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WO2003066714A1 - Procede pour ameliorer la qualite de surface d'articles a hydrogel - Google Patents

Procede pour ameliorer la qualite de surface d'articles a hydrogel Download PDF

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Publication number
WO2003066714A1
WO2003066714A1 PCT/AU2003/000134 AU0300134W WO03066714A1 WO 2003066714 A1 WO2003066714 A1 WO 2003066714A1 AU 0300134 W AU0300134 W AU 0300134W WO 03066714 A1 WO03066714 A1 WO 03066714A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogel
hydrophilic plasticizer
volatile hydrophilic
art
crosslinked
Prior art date
Application number
PCT/AU2003/000134
Other languages
English (en)
Inventor
Traian V Chirila
Xia Lou
Celia Rachel Hicks
James Howard Williams
Original Assignee
Lions Eye Institute Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lions Eye Institute Limited filed Critical Lions Eye Institute Limited
Priority to AU2003202321A priority Critical patent/AU2003202321A1/en
Publication of WO2003066714A1 publication Critical patent/WO2003066714A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/056—Forming hydrophilic coatings
    • 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 or corneal implants; Artificial eyes
    • A61F2/145—Corneal inlays, onlays, or lenses for refractive correction
    • 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
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/502—Plasticizers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/52—Hydrogels or hydrocolloids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C71/00—After-treatment of articles without altering their shape; Apparatus therefor
    • B29C71/0009—After-treatment of articles without altering their shape; Apparatus therefor using liquids, e.g. solvents, swelling agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C71/00—After-treatment of articles without altering their shape; Apparatus therefor
    • B29C71/0063—After-treatment of articles without altering their shape; Apparatus therefor for changing crystallisation
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/18—Plasticising macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/06—Coating with compositions not containing macromolecular substances
    • C08J7/065—Low-molecular-weight organic substances, e.g. absorption of additives in the surface of the article
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
    • B29K2995/0037—Other properties
    • B29K2995/0092—Other properties hydrophilic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2011/00—Optical elements, e.g. lenses, prisms
    • B29L2011/0008—Artificial eyes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2011/00—Optical elements, e.g. lenses, prisms
    • B29L2011/0016—Lenses
    • B29L2011/0041—Contact lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2300/00—Characterised by the use of unspecified polymers
    • C08J2300/14—Water soluble or water swellable polymers, e.g. aqueous gels

Definitions

  • This invention relates broadly to a method of improving the surface quality of hydrogel articles.
  • the invention relates to a method of treating hydrogel articles prior to lathing, which treatment improves the surface quality of the lathed article.
  • the invention relates to articles produced according to the method.
  • Polymeric hydrogels are extensively used for manufacturing soft, hydrophilic ocular devices such as contact lenses, intraocular lenses or artificial corneas. In all these applications, the anterior and posterior surfaces must be smooth and optically clear to the best possible level. Broadly, these devices may be made by two procedures.
  • the polymerisation of appropriate monomers is performed in casting moulds in the absence of solvents or diluents providing rigid articles generally termed "xerogels".
  • xerogels Upon hydration, the xerogels become hydrogels, the latter being in the soft, pliable state in which the ocular devices are generally used.
  • mechanical processing which in the context of the specification is understood to mean processes performed on polymeric articles designed to modify or improve its shape, profile or surface such as lathing, cutting, grinding or polishing.
  • the articles are cast in moulds in the presence of solvents or diluents, (commonly water or/and water soluble organic solvents), preserving the hydrogel state during all stages of the manufacture.
  • solvents or diluents commonly water or/and water soluble organic solvents
  • additional machining of the surfaces of the resulting articles is generally required, because of possible surface irregularities and in order to achieve the desired dimensional and optical parameters.
  • Mechanical processing can only be conducted on articles that are in a rigid state. Hydrogels that are soft and pliable at room temperature must be cooled to such a state before mechanical processing. Hydrogels must be cooled to temperatures less than the freezing point of the solvents comprising said hydrogels to become rigid. Hydrogels lathed under these conditions however typically comprise surfaces with irregular crevices of microscopic dimensions.
  • both U.S. Pat. No. 4,322,139 and its division, U.S. Pat. No. 4,512,461 both issued to Wichterle, disclose the use of water-soluble agents including glycerol, glycols, or polyglycols as components of the swelling agents for treating hydrogel contact lenses. After swelling, the said contact lenses were planarized, dried, grinded or polished in order to remove defects and re-hydrated to the initial convex shape. It is disclosed in the aforementioned patents that the presence of the water-soluble agents reduces the brittleness of the dried planarized contact lenses, such assuring better mechanical processability by grinding, polishing or cutting. The aforementioned patents do not disclose mechanical processing of frozen hydrogels. According to the teaching of these patents, the improvement of mechanical properties of the contact lenses as xerogels was based entirely upon the plasticising effect of the agents added to the swelling agent.
  • U.S. Pat. No. 4,093,361 issued to Erickson and Neogi relates to a method for eliminating the distortions and stresses occurring upon hydration of composite hydrogel articles such as contact lenses with a hard core and a soft skirt.
  • certain water-soluble agents were incorporated into the hydrogels prior to polymerisation and hydration.
  • the agents include polyethylene glycol and derivatives, aromatic acids, soaps and surfactants, and water-soluble synthetic polymers.
  • the patent does not disclose mechanical processing of frozen hydrogels, and does not relate to the cryoprotective properties of the agents.
  • U.S. Pat. No. 4,956,432 issued to Vacik, Obereigner and Souckova discloses the preparation of hydrogels by copolymerisation of N-substituted pyrrolidone derivatives with acrylic monomers. It is disclosed in this reference that the addition of polar solvents such as glycerol or glycols in the monomer mixture can result in materials devoid of stress, after swelling/washing in water and drying to xerogels. According to the aforementioned patent, the presence of the said agents at the time of polymerisation induced a more ordered structure of the crosslinked polymers network, such reducing the stress. The said agents are removed from materials by washing prior to drying and machining. The patent neither discloses the effects of the said agents on frozen hydrogels, nor their machining in such state.
  • Jap. Pat. 56-94240 issued to Suzuki discloses embedding agents for slicing large sections of organ tissue for histopathological examination (microscopy, autoradiography).
  • the common embedding agent for large organ sections was carboxymethyl cellulose, which presented several shortcomings such as formation and build-up of crystals upon freezing, fragility, and disintegration to a powder upon slicing with the tools of the art.
  • the patent discloses compositions based on poly(vinyl alcohol) of a particular degree of polymerisation, capable of eliminating these shortcomings during slicing at temperatures between -15°C and -20°C.
  • the compositions disclosed are solutions in water of PVA, sodium alginate, glycerol and sucrose.
  • sodium alginate reduces friction during the cutting, while glycerol and sucrose prevent the build-up of crystals upon freezing.
  • the invention relates to aqueous solutions, not to hydrogels, which are insoluble in water. Further, the invention does not relate to machining the polymers as such, but to the slicing of biological matter where the solution of a polymer serves only as an embedding medium (support) during freezing and subsequent cutting. This invention seeks to provide a method of ameliorating these problems of the cryogenic lathing process and more specifically to provide an article with a high quality smooth finish.
  • hydrogel articles treated with a non-volatile hydrophilic plasticizer are much less brittle, cutting has a uniform course and the resulting surfaces are much smoother than in the case of hydrogel articles that were not treated with non-volatile hydrophilic plasticizer prior to lathing.
  • This effect is believed to be a combined result of the reduction of stress to the polymer mass associated with its preparation in a workable state, of a smaller size of ice crystals and of the presence of non-volatile hydrophilic plasticizer in a fluid state within the intercrystalline voids.
  • non-volatile hydrophilic plasticizer strongly hinders or even arrests nucleation and growth of ice crystals as well as depressing the temperature at which freezing of water occurs.
  • the ice crystals form in reduced amounts, they are smaller and have shapes different from the shape of the ice crystals formed by normal freezing. Further, the formation, propagation, distribution and dissolution of the ice crystals formed in the presence of non- volatile hydrophilic plasticizer are much slower than in their absence.
  • the invention relates to a method of treating hydrogel articles prior to lathe machining in a workable state, which treatment improves the surface quality of the lathed product.
  • the invention also relates to products produced according to the method.
  • Figure 1 is a frontal photograph of the lathed surface of a polyHEMA hydrogel blank that was not subjected to treatment in glycerol;
  • Figure 2 is a frontal photograph of the lathed surface of a polyHEMA hydrogel blank that was treated in a solution of 15% by weight glycerol in water.
  • a method of improving the surface quality of hydrogel articles comprising the step of: processing the article in a workable state in the presence of a non-volatile hydrophilic plasticizer.
  • processing of the hydrogel refers to any process that is capable of shaping, cutting, grinding or polishing of a hydrogel. Usually such processing will be carried out by mechanical means that are capable of modifying or improving a hydrogel's shape, profile or surface. An alternate form of processing might be through the use of high-pressure fluid jets. Preferably, the processing that is referred to will include the mechanical lathing of the hydrogel followed by processes which grind and or polish the hydrogel.
  • workable state refers to the state of the hydrogel at the time of processing. While hydrogels may be processed in many forms, the present invention is preferably employed for the processing of hydrogels in a rigid or semi- rigid form as might arise from the process of freezing. Generally the hydrogels will display sufficient rigidity to permit lathing and or grinding and or polishing.
  • the advantages associated with the present invention include for example: (a) providing a means for reducing or eliminating stress and distortion of hydrogel articles upon exposure to reduced temperatures; and (b) providing a means for improving the quality of the surface of hydrogel articles lathed in a rigid state.
  • the invention provides a method of improving the surface quality of hydrogel articles comprising the step of: mechanically processing the article in a rigid or semi-rigid state in the presence of a non-volatile hydrophilic plasticizer.
  • hydrogel articles that may be processed according to the present invention are not limited in any context other than they must be capable of being placed in a workable state for processing.
  • the hydrogel articles will be ocular lenticular devices such as contact lenses, intraocular lenses and artificial corneas or the like.
  • Representative of the hydrogels useful in conjunction with the cryoprotective agents and method of the present invention are: a. Hydrogels derived from 2-hydroxyethyl methacrylate (henceforth designated as HEMA), crosslinked with any of the agents known in the art. b.
  • f. Polymers and copolymers derived from N-vinylpyrrolidone and its derivatives, and various combinations with hydroxylated methacrylates and acrylates, or with acrylamide and derivatives, crosslinked with any of the agents known in the art.
  • methacrylates or acrylates of poly(ethylene glycols) crosslinked with any of the agents known in the art.
  • Silicone acrylate hydrogels cross linked with any of the agents known in the art.
  • the non-volatile hydrophilic plasticizer is a water-soluble cryoprotective agent known in the art.
  • Water-soluble cryoprotective agents suitable for use according to the present invention include, for example: glycerol, glycols, poly(ethylene glycols), polyols, water-soluble synthetic polymers (e.g. polyvinylpyrrolidone), gelatin, albumin, natural gums, monosaccharides and polysaccharides.
  • nonvolatile hydrophilic plasticizer While the present invention is described in the context of using a single nonvolatile hydrophilic plasticizer, those skilled in the art will appreciate that combinations of non-volatile hydrophilic plasticizers may be employed in the method of the invention. Where combinations of plasticizers are used in the invention they will preferably be miscible when in the presence of each other.
  • the hydrogel article is contacted with enough non-volatile hydrophilic plasticizer to ameliorate the stress and distortion of hydrogel articles upon cooling and/or to improve the quality of the surface of hydrogel articles upon lathing of the article.
  • non-volatile hydrophilic plasticizer may be used as a neat liquid or may be diluted. Where the non-volatile hydrophilic plasticizer is diluted, the resultant solution preferably ameliorates the stress and distortion of hydrogel articles upon cooling and/or improves the quality of the surface of hydrogel articles upon lathing of the article.
  • the non-volatile hydrophilic plasticizer may be diluted in any fluid with which the non-volatile hydrophilic plasticizer is miscible.
  • the fluid will be physiologically acceptable.
  • Physiologically acceptable solutions might include for example purified (e.g. distilled and deionised) water.
  • the non-volatile hydrophilic plasticizer is glycerol
  • it is present at a concentration in water such that the resultant solution ameliorates the stress and distortion of hydrogel articles upon cooling and/or improves the quality of the surface of hydrogel articles upon lathing of the articles.
  • it is present at a concentration of between 5 and 80% by weight. More preferably, it is present at a concentration of between 10 and 50% by weight. Even more preferably the concentration ranges is from 15 to 25% by weight.
  • glycerol is provided at a concentration of 15% by weight.
  • the non-volatile hydrophilic plasticizer may be contacted with the hydrogel article at the time of machining or prior to the machining process. Whether the hydrogel article is contacted with the nonvolatile hydrophilic plasticizer prior to or at the time of machining will depend on such factors as the machining process used, the finish required on the hydrogel article and the non-volatile hydrophilic plasticizer selected. Preferably hydrogel articles such as ocular lenticular devices are contacted with the non-volatile hydrophilic plasticizer prior to their machining.
  • the method of the invention will include the step of: treating the hydrogels in an aqueous solution including at least a non-volatile hydrophilic plasticizer prior to their machining in a rigid or semi rigid state.
  • the hydrogel article will be treated in an aqueous solution including at least a nonvolatile hydrophilic plasticizer, after which it will be frozen and then lathed in the presence of a non-volatile hydrophilic plasticizer.
  • non-volatile hydrophilic plasticizer is brought in contact with the hydrogel article prior to the lathing process, factors such as the finish required, the non-volatile hydrophilic plasticizer used and its concentration will dictate the time that the hydrogel article should be left in contact with the non-volatile hydrophilic plasticizer.
  • the hydrogel article is to be lathed to form an ocular lenticular device it is preferentially stored at a suitable temperature in the non-volatile hydrophilic plasticizer for between 1 day and 1 month prior to the lathing process. More preferably, the hydrogel article is stored at a suitable temperature in the non-volatile hydrophilic plasticizer for at least 2 weeks prior to lathing.
  • Suitable storage temperatures for use in the method of the invention will generally be between 0°C and 40°C.
  • the storage temperature will be between 10°C and 30°C, more preferably 20°C and 27°C and desirably it will be room temperature.
  • the time period over which the hydrogel article is maintained at a temperature to render it sufficiently rigid for mechanical processing will vary depending on the type of hydrogel used, the type of non-volatile hydrophilic plasticizer that has been contacted with the hydrogel article and the size of the hydrogel article specimen.
  • a time period will be between 30 and 120 minutes, however those of ordinary skill will be able to recognise precise times through practical examination of the hydrogel and the non-volatile hydrophilic plasticizer over the course of its contact with the low temperature conditions.
  • hydrogel articles of PHEMA are placed in a freezer at approximately -80°C where they are kept for a period of time suitable for them to become rigid.
  • a jet of dry ice is directed to the hydrogel article during lathing to maintain the rigid state.
  • the method may include another pre- treatment step, which involves pre-treating the hydrogel article in an aqueous solution of the non-volatile hydrophilic plasticizer at elevated temperatures to cure the hydrogel article.
  • the hydrogel article is maintained at the elevated temperature for between about 1 to 24 hours. More' preferably, the hydrogel article is maintained at the elevated temperature for between about 2 to 12 hours and more preferably still, the hydrogel article is maintained at the elevated temperature for between about 6 to 10 hours.
  • a step will be employed as part of the curing process for the hydrogel.
  • the elevated temperatures will be less than those required to damage the hydrogel. More preferably the temperature will be between room temperature and 80°C, most preferably between 50°C and 80°C.
  • the non- volatile hydrophilic plasticizer may be contacted with the hydrogel article prior to curing.
  • the non-volatile hydrophilic plasticizer is brought in contact with the hydrogel article prior to curing, the non-volatile hydrophilic plasticizer is selected to withstand the curing process without chemical decomposition.
  • a particular nonvolatile hydrophilic plasticizer suitable for this step in the method would be glycerol.
  • the hydrogel article After curing preferably the hydrogel article is contacted with the non-volatile hydrophilic plasticizer for between 1 day and 1 month, after which it is frozen and then machined by lathing.
  • the present invention may be incorporated into any hydrogel lathing process, preferably the method is used to provide ocular lenticular devices with improved surface smoothness and improved optical quality.
  • the method comprises the following steps: a Hydrogel articles are placed in water comprising 5 % to 80 % by weight of a non-volatile hydrophilic plasticizer and stored for at least 2 weeks at room temperature; b The articles are placed in a freezer at approximately -80 °C where they are kept for 30 to 120 minutes; and c The articles are mounted on a lathe and machined to the desired dimensional parameters while the rigid state of the article is maintained by the direction of a jet of dry ice onto the article.
  • improved ocular lenticular devices produced according to the methods of the present invention.
  • Such ocular lenticular devices will be identified by their superior surface smoothness and improved optical quality compared to ocular lenticular devices that have not been processed according to the method of the invention.
  • the artificial cornea is manufactured according to the methods described in Australian Patent 650156, and U.S. Patents 5,300,116 and 5,458,819, all issued to the present applicant. Specifically, these methods describe an artificial cornea, or a keratoprosthesis, as a one-piece core-and-skirt device, comprised of intimately attached central and peripheral portions.
  • the core is a transparent lenticular part composed essentially of a hydrogel, while the peripheral portion is an annular skirt composed of a like hydrogel but in a porous form.
  • a suitable material for both parts is, for example, a polymer of HEMA, commonly designated as PHEMA.
  • the porous skirt was made in a specially designed mould by polymerising an aqueous solution of 20% by weight HEMA (with a purity of 99% by weight) in the presence of divinyl glycol as a crossliking agent, and of ammonium persulfate solution and tetramethylethylenediamine as initiators, at room temperature for at least 22 hours.
  • HEMA divinyl glycol
  • ammonium persulfate solution and tetramethylethylenediamine as initiators
  • the transparent core was made in the central zone of the same mould by polymerising an aqueous solution of 70% by weight HEMA, in the presence of ethylene dimethacrylate as a crosslinking agent, and of the aforementioned initiators, at 50°C for at least 22 hours.
  • the resulting blank was then placed in a solution of 15% by weight glycerol in distilled and deionised water and kept in an oven at 60°C for 8 hours to cure.
  • the blank was then stored in the aforementioned glycerol solution for at least a further 2 weeks.
  • the blank was mounted onto a chuck and stored in a freezer at -80°C for 45 minutes.
  • the blank was inserted in the lathe and lathed.
  • low temperature was maintained by using a source of dry ice jet directed to the blank.
  • the final hydrogel article was then subjected to operations known in the art, including Soxhlet extraction, sterilization, and packing.
  • FIG. 2 shows the quality of the resulting surface.
  • FIG. 1 shows the lathed surface of a blank that was not subjected to treatment with glycerol.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
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  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Polymers & Plastics (AREA)
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  • Heart & Thoracic Surgery (AREA)
  • Crystallography & Structural Chemistry (AREA)
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  • Processes Of Treating Macromolecular Substances (AREA)
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Abstract

L'invention concerne un procédé pour améliorer la qualité de surface d'articles à hydrogel comprenant l'étape consistant à traiter l'article dans un état usinable en la présence d'un plastifiant hydrophile non volatil.
PCT/AU2003/000134 2002-02-07 2003-02-07 Procede pour ameliorer la qualite de surface d'articles a hydrogel WO2003066714A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003202321A AU2003202321A1 (en) 2002-02-07 2003-02-07 Method for improving the surface quality of hydrogel articles

Applications Claiming Priority (2)

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US35538502P 2002-02-07 2002-02-07
US60/355,385 2002-02-07

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WO2003066714A1 true WO2003066714A1 (fr) 2003-08-14

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6926965B2 (en) 2002-09-11 2005-08-09 Novartis Ag LbL-coated medical device and method for making the same
US6940580B2 (en) 2002-01-09 2005-09-06 Novartis Ag Polymeric articles having a lubricious coating and method for making the same
EP1623269A4 (fr) * 2003-04-24 2006-08-30 Ocular Sciences Inc Lentilles de contact a base d'hydrogel, systemes d'emballage et procedes de production associes
US7297725B2 (en) 1998-01-09 2007-11-20 Novartis Ag Biomedical devices having improved surface characteristics
US8044112B2 (en) 2006-03-30 2011-10-25 Novartis Ag Method for applying a coating onto a silicone hydrogel lens
US8158192B2 (en) 2006-12-21 2012-04-17 Novartis Ag Process for the coating of biomedical articles
US8460743B2 (en) 2008-03-18 2013-06-11 Novartis Ag Coating process for ophthalmic lenses
US9005700B2 (en) 2011-10-12 2015-04-14 Novartis Ag Method for making UV-absorbing ophthalmic lenses
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US7297725B2 (en) 1998-01-09 2007-11-20 Novartis Ag Biomedical devices having improved surface characteristics
US7566746B2 (en) 1998-01-09 2009-07-28 Novartis Ag Biomedical devices having improved surface characteristics
US7705067B2 (en) 1998-01-09 2010-04-27 Novartis Ag Biomedical device having improved surface characteristics
US7798639B2 (en) 2002-01-09 2010-09-21 Novartis Ag Method for applying lubricious coating to a polymeric article
US6940580B2 (en) 2002-01-09 2005-09-06 Novartis Ag Polymeric articles having a lubricious coating and method for making the same
US6926965B2 (en) 2002-09-11 2005-08-09 Novartis Ag LbL-coated medical device and method for making the same
US7582327B2 (en) 2002-09-11 2009-09-01 Novartis Ag LbL-coated medical device and method for making the same
US7431152B2 (en) 2003-04-24 2008-10-07 Coopervision International Holding Company, Lp Hydrogel contact lenses and package systems and production methods for same
US7816455B2 (en) 2003-04-24 2010-10-19 Coopervision International Holding Company, Lp Hydrogel contact lenses and package systems and production methods for same
EP1623269A4 (fr) * 2003-04-24 2006-08-30 Ocular Sciences Inc Lentilles de contact a base d'hydrogel, systemes d'emballage et procedes de production associes
US8044112B2 (en) 2006-03-30 2011-10-25 Novartis Ag Method for applying a coating onto a silicone hydrogel lens
US9052442B2 (en) 2006-10-30 2015-06-09 Novartis Ag Method for applying a coating onto a silicone hydrogel lens
US8158192B2 (en) 2006-12-21 2012-04-17 Novartis Ag Process for the coating of biomedical articles
US8460743B2 (en) 2008-03-18 2013-06-11 Novartis Ag Coating process for ophthalmic lenses
US9623614B2 (en) 2010-11-10 2017-04-18 Novartis Ag Method for making contact lenses
US9005700B2 (en) 2011-10-12 2015-04-14 Novartis Ag Method for making UV-absorbing ophthalmic lenses
US10338408B2 (en) 2012-12-17 2019-07-02 Novartis Ag Method for making improved UV-absorbing ophthalmic lenses

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