UV / HEVL filtering contact lens

Abstract

The present invention relates to a UV / HEVL absorbing contact lens comprising a bulk hydrogel material containing repeating units of at least one UV absorbing vinyl monomer, repeating units of at least one UV / HEVL absorbing vinyl monomer, and a derivative of reactive Cu(II)-porphyrin present in a selected amount and a selected ratio. The UV / HEVL filtering contact lens of the present invention can not only provide Class I UV protection against UVA and UVB light rays (i.e., filtering more than 90% of UVA light rays and more than 99% of UVB light rays), but also mimic the natural lens of the human eye in providing HEVL protection.

Description

Technical Field

[0001] The present invention relates to a contact lens capable of filtering UV light and high - energy visible light (HEVL) having a wavelength of 380 nm to 450 nm, preferably a silicone hydrogel contact lens.

Background Art

[0002] LED lighting and electronic devices, such as smartphones, computer screens, LCD and LED TVs, etc., are widely used. These can typically emit short-wavelength visible light including violet light (380 - 450 nm) and blue light (450 - 495 nm). Such short-wavelength visible light has been shown to damage cells in both in vitro and in vivo studies reported in Experimental Eye Research 2006, 83, 1493; J. Cataract Refrac Surg 2009, 35, 354; Graefe’s Arch Clin Exp Ophthalmol 2008, 246, 671; Acta Ophthalmologica Scandinavica 2006, 84, 4; Br J Ophthalmol 2006, 90, 784; Optometry and Vision Science 2011, 88(6), 1.With the popularization of LED lighting and LED displays, such as smartphones, TVs, and computer monitors, significant efforts have been made to develop HEVL filtering ophthalmic lenses, such as glasses, contact lenses, and intraocular lenses, to protect the eyes from increasing HEVL exposure (see, for example, U.S. Patent Nos. 4,612,358; 4,528,311; 4,716,234; 4,878,748; 5,400,175; 5,662,707; 6,158,862; 6,955,430; 7,556,376; 7,803,359; 8,153,703; 8,232,326; 8,360,574; 8,585,938; 8,882,267; 9,377,569; 9,683,102; 9,814,658; 10,551,637; and 10,610,472; and U.S. Patent Application Publication Nos. 2017 / 0242274; 2018 / 0371139; 2019 / 0002415; 2019 / 0002459; 2019 / 0271798; 2019 / 0339544; 2020 / 0002267; 2020 / 0095187; 2020 / 0407324; and 2020 / 0407337).

[0003] The TOTAL30 (registered trademark) contact lens (manufactured by Alcon) contains Class I UV absorption for protection against UVA and UVB light (i.e., filtering more than 90% of UVA and more than 99% of UVB light), and can filter approximately 34% of the HEV light (380 - 450 nm) entering the eye. TOTAL30 (registered trademark) is the first contact lens that always has effective HEVL filtering performance while wearing the lens, regardless of lighting conditions. SUMMARY OF THE INVENTION PROBLEMS TO BE SOLVED BY THE INVENTION

[0004] However, in order to better protect the wearer's eyes from damage to HEVL, especially damage from violet light, a contact lens product having much higher HEVL filtering performance than the TOTAL30 (registered trademark) contact lens is desirable.

Means for Solving the Problems

[0005] The present invention provides a UV / HEVL filtering contact lens comprising a bulk hydrogel material containing (1) repeating units of at least one hydrophilic vinyl monomer, (2) repeating units of at least one vinyl crosslinking agent, (3) repeating units of at least one UV-absorbing vinyl monomer that absorbs UV light of 280 nm to 380 nm, (4) repeating units of at least one UV / HEVL-absorbing vinyl monomer that absorbs UV light of 280 nm to 380 nm and HEVL of 380 nm to 450 nm, and (5) at least one Cu(II)-porphyrin derivative, wherein the derivative is covalently bonded to the bulk hydrogel material and has an absorption peak (i.e., Soret peak or band) in the region from 395 nm to 435 nm in the visible absorption spectrum, and the components (3), (4), and (5) are present in the bulk hydrogel material in amounts and ratios such that the UV / HEVL filtering contact lens has less than 10% UVA%T, less than 1% UVB%T, about 60% or less HEVL%T, about 40% or less %T at 420 nm, and about 80% or more %T at wavelengths between 450 nm and 500 nm.

Brief Description of the Drawings

[0006]

Figure 1

Figure 2

Figure 3

Figure 4

Mode for Carrying Out the Invention

[0007] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In general, the nomenclature and laboratory procedures used herein are known to those of ordinary skill in the art and are generally employed. In those procedures, conventional methods are used, such as those implemented by one of ordinary skill in the art and various commonly cited methods. Even when a term is given in the singular, the inventors also consider the plural form of that term. The nomenclature used herein and the laboratory procedures described below are well known and generally employed in the art.

[0008] As used herein, "about" means that the number so recited includes the recited number plus or minus 1 to 10% of the recited number.

[0009] The terms "optional" or "optionally" mean that the event or circumstance described thereafter may or may not occur, and that the description includes both the case where the event or circumstance occurs and the case where it does not occur.

[0010] As used herein, "ophthalmic device" refers to contact lenses (hard or soft), intraocular lenses, corneal anrles, and other ophthalmic devices (e.g., stents, glaucoma shunts, etc.) used on or near or around the eyeball.

[0011] "Contact lens" refers to a structure that can be placed on or in the wearer's eye. A contact lens can correct, improve, or change the wearer's vision, but it does not have to. A contact lens can be made of any suitable material known in the art or developed later, and can be a soft lens, a hard lens, or a hybrid lens.

[0012] "Hydrogel contact lens" refers to a contact lens containing a hydrogel bulk (core) material. The hydrogel bulk material can be a non-silicone hydrogel material or preferably a silicone hydrogel material.

[0013] "Hydrogel" or "hydrogel material" refers to a cross-linked polymer material that has a three-dimensional polymer network (i.e., a polymer matrix), is insoluble in water, but can retain at least 10% by weight of water in its polymer matrix when fully hydrated (or equilibrated).

[0014] Siloxane, often also described as silicone in many cases, refers to a molecule having at least one moiety of -Si-O-Si- in which each Si atom has two organic groups as substituents.

[0015] "Silicone hydrogel" or "SiHy" refers to a silicone-containing hydrogel obtained by copolymerization of a polymerizable composition containing at least one silicone-containing monomer or at least one silicone-containing macromer or at least one crosslinkable silicone-containing prepolymer.

[0016] As used in this application, the term "non-silicone hydrogel" refers to a hydrogel that theoretically does not contain silicon.

[0017] "Hydrophilic", as used herein, refers to a material or a part thereof that associates more readily with water than with lipids.

[0018] The term "room temperature" refers to a temperature of about 22°C to about 26°C.

[0019] The term "soluble" with respect to a compound or substance in a solvent means that the compound or substance can dissolve in the solvent to give a solution having a concentration of at least about 0.5% by weight at room temperature (i.e., about 22°C to about 26°C).

[0020] In connection with a compound or material in a solvent, the term "insoluble" means that the compound or material is capable of dissolving in the solvent at room temperature (as defined above) to give a solution having a concentration of less than about 0.01% by weight.

[0021] "Vinyl monomer" refers to a compound having one and only one ethylenically unsaturated group, being soluble in a solvent, and being capable of polymerizing either chemically or thermally.

[0022] The term "ethylenically unsaturated group" is used herein in a broad sense and is intended to encompass any group containing at least one >C=CH 2 group. Exemplary ethylenically unsaturated groups include, but are not limited to, (meth)acryloyl (

Chem.

Chem.

Chem.

[0023] As used herein, "chemically" with respect to the curing, crosslinking, or polymerization of a polymerizable composition, prepolymer, or material means that the curing (e.g., crosslinking and / or polymerization) is effected by irradiation with actinic radiation, such as UV / visible light irradiation, etc. Thermal curing or actinic radiation curing methods are well known to those skilled in the art.

[0024] The term "acrylic monomer" refers to a vinyl monomer having one single (meth)acryloyl group. Examples of acrylic monomers include (meth)acryloxy [or (meth)acryloyloxy] monomers and (meth)acrylamide monomers.

[0025] The term "(meth)acryloxy monomer" or "(meth)acryloyloxy monomer" refers to

Chem.

[0026] The term "(meth)acrylamide monomer" refers to

Chem.

[0027] The term "(meth)acrylamide" refers to methacrylamide and / or acrylamide.

[0028] The term "(meth)acrylate" refers to methacrylate and / or acrylate.

[0029] The term "N-vinylamide monomer" refers to an amide compound having a vinyl group (-CH=CH 2 ) directly bonded to the nitrogen atom of the amide group.

[0030] The term "ene group" refers to a monovalent radical of CH 2 =CH- or CH 2 =CCH 3 - that is not covalently bonded to an oxygen or nitrogen atom or a carbonyl group.

[0031] "Monomer" refers to a vinyl monomer having one and only one ene group.

[0032] "Vinyloxycarbonylamino monomer" refers to a vinyl monomer having one and only one vinyloxycarbonylamino group.

[0033] "Vinylaminocarbonyloxy monomer" refers to a vinyl monomer having one and only one vinylaminocarbonyloxy group.

[0034] "Vinylaminocarbonylamino monomer" refers to a vinyl monomer having one and only one vinylaminocarbonylamino group.

[0035] "Hydrophilic vinyl monomer" refers to a vinyl monomer that is water-soluble or typically produces a homopolymer that can absorb at least 10 weight percent of water.

[0036] "Hydrophobic vinyl monomer" refers to a vinyl monomer that is insoluble in water and typically produces a homopolymer that can absorb less than 10 weight percent of water.

[0037] As used in this application, the term "vinyl crosslinking agent" refers to an organic compound having at least two ethylenically unsaturated groups. "Vinyl crosslinking agent" refers to a vinyl crosslinking agent having a molecular weight of 700 Daltons or less.

[0038] "Acrylic crosslinking agent" refers to a vinyl crosslinking agent having at least two (meth)acryloyl groups.

[0039] The term "acrylic repeating unit" refers to a repeating unit of a polymer material each of which is derived from an acrylic monomer or crosslinking agent by free radical polymerization to form a polymer material.

[0040] The term "terminal (meth)acryloyl group" refers to one (meth)acryloyl group located at one of the two terminals of the main chain (or skeleton) of an organic compound.

[0041] As used in this application, the term "polymer" means a material formed by polymerizing or crosslinking one or more monomers or macromers or prepolymers or combinations thereof.

[0042] "Macromer" or "prepolymer" refers to a compound or polymer containing ethylenically unsaturated groups and having a number average molecular weight exceeding 700 daltons.

[0043] As used in this application, the term "molecular weight" of a polymer material (including monomer material or macromer material) refers to the number average molecular weight unless otherwise specified or the test conditions are otherwise indicated. Those skilled in the art know methods for determining the molecular weight of polymers according to known methods, such as GPC (gel permeation chromatography) with one or more of a refractive index detector, a low angle laser light scattering detector, a multi-angle laser light scattering detector, a differential viscosity measurement detector, a UV detector, and an infrared (IR) detector; MALDI-TOF MS (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry), 1 1H NMR (proton nuclear magnetic resonance) spectroscopy, etc.

[0044] "Polysiloxane segment" or "polydiorganosiloxane segment"

Chemical formula

[0045] "Polydiorganosiloxane vinyl monomer" or "polysiloxane vinyl monomer" has the same meaning and refers to a compound containing at least one polysiloxane segment and one sole ethylenically unsaturated group.

[0046] "Polydiorganosiloxane vinyl crosslinking agent" or "polysiloxane vinyl crosslinking agent" refers to a compound containing at least one polysiloxane segment and at least two ethylenically unsaturated groups, in the same sense.

[0047] "Linear polydiorganosiloxane vinyl crosslinking agent" or "linear polysiloxane vinyl crosslinking agent" interchangeably refers to a compound containing a main chain including at least one polysiloxane segment, and terminated with one ethylenically unsaturated group at each of the two ends of the main chain.

[0048] "Chain-extended polydiorganosiloxane vinyl crosslinking agent" or "chain-extended polysiloxane vinyl crosslinking agent" interchangeably refers to a compound containing at least two ethylenically unsaturated groups and at least two polysiloxane segments, each pair of which is linked by one divalent radical.

[0049] The term "photochromic compound" refers to a compound having one colorless (or light-colored) form and one colored form, and capable of undergoing a reversible change from the colorless form (or light-colored form) (or so-called "deactivated form") to the colored form (or so-called "activated form") upon exposure to UV or HEVL irradiation.

[0050] The term "colorless or light-colored state" or "deactivated state" with respect to a photochromic contact lens means the initial state of the photochromic contact lens before it is irradiated with UV and / or HEVL. In this state, the photochromic contact lens is typically colorless or exhibits a light color as observed by the naked eye.

[0051] The term "colored state" or "activated state" with respect to a photochromic contact lens means the state when the photochromic contact lens is being irradiated with UV and / or HEVL. In this state, the photochromic contact lens typically exhibits a dark color as observed by the naked eye.

[0052] As used herein, the term "fluid" indicates that the material can flow like a liquid.

[0053] As used in this application, the term "transparent" with respect to a polymerizable composition means that the polymerizable composition is a transparent solution or liquid mixture having a light transmittance of 85% or more in the range of 400 to 700 nm.

[0054] The free radical initiator can be either a photoinitiator or a thermal initiator. "Thermal initiator" or "thermal free radical initiator" interchangeably refers to a chemical substance that initiates a free radical crosslinking / polymerization reaction by using thermal energy. "Photoinitiator" refers to a chemical substance that initiates a free radical crosslinking / polymerization reaction by using light.

[0055] The term "monovalent radical" refers to an organic radical obtained by removing a hydrogen atom from an organic compound and forming one bond with another group in the organic compound. Examples include, without limitation, alkyl (by removal of a hydrogen atom from an alkane), alkoxy (or alkoxyl) (by removal of one hydrogen atom from the hydroxyl group of an alkyl alcohol), thioyl (by removal of one hydrogen atom from the thiol group of an alkyl thiol), cycloalkyl (by removal of a hydrogen atom from a cycloalkane), cycloheteroalkyl (by removal of a hydrogen atom from a cycloheteroalkane), aryl (by removal of a hydrogen atom from the aromatic ring of an aromatic hydrocarbon), heteroaryl (by removal of a hydrogen atom from any ring atom), amino (by removal of one hydrogen atom from an amine), etc.

[0056] The term "divalent radical" refers to an organic radical that is obtained by removing two hydrogen atoms from an organic compound and that forms two bonds with two other groups in the organic compound. For example, an alkylene divalent radical (i.e., alkenyl) is obtained by removing two hydrogen atoms from an alkane, and a cycloalkylene divalent radical (i.e., cycloalkenyl) is obtained by removing two hydrogen atoms from a cyclic ring.

[0057] In the present application, the term "substituted" in relation to alkyl or alkenyl means that the alkyl or alkenyl is replaced with one hydrogen atom of the alkyl or alkenyl and contains at least one substituent selected from the group consisting of hydroxyl (-OH), carboxyl (-COOH), -NH 2 , sulfhydryl (-SH), C 1 ~C 4 alkyl, C 1 ~C 4 alkoxy, C 1 ~C 4 alkylthio (alkyl sulfide), C 1 ~C 4 acylamino, C 1 ~C 4 alkylamino, di-C 1 ~C 4 alkylamino, and combinations thereof.

[0058] In relation to a SiHy lens bulk material or a SiHy contact lens, "post-cure surface treatment" means a surface treatment process that is performed after a SiHy lens formulation has been cured (i.e., polymerized thermally or by actinic radiation) to form the SiHy lens bulk material or the SiHy contact lens.

[0059] The terms "silicone hydrogel lens formulation" or "SiHy lens formulation" are interchangeable and refer to a polymerizable composition that contains all the necessary polymerizable components for manufacturing a SiHy contact lens or a SiHy lens bulk material.

[0060] "UV-absorbing vinyl monomer" refers to a compound that contains one and only one ethylenically unsaturated group and can mainly absorb UV light in the range of 280 nm to 380 nm. It is understood that the UV-absorbing vinyl monomer does not absorb, or hardly absorbs, light having a wavelength exceeding 400 nm (i.e., when tested with a solution of the UV-absorbing vinyl monomer at a concentration of 0.1 mM and an optical path length of 1 cm, the %T at 400 nm exceeds 90%).

[0061] "UV / HEVL-absorbing vinyl monomer" refers to a compound that has one and only one ethylenically unsaturated group and can absorb UV light in the range of 280 nm to 380 nm and HEVL in the range of 380 nm to 450 nm.

[0062] "UVA" refers to radiation generated at wavelengths of 315 to 380 nanometers; "UVB" refers to radiation generated in the range of 280 to 315 nanometers; "HEVL" refers to radiation generated at wavelengths of 380 to 450 nanometers.

[0063] "UVA transmittance" (or "UVA %T"), "UVB transmittance" or "UVB %T", and "HEVL transmittance" or "HEVL %T" are calculated by the following formulas. UVA %T = Average transmittance % in the range of 315 nm to 380 nm × 100 UVB %T = Average transmittance % in the range of 280 nm to 315 nm × 100 HEVL %T = Average transmittance % in the range of 380 nm to 450 nm × 100 HEVL % filtering = 100% - HEVL %T

[0064] "%T at a wavelength" means the transmittance at the wavelength.

[0065] The "derivative" with respect to Cu(II)-porphyrin means the product of Cu(II)-porphyrin after participating in the free radical polymerization of a polymerizable composition containing Cu(II)-porphyrin for forming a polymer, which is covalently bonded to the obtained polymer, and has a part having an aromatic π-electron system substantially similar to the aromatic π-electron system of the starting Cu(II)-porphyrin, as indicated by having a strong peak (i.e., Soret peak or band) in the blue wavelength region of the visible spectrum.

[0066] The "oxygen permeability" Dk of the material i is the rate at which oxygen passes through the material and can be measured at about 34 - 35 °C according to the procedure described in Example 1. The oxygen permeability is usually expressed in units of Barrers, and a "Barrier" is defined as [(cm 3 oxygen)(mm) / (cm 2 )(sec)(mmHg)]×10 -10 as defined.

[0067] The "oxygen transmission rate" Dk / t of a lens or material is the rate at which oxygen passes through a specific lens or material with an average thickness t [in mm] over the entire region being measured. The oxygen transmission coefficient is usually expressed in units of Barrer / mm, and a "Barrer / mm" is defined as [(cm 3 oxygen) / (cm 2 )(sec)(mmHg)]×10 -9 as defined.

[0068] The term "modulus" or "elastic modulus" with respect to a contact lens or substance means the tensile modulus, i.e., Young's modulus, which is a measure of the indentation of the contact lens or substance. The modulus can be measured according to the procedure described in Example 1.

[0069] The "coating" with respect to a contact lens means that the contact lens has a thin layer of a material on its surface that is different from the bulk material of the contact lens and is obtained by surface treating the contact lens.

[0070] As used herein, "surface modification" or "surface treatment" means that an article has been treated in a surface treatment process, in which (1) a coating is provided on the surface of the article, (2) a chemical species is adsorbed on the surface of the article, (3) the chemical properties (e.g., electrostatic charge) of the chemical groups on the surface of the article are changed, or (4) the surface characteristics of the article are changed in other ways. Exemplary surface treatment processes include, but are not limited to, surface treatment by energy (e.g., plasma, electrostatic charge, irradiation or other energy sources), chemical treatment, grafting of hydrophilic vinyl monomers or macromers onto the article surface, the mold transfer coating process disclosed in U.S. Patent No. 6,719,929, the incorporation of wetting agents into lens formulations for making contact lenses proposed in U.S. Patent Nos. 6,367,929 and 6,822,016, the enhanced mold transfer coating disclosed in U.S. Patent No. 7,858,000, and the covalent or physical deposition of one or more layers of one or more hydrophilic polymers disclosed in U.S. Patent Nos. 8,147,897, 8,409,599, 8,557,334, 8,529,057 and 9,505,184 onto the contact lens surface to form a hydrophilic coating.

[0071] The "hydrophilic surface" with respect to the SiHy material or contact lens means that the SiHy material or contact lens has surface hydrophilicity characterized by having an average water contact angle of about 90 degrees or less, preferably about 80 degrees or less, more preferably about 70 degrees or less, and even more preferably about 60 degrees or less.

[0072] The "average contact angle" refers to the water contact angle (the static water contact angle measured by the sessile drop method), which is obtained by averaging the measured values of at least three individual contact lenses.

[0073] In the present application, "Cu(II)-meso-aryl-substituted porphyrin" refers to a copper porphyrin containing four aryl groups (substituents) at the 5, 10, 15, and 20 positions (i.e., the so-called meso positions) of porphyrin, as is well known to those skilled in the art.

[0074] Generally, the present invention relates to UV / HEVL filtering contact lenses, and more particularly, to UV / HEVL filtering SiHy contact lenses having a desirable UV / HEVL absorption profile including less than 10% UVA%T, less than 1% UVB%T, about 60% or less HEVL%T, about 40% or less %T at 420 nm, and about 80% or more %T at 450 nm. The present invention is based in part on the discovery that by selectively adding a UV-absorbing vinyl monomer, a UV / HEVL-absorbing vinyl monomer, and a reactive Cu(II) porphyrin (preferably a Cu(II)-meso-aryl substituted porphyrin) to a polymerizable composition for contact lens manufacture in specific amounts and selected ratios, a UV / HEVL filtering contact lens having the above-described desirable UV / HEVL absorption profile can be obtained.

[0075] The contact lenses of the present invention can not only provide Class I UV protection against UVA and UVB light (i.e., filtering more than 90% of UVA and more than 99% of UVB), but can also mimic the natural lens of the human eye in providing HEVL protection. The natural lens of the human eye typically blocks most of the HEVL light up to 410 nm, but its %T filtering performance gradually decreases beyond this wavelength. Similar to the natural lens of the human eye, the UV / HEVL filtering contact lenses according to the present invention can provide improved protection against eye damage by UV and violet light while causing a minimal change in color perception, a minimal decrease in color vision, a minimal decrease in scotopic visual function, a minimal decrease in contrast sensitivity in light and dark, and a minimal disruption of circadian light synchronization.

[0076] The present invention provides a UV / HEVL filtering contact lens comprising a bulk hydrogel material containing (1) repeating units of at least one hydrophilic vinyl monomer, (2) repeating units of at least one vinyl crosslinking agent, (3) repeating units of at least one UV-absorbing vinyl monomer that absorbs UV light in the range of 280 nm to 380 nm, (4) repeating units of at least one UV / HEVL-absorbing vinyl monomer that absorbs UV light in the range of 280 nm to 380 nm and HEVL in the range of 380 nm to 450 nm, and (5) at least one Cu(II)-porphyrin derivative, wherein the derivative is covalently bonded to the bulk hydrogel material and has an absorption peak (i.e., Soret peak or band) in the region from 395 nm to 435 nm in the visible absorption spectrum, and the components (3), (4) and (5) are present in the bulk hydrogel material in amounts and ratios such that the UV / HEVL filtering contact lens has less than 10% UVA%T, less than 1% UVB%T, at most about 60% (preferably at most about 55%, more preferably at most about 50%, even more preferably at most about 45%) HEVL%T, at most about 40% (preferably at most about 30%, more preferably at most about 25%, even more preferably at most about 20%) %T at 420 nm, and at least about 80% (preferably at least about 85%, more preferably at least about 90%) %T at wavelengths between 450 nm and 500 nm.

[0077] According to the present invention, any UV-absorbing vinyl monomer can be used in the present invention as long as it can provide Class I UV protection in combination with the UV / HEVL-absorbing vinyl monomer. The UV-absorbing vinyl monomer can be a benzotriazole-containing vinyl monomer (i.e., each having a benzotriazole moiety) and / or a benzophenone-containing vinyl monomer (i.e., each having a benzophenone moiety) well known to those skilled in the art.

[0078] Examples of benzophenone-containing vinyl monomers include, but are not limited to, the following: 2-hydroxy-4-acryloxybenzophenone; 2-hydroxy-4-methacryloxybenzophenone; 2-hydroxy-4-acryloxyethoxybenzophenone; 2-hydroxy-4-methacryloxyethoxybenzophenone; 4-allyloxy-2-hydroxybenzophenone; 4-allyloxyethoxy-2-hydroxybenzophenone; aminobenzophenone vinyl monomers disclosed in U.S. Patent No. 10268053 (e.g., N-(2-benzoyl-4-chlorophenyl)methacrylamide, etc.), 2-hydroxy-4-methoxy-4'-(acrylamido-N,N-dimethylpropylaminomethyl)-benzophenone and other hydroxybenzophenone vinyl monomers disclosed in U.S. Patent No. 10254567, benzophenone-containing UV-absorbing vinyl monomers disclosed in U.S. Patent No. 3162676. Benzophenone-containing vinyl monomers can be obtained from commercial suppliers or prepared according to the procedures described in U.S. Patent No. 3162676, U.S. Patent No. 10254567, and U.S. Patent No. 10268053.

[0079] In a preferred embodiment, the at least one UV-absorbing vinyl monomer comprises a benzotriazole-containing vinyl monomer, preferably a vinyl monomer of formula (1). [Chemical formula] (In the formula: R 1 and R 2 One of them is H, and R 1 and R 2 The other is -L 1 -E 1 is a monovalent radical; E 1 is vinyl, vinyloxy, allyl, allyloxy, (meth)acryloxy, or (meth)acrylamide; L 1 is a direct bond, C 1 ~C 6 alkylene divalent radical, or -L2 -X 1 -L 3 - is a bond; L 2 is a direct bond, C 1 ~C 3 an alkylene divalent radical, [Chem.] and; X 1 is O, NH, or [Chem.] and R 3 and R 4 are methyl or ethyl; L 3 is C 1 ~C 6 an alkylene divalent radical.)

[0080] Preferred examples of the UV-absorbing vinyl monomer of formula (1) include, but are not limited to, 2-(2'-hydroxy-5'-vinylphenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-methacryloyloxyphenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-acryloyloxyphenyl)-2H-benzotriazole, 2-[2'-hydroxy-5'-(2-methacryloyloxyethyl)phenyl)]-2H-benzotriazole (Norbloc), 2-[2'-hydroxy-5'-(2-acryloyloxyethyl)-phenyl)]-2H-benzotriazole, 2-(2'-hydroxy-5'-methacryloyloxypropylphenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-acryloyloxypropylphenyl)-2H-benzotriazole.

[0081] The benzotriazole-containing UV-absorbing vinyl monomer can be prepared according to the procedures described in U.S. Patent Nos. 3,299,173; 4,612,358; 4,716,234; 4,528,311; 10,254,567, or can be obtained from commercial suppliers.

[0082] According to the present invention, any UV / HEVL absorbing vinyl monomer can be used in the present invention as long as it can provide the desired HEVL filtering profile in combination with copper (II) porphyrin. The UV / HEVL absorbing vinyl monomer can be a benzotriazole-containing vinyl monomer and / or a benzophenone-containing vinyl monomer (i.e., one having a benzophenone moiety) well-known to those skilled in the art.

[0083] In a preferred embodiment, the at least one UV / HEVL absorbing vinyl monomer includes a benzotriazole-containing vinyl monomer, preferably a benzotriazole-containing vinyl monomer of formula (2).

Chemical formula

[0084] Examples of preferred UV / HEVL-absorbing vinyl monomers of formula (2) include, but are not limited to, 2-(2'-hydroxy-3'-methacrylamidomethyl-5'-tert-octylphenyl)-2-benzotriazole, 2-(2'-hydroxy-5'-methacrylamidophenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-methacrylamidophenyl)-5-methoxybenzotriazole, 2-(2'-hydroxy-5'-glycidoxypropyl-3'-t-butylphenyl)-5-chlorobenzotriazole, 2-hydroxy-5-methoxy-3-(5-(trifluoromethyl)-2H-benzotriazol-2-yl)benzyl methacrylate (WL-1), 2-hydroxy-5-methoxy-3-(5-methoxy-2H-benzotriazol-2-yl)benzyl methacrylate (WL-5), 3-(5-fluoro-2H-benzotriazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate (WL-2), 3-(2H-benzotriazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate (WL-3), 3-(5-chloro-2H-benzotriazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate (WL-4), 2-hydroxy-5-methoxy-3-(5-methyl-2H-benzotriazol-2-yl)benzyl methacrylate (WL-6), 2-hydroxy-5-methyl-3-(5-(trifluoromethyl)-2H-benzotriazol-2-yl)benzyl methacrylate (WL-7), 4-allyl-2-(5-chloro-2H-benzotriazol-2-yl)-6-methoxyphenol (WL-8), 2{2'-hydroxy-3'-tert-butyl-5'-[3''-(4''-vinylbenzyloxy)propoxy]phenyl}-5-methoxy-2H-benzotriazole, 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-(1,1-dimethylethyl)-4-ethenyl-phenol (UVAM), 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-2H-benzotriazole, 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-methoxy-2H-benzotriazole (UV13), 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole (UV28), 2-[2'-hydroxy-3'-tert-butyl-5'-(3'-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole (UV23), 2-(2'-hydroxy-5-methacrylamidophenyl)-5-methoxybenzotriazole (UV6), 2-(3-allyl-2-hydroxy-5-methylphenyl)-2H-benzotriazole (UV9), 2-(2-hydroxy-3-methallyl-5-methylphenyl)-2H-benzotriazole (UV12), 2-3'-t-butyl-2'-hydroxy-5'-(3''-dimethylvinylsilylpropoxy)-2'-hydroxyphenyl)-5-methoxybenzotriazole (UV15), 2-(2'-hydroxy-5'-methacryloylpropyl-3'-tert-butylphenyl)-5-methoxy-2H-benzotriazole (UV16), 2-(2'-hydroxy-5'-acryloylpropyl-3'-tert-butylphenyl)-5-methoxy-2H-benzotriazole (UV16A), 2-methylacrylic acid 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]-propyl ester (16-100, CAS#96478-15-8), 2-(3-(tert-butyl)-4-hydroxy-5-(5-methoxy-2H-benzo[d][1,2,3](Triazol-2-yl)phenoxy)ethyl methacrylate (16-102); 2-(5-chloro-2H-benzotriazol-2-yl)-6-methoxy-4-(2-propen-1-yl)-phenol (CAS#1260141-20-5); 2-[2-hydroxy-5-[3-(methacryloyloxy)propyl]-3-tert-butylphenyl]-5-chloro-2H-benzotriazole; Benzotriazole-containing vinyl monomers disclosed in U.S. Patent No. 10254567 are exemplified.,

[0085] According to the present invention, the derivative of the at least one Cu(II)-porphyrin derivative has a Soret peak (i.e., an absorption peak in the region of 395 nm to 435 nm) in the visible absorption spectrum.,

[0086] As long as it can participate in the free radical polymerization of the polymerizable composition containing Cu(II)-porphyrin, covalently bond to the polymer substance formed from the polymerizable composition, and generate a Cu(II)-porphyrin derivative having a Soret peak (i.e., an absorption peak in the region of 395 nm to 435 nm) in the visible absorption spectrum, Cu(II)-porphyrin can be used in the present invention.,

[0087] Preferably, the Cu(II)-porphyrin is a Cu(II)-meso-aryl substituted porphyrin. The aromatic π-electron system of the Cu(II)-meso-aryl substituted porphyrin is considered to be able to remain even during free radical polymerization, and the Cu(II)-meso-aryl substituted porphyrin derivative obtained from free radical polymerization may still have a Soret peak (i.e., an absorption peak in the region of 395 nm to 435 nm) in the visible absorption spectrum.,

[0088] In a preferred embodiment, the Cu(II)-meso-aryl substituted porphyrin is represented by formula (3).

Chemical formula

[0089] Due to the presence of the ethylenically unsaturated group, the Cu(II)-meso-aryl substituted porphyrin of formula (3) can be added to the polymerizable composition for producing the UV / HEVL filtering contact lens of the present invention.

[0090] Examples of preferred Cu(II)-meso-aryl substituted porphyrins of formula (3) include, but are not limited to, those disclosed in U.S. Patent Application No. 63 / 275159. These are available from commercial suppliers (e.g., High Performance Optics, Inc.) or can be prepared according to the procedures described in U.S. Patent Application No. 63 / 275159.

[0091] In another preferred embodiment, the Cu(II)-meso-aryl substituted porphyrin is represented by formula (4). [Chemical formula] (Wherein: each R 9are each independently H, Cl, F, substituted or unsubstituted C 1 ~C 20 alkyl, substituted or unsubstituted C 1 ~C 20 alkenyl, substituted or unsubstituted C 1 ~C 20 alkynyl, or two adjacent R 8 groups, together with the atoms to which they are attached and the atoms to which those atoms are attached, form substituted or unsubstituted C 6 ~C 14 aryl, substituted or unsubstituted C 3 ~C 14 carbocyclic, substituted or unsubstituted C 5 ~C 14 heteroaryl, or substituted or unsubstituted C 3 ~C 14 heterocyclyl; A 7 and A 11 are each independently Cl, F, CCl 3 、CF 3 、CH 3 、CH(CH 3 ) 2 、C(CH 3 ) 3 、OCH 3 、OH, or NO 2 (preferably Cl, F, or NO 2 ); A 8 、A 9 and A 10 are each independently H, Cl, F, CCl 3 、CF 3 、CH 3 、CH(CH 3 ) 2 、C(CH 3 ) 3 、OCH 3 、OH, NH 2 or NO 2 .)

[0092] In a preferred embodiment, A 7 、A 8 、A 9 、A 10 、and A 11are identical to each other and are Cl or F; in another preferred embodiment, A 7 and A 11 are independently of each other Cl or F; A 9 and A 10 are H; and A 8 is Cl, F, CCl 3 、CF 3 、CH 3 、CH(CH 3 ) 2 、C(CH 3 ) 3 、OCH 3 、OH、NH 2 、or NO 2 。In another preferred embodiment, A 7 and A 11 are independently of each other Cl or F; A 8 and A 10 are H; A 9 is Cl, F, CCl 3 、CF 3 、CH 3 、CH(CH 3 ) 2 、C(CH 3 ) 3 、OCH 3 、OH、NH 2 、or NO 2 。

[0093] Examples of preferred Cu(II)-meso-aryl substituted porphyrins of formula (4) include, but are not limited to, 5,10,15,20-tetrakis(2,6-dichlorophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2,6-difluorophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2-chloro-6-fluorophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2,6-dinitrophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2,3,6-trichlorophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2,3,6-trifluorophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2,4,6-trinitrophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2,4,6-trimethylphenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2,6-dichloro-3-aminophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(4-bromo-2,6-dichlorophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2,6-dichloro-4-nitrophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2,6-dichloro-3-nitrophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2,6-dihydroxyphenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(2,6-dimethoxyphenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(pentachlorophenyl)-porphyrin-Cu(II), 5,10,15,20-tetrakis(pentafluorophenyl)-porphyrin-Cu(II), 10,15,20-tris(2,6-dichlorophenyl)-5-(2,3,4,5,6-pentafluorophenyl)-porphyrin-Cu(II), 5,10,15-tris(pentafluorophenyl)-20-(2.Examples include (6-dichlorophenyl)-porphyrin-Cu(II) and 10,20-bis(2,6-dichlorophenyl)-5,15-bis(2,3,4,5,6-pentafluorophenyl)-porphyrin-Cu(II).

[0094] Cu(II)-meso-aryl substituted porphyrins (e.g., 5,10,15,20-tetrakis-(2,6-dichlorophenyl) porphyrin-Cu(II)) have been found to participate in the free radical polymerization of a polymerizable composition containing a sufficient amount of an N-vinylamide monomer (e.g., N-vinylpyrrolidone), even when such Cu(II)-meso-aryl substituted porphyrins do not contain any ethylenically unsaturated groups. It has also been found that even when Cu(II)-meso-aryl substituted porphyrins participate in free radical polymerization, it has no adverse effect on the properties of the resulting polymer material, nor does it have a significant effect. The resulting polymer material grafted with Cu(II)-meso-aryl substituted porphyrins exhibits HEVL filtering (i.e., HEVL absorption) characteristics almost equivalent to those of the starting Cu(II)-meso-aryl substituted porphyrins, indicating that there is no significant decomposition or damage to the aromatic π-electron system of the Cu(II)-meso-aryl substituted porphyrins during free radical polymerization. According to the present invention, there is no need to chemically modify the HEVL absorption compound to introduce one or more ethylenically unsaturated groups.

[0095] According to a preferred embodiment of the present invention, the bulk hydrogel material (dry state) of the UV / HEVL filtering contact lens constitutes about 0.6% to about 3.5%, preferably about 0.7% to about 3.0%, more preferably about 0.8% to about 2.5% based on the weight of all components (3), (4) and (5). It is understood that the weight percentages of components (3), (4) and (5) in the bulk hydrogel material in the dry state can be determined based on their weight percentages in the polymerizable composition for forming the bulk hydrogel material relative to the total weight of all polymerizable components in the polymerizable composition.

[0096] In a preferred embodiment, in the dry bulk hydrogel material, the weight ratio of component (3) to component (4) is at least 1.2 (preferably at least 1.6, more preferably at least 2.0, still more preferably at least 2.4); the weight ratio of component (5) to component (4) is at least 1.5 (preferably at least 2.0, more preferably at least 2.5, still more preferably at least 3.0). It is understood that the weight ratio of component (3) to (4) to (5) in the dry bulk hydrogel material can be determined based on their weight percentages in the polymerizable composition for forming the bulk hydrogel material relative to the total weight of all polymerizable components in the polymerizable composition.

[0097] With such a weight ratio of component (3) to (4) to (5) in the dry bulk hydrogel material, the UV / HEVL absorbing contact lens can provide Class I UV protection and enhanced HEVL protection while minimizing the impact on color balance, color vision, and coloring.

[0098] Any hydrophilic vinyl monomer can be used in the present invention. Examples of preferred hydrophilic vinyl monomers include alkyl (meth)acrylamide (as described later in this application), hydroxyl-containing acrylic monomers (as described below), amino-containing acrylic monomers (as described later in this application), carboxyl-containing acrylic monomers (as described later in this application), N-vinylamide monomers (as described later in this application), methylene-containing pyrrolidone monomers (i.e., pyrrolidone derivatives each having a methylene group bonded to the pyrrolidone ring at the 3- or 5-position) (as described later in this application), C 1 ~C 4An acrylic monomer having an alkoxyethoxy group (as described later in the present application), a vinyl ether monomer (as described later in the present application), an allyl ether monomer (as described later in the present application), a phosphorylcholine-containing vinyl monomer (as described later in the present application), N-2-hydroxyethyl vinyl carbamate, N-carboxyvinyl-β-alanine (VINAL), N-carboxyvinyl-α-alanine, and combinations thereof.

[0099] In one embodiment, the bulk hydrogel material is a non-silicone hydrogel material, and the at least one hydrophilic vinyl monomer includes at least one hydroxyl-containing acrylic monomer (any of those described later in the present application), at least one hydrophilic (meth)acrylamide monomer (any of those described later in the present application), at least one N-vinylamide monomer (any of those described later in the present application), at least one methylene-containing pyrrolidone monomer (any of those described later in the present application), or combinations thereof; and the at least one vinyl crosslinking agent includes at least one non-silicone vinyl crosslinking agent.

[0100] Examples of preferred hydrophilic N-vinylamide monomers include, but are not limited to, N-vinylpyrrolidone, N-vinylpiperidone, N-vinylcaprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, and mixtures thereof. Preferably, the N-vinylamide monomer is N-vinylpyrrolidone, N-vinyl-N-methylacetamide, or a combination thereof.

[0101] According to the present invention, any non-silicone vinyl crosslinking agent can be within the scope of the present invention. Examples of preferred non-silicone vinyl crosslinking agents are described later in the present application.

[0102] In another embodiment, the bulk hydrogel material is a silicone hydrogel material, further comprising (6) repeating units of at least one siloxane-containing vinyl monomer and / or at least one polysiloxane vinyl crosslinking agent, wherein the at least one vinyl crosslinking agent comprises the polysiloxane vinyl crosslinking agent and / or at least one non-silicone vinyl crosslinking agent.

[0103] Any siloxane-containing vinyl monomer can be used in the present invention. Examples of preferred siloxane-containing vinyl monomers can be siloxane-containing (meth)acrylamide monomers, siloxane-containing (meth)acryloxy monomers, siloxane-containing vinyloxycarbonyloxy monomers, siloxane-containing vinyloxycarbonylamino monomers, siloxane-containing vinylaminocarbonylamino monomers, or siloxane-containing vinylaminocarbonyloxy monomers, each having a bis(trialkylsilyloxy)alkylsilyl group, a tris(trialkylsilyloxy)silyl group, or a polysiloxane chain having 2 to 30 siloxane units and terminated with an alkyl, hydroxyalkyl or methoxyalkyl group. Such preferred siloxane-containing vinyl monomers can be obtained from commercial suppliers or can be prepared according to known procedures similar to those described in, for example, U.S. Patent Nos. 5,070,215; 6,166,236; 6,867,245; 7,214,809; 8,415,405; 8,467,031; 8,614,261; 8,658,748; 9,097,840; 9,103,965; 9,217,813; 9,315,669; and 9,475,827, or by reacting a vinyl monomer having a reactive functional group (e.g., an acid chloride, an acid anhydride, a carboxyl group, a hydroxyl group, an amino group, an epoxy group, an isocyanate group, an aziridine group, an azlactone group, or an aldehyde group) with a siloxane-containing compound having a reactive group selected from the group consisting of hydroxyalkyl, aminoalkyl, alkylaminoalkyl, carboxyalkyl, isocyanatoalkyl, epoxyalkyl, and aziridinylalkyl in the presence or absence of a coupling agent under coupling reaction conditions well known to those skilled in the art.

[0104] According to the present invention, any polysiloxane vinyl crosslinking agent can be used in the present invention. Examples of preferred polysiloxane vinyl crosslinking agents include, but are not limited to, α,ω-(meth)acryloxy-terminated polydimethylsiloxanes of various molecular weights; α,ω-(meth)acrylamide-terminated polydimethylsiloxanes of various molecular weights; α,ω-vinyl carbonate-terminated polydimethylsiloxanes of various molecular weights; α,ω-vinyl carbamate-terminated polydimethylsiloxanes of various molecular weights; bis-3-methacryloxy-2-hydroxypropyl oxypropyl polydimethylsiloxanes of various molecular weights; N,N,N’,N’-tetrakis(3-methacryloxy-2-hydroxypropyl)-alpha,omega-bis-3-aminopropyl-polydimethylsiloxane of various molecular weights; reaction products of glycidyl methacrylate and amino-functional polydimethylsiloxane; reaction products of azlactone-containing vinyl monomers (any of those described above) and hydroxyl-functional polydimethylsiloxane; polysiloxane-containing macromers selected from the group consisting of macromer A, macromer B, macromer C and macromer D described in U.S. Patent No. 5,760,100;Examples of the polysiloxane vinyl crosslinking agents disclosed in U.S. Patent No. 4,136,250, No. 4,153,641, No. 4,182,822, No. 4,189,546, No. 4,259,467, No. 4,260,725, No. 4,261,875, No. 4,343,927, No. 4,254,248, No. 4,355,147, No. 4,276,402, No. 4,327,203, No. 4,341,889, No. 4,486,577, No. 4,543,398, No. 4,605,712, No. 4,661,575, No. 4,684,538, No. 4,703,097, No. 4,833,218, No. 4,837,289, No. 4,954,586, No. 4,954,587, No. 5,010,141, No. 5,034,461, No. 5,070,170, No. 5,079,319, No. 5,039,761, No. 5,346,946, No. 5,358,995, No. 5,387,632, No. 5,416,132, No. 5,449,729, No. 5,451,617, No. 5,486,579, No. 5,962,548, No. 5,981,675, No. 6,039,913, No. 6,762,264, No. 7,423,074, No. 8,163,206, No. 8,480,227, No. 8,529,057, No. 8,835,525, No. 8,993,651, No. 9,187,601, No. 10,081,697, No. 10,301,451 and No. 10,465,047 are included.;

[0105] One class of preferred polysiloxane vinyl crosslinking agents is a di-(meth)acryloyloxy-terminated polysiloxane vinyl crosslinking agent having dimethylsiloxane units and hydrophilic siloxane units each having one methyl substituent and one monovalent C 4 ~C 40 organic radical substituent and 2 to 6 hydroxyl groups, more preferably a polysiloxane vinyl crosslinking agent of formula (I); It can be prepared according to the procedures described later in this application and disclosed in U.S. Patent No. 10,081,697.

[0106] Another class of preferred polysiloxane vinyl crosslinkers are vinyl crosslinkers each containing one unique polysiloxane segment and two terminal (meth)acryloyl groups, which are commercially available; can be prepared by reacting glycidyl (meth)acrylate (meth)acryloyl chloride with diamino-terminated polydimethylsiloxane or dihydroxyl-terminated polydimethylsiloxane; can be prepared by reacting isocyanatoethyl (meth)acrylate with dihydroxyl-terminated polydimethylsiloxane; can be prepared by reacting an amino-containing acrylic monomer with a dicarboxyl-terminated polydimethylsiloxane in the presence of a coupling agent (carbodiimide); can be prepared by reacting a carboxyl-containing acrylic monomer with a diamino-terminated polydimethylsiloxane in the presence of a coupling agent (carbodiimide); or can be prepared by reacting a hydroxyl-containing acrylic monomer with a dihydroxy-terminated polysiloxane in the presence of a diisocyanate or diepoxy coupling agent.

[0107] Another class of preferred polysiloxane vinyl crosslinkers are chain-extended polysiloxane vinyl crosslinkers each having at least two polysiloxane segments linked by a linker between each pair of polysiloxane segments and two terminal ethylenically unsaturated groups; which can be prepared according to the procedures described in U.S. Patent Nos. 5,034,461; 5,416,132; 5,449,729; 5,760,100; 7,423,074; 8,529,057; 8,835,525; 8,993,651; 9,187,601; 10,301,451; and 10,465,047.

[0108] The bulk non-silicone hydrogel material or the bulk silicone hydrogel material can further contain repeating units of at least one hydrophobic non-silicone vinyl-based monomer.

[0109] Any hydrophobic non-silicone vinyl-based monomer can be used in the present invention. Examples of preferred hydrophobic non-silicone vinyl-based monomers include C 1 ~C 10 alkyl (meth) acrylates (e.g., methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, etc.), cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl valerate, styrene, chloroprene, vinyl chloride, vinylidene chloride, (meth) acrylonitrile, 1-butene, butadiene, vinyl toluene, vinyl ethyl ether, perfluorohexylethyl-thio-carbonyl-aminoethyl-methacrylate, isobornyl (meth) acrylate, trifluoroethyl (meth) acrylate, hexafluoroisopropyl (meth) acrylate, hexafluorobutyl (meth) acrylate, and combinations thereof.

[0110] In a preferred embodiment, the bulk hydrogel material contains repeating units of at least one polymerizable dye for coloring the bulk hydrogel material. Examples of preferred polymerizable dyes include, but are not limited to, 1,4-bis(4-(2-methacryloxyethyl)phenylamino)anthraquinone (Reactive Blue 246), 1,4-bis((2-hydroxyethyl)amino)-9,10-anthracenedione-bis(2-propenoic acid) ester (Reactive Blue 247).

[0111] According to the present invention, the lens bulk material of the contact lens of the present invention can be directly obtained from a preformed contact lens. The preformed contact lens can be any contact lens that has not undergone surface treatment after being manufactured according to any lens manufacturing process, or any contact lens that has been plasma treated, or any commercially available contact lens as long as it does not have a water gradient structure. Those skilled in the art are very familiar with the method of manufacturing a preformed contact lens. Those skilled in the art are very familiar with the method of manufacturing a preformed contact lens. For example, the preformed contact lens can be manufactured, for example, in a conventional "spin casting mold" as described in U.S. Patent No. 3,408,429 or by a full cast molding process in a static form as described in U.S. Patent Nos. 4,347,198, 5,508,317, 5,583,463, 5,789,464, and 5,849,810, or by lathe cutting of a polymer material button as used in the manufacture of customized contact lenses. In cast molding, the polymerizable composition (i.e., the lens formulation) is typically dispensed into a mold and cured (i.e., polymerized and / or crosslinked) in the mold to produce a contact lens.

[0112] Lens molds for manufacturing contact lenses such as SiHy contact lenses are well known to those skilled in the art and are used, for example, in cast molding or spin casting. For example, a mold (for injection molding) generally includes at least two mold pieces (or parts) or mold halves, i.e., a first and a second mold half. The first mold half defines a first molding (or optical) surface, and the second mold half defines a second molding (or optical) surface. The first and second mold halves are configured to receive each other such that a lens forming cavity is formed between the first molding surface and the second molding surface. The molding surface of the mold half is the cavity forming surface of the mold and is in direct contact with the polymerizable composition.

[0113] The mold half can be formed by various techniques such as injection molding. Methods for manufacturing a mold half for casting a contact lens are generally well known to those skilled in the art. The method of the present invention is not limited to a specific method of forming the mold. In fact, in the present invention, any method for forming the mold can be used. The mold half can be formed by various techniques such as injection molding or lathe work. Examples of suitable processes for forming the mold half are disclosed in U.S. Patent Nos. 4,444,711, 4,460,534, 5,843,446, and 5,894,002.

[0114] Virtually all materials known in the art for manufacturing a mold can be used for manufacturing a mold for making a contact lens. For example, polymeric materials such as polyethylene, polypropylene, polystyrene, PMMA, Topas® COC grade 8007 - S10 (a transparent amorphous copolymer of ethylene and norbornene manufactured by Ticona GmbH, Frankfurt, Germany and Summit, New Jersey) can be used. Other materials that are transmissive to UV light, such as quartz glass and sapphire, could be used.

[0115] According to the present invention, the polymerizable composition can be introduced (dispensed) into a cavity formed by a mold according to any known method.

[0116] After the polymerizable composition has been dispensed into the mold, it is polymerized to produce a contact lens. Crosslinking can be initiated thermally or by actinic radiation to crosslink the polymerizable components in the polymerizable composition.

[0117] Thermal polymerization is conveniently carried out, for example, at a temperature of 25 to 120 °C, preferably 40 to 100 °C. The reaction time can vary within a wide range, but conveniently, for example, it is 30 minutes to 4 hours or preferably 1 to 2 hours. It is advantageous to degas the components and solvents used in the polymerization reaction in advance and to carry out the copolymerization reaction under an inert atmosphere, for example, under an atmosphere of nitrogen or argon.

[0118] Subsequently, chemical radiation polymerization can be induced by chemical radiation, for example, light, particularly preferably UV light or visible light of a suitable wavelength. If necessary, the spectral requirements can be appropriately controlled by adding a suitable photosensitizer.

[0119] After the curing step, the steps of mold release (i.e., separating the male mold half from the female mold half with the contact lens attached to one of the male and female mold halves) and lens removal (i.e., removing the contact lens from the mold half to which the lens is attached) are carried out according to any technique known to those skilled in the art.

[0120] After taking out the molded contact lens, it is typically extracted with an extraction medium well-known to those skilled in the art. The extraction liquid medium is any solvent capable of dissolving the diluent, unpolymerized polymerizable material, and oligomers in the lens precursor. Water, any organic solvent described above or known to those skilled in the art, or a mixture thereof can be used in the present invention.

[0121] Subsequently, the extracted contact lens can be hydrated by any method known to those skilled in the art.

[0122] The extracted and / or hydrated contact lens can be further subjected to additional processes such as surface treatment, packaging in a lens package using a packaging solution well-known to those skilled in the art, and sterilization such as autoclaving at 118 to 124 °C for at least about 30 minutes.

[0123] Lens packages (or containers) are well known to those skilled in the art with respect to autoclaving and storing soft contact lenses. Any lens package can be used in the present invention. Preferably, the lens package is a blister package including a base and a cover; here, the cover is sealed to be detachable from the base, and here, the base includes a cavity for receiving a sterilization packaging solution and a contact lens.

[0124] The lenses are packaged, sealed in individual packages, and sterilized (e.g., by autoclaving at about 120 °C or higher for at least 30 minutes under pressure) before being dispensed to the user. Those skilled in the art will well understand the methods of sealing and sterilizing the lens packages.

[0125] According to the present invention, a bulk non-silicone hydrogel material can be formed from a polymerizable composition (i.e., a lens formulation) for forming a non-silicone hydrogel contact lens. Typically, the polymerizable composition for forming the bulk non-silicone hydrogel material of the present invention comprises (I) (1) at least one hydrophilic vinyl monomer (e.g., a hydroxyl-containing vinyl monomer, an N-vinylamide monomer, a (meth)acrylamide monomer, or a combination thereof), (2) at least one non-silicone vinyl crosslinking agent, (3) at least one UV-absorbing vinyl monomer, (4) at least one UV / HEVL-absorbing vinyl monomer, (5) at least one Cu(II)-porphyrin, and (6) a hydrophobic non-silicone vinyl monomer, a free radical initiator (a photoinitiator or a thermal initiator), a polymerizable visibility colorant (i.e., a polymerizable dye), and at least one component selected from the group consisting of combinations thereof; or (II) one or more water-soluble prepolymers, at least one UV-absorbing vinyl monomer, at least one UV / HEVL-absorbing vinyl monomer, at least one Cu(II)-porphyrin, and a hydrophilic vinyl monomer, a non-silicone vinyl crosslinking agent, a hydrophobic non-silicone vinyl monomer, a free radical initiator (a photoinitiator or a thermal initiator), a polymerizable visibility colorant (i.e., a polymerizable dye), and a small amount of at least one component selected from the group consisting of combinations thereof.

[0126] Examples of water-soluble prepolymers include, but are not limited to, water-soluble crosslinkable poly(vinyl alcohol) prepolymers described in U.S. Patent Nos. 5,583,163 and 6,303,687; water-soluble vinyl group-terminated polyurethane prepolymers described in U.S. Patent No. 6,995,192; derivatives of polyvinyl alcohol, polyethyleneimine, or polyvinylamine disclosed in U.S. Patent No. 5,849,841; water-soluble crosslinkable polyurea prepolymers described in U.S. Patent Nos. 6,479,587 and 7,977,430; crosslinkable polyacrylamide; crosslinkable statistical copolymers of vinyl lactam, MMA, and comonomers disclosed in U.S. Patent No. 5,712,356; crosslinkable copolymers of vinyl lactam, vinyl acetate, and vinyl alcohol disclosed in U.S. Patent No. 5,665,840; polyether-polyester copolymers having crosslinkable side chains disclosed in U.S. Patent No. 6,492,478; branched polyalkylene glycol-urethane prepolymers disclosed in U.S. Patent No. 6,165,408; polyalkylene glycol-tetra(meth)acrylate prepolymers disclosed in U.S. Patent No. 6,221,303; and crosslinkable polyallylamine gluconolactone prepolymers disclosed in U.S. Patent No. 6,472,489.

[0127] Numerous lens formulations (polymerizable compositions) for forming non-silicone hydrogel materials have been described in numerous patents and patent applications published prior to the filing date of this application and have been used in the manufacture of commercially available non-silicone hydrogel contact lenses. Examples of commercially available non-silicone hydrogel contact lenses include, but are not limited to, alphafilcon A, acofilcon A, deltafilcon A, etafilcon A, focofilcon A, hilafilcon A, hilafilcon B, hifilcon B, hioxifilcon A, hioxifilcon B, hioxifilcon D, metafilcon A, metafilcon B, nerfilcon A, nesofilcon A, ocufilcon A, ocufilcon B, ocufilcon C, ocufilcon D, omafilcon A, femfilcon A, polymacon, samfilcon A, terfilcon A, tetrafilcon A, and bifilcon A. These can be used as a base formulation for preparing a polymerizable composition for forming the bulk non-silicone hydrogel material of the present invention by adding at least one UV-absorbing vinyl monomer, at least one UV / HEVL-absorbing vinyl monomer, and at least one Cu(II)-porphyrin to the base formulation.

[0128] Preferably, the bulk non-silicone hydrogel material contains at least 50 mol% of repeating units of at least one hydroxyl-containing vinyl monomer selected from the group consisting of hydroxyethyl (meth)acrylate, glycerol (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-amino-2-hydroxypropyl (meth)acrylate, N-2-hydroxyethyl (meth)acrylamide, N-3-hydroxypropyl (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide, N-2,3-dihydroxypropyl (meth)acrylamide, N-tris(hydroxymethyl)methyl (meth)acrylamide, vinyl alcohol, allyl alcohol, and combinations thereof, more preferably preferably selected from the group consisting of hydroxyethyl (meth)acrylate, glycerol (meth)acrylate, and vinyl alcohol.

[0129] According to the present invention, a bulk silicone hydrogel material can be formed from a lens formulation (i.e., a polymerizable composition) for forming a silicone hydrogel contact lens. Typically, the polymerizable composition for forming the bulk silicone hydrogel material of the present invention comprises (1) at least one hydrophilic vinyl monomer (e.g., at least one hydroxyl-containing acrylic monomer, at least one N-vinylamide monomer, at least one (meth)acrylamide monomer, at least one methylene-containing pyrrolidone monomer, or combinations thereof), (2) at least one vinyl-based crosslinking agent comprising at least one polysiloxane vinyl-based crosslinking agent and / or at least one non-silicone vinyl-based crosslinking agent, (3) at least one UV-absorbing vinyl monomer, (4) at least one UV / HEVL-absorbing vinyl monomer, (5) at least one Cu(II)-porphyrin, (6) at least one siloxane-containing vinyl monomer, and (7) a hydrophobic non-silicone vinyl monomer, a free radical initiator (photoinitiator or thermal initiator), a polymerizable visible colorant (i.e., a polymerizable dye), and at least one component selected from the group consisting of combinations thereof.

[0130] Numerous lens formulations for forming silicone hydrogel contact lenses have been described in a number of patents and patent applications published prior to the filing date of the present application and have been used in the manufacture of commercially available SiHy contact lenses. Examples of commercially available SiHy contact lenses include, but are not limited to, asmofilcon A, balafilcon A, confilcon A, delefilcon A, efrofilcon A, enfilcon A, fanfilcon A, galyfilcon A, lotrafilcon A, lotrafilcon B, narafilcon A, narafilcon B, senofilcon A, senofilcon B, senofilcon C, sumafilcon A, somofilcon A, and stenfilcon A. These can be used as a base formulation for forming a polymerizable composition for forming the bulk silicone hydrogel material of the present invention by adding at least one UV-absorbing vinyl monomer, at least one UV / HEVL-absorbing vinyl monomer, and at least one Cu(II)-porphyrin to the base formulation.

[0131] According to the present invention, any thermal free radical initiator can be used in the present invention. Suitable thermal free radical initiators are known to those skilled in the art and include, for example, peroxides, hydroperoxides, azo-bis(alkyl- or cycloalkylnitrile), persulfates, percarbonates, or mixtures thereof.Examples of preferred thermal free radical initiators include, but are not limited to, benzoyl peroxide, t-butyl peroxide, t-amyl peroxybenzoate, 2,2-bis(tert-butylperoxy)butane, 1,1-bis(tert-butylperoxy)cyclohexane, 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane, 2,5-bis(tert-butylperoxy)-2,5-dimethyl-3-hexyne, bis(1-(tert-butylperoxy)-1-methylethyl)benzene, 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, di-t-butyl diperoxyphthalate, t-butyl hydroperoxide, t-butyl peracetate, t-butyl peroxybenzoate, t-butyl peroxyisopropyl carbonate, acetyl peroxide, lauroyl peroxide, decanoyl peroxide, dicetyl peroxydicarbonate, di(4-t-butylcyclohexyl) peroxydicarbonate (Perkadox 16S), di(2-ethylhexyl) peroxydicarbonate, t-butyl peroxypivalate (Lupersol 11); t-butyl peroxy-2-ethylhexanoate (Trigonox 21-C50), 2,4-pentanedione peroxide, dicumyl peroxide, peracetic acid, potassium persulfate, sodium persulfate, ammonium persulfate, 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) (VAZO 33), 2,2'-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride (VAZO 44), 2,2'-azobis(2-amidinopropane) dihydrochloride (VAZO 50), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO 52), 2,2'-azobis(isobutyronitrile) (VAZO 64 or AIBN), 2,2'-azobis-2-methylbutyronitrile (VAZO 67), 1,1-azobis(1-cyclohexanecarbonitrile) (VAZO 88); 2,2'-azobis(2-cyclopropylpropionitrile), 2,2'-azobis(methyl isobutyrate), 4,4'-azobis(4-cyanovaleric acid), and combinations thereof.Preferably, the thermal initiator is 2,2'-azobis(isobutyronitrile) (AIBN or VAZO 64).

[0132] According to the present invention, any photoinitiator can be used in the present invention. Suitable photoinitiators are benzoin methyl ether, diethoxyacetophenone, benzoyl-phosphine oxide, 1-hydroxycyclohexyl phenyl ketone and Darocur and Irgacur types, preferably Darocur 1173 (registered trademark) and Darocur 2959 (registered trademark), germanium-based Norrish type I photoinitiators (for example, those described in US Patent No. 7,605,190). Examples of benzoylphosphine initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide; bis-(2,6-dichlorobenzoyl)-4-N-propylphenyl-phosphine oxide; and bis-(2,6-dichlorobenzoyl)-4-N-butylphenylphosphine oxide. For example, reactive photoinitiators that can be incorporated into macromers or used as special monomers are also suitable. Examples of reactive photoinitiators are those disclosed in European Patent No. 632,329.

[0133] The polymerizable composition of the present invention can further contain, for example, an antimicrobial agent (for example, silver nanoparticles), a bioactive agent (for example, a drug, an amino acid, a polypeptide, a protein, a nucleic acid, 2-pyrrolidone-5-carboxylic acid (PCA), an alpha hydroxyl acid, linoleic acid and gamma linolenic acid, a vitamin, or any combination thereof), a leachable lubricant (for example, a non-crosslinked hydrophilic polymer having an average molecular weight of 5,000 to 500,000, preferably 10,000 to 300,000, more preferably 20,000 to 100,000 daltons), a leachable tear stabilizer (for example, a phospholipid, a monoglyceride, a diglyceride, a triglyceride, a glycolipid, a glyceroglycolipid, a sphingolipid, a sphingoglycolipid, a fatty acid having 8 to 36 carbon atoms, a fatty alcohol having 8 to 36 carbon atoms, or a mixture thereof), or a combination thereof.

[0134] According to the present invention, the polymerizable composition of the present invention is a fluid composition, which can be a solution, a solvent-free blend (i.e., a fluid composition that does not contain any non-reactive diluent - organic solvent).

[0135] When the polymerizable composition of the present invention is a solution, it can be prepared by dissolving all the desired components in any suitable solvent known to those skilled in the art. Examples of suitable solvents include, but are not limited to, water, tetrahydrofuran, tripropylene glycol methyl ether, dipropylene glycol methyl ether, ethylene glycol n-butyl ether, ketones (e.g., acetone, methyl ethyl ketone, etc.), diethylene glycol n-butyl ether, diethylene glycol methyl ether, ethylene glycol phenyl ether, propylene glycol methyl ether, propylene glycol methyl ether acetate, dipropylene glycol methyl ether acetate, propylene glycol n-propyl ether, dipropylene glycol n-propyl ether, tripropylene glycol n-butyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, tripropylene glycol n-butyl ether, propylene glycol phenyl ether, dipropylene glycol dimethyl ether, polyethylene glycol, polypropylene glycol, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, i-propyl lactate, methylene chloride, 2-butanol, 1-propanol, 2-propanol, menthol, cyclohexanol, cyclopentanol and exo-norborneol, 2-pentanol, 3-pentanol, 2-hexanol, 3-hexanol, 3-methyl-2-butanol, 2-heptanol, 2-octanol, 2-nonanol, 2-decanol, 3-octanol, norborneol, tert-butanol, tert-amyl alcohol, 2-methyl-2-pentanol, 2,3-dimethyl-2-butanol, 3-methyl-3-pentanol, 1-methylcyclohexanol, 2-methyl-2-hexanol, 3,7-dimethyl-3-octanol, 1-chloro-2-methyl-2-propanol, 2-methyl-2-heptanol, 2-methyl-2-octanol, 2,2-methyl-2-nonanol, 2-methyl-2-decanol, 3-methyl-3-hexanol, 3-methyl-3-heptanol, 4-methyl-4-heptanol, 3-methyl-3-octanol, 4-methyl-4-octanol, 3-methyl-3-nonanol, 4-methyl-4-nonanol, 3-methyl-3-octanol, 3-ethyl-3-hexanol, 3-methyl-3-heptanol, 4-ethyl-4-heptanol, 4-propyl-4-heptanol, 4-isopropyl-4-heptanol, 2,4-dimethyl-2-pentanol, 1-methylcyclopentanol, 1-ethylcyclopentanol, 1-ethylcyclopentanol, 3-hydroxy-3-methyl-1-butene, 4-hydroxy-4-methyl-1-cyclopentanol, 2-phenyl-2-propanol, 2-methoxy-2-methyl-2-propanol, 2,3,4-trimethyl-3-pentanol, 3,7-dimethyl-3-octanol, 2-phenyl-2-butanol, 2-methyl-1-phenyl-2-propanol and 3-ethyl-3-pentanol, 1-ethoxy-2-propanol, 1-methyl-2-propanol, t-amyl alcohol, isopropyl alcohol, 1-methyl-2-pyrrolidone, N,N-dimethylpropionamide, dimethylformamide, dimethylacetamide, dimethylpropionamide, N-methylpyrrolidone, and mixtures thereof are included. Preferably, the polymerizable composition is a solution of all desired components in water, 1,2-propylene glycol, polyethylene glycol having a molecular weight of about 400 daltons or less, or mixtures thereof.,

[0136] When the polymerizable composition of the present invention is a solvent-free blend, it can be prepared by mixing all the polymerizable components and other necessary components. The solvent-free polymerizable composition typically contains at least one blending vinyl monomer as a reactive solvent for dissolving all the other polymerizable components of the solvent-free polymerizable composition. Examples of preferred blending vinyl monomers are described later in this application. Preferably, methyl methacrylate is used as the blending vinyl monomer when preparing the solvent-free polymerizable composition.

[0137] The contact lens of the present invention preferably has an oxygen permeability of at least about 40 barrers, more preferably at least about 60 barrers, and even more preferably at least about 80 barrers (at about 35 °C).

[0138] The contact lens of the present invention has a modulus of elasticity of about 1.5 MPa or less, preferably about 1.2 MPa or less, and more preferably about 0.3 MPa to about 1.0 MPa (at a temperature of about 22 °C to about 28 °C).

[0139] The contact lens of the present invention further has an equilibrium water content of about 15 wt% to about 75 wt%, more preferably about 20 wt% to about 70 wt%, and even more preferably about 25 wt% to about 65 wt% in a fully hydrated state (at room temperature). The equilibrium water content of the photochromic SiHy contact lens can be measured according to the procedure disclosed in Example 1.

[0140] All of the various embodiments of the mold, polymerizable composition, curing, and contact lens of the present invention described above can be used in this aspect of the present invention.

[0141] Although various embodiments of the present invention have been described using specific terms, devices, and methods, such descriptions are for illustrative purposes only. The terms used are rather for explanatory purposes than for a limiting meaning. It is understood that those skilled in the art may make changes and modifications without departing from the spirit or scope of the present invention as set forth in the following claims. In addition, as shown below, it should be understood that aspects of various embodiments may be wholly or partially exchanged, or combined in any manner, and / or used together.

[0142] 1. (1) repeating units of at least one hydrophilic vinyl monomer; (2) repeating units of at least one vinyl crosslinking agent; (3) repeating units of at least one UV-absorbing vinyl monomer that absorbs UV light of 280 nm to 380 nm; (4) repeating units of at least one UV / HEVL-absorbing vinyl monomer that absorbs UV light of 280 nm to 380 nm and HEVL of 380 nm to 450 nm; (5) at least one Cu(II)-porphyrin derivative A UV / HEVL filtering contact lens comprising a bulk hydrogel material, wherein the derivative is covalently bonded to the bulk hydrogel material and has an absorption peak (i.e., Soret peak or band) in the region from 395 nm to 435 nm in the visible absorption spectrum. The component (3), (4), and (5) are present in the bulk hydrogel material in an amount and ratio such that the UV / HEVL filtering contact lens has less than 10% UVA%T, less than 1% UVB%T, about 60% or less HEVL%T, about 40% or less %T at 420 nm, and about 80% or more %T at wavelengths between 450 nm and 500 nm.

[0143] 2. The UV / HEVL filtering contact lens according to Embodiment 1, having an HEVL%T of about 55% or less.

[0144] 3. The UV / HEVL filtering contact lens according to Embodiment 1, having an HEVL%T of about 50% or less.

[0145] 4. The UV / HEVL filtering contact lens according to Embodiment 1, having an HEVL%T of about 45 or less.

[0146] 5. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 4, having a %T at 420 nm of about 30% or less.

[0147] 6. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 4, having a %T at 420 nm of about 25% or less.

[0148] 7. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 4, having a %T at 420 nm of about 20% or less.

[0149] 8. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 7, having a %T of about 85% or more.

[0150] 9. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 7, having a %T of about 90% or more at any wavelength between 450 nm and 500 nm.

[0151] 10. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 9, wherein the at least one UV-absorbing vinyl monomer comprises a benzotriazole-containing vinyl monomer and / or a benzophenone-containing vinyl monomer.

[0152] 11. The UV / HEVL filtering contact lens according to Embodiment 10, wherein the benzophenone-containing vinyl monomer is 2-hydroxy-4-acryloxybenzophenone, 2-hydroxy-4-methacryloxybenzophenone, 2-hydroxy-4-acryloxyethoxybenzophenone, 2-hydroxy-4-methacryloxyethoxybenzophenone, 4-allyloxy-2-hydroxybenzophenone, 4-allyloxyethoxy-2-hydroxybenzophenone, N-(2-benzoyl-4-chlorophenyl)methacrylamide, 2-hydroxy-4-methoxy-4'-(acrylamido-N,N-dimethylpropylaminomethyl)benzophenone, or a combination thereof.

[0153] 12. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 11, wherein the at least one UV-absorbing vinyl monomer includes a benzotriazole-containing vinyl monomer.

[0154] 13. The at least one UV-absorbing vinyl monomer has the formula (1) [Chemical formula] (In the formula: R 1 and R 2 One of them is H, and R 1 and R 2 The other is a monovalent radical of -L 1 -E 1 ; E 1 is vinyl, vinyloxy, allyl, allyloxy, (meth)acryloxy, or (meth)acrylamide; L 1 is a direct bond, a C 1 ~C 6 alkylene divalent radical, or a bond of -L 2 -X 1 -L 3 -; L 2 is a direct bond, a C 1 ~C 3 alkylene divalent radical, [Chemical formula] and X 1 is O, NH, or

Chemical formula

[0155] 14. The at least one UV-absorbing vinyl monomer is 2-(2'-hydroxy-5'-vinylphenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-methacryloyloxyphenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-acryloyloxyphenyl)-2H-benzotriazole, 2-[2'-hydroxy-5'-(2-methacryloyloxyethyl)phenyl)]-2H-benzotriazole (Norbloc), 2-[2'-hydroxy-5'-(2-acryloyloxyethyl)-phenyl)]-2H-benzotriazole, 2-(2'-hydroxy-5'-methacryloyloxypropylphenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-acryloyloxypropylphenyl)-2H-benzotriazole, or a combination thereof, a UV / HEVL filtering contact lens according to any one of Embodiments 1 to 11.

[0156] 15. The at least one UV / HEVL-absorbing vinyl monomer contains a benzotriazole-containing vinyl monomer, a UV / HEVL filtering contact lens according to any one of Embodiments 1 to 14.

[0157] 16. The at least one UV / HEVL-absorbing vinyl monomer is of formula (2) [Chemical formula] (wherein: R 5 is H, F, Cl, CF 3 , CCl 3 , CH 3 , or OCH 3 , and one of R 6 and R 7 is H, OCH 3 , F, Cl, CF 3 , CCl 3 , or C 1 ~C 10 alkyl; and the other of R 6 and R 7 is a monovalent radical of -L 1 -E 1 ; E 1 is vinyl, vinyloxy, allyl, allyloxy, (meth)acryloxy, or (meth)acrylamide; and L 1 is a direct bond, a C 1 ~C 6 alkylene divalent radical, or a bond of -L 2 -X 1 -L 3 -; L 2 is a direct bond, a C 1 ~C 3 alkylene divalent radical, [Chemical formula] ; X 1 is O, NH, or [Chemical formula] , and R 3 and R 4 are methyl or ethyl; L 3 is a C 1 ~C 6 alkylene divalent radical, provided that R 5, R 6 , and R 7The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 14, comprising a benzotriazole-containing vinyl monomer in which at least two of them are not H).

[0158] 17. The at least one UV / HEVL absorbing vinyl monomer is 2-(2’-hydroxy-3’-methacrylamidomethyl-5’-tert-octylphenyl)-2-benzotriazole, 2-(2’-hydroxy-5’-methacrylamidophenyl)-5-chlorobenzotriazole, 2-(2’-hydroxy-5’-methacrylamidophenyl)-5-methoxybenzotriazole, 2-(2’-hydroxy-5’-glycidoxypropyl-3’-t-butylphenyl)-5-chlorobenzotriazole, 4-allyl-2-(5-chloro-2H-benzotriazol-2-yl)-6-methoxyphenol, 2{2’-hydroxy-3’-tert-butyl-5’-[3”-(4”-vinylbenzyloxy)propoxy]phenyl}-5-methoxy-2H-benzotriazole, 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-(1,1-dimethylethyl)-4-ethenyl-phenol, 2-[2'-hydroxy-3'-tert-butyl-5'-(3'-methacryloyloxypropoxy)phenyl]-2H-benzotriazole, 2{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-methoxy-2H-benzotriazole, 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole, 2[2'-hydroxy-3'-tert-butyl-5'-(3'-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole, 2-(2'-hydroxy-5-methacrylamidophenyl)-5-methoxybenzotriazole, 2-(3-allyl-2-hydroxy-5-methylphenyl)-2H-benzotriazole, 2-(2-hydroxy-3-methallyl-5-methylphenyl)-2H-benzotriazole, 2-3'-t-butyl-2'-hydroxy-5'-(3''-dimethylvinylsilylpropoxy)-2'-hydroxyphenyl)-5-methoxybenzotriazole, 2-(2'-hydroxy-5'-methacryloylpropyl-3'-tert-butylphenyl)-5-methoxy-2H-benzotriazole, 2-(2'-hydroxy-5'-acryloylpropyl-3'-tert-butylphenyl)-5-methoxy-2H-benzotriazole, 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]-propyl 2-methylacrylate, 2-(3-(tert-butyl)-4-hydroxy-5-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenoxy)ethyl methacrylate; 2-(5-chloro-2H-benzotriazol-2-yl)-6-methoxy-4-(2-propen-1-yl)-phenol; 2-[2-hydroxy-5-[3-(methacryloyloxy)propyl]-3-tert-butylphenyl]-5-chloro-2H-benzotriazole; or a combination thereof, the UV / HEVL filtering contact lens according to any one of Embodiments 1 to 14.,

[0159] 18. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 17, wherein the at least one Cu(II)-porphyrin includes a Cu(II)-meso-aryl substituted porphyrin.

[0160] 19. The at least one Cu(II)-porphyrin is of formula (3) or (4)

Chemical formula

Chemical formula

Chemical formula

[0161] 20. The UV / HEVL filtering contact lens of any one of embodiments 1-19, wherein the bulk hydrogel material in the dry state constitutes from about 0.6% to about 3.5% by weight of the total components (3), (4), and (5).

[0162] 21. The UV / HEVL filtering contact lens of any one of embodiments 1 to 19, wherein the bulk hydrogel material in the dry state constitutes from about 0.7% to about 3.0% by weight of all components (3), (4), and (5).

[0163] 22. The UV / HEVL filtering contact lens of any one of embodiments 1-19, wherein the bulk hydrogel material in its dry state constitutes from about 0.8% to about 2.5% by weight of the total components (3), (4), and (5).

[0164] 23. The at least one hydrophilic vinyl monomer is selected from the group consisting of: (1) alkyl (meth) acrylamides selected from the group consisting of (meth) acrylamide, N,N-dimethyl (meth) acrylamide, N-ethyl (meth) acrylamide, N,N-diethyl (meth) acrylamide, N-propyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-3-methoxypropyl (meth) acrylamide, and combinations thereof; (2) hydroxyl-containing acrylic monomers selected from the group consisting of N-2-hydroxyethyl (meth) acrylamide, N,N-bis (hydroxyethyl) (meth) acrylamide, N-3-hydroxypropyl (meth) acrylamide, N-2-hydroxypropyl (meth) acrylamide, N-2,3-dihydroxypropyl (meth) acrylamide, N-tris (hydroxymethyl) methyl (meth) acrylamide, 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycerol methacrylate (GMA), di (ethylene glycol) (meth) acrylate, tri (ethylene glycol) (meth) acrylate, tetra (ethylene glycol) (meth) acrylate, poly (ethylene glycol) (meth) acrylate having a number average molecular weight of up to 1500, poly (ethylene glycol) ethyl (meth) acrylamide having a number average molecular weight of up to 1500, and combinations thereof; (3) carboxyl-containing acrylic monomers selected from the group consisting of 2- (meth) acrylamidoglycolic acid, (meth) acrylic acid, ethylacrylic acid, 3- (meth) acrylamidopropionic acid, 5- (meth) acrylamidopentanoic acid, 4- (meth) acrylamidobutanoic acid, 3- (meth) acrylamido-2-methylbutanoic acid, 3- (meth) acrylamido-3-methylbutanoic acid, 2- (meth) acrylamido-2-methyl-3,3-dimethylbutanoic acid, 3- (meth) acrylamidohexanoic acid, 4- (meth) acrylamido-3,3-dimethylhexanoic acid, and combinations thereof.(4) Amino-containing acrylic monomers selected from the group consisting of N-2-aminoethyl (meth) acrylamide, N-2-methylaminoethyl (meth) acrylamide, N-2-ethylaminoethyl (meth) acrylamide, N-2-dimethylaminoethyl (meth) acrylamide, N-3-aminopropyl (meth) acrylamide, N-3-methylaminopropyl (meth) acrylamide, N-3-dimethylaminopropyl (meth) acrylamide, 2-aminoethyl (meth) acrylate, 2-methylaminoethyl (meth) acrylate, 2-ethylaminoethyl (meth) acrylate, 3-aminopropyl (meth) acrylate, 3-methylaminopropyl (meth) acrylate, 3-ethylaminopropyl (meth) acrylate, 3-amino-2-hydroxypropyl (meth) acrylate, trimethylammonium 2-hydroxypropyl (meth) acrylate hydrochloride, dimethylaminoethyl (meth) acrylate, and combinations thereof;(5) N-vinylpyrrolidone (alias, N-vinyl-2-pyrrolidone), N-vinyl-3-methyl-2-pyrrolidone, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-6-methyl-2-pyrrolidone, N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, N-vinyl-5,5-dimethyl-2-pyrrolidone, N-vinyl-3,3,5-trimethyl-2-pyrrolidone, N-vinylpiperidone (alias, N-vinyl-2-piperidone), N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-5-methyl-2-piperidone, N-vinyl-6-methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone, N-vinyl-3,5-dimethyl-2-piperidone, N-vinyl-4,4-dimethyl-2-piperidone, N-vinylcaprolactam (alias, N-vinyl-2-caprolactam), N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, and an N-vinylamide monomer selected from the group consisting of mixtures thereof;(6) A methylene-containing pyrrolidone monomer selected from the group consisting of 1-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-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, 1-n-butyl-3-methylene-2-pyrrolidone, 1-tert-butyl-3-methylene-2-pyrrolidone, and combinations thereof; (7) Ethylene glycol methyl ether (meth)acrylate, di(ethylene glycol) methyl ether (meth)acrylate, tri(ethylene glycol) methyl ether (meth)acrylate, tetra(ethylene glycol) methyl ether (meth)acrylate, C having a number average molecular weight of up to 1500; 1 ~C 4 -alkoxypoly(ethylene glycol)(meth)acrylate, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, and combinations thereof selected from the group consisting of C 1 ~C 4Acrylic monomers having an alkoxyethoxy group; (8) vinyl ether monomers selected from the group consisting of ethylene glycol monovinyl ether, di(ethylene glycol) monovinyl ether, tri(ethylene glycol) monovinyl ether, tetra(ethylene glycol) monovinyl ether, poly(ethylene glycol) monovinyl ether, ethylene glycol methyl vinyl ether, di(ethylene glycol) methyl vinyl ether, tri(ethylene glycol) methyl vinyl ether, tetra(ethylene glycol) methyl vinyl ether, poly(ethylene glycol) methyl vinyl ether, and combinations thereof; (9) allyl ether monomers selected from the group consisting of ethylene glycol monoallyl ether, di(ethylene glycol) monoallyl ether, tri(ethylene glycol) monoallyl ether, tetra(ethylene glycol) monoallyl ether, poly(ethylene glycol) monoallyl ether, ethylene glycol methyl allyl ether, di(ethylene glycol) methyl allyl ether, tri(ethylene glycol) methyl allyl ether, tetra(ethylene glycol) methyl allyl ether, poly(ethylene glycol) methyl allyl ether, and combinations thereof; (10) (meth)acryloyloxyethyl phosphorylcholine, (meth)acryloyloxypropyl phosphorylcholine, 4-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethyl phosphate, 2-[(meth)acryloylamino]ethyl-2'-(trimethylammonio)-ethyl phosphate, 3-[(meth)acryloylamino]propyl-2'-(trimethylammonio)ethyl phosphate, 4-[(meth)acryloylamino]butyl-2'-(trimethylammonio)ethyl phosphate, 5-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 6-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)-ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(triethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(tripropylammonio)ethyl phosphate,2-((Meth)acryloyloxy)ethyl-2'-(tributylammonio)ethyl phosphate, 2-((meth)acryloyloxy)propyl-2'-(trimethylammonio)-ethyl phosphate, 2-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxycarbonyl)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonyl)ethyl-2'-(trimethylammonio)-ethyl phosphate, 2-(vinylcarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(butenoyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, and a phosphorylcholine-containing vinyl monomer selected from the group consisting of combinations thereof; (11) allyl alcohol; (12) N-2-hydroxyethyl vinyl carbamate; (13) N-carboxyvinyl-β-alanine (VINAL); (14) N-carboxyvinyl-α-alanine; (15) or a combination thereof, the UV / HEVL filtering contact lens according to any one of Embodiments 1 to 22.

[0165] 24. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 23, wherein the bulk hydrogel material is a non-silicone hydrogel material.

[0166] 25. The UV / HEVL filtering contact lens according to Embodiment 24, wherein the non-silicone hydrogel material contains at least 50 mol% of repeating units of at least one hydroxyl-containing vinyl monomer.

[0167] 26. The at least one hydroxyl-containing vinyl monomer is selected from the group consisting of hydroxyethyl (meth)acrylate, glycerol (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-amino-2-hydroxypropyl (meth)acrylate, N-2-hydroxyethyl (meth)acrylamide, N-3-hydroxypropyl (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide, N-2,3-dihydroxypropyl (meth)acrylamide, N-tris(hydroxymethyl)methyl (meth)acrylamide, vinyl alcohol, allyl alcohol, and combinations thereof, and the UV / HEVL filtering contact lens according to Embodiment 25.

[0168] 27. The bulk hydrogel material is a silicone hydrogel material, and the UV / HEVL filtering contact lens according to any one of Embodiments 1 to 23.

[0169] 28. The silicone hydrogel material contains repeating units of at least one siloxane-containing vinyl monomer, and the UV / HEVL filtering contact lens according to Embodiment 27.

[0170] 29. The at least one siloxane-containing vinyl monomer is α-(meth)acryloxypropyl-terminated ω-C 1 ~C 4 -alkyl-terminated polydimethylsiloxane, α-(meth)acryloxy-2-hydroxypropyloxypropyl-terminated ω-C 1 ~C 4 -alkyl-terminated polydimethylsiloxane, α-(2-hydroxyl-methacryloxypropyloxypropyl)-ω-C 1 ~C 4 -alkyl-decamethylpentasiloxane, α-[3-(meth)acryloxyethoxy-2-hydroxypropyloxypropyl]-terminated ω-C 1 ~C 4-Alkyl-terminated polydimethylsiloxane, α-[3-(meth)acryloyloxy-propyl-oxy-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[3-(meth)acryloyloxyisopropyl-oxy-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[3-(meth)acryloyloxybutyl-oxy-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[3-(meth)acryloyloxyethylamino-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[3-(meth)acryloyloxypropylamino-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[3-(meth)acryloyloxy-butylamino-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-(meth)acryloyloxy(polyethyleneoxy)-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[(meth)acryloyloxy-2-hydroxypropyl-oxy-ethoxypropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[(meth)acryloyloxy-2-hydroxypropyl-N-ethylaminopropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[(meth)acryloyloxy-2-hydroxypropyl-amino-propyl]-terminated ω-C 1 ~C 4-Alkyl-terminated polydimethylsiloxane, α-[(meth)acryloxy-2-hydroxypropyl-oxy-(polyethyleneoxy)propyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-(meth)acryloylamidopropyl-oxypropyl-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-N-methyl-(meth)acryloylamidopropyl-oxypropyl-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[3-(meth)acrylamidoethoxy-2-hydroxypropyl-oxy-propyl]-terminated ω-C 1 ~C 4 -Alkyl polydimethylsiloxane, α-[3-(meth)acrylamidopropyl-oxy-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[3-(meth)acrylamidoisopropyl-oxy-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[3-(meth)acrylamidobutyl-oxy-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-[3-(meth)acryloylamido-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4 -Alkyl polydimethylsiloxane, α-[3-[N-methyl-(meth)acryloylamido]-2-hydroxypropyl-oxypropyl]-terminated ω-C 1 ~C 4-Alkyl-terminated polydimethylsiloxane, N-methyl-N'-(propyltetra(dimethylsiloxy)dimethylbutylsilane)(meth)acrylamide, N-(2,3-dihydroxypropane)-N'-(propyltetra(dimethylsiloxy)dimethylbutylsilane)(meth)acrylamide, (meth)acryloylamidopropyltetra(dimethylsiloxy)dimethylbutylsilane, α-vinyl carbonate-terminated ω-C 1 ~C 4 -Alkyl-terminated polydimethylsiloxane, α-vinyl carbamate-terminated ω-C 1 ~C 4 The UV / HEVL filtering contact lens according to embodiment 28, which is selected from the group consisting of -alkyl-terminated polydimethylsiloxane and mixtures thereof.

[0171] 30. The UV / HEVL filtering contact lens according to embodiment 28, wherein the at least one siloxane-containing vinyl monomer is selected from the group consisting of vinyl monomers having a bis(trialkylsilyloxy)alkylsilyl group, vinyl monomers having a tris(trialkylsilyloxy)silyl group, polysiloxane vinyl monomers, 3-methacryloxypropylpentamethyldisiloxane, t-butyldimethyl-siloxyethyl vinyl carbonate, trimethylsilylethyl vinyl carbonate, trimethylsilylmethyl vinyl carbonate, and combinations thereof.

[0172] 31. The at least one siloxane-containing vinyl monomer has the formula (M1) or (M2)

Chemical formula

[0173] 32. The at least one siloxane-containing vinyl monomer is tris(trimethylsilyloxy)silylpropyl (meth)acrylate, [3-(meth)acryloyloxy-2-hydroxypropyl-oxy]propylbis(trimethylsiloxy)methylsilane, [3-(meth)acryloyloxy-2-hydroxypropyl-oxy]propylbis(trimethylsiloxy)butylsilane, 3-(meth)acryloyloxy-2-(2-hydroxyethoxy)-propyl-oxy)propylbis(trimethylsiloxy)methylsilane, 3-(meth)acryloyloxy-2-hydroxypropyl-oxy)propyltris(trimethylsiloxy)silane, N-[tris(trimethylsiloxy)silylpropyl]-(meth)acrylamide, N-(2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyl-oxy)propyl)-2-methyl(meth)acrylamide, N-(2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyl-oxy)-propyl)(meth)acrylamide, N-(2-hydroxy-3-(3-(tris(trimethylsiloxy)silyl)propyl-oxy)propyl)-2-methylacrylamide, N-(2-hydroxy-3-(3-(tris(trimethylsiloxy)silyl)propyl-oxy)propyl)(meth)acrylamide, N-[tris(dimethylpropylsiloxy)silylpropyl]-(meth)acrylamide, N-[tris(dimethylphenylsiloxy)-silylpropyl](meth)acrylamide, N-[tris(dimethylethylsiloxy)-silylpropyl](meth)acrylamide, N,N-bis[2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)-propyl-oxy)propyl]-2-methyl(meth)acrylamide, N,N-bis[2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyl-oxy)-propyl](meth)acrylamide, N,N-bis[2-hydroxy-3-(3-(tris(trimethylsiloxy)silyl)propyl-oxy)propyl]-2-methyl(meth)acrylamide, N,N-N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)-propyloxy)propyl](meth)acrylamide, N-[2-hydroxy-3-(3-(t-butyldimethylsilyl)propyloxy)-propyl]-2-methyl(meth)acrylamide, N-[2-hydroxy-3-(3-(t-butyldimethylsilyl)propyloxy)propyl](meth)acrylamide, N,N-bis[2-hydroxy-3-(3-(t-butyldimethylsilyl)propyloxy)propyl]-2-methyl(meth)acrylamide, N-2-(meth)acryloxyethyl-O-(methyl-bis-trimethylsiloxy-3-propyl)silyl carbamate, 3-(trimethylsilyl)propyl vinyl carbonate, 3-(vinyloxycarbonylthio)-propyl-tris(trimethylsiloxy)silane, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate, 3-[tris(trimethylsiloxy)silyl]propyl allyl carbamate, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate, or a combination thereof, the UV / HEVL filtering contact lens according to Embodiment 28.,

[0174] 33. The UV / HEVL filtering contact lens according to any one of Embodiments 27 to 32, wherein the at least one vinyl-based crosslinking agent includes at least one polysiloxane vinyl-based crosslinking agent.,

[0175] 34. The UV / HEVL filtering contact lens according to Embodiment 33, wherein the at least one polysiloxane vinyl-based crosslinking agent has dimethylsiloxane units and a hydrophilic siloxane unit having one methyl substituent and one monovalent C 4 ~C 40 organic group substituent, and having 2 to 6 hydroxyl groups, and includes a di-(meth)acryloyloxy-terminated polysiloxane vinyl-based crosslinking agent.,

[0176] 35. The at least one polysiloxane vinyl-based crosslinking agent has the formula (G) [Chemical formula] (wherein: d1 is an integer from 30 to 500 and d2 is an integer from 1 to 75, provided that d2 / d1 is from about 0.035 to about 0.15; X 01 is O or NR IN wherein R IN is hydrogen or C 1 ~C 10 -alkyl; R I0 is hydrogen or methyl; R I1 and R I2 are each independently a substituted or unsubstituted C 1 ~C 10 alkylene divalent group or -R I4 -O-R I5 - divalent group, wherein R I4 and R I5 are each independently a substituted or unsubstituted C 1 ~C 10 alkylene divalent group; R I3 is a monovalent group of any one of formulas (G-1) to (G-5)

Chemical formula

Chemical formula

[0177] 36. The at least one polysiloxane vinyl-based crosslinking agent is (i) a vinyl crosslinking agent containing one unique polydiorganosiloxane segment and two terminal ethylenically unsaturated groups selected from the group consisting of (meth)acryloyloxy group, (meth)acryloylamino group, vinyl carbonate group, and vinyl carbamate group, and / or (ii) a chain-extended polysiloxane vinyl crosslinking agent containing at least two polydiorganosiloxane segments and a covalent bond linker between each pair of the polydiorganosiloxane segments and two terminal ethylenically unsaturated groups selected from the group consisting of (meth)acryloyloxy group, (meth)acryloylamino group, vinyl carbonate group, and vinyl carbamate group. The UV / HEVL filtering contact lens according to Embodiment 33.

[0178] 37. The at least one polysiloxane vinyl crosslinking agent is α,ω-bis[3-(meth)acrylamidopropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxy-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxyethoxy-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxypropyloxy-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxy-isopropyloxy-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxybutyloxy-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidoethoxy-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidopropyloxy-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidoisopropyloxy-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidobutyloxy-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxyethylamino-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxypropylamino-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxybutylamino-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[(meth)acrylamidoethylamino-2-hydroxypropyloxy-propyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidopropylamino-2-hydroxypropyloxypropyl] terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamido-butylamino-2-hydroxypropyl-oxypropyl] terminated polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2-hydroxypropyl-oxy-ethoxypropyl] terminated polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2-hydroxypropyl-N-ethylaminopropyl] terminated polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2-hydroxypropyl-amino-propyl]-polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2-hydroxypropyl-oxy-(polyethyleneoxy)propyl] terminated polydimethylsiloxane, α,ω-bis[(meth)acryloxyethylamino-carbonyl-oxy-ethoxypropyl] terminated polydimethylsiloxane, α,ω-bis[(meth)acryloxyethylamino-carbonyl-oxy-(polyethyleneoxy)propyl] terminated polydimethylsiloxane, or a combination thereof, the UV / HEVL filtering contact lens according to Embodiment 33.,

[0179] 38. The at least one hydrophilic vinyl monomer includes at least one hydrophilic N-vinylamide monomer selected from the group consisting of N-vinylpyrrolidone, N-vinylpiperidone, N-vinylcaprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, and mixtures thereof, the UV / HEVL filtering contact lens according to any one of Embodiments 27 to 37.

[0180] 39. The at least one hydrophilic vinyl monomer includes N-vinylpyrrolidone and / or N-vinyl-N-methylacetamide, the UV / HEVL filtering contact lens according to any one of Embodiments 27 to 37.

[0181] 40. The at least one hydrophilic vinyl monomer includes a hydrophilic (meth)acrylamide monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N-ethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-propyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-3-methoxypropyl(meth)acrylamide, N-2-hydroxyethyl(meth)acrylamide, N,N-bis(hydroxyethyl)(meth)acrylamide, N-3-hydroxypropyl(meth)acrylamide, N-2-hydroxypropyl(meth)acrylamide, N-2,3-dihydroxypropyl(meth)acrylamide, N-tris(hydroxymethyl)methyl(meth)acrylamide, poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, 2-(meth)acrylamidoglycolic acid, 3-(meth)acrylamidopropionic acid, 5-(meth)acrylamidopentanoic acid, 4-(meth)acrylamidobutanoic acid, 3-(meth)acrylamide-2-methylbutanoic acid, 3-(meth)acrylamide-3-methylbutanoic acid, 2-(meth)acrylamide-2-methyl-3,3-dimethylbutanoic acid, 3-(meth)acrylamidohexanoic acid, 4-(meth)acrylamide-3,3-dimethylhexanoic acid, N-2-aminoethyl(meth)acrylamide, N-2-methylaminoethyl(meth)acrylamide, N-2-ethylaminoethyl(meth)acrylamide, N-2-dimethylaminoethyl(meth)acrylamide, N-3-aminopropyl(meth)acrylamide, N-3-methylaminopropyl(meth)acrylamide, N-3-dimethylaminopropyl(meth)acrylamide, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, and combinations thereof, the UV / HEVL filtering contact lens according to any one of Embodiments 27 to 39.

[0182] 41. The UV / HEVL filtering contact lens according to any one of Embodiments 27 to 39, wherein the at least one hydrophilic vinyl monomer comprises a hydrophilic (meth)acrylamide monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N-ethyl(meth)acrylamide, N-propyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-3-methoxypropyl(meth)acrylamide, N-2-hydroxyethyl(meth)acrylamide, N-3-hydroxypropyl(meth)acrylamide, and combinations thereof.

[0183] 42. The UV / HEVL filtering contact lens according to any one of Embodiments 27 to 41, wherein the at least one hydrophilic vinyl monomer comprises a hydroxyl-containing vinyl monomer selected from the group consisting of hydroxyethyl (meth)acrylate, glycerol (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-amino-2-hydroxypropyl (meth)acrylate, N-2-hydroxyethyl (meth)acrylamide, N-3-hydroxypropyl (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide, N-2,3-dihydroxypropyl (meth)acrylamide, N-tris(hydroxymethyl)methyl (meth)acrylamide, vinyl alcohol, allyl alcohol, and combinations thereof.

[0184] 43. The UV / HEVL filtering contact lens according to any one of Embodiments 27 to 42, wherein the at least one hydrophilic vinyl monomer comprises a methylene-containing pyrrolidone monomer selected from the group consisting of 1-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-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, 1-n-butyl-3-methylene-2-pyrrolidone, 1-tert-butyl-3-methylene-2-pyrrolidone, and combinations thereof.

[0185] 44. The UV / HEVL filtering contact lens according to any one of Embodiments 27 to 43, having an oxygen permeability of at least 40 barr in a fully hydrated state (at about 35 °C).

[0186] 45. The UV / HEVL filtering contact lens according to any one of Embodiments 27 to 43, having an oxygen permeability of at least 60 barr in a fully hydrated state (at about 35 °C).

[0187] 46. The UV / HEVL filtering contact lens according to any one of Embodiments 27 to 43, having an oxygen permeability of at least 80 barr in a fully hydrated state (at about 35 °C).

[0188] 47. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 46, wherein the at least one vinyl crosslinking agent comprises at least one non-silicone-based vinyl crosslinking agent.

[0189] 48. The at least one non-silicone vinyl-based crosslinking agent is ethylene glycol di-(meth)acrylate, diethylene glycol di-(meth)acrylate, triethylene glycol di-(meth)acrylate, tetraethylene glycol di-(meth)acrylate, glycerol di-(meth)acrylate, 1,3-propanediol di-(meth)acrylate, 1,3-butanediol di-(meth)acrylate, 1,4-butanediol di-(meth)acrylate, glycerol 1,3-diglycerolate di-(meth)acrylate, ethylene bis[oxy(2-hydroxypropane-1,3-diyl)] di-(meth)acrylate, bis[2-(meth)acryloxyethyl] phosphate, trimethylolpropane di-(meth)acrylate, and 3,4-bis[(meth)acryloyl]tetrahydrofuran, diacrylamide, dimethacrylamide, N,N-di(meth)acryloyl-N-methylamine, N,N-di(meth)acryloyl-N-ethylamine, N,N'-methylenebis(meth)acrylamide, N,N'-ethylenebis(meth)acrylamide, N,N'-dihydroxyethylenebis(meth)acrylamide, N,N'-propylenebis(meth)acrylamide, N,N'-2-hydroxypropylenebis(meth)acrylamide, N,N'-2,3-dihydroxybutylenebis(meth)acrylamide, 1,3-bis(meth)acrylamidepropane-2-yl dihydrogen phosphate, piperazine diacrylamide, tetraethylene glycol divinyl ether, triethylene glycol divinyl ether, diethylene glycol divinyl ether, ethylene glycol divinyl ether, triallyl isocyanurate, triallyl cyanurate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, bisphenol A dimethacrylate, allyl methacrylate, allyl acrylate, N-allyl-methacrylamide, N-allyl-acrylamide, or a combination thereof, and the UV / HEVL filtering contact lens according to Embodiment 47.

[0190] 49. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 48, wherein the bulk hydrogel material further comprises repeating units of at least one hydrophilic non-silicone vinyl-based monomer.

[0191] 50. The at least one hydrophilic vinyl-based monomer is C 1 ~C 10 alkyl (meth)acrylate, cyclopentyl acrylate, cyclohexyl methacrylate, cyclohexyl acrylate, isobornyl (meth)acrylate, styrene, 4,6-trimethylstyrene (TMS), t-butylstyrene (TBS), trifluoroethyl (meth)acrylate, hexafluoro-isopropyl (meth)acrylate, hexafluorobutyl (meth)acrylate, or a combination thereof, and the UV / HEVL filtering contact lens according to Embodiment 46.

[0192] 51. The UV / HEVL filtering contact lens according to any one of Embodiments 1 to 50, wherein the bulk hydrogel material further comprises repeating units of a polymerizable dye.

[0193] 52. The polymerizable dye is 1,4-bis(4-(2-methacryloyloxyethyl)phenylamino)anthraquinone (Reactive Blue 246), 1,4-bis((2-hydroxyethyl)amino)-9,10-anthracenedione-bis(2-propenoic acid)ester (Reactive Blue 247), or a combination thereof, and the UV / HEVL filtering contact lens according to Embodiment 51.

[0194] 53. The weight ratio of component (3) to component (4) in the dry bulk hydrogel material is at least 1.2, and the weight ratio of component (4) to component (5) is at least 1.5, and the UV / HEVL filtering contact lens according to any one of Embodiments 1 to 52.

[0195] 54. The UV / HEVL filtering contact lens according to embodiment 53, wherein the weight ratio of component (3) to component (4) in the bulk hydrogel material in the dry state is at least 1.6.

[0196] 55. The UV / HEVL filtering contact lens according to embodiment 53, wherein the weight ratio of component (3) to component (4) in the bulk hydrogel material in the dry state is at least 2.0.

[0197] 56. The UV / HEVL filtering contact lens according to embodiment 53, wherein the weight ratio of component (3) to component (4) in the bulk hydrogel material in the dry state is at least 2.4.

[0198] 57. The UV / HEVL filtering contact lens according to any one of embodiments 53 to 56, wherein the weight ratio of component (4) to component (5) is at least 2.0.

[0199] 58. The UV / HEVL filtering contact lens according to any one of embodiments 53 to 56, wherein the weight ratio of component (4) to component (5) is at least 2.5.

[0200] 59. The UV / HEVL filtering contact lens according to any one of embodiments 53 to 56, wherein the weight ratio of component (4) to component (5) is at least 3.0.

[0201] 60. The UV / HEVL filtering contact lens according to any one of embodiments 1 to 59, having an elastic modulus of about 2.0 MPa or less in the fully hydrated state (at a temperature of 22°C to 28°C).

[0202] 61. The UV / HEVL filtering contact lens according to any one of embodiments 1 to 59, having an elastic modulus of about 1.5 MPa or less in the fully hydrated state (at a temperature of 22°C to 28°C).

[0203] 62. An UV / HEVL filtering contact lens according to any one of Embodiments 1 to 59, having an elastic modulus of about 1.2 MPa or less in a fully hydrated state (at a temperature of 22°C to 28°C).

[0204] 63. An UV / HEVL filtering contact lens according to any one of Embodiments 1 to 59, having an elastic modulus of about 0.4 MPa to about 1.0 MPa in a fully hydrated state (at a temperature of 22°C to 28°C).

[0205] 64. An UV / HEVL filtering contact lens according to any one of Embodiments 1 to 63, having a water content of about 15% to about 70% in a fully hydrated state (at a temperature of 22°C to 28°C).

[0206] 65. An UV / HEVL filtering contact lens according to any one of Embodiments 1 to 63, having a water content of about 20% to about 70% in a fully hydrated state (at a temperature of 22°C to 28°C).

[0207] 66. An UV / HEVL filtering contact lens according to any one of Embodiments 1 to 63, having a water content of about 25% to about 70% in a fully hydrated state (at a temperature of 22°C to 28°C).

[0208] 67. An UV / HEVL filtering contact lens according to any one of Embodiments 1 to 63, having a water content of about 30% to about 65% in a fully hydrated state (at a temperature of 22°C to 28°C).

[0209] Based on the above disclosure, those skilled in the art can implement the present invention. Various modifications, changes, and combinations can be made to the various embodiments described in this specification. To make it more possible for the reader to fully understand a specific embodiment and its advantages, reference to the following examples is proposed. The specification and examples are intended to be considered illustrative.

Examples

[0210] Example 1 Measurement of Oxygen Permeability Unless otherwise specified, the oxygen permeability coefficient (Dk / t), the intrinsic (or edge-corrected) oxygen permeability (Dk i or Dk c ) of the lens and lens material is measured according to the procedure described in ISO 18369-4.

[0211] Equilibrium Water Content The equilibrium water content (EWC) of the contact lens is measured as follows.

[0212] The amount of water present in the hydrated hydrogel contact lens (expressed as a weight percentage) that is completely equilibrated in physiological saline is measured at room temperature. The lenses are quickly stacked, and after wiping the lenses with a cloth, the lens stack is transferred to an aluminum pan on an analytical balance. The number of lenses for each sample pan is typically five. Record the hydrated weight of the pan + lenses. Cover the pan with aluminum foil. Place the pan in a laboratory oven at 100 ± 2 °C and dry for 16 - 18 hours. Remove the pan + lenses from the oven and cool in a desiccator for at least 30 minutes. Remove only one pan from the desiccator and discard the aluminum foil. Weigh the pan + dry lens sample on an analytical balance. Repeat for all pans. The wet weight and dry weight of the lens sample can be calculated by subtracting the weight of the empty weighing pan.

[0213] Elastic Modulus The elastic modulus of the contact lens is measured using an MTS Insight instrument. The contact lens is first cut into strips 3.12 mm wide using a Precision Concept two-stage cutter. Five thickness values are measured within a 6.5 mm gauge length. The strip is attached to the instrument grip and submerged in PBS (phosphate buffered saline) at a temperature controlled to 21 ± 2 °C. Typically, a 5 N load cell is used for the test. A constant force and speed are applied to the sample until it breaks. Force and displacement data are collected by TestWorks software. The elastic modulus value is calculated by TestWorks software, which is the slope or tangent of the stress-strain curve near zero elongation in the elastic deformation region.

[0214] Transmittance The contact lens is manually placed in a specially manufactured sample holder that can maintain the lens shape in the same way as when placed on the eye. This holder is then immersed in a 1 cm path length quartz cell containing phosphate buffered saline (PBS, pH approximately 7.0 - 7.4) as a reference. For this measurement, a UV / Visible spectrophotometer such as a Varian Cary 3E UV-Visible spectrophotometer equipped with a LabSphere DRA-CA-302 beam splitter can be used. The percent transmittance spectrum is collected in the wavelength range of 250 - 800 nm, and the %T values are collected at 0.5 nm intervals. This data is transferred to an Excel spreadsheet and used to determine whether the lens meets Class 1 UV absorbance. Transmittance is calculated using the following formula: UVA %T = Average transmittance % from 315 nm to 380 nm × 100 UVB %T = Average transmittance % from 280 nm to 315 nm × 100 HEVL %T = Average transmittance % from 380 nm to 450 nm × 100

[0215] Chemical substances CE-PDMS is a polysiloxane vinyl crosslinker (Mw = 10.1K, H determined by 1H NMR spectroscopy) having three polydimethylsiloxane (PDMS) segments linked via diurethane bonds between two PDMS segments and two urethane bonds located between one terminal methacrylate group and one PDMS segment, respectively, and prepared according to a method similar to that described in Example 2 of U.S. Patent No. 9,315,669; TRIS-Am represents N-[tris(trimethylsiloxy)-silylpropyl]acrylamide; DMA represents N,N-dimethylacrylamide; L-PEG2000 represents N-(carbonyl-methoxypolyethylene glycol-2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine, sodium salt; DMPC represents 1,2-dimyristoyl-sn-glycero-3-phosphocholine; H-TEMPO represents 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl; Norbloc is 2-[2'-hydroxy-5'-(2-methacryloxyethyl)phenyl)]-2H-benzotriazole from Aldrich; PrOH represents n-propanol; UV28 represents 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole; Cu-TBP-MAm represents Cu(II)-tetra(dimethylaminopropyl-methacrylamidephenyl)porphine; GePI represents bis(4-methoxybenzoyl)diethylgermanium; RB247 represents 1,4-bis((2-hydroxyethyl)amino)-9,10-anthracenedione-bis(2-propenoic acid) ester (Reactive Blue 247); MEK represents methyl ethyl ketone; PBS has a pH of 7.2 ± 0.2 at 25°C and contains approximately 0.044 wt% NaH 1 NMR spectroscopy; TRIS-Am represents N-[tris(trimethylsiloxy)-silylpropyl]acrylamide; DMA represents N,N-dimethylacrylamide; L-PEG2000 represents N-(carbonyl-methoxypolyethylene glycol-2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine, sodium salt; DMPC represents 1,2-dimyristoyl-sn-glycero-3-phosphocholine; H-TEMPO represents 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl; Norbloc is 2-[2'-hydroxy-5'-(2-methacryloxyethyl)phenyl)]-2H-benzotriazole from Aldrich; PrOH represents n-propanol; UV28 represents 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole; Cu-TBP-MAm represents Cu(II)-tetra(dimethylaminopropyl-methacrylamidephenyl)porphine; GePI represents bis(4-methoxybenzoyl)diethylgermanium; RB247 represents 1,4-bis((2-hydroxyethyl)amino)-9,10-anthracenedione-bis(2-propenoic acid) ester (Reactive Blue 247); MEK represents methyl ethyl ketone; PBS has a pH of 7.2 ± 0.2 at 25°C and contains approximately 0.044 wt% NaH 2 PO 4 ·H 2 O, approximately 0.388 wt% Na 2 HPO 4 ·2H 2Phosphate buffered saline containing O, about 0.79 wt% NaCl and 98.78% water; wt% represents weight percent.

[0216] PAA coating solution. The polyacrylic acid (PAA) coating solution is prepared by dissolving PAA (M.W.: 450 kDa, from Lubrizol) in a predetermined amount of 1-propanol (1-PrOH) to a concentration of about 0.44 wt%, and adjusting the pH to about 2.0 with formic acid.

[0217] Preparation of in-package-coating solution (IPC saline). Poly(AAm-co-AA)(90 / 10) partial sodium salt (about 90% solids, poly(AAm-co-AA) 90 / 10, Mw 200,000) was purchased from Polysciences, Inc. and used as received. Polyamidoamine epichlorohydrin (PAE) (Kymene, azetidinium content 0.46 as analyzed by NMR) was purchased from Ashland as an aqueous solution and used as received. IPC saline is prepared by dissolving about 0.07% w / w of poly(AAm-co-AA)(90 / 10) and about 0.10% of PAE (initial azetidinium milliequivalent about 8.8 mmol) in phosphate buffered saline (PBS) (about 0.044 w / w% Na 2 PO 4 ·H 2 O, about 0.388 w / w% Na 2 HPO 4 ·2H 2 O, about 0.79 w / w% NaCl), and adjusting the pH to 7.2 - 7.6. Next, the IPC is heat pretreated at about 60 °C for about 6 hours (heat pretreatment). During this heat pretreatment, poly(AAm-co-AA) and PAE are partially crosslinked with each other (i.e., not all azetidinium groups of PAE are consumed), forming a water-soluble and thermally crosslinkable hydrophilic polymer material containing azetidinium groups in a branched polymer network in the IPC saline. After heat pretreatment, the IPC is cooled to room temperature and filtered through a 0.22 micron PES membrane filter.

[0218] Example 2 Preparation of a lens formulation containing 0.2% UV28 Prepare a lens formulation to have the following composition: 0.20 parts by weight of UV28; 23.12 parts by weight of DMA; 22.49 parts by weight of PrOH; 0.02 parts by weight of RB247; 31.67 parts by weight of CE-PDMS; 19.66 parts by weight of TRIS-Aam; 0.76 parts by weight of DMPC; 0.61 parts by weight of L-PEG2000; 0.04 parts by weight of H-TEMPO; 0.90 parts by weight of Norbloc; and 0.60 parts by weight of GePI.

[0219] Add UV28, DMA, PrOH, RB247, CE-PDMS, Tris-Aam, DMPC, L-PEG2000, H-TEMPO and Norbloc to an amber vial. Then add GePI to the vial under yellow light and mix all the components in a water bath preheated to 40 °C for 30 minutes. After all the solids have dissolved, filter the formulation through a glass microfilter (5.0 μm Millex®-SV filter).

[0220] Lens manufacturing The lens is prepared by casting from the lens-forming composition prepared above using a reusable mold (quartz female molding half and glass male molding half) similar to the mold shown in Figures 1-6 of U.S. Patent Nos. 7,384,590 and 7,387,759 (Figures 1-6). Cure the lens formulation in the mold with 452 nm LED light of intensity 55.4 mW / cm 2 for 30 seconds. After demolding and delensing, extract the cast contact lens and coat it by immersion in the following series of baths: 3 methyl ethyl ketone (MEK) baths (each about 22 seconds, about 78 seconds, about 224 seconds); DI water bath (56 seconds); PAA dip solution prepared in Example 1 (44 seconds); 50 / 50 n-propanol / water bath (56 seconds); 3 DI water baths 3 times (each 56 seconds), and then equilibrate in PBS solution.

[0221] The obtained silicone hydrogel contact lenses are packaged / sealed in polypropylene lens packaging shells (or blisters) (1 lens per 1 shell) containing 0.65 mL of IPC saline prepared in Example 1 and autoclaved at 121 °C for 45 minutes.

[0222] The UV-vis spectra of lenses containing 0.2% of UV28 (UV / HEVL blocker) were recorded and are shown in Figure 1. Based on the preparation of lenses containing 0.2% of UV28, the UV-VIS spectra of lenses containing 0.3% and 0.4% of UV28 were created. For the 0.3% UV28 lens, the absorbance of the 0.2% UV28 lens was multiplied by 1.5 and converted to %T. Similarly, for the 0.4% UV28 lens, the absorbance of the 0.2% UV28 lens was multiplied by 2 and converted to %T. Both graphs were plotted and are shown in Figure 1. All lens properties are shown in the table below.

[0223]

Table 1

[0224] Example 3 Preparation of lens formulations containing 300, 500, and 700 ppm of Cu-TBP-MAm Prepare the lens formulation to have the following composition: 0.03 - 0.07 parts by weight of Cu-TBP-MAm; 23.12 parts by weight of DMA; 22.49 parts by weight of PrOH; 0.02 parts by weight of RB247; 31.67 parts by weight of CE-PDMS; 19.66 parts by weight of TRIS-Aam; 0.76 parts by weight of DMPC; 0.61 parts by weight of L-PEG2000; 0.04 parts by weight of H-TEMPO; 0.90 parts by weight of Norbloc; and 0.60 parts by weight of GePI.

[0225] Add Cu-TBP-MAm, DMA, and PrOH to a first amber vial equipped with a stir bar and mix at 300 rpm for 30 minutes at room temperature. Add RB247, CE-PDMS, Tris-Aam, DMPC, L-PEG2000, H-TEMPO, and Norbloc to a second amber vial. Then, add GePI to the second vial under yellow light and mix all components at 300 rpm for 30 minutes at room temperature. When all solids are dissolved, transfer the contents of the first vial to the second vial using a disposable glass pipette under yellow light. Stir the mixture in a water bath preheated to 40 °C for at least 30 minutes. After all solids are dissolved, filter the formulation through a glass microfilter (5.0 μm Millex®-SV filter).

[0226] Lens manufacturing The lens is prepared by casting from a lens-forming composition prepared above using a reusable mold (quartz female mold half and glass male mold half) similar to the mold shown in Figures 1-6 of US Patent Nos. 7,384,590 and 7,387,759 (Figures 1-6). Cure the lens formulation in the mold with 452 nm LED light at an intensity of 55.4 mW / cm 2 for 30 seconds. After demolding and delensing, extract the cast contact lens and coat it by immersion in the following series of baths: three methyl ethyl ketone (MEK) baths (each about 22 seconds, about 78 seconds, about 224 seconds); DI water bath (56 seconds); PAA dip solution prepared in Example 1 (44 seconds); 50 / 50 n-propanol / water bath (56 seconds); three DI water baths three times (each 56 seconds), and then equilibrate in PBS solution.

[0227] The resulting silicone hydrogel contact lens is packaged / sealed in a polypropylene lens packaging shell (or blister) (1 lens per shell) containing 0.65 mL of IPC saline prepared in Example 1 and autoclaved at 121 °C for 45 minutes.

[0228] The lens contains 300, 500, and 700 ppm of Cu-TBP-MAm (HEVL blocker). The UV-vis spectrum was recorded and is shown in Figure 2. The lens properties are shown in the table below.

[0229]

Table 2

[0230] Example 4 Preparation of a lens formulation containing 300 ppm of Cu-TBP-MAm and 0.2% of UV28 Prepare the lens formulation to have the following composition: 0.03 parts by weight of Cu-TBP-MAm; 23.12 parts by weight of DMA; 22.49 parts by weight of PrOH; 0.02 parts by weight of RB247; 31.67 parts by weight of CE-PDMS; 19.66 parts by weight of Tris-Aam; 0.76 parts by weight of DMPC; 0.61 parts by weight of L-PEG2000; 0.04 parts by weight of H-TEMPO; 0.90 parts by weight of Norbloc; 0.20 parts by weight of UV28 and 0.60 parts by weight of GePI.

[0231] Add Cu-TBP-MAm, DMA, and PrOH to a first amber vial equipped with a stir bar and mix at 300 rpm for 30 minutes at room temperature. Add RB247, CE-PDMS, Tris-Aam, DMPC, L-PEG2000, H-TEMPO, UV28, and Norbloc to a second amber vial. Then, add GePI to the second vial under yellow light and mix all the components at 300 rpm for 30 minutes at room temperature. When all the solids are dissolved, transfer the contents of the first vial to the second vial using a disposable glass pipette under yellow light. Stir the mixture in a water bath preheated to 40 °C for at least 30 minutes. After all the solids are dissolved, filter the formulation through a glass microfilter (5.0 μm Millex®-SV filter).

[0232] Lens production The lens is a reusable mold (quartz female mold half and glass male mold half) similar to the mold shown in Figures 1 - 6 of US Patent Nos. 7,384,590 and 7,387,759 (Figures 1 - 6), and is prepared by casting from the lens-forming composition prepared above. The lens formulation in the mold is cured for 30 seconds with 452 nm LED light of intensity 55.4 mW / cm 2 After demolding and delensing, the cast contact lens is extracted and coated by immersion in the following series of baths: three methyl ethyl ketone (MEK) baths (each about 22 seconds, about 78 seconds, about 224 seconds); DI water bath (56 seconds); PAA dip solution prepared in Example 1 (44 seconds); 50 / 50 n-propanol / water bath (56 seconds); three DI water baths three times (each 56 seconds), and then equilibrated in PBS solution.

[0233] The resulting silicone hydrogel contact lens is packaged / sealed in a polypropylene lens packaging shell (or blister) (1 lens per 1 shell) containing 0.65 mL of IPC saline prepared in Example 1 and autoclaved at 121 °C for 45 minutes.

[0234] The lens contains 300 ppm of Cu-TBP-MAm (HEVL blocker) and 0.2% of UV28 (UV / HEVL blocker). The UV-vis spectrum is recorded and shown in Figure 4. The lens properties are shown in the table below.

[0235] Preparation of a lens formulation containing 500 ppm of Cu-TBP-MAm and 0.3% of UV28 Prepare the lens formulation to have the following composition: 0.05 parts by weight of Cu-TBP-MAm; 23.12 parts by weight of DMA; 22.49 parts by weight of PrOH; 0.02 parts by weight of RB247; 31.67 parts by weight of CE-PDMS; 19.66 parts by weight of TRIS-Aam; 0.76 parts by weight of DMPC; 0.61 parts by weight of L-PEG2000; 0.04 parts by weight of H-TEMPO; 0.90 parts by weight of Norbloc; 0.30 parts by weight of UV28 and 0.60 parts by weight of GePI.

[0236] Add Cu-TBP-MAm, DMA, and PrOH to a first amber vial equipped with a stir bar and mix at 300 rpm for 30 minutes at room temperature. Add RB247, CE-PDMS, Tris-Aam, DMPC, L-PEG2000, H-TEMPO, UV28, and Norbloc to a second amber vial. Then, add GePI to the second vial under yellow light and mix all components at 300 rpm for 30 minutes at room temperature. When all solids are dissolved, transfer the contents of the first vial to the second vial using a disposable glass pipette under yellow light. Stir the mixture in a water bath preheated to 40 °C for at least 30 minutes. After all solids are dissolved, filter the formulation through a glass microfilter (5.0 μm Millex®-SV filter).

[0237] Lens manufacturing The lens is prepared by cast molding from the lens-forming composition prepared above using a reusable mold (quartz female molding half and glass male molding half) similar to the mold shown in FIGS. 1-6 of U.S. Patent Nos. 7,384,590 and 7,387,759 (FIGS. 1-6). Cure the lens formulation in the mold for 30 seconds with 452 nm LED light at an intensity of 55.4 mW / cm 2 . After demolding and delensing, extract the cast contact lens and coat it by immersion in the following series of baths: 3 methyl ethyl ketone (MEK) baths (each about 22 seconds, about 78 seconds, about 224 seconds); DI water bath (56 seconds); PAA dip solution prepared in Example 1 (44 seconds); 50 / 50 n-propanol / water bath (56 seconds); 3 DI water baths 3 times (each 56 seconds), and then equilibrate in PBS solution.

[0238] The resulting silicone hydrogel contact lens is packaged / sealed in a polypropylene lens packaging shell (or blister) (1 lens per shell) containing 0.65 mL of IPC saline prepared in Example 1 and autoclaved at 121 °C for 45 minutes.

[0239] The lens contains 500 ppm of Cu-TBP-MAm (HEVL blocker) and 0.3% of UV28 (UV / HEVL blocker). The UV-vis spectrum was recorded and is shown in Figure 3. The lens characteristics are shown in the table below.

[0240]

Table 3

[0241] All publications and patents cited in this specification are hereby incorporated by reference in their entirety.

Claims

**Claim 1** (1) repeating units of at least one hydrophilic vinyl monomer; (2) repeating units of at least one vinyl crosslinking agent; (3) repeating units of at least one UV-absorbing vinyl monomer that absorbs UV light in the range of 280 nm to 380 nm; (4) at least one UV / HEVL-absorbing vinyl monomer that absorbs UV light in the range of 280 nm to 380 nm and HEVL in the range of 380 nm to 450 nm; (5) at least one Cu(II)-porphyrin derivative A UV / HEVL filtering contact lens comprising a bulk hydrogel material, wherein the derivative is covalently bonded to the bulk hydrogel material and has an absorption peak (i.e., Soret peak or band) in the region from 395 nm to 435 nm in the visible absorption spectrum. The UV / HEVL filtering contact lens, wherein the components (3), (4) and (5) are present in the bulk hydrogel material in an amount and ratio such that the UV / HEVL filtering contact lens has less than 10% UVA%T, less than 1% UVB%T, about 60% or less HEVL%T, about 40% or less %T at 420 nm, and about 80% or more %T at wavelengths between 450 nm and 500 nm. **Claim 2** The UV / HEVL filtering contact lens according to claim 1, wherein the at least one UV-absorbing vinyl monomer comprises a benzotriazole-containing vinyl monomer and / or a benzophenone-containing vinyl monomer. **Claim 3** The at least one UV-absorbing vinyl monomer has the formula (1) 【Chemical 1】 (wherein: R １ and R ２ One of them is H, and R １ and R ２ The other is -L １ -E １ is a monovalent radical; E １ is vinyl, vinyloxy, allyl, allyloxy, (meth)acryloxy, or (meth)acrylamide; L １ is a direct bond, C １ ~C ６ alkylene divalent radical, or -L ２ -X １ -L ３ - bond; L ２ is a direct bond, C １ ~C ３ alkylene divalent radical, [Chemical 2] and; X １ is O, NH, or 【Chemical Formula 3】 and R ３ and R ４ are methyl or ethyl; L ３ is C １ to C ６ alkylene divalent radical), and contains a benzotriazole-containing vinyl monomer The at least one UV / HEVL-absorbing vinyl monomer has the formula (2) 【Chemical Formula 4】 (wherein: R ５ is H, F, Cl, CF ３ , CCl ３ , CH ３ , or OCH ３ , and R ６ and R ７ one of which is H, OCH ３ , F, Cl, CF ３ , CCl ３ , or C １ ~C １０ alkyl, and R ６ and R ７ the other is -L １ -E １ a monovalent radical; E １ is vinyl, vinyloxy, allyl, allyloxy, (meth)acryloxy, or (meth)acrylamide; L １ is a direct bond, C １ ~C ６ alkylene divalent radical, or -L ２ -X １ -L ３ - bond; L ２ is a direct bond, C １ ~C ３ alkylene divalent radical, [Chemical Formula 5] and; X １ is O, NH, or [[Chemical Formula 6]] and R ３ and R ４ are methyl or ethyl; L ３ is C １ to C ６ an alkylene divalent radical, provided that Ｒ 5, R ６ , and R ７ at least two of which are not H), a UV / HEVL filtering contact lens according to claim 1 containing a benzotriazole-containing vinyl monomer. **Claim 4** The at least one UV-absorbing vinyl monomer includes 2-(2'-hydroxy-5'-vinylphenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-methacryloxyphenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-acryloyloxyphenyl)-2H-benzotriazole, 2-[2'-hydroxy-5'-(2-methacryloxyethyl)phenyl)]-2H-benzotriazole (Norbloc), 2-[2'-hydroxy-5'-(2-acryloxyethyl)-phenyl)]-2H-benzotriazole, 2-(2'-hydroxy-5'-methacryloxypropylphenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-acryloxypropylphenyl)-2H-benzotriazole, or a combination thereof, and the at least one UV / HEVL-absorbing vinyl monomer includes 2-(2'-hydroxy-3'-methacrylamidomethyl-5'-tert-octylphenyl)-2-benzotriazole, 2-(2'-hydroxy-5'-methacrylamidophenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-methacrylamidophenyl)-5-methoxybenzotriazole, 2-(2'-hydroxy-5'-glycidyloxypropyl-3'-t-butylphenyl)-5-chlorobenzotriazole, 4-allyl-2-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-6-methoxyphenol, 2{2'-hydroxy-3'-tert-butyl-5'-[3"-(4"-vinylbenzyloxy)propoxy]phenyl}-5-methoxy-2H-benzotriazole, 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-(dimethyl ethyl)-4-ethenyl-phenol, 2-[2'-hydroxy-3'-tert-butyl-5'-(3'-methacryloyloxypropoxy)phenyl]-2H-benzotriazole, 2{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-methoxy-2H-benzotriazole, 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole, 2[2'-hydroxy-3'-tert-butyl-5'-(3'-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole, 2-(2'-hydroxy-5-methacrylamidophenyl)-5-methoxybenzotriazole, 2-(3-allyl-2-hydroxy-5-methylphenyl)-2H-benzotriazole, 2-(2-hydroxy-3-methallyl-5-methylphenyl)-2H-benzotriazole, 2-3'-t-butyl-2'-hydroxy-5'-(3"-dimethylvinylsilylpropoxy)-2'-hydroxyphenyl)-5-methoxybenzotriazole, 2-(2'-hydroxy-5'-methacryloylpropyl-3'-tert-butylphenyl)-5-methoxy-2H-benzotriazole, 2-(2'-hydroxy-5'-acryloylpropyl-3'-tert-butylphenyl)-5-methoxy-2H-benzotriazole, 2-methylacrylic acid 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]-propyl ester, 2-(3-(tert-butyl)-4-hydroxy-5-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenoxy)ethyl methacrylate; 2-(5-chloro-2H-benzotriazol-2-yl)-6-methoxy-4-(2-propen-1-yl)-phenol; 2-[2-hydroxy-5-[3-(methacryloyloxy)propyl]-3-tert-butylphenyl]-5-chloro-2H-benzotriazole; or a combination thereof, the UV / HEVL filtering contact lens according to claim 3. **Claim 5** The UV / HEVL filtering contact lens according to any one of claims 1 to 4, wherein the at least one Cu(II)-porphyrin comprises a Cu(II)-meso-aryl substituted porphyrin. **Claim 6** The at least one Cu(II)-porphyrin has the formula (3) or (4) 【Chemical 7】 (wherein: Each R ８ and R ９ are, independently, H, Cl, F, substituted or unsubstituted C １ to C ２０ alkyl, substituted or unsubstituted C １ to C ２０ alkenyl, substituted or unsubstituted C １ to C ２０ alkynyl, or two adjacent R ８ groups, together with the atom to which they are attached and the atom to which they are bonded, form a substituted or unsubstituted C ６ to C １４ aryl, substituted or unsubstituted C ３ to C １４ carbocyclic, substituted or unsubstituted C ５ to C １４ heteroaryl, or substituted or unsubstituted C ３ to C １４ heterocyclyl; A ２ 、 A ３ 、 A ４ 、 A ５ 、 and A ６ are each independently H, Cl, F, CCl ３ 、 CF ３ 、 CH ３ 、 CH(CH ３ ) ２ 、 C(CH ３ ) ３ 、 OCH ３ 、 OH, NO ２ 、 or -L １ -E １ is a monovalent radical; A ７ and A １１ are each independently Cl, F, CCl ３ , CF ３ , CH ３ , CH(CH ３ ), ２ , C(CH ３ ), ３ , OCH ３ , OH, or NO ２ (preferably Cl, F, or NO ２ ); A ８ 、 A ９ 、 and A １０ are each independently H, Cl, F, CCl ３ , CF ３ , CH ３ , CH(CH ３ ), ２ , C(CH ３ ), ３ , OCH ３ , OH, NH ２ or NO ２ ; E １ is vinyl, vinyloxy, allyl, allyloxy, (meth)acryloxy, or (meth)acrylamide; L １ is a direct bond, C １ to C ６ an alkylene divalent radical, or -L ２ -X １ -L ３ is a bond of -; L ２ is a direct bond, C １ to C ３ alkylene divalent radical, 【Chemical Formula 8】 and; X １ is O, NH, or 【Chemical Formula 9】 and R ３ and R ４ are methyl or ethyl; L ３ is an alkylene divalent radical of C １ to C ６ ; However, one of A ２ , A ３ , A ４ , A ５ , and A ６ is a monovalent radical of -L １ -E １ ), the UV / HEVL filtering contact lens according to any one of claims 1 to 4, comprising a Cu(II)-meso-aryl-substituted porphyrin. **Claim 7** The UV / HEVL filtering contact lens according to any one of claims 1 to 6, wherein the dry bulk hydrogel material constitutes about 0.6 wt% to about 3.5 wt% of all components (3), (4) and (5). **Claim 8** The at least one hydrophilic vinyl monomer is selected from the group consisting of: (1) alkyl (meth)acrylamides such as (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N-ethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N-propyl (meth)acrylamide, N-isopropyl (meth)acrylamide, N-3-methoxypropyl (meth)acrylamide, and combinations thereof; (2) hydroxyl-containing acrylic monomers such as N-2-hydroxyethyl (meth)acrylamide, N,N-bis(hydroxyethyl) (meth)acrylamide, N-3-hydroxypropyl (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide, N-2,3-dihydroxypropyl (meth)acrylamide, N-tris(hydroxymethyl)methyl (meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, glycerol methacrylate (GMA), di(ethylene glycol) (meth)acrylate, tri(ethylene glycol) (meth)acrylate, tetra(ethylene glycol) (meth)acrylate, poly(ethylene glycol) (meth)acrylate having a number average molecular weight of up to 1500, poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, and combinations thereof; (3) carboxyl-containing acrylic monomers such as 2-(meth)acrylamidoglycolic acid, (meth)acrylic acid, ethylacrylic acid, 3-(meth)acrylamidopropionic acid, 5-(meth)acrylamidopentanoic acid, 4-(meth)acrylamidobutanoic acid, 3-(meth)acrylamido-2-methylbutanoic acid, 3-(meth)acrylamido-3-methylbutanoic acid, 2-(meth)acrylamido-2-methyl-3,3-dimethylbutanoic acid, 3-(meth)acrylamidohexanoic acid, 4-(meth)acrylamido-3,3-dimethylhexanoic acid, and combinations thereof.(4) an amino-containing acrylic monomer selected from the group consisting of N-2-aminoethyl (meth) acrylamide, N-2-methylaminoethyl (meth) acrylamide, N-2-ethylaminoethyl (meth) acrylamide, N-2-dimethylaminoethyl (meth) acrylamide, N-3-aminopropyl (meth) acrylamide, N-3-methylaminopropyl (meth) acrylamide, N-3-dimethylaminopropyl (meth) acrylamide, 2-aminoethyl (meth) acrylate, 2-methylaminoethyl (meth) acrylate, 2-ethylaminoethyl (meth) acrylate, 3-aminopropyl (meth) acrylate, 3-methylaminopropyl (meth) acrylate, 3-ethylaminopropyl (meth) acrylate, 3-amino-2-hydroxypropyl (meth) acrylate, trimethylammonium 2-hydroxypropyl (meth) acrylate hydrochloride, dimethylaminoethyl (meth) acrylate, and combinations thereof;(5)N-vinylpyrrolidone (alias, N-vinyl-2-pyrrolidone), N-vinyl-3-methyl-2-pyrrolidone, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-6-methyl-2-pyrrolidone, N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, N-vinyl-5,5-dimethyl-2-pyrrolidone, N-vinyl-3,3,5-trimethyl-2-pyrrolidone, N-vinylpiperidone (alias, N-vinyl-2-piperidone), N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-5-methyl-2-piperidone, N-vinyl-6-methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone, N-vinyl-3,5-dimethyl-2-piperidone, N-vinyl-4,4-dimethyl-2-piperidone, N-vinylcaprolactam (alias, N-vinyl-2-caprolactam), N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, and an N-vinylamide monomer selected from the group consisting of mixtures thereof;(6) A methylene-containing pyrrolidone monomer selected from the group consisting of 1-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-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, 1-n-butyl-3-methylene-2-pyrrolidone, 1-tert-butyl-3-methylene-2-pyrrolidone, and combinations thereof; (7) Ethylene glycol methyl ether (meth)acrylate, di(ethylene glycol) methyl ether (meth)acrylate, tri(ethylene glycol) methyl ether (meth)acrylate, tetra(ethylene glycol) methyl ether (meth)acrylate, C having a number average molecular weight of up to 1500; １ ~C ４ -alkoxypoly(ethylene glycol) (meth)acrylate, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, and combinations thereof selected from the group consisting of C １ ~C ４ An acrylic monomer having an alkoxyethoxy group; (8) a vinyl ether monomer selected from the group consisting of ethylene glycol monovinyl ether, di(ethylene glycol) monovinyl ether, tri(ethylene glycol) monovinyl ether, tetra(ethylene glycol) monovinyl ether, poly(ethylene glycol) monovinyl ether, ethylene glycol methyl vinyl ether, di(ethylene glycol) methyl vinyl ether, tri(ethylene glycol) methyl vinyl ether, tetra(ethylene glycol) methyl vinyl ether, poly(ethylene glycol) methyl vinyl ether, and combinations thereof; (9) an allyl ether monomer selected from the group consisting of ethylene glycol monoallyl ether, di(ethylene glycol) monoallyl ether, tri(ethylene glycol) monoallyl ether, tetra(ethylene glycol) monoallyl ether, poly(ethylene glycol) monoallyl ether, ethylene glycol methyl allyl ether, di(ethylene glycol) methyl allyl ether, tri(ethylene glycol) methyl allyl ether, tetra(ethylene glycol) methyl allyl ether, poly(ethylene glycol) methyl allyl ether, and combinations thereof; (10) (meth)acryloyloxyethyl phosphorylcholine, (meth)acryloyloxypropyl phosphorylcholine, 4-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethyl phosphate, 2-[(meth)acryloylamino]ethyl-2'-(trimethylammonio)-ethyl phosphate, 3-[(meth)acryloylamino]propyl-2'-(trimethylammonio)ethyl phosphate, 4-[(meth)acryloylamino]butyl-2'-(trimethylammonio)ethyl phosphate, 5-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 6-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)-ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(triethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(tripropylammonio)ethyl phosphate,2-((Meth)acryloyloxy)ethyl-2'-(tributylammonio)ethyl phosphate, 2-((Meth)acryloyloxy)propyl-2'-(trimethylammonio)-ethyl phosphate, 2-((Meth)acryloyloxy)butyl-2'-(trimethylammonio)ethyl phosphate, 2-((Meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 2-((Meth)acryloyloxy)hexyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxycarbonyl)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonyl)ethyl-2'-(trimethylammonio)-ethyl phosphate, 2-(vinylcarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(butenoyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, and a phosphorylcholine-containing vinyl monomer selected from the group consisting of combinations thereof; (11) allyl alcohol; (12) N-2-hydroxyethyl vinyl carbamate; (13) N-carboxyvinyl-β-alanine (VINAL); (14) N-carboxyvinyl-α-alanine; (15) or a combination thereof, the UV / HEVL filtering contact lens according to any one of claims 1 to 7. **Claim 9** The UV / HEVL filtering contact lens according to any one of claims 1 to 8, wherein the non-silicone hydrogel material contains at least 50 mol% of repeating units of the at least one hydroxyl-containing vinyl monomer.

10. The bulk hydrogel material is (1) repeating units of at least one siloxane-containing vinyl monomer selected from the group consisting of vinyl monomers having a bis(trialkylsilyloxy)alkylsilyl group, vinyl monomers having a tris(trialkylsilyloxy)silyl group, polysiloxane vinyl monomers, 3-methacryloxypropylpentamethyldisiloxane, t-butyldimethoxysilylethyl vinyl carbonate, trimethylsilylethyl vinyl carbonate, trimethylsilylmethyl vinyl carbonate, and combinations thereof; and / or (2) repeating units of at least one vinyl crosslinking agent containing at least one polysiloxane-containing vinyl crosslinking agent, (i)A monovalent C having one methyl substituent and 2 to 6 hydroxyl groups each ４ ~C ４０ A di(meth)acryloyloxy-terminated polysiloxane vinyl crosslinking agent having dimethylsiloxane units and hydrophilic siloxane units, having an organic radical substituent (ii) Formula (G) 【Chemical Formula 10】 (wherein: d2 / d1 is from about 0.035 to about 0.15, provided that d1 is an integer from 30 to 500 and d2 is an integer from 1 to 75; X ０１ is O or NR ＩＮ wherein R ＩＮ is hydrogen or C １ to C １０ -alkyl; R Ｉ０ is hydrogen or methyl; R Ｉ１ and R Ｉ２ are, independently of each other, a substituted or unsubstituted C １ -C １０ alkylene divalent group or -R Ｉ４ -O-R Ｉ５ - divalent group, where R Ｉ４ and R Ｉ５ are, independently of each other, a substituted or unsubstituted C １ -C １０ alkylene divalent group; R Ｉ３ is the formulas (G-1) to (G-5) 【Chemical 11】 is any one of the monovalent groups of k1 is zero or 1; m1 is an integer from 2 to 4; m2 is an integer from 1 to 5; m3 is an integer from 3 to 6; m4 is an integer from 2 to 5; R Ｉ６ is hydrogen or methyl; R Ｉ７ is a C having a valence of (m2 + 1) ２ to C ６ hydrocarbon group; R Ｉ８ is a C having a valence of (m4 + 1) ２ to C ６ hydrocarbon group; R Ｉ９ is ethyl or hydroxymethyl; R Ｉ１０ is methyl or hydroxymethyl, R Ｉ１１ is hydroxyl or methoxy; X Ｉ１ is a sulfur bond of -S- or a tertiary amino bond of -NR Ｉ１２ -, where R Ｉ１２ is C １ to C １ alkyl, hydroxyethyl, hydroxypropyl, or 2,3-dihydroxypropyl; X Ｉ２ is 【Chemical 12】 is an amide bond, and R Ｉ１３ is hydrogen or C １ to C １０ alkyl), a hydrophilic polysiloxane vinyl crosslinking agent (iii) a vinyl crosslinking agent containing one single polydiorganosiloxane segment and two terminal ethylenically unsaturated groups selected from the group consisting of (meth)acryloyloxy group, (meth)acryloylamino group, vinyl carbonate group, and vinyl carbamate group, (iv) a chain-extended polysiloxane vinyl crosslinking agent containing at least two polydiorganosiloxane segments, a covalent linker between each pair of polydiorganosiloxane segments, and two terminal ethylenically unsaturated groups selected from the group consisting of (meth)acryloyloxy group, (meth)acryloylamino group, vinyl carbonate group, and vinyl carbamate group, (v) α,ω-bis[3-(meth)acrylamidopropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxy-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxyethoxy-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxypropyl-oxy-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxy-isopropyl-oxy-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxybutyloxy-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidoethoxy-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidopropyl-oxy-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidoisopropyl-oxy-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidobutyloxy-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxyethylamino-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxypropylamino-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acryloxybutylamino-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acrylamidoethylamino-2-hydroxypropyl-oxy-propyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidopropylamino-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamido-butylamino-2-hydroxypropyl-oxypropyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acryloyloxy-2-hydroxypropyloxy-ethoxypropyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acryloyloxy-2-hydroxypropyl-N-ethylaminopropyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acryloyloxy-2-hydroxypropyl-aminopropyl]-polydimethylsiloxane, α,ω-bis[(meth)acryloyloxy-2-hydroxypropyloxy-(polyethyleneoxy)propyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acryloyloxyethylamino-carbonyl-oxy-ethoxypropyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acryloyloxyethylamino-carbonyl-oxy-(polyethyleneoxy)propyl]-terminated polydimethylsiloxane or a combination thereof, a first polysiloxane vinyl-based crosslinking agent selected from the group consisting of, or (vi) combinations thereof The silicone hydrogel material containing the above is the UV / HEVL filtering contact lens according to any one of claims 1 to 8.

11. The UV / HEVL filtering contact lens according to claim 10, having an oxygen permeability of at least 40 barr at about 35 °C, a modulus of elasticity of about 2.0 MPa or less at a temperature of 22 °C to 28 °C, and a water content of about 15% to about 70% at a temperature of 22 °C to 28 °C in a fully hydrated state.

12. The UV / HEVL filtering contact lens according to any one of claims 1 to 11, wherein the at least one vinyl-based crosslinking agent includes at least one non-silicone vinyl-based crosslinking agent.

13. The UV / HEVL filtering contact lens according to any one of claims 1 to 12, wherein the bulk hydrogel material includes repeating units of at least one hydrophobic non-silicone vinyl-based monomer; and / or repeating units of a polymerizable dye.

14. wherein the at least one hydrophilic vinyl monomer is C １ to C １０ alkyl (meth)acrylate, cyclopentyl acrylate, cyclohexyl methacrylate, cyclohexyl acrylate, isobornyl (meth)acrylate, styrene, 4,6-trimethylstyrene (TMS), t-butylstyrene (TBS), trifluoroethyl (meth)acrylate, hexafluoro-isopropyl (meth)acrylate, hexafluorobutyl (meth)acrylate, or a combination thereof, and the polymerizable dye is 1,4-bis(4-(2-methacryloxyethyl)phenylamino)anthraquinone (Reactive Blue 246), 1,4-bis((2-hydroxyethyl)amino)-9,10-anthracenedione-bis(2-propenoic acid) ester (Reactive Blue 247), or a combination thereof, the UV / HEVL filtering contact lens according to claim 13.

15. The UV / HEVL filtering contact lens according to any one of claims 1 to 14, wherein the weight ratio of component (3) to component (4) in the dry bulk hydrogel material is at least 1.2, and the weight ratio of component (4) to component (5) is at least 1.5.

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