US20180153682A1 - Intraocular lens materials and components - Google Patents

Intraocular lens materials and components Download PDF

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Publication number
US20180153682A1
US20180153682A1 US15/575,405 US201615575405A US2018153682A1 US 20180153682 A1 US20180153682 A1 US 20180153682A1 US 201615575405 A US201615575405 A US 201615575405A US 2018153682 A1 US2018153682 A1 US 2018153682A1
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Prior art keywords
intraocular lens
silicone oil
polymer
polymeric material
adhesive
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Abandoned
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US15/575,405
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Inventor
Sharad Hajela
Gomaa Abdelsadek
Sean HALENBECK
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Alcon Inc
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PowerVision Inc
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Priority to US15/575,405 priority Critical patent/US20180153682A1/en
Publication of US20180153682A1 publication Critical patent/US20180153682A1/en
Assigned to POWERVISION, INC. reassignment POWERVISION, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ABDELSADEK, GOMAA, HALENBECK, Sean, HAJELA, SHARAD
Assigned to ALCON INC. reassignment ALCON INC. CONFIRMATORY DEED OF ASSIGNMENT EFFECTIVE APRIL 8, 2019 Assignors: POWERVISION, INC.
Abandoned legal-status Critical Current

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    • 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
    • A61L27/14—Macromolecular materials
    • A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/14—Eye parts, e.g. lenses, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
    • A61F2/16—Intraocular lenses
    • A61F2/1613—Intraocular lenses having special lens configurations, e.g. multipart lenses; having particular optical properties, e.g. pseudo-accommodative lenses, lenses having aberration corrections, diffractive lenses, lenses for variably absorbing electromagnetic radiation, lenses having variable focus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/14—Eye parts, e.g. lenses, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
    • A61F2/16—Intraocular lenses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/14—Eye parts, e.g. lenses, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
    • A61F2/16—Intraocular lenses
    • A61F2/1613—Intraocular lenses having special lens configurations, e.g. multipart lenses; having particular optical properties, e.g. pseudo-accommodative lenses, lenses having aberration corrections, diffractive lenses, lenses for variably absorbing electromagnetic radiation, lenses having variable focus
    • A61F2/1624—Intraocular lenses having special lens configurations, e.g. multipart lenses; having particular optical properties, e.g. pseudo-accommodative lenses, lenses having aberration corrections, diffractive lenses, lenses for variably absorbing electromagnetic radiation, lenses having variable focus having adjustable focus; power activated variable focus means, e.g. mechanically or electrically by the ciliary muscle or from the outside
    • A61F2/1635—Intraocular lenses having special lens configurations, e.g. multipart lenses; having particular optical properties, e.g. pseudo-accommodative lenses, lenses having aberration corrections, diffractive lenses, lenses for variably absorbing electromagnetic radiation, lenses having variable focus having adjustable focus; power activated variable focus means, e.g. mechanically or electrically by the ciliary muscle or from the outside for changing shape
    • 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
    • A61L27/14—Macromolecular materials
    • A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • A61L27/14—Macromolecular materials
    • A61L27/26—Mixtures of macromolecular compounds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/32—Post-polymerisation treatment
    • C08G77/34—Purification
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • 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
    • G02C7/08—Auxiliary lenses; Arrangements for varying focal length
    • G02C7/081—Ophthalmic lenses with variable focal length
    • G02C7/085—Fluid-filled lenses, e.g. electro-wetting lenses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2240/00—Manufacturing or designing of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2240/00—Manufacturing or designing of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof
    • A61F2240/001—Designing or manufacturing processes
    • 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
    • A61L2430/00—Materials or treatment for tissue regeneration
    • A61L2430/16—Materials or treatment for tissue regeneration for reconstruction of eye parts, e.g. intraocular lens, cornea

Definitions

  • Presbyopia is a condition where the eye loses its ability to focus on nearby objects. It is a natural part of aging and often become noticeable for those in their mid-40's and the condition may continue to worsen until about the age of 65. In order for the eye to see nearby objects clearly, the refractive index of the eye lens needs to be increased, or the shape needs to become more convex, to allow bettering focusing on close objects.
  • cataracts which is a major cause of blindness in the world and the most prevalent ocular disease
  • this visual disability accounts for more than 8 million physician office visits per year.
  • surgical lens removal with intraocular lens (IOL) implantation is the preferred method of treating the related visual limitations.
  • IOL intraocular lens
  • a cataract is defined as an opacity of a patient's lens, whether it is a localized opacity or a diffuse general loss of transparency. To be clinically significant, however, the cataract must cause a significant reduction in visual acuity or a functional impairment.
  • a cataract occurs as a result of aging or secondary to hereditary factors, trauma, inflammation, metabolic or nutritional disorders, or radiation. Age related cataract conditions are the most common.
  • IOL intraocular lens
  • Some intraocular lenses include optics, one or more components of which are polymers.
  • the polymer may have properties that allow the intraocular lens to be deformed to a delivery configuration to enable its implantation in the eye, yet return to a pre-implantation configuration after being implanted in the eye.
  • the polymeric composition may also be desirable that the polymeric composition have a sufficiently high refractive index.
  • Some intraocular lenses herein include a fluid therein, such as a silicone fluid.
  • a fluid therein such as a silicone fluid.
  • some accommodating IOLs use fluid movement within the IOL, or a change in fluid pressure within the IOL, to effect optical power change in the IOL during accommodation.
  • fluids such as silicone oil
  • the fluid over time, may tend to swell into the bulk polymeric material of the intraocular lens. This can reduce the amount of silicone oil available to drive the optical power change in the IOL. It is therefore desirable to minimize the amount of swelling into the bulk material. It may also be important to provide silicone oil that does not reduce the response time of the accommodating IOL. It would be desirable for the polymer and/or fluid to be adapted such that swelling of the fluid into the polymeric material is minimized, or even prevented.
  • IOLs that include different types of material therein (e.g., cured polymers and silicone oils), there may be a desire to substantially index-match the different types of material (i.e. have the same or substantially the same index of refraction). It may therefore also be beneficial to provide a fluid that has a refractive index that is as close to the refractive index of the bulk polymeric material as possible.
  • material e.g., cured polymers and silicone oils
  • One aspect of the disclosure is an intraocular lens comprising a polymeric material, the polymeric material comprising: butyl acrylate present in the amount from 2% to 20%, trifluoroethyl methacrylate present in the amount from 10% to 35%, and phenylethyl acrylate present in the amount from 50% to 80%.
  • the refractive index of the polymeric material is between 1.48 and 1.53. In some embodiments the refractive index of the polymeric material is between 1.50 and 1.53.
  • the polymeric material defines a fluid channel, the intraocular lens further comprising a silicone oil in the fluid channel.
  • the silicone oil is index matched with the polymeric material.
  • the silicone oil has a polydispersity less than 1.2.
  • One aspect of the disclosure is a polymeric material for an ophthalmic device, the polymeric material comprising: an alkyl acrylate present in the amount from 3% to 20%; a fluoroacrylate present in the amount from 10% to 35%; and a phenyl acrylate present in the amount from 50% to 80%.
  • One aspect of the disclosure is an accommodating intraocular lens, comprising: an optic portion adapted to refract light onto a retina, the optic portion comprising a polymeric material; and a silicone oil disposed within the optic portion, wherein the silicone oil has a polydispersity index less than about 1.2.
  • the mean average molecular weight of the silicone oil is between 4500 and 6500.
  • the viscosity is no more than 2400 cP.
  • the silicone oil comprises diphenyl siloxane units.
  • the silicone oil is made from a cyclotrisiloxane comprising a ratio of two dimethyl siloxane units to one diphenyl siloxane unit.
  • the refractive index of the silicone oil is between 1.47 and 1.53, optionally between 1.50 and 1.53.
  • One aspect of the disclosure is an adhesive for an accommodating intraocular lens, wherein the adhesive comprises a first component that is the same or has substantially similar properties as the polymeric material of a first body of the accommodating intraocular lens.
  • the adhesive comprises a second primary component that is a reactive acrylic diluent.
  • the adhesive comprises a first component that is not the same but is substantially similar to the polymeric material of the first body of the accommodating intraocular lens.
  • One aspect of the disclosure is a method of manufacturing a polymeric component of an intraocular lens that includes a plurality of monomers, comprising: forming pre-polymer of the polymer, the pre-polymer comprising the plurality of monomers; and curing the pre-polymer to form the polymeric component.
  • forming the pre-polymer comprises combining a plurality of monomers with a monomer comprising a hydroxy moiety.
  • the method can further comprise creating a crosslinkable polymer from the pre-polymer, wherein creating the crosslinkable polymer comprises changing the hydroxyl moiety to a methacrylate moiety.
  • FIGS. 1A and 1B illustrate an exemplary accommodating intraocular lens.
  • FIG. 1C illustrates a sectional view of the accommodating intraocular lens from FIGS. 1A and 1B .
  • FIG. 1D is a top view of an exemplary posterior element of an accommodating intraocular lens.
  • FIG. 1E is a sectional assembly view of an exemplary optic portion of an accommodating intraocular lens.
  • FIGS. 2A and 2B illustrate the deformation of an exemplary haptic in response to exemplary forces.
  • FIG. 3 illustrates a curing process
  • FIG. 4 illustrates the synthesis of a pre-polymer.
  • FIGS. 5A and 5B illustrate exemplary hydrophilic materials.
  • FIGS. 6A and 6B show crosslinked polymer formation and exemplary adhesive design.
  • the disclosure relates generally to intraocular lenses, optionally accommodating intraocular lenses, and exemplary materials and their properties to impart desired characteristics of the intraocular lens.
  • the intraocular lenses herein are merely examples of intraocular lenses that can include any of the materials herein, and the disclosure is not in any way limited to the exemplary intraocular lenses herein.
  • FIG. 1A is a top view illustrating a merely exemplary accommodating intraocular lens 10 that includes optic portion 12 and a peripheral portion that in this embodiment includes first and second haptics 14 coupled to and extending peripherally from optic portion 12 .
  • Optic portion 12 is adapted to refract light that enters the eye onto the retina.
  • Haptics 14 are configured to engage a capsular bag and are adapted to deform in response to ciliary muscle related capsular bag reshaping.
  • FIG. 1B is a perspective view of intraocular lens 10 showing optic portion 12 and haptics 14 coupled to optic portion 12 .
  • FIG. 1C is a side sectional view through Section A-A indicated in FIG. 1A .
  • Optic portion 12 includes deformable anterior element 18 secured to deformable posterior element 20 .
  • Each haptic 14 includes a fluid chamber 22 that is in fluid communication with optic fluid chamber 24 in optic portion 12 . Only the coupling between the haptic 14 to the left in the figure and option portion 12 is shown (although obscured) in the sectional view of FIG. 1C .
  • the haptic fluid chamber 22 to the left in the figure is shown in fluid communication with optic fluid chamber 24 via two apertures 26 , which are formed in posterior element 20 .
  • the haptic 14 to the right in FIG. 1C is in fluid communication with optic chamber 24 via two additional apertures also formed in posterior element (not shown) substantially 180 degrees from the apertures shown.
  • FIG. 1E is a side assembly view through section A-A of optic portion 12 , which includes anterior element 18 and posterior element 20 (haptics not shown for clarity).
  • posterior element 20 needs to have enough structure through which the channels 32 can be formed.
  • Buttress portions 29 provide that structures in which channels 32 can be formed.
  • anterior element 18 rather than posterior element 20 .
  • the anterior element would include buttress portions 29 or other similar structure to provide structure in which the channels can be formed.
  • the posterior element could be formed similarly to anterior element 18 .
  • posterior element 20 is secured to anterior element 18 at peripheral surface 28 , which extends around the periphery of posterior element 20 and is a flat surface.
  • Elements 18 and 20 can be secured together using known biocompatible adhesives, or adhesives as described elsewhere herein, and using known methods or any of the methods of adhering first and second components herein.
  • Anterior element 18 and posterior element 20 can also be formed from one material to eliminate the need to secure two elements together.
  • the diameter of the region at which anterior element 18 and posterior element 20 are secured to one another is about 5.4 mm to about 6 mm in diameter.
  • haptics (or other type of peripheral portion, if a separate component) can be adhered to the optic using any of the adhesives herein or any methods of adhering first and second components together described herein.
  • This stretching pulls the capsular bag in the generally radially outward direction due to radially outward forces “R” due to the general equatorial connection location between the capsular bag and the zonules.
  • the zonular stretching causes a general elongation and thinning of the capsular bag.
  • the native lens becomes flatter (in the anterior-to-posterior direction) and taller in the radial direction, which gives the lens less power. Relaxation of the ciliary muscle, as shown in FIG. 2A , provides for distance vision.
  • the peripheral region of the elastic capsular bag reshapes and applies radially inward forces “R” on radially outer portion 42 of haptic 14 .
  • the radially outer portion 42 is adapted to deform in response to this capsular reshaping. The deformation decreases the volume of fluid channel 22 , which forces fluid from haptic chamber 22 into optic chamber 24 . This increases the fluid pressure in optic chamber 42 .
  • the increase in fluid pressure causes flexible anterior element 18 and flexible posterior element 20 to deform, increasing in curvature, and thus increasing the power of the intraocular lens.
  • the accommodating intraocular lenses herein can also be adapted to be positioned outside of a native capsular bag.
  • the accommodating intraocular lenses can be adapted to be positioned in front of, or anterior to, the capsular bag after the native lens has been removed or while the native lens is still in the capsular bag, wherein the peripheral portion of the lens is adapted to respond directly with ciliary muscle rather than rely on capsular bag reshaping.
  • the polymeric materials have improved resistance to the diffusion of fluid, relatively high refractive indexes, and are adapted to assume an initial configuration after being deformed during implantation in the human body. While the polymeric materials can be used in a wide variety of applications, the polymers are described herein in their use in an ophthalmic device such as an intraocular lens (“IOL”). While one use of the polymers is for a fluid-driven, accommodating IOL, the polymers can be used in a non-accommodating or non-fluid driven IOL.
  • IOL intraocular lens
  • the polymeric compositions of the present invention can also be used in other ophthalmic devices such as, but not limited to, contact lenses, keratoprostheses, capsular bag extension rings, corneal inlays, corneal rings, or other ophthalmic devices.
  • ophthalmic devices such as, but not limited to, contact lenses, keratoprostheses, capsular bag extension rings, corneal inlays, corneal rings, or other ophthalmic devices.
  • An exemplary alternative use would be in the field of breast implants, such that the polymers can be used as an exterior shell-like material to prevent leakage of an internal material.
  • the polymeric compositions described herein may be used in an IOL, such as any of the fluid-driven IOLs described in U.S. Patent Application No. 60/433,046, filed Dec. 12, 2002, U.S. patent application Ser. No. 10/734,514, filed Dec. 12, 2003, U.S. patent application Ser. No. 10/971,598, filed Oct. 22, 2004, U.S. patent application Ser. No. 11/173,961, filed Jul. 1, 2005, U.S. patent application Ser. No. 11/252,916, filed Oct. 17, 2005, U.S. patent application Ser. No. 11/642,388, filed Dec. 19, 2006, and U.S. patent application Ser. No. 11/646,913, filed Dec. 27, 2006, the disclosures of which are hereby incorporated by reference in their entirety.
  • the compositions may also, however, be used in a non fluid-driven IOL or a non-accommodating IOL.
  • a device implanted in the eye becomes exposed to the fluid in the eye.
  • the fluid in the eye can, over time, diffuse through the device and have unintended and/or undesired effects on the physical characteristics of the device.
  • a polymeric IOL that is implanted in the eye may suffer from the diffusion of eye fluid into the IOL's polymeric material.
  • an ophthalmic device contains a chamber or channel within the device which contains a fluid, there is a risk that that fluid can diffuse out of its fluid chamber and into the polymeric material.
  • the inventive bulk polymers described herein can be used in ophthalmic devices to resist the diffusion of fluid into or out of the device.
  • the incision in the sclera be as small as possible while still being able to deform the device without damaging it.
  • the device must also be able to reform to its initial configuration after delivery.
  • the inventive polymers described herein can therefore be used in ophthalmic device that need to be deformed to be delivered through an incision, yet will return to their initial configuration once implanted in the eye.
  • Improved properties of the polymers described herein include, without limitation, the modulus of elasticity, the index of refraction, the resistance to the diffusion of fluids, the responsiveness of the composition, mechanical strength, rigidity, wettability, and optical clarity. These properties are not necessarily mutually exclusive and the list is not intended to be exhaustive.
  • Some embodiments of the disclosure include a polymeric material for an ophthalmic device.
  • the polymer comprises a first component, a second component, and a third or more components.
  • the composition comprises butyl acrylate, trifluoroethyl methacrylate, phenylethyl acrylate, and a cross-linker such as ethylene glycol dimethacrylate. These monomers are not intended to be limiting and are provided by way of example.
  • butyl acrylate for example, a rubbery material, generally enhances the responsiveness of the polymeric material.
  • Alternatives for butyl acrylate include alkyl acrylates and other monomers with suitable responsiveness properties.
  • Alternatives for butyl acrylate which may demonstrate responsive properties include, without limitation, octyl acrylate, dodecyl methacrylate, n-hexyl acrylate, n-octyl methacrylate, n-butyl methacrylate, n-hexyl methacrylate, n-octyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, 2,2-dimethylpropyl acrylate, 2,2-dimethylpropyl methacrylate, trimethylcyclohexyl acrylate, trimethylcyclohexyl methacrylate, isobutyl acrylate, isobutyl methacrylate, isopen
  • butyl acrylate may include a branched chain alkyl ester, e.g. 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, 2,2-dimethylpropyl acrylate, 2,2-dimethylpropyl methacrylate, trimethylcyclohexyl acrylate, trimethylcyclohexyl methacrylate, isobutyl acrylate, isobutyl methacrylate, isopentyl acrylate, isopentyl methacrylate and mixtures thereof.
  • 2-ethylhexyl acrylate 2-ethylhexyl methacrylate
  • 2,2-dimethylpropyl acrylate 2,2-dimethylpropyl methacrylate
  • trimethylcyclohexyl acrylate trimethylcyclohexyl methacrylate
  • isobutyl acrylate isobutyl methacrylate
  • isopentyl acrylate isopenty
  • butyl acrylate is present in the range from about 10% to about 80% by volume, and in some embodiments is present in the range from about 20% to about 70% by volume. In preferred embodiments butyl acrylate is present in the range from about 35% to about 65% by volume, and in more preferred embodiments from about 45% to about 65% by volume. All percentages recited herein are considered to be “by volume,” unless specifically stated otherwise.
  • the polymer has a modulus of elasticity ranging from about 0.1 to about 0.6 Mpa. In some embodiments the modulus is between about 0.1 to about 0.3 Mpa.
  • Trifluoroethyl methacrylate can be added to the polymeric material to enhance the polymer's resistance to the diffusion of fluids as described herein. Generally, using a monomer with more fluorine atoms will enhance the polymer's resistance to the diffusion of fluid.
  • trifluoroethyl methacrylate will provide a desired balance between the polymer's resistance to diffusion and the polymer's refractive index.
  • Fluorocarbon monomers can enhance the polymer's resistance to the diffusion of fluid and some can be used as substitutes for trifluoroethyl methacrylate.
  • Alternatives for trifluoroethyl methacrylate include fluoroacrylates and other monomers with that provide that polymer with suitable resistance to diffusion properties.
  • trifluoroethyl methacrylate examples include, without limitation, heptadecafluorodecyl acrylate, heptadecafluorodecyl methacrylate, hexafluorobutyl acrylate, hexafluorobutyl methacrylate, tetrafluoropropyl methacrylate, octafluoropentyl acrylate, octafluoropentyl methacrylate, dodecafluoropheptyl methacrylate, heptafluorobutyl acrylate, trifluoroethyl acrylate, hexafluoro-iso-propyl methacrylate, pentafluorophenyl acrylate, and pentafluorophenyl methacrylate.
  • Phenylethyl acrylate can be included in the polymeric composition to increase the refractive index of the polymer.
  • Phenyl groups in general can increase the refractive index of the polymer.
  • Alternatives for Phenylethyl acrylate include phenyl acrylates and other monomers with that provide that polymer with suitably high refractive index.
  • benzyl (benzoyl), carbazole-9-yl, tribromophenyl, chlorophenyl, and pentabromophenyl.
  • exemplary monomers that can be used as alternatives to phenylethyl acrylate include, without limitation, tribromophenyl acrylate, 2-(9H-Carazole-9-yl)ethyl methacrylate, 3-chlorostyrene, 4-chlorophenyl acrylate, benzyl acrylate, benzyl methacrylate, benzyl methacrylamide, n-vinyl-2-pyrrolidone, n-vinylcarbazole, pentabromophenyl acrylate, and pentabromophenyl methacrylate, phenylethyl methacrylate, 2-phenylpropyl acrylate, or 2-phenylpropyl methacrylate.
  • phenylethyl acrylate is present in the range from about 5% to about 60%, while in some embodiments it is present in the range of about 10% to about 50%. In preferred embodiments it is present in the range of about 20% to about 40%, and in more preferred embodiments it is present in the range of about 26% to about 34%.
  • the polymer has a refractive index of between about 1.44 to about 1.52. In some embodiments the refractive index is between about 1.47 and about 1.52. In some embodiments the refractive index is between about 1.47 and about 1.5.
  • the composition also includes a cross-linking agent, such as ethylene glycol dimethacrylate.
  • a cross-linking agent such as ethylene glycol dimethacrylate.
  • suitable crosslinking agents include but are not limited to diacrylates and dimethacrylates of triethylene glycol, butylene glycol, neopentyl glycol, ethylene glycol, hexane-1,6-diol and thio-diethylene glycol, trimethylolpropane triacrylate, N,N′-dihydroxyethylene bisacrylamide, diallyl phthalate, triallyl cyanurate, divinylbenzene; ethylene glycol divinyl ether, N,N′-methylene-bis-(meth)acrylamide, sulfonated divinylbenzene, divinylsulfone, ethylene glycol diacrylate, 1,3-butanediol dimethacrylate, 1,6 hexanediol diacrylate, te
  • Cross-linking agents may be present in amounts less than about 10%, less than about 5%, less than about 2%, or less than about 1%.
  • the cross-linking agent(s) can cause the polymers to become interlaced within a tri-dimensional space, providing for a compact molecular structure having an improved elastic memory, or responsiveness, over the non-crosslinked composition.
  • the polymeric compositions also includes one or more ultraviolet (UV) light absorbing materials, such as an acrylate or methacrylate functionalized benzotriazole or benzophenone, in amounts less about 5%.
  • UV light absorbing material(s) is present in the range from about 0.05% to about 2%.
  • Suitable ultraviolet light absorbers for use in the present invention include, without limitation, ⁇ -(4-benzotriazoyl-3-hydroxyphenoxy)ethyl acrylate, 4-(2-acryloyloxyethoxy)-2-hydroxybenzophenone, 4-methacryloyloxy-2-hydroxybenzophenone, 2-(2′-methacryloyloxy-5′-methylphenyl)benzotriazole, 2-(2′-hydroxy-5′-methacryloyloxyethylphenyl)-2H-benzotriazole, 2-[3′-tert-butyl-2′-hydroxy-5′-(3′′-methacryloyloxypropyl)phenyl]-5-chloro-benzotriazole, 2-[3′-tert-butyl-5′-(3′′-dimethylvinylsilylpropoxy)-2′-hydroxyphenyl]-5-m-ethoxybenzotriazole, 2-(3′-allyl-2′-hydroxy-5′-methylphen
  • One or more suitable free radical thermal polymerization initiators may be added to the polymeric compositions described herein.
  • suitable free radical thermal polymerization initiators include but are not limited to organic peroxides, such as acetyl peroxide, lauroyl peroxide, decanoyl peroxide, stearoyl peroxide, benzoyl peroxide tert-butyl peroxypivalate, peroxydicarbonate, and the like.
  • Such an initiator can be added in the range of about 0.01% to about 1% of the total polymer mixture.
  • UV initiators include those known in the field such as, for example but not limited to, benzoin methyl ether, benzoin ethyl ether, Darocur® 1173, 1164, 2273, 1116, 2959, 3331 (EM Industries) and Irgacur® 651 and 184 (Ciba-Geigy, Basel, Switzerland).
  • the diffusion resistant properties of the inventive polymers described herein may be further enhanced by providing a barrier layer on the exterior surface of the ophthalmic device.
  • the device comprises a fluid chamber disposed within the device (such as a fluid chamber disposed in a fluid-driven accommodating IOL)
  • the device can also have a barrier layer on the inner surface of the fluid chamber to increase the resistance to diffusing out of the fluid chamber.
  • the layers formed by plasma deposition will generally be very thin, for example, from about 20 to about 100 nanometers. Because fluorocarbon polymers generally have low refraction indices, a barrier layer with a thickness that is less than a quarter of the wavelength of visible light will not be seen with the naked eye.
  • the inventive polymers described herein may be used in an IOL with fluid disposed therein, such as in fluid chambers.
  • the viscosity of a fluid is related to the diffusion properties of the fluid; a low viscosity fluid can more easily diffuse through the polymer.
  • An ophthalmic device may contain silicone oil.
  • the amount of silicone oil that diffuses through the polymer can be reduced by selecting a silicone oil with narrow molecular weight distribution, in particular with the removal of low molecular weight silicone oil molecules.
  • a sequence of stripping processes is commonly used to remove low molecular weight components in silicone oil.
  • low molecular weight components will diffuse faster than higher molecular components.
  • higher molecular weight components contribute to an increase in the viscosity which requires a greater force to drive the fluid throughout the IOL. Therefore, silicone oil with a narrow molecular weight distribution is preferred.
  • the fluid disposed within the ophthalmic device is not limited to silicone oil and can be, for example, a saline solution.
  • the IOL components are substantially index matched, such that the deflection of one of the surfaces of the IOL contributes significantly to any change in power during accommodation.
  • the bulk polymer will be substantially indexed matched to any fluid within the IOL.
  • Substantially index-matched, as that phrase is used herein, include minimal differences in refractive indexes between components of the IOL. For example, if adhesives are used in the manufacturing of an IOL, those adhesives may have different refractive indexes but those differences will be negligible when considering the overall power changes of the accommodating IOL.
  • the T G of the polymer is about ⁇ 20° C., and can stretch to about 4 ⁇ the length without breaking.
  • the polymer can be manufactured by pour the formulation into a mold and curing the polymer, with either UV or thermal curing.
  • the resulting polymer had a swell fraction of 0 in silicone oil, a refractive index of 1.477, and a modulus of elasticity of 0.163 Mpa.
  • the resulting polymer had a swell fraction of 0.019, a refractive index of 1.473, and a modulus of elasticity of 0.27 Mpa.
  • the refractive index of the polymeric material of the intraocular lens is between approximately 1.48 and approximately 1.53, optionally between 1.50 and 1.53.
  • the refractive index of the bulk polymer may be increased by increasing the concentration of phenylethyl acrylate as a percentage of weight of the polymer.
  • Other components can be modified to compensate for increased concentrations of the monomer comprising a phenyl group.
  • Table 1 illustrates additional exemplary polymeric formulations for use in ophthalmic devices and their components, wherein the refractive index is higher than some embodiments above.
  • the first three formulations have refractive index values very close to 1.5180 at 532 nm and 35 C, which is an example of a RI between 1.50 and 1.53.
  • the fourth formulation is similar to some examples provided above. All four formulations in Table 1 include BA, PEA, and TFEMA.
  • Formulations 1-3 in Table 1 can be used in, for example, an optic portion of an accommodating intraocular lens (“AIOL”), wherein the accommodating intraocular lens is a fluid-driven, or a peripheral portion of an AIOL.
  • AIOL accommodating intraocular lens
  • the percentage of BA is between 2 and 20%, such as between 3 and 17%.
  • the percentage of PEA is between 50 and 80%, such as between 60 and 75%.
  • the percentage of TFEMA is between 10 and 35%, such as between 15 and 30%.
  • the first three formulations in Table 3 are also examples of polymeric materials that comprise an alkyl acrylate present in the amount from 3% to 20%, a fluoroacrylate present in the amount from 10% to 35%, and a phenyl acrylate present in the amount from 50% to 80%.
  • the polymeric materials can be manufactured, including curing, using a variety of manufacturing steps.
  • FIG. 3 illustrate an exemplary process of curing three monomers (i.e., BA, PEA, and TFEMA), a UV blocker, and a cross-linker such as EGDMA, resulting in a cured polymeric material that includes the three monomers. Any of the polymeric materials can be manufactured in this manner.
  • FIG. 4 illustrates an alternative manufacturing process, wherein pre-polymers are first created with a plurality of monomers (in this example they are the same as in FIG. 3 , but need not be), wherein the pre-polymers are not yet cross-linked (not yet fully cured), as is shown in FIG. 4 .
  • the monomers are first combined with a monomer that includes a hydroxyl moiety, which is subsequently converted to a crosslinkable methacrylate, which allows the cross-linkable polymer to be fully cured.
  • the monomer that includes the hydroxyl moiety is a methacrylate (e.g., hydroxyethyl methacrylate (“HEMA”)) or an acrylate (e.g., hydroxyethyl acrylate (“HEA”), hydroxybutyl acrylate (“HBA”)).
  • HEMA hydroxyethyl methacrylate
  • HBA hydroxybutyl acrylate
  • FIG. 6A illustrates an exemplary process of making a cross-linkable polymer from a pre-polymer (such as the pre-polymer in FIG. 4 ), in which the hydroxyl moiety is converted into a methacrylate (bottom right in FIG. 6A ), which can then be crosslinked to form a cured polymeric material, which can be used to make any of the components of any exemplary IOL herein.
  • the cross-linkable polymers can be combined with a hydrophilic reactive diluent.
  • a hydrophilic monomers e.g., HEMA, HBA
  • HEMA hydrophilic monomers
  • HBA hydrophilic monomers
  • Blocks can increase efficacy of hydrophilic components relative functionality in random copolymers.
  • the polymer is developed by using about 25-35% (e.g., 30%) HEMA or HBA as a reactive diluent for the cross-linkable polymer.
  • HEMA or HBA a reactive diluent for the cross-linkable polymer.
  • no phase separation occurred upon curing and the cured polymeric material was clear.
  • These cross linkable polymer-based formulations are well suited for high precision (very low shrinkage) production of directly molded parts, such as with haptics and optic portions or any of the accommodating intraocular lenses described or incorporated by reference herein.
  • An additionally exemplary advantage of incorporating one or more hydrophilic monomers (e.g., HEMA, HBA) into the polymeric material as the reactive diluent is that it can reduce water-induced haze or glistenings (i.e., water vacuoles in the material).
  • hydrophilic monomers e.g., HEMA, HBA
  • FIGS. 5A and 5B illustrates the polymerization of exemplary hydrophilic materials, with HEMA being shown in FIG. 5A , and FIG. 5B showing HBA.
  • One aspect of this disclosure describes adhesives that can be used to bond first and second polymers together, optionally first and second polymers in an intraocular lens. While the disclosure describes the adhesives and polymers for use in ophthalmic applications, it is not intended to be so limited.
  • the materials described herein can be used in other suitable applications.
  • the exemplary polymeric materials described above e.g., example 1, example, 2, and Table 1 are merely examples of formulation of polymers for the first and second components that are bonded together.
  • the adhesives described herein will be described in reference to polymers described herein, but the concepts herein can be applied to other polymeric materials and other adhesives.
  • the examples provided herein are merely exemplary and the disclosure is not intended to be limited to the specific adhesives or the specific polymers herein.
  • two or more polymeric bodies are adhered, or glued, together.
  • the bond(s) should be strong enough so that the two or more bodies remain adhered together during use and during the implantation procedure. For example, the bonds must hold even if the device needs to be reconfigured or deformed during loading and/or delivery into the eye. Additionally, the presence of the adhesive should not cause the optical clarity of the device, such as at or near the bond, to decrease to an unacceptable level.
  • the adhesive and polymer combinations herein improve or maintain the mechanical integrity of the adhesive/polymer bond, as well as maintain an acceptable level of optical clarity.
  • One aspect of the disclosure is an adhesive that has a first component that is the same or substantially the same material, or has substantially similar properties, as first and second polymeric bodies that are adhered together.
  • the first and second bodies alternatively can have different formulations.
  • the adhesives are used to adhere a “first body” to a “second body.”
  • first and second bodies are first cured, then adhered together using adhesion techniques herein.
  • the adhesive includes first and second primary components and a curative additive (e.g, a photoinitiator).
  • the first primary component e.g., about 50-75%) is a crosslinkable polymer (“CLP”; the discussion above on cross-linkable polymers is incorporated into this aspect of the disclosure) that has the same, or similar composition as, or substantially similar properties as, the first and second bodies. Because the CLP is not yet cross-linked, it behaves as a flowable, dissolvable, thermoplastic material, rather than a thermoset material.
  • the CLP is then compounded with a second primary component, a reactive acrylic monomer diluent (such as ADMA, shown in FIG.
  • ADMA reactive acrylic monomer diluent
  • the CLP is too big/bulky to be able to migrate into either body, whereas the reactive acrylic monomer diluent and photoinitiators can migrate/diffuse across the bond line and into both cured polymeric bodies.
  • the reactive acrylic monomer diluent and initiators diffuse to a certain (controllable) extent and are subsequently cured (e.g., by UV light), creating an interpenetrating network of reactive acrylic monomer diluent (e.g., ADMA) in the first and second bodies, as well as a now crosslinked polymer (that is the same as or similar to, or has similar properties to the first and second bodies) also with a permeating reactive acrylic monomer diluent network. If the extent of diffusion is such that the reactive acrylic monomer diluent concentration is essentially equal across and within the bond line, then properties of the materials across the region will be substantially the same.
  • reactive acrylic monomer diluent concentration is essentially equal across and within the bond line
  • the first primary component (that optionally has the same or similar composition as the first and/or second bodies) is about 55% to about 80% (such as about 55% to about 75%) of the adhesive.
  • the second primary component reactive acrylic monomer diluent
  • the adhesive is about 18% to about 43% (such as about 23% to about 43%) of the adhesive.
  • the adhesives herein provide some mechanical advantages. In general, the bond strength is better over time, which increases the life expectancy of the device. When using substantially the same materials, or materials with substantially similar properties, an interpenetrating network of materials is formed between the polymer and the adhesive where the resulting bonded material is substantially the same throughout. Additionally, the mechanical and thermal properties of the materials can be substantially the same as well. For example, the modulus of elasticity of the polymer and adhesive can be designed to be the same or substantially the same. Additionally, the surfaces energies can be substantially the same, which can help keep ambient water out of the bond and prevent it from migrating into the device and forming water droplets.
  • first component of the adhesive that is the same or substantially the same as a first body material
  • Shrinkage invariably occurs when monomers are cured (typically about 10% by volume for most acrylic monomers), but the crosslinking of the CLP occurs with almost no shrinkage since this can be considered as the final about 1% of the cure of the essentially all pre-cured material, thus the more CLP that is used in the adhesive formulation, the less shrinkage that that formulation will exhibit upon cure.
  • the diffusion of, for example, ADMA into the acrylic adhered ensues with concomitant swelling that may offset some or all of the cure-induced shrinkage.
  • the surface energies can be substantially the same, and there are substantially no hydrophobic sites. Substantially the same surface energy prevents water droplets from forming, which prevents the optical clarity from decreasing. Additionally, by using substantially the same material, the refractive index of the adhesive and the bonded polymers can be substantially the same. While a difference in refractive index between an adhesive and polymer may not create any noticeable optical disturbances, creating the materials with substantially the same refractive index can reduce the likelihood of such disturbances.
  • the cross-linkable polymer of the adhesive need not have the same formulation (same monomers and same percentages), or even the same monomers, as the polymeric formulation as the first and/or second polymeric bodies being bonded together. It is advantageous that the cross-linkable polymer formulation have similar properties to the formulation of the first and/or second polymeric bodies, which are described above, but in other embodiments the can be quite different.
  • formulation #4 from Table has been used as a crosslinkable polymer in an adhesive formulation, and has been used to adhere polymeric bodies that have formulations as set forth in any of formulations #1-#3 in Table 1.
  • the adhesive cross linkable polymer and polymeric formulation for the first and second bodies both include three monomers that are the same, but at different percentages. This is an example of being the substantially the same or having substantially similar properties. The bond strength in this example was very strong.
  • the adhesive cross linkable polymer and polymeric formulation for the first and second bodies can be the same.
  • Any intraocular lens that includes first and second components being bonded together can be adhered together using concepts herein.
  • the disclosure herein also describes exemplary fluids that can be used in intraocular lenses.
  • the fluids are silicone oils, and in some embodiments the intraocular lenses are accommodating intraocular lenses.
  • An ophthalmic device may contain one or more silicone oils.
  • Silicon oil may be used in accommodating intraocular lens that uses fluid movement to effect optical power change in the IOL. Silicon oil may also be used in non-accommodating intraocular lenses as well.
  • silicone oil is used in accommodating IOL with a bulk material such as a polymeric material, some of the oil components can pass into the bulk material, causing the bulk material to swell. The selected silicone oil or oils therefore avoids the undesirable swelling of the bulk polymer.
  • Exemplary polymeric materials that can be used for the bulk material of the IOL can be found herein.
  • the amount of silicone oil that diffuses through the polymer can be reduced by selecting a silicone oil with narrow molecular weight distribution, in particular with the removal of low molecular weight silicone oil molecules.
  • a sequence of stripping processes can be used to remove low molecular weight components in silicone oil.
  • low molecular weight components will diffuse faster than higher molecular components.
  • higher molecular weight components contribute to an increase in the viscosity which requires a greater force to drive the fluid throughout the IOL. Therefore, silicone oil with a narrow molecular weight distribution is preferred.
  • the fluid disposed within the ophthalmic device is not limited to silicone oil and can be, for example, a saline solution.
  • PDI polydispersity index
  • silicone oils described herein have a PDI less than about 1.5, and more particularly less than or equal to about 1.3. In other instances, the PDI of the silicon oils is less than about 1.2
  • a second characteristic of the silicone oil that helps ensure an adequate response and avoids undesirable swelling is the mean molecular weight of the silicone oil.
  • a greater number of low molecular weight components pass into the bulk material of the IOL causing the swelling of the bulk material.
  • the concentration of relatively low molecular weight components should be minimized.
  • the PDI of the silicone oil and the mean molecular weight of the oil are related—by lowering the PDI of the silicone oil while providing silicone oil with high concentrations of relatively high molecular weight components and low concentrations of low molecular weight components, the response of the IOL is maintained (by providing a silicone oil with suitable viscosity) and undesirable swelling is avoided. Additionally, providing silicone oil with a low PDI and very low concentrations of small molecular weight components means that the silicone oil has a molecular weight just large enough to avoid swelling of the polymer.
  • silicone oil has a mean molecular weight between about 4500 and about 6500 Daltons, or having a mean molecular weight of about 5000 and about 6500 Daltons. Silicon oils having molecular weights within this range are large enough to substantially avoid swelling of the bulk polymeric material. This is preferable to the alternative, which is using a higher molecular weight silicone oil which has inherently fewer small molecule components because almost all molecules comprising it are large. High molecular weight silicone oils can have a correspondingly high viscosity, which can reduce the response time of the accommodating IOL.
  • the silicone oils described herein have a very low concentration of relatively low molecular weight components.
  • the very low molecular weight components are present in an amount less than about 200 ppm of each component, and in some embodiments less than about 100 ppm. In some particular embodiments the very low molecular weight components are present in an amount less than about 50 ppm.
  • the relatively low molecular weight components include those less than or equal to about 1000 Daltons.
  • concentration of components less than or equal to about 1000 Daltons is not more than about 50 ppm.
  • silicone oil is provided in which no more than 20% of the total silicone by weight is comprised of components below about 4000 Daltons; no more than 10% of the total polymer fluid by weight is comprised of components below 3000 Daltons; and no more than 50 ppm of any components below 1000 Daltons.
  • the estimated molecular weights and polydispersities described herein are relative to polystyrene molecular weights standards.
  • the silicone oil generally needs to be designed in such a way as to avoid adverse interactions with the surrounding bulk IOL material, such as swelling, fogging, dissolving or reacting with the material (e.g., poly acrylate) in some IOLs.
  • the degree of solubility of the silicone oil in the bulk material is dependent on the chemical structure and molecular weight distribution of the silicone oil. Other parameters that influence this interaction are the composition and properties of the bulk material such as homogeneity, chemical structure, hydrophobicity, modulus, and crosslink density.
  • the viscosity of the silicone oil also generally needs to be defined and minimized because, in embodiments in which the fluid-driven accommodating IOL operates dynamically, the IOL must have an appropriate response time. In some embodiments, the viscosity of the silicone oil is no more than 2400 cP.
  • the silicone oil is made from a cyclotrisiloxane comprising a ratio of two dimethyl siloxane units to one diphenyl siloxane unit. In some embodiments the oil is at least 95% (e.g., 100%) of a single cyclotrisiloxane comprising a ratio of two dimethyl siloxane units to one diphenyl siloxane unit.
  • the silicon oil may be a single component of diphenyl siloxane (e.g. approximately 100%). In other embodiments, the percentage of diphenyl siloxane is approximately 95% or more. In these embodiments the refractive index of the silicone oil is about 1.5180, which is an example of between 1.50 and 1.53. In some embodiments a silicone oil that is approximately 100% diphenyl siloxane can be used in an accommodating intraocular lens that has formulations such as #1-#3 in Table above. In these embodiments the fluid and polymer were index matched to about 1.518.
  • the diphenyl siloxane polymeric compound has a mean molecular weight of between approximately 4500 and approximately 6500 Daltons.
  • the refractive index of the silicone oil can be varied between the refractive index of either pure homopolymer alone (i.e., between pure diphenyl polysiloxane and pure dimethyl polysiloxane).
  • the refractive index of the silicone oil composition can be varied by varying the ratio of a tetramethyl-diphenyl-cyclotrisiloxane to hexamethyl cyclotrisiloxanes. Varying this ratio can provide different refractive indexes between about 1.40 and about 1.54, including those between about 1.47 and 1.49.
  • Supercritical CO 2 extraction is one exemplary purification method that can be used to selectively remove fractions of silicone oil based on molecular weight and based on chemical affinity.
  • Supercritical CO 2 extraction to purify silicone oils to produce silicone vitreoretinal tamponades is described in U.S. Pat. No. 7,276,619, the entire disclosure of which is incorporated by reference herein. These oils are not used for IOLs, are particularly not in fluid-drive accommodating IOLs. Pressure, temperature, rate of extraction conditions, and the use of co-eluting solvents such as, for example, acetone, can be varied to yield fractions that have a narrow molecular weight distribution (i.e., a low PDI).
  • blended high- and low-refractive index oil components such as in Tables 5 and 6 below (e.g., blended dimethyl siloxane vs. diphenyl siloxane), is that although the fractionated oils have higher molecular weights, the blended index-matched system (index matched with the polymeric material of the lens) actually does not increase much in viscosity due to the change in blending ratios working with the inherent viscosity changes as a function of the content of the components (e.g., oil components being dimethyl siloxane and diphenyl siloxane).
  • Tables 6 and 7 show examples of unfractionated and fractionated blends (of high RI and lower RI), respectively, of exemplary silicone oils.
  • the exemplary blended oils in Tables 5 and 6 have viscosities less than 1000 cPs, and blended Refractive Indexes between 1.47 and 1.50.
  • fractionation process can allow for creating otherwise unattainable property matching of the silicone fluids to the lens acrylic materials, thereby minimizing swelling-induced power shifts while retaining desirable low viscosity fluids which allow acceptably fast response times, both of which are described herein.
  • the oil includes blended dimethyl siloxane and diphenyl siloxane, examples of which are described herein, such as in the Tables.
  • the oil comprises copolymers of dimethyl siloxane and diphenyl siloxane, and in some embodiments the ratio of the two can vary from 1:1 to 3:1.
  • Table 8 lists exemplary silicone oils, including mean molecular weight, polydispersity, and change in power.
  • the polydispersities of these examples are all under 1.3, which is an example of under 1.5.
  • the mean molecular weight of the oil is about 4500 Da to about 6500 Da, and in some embodiments is between 5000 Da and 6000 Da, such as about 5200 Da and 5800 Da. In some embodiments the viscosity is less than 2400 cPs.
  • silicone oils used in accommodating IOLs are primarily described herein, it is possible to use any of the silicone oils in a non-accommodating IOL.
  • a non-accommodating IOL can have a relatively rigid outer polymeric shell surrounding a silicone oil core. Swelling of the bulk polymeric material would still need to be taken into consideration, and hence the methods of manufacturing desired silicone oil described herein could be utilized.
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EP4245327A3 (fr) 2023-12-27
JP2022179785A (ja) 2022-12-02
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EP3307206A1 (fr) 2018-04-18
US20200246134A1 (en) 2020-08-06
CA3219515A1 (fr) 2016-12-15
JP2018527038A (ja) 2018-09-20
AU2016275073B2 (en) 2021-02-25
JP6839100B2 (ja) 2021-03-03
WO2016201351A1 (fr) 2016-12-15
EP3307206A4 (fr) 2019-02-20
AU2016275073A1 (en) 2018-01-18
AU2023204633A1 (en) 2023-08-03
AU2021203350B2 (en) 2023-04-27
CA2987311A1 (fr) 2016-12-15
CA2987311C (fr) 2024-01-02
EP3307206B1 (fr) 2023-09-20
JP7165219B2 (ja) 2022-11-02
CN114452440A (zh) 2022-05-10
JP2021065748A (ja) 2021-04-30
EP4245327A2 (fr) 2023-09-20
AU2021203350A1 (en) 2021-06-24

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