Multifocal contact lenses exhibiting improved vision attributes - Patents.com

Abstract

Multifocal contact lenses containing high-energy visible (HEV) light absorbing compounds and their use to improve one or more vision attributes are described.

Description

[Technical field]

[0001] (CROSS REFERENCE TO RELATED APPLICATIONS) This application claims priority to U.S. Patent Application No. 16 / 938,145, filed July 24, 2020, and U.S. Provisional Patent Application No. 62 / 894,015, filed August 30, 2019, both of which are incorporated by reference in their entireties.

[0002] FIELD OF THEINVENTION The present invention relates to multifocal contact lenses containing high energy visible (HEV) light absorbing compounds and their use to improve one or more vision attributes. [Background technology]

[0003] As a person ages, the eye has more difficulty accommodating, i.e., bending the natural lens, or crystalline lens, to focus on objects that are relatively close to the observer. This condition is known as presbyopia. More specifically, when a person is born, their crystalline lens is flexible, which allows a high degree of accommodation. As a person ages, the crystalline lens gradually becomes more rigid and therefore less able to accommodate. Similarly, for a person who has had their natural lens, or crystalline lens, removed and replaced with an intraocular lens, or IOL, the ability to accommodate is lost.

[0004] Various types of multifocal contact lens designs have been provided for the treatment of presbyopia. These include bifocal contact lenses, trifocal contact lenses, and lenses with concentric rings, aspheric designs, and diffractive designs. For example, a multifocal contact lens, with or without astigmatism correction, may include a region in which the power increases continuously from far to near optical power or decreases continuously from near to far optical power radially from the lens center to the edge of the optical zone. Summary of the Invention [Problem to be solved by the invention]

[0005] Although multifocal lenses are effective in improving vision for presbyopic patients, many drawbacks remain. For example, many presbyopic patients remain dissatisfied with multifocal contact lenses due to issues such as clarity and quality of vision, glare, etc. Therefore, it would be an advance in the art to develop new technologies that would further improve the experience of presbyopic patients with multifocal contact lenses. [Means for solving the problem]

[0006] The present invention relates to a multifocal contact lens. The contact lens substantially transmits (e.g., transmits more than 80%) wavelengths longer than about 450 nm, while filtering high energy visible (HEV) light and, optionally, UV light. It has been discovered that such lenses provide many improved vision attributes, including one or more of the following improvements: quality of vision at different convergences, clarity of vision, reduced glare, reduced strabismus, and color contrast, when compared to multifocal contact lenses that do not filter HEV light.

[0007] Thus, in one aspect, the invention provides a contact lens, the contact lens being a free radical reaction product of a reactive mixture, the reactive mixture including one or more polymerizable compounds suitable for making a contact lens and a high energy visible (HEV) light absorbing compound, which may be a polymerizable HEV light absorbing compound, the contact lens being a multifocal contact lens. The contact lens is capable of transmitting between 0 percent and 70 percent, or between 1 percent and 70 percent, of light over the wavelength range of 400 to 409 nm.

[0008] In another aspect, the invention provides a method for improving vision attributes in a presbyopic contact lens wearer, the method comprising providing to a presbyopic contact lens wearer a multifocal contact lens that is a free radical reaction product of a reactive mixture, the reactive mixture comprising one or more polymerizable compounds suitable for making contact lenses and a high energy visible (HEV) light absorbing compound in an amount that improves a vision attribute, the vision attribute being selected from one or more of quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast.

[0009] In a further aspect, the invention provides use of a multifocal contact lens for improving at least one vision attribute selected from quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast, the multifocal contact lens being a free radical reaction product of a reactive mixture comprising one or more polymerizable compounds suitable for making contact lenses and an attribute-improving amount of a high energy visible light absorbing compound. [Brief description of the drawings]

[0010] [Figure 1] FIG. 1 shows the UV-VIS transmission spectrum of a silicone hydrogel contact lens containing an HEV light absorbing compound as described in Example 5. [Diagram 2] FIG. 1 shows the results of a clinical trial conducted according to Example 6. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] It is to be understood that the invention is not limited to the details of construction or process steps set forth in the following description, as the invention is capable of other embodiments and of being practiced or carried out in various ways using the teachings herein.

[0012] The following definitions are provided for terms used in this disclosure.

[0013] Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which this invention belongs. The definition of polymer is consistent with the definition disclosed in Compendium of Polymer Terminology and Nomenclature, IUPAC Recommendations 2008, edited by: Richard G. Jones, Jaroslav Kahovec, Robert Stepto, Edward S. Wilks, Michael Hess, Tatsuki Kitayama, and W. Val Metanomski. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference.

[0014] As used herein, the term "(meth)" refers to optional methyl substitution. Thus, a term such as "(meth)acrylate" refers to both methacrylate and acrylate.

[0015] Wherever a chemical structure is depicted, it should be understood that the disclosed options for the substituents in the structure may be combined in any combination. * and R ** and each of these contains a list of three possible groups, then nine combinations are disclosed. The same is true for combinations of features.

[0016] General formula [ *** ] n When a subscript, such as "n" in: is used to denote the number of repeat units in a chemical formula for a polymer, the formula should be interpreted as representing the number average molecular weight of the polymer.

[0017] The term "individual" includes humans and vertebrate animals.

[0018] The term "contact lens" refers to an ophthalmic device that can be placed on the cornea of ​​an individual's eye. A contact lens can provide corrective, cosmetic, or therapeutic benefits, including wound healing, delivery of drugs or nutritional supplements, diagnostic evaluation or monitoring, ultraviolet light absorption, reduction of visible light or glare, or any combination thereof. A contact lens can be of any suitable material known in the art and can be a soft lens, a hard lens, or a hybrid lens that contains at least two separate portions with different physical, mechanical, or optical properties, such as elastic modulus, water content, light transmission, or a combination thereof.

[0019] The present lenses may be composed of silicone hydrogels or conventional hydrogels. Silicone hydrogels typically contain at least one hydrophilic monomer and at least one silicone-containing component covalently bonded to each other in the cured device.

[0020] "Target polymer" refers to a polymer that has been synthesized from a reactive monomer mixture that includes monomers, macromers, prepolymers, crosslinkers, initiators, additives, diluents, and the like.

[0021] The term "polymerizable compound" means a compound that contains one or more polymerizable groups. This term includes, for example, monomers, macromers, oligomers, prepolymers, crosslinkers, and the like.

[0022] A "polymerizable group" is a group capable of undergoing free radical and / or cationic polymerization, e.g., chain growth polymerization, such as a carbon-carbon double bond that can polymerize when subjected to radical polymerization initiation conditions. Non-limiting examples of free radical polymerizable groups include (meth)acrylates, styrenes, vinyl ethers, (meth)acrylamides, N-vinyl lactams, N-vinyl amides, O-vinyl carbamates, O-vinyl carbonates, and other vinyl groups. Preferably, the free radical polymerizable group comprises (meth)acrylates, (meth)acrylamides, N-vinyl lactams, N-vinyl amides, and styryl functional groups, and mixtures of any of the foregoing. More preferably, the free radical polymerizable group comprises (meth)acrylates, (meth)acrylamides, and mixtures thereof. The polymerizable group may be unsubstituted or substituted. For example, the nitrogen atom in (meth)acrylamides may be bonded to hydrogen, or the hydrogen may be substituted with alkyl or cycloalkyl (which may themselves be further substituted).

[0023] Any type of free radical polymerization can be used, including but not limited to bulk, solution, suspension, and emulsion, as well as any of the controlled radical polymerization techniques, such as stable free radical polymerization, nitric oxide mediated living polymerization, atom transfer radical polymerization, reversible addition-fragmentation chain transfer polymerization, organotellurium mediated living radical polymerization, etc.

[0024] A "monomer" is a monofunctional molecule that can undergo chain growth polymerization, particularly free radical polymerization, thereby creating repeat units within the chemical structure of a target macromolecule. Some monomers have difunctional impurities that can act as crosslinkers. A "hydrophilic monomer" is also a monomer that, when mixed with deionized water at a concentration of 5% by weight at 25°C, gives a clear, single-phase solution. A "hydrophilic component" is a monomer, macromer, prepolymer, initiator, crosslinker, additive, or polymer that, when mixed with deionized water at a concentration of 5% by weight at 25°C, gives a clear, single-phase solution. A "hydrophobic component" is a monomer, macromer, prepolymer, initiator, crosslinker, additive, or polymer that is slightly soluble or insoluble in deionized water at 25°C.

[0025] A "polymer" is an organic compound having a number average molecular weight greater than 1500 and may be reactive or non-reactive.

[0026] A "macromonomer" or "macromer" is a polymer having one group capable of undergoing chain growth polymerization, particularly free radical polymerization, thereby creating repeat units within the chemical structure of a target macromolecule. Generally, the chemical structure of a macromer is different from the chemical structure of the target macromolecule, i.e., the repeat units of the pendant group of the macromer are different from the repeat units of the target macromolecule or its backbone. The only difference between a monomer and a macromer is one of the chemical structure of the pendant group, the molecular weight, and the molecular weight distribution. As a result, and as used herein, the patent literature sometimes defines a monomer as a polymerizable compound having a relatively low molecular weight of about 1,500 daltons or less, which essentially includes some macromers. Specifically, monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane (molecular weight = 500-1500 g / mol) (mPDMS) and mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether terminated mono-n-butyl terminated polydimethylsiloxane (molecular weight = 500-1500 g / mol) (OH-mPDMS) may be referred to as monomers or macromers. Additionally, the patent literature sometimes defines macromers as having one or more polymerizable groups, essentially expanding the general definition of macromer to include prepolymers. As a result, and as used herein, difunctional and multifunctional macromers, prepolymers, and crosslinkers may be used interchangeably.

[0027] A "silicone-containing component" is a monomer, macromer, prepolymer, crosslinker, initiator, additive, or polymer in the reactive mixture that has at least one silicon-oxygen bond, usually in the form of a siloxy group, a siloxane group, a carbosiloxane group, and mixtures thereof.

[0028] Examples of silicone-containing components useful in the present invention are disclosed in U.S. Pat. Nos. 3,808,178, 4,120,570, 4,136,250, 4,153,641, 4,740,533, 5,034,461, 5,070,215, 5,244,981, 5,314,960, 5,331,067, 5,371,147, 5,760,100, 5,849,811, 5,96 2,548, 5,965,631, 5,998,498, 6,367,929, 6,822,016, 6,943,203, 6,951,894, 7,052,131, No. 7,247,692, No. 7,396,890, No. 7,461,937, No. 7,468,398, No. 7,538,146, No. 7,553,880, No. 7,572,841, No. 7,666,921 , No. 7,691,916, No. 7,786,185, No. 7,825,170, No. 7,915,323, No. 7,994,356, No. 8,022,158, No. 8,163,206, No. 8,273, No. 802, No. 8,399,538, No. 8,415,404, No. 8,420,711, No. 8,450,387, No. 8,487,058, No. 8,568,626, No. 8,937,110, No. 8,9 37,111, 8,940,812, 8,980,972, 9,056,878, 9,125,808, 9,140,825, 9,156,934, 9,170,349, 9,217,813, 9,244,196, 9,244,197, 9,260,544, 9,297,928, 9,297,929, and European Patent No. 080539. These patents are incorporated herein by reference in their entirety.

[0029] A "polymer" is a target macromolecule made up of repeating units of the monomers used during polymerization.

[0030] A "homopolymer" is a polymer made from one monomer, a "copolymer" is a polymer made from two or more monomers, and a "terpolymer" is a polymer made from three monomers. A "block copolymer" consists of compositionally distinct blocks or segments. A diblock copolymer has two blocks. A triblock copolymer has three blocks. A "comb or graft copolymer" is made from at least one macromer.

[0031] A "repeating unit" is the smallest grouping of atoms in a polymer that corresponds to the polymerization of a particular monomer or macromer.

[0032] An "initiator" is a molecule that is decomposable into radicals that can subsequently react with monomers to initiate a free radical polymerization reaction. Thermal initiators decompose at a specific rate depending on the temperature, and typical examples are azo compounds such as 1,1'-azobisisobutyronitrile and 4,4'-azobis(4-cyanovaleric acid), peroxides such as benzoyl peroxide, tert-butyl peroxide, tert-butyl hydroperoxide, tert-butyl peroxybenzoate, dicumyl peroxide, and lauroyl peroxide, peracids such as peracetic acid and potassium persulfate, and various redox systems. Photoinitiators decompose by a photochemical process, and typical examples are derivatives of benzil, benzoin, acetophenone, benzophenone, camphorquinone, and mixtures thereof, as well as various monoacyl and bisacylphosphine oxides, and combinations thereof.

[0033] A "crosslinker" is a di- or polyfunctional monomer or macromer that can undergo free radical polymerization at two or more positions on the molecule, thereby creating branch points and polymer networks. Common examples are ethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, methylene bisacrylamide, triallyl cyanurate, etc.

[0034] A "prepolymer" is a reaction product of monomers that contain remaining polymerizable groups that can be further reacted to form a polymer.

[0035] A "polymer network" is a cross-linked macromolecule that can swell but cannot be dissolved in a solvent. A "hydrogel" is a polymer network that swells in water or an aqueous solution, typically absorbing at least 10% by weight of water. A "silicone hydrogel" is a hydrogel made from at least one silicone-containing component together with at least one hydrophilic component. The hydrophilic component may also include a non-reactive polymer.

[0036] "Conventional hydrogel" refers to a polymer network made from components that do not have any siloxy, siloxane, or carbosiloxane groups. Conventional hydrogels are prepared from reactive mixtures that include hydrophilic monomers. Examples include 2-hydroxyethyl methacrylate ("HEMA"), N-vinylpyrrolidone ("NVP"), N,N-dimethylacrylamide ("DMA"), or vinyl acetate. U.S. Patent Nos. 4,436,887, 4,495,313, 4,889,664, 5,006,622, 5,039459, 5,236,969, 5,270,418, 5,298,533, 5,824,719, 6,420,453, 6,423,761, 6,767,979, 7,934,830, 8,138,290, and 8,389,597 disclose the formation of conventional hydrogels. Commercially available conventional hydrogels include, but are not limited to, etafilcon, genfilcon, hilafilcon, lenefilcon, nesofilcon, omafilcon, polymacon, and vifilcon (including all variations thereof).

[0037] "Silicone hydrogel" refers to a polymer network made from at least one hydrophilic component and at least one silicone-containing component. Examples of silicone hydrogels include acquafilcon, asmofilcon, balafilcon, comfilcon, delefilcon, enfilcon, fanfilcon, formofilcon, galyfilcon, lotrafilcon, narafilcon, and nafilcon. In addition to arafilcon, riofilcon, samfilcon, senofilcon, somofilcon, and stenfilcon (including all variations thereof), U.S. Pat. Nos. 4,659,782, 4,659,783, 5,244,981, 5,314,960, 5,331,067, 5,371,147, 5,998,498, 6,087,4 No. 15, No. 5,760,100, No. 5,776,999, No. 5,789,461, No. 5,849,811, No. No. 5,965,631, No. 6,367,929, No. 6,822,016, No. 6,867,245, No. 6,943, No. 203, No. 7,247,692, No. 7,249,848, No. 7,553,880, No. 7,666,921, No. No. 7,786,185, No. 7,956,131, No. 8,022,158, No. 8,273,802, No. 8,399, 538, 8,470,906, 8,450,387, 8,487,058, 8,507,577, No. 8,637,621, No. 8,703,891, No. 8,937,110, No. 8,937,111, No. 8,940 , No. 812, No. 9,056,878, No. 9,057,821, No. 9,125,808, No. 9,140,825, No. 9156,934, No. 9,170,349, No. 9,244,196, No. 9,244,197, No. 9,260,544, 9,297,928, 9,297,929, and silicone hydrogels such as those prepared in WO 03 / 22321, WO 2008 / 061992, and U.S. Patent Application Publication No. 2010 / 0048847, which are incorporated herein by reference in their entireties.

[0038] An "interpenetrating polymer network" comprises two or more networks that are at least partially entangled on a molecular scale, but are not covalently bonded to each other and cannot be separated without a blocking chemical bond. A "semi-interpenetrating polymer network" comprises one or more networks and one or more polymers that are characterized by some intermixing at the molecular level between at least one network and at least one polymer. A mixture of different polymers is a "polymer blend." Although semi-interpenetrating networks are technically polymer blends, in some cases the polymers are so entangled that they cannot be easily removed.

[0039] The terms "reactive mixture" and "reactive monomer mixture" refer to a mixture of components (both reactive and non-reactive) that, when mixed together and exposed to polymerization conditions, form a conventional or inventive silicone hydrogel and contact lenses made therefrom. The reactive monomer mixture can include reactive components such as monomers, macromers, prepolymers, crosslinkers, and initiators, additives such as wetting agents, polymers, dyes, light absorbing compounds such as UV absorbers, pigments, dyes, and photochromic compounds, any of which may be reactive or non-reactive and can be retained in the resulting contact lens, as well as pharmaceutical and nutraceutical compounds, and optional diluents. It is understood that a wide range of additives can be added depending on the contact lens to be produced and the intended use. The concentrations of the components of the reactive mixture are expressed as weight percents of all components in the reactive mixture, excluding the diluent. If diluents are used, their concentrations are expressed as weight percents based on the amount of all components and diluent in the reactive mixture.

[0040] A "reactive component" is a component of the reactive mixture that becomes part of the chemical structure of the polymer network of the resulting hydrogel through covalent bonds, hydrogen bonding, electrostatic interactions, formation of an interpenetrating polymer network, or any other means.

[0041] The term "silicone hydrogel contact lenses" refers to hydrogel contact lenses made from at least one silicone-containing compound. Silicone hydrogel contact lenses generally have increased oxygen permeability compared to traditional hydrogels. Silicone hydrogel contact lenses utilize both their water content and polymer content to deliver oxygen to the eye.

[0042] The term "multifunctional" refers to a component having two or more polymerizable groups. The term "monofunctional" refers to a component having one polymerizable group.

[0043] The terms "halogen" or "halo" refer to fluorine, chlorine, bromine, and iodine.

[0044] "Alkyl" refers to an optionally substituted straight or branched chain alkyl group containing the specified number of carbon atoms. If no number is specified, the alkyl (including the optional substituents on the alkyl) may contain 1 to 16 carbon atoms. Preferably, the alkyl group contains 1 to 10 carbon atoms, alternatively 1 to 8 carbon atoms, alternatively 1 to 6 carbon atoms, alternatively 1 to 4 carbon atoms. Examples of alkyl include methyl, ethyl, propyl, isopropyl, butyl, iso-, sec- and tert-butyl, pentyl, hexyl, heptyl, 3-ethylbutyl, and the like. Examples of substituents on alkyl include one, two, or three groups independently selected from hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, thioalkyl, carbamate, carbonate, halogen, phenyl, benzyl, and combinations thereof. "Alkylene" means a divalent alkyl group, such as -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH(CH3)CH2-, and -CH2CH2CH2CH2-.

[0045] "Haloalkyl" refers to an alkyl group as defined above substituted with one or more halogen atoms, each halogen being independently F, Cl, Br, or I. A preferred halogen is F. Preferred haloalkyl groups contain 1 to 6 carbons, more preferably 1 to 4 carbons, and even more preferably 1 to 2 carbons. "Haloalkyl" includes perhaloalkyl groups such as -CF3- or -CF2CF3-. "Haloalkylene" refers to a divalent haloalkyl group such as -CH2CF2-.

[0046] "Cycloalkyl" refers to an optionally substituted cyclic hydrocarbon containing the specified number of ring carbon atoms. If no number is indicated, cycloalkyl may contain 3 to 12 ring carbon atoms. Preferably, it is a C3-C8 cycloalkyl group, a C3-C7 cycloalkyl, more preferably a C4-C7 cycloalkyl, and even more preferably a C5-C6 cycloalkyl. Examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of substituents on cycloalkyl include one, two, or three groups independently selected from alkyl, hydroxy, amino, amido, oxa, carbonyl, alkoxy, thioalkyl, amido, carbamate, carbonate, halo, phenyl, benzyl, and combinations thereof. "Cycloalkylene" refers to a divalent cycloalkyl group, such as 1,2-cyclohexylene, 1,3-cyclohexylene, or 1,4-cyclohexylene.

[0047] "Heterocycloalkyl" refers to a cycloalkyl ring or ring system as defined above in which at least one ring carbon is replaced with a heteroatom selected from nitrogen, oxygen, and sulfur. The heterocycloalkyl ring is optionally fused or otherwise attached to other heterocycloalkyl rings and / or non-aromatic hydrocarbon rings and / or phenyl rings. Preferred heterocycloalkyl groups have 5 to 7 members. More preferred heterocycloalkyl groups have 5 or 6 members. Heterocycloalkylene refers to a divalent heterocycloalkyl group.

[0048] "Aryl" refers to an optionally substituted aromatic hydrocarbon ring system containing at least one aromatic ring. The aryl group contains the indicated number of ring carbon atoms. If no number is indicated, the aryl may contain 6 to 14 ring carbon atoms. The aromatic ring may be optionally fused or otherwise attached to other aromatic or non-aromatic hydrocarbon rings. Examples of aryl groups include phenyl, naphthyl, and biphenyl. Preferred examples of aryl groups include phenyl. Examples of substituents on an aryl include one, two, or three groups independently selected from alkyl, hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, thioalkyl, carbamate, carbonate, halo, phenyl, benzyl, and combinations thereof. "Arylene" refers to a divalent aryl group, such as 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.

[0049] "Heteroaryl" refers to an aryl ring or ring system, as defined above, in which at least one ring carbon atom is replaced with a heteroatom selected from nitrogen, oxygen, and sulfur. The heteroaryl ring may be fused or otherwise bonded to one or more heteroaryl rings, aromatic or non-aromatic hydrocarbon rings, or heterocycloalkyl rings. Examples of heteroaryl groups include pyridyl, furyl, and thienyl. "Heteroarylene" refers to a divalent heteroaryl group.

[0050] "Alkoxy" refers to an alkyl group attached to the parent molecular moiety through an oxygen bridge. Examples of alkoxy groups include, for example, methoxy, ethoxy, propoxy, and isopropoxy. "Thioalkyl" refers to an alkyl group attached to the parent molecular moiety through a sulfur bridge. Examples of thioalkyl groups include, for example, methylthio, ethylthio, n-propylthio, and isopropylthio. "Aryloxy" refers to an aryl group attached to the parent molecular moiety through an oxygen bridge. Examples include phenoxy. "Cyclic alkoxy" refers to a cycloalkyl group attached to the parent moiety through an oxygen bridge.

[0051] "Alkylamine" refers to an alkyl group attached to the parent molecular moiety through an -NH bridge. Alkyleneamine refers to a divalent alkylamine group, such as -CHCHNH-.

[0052] "Siloxanyl" refers to a structure having at least one Si-O-Si bond. Thus, for example, a siloxanyl group refers to a group having at least one Si-O-Si group (i.e., a siloxane group), and a siloxanyl compound refers to a compound having at least one Si-O-Si group. "Siloxanyl" refers to monomeric (e.g., Si-O-Si) as well as oligomeric / polymeric structures (e.g., -[Si-O] n -, where n is 2 or 3 or more. Each silicon atom in the siloxanyl group is independently selected to complete their valence. A Group (R A is replaced by (as defined in options (b) to (i) of Formula A).

[0053] "Silyl" refers to a structure of formula RSi- and "siloxy" refers to a structure of formula RSi-O-, where each R in silyl or siloxy is independently selected from trimethylsiloxy, C1-C8 alkyl (preferably C1-C3 alkyl, more preferably ethyl or methyl), and C3-C8 cycloalkyl.

[0054] "Alkyleneoxy" refers to a group having the general formula -(alkylene-O-) p -or-(O-alkylene) p - groups, where one or more alkylenes are as defined above, p is 1-200, or 1-100, or 1-50, or 1-25, or 1-20, or 1-10, and each alkylene is independently optionally substituted with a group independently selected from hydroxyl, halo (e.g., fluoro), amino, amido, ether, carbonyl, carboxyl, and combinations thereof. When p is greater than 1, each alkylene may be the same or different, and the alkyleneoxy may be in a block or random configuration. When the alkyleneoxy forms a terminal group in a molecule, the terminus of the alkyleneoxy may be, for example, hydroxy or alkoxy (e.g., HO-[CH2CHO] p - or CH3O-[CH2CH2O] p Examples of alkyleneoxy include polyethyleneoxy, polypropyleneoxy, polybutyleneoxy, and poly(ethyleneoxy-co-propyleneoxy).

[0055] "Oxaalkylene" refers to an alkylene group as defined above in which one or more non-adjacent CH groups are replaced with an oxygen atom, such as -CHCHOCH(CH)CH-. "Thiaalkylene" refers to an alkylene group as defined above in which one or more non-adjacent CH groups are replaced with a sulfur atom, such as -CHCHSCH(CH)CH-.

[0056] The term "linking group" refers to a moiety that connects a polymerizable group to a parent molecule. The linking group may be any moiety that is compatible with the compound of which it is a part, does not undesirably interfere with the polymerization of the compound, and is stable under the polymerization conditions as well as the conditions of processing and storage of the final product. For example, the linking group may be a bond or may include one or more alkylenes, haloalkylenes, amides, amines, alkyleneamines, carbamates, esters (-CO2-), arylenes, heteroarylenes, cycloalkylenes, heterocycloalkylenes, alkyleneoxys, oxaalkylenes, thiaalkylenes, haloalkyleneoxys (alkyleneoxys substituted with one or more halo groups, e.g., -OCF2-, -OCF2CF2-, -OCF2CH2-), siloxanyls, alkylenesiloxanyls, or combinations thereof. The linking group may be optionally substituted with one or more substituents. Suitable substituents can include those independently selected from alkyl, halo (e.g., fluoro), hydroxyl, HO-alkyleneoxy, MeO-alkyleneoxy, siloxanyl, siloxy, siloxy-alkyleneoxy-, siloxy-alkylene-alkyleneoxy- (wherein more than one alkyleneoxy group can be present, and each methylene in the alkylene and alkyleneoxy is independently optionally substituted with hydroxyl), ether, amine, carbonyl, carbamate, and combinations thereof. The linking group can also be substituted with a polymerizable group (in addition to the polymerizable group to which it is attached), such as (meth)acrylate.

[0057] Preferred linking groups include C1-C8 alkylene (preferably C2-C6 alkylene) and C1-C8 oxaalkylene (preferably C2-C6 oxaalkylene), each of which is optionally substituted with one or two groups independently selected from hydroxyl and siloxy. Preferred linking groups also include carboxylate, amide, C1-C8 alkylene-carboxylate-C1-C8 alkylene, or C1-C8 alkylene-amide C1-C8 alkylene.

[0058] When the linking group is comprised of a combination of moieties as described above (e.g., alkylene and cycloalkylene), the moieties may be present in any order. For example, in formula E below, when L is shown to be -alkylene-cycloalkylene-, Rg-L may be either Rg-alkylene-cycloalkylene- or Rg-cycloalkylene-alkylene-. Regardless, the order listed represents the preferred order in which the moieties appear in the compound, starting from the terminal polymerizable group (Rg or Pg) to which the linking group is attached. For example, in formula E, L and L 2 and -L are preferably Rg-alkylene-cycloalkylene-, where -L 2 -Rg is preferably -cycloalkylene-alkylene-Rg.

[0059] The term "electron withdrawing group" (EWG) refers to a chemical group that withdraws electron density from the atom or group of atoms to which it is bonded. Examples of EWGs include, but are not limited to, cyano, amide, ester, keto, or aldehyde. A preferred EWG is cyano (CN).

[0060] The term "high energy visible light absorbing compound" or "HEV light absorbing compound" refers to a chemical material that absorbs one or more wavelengths of high energy visible light, for example in the range of 400-450 nm. The ability of a material to absorb light at a particular wavelength can be determined by measuring its UV / Vis transmission spectrum. A compound that exhibits no absorption at a particular wavelength will exhibit substantially 100 percent transmission at that wavelength. Conversely, a compound that absorbs completely at a particular wavelength will exhibit substantially 0% transmission at that wavelength. As used herein, when the transmission of a contact lens is given as a percentage over a particular wavelength range, it should be understood that the contact lens exhibits a percentage transmission at all wavelengths over that range. For purposes of the present invention, a material that has a transmission of greater than 90 percent over the wavelength range of 400-450 nm is not an HEV light absorbing compound.

[0061] The term "photostable", "photostability" or similar expressions means that a contact lens (containing an HEV light absorbing compound) exhibits no substantial change in its visible light transmission spectrum after exposure to light when packaged in a clear blister pack under the conditions of the International Conference on Harmonization of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH) guidelines, Q1B photostability testing of new drug substances and new drug products, published in November 1996. Preferably, the exposure is at least 1.5192 x 10 6 Estimated illuminance exposure in lux hours (168.8 hours exposure time) and 259.4 watt-hours / m 2The test is performed under ICH photostability guidelines, preferably in a photostability chamber controlled at 25°C / Amb RH, using an Option2 light source with an estimated UV radiation exposure of 100 nm (16.2 hours exposure time). When measuring lenses in blister packs, the blister packs are exposed foil side down to maximize irradiance from the light source during light exposure. After exposure, the UV / Vis spectrum of the test lens is collected and compared to a control lens (a lens not exposed to Q1B conditions). Photostability can be expressed as the percentage change in average transmission of the test lens relative to the control lens over a selected wavelength range. This change can be calculated as the absolute value of the difference in average transmission (over the selected wavelength range) between the control lens and the test lens divided by the average transmission of the control lens (over the selected wavelength range). For purposes of the present invention, a contact lens is considered photostable if the change in average transmission over a selected wavelength range (e.g., 380-450 nm) is 20 percent or less, or 15 percent or less, or 10 percent or less, or 7 percent or less, or 5 percent or less, or 2 percent or less. Measurements can be made, for example, with -1.00 diopter contact lenses.

[0062] The term "photochromic compound" refers to a material that, upon exposure to electromagnetic radiation of a particular wavelength, reversibly changes its absorption characteristics (i.e., color) caused by a photochemical reaction within the material. As an example, a photochromic compound may exhibit a reversible change in average transmittance of 5% or more, or 10% or more, or 20% or more in the visible portion of the electromagnetic spectrum (e.g., wavelength range from about 380 nm to about 760 nm) upon exposure to UV or HEV light. A "static compound" is a material that is not photochromic, and thus the material does not undergo a photochemical reaction that reversibly changes its transmittance.

[0063] The term "multifocal" encompasses any type of intraocular lens or contact lens designed for presbyopic patients. For example, the term encompasses any type of multifocal contact lens designed for presbyopic patients, including, but not limited to, bifocal contact lenses, trifocal contact lenses, translation lenses, and lenses that include concentric rings, aspheric or extended depth of focus designs, and diffractive designs. For example, a multifocal contact lens, with or without astigmatism correction, may include a region in which the power increases continuously from far to near optical power or decreases continuously from near to far optical power radially from the lens center to the edge of the optical zone. A multifocal lens may address vision problems other than presbyopia. For example, the lens may also be a toric lens for patients who are both presbyopic and astigmatic.

[0064] Unless otherwise stated, ratios, percentages, parts, etc. are by weight.

[0065] Unless otherwise stated, a numerical range such as, for example, "2 to 10" is inclusive of the numbers defining the range (eg, 2 and 10).

[0066] As noted above, one aspect of the present invention provides a multifocal contact lens that is the free radical reaction product of a reactive mixture including one or more polymerizable compounds suitable for making contact lenses and a high energy visible (HEV) light absorbing compound.

[0067] The contact lens may transmit 0 percent to 70 percent, or 1 percent to 70 percent of light over the wavelength range of 400-409 nm. The transmission of the contact lens over the wavelength range of 400-409 nm may be at least 2 percent, or at least 3 percent, or at least 4 percent. The transmission of the contact lens over the range of 400-409 nm may be up to 60 percent, or up to 50 percent, or up to 40 percent, or up to 30 percent, or up to 20 percent.

[0068] The contact lens may transmit no more than 10 percent of light over the wavelength range of 200-279 nm. The transmission of the contact lens over the wavelength range of 200-279 nm may be no more than 5 percent, or no more than 1 percent, or less than 1 percent.

[0069] The contact lens can transmit 45 percent or less of light over the wavelength range of 280 to 399 nm. The transmission of the contact lens over the wavelength range of 280 to 399 nm can be 35 percent or less, or 25 percent or less, or 20 percent or less, or 10 percent or less, or 5 percent or less, or 1 percent or less.

[0070] The contact lens can transmit at least 10 percent light over the wavelength range of 410-424 nm. The transmission of the contact lens over the wavelength range of 410-424 nm can be at least 15 percent. The transmission of the contact lens over the wavelength range of 410-424 nm can be up to 95 percent, up to 85 percent, up to 75 percent, or up to 65 percent.

[0071] The contact lens can transmit at least 50 percent light over the wavelength range of 425 to 449 nm. The transmission of the contact lens over the range of 425 to 449 nm can be at least 60 percent.

[0072] The contact lens can transmit at least 80 percent light over the wavelength range of 450-800 nm. The transmission of the contact lens over the wavelength range of 450-800 nm can be at least 85 percent.

[0073] The contact lenses can transmit between 1 and 70 percent of light over the wavelength range of 400 to 409 nm, and up to 45 percent of light over the wavelength range of 280 to 399 nm.

[0074] The contact lenses can transmit between 1 and 70 percent of light over the wavelength range of 400 to 409 nm, no more than 45 percent of light over the wavelength range of 280 to 399 nm, and at least 80 percent of light over the wavelength range of 450 to 800 nm.

[0075] The contact lenses can transmit between 1 and 70 percent of light over the wavelength range of 400 to 409 nm, no more than 45 percent of light over the wavelength range of 280 to 399 nm, between 10 and 95 percent of light over the wavelength range of 410 to 424 nm, at least 50 percent of light over the wavelength range of 425 to 449 nm, and at least 80 percent of light over the wavelength range of 450 to 800 nm.

[0076] The contact lenses may be soft hydrogel contact lenses, preferably silicone hydrogel contact lenses. The aforementioned transmission wavelengths and percentages may be measured on lenses of various thicknesses. For example, the center thickness may be 70-300 microns, or 80-230 microns, or 80-110 microns, or 90-110 microns. The concentration of the one or more high energy visible light absorbing compounds may be adjusted to achieve the aforementioned transmission characteristics. For example, the concentration may range from at least 0.01 percent, or at least 0.1 percent, or at least 1 percent, or at least 2 percent to a maximum of 10 percent or a maximum of 5 percent, based on the weight percent of all components in the reactive mixture excluding the diluent. Typical concentrations may range from 1 to 5 percent.

[0077] HEV light absorbing compounds for use in the multifocal contact lenses of the present invention have Formula I:

[0078] [ka] The compound may include: During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; Y is a linking group; P g is a polymerizable group, R, at each occurrence, is independently H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or YP g and R 1 and R 2 is, when present, independently at each occurrence C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halo), halo, hydroxy, amino, NR 3 R 4 or benzyl, R 3 and R 4 are independently H or C1-C6 alkyl, or two adjacent R 1 Or R 2 The groups, together with the carbon atom to which they are attached, are linked to form a cycloalkyl or aryl ring. The compounds of formula I preferably contain one or two Y-Pg groups. More preferably, the compounds contain one YP g Contains a group.

[0079] I-1. Compounds of formula I may include compounds of formula I-1, which are compounds of formula I, where m and n are independently 0 or 1, or both are 0.

[0080] I-2. Compounds of formula I and I-1 may include compounds of formula I-2, which are compounds of formula I or I-1, wherein m is 1 and R 1 is C1-C6 alkyl, preferably ethyl or methyl.

[0081] I-3. Compounds of formula I, I-1 and I-2 may include compounds of formula I-3, which are compounds of formula I, I-1 or I-2, wherein n is 1 and R 2 is C1-C6 alkyl, preferably ethyl or methyl.

[0082] I-4. The compounds of formula I, I-1, I-2 and I-3 may include compounds of formula I-4, which are compounds of formula I, I-1, I-2 or I-3, where R is H or C1-C6 alkyl. Preferably, R in the group T is H.

[0083] I-5. Compounds of formula I, I-1, I-2, I-3 and I-4 may include compounds of formula I-5, which are compounds of formula I, I-1, I-2, I-3 or I-4, wherein P g (Polymerizable group) at each occurrence independently includes styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinyl amide, (meth)acrylate, or (meth)acrylamide. The polymerizable group allows the compound of the present invention to form a covalent bond when reacted with monomers, crosslinkers, and other components commonly used to make contact lenses. The compatibility of the compound with the reactive mixture can be controlled by the selection of the polymerizable group (and linking group). Preferred polymerizable groups include (meth)acrylate or (meth)acrylamide. More preferred polymerizable groups are methacrylates.

[0084] I-6. Compounds of formula I, I-1, I-2, I-3, I-4 and I-5 may include compounds of formula I-6, which are compounds of formula I, I-1, I-2, I-3, I-4 or I-5, where Y (the linking group) is alkylene, cycloalkylene, heterocycloalkylene, arylene (e.g., phenylene), heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or any combination of the aforementioned groups. Preferred linking groups include C1-C8 alkylene (e.g., ethylene or propylene), C1-C8 oxaalkylene, C1-C8 alkylene-amide-C1-C8 alkylene, and C1-C8 alkylene-amine-C1-C8 alkylene. Particularly preferred is C1-C8 alkylene, especially ethylene (-CH2CH2-). When T in a compound of formula I is O, it is preferred that the carbon atom of the linking group to which O is attached is interrupted. For example, when T is O and Y is alkylene, a preferred alkylene is -C(R H )2(CH-2) x -(In the formula, R H are independently C1 to C6 alkyl (preferably independently methyl or ethyl), and x is 1 to 5).

[0085] I-7. Compounds of formula I, I-1, I-2, I-3, I-4, I-5 and I-6 may include compounds of formula I-7, which are compounds of formula I, I-1, I-2, I-3, I-4, I-5 or I-6, wherein T is a bond or NR (preferably NH).

[0086] The compound of formula I has formula II:

[0087] [ka] The compound may include: During the ceremony, m and n are independently 0, 1, 2, 3, or 4; Y is a linking group; P g is a polymerizable group, R, at each occurrence, is independently H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or YP g and R 1 and R 2 is, when present, independently at each occurrence C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halo), halo, hydroxy, amino, NR 3 R 4 or benzyl, R 3 and R 4 are independently H or C1-C6 alkyl, or two adjacent R 1 Or R 2 The groups, together with the carbon atom to which they are attached, are linked to form a cycloalkyl or aryl ring. Compounds of formula II preferably contain one or two YP g More preferably, the compound contains one YP group. g Contains a group.

[0088] II-1. Compounds of formula II may include compounds of formula II-1, which are compounds of formula II, where m and n are independently 0 or 1, or both are 0.

[0089] II-2. Compounds of formula II and II-1 may include compounds of formula II-2, which are compounds of formula II or II-1, wherein m is 1 and R 1 is C1-C6 alkyl, preferably ethyl or methyl.

[0090] II-3. Compounds of formula II, II-1 and II-2 may include compounds of formula II-3, which are compounds of formula II, II-1 or II-2, wherein n is 1 and R 2 is C1-C6 alkyl, preferably ethyl or methyl.

[0091] II-4. The compounds of formula II, II-1, II-2 and II-3 may include compounds of formula II-4, which are compounds of formula II, II-1, II-2 or II-3, wherein R is independently H or C1-C6 alkyl at each occurrence. Preferably, R is H at each occurrence. Preferably, R in the group T is H.

[0092] II-5. Compounds of formula II, II-1, II-2, II-3 and II-4 may include compounds of formula II-5, which are compounds of formula II, II-1, II-2, II-3 or II-4, wherein P g (Polymerizable group) at each occurrence independently includes styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinyl amide, (meth)acrylate, or (meth)acrylamide. The polymerizable group allows the compounds of the present invention to form covalent bonds when reacted with monomers, crosslinkers, and other components commonly used in the fabrication of polymeric devices. The compatibility of the compounds with reactive mixtures can be controlled by the selection of the polymerizable group (and linking group). Preferred polymerizable groups include (meth)acrylate or (meth)acrylamide. More preferred polymerizable groups are methacrylates.

[0093] II-6. Compounds of formula II, II-1, II-2, II-3, II-4 and II-5 may include compounds of formula II-6, which are compounds of formula II, II-1, II-2, II-3, II-4 or II-5, where Y (linking group) is alkylene, cycloalkylene, heterocycloalkylene, arylene (e.g., phenylene), heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or any combination of the aforementioned groups. Preferred linking groups include C1-C8 alkylene (e.g., ethylene or propylene), C1-C8 oxaalkylene, C1-C8 alkylene-amide-C1-C8 alkylene, and C1-C8 alkylene-amine-C1-C8 alkylene. Particularly preferred is C1-C8 alkylene, especially ethylene (-CH2CH2-).

[0094] Specific examples of compounds of Formula I include, but are not limited to, those shown in Table 1.

[0095] [Table 1-1]

[0096] [Table 1-2]

[0097] High energy visible (HEV) light absorbing compounds for use in the present invention are preferably photostable. Thus, contact lenses of the present invention comprising a HEV light absorbing compound preferably exhibit a change in average transmittance over the wavelength range of 380-450 nm of no more than 20%, alternatively no more than 15%, alternatively no more than 10%, alternatively no more than 7%, alternatively no more than 5%, alternatively no more than 2% compared to a control lens after exposure under ICH Q1B conditions.

[0098] The contact lenses of the present invention may contain other absorbing compounds in addition to the HEV light absorbing compound to provide desired absorbing properties. For example, a preferred composition may contain a HEV light absorbing compound and a compound that absorbs UV. Suitable UV absorbing compounds are known in the art and are classified into several classes, including, but not limited to, benzophenones, benzotriazoles, triazines, substituted acrylonitriles, salicylic acid derivatives, benzoic acid derivatives, cinnamic acid derivatives, chalcone derivatives, dipnone derivatives, crotonic acid derivatives, or any mixture thereof. A preferred class of UV absorbing compounds are benzotriazoles, such as Norbloc (2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole).

[0099] A particularly preferred composition comprises 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate and a UV absorbing compound such as a benzotriazole, for example, (2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole).

[0100] Compounds of formula I can be prepared by those skilled in the art using literature methods. For example, various compounds of formula I can be prepared as shown in Scheme 1 and the associated description. Exemplary reagents and procedures for these reactions are shown in the Examples.

[0101] [ka]

[0102] Scheme 1 shows a method for preparing exemplary compounds of the present invention. Thus, the carbonyl moiety of the starting material is converted to a reactive dihalide intermediate, which is further reacted with an active methylene compound without further purification or separation. The reactive mixture is protected from air and moisture until the reaction with the cyanomethylamide derivative is completed. Other compounds of the present invention can be prepared by those skilled in the art using procedures similar to those shown in Scheme 1 with appropriate substitution of reagents.

[0103] High energy visible light absorbing compounds, such as compounds of formula I, may be included in the reactive mixture to form contact lenses. In general, the high energy visible light absorbing compounds can be present in any amount, usually up to their solubility limits. For example, the compounds can be present in an amount ranging from about 0.1% to about 10% by weight, or from about 0.5 to about 5% by weight, or from about 0.75% to about 4% by weight. The upper limit is typically determined by the solubility of the compounds with other comonomers and / or diluents in the reactive monomer mixture.

[0104] A variety of contact lenses can be made, including hard contact lenses and soft contact lenses. Preferably, the contact lenses are soft contact lenses, which can be made from conventional or silicone hydrogel formulations. In addition to being multifocal, the contact lenses can also be toric. Thus, the contact lenses of the present invention can be multifocal toric contact lenses.

[0105] The present contact lenses comprise the free radical reaction product of a reactive mixture comprising one or more high energy visible (HEV) light absorbing compounds, such as compounds of formula I, one or more polymerizable compounds suitable for making the desired ophthalmic device (also referred to herein as device-forming or hydrogel-forming polymerizable compounds), and optional components. Thus, in addition to the high energy visible light absorbing compounds, such as those described above, the reactive mixture may comprise one or more of a hydrophilic component, a hydrophobic component, a silicone-containing component, a wetting agent such as a polyamide, a crosslinking agent, and additional components such as a diluent or initiator.

[0106] hydrophilic component Examples of suitable families of hydrophilic monomers include (meth)acrylates, styrenes, vinyl ethers, (meth)acrylamides, N-vinyl lactams, N-vinyl amides, N-vinyl imides, N-vinyl ureas, O-vinyl carbamates, O-vinyl carbonates, other hydrophilic vinyl compounds, and mixtures thereof.

[0107] Non-limiting examples of hydrophilic (meth)acrylate and (meth)acrylamide monomers include acrylamide, N-isopropylacrylamide, N,N-dimethylaminopropyl(meth)acrylamide, N,N-dimethylacrylamide (DMA), 2-hydroxyethyl methacrylate (HEMA), 2-hydroxypropyl(meth)acrylate, 3-hydroxypropyl(meth)acrylate, 2,3-dihydroxypropyl(meth)acrylate, 2-hydroxybutyl(meth)acrylate, 3-hydroxybutyl(meth)acrylate, 4-hydroxybutyl(meth)acrylate, N-(2-hydroxyethyl)(meth)acrylamide, N,N-bis(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, N,N-bis(2-hydroxypropyl)(meth)acrylamide, N-(3 ... N-hydroxypropyl)(meth)acrylamide, N-(2-hydroxybutyl)(meth)acrylamide, N-(3-hydroxybutyl)(meth)acrylamide, N-(4-hydroxybutyl)(meth)acrylamide, 2-aminoethyl(meth)acrylate, 3-aminopropyl(meth)acrylate, 2-aminopropyl(meth)acrylate, N-2-aminoethyl(meth)acrylamide), N-3-aminopropyl(meth)acrylamide, N-2-aminopropyl(meth)acrylamide, N,N-bis-2-aminoethyl(meth)acrylamide, N,N-bis-3-aminopropyl(meth)acrylamide), N,N-bis-2-aminopropyl(meth)acrylamide, glycerol methacrylate, polyethylene glycol monomethacrylate, (meth)acrylic acid, vinyl acetate, acrylonitrile, and mixtures thereof.

[0108] The hydrophilic monomers may also be ionic, such as anionic, cationic, zwitterionic, betaine, and mixtures thereof. Non-limiting examples of such charged monomers include (meth)acrylic acid, N-[(ethenyloxy)carbonyl]-β-alanine (VINAL), 3-acrylamidopropanoic acid (ACA1), 5-acrylamidopropanoic acid (ACA2), 3-acrylamido-3-methylbutanoic acid (AMBA), 2-(methacryloyloxy)ethyltrimethylammonium chloride (Q salt or METAC), 2-acrylamido-2-methylpropanesulfonic acid (AMPS), 1-propanaminium, N-(2-carboxyethyl)-N,N-dimethyl-3-[(1-oxo-2-propen-1-yl)amino]-, inner salt (CBT), 1-propanaminium, N,N-dimethyl-N-[3-[(1-oxo-2-propen-1-yl)amino]propyl]-3-sulfo-, inner salt (SBT), 3,5-dioxa- 8-Aza-4-phosphanedec-10-ene-1-aminium, 4-hydroxy-N,N,N-trimethyl-9-oxo-, inner salt, 4-oxide (9CI) (PBT), 2-methacryloyloxyethyl phosphorylcholine, 3-(dimethyl(4-vinylbenzyl)ammonio)propane-1-sulfonate (DMVBAPS), 3-((3-acrylamidopropyl)dimethylammonio)propane-1-sulfonate (AMPDAPS), 3-((3-methacrylamidopropyl)dimethylammonio)propane-1-sulfonate (MAMPDAPS), 3-((3-(acryloyloxy)propyl)dimethylammonio)propane-1-sulfonate (APDAPS), and methacryloyloxy)propyl)dimethylammonio)propane-1-sulfonate (MAPDAPS).

[0109] Non-limiting examples of hydrophilic N-vinyl lactam and N-vinyl amide monomers include N-vinyl pyrrolidone (NVP), N-vinyl-2-piperidone, N-vinyl-2-caprolactam, N-vinyl-3-methyl-2-caprolactam, N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-4-methyl-2-caprolactam, N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, N-vinyl acetamide (NVA), N-vinyl-N-methyl acetamide (VMA), N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide, N-vinyl-N-methyl propionamide, N-vinyl-N-methyl-2-methyl propionamide, N-vinyl ... N-methylpropionamide, N-vinyl-N,N'-dimethylurea, 1-methyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, N-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 1-N-propyl-3-methylene-2-pyrrolidone, 1-N-propyl-5-methylene-2-pyrrolidone, 1-isopropyl-3-methylene-2-pyrrolidone, 1-isopropyl-5-methylene-2-pyrrolidone, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, N-vinylformamide, N-vinylisopropylamide, N-vinylcaprolactam, N-vinylimidazole, and mixtures thereof.

[0110] Non-limiting examples of hydrophilic O-vinyl carbamate and O-vinyl carbonate monomers include N-2-hydroxyethyl vinyl carbamate and N-carboxy-β-alanine N-vinyl ester. Further examples of hydrophilic vinyl carbonate or vinyl carbamate monomers are disclosed in U.S. Patent No. 5,070,215. Hydrophilic oxazolone monomers are disclosed in U.S. Patent No. 4,910,277.

[0111] Other hydrophilic vinyl compounds include ethylene glycol vinyl ether (EGVE), di(ethylene glycol) vinyl ether (DEGVE), allyl alcohol, and 2-ethyloxazoline.

[0112] The hydrophilic monomer may also be a macromer or prepolymer of linear or branched poly(ethylene glycol), poly(propylene glycol), or statistical random or block copolymers of ethylene oxide and propylene oxide, having polymerizable moieties such as (meth)acrylates, styrenes, vinyl ethers, (meth)acrylamides, N-vinyl amides, etc. Macromers of these polyethers have one polymerizable group and prepolymers may have two or more polymerizable groups.

[0113] Preferred hydrophilic monomers of the present invention are DMA, NVP, HEMA, VMA, NVA, and mixtures thereof. Preferred hydrophilic monomers include mixtures of DMA and HEMA. Other suitable hydrophilic monomers will be apparent to those skilled in the art.

[0114] Generally, there is no particular limitation regarding the amount of hydrophilic monomer present in the reactive monomer mixture. The amount of hydrophilic monomer can be selected based on the desired properties of the resulting hydrogel, including water content, transparency, wettability, protein uptake, and the like. Wettability can be measured by contact angle, with desirable contact angles being less than about 100°, less than about 80°, and less than about 60°. The hydrophilic monomer can be present in an amount ranging from about 0.1 to about 100 weight percent, alternatively from about 1 to about 80 weight percent, alternatively from about 5 to about 65 weight percent, alternatively from about 40 to about 60 weight percent, alternatively from about 55 to about 60 weight percent, based on the total weight of the reactive components in the reactive monomer mixture.

[0115] Silicone-containing ingredients Silicone-containing components suitable for use in the present invention include one or more polymerizable compounds, each compound independently including at least one polymerizable group, at least one siloxane group, and one or more linking groups connecting the polymerizable group(s) to the siloxane group(s). The silicone-containing component may contain, for example, 1 to 220 siloxane repeat units, such as those defined below. The silicone-containing component may also contain at least one fluorine atom.

[0116] The silicone-containing component may include one or more polymerizable groups as defined above, one or more optional repeating siloxane units, and one or more linking groups connecting the polymerizable groups to the siloxane units. The silicone-containing component may include one or more polymerizable groups, one or more optional repeating siloxane units, and one or more linking groups connecting the polymerizable groups to the siloxane units, which are independently (meth)acrylate, styryl, vinyl ether, (meth)acrylamide, N-vinyl lactam, N-vinyl amide, O-vinyl carbamate, O-vinyl carbonate, vinyl groups, or mixtures thereof.

[0117] The silicone-containing component may include, independently, one or more polymerizable groups that are (meth)acrylate, (meth)acrylamide, N-vinyl lactam, N-vinyl amide, styryl, or mixtures of the foregoing, one or more optionally repeating siloxane units, and one or more linking groups connecting the polymerizable groups to the siloxane units.

[0118] The silicone-containing component may independently comprise one or more polymerizable groups that are (meth)acrylate, (meth)acrylamide, or mixtures of the foregoing, one or more optionally repeating siloxane units, and one or more linking groups connecting the polymerizable groups to the siloxane units.

[0119] Formula A. The silicone-containing component has Formula A:

[0120] [ka] and During the ceremony, At least one R A is the formula R g -L group, R g is a polymerizable group, L is a linking group, and the remaining R A are each independently (a)R g -L-, (b) C1-C optionally substituted with one or more hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, amido, carbamate, carbonate, halo, phenyl, benzyl, or combinations thereof. 16 Alkyl, (c) C-C optionally substituted with one or more alkyl, hydroxy, amino, amido, oxa, carbonyl, alkoxy, amido, carbamate, carbonate, halo, phenyl, benzyl, or combinations thereof. 12 Cycloalkyl, (d) C-C optionally substituted with one or more alkyl, hydroxy, amino, amido, oxa, carboxy, alkylcarboxy, carbonyl, alkoxy, amido, carbamate, carbonate, halo, phenyl, benzyl, or combinations thereof. 14 Aryl groups, (e) halo, (f) alkoxy, cyclic alkoxy, or aryloxy, (g) siloxy, (h) alkyleneoxy-alkyl or alkoxy-alkyleneoxy-alkyl, such as polyethyleneoxyalkyl, polypropyleneoxyalkyl, or poly(ethyleneoxy-co-propyleneoxyalkyl); or (i) a monovalent siloxane chain comprising 1 to 100 siloxane repeat units optionally substituted with alkyl, alkoxy, hydroxy, amino, oxa, carboxy, alkylcarboxy, alkoxy, amido, carbamate, halo, or combinations thereof; n is 0 to 500, or 0 to 200, or 0 to 100, or 0 to 20, and when n is other than 0, it is understood that n is a distribution having a mode equivalent to the indicated value. When n is 2 or more, the SiO units may be the same or different R A may carry substituents, different R A When substituents are present, the n groups may be in a random or block configuration.

[0121] In formula A, three R A may each contain a polymerizable group, alternatively two R A may each contain a polymerizable group, or alternatively one R A may contain a polymerizable group.

[0122] Examples of silicone-containing components suitable for use in the present invention include, but are not limited to, the compounds listed in Table 2. When a compound in Table 2 contains a polysiloxane group, the number of SiO repeat units in such compound is preferably 3 to 100, more preferably 3 to 40, or even more preferably 3 to 20, unless otherwise specified.

[0123] [Table 2-1]

[0124] [Table 2-2]

[0125] Additional non-limiting examples of suitable silicone-containing components are listed in Table 3. Unless otherwise stated, where applicable, j2 is preferably 1-100, more preferably 3-40, or even more preferably 3-15. In compounds containing j1 or j2, the sum of j1 and j2 is preferably 2-100, more preferably 3-40, or even more preferably 3-15.

[0126] [Table 3-1]

[0127] [Table 3-2]

[0128] Mixtures of silicone-containing components may also be used.For example, suitable mixtures may include, but are not limited to, mixtures of mono-(2-hydroxy-3-methacryloxypropyloxy)-propyl-terminated mono-n-butyl-terminated polydimethylsiloxanes (OH-MPDMS) with different molecular weights, such as mixtures of OH-mPDMS containing 4 and 15 repeating SiO units; mixtures of OH-mPDMS with different molecular weights (e.g., containing 4 and 15 repeating SiO units) and silicone-based crosslinkers, such as bis-3-acryloxy-2-hydroxypropyloxypropyl polydimethylsiloxanes (ac-PDMS); mixtures of 2-hydroxy-3-[3-methyl-3,3-di(trimethylsiloxy)silylpropoxy]-propyl methacrylate (SiMAA) and mono-methacryloxypropyl-terminated mono-n-butyl-terminated polydimethylsiloxanes (mPDMS), such as mPDMS1000.

[0129] The silicone-containing component used in the present invention can have an average molecular weight of from about 400 to about 4000 Daltons.

[0130] The silicone-containing component(s) may be present in an amount up to about 95%, or from about 10 to about 80%, or from about 20 to about 70% by weight of the reactive mixture (excluding diluent), based on all reactive components.

[0131] polyamide The reactive mixture may include at least one polyamide. As used herein, the term "polyamide" refers to polymers and copolymers that include repeating units that contain amide groups. The polyamide may include cyclic amide groups, non-cyclic amide groups, and combinations thereof, and may be any polyamide known to those skilled in the art. Non-cyclic polyamides include pendant non-cyclic amide groups and are capable of association with hydroxyl groups. Cyclic polyamides include cyclic amide groups and are capable of association with hydroxyl groups.

[0132] Examples of suitable acyclic polyamides include those of formulae G1 and G2:

[0133] [ka] and polymers and copolymers comprising the repeat unit In the formula, X is a direct bond, -(CO)-, or -(CONHR 44 )-, where R 44 is a C1-C3 alkyl group, R 40 is selected from H, a linear or branched, substituted or unsubstituted C1-C4 alkyl group, R 41 is selected from H, a straight or branched chain, substituted or unsubstituted C1-C4 alkyl group, an amino group having up to 2 carbon atoms, an amido group having up to 4 carbon atoms, and an alkoxy group having up to 2 carbon atoms; R 42 is selected from H, a linear or branched, substituted or unsubstituted C1-C4 alkyl group, or selected from methyl, ethoxy, hydroxyethyl, and hydroxymethyl; R 43 is selected from H, a linear or branched, substituted or unsubstituted C1-C4 alkyl group, or methyl, ethoxy, hydroxyethyl, and hydroxymethyl; R 40 and R 41 The total number of carbon atoms in R is 8 or less, including 7, 6, 5, 4, 3, or less; 42 and R 43 The total number of carbon atoms in R is 8 or less, including 7, 6, 5, 4, 3, or less. 40 and R41 The total number of carbon atoms in R may be 6 or less, or 4 or less. 42 and R 43 may have a total of up to 6 carbon atoms. As used herein, a substituted alkyl group includes an alkyl group substituted with an amine group, an amide group, an ether group, a hydroxyl group, a carbonyl group, or a carboxyl group, or combinations thereof.

[0134] R 40 and R 41 may be independently selected from H, a substituted or unsubstituted C1-C2 alkyl group; X may be a direct bond, and R 40 and R 41 R may be independently selected from H, a substituted or unsubstituted C1-C2 alkyl group. 42 and R 43 may be independently selected from H, substituted or unsubstituted C1-C2 alkyl groups, methyl, ethoxy, hydroxyethyl, and hydroxymethyl.

[0135] The acyclic polyamides of the invention may comprise a majority of repeat units of formula LV or formula LVI, or the acyclic polyamides may comprise at least 50 mol %, such as at least about 70 mol %, and at least 80 mol %, of repeat units of formula G or formula G1. Specific examples of repeat units of formula G and formula G1 include N-vinyl-N-methylacetamide, N-vinylacetamide, N-vinyl-N-methylpropionamide, N-vinyl-N-methyl-2-methylpropionamide, N-vinyl-2-methyl-propionamide, N-vinyl-N,N'-dimethylurea, N,N-dimethylacrylamide, methacrylamide, and repeat units of formula G2 and G3:

[0136] [ka] Examples of repeating units derived from acyclic amides include:

[0137] Examples of suitable cyclic amides that can be used to form the cyclic polyamides include α-lactams, β-lactams, γ-lactams, δ-lactams, and ε-lactams. Examples of suitable cyclic polyamides include those represented by formula G4:

[0138] [ka] Polymers and copolymers containing repeat units of In the formula, R 45 is a hydrogen atom or a methyl group, f is a number from 1 to 10, and X is a direct bond, -(CO)-, or -(CONHR 46 )- and R 46 is a C1-C3 alkyl group. In formula LIX, f can be 8 or less, including 7, 6, 5, 4, 3, 2, or 1. In formula G4, f can be 6 or less, including 5, 4, 3, 2, or 1. In formula G4, f can be 2-8, including 2, 3, 4, 5, 6, 7, or 8. In formula LIX, f can be 2 or 3. When X is a direct bond, f can be 2. In such cases, the cyclic polyamide can be polyvinylpyrrolidone (PVP).

[0139] The cyclic polyamides of the present invention may comprise 50 mol % or more of repeat units of formula G4, or the cyclic polyamides may comprise at least 50 mol % of repeat units of formula G4, such as at least 70 mol %, and at least 80 mol %.

[0140] Polyamides may also be copolymers containing both cyclic and non-cyclic amide repeat units. The additional repeat units may be formed from monomers selected from hydroxyalkyl (meth)acrylates, alkyl (meth)acrylates, other hydrophilic monomers, and siloxane-substituted (meth)acrylates. Any of the monomers listed as suitable hydrophilic monomers may be used as comonomers to form the additional repeat units. Specific examples of additional monomers that may be used to form polyamides include 2-hydroxyethyl (meth)acrylate, vinyl acetate, acrylonitrile, hydroxypropyl (meth)acrylate, methyl (meth)acrylate and hydroxybutyl (meth)acrylate, dihydroxypropyl (meth)acrylate, polyethylene glycol mono(meth)acrylate, and the like, and mixtures thereof. Ionic monomers may also be included.Examples of ionic monomers include (meth)acrylic acid, N-[(ethenyloxy)carbonyl]-β-alanine (VINAL, CAS#148969-96-4), 3-acrylamidopropanoic acid (ACA1), 5-acrylamidopentanoic acid (ACA2), 3-acrylamido-3-methylbutanoic acid (AMBA), 2-(methacryloyloxy)ethyltrimethylammonium chloride (Q salt or METAC), 2-acrylamido-2-methylpropanesulfonic acid (AMPS), 1-propanaminium, N-(2-carboxyethyl)-N,N-dimethyl-3-[(1-oxo-2-propen-1-yl)amino]-, inner salt (CBT, carboxybetaine, CAS 79704-35-1), 1-propanaminium, N,N-dimethyl-N-[3-[(1-oxo-2-propen-1-yl)amino]propyl]-3-sulfo-, inner salt (SBT, sulfobetaine, CAS 80293-60-3), 3,5-dioxa-8-aza-4-phosphanundeca-10-ene-1-aminium, 4-hydroxy-N,N,N-trimethyl-9-oxo-, inner salt, 4-oxide (9CI) (PBT, phosphobetaine, CAS 163674-35-9, 2-methacryloyloxyethyl phosphorylcholine, 3-(dimethyl(4-vinylbenzyl)ammonio)propane-1-sulfonate (DMVBAPS), 3-((3-acrylamidopropyl)dimethylammonio)propane-1-sulfonate (AMPDAPS), 3-((3-methacrylamidopropyl)dimethylammonio)propane-1-sulfonate (MAMPDAPS), 3-((3-(acryloyloxy)propyl)dimethylammonio)propane-1-sulfonate (APDAPS), methacryloyloxy)propyl)dimethylammonio)propane-1-sulfonate (MAPDAPS).

[0141] The reactive monomer mixture may include both acyclic and cyclic polyamides or copolymers thereof. The acyclic polyamide may be any of the acyclic polyamides or copolymers thereof described herein, and the cyclic polyamide may be any of the cyclic polyamides or copolymers thereof described herein. The polyamide may be selected from the group of polyvinylpyrrolidone (PVP), polyvinylmethylacetamide (PVMA), polydimethylacrylamide (PDMA), polyvinylacetamide (PNVA), poly(hydroxyethyl(meth)acrylamide), polyacrylamide, and copolymers and mixtures thereof. The polyamide may be a combination of PVP (e.g., PVP K90) and PVMA (e.g., PVMA with an M of about 570 KDa). w The mixture may be

[0142] The total amount of all polyamides in the reactive mixture can be in the range of 1% to about 35% by weight, such as in the range of 1% to about 15% by weight, and such as in the range of about 5% to about 15% by weight, in all cases based on the total weight of the reactive components of the reactive monomer mixture.

[0143] Without being bound by theory, when used with silicone hydrogels, polyamides function as internal wetting agents. The polyamides of the present invention may be non-polymeric, in which case they are incorporated into the silicone hydrogel as a semi-interpenetrating network. The polyamides are encapsulated or physically held within the silicone hydrogel. Alternatively, the polyamides of the present invention may be polymeric, for example as polyamide macromers or prepolymers, in which case they are covalently incorporated into the silicone hydrogel. Mixtures of polymeric and non-polymeric polyamides may also be used.

[0144] When a polyamide is incorporated within the reactive monomer mixture, the polyamide may have a weight average molecular weight of at least 100,000 Daltons, greater than about 150,000, from about 150,000 to about 2,000,000 Daltons, from about 300,000 Daltons to about 1,800,000 Daltons. Higher molecular weight polyamides can be used if compatible with the reactive monomer mixture.

[0145] Crosslinking Agent Generally, it is desirable to add one or more crosslinking agents, also referred to as crosslinking monomers, multifunctional macromers, and prepolymers, to the reactive mixture. The crosslinking agents may be selected from difunctional crosslinkers, trifunctional crosslinkers, tetrafunctional crosslinkers, and mixtures thereof, including silicone-containing and non-silicone-containing crosslinkers. Non-silicone-containing crosslinkers include ethylene glycol dimethacrylate (EGDMA), tetraethylene glycol dimethacrylate (TEGDMA), trimethylolpropane trimethacrylate (TMPTMA), triallyl cyanurate (TAC), glycerol trimethacrylate, methacryloxyethyl vinyl carbonate (HEMAVc), allyl methacrylate, methylene bisacrylamide (MBA), and polyethylene glycol dimethacrylate, where the polyethylene glycol has a molecular weight of up to about 5000 Daltons. The crosslinking agents are used in the reactive mixture in conventional amounts, for example, from about 0.000415 to about 0.0156 moles per 100 grams of reactive formulation. Alternatively, if the hydrophilic monomer and / or silicone-containing component is multifunctional due to molecular design or impurities, adding a crosslinker to the reactive mixture is optional. Examples of hydrophilic monomers and macromers that can act as crosslinkers and do not require the addition of additional crosslinkers to the reactive mixture when present include (meth)acrylate and (meth)acrylamide end-capped polyethers. Other crosslinkers will be known to those skilled in the art and can be used to make the silicone hydrogel of the present invention.

[0146] It may be desirable to select a crosslinker that has a similar reactivity to one or more of the other reactive components in the formulation. In some cases, it may be desirable to select a mixture of crosslinkers with different reactivities to control some physical, mechanical, or biological properties of the resulting silicone hydrogel. The structure and morphology of the silicone hydrogel may also be affected by the diluent(s) and curing conditions used.

[0147] Multifunctional silicone-containing components, including macromers, crosslinkers, and prepolymers, may also be included to further increase modulus and maintain tensile strength. Silicone-containing crosslinkers may be used alone or in combination with other crosslinkers. An example of a silicone-containing component that can act as a crosslinker and does not require the addition of a crosslinking monomer to the reactive mixture when present includes α,ω-bismethacryloylpropyl polydimethylsiloxane. Another example is bis-3-acryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane (ac-PDMS).

[0148] Crosslinkers with hard chemical structures and polymerizable groups that undergo free radical polymerization may also be used. Non-limiting examples of suitable hard structures include crosslinkers containing phenyl and benzyl rings, such as 1,4-phenylenediacrylate, 1,4-phenylenedimethacrylate, 2,2-bis(4-methacryloxyphenyl)-propane, 2,2-bis[4-(2-acryloxyethoxy)phenyl]propane, 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane, and 4-vinylbenzyl methacrylate, and combinations thereof. Hard crosslinkers may be included in an amount of about 0.5 to about 15, or about 2 to 10, 3 to 7, based on the total weight of all reactive components. The physical and mechanical properties of the silicone hydrogels of the present invention may be optimized for a particular application by adjusting the components in the reactive mixture.

[0149] Non-limiting examples of silicone crosslinkers also include the multifunctional silicone-containing components described above, such as the compounds of Formula E (and subformulas thereof) and the multifunctional compounds shown in Table 3.

[0150] Further components The reactive mixture may contain additional components such as, but not limited to, diluents, initiators, UV absorbers, visible light absorbers, photochromic compounds, pharmaceuticals, nutritional supplements, antimicrobial substances, colorants, pigments, copolymerizable dyes, non-polymerizable dyes, release agents, and combinations thereof.

[0151] Suitable types of diluents for the silicone hydrogel reactive mixture include alcohols having 2 to 20 carbon atoms, amides derived from primary amines having 10 to 20 carbon atoms, and carboxylic acids having 8 to 20 carbon atoms. The diluents can be primary, secondary, and tertiary alcohols.

[0152] Generally, the reactive components are mixed in a diluent to form a reactive mixture. Suitable diluents are known in the art. For silicone hydrogels, suitable diluents are disclosed in WO 03 / 022321 and U.S. Pat. No. 6,020,445, the disclosures of which are incorporated herein by reference. Suitable diluent types for silicone hydrogel reactive mixtures include alcohols having 2-20 carbons, amides having 10-20 carbon atoms derived from primary amines, and carboxylic acids having 8-20 carbon atoms. Primary and tertiary alcohols may be used. Preferred types include alcohols having 5-20 carbons and carboxylic acids having 10-20 carbon atoms. Specific diluents that may be used include 1-ethoxy-2-propanol, diisopropylaminoethanol, isopropanol, 3,7-dimethyl-3-octanol, 1-decanol, 1-dodecanol, 1-octanol, 1-pentanol, 2-pentanol, 1-hexanol, 2-hexanol, 2-octanol, 3-methyl-3-pentanol, tert-amyl alcohol, tert-butanol, 2-butanol, 1-butanol, 2-methyl-2 ... Examples of diluents include ethanol, 2-propanol, 1-propanol, ethanol, 2-ethyl-1-butanol, (3-acetoxy-2-hydroxypropyloxy)-propylbis(trimethylsiloxy)methylsilane, 1-tert-butoxy-2-propanol, 3,3-dimethyl-2-butanol, tert-butoxyethanol, 2-octyl-1-dodecanol, decanoic acid, octanoic acid, dodecanoic acid, 2-(diisopropylamino)ethanol, mixtures thereof, and the like. Examples of amide diluents include N,N-dimethylpropionamide and dimethylacetamide.

[0153] Preferred diluents include 3,7-dimethyl-3-octanol, 1-dodecanol, 1-decanol, 1-octanol, 1-pentanol, 1-hexanol, 2-hexanol, 2-octanol, 3-methyl-3-pentanol, 2-pentanol, t-amyl alcohol, tert-butanol, 2-butanol, 1-butanol, 2-methyl-2-pentanol, 2-ethyl-1-butanol, ethanol, 3,3-dimethyl-2-butanol, 2-octyl-1-dodecanol, decanoic acid, octanoic acid, dodecanoic acid, mixtures thereof, and the like.

[0154] More preferred diluents include 3,7-dimethyl-3-octanol, 1-dodecanol, 1-decanol, 1-octanol, 1-pentanol, 1-hexanol, 2-hexanol, 2-octanol, 1-dodecanol, 3-methyl-3-pentanol, 1-pentanol, 2-pentanol, t-amyl alcohol, tert-butanol, 2-butanol, 1-butanol, 2-methyl-2-pentanol, 2-ethyl-1-butanol, 3,3-dimethyl-2-butanol, 2-octyl-1-dodecanol, mixtures thereof, and the like. When a diluent is present, there is generally no particular restriction on the amount of diluent present. When a diluent is used, the diluent may be present in an amount ranging from about 2 to about 70 percent by weight, such as from about 5 to about 50 percent by weight and from about 15 to about 40 percent by weight, based on the total weight of the reactive mixture (including reactive and non-reactive compounds). Mixtures of diluents may be used.

[0155] A polymerization initiator may be used in the reactive mixture. The polymerization initiator may include at least one of those that generate free radicals at moderately high temperatures, such as lauryl peroxide, benzoyl peroxide, iso-propyl percarbonate, azobisisobutyronitrile, and photoinitiator systems, such as aromatic α-hydroxyketones, alkoxyoxybenzoins, acetophenones, acylphosphine oxides, bisacylphosphine oxides, and tertiary amines + diketones, mixtures thereof. Specific examples of photoinitiators include 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, bis(2,6-dimethoxybenzoyl)-2,4-4-trimethylpentylphosphine oxide (DMBAPO), bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (Irgacure 819), 2,4,6-trimethylbenzyldiphenylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide, benzoin methyl ester, and a combination of camphorquinone and ethyl 4-(N,N-dimethylamino)benzoate.

[0156] Commercially available (from IGM Resins BV, The Netherlands) visible light initiator systems include Irgacure® 819, Irgacure® 1700, Irgacure® 1800, Irgacure® 819, Irgacure® 1850, and Lucrin® TPO initiators. Commercially available (from IGM Resins BV) UV photoinitiators include Darocur® 1173 and Darocur® 2959. These and other photoinitiators that may be used are disclosed in "Photoinitiators for Free Radical Cationic & Anionic Photopolymerization" 2nd Edition, Vol. III, by JV Crivello & K. Dietliker, edited by G. Bradley, John Wiley and Sons, New York, 1998. The initiator is used in the reactive mixture in an amount effective to initiate photopolymerization of the reactive mixture, for example, from about 0.1 to about 2 parts by weight per 100 parts of the reactive monomer mixture. Polymerization of the reactive mixture can be initiated using heat or visible or ultraviolet light or other means, appropriately selected depending on the polymerization initiator used. Alternatively, initiation can be carried out using an electron beam without a photoinitiator. However, when a photoinitiator is used, the preferred initiator is a bisacylphosphine oxide, such as bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (Irgacure® 819), or a combination of 1-hydroxycyclohexyl phenyl ketone and bis(2,6-dimethoxybenzoyl)-2,4-4-trimethylpentylphosphine oxide (DMBAPO).

[0157] The reactive mixture for making the ophthalmic devices of the present invention may include, in addition to the high energy visible light absorbing compound, any of the polymerizable compounds and optional ingredients described above.

[0158] A preferred reactive mixture can include a high energy visible light absorbing compound, such as a compound of formula I, and a hydrophilic component.

[0159] A preferred reactive mixture may include a high energy visible light absorbing compound, such as a compound of formula I, and a hydrophilic component selected from DMA, NVP, HEMA, VMA, NVA, methacrylic acid, and mixtures thereof. A mixture of HEMA and methacrylic acid is preferred.

[0160] A preferred reactive mixture can include a high energy visible light absorbing compound, such as a compound of formula I, a hydrophilic component, and a silicone-containing component.

[0161] A preferred reactive mixture may include a high energy visible light absorbing compound, such as a compound of Formula I, a hydrophilic component, and a silicone-containing component that includes a compound of Formula A.

[0162] A preferred reactive mixture may include a high energy visible light absorbing compound, such as a compound of formula I, a hydrophilic component selected from DMA, NVP, HEMA, VMA, NVA, and mixtures thereof, a silicone-containing component, such as a compound of formula A, and an internal wetting agent.

[0163] A preferred reactive mixture may include a high energy visible light absorbing compound such as a compound of formula I, a hydrophilic component selected from DMA, HEMA, and mixtures thereof, a silicone-containing component selected from 2-hydroxy-3-[3-methyl-3,3-di(trimethylsiloxy)silylpropoxy]-propyl methacrylate (SiMAA), mono-methacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane (mPDMS), mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether terminated mono-n-butyl terminated polydimethylsiloxane (OH-mPDMS), and mixtures thereof, and a wetting agent (preferably PVP or PVMA).For the hydrophilic component, a mixture of DMA and HEMA is preferred.For the silicone-containing component, a mixture of SiMAA and mPDMS is preferred.

[0164] A preferred reactive mixture may include a high energy visible light absorbing compound, such as a compound of formula I, a hydrophilic component including a mixture of DMA and HEMA, and a silicone-containing component including a mixture of OH-mPDMS having 2-20 repeat units, preferably a mixture of 4 and 15 repeat units. Preferably, the reactive mixture further includes a silicone-containing crosslinker, such as ac-PDMS. Also preferably, the reactive mixture includes a wetting agent, preferably DMA, PVP, PVMA, or a mixture thereof.

[0165] A preferred reactive mixture comprises a high energy visible light absorbing compound, such as a compound of Formula I, from about 1 to about 15 weight percent of at least one polyamide (e.g., acyclic polyamide, cyclic polyamide, or mixtures thereof), at least one first monofunctional hydroxyl-substituted poly(disubstituted siloxane) having 4 to 8 siloxane repeat units (e.g., OH-mPDMS, where n is 4 to 8, preferably n is 4), and at least one second hydroxyl-substituted poly(disubstituted siloxane) that is a monofunctional hydroxyl-substituted poly(disubstituted siloxane) having 10 to 200, or 10 to 100, or 10 to 50, or 10 to 20 siloxane repeat units (e.g., OH-mPDMS, where n is 10 to 20). 00, or 10-100, or 10-50, or 10-20, preferably n is 15), about 5 to about 35 weight percent of at least one hydrophilic monomer, and optionally a multifunctional hydroxyl-substituted poly(disubstituted siloxane) (e.g., ac-PDMS) having 10-200 or 10-100 siloxane repeat units. Preferably, the first monofunctional hydroxyl-substituted poly(disubstituted siloxane) and the second hydroxyl-substituted poly(disubstituted siloxane) are present in concentrations to provide a ratio of the weight percent of the first monofunctional hydroxyl-substituted poly(disubstituted siloxane) to the weight percent of the second hydroxyl-substituted poly(disubstituted siloxane) of 0.4 to 1.3, or 0.4 to 1.0.

[0166] The aforementioned reactive mixture may contain optional components such as, but not limited to, one or more initiators, internal wetting agents, crosslinkers, other UV or HEV absorbers, and diluents.

[0167] Curing of Hydrogels and Manufacturing of Lenses The reactive mixture may be formed by any method known in the art, such as by shaking or stirring, and used to form a polymeric article or device by known methods. The reactive components are mixed together, either with or without a diluent, to form the reactive mixture.

[0168] For example, an ophthalmic device can be prepared by mixing the reactive components and optionally a diluent(s) with a polymerization initiator and curing under appropriate conditions to form a product that can later be molded into a suitable shape by lathing, cutting, etc. Alternatively, the reactive mixture can be placed into a mold and then cured into a suitable article.

[0169] A method of making a molded ophthalmic device such as a silicone hydrogel contact lens may include preparing a reactive monomer mixture, transferring the reactive monomer mixture to a first mold, placing a second mold over the first mold filled with the reactive monomer mixture, and curing the reactive monomer mixture by free radical copolymerization to form a silicone hydrogel in the shape of a contact lens.

[0170] The reactive mixture may be cured through any known process for shaping the reactive mixture in making contact lenses, including rotational molding and static molding. Rotational molding methods are disclosed in U.S. Patents 3,408,429 and 3,660,545, and static molding methods are disclosed in U.S. Patents 4,113,224 and 4,197,266. The contact lenses of the present invention may be formed by direct molding of silicone hydrogels, which is economical and allows precise control of the final shape of the hydrated lens. In this method, the reactive mixture is placed into a mold having the shape of the desired final silicone hydrogel, and the reactive mixture is subjected to conditions that polymerize the monomers, thereby producing a polymer of the approximate shape of the desired final product.

[0171] After curing, the lens may be subjected to extraction to remove unreacted components and to remove the lens from the lens mold. Extraction may be performed using conventional extraction fluids, such as organic solvents, such as alcohols, or may be extracted using aqueous solutions.

[0172] An aqueous solution is a solution that contains water. The aqueous solution of the present invention may contain at least about 20% water by weight, or at least about 50% water by weight, or at least about 70% water by weight, or at least about 95% water by weight. The aqueous solution may also contain additional water-soluble ingredients, such as inorganic salts or release agents, wetting agents, slip agents, pharmaceutical ingredients and nutritional supplements, combinations thereof. A release agent is a compound or mixture of compounds that, when combined with water, reduces the time required to remove a contact lens from a mold when compared to the time required to remove a contact lens using an aqueous solution that does not contain a release agent. The aqueous solution may not require special handling, such as purification, recycling, or special waste disposal.

[0173] Extraction can occur, for example, via immersion of the lens in an aqueous solution or exposure of the lens to a stream of an aqueous solution. Extraction can also include, for example, one or more of heating the aqueous solution, agitating the aqueous solution, increasing the concentration of a release agent in the aqueous solution to a level sufficient to cause release of the lens, mechanical or ultrasonic agitation of the lens, and incorporating at least one filter aid or extraction aid into the aqueous solution to a sufficient concentration to facilitate adequate removal of unreacted components from the lens. The foregoing, with or without the addition of heat, vibration, or both, may be performed in a batch or continuous process.

[0174] To facilitate leaching and demolding, it may be desirable to apply physical agitation. For example, the lens mold part to which the lens is attached can be vibrated or moved back and forth in the aqueous solution. Other methods may include passing ultrasound through the aqueous solution.

[0175] The lenses may be sterilized by known means, such as, but not limited to, high pressure steam treatment.

[0176] The transmission wavelengths and percentages described herein can be measured on lenses of various thicknesses, for example, using the methods described in the Examples. By way of example, a preferred center thickness for measuring transmission spectra in soft contact lenses can be 80-110 microns, or 90-105 microns, or 95-105 microns. Measurements can be made at the center of the lens, for example, using an instrument slit width of 4 nm. The concentration of one or more high energy visible light absorbing compounds can be adjusted to achieve the transmission characteristics described herein. By way of example, the concentration can range from at least 0.01 percent, or at least 0.1 percent, or at least 1 percent, or at least 2 percent to a maximum of 10 percent or a maximum of 5 percent, based on the weight percent of all components in the reactive mixture excluding the diluent. Typical concentrations can range from 1 to 5 percent.

[0177] Silicone hydrogel ophthalmic devices (e.g., contact lenses) according to the present invention preferably exhibit the following properties. All values ​​are preceded by "about" and the device can have any combination of the listed properties. Properties can be determined by methods known to those of skill in the art, for example, as described in U.S. Pregrant Publication No. 20180037690, which is incorporated herein by reference.

[0178] Water concentration %: at least 20%, or at least 25% and at most 80%, or at most 70% Haze: 30% or less, or 10% or less Advancing dynamic contact angle (Wilhelmy plate method): 100° or less, or 80° or less, or 50° or less Elastic modulus (psi): 150 or less, or 135 or less, or 120 or less, or 80 to 135 Oxygen permeability (Dk, Barrer): at least 60 Barrer, or at least 80, or at least 100, or at least 150, or at least 200 Elongation at break: at least 100 With respect to ionic silicone hydrogels, the following properties may also be preferred (in addition to those mentioned above): Lysozyme uptake (μg / lens): at least 100, or at least 150, or at least 500, or at least 700 Polyquaternium 1 (PQ1) uptake (%): ≦15, or ≦10, or ≦5.

[0179] The multifocal contact lenses of the present invention can be used to improve one or more vision attributes of a presbyopic contact lens wearer when compared to a multifocal contact lens that does not include an HEV light absorbing compound. The vision attribute can be overall vision quality, such as indoor and / or outdoor vision quality. The vision attribute can be vision clarity, such as distance vision clarity (seeing objects 5 feet or more away, such as road signs), intermediate vision clarity (seeing objects 2-3 feet away, such as a computer screen), near vision clarity (seeing objects close up, such as reading a book), end of day vision clarity, and / or vision clarity during daily activities. The vision attribute can be glare reduction, such as reduced glare while driving at night, reduced glare while driving during the day, reduced glare from bright indoor lights, reduced glare from bright lights through windows, reduced glare from bright sunlight, and / or reduced glare from a computer screen. The vision attribute can be strabismus reduction, such as reduced strabismus in bright sunlight, and / or reduced strabismus while working on a computer. The vision attribute can be visual comfort. The visual acuity attribute can be logmar visual acuity. The attribute can be ease of use. The visual acuity attribute can be improved color contrast.

[0180] The following items list non-limiting embodiments of the present disclosure. 1. A method for improving vision attributes in a presbyopic contact lens wearer, comprising providing to the contact lens wearer a contact lens that is a free radical reaction product of a reactive mixture, the reactive mixture comprising one or more polymerizable compounds suitable for making contact lenses and a high energy visible (HEV) light absorbing compound, wherein the vision attributes are selected from one or more of quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast. 2. The method of claim 1, wherein the contact lens transmits between 0 percent and 70 percent of light over the wavelength range of 400 to 409 nm. 3. The method according to claim 1 or 2, wherein the contact lens transmits 45 percent or less of light over the wavelength range of 280 to 399 nm. 4. The method according to any one of claims 1 to 3, wherein the contact lens transmits at least 80 percent of light over the wavelength range of 450 to 800 nm. 5. The method according to any one of paragraphs 1 to 4, wherein the contact lens is photostable. 6. The method according to any one of items 1 to 5, wherein the high-energy visible light absorbing compound is a static compound. 7. The high energy visible light absorbing compound has the formula I:

[0181] [ka] The compound includes During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; Y is a linking group; P g is a polymerizable group, R, at each occurrence, is independently H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or YP g and R 1 and R 2 is, when present, independently at each occurrence C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halo), halo, hydroxy, amino, NR 3 R 4 or benzyl, R 3 and R 4 are independently H or C1-C6 alkyl, or two adjacent R 1 Or R 2 The method according to any one of clauses 1 to 6, wherein the groups, together with the carbon atom to which they are attached, are linked to form a cycloalkyl or aryl ring. The compound of formula I preferably comprises one or two YP g More preferably, the compound contains one YP group. gContains a group. 8. The method according to item 7, wherein m and n are each independently 0 or 1. 9. The method of claim 7 or 8, wherein Y, at each occurrence, is independently alkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or a combination thereof. 10.P g Item 10. The method according to any one of items 7 to 9, wherein the monomer unit includes styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinyl amide, (meth)acrylate, or (meth)acrylamide. 11. Use of a multifocal contact lens for improving at least one vision attribute selected from quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast, wherein the contact lens is a free radical reaction product of a reactive mixture comprising one or more polymerizable compounds suitable for making contact lenses and a high energy visible light absorbing compound. 12. The use according to item 11, wherein the contact lens transmits 0 to 70 percent of light over the wavelength range of 400 to 409 nm. 13. The use according to item 11 or 12, wherein the contact lens transmits 45 percent or less of light over the wavelength range of 280 to 399 nm. 14. The use according to any one of items 11 to 13, wherein the contact lens transmits at least 80 percent of light over the wavelength range of 450 to 800 nm. 15. The use according to any one of items 11 to 14, wherein the contact lenses are photostable. 16. The use according to any one of items 11 to 15, wherein the high-energy visible light absorbing compound is a static compound. 17. A high energy visible light absorbing compound having formula I:

[0182] [ka] The compound includes During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; Y is a linking group; P g is a polymerizable group, R, at each occurrence, is independently H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or YP g and R 1 and R 2 is, when present, independently at each occurrence C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halo), halo, hydroxy, amino, NR 3 R 4 or benzyl, R 3 and R 4 are independently H or C1-C6 alkyl, or two adjacent R 1 Or R 2 The use according to any one of clauses 11 to 16, wherein the groups, together with the carbon atom to which they are attached, are linked to form a cycloalkyl or aryl ring. The compound of formula I preferably comprises one or two YP g More preferably, the compound contains one YP group. g Contains a group. 18. The use according to item 17, wherein m and n are each independently 0 or 1. 19. The use according to paragraph 17 or 18, wherein Y, at each occurrence, is independently alkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or a combination thereof. 20.P g20. The use according to any one of items 17 to 19, wherein the compound comprises styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinyl amide, (meth)acrylate, or (meth)acrylamide. 21. An intraocular lens that is a free radical reaction product of a reactive mixture, the reactive mixture comprising: one or more polymerizable compounds suitable for making an intraocular lens; a high energy visible (HEV) light absorbing compound; The intraocular lens is a multifocal intraocular lens. 22. The intraocular lens according to item 21, which transmits 0 to 70 percent of light over a wavelength range of 400 to 409 nm. 23. The intraocular lens according to item 21 or 22, which transmits 45 percent or less of light over a wavelength range of 280 to 399 nm. 24. The intraocular lens according to any one of items 21 to 23, which transmits at least 80 percent of light over a wavelength range of 450 to 800 nm. 25. The intraocular lens according to any one of items 21 to 24, which is photostable. 26. The intraocular lens according to any one of items 21 to 25, which is a multifocal toric intraocular lens. 27. The intraocular lens according to any one of items 21 to 26, wherein the high-energy visible light absorbing compound is a static compound. 28. A high energy visible light absorbing compound having formula I:

[0183] [ka] The compound includes During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; Y is a linking group; P g is a polymerizable group, R, at each occurrence, is independently H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or YP g and R 1 and R 2 is, when present, independently at each occurrence C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halo), halo, hydroxy, amino, NR 3 R 4 or benzyl, R 3 and R 4 are independently H or C1-C6 alkyl, or two adjacent R 1 Or R 2 28. The intraocular lens according to any one of items 21 to 27, wherein the groups, together with the carbon atom to which they are attached, are bonded to form a cycloalkyl or aryl ring. 29. The intraocular lens according to item 28, wherein m and n are each independently 0 or 1. 30. The intraocular lens of paragraph 28 or 29, wherein Y, at each occurrence, is independently alkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or a combination thereof. 31.P g Item 31. The intraocular lens according to any one of Items 28 to 30, wherein comprises styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinyl amide, (meth)acrylate, or (meth)acrylamide. 32. The intraocular lens according to any one of items 21 to 31, further comprising a UV absorbing compound. 33. The intraocular lens of item 32, wherein the UV absorbing compound comprises a compound of formula I, a benzophenone, a benzotriazole, a triazine, a substituted acrylonitrile, a salicylic acid derivative, a benzoic acid derivative, a cinnamic acid derivative, a chalcone derivative, a dipnone derivative, a crotonic acid derivative, or a mixture thereof. 34. The intraocular lens according to any one of items 21 to 33, wherein the polymerizable compound suitable for preparing the intraocular lens comprises a hydrophilic component, a silicone-containing component, or a mixture thereof. 35. A method for improving a vision attribute in a presbyopic intraocular lens wearer, comprising providing to the presbyopic intraocular lens wearer an intraocular lens described in any one of paragraphs 21 to 34, wherein the vision attribute is selected from one or more of quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast. 36. Use of a multifocal intraocular lens according to any one of claims 21 to 34 to improve at least one vision attribute in a presbyopic intraocular lens wearer, wherein the vision attribute is selected from one or more of quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast. 37. A method for improving a visual acuity attribute in a presbyopic intraocular lens wearer, comprising: providing to a presbyopic intraocular lens wearer a multifocal intraocular lens that is a free radical reaction product of a reactive mixture, the reactive mixture comprising: one or more polymerizable compounds suitable for making an intraocular lens; a high energy visible (HEV) light absorbing compound; The method, wherein the vision attribute is selected from one or more of vision quality, vision clarity, glare reduction, strabismus reduction, and color contrast. 38. Use of a multifocal intraocular lens for improving at least one vision attribute selected from quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast, wherein the multifocal intraocular lens is a free radical reaction product of a reactive mixture comprising one or more polymerizable compounds suitable for making an intraocular lens and a high energy visible light absorbing compound.

[0184] Some embodiments of the present invention are described in detail in the following examples. EXAMPLES

[0185] Test Method The ultraviolet-visible spectra of the compounds in solution were measured on a Perkin Elmer Lambda 45 or Agilent Cary 6000i UV / VIS scanning spectrometer. Prior to use, the instruments were allowed to thermally equilibrate for at least 30 min. For the Perkin Elmer instruments, the scan range was 200-800 nm, the scan speed was 960 nm per minute, the slit width was 4 nm, the mode was set to transmission or absorbance, and baseline correction was selected. For the Cary instruments, the scan range was 200-800 nm, the scan speed was 600 nm / min, the slit width was 2 nm, the mode was transmission or absorbance, and baseline correction was selected. Baseline correction was performed before analyzing the samples using the autozero function.

[0186] The UV-visible spectra of contact lenses partially formed from the claimed compositions were measured using a packing solution on a Perkin Elmer Lambda 45 UV / VIS or Agilent Cary 6000i UV / VIS scanning spectrometer. The instruments were allowed to thermally equilibrate for at least 30 minutes prior to use. For the Perkin Elmer instruments, the scan range was 200-800 nm, the scan speed was 960 nm per minute, the slit width was 4 nm, the mode was set to transmission, and baseline correction was selected. Baseline correction was performed using a plastic two-piece lens holder and a cuvette containing the same solvent. These two-piece contact lens holders were designed to hold the sample in the quartz cuvette at a position traversed by the incident light beam. A reference cuvette also housed the two-piece holder. To ensure that the sample thickness was consistent, all lenses were made using the same mold. The center thickness of the contact lenses was measured using an electronic thickness gauge. The reported center thickness and transmission spectra are obtained by averaging three individual lens data.

[0187] It is important to ensure that the exterior surface of the cuvette is completely clean and dry and that there are no air bubbles within the cuvette. Measurement reproducibility is improved when the reference cuvette and its lens holder remain constant and all samples use the same sample cuvette and its lens holder, ensuring that both cuvettes are properly inserted into the instrument.

[0188] The following abbreviations are used throughout the examples and figures and have the following meanings: BC: Back or base curve plastic mold FC: Front curve plastic mold DMA: N,N-dimethylacrylamide (Jarchem) HEMA: 2-hydroxyethyl methacrylate (Bimax) PVP: Poly(N-vinylpyrrolidone) (ISP Ashland) PDMA: Polydimethylacrylamide PVMA: Polyvinylmethyacetamide EGDMA: Ethylene glycol dimethacrylate (Esstech) TEGDMA: Tetraethylene glycol dimethacrylate (Esstech) Irgacure 819: Bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (BASF or Ciba Specialty Chemicals) Irgacure 1870: A blend of bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide and 1-hydroxycyclohexyl phenyl ketone (BASF or Ciba Specialty Chemicals) mPDMS: mono-n-butyl terminated, monomethacryloxypropyl terminated polydimethylsiloxane (M n =800~1000 Daltons) (Gelest) HO-mPDMS: mono-n-butyl terminated mono-(2-hydroxy-3-methacryloxypropyloxy)-propyl terminated polydimethylsiloxane (M n =400~1500 Daltons) (Ortec or DSM-Polymer Technology Group) ac-PDMS: bis-3-acryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane (Tegomer V-Si 2250 from Evonik) Blue HEMA: 1-amino-4-[3-(4-(2-methacryloyloxyethoxy)-6-chlorotriazin-2-ylamino)-4-sulfophenylamino]anthraquinone-2-sulfonic acid, as described in U.S. Pat. No. 5,944,853. Da: Daltons or g / mol kDa: kilodalton, or atomic mass unit equal to 1,000 daltons SiMAA: 2-Propenoic acid, 2-methyl-2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester (Toray), or 3-(3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)propoxy)-2-hydroxypropyl methacrylate RB247: 1,4-Bis[2-methacryloxyethylamino]-9,10-anthraquinone BHT: Butylated hydroxytoluene D3O: 3,7-dimethyl-3-octanol (Vigon) DIW: Deionized water MeOH: Methanol IPA: Isopropyl alcohol HCl: Hydrochloric acid CH2Cl2 or DCM: methylene chloride or dichloromethane SOCl2: Thionyl chloride mCPBA: m-chloroperbenzoic acid EtOAc: ethyl acetate NH2CH2CH2OH: Ethanolamine or 2-aminoethanol Norbloc: 2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole (Janssen) PP: Polypropylene, a homopolymer of propylene TT: Tuftec (Asahi Kasei Chemicals), a hydrogenated styrene butadiene block copolymer Z: Zeonor (Nippon Zeon Co Ltd), a polycycloolefin thermoplastic polymer TL03 Light: Phillips TLK 40W / 03 bulb LED: Light Emitting Diode 1 N NMR: Proton nuclear magnetic resonance spectroscopy UV-VIS: Ultraviolet-visible spectroscopy L: Liters mL: milliliter Equiv. or eq.: equivalent kg: kilogram g: grams mol: mole mmol: millimolar min:minutes nm: nanometer TLC: Thin Layer Chromatography Borate Buffer Packing Solution: 18.52 grams (300 mmol) of boric acid, 3.7 grams (9.7 mmol) of sodium borate decahydrate, and 28 grams (197 mmol) of sodium sulfate were dissolved in enough deionized water to fill a 2 liter volumetric flask.

[0189] Example 1 - Synthesis of 2-(2-cyanoacetamido)ethyl methacrylate (A) and 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate (B) as shown in Scheme 2

[0190] [ka]

[0191] Methyl cyanoacetate (40 grams, 0.4037 moles) and 25 mL of dichloromethane were stirred in a three-necked 500 mL round bottom flask equipped with a reflux condenser under a nitrogen environment. After 2-aminoethanol (23.8 grams, 0.3897 moles, approximately 0.97 equivalents) was added to the solution via an addition funnel, the temperature rose and the methylene chloride began to reflux. After the exotherm ceased, external heat was applied to continue the gentle reflux for a total of 2 hours after which no ethanolamine was observed by thin layer chromatography.

[0192] The reaction may also be carried out at room temperature and is complete within a few hours.

[0193] The mixture was cooled to room temperature and all methylene chloride was evaporated under reduced pressure. The residual oil was washed with 50 mL of ethyl acetate three times to remove unreacted starting material and non-polar impurities. The residual ethyl acetate was then removed under reduced pressure and the resulting oil was used for acylation without further purification.

[0194] The crude N-2-hydroxyethylacetamide derivative was dissolved in 150 mL of dichloromethane containing 40 grams of pyridine (about 0.5 moles) in a three-necked round-bottom flask equipped with a reflux condenser, an addition funnel, and a magnetic stir bar. The flask was immersed in an ice bath and cooled to about 0° C. Methacryloyl chloride (45.76 g, about 0.44 moles) was added dropwise through the addition funnel, and the resulting reactive mixture was allowed to warm to room temperature while the system was constantly stirred. Methanol (20 mL) was added to the flask to quench any unreacted methacryloyl chloride. The volatile components were removed by rotary evaporation under reduced pressure, and the crude product was dissolved in 800 mL of dilute aqueous HCl. The resulting aqueous solution was extracted three times with 100 mL of hexane in a separatory funnel to remove any non-polar impurities. The organic layer was discarded. Sodium chloride was added to the aqueous layer, which was then extracted three times with 300 mL of ethyl acetate. Approximately 50 milligrams of BHT was added as an inhibitor to the combined organic fractions, and the ethyl acetate was removed by rotary evaporation under reduced pressure. The crude product crystallized out of solution during solvent removal. When approximately 100 mL of ethyl acetate remained in the flask, 250 mL of hexane was added, and the crude product was isolated by vacuum filtration using a fritted glass funnel. Thin layer chromatography indicated the presence of a single compound. The filter cake was washed twice with 150 mL of hexane, then dried under vacuum at 40° C. to give 53 grams (approximately 70% yield) of 2-(2-cyanoacetamido)ethyl methacrylate (A). 1 H NMR (500MHz, CDCl3) δ1.93(3H,s,CH3),3.36(2H,s,CNCH2),3.60(2H,dd,CH2NH),4.26(2H,t,CH2OC=O),5.59(1H,m,vinylic),6.11(1H,bs,vinylic),6.52(1H,bs,NH).

[0195] A mixture of 9H-thioxanthen-9-one (2.12 grams, 0.01 mole) and thionyl chloride (5 mL, 8.2 grams, approximately 0.07 mole) was refluxed in a 50 mL round bottom flask under constant stirring under a nitrogen atmosphere. After 2 hours, the red solution was evaporated to dryness to ensure that all unreacted thionyl chloride was removed from the system. 2-(2-cyanoacetamido)ethyl methacrylate (A) (2.3 grams, 0.0117 mole, approximately 1.17 equivalents) and 15 mL of dichloromethane were added and the resulting reactive mixture was heated to reflux under a nitrogen blanket. The reaction was monitored by thin layer chromatography. After 2 hours, no change was observed in the chromatogram so the reactive mixture was cooled to room temperature. After passage through a short silica gel column (CHCl followed by 8 wt% EtOAc in CHCl), 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate (B) was isolated as yellow crystals (3.2 grams, 82% yield). The UV-VIS transmission spectrum of a 0.2 mM solution of compound B in methanol is shown in Figure 1. 1 H NMR(500MHz,CDCl3)δ1.84(3H,s,CH3),3.47(2H,m,CH2NH),4.01(2H,t,CH2OC=O),5.55(1H,m,vinylic),5.91(1H,bs,NH),5.98(1H,bs,vin ylic),7.24(1H,t,Ar-H),7.31(1H,t,Ar-H),7.39(2H,m,Ar-H),7.49(1H,d,Ar-H),7.55(1H,m,Ar-H),7.61(1H,d,Ar-H),8.04(1H,m,Ar-H).

[0196] Example 2 - Synthesis of 2-(2-cyanoacetamido)ethyl methacrylate (F) and N-(2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl)methacrylamide (G) as shown in Scheme 3

[0197] [ka]

[0198] Methyl cyanoacetate (22 grams, 0.22 moles) and 250 mL of dichloromethane were stirred in a three-necked 500 mL round bottom flask equipped with a reflux condenser under a nitrogen atmosphere. The solution was cooled in a water bath and 1,2-diaminoethane (12 grams, 0.2 moles, approximately 0.9 equivalents) was added to the mixture. As the reaction proceeded, the mixture appeared increasingly heterogeneous and the product crashed out of solution. After stirring at room temperature for 4 hours, the volatiles were evaporated under reduced pressure and the residue was washed with ethyl acetate on a fritted glass funnel and dried at 50° C. before further use. 1 H NMR(500MHz,D2O)δ2.74(2H,t,CH2NH2),3.29(2H,t,CH2NH),3.38(2H,s,CH2CN).

[0199] 2-Aminoethylcyanoacetamide (12.7 g, 0.1 moles) and 12.0 grams of sodium carbonate are stirred in 150 mL of methanol while cooling in an ice bath. Methacryloyl chloride (11.5 g, 1.1 equiv.) is added dropwise to the suspension while maintaining the reaction temperature below 30° C. at all times. Once the reaction is complete, all volatiles are evaporated under reduced pressure, the product is redissolved in acetonitrile, and the solution is filtered to remove any salts present. The acetonitrile is evaporated under reduced pressure, and the resulting solid is washed with ethyl acetate on a fritted glass funnel to give the desired 2-(2-cyanoacetamido)ethyl methacrylamide (F). 1 H NMR(500MHz,CD3OD)δ1.86(3H,s,CH3),3.22-3.26(4H,m,NH,CH2CN),3.29(4H,m,CH2NH),5.31(1H,m,vinylic),5.63(1H,m,vinylic).

[0200] A mixture of thioxanthone (4.24 g, 0.02 mol) and 8 mL of thionyl chloride (13.12 g, ca. 0.11 mol) was gently refluxed under nitrogen atmosphere with constant stirring. After heating for 2 hours, the solution was evaporated to dryness under reduced pressure to ensure removal of all unreacted thionyl chloride. 2-(2-cyanoacetamido)ethylmethacrylamide (F) (4.2 grams, ca. 1.1 eq.) and 20 mL of degassed methylene chloride were added to the flask and the mixture was gently refluxed under nitrogen atmosphere for 3 hours while monitoring the progress by TLC. Evaporate the volatiles under reduced pressure and wash the organics with ethyl acetate. A large amount of precipitate was observed, concentrating the main product. The suspension was filtered and the remaining solid was washed with ethyl acetate before drying in a vacuum oven. The UV-VIS transmission spectrum of a 0.2 mM solution of compound G in methanol is shown in Figure 2. 1 H NMR(500MHz,CDCl3)δ1.89(3H,s,CH3),3.26(2H,m,CH2NH),3.32(2H,m,CH2NH),5.33(1H,m,vinylic),5.68(1H,m,vinylic),6.63 (1H,m,NH),6.49(1H,m,NH),7.25(1H,m,Ar-H),7.33(1H,dt,Ar-H),7.39(2H,m,Ar-H),7.51-7.59(3H,m,Ar-H),8.05(1H,m,Ar-H).

[0201] Example 3 - Synthesis of 2-(2-cyanoacetoxy)ethyl methacrylate (K) and 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetoxy)ethyl methacrylate (L) as shown in Scheme 4

[0202] [ka]

[0203] 2-(2-cyanoacetoxy)ethyl methacrylate (K) was prepared by coupling cyanoacetic acid with 2-hydroxyethyl methacrylate as follows: Cyanoacetic acid (9 g, 0.106 mol) and 13 g of 2-hydroxyethyl methacrylate (HEMA) are stirred in 250 mL of dichloromethane and ethyl dimethylaminopropylcarbodiimide hydrochloride (EDC) is added to the suspension in four batches of 5 grams each (20 g, 0.104 mol). The mixture gradually becomes more homogeneous as less polar derivatives are formed and after completion of the reaction the volatiles are evaporated under reduced pressure. The product is redissolved in a 25:75 (by weight) mixture of ethyl acetate and hexane and extracted several times with deionized water to remove any residual salts and unreacted HEMA. A small amount of 4-methoxyhydroquinone (<20 mg) is added to the organic layer and the pure product is obtained after evaporation of the solvent under reduced pressure. 1 H NMR (500MHz, CDCl3) δ1.92(3H,m,CH3),3.47(2H,S,NCCH2),4.36(2H,m,OCH2),4.44(2H,m,OCH2),4.59(1H,m,vinylic),6.10(1H,m,vinylic).

[0204] A mixture of thioxanthone (4.24 g, 0.02 mol) and 8 mL of thionyl chloride (13.12 g, ca. 0.11 mol) was gently refluxed under nitrogen atmosphere with constant stirring. After heating for 2 hours, the solution was evaporated to dryness under reduced pressure to ensure removal of all unreacted thionyl chloride. A solution of 2-(2-cyanoacetoxy)ethyl methacrylate (K) (4.33 grams, ca. 1.1 equiv.) in 20 mL of degassed methylene chloride was added to the flask and the mixture was gently refluxed under nitrogen atmosphere for 3 hours while monitoring the progress by TLC. The residue was washed with methanol to remove most of the unreacted starting thioxanthone, reconcentrated, and the crude product was purified by chromatography on a silica gel plug and dried in vacuum overnight. The UV-VIS transmission spectrum of a 0.2 mM solution of compound L in dichloromethane is shown in Figure 2. 1H NMR(500MHz,CDCl3)δ1.92(3H,s,CH3),4.36(2H,m,CH2),4.44(2H,m,CH2),5.59( 1H,m,vinylic),6.10(1H,m,vinylic),7.24-7.62(7H,m,Ar-H),8.1(1H,m,Ar-H).

[0205] Example 4 - Light Stability Non-multifocal silicone hydrogel contact lenses made from reactive mixtures containing compound (B) were subjected to photostability testing as described above. The results of the spectral transmittance at various wavelengths for contact lenses containing compound (B) that were light exposed under ICH-Q1B conditions and those that were not light exposed are shown in Table 4. The data indicate that lenses containing the HEV light absorbing compounds described herein are photostable.

[0206] [Table 4]

[0207] Example 5 - Multifocal silicone hydrogel lenses with and without compound (B) Test lenses, which are multifocal silicone hydrogel lenses containing a HEV light absorbing compound (compound (B)), and control lenses (multifocal silicone hydrogel lenses without compound (B)) were made consisting of 77 weight percent of the formulations listed in Table 5 and 23 weight percent of diluent DO. The formulations were degassed, poured into molds, cured, and fabricated into contact lenses. Figure 1 shows the UV-Vis transmission spectrum of an exemplary multifocal silicone hydrogel lens containing compound (B).

[0208] [Table 5]

[0209] Example 6 - Clinical Trials Test and control lenses were made substantially as described in Example 5. The lenses were clinically tested in a single-blind, crossover randomized distribution clinical trial. A total of about 30 eligible subjects completed the study. Subjects were asked to evaluate various vision attributes of the lenses using a Patient Reported Outcomes (PRO) questionnaire. The results are shown in Figure 2. The left bar of each question is for the control lens, and the right bar is for the test lens.

[0210] The results show that the lenses of the present invention (the test lenses) were preferred over the control lenses for many vision attributes. Significant differences were observed for overall vision quality, overall vision quality indoors and outdoors, clarity of distance vision, clarity of vision at the end of the day, clarity of vision during daily activities, reduction in glare while driving at night, reduction in glare from bright indoor lights, and reduction in glare from computer screens.

[0211] [Embodiment] (1) A contact lens that is a free radical reaction product of a reactive mixture, said reactive mixture comprising: one or more polymerizable compounds suitable for making said contact lenses; a high energy visible (HEV) light absorbing compound; The contact lens is a multifocal contact lens. (2) The contact lens of embodiment 1, which transmits between 0 percent and 70 percent of light over the wavelength range of 400 to 409 nm. (3) The contact lens of embodiment 1 or 2, which transmits 45 percent or less of light over the wavelength range of 280 to 399 nm. (4) A contact lens according to any one of the preceding embodiments, which transmits at least 80 percent of light over the wavelength range of 450 to 800 nm. (5) The contact lens of any one of embodiments 1 to 4, which is photostable.

[0212] (6) The contact lens of any one of embodiments 1 to 5, which is a multifocal toric contact lens. (7) The contact lens of any one of the preceding claims, wherein the high energy visible light absorbing compound is a static compound. (8) The high energy visible light absorbing compound is represented by Formula I:

[0213] [ka] The compound includes During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; Y is a linking group; P g is a polymerizable group, R, at each occurrence, is independently H, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or YP g and R 1 and R 2 is, when present, independently at each occurrence C1-C6 alkyl, C1-C6 alkoxy, C1-C6 thioalkyl, C3-C7 cycloalkyl, aryl (preferably unsubstituted phenyl or phenyl substituted with alkyl or halo), halo, hydroxy, amino, NR 3 R 4 or benzyl, R 3 and R 4 are independently H or C1-C6 alkyl, or two adjacent R 1 Or R 2 The contact lens of any one of the preceding embodiments, wherein the groups, together with the carbon atom to which they are attached, are linked to form a cycloalkyl or aryl ring. (9) The contact lens of embodiment 8, wherein m and n are each independently 0 or 1. (10) The contact lens of any one of embodiments 8 to 9, wherein Y, at each occurrence, is independently alkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or a combination thereof.

[0214] (11) P g The contact lens of any one of embodiments 8 to 10, wherein comprises a styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinyl amide, (meth)acrylate, or (meth)acrylamide. (12) The contact lens of any one of the preceding embodiments, further comprising a UV absorbing compound. 13. The contact lens of claim 12, wherein the UV absorbing compound comprises a compound of Formula I, a benzophenone, a benzotriazole, a triazine, a substituted acrylonitrile, a salicylic acid derivative, a benzoic acid derivative, a cinnamic acid derivative, a chalcone derivative, a dipnone derivative, a crotonic acid derivative, or a mixture thereof. (14) The contact lens of any one of the preceding claims, wherein the polymerizable compound suitable for making the contact lens comprises a hydrophilic component, a silicone-containing component, or a mixture thereof. (15) A method for improving a vision attribute in a presbyopic contact lens wearer, comprising providing to the presbyopic contact lens wearer a contact lens according to any one of embodiments 1 to 14, wherein the vision attribute is selected from one or more of quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast.

[0215] (16) Use of a multifocal contact lens according to any one of embodiments 1 to 14 to improve at least one vision attribute in a presbyopic contact lens wearer, wherein the vision attribute is selected from one or more of quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast. (17) A method for improving a visual acuity attribute in a presbyopic contact lens wearer, comprising: providing to the presbyopic contact lens wearer a multifocal contact lens that is a free radical reaction product of a reactive mixture, the reactive mixture comprising: one or more polymerizable compounds suitable for making said contact lenses; a high energy visible (HEV) light absorbing compound; The method, wherein the vision attribute is selected from one or more of quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast. (18) Use of a multifocal contact lens to improve at least one vision attribute selected from quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast, said multifocal contact lens being a free radical reaction product of a reactive mixture comprising one or more polymerizable compounds suitable for making said contact lens and a high energy visible light absorbing compound. (19) The method or use of any of embodiments 15 to 18, wherein the improved visual acuity attribute comprises an improvement in said visual acuity attribute observed by a presbyopic contact lens wearer when compared to a multifocal contact lens that does not contain the HEV light absorbing compound. (20) A contact lens according to any one of embodiments 1 to 14, which is imported into a country.

[0216] (21) The contact lens of embodiment 20, wherein the country is the United States of America. (22) The HEV light absorbing compound is selected from the group consisting of 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl acrylate, N-(2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl)methacrylamide, N-(2-(2-cyano-2-(9H -thioxanthen-9-ylidene)acetamido)ethyl)acrylamide, 2-(2-cyano-N-methyl-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-cyano-2-(9H-thioxanthen-9-ylidene)-N-(2-(N-vinylacetamido)ethyl)acetamide, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl 20. The contact lens, method or use of any of the preceding claims, comprising (E)-2-(2-cyano-2-(2,4-dichloro-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, (E)-2-(2-(2-chloro-9H-thioxanthen-9-ylidene)-2-cyanoacetamido)ethyl methacrylate, (E)-2-(2-cyano-2-(2-isopropyl-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, (E)-2-(2-cyano-2-(4-isopropyl-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetoxy)ethyl methacrylate, or mixtures thereof.

Claims

1. 1. A contact lens that is a free radical reaction product of a reactive mixture, the reactive mixture comprising: one or more polymerizable compounds suitable for making said contact lenses; a high energy visible (HEV) light absorbing compound; the contact lens is a multifocal contact lens; The high energy visible light absorbing compound has Formula I: 【Chemistry 1】 The compound includes During the ceremony, m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; Y is a linking group; P g comprises a styryl, a vinyl carbonate, a vinyl ether, a vinyl carbamate, an N-vinyl lactam, an N-vinyl amide, a (meth)acrylate, or a (meth)acrylamide; R, at each occurrence, is independently H, C 1 -C 6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or Y-P g ; A contact lens, wherein R 1 and R 2 , when present, are independently at each occurrence C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 thioalkyl, C 3 -C 7 cycloalkyl, aryl, halo, hydroxy, amino, NR 3 R 4 , or benzyl, and R 3 and R 4 are independently H or C 1 -C 6 alkyl, or two adjacent R 1 or R 2 groups, together with the carbon atom to which they are attached, are joined to form a cycloalkyl or aryl ring.

2. 10. The contact lens of claim 1, which transmits between 0 percent and 70 percent of light over the wavelength range of 400 to 409 nm.

3. 3. The contact lens of claim 1, which transmits no more than 45 percent of light over the wavelength range of 280 to 399 nm.

4. A contact lens according to any one of claims 1 to 3, which transmits at least 80 percent of light over the wavelength range of 450 to 800 nm.

5. The contact lens of any one of claims 1 to 4, which is a multifocal toric contact lens.

6. The contact lens of any one of claims 1 to 5, wherein the high energy visible light absorbing compound is a static compound.

7. The contact lens of any one of claims 1 to 6, wherein m and n are each independently 0 or 1.

8. 8. The contact lens of any one of claims 1 to 7, wherein Y, at each occurrence, is independently alkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or combinations thereof.

9. The contact lens of any one of claims 1 to 8, further comprising a UV absorbing compound.

10. 10. The contact lens of claim 9, wherein the UV absorbing compound comprises a compound of Formula I, a benzophenone, a benzotriazole, a triazine, a substituted acrylonitrile, a salicylic acid derivative, a benzoic acid derivative, a cinnamic acid derivative, a chalcone derivative, a dipnone derivative, a crotonic acid derivative, or a mixture thereof.

11. The contact lens of any one of claims 1 to 10, wherein the polymerizable compound suitable for making the contact lens comprises a hydrophilic component, a silicone-containing component, or a mixture thereof.

12. 12. A method for improving a vision attribute in a presbyopic contact lens wearer, comprising providing to said presbyopic contact lens wearer a contact lens according to any one of claims 1 to 11, said vision attribute being selected from one or more of quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast.

13. 12. Use of a contact lens according to any one of claims 1 to 11 for improving at least one vision attribute in a presbyopic contact lens wearer, said vision attribute being selected from one or more of quality of vision, clarity of vision, reduction of glare, reduction of strabismus, and color contrast.

14. Use of a contact lens according to any one of claims 1 to 11 for improving at least one vision attribute selected from quality of vision, clarity of vision, reduction of glare, reduction of strabismus and colour contrast.

15. A method or use described in any one of claims 12 to 14, wherein the improvement in vision attributes includes an improvement in the vision attributes observed by a presbyopic contact lens wearer when compared to a multifocal contact lens that does not contain an HEV light absorbing compound.

16. A contact lens according to any one of claims 1 to 11, which is imported into a country.

17. The contact lens of claim 16, wherein the country is the United States of America.

18. The HEV light absorbing compound is 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl acrylate, N-(2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl)methacrylamide, N-(2-(2-cyano-2-(9H -thioxanthen-9-ylidene)acetamido)ethyl)acrylamide, 2-(2-cyano-N-methyl-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-cyano-2-(9H-thioxanthen-9-ylidene)-N-(2-(N-vinylacetamido)ethyl)acetamide, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl 16. The contact lens, method or use of any one of claims 1 to 15, comprising (E)-2-(2-(2-cyano-2-(2,4-dichloro-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, (E)-2-(2-(2-chloro-9H-thioxanthen-9-ylidene)-2-cyanoacetamido)ethyl methacrylate, (E)-2-(2-cyano-2-(2-isopropyl-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, (E)-2-(2-cyano-2-(4-isopropyl-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetoxy)ethyl methacrylate, or mixtures thereof.

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