US3700761A - Fabrication of soft plastic contact lens blank - Google Patents

Fabrication of soft plastic contact lens blank Download PDF

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US3700761A
US3700761A US880828A US3700761DA US3700761A US 3700761 A US3700761 A US 3700761A US 880828 A US880828 A US 880828A US 3700761D A US3700761D A US 3700761DA US 3700761 A US3700761 A US 3700761A
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lens
cut
percent
mass
water
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Kenneth F O'driscoll
Allan A Isen
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GRIFFIN LAB Inc
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GRIFFIN LAB Inc
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    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/00009—Production of simple or compound lenses
    • B29D11/00038—Production of contact lenses
    • B29D11/00067—Hydrating contact lenses
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/00009—Production of simple or compound lenses
    • B29D11/00038—Production of contact lenses
    • B29D11/00125—Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere
    • B29D11/00134—Curing of the contact lens material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/00865—Applying coatings; tinting; colouring
    • 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
    • C08F271/00—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
    • C08F271/02—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00 on to polymers of monomers containing heterocyclic nitrogen

Definitions

  • the lenses may be equilibrated in the wet state by hydrating with normal saline solution.
  • the lenses may be maintained by treatment with hydrogen peroxide.
  • Steps (3) and (4) toughen the lens, increase its elasticity and its elastic recovery and improve its dimensional stability.
  • From 20 to percent by weight of polyvinyl pyrrolidone imparts hygroscopic and unusual water-swelling characteristics while retaining elastic recovery.
  • the water-swollen lens contains from 40-80 percent water, preferably from -55 percent, and in isotonic saline, the water content changes to about 5258 percent.
  • the polyvinyl pyrrolidone incorporation the lens is readily cleaned after use in the eye with dilute hydrogen peroxide to rid it of imbibed muco-protein, catalase and the like.
  • the invention relates to a method of shaping and polymerizing, at low (4060 C.) and medium temperatures (90-l20 C.), a monomer-polymer dispersion by casting in a mold and continuing the polymerization after removal from the mold, the dispersion consisting preferably of 20 -45 percent of polymerized vinyl pyrrolidone and 80-55 percent of monomethacrylate ester of a glycol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol and dipropylene glycol, there being present no more than about 1 percent by weight of methacrylic acid and no more than 0.2 percent by weight of the dimethacrylate of the aforesaid glycols.
  • the monomer is essentially pure hydroxy alkyl methacrylate ester.
  • An essential feature of the method of the present invention is the stagewise post-polymerization of the bulk polymerized solid casting after free radical initiation at low (40-60 C.) and medium (90-120 C.) temperatures by means of (a) polymerizing radiation'of the dry solid.
  • the hydrogen peroxide treatment of the waterswollen product in an isotonic salt solution toughens the solid post-polymerized product into completely hydrated condition (swollen with from 45-80 percent water which is proportional to the polyvinyl pyrrolidone content).
  • Armen et al. US. Pat. No. 3,086,956, in Example 7 shows polymerization of polyglycol monomethacrylate with polyvinyl pyrrolidone and ammonium persulfate initiator at pH 5 in the presence of water to provide a graft copolymer in the form of a turbid aqueous solution containing 19.7 percent solids.
  • Ackerman et al. US. Pat. No. 2,923,692 shows lightly cross-linked copolymers of esters of methacrylic acid and vinyl pyrrolidone (see column 7, line 32).
  • the products of Ackerman et al. contain highly water-sensitive, cross-linked acrylic acid groups which can be neutralized with alkali to form a smooth, non-grainy mucilage after the product has been purified by washing, dried and then ground in a homogenizer or colloid mill.
  • Robinson US. Pat. No. 2,941,980 shows water-soluble polymers and copolymers of pyrrolidone with various monomers, such as acrylic acid, vinyl acetate and the like, and these water-soluble polymers are mixed with alkylated phenols serving as plasticizers to provide coatings for basis of metal, paper, glass, etc., to afford protection against water.
  • Copolymers of vinyl pyrrolidone and acrylic acid, as in Robinson, or graft polymers of polyglycol methacrylate with polyvinyl pyrrolidone, as in Armen et al. are not satisfactory as water-swollen, tough contact lens blanks. These products form low-strength films which, when wet with water, are easily distorted by tensile forces and exhibit poor recovery, inadequate elongation and inadequate toughness.
  • the method converts a free radial initiated solid polymer containing polyvinyl pyrrolidone and polyhydroxy alkyl methacrylate to a highly permeable, soft, hydrated, shaped mass having improved toughness, elasticity and recovery by treating the dry solid mass with radiation to aid densification and thereafter hydrating the mass in saline solution and treating with hydrogen peroxide to cause further toughening by chemical interaction between the polyvinyl pyrrolidone and polymerized methacrylate.
  • a tough, soft, hydrated, fluidpermeable contact lens cut from a hard blank is prepared by casting a composition consisting essentially of 20-45 percent of solid, high molecular weight polyvinyl pyrrolidone in a network of -5 5 percent of hydroxy ethylmethacrylate, hydroxy propylmethacrylate, or diethylene glycol monomethacrylate which may contain, as impurities, less than 1 percent of methacrylic acid, preferably not more than 0.2 percent, and up to 0.2 percent of ethylene glycol dimethacrylate.
  • the polymerization of the bulk matrix and preformed polymer is carried out in stages, first in a casting mold and then outside of the mold, as follows:
  • a lowtemperature peroxide such as acetyl peroxide, disecondary butyl peroxy dicarbonate, cyclohexanone peroxide, etc.
  • Step (3) increases the toughness of the lens in hydrated condition, as measured by a bubble bursting test which blows compressed air against the lens to break or burst it and step (4) further increases the toughness of the water-swollen lens and aids in cleaning the lens of debris which accumulates thereon from the eye.
  • polyvinyl pyrrolidone in responding to hydrogen peroxide treatment which, in the preferred embodiment of the invention, has a Fikentscher K value of from 30 to 90, appears to be a critical aspect of the new and unexpected properties of toughness, elastic recovery and elasticity developed by the graft copolymer with hydroxy alkyl acrylate.
  • Polyvinyl pyrrolidone is comparable to gelatin and albumen in respect to its high affinity for water and its low toxicity and general biochemical inertness.
  • the polyvinyl pyrrolidone which is preferred for the present contact lens manufacture has a Fikentscher K value of 33, corresponding to a molecular weight between about 25,000 and 50,000, the number average molecular weight by osmosis being about 37,000 which is about half of that of bovine serum albumen.
  • the carbonamide groups present in gelation are responsible for thread like structures in the hydration of gelatin emulsions which have been detected under the ultramicroscope in grainless photographic emulsions containing from 5-10 percent of gelatin in solutions adjusted to the isoelectric point.
  • the hydrogen peroxide has the effect of clearing the lens of any catalase or of any other mucoprotein of the which not only sterilizes the lenses but maintains clarity, transparency and fluid permeability.
  • this treatment permits freedom from eye irritation and prevents the development of edema under the lens when the lens is worn continuously for 24 hours and longer.
  • the hydrated hydrogen peroxide-treated product of the present invention appears to possess significantly different properties from gelatin in its resistance to change by acids, alkalis and relatively high temperatures in the wet condition.
  • Gelatin being amphoteric, reacts with acid and alkali and reversibly dissolves on heating unless it is denatured and flocculated by overheating when wet.
  • the present product withstands boiling water for periods up to 72 hours without alteration of its desirable permeable characteristics.
  • FIG. 1 is a flow diagram showing mixing of ingredients, stirring, degassing, pouring into the mold and placing the filled mold into the oven for the first and second stage curings at low and medium temperatures, respectively, to produce a hard, transparent, shaped mass which is cut and polished;
  • FIG. 2 is a diagrammatic view showing the placement of male and female mold parts to shape the hard, transparent solid which is subsequently cut;
  • FIG. 3 is a flow diagram showing the manufacturing steps taken in a particularly preferred embodiment whereby radiation treatment, water-swelling in alkaline medium, osmotic swelling and hydrogen peroxide hardening are carried out to improve the physical properties and water permeability and to diminish osmotic swelling of the cut and polished lens;
  • FIG. 5 is a sectional view which shows the relation of the mold parts and the hard, transparent, shaped mass after one-stage curing and before ejection from the mold.
  • HEMA liquid methacrylate
  • catalyst e.g. 0.2 grams of benzoyl peroxide in powdered form and 0.2 grams of di-secondary butyl peroxy dicarbonatc, available under the trade name of Lupersol 225 from Lucidol Chemical Corporation, Buffalo, New York.
  • the catalyst-liquid mixture, 40 parts was added to the PVP-HEMA mixture, 120 parts, and was mixed carefully to provide 160 parts of monomer with 40 parts of polymer dispersion or slurry. These proportions cut down the shrinkage as compared with liquid HEMA alone.
  • the amount of secondary butyl peroxy dicarbonate catalyst which is particularly effective at a temperature of 40-60 C. and of benzoyl peroxide catalyst which is particularly effective at a temperature of 90-120 C. is 0.2 part of each catalyst per 200 parts of liquid PVP mixture containing 160 parts of liquid monomer and 40 parts of PVP, e-.g. a proportion of about 0.1 percent for each of these catalysts.
  • PVP was present in an amount of percent by weight of the dispersion
  • the dispersion was de-aerated to permit air bubbles to escape, and the mold was filled in the manner shown diagrammatically in FIG. 1.
  • the tray of molds was then placed in an air circulating oven for 20 hours at a temperature of 40 C.
  • the molds were removed from the oven and taken apart by using a small arbor press against the flat end of the Teflon core at the bottom of the mold unit. This forced the cast blank out of the other end of the sleeve.
  • the cast blanks were placed on aluminum sheets and returned to the oven where they were post-cured at a temperature of 110 C. for 1% hours.
  • the finished cast plastic blanks were a polymer consisting of PVP to which poly- HEMA had been grafted.
  • Example 2 The casting procedure set out in Example 1 was carried out, but instead of using 20 percent by weight of PVP, 30 percent by weight was used.
  • the lens made by the technique of Example 1 contained about 55 percent of water as measured in isotonic saline and resulted in a lens that came up to the exacting standards set for Example 1.
  • EXAMPLE 3 The process of Example 1 was repeated, except that diethylene glycol monomethacrylate was used with 25 percent by weight of PVP. This lens, too, met the standards set in Example 1.
  • Example 4 The process of Example 1 was repeated except that instead of 20 percent of PVP, 35 percent by weight was used. The resulting lens came up to the standards set for Example 1.
  • EXAMPLE 5 A mixture of parts of hydroxy propyl methacrylate and 80 parts of HEMA was used for the monomer phase with 20 percent by weight of PVP and the process of Example 1 was repeated. The resulting lens came up to the high standards set for Example 1.
  • the water content of the lens made and tested in Example l was about 51 percent in water and about 49.5 percent in 0.9 percent saline solution.
  • the water content of poly-HEMA from which PVP has been excluded is about 38 percent and 36 percent.
  • the water content of the remaining examples was substantially the same as that in Example 1.
  • the main differences imparted by substituting propylene glycol monomethacrylate or diethylene glycol monomethacrylate is to lower the refractive index and to make the polymerized solid slightly more flexible.
  • PVP is used in an amount less than 20 percent, the water uptake value of about 50-60 percent is not achieved in the hydrated water-swollen polymerized mass and the desired toughening and increase instrength are not achieved by subsequent hydrogen peroxide treatment.
  • the low temperature initiator is omitted and polymerization is carried out at -l20 C. for onehalf to 2 hours, the solid product is not uniform in physical properties nor does it provide the toughening and improved strength necessary to come up to the desired standard. Without both low and medium temperature initiators, the improvement in permeability over the commercial Soflens made under the Wichterle patents is not achieved, nor is consistent reproducibility possible.
  • the critical two-stage initiation at temperatures of 4060 C. in the mold to form the solid rod and at 90-l20'C. out of the mold, in a tray in an oven, to harden the self-sustaining rod provides a rod of stock material of Shore A Hardness value between 70 and 90 which can be cut and polished into lenses by the familiar technique used with hard acrylic material. Even without further treatment, such lenses can be hydrated and water-swollen to surpass the performance of the presently commercially available hydrophilic lenses.
  • the mass after hydration becomes excessively soft. Even after post-polymerization, the product cannot be toughened to match the high strength and elasticity values of the preferred examples above. Only in the range of 20-45 percent PVP can the present polymerized composition, free from crosslinker, match the strength properties of the commercial Soflens.
  • the Soflens material does not possess the same high permeability rate of diffusion which in the present examples is from l-l5times that of the Soflens material.
  • the lenses are made by cutting and polishing the shaped masses in the hard state, as shown in the flow diagram of FIG. 1 and in the views of FIGS. 2, 4a-4d, and 5, so that they appear to be exactly like a hard acrylic contact lens.
  • the molding ingredients comprising the mixture of hydroxy alkyl methacrylate, PVP, low and medium temperature initiators, cure in the first stage in the molds and in the second stage in the trays to produce hard, transparent, shaped, plano-concave cylinders .20, as illustrated in FIG. 2.
  • the concave surface is formed by male mold member fitting into female'mold member 1 l.
  • the interior surface of the female member 11 is coated with Teflon, as is the outer surface of the male member 10.
  • the Shore A Hardness value of the shaped mass 20 is between about 80 and 90. Subsequent post-polymerization treatment increases the Shore A Hardness value by from 3 to 10 points. At higher PVP concentrations, lower initial Shore A Hardness values are obtained.
  • Subsequent treatment, e.g., post-polymerization, by radiation causes a greater increase in Shore A Hardness at these higher PVP concentrations and this demonstrates that radiation is especially effective in post-polymerization of the PVP moiety in the product. Radiation also tends to cause slight embrittlement so that if is easier to cut the entire mass 20 before radiation treatment.
  • the present material contains no cross-linker as is required in the lens composition of this patent and it is surprising that the substantially pure poly-HEMA matrix of the present invention, having a Shore A Hardness value close to 90, can be easily cut in the dry state to very small tolerances of about one one-hundredth mm. and thereafter can be hydrated to imbibe at least 50 percent more water than the prior art lens. This cutting in the dry state permits thinner edge sections to be produced and permits uniformity in lens manufacture which cannot be achieved in' the prior art manufacturing methods.
  • the index of refraction of the cast blank 20 is approximately 1.49. In the hydrated state, the index of refraction of the lens is approximately 1.39
  • the lens blank 20 is a small cylinder with a concave curve at one end which must be optically finished and a small amount of stock is removed from this surface, e.g., a minimum amount of about 0.2 mm. in thickness and a maximum of 0.5 mm., the removal being symmetrical and from the entire surface.
  • the blank 20 is removed in the manner shown in FIG. 5 wherein ram 13 pushes against the planar surface of the blank STEP eject the blank from the female mold member 10.
  • the blank is removed from the same end into which the dispersion or slurry was poured and this removal is completely different from that which is carried out in US. Pat. No. 3,361,858, wherein the lens is molded to size on a mount and is removed from the mount by immersing in water to swell it and allow it to be peeled from the mount.
  • the blank of the present invention is cured in the medium temperature stage on trays and the steps below are followed:
  • FIGS. 4a-4d The cutting steps are shown diagrammatically in FIGS. 4a-4d.
  • the dotted lines in FIG. 4a show removal of peripheral'or radial portions of the blank in order to cut the 180 arc down to about as shown in FIG. 4a and in FIG. 4b.
  • the planar surface is then cut along the dotted line shown at the bottom of FIG. 4b in order to faciliate mounting the blank on a lathe, and this blank is shown in FIG. 4c.
  • the planar cut shown in FIG. 40 is not required.
  • the concave cut is made along the dotted line shown in FIG. 4c and cut lens is shown in FIG. 4d.
  • the flat surface on the back of the blank is faced off in the manner shown in FIGS. 4b and 4c and the center of the flat surface is tapped to make a pivot depression on a small jewelers lathe.
  • the diameter of the blank was reduced in a Levin lathe to a size 0.1 mm. larger than the desired finished lens size (see FIG. 4a).
  • the radius cut on the concave surface matched the surface.
  • finish cutting produced a highly smooth radius cut and an exact center thickness.
  • the thickness was measured by a regular plunger thickness gauge through the small diameter hole in the center of the chuck, which was also used for evaluating the optics as the lens was being finished.
  • the front surface was then polished on an optical polishing machine.
  • the chuck mounted on a vertical spindle and rotated as a polishing lap coated with adhesive tape rocked back and forth over the surface, spinning at the same time.
  • the polish used was Snow Floss Compound mixed with odorless kerosene to the consistency of this paste. It required 3 minutes to complete the surface, and the optical quality was judged by removing the chuck from the spindle and viewing the optics in a lensometer through the hole in the chuck.
  • the finishing of the lens included the addition of a small flat bevel to the inside aspect of the edge approximately 0.3 mm. wide. This was put on by grinding against an emery sphere or a diamond impregnated lap, and polishing against a matching felt lap. Following this, the edge was rounded and polished against a polyurethane sponge saturated with the polish mixture or zinc oxide and odorless kerosene. The lens was then recleaned in Xylene in the ultrasonic cleaner. It was measured and inspected for base curve radius, optical value and quality, thickness and surface scratches.
  • Irradiation is preferably carried out under an ultraviolet lamp which provides a high energy source in the spectral range of 2,000 to 4,000 Angstrom units, for at least one-half hour, preferably 2-4 hours.
  • the bursting strength is increased from 7 p.s.i. gauge to 10.5-11.0 p.s.i. gauge, an increase of at least about 50 percent of the originalvalue and the hydrated lens loses practically none of its elasticity and rapid recovery.
  • the commercial Sofiens the lens of the prior art, does not improve under irradiation in its bursting strength. Therefore, it is clear that the PVP component in the original composition, as well as the unique two-step polymerizing procedure, 'e.g., the low temperature initiation and the medium temperature initiation referred to in FIG. 1, coact in a new way with irradiation treatment in the solid polymerized state to produce this new and unexpected result.
  • Utraviolet sources such as the mercury vapor tube, a Xenon lamp, or a carbon arc tube, may be used.
  • irradiation sources which may be used are a cobalt 60 source which emits gamma radiation, spent reactor elements from a uranium pile which also emit gamma radiation, or high energy ionizing radiation from a commercially available source, e.g., Radiation Dynamics, Long Island, New York X-Rays may be used at exposure dosages of 10 roentgens for a period of 15 minutes to 1 hour.
  • Gamma radiation dosage for postpolymerization treatment is preferably from about 5 to about megarads for 5 minutes to 1 hour. All treatments by irradiation are carried out'at room temperature.
  • the hard finished lens was placed under a pure ultraviolet light for a period of 3% hours.
  • the light source was 6 inches from the lens.
  • the unit was covered to prevent light loss and the polymerization of poly-HEMA and PVP was completed in 2 hours.
  • the light source was a 250 watt Spectraline utraviolet lamp.
  • the lenses were then placed, for 4 hours, in a bath of 10 volume reagent grade hydrogen peroxide (3% H 0 to which had been added sufficient pure sodium chloride to produce the equivalent of a normal saline solution. This caused the lenses to shrink in size and become hypertonic. Following this, they were boiled in the pressure cooker in distilled water for 2 hours andagain in normal saline for 2 hours. See FIG. 3.
  • the hard cut lens resulting from the manufacturing operations shown in FIGS. 1 and 4a-4d can be tested for bursting strength by binding the edges about the opening of one-fourth inches pipe and measuring the air pressure required to burst the lens which has been boiled in water of 4 hours to hydrate it.
  • This test carried out with the cut lens of FIGS. 1 and 4a-4d of the invention showed a bursting strength of 7 p.s.i. gauge pressure.
  • the bursting strength by the above mentioned test is increased from 10.5-11 p.s.i. up to 16-17 p.s.i., an increase of at least 250 percent based upon the original bursting strength and an increase of about 100 percent f the original value as compared with the 50 percent increase achieved by irradiation.
  • the hydrogen peroxide treatment accomplishes the most surprising improvements in the physical properties of the hydrated, water-swollen lens which facilitate maintenance and cleaning of the lens by the patient.
  • This treatment there is accomplished, as mentioned above, an increase in bursting strength after irradiation of 10.5-11 p.s.i. up to 16-17 p.s.i., gauge pressure. If alkaline bicarbonate solution (1 percent) at pH 8 is repeatedly applied to the lens, a slight softening occurs and the bursting strength falls to about 12.5-13.5 p.s.i.
  • An objective slit lamp fluorophotometer measured fluorescein concentration in the lenses, in the interior segment of the eye, and in the solution.
  • the fluorophotometer consists of a light sensing device built into the eye piece of the lamp and measures the fluorescein concentration in an area 0.08 mm. across. The instrument is accurate to within plus or minus 2 percent. The unknown is compared with a fresh, stable, standard fluorescein solution.
  • the lenses themselves absorb less than 3 percent of the emitted light and do not interfere with the test by reason of light absorption.
  • the volume of the soaking solution is large in comparison to the lens volume.
  • Lenses fluoresced uniformly under the slit lamp after 90 seconds of soaking on a fluorescein (5 X 10 mg ./ml.) solution. Three distinct zones were observed in the Soflens lenses soaked for 30 minutes due to the fluorescein slowly diffusing to the interior of the lenses.
  • the lenses of the present invention take up fluorescein quite rapidly; uptake is complete in about 2 hours.
  • the Bausch & Lomb lenses (Soflens) take up fluorescein slowly and continue to do so for over 24 hours, reaching a final concentration approximately 2.3 times that in the lenses of the present invention.
  • the total uptake or fluorescein was linearly related to the concentration of the soaking solution over a 4,000-fold concentration range between 5 X 10- and 20 mg./ml.
  • the present lenses were air dried, place in fluorescein solution and the uptake by the dried lenses was substantially identical to the fully hydrated lenses.
  • the corneal and anterior chamber concentrations of fluorescein are shown in Tables 1 and 2 below.
  • the corneal and anterior chamber concentrations were higher with the lens of the present invention than with the other lenses. There was essentially no difference between using no. lens, standard methacrylate lens, or the Bausch & Lomb lens.
  • the corneal and anterior chamber concentrations of fluorescein in the eye with the lens of the present invention were six to eight times that attained with any other mode of treatment.
  • the lens of the present invention was able to maintain the fluorescein concentration in the ocular tissues for 24 hours despite the known rapid exit of fluorescein from the eye. It should be noted that the lens had not been presoaked in fluorescein prior to insertion.
  • the present lenses were presoaked in solutions of 0.1 percent and 0.01 percent fluorescein and inserted into the right eyes of three rabbits. At the same time, a drop of the 0.01 percent solution was put into each of the left eyes. 90 minutes later, the lenses were removed, the eyes were irrigated with saline and the corneal and anterior chamber concentrations were determined. The lenses were the reinserted and the rabbits received one drop of the 0.01 percent solution in the left eye every 30 minutes for 2 additional hours. Saline solution was instilled into the right eye.
  • the corneal and aqueous humor concentrations of fluorescein at l A and 3 Va hours are shown in Tables 3 and 4 below.
  • the ocular concentrations attained with the presoaked lenses were four times higher than those attained with frequent drops. Increasing the concentration of the soaking solution ten-fold resulted in an 800 percent increase in the ocular concentrations. It took much less fluorescein to get the same ocular concentration if the fluorescein was permeated into a lens that if it was instilled topically.
  • the lens of the present invention appears to permit higher transmission of oxygen than the commercially available hydrophilic lens and, as a consequence, is of value in permitting oxygen access across the lens to the cornea.
  • the lenses of the present invention made by the twostage initiation process shown in FIG. 1 without the further steps of irradiation and hydrogen peroxide treatment, exhibit permeability and diffusion characteristics comparable to those pointed out in the studies above; and these lenses, cut from the polymerized rod, as shown in FIGS. 4a-4d, respond to hydrogen peroxide toughening and cleaning, althouth to a degree substantially less than the lenses which are made by the preferred method of the invention as shown in FIG. 3.
  • the diffusibility of solutes through the lenses made by the methods of FIGS. 1 and 3 is from about 6 toabout times as great as the diffusibility of the commercially available Soflens, this diffusibility being expressed as the rate of elution of a dilute tracer material through the lens.
  • a comparative diffusion value is demonstrated where a dye is seen to completely diffuse in a few hours through the lens of the present invention, while such diffusion through the presently commercially available lenses takes 24 hours or longer.
  • novel circular lens of our copending application is placed in contact with the cornea, over the super-sensitive limbal area, with its thin flap or edge extending a few millimeters beyond the limbus, the limbal area of the lens defining a circular tear vesicle which is cut out from the material of the lens adjacent the flap.
  • This novel lens vesicle provides a clear solution of liquid tears adjacent the cornea and osmotic pressure is created in a direction from the less dense tear liquid to the more dense liquid in the cornea to aid in bathing the eye.
  • the semi-scleral flap is held to the scleral portion of the eye by capillary attraction.
  • Tears can enter under the flap to replenish the vesicle well which is immediately adjacent the inner edge of the lens.
  • Hypertonic eyedrops instilled into the eye stimulate the washing and cleaning function of the tears, and any medication in these eyedrops diffuses rapidly, in mere minutes, through the permeable structure of the lens.
  • the hydrogen peroxide treatment appears not only to toughen the lens and raise the bursting strength values, as mentioned above, from 16 p.s.i. gauge to 19-20 p.s.i. gauge, but it also opens and cleans the pores or microvoids in the lens material through which diffusion takes place. Therefore, hydrogen peroxide at 3 percent dilution constitutes a maintenance fluid which is used in conjunction with 1 percent sodium bicarbonate solution, the latter relaxing the pores and softening the lens to aid in cleaning and reducing the burstingstrength by 3 or 4 p.s.i. gauge units and the former reversing this decrease to bring the lens back to its maximum toughness after cleaning.
  • aging of the lens through normal use e.g., wearing and cleaning, has been found to slightly increase the bursting strength value of the lens by 2 or 3 p.s.i. gauge.
  • the lens is a newly manufactured lens having a bursting strength of 16 p.s.i. gauge or an aged lens with bursting strength of 20 p.s.i. gauge, no difference is found in the corrective function of the lens or in its comfort.
  • the lenses of the present invention resist the substantial dimensional changes which ordinarily occur when different osmotic salt concentrations are applied.
  • the anisotropic swelling and shrinking characteristics at 50-55 percent water uptake appear to provide a unique environment for resisting osmotic dimensional change which would cause the lens to shift its position or to flex in response to normal movement of the eyelid or illumination by strong light, irritation and the like.
  • the inside curve of the lens must be steeper than the curve of the cornea with a space under the lens in the central region 16 in order to shape the lens to the cornea. If is this space which flexes with each blink.
  • the edge of the hydrophilic lens grabs the cornea at the sensitive limbal area.
  • the chemical composition of the present hygroscopic lens e. g.,' the critical PVP and I-IEMA content, combined with the critical method of two-step polymerization to permit precision grinding and uniformity, and the post-polymerization with radiation and hydrogen peroxide, provide precision fitting, maximum strength, elasticity and elastic recovery properties, all of which are essential to eye comfort when the lens is worn for long periods of time.
  • the composition also has utility as a liquid, hygroscopic coating material which strongly adheres to glass, plastic or metal when cured, after application, in two stages under the temperature condition shown in FIG. 1.
  • the liquid slurry can be applied in a thickness .of l-lO mils onto a glass tumbler to provide a frost-free drinking glass for cold drinks, the glass being free from outside condensation.
  • the coating may be applied to an automobile windshield to make it fog-free on the inside.
  • the coating may be applied to the polycarbonate lenses used in ski goggles or to contact lenses made of CR-39 (polycarbonate) plastic.
  • the membrane composition may be cast as 'a desalination membrane and used to remove salt by reverse osmosis.
  • the membrane may be used as a germicide-carrying bandage for internal and external wounds.
  • these drugs include pilocarpine, belladonna alkaloids, dibenzyline, hydergine, methacholine, carbachol, bethanechol, a sulfonamide and similar medicaments.
  • the precision fitting advantage of the lens of the present invention carries over to prevent liquid buildup behind the bandage when a medicament-carrying bandage is formed for the eyeball which extends over the scleral area under the lid. Edema which is encountered with hard, impermeable acrylic bandages is eliminated.
  • the medicines are not concentrated in the present hydrated plastic membrane to cause osmotic swelling thereof, but are readily diffused to bathe the affected eye portion with the proper concentrations for therapeutic effectiveness. There is no dimensional change of the bandage when hypertonic concentrations of salts and medicines are applied to the eye, and this aids in the healing process.
  • the liquid slurry composition may be used to cast or coat an artificial eye, limb or appendage without shrinkage and to precise dimensions. In all of these uses, the coating, membrane, casting, etc. can be cleaned with hydrogen peroxide at an appropriate time.
  • a method of shaping and cutting a contact lens comprising:
  • a method of shaping and cutting a contact lens comprising:
  • a hard concave-planar cylinder consisting essentially of a reaction product of 20 percent up to 45 percent of a solid, high molecular weight polyvinyl pyrrolidone of Fikentscher K value of 30-90 with -55 percent of monomethacrylate ester of a glycol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol and dipropylene glycol, there being present no more than about 1 percent by weight of methacrylic acid and no more thanabout 0.2 percent by weight of dimethacrylate of the aforesaid LII-P glycols as impurities and two free radical initiators,
  • the first initiator polymerizing said cylinder at a temperature of 4 O-60 C. to form a self-supporting mass which is hygroscopic and which will swell anisotropically when placed in a water medium and the second initiator polymerizing said cylinder to polymerize unreacted material from the polymerization with the first free radical initiator, each of said two free radical initiators being present in an amount of about 0.1 percent by weight of said slurry at a temperature of l 20 C. to complete the hardening of the cylinder;
  • the lens is cut and polished to besubstantially the same thickness at its center and at its corneal edges, to thereby provide zero correction and produce a lens useful as a corneal bandage through which eye medicaments may be diffused.
US880828A 1969-11-28 1969-11-28 Fabrication of soft plastic contact lens blank Expired - Lifetime US3700761A (en)

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JP (1) JPS4832778B1 (fr)
BE (1) BE759530A (fr)
CA (1) CA936300A (fr)
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Cited By (59)

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US3807398A (en) * 1972-09-19 1974-04-30 B Grucza Ocular implant
DE2411895A1 (de) * 1973-03-15 1974-09-19 American Optical Corp Verfahren zum herstellen eines spannungsfreien hydroskopischen festen polymerisats fuer haftglaeser
US3839304A (en) * 1973-02-12 1974-10-01 American Optical Corp Soft contact lens and method of production thereof
US3841598A (en) * 1972-09-19 1974-10-15 B Grucza A mold for casting a hydrophilic contact lens blank
DE2443147A1 (de) * 1973-10-12 1975-04-17 Flow Pharma Inc Verfahren zur reinigung von kunststoffgegenstaenden
US3901969A (en) * 1973-09-10 1975-08-26 Union Corp Sustained release of methantheline
US3912451A (en) * 1973-06-04 1975-10-14 Warner Lambert Co Method for removing hydrogen peroxide from soft contact lenses
US3916033A (en) * 1971-06-09 1975-10-28 High Voltage Engineering Corp Contact lens
US3959102A (en) * 1973-08-06 1976-05-25 Essilor International (Compagnie Generale D'optique S.A.) Method for preparing a crosslinked graft copolymer of silicone and polyvinylpyrrolidone for use as a contact lens, and a contact lens produced thereby
US3966847A (en) * 1969-07-28 1976-06-29 Maurice Seiderman Contact lens from hydrophilic gel polymers of polyvinylpyrrolidone and hydroxyalkyl methacrylate
US3979891A (en) * 1975-03-07 1976-09-14 Patton Orvil D Pneumatic fruit harvester
US3980084A (en) * 1974-01-09 1976-09-14 Hydro Optics, Inc. Ostomy gasket
US3983083A (en) * 1973-12-11 1976-09-28 Japan Atomic Energy Research Institute Soft contact lenses and process for preparation thereof
US4042552A (en) * 1972-09-19 1977-08-16 Warner-Lambert Company Composition for hydrophilic lens blank and method of casting
US4045547A (en) * 1974-11-21 1977-08-30 Warner-Lambert Company Fabrication of soft contact lens and composition therefor
US4063890A (en) * 1973-02-12 1977-12-20 Baron Neville A Method and apparatus for sterilizing and storing contact lenses
DE2740545A1 (de) * 1976-09-13 1978-03-16 American Optical Corp Verfahren zum giessen von polymerenstaeben
US4099859A (en) * 1974-12-02 1978-07-11 High Voltage Engineering Corporation Contact lens having a smooth surface layer of a hydrophilic polymer
US4123408A (en) * 1976-11-26 1978-10-31 American Optical Corporation Hydrogel contact lens
US4126138A (en) * 1974-06-14 1978-11-21 Warner-Lambert Company Soft contact lens
US4189364A (en) * 1972-05-12 1980-02-19 Hydroplastics, Inc. Method for preparing hydrophilic polymers and polymer grafts including irradiation
US4212107A (en) * 1978-06-09 1980-07-15 Orazio Mezzasalma Lens measuring method and apparatus
US4260564A (en) * 1979-02-14 1981-04-07 Intercast Europe S.P.A. Process for the manufacture of spectacle lenses made of diglycol allyl carbonate or the like
FR2470638A1 (fr) * 1979-12-05 1981-06-12 Kendall & Co Composition absorbant l'eau, catheter, suture ou plaque de verre enduits de cette composition
FR2471213A1 (fr) * 1979-12-05 1981-06-19 Kendall & Co Composition absorbant l'eau, catheter, suture ou plaque de verre enduits de cette composition
US4330383A (en) * 1978-07-18 1982-05-18 Polymer Technology Corporation Dimensionally stable oxygen permeable hard contact lens material and method of manufacture
US4368310A (en) * 1981-10-23 1983-01-11 Ppg Industries, Inc. Method of polymerizing sheets
US4395496A (en) * 1981-11-16 1983-07-26 Uco Optics, Inc. Cured cellulose ester, method of curing same, and use thereof
US4550001A (en) * 1981-06-22 1985-10-29 Japan Synthetic Rubber Co., Ltd. Process for producing shaped articles having improved surfaces
US4562018A (en) * 1985-01-28 1985-12-31 Neefe Charles W Method of casting optical surfaces on lens blanks
US4585488A (en) * 1981-12-21 1986-04-29 Ciba Vision Care Corporation Method for disinfecting contact lenses
US4678838A (en) * 1986-08-04 1987-07-07 Ciba-Geigy Corporation Particulate hydroperoxidized poly-N-vinyl lactam, its preparation and use thereof
US4693446A (en) * 1985-09-20 1987-09-15 Techna Vision, Inc. Gasket for molding plastic lenses
US4729892A (en) * 1986-03-21 1988-03-08 Ciba-Geigy Corporation Use of cross-linked hydrogel materials as image contrast agents in proton nuclear magnetic resonance tomography and tissue phantom kits containing such materials
US4791175A (en) * 1986-08-04 1988-12-13 Ciba-Geigy Corporation Particulate hydroperoxidized poly-n-vinyl lactam, its preparation and use thereof
US4826889A (en) * 1978-07-18 1989-05-02 Polymer Technology, Corp. Dimensionally stable oxygen permeable hard contact lens material and method of manufacture
US4829126A (en) * 1985-01-09 1989-05-09 Toyo Contact Lens Co., Ltd. High water-absorptive soft contact lens
US4833196A (en) * 1986-08-04 1989-05-23 Ciba-Geigy Corporation Particulate hydroperoxidized poly-N-vinyl lactam, its preparation and use thereof
US4931228A (en) * 1989-04-05 1990-06-05 Coastvision Method of manufacturing soft contact lens buttons
US5058207A (en) * 1989-11-15 1991-10-22 Winfried Altinger Viewing window for heat protective clothing
EP0453232A2 (fr) * 1990-04-17 1991-10-23 JOHNSON & JOHNSON VISION PRODUCTS, INC. Récipient pour l'hydratation de lentilles de contact
GR910100141A (el) * 1990-04-17 1992-07-30 Johnson & Johnson Vision Prod Μέ?οδος ενυδατώσεως μαλακών φακών επαφής.
US5318853A (en) * 1992-07-22 1994-06-07 Resikast Corporation Adhesive polyester prepolymer which does not etch polycarbonate sheets, and method of preparing same
EP0686488A2 (fr) * 1994-06-10 1995-12-13 JOHNSON & JOHNSON VISION PRODUCTS, INC. Procédé automatisé et dispositif pour l'hydratation de lentilles de contact souples
EP0740998A2 (fr) * 1995-05-01 1996-11-06 JOHNSON & JOHNSON VISION PRODUCTS, INC. Procédé automatisé et dispositif pour l'hydration de lentilles de contact souples
WO2000024568A2 (fr) * 1998-10-26 2000-05-04 Bausch & Lomb Incorporated Procede et dispositif de durcissement pour lentilles de contact
US6642333B2 (en) * 2002-04-04 2003-11-04 Nippon Shokubai Co., Ltd. Vinylpyrrolidone (co)polymer
US20040170666A1 (en) * 2001-05-14 2004-09-02 Richard Keates Eye coverings
US20060117919A1 (en) * 2004-12-06 2006-06-08 Hank Stute Method and apparatus for manufacturing contact lenses
US20060120705A1 (en) * 2004-12-06 2006-06-08 Hank Stute Method and apparatus for manufacturing contact lenses
US20070010595A1 (en) * 2005-02-14 2007-01-11 Mccabe Kevin P Comfortable ophthalmic device and methods of its production
US20080113935A1 (en) * 2004-03-02 2008-05-15 Saul Yedgar Use of lipid conjugates in the treatment of diseases or disorders of the eye
US20080113002A1 (en) * 2006-11-14 2008-05-15 Saul Yedgar Contact lens compositions
US20090051060A1 (en) * 2007-03-30 2009-02-26 Yongcheng Li Preparation of antimicrobial contact lenses with reduced haze using swelling agents
US7618142B2 (en) 2000-03-31 2009-11-17 Cooper Vision International Holding Company, Lp Contact lenses
US7628485B2 (en) 2000-03-31 2009-12-08 Coopervision International Holding Company, Lp Contact lens having a uniform horizontal thickness profile
US20110130555A1 (en) * 2009-05-11 2011-06-02 Saul Yedgar Lipid-polymer conjugates, their preparation and uses thereof
WO2011123180A1 (fr) 2010-04-03 2011-10-06 Praful Doshi Dispositifs médicaux comprenant des médicaments et procédés de fabrication et d'utilisation associés
US9052529B2 (en) 2006-02-10 2015-06-09 Johnson & Johnson Vision Care, Inc. Comfortable ophthalmic device and methods of its production

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US3978164A (en) * 1974-11-21 1976-08-31 Warner-Lambert Company Pyrrolidone-methacrylate graft copolymers from 3-stage polymerization process
KR20230164016A (ko) * 2021-04-02 2023-12-01 오츠카 가가쿠 가부시키가이샤 블록 공중합체, 분산제, 및, 착색 조성물

Cited By (83)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966847A (en) * 1969-07-28 1976-06-29 Maurice Seiderman Contact lens from hydrophilic gel polymers of polyvinylpyrrolidone and hydroxyalkyl methacrylate
US3916033A (en) * 1971-06-09 1975-10-28 High Voltage Engineering Corp Contact lens
US4189364A (en) * 1972-05-12 1980-02-19 Hydroplastics, Inc. Method for preparing hydrophilic polymers and polymer grafts including irradiation
US3807398A (en) * 1972-09-19 1974-04-30 B Grucza Ocular implant
US3841598A (en) * 1972-09-19 1974-10-15 B Grucza A mold for casting a hydrophilic contact lens blank
US4042552A (en) * 1972-09-19 1977-08-16 Warner-Lambert Company Composition for hydrophilic lens blank and method of casting
US3839304A (en) * 1973-02-12 1974-10-01 American Optical Corp Soft contact lens and method of production thereof
US4063890A (en) * 1973-02-12 1977-12-20 Baron Neville A Method and apparatus for sterilizing and storing contact lenses
DE2411895A1 (de) * 1973-03-15 1974-09-19 American Optical Corp Verfahren zum herstellen eines spannungsfreien hydroskopischen festen polymerisats fuer haftglaeser
US3894129A (en) * 1973-03-15 1975-07-08 American Optical Corp Method of manufacture of strain free contact lenses
US3912451A (en) * 1973-06-04 1975-10-14 Warner Lambert Co Method for removing hydrogen peroxide from soft contact lenses
US3959102A (en) * 1973-08-06 1976-05-25 Essilor International (Compagnie Generale D'optique S.A.) Method for preparing a crosslinked graft copolymer of silicone and polyvinylpyrrolidone for use as a contact lens, and a contact lens produced thereby
US3901969A (en) * 1973-09-10 1975-08-26 Union Corp Sustained release of methantheline
DE2443147A1 (de) * 1973-10-12 1975-04-17 Flow Pharma Inc Verfahren zur reinigung von kunststoffgegenstaenden
US3983083A (en) * 1973-12-11 1976-09-28 Japan Atomic Energy Research Institute Soft contact lenses and process for preparation thereof
US3980084A (en) * 1974-01-09 1976-09-14 Hydro Optics, Inc. Ostomy gasket
US4126138A (en) * 1974-06-14 1978-11-21 Warner-Lambert Company Soft contact lens
US4045547A (en) * 1974-11-21 1977-08-30 Warner-Lambert Company Fabrication of soft contact lens and composition therefor
US4099859A (en) * 1974-12-02 1978-07-11 High Voltage Engineering Corporation Contact lens having a smooth surface layer of a hydrophilic polymer
US3979891A (en) * 1975-03-07 1976-09-14 Patton Orvil D Pneumatic fruit harvester
US4127638A (en) * 1976-09-13 1978-11-28 American Optical Corporation Process for casting polymer rods
DE2740545A1 (de) * 1976-09-13 1978-03-16 American Optical Corp Verfahren zum giessen von polymerenstaeben
US4123408A (en) * 1976-11-26 1978-10-31 American Optical Corporation Hydrogel contact lens
US4212107A (en) * 1978-06-09 1980-07-15 Orazio Mezzasalma Lens measuring method and apparatus
US4826889A (en) * 1978-07-18 1989-05-02 Polymer Technology, Corp. Dimensionally stable oxygen permeable hard contact lens material and method of manufacture
US4330383A (en) * 1978-07-18 1982-05-18 Polymer Technology Corporation Dimensionally stable oxygen permeable hard contact lens material and method of manufacture
US4300820A (en) * 1978-11-06 1981-11-17 The Kendall Company Water absorptive composition
US4260564A (en) * 1979-02-14 1981-04-07 Intercast Europe S.P.A. Process for the manufacture of spectacle lenses made of diglycol allyl carbonate or the like
FR2471213A1 (fr) * 1979-12-05 1981-06-19 Kendall & Co Composition absorbant l'eau, catheter, suture ou plaque de verre enduits de cette composition
FR2470638A1 (fr) * 1979-12-05 1981-06-12 Kendall & Co Composition absorbant l'eau, catheter, suture ou plaque de verre enduits de cette composition
US4550001A (en) * 1981-06-22 1985-10-29 Japan Synthetic Rubber Co., Ltd. Process for producing shaped articles having improved surfaces
US4368310A (en) * 1981-10-23 1983-01-11 Ppg Industries, Inc. Method of polymerizing sheets
US4395496A (en) * 1981-11-16 1983-07-26 Uco Optics, Inc. Cured cellulose ester, method of curing same, and use thereof
US4585488A (en) * 1981-12-21 1986-04-29 Ciba Vision Care Corporation Method for disinfecting contact lenses
US4829126A (en) * 1985-01-09 1989-05-09 Toyo Contact Lens Co., Ltd. High water-absorptive soft contact lens
US4562018A (en) * 1985-01-28 1985-12-31 Neefe Charles W Method of casting optical surfaces on lens blanks
US4693446A (en) * 1985-09-20 1987-09-15 Techna Vision, Inc. Gasket for molding plastic lenses
US4729892A (en) * 1986-03-21 1988-03-08 Ciba-Geigy Corporation Use of cross-linked hydrogel materials as image contrast agents in proton nuclear magnetic resonance tomography and tissue phantom kits containing such materials
US4833196A (en) * 1986-08-04 1989-05-23 Ciba-Geigy Corporation Particulate hydroperoxidized poly-N-vinyl lactam, its preparation and use thereof
US4791175A (en) * 1986-08-04 1988-12-13 Ciba-Geigy Corporation Particulate hydroperoxidized poly-n-vinyl lactam, its preparation and use thereof
US4678838A (en) * 1986-08-04 1987-07-07 Ciba-Geigy Corporation Particulate hydroperoxidized poly-N-vinyl lactam, its preparation and use thereof
US4931228A (en) * 1989-04-05 1990-06-05 Coastvision Method of manufacturing soft contact lens buttons
US5058207A (en) * 1989-11-15 1991-10-22 Winfried Altinger Viewing window for heat protective clothing
EP0453232B1 (fr) * 1990-04-17 1997-03-05 JOHNSON & JOHNSON VISION PRODUCTS, INC. Récipient pour l'hydratation de lentilles de contact
USRE36302E (en) * 1990-04-17 1999-09-14 Johnson & Johnson Vision Products, Inc. Chamber for hydrating contact lenses
GR910100130A (el) * 1990-04-17 1992-07-30 Johnson & Johnson Vision Prod Θάλαμος ενυδατώσεως φακών επαφής.
GR910100141A (el) * 1990-04-17 1992-07-30 Johnson & Johnson Vision Prod Μέ?οδος ενυδατώσεως μαλακών φακών επαφής.
US5094609A (en) * 1990-04-17 1992-03-10 Vistakon, Inc. Chamber for hydrating contact lenses
EP0453232A2 (fr) * 1990-04-17 1991-10-23 JOHNSON & JOHNSON VISION PRODUCTS, INC. Récipient pour l'hydratation de lentilles de contact
US5318853A (en) * 1992-07-22 1994-06-07 Resikast Corporation Adhesive polyester prepolymer which does not etch polycarbonate sheets, and method of preparing same
US5445890A (en) * 1992-07-22 1995-08-29 Resikast Corporation Bullet resistant glass/glass, glass/plastic, and plastic/plastic laminate composites
EP0686488A2 (fr) * 1994-06-10 1995-12-13 JOHNSON & JOHNSON VISION PRODUCTS, INC. Procédé automatisé et dispositif pour l'hydratation de lentilles de contact souples
EP0686488A3 (fr) * 1994-06-10 1996-11-20 Johnson & Johnson Vision Prod Procédé automatisé et dispositif pour l'hydratation de lentilles de contact souples
EP0740998A2 (fr) * 1995-05-01 1996-11-06 JOHNSON & JOHNSON VISION PRODUCTS, INC. Procédé automatisé et dispositif pour l'hydration de lentilles de contact souples
EP0740998A3 (fr) * 1995-05-01 1996-11-20 JOHNSON & JOHNSON VISION PRODUCTS, INC. Procédé automatisé et dispositif pour l'hydration de lentilles de contact souples
WO2000024568A2 (fr) * 1998-10-26 2000-05-04 Bausch & Lomb Incorporated Procede et dispositif de durcissement pour lentilles de contact
WO2000024568A3 (fr) * 1998-10-26 2000-07-27 Bausch & Lomb Procede et dispositif de durcissement pour lentilles de contact
US7625084B2 (en) 2000-03-31 2009-12-01 Coopervision International Holding Company, Lp Contact lens
US7628485B2 (en) 2000-03-31 2009-12-08 Coopervision International Holding Company, Lp Contact lens having a uniform horizontal thickness profile
US7618142B2 (en) 2000-03-31 2009-11-17 Cooper Vision International Holding Company, Lp Contact lenses
US20040170666A1 (en) * 2001-05-14 2004-09-02 Richard Keates Eye coverings
US6642333B2 (en) * 2002-04-04 2003-11-04 Nippon Shokubai Co., Ltd. Vinylpyrrolidone (co)polymer
US20080113935A1 (en) * 2004-03-02 2008-05-15 Saul Yedgar Use of lipid conjugates in the treatment of diseases or disorders of the eye
US8865681B2 (en) 2004-03-02 2014-10-21 Yissum Research Development Company of the Hebrew Unitersity of Jerusalem Use of lipid conjugates in the treatment of diseases or disorders of the eye
US20060117919A1 (en) * 2004-12-06 2006-06-08 Hank Stute Method and apparatus for manufacturing contact lenses
US20060120705A1 (en) * 2004-12-06 2006-06-08 Hank Stute Method and apparatus for manufacturing contact lenses
US7187859B2 (en) 2004-12-06 2007-03-06 Paragon Vision Sciences, Inc. Method and apparatus for manufacturing contact lenses
US20070010595A1 (en) * 2005-02-14 2007-01-11 Mccabe Kevin P Comfortable ophthalmic device and methods of its production
US9395559B2 (en) 2005-02-14 2016-07-19 Johnson & Johnson Vision Care, Inc. Comfortable ophthalmic device and methods of its production
US7841716B2 (en) 2005-02-14 2010-11-30 Johnson & Johnson Vision Care, Inc. Comfortable ophthalmic device and methods of its production
US11953651B2 (en) 2005-02-14 2024-04-09 Johnson & Johnson Vision Care, Inc. Comfortable ophthalmic device and methods of its production
US11150383B2 (en) 2005-02-14 2021-10-19 Johnson & Johnson Vision Care, Inc. Comfortable ophthalmic device and methods of its production
US10267952B2 (en) 2005-02-14 2019-04-23 Johnson & Johnson Vision Care, Inc. Comfortable ophthalmic device and methods of its production
US8696115B2 (en) 2005-02-14 2014-04-15 Johnson & Johnson Vision Care, Inc. Comfortable ophthalmic device and methods of its production
US9052529B2 (en) 2006-02-10 2015-06-09 Johnson & Johnson Vision Care, Inc. Comfortable ophthalmic device and methods of its production
US20080113002A1 (en) * 2006-11-14 2008-05-15 Saul Yedgar Contact lens compositions
US8361355B2 (en) * 2007-03-30 2013-01-29 Johnson & Johnson Vision Care, Inc. Preparation of antimicrobial contact lenses with reduced haze using swelling agents
US20090051060A1 (en) * 2007-03-30 2009-02-26 Yongcheng Li Preparation of antimicrobial contact lenses with reduced haze using swelling agents
US20110111120A1 (en) * 2007-03-30 2011-05-12 Yongcheng Li Preparation of antimicrobial contact lenses with reduced haze using swelling agents
US11013811B2 (en) 2009-05-11 2021-05-25 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Lipid-polymer conjugates, their preparation and uses thereof
US20110130555A1 (en) * 2009-05-11 2011-06-02 Saul Yedgar Lipid-polymer conjugates, their preparation and uses thereof
EP3195858A1 (fr) 2010-04-03 2017-07-26 Praful Doshi Dispositifs médicaux comprenant des médicaments et procédés de fabrication et d'utilisation associés
WO2011123180A1 (fr) 2010-04-03 2011-10-06 Praful Doshi Dispositifs médicaux comprenant des médicaments et procédés de fabrication et d'utilisation associés

Also Published As

Publication number Publication date
BE759530A (fr) 1971-04-30
FR2113535A5 (fr) 1972-06-23
CA936300A (en) 1973-10-30
FR2077538A1 (fr) 1971-10-29
GB1339273A (en) 1973-11-28
JPS4832778B1 (fr) 1973-10-09

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