Ophthalmic device and method of manufacture

Abstract

A method for preparing an ophthalmic device for slowing, inhibiting, or preventing the progression of myopia includes: (a) immersing the ophthalmic device in one or more first solvent solutions to swell the ophthalmic device; (b) immersing the swollen ophthalmic device in one or more second solvent solutions containing 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 nanometers (nm) to about 800 nm to deswell the swollen ophthalmic device and encapsulate the one or more red light blocking compounds within the deswelled ophthalmic device; and (c) sterilizing the deswelled ophthalmic device.

Description

[Technical field]

[0001] Claiming priority This application claims priority to U.S. Provisional Patent Application No. 63 / 239,246, 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, a method for making an ophthalmic device for slowing, inhibiting or preventing the progression of myopia includes: (a) immersing the ophthalmic device in one or more first solvent solutions to cause the ophthalmic device to swell; (b) immersing the swollen ophthalmic device in one or more second solvent solutions containing 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 nanometers (nm) and about 800 nm to deswell the swollen ophthalmic device and encapsulate the one or more red light blocking compounds within the deswelled ophthalmic device; (c) sterilizing the deswelled ophthalmic device.

[0006] According to another exemplary embodiment, an ophthalmic device for slowing, inhibiting, or preventing the progression of myopia 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 and are encapsulated in a polymerization product of a monomer mixture including one or more ophthalmic device-forming monomers.

[0007] According to yet another exemplary embodiment, a method for slowing, inhibiting, or preventing the progression of myopia in a subject in need thereof includes (a) providing an ophthalmic device comprising 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, and that are encapsulated in a polymerization product of a monomer mixture comprising one or more ophthalmic device-forming monomers; 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. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] Various exemplary embodiments described herein are directed to an ophthalmic device that captures one or more red light blocking compounds in a subject (e.g., a human) in need of such a device 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 and the lenses 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 slowing, 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 between about 550 nanometers (nm) and about 800 nm. In a non-limiting exemplary embodiment, an ophthalmic device for slowing, inhibiting, or preventing the progression of myopia in a subject in need of such a device 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 and are encapsulated in a polymerization product of a monomer mixture comprising one or more ophthalmic device-forming monomers.

[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] 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.

[0016] The ophthalmic device may be formed from any material known in the art that can form an ophthalmic device. In one embodiment, the ophthalmic device includes a device formed from a material that is not hydrophilic in itself. Such devices are formed from materials known in the art, including, for example, polysiloxanes, perfluoropolyethers, fluorinated poly(meth)acrylates, or equivalent fluorinated polymers derived from other polymerizable carboxylic acids, polyalkyl(meth)acrylates, or equivalent alkyl ester polymers derived from other polymerizable carboxylic acids, or fluorinated polyolefins, such as fluorinated ethylene propylene polymers, or tetrafluoroethylene, preferably in combination with a dioxole, such as perfluoro-2,2-dimethyl-1,3-dioxole. Representative examples of suitable bulky materials include, but are not limited to, Lotrafilcon A, Neofocon, Pasifocon, Telefocon, Silafocon, Fluorosilfocon, Paflufocon, Silafocon, Elastofilcon, Fluorofocon, or Teflon® AF materials, such as Teflon® AF1600 or Teflon® AF2400, which are copolymers of about 63 to about 73 mol % perfluoro-2,2-dimethyl-1,3-dioxole and about 37 to about 27 mol % tetrafluoroethylene, or copolymers of about 80 to about 90 mol % perfluoro-2,2-dimethyl-1,3-dioxole and about 20 to about 10 mol % tetrafluoroethylene.

[0017] In another embodiment, the ophthalmic device includes devices formed from materials that are themselves hydrophilic, for example, reactive groups such as carboxy, carbamoyl, sulfate, sulfonate, phosphate, amine, ammonium or hydroxyl groups are inherently present in the material and therefore present on the surface of the ophthalmic device made therefrom. Such devices are formed from materials known in the art, including, by way of 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-vinyl caprolactam, N-vinyl-2-piperidone, and the like, and mixtures thereof. Representative examples of hydroxyl-containing (meth)acrylates include 2-hydroxyethyl methacrylate, glycerol methacrylate, and the like, 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 mixtures herein.

[0018] Representative examples of suitable hydrophilic and bulky materials include, but are not limited to, polymafilcon, tefilcon, metafilcon, deltafilcon, bufilcon, femfilcon, ocufilcon, ocofilcon, etafilcon, hefilcon, vifilcon, tetrafilcon, perfilcon, droxifilcon, dimefilcon, isofilcon, mafilcon, nelfilcon, atlafilcon, etc. Other suitable examples of bulky materials include balafilcon A, hilafilcon A, alphafilcon A, bilafilcon B, etc.

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

[0020] In an exemplary embodiment, the one or more hydrophobic monomers can be present in the monomer mixture in an amount ranging from about 25% to about 90% by weight, based on the total weight of the monomer mixture. In another exemplary embodiment, the one or more hydrophobic monomers can be present in the monomer mixture in an amount ranging from about 30% to about 75% by weight, based on the total weight of the monomer mixture.

[0021] In another embodiment, the ophthalmic device includes a device formed from a material that is an amphiphilic segmented copolymer containing at least one hydrophobic segment and at least one hydrophilic segment connected via bonds or crosslinking members.

[0022] It is particularly useful to use the biocompatible materials herein, including both soft and hard materials commonly used in ophthalmic lenses, including contact lenses.In general, non-hydrogel materials are hydrophobic polymeric materials that do not contain water in their equilibrium state.Typical non-hydrogel materials include silicone acrylics, such as those formed from bulky silicone monomers (e.g., tris(trimethylsiloxy)silylpropyl methacrylate, commonly known as "TRIS" monomers), poly(dimethylsiloxane) prepolymers end-capped with methacrylate, or silicones with fluoroalkyl side groups (polysiloxanes are also commonly known as silicone polymers).

[0023] In general, hydrogels are a well-known class of materials that contain hydrated crosslinked polymer systems that contain water in equilibrium. Thus, hydrogels are copolymers prepared from hydrophilic monomers. In the case of silicone hydrogels, hydrogel copolymers are generally prepared by polymerizing a mixture containing at least one device-forming silicone-containing monomer and at least one device-forming hydrophilic monomer. Either the silicone-containing monomer or the hydrophilic monomer can function as a crosslinker (a crosslinker defined as a monomer having multiple polymerizable functional groups), or a separate crosslinker may be used. Silicone hydrogels typically have a water content of about 10 to about 80% by weight.

[0024] The monomer mixture may also include a second device-forming monomer that includes a copolymerizable group and a reactive functional group. The copolymerizable group is preferably an ethylenically unsaturated group, such that this device-forming monomer copolymerizes with the hydrophilic device-forming monomer and any other device-forming monomers in the initial device-forming monomer mixture. Additionally, the second monomer may include a reactive functional group that reacts with a complementary reactive group of the resulting copolymer. In other words, after the device is formed by copolymerizing the device-forming monomer mixture, the reactive functional group provided by the second device-forming monomer remains to react with the complementary reactive moiety of the copolymer.

[0025] In one embodiment, the reactive group of the second device-forming monomer comprises an epoxide group. Thus, the second device-forming monomer comprises both an ethylenically unsaturated group (allowing the monomer to copolymerize with the hydrophilic device-forming monomer) and an epoxide group (not reacting with the hydrophilic device-forming monomer but remaining reactive with the copolymer, for example, the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers). Suitable second device-forming monomers include, for example, glycidyl methacrylate, glycidyl acrylate, glycidyl vinyl carbonate, glycidyl vinyl carbamate, and 4-vinyl-1-cyclohexene-1,2-epoxide.

[0026] As mentioned above, one type of ophthalmic device substrate material is silicone hydrogel.In this case, initial device forming monomer mixture further comprises silicone-containing monomer.Applicable silicone-containing monomer materials for use in forming silicone hydrogel are well known in the art, and numerous examples are provided in U.S. Patent Nos. 4,136,250, 4,153,641, 4,740,533, 5,034,461, 5,070,215, 5,260,000, 5,310,779 and 5,358,995. Specific examples of suitable materials for use herein include those disclosed in U.S. Pat. Nos. 5,310,779, 5,387,662, 5,449,729, 5,512,205, 5,610,252, 5,616,757, 5,708,094, 5,710,302, 5,714,557, and 5,908,906, the contents of which are incorporated herein by reference.

[0027] Representative examples of applicable silicone-containing monomers include 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 non-bulky organosilicon-containing monomers are represented by the following formula (Ia): [ka] wherein L is an ethylenically unsaturated polymerizable group, V 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 9are independently hydrogen, an alkyl group, a haloalkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkenyl group, a haloalkenyl group, or an aromatic group; R 10 and R 11 is independently hydrogen or alkyl; R 10 and R 11 at least one of is hydrogen, y is 2 to 7, and n is 1 to 100 or 1 to 20).

[0028] 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.

[0029] The linker group may be any divalent group or moiety, for example, a substituted or unsubstituted C1-C 12 These include alkyl, alkyl ether, alkenyl, alkenyl ether, haloalkyl, substituted or unsubstituted siloxanes, and monomers capable of propagating ring opening.

[0030] 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.

[0031] 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 , R6 , 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.

[0032] Non-bulky organosilicon-containing monomers represented by the structure of formula Ia 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.

[0033] In an exemplary embodiment, the one or more non-bulky organosilicon-containing monomers may include a compound represented by the structure of Formula Ib below: [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, R15 is C1-C4 alkyl and a is 2-50, and in some embodiments, 5-15.

[0034] Non-bulky organosilicon-containing monomers represented by the structure of formula Ib 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.

[0035] In one 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.

[0036] Representative examples of applicable silicone-containing monomers also include bulky polysiloxanyl alkyl (meth)acrylic monomers. One example of the bulky polysiloxanyl alkyl (meth)acrylic monomer is represented by the structure of formula (II): [ka] (Wherein, X is —O— or —NR 19 - represents each R 19 is hydrogen or C1-C4 alkyl, R 17 each independently represents hydrogen or methyl; 18 are independently a lower alkyl radical, such as a C1-C6 group, a phenyl radical, or a group represented by the structure: [ka] (In the formula, each R 18′represents independently a lower alkyl radical or a phenyl radical, and h is 1 to 10), or the following structure of formula (III): [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 lower alkyl radical, a phenyl radical, or a group represented by the structure: [ka] In the formula, each R 18′ independently represents a lower alkyl radical or a phenyl radical, and h is 1 to 10.

[0037] Examples of bulky monomers include methacryloxypropyl tris(trimethyl-siloxy)silane or tris(trimethylsiloxy)silylpropyl methacrylate (sometimes referred to as TRIS), and tris(trimethylsiloxy)silylpropyl vinylcarbamate (sometimes referred to as TRIS-VC).

[0038] Such bulky monomers may be copolymerized with silicone macromonomers, which are poly(organosiloxanes) capped with unsaturated groups at two or more ends of the molecule. U.S. Patent No. 4,153,641 discloses various unsaturated groups, such as acryloxy or methacryloxy groups.

[0039] Another class of representative silicone-containing monomers includes, for example, silicone-containing vinyl carbonate or vinyl carbamate monomers such as 1,3-bis[4-vinyloxycarbonyloxy)but-1-yl]tetramethyl-disiloxane; 3-(trimethylsilyl)propyl vinyl carbonate; 3-(vinyloxycarbonylthio)propyl-[tris(trimethylsiloxy)silane]; 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate; 3-[tris(trimethylsiloxy)silyl]propyl allyl carbamate; 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate; t-butyldimethylsiloxyethyl vinyl carbonate; trimethylsilylethyl vinyl carbonate; trimethylsilylmethyl vinyl carbonate, and the like, and mixtures thereof.

[0040] Another type of silicone-containing monomer includes polyurethane-polysiloxane macromonomers (sometimes called prepolymers), which may have hard-soft-hard blocks like conventional urethane elastomers. These may be endcapped with hydrophilic monomers such as HEMA. Examples of such silicone urethanes are disclosed in various publications, including Lai, Yu-Chin, "The Role of Bulky Polysiloxanylalkyl Methacryates in Polyurethane-Polysiloxane Hydrogels," Journal of Applied Polymer Science, Vol. 60, 1193-1199 (1996). PCT Published Application No. WO 96 / 31792 discloses examples of such monomers, the disclosure of which is incorporated herein by reference in its entirety. Further examples of silicone urethane monomers are represented by formulae (IV) and (V): E(*D*A*D*G) a *D*A*D*E', or (IV) E(*D*G*D*A) a *D*A*D*E', or (V) During the ceremony, D independently represents an alkyl di-group, an alkylcycloalkyl di-group, a cycloalkyl di-group, an aryl di-group, or an alkylaryl di-group having 6 to about 30 carbon atoms; G independently represents an alkyl, cycloalkyl, alkylcycloalkyl, aryl, or alkylaryl group having 1 to about 40 carbon atoms, which may contain an ether, thio, or amine bond in the main chain; * represents a urethane or ureido bond, a is at least 1, A independently represents a divalent polymer radical of formula (VI), [ka] In the formula, each R S independently represent an alkyl or fluoro-substituted alkyl group having 1 to about 10 carbon atoms which may contain ether linkages between the carbon atoms; m' is at least 1; and p is a number providing a site weight of from about 400 to about 10,000; Each of E and E′ independently represents a polymerizable unsaturated organic group represented by formula (VII), [ka] In the formula, R 3 is hydrogen or methyl; R 4 is hydrogen, an alkyl group having 1 to 6 carbon atoms, or -CO-YR 6 group, Y is -O-, -S-, or -NH-; R 5 is a divalent alkylene radical having 1 to about 10 carbon atoms, R 6 is an alkyl radical having 1 to about 12 carbon atoms, X represents -CO- or -OCO-; Z represents -O- or -NH-; Ar represents an aromatic group having from about 6 to about 30 carbon atoms; w is an integer of 0 to 6, x is 0 or 1, y is 0 or 1, and z is 0 or 1.

[0041] In one embodiment, the silicone-containing urethane monomer is represented by formula (VIII): [ka] In the formula, m is at least 1, preferably 3 or 4, a is at least 1, preferably 1, p is a number providing a site weight of about 400 to about 10,000, preferably at least about 30, and R 7 is the diradical of a diisocyanate after removal of an isocyanate group, such as the diradical of isophorone diisocyanate, and each E is a group represented by: [ka]

[0042] In another embodiment, the silicone hydrogel material comprises (in bulk, i.e., in the copolymerized monomer mixture) about 5 to about 50% by weight, or about 10 to about 25% by weight, of one or more silicone macromonomers, about 5 to about 75% by weight, or about 30 to about 60% by weight, of one or more polysiloxanylalkyl(meth)acrylic monomers, and about 10 to about 50% by weight, or about 20 to about 40% by weight, of a hydrophilic monomer. Generally, silicone macromonomers are poly(organosiloxanes) capped with unsaturated groups at two or more ends of the molecule. In addition to the end groups in the above structural formula, U.S. Pat. No. 4,153,641 discloses additional unsaturated groups, including acryloxy or methacryloxy. Fumarate-containing materials, such as those disclosed in U.S. Patent Nos. 5,310,779, 5,449,729, and 5,512,205, are also useful substrates according to non-limiting embodiments described herein. The silane macromonomer may be a silicone-containing vinyl carbonate or vinyl carbamate, or a polyurethane-polysiloxane having one or more hard-soft-hard blocks and endcapped with a hydrophilic monomer.

[0043] In another embodiment, another class of silicone-containing monomers includes monomers of formula (IX). [ka] In the formula, X is a residue of a ring-opening agent; L is the same or different and is a linker group or a bond; V is an ethylenically unsaturated polymerizable group; R1, R2, R3, R4, R5, and R6 are independently a halogen, an alkyl group, a haloalkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkenyl group, a haloalkenyl group, or an aromatic group; R7 and R8 are independently a halogen or an alkyl group; at least one of R7 or R8 is hydrogen; y is 2 to 7; and n is 1 to 100.

[0044] Ring openers are well known in the literature. Non-limiting examples of anionic ring openers include alkyllithiums, alkoxides, trialkylsiloxyllithiums, where the alkyl groups may or may not contain halo atoms.

[0045] The linker group can be any divalent radical or moiety, including substituted or unsubstituted alkyl, alkyl ether, alkenyl, alkenyl ether, haloalkyl, substituted or unsubstituted siloxane, and monomers capable of propagating ring opening.

[0046] Ethylenically unsaturated polymerizable groups are well known to those skilled in the art. Non-limiting examples of ethylenically unsaturated polymerizable groups can include methacrylates, vinyl carbonates, O-vinyl carbamates, N-vinyl carbamates, acrylamides, and methacrylamides.

[0047] In another embodiment, one class of silicone-containing monomers includes monomers of formula (X). [ka] In the formula, L is the same or different and is a linker group or a bond; V is the same or different and is an ethylenically unsaturated polymerizable group; R1, R2, R3, R4, R5, R6, and R9 are independently hydrogen, an alkyl group, a haloalkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkenyl group, a haloalkenyl group, or an aromatic group; R7 or R8 are independently halogen or an alkyl group, and at least one of R7 or R8 is hydrogen; y is 2 to 7; and n is 1 to 100.

[0048] In another embodiment, one class of silicone-containing monomers includes monomers of formula (XI) and (XII): [ka] In the formula, R9, R 10 , and R 11 is independently a halogen, an alkyl group, a haloalkyl group, or other substituted alkyl group, n is as defined above, and n 1 is between 0 and 10, [ka] n is an integer from 1 to 100, or n is an integer from 2 to 80, or n is an integer from 3 to 20, or n is an integer from 5 to 15.

[0049] In another embodiment, one class of silicone-containing monomers includes monomers of formulae (XIII)-(XVII): [ka]

[0050] In another embodiment, one type of silicone-containing monomer includes monomers of formulae (XVIII)-(XX): [ka] In the formula, R9, R 10 , and R 11are independently a halogen, an alkyl group, a haloalkyl group, or other substituted alkyl group; n and n 1 is as defined above.

[0051] In another embodiment, one class of silicone-containing monomers includes monomers of formulae (XXI)-(XXIII). [ka] In the formula, n is as defined above, and X - is a counter ion to provide an overall neutral charge.

[0052] Counterions capable of providing an overall neutral charge are well known to those of skill in the art and can include, for example, halide ions.

[0053] In another embodiment, one class of silicone-containing monomers includes monomers of formula (XXIV). [ka]

[0054] Representative examples of alkyl groups for use herein include, by way of example, straight or branched alkyl chain groups containing carbon and hydrogen atoms, with or without unsaturation, relative to the remainder of the molecule, having from 1 to about 30 carbon atoms, or from 1 to about 12 carbon atoms, or from 1 to about 6 carbon atoms, such as methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, n-pentyl, methylene, ethylene, etc. The alkyl group may optionally contain one or more heteroatoms, such as O and N, to form haloalkyl groups.

[0055] 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 haloalkyl group.

[0056] Representative examples of aromatic groups for use herein include 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 O and N, forming haloaromatic groups, e.g., phenyl, naphthyl, tetrahydronaphthyl, indenyl, and biphenyl.

[0057] Representative examples of cycloalkenyl groups for use herein include, by way of example, substituted or unsubstituted alkyl groups containing from about 2 to about 30 carbon atoms, or from 3 to about 12 carbon atoms, and having at least one carbon-carbon double bond, such as, for example, propenyl, butenyl, pentenyl, and the like, where the alkyl group may optionally contain one or more heteroatoms, such as, for example, O and N, to form a haloalkyl group.

[0058] Another type of representative silicone-containing monomer comprises fluorinated monomer.Such monomer has been used in the formation of fluorosilicone hydrogels to reduce the accumulation of deposits on contact lenses made therefrom, as disclosed in, for example, U.S. Pat. Nos. 4,954,587, 5,010,141 and 5,079,319.Also, it has been found that the use of silicone-containing monomers with certain fluorinated side groups, i.e., -(CF2)-H, improves the compatibility between hydrophilic monomer units and silicone-containing monomer units.See, for example, U.S. Pat. Nos. 5,321,108 and 5,387,662.

[0059] The silicone materials mentioned above are merely exemplary, and other materials for use as substrates may also be used, as they have been disclosed in various publications and are continually being developed for use in contact lenses and other ophthalmic devices. For example, the ophthalmic device may be formed from at least one cationic monomer, such as a cationic silicone-containing monomer or a cationic fluorinated silicone-containing monomer.

[0060] Contact lenses for use in the illustrated embodiments described herein can be manufactured using a variety of conventional techniques to obtain a plastic article having the desired posterior and anterior lens surfaces. Spin casting methods are disclosed in U.S. Pat. Nos. 3,408,429 and 3,660,545, and static casting methods are disclosed in U.S. Pat. Nos. 4,113,224, 4,197,266, and 5,271,876. Machining operations can be performed following the curing of the monomer mixture to provide a contact lens having a desired final configuration. As an example, U.S. Pat. No. 4,555,732 discloses a process in which the excess of the monomer mixture is cured by spin casting in a mold to form a plastic article having an anterior lens surface and a relatively large thickness. The posterior surface of the cured spin cast article is then lathe cut to provide a contact lens having the desired thickness and posterior lens surface. Further machining operations can be performed after lathe cutting of the lens surface (e.g., edge finishing operations).

[0061] Once ophthalmic devices such as contact lenses are dry demolded, they can then be subjected to optional machining operations. Other optional machining steps can include buffing or polishing the edges and / or surfaces of the lenses. In general, such machining processes can be performed before or after the product is demolded from the mold parts, for example, a 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 can then be flipped over to machine the other side of the lens.

[0062] The resulting ophthalmic device thus formed is then subjected to the steps of the method according to the exemplary non-limiting embodiments described herein, so that one or more red light blocking compounds are trapped within the ophthalmic device. For example, in one step, the ophthalmic device is first immersed in one or more first solvent solutions for a period of time sufficient to swell the ophthalmic device. In general, the one or more first solvent solutions include a solvent capable of swelling the ophthalmic device. In one embodiment, the one or more first solvent solutions include, for example, low molecular weight alcohol solvents, aliphatic hydrocarbon solvents, alicyclic hydrocarbon solvents, ketone solvents, nitrile solvents, ether solvents, amide group-containing solvents, and mixtures thereof.

[0063] Suitable low molecular weight alcohols include, for example, low molecular weight alcohols having about 1 to about 13 carbon atoms and / or a molecular weight of about 200 or less. Suitable low molecular weight alcohols can be selected from a variety of low molecular weight monohydric alcohols, each containing about 1 to about 13 carbon atoms. Suitable monohydric alcohols include, for example, methanol, ethanol, propanol, isopropyl alcohol, butanol, isobutyl alcohol, tert-butyl alcohol, hexanol, 2-ethylhexanol, and dodecanol. Suitable aliphatic or alicyclic hydrocarbon solvents include, for example, pentane, hexane, heptane, and cyclohexane.

[0064] Suitable ketone solvents are, for example, acetone, methyl ethyl ketone, diethyl ketone, methyl propyl ketone, methyl isopropyl ketone, ethyl propyl ketone, ethyl isopropyl ketone, dipropyl ketone, diisopropyl ketone, methyl butyl ketone, methyl isobutyl ketone, methyl sec-butyl ketone, methyl tert-butyl ketone, ethyl butyl ketone, ethyl isobutyl ketone, ethyl sec-butyl ketone, ethyl tert-butyl ketone, propyl butyl ketone, isopropyl butyl ketone, propyl isobutyl ketone, propyl sec-butyl ketone, propyl tert-butyl ketone, isopropyl isobutyl ketone, isopropyl sec-butyl ketone, isopropyl tert-butyl ketone, dibutyl ketone, diisobutyl ketone, di-sec-butyl ketone, di-tert-butyl ketone, butyl isobutyl ketone, butyl tert-butyl ketone, isobutyl sec-butyl ketone, isobutyl tert-butyl ketone, sec-butyl tert -Butyl ketone, 5-heptanone, 5-methyl-2-hexanone (methyl isoamyl ketone), 4-methyl-2-hexanone, 3-methyl-2-hexanone, 3,4-dimethyl-2-pentanone, 3,3-dimethyl-2-pentanone, 4,4-dimethyl-2-pentanone, 3-octanone, 4-methyl-3-heptanone, 5-methyl-3-heptanone, 6-methyl-3-heptanone, 4,4-dimethyl-3-hexanone, 4,5-dimethyl-3-hexanone, 5,5-dimethyl-3-hexanone cyclopropanone, 4-nonanone, 5-methyl-4-octanone, 6-methyl-4-octanone, 7-methyl-4-octanone, 5,5-dimethyl-4-neptanone, 5,6-dimethyl-4-heptanone, 6,6-dimethyl-4-heptanone, 2-undecanone, cyclopropanone, cyclobutanone, cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone, cyclononanone, cyclodecanone, cycloundecanone, and cyclododecanone, and the like, and combinations thereof. In one embodiment, the ketone solvent is acetone.

[0065] Suitable nitrile solvents include, for example, saturated or unsaturated aliphatic, alicyclic, or aromatic compounds containing a nitrile group. Nitriles include compounds containing heteroatoms, such as those selected from Groups 13, 14, 15, 16, and 17 of the Periodic Table of the Elements. Representative examples of nitriles for use herein include acetonitrile, propionitrile, isopropionitrile, butyronitrile, isobutyronitrile, valeronitrile, isovaleronitrile, trimethylacetonitrile, hexanenitrile, heptanenitrile, heptyl cyanide, octanenitrile, undecanenitrile, malononitrile, succinonitrile, glutaronitrile, adiponitrile, sebaconitrile, allyl cyanide, acrylonitrile, crotononitrile, methacrylonitrile, fumaronitrile, tetracyanoethylene, cyclopentanecarbonitrile, cyclohexanecarbonitrile, dichloroacetonitrile, fluoroacetonitrile, trichloroacetonitrile, benzonitrile, benzyl cyanide, 2-methylbenzyl cyanide, 2-chlorobenzonitrile, 3-chlorobenzonitrile, 4-chlorobenzonitrile, o-tolunitrile, m-tolunitrile, and p-tolunitrile, and the like, and mixtures thereof. In one embodiment, the nitrile solvent is acetonitrile.

[0066] Suitable ether solvents include, for example, dialkyl ethers, where the alkyl groups are the same or different and have 1 to about 12 carbon atoms. Representative examples of ether solvents include dimethyl ether, diethyl ether, di-i-propyl ether, dioxane, tetrahydrofuran, pyran, and the like, and mixtures thereof. In one embodiment, the ether solvent is tetrahydrofuran.

[0067] Suitable amide group-containing solvents include, for example, dimethylformamide, N-methylformanilide, N-formylpiperidine, N-formylmorpholine, dimethylacetamide, N-methylpyrrolidone, N,N-dimethylbenzamide, and mixtures thereof. In one embodiment, the amide group-containing solvent is N-methylpyrrolidone.

[0068] In one embodiment, the one or more first solvent solutions can further include water in combination with any of the aforementioned first solvents. For example, the one or more first solvent solutions can be a blend containing about 25% to about 75% by weight of the one or more first solvent solutions and about 75% to about 25% by weight of water. In another embodiment, the blend can contain about 40% to about 60% by weight of the one or more first solvent solutions and about 60% to about 40% by weight of water.

[0069] The ophthalmic device is immersed in the one or more first solvent solutions for a period of time sufficient to swell the ophthalmic device. Typically, the ophthalmic device is immersed in the one or more first solvent solutions for a period of time ranging from about 5 minutes to about 120 minutes. In one embodiment, the ophthalmic device is immersed in the one or more first solvent solutions for a period of time ranging from about 5 minutes to about 60 minutes. In one embodiment, the ophthalmic device is immersed in the one or more first solvent solutions for a period of time ranging from about 10 minutes to about 35 minutes.

[0070] In an exemplary embodiment, the ophthalmic device is immersed in a series of one or more first solvent solutions. For example, the ophthalmic device is first immersed in one or more first solvent solutions or blends of one or more first solvents and water as described herein above for a period ranging from about 5 minutes to about 30 minutes, or from about 5 minutes to about 20 minutes. The ophthalmic device is then removed from the solution or blend and immersed in another solvent solution of any of the one or more first solvents described above or blends of one or more first solvents and water as described above for a period ranging from about 5 minutes to about 120 minutes. In one embodiment, the ophthalmic device is immersed in another solvent solution of any of the one or more first solvents described above or blends of one or more first solvents and water as described above for a period ranging from about 5 minutes to about 60 minutes. In another embodiment, the ophthalmic device is immersed in another solvent solution of any of the one or more first solvents described above or blends of one or more first solvents and water as described above for a period ranging from about 10 minutes to about 35 minutes.

[0071] In another step, the swollen ophthalmic device is immersed in one or more second solvent solutions containing one or more red light blocking compounds to deswell the ophthalmic device and encapsulate the one or more red light blocking compounds in the ophthalmic device. In an exemplary embodiment, the one or more second solvent solutions include any solvent that can dissolve one or more red light blocking compounds. Suitable second solvent solutions include, for example, only water or any of the low molecular weight alcohol solvents, aliphatic hydrocarbon solvents, cycloaliphatic hydrocarbon solvents, ketone solvents, nitrile solvents, ether solvents, and amide group-containing solvents described hereinabove. In an exemplary embodiment, the second solvent solution is only water.

[0072] In one embodiment, the one or more second solvent solutions include a blend of water together with any of low molecular weight alcohol solvents, aliphatic hydrocarbon solvents, alicyclic hydrocarbon solvents, ketone solvents, nitrile solvents, ether solvents, and amide group-containing solvents. For example, the one or more second solvent solutions can be a blend containing about 25% to about 75% by weight of one or more second solvent solutions, such as low molecular weight alcohols, and about 75% to about 25% by weight of water. In another embodiment, the blend can contain about 40% to about 60% by weight of one or more second solvent solutions, such as low molecular weight alcohols, and about 60% to about 40% by weight of water. When using a blend, the one or more red light blocking compounds are first added into the one or more second solvent solutions to form a solution. Then, water is added into the solution in an amount such that the one or more red light blocking compounds do not precipitate out of the solution.

[0073] In a non-limiting exemplary embodiment, when the swollen ophthalmic device is immersed in one or more second solvent solutions containing one or more red light blocking compounds to deswell the ophthalmic device, at least a portion of the one or more red light blocking compounds may be covalently bonded to the reactive functional groups on the lens through hydrogen bonds. For example, if the ophthalmic device is derived from the polymerization product of a monomer mixture containing one or more non-silicone hydrophilic monomers having OH reactive groups present on the surface of the lens or within the lens, such as 2-hydroxyethyl methacrylate and glycidyl methacrylate, the OH group of the one or more non-silicone hydrophilic monomers may react with the reactive functional groups complementary to the OH group through hydrogen bonds. This is illustrated below in a non-limiting embodiment of Scheme I. [ka]

[0074] In exemplary embodiments, the one or more red light blocking compounds are present in the one or more second solvent solutions in an amount ranging from about 0.05 to about 5% by weight, based on the total weight of the solution. In exemplary embodiments, the one or more red light blocking compounds are present in the one or more second solvent solutions in an amount ranging from about 0.50 to about 1.5% by weight, based on the total weight of the solution.

[0075] The ophthalmic device is immersed in the one or more second solvent solutions for a period of time sufficient to deswell the ophthalmic device and encapsulate the one or more red light blocking compounds. In an exemplary embodiment, the ophthalmic device is immersed in the one or more second solvent solutions for a period of time ranging from about 5 minutes to about 120 minutes. In another exemplary embodiment, the ophthalmic device is immersed in the one or more second solvent solutions for a period of time ranging from about 10 minutes to about 18 minutes.

[0076] In an exemplary embodiment, the ophthalmic device can be immersed in a series of one or more second solvent solutions. For example, the ophthalmic device is first immersed in one or more second solvent solutions containing only water or a low molecular weight alcohol solvent with one or more red light blocking compounds for a period ranging from about 5 minutes to about 30 minutes or from about 10 minutes to about 18 hours. The ophthalmic device is then removed from the solvent solution and further immersed in one or more additional solvent solutions containing one or more red light blocking compounds for a period ranging from about 5 minutes to about 30 minutes. In one embodiment, the one or more additional solvent solutions can include a blend of the same or different low molecular weight alcohol solvents and water, one or more of the red light blocking compounds, another solvent solution of water, and one or more of the red light blocking compounds.

[0077] In an exemplary embodiment, the one or more red light blocking compounds include 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. In an exemplary embodiment, the one or more red light blocking compounds include 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. In an exemplary embodiment, the one or more red light blocking compounds include 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.

[0078] 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. 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. In an exemplary embodiment, the one or more red light blocking compounds include one or more red light blocking compounds that block greater 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.

[0079] In exemplary embodiments, representative examples of suitable red light blocking compounds for use herein are represented by the following compounds I-IX. [ka] [ka] wherein X1 and X2 are independently CH2 or C(CH3)2, R1 and R2 are independently H or (CH2)4SO3Na, and R3 is H or SO3Na.

[0080] 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 LI-COR Biosciences, Inc.

[0081] After the ocular device has been deswelled, it is removed and optionally immersed in a series of one or more aqueous solutions to further deswell the device, in an exemplary embodiment, the ocular device is each immersed in one or more of the aqueous solutions for a period ranging from about 5 minutes to about 20 minutes.

[0082] In another step, the deswelled ophthalmic device is sterilized. In an exemplary embodiment, the deswelled ophthalmic device is sterilized by submerging it in a suitable buffered saline, such as borate buffered saline, and then subjecting it to autoclave conditions for at least about 5 minutes. In an exemplary embodiment, the deswelled ophthalmic device is subjected to autoclave conditions for at least about 20 minutes. In another exemplary embodiment, the deswelled ophthalmic device is subjected to autoclave conditions for at least 1 hour. The sterilized ophthalmic devices are then rinsed with water and placed in their package with borate buffered saline. The package is sealed and the ophthalmic device is again subjected to autoclave conditions.

[0083] Alternatively, the deswelled ophthalmic device may be placed in a container that includes a receptacle portion for holding the deswelled ophthalmic device and a sterile packaging solution. An example of a container is a conventional ophthalmic device blister package. This receptacle containing the deswelled ophthalmic device immersed in the solution is hermetically sealed, for example, by sealing a lid on the package over the receptacle. For example, the lid is sealed around the receptacle. The solution and the deswelled ophthalmic device are sterilized while sealed in the package receptacle. Examples of sterilization techniques include subjecting the solution and the deswelled ophthalmic device to thermal energy, microwave radiation, gamma radiation, or ultraviolet radiation. A specific example involves heating the solution and the deswelled ophthalmic device while sealed in the package container, such as by autoclaving, to a temperature of at least about 100° C., or at least about 121° C.

[0084] 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.

[0085] In the examples, the following abbreviations are used:

[0086] DMA: N,N-dimethylacetamide.

[0087] HEMA: 2-hydroxyethyl methacrylate.

[0088] NVP: N-vinyl-2-pyrrolidone.

[0089] EGDMA: ethylene glycol dimethacrylate.

[0090] SIGMA: (3-methacryloxy-2-hydroxypropoxy)propylbis(trimethylsiloxy)methylsilane

[0091] TRIS: 3-[tris(trimethylsiloxy)silyl]propyl methacrylate.

[0092] Irgacure 819: Photoinitiator for free radical polymerization available from Sigma Aldrich.

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

[0094] Ma2D37: A compound having the following structure and available from Shin-Etsu or Gelest: [ka]

[0095] M1EDS6: A compound having the following structure and available from Gelest: [ka]

[0096] Example 1 In this example, a red light blocking compound having the following structure was used: [ka]

[0097] The ophthalmic lenses used in this example were prepared according to methods known in the art from the formulations shown in Table 1 below, with the components listed by amount by weight. [Table 1]

[0098] The ophthalmic lenses were immersed in a series of solutions, starting with a 50:50 isopropyl alcohol (IPA):H2O solution for 10 minutes, followed by 100% IPA for 30 minutes, followed by a 50:50 IPA:H2O solution for 10 minutes, followed by 2x100% water for 10 minutes each. The lenses were then immersed in an aqueous solution of 0.5% by weight of a red light blocking compound for 18 hours with stirring. The lenses were then extracted in water three times for 20 minutes each. The lenses were then placed in vials containing borate buffer and autoclaved. The lenses were then individually placed on a horizontal integrating sphere for contact lens measurement. Transmission spectra were obtained from 200 nm to 800 nm. Figure 1 is a graph showing the transmission of red light through lenses subjected to the steps of Example 1.

[0099] Example 2 In this example, a red light blocking compound having the following structure was used: [ka]

[0100] The ophthalmic lenses used in this example were prepared according to methods known in the art from the formulations shown in Table 2 below, with the components listed by amount by weight. [Table 2]

[0101] The ophthalmic lenses are soaked in a series of solutions, starting with a 50:50 IPA:H2O solution for 10 minutes, followed by 100% IPA for 30 minutes, followed by a 50:50 IPA:H2O solution for 10 minutes, followed by 3x100% water for 20 minutes. The lenses are then soaked in an aqueous solution of 0.2% by weight of a red light blocking compound at room temperature for 18 hours, followed by a 50:50 IPA:H2O solution for 10 minutes, followed by 3x100% water for 20 minutes. The lenses are then placed in vials containing borate buffer and autoclaved.

[0102] 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.

[0103] It will be understood that various modifications can be made to the exemplary non-limiting embodiments disclosed herein. Therefore, the above description should not be construed as limiting, but only as an example of a preferred embodiment. For example, the functions implemented as the best mode for operating the exemplary non-limiting embodiments described above are for illustrative purposes only. Other configurations and methods can be implemented by those skilled in the art without departing from the scope and spirit of the present specification. Furthermore, those skilled in the art will envision other modifications within the scope and spirit of the features and advantages added herein.

Claims

1. 1. A method for preparing an ophthalmic device containing one or more red light blocking compounds, the method comprising: (a) immersing an ophthalmic device in one or more first solvent solutions to cause the ophthalmic device to swell; (b) immersing the swollen ophthalmic device in one or more second solvent solutions containing 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 to deswell the swollen ophthalmic device and encapsulate the one or more red light blocking compounds within the deswelled ophthalmic device; (c) sterilizing the deswelled ophthalmic device.

2. 10. The method of claim 1, wherein the one or more first solvent solutions comprise a blend of a low molecular weight alcohol solvent and water, and the ophthalmic device is immersed in the one or more first solvent solutions for a period ranging from 5 minutes to 120 minutes, and the one or more second solvent solutions comprise water or a blend of a low molecular weight alcohol solvent and water, and the ophthalmic device is immersed in the one or more second solvent solutions for a period ranging from 10 minutes to 18 hours.

3. Step (a) (i) immersing the ophthalmic device in the one or more first solvent solutions comprising a blend of a low molecular weight alcohol solvent and water for a period ranging from 5 minutes to 120 minutes; 13. The method of claim 1, comprising: (ii) immersing the ophthalmic device of step (i) in one or more additional solvent solutions, each comprising one or more of the same or different low molecular weight alcohol solvents, aliphatic hydrocarbon solvents, cycloaliphatic hydrocarbon solvents, ketone solvents, nitrile solvents, ether solvents, amide group-containing solvents, and water, for a period ranging from 5 minutes to 60 minutes.

4. 4. The method of any one of claims 1 to 3, 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.

5. The one or more red light blocking compounds are selected from the group consisting of the following compounds: 【Chemistry 1-1】 【Chemistry 1-2】 (In the formula, X １ and X ２ But independently, CH ２ or C(CH ３ ) ２ and R １ and R ２ are independently H or (CH ２ ) ４ SO ３ Na, R ３ is H or SO ３ The method according to any one of claims 1 to 3, wherein said at least one cation is selected from the group consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27,

6. 4. The method of any one of claims 1 to 3, wherein the one or more red light blocking compounds are present in the one or more second solvent solutions in an amount ranging from 0.05 to 5 wt %, based on a total weight of the one or more second solvent solutions.

7. The method of any one of claims 1 to 3, wherein step (c) comprises autoclaving the deswelled ophthalmic device.

8. The method of any one of claims 1 to 3, wherein the ophthalmic device is one or more of a contact lens, an intraocular lens, and a corneal implant.

9. An ophthalmic device for slowing, inhibiting, or preventing the progression of myopia, the ophthalmic device comprising 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, and that are encapsulated in a polymerization product of a monomer mixture comprising one or more ophthalmic device-forming monomers.

10. The one or more red light blocking compounds are selected from the group consisting of the following compounds: 【Chemistry 2-1】 【Chemistry 2-2】 (In the formula, X １ and X ２ But independently, CH ２ or C(CH ３ ) ２ and R １ and R ２ are independently H or (CH ２ ) ４ SO ３ Na, R ３ is H or SO ３ The ophthalmic device of claim 9 , wherein the ophthalmic device is represented by one or more of the following:

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