Contact lens having a lubricious coating thereon

Abstract

The present invention relates generally to a soft contact lens comprising a hydrogel lens body and a coating of a hydrophilic copolymer thereon, and to a method of producing the same. The hydrogel lens body comprises or is made of a polymeric material having 1,2-diol and / or 1,3-diol moieties, and the hydrophilic copolymer comprises arylboronate-containing repeating units each having a boronic acid group. The coating is covalently attached to the hydrogel lens body by cyclic boronate linkages each formed between one boronic acid group and one 1,2-diol or 1,3-diol group. The soft contact lens has a surface lubricity higher than that of the lens body.

Description

[0001] This application is a divisional application of application number 201980006769.5. TECHNICAL FIELD

[0002] The present invention relates to soft contact lenses each having a lubricious coating thereon. In addition, the present invention provides a method for manufacturing such contact lenses, an aqueous solution for forming a lubricious coating on a hydrogel contact lens, and an ophthalmic product containing the soft contact lenses of the present invention. BACKGROUND

[0003] Most commercially available non-silicone hydrogel contact lenses are produced according to conventional cast-molding techniques involving the use of disposable plastic molds and a mixture of vinylic monomers and crosslinking agents. There are several drawbacks with conventional cast-molding techniques. For example, the traditional cast-molding manufacturing process often includes lens extraction, where unpolymerized monomers must be removed from the lens by using organic solvents. The use of organic solvents can be expensive and not environmentally friendly. In addition, disposable plastic molds inherently have unavoidable dimensional variations because, during the injection molding process of the plastic mold, fluctuations in mold dimensions can occur due to fluctuations in the production process (temperature, pressure, material properties), and also because the resulting mold can undergo non-uniform shrinkage after injection molding. These dimensional variations in the mold can result in fluctuations in the parameters of the contact lens to be produced (peak refractive index, diameter, base curve, center thickness, etc.) and in low fidelity in replicating complex lens designs.

[0004] The above-described drawbacks encountered in conventional cast-molding techniques can be overcome by using the so-called Lightstream Technology TM (Alcon), which involves (1) lens-forming compositions that are essentially free of monomers and comprise essentially purified water-soluble polyvinyl alcohol prepolymers having ethylenically unsaturated groups, (2) reusable molds produced with high precision, and (3) curing under spatial confinement of actinic radiation (e.g., UV or visible light), as described in U.S. Patent Nos. 5,508,317, 5,583,163, 5,789,464, 5,849,810, 6,800,225, and 8,088,313. Because of the use of reusable, high-precision molds, contact lenses produced according to the Lightstream Technology TM (e.g., AquaComfort Non-silicone hydrogel lenses produced can have high consistency and high fidelity to the initial lens design. Furthermore, due to the short curing time, high productivity, and the absence of lens extraction, lenses with high optical quality can be produced at relatively low cost and in an environmentally friendly manner because water is used as a solvent for preparing the lens formulation. However, despite AquaComfort Lenses have good optical quality and good surface wettability, but they can not have the desired surface lubricity for ensuring superior wearing comfort.

[0005] Thus, there is still a need for new hydrogel contact lenses, in particular PVA-based hydrogel contact lenses, having superior surface lubricity, as well as methods capable of producing such contact lenses. SUMMARY

[0007] In one aspect, the present invention provides a soft contact lens comprising a hydrogel lens body and a coating thereon, wherein the hydrogel lens body comprises or is made of a polymeric material having 1,2-diol and / or 1,3-diol moieties, wherein the coating comprises a layer of a hydrophilic copolymer comprising (a) arylboronate-containing repeating units each having a boronic acid group and (b) repeating units of at least one hydrophilic vinylic monomer, wherein the coating is covalently attached to the hydrogel lens body by linkages each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material. The soft contact lens has a surface lubricity better than that of the surface of the hydrogel lens body.

[0008] In another aspect, the present invention provides a method for producing a soft contact lens, the method comprising the steps of: (1) obtaining a preformed hydrogel contact lens, wherein the preformed hydrogel contact lens comprises or is made of a polymeric material having 1,2-diol and / or 1,3-diol moieties; (2) contacting the preformed hydrogel contact lens with an aqueous solution of a hydrophilic copolymer comprising (a) arylboronate-containing repeating units each having a boronic acid group and (b) repeating units of at least one hydrophilic vinylic monomer for a period of time to allow a layer (or coating) of the hydrophilic copolymer to be covalently attached to the preformed hydrogel contact lens by linkages each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material.

[0009] In yet another aspect, the present application provides a method for treating, storing or packaging an aqueous solution comprising a polymeric material comprising 1,2-diol and 1,3-diol moieties or made therefrom, the aqueous solution comprising one or more buffers in an amount sufficient to maintain a pH from about 6 to about 8 and a hydrophilic copolymer comprising (a) repeating units each having an arylboronate-containing repeating unit of a boronic acid and (b) repeating units of at least one hydrophilic vinylic monomer, wherein the hydrophilic copolymer is capable of being covalently attached to the hydrogel contact lens by a linkage each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material, thereby forming a hydrophilic copolymer layer or coating on the hydrogel contact lens.

[0010] In another aspect, the present application provides an ophthalmic product comprising a sealed and sterile package comprising a packaging solution and a soft hydrogel contact lens that has been immersed in and autoclaved in the packaging solution in the sealed package, wherein the packaging solution has a pH from about 6.0 to about 8.0, a tonicity from about 200 to about 450 mOsm / kg, and a viscosity up to about 5.0 centipoise at 25 °C, wherein the soft contact lens comprises a hydrogel lens body and a coating thereon, wherein the hydrogel lens body comprises a polymeric material having or made from 1,2-diol and 1,3-diol moieties, wherein the coating comprises a hydrophilic copolymer layer, the hydrophilic copolymer comprising (a) repeating units each having an arylboronate-containing repeating unit of a boronic acid and (b) repeating units of at least one hydrophilic vinylic monomer, wherein the coating is covalently attached to the hydrogel lens body by a linkage each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material. SUMMARY

[0011] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as is commonly understood by one of ordinary skill in the art to which this application belongs. Generally, the nomenclature used herein and the laboratory procedures are well-known and commonly employed in the art. Conventional methods are used for these procedures, such as those provided in the art and various general references. Where a term is provided in the singular, the inventors also contemplate the plural of that term. The nomenclature used herein and the laboratory procedures described below are those well-known and commonly employed in the art.

[0012] As used herein, "about" means that the number called "about" includes the recited number plus or minus 1-10% of that recited number.

[0013] "Optional" or "optionally" means that the subsequently described event or circumstance can or can not occur, and that the description includes instances where the event or circumstance occurs and instances where it does not.

[0014] "Contact lens" means a structure that can be placed on or in the eye of the wearer. A contact lens can correct, improve, or change the vision of the wearer, but is not necessarily so.

[0015] "Soft contact lens" means a contact lens having an elastic modulus (i.e., Young's modulus) of less than 2.5 MPa.

[0016] As used in this application, the term "hydrogel lens body" or "body material" with respect to a soft contact lens interchangeably means a layer of hydrogel material having the three-dimensional shape of a soft contact lens and including a central curved plane (which divides the contact lens into two portions, one containing the front surface and the other containing the back surface) and having a variable thickness.

[0017] As used in this application, the term "hydrogel" or "hydrogel material" means a crosslinked polymeric material that is insoluble in water, but when fully hydrated, is capable of containing at least 10 weight percent of water in its three-dimensional polymeric network (i.e., polymer matrix). The hydrogel material can be a non-silicone hydrogel material (which theoretically contains no silicone whatsoever) or a silicone hydrogel material (which is a hydrogel material containing silicone).

[0018] "Ethylene-based monomer" means a compound having a single ethylenically unsaturated group.

[0019] The term "soluble" with respect to a compound or material in a solvent means that the compound or material is soluble in the solvent at room temperature (i.e., from about 20°C to about 30°C) to give a solution having a concentration of at least about 0.1% by weight.

[0020] The term "insoluble" with respect to a compound or material in a solvent means that the compound or material is soluble in the solvent at room temperature (as defined above) to give a solution having a concentration of less than 0.005% by weight.

[0021] The term "ethylenically unsaturated group" is used herein in a broad sense and is intended to encompass any group containing at least one >C=C< group. Exemplary ethylenically unsaturated groups include, but are not limited to, (meth)acryloyl allyl, vinyl (-CH=CH2), 1 -methylvinyl styryl, or the like.

[0022] The term "(meth)acrylamide" means a methyl acrylamide and / or an acrylamide.

[0023] The term "(meth)acrylate" means methacrylate and / or acrylate.

[0024] As used herein, "hydrophilic vinylic monomer" means a vinylic monomer that can polymerize to form a homopolymer that is water soluble or can absorb at least 10 weight percent water.

[0025] "Hydrophobic vinylic monomer" means a vinylic monomer that can polymerize to form a homopolymer that is insoluble in water and can absorb less than 10 weight percent water.

[0026] "Acrylic monomer" means a vinylic monomer having one unique (meth)acryloyl group.

[0027] As used in this application, the term "macromonomer" or "prepolymer" means a medium and high molecular weight compound or polymer containing two or more ethylenically unsaturated groups. Medium molecular weight and high molecular weight typically mean an average molecular weight greater than 700 Daltons.

[0028] As used in this application, the term "vinylic crosslinker" means a compound having at least two ethylenically unsaturated groups. "Vinylic crosslinker" means a vinylic crosslinker having a molecular weight of about 700 Daltons or less.

[0029] As used in this application, the term "polymer" means a material formed by polymerization / crosslinking of one or more monomers or macromonomers or prepolymers.

[0030] As used in this application, the term "molecular weight" of a polymeric material, including monomeric or macromonomeric materials, means weight average molecular weight, unless specifically indicated otherwise or unless the test conditions indicate otherwise.

[0031] The term "alkyl" means a monovalent radical obtained by removing a hydrogen atom from a straight chain or branched alkane compound. An alkyl group forms one bond with another group in an organic compound.

[0032] The terms "alkylene divalent radical" or "alkylene di-radical" or "alkyl di-radical" interchangeably mean a divalent radical obtained by removing one hydrogen atom from an alkyl group. An alkylene divalent radical forms two bonds with other groups in an organic compound.

[0033] The term "alkyl tri-radical" means a trivalent radical obtained by removing two hydrogen atoms from an alkyl group. An alkyl tri-radical forms three bonds with other groups in an organic compound.

[0034] The term "alkoxy" or "alkoxyl" refers to a monovalent radical obtained by removing a hydrogen atom from the hydroxyl group of a straight-chain or branched alkyl alcohol. The alkoxy group forms a bond with one other group in an organic compound.

[0035] In the present application, the term "substituted" in relation with an alkyl diyl or an alkyl means that said alkyl diyl or said alkyl comprises at least one substituent which replaces one hydrogen atom of said alkyl diyl or said alkyl and is selected from the group consisting of a hydroxyl group (-OH), a carboxyl group (-COOH), -NH2, a mercapto group (-SH), a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 alkylthio group (alkyl sulfide), a C1-C4 acylamino group, a C1-C4 alkylamino group, a di-C1-C4 alkylamino group, a halogen atom (Br or CI), and combinations thereof.

[0036] In the present application, "arylboronate-containing vinylic monomer" means a vinylic monomer comprising one unique arylboronate group connected to its unique ethylenically unsaturated group by one bond.

[0037] In the present application, "arylboronate" group means a substituted phenyl group having one boronic acid group (i.e., -B(OH)2) and optionally one or more other groups as substituents each replacing one hydrogen atom of said phenyl group.

[0038] As used in the present application, the term "phosphorylcholine" means a monovalent zwitterionic group wherein t1 is an integer from 1 to 5, and R2, R2' and R2" are independently of each other a C1-C8 alkyl group or a C1-C8 hydroxyalkyl group.

[0039] "Initiator" means a chemical capable of initiating a free radical crosslinking / polymerization reaction.

[0040] "Spatial confinement of actinic radiation" refers to an act or process in which energy in the form of radiation is directed, e.g., through a mask or a barrier or a combination thereof, to impinge in a spatially confined manner onto a region having a well-defined peripheral boundary. Spatial confinement of UV radiation is obtained by using a mask or a barrier having a region that is transparent to the radiation (e.g., UV and / or visible light), a region that is not transparent to the radiation (e.g., UV and / or visible light) surrounding the region that is transparent to the radiation, and a projected outline of the boundary between the region that is not transparent to the radiation and the region that is transparent to the radiation, as schematically shown in the drawings of U.S. Patent Nos. 6,800,225 (Figures 1-11), and 6,627,124 (Figures 1-9), 7,384,590 (Figures 1-6), and 7,387,759 (Figures 1-6). The mask or barrier allows spatial projection of a beam of radiation (e.g., UV radiation and / or visible light radiation) having a cross-sectional profile defined by the projected outline of the mask or barrier. The projected beam of radiation (e.g., UV radiation and / or visible light radiation) limits the radiation that impinges on the lens formulation located in the path of the projected beam from the first molding surface to the second molding surface of the mold. The resulting contact lens includes a front surface defined by the first molding surface, an opposing back surface defined by the second molding surface, and a lens edge defined by the cross-sectional profile of the projected beam of UV and / or visible light (i.e., the spatial confinement of radiation). The radiation used for the crosslinking is radiant energy, especially UV radiation (and / or visible light radiation), gamma radiation, electron radiation, or thermal radiation, which is preferably in the form of a substantially parallel beam in order to achieve good confinement on the one hand and efficient use of the energy on the other hand.

[0041] The term "modulus" or "elastic modulus" with respect to a contact lens or a material means tensile modulus or Young's modulus as a measure of the stiffness of the contact lens or the material. The modulus can be measured using the method according to the ANSI Z80.20 standard. It is well known to the person skilled in the art how to determine the elastic modulus of a silicone hydrogel material or a contact lens. For example, all commercial contact lenses have reported values of the elastic modulus.

[0042] In general, the present invention relates to a method for producing soft contact lenses each comprising a hydrogel lens body and a lubricious coating covalently attached to the hydrogel lens body, the hydrogel lens body comprising or being made of a polymeric material having 1,2-diol and / or 1,3-diol moieties (e.g., a crosslinked polyvinyl alcohol or a polymeric material comprising diol-containing repeating units each having a 1,2-diol or a 1,3-diol); and to such soft contact lenses. The present invention is based, in part, on the discovery that such a hydrogel contact lens (e.g., a polyvinyl alcohol-based hydrogel contact lens) can be coated with a hydrophilic copolymer having arylboronate-containing repeating units each capable of reacting with one of the 1,2-diol or 1,3-diol moieties in the hydrogel lens body to form one reversible covalent bond (i.e., a cyclic boronate linkage), as shown in Scheme I, to attach a hydrophilic copolymer layer (or coating) to the surface of the hydrogel contact lens in a water-based coating process. The formed cyclic boronate linkage can be stable in a sealed and autoclaved lens package in the pH range of a typical lens packaging solution. The resulting hydrogel contact lens having a hydrophilic copolymer coating thereon can enhance the surface lubricity of the hydrogel contact lens. It was further discovered that the water-based coating process has no or minimal impact on the properties of the preformed hydrogel contact lens (e.g., a preformed polyvinyl alcohol-based hydrogel contact lens) so as to maintain all the beneficial attributes of the preformed hydrogel contact lens (e.g., a preformed polyvinyl alcohol-based hydrogel contact lens), such as, for example, softness, balanced water content, elongation, etc.

[0043]

[0044] In one aspect, the present invention provides a method for producing soft contact lenses, the method comprising the steps of: (1) obtaining a preformed hydrogel contact lens, wherein the preformed hydrogel contact lens comprises or is made of a polymeric material having 1,2-diol and / or 1,3-diol moieties; (2) contacting the preformed hydrogel contact lens with an aqueous solution of a hydrophilic copolymer comprising (a) arylboronate-containing repeating units each having a boronic acid and (b) repeating units of at least one hydrophilic vinylic monomer for a period of time to covalently attach a layer (or coating) of the hydrophilic copolymer to the preformed hydrogel contact lens through linkages each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material.

[0045] Any suitable preformed hydrogel contact lens can be used in the present application, so long as they comprise or are made from a polymeric material having 1,2-diol and / or 1,3-diol moieties. In one preferred embodiment, the preformed hydrogel contact lens comprises or is made from a polymeric material comprising at least 50% by moles (preferably at least 60% by moles, more preferably at least 70% by moles, even more preferably at least 75% by moles) of vinyl alcohol repeat units. In another preferred embodiment, the preformed hydrogel contact lens comprises or is made from a polymeric material comprising at least one type of diol-containing repeat unit each having one or more 1,2-diol and / or 1,3-diol moieties and having at least 5% by repeat unit equivalent (preferably at least 10%, more preferably at least 15%, even more preferably at least 20%) of 1,2-diol and 1,3-diol moieties.

[0046] According to the present application, the repeat unit equivalent percentage of 1,2-diol and 1,3-diol moieties may be calculated according to the following equation

[0047]

[0048] where "n" is the total number of different types of diol-containing repeat units, is the mole percentage of diol-containing repeat units of a particular type "i", is the number of 1,2-diol and 1,3-diol per repeat unit of each type i.

[0049] According to the present application, the mole percentage of each type of repeat unit in the polymeric material of the hydrogel contact lens can be determined based on the mole percentage of vinylic monomers or crosslinking agents that derive this type of repeat unit in the polymerization in the lens forming composition used to form the hydrogel contact lens.

[0050] According to the present application, the preformed hydrogel contact lens is a contact lens that has not undergone any surface modification after the lens forming process well known to those skilled in the art. For example, the preformed contact lens can be produced in a conventional "spin-cast mold" as described, for example, in U.S. Patent No. 3,408,429, or in a static form by full cast molding methods as described in U.S. Patent Nos. 4,347,198; 5,508,317; 5,583,463; 5,789,464; and 5,849,810, or by a button lathe style cutting as used in the manufacture of custom contact lenses. In the cast molding process, the lens formulation is typically dispensed into a disposable or reusable mold and cured (i.e., polymerized and / or crosslinked) in the mold used to manufacture the contact lens.

[0051] To produce the preformed hydrogel contact lenses to be used in the present application, the hydrogel lens formulation (composition) comprises all the necessary polymerizable components and at least one free radical initiator (photo-initiator or thermal initiator) known to those skilled in the art, provided that the hydrogel lens formulation (composition) necessarily comprises at least one polymerizable component comprising at least one 1,2-diol or 1,3-diol moiety. It should be understood that the hydrogel lens formulation can also contain other polymerizable or non-polymerizable components, such as lubricants (or so-called internal wetting agents incorporated into the lens formulation), UV absorbers, visibility tinting agents (e.g., dyes, pigments, or mixtures thereof), antimicrobial agents (e.g., preferably silver nanoparticles), bioactive agents, and combinations thereof.

[0052] The polymerizable components used to make the preformed hydrogel contact lenses are well known to those skilled in the art. Typically, the hydrogel lens formulation used to make contact lenses comprises polymerizable components selected from the group consisting of one or more hydrophilic vinylic monomers, one or more hydrophobic vinylic monomers, one or more siloxane-containing vinylic monomers, one or more vinylic crosslinkers, one or more ethylenically crosslinkable prepolymers, and combinations thereof.

[0053] The resulting preformed hydrogel contact lenses can then be subjected to extraction with an extraction solvent to remove unpolymerized components from the resulting lenses, to a hydration process, and to other post-molding processes, as known to those skilled in the art.

[0054] In a preferred embodiment, the preformed hydrogel contact lenses are polyvinyl alcohol-based hydrogel contact lenses, which are preferably obtained by polymerizing a water-soluble, actinically crosslinkable polyvinyl alcohol prepolymer comprising:

[0055] repeating units of vinyl alcohol (i.e., ) ;

[0056] repeating units of formula (I); and

[0057]

[0058] wherein:

[0059] R3may be hydrogen or C1-C6alkyl (preferably hydrogen);

[0060] R4is a C1-C6alkylene divalent radical (preferably a C1-C4alkylene divalent radical, more preferably a methylene or butylene divalent radical, even more preferably a methylene divalent radical);

[0061] R5 is hydrogen or C1-C6 alkyl (preferably hydrogen or C1-C4 alkyl, more preferably hydrogen or methyl or ethyl, even more preferably hydrogen or methyl);

[0062] R6 is The olefinic unsaturated groups, wherein q1 and q2 are independently zero or one, and R7 and R8 are independently C2-C8 alkylene divalent groups, and R9 is a C2-C8 alkenyl group.

[0063] In another preferred embodiment, R4 is a methylene divalent group, R5 is H or a C1-C4 alkyl group, R3 is H, and R6 is a group. Where q2 is 0, and R9 is vinyl ( * -CH=CH2) or 1-methylvinyl ( * -C(CH3)=CH2).

[0064] In another preferred embodiment, the polyvinyl alcohol prepolymer has a weight-average molecular weight of at least about 2,000 Daltons and contains repeating units of formula (I) ranging from about 1% to about 25% by molar, preferably from about 2% to about 15% by molar.

[0065] Water-soluble, photocrosslinkable polyvinyl alcohol prepolymers can be prepared using techniques known in the art, such as those described in U.S. Patent Nos. 5,583,163 and 6,303,687.

[0066] Preferably, with As such Known methods for purifying the polyvinyl alcohol prepolymer include precipitation with an organic solvent such as acetone, filtration and washing, extraction in a suitable solvent, dialysis, or ultrafiltration, with ultrafiltration being particularly preferred. Through these purification processes, the prepolymer can be obtained in an extremely pure form, for example, as a concentrated aqueous solution with no or at least substantially no reaction products (such as salts) and starting materials (such as non-polymer components).

[0067] The preferred purification process, ultrafiltration, can be used to... As such The process can be performed in a known manner. It is possible to repeat the ultrafiltration process, for example, from 2 to 10 times. Alternatively, ultrafiltration can be performed continuously until the desired purity is achieved. The desired purity can, in principle, be as high as desired. A suitable measure of purity is, for example, the concentration of the dissolved salt obtained as a byproduct, which can be easily determined in a known manner.

[0068] It would be advantageous for the water-soluble, actinically crosslinkable polyvinyl alcohol prepolymer to be in a substantially pure form (e.g., purified by ultrafiltration to remove most of the reactants used to form the prepolymer). Thus, after crosslinking by actinic radiation, the contact lenses can not actually require subsequent purification, such as particularly complex unpolymerized component extraction. In addition, the crosslinking can be performed in an aqueous solution, such that subsequent solvent exchange or hydration steps are unnecessary.

[0069] Preferably, the preformed polyvinyl alcohol-based hydrogel contact lens is obtained by introducing an aqueous lens forming composition comprising the above-described water-soluble, actinically crosslinkable polyvinyl alcohol prepolymer into a reusable mold and curing the aqueous lens forming composition under spatial confinement of actinic radiation.

[0070] Preferably, a reusable mold suitable for spatial confinement of radiation is used in the present application, the projected radiation (e.g., radiation from a light source comprising light in the region of 360 nm to 550 nm) beam limits the radiation (e.g., UV / visible radiation) impinging on the mixture of lens forming material located in the projected beam path from the first molding surface to the second molding surface of the reusable mold. The resulting contact lens comprises a front surface defined by the first molding surface, an opposing back surface defined by the second molding surface, and a lens edge (with sharp edges and high quality) defined by the cross-sectional profile of the projected radiation beam (i.e., spatial confinement of radiation). Examples of reusable molds suitable for spatial confinement of radiation include, but are not limited to, those disclosed in U.S. Patent Nos. 6,627,124, 6,800,225, 7,384,590, and 7,387,759.

[0071] For example, a preferred reusable mold comprises a first mold half having a first molding surface and a second mold half having a second molding surface. The two mold halves of the preferred reusable mold do not contact each other, but rather there is a thin gap having an annular design arranged between the two mold halves. The gap is in communication with the mold cavity formed between the first molding surface and the second molding surface, such that excess mixture can flow into the gap. It should be understood that a gap having any design can be used in the present application.

[0072] In preferred embodiments, at least one of the first molding surface and the second molding surface is permeable to crosslinking radiation. More preferably, one of the first molding surface and the second molding surface is permeable to crosslinking radiation, while the other molding surface is less permeable to crosslinking radiation.

[0073] The reusable mold includes a mask that is fixed, constructed, or arranged in, on, or within a half-mold having a radially permeable molding surface. The mask is opaque or has at least a lower transmittance compared to the transmittance of the radially permeable molding surface. The mask extends inward into and surrounds the mold cavity to shield all areas behind the mask except for the mold cavity.

[0074] The mask is preferably a thin chromium layer, which can be formed according to processes known, for example, photolithography and ultraviolet lithography. Other metals or metal oxides may also be suitable mask materials. If the material used for the mold or half-mold is quartz, the mask may also be coated with a protective layer (e.g., silicon dioxide).

[0075] Alternatively, the mask can be, as described in U.S. Patent No. 7,387,759, a mask ring made of a material containing a UV / visible light absorber and substantially blocking curing energy passing through it. In this preferred embodiment, the half-mold having the mask comprises a generally disk-shaped transmissive portion and a mask ring having an inner diameter adapted to fit tightly into the transmissive portion, wherein the transmissive portion is made of an optically transparent material and allows curing energy to pass through therethrough, and wherein the mask ring is made of a material containing a light-blocking agent and substantially blocks curing energy from passing through therethrough, wherein the mask ring is generally similar to a washer or dollop and has a central hole for receiving the transmissive portion, wherein the transmissive portion is pressed into the central opening of the mask ring and the mask ring is mounted within a sleeve.

[0076] Reusable molds can be made of quartz, glass, sapphire, CaF2, or cyclic olefin copolymers (such as those from Ticona GmbH of Frankfurt, Germany and Summit, New Jersey). COC grade 8007-S10 (a transparent amorphous copolymer of ethylene and norbornene), from Zeon Chemicals LP, Louisville, KY, Kentucky. and Polymethyl methacrylate (PMMA), polyoxymethylene (Delrin) from DuPont, and polyoxymethylene (GE Plastics) from GE Plastics. (polyetherimide) The mold halves are produced with a high degree of precision and reproducibility. Because of the reusability of the mold halves, they can be produced with a high expense to obtain a mold with a very high precision and reproducibility. Since the mold halves do not contact each other in the area of the lens to be produced, i.e. the mold cavity or the actual molding surface, damage caused by contact is eliminated. This ensures a high service life of the mold, which in particular also ensures a high reproducibility of the contact lenses to be produced and a high fidelity of the lens design.

[0077] In another preferred embodiment, the preformed hydrogel contact lens comprises or is made of a polymeric material comprising at least one type of diol-containing repeat unit each having one or more 1,2-diol and / or 1,3-diol moieties and having at least 5% (preferably at least 10%, more preferably at least 15%, even more preferably at least 20%) of 1,2-diol and 1,3-diol moieties by repeat unit equivalent weight. It is understood that the diol-containing repeat units can be derived in polymerization from at least one diol-containing vinylic monomer having at least one 1,2-diol and / or 1,3-diol moiety, or from at least one diol-containing vinylic crosslinker having at least one 1,2-diol and / or 1,3-diol moiety.

[0078] Any diol-containing vinylic monomer can be used in the present application, as long as they each contain at least one 1,2-diol and / or 1,3-diol moiety. Examples of preferred diol-containing vinylic monomers include, but are not limited to, N-2,3-dihydroxypropyl (meth)acrylamide, N-tris(hydroxymethyl)methyl (meth)acrylamide, 2-glucamidoethyl (meth)acrylamide, 3-glucamidopropyl (meth)acrylamide, glyceryl (meth)acrylate, glucosyl (meth)acrylate, glucosyloxyethyl (meth)acrylate, sugar acrylate monomers (disclosed in U.S. Patent Application Publication No. 2012 / 0264214 and U.S. Patent No. 4721760, among others), 3-allyloxy-1,2-propanediol, 2-allyloxymethyl-2-(hydroxymethyl)-1,3-propanediol, 2-allyloxymethyl-2-ethyl-1,3-propanediol (i.e., trimethylolpropane allyl ether), allyl a-D-mannopyranoside, allyl a-D-galactopyranoside, allyl 6-deoxyhexopyranoside, allyl 6-deoxy-2-O-methylhexopyranoside, and combinations thereof.

[0079] Any diol-containing vinylic crosslinker can be used in the present application, so long as they each contain at least one 1,2-diol and / or 1,3-diol moiety. Examples of preferred diol-containing vinylic crosslinkers include, but are not limited to, N,N'-(1,2-dihydroxyethylidene)bis-(meth)acrylamide, N,N'-(2,3-dihydroxybutylidene)bis-(meth)acrylamide, those polydimethylsiloxane vinylic crosslinkers comprising siloxane units each having a methyl substituent and one diol-containing substituent as disclosed in U.S. Patent Application Publication No. 2017 / 01666673, and combinations thereof.

[0080] According to the present application, the hydrophilic copolymer used to coat the hydrogel contact lenses of the present application must be water-soluble.

[0081] In a preferred embodiment, the hydrophilic copolymer comprises (a) from about 0.5% by mole to about 25% by mole (preferably from about 1% to about 20% by mole, more preferably from about 2% to about 18% by mole, even more preferably from about 3% to about 15% by mole) of repeating units each having an aryl-containing dihydroxyl boron-containing group of boric acid and (b) from about 75% by mole to about 99.5% by mole (preferably from about 80% to about 99% by mole, more preferably from about 82% to about 98% by mole, even more preferably from about 85% to about 97% by mole) of repeating units of at least one hydrophilic vinylic monomer, with the proviso that the sum of the mole percentages of components (a) and (b) and other components not listed above is 100%.

[0082] In another preferred embodiment, the hydrophilic copolymer comprises (a) from about 1% to about 20% by mole (preferably from about 1% to about 20% by mole, more preferably from about 2% to about 15% by mole) of repeating units each having an aryl-containing dihydroxyl boron-containing group of boric acid, (b) from about 60% to about 98% by mole (preferably from about 60% to about 97% by mole, more preferably from about 70% to about 95% by mole) of repeating units of at least one phosphorylcholine-containing vinylic monomer, and (c) from about 1% to about 20% by mole (preferably from about 2% to about 20% by mole, more preferably from about 3% to about 15% by mole) of at least one acrylic monomer unit of an acrylic monomer having from 3 to 16 (preferably from 3 to 14, more preferably from 3 to 12, even more preferably from 3 to 10) carbon atoms, with the proviso that the sum of the mole percentages of components (a), (b), and (c) and other components not listed above is 100%.

[0083] According to the present application, the mole percentage of each type of repeating unit (i.e., monomeric unit) of the hydrophilic copolymer can be determined based on the mole percentage of the vinylic monomer that derives such type of repeating unit in the polymerizable composition used to form the hydrophilic copolymer.

[0084] According to the present application, each type of aryl-dihydroxyl-boryl-containing repeating unit can be directly derived from an aryl-dihydroxyl-boryl-containing vinylic monomer, preferably from an aryl-dihydroxyl-boryl-containing vinylic monomer having formula (II)

[0085]

[0086] wherein: R1is H, NO2, F, Cl, or CF3; Q is or a monovalent radical of -CH=CH2; L is a direct bond, a C1-C4 alkylene divalent radical, a divalent radical of -Y1-C(O)-Y2-, wherein Y1is CH(OH) or a C1-C4 alkylene divalent radical, Y2is a C1-C4 alkylene divalent radical, and R o is H or a C1-C4 alkyl group.

[0087] Examples of preferred aryl-dihydroxyl-boryl-containing vinylic monomers having formula (II) include, but are not limited to, 3-vinylphenylboronic acid, 4-vinylboronic acid, 3- (meth)acrylamidophenylboronic acid, 4-(meth)acrylamidophenylboronic acid, reaction products of an amino-containing phenylboronic acid derivative with a (meth)acrylic acid halide, reaction products of an amino-containing phenylboronic acid derivative with a carboxyl-containing vinylic monomer in the presence of a carbodiimide (e.g., 1-ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDC), N,N’-dicyclohexylcarbodiimide (DCC), 1- cyclohexyl-3-(2-morpholinoethyl)carbodiimide, diisopropylcarbodiimide, or a mixture thereof) and N-hydroxysuccinimide, reaction products of a carboxyl-containing phenylboronic acid derivative with an amino-containing vinylic monomer in the presence of a carbodiimide (e.g., 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), N,N’-dicyclohexylcarbodiimide (DCC), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide, diisopropylcarbodiimide, or a mixture thereof) and N-hydroxysuccinimide, and combinations thereof.

[0088] Examples of preferred carboxyl-containing phenylboronic acid derivatives include, but are not limited to, 3-carboxyphenylboronic acid, 4-carboxyphenylboronic acid, 3- dihydroxyboronylphenylacetic acid, 4-dihydroxyboronylphenylacetic acid, 2-(4- dihydroxyboronylphenyl)-2-methylpropanoic acid, 3-(4-dihydroxyboronylphenyl)propanoic acid, 3-(3-dihydroxyboronylphenyl)propanoic acid, 5-(3- dihydroxyboronylphenyl)pentanoic acid, 5-(4-dihydroxyboronylphenyl)pentanoic acid, 4-(2-carboxyethyl)-3-nitrophenylboronic acid, 3-(3-carboxypropanoylamino)phenylboronic acid, 3-amino-3-(4-dihydroxyboronylphenyl)propanoic acid, and combinations thereof.

[0089] Examples of preferred amino-containing phenylboronic acid derivatives include, but are not limited to, 3-aminophenylboronic acid, 4-aminophenylboronic acid, 4-amino-3- nitrophenylboronic acid, 4-amino-4-fluorophenylboronic acid, 2-(aminomethyl)-5- nitrophenylboronic acid, 3-(aminomethyl)-phenylboronic acid, 3-amino-5- nitrophenylboronic acid, 3-amino-3-(4-dihydroxyboronylphenyl)propanoic acid, and combinations thereof.

[0090] Examples of preferred carboxyl-containing vinylic monomers include, but are not limited to, 2-acrylamidoglycolic acid, 3-acrylamidopropionic acid, 4-acrylamidobutanoic acid, 5- acrylamidopentanoic acid, 3-acryloyloxypropanoic acid, 4-acryloyloxybutanoic acid, 5- acryloyloxypentanoic acid, and combinations thereof.

[0091] Examples of preferred amino-containing vinylic monomers include, but are not limited to, amino-C2-C4 alkyl (meth)acrylate, C1-C3 alkylamino-C2-C4 alkyl (meth)acrylate, amino-C2-C4 alkyl (meth)acrylamide, C1-C3 alkylamino-C2-C4 alkyl (meth)acrylamide, vinyl amine, allyl amine, and combinations thereof.

[0092] Any suitable hydrophilic vinylic monomer can be used to make the hydrophilic copolymer. Examples of suitable hydrophilic vinylic monomers include, but are not limited to, carboxyl-containing vinylic monomers, primary amine-containing vinylic monomers, secondary amine-containing vinylic monomers, non-reactive hydrophilic vinylic monomers, phosphorylcholine-containing vinylic monomers, and combinations thereof.

[0093] Examples of preferred hydrophilic vinylic monomers are alkyl (meth) acrylamides (described below), hydroxyl-containing acrylic monomers (described below), amino-containing acrylic monomers (described below), carboxyl-containing acrylic monomers (described below), N-vinyl amide monomers (described below), methylene-containing pyrrolidone monomers (i.e., pyrrolidone derivatives each having a methylene group attached to the pyrrolidone ring at either the 3- or 5-position) (described below), acrylic monomers having Ci-C4alkoxyethoxy groups (described below), vinyl ether monomers (described below), allyl ether monomers (described below), phosphorylcholine-containing vinylic monomers (described below), N-2-hydroxyethyl vinyl carbamate, N-carboxy vinyl- -alanine (VINAL), N-carboxy vinyl- -alanine, and combinations thereof.

[0094] Examples of alkyl (meth) acrylamides include, but are not limited to, (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.

[0095] Examples of hydroxyl-containing acrylic monomers include, but are not limited to, N-2-hydroxyethyl (meth) acrylamide, N,N-bis(hydroxyethyl) (meth) acrylamide, N-3-hydroxypropyl (meth) acrylamide, N-2-hydroxypropyl (meth) acrylamide, 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 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.

[0096] Examples of amino-containing acrylic monomers include, but are not limited to, 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, 2- hydroxypropyl (meth)acrylate trimethylammonium hydrochloride, dimethylaminoethyl (meth)acrylate, and combinations thereof.

[0097] Examples of carboxyl-containing acrylic monomers include, but are not limited to, 2- (meth)acrylamidoglycolic acid, (meth)acrylic acid, ethylacrylic acid, propylacrylic acid, 3- (meth)acrylamidopropionic acid, 4-(meth)acrylamidobutanoic acid, 5- (meth)acrylamidopentanoic acid, 3-(meth)acryloyloxypropionic acid, 4- (meth)acryloyloxybutanoic acid, 5-(meth)acryloyloxy pentanoic acid, and combinations thereof.

[0098] Examples of preferred N-vinyl amide monomers include, but are not limited to, N-vinyl pyrrolidone (also known as N-vinyl-2-pyrrolidone), N-vinyl-3-methyl-2-pyrrolidone, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-6-methyl-2-pyrrolidone, N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, N-vinyl-5,5-dimethyl-2-pyrrolidone, N-vinyl-3,3,5-trimethyl-2-pyrrolidone, N-vinyl piperidone (also known as N-vinyl-2-piperidone), N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-5-methyl-2-piperidone, N-vinyl-6-methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone, N-vinyl-3,5-dimethyl-2-piperidone, N-vinyl-4,4-dimethyl-2-piperidone, N-vinyl caprolactam (also known as N-vinyl-2-caprolactam), N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methyl acetamide, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, and mixtures thereof. Preferably, the N-vinyl amide monomer is N-vinyl pyrrolidone, N-vinyl-N-methyl acetamide, or a combination thereof.

[0099] Examples of preferred methylene (=CH2)-containing pyrrolidone monomers include, but are not limited to, 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-iso-propyl-3-methylene-2-pyrrolidone, 1-iso-propyl-5-methylene-2-pyrrolidone, 1-n-butyl-3-methylene-2-pyrrolidone, 1-t-butyl-3-methylene-2-pyrrolidone, and combinations thereof.

[0100] Examples of preferred acrylic monomers having C1-C4-alkoxyethyl groups include, but are not limited to, 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-alkoxy poly(ethylene glycol) (meth)acrylate having a weight average molecular weight of up to 1500, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, and combinations thereof.

[0101] Examples of preferred vinyl ether monomers include, but are not limited to, ethylene glycol mono vinyl ether, di(ethylene glycol) mono vinyl ether, tri(ethylene glycol) mono vinyl ether, tetra(ethylene glycol) mono vinyl ether, poly(ethylene glycol) mono vinyl 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.

[0102] Examples of preferred allyl ether monomers include, but are not limited to, allyl alcohol, ethylene glycol mono allyl ether, di(ethylene glycol) mono allyl ether, tri(ethylene glycol) mono allyl ether, tetra(ethylene glycol) mono allyl ether, poly(ethylene glycol) mono allyl ether, ethylene glycol methyl allyl ether, di(ethylene glycol) methyl allyl ether, tri(ethylene glycol) methyl allyl ether, tetra(ethylene glycol) methyl allyl ether, poly(ethylene glycol) methyl allyl ether, and combinations thereof.

[0103] Examples of preferred phospholyl-containing vinylic monomers include, but are not limited to, (meth)acryloyloxyethyl phosphocholine (also known as MPC, or 2-((meth)acryloyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate), (meth)acryloyloxypropyl phosphocholine (also known as 3-((meth)acryloyloxy)propyl-2'-(trimethylammonio)ethyl phosphate), 4-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethyl phosphate, 2-[(meth)acryloylamino]ethyl-2'-(trimethylammonio)-ethyl phosphate, 3-[(meth)acryloylamino]propyl-2'-(trimethylammonio)ethyl phosphate, 4-[(meth)acryloylamino]butyl-2'-(trimethylammonio)ethyl phosphate, 5-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 6-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)-ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(triethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(tripropylammonio)ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(tributylammonio)ethyl phosphate, 2-((meth)acryloyloxy)propyl-2'-(trimethylammonio)-ethyl phosphate, 2-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxycarbonyl)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonyl)ethyl-2'-(trimethylammonio)-ethyl phosphate, 2-(vinylcarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(butenoyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, and combinations thereof.

[0104] Examples of preferred acrylic monomers having 3 to 16 carbon atoms include, but are not limited to, (meth)acrylic acid C1-C 12 alkyl esters, (meth)acrylic acid hydroxy-substituted C2-C 12 alkyl esters, (meth)acrylic acid carboxy-substituted C2-C 12 alkyl esters, (meth)acrylic acid NH2-substituted C2-C 12 alkyl esters, (meth)acrylic acid methylamino-substituted C2-C 12Alkyl esters, dimethylamino-substituted (meth)acrylates, C2-C 12 Alkyl esters, (meth)acrylates, ethylamino-substituted C2-C 10 Alkyl esters, diethylamino-substituted C2-C8 alkyl esters of (meth)acrylate, C2-C 12 Alkyl (meth)acrylamide, hydroxy-substituted C2-C 12 Alkyl (meth)acrylamide, carboxyl-substituted C2-C 12 Alkyl (meth)acrylamide, NH2-substituted C2-C 12 Alkyl (meth)acrylamide, methylamino-substituted C2-C 12 Alkyl (meth)acrylamide, dimethylamino-substituted C2-C 12 Alkyl (meth)acrylamide, ethylamino-substituted C2-C 10 Alkyl (meth)acrylamide, diethylamino-substituted C2-C8 alkyl (meth)acrylamide, ethylene glycol (meth)acrylate, di(ethylene glycol)(meth)acrylate, tri(ethylene glycol)(meth)acrylate, tetra(ethylene glycol)(meth)acrylate, 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 combinations thereof.

[0105] According to the present invention, the hydrophilic copolymer used for coating the hydrogel contact lenses of the present invention has a weight-average molecular weight of at least about 100,000 Daltons, preferably at least about 125,000 Daltons, more preferably at least about 250,000 Daltons, and even more preferably at least about 400,000 Daltons. It is believed that high molecular weight hydrophilic copolymers will be more suitable for forming relatively stable and thicker coatings and thus will provide higher lubricity for the coated contact lenses.

[0106] According to the present invention, contact between a pre-formed hydrogel contact lens and an aqueous solution of a hydrophilic copolymer can occur by immersing the pre-formed hydrogel contact lens in the aqueous solution or by spraying the pre-formed hydrogel contact lens with the aqueous solution. One contact method involves immersing the pre-formed hydrogel contact lens individually in a bath of aqueous solution for a period of time, or alternatively, sequentially immersing the pre-formed hydrogel contact lens in a series of baths of aqueous solution (for each bath for a fixed short period of time). Another contact method involves spraying the aqueous solution individually. However, many alternatives involve various combinations of spraying-and immersion-steps that can be designed by those skilled in the art. Preferably, the contact step is performed by immersing the pre-formed hydrogel contact lens in an aqueous solution within the lens packaging, and the aqueous solution is the packaging solution.

[0107] The aqueous solution has a pH from about 6.5 to about 9.0.

[0108] In any of the above preferred embodiments, the aqueous solution comprises from about 0.01% to about 2.5% by weight (preferably from about 0.02% to about 2.0% by weight, more preferably from about 0.05% to about 1.5% by weight, even more preferably from about 0.1% to about 1% by weight) of at least one hydrophilic copolymer (any of those described above).

[0109] The contact period is preferably at least 1 minute, preferably at least 5 minutes, more preferably at least 10 minutes, even more preferably from about 20 minutes to 5 hours.

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

[0111] The lens package is packaged in a separate package, sealed and sterilized (e.g., by autoclaving at about 120°C or higher under pressure for 30 to 90 minutes) prior to distribution to the user. Those skilled in the art will well understand how to seal and sterilize the lens package.

[0112] In preferred embodiments, the aqueous solution is a packaging solution containing at least one buffering agent and one or more other ingredients known to those skilled in the art. Examples of other ingredients include, but are not limited to, tonicity agents, surfactants, antimicrobial agents, preservatives, and lubricants (e.g., cellulose derivatives, polyvinyl alcohol, polyvinyl pyrrolidone).

[0113] The packaging solution contains a buffering agent in an amount sufficient to maintain the pH of the packaging solution within the desired range. Any known physiologically compatible buffering agent can be used. Suitable buffering agents as components of the contact lens care composition according to the present application are known to those skilled in the art. Examples are boric acid, borates (e.g. sodium borate), citric acid, citrates (e.g. potassium citrate), bicarbonates (e.g. sodium bicarbonate), TRIS (2-amino-2-hydroxymethyl-1,3-propanediol), Bis-Tris (bis-(2-hydroxyethyl)-imino-tris-(hydroxymethyl)- methane), bis-amino polyols, triethanolamine, ACES (N-(2-hydroxyethyl)-2- aminoethanesulfonic acid), BES (N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid), HEPES (4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid), MES (2-(N- morpholino)ethanesulfonic acid), MOPS (3-[N-morpholino]-propanesulfonic acid), PIPES (piperazine-N,N'-bis(2-ethanesulfonic acid), TES (N-[tris(hydroxymethyl)methyl]- 2-aminoethanesulfonic acid), salts thereof, phosphate buffers (e.g. Na2HP04, NaH2P04, and KH2P04) or mixtures thereof. Preferably, the buffering agent is a phosphate buffer, a borate buffer, or a combination thereof. The amount of each buffering agent in the packaging solution is preferably from 0.001% to 2%, preferably from 0.01% to 1% by weight; most preferably from about 0.05% to about 0.30%.

[0114] The packaging solution has a tonicity from about 200 to about 450 milliosmole (mOsm), preferably from about 250 to about 350 mOsm. The tonicity of the packaging solution can be adjusted by the addition of organic or inorganic substances that affect tonicity. Suitable ocularly acceptable tonicity agents include, but are not limited to, sodium chloride, potassium chloride, and mixtures thereof.

[0115] The packaging solution of the present application has a viscosity from about 1 centipoise to about 5 centipoise at 25°C.

[0116] In a preferred embodiment, the packaging solution comprises, preferably from about 0.01% to about 2%, more preferably from about 0.05% to about 1.5%, even more preferably from about 0.1% to about 1%, most preferably from about 0.2% to about 0.5% by weight of a hydrophilic copolymer.

[0117] In another embodiment, the method of the present application further comprises the step of sealing a preformed hydrogel contact lens immersed in the aqueous solution in the lens package and autoclaving the sealed lens package at a temperature from about 115°C to about 125°C for about 20-90 minutes.

[0118] In another aspect, the present application provides a soft contact lens comprising a hydrogel lens body and a coating thereon, wherein the hydrogel lens body comprises or is made of a polymeric material having 1,2-diol and / or 1,3-diol moieties, wherein the coating comprises a hydrophilic copolymer layer, the hydrophilic copolymer comprising (a) arylboronate-containing repeating units each having a boronic acid group and (b) repeating units of at least one hydrophilic vinylic monomer, wherein the coating is covalently attached to the hydrogel lens body by linkages each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the hydrogel lens body, wherein the soft contact lens has a surface lubricity better than that of the hydrogel lens body.

[0119] The hydrogel lens body has the 3-dimensional shape of a hydrogel contact lens. According to the present application, a preformed hydrogel contact lens (any one of those described above) becomes a hydrogel lens body after being subjected to a surface treatment for forming a coating (or layer) of a hydrophilic copolymer (any one of those described above) on the preformed hydrogel contact lens (i.e., the hydrogel lens body), as described above.

[0120] According to the present application, the soft contact lens, when fully hydrated, has a water content of preferably from about 15% to about 80% by weight, more preferably from about 30% to about 70%, an elastic modulus of from about 0.2 MPa to about 1.5 MPa (preferably from about 0.3 MPa to about 1.3 MPa, more preferably from about 0.4 MPa to about 1.1 MPa, even more preferably from about 0.5 MPa to about 1.0 MPa) at room temperature, about 22°C to 28°C, and a friction rating of about 2.5 or less (preferably about 2.0 or less, more preferably about 1.5 or less, even more preferably about 1.0 or less).

[0121] The soft contact lens of the present application can find a particular use as a daily disposable hydrogel contact lens with improved surface lubricity to provide improved wearing comfort. It is believed that such a soft contact lens has built-in wearing compliance due to the reversible nature of the cyclic boronate linkages responsible for anchoring the lubricious coating on the surface of the soft contact lens of the present application. It is believed that when the patient wears such a lens, the cyclic boronate linkages can be gradually broken over a long period of time (e.g., over 10 to 16 hours) due to pH changes and the presence of sugars in the tear fluid, and the hydrophilic copolymer can be gradually released into the patient’s eye as a lubricant. The deterioration of the surface lubricity of the soft contact lens after a day of wear can act as a built-in daily wearing compliance.

[0122] In yet another aspect, the present application provides an aqueous solution for treating, storing or packaging a hydrogel contact lens made of a polymeric material comprising 1,2-diol and 1,3-diol moieties, the aqueous solution comprising one or more buffering agents in an amount sufficient to maintain a pH from about 6 to about 8 and a hydrophilic copolymer comprising (a) repeating units each having an arylboronate-containing dihydroxyboron group and (b) repeating units of at least one hydrophilic vinylic monomer, wherein the hydrophilic copolymer is capable of being covalently attached to the hydrogel contact lens through linkages each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material, thereby forming a hydrophilic copolymer layer or coating on the hydrogel contact lens.

[0123] All of the various embodiments of the hydrophilic copolymer, the buffering agent, the tonicity agent, the tonicity and the viscosity described above are incorporated into this aspect of the present application.

[0124] The aqueous solution of the present application can find a specific use for treating, in particular storing or packaging, a hydrogel contact lens made of a polymeric material having 1,2-diol and / or 1,3-diol moieties, in order to improve the surface lubricity of the hydrogel contact lens.

[0125] In another aspect, the present application provides an ophthalmic product comprising a sealed and sterile package comprising a packaging solution and a soft hydrogel contact lens having been immersed in and autoclaved in the packaging solution in the sealed package, wherein the packaging solution has a pH from about 6.0 to about 8.0, a tonicity from about 200 to about 450 mOsm / kg, and a viscosity up to about 5.0 centipoise at 25°C, wherein the soft contact lens comprises a hydrogel lens body and a coating thereon, wherein the hydrogel lens body comprises or is made of a polymeric material having 1,2-diol and 1,3-diol moieties, wherein the coating comprises a hydrophilic copolymer layer, the hydrophilic copolymer comprising (a) repeating units each having an arylboronate-containing dihydroxyboron group and (b) repeating units of at least one hydrophilic vinylic monomer, wherein the coating is covalently attached to the hydrogel lens body through linkages each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material.

[0126] All of the various embodiments of the soft contact lens, the hydrophilic copolymer, the packaging solution, the buffering agent, the tonicity agent, the tonicity and the viscosity described above are incorporated into this aspect of the present application.

[0127] The ophthalmic product of the present invention can find particular use as a daily disposable hydrogel contact lens having improved surface lubricity to provide improved wearing comfort.

[0128] While specific terminology, devices and methods have been described herein for the purpose of describing various embodiments of the present invention, such description is not intended to be limiting. The word "comprising" is used herein to mean "including" but not necessarily "consisting of" or "composed of." It is understood that where the word "comprise" is used, it is intended to encompass the words "comprise", "comprises", "comprising", "include", "includes", "including" and "comprised of". It is further understood that where this term is used, it is intended to encompass the words "comprise", "comprises", "comprising", "include", "includes", "including" and "comprised of". It is intended that the present invention encompass all such variations and modifications without departing from the spirit or scope of the present invention as set forth in the following claims. Furthermore, it is understood that aspects of the various embodiments can be interchanged either in whole or in part or can be combined and / or used together in any manner, as will be apparent to those skilled in the art, as follows:

[0129] 1. A method for producing a soft contact lens, the method comprising the steps of:

[0130] (1) obtaining a preformed hydrogel contact lens, wherein the preformed hydrogel contact lens comprises or is made of a polymeric material having 1,2-diol and / or 1,3-diol moieties; and

[0131] (2) contacting the preformed hydrogel contact lens with an aqueous solution comprising (a) a hydrophilic copolymer of aryl-containing dihydroxylboron-containing repeating units each having a boronic acid and (b) repeating units of at least one hydrophilic vinylic monomer for a period of time to covalently attach a layer or coating of the hydrophilic copolymer to the preformed hydrogel contact lens through linkages each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material.

[0132] 2. The method of embodiment 1, wherein the preformed hydrogel contact lens has a first surface lubricity, wherein the soft contact lens has a second surface lubricity that is better than the first surface lubricity of the preformed hydrogel contact lens.

[0133] 3. The method of embodiment 1 or 2, wherein the aqueous solution has a pH from about 6.5 to about 9.0.

[0134] 4. The method of embodiment 1 or 2, wherein the aqueous solution has a pH from about 6.5 to about 8.5.

[0135] 5. The method of embodiment 1 or 2, wherein the aqueous solution has a pH from about 6.8 to about 8.0.

[0136] 6. The method of any one of embodiments 1 to 5, wherein the aqueous solution comprises from about 0.01% to about 2.5% by weight of the hydrophilic copolymer.

[0137] 7. The method of any one of embodiments 1 to 5, wherein the aqueous solution comprises from about 0.02% to about 2.0% by weight of the hydrophilic copolymer.

[0138] 8. The method of any one of embodiments 1 to 5, wherein the aqueous solution comprises from about 0.05% to about 1.5% by weight of the hydrophilic copolymer.

[0139] 9. The method of any one of embodiments 1 to 5, wherein the aqueous solution comprises from about 0.05% to about 1% by weight of the hydrophilic copolymer.

[0140] 10. The method of any one of embodiments 1 to 9, wherein the contact period is at least 1 minute.

[0141] 11 The method of any one of embodiments 1 to 9, wherein the contact period is at least 5 minutes.

[0142] 12. The method of any one of embodiments 1 to 9, wherein the contact period is at least 10 minutes.

[0143] 13. The method of any one of embodiments 1 to 9, wherein the contact period is from about 20 minutes to about 5 hours.

[0144] 14. The method of any one of embodiments 1 to 13, wherein the contacting step is performed by immersing the preformed hydrogel contact lens in an aqueous solution directly in the lens package, wherein the aqueous solution is a package solution.

[0145] 15. The method of embodiment 14, wherein the package solution contains a buffer for maintaining the pH of the package solution.

[0146] 16. The method of embodiment 14 or 15, wherein the package solution has a tonicity from about 200 to about 450 milliosmoles (mOsm).

[0147] 17. The method of embodiment 14 or 15, wherein the package solution has a tonicity from about 250 to about 350 mOsm.

[0148] 18. The method of any one of embodiments 14 to 17, further comprising the step of sealing the lens package and autoclaving the sealed lens package at a temperature from about 115 °C to about 125 °C for about 20-90 minutes.

[0149] 19. The method of any one of embodiments 1 to 18, wherein the preformed hydrogel contact lens is obtained by introducing a lens-forming composition (or formulation) into a reusable mold and curing the lens-forming composition (or formulation) in the reusable mold under spatial confinement of actinic radiation.

[0150] 20. The method of any one of embodiments 1 to 18, wherein the preformed hydrogel contact lens is obtained by introducing a lens-forming composition (or formulation) into a disposable mold and curing the lens-forming composition (or formulation) in the disposable mold.

[0151] 21. A soft contact lens comprising: a hydrogel lens body and a coating thereon,

[0152] wherein the hydrogel lens body comprises or is made of a polymeric material having 1,2-diol and / or 1,3-diol moieties,

[0153] wherein the coating comprises a layer of a hydrophilic copolymer comprising (a) arylboronate-containing repeating units each having a boronic acid group and (b) repeating units of at least one hydrophilic vinylic monomer, wherein the coating is covalently attached to the hydrogel lens body by linkages each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material.

[0154] 22. The method of any one of embodiments 1 to 20 or the soft contact lens of embodiment 21, wherein the preformed hydrogel contact lens or the hydrogel lens body comprises or is made of a polymeric material comprising at least 50% by moles of vinyl alcohol repeating units.

[0155] 23. The method of any one of embodiments 1 to 20 or the soft contact lens of embodiment 21, wherein the preformed hydrogel contact lens or the hydrogel lens body comprises or is made of a polymeric material comprising at least 60% by moles of vinyl alcohol repeating units.

[0156] 24. The method of any one of embodiments 1 to 20 or the soft contact lens of embodiment 21, wherein the preformed hydrogel contact lens or the hydrogel lens body comprises or is made of a polymeric material comprising at least 70% by moles of vinyl alcohol repeating units.

[0157] 25. The method of any one of embodiments 1 to 20 or the soft contact lens of embodiment 21, wherein the preformed hydrogel contact lens or the hydrogel lens body comprises or is made of a polymeric material comprising at least 75% by moles of vinyl alcohol repeat units.

[0158] 26. The method of any one of embodiments 1 to 20 and 22 to 25 or the soft contact lens of any one of embodiments 21 to 25, wherein the preformed hydrogel contact lens or the hydrogel lens body comprises or is made of a polymeric material that is a polymerization product of a water-soluble, actinically crosslinkable polyvinyl alcohol prepolymer comprising repeat units of vinyl alcohol and repeat units of formula (I)

[0159]

[0160] wherein:

[0161] R3may be hydrogen or C1-C6alkyl (preferably hydrogen);

[0162] R4is a C1-C6alkylene divalent radical (preferably a C1-C4alkylene divalent radical, more preferably a methylene or butylene divalent radical, even more preferably a methylene divalent radical);

[0163] R5is hydrogen or C1-C6alkyl (preferably hydrogen or C1-C4alkyl, more preferably hydrogen or methyl or ethyl, even more preferably hydrogen or methyl);

[0164] R6is an ethylenically unsaturated radical of formula (II) wherein q1and q2are independently of each other zero or one, and R7and R8are independently of each other a C2-C8alkylene divalent radical, and R9is a C2-C8alkenyl radical.

[0165] 27. The method or soft contact lens of embodiment 26, wherein in formula (I) R4is a methylene divalent radical, R5is hydrogen or C1-C4alkyl, R3is hydrogen, and R6is a radical of formula (II) wherein q2is zero, R9is an ethenyl * -CH=CH2) or a 1-methylethenyl * -C(CH3)=CH2) radical.

[0166] 28. The method or soft contact lens of embodiment 26 or 27, wherein the polyvinyl alcohol prepolymer has a weight average molecular weight of at least about 2,000 Daltons, and comprises from about 1% to about 25% by moles (preferably from about 2% to about 15% by moles) of the repeat units of formula (I).

[0167] 29. The method of any one of embodiments 1 to 20 and 22 to 25 or the soft contact lens of any one of embodiments 21 to 25, wherein the preformed hydrogel contact lens or the hydrogel lens body comprises or is made of a polymeric material comprising at least one type of diol-containing repeat unit each having one or more 1,2-diol and / or 1,3-diol moieties and having at least 5% of 1,2-diol and 1,3-diol moieties by repeat unit equivalent.

[0168] 30. The method of any one of embodiments 1 to 20 and 22 to 25 or the soft contact lens of any one of embodiments 21 to 25, wherein the preformed hydrogel contact lens or the hydrogel lens body comprises or is made of a polymeric material comprising at least one type of diol-containing repeat unit each having one or more 1,2-diol and / or 1,3-diol moieties and having at least 10% of 1,2-diol and 1,3-diol moieties by repeat unit equivalent.

[0169] 31. The method of any one of embodiments 1 to 20 and 22 to 25 or the soft contact lens of any one of embodiments 21 to 25, wherein the preformed hydrogel contact lens or the hydrogel lens body comprises or is made of a polymeric material comprising at least one type of diol-containing repeat unit each having one or more 1,2-diol and / or 1,3-diol moieties and having at least 15% of 1,2-diol and 1,3-diol moieties by repeat unit equivalent.

[0170] 32. The method of any one of embodiments 1 to 20 and 22 to 25 or the soft contact lens of any one of embodiments 21 to 25, wherein the preformed hydrogel contact lens or the hydrogel lens body comprises or is made of a polymeric material comprising at least one type of diol-containing repeat unit each having one or more 1,2-diol and / or 1,3-diol moieties and having at least 20% of 1,2-diol and 1,3-diol moieties by repeat unit equivalent.

[0171] 33. The method of any one of embodiments 1 to 20 and 22 to 25 or the soft contact lens of any one of embodiments 21 to 25, wherein the polymeric material comprises repeat units of at least one diol-containing vinylic monomer.

[0172] 34. The method or soft contact lens of embodiment 33, wherein the at least one diol- containing vinylic monomer is selected from the group consisting of N-2,3-dihydroxypropyl (meth)acrylamide, N-tris(hydroxymethyl)methyl (meth)acrylamide, 2- glucamidoethyl (meth)acrylamide, 3-glucamidopropyl (meth)acrylamide, glyceryl (meth)acrylate, glucosyl (meth)acrylate, glucosyloxyethyl (meth)acrylate, 3- allyloxy-1,2-propanediol, 2-allyloxymethyl-2-(hydroxymethyl)-1,3-propanediol, 2- allyloxymethyl-2-ethyl-1,3-propanediol (i.e., trimethylolpropane allyl ether), allyl a-D- mannoside, allyl a-D-galactoside, allyl 6-deoxyhexopyranoside, allyl 6-deoxy-2-O- methylhexopyranoside, and combinations thereof.

[0173] 35. The method of any one of embodiments 1 to 20, 22 to 25, 33, and 34 or the soft contact lens of any one of embodiments 21 to 25, 33, and 34, wherein the polymeric material comprises repeat units of at least one diol-containing vinylic crosslinker.

[0174] 36. The method or soft contact lens of embodiment 35, wherein the at least one diol- containing vinylic crosslinker is selected from the group consisting of N,N’-(1,2- dihydroxyethylidene)bis-(meth)acrylamide, N,N’-(2,3-dihydroxybutylidene)bis- (meth)acrylamide, a polydimethylsiloxane vinylic crosslinker comprising siloxane units each having a methyl substituent and one diol-containing substituent, and combinations thereof.

[0175] 37. The method of any one of embodiments 1 to 20 and 22 to 36 or the soft contact lens of any one of embodiments 21 to 36, wherein the hydrophilic copolymer comprises (a) from about 0.5% by mole to about 25% by mole of the arylboronate-containing repeat units and (b) from about 75% by mole to about 99.5% by mole of the repeat units of the at least one hydrophilic vinylic monomer, with the proviso that the sum of the mole percentages of components (a) and (b) and other components not listed above is 100%.

[0176] 38. The method of any one of embodiments 1 to 20 and 22 to 36 or the soft contact lens of any one of embodiments 21 to 36, wherein the hydrophilic copolymer comprises (a) from about 1% to about 20% by moles of the aryl-dihydroxyl boron-containing repeat unit and (b) from about 80% to about 99% by moles of the repeat unit of the at least one hydrophilic vinylic monomer, with the proviso that the sum of the mole percentages of components (a) and (b) and other components not listed above is 100%.

[0177] 39. The method of any one of embodiments 1 to 20 and 22 to 36 or the soft contact lens of any one of embodiments 21 to 36, wherein the hydrophilic copolymer comprises (a) from about 2% to about 18% by moles of the aryl-dihydroxyl boron-containing repeat unit and (b) from about 82% to about 98% by moles of the repeat unit of the at least one hydrophilic vinylic monomer, with the proviso that the sum of the mole percentages of components (a) and (b) and other components not listed above is 100%.

[0178] 40. The method of any one of embodiments 1 to 20 and 22 to 36 or the soft contact lens of any one of embodiments 21 to 36, wherein the hydrophilic copolymer comprises (a) from about 3% to about 15% by moles of the aryl-dihydroxyl boron-containing repeat unit and (b) from about 85% to about 97% by moles of the repeat unit of the at least one hydrophilic vinylic monomer, with the proviso that the sum of the mole percentages of components (a) and (b) and other components not listed above is 100%.

[0179] 41. The method of any one of embodiments 1 to 20 and 22 to 40 or the soft contact lens of any one of embodiments 21 to 40, wherein the at least one aryl-dihydroxyl boron-containing vinylic monomer is a vinylic monomer having the formula (II)

[0180]

[0181] wherein:

[0182] R1is H, NO2, F, Cl, or CF3; Q is a monovalent radical of -CH2-CH=CH2, or -CH=CH2; L is a direct bond, a C1-C4 alkylene divalent radical, a divalent radical of -Y1-C(O)-Y2-, wherein Y1is CH(OH) or a C1-C4 alkylene divalent radical, Y2is a C1-C4 alkylene divalent radical, and R o is H or C1-C4 alkyl.

[0183] 42. The method of any one of embodiments 1 to 20 and 22 to 40 or the soft contact lens of any one of embodiments 21 to 40, wherein the at least one aryl-dihydroxyboryl-containing vinylic monomer is selected from the group consisting of 3-vinylphenylboronic acid, 4-vinylboronic acid, 3-(meth)acrylamidophenylboronic acid, 4-(meth)acrylamidophenylboronic acid, and combinations thereof.

[0184] 43. The method of any one of embodiments 1 to 20 and 22 to 40 or the soft contact lens of any one of embodiments 21 to 40, wherein the at least one aryl-dihydroxyboryl-containing vinylic monomer is selected from the group consisting of reaction products of an amino-containing phenylboronic acid derivative with a (meth)acrylic acid halide, reaction products of an amino-containing phenylboronic acid derivative with a carboxyl-containing vinylic monomer in the presence of a carbodiimide (e.g., 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), N,N’-dicyclohexylcarbodiimide (DCC), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide, diisopropylcarbodiimide, or mixtures thereof) and N-hydroxysuccinimide, reaction products of a carboxyl-containing phenylboronic acid derivative with an amino-containing vinylic monomer in the presence of a carbodiimide (e.g., 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), N,N’-dicyclohexylcarbodiimide (DCC), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide, diisopropylcarbodiimide, or mixtures thereof) and N-hydroxysuccinimide, and combinations thereof.

[0185] 44. The method or soft contact lens of embodiment 43, wherein the carboxyl-containing phenylboronic acid derivative is selected from the group consisting of 3-carboxyphenylboronic acid, 4-carboxyphenylboronic acid, 3-dihydroxyborylphenylacetic acid, 4-dihydroxyborylphenylacetic acid, 2-(4-dihydroxyborylphenyl)-2-methylpropanoic acid, 3-(4-dihydroxyborylphenyl)propanoic acid, 3-(3-dihydroxyborylphenyl)propanoic acid, 5-(3-dihydroxyborylphenyl)pentanoic acid, 5-(4-dihydroxyborylphenyl)pentanoic acid, 4-(2-carboxyethyl)-3-nitrophenylboronic acid, 3-(3-carboxypropanoylamino)phenylboronic acid, 3-amino-3-(4-dihydroxyborylphenyl)propanoic acid, and combinations thereof,

[0186] wherein the amino-containing phenylboronic acid derivative is selected from the group consisting of 3-aminophenylboronic acid, 4-aminophenylboronic acid, 4-amino-3-nitrophenylboronic acid, 4-amino-4-fluorophenylboronic acid, 2-(aminomethyl)-5-nitrophenylboronic acid, 3-(aminomethyl)-phenylboronic acid, 3-amino-5-nitrophenylboronic acid, 3-amino-3-(4-dihydroxyborylphenyl)propanoic acid, and combinations thereof,

[0187] wherein the carboxyl group-containing vinylic monomer is selected from the group consisting of 2-acrylamidoglycolic acid, 3-acrylamidopropionic acid, 4- acrylamidobutanoic acid, 5-acrylamidopentanoic acid, 3-acryloyloxypropanoic acid, 4-acryloyloxybutanoic acid, 5-acryloyloxypentanoic acid, and combinations thereof,

[0188] wherein the amino group-containing vinylic monomer is selected from the group consisting of (meth)acrylic acid amino-C2-C4 alkyl ester, (meth)acrylic acid C1-C3 alkylamino-C2-C4 alkyl ester, amino-C2-C4 alkyl(meth)acrylamide, C1-C3 alkylamino-C2-C4 alkyl(meth)acrylamide, vinyl amine, allyl amine, and combinations thereof.

[0189] 45. The method of any one of embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of embodiments 21 to 44, wherein the at least one hydrophilic vinylic monomer comprises a phosphorylcholine-containing vinylic monomer.

[0190] 46. The method or soft contact lens of embodiment 45, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N- ethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-propyl(meth)acrylamide, N- isopropyl(meth)acrylamide, N-3-methoxypropyl(meth)acrylamide, and combinations thereof.

[0191] 47. The method or soft contact lens of embodiment 45, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of N-2-hydroxyethyl(meth)acrylamide, N,N-bis(hydroxyethyl)(meth)acrylamide, N-3-hydroxypropyl(meth)acrylamide, N-2-hydroxypropyl(meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 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.

[0192] 48. The method or soft contact lens of embodiment 45, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of N-2-aminoethyl (meth)acrylamide, N-2-methylaminoethyl (meth)acrylamide, N-2-ethylaminoethyl (meth)acrylamide, N-2-dimethylaminoethyl (meth)acrylamide, N-3-aminopropyl (meth)acrylamide, N-3-methylaminopropyl (meth)acrylamide, N-3-dimethylaminopropyl (meth)acrylamide, 2-aminoethyl (meth)acrylate, 2-methylaminoethyl (meth)acrylate, 2-ethylaminoethyl (meth)acrylate, 3-aminopropyl (meth)acrylate, 3-methylaminopropyl (meth)acrylate, 3-ethylaminopropyl (meth)acrylate, 3-amino-2-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylic acid trimethylammonium hydrochloride salt, dimethylaminoethyl (meth)acrylate, and combinations thereof.

[0193] 49. The method or soft contact lens of embodiment 45, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of 2-(meth)acrylamidoglycolic acid, (meth)acrylic acid, ethylacrylic acid, propylacrylic acid, 3-(meth)acrylamidopropionic acid, 4-(meth)acrylamidobutyric acid, 5-(meth)acrylamidopentanoic acid, 3-(meth)acryloyloxypropionic acid, 4-(meth)acryloyloxybutyric acid, 5-(meth)acryloyloxyvaleric acid, and combinations thereof.

[0194] 50. The method or soft contact lens of embodiment 45, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of N-vinylpyrrolidone (also known as N-vinyl-2-pyrrolidone), N-vinyl-3-methyl-2-pyrrolidone, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-6-methyl-2-pyrrolidone, N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, N-vinyl-5,5-dimethyl-2-pyrrolidone, N-vinyl-3,3,5-trimethyl-2-pyrrolidone, N-vinylpiperidone (also known as N-vinyl-2-piperidone), N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-5-methyl-2-piperidone, N-vinyl-6-methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone, N-vinyl-3,5-dimethyl-2-piperidone, N-vinyl-4,4-dimethyl-2-piperidone, N-vinylcaprolactam (also known as N-vinyl-2-caprolactam), N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, and mixtures thereof.

[0195] 51. The method or soft contact lens of embodiment 45, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of 1 -methyl-3-methylene-2-pyrrolidinone, 1 -ethyl-3-methylene-2-pyrrolidinone, 1 -methyl-5-methylene-2-pyrrolidinone, 1 -ethyl-5-methylene-2-pyrrolidinone, 5-methyl-3-methylene-2-pyrrolidinone, 5-ethyl-3-methylene-2-pyrrolidinone, 1 -n-propyl-3-methylene-2-pyrrolidinone, 1 -n-propyl-5-methylene-2-pyrrolidinone, 1 -isopropyl-3-methylene-2-pyrrolidinone, 1 -isopropyl-5-methylene-2-pyrrolidinone, 1 -n-butyl-3-methylene-2-pyrrolidinone, 1 -t-butyl-3-methylene-2-pyrrolidinone, and combinations thereof.

[0196] 52. The method or soft contact lens of Embodiment 45, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of 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-alkoxy poly(ethylene glycol) (meth)acrylate having a weight average molecular weight of up to 1500, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, and combinations thereof.

[0197] 53. The method or soft contact lens of Embodiment 45, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of ethylene glycol mono vinyl ether, di(ethylene glycol) mono vinyl ether, tri(ethylene glycol) mono vinyl ether, tetra(ethylene glycol) mono vinyl ether, poly(ethylene glycol) mono vinyl 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.

[0198] 54. The method or soft contact lens of Embodiment 45, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of allyl alcohol, ethylene glycol mono allyl ether, di(ethylene glycol) mono allyl ether, tri(ethylene glycol) mono allyl ether, tetra(ethylene glycol) mono allyl ether, poly(ethylene glycol) mono allyl ether, ethylene glycol methyl allyl ether, di(ethylene glycol) methyl allyl ether, tri(ethylene glycol) methyl allyl ether, tetra(ethylene glycol) methyl allyl ether, poly(ethylene glycol) methyl allyl ether, and combinations thereof.

[0199] 55. The method of any one of Embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of Embodiments 21 to 44, wherein the hydrophilic copolymer comprises (a) from about 1% to about 20% by moles of the aryl-containing dihydroxyl boron-containing repeat unit, (b) from about 60% to about 98% by moles of repeat units of at least one phosphorylcholine-containing vinylic monomer, and (c) from about 1% by moles to about 20% by moles of at least one acrylic monomer unit of an acrylic monomer having 3 to 16 carbon atoms, with the proviso that the sum of the mole percentages of components (a), (b), and (c) and other components not listed above is 100%.

[0200] 56. The method of any one of embodiments 1 to 20 and 22 to 44, or the soft contact lens of any one of embodiments 21 to 44, wherein the hydrophilic copolymer comprises (a) from about 1% to about 20% of the repeating unit of the aryl dihydroxyboron group, (b) from about 60% to about 97% of the repeating unit of at least one phosphorylcholine-containing vinyl monomer, and (c) from about 2% to about 20% of the acrylic monomer unit of at least one acrylic monomer having 3 to 16 carbon atoms, provided that the sum of the molar percentages of components (a), (b), and (c) and other components not listed above is 100%.

[0201] 57. The method of any one of embodiments 1 to 20 and 22 to 44, or the soft contact lens of any one of embodiments 21 to 44, wherein the hydrophilic copolymer comprises (a) from about 2% to about 15% of the repeating unit of the aryl dihydroxyboron group, (b) from about 70% to about 95% of the repeating unit of at least one phosphorylcholine-containing vinyl monomer, and (c) from about 3% to about 15% of the acrylic monomer unit of at least one acrylic monomer having 3 to 16 carbon atoms, provided that the sum of the molar percentages of components (a), (b), and (c) and other components not listed above is 100%.

[0202] 58. The method or soft contact lens as described in any one of embodiments 55 to 57, wherein the at least one acrylic monomer has 3 to 14 carbon atoms.

[0203] 59. The method or soft contact lens as described in any one of embodiments 55 to 57, wherein the at least one acrylic monomer has 3 to 12 carbon atoms.

[0204] 60. The method or soft contact lens as described in any one of embodiments 55 to 57, wherein the at least one acrylic monomer has 3 to 10 carbon atoms.

[0205] 61. The method or soft contact lens according to any one of embodiments 55 to 57, wherein the at least one acrylic monomer is selected from the group consisting of (meth)acrylic acid C1-C 12 Alkyl esters, (meth)acrylic acid hydroxy-substituted C2-C 12 Alkyl esters, C2-C carboxyl-substituted (meth)acrylic acid esters 12 Alkyl esters, (meth)acrylic acid NH2-substituted C2-C 12 Alkyl esters, methylamino-substituted C2-C (meth)acrylates 12 Alkyl esters, dimethylamino-substituted (meth)acrylates, C2-C12 Alkyl esters, (meth)acrylates, ethylamino-substituted C2-C 10 Alkyl esters, diethylamino-substituted C2-C8 alkyl esters of (meth)acrylate, C2-C 12 Alkyl (meth)acrylamide, hydroxy-substituted C2-C 12 Alkyl (meth)acrylamide, carboxyl-substituted C2-C 12 Alkyl (meth)acrylamide, NH2-substituted C2-C 12 Alkyl (meth)acrylamide, methylamino-substituted C2-C 12 Alkyl (meth)acrylamide, dimethylamino-substituted C2-C 12 Alkyl (meth)acrylamide, ethylamino-substituted C2-C 10 Alkyl (meth)acrylamide, diethylamino-substituted C2-C8 alkyl (meth)acrylamide, ethylene glycol (meth)acrylate, di(ethylene glycol)(meth)acrylate, tri(ethylene glycol)(meth)acrylate, tetra(ethylene glycol)(meth)acrylate, 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 combinations thereof.

[0206] 62. The method or soft contact lens according to any one of embodiments 55 to 57, wherein the at least one acrylic monomer is n-butyl (meth)acrylate and / or di(ethylene glycol) methyl ether (meth)acrylate.

[0207] 63. The method or soft contact lens of any one of embodiments 45 to 62, wherein the phosphorylcholine-containing vinylic monomer is selected from the group consisting of (meth)acryloyloxyethylphosphorylcholine, (meth)acryloyloxypropylphosphorylcholine, 4-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethylphosphate, 2-[(meth)acryloylamino]ethyl-2'-(trimethylammonio)-ethylphosphate, 3-[(meth)acryloylamino]propyl-2'-(trimethylammonio)ethylphosphate, 4-[(meth)acryloylamino]butyl-2'-(trimethylammonio)ethylphosphate, 5-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethylphosphate, 6-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)-ethylphosphate, 2-((meth)acryloyloxy)ethyl-2'-(triethylammonio)ethylphosphate, 2-((meth)acryloyloxy)ethyl-2'-(tripropylammonio)ethylphosphate, 2-((meth)acryloyloxy)ethyl-2'-(tributylammonio)ethylphosphate, 2-((meth)acryloyloxy)propyl-2'-(trimethylammonio)-ethylphosphate, 2-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethylphosphate, 2-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethylphosphate, 2-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)ethylphosphate, 2-(vinyloxy)ethyl-2'-(trimethylammonio)ethylphosphate, 2-(allyloxy)ethyl-2'-(trimethylammonio)ethylphosphate, 2-(vinyloxycarbonyl)ethyl-2'-(trimethylammonio)ethylphosphate, 2-(allyloxycarbonyl)ethyl-2'-(trimethylammonio)-ethylphosphate, 2-(vinylcarbonylamino)ethyl-2'-(trimethylammonio)ethylphosphate, 2-(allyloxycarbonylamino)ethyl-2'-(trimethylammonio)ethylphosphate, 2-(butenoyloxy)ethyl-2'-(trimethylammonio)ethylphosphate, and combinations thereof.

[0208] 64. The method of any one of embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of embodiments 21 to 44, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N-ethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-propyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-3-methoxypropyl(meth)acrylamide, N-2-hydroxyethyl(meth)acrylamide, N,N-bis(hydroxyethyl)(meth)acrylamide, N-3-hydroxypropyl(meth)acrylamide, N-2-hydroxypropyl(meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 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, 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, 2-hydroxypropyl (meth)acrylic acid trimethylammonium hydrochloride, dimethylaminoethyl (meth)acrylate, 2-(meth)acrylamidoglycolic acid, (meth)acrylic acid, ethylacrylic acid, propylacrylic acid, 3-(meth)acrylamidopropionic acid, 4-(meth)acrylamidobutanoic acid, 5-(meth)acrylamidopentanoic acid, 3-(meth)acryloyloxypropionic acid, 4-(meth)acryloyloxybutanoic acid, 5-(meth)acryloyloxypentanoic acid, N-vinylpyrrolidone (also known as N-vinyl-2-pyrrolidone), N-vinyl-3-methyl-2-pyrrolidone, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-6-methyl-2-pyrrolidone, N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, N-vinyl-5,5-dimethyl-2-pyrrolidone, N-vinyl-3,3,5-trimethyl-2-pyrrolidone, N-vinylpiperidone (also known as N-vinyl-2-piperidone), N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-5-methyl-2-piperidone, N-vinyl-6-methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone, N-vinyl-3,5-dimethyl-2-piperidone, N-vinyl-4,4-dimethyl-2-piperidone, N-vinyl caprolactam (also known as N-vinyl-2-caprolactam), N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, 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-alkoxy poly(ethylene glycol) (meth)acrylates having a weight average molecular weight of up to 1500, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, 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 methylvinyl ether, di(ethylene glycol) methylvinyl ether, tri(ethylene glycol) methylvinyl ether, tetra(ethylene glycol) methylvinyl ether, poly(ethylene glycol) methylvinyl ether, allyl alcohol, 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 methylallyl ether, di(ethylene glycol) methylallyl ether, tri(ethylene glycol) methylallyl ether, tetra(ethylene glycol) methylallyl ether, poly(ethylene glycol) methylallyl ether, N-2-hydroxyethyl vinylcarbamate, N-carboxyvinyl-β-alanine (VINAL), N-carboxyvinyl-α-alanine, and combinations thereof.

[0209] 65. The method of any one of embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of embodiments 21 to 44, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N-ethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-propyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-3-methoxypropyl(meth)acrylamide, and combinations thereof.

[0210] 66. The method of any one of embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of embodiments 21 to 44, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of N-2-hydroxyethyl(meth)acrylamide, N,N-bis(hydroxyethyl)(meth)acrylamide, N-3-hydroxypropyl(meth)acrylamide, N-2-hydroxypropyl(meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 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.

[0211] 67. The method of any one of embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of embodiments 21 to 44, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of N-2-aminoethyl(meth)acrylamide, N-2-methylaminoethyl(meth)acrylamide, N-2-ethylaminoethyl(meth)acrylamide, N-2-dimethylaminoethyl(meth)acrylamide, N-3-aminopropyl(meth)acrylamide, N-3-methylaminopropyl(meth)acrylamide, N-3-dimethylaminopropyl(meth)acrylamide, 2-aminoethyl (meth)acrylate, 2-methylaminoethyl (meth)acrylate, 2-ethylaminoethyl (meth)acrylate, 3-aminopropyl (meth)acrylate, 3-methylaminopropyl (meth)acrylate, 3-ethylaminopropyl (meth)acrylate, 3-amino-2-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate trimethylammonium hydrochloride, dimethylaminoethyl (meth)acrylate, vinyl amine, allyl amine, and combinations thereof.

[0212] 68. The method of any one of embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of embodiments 21 to 44, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of acrylic acid, methacrylic acid, ethylacrylic acid, propylacrylic acid, 2-acrylamidoglycolic acid, 3-acrylamidopropionic acid, 4-acrylamidobutanoic acid, 5-acrylamidopentanoic acid, 3-acryloyloxypropionic acid, 4-acryloyloxybutanoic acid, 5-acryloyloxypentanoic acid, and combinations thereof.

[0213] 69. The method of any one of embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of embodiments 21 to 44, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of N-vinylpyrrolidone (also known as N-vinyl-2-pyrrolidone), N-vinyl-3-methyl-2-pyrrolidone, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-6-methyl-2-pyrrolidone, N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, N-vinyl-5,5-dimethyl-2-pyrrolidone, N-vinyl-3,3,5-trimethyl-2-pyrrolidone, N-vinylpiperidone (also known as N-vinyl-2-piperidone), N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-5-methyl-2-piperidone, N-vinyl-6-methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone, N-vinyl-3,5-dimethyl-2-piperidone, N-vinyl-4,4-dimethyl-2-piperidone, N-vinylcaprolactam (also known as N-vinyl-2-caprolactam), N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, and mixtures thereof. Preferably, the N-vinyl amide monomer is N-vinylpyrrolidone, N-vinyl-N-methylacetamide, or a combination thereof.

[0214] 70. The method of any one of embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of embodiments 21 to 44, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of 1 -methyl-3-methylene-2-pyrrolidinone, 1 -ethyl-3-methylene-2-pyrrolidinone, 1 -methyl-5-methylene-2-pyrrolidinone, 1 -ethyl-5-methylene-2-pyrrolidinone, 5-methyl-3-methylene-2-pyrrolidinone, 5-ethyl-3-methylene-2-pyrrolidinone, 1 -n-propyl-3-methylene-2-pyrrolidinone, 1 -n-propyl-5-methylene-2-pyrrolidinone, 1 -i-propyl-3-methylene-2-pyrrolidinone, 1 -i-propyl-5-methylene-2-pyrrolidinone, 1 -n-butyl-3-methylene-2-pyrrolidinone, 1 -t-butyl-3-methylene-2-pyrrolidinone, and combinations thereof.

[0215] 71. The method of any one of embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of embodiments 21 to 44, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of 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-alkoxy poly(ethylene glycol) (meth)acrylate having a weight average molecular weight of up to 1500, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, and combinations thereof.

[0216] 72. The method of any one of embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of embodiments 21 to 44, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of ethylene glycol monovinyl ether, di(ethylene glycol) monovinyl ether, tri(ethylene glycol) monovinyl ether, tetra(ethylene glycol) monovinyl ether, poly(ethylene glycol) monovinyl ether, ethylene glycol methylvinyl ether, di(ethylene glycol) methylvinyl ether, tri(ethylene glycol) methylvinyl ether, tetra(ethylene glycol) methylvinyl ether, poly(ethylene glycol) methylvinyl ether, and combinations thereof.

[0217] 73. The method of any one of embodiments 1 to 20 and 22 to 44 or the soft contact lens of any one of embodiments 21 to 44, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of allyl alcohol, 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 methylallyl ether, di(ethylene glycol) methylallyl ether, tri(ethylene glycol) methylallyl ether, tetra(ethylene glycol) methylallyl ether, poly(ethylene glycol) methylallyl ether, and combinations thereof.

[0218] 74. The method of any one of embodiments 1 to 20 and 22 to 73 or the soft contact lens of any one of embodiments 21 to 73, wherein the soft contact lens has an equilibrium water content, when fully hydrated, of from about 15% to about 80% by weight (at room temperature, about 22°C to 28°C).

[0219] 75. The method of any one of embodiments 1 to 20 and 22 to 74 or the soft contact lens of any one of embodiments 21 to 74, wherein the soft contact lens has an elastic modulus, when fully hydrated, of from about 0.2 MPa to about 1.5 MPa.

[0220] 76. The method of any one of embodiments 1 to 20 and 22 to 74 or the soft contact lens of any one of embodiments 21 to 74, wherein the soft contact lens has an elastic modulus, when fully hydrated, of from about 0.3 MPa to about 1.3 MPa.

[0221] 77. The method of any one of embodiments 1 to 20 and 22 to 74 or the soft contact lens of any one of embodiments 21 to 74, wherein the soft contact lens has an elastic modulus, when fully hydrated, of from about 0.4 MPa to about 1.1 MPa.

[0222] 78. The method of any one of embodiments 1 to 20 and 22 to 74 or the soft contact lens of any one of embodiments 21 to 74, wherein the soft contact lens has an elastic modulus, when fully hydrated, of from about 0.5 MPa to about 1.0 MPa.

[0223] 79. The method of any one of embodiments 1 to 20 and 22 to 78 or the soft contact lens of any one of embodiments 21 to 78, wherein the hydrophilic copolymer has a weight average molecular weight of at least about 100,000 Daltons.

[0224] 80. The method of any one of embodiments 1 to 20 and 22 to 78 or the soft contact lens of any one of embodiments 21 to 78, wherein the hydrophilic copolymer has a weight average molecular weight of at least about 125,000 Daltons.

[0225] 81. The method of any one of embodiments 1 to 20 and 22 to 78 or the soft contact lens of any one of embodiments 21 to 78, wherein the hydrophilic copolymer has a weight average molecular weight of at least about 250,000 Daltons.

[0226] 82. The method of any one of embodiments 1 to 20 and 22 to 78 or the soft contact lens of any one of embodiments 21 to 78, wherein the hydrophilic copolymer has a weight average molecular weight of at least about 400,000 Daltons.

[0227] 83. The method of any one of embodiments 1 to 20 and 22 to 82 or the soft contact lens of any one of embodiments 21 to 82, wherein the soft contact lens has a friction rating of about 2.5 or lower.

[0228] 84. The method of any one of embodiments 1 to 20 and 22 to 82 or the soft contact lens of any one of embodiments 21 to 82, wherein the soft contact lens has a friction rating of about 2.0 or lower.

[0229] 85. The method of any one of embodiments 1 to 20 and 22 to 82 or the soft contact lens of any one of embodiments 21 to 82, wherein the soft contact lens has a friction rating of about 1.5 or lower.

[0230] 86. The method of any one of embodiments 1 to 20 and 22 to 82 or the soft contact lens of any one of embodiments 21 to 82, wherein the soft contact lens has a friction rating of about 1.0 or lower.

[0231] 87. An ophthalmic product comprising a sealed and sterile package, the package including a packaging solution and a soft contact lens of any one of embodiments 21 to 86, wherein the soft contact lens has been immersed in and autoclaved in the packaging solution in the sealed package, wherein the packaging solution has a pH of from about 6.0 to about 8.0, a tonicity of from about 200 to about 450 mOsm / kg, and a viscosity of up to about 5.0 centipoise at 25 °C.

[0232] 88. An aqueous solution for handling, storing, or packaging a hydrogel lens contact lens comprising or made from a polymeric material comprising 1,2-diol and 1,3-diol moieties, the aqueous solution comprising:

[0233] one or more buffers in an amount sufficient to maintain a pH from about 6 to about 8; and a hydrophilic copolymer,

[0234] wherein the hydrophilic copolymer comprises (a) repeating units each having an aryl- containing dihydroxylboron group of boric acid and (b) repeating units of at least one hydrophilic vinylic monomer,

[0235] wherein the hydrophilic copolymer is covalently attached to the hydrogel contact lens by linkages each formed between one of the boric acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material when in contact with the hydrogel contact lens, thereby forming a layer or coating of the hydrophilic copolymer on the hydrogel contact lens,

[0236] wherein the aqueous solution has a tonicity from about 200 to about 450 milliosmole (mOsm).

[0237] 89. The aqueous solution of embodiment 88, wherein the aqueous solution comprises from about 0.01% to about 2.5% by weight of the hydrophilic copolymer.

[0238] 90. The aqueous solution of embodiment 88, wherein the aqueous solution comprises from about 0.02% to about 2.0% by weight of the hydrophilic copolymer.

[0239] 91. The aqueous solution of embodiment 88, wherein the aqueous solution comprises from about 0.05% to about 1.5% by weight of the hydrophilic copolymer.

[0240] 92. The aqueous solution of embodiment 88, wherein the aqueous solution comprises from about 0.05% to about 1% by weight of the hydrophilic copolymer.

[0241] 93. The aqueous solution of any one of embodiments 88 to 92, wherein the hydrophilic copolymer comprises (a) from about 0.5% by mole to about 25% by mole of the aryl-containing dihydroxylboron group repeating units and (b) from about 75% by mole to about 99.5% by mole of the repeating units of the at least one hydrophilic vinylic monomer, with the proviso that the sum of the mole percentages of components (a) and (b) and other components not listed above is 100%.

[0242] 94. An aqueous solution as described in any one of embodiments 88 to 92, wherein the hydrophilic copolymer comprises (a) from about 1% to about 20% of the repeating unit containing aryl dihydroxyboron on a molar basis and (b) from about 80% to about 99% of the repeating unit of the at least one hydrophilic ethylene monomer on a molar basis, provided that the sum of the molar percentages of components (a) and (b) and other components not listed above is 100%.

[0243] 95. An aqueous solution as described in any one of embodiments 88 to 92, wherein the hydrophilic copolymer comprises (a) from about 2% to about 18% of the repeating unit containing aryl dihydroxyboron on a molar basis and (b) from about 82% to about 98% of the repeating unit of the at least one hydrophilic ethylene monomer on a molar basis, provided that the sum of the molar percentages of components (a) and (b) and other components not listed above is 100%.

[0244] 96. An aqueous solution as described in any one of embodiments 88 to 92, wherein the hydrophilic copolymer comprises (a) from about 3% to about 15% of the repeating unit containing aryl dihydroxyboron on a molar basis and (b) from about 85% to about 97% of the repeating unit of the at least one hydrophilic ethylene monomer on a molar basis, provided that the sum of the molar percentages of components (a) and (b) and other components not listed above is 100%.

[0245] 97. An aqueous solution as described in any one of embodiments 88 to 96, wherein the at least one aryldihydroxyboronyl ethylene monomer is an ethylene monomer having formula (II).

[0246]

[0247] in:

[0248] R1 is H, NO2, F, Cl, or CF3; Q is -CH2-CH=CH2 or -CH=CH2 is a monovalent group; L is a direct bond, and it is a C1-C4 alkylene divalent group. The divalent groups, wherein Y1 is CH(OH) or a C1-C4 alkylene divalent group, Y2 is a C1-C4 alkylene divalent group, and R o It is H or C1-C4 alkyl.

[0249] 98. An aqueous solution as described in any one of embodiments 88 to 96, wherein the at least one aryl dihydroxyboronic ethylene monomer is selected from the group consisting of: 3-vinylphenylboronic acid, 4-vinylboronic acid, 3-(meth)acrylamidophenylboronic acid, 4-(meth)acrylamidophenylboronic acid, and combinations thereof.

[0250] 99. The aqueous solution of any one of embodiments 88-96, wherein the at least one aryl- containing dihydroxyboryl-containing vinylic monomer is selected from the group consisting of: a reaction product of an amino-containing phenylboronic acid derivative and a (meth)acrylic acid halide, a reaction product of an amino-containing phenylboronic acid derivative and a carboxyl-containing vinylic monomer in the presence of a carbodiimide (e.g., 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), N,N’-dicyclohexylcarbodiimide (DCC), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide, diisopropylcarbodiimide, or a mixture thereof) and N-hydroxysuccinimide, a reaction product of a carboxyl-containing phenylboronic acid derivative and an amino-containing vinylic monomer in the presence of a carbodiimide (e.g., 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), N,N’-dicyclohexylcarbodiimide (DCC), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide, diisopropylcarbodiimide, or a mixture thereof) and N-hydroxysuccinimide, and combinations thereof.

[0251] 100. The aqueous solution of embodiment 99, wherein the carboxyl-containing phenylboronic acid derivative is selected from the group consisting of: 3-carboxyphenylboronic acid, 4-carboxyphenylboronic acid, 3-dihydroxyborylphenylacetic acid, 4-dihydroxyborylphenylacetic acid, 2-(4-dihydroxyborylphenyl)-2-methylpropanoic acid, 3-(4-dihydroxyborylphenyl)propanoic acid, 3-(3-dihydroxyborylphenyl)propanoic acid, 5-(3-dihydroxyborylphenyl)pentanoic acid, 5-(4-dihydroxyborylphenyl)pentanoic acid, 4-(2-carboxyethyl)-3-nitrophenylboronic acid, 3-(3-carboxypropanoylamino)phenylboronic acid, 3-amino-3-(4-dihydroxyborylphenyl)propanoic acid, and combinations thereof,

[0252] wherein the amino-containing phenylboronic acid derivative is selected from the group consisting of: 3-aminophenylboronic acid, 4-aminophenylboronic acid, 4-amino-3-nitrophenylboronic acid, 4-amino-4-fluorophenylboronic acid, 2-(aminomethyl)-5-nitrophenylboronic acid, 3-(aminomethyl)-phenylboronic acid, 3-amino-5-nitrophenylboronic acid, 3-amino-3-(4-dihydroxyborylphenyl)propanoic acid, and combinations thereof,

[0253] wherein the carboxyl-containing vinylic monomer is selected from the group consisting of: 2-acrylamido glycolic acid, 3-acrylamidopropionic acid, 4-acrylamidobutanoic acid, 5-acrylamidopentanoic acid, 3-acryloyloxypropanoic acid, 4-acryloyloxybutanoic acid, 5-acryloyloxy pentanoic acid, and combinations thereof,

[0254] wherein the amino-containing vinylic monomer is selected from the group consisting of amino-C2-C4 alkyl (meth)acrylate, C1-C3 alkylamino-C2-C4 alkyl (meth)acrylate, amino-C2-C4 alkyl (meth)acrylamide, C1-C3 alkylamino-C2-C4 alkyl (meth)acrylamide, vinyl amine, allyl amine, and combinations thereof.

[0255] 101. The aqueous solution of any one of embodiments 88-100, wherein the at least one hydrophilic vinylic monomer comprises a phosphorylcholine-containing vinylic monomer.

[0256] 102. The aqueous solution of embodiment 101, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N-ethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N-propyl (meth)acrylamide, N-isopropyl (meth)acrylamide, N-3-methoxypropyl (meth)acrylamide, and combinations thereof.

[0257] 103. The aqueous solution of embodiment 101, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of N-2-hydroxyethyl (meth)acrylamide, N,N-bis(hydroxyethyl) (meth)acrylamide, N-3-hydroxypropyl (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 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.

[0258] 104. The aqueous solution of embodiment 101, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of N-2-aminoethyl (meth)acrylamide, N-2-methylaminoethyl (meth)acrylamide, N-2-ethylaminoethyl (meth)acrylamide, N-2-dimethylaminoethyl (meth)acrylamide, N-3-aminopropyl (meth)acrylamide, N-3-methylaminopropyl (meth)acrylamide, N-3-dimethylaminopropyl (meth)acrylamide, 2-aminoethyl (meth)acrylate, 2-methylaminoethyl (meth)acrylate, 2-ethylaminoethyl (meth)acrylate, 3-aminopropyl (meth)acrylate, 3-methylaminopropyl (meth)acrylate, 3-ethylaminopropyl (meth)acrylate, 3-amino-2-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylic acid trimethylammonium hydrochloride salt, dimethylaminoethyl (meth)acrylate, and combinations thereof.

[0259] 105. The aqueous solution of embodiment 101, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of 2-(meth)acrylamidoglycolic acid, (meth)acrylic acid, ethylacrylic acid, propylacrylic acid, 3-(meth)acrylamidopropionic acid, 4-(meth)acrylamidobutyric acid, 5-(meth)acrylamidopentanoic acid, 3-(meth)acryloyloxypropionic acid, 4-(meth)acryloyloxybutyric acid, 5-(meth)acryloyloxyvaleric acid, and combinations thereof.

[0260] 106. The aqueous solution of embodiment 101, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of N-vinylpyrrolidone (also known as N-vinyl-2-pyrrolidone), N-vinyl-3-methyl-2-pyrrolidone, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-6-methyl-2-pyrrolidone, N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, N-vinyl-5,5-dimethyl-2-pyrrolidone, N-vinyl-3,3,5-trimethyl-2-pyrrolidone, N-vinylpiperidone (also known as N-vinyl-2-piperidone), N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-5-methyl-2-piperidone, N-vinyl-6-methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone, N-vinyl-3,5-dimethyl-2-piperidone, N-vinyl-4,4-dimethyl-2-piperidone, N-vinylcaprolactam (also known as N-vinyl-2-caprolactam), N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, and mixtures thereof. Preferably, the N-vinylamide monomer is N-vinylpyrrolidone, N-vinyl-N-methylacetamide, N-2-hydroxyethylvinylcarbamate, N-carboxyvinyl-β-alanine (VINAL), N-carboxyvinyl-α-alanine, and combinations thereof.

[0261] 107. The aqueous solution of embodiment 101, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of 1 -methyl-3-methylene-2-pyrrolidinone, 1 -ethyl-3-methylene-2- pyrrolidinone, 1 -methyl-5-methylene-2-pyrrolidinone, 1 -ethyl-5-methylene-2- pyrrolidinone, 5-methyl-3-methylene-2-pyrrolidinone, 5-ethyl-3-methylene-2- pyrrolidinone, 1 -n-propyl-3-methylene-2-pyrrolidinone, 1 -n-propyl-5-methylene-2- pyrrolidinone, 1 -i-propyl-3-methylene-2-pyrrolidinone, 1 -i-propyl-5-methylene-2- pyrrolidinone, 1 -n-butyl-3-methylene-2-pyrrolidinone, 1 -t-butyl-3-methylene-2- pyrrolidinone, and combinations thereof.

[0262] 108. The aqueous solution of embodiment 101, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of 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-alkoxy poly(ethylene glycol) (meth)acrylate having a weight average molecular weight of up to 1500, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, and combinations thereof.

[0263] 109. The aqueous solution of embodiment 101, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of ethylene glycol monovinyl ether, di(ethylene glycol) monovinyl ether, tri(ethylene glycol) monovinyl ether, tetra(ethylene glycol) monovinyl ether, poly(ethylene glycol) monovinyl ether, ethylene glycol methylvinyl ether, di(ethylene glycol) methylvinyl ether, tri(ethylene glycol) methylvinyl ether, tetra(ethylene glycol) methylvinyl ether, poly(ethylene glycol) methylvinyl ether, and combinations thereof.

[0264] 110. The aqueous solution of embodiment 101, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of allyl alcohol, 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 methylallyl ether, di(ethylene glycol) methylallyl ether, tri(ethylene glycol) methylallyl ether, tetra(ethylene glycol) methylallyl ether, poly(ethylene glycol) methylallyl ether, and combinations thereof.

[0265] 111. The aqueous solution of embodiment 101, wherein the hydrophilic copolymer comprises (a) from about 1% to about 20% by moles of the aryl-dihydroxyl boron group containing repeat unit, (b) from about 60% to about 98% by moles of repeat units of at least one phosphoryl choline containing vinylic monomer, and (c) from about 1% by moles to about 20% by moles of at least one acrylic monomer unit of an acrylic monomer having 3 to 16 carbon atoms, with the proviso that the sum of the mole percentages of components (a), (b), and (c) and other components not listed above is 100%.

[0266] 112. The aqueous solution of embodiment 101, wherein the hydrophilic copolymer comprises (a) from about 1% to about 20% by moles of the aryl-dihydroxyl boron group containing repeat unit, (b) from about 60% to about 97% by moles of repeat units of at least one phosphoryl choline containing vinylic monomer, and (c) from about 2% by moles to about 20% by moles of at least one acrylic monomer unit of an acrylic monomer having 3 to 16 carbon atoms, with the proviso that the sum of the mole percentages of components (a), (b), and (c) and other components not listed above is 100%.

[0267] 113. The aqueous solution of embodiment 101, wherein the hydrophilic copolymer comprises (a) from about 2% to about 15% by moles of the aryl-dihydroxyl boron group containing repeat unit, (b) from about 70% to about 95% by moles of repeat units of at least one phosphoryl choline containing vinylic monomer, and (c) from about 3% by moles to about 15% by moles of at least one acrylic monomer unit of an acrylic monomer having 3 to 16 carbon atoms, with the proviso that the sum of the mole percentages of components (a), (b), and (c) and other components not listed above is 100%.

[0268] 114. The aqueous solution of any one of embodiments 111 to 113, wherein the at least one acrylic monomer has 3 to 14 carbon atoms.

[0269] 115. The aqueous solution of any one of embodiments 111 to 113, wherein the at least one acrylic monomer has 3 to 12 carbon atoms.

[0270] 116. The aqueous solution of any one of embodiments 111 to 113, wherein the at least one acrylic monomer has 3 to 10 carbon atoms.

[0271] 117. The aqueous solution of any one of embodiments 111 to 113, wherein the at least one acrylic monomer is selected from the group consisting of (C1-C4 alkyl)acrylic acid, (C1-C4 alkyl)acrylate, (C1-C4 alkyl)acrylamide, (C1-C4 alkyl)acrylonitrile, and combinations thereof. 12Alkyl esters, (meth)acrylic acid hydroxy-substituted C2-C 12 Alkyl esters, C2-C carboxyl-substituted (meth)acrylic acid esters 12 Alkyl esters, (meth)acrylic acid NH2-substituted C2-C 12 Alkyl esters, methylamino-substituted C2-C (meth)acrylates 12 Alkyl esters, dimethylamino-substituted (meth)acrylates, C2-C 12 Alkyl esters, (meth)acrylates, ethylamino-substituted C2-C 10 Alkyl esters, diethylamino-substituted C2-C8 alkyl esters of (meth)acrylate, C2-C 12 Alkyl (meth)acrylamide, hydroxy-substituted C2-C 12 Alkyl (meth)acrylamide, carboxyl-substituted C2-C 12 Alkyl (meth)acrylamide, NH2-substituted C2-C 12 Alkyl (meth)acrylamide, methylamino-substituted C2-C 12 Alkyl (meth)acrylamide, dimethylamino-substituted C2-C 12 Alkyl (meth)acrylamide, ethylamino-substituted C2-C 10 Alkyl (meth)acrylamide, diethylamino-substituted C2-C8 alkyl (meth)acrylamide, ethylene glycol (meth)acrylate, di(ethylene glycol)(meth)acrylate, tri(ethylene glycol)(meth)acrylate, tetra(ethylene glycol)(meth)acrylate, 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 combinations thereof.

[0272] 118. An aqueous solution as described in any one of embodiments 111 to 113, wherein the at least one acrylic monomer is n-butyl (meth)acrylate and / or di(ethylene glycol) methyl ether (meth)acrylate.

[0273] 119. The aqueous solution of any one of embodiments 101-118, wherein the phosphorylcholine-containing vinylic monomer is selected from the group consisting of (meth)acryloyloxyethyl phosphorylcholine, (meth)acryloyloxypropyl phosphorylcholine, 4-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethyl phosphate, 2-[(meth)acryloylamino]ethyl-2'-(trimethylammonio)-ethyl phosphate, 3-[(meth)acryloylamino]propyl-2'-(trimethylammonio)ethyl phosphate, 4-[(meth)acryloylamino]butyl-2'-(trimethylammonio)ethyl phosphate, 5-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 6-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)-ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(triethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(tripropylammonio)ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(tributylammonio)ethyl phosphate, 2-((meth)acryloyloxy)propyl-2'-(trimethylammonio)-ethyl phosphate, 2-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxycarbonyl)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonyl)ethyl-2'-(trimethylammonio)-ethyl phosphate, 2-(vinylcarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(butenoyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, and combinations thereof.

[0274] 120. The aqueous solution of any one of embodiments 88-119, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N-ethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-propyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-3-methoxypropyl(meth)acrylamide, N-2-hydroxyethyl(meth)acrylamide, N,N-bis(hydroxyethyl)(meth)acrylamide, N-3-hydroxypropyl(meth)acrylamide, N-2-hydroxypropyl(meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 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, 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, 2- hydroxypropyl (meth)acrylate trimethylammonium hydrochloride, dimethylaminoethyl (meth)acrylate, 2-(meth)acrylamidoglycolic acid, (meth)acrylic acid, ethyl acrylate, propyl acrylate, 3-(meth)acrylamidopropionic acid, 4- (meth)acrylamidobutanoic acid, 5-(meth)acrylamidopentanoic acid, 3- (meth)acryloyloxypropionic acid, 4-(meth)acryloyloxybutanoic acid, 5- (meth)acryloyloxypentanoic acid, N-vinylpyrrolidone (also known as N-vinyl-2- pyrrolidone), N-vinyl-3-methyl-2-pyrrolidone, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-6-methyl-2-pyrrolidone, N-vinyl-3- ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, N-vinyl-5,5-dimethyl-2- pyrrolidone, N-vinyl-3,3,5-trimethyl-2-pyrrolidone, N-vinylpiperidone (also known as N-vinyl-2-piperidone), N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-5-methyl-2-piperidone, N-vinyl-6-methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone, N-vinyl-3,5-dimethyl-2-piperidone, N-vinyl-4,4-dimethyl-2-piperidone, N-vinylcaprolactam (also known as N-vinyl-2-caprolactam), N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, and mixtures thereof. Preferably, the N-vinylamide monomer is N-vinylpyrrolidone, N-vinyl-N-methylacetamide, 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 -t-butyl-3-methylene-2-pyrrolidone, 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-alkoxy poly(ethylene glycol) (meth)acrylate having a weight average molecular weight of up to 1500, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, 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 methylvinyl ether, di(ethylene glycol) methylvinyl ether, tri(ethylene glycol) methylvinyl ether, tetra(ethylene glycol) methylvinyl ether, poly(ethylene glycol) methylvinyl ether, allyl alcohol, 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 methylallyl ether, di(ethylene glycol) methylallyl ether, tri(ethylene glycol) methylallyl ether, tetra(ethylene glycol) methylallyl ether, poly(ethylene glycol) methylallyl ether, N-2-hydroxyethyl vinylcarbamate, N-carboxyvinyl-β-alanine (VINAL), N-carboxyvinyl-α-alanine, and combinations thereof.

[0275] 121. The aqueous solution of any one of embodiments 88 to 100, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N-ethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-propyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-3-methoxypropyl(meth)acrylamide, and combinations thereof.

[0276] 122. The aqueous solution of any one of embodiments 88-100, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of N-2-hydroxyethyl (meth)acrylamide, N,N-bis(hydroxyethyl) (meth)acrylamide, N-3-hydroxypropyl (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 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.

[0277] 123. The aqueous solution of any one of embodiments 88-100, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of N-2-aminoethyl (meth)acrylamide, N-2-methylaminoethyl (meth)acrylamide, N-2-ethylaminoethyl (meth)acrylamide, N-2-dimethylaminoethyl (meth)acrylamide, N-3-aminopropyl (meth)acrylamide, N-3-methylaminopropyl (meth)acrylamide, N-3-dimethylaminopropyl (meth)acrylamide, 2-aminoethyl (meth)acrylate, 2-methylaminoethyl (meth)acrylate, 2-ethylaminoethyl (meth)acrylate, 3-aminopropyl (meth)acrylate, 3-methylaminopropyl (meth)acrylate, 3-ethylaminopropyl (meth)acrylate, 3-amino-2-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate trimethylammonium hydrochloride, dimethylaminoethyl (meth)acrylate, vinyl amine, allyl amine, and combinations thereof.

[0278] 124. The aqueous solution of any one of embodiments 88-100, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of acrylic acid, methacrylic acid, ethylacrylic acid, propylacrylic acid, 2-acrylamidoglycolic acid, 3-acrylamidopropionic acid, 4-acrylamidobutanoic acid, 5-acrylamidopentanoic acid, 3-acryloyloxypropionic acid, 4-acryloyloxybutanoic acid, 5-acryloyloxypentanoic acid, and combinations thereof.

[0279] 125. The aqueous solution of any one of embodiments 88-100, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of N-vinylpyrrolidone (also known as N-vinyl-2-pyrrolidone), N-vinyl-3-methyl-2-pyrrolidone, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-6-methyl-2-pyrrolidone, N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, N-vinyl-5,5-dimethyl-2-pyrrolidone, N-vinyl-3,3,5-trimethyl-2-pyrrolidone, N-vinylpiperidone (also known as N-vinyl-2-piperidone), N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-5-methyl-2-piperidone, N-vinyl-6-methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone, N-vinyl-3,5-dimethyl-2-piperidone, N-vinyl-4,4-dimethyl-2-piperidone, N-vinylcaprolactam (also known as N-vinyl-2-caprolactam), N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, and mixtures thereof. Preferably, the N-vinyl amide monomer is N-vinylpyrrolidone, N-vinyl-N-methylacetamide, or a combination thereof.

[0280] 126. The aqueous solution of any one of embodiments 88-100, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of 1-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 1-n-propyl-3-methylene-2-pyrrolidone, 1-n-propyl-5-methylene-2-pyrrolidone, 1-iso-propyl-3-methylene-2-pyrrolidone, 1-iso-propyl-5-methylene-2-pyrrolidone, 1-n-butyl-3-methylene-2-pyrrolidone, 1-t-butyl-3-methylene-2-pyrrolidone, and combinations thereof.

[0281] 127. The aqueous solution of any one of embodiments 88-100, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of 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-alkoxy poly(ethylene glycol) (meth)acrylate having a weight average molecular weight of up to 1500, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, and combinations thereof.

[0282] 128. The aqueous solution of any one of embodiments 88-100, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of ethylene glycol monovinyl ether, di(ethylene glycol) monovinyl ether, tri(ethylene glycol) monovinyl ether, tetra(ethylene glycol) monovinyl ether, poly(ethylene glycol) monovinyl ether, ethylene glycol methylvinyl ether, di(ethylene glycol) methylvinyl ether, tri(ethylene glycol) methylvinyl ether, tetra(ethylene glycol) methylvinyl ether, poly(ethylene glycol) methylvinyl ether, and combinations thereof.

[0283] 129. The aqueous solution of any one of embodiments 88-100, wherein the at least one hydrophilic vinylic monomer comprises at least one vinylic monomer selected from the group consisting of allyl alcohol, 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 methylallyl ether, di(ethylene glycol) methylallyl ether, tri(ethylene glycol) methylallyl ether, tetra(ethylene glycol) methylallyl ether, poly(ethylene glycol) methylallyl ether, and combinations thereof.

[0284] 130. The aqueous solution of any one of embodiments 88-129, wherein the hydrophilic copolymer has a weight average molecular weight of at least about 100,000 Daltons.

[0285] 131. The aqueous solution of any one of embodiments 88-129, wherein the hydrophilic copolymer has a weight average molecular weight of at least about 125,000 Daltons.

[0286] 132. The aqueous solution of any one of embodiments 88-129, wherein the hydrophilic copolymer has a weight average molecular weight of at least about 250,000 Daltons.

[0287] 133. The aqueous solution of any one of embodiments 88 to 129, wherein the hydrophilic copolymer has a weight average molecular weight of at least about 400,000 Daltons.

[0288] 134. The aqueous solution of any one of embodiments 88 to 133, wherein the aqueous solution is a packaging solution for packaging a hydrogel lens contact lens comprising or made from a polymeric material comprising 1,2-diol and 1,3-diol moieties.

[0289] 135. The aqueous solution of any one of embodiments 88 to 133, wherein the aqueous solution is a storage solution for storing a hydrogel lens contact lens comprising or made from a polymeric material comprising 1,2-diol and 1,3-diol moieties.

[0290] 136. The aqueous solution of any one of embodiments 88 to 133, wherein the aqueous solution is a treatment solution for forming a coating on a hydrogel lens contact lens comprising or made from a polymeric material comprising 1,2-diol and 1,3-diol moieties.

[0291] The foregoing disclosure is intended to enable the ordinarily skilled person to practice the application. Various modifications, alterations, and combinations can be made with the embodiments described herein. It is intended that the specification and examples be considered exemplary.

[0292] Example 1

[0293] Surface wettability test

[0294] Water contact angle (WCA) on a contact lens is a general measure of the surface wettability of the contact lens. In particular, a low water contact angle corresponds to a more wettable surface.

[0295] Dynamic captive bubble contact angles of contact lenses were measured using FDS instrument apparatus from FDS Future Digital Scientific Corp. The FDS equipment is capable of measuring advancing and receding contact angles. The measurements were performed on hydrated contact lenses at room temperature. The contact lenses were removed from vials and soaked in about 40 mL of fresh phosphate buffered saline (PBS) and shaken for at least 30 minutes, then replaced with fresh PBS, soaked and shaken for another 30 minutes (unless otherwise indicated). The contact lenses were then placed on a lens paper and lightly wiped to remove surface water, then placed onto the top of a lens holder that was curved forward, then the lens holder top was twisted on. The secured lens holder was placed in a glass cell cuvette filled with filtered PBS. The glass cell cuvette was placed on the stage of the FDS instrument. The stage height and syringe needle were adjusted to dispense a bubble onto the lens surface. The dispensing / withdrawal was repeated for 3 cycles for each lens to obtain advancing and receding contact angles. The receding contact angles are reported in the following examples.

[0296] The average contact angle (sessile drop method) of contact lenses was measured using a VCA 2500 XE contact angle measurement apparatus (from AST, Inc. located in Boston, MA). This equipment is capable of measuring advancing or receding contact angles or sessile (static) contact angles. These measurements were performed on fully hydrated contact lenses and immediately after blotting as follows. The contact lenses were removed from vials and washed 3 times in about 200 ml of fresh DI water to remove loosely bound packaging additives from the lens surface. The lenses were then placed on top of a piece of lint-free clean cloth (Alpha Wipe TX1009), lightly wiped to remove surface water, mounted on the contact angle measurement pedestal, blown dry with a stream of dry air and finally the sessile drop method contact angle was measured automatically using software provided by the manufacturer. The DI water used to measure the contact angle had a resistivity of >18 MΩ cm and the drop volume used was 2 μΐ. The tweezers and pedestal were thoroughly washed with isopropyl alcohol and rinsed with DI water before making contact with the contact lenses.

[0297] Lubricity Evaluation

[0298] The lubricity of contact lenses was evaluated by using a finger feel lubricity test that qualitatively characterizes the slipperiness of the lens surface on a scale of friction ratings from 0 to 4. The higher the friction rating, the lower the slipperiness (or lubricity).

[0299] Commercial Lenses: OASYS TM ; ADVANCE PLUS TM; Aqua Comfort and AIR The abrasion ratings (hereinafter referred to as "FR") are assigned as 0, 1, 2, 3, and 4, respectively. These are used as standard lenses to determine the abrasion rating of the lens being tested.

[0300] Rinse the sample in PBS for at least two 30-minute washes, then transfer it to fresh PBS for evaluation. Before evaluation, wash hands with soap, rinse thoroughly with DI water, and then... Dry with a towel. Process these samples between your fingers and assign values ​​to each sample relative to the standard lenses described above. For example, if a lens is determined to be only slightly better than AIR... For lenses, they are assigned the number 3. The friction rating value is obtained by averaging the results of at least two friction ratings of contact lenses by two or more individuals and / or by averaging the friction ratings of two or more contact lenses (from the same batch of lenses produced) by one person.

[0301] The finger lubricity (i.e., friction rating) of contact lenses can be determined according to the procedure described above: directly without packaging (OOP), after removal from the packaging and subsequent immersion in PBS for ≥30 min, or after i cycles (e.g., 7, 14, 21, or 30 cycles) of manual rubbing treatment.

[0302] chemicals

[0303] The following abbreviations are used in the following examples: NVP represents N-vinylpyrrolidone; VPBA represents 4-vinylphenylboronic acid; PVA represents polyvinyl alcohol; MPC represents 2-methacryloyloxyethylphosphorylcholine; PBS represents phosphate-buffered saline having a pH of 7.2 ± 0.2 at 25°C and containing approximately 0.044 wt.% NaH₂PO₄·H₂O, approximately 0.388 wt.% Na₂HPO₄·2H₂O, and approximately 0.79 wt.% NaCl, where wt.% represents weight percentage; TAA represents tert-amyl alcohol; PrOH represents 1-propanol; IPA represents isopropanol; PEG 200 MA indicates polyethylene glycol monomethacrylate with a number-average molecular weight Mn of 200 Daltons; PEG 300 MA indicates polyethylene glycol monomethacrylate with a number-average molecular weight Mn of 300 Daltons; PEG 950MA represents polyethylene glycol monomethacrylate having a number average molecular weight Mn of 950 Dalton; DMA represents N,N-dimethylacrylamide; BMA represents n-butyl methacrylate; DGMEMA represents di(ethylene glycol) methacrylate; AAPH (Vazo-56) represents 2,2'-azobis-(2-amidinopropane dihydrochloride; DI water represents deionized water; bME represents b-mercaptoethanol; HPMC represents hydroxypropyl methylcellulose; PEG400 represents polyethylene glycol having a number average molecular weight of 400 Dalton; D9 represents monobutyl terminated monomethacryloxypropyl terminated polydimethylsiloxane (Mw of about 984 g / mol from Shin-Etsu); MMA represents methyl methacrylate; TEGDMA represents triethylene glycol dimethacrylate; VAZO 64 represents 2,2'-dimethyl-2,2'azobispropionitrile; Nobloc is 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl methacrylate; UV28 represents 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropyloxy]phenyl}-5-chloro-2H-benzotriazole; “G4” macromonomer represents a di-methacryloxypropyl terminated polysiloxane having formula (A) (Mn of about 13.5 Kg / mol, OH content of about 1.8 meq / g).

[0304]

[0305] from of AquaComfort (DACP) contact lenses are polyvinyl alcohol contact lenses. They were produced from an aqueous lens formulation comprising a polyvinyl alcohol prepolymer having repeating units of formula (I) and according to the procedure described in Example 3 of WO 02 / 071106, according to the automated lens manufacturing method described in Examples 8-8d of WO 2002071106. The DACP contact lenses were removed from their propylene lens packages and soaked in deionized water (DI water) overnight or longer before use in the following examples of the present application.

[0306] Example 3

[0307] Preparation of the polymerizable composition

[0308] Lens formulations (polymerizable compositions) III to VI having the composition (in units of parts) as shown in Table 1 were prepared.

[0309] Table 1

[0310]

[0311] The formulation was prepared by adding the listed components in their target amounts to a clean bottle, mixing at 600 rpm with a stir bar at room temperature for 30 minutes. After all solids were dissolved, the formulation was filtered by using a 2.7 pm glass microfiber filter.

[0312] Cast molded silicone hydrogel contact lenses

[0313] The lens formulation was purged with nitrogen gas at room temperature for 30 to 35 minutes. The N2 purged lens formulation was introduced into a polypropylene mold and heat cured in an oven under the following curing conditions: ramp from room temperature to a first temperature and then hold at the first temperature for a first curing time period; ramp from the first temperature to a second temperature and hold at the second temperature for a second curing time period; optionally ramp from the second temperature to a third temperature and hold at the third temperature for a third curing time period; and optionally ramp from the third temperature to a fourth temperature and hold at the fourth temperature for a fourth curing time period.

[0314] The lens mold was opened by using a demolding machine with a push pin. The lens was pushed to the bottom curve mold with the push pin and then the mold was separated into a bottom curve half mold and a front curve half mold. The bottom curve half mold with the lens on it was placed in an ultrasonic device (e.g., single horn ultrasonic device by Dukane). With a certain energy force, the lens in dry state was released from the mold. The lens in dry state was loaded into a designed extraction tray. Alternatively, the lens can be removed from the bottom curve half mold by floating (i.e., soaking in organic solvent such as IPA without ultrasonic).

[0315] The obtained silicone hydrogel (SiHy) contact lenses were subjected to the following post-molding processes before lens characterization. After demolding, the SiHy lenses prepared above were extracted with 100% IPA at room temperature for 15 minutes, soaked in 50% / 50% IPA / water mixture for 30 minutes and then soaked in DI water for 30 minutes, and finally rinsed with PBS saline for about 60 minutes. After rinsing in PBS for 5 min, the lenses were then ready for use in the following examples of the present application.

[0316] The obtained SiHy lenses are referred to as glycerol-containing SiHy lenses because they comprise repeating units of the polydimethylsiloxane vinylic crosslinker of Formula (A) and each of the repeating units of the polydimethylsiloxane vinylic crosslinker of Formula (A) comprises a siloxane unit having one glycerol-containing organic substituent.

[0317] Example 4

[0318] Preparation of NVP-VPBA copolymer

[0319] In a 100 ml round bottom flask, 1-phenylvinylboronic acid 0.32 g, NVP 4.47 g and 0.047 g Vazo 64 were added. Nitrogen inlet and water condenser were attached to the flask. The flask was placed in an oil bath under magnetic stirring and heated at 75 °C for 5 hours. After the reaction mixture was cooled to room temperature, it was transferred to a 20 ml glass vial. Nitrogen was blown through the needle into the liquid overnight and an amber very sticky liquid was obtained. An aqueous solution of the obtained product (2% by weight) was completely transparent. The aqueous GPC test showed a number average molecular weight of 367 K Da and a polydispersity of 2.6.

[0320] Preparation of aqueous solution of poly(NVP-co-VPBA)

[0321] The coating solution was prepared by dissolving the NVP-VPBA copolymer prepared above in DI water to have a concentration of about 2% by weight and then adjusted to a pH of about 9.

[0322] Preparation of poly(NVP-co-VPBA) coated PVA contact lenses

[0323] The PVA contact lenses prepared in Example 2 were soaked in the coating solution prepared above at room temperature overnight. The resulting PVA contact lenses were tested by XPS test. The XPS results in Table 1 show that the resulting PVA contact lenses have a relatively higher N content on the lens surface compared to the uncoated lenses, indicating the presence of a poly(NVP-co-VPBA) layer (or coating) on the lens surface.

[0324] Table 2

[0325] Sample Atomic % C Atomic % N Atomic % O Coated PVA lens 65.29 3.62 31.09 Uncoated lens 55.22 1.15 43.63

[0326] Example 5

[0327] Synthesis of binary copolymer - poly(PEG 200 MA-co-VPBA)

[0328] About 1.133 g of VPBA was dissolved in 25.0 g of PrOH to obtain a VPBA solution, which was introduced into a 500 mL reactor equipped with a N2 inlet, an overhead stirrer, a thermocouple, a condenser, and a bubbler, by a syringe equipped with a 5 pm nylon filter. About 18.88 g of PEG 200MA was dissolved in 20.0 g DI water, poured into the reactor and rinsed with an additional 2 x 20.0 g DI water. About 00693 g of AAPH was dissolved in 5.0 g DI water, poured into the reactor and rinsed with an additional 2 x 5.0 DI water, followed by a rinse with 15.0 g DI water and 65.0 g PrOH. About 3.65 mL of a mercaptoethanol (bME) solution (0.274 g bME in 100 mL of DI water) was added with a micropipette.

[0329] The reaction solution was purged with nitrogen (200 mL / minute) at 20 °C for 30 minutes while stirring at 150 rpm. The nitrogen flow was reduced to a blanket and the copolymer solution was heated according to the following schedule: it took two hours to reach 61 °C; it was held at 61 °C for about 8 hours; and it took 2 hours to cool to 20 °C.

[0330] Ternary copolymer - poly(PEG 200 Synthesis of MA-co-MPC-co-VPBA) ternary copolymer

[0331] About 1.011 g of VPBA was dissolved in 25.0 g PrOH to obtain a VPBA solution, which was introduced into a 500 mL reactor equipped with a N2 inlet, overhead stirrer, thermocouple, condenser, and bubbler, via a syringe equipped with a 5 pm nylon filter. About 12.278 g of PEG 200 MA was dissolved in 20.0 g DI water, poured into the reactor and rinsed with an additional 2 x 20.0 g DI water. About 00693 g of AAPH was dissolved in 5.0 g DI water, poured into the reactor and rinsed with an additional 2 x 5.0 DI water, followed by a rinse with 15.0 g DI water and 65.0 g PrOH. About 3.65 mL of a mercaptoethanol (bME) solution (0.274 g bME in 100 mL of DI water) was added with a micropipette.

[0332] The reaction solution was purged with nitrogen (200 mL / minute) at 20 °C for 30 minutes while stirring at 150 rpm. The nitrogen flow was reduced to a blanket and the copolymer solution was heated according to the following schedule: it took two hours to reach 61 °C; it was held at 61 °C for about 8 hours; and it took 2 hours to cool to 20 °C.

[0333] Various copolymers (binary or ternary) were prepared according to the procedure described above, except for different amounts and different types of vinylic monomers as shown in Table 3.

[0334] Table 3

[0335]

[0336] *The concentration (milliequivalents) of boronic acid (BA) groups in the copolymer was determined by titration Example 6

[0337] The VPBA, DMA, PEG 200 Copolymers and terpolymers of MA and MPC were added to packaged saline solutions (consisting of about 0.15 wt% HPMC, about 1.0 wt% PEG 400, about 0.294 wt% sodium citrate dihydrate, about 0.19 wt% NaCl, about 1.157 wt% disodium phosphate dihydrate, about 0.0034 wt% poloxamer, and about 97.2056 wt% water) at concentrations ranging from 0.05-1 wt%. The pH of the packaged saline varied from 8 to 9.5 and the buffer NaH2PO4·2H2O varied from 46 to 92 mmol / L.

[0338] The PVA contact lenses prepared in Example 2, the glycerol-containing SiHy contact lenses prepared in Example 3, and silicon wafers served as substrates for coating and were individually packaged in polypropylene packaging shells containing about 0.55-0.65 ml of the above-prepared coating solution or about 0.65 ml of PBS as a control, the shells were sealed with AI foil and autoclaved (30-45 minutes; 121 °C; 2 atmospheres).

[0339] The above-treated substrates were removed from the packaging and thoroughly rinsed with DI water and then dried. The surface atomic composition of the dried, treated substrates was analyzed with XPS.

[0340] Table 4 shows comparative XPS results with and without copolymer on two test lenses and a Si wafer. Pure copolymer was tested without lenses on a Si wafer and the surface composition was also tested.

[0341] Table 4

[0342]

[0343] *Theoretical value based on copolymer structure calculations.

[0344] The phosphorous levels on the PVA lens surface were found to be comparable to both the theoretical and experimental values (from Si wafer of pure copolymer). This indicates binding on the lens even after standard rinsing and drying. Significant boron binding was also observed, confirming the presence of a surface film.

[0345] It was also found that the levels of phosphorous and boron on the glycerol-containing SiHy lenses were practically negligible, indicating little incorporation in the lens. This can be a result of the lower OH concentration on the surface.

[0346] It is believed that the low levels of Si observed for the uncoated and coated PVA contact lenses is due to an artifact of extraneous silicon contamination in the XPS experiment.

[0347] Example 7

[0348] The copolymer 2 [i.e., poly(VPBA-co-DMA)] prepared in Example 5, the terpolymer 3 [i.e., poly(VPBA-co-PEG 200 MA-co-MPC)] prepared in Example 5, and the terpolymer 4 [i.e., poly(VPBA-co-PEG 200 MA-co-MPC)] prepared in Example 5 were added to the packaging saline solution at a concentration of 1 wt.%. The pH of the packaging saline was about 9.0 and the concentration of NaH2PO4-2H2O was about 92 mmol / L.

[0349] The PVA contact lenses prepared in Example 2 and the glycerol-containing SiHy contact lenses prepared in Example 3 were individually packaged in polypropylene packaging shells containing about 0.65 ml of packaging saline without any copolymer (control) or with 0.5 wt.% of the copolymer prepared above, the shells were sealed with AI foil and autoclaved (30-45 min; 121 °C; 2 atmospheres).

[0350] The lubricity (friction rating) and water contact angle (static sessile drop method) of the contact lenses obtained were determined directly out of the package (OOP) but after soaking in PBS for >30 min and are reported in Table 5.

[0351] Table 5

[0352]

[0353] Example 8

[0354] Synthesis of binary and terpolymer

[0355] Poly(MPC 0.9 co-VPBA 0.1 )

[0356] In a 20 ml vial, 1.18 g (4 mmol) of MPC, 0.556 g (5 mmol) of NVP and 0.148 g (1 mmol) of VPBA and 10 ml of ethanol, vazo 64 1.64 mg (0.01 mmol) were added. Nitrogen was gently bubbled into the solution for 5 min to purge the oxygen and then the vial was sealed. The polymerization was carried out at 60°C for 6 hours. After cooling the vial, the content was poured into a large amount of a mixture of diethyl ether and chloroform (8 / 2 by volume) to purge any remaining monomers and to precipitate the polymer. The precipitate was filtered out using a glass filter and dried in vacuum.

[0357] Poly(MPC 0.4 - co-NVP 0.5 - co-VPBA 0.1 )

[0358] In a 20 ml vial, 1.18 g (4 mmol) of MPC, 0.556 g (5 mmol) of NVP and 0.148 g (1 mmol) of VPBA and 10 ml of ethanol, vazo 64 1.64 mg (0.01 mmol) were added. Nitrogen was gently bubbled into the solution for 5 min to purge the oxygen and then the vial was sealed. The polymerization was carried out at 60°C for 6 hours. After cooling the vial, the content was poured into a large amount of a mixture of diethyl ether and chloroform (8 / 2 by volume) to purge any remaining monomers and to precipitate the polymer. The precipitate was filtered out using a glass filter and dried in vacuum.

[0359] Poly(MPC 0.6 - co-BMA 0.3 - co-VPBA 0.1 )

[0360] In a 20 ml vial, 1.18 g (4 mmol) of MPC, 0.556 g (5 mmol) of NVP and 0.148 g (1 mmol) of VPBA and 10 ml of ethanol, vazo 64 1.64 mg (0.01 mmol) were added. Nitrogen was gently bubbled into the solution for 5 min to purge the oxygen and then the vial was sealed. The polymerization was carried out at 60°C for 6 hours. After cooling the vial, the content was poured into a large amount of a mixture of diethyl ether and chloroform (8 / 2 by volume) to purge any remaining monomers and to precipitate the polymer. The precipitate was filtered out using a glass filter and dried in vacuum. It was determined that the copolymer obtained had a weight average molecular weight Mw of 150 KDa.

[0361] Poly(MPC 0.8 - co-BMA 0.1 - co-VPBA 0.1 )

[0362] In a 20 ml vial, 2.36 g (8 mmol) of MPC, 0.142 g (1 mmol) of BMA and 0.148 g (1 mmol) of VPBA and 10 ml of ethanol, vazo 64 1.64 mg (0.01 mmol) were added. Nitrogen was gently bubbled into the solution for 5 min to purge the oxygen and then the vial was sealed. The polymerization was carried out at 60°C for 6 hours. After cooling the vial, the content was poured into a large amount of a mixture of diethyl ether and chloroform (8 / 2 by volume) to purge any remaining monomers and to precipitate the polymer. The precipitate was filtered out using a glass filter and dried in vacuum. The copolymer obtained was determined to have a weight average molecular weight Mw of 160 KDa.

[0363] Poly(MPC 0.8 - co-BMA 0.1 - co-VPBA 0.1 )

[0364] In a 40 ml vial, 4.72 g (16 mmol) of MPC, 0.285 g (2 mmol) of BMA and 0.296 g (2 mmol) of VPBA and 20 ml of ethanol, vazo 64 3.2 mg (0.02 mmol) were added. Nitrogen was gently bubbled into the solution for 5 min to purge the oxygen and then the vial was sealed. The polymerization was carried out at 60°C for 6 hours. After cooling the vial, the content was poured into a large amount of a mixture of diethyl ether and chloroform (8 / 2 by volume) to purge any remaining monomers and to precipitate the polymer. The precipitate was filtered out using a glass filter and dried in vacuum. The copolymer obtained was determined to have a weight average molecular weight Mw of 286 KDa.

[0365] Poly(MPC 0.8 - co-BMA 0.1 - co-VPBA 0.1 )

[0366] In a 40 ml vial, 4.72 g (16 mmol) of MPC, 0.285 g (2 mmol) of BMA and 0.296 g (2 mmol) of VPBA and 20 ml of ethanol, vazo 64 1.3 mg (0.01 mmol) were added. Nitrogen was gently bubbled into the solution for 5 min to purge the oxygen and then the vial was sealed. The polymerization was carried out at 60°C for 6 hours. After cooling the vial, the content was poured into a large amount of a mixture of diethyl ether and chloroform (8 / 2 by volume) to purge any remaining monomers and to precipitate the polymer. The precipitate was filtered out using a glass filter and dried in vacuum. The copolymer obtained was determined to have a weight average molecular weight Mw of 386 KDa.

[0367] Poly(MPC 0.8 - co-BMA 0.1 - co-VPBA 0.1 )

[0368] In a 40 ml vial, 4.72 g (16 mmol) of MPC, 0.285 g (2 mmol) of BMA and 0.296 g (2 mmol) of VPBA and 10 ml of ethanol, vazo 64 3.2 mg (0.02 mmol) were added. Nitrogen was gently bubbled into the solution for 5 min to purge oxygen and then the vial was sealed. Polymerization was carried out at 60 °C for 6 hours. After the vial was cooled, the contents were poured into a large mixture of diethyl ether and chloroform (8 / 2 by volume) to purge any remaining monomers and to precipitate the polymer. The precipitate was filtered out using a glass filter and dried in vacuum. The copolymer obtained was determined to have a weight average molecular weight Mw of 688 KDa.

[0369] Preparation of packaged saline

[0370] Phosphate buffered saline (PBS)

[0371] The PBS was prepared by dissolving all the required components to have the following composition: about 0.044 wt.% NaH2PO4·H2O, about 0.388 wt.% Na2HPO4·2H2O, and about 0.79 wt.% NaCl; and a pH of 7.2 ± 0.2 at 25 °C.

[0372] Base packaging saline (BPS)

[0373] The base saline was prepared by dissolving all the required components to have the following composition: about 0.15 wt% HPMC, about 1.0 wt% PEG400, about 0.294 wt% sodium citrate dihydrate, about 0.19 wt% NaCl, about 1.157 wt% disodium hydrogen phosphate dihydrate, about 0.0034 wt% poloxamer, and about 97.2056 wt% water.

[0374] Test packaging saline (TPS)

[0375] Several test packaging solutions (TPS1-TPS8) were prepared by dissolving the copolymer prepared above in the BPS prepared above to have the following composition shown in Table 6.

[0376] Table 6

[0377]

[0378] Lens preparation and packaging:

[0379] The PVA contact lenses prepared in Example 2 were individually packaged in polypropylene packaging shells containing about 0.65 ml of packaging saline (one of PBS, BPS and TPS1-TPS8 prepared above), the shells were sealed with AI foil and autoclaved (30-45 minutes; 121 °C; 2 atmospheres).

[0380] The lubricity (friction rating) of the contact lenses obtained was determined directly out of package (OOP) but after soaking in PBS for at least about 30 minutes, and the results are reported in Table 7.

[0381] The autoclaved lenses were removed from the package and desalted, and then dried at room temperature. Desalting was performed by rinsing the lenses in 3 successive washes in DI water, each wash lasting a minimum of 10 minutes. The lenses were then placed in a room temperature desiccator with flowing nitrogen for a minimum of 12 hours to obtain sufficient dryness for XPS. The samples were loaded into a Sage-Sun XPS (10 kV source, 0.2 eV step, 20 eV pass, 3 mm spot size) for surface elemental analysis. The percentage of phosphorous atoms on the surface of the lenses is reported in Table 7. Detection of phosphorous by XPS indicates the presence of a layer of MPC-containing copolymer on the surface of the lenses.

[0382] Table 7

[0383]

[0384] Example 9

[0385] Synthesis of binary and ternary copolymers

[0386] 2-Methacryloyloxyethylphosphorylcholine (MPC) (Mw = 295.27), 4-vinylphenylboronic acid (VPBA, Mw = 147.97), and optionally a third monomer (n-butyl methacrylate (BMA, Mw = 142.20) or di(ethylene glycol) methyl ether methacrylate (DGMEMA, Mw = 188.22), ethanol, and DI water were added to a 1 L jacketed reactor in the amounts shown in Table 8. The solution was degassed with a nitrogen flow rate of 250 mL / min for 30 minutes. Vazo-56 was dissolved into 20 to 30 g of DI water. The initiator solution was degassed in a dropping funnel with a nitrogen flow rate of about 50 mL / min for 30 minutes. The solution was heated to 49 °C in the reactor. The initiator solution was added and the solution temperature was maintained for 16 hours.

[0387] Purification:

[0388] The post-reaction solution was diluted to approximately 10% solids with DI water. The solution from the synthesis step was filtered through a course-fritted filter. The solution was diluted to 7.5-5.0% solids for purification by ultrafiltration using polyethersulfone membranes with a 30 kDa molecular weight cut-off. 8 to 10 bed volumes of water were used to remove residual monomer and solvent.

[0389] Polymer Characterization:

[0390] The boronic acid content of the copolymers was determined by acid-base titration in the presence of mannitol. The results are reported in Table 8.

[0391] The weight average molecular weight of the copolymers was determined using GPC with an RI detector and PEG standards. The results are reported in Table 8.

[0392] Table 8

[0393]

[0394] Example 10

[0395] Preparation of Packaging Saline

[0396] Phosphate buffered saline (PBS) and base packaging saline (BPS) prepared in Example 8 were used in this example.

[0397] Fourteen test packaging solutions (TPS1-TPS8) were prepared by dissolving one of the copolymers 9A to 9D prepared in Example 9 in the BPS prepared in Example 8 to have the following compositions shown in Table 9.

[0398] Table 9

[0399]

[0400] Lens Preparation and Packaging:

[0401] The PVA contact lenses prepared in Example 2 were individually packaged in polypropylene packaging shells containing about 0.65 ml of packaging saline (base packaging saline and one of the fourteen test packaging salines prepared above), the shells were sealed with AI foil and autoclaved (30-45 minutes; 121 °C; 2 atmospheres).

[0402] The lubricity (friction rating) of the contact lenses obtained was determined directly after removal from packaging (designated "OOP") and after soaking in PBS for at least about 30 minutes (designated "PBS"), and the results are reported in Table 10.

[0403] Sterilized lenses were removed from packaging and desalted, and then dried at room temperature. Desalting was performed by rinsing the lenses in 3 consecutive washes in DI water, each wash lasting a minimum of 10 minutes. The lenses were then placed in a room temperature desiccator with flowing nitrogen for a minimum of 12 hours to achieve sufficient dryness for XPS. The samples were loaded into a Sage-Sun XPS (10 kV source, 0.2 eV step, 20 eV pass, 3 mm spot size) for surface elemental analysis. The percentage of phosphorous atoms on the surface of the lenses is reported in Table 10. Detection of phosphorous by XPS indicates the presence of a layer of MPC-containing copolymer on the surface of the lenses.

[0404] Table 10

[0405]

[0406] Example 11

[0407] Binary and ternary copolymers

[0408] Binary and ternary copolymers were synthesized from the reactive compositions shown in Table 11 according to the procedure described in Example 9, except that the polymerization reactions were carried out at 52 °C. The resulting copolymers were purified and characterized according to the procedure described in Example 9. The results are reported in Table 11.

[0409] Table 11

[0410]

[0411] All publications, patents, and patent applications cited herein are hereby incorporated by reference in their entirety.

Claims

1. A method of producing a soft contact lens comprising the steps of: (1) obtaining a preformed hydrogel contact lens, wherein the preformed hydrogel contact lens is made of a polymeric material having at least 10% of repeat unit equivalents of 1,2-diol and 1,3-diol moieties, wherein the percentage of repeat unit equivalents of 1,2-diol and 1,3-diol moieties is calculated according to the following equation: where n is the total number of different types of diol containing repeat units, is the mole percentage of a particular type i diol containing repeat unit, is the number of 1,2-diols and 1,3-diols in each type i repeat unit; wherein the polymeric material comprises (i) at least 50% by moles of repeat units of vinyl alcohol, or (ii) repeat units of at least one glycol-containing vinylic monomer selected from the group consisting of N-2,3-dihydroxypropyl (meth)acrylamide, N-tris(hydroxymethyl)methyl (meth)acrylamide, glyceryl (meth)acrylate, 3-allyloxy- 1,2-propanediol, 2-allyloxymethyl-2-(hydroxymethyl)-l,3-propanediol, 2-allyloxymethyl-2-ethyl-l,3-propanediol, and combinations thereof, and / or repeat units of at least one glycol-containing vinylic crosslinker selected from the group consisting of N,N'-(l,2-dihydroxyethylidene)bis-(meth)acrylamide, N,N'-(2,3-dihydroxybutylidene)bis-(meth)acrylamide, a polydimethylsiloxane vinylic crosslinker comprising siloxane units each having a methyl substituent and one glycol-containing substituent, and combinations thereof; and (2) contacting the preformed hydrogel contact lens with an aqueous solution comprising a hydrophilic copolymer of (a) repeat units each having an aryl-dihydroxylboron-containing repeat unit of a boronic acid and (b) repeat units of at least one hydrophilic vinylic monomer comprising a phosphoryl-choline-containing vinylic monomer for a period of time to covalently attach a layer or coating of the hydrophilic copolymer to the preformed hydrogel contact lens through cyclic boronate linkages each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material; wherein the preformed hydrogel contact lens has a first surface lubricity, wherein the soft contact lens has a second surface lubricity that is better than the first surface lubricity of the preformed hydrogel contact lens.

2. The method of claim 1, wherein the aqueous solution has a pH of 6.8 to 8.

0.

3. The method of claim 2, wherein the aqueous solution comprises 0.01% to 2.5% by weight of the hydrophilic copolymer.

4. The method of claim 3, wherein the contacting period of time is at least 10 minutes.

5. The method of claim 4, the contacting step is performed by immersing the preformed hydrogel contact lens in the aqueous solution directly in the lens package, wherein the aqueous solution is a package solution containing a buffering agent for maintaining the pH of the aqueous solution.

6. The method of claim 5, wherein the package solution has a tonicity of 200 to 450 milliosmoles (mOsm).

7. The method of claim 6, further comprising the step of: sealing the lens package and autoclaving the sealed lens package at a temperature of 115°C to 125°C for 20-90 minutes.

8. The method of claim 7, wherein the preformed hydrogel contact lens is obtained by introducing a lens-forming composition into a reusable mold and curing the lens-forming composition in the reusable mold under spatial confinement of actinic radiation.

9. The method of claim 8, wherein the lens forming composition comprises a water-soluble, actinically crosslinkable polyvinyl alcohol prepolymer comprising: repeating units of vinyl alcohol and repeating units having the following formula (I): wherein: R3 is hydrogen or Ci-C6 alkyl; R4 is a Ci-C6 alkylene divalent radical; and R5 is hydrogen or Ci-C6 alkyl.

10. The method of claim 7, wherein the preformed hydrogel contact lens is obtained by introducing a lens forming composition into a disposable mold and curing the lens forming composition in the disposable mold.

11. The method of claim 10, wherein the lens forming composition comprises at least one glycol-containing vinylic monomer selected from the group consisting of N-2,3- dihydroxypropyl(meth)acrylamide, N-tris(hydroxymethyl)methyl(meth)acrylamide, glyceryl (meth)acrylate, 3-allyloxy-l,2-propanediol, 2-allyloxymethyl-2- (hydroxymethyl)-l,3-propanediol, 2-allyloxymethyl-2-ethyl-l,3-propanediol, and combinations thereof, and / or at least one repeating unit of a glycol-containing vinylic crosslinker selected from the group consisting of N,N'-(l,2-dihydroxyethylene)bis- (meth)acrylamide, N,N'-(2,3-dihydroxybutylene)bis-(meth)acrylamide, a polydimethylsiloxane vinylic crosslinker comprising siloxane units each having a methyl substituent and one glycol-containing substituent, and combinations thereof.

12. The method of any one of claims 1-11, wherein the at least one arylboronate- containing repeating unit is derived from at least one arylboronate-containing vinylic monomer of the following formula (II): wherein:

13. The method of claim 12, wherein the at least one arylboronate-containing repeating unit is derived from at least one arylboronate-containing vinylic monomer selected from the group consisting of 3-vinylphenylboronic acid, 4-vinylboronic acid, 3- (meth)acrylamidophenylboronic acid, 4-(meth)acrylamidophenylboronic acid, and combinations thereof. R6is an ethylenically unsaturated group of the formula (R7)q1O(CR8R9)q2R10wherein q1and q2are independently of each other 0 or 1, R7and R8are independently of each other a C2-C8alkylene divalent radical, and R9is a C2-C8alkylene. ​ ​ ​ ​ R1is H, NO2, F, Cl, or CF3; Q is CH2-CH=CH2, or -CH=CH2; L is a direct bond, a C1-C4 alkylene divalent radical, a divalent radical wherein Y1is CH(OH) or a C1-C4 alkylene divalent radical, Y2is a C1-C4 alkylene divalent radical, R o is H or C1-C4 alkyl. ​ 14. The method of any one of claims 1-11, wherein the arylboronate-containing repeat unit is derived from at least one arylboronate-containing vinylic monomer selected from the group consisting of reaction products of an amino-containing phenyl boronic acid derivative and a (meth)acrylic acid halide, reaction products of an amino-containing phenyl boronic acid derivative and a carboxyl-containing vinylic monomer in the presence of a carbodiimide and N-hydroxysuccinimide, reaction products of a carboxyl-containing phenyl boronic acid derivative and an amino-containing vinylic monomer in the presence of a carbodiimide and N-hydroxysuccinimide, and combinations thereof, wherein the carboxyl-containing phenyl boronic acid derivative is selected from the group consisting of 3-carboxyphenyl boronic acid, 4-carboxyphenyl boronic acid, 3- boronatephenyl acetic acid, 4-boronatephenyl acetic acid, 2-(4-boronatephenyl)-2- methylpropanoic acid, 3-(4-boronatephenyl)propanoic acid, 3-(3-boronatephenyl)propanoic acid, 5-(3-boronatephenyl)pentanoic acid, 5-(4-boronatephenyl)pentanoic acid, 4-(2-carboxyethyl)-3-nitrophenyl boronic acid, 3-(3-carboxypropanoylamino)phenyl boronic acid, 3-amino-3-(4-boronatephenyl)propanoic acid, and combinations thereof, wherein the amino-containing phenyl boronic acid derivative is selected from the group consisting of 3-aminophenyl boronic acid, 4-aminophenyl boronic acid, 4-amino-3- nitrophenyl boronic acid, 4-amino-4-fluorophenyl boronic acid, 2-(aminomethyl)-5- nitrophenyl boronic acid, 3-(aminomethyl)-phenyl boronic acid, 3-amino-5- nitrophenyl boronic acid, 3-amino-3-(4-boronatephenyl)propanoic acid, and combinations thereof, wherein the carboxyl-containing vinylic monomer is selected from the group consisting of 2-acrylamidoglycolic acid, 3-acrylamidopropionic acid, 4-acrylamidobutanoic acid, 5- acrylamidopentanoic acid, 3-acryloyloxypropanoic acid, 4-acryloyloxybutanoic acid, 5- acryloyloxypentanoic acid, and combinations thereof, wherein the amino-containing vinylic monomer is selected from the group consisting of (meth)acrylic acid amino-C2-C4 alkyl ester, (meth)acrylic acid C1-C3 alkylamino-C2-C4 alkyl ester, amino-C2-C4 alkyl(meth)acrylamide, C1-C3 alkylamino-C2-C4 alkyl(meth)acrylamide, vinyl amine, allyl amine, and combinations thereof.

15. The method of claim 14, wherein the hydrophilic copolymer comprises (a) 0.5% to 25% by mole of the arylboronate-containing repeat unit and (b) 75% to 99.5% by mole of repeat units of the at least one hydrophilic vinylic monomer, with the proviso that the sum of the mole percentages of components (a) and (b) and other components not listed above is 100%.

16. The method of claim 15, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N-ethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-propyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-3-methoxypropyl(meth)acrylamide, N-2-hydroxyethyl(meth)acrylamide, N,N-bis(hydroxyethyl)(meth)acrylamide, N-3-hydroxypropyl(meth)acrylamide, N-2-hydroxypropyl(meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 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, 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, 2-hydroxypropyl (meth)acrylic acid trimethylammonium hydrochloride, dimethylaminoethyl (meth)acrylate, 2-(meth)acrylamidoglycolic acid, (meth)acrylic acid, ethylacrylic acid, propylacrylic acid, 3-(meth)acrylamidopropionic acid, 4-(meth)acrylamidobutanoic acid, 5-(meth)acrylamidopentanoic acid, 3-(meth)acryloyloxypropionic acid, 4-(meth)acryloyloxybutanoic acid, 5-(meth)acryloyloxypentanoic acid, 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-vinyl caprolactam, N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, 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-alkoxy poly(ethylene glycol) (meth)acrylate having a weight average molecular weight of up to 1500, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, 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 methylvinyl ether, di(ethylene glycol) methylvinyl ether, tri(ethylene glycol) methylvinyl ether, tetra(ethylene glycol) methylvinyl ether, poly(ethylene glycol) methylvinyl ether, allyl alcohol, 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 methylallyl ether, di(ethylene glycol) methylallyl ether, tri(ethylene glycol) methylallyl ether, tetra(ethylene glycol) methylallyl ether, poly(ethylene glycol) methylallyl ether, N-2-hydroxyethyl vinylcarbamate, N-carboxyvinyl-β-alanine, N-carboxyvinyl-α-alanine, and combinations thereof.

17. The method of claim 14, wherein the hydrophilic copolymer comprises (a) 1 to 20 percent by moles of the aryl-containing dihydroxysilyl-containing repeat unit, (b) 60 to 98 percent by moles of repeat units of at least one phosphorylcholine-containing vinylic monomer, and (c) 1 to 20 percent by moles of at least one acrylic monomer having 3 to 16 carbon atoms, with the proviso that the sum of the percent by moles of components (a), (b), and (c) and other components not listed above is 100 percent.

18. The method of claim 17, wherein the at least one acrylic monomer is selected from (meth)acrylic acid C1-C. 12 Alkyl esters, (meth)acrylic acid hydroxy-substituted C2-C 12 Alkyl esters, C2-C carboxyl-substituted (meth)acrylic acid esters 12 Alkyl esters, (meth)acrylic acid NH2-substituted C2-C 12 Alkyl esters, methylamino-substituted C2-C (meth)acrylates 12 Alkyl esters, dimethylamino-substituted (meth)acrylates, C2-C 12 Alkyl esters, (meth)acrylates, ethylamino-substituted C2-C 10 Alkyl esters, diethylamino-substituted C2-C8 alkyl esters of (meth)acrylate, C2-C 12 Alkyl (meth)acrylamide, hydroxy-substituted C2-C 12 Alkyl (meth)acrylamide, carboxyl-substituted C2-C 12 Alkyl (meth)acrylamide, NH2-substituted C2-C 12 Alkyl (meth)acrylamide, methylamino-substituted C2-C 12 Alkyl (meth)acrylamide, dimethylamino-substituted C2-C 12 Alkyl (meth)acrylamide, ethylamino-substituted C2-C 10 Alkyl (meth)acrylamide, diethylamino-substituted C2-C8 alkyl (meth)acrylamide, ethylene glycol (meth)acrylate, di(ethylene glycol)(meth)acrylate, tri(ethylene glycol)(meth)acrylate, tetra(ethylene glycol)(meth)acrylate, 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 combinations thereof.

19. The method of claim 18, wherein the phosphorylcholine-containing vinylic monomer is selected from the group consisting of (meth)acryloyloxyethyl phosphorylcholine, (meth)acryloyloxypropyl phosphorylcholine, 4-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethyl phosphate, 2-[(meth)acryloylamino]ethyl-2'-(trimethylammonio)-ethyl phosphate, 3-[(meth)acryloylamino]propyl-2'-(trimethylammonio)ethyl phosphate, 4-[(meth)acryloylamino]butyl-2'-(trimethylammonio)ethyl phosphate, 5-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 6-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)-ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(triethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(tripropylammonio)ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(tributylammonio)ethyl phosphate, 2-((meth)acryloyloxy)propyl-2'-(trimethylammonio)-ethyl phosphate, 2-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxycarbonyl)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonyl)ethyl-2'-(trimethylammonio)-ethyl phosphate, 2-(vinylcarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(butenoyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, and combinations thereof.

20. The method of claim 19, wherein the at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N-ethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-propyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-3-methoxypropyl(meth)acrylamide, N-2-hydroxyethyl(meth)acrylamide, N,N-bis(hydroxyethyl)(meth)acrylamide, N-3-hydroxypropyl(meth)acrylamide, N-2-hydroxypropyl(meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 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, 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, 2-hydroxypropyl (meth)acrylic acid trimethylammonium hydrochloride, dimethylaminoethyl (meth)acrylate, 2-(meth)acrylamidoglycolic acid, (meth)acrylic acid, ethylacrylic acid, propylacrylic acid, 3-(meth)acrylamidopropionic acid, 4-(meth)acrylamidobutanoic acid, 5-(meth)acrylamidopentanoic acid, 3-(meth)acryloyloxypropionic acid, 4-(meth)acryloyloxybutanoic acid, 5-(meth)acryloyloxypentanoic acid, 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-vinyl caprolactam, N-vinyl-3-methyl-2-caprolactam, N-vinyl-4-methyl-2-caprolactam, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam, N-vinyl-3,5-dimethyl-2-caprolactam, N-vinyl-4,6-dimethyl-2-caprolactam, N-vinyl-3,5,7-trimethyl-2-caprolactam, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, 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-alkoxy poly(ethylene glycol) (meth)acrylate having a weight average molecular weight of up to 1500, methoxy-poly(ethylene glycol) ethyl (meth)acrylamide having a number average molecular weight of up to 1500, 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 methylvinyl ether, di(ethylene glycol) methylvinyl ether, tri(ethylene glycol) methylvinyl ether, tetra(ethylene glycol) methylvinyl ether, poly(ethylene glycol) methylvinyl ether, allyl alcohol, 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 methylallyl ether, di(ethylene glycol) methylallyl ether, tri(ethylene glycol) methylallyl ether, tetra(ethylene glycol) methylallyl ether, poly(ethylene glycol) methylallyl ether, N-2-hydroxyethyl vinylcarbamate, N-carboxyvinyl-β-alanine, N-carboxyvinyl-α-alanine, and combinations thereof; wherein the hydrophilic copolymer has a weight average molecular weight of at least 100,000 Daltons.

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