UV / HEVL filtering silicone hydrogel contact lenses

Abstract

This specification describes UV / HEVL filtering SiHy contact lenses that not only have relatively high UV / HEVL filtering capabilities but also aesthetically attractive colors. The bulk silicone hydrogel of the UV / HEVL filtering SiHy contact lenses comprises (1) at least one hydrophilic vinyl monomer, (2) at least one siloxane-containing vinyl monomer and / or at least one polysiloxane vinyl crosslinking agent, (3) at least one UV-absorbing vinyl monomer having absorption peaks at wavelengths from 280 nm and 380 nm, (4) a first HEVL-absorbing benzotriazole-containing vinyl monomer having absorption peaks at wavelengths from 410 nm and 420 nm, (5) repeating units of a second HEVL-absorbing benzotriazole-containing vinyl monomer having absorption peaks at wavelengths from 415 nm and 425 nm, and (6) repeating units of at least one polymerizable blue dye in an amount of about 90 ppm to about 300 ppm.

Description

[Technical Field]

[0001] The present invention relates to a method for manufacturing contact lenses, preferably silicone hydrogel contact lenses, that can significantly filter UV light and high-energy visible light (HEVL) having wavelengths of 380 nm to 450 nm, and to contact lenses manufactured according to the method of the present invention. [Background technology]

[0002] LED lighting and electronic devices, such as smartphones, computer screens, LCDs, and LED televisions, are widely used. These 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; and Optometry and Vision Science 2011,88(6),1.With the widespread use of LED lighting and LED displays, such as smartphones, televisions, and computer monitors, significant efforts are being made to develop HEVL-filtering ophthalmic lenses, such as eyeglasses, contact lenses, and intraocular lenses, to protect the eyes from increasing HEVL exposure (for example, U.S. Patent Nos. 4612358, 4528311, 4716234, 4878748, 5400175, 5662707, 6158862, 6955430, 7556376, 7803359, 8153703, 8232326, etc.). Specifications No. 8360574, No. 8585938, No. 8882267, No. 9377569, No. 9683102, No. 9814658, No. 10551637, and No. 10610472, U.S. Patent Application Publication No. 20170242274, and No. 20180371139 See the following specifications: (See the document, and specifications No. 20190002415, No. 20190002459, No. 20190271798, No. 20190339544, No. 20200002267, No. 20200095187, No. 20200407324, and No. 20200407337).

[0003] TOTAL30® (manufactured by Alcon) is the first contact lens that maintains effective HEVL filtering performance while the lens is being worn, regardless of lighting conditions. TOTAL30® not only includes Class I UV absorption for protection against UVA and UVB rays (i.e., filtering over 90% of UVA and 99% of UVB rays), but can also filter approximately 33% of HEVL rays (380-450nm) that enter the eye. Alcon subsequently launched a second product, TOTAL1®, which, like TOTAL30®, can block 90% of UVA, 99% of UVB, and 33% of HEVL. Johnson & Johnson Vision Care recently launched ACUVUE® OASYS MAX 1-DAY, which, according to its published 510(k) Premarket Notification (K210930), can block up to 45% of HEVL.

[0004] However, to better protect the wearer's eyes from HEVL damage, particularly violet light damage, contact lens products with significantly higher HEVL filtering performance than currently available commercially are desirable. However, finding a suitable polymerizable HEVL-absorbing dye that can absorb a considerable amount of HEVL light, has good solubility in the lens-forming composition, good compatibility with other polymerizable components in the lens-forming composition, and good lightfastness is extremely difficult. Furthermore, increasing the amount of HEVL absorber added to the contact lens will negatively affect the aesthetic appearance of the contact lens, making it a less attractive yellow. The addition of reactive blue dyes (e.g., RB246 or RB247) could counteract the yellowness of the contact lens, but would contribute to an increase in the darkness of the contact lens. [Overview of the project] [Problems that the invention aims to solve]

[0005] Therefore, there is a need for contact lenses that can significantly filter HEVL, particularly silicone hydrogel contact lenses and such high HEVL filtering contact lenses. [Means for solving the problem]

[0006] The present invention relates to a UV / HEVL filtering contact lens comprising: (1) repeating units of at least one hydrophilic vinyl monomer; (2) repeating units of at least one silicone-containing vinyl monomer and / or at least one polysiloxane vinyl crosslinking agent; (3) repeating units of at least one UV-absorbing vinyl monomer having UV absorption peaks at wavelengths from 280 nm and 380 nm; (4) repeating units of a first HEVL-absorbing benzotriazole vinyl monomer having a first HEVL absorption peak at wavelengths from 410 nm and 420 nm; (5) repeating units of a second HEVL-absorbing benzotriazole vinyl monomer having a second HEVL absorption peak at wavelengths from 415 nm and 425 nm, wherein the wavelength of the second HEVL absorption peak is longer than the wavelength of the first HEVL absorption peak; and (6) reactive blue light of approximately 90 ppm to approximately 300 ppm. The bulk silicone hydrogel material comprises repeating units of at least one polymerizable blue dye, which is 247 (1,4-bis((2-methoxyethyl)amino)-anthraquinone) and / or reactive blue 246 (1,4-bis(4-(2-methacrylateoxyethyl)phenylamino)-anthraquinone), wherein 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 5% UVA%T, about 1% or less UVB%T, about 35% or less HEVL%T, about 15% or less %T at 410 nm, about 60% or less %T at 430 nm and about 90% or more %T at 450 nm, and the UV / HEVL filtering contact lens is a * ≤ -5 and b *We provide UV / HEVL filtering contact lenses having a color represented by ≤ +18. [Brief explanation of the drawing]

[0007] [Figure 1] The UV / Visible transmission spectra (A) and absorption spectra (B) of diluted solutions of three HEVL-absorbing benzotriazole-containing vinyl monomers (UV29, UV28, and UV23), measured in a 1 cm cuvette, are shown: Curve 1 - 40 ppm UV29, Curve 2 - 40 ppm UV28, Curve 3 - 40 ppm UV23. [Figure 2] The UV / visible transmission spectra of HEVL filtering SiHy contact lenses (-3.0D) are shown: Curve 1 - Precision 1 (HEVL%T=95%), Curve 2 - Dailies Total 1 for astigmatism (HEVL%T=67%), Curve 3 - 1.8% Norbloc and 1.5% UV28 (HEVL%T=35%), and Curve 4 - 1.8% Norbloc and 1.5% UV23 (HEVL%T=28%). [Figure 3] The UV / visible transmission spectra of HEVL filtering SiHy contact lenses (-3.0D) are shown: Curve 1 - Precision 1 (HEVL %T=95%), Curve 2 - Astigmatism DAILIES TOTAL 1 (HEVL %T=67%), Curve 3 - 1.8% Norbloc, 1.0% UV28 and 0.75% UV23 (HEVL %T=35%), and Curve 4 - 1.8% Norbloc, 1.25% UV28 and 0.75 wt% UV23 (HEVL %T=28%). [Figure 4] X-rite color measurement of HEVL filtering SiHy contact lenses (-3.0D) is shown: The first, second, and third numbers next to each point represent the amounts of UV23 (wt%), UV28 (wt%), and RB247 (ppm). [Figure 5]The UV / visible transmission spectra of HEVL filtering SiHy contact lenses (-3.0D) are shown: Curve 1 - Lens formulation 5-1, Curve 2 - Lens formulation 5-2, Curve 3 - Lens formulation 5-3, Curve 4 - Lens formulation 5-4, and Curve 5 - Lens formulation 5-5. [Modes for carrying out the invention]

[0008] Unless otherwise specified, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art to which this invention pertains. Generally, the nomenclature and experimental procedures used herein are well known and commonly used in the art. Conventional methods, such as those provided in the art and various general references, are used for these procedures. Where a term is given in the singular form, the inventors also assume that the plural form of that term exists. The nomenclature and laboratory procedures described below herein are well known and commonly adopted in the art.

[0009] As used herein, "approximately" means that the number referred to as "approximately" includes an enumerated number that is plus or minus 1 to 10% of the enumerated number.

[0010] The terms "optional" or "optional" mean that the event or situation described thereafter may or may not occur, and that the description includes both cases in which the event or situation occurs and cases in which it does not occur.

[0011] As used herein, “ophthalmic device” means contact lenses (hard or soft), intraocular lenses, corneal onlays, and other ophthalmic devices used in or near the eyeball or its periphery.

[0012] "Contact lenses" refer to structures that can be placed on or inside the eye of a wearer. Contact lenses may, but are not required to, correct, improve, or alter the wearer's vision. Contact lenses may be made of any suitable material known or subsequently developed in the art, and may be soft lenses, hard lenses, or hybrid lenses.

[0013] "Hydrogel contact lenses" refer to contact lenses that contain a hydrogel bulk (core) material. The hydrogel bulk material may be a non-silicone hydrogel material or, preferably, a silicone hydrogel material.

[0014] A "hydrogel" or "hydrogel material" refers to a crosslinked polymer material having a three-dimensional polymer network (i.e., a polymer matrix), which is insoluble in water but can hold at least 10% by weight of water in its polymer matrix when fully hydrated (or in equilibrium).

[0015] Siloxanes, often also referred to as silicones, are molecules that have at least one -Si-O-Si- moiety, where each Si atom has two organic groups as substituents.

[0016] "Silicone hydrogel" or "SiHy" refers to a silicone-containing hydrogel obtained by copolymerization of a polymerizable composition comprising at least one silicone-containing monomer, at least one silicone-containing macromer, or at least one crosslinkable silicone-containing prepolymer.

[0017] As used in this application, the term "non-silicone hydrogel" refers to a hydrogel that theoretically does not contain silicon.

[0018] As used herein, "hydrophilic" refers to a material or part thereof that associates more readily with water than with lipids.

[0019] The term "room temperature" refers to a temperature between approximately 22°C and 26°C.

[0020] With respect to a compound or substance in a solvent, the term "soluble" means that the compound or substance can dissolve in the solvent to yield a solution with a concentration of at least about 0.5% by weight at room temperature (i.e., at a temperature of about 22°C to about 26°C).

[0021] In relation to compounds or materials in a solvent, the term "insoluble" means that the compound or material can dissolve in the solvent at room temperature (as defined above) to give a solution with a concentration of less than about 0.01% by weight.

[0022] A "vinyl monomer" refers to a compound that has a single ethylenically unsaturated group, is soluble in solvents, and can be polymerized linearly or thermally.

[0023] The term "ethylenically unsaturated group" is used herein in a broad sense and is intended to encompass any group containing at least one >C=CH2 group. Exemplary ethylenically unsaturated groups include, without limitation, (meth)acryloyl [ka] , vinyloxycarbonylamino( [ka] (In the formula, R o (It is H or C1-C4 alkyl)), vinyloxycarbonyloxy [ka] It contains allyl, vinyl, styrenyl, or other C=C-containing groups.

[0024] As used herein, “chemically ray curing” with respect to curing, crosslinking, or polymerization of polymerizable compositions, prepolymers, or materials means that curing (e.g., crosslinking and / or polymerization) is carried out by chemical ray irradiation, such as UV / visible light irradiation. Thermal curing and chemical ray curing methods are well known to those skilled in the art.

[0025] "Acrylic monomer" refers to a vinyl monomer having a single (meth)acryloyl group. Examples of acrylic monomers include (meth)acryloyloxy [or (meth)acryloyloxy] monomers and (meth)acrylamide monomers.

[0026] "(meth)acryloyloxymonomer" or "(meth)acryloyloxymonomer" is [ka] This refers to a vinyl monomer that has only one group.

[0027] "(meth)acrylamide monomer" is [ka] (In the formula, R o (It is H or C1-C4 alkyl) This refers to a vinyl monomer that has only one group.

[0028] The term "(meth)acrylamide" refers to methacrylamide and / or acrylamide.

[0029] The term "(meth)acrylate" refers to methacrylate and / or acrylate.

[0030] "N-vinylamide monomer" refers to an amide compound that has a vinyl group (-CH=CH2) directly bonded to the nitrogen atom of the amide group.

[0031] The term "ene group" refers to a monovalent group of CH2=CH- or CH2=CCH3- that is not covalently bonded to an oxygen or nitrogen atom or a carbonyl group.

[0032] "En monomer" refers to a vinyl monomer that has only one ene group.

[0033] "Vinyloxycarbonylamino monomer" refers to a vinyl monomer that has a single vinyloxycarbonylamino group.

[0034] "Vinylaminocarbonyloxy monomer" refers to a vinyl monomer that has a single vinylaminocarbonyloxy group.

[0035] "Vinylaminocarbonylamino monomer" refers to a vinyl monomer that has a single vinylaminocarbonylamino group.

[0036] "Hydrophilic vinyl monomers" refer to vinyl monomers that typically produce homopolymers that are water-soluble or capable of absorbing at least 10 weight percent of water.

[0037] "Hydrophobic vinyl monomers" refer to vinyl monomers that are insoluble in water and typically produce homopolymers capable of absorbing less than 10% by weight of water.

[0038] 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.

[0039] "Acrylic crosslinking agent" refers to a vinyl crosslinking agent having at least two (meth)acryloyl groups.

[0040] 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 through free radical polymerization to form a polymer material.

[0041] The term "terminal (meth)acryloyl group" refers, as is known to those skilled in the art, to a single (meth)acryloyl group at one of the two ends of the main chain (or skeleton) of an organic compound.

[0042] As used in this application, the term "polymer" means a material formed by polymerizing / crosslinking one or more monomers, macromers, or prepolymers, or combinations thereof.

[0043] "Macromer" or "prepolymer" refers to a compound or polymer containing ethylenically unsaturated groups and having a number-average molecular weight greater than 700 daltons.

[0044] As used in this application, the term "molecular weight" of a polymer material (including monomer materials or macromer materials) refers to the number-average molecular weight unless otherwise specified or indicated by the test conditions. Those skilled in the art will know of known methods, such as GPC (gel permeation chromatography) having one or more of the following: refractive index detector, low-angle laser light scattering detector, multi-angle laser light scattering detector, differential viscosity detector, UV detector and infrared (IR) detector, MALDI-TOF MS (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry), 1 I know how to determine the molecular weight of a polymer using methods such as 1H NMR (proton nuclear magnetic resonance) spectroscopy.

[0045] "Polysiloxane segments" or "polydiorganosiloxane segments" are [ka] (In the formula, SN is an integer greater than or equal to 3, and R is independent of each other.) S1 and R S2 Each of these is C1~C 10 Alkyl, phenyl, C1-C4 alkyl-substituted phenyl, C1-C4 alkoxy-substituted phenyl, phenyl-C1-C6-alkyl, C1-C10 Fluoroalkyl, C1-C 10 Fluoroether, aryl, aryl C1-C 18 Alkyl, -alk-(OC2H4) γ1 -OR o (where alk is a C1-C6 alkylene di group, R o is H or C1-C4 alkyl, and γ1 is an integer from 1 to 10), hydroxyl group (-OH), carboxyl group (-COOH), amino group (-NR N1 R N1 ’), -NR N1 - amino bond, -CONR N1 - amide bond, -CONR N1 R N1 ’ amide, -OCONH- urethane bond and at least one functional group selected from the group consisting of C1-C4 alkoxy groups, having a C2-C 40 organic group or linear hydrophilic polymer chain (where R N1 and R N1 ’ are, independently of each other, hydrogen or C1-C 15 alkyl), and a photochromic organic group having a photochromic group) refers to the polymer chain segment (i.e., divalent group) that can be exchanged.

[0046] "Polydiorganosiloxane vinyl monomer" or "polysiloxane vinyl monomer" refers to a compound containing at least one polysiloxane segment and one unique ethylenically unsaturated group that can be exchanged.

[0047] "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 that can be exchanged.

[0048] "Linear polydiorganosiloxane vinyl crosslinking agent" or "linear polysiloxane vinyl crosslinking agent" interchangeably refers to a compound comprising a main chain containing at least one polysiloxane segment, each of which is terminated with one ethylenically unsaturated group at each of the two ends of the main chain.

[0049] "Chain-extended polydiorganosiloxane vinyl crosslinking agent" or "Chain-extended polysiloxane vinyl crosslinking agent" interchangeably refers to a compound comprising at least two ethylenically unsaturated groups and at least two polysiloxane segments, each pair of which is linked by one divalent group.

[0050] As used herein, the term "fluid" indicates that a material can flow like a liquid.

[0051] As used in this application, the term "transparent" in relation to a polymerizable composition means that the polymerizable composition is a transparent solution or liquid mixture having a light transmittance of 85% or more (preferably 90% or more) in the range of 400 to 700 nm.

[0052] Free radical initiators can be either photoinitiators or thermal initiators. A "photoinitiator" refers to a chemical substance that initiates a free radical crosslinking / polymerization reaction using light. A "thermal initiator" or "thermal free radical initiator" is interchangeable for a chemical substance that initiates a free radical crosslinking / polymerization reaction using thermal energy.

[0053] The term "monovalent group" refers to an organic group obtained by removing a hydrogen atom from an organic compound and which forms one bond with one other group in the organic compound. Examples include, but are not limited to, alkyl (by removing a hydrogen atom from an alkane), alkoxy (or alkoxyl) (by removing one hydrogen atom from the hydroxyl group of an alkyl alcohol), thiyl (by removing one hydrogen atom from the thiol group of an alkylthiol), cycloalkyl (by removing a hydrogen atom from a cycloalkane), cycloheteroalkyl (by removing a hydrogen atom from a cycloheteroalkane), aryl (by removing a hydrogen atom from the aromatic ring of an aromatic hydrocarbon), heteroaryl (by removing a hydrogen atom from any ring atom), and amino (by removing one hydrogen atom from an amine).

[0054] The term "divalent group" refers to an organic group obtained by removing two hydrogen atoms from an organic compound and forming two bonds with two other groups in the organic compound. For example, an alkylene divalent group (i.e., alkylenyl) is obtained by removing two hydrogen atoms from an alkane, and a cycloalkylene divalent group (i.e., cycloalkylenyl) is obtained by removing two hydrogen atoms from a cyclic ring.

[0055] In this application, the term “substituted” in relation to alkyl or alkylenyl means that the alkyl or alkylenyl replaces one hydrogen atom of the alkyl or alkylenyl and includes at least one substituent selected from the group consisting of hydroxyl (-OH), carboxyl (-COOH), -NH2, sulfhydryl (-SH), C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio (alkyl sulfide), C1-C4 acylamino, C1-C4 alkylamino, di-C1-C4 alkylamino and combinations thereof.

[0056] In relation to SiHy lens bulk materials or SiHy contact lenses, "post-curing surface treatment" means a surface treatment process performed after the SiHy lens bulk material or SiHy contact lens has been formed by curing (i.e., thermally or chemically polymerizing) the SiHy lens compound.

[0057] The terms “silicone hydrogel lens formulation” or “SiHy lens formulation” are interchangeable terms for polymerizable compositions containing all the necessary polymerizable components for manufacturing SiHy contact lenses or SiHy lens bulk materials, as is well known to those skilled in the art.

[0058] A "UV-absorbing vinyl monomer" refers to a compound that contains a single ethylenically unsaturated group and can primarily absorb UV light in the 280 nm to 380 nm range. It is understood that UV-absorbing vinyl monomers do not absorb or hardly absorb light with wavelengths above 400 nm (i.e., when tested with a 0.1 mM solution of UV-absorbing vinyl monomer and a 1 cm optical path length, the %T at 400 nm is greater than 90%).

[0059] A "HEVL-absorbing vinyl monomer" refers to a compound that contains a single ethylenically unsaturated group and can primarily absorb UV light in the 380nm to 450nm range. It is understood that HEVL-absorbing vinyl monomers can also absorb UV light in the 280nm to 380nm range.

[0060] "UVA" refers to radiation that occurs at wavelengths of 315 to 380 nanometers, "UVB" refers to radiation that occurs in the range of 280 to 315 nanometers, and "HEVL" refers to radiation that occurs at wavelengths of 380 to 450 nanometers.

[0061] "UVA transmittance" (or "UVA%T"), "UVB transmittance" or "UVB%T", and "HEVL transmittance" or "HEVL%T" are calculated using the following formulas. UVA%T=315nm~380nm average % transmittance x 100 UVB%T=280nm~315nm average % transmittance x 100 HEVL%T=380nm~450nm average % transmittance x 100 HEVL% filtering = 100% - HEVL%T

[0062] "%T at wavelength" refers to the transmittance at a specific wavelength.

[0063] The oxygen permeability of the material (Dk) i Oxygen permeability is the rate at which oxygen passes through the material and can be measured at approximately 34-35°C following the procedure described in Example 1. Oxygen permeability is usually expressed in units of valors, where "valor" is [(cm 3 Oxygen) (mm) / (cm 2 )(sec)(mmHg)]×10 -10 It is defined as follows.

[0064] The "oxygen permeability" Dk / t of a lens or material is the percentage of oxygen that will pass through a particular lens or material with an average thickness of t [in mm] over the area being measured. Oxygen permeability is usually expressed in units of valor / mm, where "valor / mm" is [(cm 3 Oxygen) / (cm 2 )(sec)(mmHg)]×10 -9 It is defined as follows.

[0065] In relation to contact lenses or materials, the term "elastic modulus" or "elastic modulus" refers to the tensile modulus, i.e., Young's modulus, which is a measure of the embedding of the contact lens or material. The elastic modulus can be measured according to the procedure described in Example 1.

[0066] In relation to contact lenses, "coating" means that the contact lens has a thin layer on its surface made of a material different from the bulk material of the contact lens, which is obtained by subjecting the contact lens to a surface treatment.

[0067] As used herein, “surface modification” or “surface treatment” means that an article is treated in a surface treatment process in which, in the process, (1) a coating is applied to the surface of the article, (2) chemical species are adsorbed onto the surface of the article, (3) the chemical properties (e.g., static charge) of chemical groups on the surface of the article are altered, or (4) the surface properties of the article are otherwise modified. Examples of surface treatment processes include, but are not limited to, surface treatments using energy (e.g., plasma, electrostatic charge, irradiation, or other energy sources), chemical treatments, grafting of hydrophilic vinyl monomers or macromers onto article surfaces, mold transfer coating processes disclosed in U.S. Patent No. 6,719,929, the incorporation of wetting agents into lens formulations for manufacturing contact lenses as proposed in U.S. Patents No. 6,367,929 and No. 6,822,016, reinforced mold transfer coatings disclosed in U.S. Patent No. 7,858,000, and hydrophilic coatings comprising covalent bonding or physical deposition of one or more layers of one or more hydrophilic polymers onto the surface of a contact lens, as disclosed in U.S. Patents No. 8,147,897, No. 8,409,599, No. 8,557,334, No. 8,529,057 and No. 9,505,184.

[0068] With respect to SiHy materials or contact lenses, "hydrophilic surface" 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.

[0069] "Average contact angle" refers to the water contact angle (static water contact angle measured by the sessile drop method), which is obtained by averaging the measurements of at least three individual contact lenses.

[0070] Generally, the present invention relates to UV / HEVL filtering contact lenses, more specifically, those having relatively high UV / HEVL filtering capabilities (less than 5% UVA%T, about 1% or less UVB%T, about 35% or less HEVL%T, about 15% or less %T at 410nm, about 60% or less %T at 430nm, and about 90% or more %T at 450nm), but with aesthetically pleasing colors (a on the CIELAB color scale). * ≤ -5 and b * The present invention provides UV / HEVL filtering contact lenses that also have a UV absorption peak (represented by ≤ +18). The present invention is partly based on the discovery that by selecting and combining a UV-absorbing vinyl monomer having a UV absorption peak at wavelengths of 280 nm to 380 nm, a first UV / HEVL-absorbing vinyl monomer with a wavelength around 315 nm, a second UV / HEVL-absorbing vinyl monomer with a wavelength around 318 nm, and a blue-colored polymerizable dye in specific amounts and selected ratios to form a polymerizable composition for contact lens manufacturing, it is possible to obtain UV / HEVL filtering contact lenses that have relatively high UV / HEVL filtering ability and aesthetically attractive colors.

[0071] The present invention relates to a UV / HEVL filtering contact lens comprising: (1) repeating units of at least one hydrophilic vinyl monomer; (2) repeating units of at least one silicone-containing vinyl monomer and / or at least one polysiloxane vinyl crosslinking agent; (3) repeating units of at least one UV-absorbing vinyl monomer having UV absorption peaks at wavelengths from 280 nm and 380 nm; (4) repeating units of a first HEVL-absorbing benzotriazole-containing vinyl monomer having a first HEVL absorption peak at wavelengths from 410 nm and 420 nm; (5) repeating units of a second HEVL-absorbing benzotriazole-containing vinyl monomer having a second HEVL absorption peak at wavelengths from 415 nm and 425 nm, wherein the wavelength of the second HEVL absorption peak is longer than the wavelength of the first HEVL absorption peak; and (6) a repeating unit of about 90 ppm to about 300 ppm, (preferably 1,4-bis((2- The bulk silicone hydrogel material comprises a repeating unit of at least one polymerizable blue dye, which is methoxyethyl)amino)-anthraquinone and / or 1,4-bis(4-(2-methacrylateoxyethyl)phenylamino)-anthraquinone, wherein components (3), (4) and (5) are present in the bulk silicone hydrogel material in amounts and ratios such that the UV / HEVL filtering contact lens has less than 5% UVA%T, about 1% or less UVB%T, about 35% or less (preferably about 32% or less, more preferably about 30% or less, even more preferably about 28% or less) HEVL%T, about 15% or less (preferably about 10% or less) %T at 410 nm, about 60% or less (preferably about 55% or less) %T at 430 nm and about 85% or more %T at 450 nm, and the UV / HEVL filtering contact lens is a * ≤ -5 (preferably a * =-20~-6) and b * We provide UV / HEVL filtering contact lenses having a color represented by ≤ +18.

[0072] The CIE (International Commission on Illumination) has a standardized color ordering system. * a * b * The color system used in this invention is for representing colors numerically. Lightness value L * It is also called "Lstar," and defines black as 0 and white as 100. * The axis is based on the opposite colors of green and magenta, with negative values ​​moving towards green and positive values ​​moving towards magenta. * The axis represents the opposite colors blue and yellow, with negative numbers pointing towards blue and positive numbers pointing towards yellow. These values ​​can be determined by color measurement using X-rite, as shown in the examples.

[0073] In accordance with the present invention, any hydrophilic vinyl monomer can be used in the present invention. Examples of preferred hydrophilic vinyl monomers include alkyl(meth)acrylamides (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 having a methylene group bonded to the pyrrolidone ring at the 3- or 5-position, respectively) (as described later in this application), acrylic monomers having C1-C4 alkoxyethoxy groups (as described later in this application), vinyl ether monomers (as described later in this application), allyl ether monomers (as described later in this application), phosphorylcholine-containing vinyl monomers (as described later in this application), N-2-hydroxyethyl vinylcarbamate, N-carboxyvinyl-β-alanine (VINAL), N-carboxyvinyl-α-alanine, and combinations thereof.

[0074] Any siloxane-containing vinyl monomer can be used in the present invention. Preferred examples of siloxane-containing vinyl monomers may 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 of which contains a polysiloxane chain having a bis(trialkylsilyloxy)alkylsilyl group, a tris(trialkylsilyloxy)silyl group, or 2 to 30 siloxane units, and terminated with an alkyl, hydroxyalkyl, or methoxyalkyl group. Such preferred siloxane-containing vinyl monomers may be obtained from commercial suppliers or, instead, prepared according to known procedures similar to those described in, for example, U.S. Patent Nos. 5070215, 6166236, 6867245, 7214809, 8415405, 8475529, 8614261, 8658748, 9097840, 9103965, 9217813, 9315669, and 9475827. Alternatively, vinyl monomers having a reactive functional group (e.g., acid chloride, acid anhydride, carboxyl, hydroxyl, amino, epoxy, isocyanate, aziridine, azulactone, or aldehyde group) can be prepared by reacting a siloxane-containing compound having a reactive group selected from the group consisting of hydroxyalkyl, aminoalkyl, alkylaminoalkyl, carboxyalkyl, isocyanatoalkyl, epoxyalkyl, and aziridinylalkyl under coupling reaction conditions well known to those skilled in the art, in or out of the presence of a coupling agent.

[0075] In accordance with 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)acrylooxy-terminated polydimethylsiloxanes of various molecular weights, α,ω-(meth)acrylamide-terminated polydimethylsiloxanes of various molecular weights, α,ω-vinylcarbonate-terminated polydimethylsiloxanes of various molecular weights, α,ω-vinylcarbamate-terminated polydimethylsiloxanes of various molecular weights, bis-3-methacrylooxy-2-hydroxypropyloxypropyl polydimethylsiloxanes of various molecular weights, N,N,N',N'-tetrakis(3-methacrylooxy-2-hydroxypropyl)-alpha,omega-bis-3-aminopropyl-polydimethylsiloxanes of various molecular weights, reaction products of glycidyl methacrylate and amino-functional polydimethylsiloxanes, reaction products of azulactone-containing vinyl monomers (any of the above) and hydroxyl-functional polydimethylsiloxanes, U.S. 5,760,Polysiloxane-containing macromers selected from the group consisting of macromer A, macromer B, macromer C, and macromer D as described in Specification No. 100, U.S. Patent No. 4,136,250, No. 4,153,641, No. 4182,822, No. 4189,546, No. 4259,467, No. 4260,725, No. 4261,875, No. 4343,927, No. 4254,248, and the same Specification No. 4355147, Specification No. 4276402, Specification No. 4327203, Specification No. 4341889, Specification No. 4486577, Specification No. 4543398, Specification No. 4605712, Specification No. Specification No. 4661575, Specification No. 4684538, Specification No. 4703097, Specification No. 4833218, Specification No. 4837289, Specification No. 4954586, Specification No. 4954587, Specification No. Specification No. 5010141, Specification No. 5034461, Specification No. 5070170, Specification No. 5079319, Specification No. 5039761, Specification No. 5346946, Specification No. 5358995, Specification No. Specification No. 5387632, Specification No. 5416132, Specification No. 5449729, Specification No. 5451617, Specification No. 5486579, Specification No. 5962548, Specification No. 5981675, Specification No. Examples include the polysiloxane vinyl crosslinking agents disclosed in Specification No. 6039913, No. 6762264, No. 7423074, No. 8163206, No. 8480227, No. 8529057, No. 8835525, No. 8993651, No. 9187601, No. 10081697, No. 10301451, and No. 10465047.

[0076] One preferred class of polysiloxane vinyl crosslinking agents is a monovalent C4-C2 crosslinking agent having a dimethylsiloxane unit and one methyl substituent and 2-6 hydroxyl groups. 40A di-(meth)acryloyloxy-terminated polysiloxane vinyl crosslinking agent having hydrophilic siloxane units each having an organic substituent, more preferably a polysiloxane vinyl crosslinking agent of formula (H), which can be prepared according to the procedure described later in this application and disclosed in U.S. Patent No. 1,0081,697.

[0077] Another class of preferred polysiloxane vinyl crosslinkers are vinyl crosslinkers, each containing one sole polysiloxane segment and two terminal (meth)acryloyl groups, which are available from commercial suppliers and can be prepared by reacting glycidyl (meth)acrylate (meth)acryloyl chloride with a diamino-terminated polydimethylsiloxane or a dihydroxyl-terminated polydimethylsiloxane; by reacting isocyanatoethyl (meth)acrylate with a dihydroxyl-terminated polydimethylsiloxane; by reacting an amino-containing acrylic monomer with a dicarboxyl-terminated polydimethylsiloxane in the presence of a coupling agent (carbodiimide); by reacting a carboxyl-containing acrylic monomer with a diamino-terminated polydimethylsiloxane in the presence of a coupling agent (carbodiimide); or by reacting a hydroxyl-containing acrylic monomer with a dihydroxyl-terminated polydisiloxane in the presence of a diisocyanate or diexope coupling agent.

[0078] Other 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, 7423,074, 852,9057, 883,5525, 8993,651, 9187,601, 10301,451 and 10465,047.

[0079] In accordance with the present invention, any UV-absorbing vinyl monomer can be used in combination with a UV / HEVL-absorbing vinyl monomer as long as it provides Class I UV protection. Preferably, at least one UV-absorbing vinyl monomer may be one or more benzotriazole-containing vinyl monomers (i.e., each having a benzotriazole moiety) selected from the group consisting of 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-acrylooxyethyl)phenyl)]-2H-benzotriazole, 2-(2'-hydroxy-5'-methacryloxypropyl-phenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-acrylooxypropylphenyl)-2H-benzotriazole, and combinations thereof. More preferably, at least one UV-absorbing vinyl monomer is 2-[2'-hydroxy-5'-(2-methacrylateoxyethyl)phenyl)]-2H-benzotriazole (Norbloc).

[0080] Benzotriazole-containing UV-absorbing vinyl monomers can be prepared according to the procedures described in U.S. Patent Nos. 3,299,173, 4612,358, 4716,234, 4528,311, and 10254567, or they can be obtained from commercial suppliers.

[0081] In accordance with the present invention, any HEVL-absorbing benzotriazole-containing vinyl monomer can be used as long as it satisfies specific requirements and provides a desired HEVL filtering profile. Preferably, the first HEVL-absorbing benzotriazole-containing vinyl monomer is 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole (UV28) (having a HEVL absorption peak at 416 nm), while the second HEVL-absorbing benzotriazole-containing vinyl monomer is 2-[2'-hydroxy-3'-tert-butyl-5'-(3'-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole (UV23) (having a HEVL absorption peak at 418 nm).

[0082] According to a preferred embodiment of the present invention, the bulk silicone hydrogel material (dry state) of the UV / HEVL filtering contact lens comprises about 1.2% to about 3.5%, preferably about 1.5% to about 3.0%, and more preferably about 1.5% 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 silicone hydrogel material are 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.

[0083] In accordance with the present invention, the weight ratio of component (4) to component (5) is about 0.25 to about 2.5 (preferably about 0.5 to about 2.0). It is understood that the weight ratio of component (4) to component (5) in the dry bulk silicone hydrogel material may 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.

[0084] Such a weight ratio in the dry bulk hydrogel material allows UV / HEVL absorbing contact lenses to provide Class I UV protection and enhanced HEVL protection while minimizing the impact on color balance, color vision, and coloration.

[0085] Examples of preferred polymerizable blue dyes include, but are not limited to, 1,4-bis(4-(2-methacrylateoxyethyl)phenylamino)anthraquinone (Reactive Blue 246) and 1,4-bis((2-methacrylateoxyethyl)amino)anthraquinone (Reactive Blue 247).

[0086] 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. The contact lenses of the present invention can be manufactured, for example, in a conventional “spin-casting mold” as described in U.S. Patent No. 3,408,429, or preferably by a static, complete casting process as described in U.S. Patents No. 4,347,198, 5,508,317, 5,583,463, 5,789,464 and 5,849,810, or by turning polymer material buttons used in the manufacture of customized contact lenses. In casting, the polymerizable composition (i.e., lens formulation) is typically dispensed into a mold and cured (i.e., thermally or chemically polymerized) within the mold to manufacture a contact lens.

[0087] 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 a combination thereof), (2) at least one siloxane-containing vinyl monomer and / or at least one polysiloxane vinyl crosslinking agent (e.g., any one of those described in this application), and (3) 280 nm and (4) a UV-absorbing vinyl monomer having a UV absorption peak at wavelengths from 380 nm (e.g., Norbloc or one of those described in this application), (5) a first HEVL-absorbing benzotriazole-containing vinyl monomer having a first HEVL absorption peak at wavelengths from 410 nm and 420 nm (e.g., UV28), (6) a second HEVL-absorbing benzotriazole-containing vinyl monomer having a second HEVL absorption peak at wavelengths from 415 nm and 425 nm (e.g., UV23), (7) a polymerizable dye being reactive blue 247 (1,4-bis((2-methoxyethyl)amino)-anthraquinone) and / or reactive blue 246 (1,4-bis(4-(2-methacrylateoxyethyl)phenylamino)-anthraquinone) in about 100 ppm to about 350 ppm, and (8) about 0.2% by weight to about 1.(8) optionally comprising 5% by weight of at least one free radical initiator (e.g., any one described in this application), and at least one component selected from the group consisting of at least one hydrophobic non-silicone vinyl monomer (e.g., any one described in this application), at least one non-silicone vinyl crosslinking agent (e.g., any one described in this application), a leaching lubricant (e.g., a non-crosslinkable 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 leaching tear fluid stabilizer (e.g., phospholipids, monoglycerides, diglycerides, triglycerides, glycolipids, glyceroglycolipids, sphingolipids, sphingoglycolipids, fatty acids having 8 to 36 carbon atoms, fatty alcohols having 8 to 36 carbon atoms, or mixtures thereof) and combinations thereof.

[0088] According to the present invention, any thermal free radical initiator can be used. Suitable thermal free radical initiators are known to those skilled in the art and include, for example, peroxides, hydroperoxides, azo-bis(alkyl- or cycloalkylnitriles), 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-hexine, and bis(1-(tert-butylperoxy)-1-methylhexane (Perkadox)benzene, 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, di-t-butyl-diperoxyphthalate, t-butylhydroperoxide, t-butylperacetate, t-butylperoxybenzoate, t-butylperoxyisopropylcarbonate, acetylperoxide, lauroylperoxide, decanoylperoxide, dicetylperoxydicarbonate, di(4-t-butylcyclohexyl)peroxydicarbonate (Perkadox 16S), di(2-ethylhexyl)peroxydicarbonate, t-butylperoxypivalate (Lupersol 11), t-butylperoxy-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 Examples include 52), 2,2'-azobis(isobutyronitrile) (VAZO 64 or AIBN), 2,2'-azobis-2-methylbutyronitrile (VAZO 67), 1,1-azobis(1-cyclohexanecarbonitride) (VAZO 88), 2,2'-azobis(2-cyclopropylpropionitrile), 2,2'-azobis(methylisobutyrate), 4,4'-azobis(4-cyanovaleric acid), and combinations thereof.

[0089] In accordance with the present invention, any photoinitiator can be used as long as it can generate free radicals to initiate a polymerization reaction when irradiated with visible light having a wavelength greater than 440 nm. Examples of preferred photoinitiators include, but are not limited to, benzoylphosphine photoinitiators, acylgermanium photoinitiators (i.e., germanium-based type I photoinitiators as described in U.S. Patent No. US7605190), and acyltin photoinitiators (e.g., tetrakis(2,4,6-trimethylbenzoyl) stannane or others as described in U.S. Patent Application Publication 18 / 308210).

[0090] Examples of preferred benzoylphosphine initiators include, but are not limited to, 2,4,6-trimethylbenzoyldiphenylphosphine oxide (TPO), 2,4,6-trimethylbenzoylethoxyphenylphosphine oxide (TPO-L), bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (BAPO), bis-(2,6-dichlorobenzoyl)-4-N-propylphenylphosphine oxide, bis-(2,6-dichlorobenzoyl)-4-N-butylphenylphosphine oxide, and lithium phenyl(2,4,6-trimethylbenzoyl)phosphine (LiTPO).

[0091] Preferred acylgermanium photoinitiators include, but are not limited to, bis(4-methoxybenzoyl)diethylgermanium (BMBDE-Ge), dibenzoyldiethylgermanium (DBDE-Ge), and tetrakis(2-ethylbenzoyl)-germanium (TEB-Ge).

[0092] Examples of preferred hydrophobic non-silicone vinyl monomers include, but are not limited to, C1-C11. 10Examples include 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, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl valerate, styrene, chloroprene, vinyl chloride, vinylidene chloride, (meth)acrylonitrile, 1-butene, butadiene, vinyltoluene, vinyl ethyl ether, perfluorohexylethyl-thio-carbonyl-aminoethyl-methacrylate, isobornyl (meth)acrylate, trifluoroethyl (meth)acrylate, hexafluoroisopropyl (meth)acrylate, hexafluorobutyl (meth)acrylate, and combinations thereof.

[0093] Examples of preferred non-silicone vinyl crosslinking agents include, but are not limited to, 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 Rolol 1,3-diglycerolate di-(meth)acrylate, ethylene bis[oxy(2-hydroxypropane-1,3-diyl)] di-(meth)acrylate, bis[2-(meth)acryloyloxyethyl]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 Examples include 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, trimethylopropane trimethacrylate, pentaerythritol tetramethacrylate, bisphenol A dimethacrylate, allyl methacrylate, allyl acrylate, N-allyl-methacrylamide, N-allyl-acrylamide, or combinations thereof.

[0094] As is well known to those skilled in the art, the polymerizable compositions of the present invention may further comprise antimicrobial agents (e.g., silver nanoparticles), bioactive agents (e.g., drugs, amino acids, polypeptides, proteins, nucleic acids, 2-pyrrolidone-5-carboxylic acid (PCA), alpha-hydroxy acids, linoleic acid and gamma-linoleic acid, vitamins or any combination thereof), or any combination thereof.

[0095] According to the present invention, the polymerizable composition of the present invention is a fluid composition, which may be a solution (i.e., one containing a non-reactive diluent-solvent) or a solvent-free blend (i.e., a fluid composition that does not contain any non-reactive diluent-solvent).

[0096] If 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, 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 Polyphenyl 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 exonorborneol, 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 Examples include 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, isopropanol, 1-methyl-2-pyrrolidone, N,N-dimethylpropionamide, dimethylformamide, dimethylacetamide, dimethylpropionamide, N-methylpyrrolidone, and mixtures thereof. Preferably, the polymerizable composition is a solution of all desirable components in water, 1,2-propylene glycol, polyethylene glycol having a molecular weight of about 400 daltons or less, or a mixture thereof.

[0097] If 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. A 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 a solvent-free polymerizable composition.

[0098] Many lens formulations for forming silicone hydrogel contact lenses are described in numerous patents and patent applications published up to the filing date of this application and are 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, Barafilcon A, Confilcon A, Derefilcon A, Ephrofilcon A, Enfilcon A, Funfilcon A, Galifilcon 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 base formulations for forming polymerizable compositions for forming the bulk silicone hydrogel material of the present invention by adding at least one UV-absorbing vinyl monomer, two HEVL-absorbing vinyl monomers, and at least one polymerizable blue dye to the base formulation.

[0099] 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 casting or spin casting. For example, a mold (for casting) generally comprises 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 so that a lens-forming cavity is formed between the first molding surface and the second molding surface. The molding surfaces of the mold halves are cavity-forming surfaces of the mold and are in direct contact with the polymerizable composition.

[0100] Mold halves can be formed by various methods, such as injection molding. Methods for manufacturing mold halves for casting contact lenses are generally well known to those skilled in the art. The method of the present invention is not limited to any particular method of forming a mold. In fact, any method of forming a mold can be used in the present invention. Mold halves can be formed by various techniques, such as injection molding or turning. Examples of preferred processes for forming mold halves are disclosed in U.S. Patent Nos. 4,444,711, 4,460,534, 5,843,446, and 5,894,002.

[0101] Virtually all materials known in the art for manufacturing molds can be used to manufacture molds for manufacturing contact lenses. For example, polymer materials such as polyethylene, polypropylene, polystyrene, PMMA, and Topas® COC grade 8007-S10 (a transparent amorphous copolymer of ethylene and norbornene, manufactured by Ticona GmbH in Frankfurt, Germany and Summit, New Jersey) can be used. Other materials that can transmit UV light, such as quartz glass and sapphire, may also be used.

[0102] In accordance with the present invention, polymerizable compositions can be introduced (distributed) into cavities formed by molds according to any known method.

[0103] After the polymerizable composition is distributed into the mold, it is polymerized to produce a contact lens. Crosslinking can be initiated thermally or chemically to crosslink the polymerizable components in the polymerizable composition.

[0104] Thermal polymerization is conveniently carried out at a temperature of, for example, 25 to 120°C, preferably 40 to 100°C. The reaction time can vary over a wide range, but is conveniently, for example, 30 minutes to 4 hours, or preferably 1 to 2 hours. It is advantageous to degas the components and solvent used in the polymerization reaction beforehand and carry out the copolymerization reaction under an inert atmosphere, for example, a nitrogen or argon atmosphere.

[0105] In that case, chemical beam polymerization can be induced by a chemical beam, for example, visible light of an appropriate wavelength.

[0106] After the curing step, the steps of mold opening (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.

[0107] After removing the molded contact lens, it is typically extracted using 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 oligomer in the lens precursor. Water, any organic solvent known to those skilled in the art, or mixtures thereof can be used in this invention.

[0108] The extracted contact lenses can then be hydrated by any method known to those skilled in the art.

[0109] The extracted and / or hydrated contact lenses may be subjected to further processes such as surface treatment, packaging in lens packages using packaging solutions well known to those skilled in the art, and sterilization such as autoclaving at 118-124°C for at least about 30 minutes.

[0110] Lens packages (or containers) are well known to those skilled in the art for autoclaving and storing soft contact lenses. Any lens package may be used in the present invention. Preferably, the lens package is a blister package comprising a base and a cover, the cover being removably sealed to the base, and the base comprising a cavity for receiving a sterile packaging solution and the contact lens.

[0111] The lenses are packaged in individual packages, sealed, and sterilized (for example, by autoclaving at approximately 120°C or higher for at least 30 minutes under pressure) before being distributed to users. Those skilled in the art will be well aware of the methods for sealing and sterilizing lens packages.

[0112] The contact lenses of the present invention preferably have an oxygen permeability of at least about 40 bar, more preferably at least about 60 bar, and even more preferably at least about 80 bar (at about 35°C).

[0113] The contact lens of the present invention has an elastic modulus 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).

[0114] The contact lenses of the present invention, when fully hydrated, further have an equilibrium water content of about 15% to about 75% by weight, more preferably about 20% to about 70% by weight, and even more preferably about 25% to about 65% by weight (at room temperature). The equilibrium water content of the photochromic SiHy contact lenses can be measured according to the procedure disclosed in Example 1.

[0115] In other embodiments, the present invention comprises (1) at least one hydrophilic vinyl monomer, (2) at least one siloxane-containing vinyl monomer and / or at least one polysiloxane vinyl crosslinking agent, (3) at least one UV-absorbing vinyl monomer having UV absorption peaks at wavelengths from 280 nm and 380 nm, (4) a first HEVL-absorbing benzotriazole-containing vinyl monomer having a first HEVL absorption peak at wavelengths from 410 nm and 420 nm, (5) a second HEVL-absorbing benzotriazole-containing vinyl monomer having a second HEVL absorption peak at wavelengths from 415 nm and 425 nm, (6) about 100 ppm to about 350 ppm of polymerizable blue dye, (7) about 0.2% to about 1.5% by weight of at least one free radical initiator, and (8) optionally, at least one hydrophobic non-silicone vinyl monomer, at least one non-silicone vinyl crosslinking agent, leaching lubricant, leaching tear stabilizer, and combinations thereof. A method for producing a UV / HEVL filtering silicone hydrogel contact lens is provided, comprising the steps of: introducing a polymerizable composition comprising at least one component selected from the group consisting of the following into a mold (wherein the mold comprises a female half having a first molding surface and a male half having a second molding surface, and the mold halves are configured to accept each other so that a lens forming cavity is formed between the first molding surface and the second molding surface); curing the polymerizable composition in the mold to form a UV / HEVL filtering silicone hydrogel contact lens precursor; removing the UV / HEVL filtering silicone hydrogel contact lens precursor from the mold; and subjecting the UV / HEVL filtering silicone hydrogel contact lens precursor to one or more post-molding processes selected from the group consisting of extraction, hydration, surface treatment, packaging, sterilization, and combinations thereof.

[0116] All of the various embodiments of polymerizable compositions, hydrophilic vinyl monomers, silicone-containing vinyl monomers, polysiloxane vinyl crosslinkers, UV-absorbing vinyl monomers, HEVL-absorbing benzotriazole-containing vinyl monomers, polymerizable blue dyes, non-silicone hydrophobic vinyl monomers, non-silicone vinyl crosslinkers, free radical initiators, leaching lubricants, leaching tear film stabilizers, antimicrobial agents, bioactive agents, non-reactive diluents (solvents), molds, thermosetting, photocuring, demolding, lens removal, extraction, hydration, surface treatment, packaging, and autoclave sterilization are described above and may be used in these embodiments of the present invention.

[0117] While 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 descriptive rather than restrictive. It should be understood that modifications and variations can be made by those skilled in the art without departing from the spirit or scope of the invention as expressed in the following claims. In addition, it should be understood that the various embodiments may be interchangeable in whole or in part, or combined and / or used together in any manner, as shown below.

[0118] 1. UV / HEVL filtering silicone hydrogel contact lenses, (1) A repeating unit of at least one hydrophilic vinyl monomer, (2) Repeating units of at least one silicone-containing vinyl monomer and / or at least one polysiloxane vinyl crosslinking agent, (3) Repeating units of at least one UV-absorbing vinyl monomer having UV absorption peaks at wavelengths from 280 nm and 380 nm, (4) Repeating units of a first HEVL-absorbing benzotriazole-containing vinyl monomer having a first HEVL absorption peak at wavelengths from 410 nm and 425 nm, (5) Repeating units of a second HEVL-absorbing benzotriazole-containing vinyl monomer having a second HEVL absorption peak at wavelengths from 410 nm and 425 nm, wherein the wavelength of the second HEVL absorption peak is longer than the wavelength of the first HEVL absorption peak, (6) Repeating units of at least one polymerizable blue dye in a concentration of approximately 90 ppm to approximately 300 ppm The bulk silicone hydrogel material comprises components (3), (4), and (5), wherein the UV / HEVL filtering contact lens is present in the bulk silicone hydrogel material in amounts and ratios such that the UV / HEVL filtering contact lens has less than 5% UVA%T, about 1% or less UVB%T, about 35% or less HEVL%T, about 15% or less %T at 410 nm, about 60% or less %T at 430 nm, and about 85% or more %T at 450 nm. * ≤ -5 and b * UV / HEVL filtering silicone hydrogel contact lenses with a color represented by ≤ +18.

[0119] 2. A UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 1, having a HEVL%T of approximately 32 or less.

[0120] 3. A UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 1, having a HEVL%T of approximately 30 or less.

[0121] 4. A UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 1, having a HEVL%T of approximately 28 or less.

[0122] 5. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 4, having a %T of approximately 10% or less at 410 nm.

[0123] 6. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 5, having a %T of approximately 55% or less at 430 nm.

[0124] 7.a * =-20~-6 and b * A UV / HEVL filtering silicone hydrogel contact lens according to any one of embodiments 1 to 6, having a color represented by ≤ +18.

[0125] 8. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 7, wherein the at least one polymerizable blue dye is 1,4-bis((2-methoxyethyl)amino)-anthraquinone and / or 1,4-bis(4-(2-methacrylateoxyethyl)phenylamino)-anthraquinone.

[0126] 9. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 8, wherein the at least one UV-absorbing vinyl monomer includes a benzotriazole-containing vinyl monomer.

[0127] 10. The UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 9, wherein 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-acrylooxyethyl)phenyl)]-2H-benzotriazole, 2-(2'-hydroxy-5'-methacryloxypropyl-phenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-acrylooxypropylphenyl)-2H-benzotriazole, or a combination thereof.

[0128] 11. The UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 9, wherein the at least one UV-absorbing vinyl monomer is 2-[2'-hydroxy-5'-(2-methacrylateoxyethyl)phenyl)]-2H-benzotriazole.

[0129] 12. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 11, wherein the first HEVL-absorbing benzotriazole-containing vinyl monomer is 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole (UV28).

[0130] 13. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 12, wherein the second HEVL-absorbing benzotriazole-containing vinyl monomer is 2-[2'-hydroxy-3'-tert-butyl-5'-(3'-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole (UV23).

[0131] 14. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 13, wherein the dry bulk silicone hydrogel material constitutes about 1.2% to about 3.5% by weight of all components (3), (4), and (5).

[0132] 15. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 13, wherein the dry bulk silicone hydrogel material constitutes about 1.5% to about 3.0% by weight of all components (3), (4), and (5).

[0133] 16. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 14, wherein the dry bulk silicone hydrogel material constitutes about 1.5% to about 2.5% by weight of all components (3), (4), and (5).

[0134] 17. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 16, wherein the weight ratio of component (4) to component (5) is approximately 0.25 to approximately 2.5.

[0135] 18. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 16, wherein the weight ratio of component (4) to component (5) is approximately 0.5 to approximately 2.0.

[0136] 19. The at least one hydrophilic vinyl monomer is (1) an alkyl(meth)acrylamide 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) N-2-hydroxylethyl(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, di(ethylene glycol)(meth)acrylate, tri(ethylene glycol)(meth)acrylate, tetra(ethylene glycol) (3) Hydroxyl-containing acrylic monomers selected from the group consisting of (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) 2-(meth)acrylamide glycolic acid, (meth)acrylic acid, ethylacrylic acid, 3-(meth)acrylamide propionic acid, 5-(meth)acrylamide pentanoic acid, 4-(meth)acrylamide butanoic acid, 3-(meth)acrylamide-2 -Methylbutanoic acid, 3-(meth)acrylamide-3-methylbutanoic acid, 2-(meth)acrylamide-2methyl-3,3-dimethylbutanoic acid, 3-(meth)acrylamidehexanoic acid, 4-(meth)acrylamide-3,3-dimethylhexanoic acid and combinations thereof selected from the group, (4)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 (5) N-vinylpyrrolidone, 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, 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, N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinylamide monomers selected from the group consisting of 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 mixtures thereof, (6) 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 (7) Methylene-containing pyrrolidone monomers selected from the group consisting of and combinations thereof, acrylic monomers having C1-C4 alkoxyethoxy groups, such as 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, C1-C4 alkoxypoly(ethylene glycol)(meth)acrylate having a number average molecular weight of up to 1500, (8) Acrylic monomers selected from the group consisting of methoxy-poly(ethylene glycol)ethyl(meth)acrylamide and combinations thereof having a number average molecular weight of 1500, 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) 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,Allyl ether monomers selected from the group consisting of 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 Acryloyl 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)acryloyl Oxy)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,A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 18, comprising: (11) allyl alcohol; (12) N-2-hydroxyethyl vinylcarbamate; (13) N-carboxyvinyl-β-alanine (VINAL); (14) N-carboxyvinyl-α-alanine; or (15) a combination thereof.

[0137] 20. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 19, wherein the bulk silicone hydrogel material comprises repeating units of at least one siloxane-containing vinyl monomer.

[0138] 21. The at least one siloxane-containing vinyl monomer is α-(meth)acrylooxypropyl-terminated ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-(meth)acrylooxy-2-hydroxypropyloxypropyl-terminated ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-(2-hydroxyl-methacrylooxypropyloxypropyl)-ω-C1~C4-alkyl-decamethyl-pentasiloxane, α-[3-(meth)acrylooxyethoxy-2-hydroxypropyloxypropyl]terminated ω-C 1-C4-alkyl-terminated polydimethylsiloxane, α-[3-(meth)acrylooxypropyloxy-2-hydroxypropyloxypropyl]-terminated ω-C1-C4-alkyl-terminated polydimethylsiloxane, α-[3-(meth)acrylooxyisopropyloxy-2-hydroxypropyloxypropyl]-terminated ω-C1-C4-alkyl-terminated polydimethylsiloxane, α-[3-(meth)acrylooxybutyloxy-2-hydroxypropyloxypropyl]-terminated ω-C1-C4-alkyl-terminated polydimethylsiloxane, α- [3-(meth)acrylooxyethylamino-2-hydroxypropyloxypropyl]terminal ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-[3-(meth)acrylooxypropylamino-2-hydroxypropyloxypropyl]terminal ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-[3-(meth)acrylooxy-butylamino-2-hydroxypropyloxypropyl]terminal ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-(meth)acrylooxy(polyethyleneoxy)-2-hydro [Hyoxypropyloxypropyl]terminal ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-[(meth)acrylooxy-2-hydroxypropyloxyethoxypropyl]terminal ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-[(meth)acrylooxy-2-hydroxypropyl-N-ethylaminopropyl]terminal ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-[(meth)acrylooxy-2-hydroxypropyl-aminopropyl]terminal ω-C1~C4-alkyl-terminated polydimethylsiloxane,α-[(meth)acryloyloxy-2-hydroxypropyloxy-(polyethyleneoxy)propyl]-terminated ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-(meth)acryloylamidopropyloxypropyl-terminated ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-N-methyl-(meth)acryloylamidopropyloxypropyl-terminated ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-[3-(meth)acryloylamidoethoxy-2-hydroxypropyloxy- [Ropil] Terminal ω-C1~C4-alkyl polydimethylsiloxane, α-[3-(meth)acrylamidepropyloxy-2-hydroxypropyloxypropyl] Terminal ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-[3-(meth)acrylamideisopropyloxy-2-hydroxypropyloxypropyl] Terminal ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-[3-(meth)acrylamidebutyloxy-2-hydroxypropyloxypropyl] Terminal ω-C1~C4- Lukyl-terminated polydimethylsiloxane, α-[3-(meth)acryloylamide-2-hydroxypropyloxypropyl]-terminated ω-C1~C4-alkylpolydimethylsiloxane, α-[3-[N-methyl-(meth)acryloylamide]-2-hydroxypropyloxypropyl]-terminated ω-C1~C4-alkyl-terminated polydimethylsiloxane, N-methyl-N'-(propyltetra-(dimethylsiloxy)dimethylbutylsilane)(meth)acrylamide, N-(2,3-dihydroxypropane)-N' A UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 20, selected from the group consisting of -(propyltetra(dimethylsiloxy)dimethylbutylsilane)(meth)acrylamide, (meth)acryloylamide propyl-tetra(dimethylsiloxy)dimethylbutylsilane, α-vinylcarbonate-terminated ω-C1~C4-alkyl-terminated polydimethylsiloxane, α-vinylcarbamate-terminated ω-C1~C4-alkyl-terminated polydimethylsiloxane, and mixtures thereof.

[0139] 22. The UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 20, 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 monomer, 3-methacrylateoxypropylpentamethyldisiloxane, t-butyldimethyl-siloxyethyl vinyl carbonate, trimethylsilylethyl vinyl carbonate, trimethylsilylmethyl vinyl carbonate, and combinations thereof.

[0140] 23. The at least one siloxane-containing vinyl monomer is of formula (M1) or (M2) [ka] (In the formula, a M1 is zero or 1, and R M0 is H or methyl, and X M0 is O or NR M1 And L M1 is a C2-C8 alkylene divalent group, or [ka] It is a divalent group of L M1 ' is a C2-C8 alkylene divalent group having zero or one hydroxyl group, L M1 '' is a C3-C8 alkylene divalent group having zero or one hydroxyl group, X M1 O, NR M1 NHCOO, OCONH, CONR M1 or NR M1 CO and R M1 These are C1-C4 alkyl groups having H or 0-2 hydroxyl groups, and R is independent of each other. t1 and R t2 It is a C1-C6 alkyl group, and X M1 ' is O or NR M1(where v1 is an integer between 1 and 30, m2 is an integer between 0 and 30, n1 is an integer between 3 and 40, and r1 is 2 or 3) A UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 20, comprising at least one vinyl monomer.

[0141] 24. The above-mentioned at least one siloxane-containing vinyl monomer is tris(trimethylsilyloxy)silylpropyl(meth)acrylate, [3-(meth)acrylooxy-2-hydroxypropyloxy]propylbis(trimethylsiloxy)-methylsilane, [3-(meth)acrylooxy-2-hydroxypropyloxy]propylbis(trimethylsiloxy)butylsilane, 3-(meth)acrylooxy-2-(2-hydroxyethoxy)-propyloxy)propylbis(trimethylsiloxy)methylsilane N, 3-(meth)acrylooxy-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(trimethylsilyloxy)-silyl)propyloxy)propyl)-2-methylacrylamide, N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)-propyloxy)propyl)(meth)acrylamide, N-[tris(dimethylpropylsiloxy)silylpropyl]-(meth)acrylamide, N-[tris(dimethylphenylsiloxy)-silylpropyl](meth)acrylamide, N-[tris(dimethylethylsiloxy)-silylpropyl N,N-bis[2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)-propyloxy)propyl]-2-methyl(meth)acrylamide, N,N-bis[2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)-propyl](meth)acrylamide, N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)-propyl]-2-methyl(meth)acrylamide, 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- UV / HEVL filtering silicone hydrogel contact lenses according to Embodiment 20, comprising O-(methyl-bis-trimethylsiloxy-3-propyl)silylcarbamate, 3-(trimethylsilyl)-propyl vinylcarbonate, 3-(vinyloxycarbonylthio)-propyl-tris(trimethyl-siloxy)silane, 3-[tris(trimethylsiloxy)silyl]propyl vinylcarbamate, 3-[tris(trimethylsiloxy)silyl]propyl allylcarbamate, 3-[tris(trimethylsiloxy)silyl]propyl vinylcarbonate, or combinations thereof.

[0142] 25. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 24, wherein the bulk silicone hydrogel material comprises repeating units of at least one polysiloxane vinyl crosslinking agent.

[0143] 26. The at least one polysiloxane vinyl crosslinking agent is a dimethylsiloxane unit and a hydrophilized siloxane unit, each having one methyl substituent and one monovalent C4-C2 having 2-6 hydroxyl groups. 40 A UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 25, comprising a di-(meth)acryloyloxy-terminated polysiloxane vinyl crosslinking agent having hydrophilized siloxane units each having an organic substituent.

[0144] 27. The at least one polysiloxane vinyl crosslinking agent is of formula (G) [ka] (In the formula, Given that d2 / d1 is approximately 0.035 to 0.15, d1 is an integer between 30 and 500, and d2 is an integer between 1 and 75. X 01 is O or NR IN And R IN is hydrogen or C1~C 10 It is alkyl, R I0 is hydrogen or methyl, R I1 and R I2 This is either substituted or non-substituted C1~C 10 Alkylene divalent group or -R I4 -OR I5 - is a divalent group and is independent of R I4 and R I5 This is substitution or non-substitution C1~C 10 It is an alkylene divalent group, R I3 This is the equation (G-1) to (G-5) [ka] It is one of the monovalent groups, 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, and m4 is an integer from 2 to 5. R I6 is hydrogen or methyl, R I7 This is a C2-C6 hydrocarbon group having a valency of (m2+1), R I8 This is a C2-C6 hydrocarbon group having a valency of (m4+1), R I9 It is ethyl or hydroxymethyl, R I10 It is methyl or hydromethyl, RI11 is hydroxyl or methoxy, X I1 is a sulfur bond of -S- or a tertiary amino bond of -NR I12 -, where R I12 is C1-C1 alkyl, hydroxyethyl, hydroxypropyl or 2,3-dihydroxypropyl, X I2 is

Chemical formula

[0145] 28. The at least one polysiloxane vinyl crosslinking agent is (i) a vinyl crosslinking agent comprising 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, vinyl carbamate group, and / or (ii) a chain extension polysiloxane vinyl crosslinking agent comprising at least two polydiorganosiloxane segments and 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, vinyl carbamate group. The UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 25.

[0146] 29. The at least one polysiloxane vinyl crosslinking agent is α,ω-bis[3-(meth)acrylamidepropyl]-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)acryloxy [Cipropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylooxyisopropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylooxybutyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamideethoxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth) [Acrylamidopropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamideisopropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidebutyloxy-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)acrylamideethylamino-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidepropylamino-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamide-butylamino-2-hydroxypropyloxypropyl]terminated polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2-hydroxypropyloxy-ethoxypropyl]terminated polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2-hydroxypropyl-N-ethylaminopropyl]terminated polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2-hydroxypropyl-aminopropyl]-polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2- A UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 25, comprising a first polysiloxane vinyl crosslinking agent selected from the group consisting of hydroxypropyloxy-(polyethyleneoxy)propyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acrylooxyethylamino-carbonyloxy-ethoxypropyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acrylooxyethylamino-carbonyloxy-(polyethyleneoxy)propyl]-terminated polydimethylsiloxane, or a combination thereof.

[0147] 30. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 29, wherein the at least one hydrophilic vinyl monomer comprises 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.

[0148] 31. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 29, wherein the at least one hydrophilic vinyl monomer comprises N-vinylpyrrolidone and / or N-vinyl-N-methylacetamide.

[0149] 32. The at least one hydrophilic vinyl monomer is (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-hydroxylethyl(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 up to 1500, 2-(meth)acrylamide glycolic acid, 3-(meth)acrylamide propionic acid, 5-(meth)acrylamide pentanoic acid, 4-(meth)acrylamide butanoic acid, 3-( A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 31, comprising a hydrophilic (meth)acrylamide monomer selected from the group consisting of meth)acrylamide-2-methylbutanoic acid, 3-(meth)acrylamide-3-methylbutanoic acid, 2-(meth)acrylamide-2-methyl-3,3-dimethylbutanoic acid, 3-(meth)acrylamidehexanoic acid, 4-(meth)acrylamide-3,3-dimethylhexanoic acid, N-2-aminoethyl(meth)acrylamide, N-2-methylaminoethyl(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 up to 1500, and combinations thereof.

[0150] 33. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 31, 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.

[0151] 34. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 33, 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.

[0152] 35. The at least one hydrophilic vinyl monomer is 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 A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 34, comprising a methylene-containing pyrrolidone monomer selected from the group consisting of roridone, 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.

[0153] 36. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 35, having an oxygen permeability of at least 60 bars (at approximately 35°C) when fully hydrated.

[0154] 37. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 35, having an oxygen permeability of at least 70 bars (at approximately 35°C) when fully hydrated.

[0155] 38. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 35, having an oxygen permeability of at least 80 bars (at approximately 35°C) when fully hydrated.

[0156] 39. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 38, having an elastic modulus of about 2.0 MPa or less (at a temperature of 22°C to 28°C) when fully hydrated.

[0157] 40. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 38, having an elastic modulus of about 1.5 MPa or less (at a temperature of 22°C to 28°C) when fully hydrated.

[0158] 41. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 38, having an elastic modulus of about 1.2 MPa or less (at a temperature of 22°C to 28°C) when fully hydrated.

[0159] 42. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 38, having an elastic modulus of about 0.4 MPa to about 1.0 MPa (at a temperature of 22°C to 28°C) when fully hydrated.

[0160] 43. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 42, having a water content of approximately 15% to approximately 70% (at a temperature of 22°C to 28°C) when fully hydrated.

[0161] 44. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 42, having a water content of approximately 20% to approximately 70% (at a temperature of 22°C to 28°C) when fully hydrated.

[0162] 45. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 42, having a water content of approximately 25% to approximately 70% (at a temperature of 22°C to 28°C) when fully hydrated.

[0163] 46. ​​A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 42, having a water content of approximately 30% to approximately 65% ​​(at a temperature of 22°C to 28°C) when fully hydrated.

[0164] 47. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 46, wherein the bulk silicone hydrogel material further comprises at least one non-silicone vinyl crosslinking agent.

[0165] 48. The at least one non-silicone vinyl 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-diglycerol Di(meth)acrylate, ethylenebis[oxy(2-hydroxypropane-1,3-diyl)]di(meth)acrylate, bis[2-(meth)acryloyloxyethyl]phosphate, trimethylolpropanedi(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 A UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 47, comprising mid, 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, trimethylopropane trimethacrylate, pentaerythritol tetramethacrylate, bisphenol A dimethacrylate, allyl methacrylate, allyl acrylate, N-allyl-methacrylamide, N-allyl-acrylamide, or a combination thereof.

[0166] 49. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 48, wherein the bulk silicone hydrogel material further comprises repeating units of at least one hydrophobic non-silicone vinyl monomer.

[0167] 50. The above at least one hydrophobic non-silicone vinyl monomer is C1-C 10 A UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 49, comprising alkyl (meth)acrylate, cyclopentyl acrylate, cyclohexyl methacrylate, cyclohexyl acrylate, isobornyl (meth)acrylate, styrene, 4,6-trimethylstyrene (TMS), t-butylstyrene (TBS), trifluoroethyl (meth)acrylate, hexafluoroisopropyl (meth)acrylate, hexafluorobutyl (meth)acrylate, or a combination thereof.

[0168] 51. The bulk silicone hydrogel material comprises repeating units of at least one polysiloxane vinyl monomer, repeating units of 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, repeating units of at least one non-silicone vinyl crosslinking agent, C1-C 10A UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 27, comprising repeating units of at least one hydrophobic non-silicone vinyl monomer selected from the group consisting of alkyl (meth)acrylate, cyclopentyl acrylate, cyclohexyl methacrylate, cyclohexyl acrylate, isobornyl (meth)acrylate, styrene, 4,6-trimethylstyrene (TMS), t-butylstyrene (TBS), trifluoroethyl (meth)acrylate, hexafluoroisopropyl (meth)acrylate, hexafluorobutyl (meth)acrylate, and combinations thereof.

[0169] 52. The UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 51, wherein the at least one hydrophilic N-vinylamide monomer is N-vinylpyrrolidone and / or N-vinyl-N-methylacetamide, the at least one hydrophobic non-silicone vinyl monomer is methyl methacrylate, and the at least one non-silicone vinyl crosslinking agent includes ethylene glycol di-(meth)acrylate, diethylene glycol di-(meth)acrylate, triethylene glycol di-(meth)acrylate, tetraethylene glycol di-(meth)acrylate, glycerol di-(meth)acrylate, triallyl isocyanurate, allyl methacrylate, or a combination thereof.

[0170] 53. A UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 1 to 18, wherein the dry bulk silicone hydrogel material comprises at least 90% by weight of (a) at least one hydrophilic (meth)acrylamide monomer as the at least one hydrophilic vinyl monomer, (b) at least one siloxane-containing (meth)acrylamide monomer as the at least one siloxane-containing vinyl monomer, and (c) repeating units of the at least one polysiloxane vinyl monomer.

[0171] 54. The at least one hydrophilic (meth)acrylamide monomer is (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-hydroxylethyl(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-4-hydroxybutyl(meth)acrylamide, N,N-bis(2-hydroxyethyl)(meth)acrylamide, N-tris(hydroxymethyl)methyl(meth)acrylamide, 2-(meth)acrylamide glycolic acid, 3-(meth)acrylamide propionic acid, 4-(meth)acrylamide butanoic acid, 3-(meth)acrylamide-2-methylbutanoic acid, 3-(meth)acrylamide-3-methylbutanoic acid, 2-(meth)acrylamide-2-methyl-3,3-dimethylbutanoic acid, 5-(meth)acrylamide pentanoic acid, 3-(meth)acrylamide hexanoic acid, 4-(meth)acrylamide-3,A UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 53, comprising 3-dimethylhexanoic acid, (3-(meth)acrylamidephenyl)boronic acid, 3-((3-methacrylamidepropyl)dimethylammonio)-propane-1-sulfonate, 3-((3-acrylamidepropyl)dimethylammonio)propane-1-sulfonate, 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, poly(ethylene glycol)ethyl(meth)acrylamide having a number average molecular weight of up to 700, methoxy-poly(ethylene glycol)ethyl(meth)acrylamide having a number average molecular weight of up to 700, or a combination thereof.

[0172] 55. The UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 53, wherein the at least one hydrophilic (meth)acrylamide monomer includes N,N-dimethyl(meth)acrylamide, N-ethyl(meth)acrylamide, N-2-hydroxyethyl(meth)acrylamide, N-3-hydroxypropyl(meth)acrylamide, N-2-hydroxypropyl(meth)acrylamide, N-2,3-dihydroxypropyl(meth)acrylamide, (meth)acrylamide, N-(2-aminoethyl)(meth)acrylamide, N-(3-aminopropyl)(meth)acrylamide, or a combination thereof.

[0173] 56. The UV / HEVL filtering silicone hydrogel contact lens according to Embodiment 53, wherein the at least one hydrophilic (meth)acrylamide monomer comprises N,N-dimethyl(meth)acrylamide.

[0174] 57. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 53 to 56, wherein the at least one siloxane-containing (meth)acrylamide monomer comprises a (meth)acrylamide monomer containing a tris(trialkylsiloxy)silyl group.

[0175] 58. (Meth)acrylamide monomers containing a tris(trialkylsiloxy)silyl group include N-[tris(trimethylsiloxy)silylpropyl](meth)acrylamide, N-[tris(dimethylethylsiloxy)-silylpropyl](meth)acrylamide, N-[tris(dimethylpropylsiloxy)silylpropyl]acrylamide, N-[tris(dimethylphenyl-siloxy)silylpropyl](meth)acrylamide, and N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)-propyl)-2-methyl UV / HEVL filtering silicone hydrogel contact lenses according to Embodiment 57, which are cylacrylamide, N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl)acrylamide, N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl]-2-methylacrylamide, N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl]acrylamide, or a combination thereof.

[0176] 59. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 53 to 56, wherein the at least one siloxane-containing (meth)acrylamide monomer comprises a (meth)acrylamide monomer containing a bis(trialkylsilyloxy)alkylsilyl group.

[0177] 60. The UV / HEVL filtering silicone hydrogel contact lens according to any one of embodiments 53 to 56, wherein the at least one siloxane-containing (meth)acrylamide monomer comprises a (meth)acrylamide monomer containing a polysiloxane segment having 2 to 20 siloxane units.

[0178] 61. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 53 to 60, wherein the at least one polysiloxane vinyl crosslinking agent includes α,ω-(meth)acrylooxy-terminated polydimethylsiloxane, α,ω-(meth)acrylamide-terminated polydimethylsiloxane, α,ω-vinylcarbonate-terminated polydimethylsiloxane, α,ω-vinylcarbamate-terminated polydimethylsiloxane, bis-3-methacryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane, 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 diamino-functionalized polydimethylsiloxane, reaction products of azulactone-containing vinyl monomer and dihydroxyl-functionalized polydimethylsiloxane, or combinations thereof.

[0179] 62. The UV / HEVL filtering silicone hydrogel contact lens according to any one of Embodiments 53 to 60, wherein the at least one polysiloxane vinyl crosslinking agent comprises (1) a vinyl crosslinking agent comprising one sole polydiorganosiloxane segment and two terminal ethylenically unsaturated groups selected from the group consisting of (meth)acryloyloxy, (meth)acryloylamino, vinyl carbonate, and vinyl carbamate groups, and / or (2) a chain-extended polysiloxane vinyl crosslinking agent comprising at least two polydiorganosiloxane segments and a covalent linker, the covalent linker between each pair of polydiorganosiloxane segments and two terminal ethylenically unsaturated groups selected from the group consisting of (meth)acrylooxy, (meth)acryloylamino, vinyl carbonate, and vinyl carbamate groups.

[0180] 63. The at least one polysiloxane vinyl crosslinking agent is α,ω-bis[3-(meth)acrylamidepropyl]-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)acryloxy [Cipropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylooxyisopropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylooxybutyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamideethoxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth) [Acrylamidopropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamideisopropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidebutyloxy-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)acrylamideethylamino-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidepropylamino-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamide-butylamino-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2-hydroxypropyloxy-ethoxypropyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2-hydroxypropyl-N-ethylaminopropyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2-hydroxypropyl-aminopropyl]-polydimethylsiloxane, α,ω-bis[(meth)acryloxy-2-hydroxypropyl A UV / HEVL filtering silicone hydrogel contact lens according to any one of embodiments 53 to 60, comprising a first polysiloxane vinyl crosslinking agent selected from the group consisting of propyloxy-(polyethyleneoxy)propyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acrylooxyethylamino-carbonyloxy-ethoxypropyl]-terminated polydimethylsiloxane, α,ω-bis[(meth)acrylooxyethylamino-carbonyloxy-(polyethyleneoxy)propyl]-terminated polydimethylsiloxane, or a combination thereof.

[0181] 64. A method for manufacturing HEVL filtering silicone hydrogel contact lenses, (I) A step of obtaining a mold having a first mold half having a first molding surface defining the front surface of a contact lens and a second mold half having a second molding surface defining the rear surface of a contact lens, wherein the first and second mold halves are configured to accept each other so that a cavity is formed between the first and second molding surfaces, (II) A step of introducing a polymerizable composition into the cavity, the polymerizable composition comprising: (1) at least one hydrophilic vinyl monomer; (2) at least one siloxane-containing vinyl monomer and / or at least one polysiloxane vinyl crosslinking agent; (3) at least one UV-absorbing vinyl monomer having UV absorption peaks at wavelengths from 280 nm and 380 nm; (4) a first HEVL-absorbing benzotriazole-containing vinyl monomer having a first HEVL absorption peak at wavelengths from 410 nm and 420 nm; (5) a second HEVL-absorbing benzotriazole-containing vinyl monomer having a second HEVL absorption peak at wavelengths from 415 nm and 425 nm; and (6) about 100 pp (3), (4), and (5) comprises a polymerizable blue dye in a concentration of m to approximately 350 ppm, (7) at least one free radical initiator in a concentration of approximately 0.2% to approximately 1.5% by weight, and (8) optionally at least one component selected from the group consisting of at least one hydrophobic non-silicone vinyl monomer, at least one non-silicone vinyl crosslinking agent, a leaching lubricant, a leaching tear stabilizer, and combinations thereof, wherein the components (3), (4), and (5) provide UV / HEVL filtering contact lenses with a UV / HEVL filtering ratio of less than 5%, UVB %T of approximately 1% or less, HEVL %T of approximately 35% or less, %T of approximately 15% or less at 410 nm, %T of approximately 60% or less at 430 nm, and %T of approximately 85% or more at 450 nm, as well as a * ≤ -5 and b * Steps include: a polymerizable composition containing an amount and ratio such that it has a color represented by ≤ +18; (III) The step of curing the polymerizable composition in a mold to form a UV / HEVL filtering silicone hydrogel contact lens precursor, and removing the UV / HEVL filtering silicone hydrogel contact lens precursor from the mold, (Iv) A step of subjecting a UV / HEVL filtering silicone hydrogel contact lens precursor to one or more post-molding processes selected from the group consisting of extraction, hydration, surface treatment, packaging, sterilization, and combinations thereof. A method that includes this.

[0182] 65. The method according to Embodiment 64, wherein the at least one polymerizable blue dye is 1,4-bis((2-methoxyethyl)amino)-anthraquinone and / or 1,4-bis(4-(2-methacrylateoxyethyl)phenylamino)-anthraquinone.

[0183] 66. The method according to Embodiment 64 or 65, wherein 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'-methacryloxypropyl-phenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-acryloxypropylphenyl)-2H-benzotriazole, or a combination thereof.

[0184] 67. The method according to Embodiment 64 or 65, wherein the at least one UV-absorbing vinyl monomer is 2-[2'-hydroxy-5'-(2-methacrylateoxyethyl)phenyl)]-2H-benzotriazole.

[0185] 68. The method according to any one of Embodiments 64 to 67, wherein the first HEVL-absorbed benzotriazole-containing vinyl monomer is 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole, and the second HEVL-absorbed benzotriazole-containing vinyl monomer is 2-[2'-hydroxy-3'-tert-butyl-5'-(3'-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole.

[0186] 69. The method according to any one of embodiments 64 to 68, wherein the polymerizable composition comprises all components (3), (4), and (5) in an amount of about 1.2% to about 3.5% by weight based on the total amount of all polymerizable components.

[0187] 70. The method according to any one of embodiments 64 to 69, wherein the weight ratio of component (4) to component (5) is about 0.25 to about 2.5.

[0188] 71. The method according to any one of embodiments 64 to 70, wherein the at least one free radical initiator is a thermal initiator, and the polymerizable composition is thermally cured.

[0189] 72. The method according to Embodiment 71, wherein the at least one hydrophilic vinyl monomer is 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, and the polymerizable composition comprises the at least one siloxane-containing vinyl monomer which is a polysiloxane vinyl monomer, the at least one polysiloxane vinyl crosslinking agent, the at least one non-silicone vinyl crosslinking agent and the at least one hydrophobic non-silicone vinyl monomer.

[0190] 73. The method according to Embodiment 72, wherein the at least one hydrophilic N-vinylamide monomer is N-vinylpyrrolidone and / or N-vinyl-N-methylacetamide, the at least one hydrophobic non-silicone vinyl monomer is methyl methacrylate, and the at least one non-silicone vinyl crosslinking agent includes ethylene glycol di-(meth)acrylate, diethylene glycol di-(meth)acrylate, triethylene glycol di-(meth)acrylate, tetraethylene glycol di-(meth)acrylate, glycerol di-(meth)acrylate, triallyl isocyanurate, allyl methacrylate, or a combination thereof.

[0191] 74. The method according to any one of embodiments 64 to 70, wherein the at least one free radical initiator is a visible light photoinitiator, and the polymerizable composition is cured with visible light having a wavelength of 450 nm to 510 nm.

[0192] 75. The method according to Embodiment 74, wherein the visible light photoinitiator is a benzoylphosphine photoinitiator, an acylgermanium photoinitiator, and / or an acyltin photoinitiator.

[0193] 76. The method according to Embodiment 74, wherein the visible light photoinitiator is an acylgermanium photoinitiator.

[0194] 77. The method according to any one of Embodiments 74 to 76, wherein the polymerizable composition comprises at least 90% by weight of (a) at least one hydrophilic (meth)acrylamide monomer as the at least one hydrophilic vinyl monomer, (b) at least one siloxane-containing (meth)acrylamide monomer as the at least one siloxane-containing vinyl monomer, and (c) repeating units of the at least one polysiloxane vinyl monomer, based on the total amount of the entire polymerizable composition.

[0195] 78. The at least one hydrophilic (meth)acrylamide monomer is (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-H Droxypropyl(meth)acrylamide, N-2,3-dihydroxypropyl(meth)acrylamide, N-4-hydroxybutyl(meth)acrylamide, N,N-bis(2-hydroxyethyl)(meth)acrylamide, N-tris(hydroxymethyl)methyl(meth)acrylamide, 2-(meth)acrylamide glycolic acid, 3-(meth)acrylamide-propionic acid, 4-(meth)acrylamide-butanoic acid, 3-(meth)acrylamide-2-methylbutanoic acid, 3-(meth)acrylamide-3-methylbutanoic acid, 2-(meth)acrylamide Lylamide-2-methyl-3,3-dimethylbutanoic acid, 5-(meth)acrylamidepentanoic acid, 3-(meth)acrylamidehexanoic acid, 4-(meth)acrylamide-3,3-dimethylhexanoic acid, (3-(meth)acrylamidephenyl)boronic acid, 3-((3-methacrylamidepropyl)dimethylammonio)propane-1-sulfonate, 3-((3-acrylamidepropyl)dimethylammonio)propane-1-sulfonate, N-2-aminoethyl(meth)acrylamide, N-2-methylaminoethyl(meth)acrylamide The method according to Embodiment 77, comprising 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, poly(ethylene glycol)ethyl(meth)acrylamide having a number average molecular weight of up to 700, methoxy-poly(ethylene glycol)ethyl(meth)acrylamide having a number average molecular weight of up to 700, or a combination thereof.

[0196] 79. The method according to Embodiment 77, wherein the at least one hydrophilic (meth)acrylamide monomer includes N,N-dimethyl(meth)acrylamide, N-ethyl(meth)acrylamide, N-2-hydroxyethyl(meth)acrylamide, N-3-hydroxypropyl(meth)acrylamide, N-2-hydroxypropyl(meth)acrylamide, N-2,3-dihydroxypropyl(meth)acrylamide, (meth)acrylamide, N-(2-aminoethyl)(meth)acrylamide, N-(3-aminopropyl)(meth)acrylamide, or a combination thereof, and more preferably N,N-dimethylacrylamide.

[0197] 80. The method according to Embodiment 77, wherein the at least one hydrophilic (meth)acrylamide monomer includes N,N-dimethyl(meth)acrylamide.

[0198] 81. The method according to any one of Embodiments 77 to 80, wherein the at least one siloxane-containing (meth)acrylamide monomer includes a (meth)acrylamide monomer containing a tris(trialkylsiloxy)silyl group.

[0199] 82. (Meth)acrylamide monomers containing a tris(trialkylsiloxy)silyl group include N-[tris(trimethylsiloxy)silylpropyl](meth)acrylamide, N-[tris(dimethylethylsiloxy)-silylpropyl](meth)acrylamide, N-[tris(dimethylpropylsiloxy)silylpropyl]acrylamide, N-[tris(dimethylphenyl-siloxy)silylpropyl](meth)acrylamide, and N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyl) The method according to Embodiment 81, wherein the acryloxy)-propyl)-2-methylacrylamide, N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl)acrylamide, N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl]-2-methylacrylamide, N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl]acrylamide, or a combination thereof.

[0200] 83. The method according to any one of Embodiments 77 to 80, wherein the at least one siloxane-containing (meth)acrylamide monomer includes a (meth)acrylamide monomer containing a bis(trialkylsilyloxy)alkylsilyl group.

[0201] 84. The method according to any one of Embodiments 77 to 80, wherein the at least one siloxane-containing (meth)acrylamide monomer comprises a (meth)acrylamide monomer containing a polysiloxane segment having 2 to 20 siloxane units.

[0202] 85. The method according to any one of Embodiments 77 to 84, wherein the at least one polysiloxane vinyl crosslinking agent includes α,ω-(meth)acrylooxy-terminated polydimethylsiloxane, α,ω-(meth)acrylamide-terminated polydimethylsiloxane, α,ω-vinylcarbonate-terminated polydimethylsiloxane, α,ω-vinylcarbamate-terminated polydimethylsiloxane, bis-3-methacryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane, 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 diamino-functionalized polydimethylsiloxane, reaction products of azulactone-containing vinyl monomer and dihydroxyl-functionalized polydimethylsiloxane, or combinations thereof.

[0203] 86. The method according to any one of Embodiments 77 to 84, wherein the at least one polysiloxane vinyl crosslinking agent comprises (1) a vinyl crosslinking agent comprising one sole polydiorganosiloxane segment and two terminal ethylenically unsaturated groups selected from the group consisting of (meth)acryloyloxy, (meth)acryloylamino, vinyl carbonate, and vinyl carbamate groups, and / or (2) a chain-extended polysiloxane vinyl crosslinking agent comprising at least two polydiorganosiloxane segments and a covalent linker, the covalent linker between each pair of polydiorganosiloxane segments and two terminal ethylenically unsaturated groups selected from the group consisting of (meth)acryloyloxy, (meth)acryloylamino, vinyl carbonate, and vinyl carbamate groups.

[0204] 87. 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)acryloxy [Cipropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylooxyisopropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylooxybutyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamideethoxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth) [Acrylamidopropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamideisopropyloxy-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidebutyloxy-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)acrylamideethylamino-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamidepropylamino-2-hydroxypropyloxypropyl]-terminated polydimethylsiloxane, α,ω-bis[3-(meth)acrylamide-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, a method according to any one of embodiments 77 to 84, comprising a first polysiloxane vinyl crosslinking agent selected from the group consisting of.,

[0205] The above disclosure will enable those skilled in the art to practice the invention. Various modifications, variations and combinations can be made to the various embodiments described herein. To better enable the reader to understand a particular embodiment and its advantages, reference to the following examples is proposed. The specification and examples are intended to be considered illustrative.,

Examples

[0206] Example 1 Measurement of oxygen permeability coefficient Unless otherwise specified, the oxygen permeability (Dk / t), intrinsic (or edge-corrected) oxygen permeability coefficient (Dk i or Dk c ) of the lens and lens material is measured according to the procedure described in ISO 18369-4.,

[0207] Equilibrium moisture content The equilibrium water content (EWC) of the contact lens is measured as follows.,

[0208] The amount of water (expressed as a weight percentage) present in a hydrated hydrogel contact lens, fully equilibrated in physiological saline, is measured at room temperature. The lenses are quickly stacked, wiped with a cloth, and then the lens stack is transferred to an aluminum pan on an analytical balance. Typically, there are 5 lenses per sample pan. The hydrated weight of the pan + lenses is recorded. The pan is covered with aluminum foil. The pan is dried in a laboratory oven at 100±2°C for 16-18 hours. The pan + lenses is removed from the oven and cooled in a desiccator for at least 30 minutes. Only one pan is removed from the desiccator, and the aluminum foil is discarded. The pan + dried lens sample is weighed on an analytical balance. Repeat for all pans. The wet and dry weights of the lens sample can be calculated by subtracting the weight of the empty weighing pan.

[0209] modulus of elasticity The elastic modulus of a contact lens is measured using the MTS Insight instrument. The contact lens is first cut into 3.12 mm wide strips using a Precision Concept two-stage cutter. Five thickness values ​​are measured within a gauge length of 6.5 mm or less. The strips are mounted on the instrument grip and immersed in PBS (phosphate-buffered saline) at a controlled temperature of 21 ± 2°C. Typically, a 5N load cell is used for the test. A constant force and velocity are applied to the sample until it breaks. Force and displacement data are collected using TestWorks software. The elastic modulus value is calculated by TestWorks software and is the slope or tangent of the stress-to-strain curve near zero elongation in the elastic deformation region.

[0210] Transmittance The contact lens is manually placed in a specially manufactured sample holder that maintains the lens shape as if it were 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. 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 for this measurement. Percentage transmission spectra are collected in the wavelength range of 250-800 nm, and %T values ​​are collected at 1.0 nm intervals. This data is transferred to an Excel spreadsheet and used to determine whether the lens matches Class 1 UV absorbance. The transmittance is calculated using the following formula: UVA%T=315nm~380nm average % transmittance x 100 UVB%T=280nm~315nm average % transmittance x 100 HEVL%T=380nm~450nm average % transmittance x 100.

[0211] chemicals CE-PDMS has three polydimethylsiloxane (PDMS) segments linked between two PDMS segments via diurethane bonds, and two urethane bonds located between one terminal methacrylate group and one PDMS segment, respectively, and is a polysiloxane vinyl crosslinking agent (H) prepared in a manner similar to that described in Example 2 of U.S. Patent No. 9,315,669. 1The following are abbreviations: Mw = 10.1K (determined by NMR spectroscopy), TRIS-Am represents N-[tris(trimethylsiloxy)-silylpropyl]acrylamide, MCR-M07 represents monomethacrylate-terminated butyl-terminated polydimethylsiloxane (Mw: 600-800 Daltons), MMA represents methyl methacrylate, NVP represents N-vinylpyrrolidone, EGMA represents ethylene glycol methyl ether methacrylate, TEGDMA represents triethylene glycol dimethacrylate, AMA represents allyl methacrylate, DMA represents N,N-dimethylacrylamide, L-PEG2000 represents N-(carbonylmethoxypolyethylene glycol-2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine, sodium salt, and DMPC represents 1,2-dimyristoyl L-sn-glycero-3-phosphocholine, H-TEMPO represents 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl, Norbloc represents 2-[2'-hydroxy-5'-(2-methacrylateoxyethyl)phenyl)]-2H-benzotriazole from Aldrich, PrOH represents n-propanol, UV28 represents 2-{2'-hydroxy-3'-tert-butyl- UV23 represents 5'-[3'-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole, UV23 represents 2-[2'-hydroxy-3'-tert-butyl-5'-(3'-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole, and RB247 represents 1,4-bis((2-methacryloyloxyethyl)amino)-anthraquinone (Reactive Blue 247) represents VAZO64, 2,2'-dimethyl-2,2'-azodipropiononitrile, BMBDE-Ge represents bis(4-methoxybenzoyl)diethylgermanium, DBDE-Ge represents dibenzoyldiethylgermanium, TEB-Ge represents tetrakis(2-ethylbenzoyl)germanium, TTMB-Sn represents tetrakis(2,4,6-trimethylbenzoyl)stannane, MEK represents methyl ethyl ketone, and PBS has a pH of 7.2±0.2 at 25°C, approximately 0.The table shows phosphate-buffered saline containing 0.44 wt% NaH2PO4·H2O, approximately 0.388 wt% Na2HPO4·2H2O, approximately 0.79 wt% NaCl, and 98.78 wt% water. "G1" represents the di-methacryloyloxypropyl-terminated polysiloxane (Mn approximately 7.5-8.1 kg / mol, OH content approximately 1.25-1.55 mol / g) of formula (A) shown below. [ka]

[0212] Example 2 In this example, the three HEVL-absorbing vinyl monomers listed in Table 1 are used. [ka] It can be represented by a structural formula.

[0213] [Table 1]

[0214] Table 1 shows that by changing the electron-withdrawing or electron-donating ability of substituents R on the aromatic ring, the HEVL absorption peak of HEVL-absorbing vinyl monomers can be shifted to longer wavelengths, thereby increasing their solubility.

[0215] The effect of changes in the electron-withdrawing or electron-donating ability of substituents on the absorption peak can be expressed using linear free energy relations, particularly the Hammett equation, as has been reported (Jaffe, HHChem. Rev., 1953, 53, 191). Table 1 shows the correlation between empirical substituent parameters (σ) and the shift in the absorbance peak. Higher electron-withdrawing ability corresponds to a larger red shift.

[0216] It has also been reported that there is a correlation between lower melting points and compound solubility (Bathori, N.B. Acta Cryst., 2014, A70, C990). By changing the R group from -Cl to -CF3, the absorbance shifts due to the greater electron-withdrawing ability, and the solubility increases due to the decreased ability of the compound to crystallize because of the bulky -CF3 group. Table 1 also shows the solubility of these monomers in 1-propanol. UV23 appears to be a good candidate as the -CF3 group further red-shifts the absorbance and significantly improves the solubility.

[0217] Figure 1 shows the UV / Vis transmittance (A) and absorption spectra of dilute solutions (in PrOH) of UV29, UV28 or UV23 (40 ppm) measured in a 1 cm cell.

[0218] Example 3 Preparation of lens formulations Two lens formulations are prepared by placing AMA, TEGDMA, MCR-M07, G1, NVP, MMA, EGMA, Norbloc, UV28 (or UV23), RB247, VAZO64 and t-AA (tert-amyl alcohol) in a clean bottle and mixing at 600 rpm for 30 minutes at room temperature using a stir bar. After all solids are dissolved, the formulation is filtered using a 2.7 μm GMF filter.

[0219] Formulation 3-1 (unit: parts by weight): AMA (0.1), TEGDMA (0.4), MCR-M07 (34), G1 (6), NVP (40), MMA (10), EGMA (10), Norbloc (1.8), UV28 (1.5), RB247 (0.015), VAZO64 (0.5) and t-AA (1).

[0220] Formulation 3-2 (unit: parts by weight): AMA (0.1), TEGDMA (0.4), MCR-M07 (34), G1 (6), NVP (40), MMA (10), EGMA (10), Norbloc (1.8), UV23 (1.5), RB247 (0.025), VAZO64 (0.5) and t-AA (1).

[0221] Both formulations remain homogeneous for several days.

[0222] Preparation of PAA aqueous solution An aqueous solution of polyacrylic acid (PAA) is prepared by adding an appropriate amount of PAA to water (distilled or deionized water). After the PAA is completely dissolved, the pH is adjusted to approximately 2 by adding approximately 1.85% formic acid to the PAA aqueous solution. The target concentration of PAA is approximately 0.1% by weight. The prepared PAA aqueous solution is filtered to remove any particulate matter or impurities.

[0223] Phosphate-buffered saline (PBS) Phosphate-buffered saline is prepared by dissolving NaH2PO4·H2O and Na2HPO4·2H2O in a predetermined amount of purified water (distilled or deionized) to have the following composition: approximately 0.044 w / w% NaH2PO4·H2O, approximately 0.388 w / w / % Na2HPO4·2H2O, and approximately 0.79 w / w% NaCl.

[0224] In-package coated saline (IPC saline) IPC saline is prepared as follows: Poly(AAm-co-AA)(90 / 10) partial sodium salt (Poly(AAm-co-AA)90 / 10, Mw200,000) is purchased from Polysciences, Inc. and used as received. Kymene or PAE solutions of different solid content are purchased as aqueous solutions from Ashland and used as received. 0.132% PAAm-PAA and approximately 0.11% PAE are mixed together in PBS and pretreated at 65°C for approximately 6 hours. After heat pretreatment, the IPC saline is cooled to room temperature. To prevent bioburden growth, up to 5 ppm of hydrogen peroxide can be added to the final IPC saline, and the IPC saline is filtered using a 0.22 micron membrane filter.

[0225] Preparation of UV / HEVL filtering SiHy contact lenses The lens compound is purged with nitrogen at room temperature for 30-35 minutes. The N2-purged lens compound is placed in a polypropylene mold and heat-cured under the following curing conditions: heating from room temperature to 55°C at a rate of approximately 7°C / min, holding at 55°C for approximately 30 minutes, heating from 55°C to 80°C at a rate of approximately 7°C / min, holding at 55°C for approximately 30 minutes, heating from 80°C to 100°C at a rate of approximately 7°C / min, and holding at 100°C for approximately 30 minutes. The mold is opened and the molded SiHy contact lens is removed from the mold. The SiHy contact lens is placed on a plastic tray. The tray containing the SiHy contact lens is then immersed in the PAA solution prepared above for approximately 2 hours, and then immersed in the PBS prepared above for approximately 5 minutes to 1 hour at room temperature to form the PAA-coated SiHy lens. Appropriate stirring (e.g., horizontal shaking or vertical motion) is used to ensure proper flow of the PAA solution and PBS during immersion.

[0226] Next, the PAA-coated SiHy lens prepared above is placed in a polypropylene lens packaging shell (one lens per shell) with 0.55 mL or 0.65 mL of the IPC saline prepared above (about half of the saline may be added before lens insertion). The blister is then sealed with foil and autoclaved at about 121°C for about 45 minutes to form a UV / HEVL filtering SiHy contact lens having a hydrogel coating thereon.

[0227] Characterization of UV / HEVL filtering SiHy contact lenses Figure 2 shows the UV / Vis transmission spectra of a UV / HEVL filtering SiHy lens (-3.0D, approximately 90 μm center thickness) and two commercially available SiHy lenses (both Precision1 and TOTAL1 from Alcon).

[0228] The UV / HEVL filtering SiHy lens with 1.5% UV28 (compound 3-1) has a HEVL%T of 35% and is light green with 150 ppm of RB247. The UV / HEVL filtering SiHy lens with 1.5% UV23 (compound 3-2) has a HEVL%T of 28%, but is yellower than the UV / HEVL filtering SiHy lens with 1.5% UV28, despite having a much higher concentration of blue dye (250 ppm of RB247).

[0229] Example 4 Preparation of lens formulations The eight lens formulations having the compositions shown in Table 2 were prepared by placing AMA, TEGDMA, MCR-M07, G1, NVP, MMA, EGMA, Norbloc, UV28, UV23, RB247, VAZO64, and t-AA into a clean bottle and mixing them at 600 rpm for 30 minutes at room temperature using a stirring bar. After all solids had dissolved, the formulation was filtered using a 2.7 μm GMF filter.

[0230] [Table 2]

[0231] Preparation of UV / HEVL filtering SiHy contact lenses UV / HEVL filtering SiHy contact lenses are prepared from the lens formulation prepared above, according to the procedure described in Example 3.

[0232] Characterization of UV / HEVL filtering SiHy contact lenses Figure 3 shows the UV / Vis transmission spectra of two types of UV / HEVL filtering SiHy lenses (-3.0D, approximately 90 μm center thickness) and two commercially available SiHy lenses (both Alcon Precision1 and TOTAL1).

[0233] The UV / HEVL filtering SiHy lens (formulation 4-1) with 1.25% UV28 + 0.5% UV23 has a HEVL%T of 33%, the UV / HEVL filtering SiHy lens (formulation 4-2) with 1.00% UV28 + 0.75% UV23 has a HEVL%T of 32%, the UV / HEVL filtering SiHy lens (formulation 4-3) with 1.25% UV28 + 0.75% UV23 has a HEVL%T of 29%, and the UV / HEVL filtering SiHy lens (formulation 4-4) with 1.00% UV28 + 1.00% UV23 has a HEVL%T of 29%.

[0234] Color measurement by X-rite is shown in Figure 4.

[0235] Example 5 Preparation of lens formulations Five lens formulations are prepared to have the compositions as shown in Table 3.

[0236]

Table 3

[0237] Add all the components (except BMBDE-Ge) listed in Table 3 to an amber vial. Then, add BMBDE-Ge 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 are dissolved, filter the formulation through a glass microfilter (5.0 μm Millex®-SV filter).

[0238] 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.

[0239] Preparation of in-package coating solution (IPC physiological saline). Poly(AAm-co-AA)(90 / 10) partial sodium salt (approximately 90% solids, poly(AAm-co-AA)90 / 10, Mw200,000) is purchased from Polysciences, Inc. and used as received. Polyamidoamine epichlorohydrin (PAE) (Kymene, azetidinium content 0.46 as analyzed by NMR) is purchased as an aqueous solution from Ashland and used as received. IPC saline is prepared by dissolving approximately 0.07% w / w poly(AAm-co-AA) (90 / 10) and approximately 0.10% PAE (initial azetidinium millimolar equivalent of approximately 8.8 mmol) in phosphate-buffered saline (PBS) (approximately 0.044 w / w% NaH2PO4·H2O, approximately 0.388 w / w% Na2HPO4·2H2O, approximately 0.79 w / w% NaCl) and adjusting the pH to 7.2-7.6. Next, the IPC is heat-pretreated at approximately 60°C for approximately 6 hours (heat pretreatment). During this heat pretreatment, the poly(AAm-co-AA) and PAE are partially crosslinked with each other (i.e., not all azetidinium groups of the PAE are consumed), forming a water-soluble and heat-crosslinkable hydrophilic polymer material containing azetidinium groups within 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.

[0240] Lens manufacturing The lenses are prepared by casting from the lens-forming composition prepared above in a reusable mold (half female mold made of quartz and half male mold made of glass) similar to the molds shown in Figures 1-6 of U.S. Patent Nos. 7,384,590 and 7,387,759 (Figures 1-6). 50 mW / cm 2The lens compound in the mold was cured for 30 seconds with full-intensity 452nm LED light. After demolding and lens removal, the cast contact lenses were extracted and coated by immersion in the following series of baths: three methyl ethyl ketone (MEK) baths (approximately 22 seconds, 78 seconds, and 224 seconds each), a DI water bath (56 seconds), the PAA dipping solution prepared above (44 seconds), a 50 / 50n-propanol / water bath (56 seconds), three DI water baths (56 seconds each), and then equilibrated in PBS solution.

[0241] The resulting silicone hydrogel contact lenses are packaged / sealed in polypropylene lens packaging shells (or blisters) containing 0.65 mL of IPC saline prepared above (one lens per shell), and autoclaved at 121°C for 45 minutes.

[0242] Characterization of UV / HEVL filtering SiHy contact lenses Figure 5 shows the UV / Vis transmission spectra of two UV / HEVL filtering SiHy lenses (-3.0D, approximately 90 μm center thickness) prepared from five different lens formulations.

[0243] The HEVL%T values ​​for HEVL-filtered SiHy contact lenses are reported in Table 4.

[0244] [Table 4]

[0245] The UV-vis spectrum of a lens containing 0.2% UV28 (UV / HEVL blocker) was recorded and is shown in Figure 5.

[0246] UV / HEVL filtering SiHy contact lens photostability test UV / HEVL filtering SiHy lenses (-3.0D, approximately 90 μm center thickness) prepared from lens formulation 5-1 were exposed to simulated sunlight for 1, 2, and 8 hours to evaluate their photostability (lightfastness). There was no change in the UV / Vis transmission spectrum from time zero over the 8-hour exposure period.

[0247] Example 6 We evaluate four different visible light photoinitiators to assess their efficiency in manufacturing high-quality lenses with shorter curing times.

[0248] Table 5 provides information regarding the photoinitiator used in this embodiment.

[0249] [Table 5]

[0250] Photorheology research Four lens formulations that do not contain HEVL-absorbing benzotriazole-containing vinyl monomers are prepared to have the following compositions shown in Table 6. The photorheological data for these four lens formulations are also reported in Table 6. TTMB-Sn is not soluble in the formulation at room temperature, but 40 o It is soluble in 1C. Therefore, photorheological experiments with this photoinitiator are performed at 40°C, instead of the typical 25°C (for the other three photoinitiators).

[0251] [Table 6]

[0252] BMBDE-Ge and TEB-Ge can provide the desired short curing time and G'. These are then formulated in combination with UV23 and UV28. Details of the formulations and photorheological data are shown in Table 7. The curing times and G' values ​​are nearly identical for each compound.

[0253] [Table 7]

[0254] All publications and patents cited herein are incorporated herein by reference in their entirety.

Claims

1. UV / HEVL filtering silicone hydrogel contact lenses, (1) A repeating unit of at least one hydrophilic vinyl monomer, (2) Repeating units of at least one silicone-containing vinyl monomer and / or at least one polysiloxane vinyl crosslinking agent, (3) Repeating units of at least one UV-absorbing vinyl monomer having UV absorption peaks at wavelengths from 280 nm and 380 nm, (4) Repeating units of a first HEVL-absorbing benzotriazole-containing vinyl monomer having a first HEVL absorption peak at wavelengths from 410 nm and 425 nm, (5) A repeating unit of a second HEVL-absorbing benzotriazole-containing vinyl monomer having a second HEVL absorption peak at wavelengths from 410 nm and 425 nm, wherein the wavelength of the second HEVL absorption peak is longer than the wavelength of the first HEVL absorption peak, (6) Repeating units of at least one polymerizable blue dye in a concentration of approximately 90 ppm to approximately 300 ppm The bulk silicone hydrogel material comprises the components (3), (4) and (5) present in the bulk silicone hydrogel material in amounts and ratios such that the UV / HEVL filtering contact lens has less than 5% UVA%T, about 1% or less UVB%T, about 35% or less HEVL%T, about 15% or less %T at 410 nm, about 60% or less %T at 430 nm, and about 85% or more %T at 450 nm, and the UV / HEVL filtering contact lens is a ＊ ≤ -5 and b ＊ UV / HEVL filtering silicone hydrogel contact lenses having a color represented by ≤ +18.

2. The UV / HEVL filtering silicone hydrogel contact lens according to claim 1, wherein the at least one polymerizable blue dye is 1,4-bis((2-methoxyethyl)amino)-anthraquinone and / or 1,4-bis(4-(2-methacrylateoxyethyl)phenylamino)-anthraquinone.

3. The UV / HEVL filtering silicone hydrogel contact lens according to claim 1 or 2, wherein the at least one UV-absorbing vinyl monomer includes a benzotriazole-containing vinyl monomer.

4. The UV / HEVL filtering silicone hydrogel contact lens according to claim 3, wherein 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 (Norblock), 2-[2'-hydroxy-5'-(2-acrylooxyethyl)phenyl)]-2H-benzotriazole, 2-(2'-hydroxy-5'-methacryloxypropyl-phenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-acrylooxypropylphenyl)-2H-benzotriazole, or a combination thereof.

5. The UV / HEVL filtering silicone hydrogel contact lens according to claim 3, wherein the at least one UV-absorbing vinyl monomer is 2-[2'-hydroxy-5'-(2-methacrylateoxyethyl)phenyl)]-2H-benzotriazole.

6. The UV / HEVL filtering silicone hydrogel contact lens according to any one of claims 1 to 5, wherein the first HEVL-absorbing benzotriazole-containing vinyl monomer is 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole (UV28).

7. The UV / HEVL filtering silicone hydrogel contact lens according to any one of claims 1 to 6, wherein the second HEVL-absorbing benzotriazole-containing vinyl monomer is 2-[2'-hydroxy-3'-tert-butyl-5'-(3'-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole (UV23).

8. The UV / HEVL filtering silicone hydrogel contact lens according to any one of claims 1 to 7, wherein the dry bulk silicone hydrogel material constitutes about 1.2% to about 3.5% by weight of all components (3), (4), and (5).

9. The UV / HEVL filtering silicone hydrogel contact lens according to any one of claims 1 to 8, wherein the weight ratio of component (4) to component (5) is approximately 0.25 to approximately 2.

5.

10. The at least one hydrophilic vinyl monomer is (1) an alkyl(meth)acrylamide 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) N-2-hydroxylethyl(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, glyc (3) Hydroxyl-containing acrylic monomers selected from the group consisting of cerol methacrylate, 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) 2-(meth)acrylamide glycolic acid, (meth)acrylic acid, ethylacrylic acid, 3-(meth)acrylamide propionic acid, 5-(meth)acrylamide pentanoic acid, 4-(meth)acrylamide butanoic acid, 3-(meth)acrylamide-2-methylbutanoic acid, 3-(meth)acrylamide-3-methylbutanoic acid, 2-(meth)acrylamide-2-methyl-3,3-dimethylbutanoic acid, 3-(meth)acrylamide hexanoic acid, 4-(meth)acrylamide-3,(4) A carboxyl-containing acrylic monomer selected from the group consisting of 3-dimethylhexanoic acid and combinations thereof; (5) 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, (6) N-vinylpyrrolidone 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, 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, 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-3,5N-vinylamide monomers selected from the group consisting of 7-trimethyl-2-caprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide and mixtures thereof, (6) 1-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone (7) C, １ ~C ４ Acrylic monomers having an alkoxyethoxy group, including 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, and C having a number average molecular weight of up to 1500. １ ~C ４ - Acrylic monomers selected from the group consisting of alkoxy poly(ethylene glycol) (meth)acrylate, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500 and combinations thereof, (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) ethylene glycol monoallyl ether, di(ethylene glycol) monoallyl ether, tri(ethylene glycol) monoallyl ether, tetra(ethylene glycol) monoallyl ether, poly(ethylene glycol) monoallyl ether , an allyl ether monomer selected from the group consisting of 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- A UV / HEVL filtering silicone hydrogel contact lens according to any one of claims 1 to 9, comprising: (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 combinations thereof; (11) allyl alcohol; (12) N-2-hydroxyethyl vinylcarbamate; (13) N-carboxyvinyl-β-alanine; (14) N-carboxyvinyl-α-alanine; or (15) combinations thereof.

11. The bulk silicone hydrogel material comprises repeating units of at least one siloxane-containing vinyl monomer selected from the group consisting of a vinyl monomer having a bis(trialkylsilyloxy)alkylsilyl group, a vinyl monomer having a tris(trialkylsilyloxy)silyl group, a polysiloxane vinyl monomer, 3-methacrylateoxypropylpentamethyldisiloxane, t-butyldimethyl-siloxyethyl vinyl carbonate, trimethylsilylethyl vinyl carbonate, trimethylsilylmethyl vinyl carbonate, and combinations thereof, according to any one of claims 1 to 10, for a UV / HEVL filtering silicone hydrogel contact lens.

12. The UV / HEVL filtering silicone hydrogel contact lens according to any one of claims 1 to 11, wherein the bulk silicone hydrogel material comprises repeating units of at least one polysiloxane vinyl crosslinking agent.

13. The at least one polysiloxane vinyl crosslinking agent comprises a dimethylsiloxane unit and a hydrophilized siloxane unit, each having one methyl substituent and one monovalent carbon having 2 to 6 hydroxyl groups. ４ ~C ４０ A UV / HEVL filtering silicone hydrogel contact lens according to claim 12, comprising a di-(meth)acryloyloxy-terminated polysiloxane vinyl crosslinking agent having hydrophilized siloxane units each having an organic substituent.

14. The UV / HEVL filtering silicone hydrogel contact lens according to claim 12, wherein the at least one polysiloxane vinyl crosslinking agent comprises (i) a vinyl crosslinking agent comprising one sole polydiorganosiloxane segment and two terminal ethylenically unsaturated groups selected from the group consisting of (meth)acryloyloxy, (meth)acryloylamino, vinyl carbonate, and vinyl carbamate groups, and / or (ii) a chain-extended polysiloxane vinyl crosslinking agent comprising at least two polydiorganosiloxane segments and a covalent linker, the covalent linker between each pair of polydiorganosiloxane segments and two terminal ethylenically unsaturated groups selected from the group consisting of (meth)acryloyloxy, (meth)acryloylamino, vinyl carbonate, and vinyl carbamate groups.

15. A UV / HEVL filtering silicone hydrogel contact lens according to any one of claims 1 to 14, having, when fully hydrated, an oxygen permeability of at least 60 bars (at about 35°C), an elastic modulus of about 1.5 MPa or less (at a temperature of 22°C to 28°C), a water content of about 15% to about 70% (at a temperature of 22°C to 28°C), or a combination thereof.

16. The UV / HEVL filtering silicone hydrogel contact lens according to any one of claims 1 to 15, wherein the bulk silicone hydrogel material further comprises repeating units of at least one non-silicone vinyl crosslinking agent and repeating units of at least one hydrophobic non-silicone vinyl monomer.

17. A method for manufacturing HEVL filtering silicone hydrogel contact lenses, (I) A step of obtaining a mold having a first mold half having a first molding surface defining the front surface of a contact lens and a second mold half having a second molding surface defining the rear surface of the contact lens, wherein the first and second mold halves are configured to accept each other so that a cavity is formed between the first and second molding surfaces, (II) introducing the curable composition into the cavity, wherein the curable composition comprises: (1) at least one hydrophilic vinyl monomer; (2) at least one siloxane-containing vinyl monomer and / or at least one polysiloxane vinyl crosslinking agent; (3) at least one UV-absorbing vinyl monomer having a UV absorption peak at wavelengths from 280 nm and 380 nm; (4) a first HEVL-absorbing benzotriazole-containing vinyl monomer having a first HEVL absorption peak at wavelengths from 410 nm and 420 nm; (5) a second HEVL-absorbing benzotriazole-containing vinyl monomer having a second HEVL absorption peak at wavelengths from 415 nm and 425 nm; (6) a curable blue dye from about 100 ppm to about 350 ppm; (7) at least one free radical initiator from about 0.2 wt% to about 1.5 wt%; and (8) optionally, at least one component selected from the group consisting of at least one hydrophobic non-silicone vinyl monomer, at least one non-silicone vinyl crosslinking agent, a leachable lubricant, a leachable tear stabilizer, and combinations thereof, wherein components (3), (4), and (5) are present in the curable composition in amounts and ratios such that the UV / HEVL filtering contact lens has less than 5% UVA %T, about 1% or less UVB %T, about 35% or less HEVL %T, about 15% or less %T at 410 nm, about 60% or less %T at 430 nm, about 85% or more %T at 450 nm, and a ＊ ≦ -5 and b ＊ ≦ +18, and the step of being present in the curable composition in amounts and ratios such that the color is represented by (III) The steps of curing the polymerizable composition in the mold to form a UV / HEVL filtering silicone hydrogel contact lens precursor, and removing the UV / HEVL filtering silicone hydrogel contact lens precursor from the mold, (iv) The step of subjecting the UV / HEVL filtering silicone hydrogel contact lens precursor to one or more post-molding processes selected from the group consisting of extraction, hydration, surface treatment, packaging, sterilization and combinations thereof. A method that includes this.

18. The at least one polymerizable blue dye is 1,4-bis((2-methoxyethyl)amino)-anthraquinone and / or 1,4-bis(4-(2-methacryloxyethyl)phenylamino)-anthraquinone, and the at least one UV-absorbing vinyl monomer is 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 (Norblock), 2-[2'-hydroxy-5'-(2-acryloxyethyl)phenyl)]-2H-benzotriazole The method according to claim 17, comprising 2-(2'-hydroxy-5'-methacryloxypropyl-phenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-acryloyloxypropylphenyl)-2H-benzotriazole, or a combination thereof, wherein the first HEVL-absorbing benzotriazole-containing vinyl monomer is 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole (UV28), and the second HEVL-absorbing benzotriazole-containing vinyl monomer is 2-[2'-hydroxy-3'-tert-butyl-5'-(3'-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole (UV23).

19. The method according to claim 17 or 18, wherein the polymerizable composition contains all components (3), (4), and (5) in an amount of about 1.2% to about 3.5% by weight relative to the total amount of all polymerizable components, and the weight ratio of component (4) to component (5) is about 0.25 to about 2.

5.

20. The method according to any one of claims 17 to 19, wherein the at least one free radical initiator is a thermal initiator, and the polymerizable composition is thermally cured.

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