EP1246652A1 - Revetement de lentilles ophtalmiques implantables permettant de reduire l'eblouissement de bord - Google Patents

Revetement de lentilles ophtalmiques implantables permettant de reduire l'eblouissement de bord

Info

Publication number
EP1246652A1
EP1246652A1 EP00989222A EP00989222A EP1246652A1 EP 1246652 A1 EP1246652 A1 EP 1246652A1 EP 00989222 A EP00989222 A EP 00989222A EP 00989222 A EP00989222 A EP 00989222A EP 1246652 A1 EP1246652 A1 EP 1246652A1
Authority
EP
European Patent Office
Prior art keywords
coating material
hydrophilic polymer
meth
hydrophobic
coating
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP00989222A
Other languages
German (de)
English (en)
Inventor
Albert R. Leboeuf
John W. Sheets
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Alcon Inc
Original Assignee
Alcon Universal Ltd
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 Alcon Universal Ltd filed Critical Alcon Universal Ltd
Publication of EP1246652A1 publication Critical patent/EP1246652A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • 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
    • A61F2002/1696—Having structure for blocking or reducing amount of light transmitted, e.g. glare reduction

Definitions

  • This invention relates to coatings for implantable ophthalmic lenses.
  • the present invention relates to hydrophilic coatings that are applied to the edge of implantable ophthalmic lenses.
  • Foldable intraocular lens (“IOL”) materials can generally be divided into three categories: silicone materials, hydrogel materials, and non-hydrogel (“hydrophobic”) (meth)acrylic materials. See, for example, Foldable Intraocular Lenses, Ed. Martin et al., Slack Incorporated, Thorofare, New Jersey (1993). For purposes of the present
  • hydrophobic (meth)acrylic materials are (meth)acrylic materials that absorb less than approximately 5% water at room temperature.
  • lOLs particularly lOLs designed for implantation through a small incision
  • the invention described in the '786 patent reduces edge glare by including means, such as a plurality of v-shaped grooves, on the optic edge's surface for reflecting visible light that contacts the edge surface away from the retina of the patient.
  • the present invention relates to hydrophilic coating compositions for surgical implants, particularly ophthalmic implants comprising silicone or hydrophobic (meth)acrylic materials. More specifically, the present invention relates to a coating material comprising an ophthalmically acceptable hydrophobic (meth)acrylic polymer and an ophthalmically acceptable hydrophilic polymer.
  • the present invention also relates to a method for reducing edge glare in implantable ophthalmic lenses.
  • the method comprises applying a coating comprising an ophthalmically acceptable hydrophobic (meth)acrylic polymer and an ophthalmically acceptable hydrophilic polymer to an implant's optic edge surface. When hydrated, the coating is hazy or opaque and reduces or eliminates edge glare.
  • hydrophobic means a hydrophobic methacrylic polymer, a hydrophobic acrylic polymer, or a hydrophobic copolymer containing both methacrylic and acrylic functional groups.
  • hydrophobic means the materials absorb less than approximately 5% water at room temperature.
  • the coating material of the present invention comprises an ophthalmically acceptable hydrophobic (meth)acrylic polymer and a hydrophilic polymer. When hydrated, the coating material has a T g less than 37 °C, and preferably less than 15 °C.
  • the hydrophobic (meth)acrylic polymer ingredient in the coating material is preferably tacky to aid in attaching the coating material to the substrate.
  • Many ophthalmically acceptable hydrophobic (meth)acrylic polymers are known, including those described in U.S. Patent Nos. 5,290,892; 5,693,095; and 5,331 ,073, the entire contents of which are hereby incorporated by reference.
  • the hydrophobic (meth)acrylate polymer preferably comprises at least one (meth)acrylic monomer that contains an 5 aromatic group, such as those materials defined in US 5,693,095:
  • Ar is any aromatic ring which can be unsubstituted or substituted with CH3, C 2 H 5 , n-C 3 H 7 , iso-C 3 H 7 , OCH3, C 6 H ⁇ ⁇ , Cl, Br, C 6 H 5 , or CH2C6H5.
  • Suitable hydrophobic (meth)acrylic polymers include copolymers of 2- D phenylethyl methacrylate (2-PEMA) and 2-phenylethyl acrylate (2-PEA).
  • the hydrophobic (meth)acrylic polymer is formed using an initiator (generally about 2% or less). Any type of polymerization initiator may be used, including thermal initiators and
  • a preferred initiator is the benzoylphosphine oxide initiator, 2,4,6-trimethyl-benzoyldiphenylophosphine oxide ("TPO”), which can be activated by blue light or UV irradiation.
  • TPO 2,4,6-trimethyl-benzoyldiphenylophosphine oxide
  • Suitable thermal initiators include the conventional peroxides t-butyl peroctoate and bis-azoisobutronitrile.
  • Suitable UV initiators include benzoin methyl ether, Darocur 1173, and Darocur 4265 UV
  • the hydrophobic (meth)acrylic polymer optionally contains one or more ingredients selected from the group consisting of UV absorbers that are copolymerizable with the other (meth)acrylic ingredients; blue-light blocking colorants that are copolymerizable with the other (meth)acrylic ingredients; and chain transfer agents to minimize cross-linking.
  • Ultraviolet absorbing chromophores can be any compound which absorbs light having a wavelength shorter than about 400 nm, but does not absorb any substantial amount of visible light.
  • Suitable copolymerizable ultraviolet absorbing compounds are the substituted 2- hydroxybenzophenones disclosed in U.S. Patent No. 4,304,895 and the 2- hydroxy-5-acryloxyphenyl-2H-benzotriazoles disclosed in U.S. Patent No. 4,528,311.
  • the most preferred ultraviolet absorbing compound is 2-(3'- methallyl-2'-hydroxy-5'-methyl phenyl) benzothazole.
  • Suitable polymehzable blue-light blocking chromophores include those disclosed in U.S. Patent No. 5,470,932. If a blue-light activated polymerization initiator is chosen and a blue- light blocking colorant is added, the polymerization initiator identity or concentration may have to be adjusted to minimize any interference.
  • Chain transfer agents if present, are typically added in an amount ranging from 0.01 to 0.4%. Many chain transfer agents are known in the art. Examples of suitable chain transfer agents include 1-dodecanethiol and 2- mercaptoethanol.
  • the hydrophilic polymer contained in the coating materials of the present invention may be any ophthalmically acceptable hydrophilic polymer.
  • Suitable hydrophilic polymers include, but are not limited to polyhydroxyethyl methacrylate (polyHEMA); polyacrylamide; polyglyceryl methacrylate and polyvinyl pyrrolidone (PVP).
  • PVP polyvinyl pyrrolidone
  • the most preferred hydrophilic polymer is PVP.
  • These hydrophilic polymers are commercially available or can be made using known methods and are preferably obtained in a purified form in order to minimize extractables upon implantation of the coated IOL.
  • the hydrophilic polymer preferably has a molecular weight (weight avg.) in the range of 2,500 - 100,000. It is important that the hydrophilic polymer's molecular weight be great enough and be present in the hydrogel coating material in a sufficient amount to form hydrophilic domains capable of dispersing light.
  • the hydrophilic polymer should not be too small, otherwise an appreciable amount of it may leach out of the coating after the coating is applied to the IOL.
  • the hydrophilic polymer should not be too large, otherwise it may affect intraocular pressure in the event that some of the polymer leaches out of the coating. In the case of PVP, a molecular weight of 10,000 is preferred.
  • the coating material is formed by preparing an ophthalmically acceptable hydrophobic (meth)acrylic polymer, then purifying (if necessary or desired) the cured hydrophobic (meth)acrylic polymer via extraction in a suitable solvent, then dissolving the hydrophobic (meth)acrylic polymer and an ophthalmically acceptable hydrophilic polymer in a suitable solvent or mixture of solvents to form a coating solution.
  • the proportion of hydrophobic (meth)acrylic polymer to hydrophilic polymer in the coating composition depends upon on the desired hydrated water content for the coating, the desired thickness of the coating, the chosen hydrophobic (meth)acrylic and hydrophilic materials, etc.
  • the proportion of hydrophobic (meth)acrylic polymer to hydrophilic polymer can be determined by routine calculations and experimentation.
  • the desired water content of the hydrated coating will range from about 20 - 70% and the desired coating thickness will range from 0.5 - 1 ⁇ m.
  • Typical concentrations of hydrophilic polymer in the coating material will therefore range from about 5 to about 50%, preferably from about 15 to about 30%.
  • the solvent or solvent mixture used to form the coating solution should be chose to give a homogeneous coating solution. Because the coatings will be used to reduce glare, it is not necessary for the coating solution to be clear. Whether or not the coating solution is clear, the coating should be translucent to opaque after being applied to the implant's edge and hydrated.
  • An example of a suitable solvent mixture in the case of a 2-PEMA/2-PEA copolymer as the hydrophobic (meth)acrylic polymer and PVP as the hydrophilic polymer is a 2- pentanone/methanol mixture.
  • polar solvents such as alcohols will be suitable when the hydrophilic polymer is polyHEMA or polyglycerylmethacrylate, and ketones, such as 2-pentanone, or methylene chloride, will be suitable when the hydrophilic polymer is polyacrylamide or PVP.
  • the coating material is preferably attached to the substrate IOL by means of one or both of the following: (1) hydrophobic or "physical” (i.e., non- covalent) cross-linking and (2) interpenetrating polymer networking.
  • the coating material is internally cross-linked by non-covalent cross-linking.
  • the coating material may be covalently cross-linked to the IOL by means of a cross-linking agent.
  • the coating solution is applied to the implant's edge surface by conventional techniques, such as spin- or dip-coating processes or casting a coating layer around a pre-formed rod of the optic material. Dip-coating is preferred.
  • the implant is preferably dipped at such a rate so as to minimize any swelling of the implant caused by the solvent in the coating solution.
  • the coating is dried.
  • a two-stage drying process is preferred. First, the coated implant is allowed to dry in air until most or all of the solvent has evaporated (generally ⁇ 15 minutes). Second, the coated implant is baked at elevated temperature, about 40 - 100 °C, to eliminate as much of the remaining solvent as possible. A preferred drying process involves room temperature air drying for 15 minutes, followed by baking at 90 °C for about 20 - 60 minutes. If a covalent cross-linking agent is added to the coating solution, the coating is dried in a way that fully activates the cross-linking agent.
  • the coating can be easily removed by a variety of organic solvents or solvent mixtures, including the same solvent used as the base in the preparation of the coating solution.
  • the coating cannot be removed by water, however.
  • the implants suitable for coating with the hydrophilic coatings of the present invention are preferably made of hydrophobic (meth)acrylic materials, but could also be constructed of silicone or silicone-(meth)acrylic copolymers.
  • Preferred hydrophobic (meth)acrylic materials are those polymeric materials described in U.S. Patent Nos. 5,290,892 and 5,693,095, the entire contents of which are hereby incorporated by reference.
  • the coatings of the present invention may be used in conjunction with substrate materials intended for use as a "hard” IOL (that is inserted in an 0 unfolded state) or a “foldable” or “soft” IOL (that is inserted in a folded or compressed state).
  • Suitable IOL materials to be coated include those disclosed in U.S. Patent Nos. 5,693,095 or 5,331 ,073.
  • "implants" includes contact lenses.
  • Suitable reactive plasma gases include oxidizing gases, such as oxygen gas.
  • Example 1 Mixture of Hydrophobic (Meth)acrylic Polymer and Hydrophilic Polymer.
  • a copolymer of 2-PEMA (1.5 parts by weight) and 2-PEA (3.24 parts by weight) was prepared using Darocur 4265 (0.06 parts by weight) as an initiator.
  • the copolymer was cured in polypropylene slab molds (10 mm x 20 mm x 0.9 mm) by exposure to blue light for one hour using a Kuizer Palatray CU blue light unit (12 - 14 mW/cm 2 ).
  • the cured copolymer (0.8345 g) was then extracted in methanol at room temperature overnight.
  • the extracted copolymer was dried in air, but not stripped of methanol solvent. Once dry, the slabs were dissolved in a mixture of 2-pentanone and methanol to form the following coating solution:
  • a copolymer comprising 65% 2-PEA; 30% 2-PEMA; 1.8% o- methallyl Tinuvin P; and 3.2% 1 ,4-butanediol diacrylate was prepared using 1.8% Perkadox-16 as a thermal initiator.
  • This copolymer (“Substrate Copolymer”) was cured in the same slab molds described above and then extracted in acetone (overnight, then dried in air for approximately 2 hours, then dried at 100 °C for approximately 2 hours). Also, commercially available ACRYSOF ® lOL's were obtained. The slabs and lOLs were then dipped in the coating solution, dried in air for approximately 5 - 10 minutes, and then baked at 90 °C for 20 - 90 minutes.
  • the cured coating was optically clear. After hydrating the coating, the coating is translucent/opaque due to the heterogeneous distribution of water within the coating composition. Coating thickness was typically 0.5 to 1 microns. After remaining hydrated for 9 months, the coating's haze or opacity did not appear to have diminished and remained attached to the substrate slab or IOL.
  • Example 2 Water Content of the Coating Material of Example 1.
  • Example 1 To determine the water content of the hydrated coating material used in Example 1 , a multi-layer film of the coating solution defined in Example 1 was cast in a polypropylene slab mold. After each layer was applied, it was allowed to dry at room temperature in air before the next layer was added. After four or five layers were made, the multi-layered film was dried at 100 °C for one hour. The dried film was weighed and then placed in de-ionized water at room temperature. The film's weight change was monitored over time. The results are shown in Table 1 below. After 184 hours of hydration, the film was removed from the de-ionized water, weighed, extracted, dried and weighed again. The film gave 5.7% (by weight) extractables and had a water content (hydrated) of 52.6% (weight). The film was replaced in the deionized water for s an additional 432 hours (616 hours total hydration time from the beginning of the experiment). The calculated water content at 616 hours was 59.5% (weight).
  • Example 3 (Comparative Example) Copolymer of Hydrophobic (Meth)acrylic Monomers and Hydrophilic Monomer.
  • the resulting copolymer was dissolved in 2-pentanone to give a coating solution with a 6 wt-% copolymer content.
  • a pre-extracted (acetone) slab of the Substrate Copolymer of Example 1 was dipped in the coating solution, air-dried at room temperature for 10 minutes, and oven-cured at 90°C for 75 minutes.
  • the coated slab was placed into deionized water and its hydration properties followed over time. The results are shown in Table 2 below.
  • Examples 1 and 3 gave significantly different results.
  • the hydrated PEMA-PVP polymer mixture coating material is opaque and of high water content, while the hydrated, random PEMA-NVP copolymer is clear and has a lower water uptake.

Landscapes

  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • Dermatology (AREA)
  • Biomedical Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Materials For Medical Uses (AREA)
  • Prostheses (AREA)
  • Eyeglasses (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)

Abstract

La présente invention concerne des revêtements hydrophiles destinés à des lentilles ophtalmiques implantables. Les revêtements, qui sont appliqués sur la surface marginale de la lentille ophtalmique, comprennent un polymère (méth)acrylique hydrophobe et un polymère hydrophile. Une fois hydratés, les revêtements permettent de réduire ou de supprimer l'éblouissement de bord.
EP00989222A 2000-01-12 2000-12-06 Revetement de lentilles ophtalmiques implantables permettant de reduire l'eblouissement de bord Withdrawn EP1246652A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US17577900P 2000-01-12 2000-01-12
US175779P 2000-01-12
PCT/US2000/033102 WO2001051103A1 (fr) 2000-01-12 2000-12-06 Revetement de lentilles ophtalmiques implantables permettant de reduire l'eblouissement de bord

Publications (1)

Publication Number Publication Date
EP1246652A1 true EP1246652A1 (fr) 2002-10-09

Family

ID=22641583

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00989222A Withdrawn EP1246652A1 (fr) 2000-01-12 2000-12-06 Revetement de lentilles ophtalmiques implantables permettant de reduire l'eblouissement de bord

Country Status (14)

Country Link
EP (1) EP1246652A1 (fr)
JP (1) JP2003519538A (fr)
KR (1) KR20020062357A (fr)
CN (1) CN1423570A (fr)
AR (1) AR034844A1 (fr)
AU (1) AU768090B2 (fr)
BR (1) BR0016998A (fr)
CA (1) CA2392593A1 (fr)
HK (1) HK1048957A1 (fr)
MX (1) MXPA02006841A (fr)
NO (1) NO20023343L (fr)
NZ (1) NZ520117A (fr)
WO (1) WO2001051103A1 (fr)
ZA (1) ZA200204972B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5324100B2 (ja) 2004-11-29 2013-10-23 ディーエスエム アイピー アセッツ ビー．ブイ． ポリマーコーティングに含まれる移行性物質の量を減少させる方法
JP2009518479A (ja) 2005-12-09 2009-05-07 ディーエスエム アイピー アセッツ ビー．ブイ． 高分子電解質を含む親水性コーティング
JP5499321B2 (ja) 2006-09-13 2014-05-21 ディーエスエム アイピー アセッツ ビー．ブイ． 医療コーティングのためのコーティング調合物
US8513320B2 (en) 2007-02-28 2013-08-20 Dsm Ip Assets B.V. Hydrophilic coating
DK2114477T3 (da) 2007-02-28 2012-08-20 Dsm Ip Assets Bv Hydrofil coating
BR112012032202A2 (pt) 2010-06-16 2016-11-22 Dsm Ip Assets Bv formulação de revestimento para a preparação de um revestimento hidrofílico.
US20130178935A1 (en) * 2012-01-11 2013-07-11 Lara Henry Polarized component ocular devices
CN109124826A (zh) * 2017-06-28 2019-01-04 爱博诺德（北京）医疗科技有限公司 眼科透镜

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US5755786A (en) * 1992-09-28 1998-05-26 Iolab Corporation Ophthalmic lens with reduced edge glare
AU696001B2 (en) * 1995-06-07 1998-08-27 Alcon Laboratories, Inc. Improved high refractive index ophthalmic lens materials
US5698192A (en) * 1996-09-25 1997-12-16 University Of Florida Ocular implants and methods for their manufacture
US6169127B1 (en) * 1996-08-30 2001-01-02 Novartis Ag Plasma-induced polymer coatings
BR9811081A (pt) * 1997-08-07 2000-08-15 Alcon Lab Inc Lente de difração intracorneal

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Title
See references of WO0151103A1 *

Also Published As

Publication number Publication date
BR0016998A (pt) 2002-10-15
NO20023343D0 (no) 2002-07-11
AU768090B2 (en) 2003-12-04
WO2001051103A1 (fr) 2001-07-19
NZ520117A (en) 2003-02-28
MXPA02006841A (es) 2003-05-23
CN1423570A (zh) 2003-06-11
NO20023343L (no) 2002-09-09
ZA200204972B (en) 2003-06-20
AU2575801A (en) 2001-07-24
KR20020062357A (ko) 2002-07-25
JP2003519538A (ja) 2003-06-24
HK1048957A1 (zh) 2003-04-25
AR034844A1 (es) 2004-03-24
CA2392593A1 (fr) 2001-07-19

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