 nm, and the one or more red light blocking compounds have one or more methacrylate-containing reactive end groups. In an exemplary embodiment, the one or more red light blocking compounds include one or more red light blocking compounds that block greater than 5% to about 25% of red light transmission through the ophthalmic device at wavelengths between about 550 nm and about 700 nm, and the one or more red light blocking compounds have one or more methacrylate-containing reactive end groups. In an exemplary embodiment, the one or more red light blocking compounds include one or more red light blocking compounds that block greater than 5% to about 25% of red light transmission through the ophthalmic device at wavelengths between about 650 nm and about 680 nm, and the one or more red light blocking compounds have one or more methacrylate-containing reactive end groups.

[0038] In an exemplary embodiment, the one or more red light blocking compounds include one or more red light blocking compounds that block about 10% to about 15% of the red light transmission through the ophthalmic device at wavelengths between about 550 nm and about 800 nm, and the one or more red light blocking compounds have one or more methacrylate-containing reactive end groups. In an exemplary embodiment, the one or more red light blocking compounds include one or more red light blocking compounds that block about 10% to about 15% of the red light transmission through the ophthalmic device at wavelengths between about 550 nm and about 700 nm, and the one or more red light blocking compounds have one or more methacrylate-containing reactive end groups. In an exemplary embodiment, the one or more red light blocking compounds include one or more red light blocking compounds that block about 10% to more than about 15% of the red light transmission through the ophthalmic device at wavelengths between about 650 nm and about 680 nm, and the one or more red light blocking compounds have one or more methacrylate-containing reactive end groups.

[0039] In exemplary embodiments, the ethylenically unsaturated reactive end group may include, by way of example, a (meth)acrylate end group, a vinyl end group, an acrylamide end group, and the like. In one embodiment, the ethylenically unsaturated reactive end group is a methacrylate-containing reactive end group. A suitable methacrylate-containing reactive end group has the structure: [ka] where R* is a linking group or a bond. Suitable linking groups include, for example, any divalent hydrocarbon radical or moiety, such as, independently, linear or branched, substituted or unsubstituted C1-C 30 Alkyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups, substituted or unsubstituted C4-C 30 Cycloalkyl groups, substituted or unsubstituted C3-C 30 Cycloalkenyl groups, substituted or unsubstituted C6-C 30 Aryl groups, substituted or unsubstituted C7-C 30 Included are any divalent hydrocarbon radicals or moieties, such as arylalkyl groups, and substituted or unsubstituted ether-containing groups. The divalent hydrocarbon radicals or moieties of the linking group may optionally contain heteroatoms in the chain, such as sulfur, e.g., sulfone.

[0040] Representative examples of alkyl groups for use herein include straight or branched alkyl chain groups containing carbon and hydrogen atoms having, for example, 1 to about 30 carbon atoms, or 1 to about 12 carbon atoms, or 1 to about 6 carbon atoms, relative to the remainder of the molecule, with or without unsaturation, such as methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, n-pentyl, methylene, ethylene, and the like, to form heteroalkyl groups.

[0041] Representative examples of cycloalkyl groups for use herein include, by way of example, substituted or unsubstituted non-aromatic monocyclic or polycyclic ring systems of about 3 to about 30 carbon atoms, or 3 to about 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, perhydronaphthyl, adamantyl, and norbornyl groups, bridged cyclic or spiro bicyclic groups, such as spiro-(4,4)-non-2-yl, and the like, optionally containing one or more heteroatoms, such as, for example, O and N, to form a heterocycloalkyl group.

[0042] Representative examples of cycloalkylalkyl groups for use herein include, by way of example, substituted or unsubstituted cyclic ring-containing groups containing from about 4 to about 30 carbon atoms, or from 3 to about 6 carbon atoms, which are attached directly to an alkyl group and then attached to the main structure of the monomer at any carbon from the alkyl group to produce a stable structure, e.g., cyclopropylmethyl, cyclobutylethyl, cyclopentylethyl, and the like, and the cyclic ring may optionally contain one or more heteroatoms, e.g., O and N, to form a heterocycloalkylalkyl group.

[0043] Representative examples of cycloalkenyl groups for use herein include, by way of example, substituted or unsubstituted cyclic ring-containing groups containing from about 3 to about 30 carbon atoms, or from 3 to about 6 carbon atoms, and having at least one carbon-carbon double bond, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and the like, where the cyclic ring can optionally contain one or more heteroatoms, such as, for example, O and N, to form a heterocycloalkenyl group.

[0044] Representative examples of aryl groups for use herein include, for example, substituted or unsubstituted monocyclic or polycyclic aromatic radicals containing from about 6 to about 30 carbon atoms, and optionally containing one or more heteroatoms, such as, for example, O and N, forming a heteroaryl group, such as, for example, phenyl, naphthyl, tetrahydronaphthyl, indenyl, and biphenyl.

[0045] Representative examples of arylalkyl groups for use herein include, by way of example, a substituted or unsubstituted aryl group, as defined herein, directly bonded to an alkyl group, as defined herein, e.g., -CH2C6H5, -C2H4C6H5, etc., where the aryl group may optionally contain one or more heteroatoms, e.g., O and N, to form a heteroarylalkyl group.

[0046] Representative examples of ether- or polyether-containing groups for use herein include, by way of example, alkyl ethers, cycloalkyl ethers, cycloalkylalkyl ethers, cycloalkenyl ethers, aryl ethers, arylalkyl ethers, where alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, aryl, and arylalkyl groups are as defined herein. Exemplary ether- or polyether-containing groups include, by way of example, alkylene oxides, poly(alkylene oxides), such as ethylene oxide, propylene oxide, butylene oxide, poly(ethylene oxide), poly(ethylene glycol), poly(propylene oxide), poly(butylene oxide), and mixtures or copolymers thereof, alkylene oxides of the general formula -(R 14 OR 15 ) t ether or polyether group, 14 is a bond, a substituted or unsubstituted alkyl, cycloalkyl, or aryl group as defined herein, and R 15 is a substituted or unsubstituted alkyl, cycloalkyl, or aryl group as defined herein, and t is at least 1.

[0047] In an exemplary embodiment, one of the one or more red light blocking compounds is one of those compounds having the structure of Formula (I): [ka] (In the formula, R 1 and R 2is hydrogen or an ethylenically unsaturated reactive end group, R 1 and R 2 At least one of R is an ethylenically unsaturated reactive end group; 3 is hydrogen or a sulfonate group.

[0048] In an exemplary embodiment, another class of the one or more red light blocking compounds is those compounds having the structure of Formula (II): [ka] (In the formula, R 1 and R 2 is hydrogen or an ethylenically unsaturated reactive end group, R 1 and R 2 At least one of R is an ethylenically unsaturated reactive end group; 3 and R 4 are independently hydrogen or a sulfonate group.

[0049] The one or more red light blocking compounds may be obtained by methods known in the art or are commercially available from sources such as Pharnorcia Inc. and Sigma Aldrich.

[0050] In an exemplary embodiment, the one or more red light blocking compounds may be present in the monomer mixture in an amount ranging from about 0.005% to about 0.30% by weight, based on the total weight of the monomer mixture. In another exemplary embodiment, the one or more red light blocking compounds may be present in the monomer mixture in an amount ranging from about 0.02% to about 0.30% by weight, based on the total weight of the monomer mixture. In another exemplary embodiment, the one or more red light blocking compounds may be present in the monomer mixture in an amount ranging from about 0.05% to about 0.30% by weight, based on the total weight of the monomer mixture. In another exemplary embodiment, the one or more red light blocking compounds may be present in the monomer mixture in an amount ranging from about 0.05% to about 0.20% by weight, based on the total weight of the monomer mixture.

[0051] The monomer mixture may further comprise one or more non-bulky organosilicon-containing monomers.As used herein, "organosilicon-containing monomers" refers to monomers, macromers, or prepolymers that contain at least one [siloxanyl] or at least one [silylalkylsiloxanyl] repeat unit.In one embodiment, the one or more non-bulky organosilicon-containing monomers are compounds represented by the structure of formula (III): [ka] where V is an ethylenically unsaturated polymerizable group, L is a linker group or a bond, and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently H, C1 to C 12 Alkyl, haloalkyl, C3~C 12 Cycloalkyl, heterocycloalkyl, C2-C 12 Alkenyl, haloalkenyl, or C6-C 12 Aromatic, R 10 and R 11 are independently H or C1-C 12 alkyl, where R 10 and R 11 At least one of the above is hydrogen, y is 2 to 7, and n is 1 to 100 or 1 to 20.

[0052] Ethylenically unsaturated polymerizable groups are well known to those skilled in the art. Suitable ethylenically unsaturated polymerizable groups include, for example, (meth)acrylates, vinyl carbonates, O-vinyl carbamates, N-vinyl carbamates, and (meth)acrylamides.

[0053] The linker group may be any divalent group or moiety, for example, a substituted or unsubstituted C1-C 12These include alkyl, alkyl ether, alkenyl, alkenyl ether, haloalkyl, substituted or unsubstituted siloxanes, and monomers capable of propagating ring opening.

[0054] In one embodiment, V is a (meth)acrylate and L is a C1-C 12 alkylene, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independent, C1~C 12 is alkyl, R 10 and R 11 is independently H, y is 2 to 7, and n is 3 to 8.

[0055] In one embodiment, V is a (meth)acrylate, L is a C1-C6 alkyl, and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently C1-C6 alkyl; R 10 and R 11 is independently H, y is 2 to 7, and n is 1 to 20.

[0056] Non-bulky organosilicon-containing monomers represented by the structure of formula III are known in the art, see, for example, U.S. Pat. Nos. 7,915,323, 7,994,356, 8,420,711, 8,827,447, and 9,039,174, the contents of which are incorporated herein by reference.

[0057] In one embodiment, the one or more non-bulky organosilicon-containing monomers are compounds represented by the structure of formula IV: [ka] In the formula, R 12 is H or methyl, and X is O or NR 16 and R 16 is selected from H, or C1-C4 alkyl, optionally further substituted with one or more hydroxyl groups, and in some embodiments is H or methyl; R 13 is a divalent alkyl group, which may be further functionalized with a group selected from the group consisting of ether groups, hydroxyl groups, carbamate groups, and combinations thereof, and in another embodiment is a C1-C6 alkylene group which may be substituted with ethers, hydroxyls, and combinations thereof, and in yet another embodiment is a C1 or C3-C4 alkylene group which may be substituted with ethers, hydroxyls, and combinations thereof, and each R 14 is independently phenyl, or C1-C4 alkyl, which may be substituted with fluorine, hydroxyl, or ether; in another embodiment, each R 14 is independently selected from ethyl and methyl groups, and in yet another embodiment, each R 14 is methyl, R 15 is C1-C4 alkyl and a is 2-50, and in some embodiments, 5-15.

[0058] Non-bulky organosilicon-containing monomers represented by the structure of formula IV are known in the art, see, for example, U.S. Pat. Nos. 8,703,891, 8,937,110, 8,937,111, 9,156,934, and 9,244,197, the contents of which are incorporated herein by reference.

[0059] In an exemplary embodiment, the one or more non-bulky organosilicon-containing monomers may be present in the monomer mixture in an amount ranging from about 5% to about 50% by weight, based on the total weight of the monomer mixture. In one embodiment, the one or more non-bulky organosilicon-containing monomers may be present in the monomer mixture in an amount ranging from about 15% to about 45% by weight, based on the total weight of the monomer mixture.

[0060] The monomer mixture may further comprise one or more bulky siloxane monomers. Representative examples of applicable siloxane monomers include bulky polysiloxanyl alkyl (meth)acrylic monomers. In one embodiment, a suitable bulky siloxane monomer has the structure of formula V: [ka] (Wherein, X is —O— or —NR 19 - (wherein R 19 is hydrogen or C1-C4 alkyl, and each R 17 each independently represents hydrogen or methyl; 18 are independently represented by a lower alkyl radical, such as a C1-C6 alkyl, a phenyl radical, or: [ka] (In the formula, each R 18′ independently represent a lower alkyl, such as a C1-C6 alkyl, or a phenyl radical, and h is 1-10.

[0061] In one embodiment, suitable bulky siloxane monomers can generally be represented by Formula VI: [ka] (Wherein, X is -NR 19 - represents R 19 represents hydrogen or C1-C4 alkyl, R 17 represents hydrogen or methyl, and each R 18 are independently a bulky polysiloxanyl alkyl carbamate monomer, such as generally represented by the formula: [ka] (In the formula, each R 18′ independently represent a lower alkyl radical, such as a C1-C6 alkyl radical, or a phenyl radical, and h is 1-10.

[0062] Suitable one or more bulky siloxane monomers include, for example, methacryloxypropyl tris(trimethylsiloxy)silane ("TRIS"), pentamethyldisiloxanylmethyl methacrylate, tris(trimethylsiloxy)methacryloxypropyl silane, phenylthrethramethyldisiloxanylethyl acrylate, methyldi(trimethylsiloxy)methacryloxymethylsilane, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate (TRIS-VC), 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate, and mixtures thereof.

[0063] In an exemplary embodiment, the one or more bulky siloxane monomers may be present in the monomer mixture in an amount ranging from about 5% to about 50% by weight, based on the total weight of the monomer mixture. In one embodiment, the one or more bulky siloxane monomers may be present in the monomer mixture in an amount ranging from about 15% to about 45% by weight, based on the total weight of the monomer mixture.

[0064] The monomer mixture can further comprise one or more hydrophobic monomers.Suitable hydrophobic monomers include, for example, ethylenically unsaturated hydrophobic monomers, such as (meth)acrylate-containing hydrophobic monomers, N-alkyl (meth)acrylamide-containing hydrophobic monomers, alkyl vinyl carbonate-containing hydrophobic monomers, alkyl vinyl carbamate-containing hydrophobic monomers, fluoroalkyl (meth)acrylate-containing hydrophobic monomers, N-fluoroalkyl (meth)acrylamide-containing hydrophobic monomers, N-fluoroalkyl vinyl carbonate-containing hydrophobic monomers, N-fluoroalkyl vinyl carbamate-containing hydrophobic monomers, silicone-containing (meth)acrylate-containing hydrophobic monomers, (meth)acrylamide-containing hydrophobic monomers, vinyl carbonate-containing hydrophobic monomers, vinyl carbamate-containing hydrophobic monomers, styrene-containing hydrophobic monomers, and polyoxypropylene (meth)acrylate-containing hydrophobic monomers, and mixtures thereof.

[0065] In an exemplary embodiment, the one or more hydrophobic monomers are represented by the structure of Formula VII: [ka] (In the formula, R 1 is methyl or hydrogen, R 2 is -O- or -NH-, R 3 and R 4 are independently -CH2-, -CHOH-, and -CHR 6 -, R 5 and R 6 are independently a branched C3 to C8 alkyl group, R 7 is hydrogen or -OH, n is an integer of at least 1, and m and p are independently 0 or an integer of at least 1, with the proviso that the sum of m, p, and n is 2, 3, 4, or 5.

[0066] Representative examples of the one or more hydrophobic monomers represented by the structure of formula VII include, but are not limited to, 4-t-butyl-2-hydroxycyclohexyl methacrylate (TBE), 4-t-butyl-2-hydroxycyclopentyl methacrylate, 4-t-butyl-2-hydroxycyclohexyl methacrylamide (TBA), 6-isopentyl-3-hydroxycyclohexyl methacrylate, 2-isohexyl-5-hydroxycyclopentyl methacrylamide, 4-t-butylcyclohexyl methacrylate, isobornyl methacrylate, adamantyl methacrylate, n-butyl methacrylate, n-hexyl methacrylate, lauryl methacrylate, and benzyl methacrylate. In one embodiment, the one or more hydrophobic monomers (b) comprise a compound of formula VII, wherein R 3 is -CH2-, m is 1 or 2, p is 0, and the sum of m and n is 3 or 4.

[0067] In an exemplary embodiment, the one or more hydrophobic monomers are present in the monomer mixture in an amount ranging from about 0.5% to about 25% by weight, based on the total weight of the monomer mixture. In one embodiment, the one or more hydrophobic monomers are present in the monomer mixture in an amount ranging from about 1% to about 10% by weight, based on the total weight of the monomer mixture.

[0068] The monomer mixture may further contain various additives such as antioxidants, wetting agents, and strengthening agents, as well as other components well known in the art, if necessary, within the limits not impairing the objectives and effects of the present disclosure.

[0069] In one embodiment, suitable wetting agents may be, for example, glycerin, propylene glycol, mono- or disaccharide sugars, polyethylene glycol, ethoxylated glucose, and combinations thereof. In one embodiment, suitable wetting agents may be, for example, polymers containing carboxylic acid functionality, such as polymers containing polyacrylic acid (PAA). Specific coating wetting agents include P(vinylpyrrolidinone (VP)-co-acrylic acid (AA)), P(methyl vinyl ether-alt-maleic acid), P(acrylic acid-graft-ethylene oxide), P(acrylic acid-co-methacrylic acid), P(acrylamide-co-AA), P(acrylamide-co-AA), P(AA-co-maleic acid), P(butadiene-maleic acid) and P(N-vinylpyrrolidone-co-vinyl acetate), and polyvinyl alcohol.

[0070] Ophthalmic devices of the exemplary embodiments disclosed herein, e.g., contact lenses or intraocular lenses, can be prepared by polymerizing the aforementioned monomer mixture to form a product that can then be formed into the appropriate shape, e.g., by lathing, injection molding, compression molding, cutting, etc. For example, in manufacturing contact lenses, the initial mixture may be polymerized in a tube to provide rod-like articles that are then cut into buttons. The buttons may then be lathed into contact lenses.

[0071] Alternatively, ophthalmic devices such as contact lenses may be poured directly from the mixture into a mold, e.g., a polypropylene mold, by, for example, spin casting and static casting. Spin casting is disclosed in U.S. Pat. Nos. 3,408,429 and 3,660,545, and static casting is disclosed in U.S. Pat. Nos. 4,113,224, 4,197,266, and 5,271,875. Spin casting involves filling a mold with the mixture to be polymerized and rotating the mold in a controlled manner while exposing the mixture to a radiation source such as UV light. Static casting involves filling a monomer mixture between two mold parts, one mold part shaped to form the anterior surface of the lens and the other mold part shaped to form the posterior surface of the lens, and curing the mixture while held in the mold assembly to form a lens, e.g., by free radical polymerization of the mixture. Examples of free radical reaction techniques for hardening lens materials include thermal radiation, infrared radiation, electron beam radiation, gamma radiation, and ultraviolet (UV) radiation, or a combination of such techniques may be used. US Patent No. 5,271,875 describes a static casting method that allows for the molding of a finished lens in a mold cavity defined by a back mold and a front mold. As an additional method, US Patent No. 4,555,732 discloses a process in which an excess of a monomer mixture is hardened by spin casting in a mold to form a shaped article having a lens anterior surface and a relatively large thickness, and the posterior surface of the hardened spin cast article is then latched to provide a contact lens having a desired thickness and lens posterior surface.

[0072] Polymerization may be accelerated by exposing the mixture to heat and / or radiation, such as ultraviolet light, visible light, or high energy radiation. A polymerization initiator may be included in the mixture to accelerate the polymerization step. 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. 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® 651 and 184 (Ciba-Geigy), 2,2' azobis(2-methylpropionitrile) (VAZO 64), and the like. In general, the initiator will be used in the monomer mixture at a concentration of about 0.01 to about 5 weight percent of the total mixture.

[0073] The polymerization is generally carried out in a reaction medium such as a solvent or dispersion using a solvent such as water or an alkanol containing 1 to 4 carbon atoms such as methanol, ethanol, or propan-2-ol. Alternatively, a mixture of any of the above solvents may be used.

[0074] Generally, the polymerization can be carried out under an inert atmosphere of, for example, nitrogen or argon, for about 15 minutes to about 72 hours. If desired, the resulting polymerization product can be dried under vacuum, for example, for about 5 to about 72 hours, or left in an aqueous solution before use.

[0075] Polymerization of the mixture results in a polymer that, when hydrated, preferably forms a hydrogel. When producing hydrogel lenses, the mixture may further include at least one diluent that will eventually be replaced with water when the polymerization product is hydrated to form a hydrogel. Generally, the water content of the hydrogel is as described hereinabove, i.e., at least about 45 weight percent or at least about 50 weight percent. The amount of diluent used must be less than about 50 weight percent, and in most cases the diluent content is less than about 30 weight percent. However, for a particular polymer system, the practical limit will be determined by the solubility of the various monomers in the diluent. To produce optically clear copolymers, it is important that no phase separation occurs between the comonomer and the diluent, or between the diluent and the final copolymer, which would result in visual opacity.

[0076] Furthermore, the maximum amount of diluent that can be used will depend on the amount of swelling that the diluent causes to the final polymer. Excessive swelling can cause or disintegrate the copolymer when the diluent is replaced by water upon hydration. Suitable diluents include, but are not limited to, ethylene glycol, glycerin, liquid poly(ethylene glycol), alcohol, alcohol / water mixtures, ethylene oxide / propylene oxide block copolymers, low molecular weight linear poly(2-hydroxyethyl methacrylate), glycol esters of lactic acid, formamides, ketones, dialkyl sulfoxides, butyl carbitol, boric acid esters of polyhydric alcohols, such as boric acid esters of glycerol, and the like, as well as mixtures thereof.

[0077] 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, if desired. 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 monomeric components, as can be readily determined by one of ordinary skill in the art. If desired, the mixture used to make hydrogel lenses may further include crosslinkers and wetting agents known in the prior art for making hydrogel materials.

[0078] In the case of intraocular lenses, the monomer mixture to be polymerized may further include a monomer to increase the refractive index of the resulting polymerization product. Examples of such monomers include aromatic (meth)acrylates, such as phenyl (meth)acrylate, 2-phenylethyl (meth)acrylate, 2-phenoxyethyl methacrylate, and benzyl (meth)acrylate.

[0079] The ophthalmic devices, such as contact lenses, obtained herein may be subjected to optional machining operations. For example, other optional machining steps may include buffing or polishing the edges and / or surfaces of the lens. In general, such machining processes may be performed before or after the product is released from the mold parts, for example, the lens is dry demolded 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.

[0080] The lenses may then be transferred to individual lens packages containing a buffered saline solution. Saline may be added to the package either before or after transfer of the lenses. 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, polymeric 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.

[0081] As one of ordinary skill 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 reusing mold halves, as well as combinations thereof.

[0082] The following examples are provided to enable one of ordinary skill in the art to practice the invention and are merely illustrative and should not be read as limiting the scope of the invention as defined by the claims.

[0083] In the examples, the following abbreviations are used:

[0084] DMA: N,N-dimethylacetamide.

[0085] HEMA: 2-hydroxyethyl methacrylate.

[0086] NVP: N-vinyl-2-pyrrolidone.

[0087] EGDMA: ethylene glycol dimethacrylate.

[0088] SIGMA: (3-methacryloxy-2-hydroxypropoxy)propylbis(trimethylsiloxy)methylsilane

[0089] TRIS: 3-[tris(trimethylsiloxy)silyl]propyl methacrylate.

[0090] Vazo™ 64: Azobis-isobutyronitrile (AIBN).

[0091] Irgacure 819: Photoinitiator for free radical polymerization available from Sigma Aldrich.

[0092] Poloxamer: Pluronic 407 dimethacrylate having the following structure: [ka]

[0093] CIX-4: A compound having the following structure: [ka]

[0094] MPEG Silane 16: A compound having the following structure and available from Momentive: [ka]

[0095] Ma2D37: A compound having the following structure and available from Shin-Etsu and Gelest: [ka]

[0096] M1EDS6: A compound having the following structure and available from Gelest: [ka]

[0097] Methacrylated Reactive Black 5: A compound having the following structure was prepared by reaction of Reactive Black 5 with HEMA: Reactive Black 5 was purchased from Sigma Aldrich and HEMA was purchased from Evonik. [ka]

[0098] Methacrylated Reactive Blue 19: A compound having the following structure was prepared by reaction of Reactive Blue 19 with HEMA: Reactive Blue 19 was purchased from Sigma Aldrich and HEMA was purchased from Evonik. [ka]

[0099] Reactive Blue 247: A compound having the following structure and available from Pharnocia: [ka]

[0100] Examples 1 and 2 A monomer mixture was made by mixing the following components listed in Table 1 in the amounts by weight: [Table 1]

[0101] The monomer mixture was cast into a contact lens by introducing the monomer mixture into a polypropylene mold assembly. The mold assembly and monomer mixture were then heat cured for about 3.0 hours to form a contact lens. The resulting contact lens was released from the mold assembly and placed in boronization buffer solution (BBS) before being extracted twice in 100% water for 10 minutes each and autoclaved.

[0102] The lenses of Examples 1 and 2 were then individually placed on a horizontal integrating sphere for contact lens measurement. Transmission spectra were obtained from 200 nm to 800 nm. Figures 1 and 2 are each graphs showing the transmittance of red light through the lenses of Examples 1 and 2, respectively.

[0103] Examples 3 to 5 A monomer mixture was made by mixing the following components in the amounts by weight listed in Table 2. [Table 2]

[0104] The monomer mixture was cast into a contact lens by introducing the monomer mixture into a polypropylene mold assembly. The mold assembly and monomer mixture were then heat cured for about 3.0 hours to form a contact lens. The resulting contact lens was released from the mold assembly and placed in boronization buffer solution (BBS) before being extracted twice in 100% water for 10 minutes each and autoclaved.

[0105] The lenses of Examples 3-5 were then individually placed on a horizontal integrating sphere for contact lens measurement. Transmission spectra were obtained from 200 nm to 800 nm. Figures 3-5 are graphs showing the red light transmittance through the lenses of Examples 3-5, respectively.

[0106] For the sake of brevity, various features disclosed herein are described in the context of a single embodiment, but may be provided separately or in any suitable subcombination.All combinations of the embodiments are specifically encompassed by the exemplary embodiments disclosed herein, as if each and every combination were individually and expressly disclosed herein.In addition, all subcombinations listed in the embodiments that describe such variations are also specifically encompassed by the composition, and are disclosed herein, as if each and every combination were individually and expressly disclosed herein.

[0107] It will be understood that various modifications can be made to the embodiments disclosed herein. Thus, 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 present invention are for illustrative purposes only. Those skilled in the art can implement other configurations and methods without departing from the scope and spirit of the present invention. Moreover, those skilled in the art will envision other modifications within the scope and spirit of the features and advantages added herein.

Claims

1. 1. An ophthalmic device that is the polymerization product of a monomer mixture, the monomer mixture comprising: (a) greater than 50 weight percent, based on the total weight of the monomer mixture, of one or more non-silicone-containing hydrophilic monomers; (b) one or more cross-linking agents; and (c) one or more red light blocking compounds that block greater than 5% to 25% of red light transmission through the ophthalmic device at wavelengths between 550 nanometers (nm) and 800 nm, the one or more red light blocking compounds having one or more ethylenically unsaturated reactive end groups.

2. 2. The ophthalmic device of claim 1, wherein the one or more non-silicone containing hydrophilic monomers are selected from the group consisting of unsaturated carboxylic acids, acrylamides, vinyl lactams, poly(alkyleneoxy)(meth)acrylates, (meth)acrylic acid, hydroxyl-containing (meth)acrylates, hydrophilic vinyl carbonates, hydrophilic vinyl carbamate monomers, hydrophilic oxazolone monomers, and mixtures thereof.

3. 10. The ophthalmic device of claim 1, wherein the one or more red light blocking compounds comprise one or more red light blocking compounds that block greater than 5% to 25% of red light transmission through the ophthalmic device at wavelengths between 550 nm and 700 nm, or between 650 nm and 680 nm, and the one or more red light blocking compounds have one or more ethylenically unsaturated reactive end groups.

4. 10. The ophthalmic device of claim 1, wherein the one or more red light blocking compounds comprise one or more red light blocking compounds that block 10% to 15% of red light transmission through the ophthalmic device at wavelengths of 550 nm to 800 nm, or at wavelengths of 550 nm to 700 nm, or at wavelengths of 650 nm to 680 nm, and the one or more red light blocking compounds have one or more ethylenically unsaturated reactive end groups.

5. 5. The ophthalmic device of any one of claims 1 to 4, wherein the one or more ethylenically unsaturated reactive end groups comprise one or more (meth)acrylate end groups, vinyl end groups, and / or acrylamide end groups.

6. The one or more red light blocking compounds have the following structure: 【Chemistry 1】 (In the formula, R １ and R ２ is hydrogen or a methacrylate-containing reactive end group; R １ and R ２ At least one of R ３ The ophthalmic device of any one of claims 1 to 4, wherein:

7. The one or more red light blocking compounds have the following structure: 【Chemistry 2】 (In the formula, R １ and R ２ is hydrogen or an ethylenically unsaturated reactive end group; R １ and R ２ At least one of R ３ and R ４ The ophthalmic device of any one of claims 1 to 4, wherein:

8. The monomer mixture is (a) greater than 50% up to 90% by weight of said one or more non-silicone containing hydrophilic monomers, based on the total weight of said monomer mixture; (b) 0.1 to 2.0 weight percent of the one or more crosslinking agents, based on the total weight of the monomer mixture; (c) 0.02 to 0.3 wt % of the one or more red light blocking compounds, based on the total weight of the monomer mixture.

9. The ophthalmic device according to any one of claims 1 to 4, wherein the ophthalmic device is a contact lens or an intraocular lens.

10. 1. A method of making an ophthalmic device, the method comprising: (a) providing a monomer mixture, the monomer mixture comprising: (i) greater than 50 weight percent of said one or more non-silicone containing hydrophilic monomers, based on the total weight of said monomer mixture; (ii) one or more cross-linking agents; and (iii) one or more red light blocking compounds that block greater than 5% to 25% of red light transmission through the ophthalmic device at wavelengths between 550 nm and 800 nm, the one or more red light blocking compounds having one or more ethylenically unsaturated reactive end groups; (b) subjecting the monomer mixture to polymerization conditions to provide a polymerized ophthalmic device; (c) hydrating the polymerized ophthalmic device.

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