Ophthalmic device and method of manufacture

Abstract

A method for preparing an ophthalmic device for slowing, inhibiting, or preventing the progression of myopia involves contacting an ophthalmic device having one or more reactive functional groups with one or more red light blocking compounds having one or more reactive functional groups complementary to one or more reactive functional groups of the ophthalmic device, in a basic solution, for a period of time sufficient to covalently bond at least one reactive functional group of the ophthalmic device to at least one reactive functional group of the one or more red light blocking compounds, wherein the one or more red light blocking compounds 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.

Description

[Technical field]

[0001] This application claims priority to U.S. Provisional Patent Application No. 63 / 239,344, 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 contacting an ophthalmic device having one or more reactive functional groups with one or more red light blocking compounds having one or more reactive functional groups complementary to the one or more reactive functional groups of the ophthalmic device, in the presence of a base, for a period of time sufficient to covalently bond at least one of the one or more reactive functional groups of the ophthalmic device to at least one of the one or more reactive functional groups of the one or more red light blocking compounds, wherein the one or more red light blocking compounds 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.

[0006] According to another exemplary embodiment, a modified ophthalmic device for slowing, inhibiting or preventing the progression of myopia comprises one or more red light blocking compounds having at least one reactive functional group covalently bonded to at least one reactive functional group of an unmodified ophthalmic device, wherein the one or more red light blocking compounds block greater than about 5% to about 25% of red light transmission through the modified ophthalmic device at wavelengths between about 550 nm and about 800 nm.

[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 a modified ophthalmic device for slowing, inhibiting, or preventing the progression of myopia, the modified ophthalmic device comprising one or more red light blocking compounds having at least one reactive functional group covalently bonded to at least one reactive functional group of an unmodified ophthalmic device, wherein the one or more red light blocking compounds block greater than about 5% to about 25% of red light transmission through the modified ophthalmic device at wavelengths between about 550 nm and about 800 nm; and (b) inserting the ophthalmic device into an eye of the subject.

[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 for slowing, inhibiting, or preventing the progression of myopia in a subject (e.g., a human) in need of such a device. 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 modified ophthalmic devices described herein overcome the aforementioned problems and advantageously provide at least one of slowing, inhibiting, or preventing the progression of myopia by covalently bonding at least one reactive functional group of an unmodified ophthalmic device to at least one reactive functional group of one or more red light blocking compounds, wherein the one or more red light blocking compounds block greater than about 5% to about 25% of red light transmission through the modified ophthalmic device at wavelengths between about 550 nanometers (nm) and about 800 nm.

[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] In a non-limiting exemplary embodiment, the ophthalmic device is obtained from the polymerization product of a monomer mixture that includes one or more ophthalmic device-forming monomers. In one exemplary embodiment, the ophthalmic device for use herein includes an ophthalmic device formed from a material that is itself hydrophilic, because reactive groups such as, for example, carboxy, carbamoyl, sulfate, sulfonate, phosphate, amine, ammonium or hydroxyl groups are inherently present in the material and also present on the surface of the ophthalmic device produced therefrom. Suitable hydrophilic monomers having such reactive groups include, for example, unsaturated carboxylic acids, amides, vinyl lactams, poly(alkyleneoxy)(meth)acrylates, (meth)acrylic-substituted alcohols, hydrophilic vinyl carbonates, hydrophilic vinyl carbamates, hydrophilic oxazolones, and poly(alkene glycols) functionalized with polymerizable groups, and mixtures thereof.

[0017] Representative examples of unsaturated carboxylic acids include methacrylic acid, acrylic acid, and the like, and mixtures thereof. Representative examples of amides include alkylamides, such as N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, and the like, and mixtures thereof. Representative examples of cyclic lactams include N-vinyl-2-pyrrolidone, N-vinylcaprolactam, N-vinyl-2-piperidone, and the like, and mixtures thereof. Representative examples of (meth)acrylic substituted alcohols include 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, glyceryl 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. Patent No. 5,070,215 and the hydrophilic oxazolone monomers disclosed in U.S. Patent No. 4,910,277. Other suitable hydrophilic monomers will be apparent to those skilled in the art. Mixtures of the aforementioned hydrophilic monomers can also be used in the monomer mixtures herein.

[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 another embodiment, the ophthalmic device includes an ophthalmic 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 a bond or crosslinking member.

[0020] In an exemplary embodiment, the ophthalmic device includes an ophthalmic device formed from a material that is not itself hydrophilic. Such ophthalmic devices are formed from materials known in the art, including, by way of example, polysiloxanes, perfluoropolyethers, fluorinated poly(meth)acrylates or equivalent fluorinated polymers derived, for example, from other polymerizable carboxylic acids, polyalkyl(meth)acrylates or equivalent alkyl ester polymers derived, for example, from other polymerizable carboxylic acids, or fluorinated polyolefins, for example, fluorinated ethylene propylene polymers, or tetrafluoroethylene, preferably in combination with a dioxole, for example, perfluoro-2,2-dimethyl-1,3-dioxole. Representative examples of suitable bulk materials include, but are not limited to, lotrafilcon A, neofocon, pasifocon, telefocon, silafocon, fluorsilfocon, paflufocon, silafocon, elastofilcon, fluorofocon, or Teflon® AF. and Teflon AF materials such as Teflon AF 1600 or Teflon AF 2400, 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. Combinations of hydrophilic and hydrophobic monomers are also contemplated herein.

[0021] In an exemplary embodiment, it is 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. Exemplary 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).

[0022] 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.

[0023] The monomer mixture may also include a second device-forming monomer that includes a copolymerizable group and a reactive functional group. The copolymerizable group may be an ethylenically unsaturated group, so that the device-forming monomer copolymerizes with the hydrophilic and / or hydrophobic device-forming monomers 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 a copolymer that is, for example, a reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers. 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.

[0024] In an exemplary embodiment, the reactive group of the second device-forming monomer may include an epoxide group. Thus, the second device-forming monomer includes 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.

[0025] 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.

[0026] 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] 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~C12 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.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] In one embodiment, V is a (meth)acrylate, L is a C1-C6 alkyl, and R 1 , R 2 , R 3 , R4 , 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.

[0031] 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.

[0032] In one embodiment, the one or more non-bulky organosilicon-containing monomers are compounds represented by the structure of formula (Ib): [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 R14 is methyl, R 15 is C1-C4 alkyl and a is 2-50, and in some embodiments, 5-15.

[0033] 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.

[0034] 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.

[0035] 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, and R 17 each independently represents hydrogen or methyl; 18 independently represent a lower alkyl radical, a phenyl radical), or the following structure: [ka] (In the formula, each R 18′independently represent 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 independently represent a lower alkyl radical, a phenyl radical), or a group represented by the following structure: [ka] (In the formula, each R 18′ independently represent a lower alkyl radical or a phenyl radical, and h is 1 to 10.

[0036] 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).

[0037] 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.

[0038] 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.

[0039] 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.

[0040] In an exemplary 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]

[0041] 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.

[0042] 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 H, alkyl, haloalkyl, cycloalkyl, heterocycloalkyl, alkenyl, haloalkenyl, or aromatic; R7 and R8 are independently H or alkyl, and at least one of R7 or R8 is hydrogen; y is 2 to 7; and n is 1 to 100.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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 H, alkyl, haloalkyl, cycloalkyl, heterocycloalkyl, alkenyl, haloalkenyl, or aromatic; R7 or R8 are independently H or alkyl, and at least one of R7 or R8 is hydrogen; y is 2 to 7; and n is 1 to 100.

[0047] 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 H, alkyl, haloalkyl, 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.

[0048] In another embodiment, one class of silicone-containing monomers includes monomers of formulae (XIII)-(XVII): [ka]

[0049] 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 H, alkyl, haloalkyl, or other substituted alkyl groups; n and n 1 is as defined above.

[0050] In another embodiment, one type of silicone-containing monomer comprises 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.

[0051] 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.

[0052] In another embodiment, one class of silicone-containing monomers includes monomers of formula (XXIV). [ka]

[0053] 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 groups may optionally contain one or more heteroatoms, such as O and N, to form haloalkyl groups.

[0054] 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.

[0055] 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 a heteroaryl group, e.g., phenyl, naphthyl, tetrahydronaphthyl, indenyl, and biphenyl.

[0056] 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.

[0057] 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.

[0058] The silicone materials mentioned above are merely exemplary, and other materials for use as substrates may also be used that have been disclosed in various publications and are continually being developed for use in contact lenses and other medical devices. For example, an 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.

[0059] As mentioned above, the ophthalmic devices used herein have reactive functional groups inherently present within the device or on the surface of the device. However, if the ophthalmic device contains too few or no functional groups, the surface of the device can be modified by known techniques, such as plasma chemistry or conventional functionalization with groups such as -OH, -NH2 or -CO2H. For example, the surface of the ophthalmic device can be treated with plasma or corona discharge to introduce or increase the population of reactive functional groups on the ophthalmic device. The type of gas introduced into the treatment chamber will depend on the type of reactive functional group desired. By way of example, in one exemplary embodiment, hydroxyl surface groups can be generated in a treatment chamber atmosphere containing water vapor or alcohol. In another exemplary embodiment, carboxyl surface groups can be generated in a treatment chamber atmosphere containing oxygen, air, or another oxygen-containing gas. In another exemplary embodiment, amino surface groups can be generated in a treatment chamber atmosphere containing ammonia or an amine source. In another exemplary embodiment, mercaptan surface groups can be generated in a treatment chamber atmosphere containing a sulfur-containing gas such as an organic mercaptan or hydrogen sulfide. As one skilled in the art would readily appreciate, any combination of the aforementioned gases may be used in the treatment chamber to generate a combination of reactive functional groups on the surface of the ophthalmic device. Methods and apparatus for surface treatment by plasma discharge are disclosed, for example, in U.S. Patent Nos. 6,550,915 and 6,794,456, the contents of which are incorporated herein by reference.

[0060] In non-limiting exemplary embodiments, suitable reactive functional groups of the ophthalmic devices described herein include a wide variety of groups known to those skilled in the art. Representative examples of such reactive functional groups include, but are not limited to, hydroxy groups, amino groups, carboxy groups, carbonyl groups, aldehyde groups, sulfonic acid groups, sulfonyl chloride groups, isocyanate groups, carboxyanhydride groups, lactone groups, azlactone groups, epoxy groups, and groups replaceable by amino or hydroxy groups, such as halo groups, or mixtures thereof. In non-limiting exemplary embodiments, the reactive functional groups of the ophthalmic devices include one or more of amino groups, hydroxy groups, and carboxy groups.

[0061] Methods for making ophthalmic devices are within the purview of those skilled in the art and / or are commercially available from such sources and Bausch & Lomb, Incorporated, Johnson & Johnson, and the like.

[0062] The one or more red light blocking compounds having one or more reactive functional groups complementary to one or more reactive functional groups of the ophthalmic device include red light blocking compounds that block greater than about 5% to about 25% of red light transmission through the modified ophthalmic device disclosed herein at wavelengths between about 550 nanometers (nm) and about 800 nm. In an exemplary embodiment, the one or more red light blocking compounds having one or more reactive functional groups complementary to one or more reactive functional groups of the ophthalmic device include one or more red light blocking compounds that block greater than about 5% to about 25% of red light transmission through the modified ophthalmic device disclosed herein at wavelengths between about 550 nm and about 700 nm. In an exemplary embodiment, the one or more red light blocking compounds having one or more reactive functional groups complementary to one or more reactive functional groups of the ophthalmic device include one or more red light blocking compounds that block greater than about 5% to about 25% of red light transmission through the modified ophthalmic device disclosed herein at wavelengths between about 650 nm and about 680 nm.

[0063] In an exemplary embodiment, the one or more red light blocking compounds having one or more reactive functional groups complementary to one or more reactive functional groups of the ophthalmic device include one or more red light blocking compounds that block about 10% to about 15% of the red light transmission through the modified ophthalmic device disclosed herein at a wavelength of about 550 nm to about 800 nm. In an exemplary embodiment, the one or more red light blocking compounds having one or more reactive functional groups complementary to one or more reactive functional groups of the ophthalmic device include one or more red light blocking compounds that block about 10% to about 15% of the red light transmission through the modified ophthalmic device disclosed herein at a wavelength of about 550 nm to about 700 nm. In an exemplary embodiment, the one or more red light blocking compounds having one or more reactive functional groups complementary to one or more reactive functional groups of the ophthalmic device include one or more red light blocking compounds that block more than about 10% to about 15% of the red light transmission through the modified ophthalmic device disclosed herein at a wavelength of about 650 nm to about 680 nm.

[0064] In an exemplary embodiment, the one or more reactive functional groups of the red light blocking compound that are complementary to the one or more reactive functional groups of the ophthalmic device are sulfonate groups or vinyl sulfone groups.For example, in an exemplary non-limiting embodiment, one class of red light blocking compounds includes halotriazine compounds for reacting with one or more reactive functional groups of the ophthalmic device.Suitable halotriazine compounds are dihalotriazine compounds, such as dichlorotriazine compounds, that have at least one sulfonic acid functional group to make the compound water-soluble.The halotriazine compounds can be anionic compounds.Such dichlorotriazine compounds are described, for example, in U.S. Pat. Nos. 4,559,059 and 4,891,046, each of which is incorporated herein by reference. An example of a dichlorotriazine compound is Color Index Reactive Blue 4, which has the chemical name 2-anthracenesulfonic acid, 1-amino-4-(3-((4,6-dichloro-s-triazin-2-yl)amino)-4-sulfoanilino)-9,10-dihydro-9,10-dioxo. Monochlorotriazine compounds with at least one sulfonic acid functional group, such as Reactive Blue #2, can also react with one or more reactive functional groups of an ophthalmic device. Additionally, water-soluble compounds that can be utilized in addition to Color Index Reactive Blue 4 include compounds sold under the name Procion Blue MRS or Fiber Reactive Brilliant Blue MRS. The dye has the chemical name 2-anthracenesulfonic acid, 1-amino-4-(3-((4,6-dichloro-s-triazin-2-yl)amino)-4-sulfoanilino)-9,10-dihydro-9,10-dioxo, disodium salt or the chemical name 2-anthracenesulfonic acid, 1-amino-4-(3-((4,6-dichloro-1,3,5-triazin-2-yl)amino)-4-sulfophenyl)amino)-9,10-dihydro-9,10-dioxo, disodium salt.

[0065] In a non-limiting exemplary embodiment, another class of red light blocking compounds includes water soluble vinyl sulfone compounds such as Color Index Reactive Black #5 (Remazol Black B, CAS17095-24-8).

[0066] Representative structures of red light blocking compounds for use herein include the following compounds: [ka]

[0067] The unmodified ophthalmic device described above having one or more reactive functional groups is contacted with one or more red light blocking compounds having one or more reactive functional groups complementary to the one or more reactive functional groups of the ophthalmic device in the presence of a base for a period of time sufficient to covalently bond at least one of the one or more reactive functional groups of the ophthalmic device to at least one of the one or more reactive functional groups of the one or more red light blocking compounds, as illustrated below in non-limiting Scheme I. [ka]

[0068] As those skilled in the art will readily understand, the base is used to activate the vinyl sulfone and neutralize any acid formed during the reaction between the ophthalmic device and one or more red light blocking compounds. For example, the vinyl sulfone reacts with nucleophilic functionality (e.g., amine, hydroxyl, etc.) on the lens in a Michael addition manner to form a covalent bond. Suitable bases can be, for example, organic or inorganic bases. In exemplary embodiments, suitable inorganic bases include, for example, alkali metal or alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide, and lithium hydroxide, alkali metal or alkaline earth metal alkoxides such as sodium methoxide, potassium methoxide, sodium tert-butoxide, and potassium tert-butoxide, alkali metal or alkaline earth metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal or alkaline earth metal bicarbonates such as sodium bicarbonate and potassium bicarbonate. In an exemplary embodiment, suitable organic bases include, for example, triethylamine, trimethylamine, pyridine, diisopropylethylamine, pyridine, and dimethylaminopyridine.

[0069] In an exemplary embodiment, the molar amount of base is equal to or greater than the molar amount of the one or more red light blocking compounds, such as from about 1:1 to about 5:1. In an exemplary embodiment, the reaction is carried out at a temperature from room temperature to about 45° C., for a period of from about 5 seconds to about 18 hours.

[0070] After reaction, removal of the extractable components from the ophthalmic device can be accomplished by contacting the lens with one or more extraction solvents for a period of time sufficient to ensure substantially complete removal of the components. Suitable extraction solvents include, for example, water, low molecular weight alcohol extraction solvents, aliphatic hydrocarbon extraction solvents, cycloaliphatic hydrocarbon extraction solvents, ketone extraction solvents, nitrile extraction solvents, ether extraction solvents, amide group-containing extraction solvents, and mixtures thereof.

[0071] Suitable low molecular weight alcohol extraction solvents 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.

[0072] Suitable ketone extraction solvents include, 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, t-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.

[0073] Suitable nitrile extractants 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.

[0074] Suitable ethereal extraction 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 ethereal solvents include dimethyl ether, diethyl ether, di-i-propyl ether, dioxane, tetrahydrofuran, pyran, and the like, and mixtures thereof. In one embodiment, the ethereal solvent is tetrahydrofuran.

[0075] Suitable amide group-containing extraction 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.

[0076] In an exemplary embodiment, the one or more extraction solvents may further include water to form an extraction solution. For example, the extraction solution may be a blend containing about 25% to about 75% by weight of one or more extraction solvents and about 75% to about 25% by weight of water. In another embodiment, the blend may contain about 40% to about 60% by weight of one or more extraction solvents and about 60% to about 40% by weight of water.

[0077] In an exemplary embodiment, the modified ophthalmic device is contacted with one or more extraction solvents or a blend of one or more extraction solvents and water for a period ranging from about 5 minutes to about 120 minutes. In another embodiment, the modified ophthalmic device is contacted with one or more extraction solvents or a blend of one or more extraction solvents and water for a period ranging from about 10 minutes to about 40 minutes.

[0078] In an exemplary embodiment, the ophthalmic device is extracted in a series of one or more extraction solvents or blends of one or more extraction solvents with water, as described herein above. For example, the modified ophthalmic device is first contacted with one or more extraction solvents or blends of one or more extraction solvents with water for a period ranging from about 5 minutes to about 120 minutes, or from about 10 minutes to about 40 minutes. The modified ophthalmic device is then removed from the solution or blend and contacted with another one or more extraction solvents or blends of one or more extraction solvents with water for a period ranging from about 5 minutes to about 120 minutes.

[0079] In an exemplary embodiment, following the aforementioned extractions, the modified ophthalmic device is contacted in a series of aqueous extractions for periods ranging from about 5 minutes to about 120 minutes for each extraction.

[0080] In another step, the extracted modified ophthalmic device is sterilized. In an exemplary embodiment, the extracted modified 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 about 5 minutes to about 60 minutes. In one exemplary embodiment, the extracted ophthalmic device is subjected to autoclave conditions for about 5 minutes to about 2 hours.

[0081] The sterilized ophthalmic device is then rinsed with water and placed in its package with borate buffered saline. The package is sealed and the ophthalmic device is again subjected to autoclave conditions.

[0082] Alternatively, the extracted modified ocular device may be placed in a container that includes a receptacle portion for holding the extracted modified ocular device and a sterile packaging solution. An example of a container is a conventional ocular device blister package. This receptacle containing the extracted ocular 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 extracted modified ocular device are sterilized while still sealed in the package receptacle.

[0083] Examples of sterilization techniques include subjecting the solution and extracted ophthalmic device to thermal energy, microwave radiation, gamma radiation, or ultraviolet radiation. Specific examples involve heating the solution and extracted ophthalmic device while sealed in a packaging 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 and 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 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 50:50 isopropyl alcohol (IPA):H2O solution for 20 minutes to swell the lenses and thereby make the internal hydroxyl groups accessible to react with the red light blocker. The lenses were then placed in a 0.1N NaOH solution containing 0.01% by weight of the red light blocker for 3 hours. The lenses were then extracted 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 10 minutes each. The lenses were then placed in vials containing borate buffer and autoclaved. The lenses of Example 1 were then individually placed on a horizontal integrating sphere for contact lens measurements. Transmission spectra were obtained from 200 nm to 800 nm. Figure 1 is a graph showing the transmission of red light through the lenses of Example 1.

[0099] 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.

[0100] 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 for slowing, inhibiting, or preventing the progression of myopia, the method comprising:

1. A method comprising contacting an ophthalmic device having one or more reactive functional groups with one or more red light blocking compounds having one or more reactive functional groups complementary to the one or more reactive functional groups of the ophthalmic device, in the presence of a base, for a period of time sufficient to covalently bond at least one of the one or more reactive functional groups of the ophthalmic device to at least one of the one or more reactive functional groups of the one or more red light blocking compounds, wherein the one or more red light blocking compounds block greater than 5% to 25% of red light transmission through the ophthalmic device at wavelengths between 550 nanometers (nm) and 800 nm.

2. 10. The method 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.

3. The one or more red light blocking compounds are selected from the group consisting of the following compounds: 【Chemistry 1】 The method of claim 1 or 2, wherein the method is represented by one or more of:

4. The one or more reactive functional groups of the ophthalmic device are selected from the group consisting of OH, NH ２ and CO ２ 3. The method of claim 1 or 2, wherein the one or more reactive functional groups of the one or more red light blocking compounds comprise one or more of a sulfonate group and the base comprises an inorganic base.

5. The method of claim 1 or 2, further comprising extracting the ophthalmic device, wherein the at least one reactive functional group of the ophthalmic device is covalently bonded to the at least one reactive functional group of the one or more red light blocking compounds in one or more extraction solvents, and further comprising autoclaving the extracted ophthalmic device.

6. The method of claim 1 or 2, wherein the ophthalmic device is one or more of a contact lens, an intraocular lens, and a corneal implant.

7. A modified ophthalmic device for slowing, inhibiting or preventing the progression of myopia, comprising one or more red light blocking compounds having at least one reactive functional group covalently bonded to at least one reactive functional group of an unmodified ophthalmic device, wherein the one or more red light blocking compounds block greater than 5% to 25% of red light transmission through the modified ophthalmic device at wavelengths between 550 nanometers (nm) and 800 nm.

8. The one or more reactive functional groups of the unmodified ophthalmic device are selected from the group consisting of OH, NH ２ , and CO ２ The modified ophthalmic device of claim 7 , wherein the one or more reactive functional groups of the one or more red light blocking compounds include one or more of a sulfonate group.

9. The modified ophthalmic device of claim 7 or 8, wherein the one or more red light blocking compounds comprise a red light blocking compound that blocks greater than 5% to 25% of red light transmission through the modified ophthalmic device at wavelengths between 550 nm and 700 nm, or between 650 nm and 680 nm.

10. The one or more red light blocking compounds are selected from the group consisting of the following compounds: 【Chemistry 2】 9. The modified ophthalmic device of claim 7 or 8, represented by one or more of:

11. The modified ophthalmic device of claim 7 or 8, wherein the unmodified ophthalmic device is one or more of a contact lens, an intraocular lens, and a corneal implant.

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