WO2009089205A1 - Solutions de conditionnement - Google Patents

Solutions de conditionnement Download PDF

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Publication number
WO2009089205A1
WO2009089205A1 PCT/US2009/030197 US2009030197W WO2009089205A1 WO 2009089205 A1 WO2009089205 A1 WO 2009089205A1 US 2009030197 W US2009030197 W US 2009030197W WO 2009089205 A1 WO2009089205 A1 WO 2009089205A1
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Prior art keywords
meth
acrylate
polymerizable
solution
packaging system
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English (en)
Inventor
Yu-Chin Lai
Weihong Lang
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Bausch and Lomb Inc
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Bausch and Lomb Inc
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
    • A61L12/02—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using physical phenomena, e.g. electricity, ultrasound or ultrafiltration
    • A61L12/04—Heat
    • A—HUMAN NECESSITIES
    • A45—HAND OR TRAVELLING ARTICLES
    • A45C—PURSES; LUGGAGE; HAND CARRIED BAGS
    • A45C11/00—Receptacles for purposes not provided for in groups A45C1/00-A45C9/00
    • A45C11/005—Contact lens cases
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65B—MACHINES, APPARATUS OR DEVICES FOR, OR METHODS OF, PACKAGING ARTICLES OR MATERIALS; UNPACKING
    • B65B25/00—Packaging other articles presenting special problems
    • B65B25/008—Packaging other articles presenting special problems packaging of contact lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/282—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing two or more oxygen atoms

Definitions

  • the present invention generally relates to packaging solutions for ophthalmic devices such as contact lenses.
  • Blister-packs and glass vials are typically used to individually package each soft contact lens for sale to a customer.
  • Saline or deionized water is commonly used to store the lens in the blister-packs, as mentioned in various patents related to the packaging or manufacturing of contact lenses.
  • packaging solutions for blister-packs have sometimes been formulated to reduce or eliminate lens folding and sticking. For this reason, polyvinyl alcohol (PVA) has been used in contact-lens packaging solutions.
  • contact lens be as comfortable as possible for wearers. Manufacturers of contact lenses are continually working to improve the comfort of the lenses. Nevertheless, many people who wear contact lenses still experience dryness or eye irritation throughout the day and particularly towards the end of the day. An insufficiently wetted lens at any point in time will cause significant discomfort to the lens wearer. Although wetting drops can be used as needed to alleviate such discomfort, it would certainly be desirable if such discomfort did not arise in the first place. Poloxamine and poloxamers are examples of non-ionic surfactants having one or more poly(oxyalkylene) chains.
  • Poloxamines and poloxamers are well-known wetting and lubricating agents for contact lenses and have been used in lens wetting drops and in lens-care solutions for treating lenses after use or while in use in the eye.
  • U.S. Patent No. 4,786,436 disclose poloxamine as a wetting agent.
  • Contact-lens rewetting drops containing surfactants such as poloxamine and poloxamer have been used to make contact lens wear more comfortable, to soothe the eyes, and to moisten lenses to minimize dryness.
  • surfactants such as poloxamine, poloxamer, and tyloxapol have been used in multi-purpose solutions, for cleaning, wetting, and storing lenses.
  • poly(oxyalkylene) surfactants have also been disclosed for use in the eye to preventively clean lenses and inhibit deposits.
  • U.S. Patent No. 5,209,865 discloses the combination of certain poloxamers and poloxamines to maintain clean lenses in the eye.
  • U.S. Patent No. 6,440,366 discloses a package containing a contact lens suitable for immediate use which comprises (a) a solution comprising a non-ionic surfactant that is a compound comprising at least 90 weight percent of poly(oxyethylene) and poly(oxypropylene) segments, in one or more block copolymer chains, and (b) an effective amount of a tonicity adjusting agent such that the solution has an osmolality of 200 to 400 m ⁇ sm/kg; wherein the solution has a pH of about 6 to 8 and is heat sterilized and lacks an effective disinfecting amount of a disinfecting agent.
  • the surfactant is a poly(oxypropylene)-poly(oxyethylene) adduct of ethylene diamine.
  • a method of preparing a package comprising a storable, sterile ophthalmic device comprising: (a) immersing an ophthalmic device in an aqueous packaging solution comprising a copolymer which is the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers, wherein the solution has an osmolality of at least about 200 m ⁇ sm/kg and a pH in the range of about 6 to about 9;
  • a packaging system for the storage of an ophthalmic device comprising a sealed container containing one or more unused ophthalmic devices immersed in an aqueous packaging solution comprising a copolymer which is the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers, wherein the solution has an osmolality of at least about 200 mOsm/kg, a pH of about 6 to about 9 and is heat sterilized.
  • a packaging system for the storage of an ophthalmic device comprising:
  • an aqueous packaging solution comprising a copolymer which is the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers, wherein the solution has an osmolality of at least about 200 m ⁇ sm/kg and a pH in the range of about 6 to about 9;
  • aqueous packaging solutions of the present invention containing at least a copolymer which is the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers is believed to provide a more uniform coating on the surface of an ophthalmic device such as a contact lens thereby resulting in improved lubricity of the lens.
  • an ophthalmic device such as a contact lens thereby resulting in improved lubricity of the lens.
  • the lens will be more comfortable to wear in actual use and would allow for the extended wear of the lens without irritation or other adverse effects to the cornea.
  • the present invention provides a packaging system for the storage of ophthalmic devices intended for direct contact with body tissue or body fluid.
  • ophthalmic device refers to devices that reside in or on the eye. These lenses can provide optical correction, wound care, drug delivery, diagnostic functionality or cosmetic enhancement or effect or a combination of these properties.
  • Representative examples of such devices include, but are not limited to, soft contact lenses, e.g., a soft, hydrogel lens; soft, non-hydrogel lens and the like, hard contact lenses, e.g., a hard, gas permeable lens material and the like, intraocular lenses, overlay lenses, ocular inserts, optical inserts and the like.
  • a lens is considered to be "soft” if it can be folded back upon itself without breaking. Any material known to produce an ophthalmic device including a contact lens can be used herein.
  • an ophthalmic device can be any material known in the art capable of forming an ophthalmic device as described above.
  • an ophthalmic device includes devices which are formed from material not hydrophilic per se.
  • Such devices are formed from materials known in the art and include, by way of example, polysiloxanes, perfluoropolyethers, fluorinated poly(meth)acrylates or equivalent fluorinated polymers derived, e.g., from other polymerizable carboxylic acids, polyalkyl (meth)acrylates or equivalent alkylester polymers derived from other polymerizable carboxylic acids, or fluorinated polyolef ⁇ ns, such as fluorinated ethylene propylene polymers, or tetrafluoroethylene, preferably in combination with a dioxol, e.g., perfluoro-2,2-dimethyl-l,3- dioxol.
  • a dioxol e.g., perfluoro-2,
  • suitable bulk materials include, but are not limited to, Lotraf ⁇ lcon A, Neofocon, Pasifocon, Telefocon, Silafocon, Fluorsilfocon, Paflufocon, Silafocon, Elastofilcon, Fluorofocon or Teflon AF materials, such as Teflon AF 1600 or Teflon AF 2400 which are copolymers of about 63 to about 73 mol % of perfluoro-2,2- dimethyl- 1,3 -dioxol and about 37 to about 27 mol % of tetrafluoroethylene, or of about 80 to about 90 mol % of perfluoro-2,2-dimethyl-l,3-dioxol and about 20 to about 10 mol % of tetrafluoroethylene.
  • Teflon AF 1600 or Teflon AF 2400 which are copolymers of about 63 to about 73 mol % of perfluoro-2,2- di
  • an ophthalmic device includes devices which are formed from material hydrophilic per se, since reactive groups, e.g., carboxy, carbamoyl, sulfate, sulfonate, phosphate, amine, ammonium or hydroxy groups, are inherently present in the material and therefore also at the surface of an ophthalmic device manufactured therefrom.
  • reactive groups e.g., carboxy, carbamoyl, sulfate, sulfonate, phosphate, amine, ammonium or hydroxy groups
  • Such devices are formed from materials known in the art and include, by way of example, polyhydroxyethyl acrylate, polyhydroxyethyl methacrylate (HEMA), polyvinyl pyrrolidone (PVP), polyacrylic acid, polymethacrylic acid, polyacrylamide, polydimethylacrylamide (DMA), polyvinyl alcohol and the like and copolymers thereof, e.g., from two or more monomers selected from hydroxyethyl acrylate, hydroxyethyl methacrylate, N-vinyl pyrrolidone, acrylic acid, methacrylic acid, acrylamide, dimethyl acrylamide, vinyl alcohol and the like.
  • suitable bulk materials include, but are not limited to, Polymacon, Tefilcon, Methafilcon, Deltafilcon, Bufilcon, Phemfilcon, Ocufilcon, Focofilcon, Etafilcon, Hefilcon, Vifilcon, Tetrafilcon, Perfilcon, Droxifilcon, Dimefilcon, Isofilcon, Mafilcon, Nelfilcon, Atlafilcon and the like.
  • suitable bulk materials include balafilcon A, hilafilcon A, alphafilcon A, bilafilcon B and the like.
  • ophthalmic devices include devices which are formed from material which are amphiphilic segmented copolymers containing at least one hydrophobic segment and at least one hydrophilic segment which are linked through a bond or a bridge member.
  • non-hydrogel materials are hydrophobic polymeric materials that do not contain water in their equilibrium state.
  • Typical non-hydrogel materials comprise silicone acrylics, such as those formed bulky silicone monomer (e.g., tris(trimethylsiloxy)silylpropyl methacrylate, commonly known as "TRIS” monomer), methacrylate end-capped poly(dimethylsiloxane) prepolymer, or silicones having fluoroalkyl side groups (polysiloxanes are also commonly known as silicone polymers).
  • Hydrogels in general are a well-known class of materials that comprise hydrated, crosslinked polymeric systems containing water in an equilibrium state. Accordingly, hydrogels are copolymers prepared from hydrophilic monomers.
  • the hydrogel copolymers are generally prepared by polymerizing a mixture containing at least one device-forming silicone-containing monomer and at least one device- forming hydrophilic monomer. Either the silicone-containing monomer or the hydrophilic monomer can function as a crosslinking agent (a crosslinker being defined as a monomer having multiple polymerizable functionalities) or a separate crosslinker may be employed. Silicone hydrogels typically have a water content between about 10 to about 80 weight percent.
  • hydrophilic monomers include, but are not limited to, amides such as N,N-dimethylacrylamide and N,N-dimethylmethacrylamide; cyclic lactams such as N-vinyl-2-pyrrolidone; and (meth)acrylated poly(alkene glycols), such as poly(diethylene glycols) of varying chain length containing monomethacrylate or dimethacrylate end caps.
  • amides such as N,N-dimethylacrylamide and N,N-dimethylmethacrylamide
  • cyclic lactams such as N-vinyl-2-pyrrolidone
  • (meth)acrylated poly(alkene glycols) such as poly(diethylene glycols) of varying chain length containing monomethacrylate or dimethacrylate end caps.
  • hydrophilic vinyl carbonate or vinyl carbamate monomers disclosed in U.S. Patent No. 5,070,215
  • hydrophilic oxazolone monomers disclosed
  • hydrophilic monomers will be apparent to one skilled in the art.
  • 2-hydroxyethylmethacrylate (HEMA) is a well-known hydrophilic monomer that may be used in admixture with the aforementioned hydrophilic monomers.
  • the monomer mixtures may also include a second device-forming monomer including a copolymerizable group and a reactive functional group.
  • the copolyermizable group is preferably an ethylenically unsaturated group, such that this device-forming monomer copolymerizes with the hydrophilic device-forming monomer and any other device-forming monomers in the initial device-forming monomer mixture.
  • the second monomer can include a reactive functional group that reacts with a complementary reactive group of the copolymer which is the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers. In other words, after the device is formed by copolymerizing the device-forming monomer mixture, the reactive functional groups provided by the second device-forming monomers remain to react with a complementary reactive moiety of the copolymer.
  • Preferred reactive groups of the second device-forming monomers include epoxide groups. Accordingly, preferred second device-forming monomers are those that include both an ethylenically unsaturated group (that permits the monomer to copolymerize with the hydrophilic device-forming monomer) and the epoxide group (that does not react with the hydrophilic device-forming monomer but remains to react with the copolymer is the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers).
  • Examples include glycidyl methacrylate, glycidyl acrylate, glycidyl vinylcarbonate, glycidyl vinylcarbamate, 4-vinyl-l-cyclohexene-l,2-epoxide and the like.
  • one preferred class of ophthalmic device substrate materials are silicone hydrogels.
  • the initial device-forming monomer mixture further comprises a silicone-containing monomer.
  • Applicable silicone-containing monomeric materials for use in the formation of silicone hydrogels are well known in the art and numerous examples are provided in U.S. Pat. Nos. 4,136,250; 4,153,641; 4,740,533; 5,034,461; 5,070,215; 5,260,000; 5,310,779; and 5,358,995.
  • suitable materials for use herein include those disclosed in U.S. Patent Nos.
  • silicon-containing monomers include bulky polysiloxanylalkyl(meth)acrylic monomers.
  • the term "monomer” and like terms as used herein denote relatively low molecular weight compounds that are polymerizable by, for example, free radical polymerization, as well as higher molecular weight compounds also referred to as “prepolymers”, “macromonomers”, and related terms.
  • the term "(meth)” as used herein denotes an optional methyl substituent. Accordingly, terms such as “(meth)acrylate” denotes either methacrylate or acrylate, and "(meth)acrylic acid” denotes either methacrylic acid or acrylic acid.
  • An example of a bulky polysiloxanylalkyl(meth)acrylic monomer is represented by the structure of Formula I:
  • X denotes — O — or — NR — ; each R 1 independently denotes hydrogen or methyl; each R 2 independently denotes a lower alkyl radical, phenyl radical or a group represented by
  • R 2' wherein each R 2 independently denotes a lower alkyl or phenyl radical; and h is 1 to 10.
  • Examples of bulky monomers are methacryloxypropyl tris(trimethyl-siloxy)silane or tris(trimethylsiloxy)silylpropyl methacrylate, sometimes referred to as TRIS and tris(trimethylsiloxy)silylpropyl vinyl carbamate, sometimes referred to as TRIS-VC and the like.
  • Such bulky monomers may be copolymerized with a silicone macromonomer, which is a poly(organosiloxane) capped with an unsaturated group at two or more ends of the molecule.
  • a silicone macromonomer which is a poly(organosiloxane) capped with an unsaturated group at two or more ends of the molecule.
  • U.S. Patent No. 4,153,641 discloses, for example, various unsaturated groups such as acryloxy or methacryloxy groups.
  • silicone-containing monomers includes, but is not limited to, silicone-containing vinyl carbonate or vinyl carbamate monomers such as, for example, 1 ,3-bis[4-vinyloxycarbonyloxy)but-l -yl]tetramethyl-disiloxane; 3- (trimethylsilyl)propyl vinyl carbonate; 3-(vinyloxycarbonylthio)propyl- [tris(trimethylsiloxy)silane]; 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate; 3- [tris(trimethylsiloxy)silyl]propyl allyl carbamate; 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate; t-butyldimethylsiloxyethyl vinyl carbonate; trimethylsilylethyl vinyl carbonate; trimethylsilylmethyl vinyl carbonate and the like and mixtures thereof.
  • silicone-containing vinyl carbonate or vinyl carbamate monomers such as, for
  • silicon-containing monomers includes polyurethane-polysiloxane macromonomers (also sometimes referred to as prepolymers), which may have hard-soft-hard blocks like traditional urethane elastomers. They may be end-capped with a hydrophilic monomer such as 2-hydroxyethyl methacrylate (HEMA).
  • HEMA 2-hydroxyethyl methacrylate
  • silicone urethanes are disclosed in a variety or publications, including Lai, Yu-Chin, "The Role of Bulky Polysiloxanylalkyl Methacryates in Polyurethane-Polysiloxane Hydrogels, "Journal of Applied Polymer Science, Vol. 60, 1193-1199 (1996).
  • PCT Published Application No. WO 96/31792 discloses examples of such monomers, which disclosure is hereby incorporated by reference in its entirety.
  • Further examples of silicone urethane monomers are represented by Formulae II and III:
  • D independently denotes an alkyl diradical, an alkyl cycloalkyl diradical, a cycloalkyl diradical, an aryl diradical or an alkylaryl diradical having 6 to about 30 carbon atoms;
  • G independently denotes an alkyl diradical, a cycloalkyl diradical, an alkyl cycloalkyl diradical, an aryl diradical or an alkylaryl diradical having 1 to about 40 carbon atoms and which may contain ether, thio or amine linkages in the main chain;
  • * denotes a urethane or ureido linkage; a is at least 1 ;
  • A independently denotes a divalent polymeric radical of Formula IV: R s R s
  • each R s independently denotes an alkyl or fluoro-substituted alkyl group having 1 to about 10 carbon atoms which may contain ether linkages between the carbon atoms; m' is at least 1 ; and p is a number that provides a moiety weight of about 400 to about 10,000; each of E and E' independently denotes a polymerizable unsaturated organic radical represented by Formula V:
  • R 3 is hydrogen or methyl
  • R 4 is hydrogen, an alkyl radical having 1 to 6 carbon atoms, or a — CO — Y — R 6 radical wherein Y is — O — , — S — or — NH — -;
  • R 5 is a divalent alkylene radical having 1 to about 10 carbon atoms
  • R 6 is a alkyl radical having 1 to about 12 carbon atoms
  • X denotes —CO— or -OCO-
  • Z denotes — O — or — NH — ;
  • Ar denotes an aromatic radical having about 6 to about 30 carbon atoms; w is 0 to 6; x is 0 or 1 ; y is 0 or 1 ; and z is 0 or 1.
  • a preferred silicone-containing urethane monomer is represented by Formula VI: wherein m is at least 1 and is preferably 3 or 4, a is at least 1 and preferably is 1 , p is a number which provides a moiety weight of about 400 to about 10,000 and is preferably at least about 30, R 7 is a diradical of a diisocyanate after removal of the isocyanate group, such as the diradical of isophorone diisocyanate, and each E" is a group represented by:
  • a silicone hydrogel material comprises (in bulk, that is, in the monomer mixture that is copolymerized) about 5 to about 50 percent, and preferably about 10 to about 25, by weight of one or more silicone macromonomers, about 5 to about 75 percent, and preferably about 30 to about 60 percent, by weight of one or more polysiloxanylalkyl (meth)acrylic monomers, and about 10 to about 50 percent, and preferably about 20 to about 40 percent, by weight of a hydrophilic monomer.
  • the silicone macromonomer is a poly(organosiloxane) capped with an unsaturated group at two or more ends of the molecule.
  • the silane macromonomer is a silicon-containing vinyl carbonate or vinyl carbamate or a polyurethane-polysiloxane having one or more hard- soft-hard blocks and end-capped with a hydrophilic monomer.
  • an ophthalmic lens for use herein can be a cationic lens such as a cationic contact lens or fluorinated silicone-containing monomers.
  • Such monomers have been used in the formation of fluorosilicone as disclosed in, for example, U.S. Patent Nos. 4,954,587; 5,010,141 and 5,079,319.
  • silicone-containing monomers having certain fluorinated side groups i.e., -(CF2)-H
  • -(CF2)-H silicone-containing monomers having certain fluorinated side groups
  • Ophthalmic devices such as contact lenses for application of the present invention can be manufactured employing various conventional techniques, to yield a shaped article having the desired posterior and anterior lens surfaces.
  • an ophthalmic device can be prepared by polymerizing the monomeric mixtures to form a product that can be subsequently formed into the appropriate shape by, for example, lathing, injection molding, compression molding, cutting and the like.
  • the initial monomeric mixture may be polymerized in tubes to provide rod-shaped articles, which are then cut into buttons. The buttons may then be lathed into contact lenses.
  • the ophthalmic devices may be cast directly in molds, e.g., polypropylene molds, from the monomeric mixtures, e.g., by spincasting and static casting methods.
  • Spincasting methods are disclosed in U.S. Patent Nos. 3,408,429 and 3,660,545, and static casting methods are disclosed in U.S. Patent Nos. 4,113,224, 4,197,266, and 5,271,875.
  • Spincasting methods involve charging the monomer mixture to a mold, and spinning the mold in a controlled manner while exposing the monomer mixture to a radiation source such as UV light.
  • Static casting methods involve charging the monomeric mixture between two mold sections, one mold section shaped to form the anterior lens surface and the other mold section shaped to form the posterior lens surface, and curing the monomeric mixture while retained in the mold assembly to form a lens, for example, by free radical polymerization of the monomeric mixture.
  • free radical reaction techniques to cure the lens material include thermal radiation, infrared radiation, electron beam radiation, gamma radiation, ultraviolet (UV) radiation, and the like; or combinations of such techniques may be used.
  • U.S. Patent No. 5,271,875 describes a static cast molding method that permits molding of a finished lens in a mold cavity defined by a posterior mold and an anterior mold. As an additional method, U.S. Patent No.
  • 4,555,732 discloses a process where an excess of a monomeric mixture is cured by spincasting in a mold to form a shaped article having an anterior lens surface and a relatively large thickness, and the posterior surface of the cured spincast article is subsequently lathed to provide a contact lens having the desired thickness and posterior lens surface.
  • Polymerization may be facilitated by exposing the mixture to heat and/or radiation, such as ultraviolet light, visible light, or high energy radiation.
  • a polymerization initiator may be included in the mixture to facilitate the polymerization step.
  • free radical thermal polymerization initiators include organic peroxides such as acetal peroxide, lauroyl peroxide, decanoyl peroxide, stearoyl peroxide, benzoyl peroxide, tertiarylbutyl peroxypivalate, peroxydicarbonate, and the like.
  • UV initiators are those known in the art and include benzoin methyl ether, benzoin ethyl ether, Darocure 1173, 1164, 2273, 1116, 2959, 3331 (EM Industries) and Igracure 651 and 184 (Ciba-Geigy), and the like. Generally, the initiator will be employed in the monomeric mixture at a concentration of about 0.01 to 1 percent by weight of the total mixture.
  • Suitable organic diluents include, for example, monohydric alcohols such as C 6 -Ci 0 straight-chained aliphatic monohydric alcohols, e.g., n-hexanol and n-nonanol; diols such as ethylene glycol; polyols such as glycerin; ethers such as diethylene glycol monoethyl ether; ketones such as methyl ethyl ketone; esters such as methyl enanthate; and hydrocarbons such as toluene.
  • the organic diluent is sufficiently volatile to facilitate its removal from a cured article by evaporation at or near ambient pressure.
  • the diluent is included at about 5 to about 60 percent by weight of the monomeric mixture, with about 10 to about 50 percent by weight being especially preferred.
  • the cured lens can then be subjected to solvent removal, which can be accomplished by evaporation at or near ambient pressure or under vacuum.
  • An elevated temperature can be employed to shorten the time necessary to evaporate the diluent.
  • the time, temperature and pressure conditions for the solvent removal step will vary depending on such factors as the volatility of the diluent and the specific monomeric components, as can be readily determined by one skilled in the art.
  • the temperature employed in the removal step is preferably at least about 50°C, for example, about 60°C to about 80 0 C.
  • a series of heating cycles in a linear oven under inert gas or vacuum may be used to optimize the efficiency of the solvent removal.
  • the cured article after the diluent removal step should contain no more than twenty percent by weight of diluent, preferably no more than about 5 percent by weight or less.
  • the lens can then be subjected to mold release and optional machining operations.
  • the machining step includes, for example, buffing or polishing a lens edge and/or surface.
  • machining processes may be performed before or after the article is released from a mold part.
  • the lens is dry released from the mold by employing vacuum tweezers to lift the lens from the mold, after which the lens is transferred by means of mechanical tweezers to a second set of vacuum tweezers and placed against a rotating surface to smooth the surface or edges. The lens may then be turned over in order to machine the other side of the lens.
  • a packaging system for the storage of an ophthalmic device according to the present invention includes at least a sealed container containing one or more unused ophthalmic devices immersed in an aqueous packaging solution.
  • the sealed container is a hermetically sealed blister-pack, in which a concave well containing an ophthalmic device such as a contact lens is covered by a metal or plastic sheet adapted for peeling in order to open the blister-pack.
  • the sealed container may be any suitable generally inert packaging material providing a reasonable degree of protection to the lens, preferably a plastic material such as polyalkylene, PVC, polyamide, and the like.
  • the aqueous packaging solution will contain at least a copolymer which is the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers.
  • the devices may either be unhydrated or prehydrated in water or an aqueous solution.
  • Suitable polymerizable polyhydric alcohols include polyhydric alcohols having one or more polymerizable ethylenically unsaturated-containing radicals attached thereto.
  • a polymerizable ethylenically unsaturated- containing radical include, by way of example, (meth)acrylate-containing radicals, (meth)acrylamide-containing radicals, vinylcarbonate-containing radicals, vinylcarbamate- containing radicals, styrene-containing radicals, itaconate-containing radicals, vinyl- containing radicals, vinyloxy-containing radicals, fumarate-containing radicals, maleimide- containing radicals, vinylsulfonyl radicals and the like.
  • a polymerizable ethylenically unsaturated radical can be represented by the general formula:
  • R is hydrogen or a alkyl group having 1 to 6 carbon atoms such as methyl; each R is independently hydrogen, an alkyl radical having 1 to 6 carbon atoms, or a -CO-Y-R 1 ' radical wherein Y is -O-, -S- or -NH- and R 11 is an alkyl radical having 1 to about 10 carbon atoms; R 1 is a linking group (e.g., a divalent alkenyl radical having 1 to about 12 carbon atoms); B denotes -O- or -NH-; Z denotes -CO-, -OCO- or -COO-; Ar denotes an aromatic radical having 6 to about 30 carbon atoms; w is 0 to 6; a is 0 or 1 ; b is 0 or 1 ; and c is 0 or 1.
  • (meth) denotes an optional methyl substituent.
  • terms such as “(meth)acrylate” denote either methacrylate or acrylate
  • (meth)acrylamide denotes either methacrylamide or acrylamide.
  • the ethylenically unsaturated-containing radicals can be attached to the polyhydric alcohols as pendent groups, terminal groups or both.
  • suitable polymerizable polyhydric alcohols include polyhydroxyl (alk)acrylates having, for example, 2 to 10 hydroxyl groups and preferably 2 to 6 hydroxyl groups and an alkyl group containing from 3 to 12 carbon atoms, polyhydroxyl (alk)acrylamides having, for example, 2 to 10 hydroxyl groups and preferably 2 to 6 hydroxyl groups and an alkyl group containing from 3 to 12 carbon atoms and the like.
  • Useful polyhydroxyl (alk)acrylates include, but are not limited to, glycerol-containing -acrylates - methacrylates, and -ethacrylates, sorbitol-containing -acrylates, -methacrylates and - ethacrylates, erythritol-containing -acrylates, -methacrylates, and -ethacrylates, xylitol- containing -acrylates, -methacrylates, -ethacrylates, derivatives thereof and the like and mixtures thereof.
  • Useful polyhydroxyl alk)acrylamides include, but are not limited to, glycerol-containing -acrylamides, -methacrylamides and -ethacrylamides, sorbitol-containing -acrylamides, -methacrylamides and -ethacrylamides, erythritol-containing -acrylamides, - methacrylamides and -ethacrylamides, xylitol-containing -acrylamides, -methacrylamides and -ethacrylamides, derivatives thereof and the like and mixtures thereof.
  • Suitable fluorine-containing monomers include fluorine-containing monomers having one or more polymerizable ethylenically unsaturated-containing radicals attached thereto.
  • Representative examples of a "polymerizable ethylenically unsaturated-containing radical” include, by way of example, (meth)acrylate-containing radicals, (meth)acrylamide-containing radicals, vinylcarbonate-containing radicals, vinylcarbamate-containing radicals, styrene- containing radicals, itaconate-containing radicals, vinyl-containing radicals, vinyloxy- containing radicals, fumarate-containing radicals, maleimide-containing radicals, vinylsulfonyl radicals and the like and as exemplified for the polyhydric alcohol discussed above.
  • the ethylenically unsaturated-containing radicals can be attached to the fluorine- containing monomer as pendent groups, terminal groups or both.
  • useful polymerizable fluorine-containing monomers include fluorine substituted hydrocarbons having one or more polymerizable ethylenically unsaturated-containing radicals attached thereto and optionally containing one or more ether linkages, e.g., fluorine substituted straight or branched Ci-Ci 8 alkyl groups having one or more polymerizable ethylenically unsaturated- containing radicals attached thereto which may include ether linkages therebetween; fluorine substituted C 3 -C 24 cycloalkyl groups having one or more polymerizable ethylenically unsaturated-containing radicals attached thereto which may include ether linkages therebetween and fluorine substituted C 6 -C 30 aryl groups having one or more polymerizable ethylenically unsaturated-containing radicals attached thereto
  • alkyl groups for use herein include, by way of example, a straight or branched hydrocarbon chain radical containing carbon and hydrogen atoms of from 1 to about 30 carbon atoms with or without unsaturation, to the rest of the molecule, e.g., methyl, ethyl, n-propyl, 1 -methylethyl (isopropyl), n-butyl, n-pentyl, etc., and the like.
  • cycloalkyl groups for use herein include, by way of example, a substituted or unsubstituted non-aromatic mono or multicyclic ring system of about 3 to about 24 carbon atoms such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, perhydronapththyl, adamantyl and norbornyl groups bridged cyclic group or sprirobicyclic groups, e.g., sprio-(4, 4)-non-2-yl and the like, optionally containing one or more heteroatoms, e.g., O and N, and the like.
  • a substituted or unsubstituted non-aromatic mono or multicyclic ring system of about 3 to about 24 carbon atoms such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, perhydronapththyl
  • aryl groups for use herein include, by way of example, a substituted or unsubstituted monoaromatic or polyaromatic radical containing from about 5 to about 30 carbon atoms such as, for example, phenyl, naphthyl, tetrahydronapthyl, indenyl, biphenyl and the like, optionally containing one or more heteroatoms, e.g., O and N, and the like.
  • Examples of such polymerizable fluorine-containing monomer include, but are not limited to, 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 2,2,3, 3,3, -pentafluoropropyl (meth)acrylate, 1 -trifluoromethyl-2,2,2-trifluoroethyl (meth)acrylate, lH,lH,5H-octafluoropentyl (meth)acrylate, hexafluoroisopropyl (meth)acrylate, 2,2,3,3,4,4-hexafluorobutyl (meth)acrylate, pentafluorophenyl (meth)acrylate, pentafluorohexyl (meth)acrylate and mixtures thereof.
  • the copolymers disclosed herein can be obtained by copolymerizing the mixture containing at least one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers by conventional techniques for polymerization, typically thermal or photochemical polymerization.
  • thermal polymerization microwave radiation may be used.
  • the temperature employed during thermal polymerization can range from about 40°C to about 120°C, and typically about 50°C to about 100°C is used.
  • photochemical polymerization radiation such as gamma, ultraviolet (UV) or visible, may be used.
  • Polymerization is generally performed in a reaction medium such as, for example, a solution or dispersion using a solvent, e.g., water, an alkanol containing from 1 to 12 carbon atoms such as methanol, ethanol, isopropanol, propan-2-ol, t-butanol, t-amyl alcohol, n- hexanol, nonanol and the like, cyclic ethers such as tetrahydrofuran and the like, aromatic hydrocarbons such as toluene and the like.
  • a solvent e.g., water, an alkanol containing from 1 to 12 carbon atoms such as methanol, ethanol, isopropanol, propan-2-ol, t-butanol, t-amyl alcohol, n- hexanol, nonanol and the like, cyclic ethers such as tetrahydrofuran and the like, aromatic hydrocarbons such
  • a polymerization initiator may be included in the mixture to facilitate the polymerization step.
  • Representative free radical thermal polymerization initiators are usually peroxides or azo initiators such as, for example, acetal peroxide, lauroyl peroxide, decanoyl peroxide, stearoyl peroxide, benzoyl peroxide, tertiarylbutyl peroxypivalate, peroxydicarbonate, 2,2'-azo-bis(2-methylpropionitrile), benzoin methyl ether and the like and mixtures thereof.
  • UV initiators are those known in the field such as, for example, benzoin methyl ether, benzoin ethyl ether, Darocure 1 173, 1 164, 2273, 1116, 2959, 3331 (EM Industries) and Igracure 651 and 184 (Ciba-Geigy), and the like and mixtures thereof.
  • Other polymerization initiators which may be used are disclosed in, for example, "Polymer Handbook", 4th edition, Ed. J. Brandrup, E. H. Immergut, E. A. Grulke, A. Abe and D. R. Bloch, Pub. Wiley-Interscience, New York, 1998.
  • the initiator will be employed in the mixture at a concentration at about 0.1 to about 5 percent by weight of the total mixture.
  • polymerization can be carried out for about 1 to about 72 hours and under an inert atmosphere of, for example, nitrogen or argon. If desired, the resulting polymer can be dried under vacuum, e.g., for about 5 to about 72 hours or left in an aqueous solution prior to use.
  • the resulting polymerization product can have a number average molecular weight from about 500 to about 500,000 and preferably from about 1,000 to about 200,000.
  • the precise proportion and nature of the various comonomers used in the mixture to prepare a copolymer disclosed herein may be adjusted to provide a copolymer which is particularly suitable for treating the surface of the device according to the present invention.
  • the mixture which is subjected to polymerization to provide a polymerization product according to the invention can contain a minimum of about 10 %, and preferably about 30 % to about 80 % by weight of one or more polymerizable polyhydric alcohols and a maximum of about 50 %, and preferably about 10 % to about 30 % by weight of one or more polymerizable fluorine-containing monomers.
  • the copolymer can be endcapped with a suitable endcapping group as known in the art.
  • a suitable end-capping group include isocyanatoethyl methacrylate ("IEM"), methacrylic anhydride, methacryloyl chloride, vinylbenzoyl chloride, and the like, to produce a copolymer having one or more terminal polymerizable olef ⁇ nic groups bonded to the copolymer through linking moieties such as carbamate or ester groups.
  • the amount of the copolymer employed in a packaging solution for storing an ophthalmic device in a packaging system of the present invention is an amount effective to improve the surface properties of the ophthalmic device.
  • concentration of a hydrophilic polymer present in the packaging solution of the invention will range from about 0.01 to about 10 % w/w.
  • the packaging solutions according to the present invention are physiologically compatible.
  • the solution must be "ophthalmically safe" for use with a lens such as a contact lens, meaning that a contact lens treated with the solution is generally suitable and safe for direct placement on the eye without rinsing, that is, the solution is safe and comfortable for daily contact with the eye via a contact lens that has been wetted with the solution.
  • An ophthalmically safe solution has a tonicity and pH that is compatible with the eye and includes materials, and amounts thereof, that are non-cytotoxic according to ISO standards and U.S. Food & Drug Administration (FDA) regulations.
  • FDA Food & Drug Administration
  • the packaging solution should also be sterile in that the absence of microbial contaminants in the product prior to release must be statistically demonstrated to the degree necessary for such products.
  • the liquid media useful in the present invention are selected to have no substantial detrimental effect on the lens being treated or cared for and to allow or even facilitate the present lens treatment or treatments.
  • the liquid media are preferably aqueous-based.
  • a particularly useful aqueous liquid medium is that derived from saline, for example, a conventional saline solution or a conventional buffered saline solution.
  • the pH of the present solutions should be maintained within the range of about 6 to about 9, and preferably about 6.5 to about 7.8.
  • Suitable buffers may be added, such as boric acid, sodium borate, potassium citrate, citric acid, sodium bicarbonate, TRIS and various mixed phosphate buffers (including combinations of Na 2 HPO 4 , NaH 2 PO 4 and KH 2 PO4) and mixtures thereof.
  • buffers will be used in amounts ranging from about 0.05 to about 2.5 percent by weight, and preferably from about 0.1 to about 1.5 percent by weight of the solution.
  • the packaging solutions of this invention preferably contain a borate buffer, containing one or more of boric acid, sodium borate, potassium tetraborate, potassium metaborate or mixtures of the same.
  • the solutions of the present invention are also adjusted with tonicity agents, to approximate the osmotic pressure of normal lacrimal fluids which is equivalent to a 0.9 percent solution of sodium chloride or 2.5 percent of glycerol solution.
  • the solutions are made substantially isotonic with physiological saline used alone or in combination, otherwise if simply blended with sterile water and made hypotonic or made hypertonic the lenses will lose their desirable optical parameters. Correspondingly, excess saline may result in the formation of a hypertonic solution which will cause stinging and eye irritation.
  • suitable tonicity adjusting agents include, but are not limited to, sodium and potassium chloride, dextrose, glycerin, calcium and magnesium chloride and the like and mixtures thereof.
  • the tonicity agent will be employed in an amount to provide a final osmotic value of at least about 200 m ⁇ sm/kg, preferably from about 200 to about 400 m ⁇ sm/kg, more preferably from about 250 to about 350 m ⁇ sm/kg, and most preferably from about 280 to about 320 m ⁇ sm/kg.
  • one or more additional components can be included in the packaging solution.
  • Such additional component or components are chosen to impart or provide at least one beneficial or desired property to the packaging solution.
  • Such additional components may be selected from components which are conventionally used in one or more ophthalmic device care compositions. Examples of such additional components include cleaning agents, wetting agents, nutrient agents, sequestering agents, viscosity builders, contact lens conditioning agents, antioxidants, and the like and mixtures thereof.
  • These additional components may each be included in the packaging solutions in an amount effective to impart or provide the beneficial or desired property to the packaging solutions.
  • such additional components may be included in the packaging solutions in amounts similar to the amounts of such components used in other, e.g., conventional, contact lens care products.
  • Useful sequestering agents include, but are not limited to, disodium ethylene diamine tetraacetate, alkali metal hexametaphosphate, citric acid, sodium citrate and the like and mixtures thereof.
  • Useful viscosity builders include, but are not limited to, hydroxyethyl cellulose, hydroxymethyl cellulose, polyvinyl pyrrolidone, polyvinyl alcohol and the like and mixtures thereof.
  • Useful antioxidants include, but are not limited to, sodium metabisulfite, sodium thiosulfate, N-acetylcysteine, butylated hydroxyanisole, butylated hydroxytoluene and the like and mixtures thereof.
  • the method of packaging and storing an ophthalmic device such as a contact lens according to the present invention includes at least packaging an ophthalmic device immersed in the aqueous packaging solution described above.
  • the method may include immersing the ophthalmic device in an aqueous packaging solution prior to delivery to the customer/wearer, directly following manufacture of the contact lens.
  • the packaging and storing in the solution of the present invention may occur at an intermediate point before delivery to the ultimate customer (wearer) but following manufacture and transportation of the lens in a dry state, wherein the dry lens is hydrated by immersing the lens in the packaging solution. Consequently, a package for delivery to a customer may include a sealed container containing one or more unused contact lenses immersed in an aqueous packaging solution according to the present invention.
  • the steps leading to the present ophthalmic device packaging system includes (1) molding an ophthalmic device in a mold comprising at least a first and second mold portion, (2) hydrating and cleaning the device in a container comprising at least one of the mold portions, (3) introducing the packaging solution with the copolymer into the container with the device supported therein, and (4) sealing the container.
  • the method also includes the step of sterilizing the contents of the container. Sterilization may take place prior to, or most conveniently after, sealing of the container and may be effected by any suitable method known in the art, e.g., by autoclaving of the sealed container at temperatures of about 120°C or higher.
  • ID2S4H A methacrylate-capped prepolymer derived from isophorone diisocyanate, diethylene glycol and ⁇ , ⁇ -bis-hydroxybutyl polydimethylsiloxane of Mn 4000 at a molar ratio of 6: 3:2 and end-capped with 2-hydroxyethyl methacrylate.
  • TRIS tris(trimethylsiloxy)silylpropyl methacrylate
  • NVP N-vinyl-2-pyrrolidone
  • HEMAVC methacryloxy ethyl vinyl carbonate
  • D 1173 2-hydroxy-2-methyl- 1 -phenylpropan- 1 -one (available as Darocur 1173 initiator)
  • AIBN azo bis-isobutylnitrile (commercially available as VazoTM 64)
  • DBTDL dibutyltin dilaurate
  • glyceryl methacrylate 9.724 g; 60.711 mmol
  • THF 200 ml
  • IH, IH, 5H- octafluropentyl methacrylate 4.481 g; 14.927 mmol
  • AIBN 0.214 g; 1.303 mmol
  • Monomer mixtures are made by mixing the following components listed in Table 1 , at amounts per weight. TABLE 1
  • the resultant monomer mixtures are cast into contact lenses by introducing the monomer mixture to a mold assembly composed of a PP mold for the anterior surface and a PP mold for the posterior surface and thermally curing the monomer mixture at 100 0 C for 2 hours.
  • the contact lenses are released from the molds.
  • aqueous packaging solution containing 1% by weight of the copolymer of Example 1 dissolved in a borate buffered saline at a pH of 7.2 is placed in a polypropylene blister package.
  • the lenses of Example 2 are immersed in the aqueous packaging solution in the polypropylene blister package.
  • the package is sealed with foil lidstock and then autoclaved for 1 cycle.
  • Monomer mixtures are made by mixing the following components listed in Table 2, at amounts per weight.
  • the resultant monomer mixtures are cast into contact lenses by introducing the monomer mixture to a mold assembly composed of a PP mold for the anterior surface and a PP mold for the posterior surface and thermally curing the monomer mixture at 100 0 C for 2 hours.
  • the contact lenses are released from the molds.
  • aqueous packaging solution containing 1% by weight of the macro monomer of Example 4 dissolved in a borate buffered saline at a pH of 7.2 is placed in a polypropylene blister package.
  • the lenses of Example 5 are immersed in the aqueous packaging solution in the polypropylene blister package.
  • the package is sealed with foil lidstock and then autoclaved for 1 cycle.
  • aqueous packaging solution containing 1% by weight of the copolymer of Example 1 dissolved in a borate buffered saline at a pH of 7.2 is placed in a polypropylene blister package.
  • a balafilcon A contact lens (a commercially available group III extended wear contact lenses from Bausch & Lomb Incorporated of Rochester, N. Y., sold under the trade name Purevision , made of a silicone hydrogel material and having an anionic charge and approximately 38% water) is immersed in the aqueous packaging solution in the polypropylene blister package.
  • the package is sealed with foil lidstock and then autoclaved for 1 cycle.
  • aqueous packaging solution containing 1% by weight of the macro monomer of Example 4 dissolved in a borate buffered saline at a pH of 7.2 is placed in a polypropylene blister package.
  • a balafilcon A contact lens (a commercially available group III extended wear contact lenses from Bausch & Lomb Incorporated of Rochester, N. Y., sold under the trade name Purevision ® , made of a silicone hydrogel material and having an anionic charge and approximately 38% water) is immersed in the aqueous packaging solution in the polypropylene blister package.
  • the package is sealed with foil lidstock and then autoclaved for 1 cycle.
  • aqueous packaging solution containing 2% by weight of the copolymer of Example 1 dissolved in a borate buffered saline at a pH of 7.2 is placed in a polypropylene blister package.
  • a balafilcon A contact lens (a commercially available group III extended wear contact lenses from Bausch & Lomb Incorporated of Rochester, N. Y., sold under the trade name Purevision ® , made of a silicone hydrogel material and having an anionic charge and approximately 38% water) is immersed in the aqueous packaging solution in the polypropylene blister package.
  • the package is sealed with foil lidstock and then autoclaved for 1 cycle.
  • aqueous packaging solution containing 2% by weight of the macro monomer of Example 4 dissolved in a borate buffered saline at a pH of 7.2 is placed in a polypropylene blister package.
  • a balafilcon A contact lens (a commercially available group III extended wear contact lenses from Bausch & Lomb Incorporated of Rochester, N. Y., sold under the trade name Purevision ® , made of a silicone hydrogel material and having an anionic charge and approximately 38% water) is immersed in the aqueous packaging solution in the polypropylene blister package.
  • the package is sealed with foil lidstock and then autoclaved for 1 cycle.

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Abstract

L'invention concerne des systèmes de conditionnement pour stocker des dispositifs ophtalmiques, tels que des lentilles de contact, et des procédés pour conditionner de tels dispositifs ophtalmiques avec des solutions pour améliorer le confort des lentilles lorsqu'elles sont portées. Un système de conditionnement inclut un dispositif ophtalmique stocké dans une solution de conditionnement aqueuse contenant un copolymère qui est le produit de réaction d'un ou plusieurs alcools polyhydriques polymérisables et d'un ou plusieurs monomères contenant du fluor polymérisables.
PCT/US2009/030197 2008-01-09 2009-01-06 Solutions de conditionnement Ceased WO2009089205A1 (fr)

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ES2423914T3 (es) 2010-07-30 2013-09-25 Novartis Ag Lentes de hidrogel de silicona con superficies ricas en agua
SG11201400228WA (en) 2011-10-12 2014-05-29 Novartis Ag Method for making uv-absorbing ophthalmic lenses by coating
CN104871036B (zh) 2012-12-17 2019-12-10 诺华股份有限公司 制备改进的uv吸收性眼用透镜的方法
HUE038809T2 (hu) 2013-12-17 2018-11-28 Novartis Ag Térhálósított hidrofíl bevonattal ellátott szilikon hidrogél lencse
EP3186070B1 (fr) 2014-08-26 2019-09-25 Novartis AG Procédé pour appliquer un revêtement stable sur des lentilles de contact en hydrogel de silicone
KR102604468B1 (ko) 2015-12-15 2023-11-22 알콘 인코포레이티드 실리콘 하이드로겔 콘택트 렌즈 상에 안정한 코팅을 적용하기 위한 방법
US10830923B2 (en) 2017-12-13 2020-11-10 Alcon Inc. Method for producing MPS-compatible water gradient contact lenses
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