WO2002062402A1 - Antimicrobial contact lenses containing activated silver and methods for their production - Google Patents
Antimicrobial contact lenses containing activated silver and methods for their production Download PDFInfo
- Publication number
- WO2002062402A1 WO2002062402A1 PCT/US2001/050582 US0150582W WO02062402A1 WO 2002062402 A1 WO2002062402 A1 WO 2002062402A1 US 0150582 W US0150582 W US 0150582W WO 02062402 A1 WO02062402 A1 WO 02062402A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- lens
- lenses
- silver
- weight percent
- activated silver
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- 229910052709 silver Inorganic materials 0.000 claims description 28
- 239000004332 silver Substances 0.000 claims description 28
- 239000007800 oxidant agent Substances 0.000 claims description 17
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 15
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
- 239000000017 hydrogel Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229920001296 polysiloxane Polymers 0.000 claims description 7
- 230000002411 adverse Effects 0.000 claims description 6
- 230000000813 microbial effect Effects 0.000 claims description 6
- NLAIHECABDOZBR-UHFFFAOYSA-M sodium 2,2-bis(2-methylprop-2-enoyloxymethyl)butyl 2-methylprop-2-enoate 2-hydroxyethyl 2-methylprop-2-enoate 2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O.CC(=C)C(=O)OCCO.CCC(COC(=O)C(C)=C)(COC(=O)C(C)=C)COC(=O)C(C)=C NLAIHECABDOZBR-UHFFFAOYSA-M 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 3
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 3
- 150000004965 peroxy acids Chemical class 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 229920001616 Polymacon Polymers 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000012286 potassium permanganate Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 abstract description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical class [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 28
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- 239000000203 mixture Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 19
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- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 239000003618 borate buffered saline Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
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- 230000001580 bacterial effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 102100035526 B melanoma antigen 1 Human genes 0.000 description 2
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- 101000874316 Homo sapiens B melanoma antigen 1 Proteins 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
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- 239000004793 Polystyrene Substances 0.000 description 2
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- JNOGVQJEBGEKMG-UHFFFAOYSA-N (1-methoxy-2-methylprop-1-enoxy)-trimethylsilane Chemical compound COC(=C(C)C)O[Si](C)(C)C JNOGVQJEBGEKMG-UHFFFAOYSA-N 0.000 description 1
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- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
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- 241000588724 Escherichia coli Species 0.000 description 1
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- 241000593989 Scardinius erythrophthalmus Species 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
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- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
-
- 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
- A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
- A61L12/088—Heavy metals
-
- 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/54—Biologically active materials, e.g. therapeutic substances
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
- A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
- A61L2300/104—Silver, e.g. silver sulfadiazine
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
Definitions
- This invention relates to optically clear lenses having antimicrobial properties as well as methods of their production, use, and storage.
- the build-up of bacteria or other microbes is not unique to soft contact lens wearer and may occur during the use of hard contact lenses as well. Therefore, there is a need to produce contact lenses which inhibit the growth of bacteria or other microbes and/or the adhesion of bacterial or other microbes on the surface of contact lenses. Further there is a need to produce contact lenses which do not promote the adhesion and/or growth of bacteria or other microbes on the surface of the contact lenses. Also there is a need to produce contact lenses which inhibit adverse responses related to the growth of bacteria or other microbes.
- This invention includes an optically clear lens having antimicrobial properties comprising, consisting essentially of, or consisting of, more than about 0.01 weight percent activated silver.
- an optically clear lens having antimicrobial properties comprising, consisting essentially of, or consisting of, more than about 0.01 weight percent activated silver.
- optically clear refers to a lens that has optical clarity comparable to currently available commercial lenses, e.g. etafilcon A, balafilcon A, and the like.
- lens refers to opthalmic devices that reside in or on the eye. These devices can provide optical correction or may be cosmetic.
- lens includes but is not limited to soft contact lenses, hard contact lenses, intraocular lenses, overlay lenses, ocular inserts, and optical inserts.
- Typical hard contact lenses are made from polymers which include but are not limited to polymers of poly(methyl)methacrylate, silicone acrylates, fluoroacrylates, fluoroethers, polyacetylenes, and polyimides, where the preparation of representative examples may be found in JP 200010055, JP 6123860, and U.S. Patent 4,330,383.
- Typical soft contact lenses are made from silicone elastomers, or hydrogels, such as but not limited to silicone hydrogels and fluorohydrogels. The preparation of representative soft contact lenses may be found in US Patent No. 5,710,302, WO 9421698, EP 406161 , JP 2000016905, U.S. Pat. No. 5,998,498, US Pat. App. No.
- Intraocular lenses of the invention can be formed using known materials.
- the lenses may be made from a rigid material including, without limitation, polymethyl methacrylate, polystyrene, polycarbonate, or the like, and combinations thereof.
- flexible materials may be used including, without limitation, hydrogels, silicone materials, acrylic materials, fluorocarbon materials and the like, or combinations thereof.
- Typical intraocular lenses are described in WO 0026698, WO 0022460, WO 9929750, WO 9927978, WO 0022459, and JP 2000107277. All of the aforementioned lenses of the invention, may be coated with a number of agents that are used to coat lens.
- the procedures, compositions, and methods of U.S. Pat. No. 6,087,415 may be used and this patent is hereby incorporated by reference for those procedures, compositions, and methods. All of the references mentioned in this application are hereby incorporated by reference in their entirety.
- activated silver refers to silver that has been incorporated into the polymer of a lens, prior to forming the lens and subsequently activated by treatment with an oxidizing agent.
- Oxidizing agents include but are not limited to hydrogen peroxide, sodium hypochlorite, peroxy acids, bromine, chlorine, chromic acid, potassium permaganate, and iodine.
- the preferred oxidizing agent is sodium hypochlorite.
- the oxidizing agent can be dispersed or dissolved in an aqueous solution, such as deionized water, and the formed lens may be washed or soaked with this solution for a period of time.
- the concentration of the oxidizing agent in aqueous solution is about 0.1 to about 50 weight percent, where the percentage is based on the weight (or volume) of the solution, preferably about 0.4 to about, 30 weight percent, and more preferably about 0.6 to about 15 weight percent.
- the period of time for the treating the lenses with the oxidizing agent is about 10 seconds to about 10 hours, preferably about 1 to about 10 minutes.
- the silver that is oxidized includes but is not limited to powdered silver having mesh size of -30, -60, or -325 or an average particle size of 2 to 8 microns; nanosize powder; and silver that is formed by reduction of ionic silver in the polymer matrix.
- the amount of silver in the lens is greater than 0.01 weight percent, where the percentage is based the weight of the components of the un-hydrated monomer.
- the weight percentage of silver is about 0.01 to about 0.3 weight percent, more preferably, about 0.02 to about 0.2 weight percent, and most preferably about 0.03 to about 0.1 weight percent.
- antimicrobial properties refers to a lenses that exhibit one or more of the following properties, the inhibition of the adhesion of bacteria or other microbes to the lenses, the inhibition of the growth of bacteria or other microbes on lenses, and the killing of bacteria or other microbes on the surface of lenses or in a radius extending from the lenses (hereinafter adhesion of bacteria or other microbes to lenses, the growth of bacteria or other microbes to lenses and the presence of bacterial or other microbes on the surface of lenses is collectively referred to as "microbial production").
- the lenses of the invention exhibit at least a 1-log reduction (> 90% inhibition) of viable bacteria or other microbes, most particularly preferably, about a 2-log reduction (> 99% inhibition) of viable bacteria or other microbes in in vitro tests.
- bacteria or other microbes include but are not limited to those organisms found in the eye, particularly Pseudomonas aeruginosa, Acanthanmoeba, Staph. aureus, E. coli, Staphyloccus epidermidus, and Serratia marcesens.
- the invention includes a method of reducing a lens wearer's adverse microbial reactions comprising, consisting essentially of, and consisting of, the step of providing an optically clear lens having antimicrobial properties, the lens comprising, consisting essentially of, or consisting of more than about 0.01 weight percent activated silver.
- lens, activated silver, optically clear, and antimicrobial properties all have their aforementioned meanings and preferred ranges.
- the preferred lens wearer is a human.
- the phrase "adverse events associated with microbial infections” include but are not limited to the following: ulcerative (microbial, infectious) keratitis, infiltrative keratitis, asymptomatic infiltrates, contact lens-induced peripheral ulcer, contact lens-induced acute red eye, and contact lens-induced papillary conjunctivitis.
- ulcerative (microbial, infectious) keratitis infiltrative keratitis, asymptomatic infiltrates
- contact lens-induced peripheral ulcer contact lens-induced acute red eye
- contact lens-induced papillary conjunctivitis any reduction in the population of bacteria or other microbes in a lens wearer's eye may alleviate the adverse effects associated with microbial infections
- the lenses of the invention inhibit the growth of bacteria and other microbes in standard in vitro tests at about 50% to about 100%, more preferably, about 80% to about 100%, most preferably, about 90% to about 100%.
- the lenses of the invention exhibit at least a 1-log reduction (> 90% inhibition
- the invention includes a method of producing an optically clear lens having antimicrobial properties, the lens comprising, consisting essentially of, or consisting of, more than about 0.01 weight percent activated silver, where the method comprises, consists essentially of, or consists of treating a lens containing silver with an oxidizing agent.
- oxidizing agents includes but is not limited to hydrogen peroxide, sodium hypochlorite, peroxy acids, bromine, chlorine, chromic acid, potassium permanganate and iodine, where the preferred oxidizing agent is sodium hypochlorite.
- the oxidizing agent can be applied to the lens in a number of ways, preferably it is dispersed or dissolved in an aqueous solution, such as deionized water, and the formed lens may be washed or soaked with this solution for a period of time.
- concentration of the oxidizing agent in aqueous solution is about 0.1 to about 50 weight percent, preferably about 0.4 to about, 30 weight percent, and more preferably about 0.6 to about 15 weight percent, where the percentage is based on the weight of the solution.
- the period of time for the treating the lenses with the oxidizing agent is about 10 seconds to about 10 hours, preferably about 1 to 10 minutes.
- the invention includes a lens case having antimicrobial properties, comprising, consisting essentially of, or consisting of, more than about 0.01 weight percent activated silver.
- lens, activated silver, optically clear, and antimicrobial properties all have their aforementioned meanings and preferred ranges.
- the term lens case refers to a container that is adapted to define a space in which to hold a lens when that lens is not in use.
- This term includes packaging for lenses, where packaging includes any unit in which a lens is stored after curing. Examples of this packaging include but are not limited to single use blister packs and the like.
- the container components may be made of a transparent, thermo-plastic polymeric material, such as polymethylmethacrylate, polyolefins, such as poly-ethylene, polypropylene and the like; polyesters, polyurethanes; acrylic polymers, such as polyacrylates and polymethacrylates; polycarbonates and the like and is made, e.g., molded, using conventional techniques as a single unit.
- a transparent, thermo-plastic polymeric material such as polymethylmethacrylate, polyolefins, such as poly-ethylene, polypropylene and the like
- polyesters, polyurethanes such as acrylic polymers, such as polyacrylates and polymethacrylates
- polycarbonates and the like is made, e.g., molded, using conventional techniques as a single unit.
- Either the lens container, the lens basket or the top may contain activated silver.
- silver can be added to the monomer mix of the other components.
- the resulting mixture is charged to molds, cured, and subsequently treated with an oxidizing agent.
- the method of treating the molded article with an oxidizing agent is analogous to the method described for the treatment of formed lenses to give lenses with activated silver.
- activated silver is present in any or all of the lens case components at about 0.01 to about 10 weight percent (based on the initial monomer mix), more preferably about 0.05 to about 3.0 percent.
- the following examples are included. These examples do not limit the invention. They are meant only to suggest a method of practicing the invention. Those knowledgeable in contact lenses as well as other specialties may find other methods of practicing the invention. However, those methods are deemed to be within the scope of this invention.
- TBACB tetrabutyl ammonium-m-chlorobenzoate mPDMS 800-1000 MW monomethacryloxypropyl terminated polydimethylsiloxane
- PVP poly(N-vinyl pyrrolidone) I PA isopropyl alcohol GMMA glycerin 1-monomethacrylate mPEG 350 poly(ethylene glycol) methyl ether D30 3,7-dimethyl-3-octanol
- the bacterial inoculum is prepared to result in a final concentration of 1 x 10 8 colony forming units (cfu)/ml.
- Three contact lenses are rinsed with phosphate buttered saline ("PBS") pH 7.4 + 0.2. Each washed contact lens is combined with two ml of the bacterial inoculum into a glass vial, which is agitated in a shaker-incubator for two hr. at 37 +°C.
- Each lens is washed with PBS, placed into 10 ml of PBS containing 0.05% TweenTM 80 and vortexed at 2000 rpm for three min. The resulting supernatant is enumerated for viable bacteria, and the results of the detectacted viable bacteria attached to three lenses are averaged.
- Example 1 A blend of 9.80 g HEMA, 0.08 g EGDMA, 0.04 g DarocurTM 1173, and nanosize activated powdered silver (99.9+%, from Aldrich Chemicals), in 9.80 g of BAGE diluent, was sonicated for 1 hour. The resulting mixture was charged to a mold subsequently exposed to UV light for 30 minutes in a polystyrene to cure the polymer. After curing, the molds were opened, and the lenses were washed out into borate-buffered saline. The resulting lenses were soaked for 10 minutes in a 5.25% v/v solution of sodium hypochlorite in water, then rinsed 5 times in 0.85% v/v physiological saline solution. The number of viable Pseudomonas aeruginosa adhered to the lenses using the microbial assay described above was reduced by 99.8% compared to the untreated contact lens.
- Example 2 The procedure of Example 1 was repeated, with addition of MAA as indicated in Table 1. In all cases the adhesion of viable bacteria was reduced when compared to a lens of the same polymer composition without silver. The results of the biological assay are shown in Table 1.
- reaction mixture was cooled to 15 °C while stirring and purging with nitrogen. After the solution reaches 15 °C, 191.75 g (1.100 mol) of 1- trimethylsiloxy-1-methoxy-2-methylpropene (1 equivalent) was injected into the reaction vessel. The reaction was allowed to exotherm to approximately 62 °C and then 30 ml of a 0.40 M solution of 154.4 g TBACB in 11 ml of dry THF was metered in throughout the remainder of the reaction. After the temperature of reaction reached 30 °C and the metering began, a solution of 467.56 g (2.311 mol) 2-(trimethylsiloxy)ethyl methacrylate (2.1 equivalents relative to the initiator), 3636.6.
- the reaction flask was maintained at approximately 110 °C and a solution of 443 g (2.201 mol) TMI and 5.7 g (0.010 mol) dibutyltin dilaurate were added. The mixture was reacted until the isocyanate peak was gone by IR. The toluene was evaporated under reduced pressure to yield an off-white, anhydrous, waxy reactive monomer.
- the macromer was placed into acetone at a weight basis of approximately 2:1 acetone to macromer. After 24 hrs, water was added to precipitate out the macromer and the macromer was filtered and dried using a vacuum oven between 45 and 60 °C for 20-30 hrs.
- a hydrogel was made from the following monomer mix (all amounts are calculated as weight percent of the total weight of the combination): macromer B (-18%), mPDMS (-28%), TRIS (-14%), DMA (-26%), HEMA (-5%), TEGDMA (-1%), PVP (-5%); CGI 1850 (-1%), glacial acetic acid (-5%), nanosize activated powdered silver (from Aldrich Chemicals ⁇ 0.13%) , with the balance comprising minor amounts of additives.
- the polymerization was conducted in the presence of 20%wt dimethyl-3-octanol diluent, and the blend was sonicated for 30 minutes before curing.
- Contact lenses were formed by adding about 0.10 g of the monomer mix to the cavity of an eight-cavity lens mold of the type described in U.S. Patent 4,640,489.
- the lenses were cured for 8 minutes at 50 C (+5) using visible light (wavelength: 380-460 nm with a peak maximum at 425 nm, dose: approx. 2.5 J/cm 2 ).
- the molds were opened, and the lenses were released into a 1 :1 blend of water and ethanol, then leached in ethanol to remove any residual monomers and diluent.
- the lenses were equilibrated in physiological borate-buffered saline. The lenses appeared transparent when examined with the naked eye, although the silver particles could be seen under magnification.
- the resulting lenses were soaked for 21 hours in a 5.25% solution of sodium hypochlorite in water, then rinsed 5 times in saline solution.
- the lenses were tested for antibacterial properties by the following method:
- Each lens was washed with Dulbecco's Phosphate Buffered Saline without calcium chloride and magnesium chloride, then placed into 1000 ⁇ l of Mueller Hinton Broth containing 10 8 cfu/ml Pseudomonas aeruginosa (ATCC 15442), and incubated at 37°C overnight.
- the resulting solutions were observed for opacity and cultured to enumerate the bacteria, and compared to similar lenses that were not reacted with sodium hypochlorite.
- the results, in Table 3, show that the number of bacteria were reduced by >99.99%.
- a blend was made of 40.67 weight % HEMA, 1.0% Darocur 1173, 1.07% TEGDMA, 26.90% GMMA and 30.36% mPEG 350 (diluent). Nanosize activated powdered silver was added to this blend in amounts indicated in Table 4. Lenses were made and treated with sodium hypochlorite following the procedure of Example 1.
- Examples 9-12 Lenses were made using the blend and method described in Example 5, except without addition of powdered silver, and without reacting with sodium . hypochlorite. These lenses were rinsed with deionized water to remove chloride ions. They were soaked in varying concentrations of AgN0 3 , as indicated in Table 4 for 30 minutes, blotted to remove surface water, and placed into a solution of 5.0% ascorbic acid in water. After one hour the lenses were rinsed in deionized water, and then soaked either in 5.25% sodium hypochlorite or 3.0% aqueous hydrogen peroxide for 10 minutes or 60 minutes respectively, as indicated in Table 5. The lenses were rinsed in borate- buffered saline, autoclave sterilized, and tested for antibacterial properties using the vortex assay described above. The results are shown in Table 5
- Example 5 The lenses of Example 5 were made, but with 0.10% nanosize silver, and instead of reacting with sodium hypochlorite, reacting with a solution of 3.0% hydrogen peroxide diluted to the indicated concentration with borate- buffered saline at room temperature for the time indicated in Table 6. The lenses were tested using the microbial assay described above. The results are shown in Table 6. Table 6
- Example 17-19 The lenses of Example 5 were made, but with 0.10% nanosize silver, and instead of reacting with sodium hypochlorite, reacting with a solution of 50% hydrogen peroxide diluted as needed to the indicated concentration with borate-buffered saline at room temperature for the time indicated in Table 7. The lenses were tested using the vortex assay described above. The results are shown in Table 7.
- EXAMPLES 20-22 The lenses of EXAMPLE 5 were made, but instead of reacting with sodium hypochlorite, reacting with an aqueous solution of 0.05M l 2 and 0.20 M Kl at room temperature for the time indicated in Table 8. The lenses were tested using the vortex assay described above. The results are shown in Table 8.
- etafilcon A lens *Compared to an etafilcon A lens.
- EXAMPLES 23-25 The lenses of EXAMPLE 5 were made, but with 0.20% nanosize silver, and instead of reacting with sodium hypochlorite, reacting with a solution of 3.0% hydrogen peroxide diluted to the indicated concentration with borate- buffered saline at room temperature for the time indicated in Table 9. The lenses were tested using the vortex assay described above. The results are shown in Table 9.
- Macromer B The procedure for Macromer B was used except that 19.1 mole parts HEMA, 7.9 mole parts TRIS, 3.3 mole parts mPDMS, and 2.0 mole parts TMI were used.
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Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE60117863T DE60117863T2 (en) | 2000-12-21 | 2001-12-21 | ACTIVATED SILVER ANTIMICROBIAL CONTACT LENS CONTAINING AND METHOD FOR THE PRODUCTION THEREOF |
CA002432796A CA2432796A1 (en) | 2000-12-21 | 2001-12-21 | Antimicrobial contact lenses containing activated silver and methods for their production |
JP2002562407A JP2004526187A (en) | 2000-12-21 | 2001-12-21 | Antibacterial contact lens containing activated silver and method for producing the same |
BR0116479-1A BR0116479A (en) | 2000-12-21 | 2001-12-21 | Antimicrobial contact lenses containing activated silver and processes for their production |
KR10-2003-7008463A KR20030063460A (en) | 2000-12-21 | 2001-12-21 | Antimicrobial contact lenses containing activated silver and method for their production |
EP01994478A EP1355681B1 (en) | 2000-12-21 | 2001-12-21 | Antimicrobial contact lenses containing activated silver and methods for their production |
HK03108941A HK1056516A1 (en) | 2000-12-21 | 2003-12-09 | Antimicrobial contact lenses containing activated silver and methods their production |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US25731700P | 2000-12-21 | 2000-12-21 | |
US60/257,317 | 2000-12-21 |
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WO2002062402A1 true WO2002062402A1 (en) | 2002-08-15 |
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PCT/US2001/050582 WO2002062402A1 (en) | 2000-12-21 | 2001-12-21 | Antimicrobial contact lenses containing activated silver and methods for their production |
Country Status (11)
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US (1) | US20020197299A1 (en) |
EP (1) | EP1355681B1 (en) |
JP (1) | JP2004526187A (en) |
KR (1) | KR20030063460A (en) |
CN (1) | CN100363061C (en) |
BR (1) | BR0116479A (en) |
CA (1) | CA2432796A1 (en) |
DE (1) | DE60117863T2 (en) |
HK (1) | HK1056516A1 (en) |
TW (1) | TWI229209B (en) |
WO (1) | WO2002062402A1 (en) |
Cited By (14)
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WO2005014074A1 (en) * | 2003-07-16 | 2005-02-17 | Novartis Ag | Antimicrobial medical devices |
WO2005033751A1 (en) * | 2003-09-30 | 2005-04-14 | Johnson & Johnson Vision Care, Inc. | Methods of preparing ophthalmic devices |
WO2005058253A1 (en) * | 2003-12-17 | 2005-06-30 | Heraeus Kulzer Gmbh | Antimicrobial nano silver additive for polymerizable dental materials |
WO2005073289A1 (en) * | 2004-01-28 | 2005-08-11 | Qinetiq Nanomaterials Limited | Method of manufacture of polymer composites |
WO2005088351A2 (en) * | 2004-03-17 | 2005-09-22 | Thorkild Andersen | Contact lens, container and insert for avoiding infection of the eye |
JP2005535478A (en) * | 2002-08-16 | 2005-11-24 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | Mold for contact lens manufacturing |
JP2006076295A (en) * | 2004-08-26 | 2006-03-23 | Johnson & Johnson Vision Care Inc | Mold form for manufacturing lens for eye |
JP2006511302A (en) * | 2002-12-23 | 2006-04-06 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | Contact lens package with additives |
WO2008094876A1 (en) | 2007-01-31 | 2008-08-07 | Novartis Ag | Antimicrobial medical devices including silver nanoparticles |
US7960465B2 (en) | 2006-06-30 | 2011-06-14 | Johnson & Johnson Vision Care, Inc. | Antimicrobial lenses, processes to prepare them and methods of their use |
EP2384772A2 (en) | 2002-11-22 | 2011-11-09 | Johnson & Johnson Vision Care, Inc. | Antimicrobial lenses, processes to prepare them and methods of their use |
US8501833B2 (en) | 2005-12-14 | 2013-08-06 | Novartis Ag | Method for preparing silicone hydrogels |
US9358317B2 (en) | 2006-10-31 | 2016-06-07 | Johnson & Johnson Vision Care, Inc. | Acidic processes to prepare antimicrobial contact lenses |
EP3248621A1 (en) | 2007-10-08 | 2017-11-29 | Johnson & Johnson Vision Care, Inc. | Methods for forming stabilized metal salt particles |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
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US8309117B2 (en) * | 2002-12-19 | 2012-11-13 | Novartis, Ag | Method for making medical devices having antimicrobial coatings thereon |
US9297928B2 (en) | 2004-11-22 | 2016-03-29 | Johnson & Johnson Vision Care, Inc. | Ophthalmic compositions comprising polyether substituted polymers |
US7319133B2 (en) * | 2005-08-09 | 2008-01-15 | Coopervision, Inc. | Contact lens extraction/hydration systems and methods of reprocessing fluids used therein |
EP1913029A1 (en) * | 2005-08-10 | 2008-04-23 | Novartis AG | Silicone hydrogels |
DE102005053295C5 (en) * | 2005-11-08 | 2013-03-07 | Spiegelberg GmbH & Co. KG | Process for producing a sterile-packed, metal-containing plastic body having an antimicrobial surface |
US20080241225A1 (en) * | 2007-03-31 | 2008-10-02 | Hill Gregory A | Basic processes to prepare antimicrobial contact lenses |
DE102007025452A1 (en) | 2007-05-31 | 2008-12-04 | Ernst-Moritz-Arndt-Universität Greifswald | Surface coating method for precipitating layers onto e.g., medical appliances, involves pre-treating surface with plasma process before applying micro- or nano-particles and then fixing |
CN102445716A (en) * | 2010-10-12 | 2012-05-09 | 鸿富锦精密工业(深圳)有限公司 | Lens and manufacturing method as well as manufacturing equipment of lens |
CN111032060A (en) | 2017-06-28 | 2020-04-17 | 科利迪恩公司 | Compositions, methods and uses for cleaning, disinfecting and/or sterilizing |
KR20200123421A (en) | 2018-01-14 | 2020-10-29 | 콜리디온, 인코포레이티드 | Compositions, kits, methods and uses for cleaning, disinfection, sterilization and/or treatment |
CN112695521B (en) * | 2020-12-25 | 2023-04-28 | 安徽工程大学 | Halamine modified antibacterial mesoporous material and synthesis method thereof |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5312586A (en) * | 1991-06-21 | 1994-05-17 | Stockel Richard F | Process for sterilizing a contact lens |
US5515117A (en) * | 1993-05-06 | 1996-05-07 | Allergan, Inc. | Antimicrobial lenses and lens care systems |
WO1998018330A1 (en) * | 1996-10-28 | 1998-05-07 | Surfacine Development Company, Llc | Contact-killing non-leaching antimicrobial materials |
WO2000038552A1 (en) * | 1998-12-31 | 2000-07-06 | Healthshield Technologies Llc | Antimicrobial contact lens case |
EP1050314A1 (en) * | 1999-05-07 | 2000-11-08 | Healthshield Technologies L.L.C. | Antimicrobial contact lens |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57500588A (en) * | 1980-03-27 | 1982-04-08 | ||
JPH0476518A (en) * | 1990-07-19 | 1992-03-11 | Sangi Co Ltd | Antibacterial contact lens |
US6267782B1 (en) * | 1997-11-20 | 2001-07-31 | St. Jude Medical, Inc. | Medical article with adhered antimicrobial metal |
-
2001
- 2001-12-20 US US10/027,740 patent/US20020197299A1/en not_active Abandoned
- 2001-12-21 WO PCT/US2001/050582 patent/WO2002062402A1/en active IP Right Grant
- 2001-12-21 TW TW090131769A patent/TWI229209B/en not_active IP Right Cessation
- 2001-12-21 DE DE60117863T patent/DE60117863T2/en not_active Expired - Lifetime
- 2001-12-21 EP EP01994478A patent/EP1355681B1/en not_active Expired - Lifetime
- 2001-12-21 BR BR0116479-1A patent/BR0116479A/en not_active Application Discontinuation
- 2001-12-21 CN CNB01822766XA patent/CN100363061C/en not_active Expired - Fee Related
- 2001-12-21 CA CA002432796A patent/CA2432796A1/en not_active Abandoned
- 2001-12-21 JP JP2002562407A patent/JP2004526187A/en active Pending
- 2001-12-21 KR KR10-2003-7008463A patent/KR20030063460A/en not_active Application Discontinuation
-
2003
- 2003-12-09 HK HK03108941A patent/HK1056516A1/en not_active IP Right Cessation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5312586A (en) * | 1991-06-21 | 1994-05-17 | Stockel Richard F | Process for sterilizing a contact lens |
US5515117A (en) * | 1993-05-06 | 1996-05-07 | Allergan, Inc. | Antimicrobial lenses and lens care systems |
WO1998018330A1 (en) * | 1996-10-28 | 1998-05-07 | Surfacine Development Company, Llc | Contact-killing non-leaching antimicrobial materials |
WO2000038552A1 (en) * | 1998-12-31 | 2000-07-06 | Healthshield Technologies Llc | Antimicrobial contact lens case |
EP1050314A1 (en) * | 1999-05-07 | 2000-11-08 | Healthshield Technologies L.L.C. | Antimicrobial contact lens |
Non-Patent Citations (1)
Title |
---|
NISSEN S ET AL: "[Antimicrobial efficacy of a silver layer on hydrogel lenses] Citation]", DER OPHTHALMOLOGE: ZEITSCHRIFT DER DEUTSCHEN OPHTHALMOLOGISCHEN GESELLSCHAFT. GERMANY SEP 2000, vol. 97, no. 9, September 2000 (2000-09-01), pages 640 - 643, XP002204043, ISSN: 0941-293X * |
Cited By (25)
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JP2005535478A (en) * | 2002-08-16 | 2005-11-24 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | Mold for contact lens manufacturing |
JP4708023B2 (en) * | 2002-08-16 | 2011-06-22 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | Mold for contact lens manufacturing |
US8292256B2 (en) | 2002-08-16 | 2012-10-23 | Johnson & Johnson Vision Care, Inc. | Molds for producing contact lenses |
EP2384772A2 (en) | 2002-11-22 | 2011-11-09 | Johnson & Johnson Vision Care, Inc. | Antimicrobial lenses, processes to prepare them and methods of their use |
EP2384773A1 (en) | 2002-11-22 | 2011-11-09 | Johnson & Johnson Vision Care, Inc. | Antimicrobial lenses, processes to prepare them and methods of their use |
JP2006511302A (en) * | 2002-12-23 | 2006-04-06 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | Contact lens package with additives |
JP4776926B2 (en) * | 2002-12-23 | 2011-09-21 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | Contact lens package with additives |
WO2005014074A1 (en) * | 2003-07-16 | 2005-02-17 | Novartis Ag | Antimicrobial medical devices |
US8425926B2 (en) | 2003-07-16 | 2013-04-23 | Yongxing Qiu | Antimicrobial medical devices |
AU2004262891B2 (en) * | 2003-07-16 | 2007-04-05 | Novartis Ag | Antimicrobial medical devices |
CN100374169C (en) * | 2003-07-16 | 2008-03-12 | 诺瓦提斯公司 | Antimicrobial medical devices |
JP2009500645A (en) * | 2003-07-16 | 2009-01-08 | ノバルティス アクチエンゲゼルシャフト | Antibacterial medical device |
WO2005033751A1 (en) * | 2003-09-30 | 2005-04-14 | Johnson & Johnson Vision Care, Inc. | Methods of preparing ophthalmic devices |
WO2005058253A1 (en) * | 2003-12-17 | 2005-06-30 | Heraeus Kulzer Gmbh | Antimicrobial nano silver additive for polymerizable dental materials |
GB2425126A (en) * | 2004-01-28 | 2006-10-18 | Qinetiq Nanomaterials Ltd | Method of manufacture of polymer composites |
WO2005073289A1 (en) * | 2004-01-28 | 2005-08-11 | Qinetiq Nanomaterials Limited | Method of manufacture of polymer composites |
WO2005088351A3 (en) * | 2004-03-17 | 2006-03-16 | Thorkild Andersen | Contact lens, container and insert for avoiding infection of the eye |
WO2005088351A2 (en) * | 2004-03-17 | 2005-09-22 | Thorkild Andersen | Contact lens, container and insert for avoiding infection of the eye |
JP2006076295A (en) * | 2004-08-26 | 2006-03-23 | Johnson & Johnson Vision Care Inc | Mold form for manufacturing lens for eye |
US8501833B2 (en) | 2005-12-14 | 2013-08-06 | Novartis Ag | Method for preparing silicone hydrogels |
US7960465B2 (en) | 2006-06-30 | 2011-06-14 | Johnson & Johnson Vision Care, Inc. | Antimicrobial lenses, processes to prepare them and methods of their use |
US9358317B2 (en) | 2006-10-31 | 2016-06-07 | Johnson & Johnson Vision Care, Inc. | Acidic processes to prepare antimicrobial contact lenses |
WO2008094876A1 (en) | 2007-01-31 | 2008-08-07 | Novartis Ag | Antimicrobial medical devices including silver nanoparticles |
EP3248621A1 (en) | 2007-10-08 | 2017-11-29 | Johnson & Johnson Vision Care, Inc. | Methods for forming stabilized metal salt particles |
US9872501B2 (en) | 2007-10-08 | 2018-01-23 | Johnson & Johnson Vision Care, Inc. | Methods for forming stabilized metal salt particles |
Also Published As
Publication number | Publication date |
---|---|
CN100363061C (en) | 2008-01-23 |
DE60117863T2 (en) | 2006-11-16 |
TWI229209B (en) | 2005-03-11 |
US20020197299A1 (en) | 2002-12-26 |
CA2432796A1 (en) | 2002-08-15 |
HK1056516A1 (en) | 2004-02-20 |
JP2004526187A (en) | 2004-08-26 |
DE60117863D1 (en) | 2006-05-04 |
EP1355681B1 (en) | 2006-03-08 |
EP1355681A1 (en) | 2003-10-29 |
CN1630536A (en) | 2005-06-22 |
KR20030063460A (en) | 2003-07-28 |
BR0116479A (en) | 2004-01-13 |
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