Connect public, paid and private patent data with Google Patents Public Datasets

High Refractive-Index, Hydrophilic Monomers and Polymers, and Ophthalmic Devices Comprising Such Polymers

Download PDF

Info

Publication number
US20080183006A1
US20080183006A1 US12060322 US6032208A US2008183006A1 US 20080183006 A1 US20080183006 A1 US 20080183006A1 US 12060322 US12060322 US 12060322 US 6032208 A US6032208 A US 6032208A US 2008183006 A1 US2008183006 A1 US 2008183006A1
Authority
US
Grant status
Application
Patent type
Prior art keywords
hydrophilic
group
aromatic
invention
ch
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.)
Abandoned
Application number
US12060322
Inventor
Joseph C. Salamone
Jay F. Kunzler
Richard M. Ozark
Original Assignee
Salamone Joseph C
Kunzler Jay F
Ozark Richard M
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

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/26Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/16Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52Amides or imides
    • C08F220/54Amides
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS, OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made
    • G02B1/04Optical elements characterised by the material of which they are made made of organic materials, e.g. plastics
    • G02B1/041Lenses
    • G02B1/043Contact lenses

Abstract

A hydrophilic, aromatic-based monomer has an aromatic group substituted with at least one hydrophilic substituent and a reactive functional group. Polymers comprising such a hydrophilic, aromatic-based monomers avoid or reduce the risk of forming vacuoles of absorbed water. Furthermore, such polymers have high refractive index, and, thus, are advantageously used for making ophthalmic devices, such as intraocular lenses, contact lenses, corneal rings, corneal inlays, and keratoprostheses.

Description

    CROSS REFERENCE
  • [0001]
    This application is a divisional of patent application Ser. No. 11/139,276 filed May 27, 2005 which is incorporated by reference herein
  • BACKGROUND OF THE INVENTION
  • [0002]
    The present invention relates to high refractive-index, hydrophilic monomers and polymers, and ophthalmic devices comprising such polymers. In particular, the present invention relates to high refractive-index, aromatic-based, hydrophilic monomers and polymers, and ophthalmic devices comprising such polymers.
  • [0003]
    Since the 1940s ophthalmic devices in the form of intraocular lens (“IOL”) implants have been utilized as replacements for diseased or damaged natural ocular lenses. In most cases, an intraocular lens is implanted within an eye at the time of surgically removing the diseased or damaged natural lens, such as for example, in the case of cataracts. For decades, the preferred material for fabricating such intraocular lens implants was poly(methyl methacrylate), which is a rigid, glassy polymer.
  • [0004]
    Softer, more flexible IOL implants have gained in popularity in more recent years due to their ability to be compressed, folded, rolled or otherwise deformed. Such softer IOL implants may be deformed prior to insertion thereof through an incision in the cornea of an eye. Following insertion of the IOL in an eye, the IOL returns to its original pre-deformed shape due to the memory characteristics of the soft material. Softer, more flexible IOL implants as just described may be implanted into an eye through an incision that is much smaller, i.e., less than 4.0 mm, than that necessary for more rigid IOLs, i.e., 5.5 to 7.0 mm. A larger incision is necessary for more rigid IOL implants because the lens must be inserted through an incision in the cornea slightly larger than the diameter of the inflexible IOL optic portion. Accordingly, more rigid IOL implants have become less popular in the market since larger incisions have been found to be associated with an increased incidence of postoperative complications, such as induced astigmatism.
  • [0005]
    With recent advances in small-incision cataract surgery, increased emphasis has been placed on developing soft, foldable materials suitable for use in artificial IOL implants. In general, the materials of current commercial IOLs fall into one of three general categories: silicones, hydrophilic acrylics and hydrophobic acrylics.
  • [0006]
    In general, high water content hydrophilic acrylics, or “hydrogels,” have relatively low refractive indices, making them less desirable than other materials with respect to minimal incision size. Low refractive-index materials require a thicker IOL optic portion to achieve a given refractive power. Silicone materials may have a higher refractive index than high-water content hydrogels, but tend to unfold explosively after being placed in the eye in a folded position. Explosive unfolding can potentially damage the corneal endothelium and/or rupture the natural lens capsule and associated zonules. Low glass-transition-temperature hydrophobic acrylic materials are desirable because they typically have a high refractive index and unfold more slowly and more controllably than silicone materials. Unfortunately, low glass-transition-temperature hydrophobic acrylic materials, which contain little or no water initially, tend to absorb water over time and form pockets of water or vacuoles in vivo, causing light reflections or “glistenings.” Furthermore, it may be difficult to achieve ideal folding and unfolding characteristics due to the temperature sensitivity of some acrylic polymers.
  • [0007]
    Because of the noted shortcomings of current polymeric materials available for use in the manufacture of ophthalmic implants, there is a need for stable, biocompatible polymeric materials having desirable physical characteristics and refractive indices.
  • SUMMARY OF THE INVENTION
  • [0008]
    In general, the present invention provides hydrophilic monomers having high refractive indices and polymeric compositions comprising such monomers.
  • [0009]
    In one aspect, the present invention provides hydrophilic, aromatic-based monomers and polymeric compositions comprising such monomers.
  • [0010]
    In another aspect, a hydrophilic, aromatic-based monomer of the present invention has a formula of
  • [0000]

    G-D-Ar  (I)
  • [0000]
    wherein Ar is a C6-C24 aromatic group having at least a hydrophilic substituent, D is a divalent linking group, and G is a reactive functional group.
  • [0011]
    In still another aspect, a polymeric composition comprises a copolymer of at least two hydrophilic, aromatic-based monomers of the present invention or a copolymer of an aromatic-based monomer of the present invention and at least one other monomer.
  • [0012]
    In still another aspect, said at least one other monomer is selected from hydrophilic monomers, hydrophobic monomers, and combinations thereof.
  • [0013]
    In yet another aspect, the present invention provides a method of making a high refractive index hydrophilic monomer. The method comprises providing a C6-C24 aromatic compound having at least one hydrophilic substituent and at least a reactive functional group; and converting said at least a reactive functional group to a polymerizable functional group.
  • [0014]
    In yet another aspect, the present invention provides a method of making a hydrophilic polymeric composition having a high refractive index. The method comprises polymerizing a hydrophilic, aromatic-based monomer or polymerizing such a monomer and at least a different monomer.
  • [0015]
    In yet another aspect, an ophthalmic device comprises a polymeric material that comprises residues of at least a hydrophilic, aromatic-based monomer of the present invention.
  • [0016]
    Other features and advantages of the present invention will become apparent from the following detailed description and claims.
  • DETAILED DESCRIPTION OF THE INVENTION
  • [0017]
    In general, the present invention provides hydrophilic monomers having high refractive indices and polymeric compositions comprising such monomers. The polymeric compositions of the present invention have refractive index of about 1.4 or greater. In some embodiments, the refractive index is in the range from about 1.4 to about 1.7. In some other embodiments, the refractive index is in the range from about 1.45 to about 1.6.
  • [0018]
    In one aspect, a polymeric composition of the present invention has an equilibrium water content of greater than about 4.5 percent (by weight), thus avoiding problems related to the formation of water vacuoles. In addition, a polymeric composition of the present invention can have a relatively high elongation, such as about 80 percent or greater. Accordingly, in many aspects, the subject polymeric compositions are more suitable for use in the manufacture of ophthalmic devices than many prior-art polymeric materials.
  • [0019]
    Current commercial acrylic-based ophthalmic products have a water content less than 4.5 percent by weight. These hydrophobic products tend to absorb water over time in vivo and form water vacuoles or “glistenings.” In contrast, a polymeric composition comprising residues of hydrophilic monomers of the present invention tend to absorb water rapidly to equilibrium level. Although, applicants do not wish to be bound to any particular theory, it is believed that the absorbed water also is distributed throughout the polymeric composition because of its association with the hydrophilic substituents in the aromatic groups. Therefore, polymeric compositions of the present invention do not present the risk of formation of water vacuoles in vivo.
  • [0020]
    A hydrophilic aromatic-based monomer of the present invention has a formula of
  • [0000]

    G-D-Ar  (I)
  • [0000]
    wherein Ar is a C6-C24 aromatic group having at least a hydrophilic substituent, D is a divalent linking group, and G is a reactive functional group. The term “C6-C24 aromatic group” means the aromatic group having 6-24 carbon atoms, excluding any carbon atoms in the substituent group.
  • [0021]
    In one embodiment, Ar is a phenyl group having at least a hydrophilic substituent.
  • [0022]
    In another embodiment, at least a hydrophilic substituent on the aromatic group is selected from the group consisting of carboxy, alcohols (including monohydric and polyhydric alcohols), and combinations thereof.
  • [0023]
    In another embodiment, at least a hydrophilic substituent on the aromatic group is selected from the group consisting of —COOH, —CH2—CH2OH, —(CHOH)2—CH2OH, —CH2—CHOH—CH2OH, and combinations thereof.
  • [0024]
    In still another embodiment, at least a hydrophilic substituent on the aromatic group is a poly(alkylene glycol), such as poly(ethylene glycol) having a formula of —(O—CH2—CH2)nOH, wherein n is an integer and 1≦n≦100, preferably 1≦n≦50, and more preferably, 1≦n≦20.
  • [0025]
    In a further embodiment, said hydrophilic substituent is selected from the group consisting of carboxamide, dialkyl-substituted carboxamide, amino, alkanolamino, sulfonate, phosphonate, sulfate, phosphate, ureido, substituted sugars, and combinations thereof.
  • [0026]
    In another aspect, G is a reactive functional group selected from the group consisting of vinyl, allyl, acryloyl, acryloyloxy, methacryloyl, methacryloyloxy, epoxide, isocyanate, isothiocyanate, amino, hydroxyl, mercapto, anhydride, carboxylic, fumaryl, styryl, and combinations thereof.
  • [0027]
    In another aspect, G is selected from the group consisting of vinyl, styryl, acryloyloxy, and methacryloyloxy.
  • [0028]
    In another aspect, D is a divalent group selected from the group consisting of saturated straight C1-C10 hydrocarbons, unsaturated straight C1-C10 hydrocarbons, saturated branched C3-C10 hydrocarbons, unsaturated branched C3-C10 hydrocarbons, saturated cyclic C3-C10 hydrocarbons, unsaturated cyclic C3-C10 hydrocarbons, and alkyloxy substituents. Preferably, D is a saturated straight C1-C10 hydrocarbon divalent group.
  • [0029]
    In one embodiment, a hydrophilic aromatic-based monomer of the present invention has a formula
  • [0000]
  • [0000]
    wherein R is hydrogen or CH3; D is a divalent group selected from the group consisting of saturated straight C1-C10 hydrocarbons, unsaturated straight C1-C10 hydrocarbons, saturated branched C3-C10 hydrocarbons, unsaturated branched C3-C10 hydrocarbons, saturated cyclic C3-C10 hydrocarbons, unsaturated C3-C10 hydrocarbons, and alkoxy substituents; E is selected from the group consisting of carboxy, carboxamide, and alcohol (including monohydric and polyhydric alcohols) substituents; and m is an integer from 1 to, and including, 5. Preferably, m is 1 or 2.
  • [0030]
    In one embodiment, a hydrophilic aromatic-based monomer of the present invention has a formula
  • [0000]
  • [0000]
    wherein R is either hydrogen or CH3.
  • [0031]
    In another embodiment, a hydrophilic aromatic-based monomer of the present invention has a formula
  • [0000]
  • [0000]
    wherein R is hydrogen or CH3.
  • [0032]
    In still another embodiment, a hydrophilic aromatic-based monomer of the present invention has a formula
  • [0000]
  • [0000]
    wherein R1 is —C(O)O—NH2 or —C(O)—N(CH3)2.
  • [0033]
    Hydrophilic, aromatic-based monomers of the present invention can be used to produce homopolymers or copolymers having high refractive indices, such as about 1.4 or greater. In some embodiments, the homopolymers or copolymers have refractive indices in the range from about 1.4 to about 1.7; in some other embodiments, from about 1.45 to about 1.6.
  • [0034]
    Alternatively, a hydrophilic, aromatic-based monomer of the present invention can be copolymerized with another hydrophilic or hydrophobic monomer to provide a polymer having high refractive index, such as about 1.4 or greater.
  • [0035]
    Non-limiting examples of other hydrophilic monomers useful for polymerization with one or more hydrophilic, aromatic-based monomers of the present invention include N,N-dimethylacrylamide, glycerol methacrylate, N-vinylpyrrolidone, and 2-hydroxyethyl methacrylate. Preferably, N,N-dimethylacrylamide is used for increased hydrophilicity.
  • [0036]
    Non-limiting examples of other hydrophobic monomers useful for polymerization with one or more hydrophilic, aromatic-based monomers of the present invention include C1-C10 alkyl methacrylates (e.g., methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, octyl methacrylate, or 2-ethylhexyl methacrylate; preferably, methyl methacrylate to control mechanical properties), C1-C10 alkyl acrylates (e.g., methyl acrylate, ethyl acrylate, propyl acrylate, or hexyl acrylate; preferably, ethyl acrylate to control mechanical properties), C6-C40 arylalkyl acrylates (e.g., phenylethyl acrylate, benzyl acrylate, 3-phenylpropyl acrylate, 4-phenylbutyl acrylate, 5-phenylpentyl acrylate, 8-phenyloctyl acrylate, or 2-phenylethoxy acrylate; preferably, 2-phenylethyl acrylate to increase refractive index), and C6-C40 arylalkyl methacrylates (e.g., 2-phenylethyl methacrylate, 3-phenylpropyl methacrylate, 4-phenylbutyl methacrylate, 5-phenylpentyl methacrylate, 8-phenyloctyl methacrylate, 2-phenoxyethyl methacrylate, 3,3-diphenylpropyl methacrylate, 2-(1-naphthylethyl)methacrylate, benzyl methacrylate, or 2-(2-naphthylethyl)methacrylate; preferably, phenylethyl methacrylate to increase refractive index). Other suitable hydrophobic monomers include silicon-containing monomers, especially aromatic-based silicon-containing monomer, such as 3-methacryloyloxypropyldiphenylmethylsilane.
  • [0037]
    The hydrophilic, aromatic-based monomer having Formula (III) can be produced by a method illustrated in Scheme 1.
  • [0000]
  • [0038]
    The hydrophilic, aromatic-based monomer having Formula (IV) can be produced by a method illustrated in Scheme 2.
  • [0000]
  • [0039]
    Homopolymers of hydrophilic, aromatic-based monomers of the present invention and copolymers comprising one or more hydrophilic, aromatic-based monomers of the present invention and at least another monomer can be produced by free radical polymerization. For example, a copolymer of the hydrophilic, aromatic-based monomer having Formula (III) and 2-phenylethyl methacrylate (or 2-phenylethyl acrylate) is produced according to the following reaction, in the presence of a thermal polymerization initiator (such as one selected from the list of thermal polymerization initiators disclosed below) at a temperature in the range from about 20° C. to about 120° C. Alternatively, the reaction can be carried out in the presence of a photoinitiator selected from the list of photoinitiators disclosed below at a temperature in the range from about 20° C. to about 60° C.
  • [0000]
  • [0000]
    wherein R and R′ are independently selected from the group consisting of hydrogen and CH3; p and q are independently selected integers greater than 1 to provide a desired molar ratio of the monomers and a desired molecular weight. For example, p and q can be in the range from about 1 to about 100,000, or from 1 to about 50,000, or from 1 to 20,000.
  • [0040]
    Another exemplary copolymer comprising the monomer having Formula (IV); N,N-dimethylacrylamide; and phenylethyl methacrylate (or phenylethyl acrylate) is made according to the following reaction, in the presence of a thermal polymerization initiator (such as one selected from the list of thermal polymerization initiators disclosed below) at a temperature in the range from about 20° C. to about 120° C. Alternatively, the reaction can be carried out in the presence of a photoinitiator selected from the list of photoinitiators disclosed below at a temperature in the range from about 20° C. to about 60° C.
  • [0000]
  • [0000]
    wherein R, R′, and R″ are independently selected from the group consisting of hydrogen and CH3; p, q, and r are independently selected integers greater than 1 to provide a desired molar ratio of the monomers and a desired molecular weight. For example, p, q, and r can be in the range from about 1 to about 100,000, or from 1 to about 50,000, or from 1 to 20,000.
  • [0041]
    A formulation for the production of a polymer comprising a hydrophilic, aromatic-based monomer of the present invention can include one or more crosslinking agents in an amount less than about 10 percent by weight of the weight of all monomers and crosslinking agents, if desired. In one embodiment, the crosslinking agents are present in an amount less than about 5 percent by weight.
  • [0042]
    Non-limiting examples of suitable crosslinking agents include ethylene glycol dimethacrylate (“EGDMA”); diethylene glycol dimethacrylate; ethylene glycol diacrylate; triethylene glycol dimethacrylate; triethylene diacrylate; allyl methacrylates; allyl acrylates; 1,3-propanediol dimethacrylate; 1,3-propanediol diacrylate; 1,6-hexanediol dimethacrylate; 1,6-hexanediol diacrylate; 1,4-butanediol dimethacrylate; 1,4-butanediol diacrylate; trimethylolpropane trimethacrylate (“TMPTMA”); glycerol trimethacrylate; poly(ethyleneoxide mono- and di-acrylate); N,N′-dihydroxyethylene bisacrylamide; diallyl phthalate; triallyl cyanurate; divinylbenzene; ethylene glycol divinyl ether; N,N-methylene-bis-(meth)acrylamide; divinylbenzene; divinylsulfone; and the like.
  • [0043]
    Although not required, homopolymers or copolymers within the scope of the present invention may optionally have one or more strengthening agents added prior to polymerization, preferably in quantities of less than about 80 weight percent but more typically from about 20 to about 60 weight percent. Non-limiting examples of suitable strengthening agents are described in U.S. Pat. Nos. 4,327,203; 4,355,147; and 5,270,418; each of which is incorporated herein in its entirety by reference. Specific examples, not intended to be limiting, of such strengthening agents include cycloalkyl acrylates and methacrylates; e.g., tert-butylcyclohexyl methacrylate and isopropylcyclopentyl acrylate.
  • [0044]
    One or more ultraviolet (“UV”) light absorbers may optionally be added to the copolymers prior to polymerization in quantities less than about 5 percent by weight. Suitable UV light absorbers for use in the present invention include for example, but are not limited to, β-(4-benzotriazoyl-3-hydroxyphenoxy)ethyl acrylate; 4-(2-acryloxyethoxy)-2-hydroxybenzophenone; 4-methacryloyloxy-2-hydroxybenzophenone; 2-(2′-methacryloyloxy-5′-methylphenyl)benzotriazole; 2-(2′-hydroxy-5′-methacryloxyethylphenyl)-2H-benzotriazole; 2-[3′-tert-butyl-2′-hydroxy-5′-(3″-methacryloyloxypropyl)phenyl]-5-chlorobenzotriazole; 2-(3′-tert-butyl-5′-(3″-dimethylvinylsilylpropoxy)-2′-hydroxyphenyl]-5-methoxybenzotriazole; 2-(3′-allyl-2′-hydroxy-5′-methylphenyl)benzotriazole; 2-[3′-tert-butyl-2′-hydroxy-5′-(3″-methacryloyloxypropoxy)phenyl]-5-methoxybenzotriazole, and 2-[3′-tert-butyl-2′-hydroxy-5′-(3″-methacryloyloxypropoxy)phenyl]-5-chlorobenzotriazole. Preferably, the UV light absorber also has a polymerizable functional group. In one embodiment, the preferred UV light absorbers are β-(4-benzotriazoyl-3-hydroxyphenoxy)ethyl acrylate and 2-[3′-tert-butyl-2′-hydroxy-5′-(3″-methacryloyloxypropoxy)phenyl]-5-chlorobenzotriazole.
  • [0045]
    One or more suitable free radical polymerization initiators may be desirably added to the copolymers of the present invention. These initiators include thermal polymerization initiators and photopolymerization initiators. Thermal polymerization initiators include organic peroxy compounds and azobis(organonitrile) compounds. Non-limiting examples of suitable organic peroxy compounds include peroxymonocarbonate esters, such as tert-butylperoxy isopropyl carbonate; peroxydicarbonate esters, such as di(2-ethylhexyl) peroxydicarbonate, di(sec-butyl)peroxydicarbonate and diisopropyl peroxydicarbonate; diacyl peroxides, such as 2,4-dichlorobenzoyl peroxide, isobutyryl peroxide, decanoyl peroxide, lauroyl peroxide, propionyl peroxide, acetyl peroxide, benzoyl peroxide, p-chlorobenzoyl peroxide; peroxyesters, such as t-butylperoxy pivalate, t-butylperoxy octylate, and t-butylperoxy isobutyrate; methylethylketone peroxide; and acetylcyclohexane sulfonyl peroxide. Non-limiting examples of suitable azobis(organonitrile) compounds include azobis(isobutyronitrile); 2,2′-azobis(2,4-dimethylpentanenitrile); 1,1′-azobiscyclohexanecarbonitrile; and azobis(2,4-dimethylvaleronitrile); and mixtures thereof. Preferably, such an initiator is employed in a concentration of approximately 0.01 to 1 percent by weight of the total monomer mixture.
  • [0046]
    Representative UV photopolymerization initiators include those known in the field, such as the classes of benzophenone and its derivatives, benzoin ethers, and phosphine oxides. Some non-limiting examples of these initiators are benzophenone; 4,4′-bis(dimethylamino)benzophenone; 4,4′-dihydroxybenzophenone; 2,2-diethoxyacetophenone; 2,2-dimethoxy-2-phenylacetophenone; 4-(dimethylamino)benzophenone; 2,5-dimethylbenzophenone; 3,4-dimethybenzophenone; 4′-ethoxyacetophenone; 3′-hydroxyacetophenone; 4′-hydroxyacetophenone; 3-hydroxybenzophenone; 4-hydroxybenzophenone; 1-hydroxycyclohexyl phenyl ketone; 2-hydroxy-2-methylpropiophenone; 2-methylbenzophenone; 3-methylbenzophenone; 4′-phenoxyacetophenone; 2-methyl-4′-(methylthio)-2-morpholinopropiophenone; benzoin methyl ether; benzoin ethyl ether; diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide. These initiators are commercially available. Other photo polymerization initiators are known under the trade names Darocur™ and Irgacure™, such as Darocur™ 1173 (2-hydroxy-2-methyl-1-phenyl-1-propanone), Irgacure™ 651 (2,2-dimethoxy-2-phenylacetophenone), Irgacure™ 819 (phenyl-bis(2,4,6-trimethyl benzoyl)phosphine oxide), and Irgacure™ 184 (1-hydroxy cyclohexyl phenyl ketone) from Ciba-Geigy, Basel, Switzerland.
  • [0047]
    The polymeric compositions of the present invention are transparent, flexible, of relatively high refractive index and of relatively high elongation. The polymeric compositions of the present invention with the desirable physical properties noted above are particularly useful in the manufacture of ophthalmic devices such as but not limited to relatively thin, foldable IOLs, contact lenses, corneal rings, corneal inlays, and keratoprostheses. Furthermore, absorbed water in the polymeric compositions of the present invention does not tend to form water vacuoles. Thus, the polymeric compositions of the present invention are more advantageously used in ophthalmic device applications than prior-art acrylic compositions.
  • [0048]
    IOLs having relatively thin optic portions are critical in enabling a surgeon to minimize surgical incision size. Keeping the surgical incision size to a minimum reduces intraoperative trauma and postoperative complications. A relatively thin IOL optic portion is also critical for accommodating certain anatomical locations in the eye such as the anterior chamber and the ciliary sulcus. IOLs may be placed in the anterior chamber for increasing visual acuity in either aphakic or phakic eyes, or placed in the ciliary sulcus for increasing visual acuity in phakic eyes.
  • [0049]
    The polymeric compositions of the present invention have the flexibility required to allow implants manufactured from the same to be folded or deformed for insertion into an eye through the smallest possible surgical incision, i.e., 3.5 mm or smaller.
  • [0050]
    In general, a method of making an ophthalmic device comprises: (a) providing a polymerizable composition comprising a hydrophilic, aromatic-based monomer of the present invention; and (b) curing the polymerizable composition at a temperature and for a time sufficient to produce the ophthalmic device. The curing can be carried out such that the polymerizable composition is solidified into the final form of the ophthalmic device or such that a solid article is first produced and the ophthalmic device is shaped therefrom.
  • [0051]
    In one embodiment, the method of making an ophthalmic device comprises: (a) providing a polymerizable composition comprising a hydrophilic, aromatic-based monomer; (b) disposing the polymerizable composition in a mold cavity, which forms a shape of the ophthalmic device; and (c) curing the polymerizable composition under a condition and for a time sufficient to form the ophthalmic device; wherein the hydrophilic, aromatic-based monomer has a formula of
  • [0000]

    G-D-Ar  (I)
  • [0000]
    wherein Ar is a C6-C24 aromatic group having at least a hydrophilic substituent, D is a divalent linking group, and G is a reactive functional group.
  • [0052]
    In one embodiment, at least a hydrophilic substituent on the aromatic group is selected from the group consisting of carboxy, carboxamide, alcohol (including monohydric and polyhydric alcohols) substituents, and combinations thereof.
  • [0053]
    In another embodiment, at least a hydrophilic substituent on the aromatic group is selected from the group consisting of —COOH, —CH2—CH2OH, —(CHOH)2—CH2OH, —CH2—CHOH—CH2OH, and combinations thereof.
  • [0054]
    In still another embodiment, at least a hydrophilic substituent on the aromatic group is a poly(alkylene glycol), such as poly(ethylene glycol) having a formula of —(O—CH2—CH2)nOH, wherein n is an integer and 1≦n≦100, preferably 1≦n≦50, and more preferably, 1≦n≦20.
  • [0055]
    In a further embodiment, said hydrophilic substituent is selected from the group consisting of carboxamide, dialkyl-substituted carboxamide, amino, alkanolamino, sulfonate, phosphonate, sulfate, phosphate, ureido, substituted sugars, and combinations thereof.
  • [0056]
    In yet another embodiment, the polymerizable composition also comprises a crosslinking agent, or a polymerization initiator, or both. The polymerization initiator is preferably a thermal polymerization initiator. The curing can be carried out at an elevated temperature such as in the range from about ambient temperature to about 120° C. In some embodiments, the curing is carried out at a temperature from slightly higher than ambient temperature to about 1001° C. A time from about 1 minute to about 48 hours is typically adequate for the curing.
  • [0057]
    In another embodiment, the method of making an ophthalmic device comprises: (a) providing polymerizable composition comprising a hydrophilic, aromatic-based monomer; (b) casting the polymerizable composition under a condition and for a time sufficient to form a solid block; and (c) shaping the block into the ophthalmic device; wherein the hydrophilic, aromatic-based monomer has a formula of
  • [0000]

    G-D-Ar  (I)
  • [0000]
    wherein Ar is a C6-C24 aromatic group having at least a hydrophilic substituent, D is a divalent linking group, and G is a reactive functional group.
  • [0058]
    In one embodiment, said at least a hydrophilic substituent is selected from the group consisting of carboxy, alcohols (including monohydric and polyhydric alcohols), and combinations thereof.
  • [0059]
    In another embodiment, at least a hydrophilic substituent on the aromatic group is selected from the group consisting of —COOH, —CH2—CH2OH, —(CHOH)2—CH2OH, —CH2—CHOH—CH2OH, and combinations thereof.
  • [0060]
    In still another embodiment, at least a hydrophilic substituent on the aromatic group is a poly(alkylene glycol), such as poly(ethylene glycol) having a formula of —(O—CH2—CH2)nOH, wherein n is an integer and 1≦n≦100, preferably 1≦n≦50, and more preferably, 1≦n≦20.
  • [0061]
    In a further embodiment, said hydrophilic substituent is selected from the group consisting of carboxamide, dialkyl-substituted carboxamide, amino, alkanolamino, sulfonate, phosphonate, sulfate, phosphate, ureido, substituted sugars, and combinations thereof.
  • [0062]
    In yet another embodiment, the polymerizable composition also comprises a crosslinking agent, or a polymerization initiator, or both. The polymerization initiator is preferably a thermal polymerization initiator. The casting can be carried out at an elevated temperature such as in the range from about 20° C. to about 120° C. In some embodiments, the casting is carried out at a temperature from slightly higher than ambient temperature to about 100° C. A time from about 1 minute to about 48 hours is typically adequate for the polymerization. The shaping can comprise cutting the solid block into wafers, and lathing or machining the wafers into the shape of the final ophthalmic device.
  • [0063]
    Ophthalmic medical devices manufactured using polymeric compositions of the present invention are used as customary in the field of opthalmology. For example, in a surgical cataract procedure, an incision is placed in the cornea of an eye. Through the corneal incision the cataractous natural lens of the eye is removed (aphakic application) and an IOL is inserted into the anterior chamber, posterior chamber or lens capsule of the eye prior to closing the incision. However, the subject ophthalmic devices may likewise be used in accordance with other surgical procedures known to those skilled in the field of opthalmology.
  • [0064]
    While specific embodiments of the present invention have been described in the foregoing, it will be appreciated by those skilled in the art that many equivalents, modifications, substitutions, and variations may be made thereto without departing from the spirit and scope of the invention as defined in the appended claims.

Claims (11)

1. A compound having a formula of

G-D-Ar  (I)
wherein Ar is a C6-C24 aromatic group having a hydrophilic substituent selected from the group consisting of —COOH, —CH2—CH2OH, —(CHOH)2—CH2OH, —CH2—CHOH—CH2OH, —C(O)O—NH2, —C(O)—N(CH3)2, poly(alkyleneglycol) and combinations thereof, D is a divalent linking group, and G is a reactive functional group.
2. The compound of claim 1, wherein the hydrophilic substituent is selected from the group consisting of —COOH, —CH2—CH2OH, and combinations thereof.
3. The compound of claim 1, wherein the hydrophilic substituent is poly(alkylene glycol).
4. The compound of claim 6, wherein said poly(alkylene glycol) is poly(ethylene glycol) having a formula of —(O—CH2—CH2)nOH, wherein n is an integer and 1≦n≦50.
5. A compound having a formula of

G-D-Ar  (I)
wherein Ar is a C6-C24 aromatic group having a hydrophilic substituent selected from the group consisting of carboxamide, dialkyl-substituted carboxamide, amino, alkanolamino, sulfonate, phosphonate, sulfate, phosphate, ureido, substituted sugars, and combinations thereof, D is a divalent linking group, and G is a reactive functional group.
6. The compound of claim 1, wherein G is selected from the group consisting of vinyl, allyl, acryloyl, acryloyloxy, methacryloyl, methacryloyloxy, epoxide, isocyanate, isothiocyanate, amino, hydroxyl, mercapto, anhydride, carboxylic, fumaryl, styryl, and combinations thereof.
7. The compound of claim 1, wherein D is selected from the group consisting of saturated straight C1-C10 hydrocarbons, unsaturated straight C1-C10 hydrocarbons, saturated branched C3-C10 hydrocarbons, unsaturated branched C3-C10 hydrocarbons, saturated cyclic C3-C10 hydrocarbons, unsaturated cyclic C3-C10 hydrocarbons, and alkyloxy substituents.
8. The compound of claim 1, wherein the compound has a formula of
wherein R is hydrogen or CH3; D is a divalent group selected from the group consisting of saturated straight C1-C10 hydrocarbons, unsaturated straight C1-C10 hydrocarbons, saturated branched C3-C10 hydrocarbons, unsaturated branched C3-C10 hydrocarbons, saturated cyclic C3-C10 hydrocarbons, unsaturated cyclic C3-C10 hydrocarbons, and alkoxy substituents; E is selected from the group consisting of carboxy, carboxamide, and monohydric and polyhydric alcohol substituents; and m is an integer from 1 to, and including, 5.
9. The compound of claim 1, wherein the compound is
wherein R is hydrogen or CH3.
10. The compound of claim 1, wherein the compound is
wherein R is hydrogen or CH3.
11. The compound of claim 1, wherein the hydrophilic, aromatic-based monomer has a formula of
wherein R is hydrogen or CH3, and R1 is —C(O)O—NH2 or —C(O)—N(CH3)2.
US12060322 2005-05-27 2008-04-01 High Refractive-Index, Hydrophilic Monomers and Polymers, and Ophthalmic Devices Comprising Such Polymers Abandoned US20080183006A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US11139276 US7495061B2 (en) 2005-05-27 2005-05-27 High refractive-index, hydrophilic monomers and polymers, and ophthalmic devices comprising such polymers
US12060322 US20080183006A1 (en) 2005-05-27 2008-04-01 High Refractive-Index, Hydrophilic Monomers and Polymers, and Ophthalmic Devices Comprising Such Polymers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12060322 US20080183006A1 (en) 2005-05-27 2008-04-01 High Refractive-Index, Hydrophilic Monomers and Polymers, and Ophthalmic Devices Comprising Such Polymers
US12273624 US7781496B2 (en) 2005-05-27 2008-11-19 High refractive-index, hydrophilic monomers and polymers, and ophthalmic devices comprising such polymers

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US11139276 Division US7495061B2 (en) 2005-05-27 2005-05-27 High refractive-index, hydrophilic monomers and polymers, and ophthalmic devices comprising such polymers

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12273624 Continuation US7781496B2 (en) 2005-05-27 2008-11-19 High refractive-index, hydrophilic monomers and polymers, and ophthalmic devices comprising such polymers

Publications (1)

Publication Number Publication Date
US20080183006A1 true true US20080183006A1 (en) 2008-07-31

Family

ID=37331447

Family Applications (3)

Application Number Title Priority Date Filing Date
US11139276 Active 2026-12-11 US7495061B2 (en) 2005-05-27 2005-05-27 High refractive-index, hydrophilic monomers and polymers, and ophthalmic devices comprising such polymers
US12060322 Abandoned US20080183006A1 (en) 2005-05-27 2008-04-01 High Refractive-Index, Hydrophilic Monomers and Polymers, and Ophthalmic Devices Comprising Such Polymers
US12273624 Active 2025-10-17 US7781496B2 (en) 2005-05-27 2008-11-19 High refractive-index, hydrophilic monomers and polymers, and ophthalmic devices comprising such polymers

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US11139276 Active 2026-12-11 US7495061B2 (en) 2005-05-27 2005-05-27 High refractive-index, hydrophilic monomers and polymers, and ophthalmic devices comprising such polymers

Family Applications After (1)

Application Number Title Priority Date Filing Date
US12273624 Active 2025-10-17 US7781496B2 (en) 2005-05-27 2008-11-19 High refractive-index, hydrophilic monomers and polymers, and ophthalmic devices comprising such polymers

Country Status (3)

Country Link
US (3) US7495061B2 (en)
EP (1) EP1885290A2 (en)
WO (1) WO2006130402A3 (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080228186A1 (en) 2005-04-01 2008-09-18 The Regents Of The University Of Colorado Graft Fixation Device
US7495061B2 (en) * 2005-05-27 2009-02-24 Bausch + Lomb Incorporated High refractive-index, hydrophilic monomers and polymers, and ophthalmic devices comprising such polymers
WO2009070438A1 (en) 2007-11-30 2009-06-04 Bausch & Lomb Incorporated Optical material and method for modifying the refractive index
EP2139931B1 (en) 2007-04-30 2011-01-19 Alcon, Inc. Ophthalmic and otorhinolaryngological device materials containing phenylene-siloxane macromers
WO2009015256A3 (en) * 2007-07-25 2009-03-12 Alcon Inc High refractive index ophthalmic device materials
RU2010116897A (en) 2007-10-02 2011-11-10 Алькон, Инк. (Ch) Materials for ophthalmic and ENT devices containing alkyl phenol
ES2362817T3 (en) 2007-10-02 2011-07-13 Alcon, Inc. Ophthalmic device materials containing otorhinolaryngological alkyl ethoxylate.
EP2192934B1 (en) 2007-10-03 2011-05-04 Alcon, Inc. Ophthalmic and otorhinolaryngological device materials
EP2192933B1 (en) 2007-10-05 2011-05-25 Alcon, Inc. Ophthalmic and otorhinolaryngological device materials
US7888403B2 (en) 2007-10-05 2011-02-15 Alcon, Inc. Ophthalmic and otorhinolaryngological device materials
CN105726166B (en) * 2011-03-07 2017-10-27 科罗拉多州立大学董事会 IOL shape memory polymer
US9427493B2 (en) 2011-03-07 2016-08-30 The Regents Of The University Of Colorado Shape memory polymer intraocular lenses
US8912300B2 (en) * 2011-06-13 2014-12-16 Dic Corporation Radical polymerizable composition, cured product, and plastic lens

Citations (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4304895A (en) * 1973-06-20 1981-12-08 Wesley-Jessen, Inc. Ultraviolet absorbing corneal contact lenses
US4528311A (en) * 1983-07-11 1985-07-09 Iolab Corporation Ultraviolet absorbing polymers comprising 2-hydroxy-5-acrylyloxyphenyl-2H-benzotriazoles
US5674960A (en) * 1990-11-07 1997-10-07 Nestle S.A. Flexible high refractive index, cross-linked, acrylic copolymers
US5693095A (en) * 1995-06-07 1997-12-02 Alcon Laboratories, Inc. High refractive index ophthalmic lens materials
US5891931A (en) * 1997-08-07 1999-04-06 Alcon Laboratories, Inc. Method of preparing foldable high refractive index acrylic ophthalmic device materials
US5922821A (en) * 1996-08-09 1999-07-13 Alcon Laboratories, Inc. Ophthalmic lens polymers
US6015842A (en) * 1997-08-07 2000-01-18 Alcon Laboratories, Inc. Method of preparing foldable hydrophilic ophthalmic device materials
US6313187B2 (en) * 1998-04-15 2001-11-06 Alcon Manufacturing, Ltd. High refractive index ophthalmic device materials prepared using a post-polymerization cross-linking method
US6353069B1 (en) * 1998-04-15 2002-03-05 Alcon Manufacturing, Ltd. High refractive index ophthalmic device materials
US6541572B2 (en) * 1998-04-23 2003-04-01 Alcon Manufacturing, Ltd. Method of making high refractive index ophthalmic device materials
US6632905B2 (en) * 1999-09-02 2003-10-14 Alcon Universal Ltd. Covalently-bound, hydrophilic coating compositions for surgical implants
US6635732B2 (en) * 1999-04-12 2003-10-21 Surgidev Corporation Water plasticized high refractive index polymer for ophthalmic applications
US6673886B2 (en) * 1998-12-11 2004-01-06 Bausch & Lomb Incorporated High refractive index hydrogel compositions for ophthalmic implants
US6689853B2 (en) * 1998-07-10 2004-02-10 Johnson Polymer, Llc Process for producing polymers by free radical polymerization and condensation reaction, and products related thereto
US6695880B1 (en) * 2000-10-24 2004-02-24 Johnson & Johnson Vision Care, Inc. Intraocular lenses and methods for their manufacture
US6703466B1 (en) * 2001-06-18 2004-03-09 Alcon, Inc. Foldable intraocular lens optics having a glassy surface
US6723815B2 (en) * 1999-09-02 2004-04-20 Alcon, Inc. Covalently-bound, hydrophilic coating compositions for surgical implants
US6737448B2 (en) * 2002-06-03 2004-05-18 Staar Surgical Company High refractive index, optically clear and soft hydrophobic acrylamide copolymers
US6767934B1 (en) * 1999-03-16 2004-07-27 Pharmacia Groningen Bv Macromolecular compounds
US6767979B1 (en) * 1998-12-11 2004-07-27 Biocompatibles Uk Limited Crosslinked polymers and refractive devices formed therefrom
US6776932B1 (en) * 1998-06-12 2004-08-17 Getronics Wang Co. Llc Polymeric optical articles
US6852793B2 (en) * 2002-06-19 2005-02-08 Bausch & Lomb Incorporated Low water content, high refractive index, flexible, polymeric compositions
US6852820B2 (en) * 1999-03-09 2005-02-08 Nidek Co., Ltd. Method for preparing acrylic copolymer materials suitable for ophthalmic devices
US20090076187A1 (en) * 2005-05-27 2009-03-19 Salamone Joseph C High Refractive-Index, Hydrophilic Monomers and Polymers, and Ophthalmic Devices Comprising Such Polymers

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3737979A (en) * 1971-08-05 1973-06-12 Anaconda American Brass Co Method of manufacturing longitudinally welded strips of different thicknesses and widths
US5236969A (en) * 1987-04-02 1993-08-17 Bausch & Lomb Incorporated Polymer compositions for contact lenses
JP3648846B2 (en) 1995-07-25 2005-05-18 ユニマテック株式会社 Acrylic copolymer elastomer, the blend rubber and rubber blend compositions
JPH09165422A (en) 1995-12-15 1997-06-24 Mitsubishi Rayon Co Ltd Composition for plastic lens
WO1997024382A1 (en) * 1996-01-02 1997-07-10 Pharmacia & Upjohn Ab Foldable intraocular lens materials
BE1011539A3 (en) * 1997-11-07 1999-10-05 Solvay Method of manufacturing organic compound.
DK1071482T3 (en) 1998-04-15 2001-12-27 Alcon Lab Inc intraocular linsecoatingsammensætninger
ES2243053T3 (en) 1998-04-15 2005-11-16 Alcon Manufacturing Ltd. Materials index ophthalmic device high refractive prepared using a method of crosslinking after polymerization.
DE69941084D1 (en) 1998-04-15 2009-08-20 Alcon Inc Material with a high refractive index ophthalmic device
WO2006095750A1 (en) * 2005-03-09 2006-09-14 Hoya Corporation (meth)acrylate compound, process for production of the compound, (meth)acrylate copolymer, process for production of the copolymer, and soft intraocular lens
US7714039B2 (en) * 2006-07-21 2010-05-11 Alcon, Inc. Low-tack ophthalmic and otorhinolaryngological device materials

Patent Citations (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4304895A (en) * 1973-06-20 1981-12-08 Wesley-Jessen, Inc. Ultraviolet absorbing corneal contact lenses
US4528311A (en) * 1983-07-11 1985-07-09 Iolab Corporation Ultraviolet absorbing polymers comprising 2-hydroxy-5-acrylyloxyphenyl-2H-benzotriazoles
US5674960A (en) * 1990-11-07 1997-10-07 Nestle S.A. Flexible high refractive index, cross-linked, acrylic copolymers
US5861031A (en) * 1990-11-07 1999-01-19 Nestle, S.A. Intraocular lens from arylalkyl(meth)acrylate polymer(s)
US5693095A (en) * 1995-06-07 1997-12-02 Alcon Laboratories, Inc. High refractive index ophthalmic lens materials
US5922821A (en) * 1996-08-09 1999-07-13 Alcon Laboratories, Inc. Ophthalmic lens polymers
US5891931A (en) * 1997-08-07 1999-04-06 Alcon Laboratories, Inc. Method of preparing foldable high refractive index acrylic ophthalmic device materials
US6015842A (en) * 1997-08-07 2000-01-18 Alcon Laboratories, Inc. Method of preparing foldable hydrophilic ophthalmic device materials
US6313187B2 (en) * 1998-04-15 2001-11-06 Alcon Manufacturing, Ltd. High refractive index ophthalmic device materials prepared using a post-polymerization cross-linking method
US6353069B1 (en) * 1998-04-15 2002-03-05 Alcon Manufacturing, Ltd. High refractive index ophthalmic device materials
US6541572B2 (en) * 1998-04-23 2003-04-01 Alcon Manufacturing, Ltd. Method of making high refractive index ophthalmic device materials
US6776932B1 (en) * 1998-06-12 2004-08-17 Getronics Wang Co. Llc Polymeric optical articles
US6689853B2 (en) * 1998-07-10 2004-02-10 Johnson Polymer, Llc Process for producing polymers by free radical polymerization and condensation reaction, and products related thereto
US6767979B1 (en) * 1998-12-11 2004-07-27 Biocompatibles Uk Limited Crosslinked polymers and refractive devices formed therefrom
US6673886B2 (en) * 1998-12-11 2004-01-06 Bausch & Lomb Incorporated High refractive index hydrogel compositions for ophthalmic implants
US6852820B2 (en) * 1999-03-09 2005-02-08 Nidek Co., Ltd. Method for preparing acrylic copolymer materials suitable for ophthalmic devices
US6767934B1 (en) * 1999-03-16 2004-07-27 Pharmacia Groningen Bv Macromolecular compounds
US6635732B2 (en) * 1999-04-12 2003-10-21 Surgidev Corporation Water plasticized high refractive index polymer for ophthalmic applications
US6723815B2 (en) * 1999-09-02 2004-04-20 Alcon, Inc. Covalently-bound, hydrophilic coating compositions for surgical implants
US6632905B2 (en) * 1999-09-02 2003-10-14 Alcon Universal Ltd. Covalently-bound, hydrophilic coating compositions for surgical implants
US6695880B1 (en) * 2000-10-24 2004-02-24 Johnson & Johnson Vision Care, Inc. Intraocular lenses and methods for their manufacture
US6703466B1 (en) * 2001-06-18 2004-03-09 Alcon, Inc. Foldable intraocular lens optics having a glassy surface
US6737448B2 (en) * 2002-06-03 2004-05-18 Staar Surgical Company High refractive index, optically clear and soft hydrophobic acrylamide copolymers
US6852793B2 (en) * 2002-06-19 2005-02-08 Bausch & Lomb Incorporated Low water content, high refractive index, flexible, polymeric compositions
US20090076187A1 (en) * 2005-05-27 2009-03-19 Salamone Joseph C High Refractive-Index, Hydrophilic Monomers and Polymers, and Ophthalmic Devices Comprising Such Polymers

Also Published As

Publication number Publication date Type
US7495061B2 (en) 2009-02-24 grant
EP1885290A2 (en) 2008-02-13 application
US7781496B2 (en) 2010-08-24 grant
WO2006130402A2 (en) 2006-12-07 application
WO2006130402A3 (en) 2007-03-08 application
US20060270749A1 (en) 2006-11-30 application
US20090076187A1 (en) 2009-03-19 application

Similar Documents

Publication Publication Date Title
US6638991B2 (en) Material for ocular lens
US5539016A (en) Fluorosilicone hydrogels
US5484863A (en) Polymeric ophthalmic lens prepared from unsaturated polyoxyethylene monomers
US5981675A (en) Silicone-containing macromonomers and low water materials
US20030109637A1 (en) Contact lens material
US6245106B1 (en) Intraocular lenses made from polymeric compositions and monomers useful in said compositions
US4182822A (en) Hydrophilic, soft and oxygen permeable copolymer composition
US6533415B2 (en) Ocular lens material having hydrophilic surface and process for preparing the same
US20070092831A1 (en) Radiation-absorbing polymeric materials and ophthalmic devices comprising same
US6277940B1 (en) Material for a soft intraocular lens
US6635732B2 (en) Water plasticized high refractive index polymer for ophthalmic applications
US6653422B2 (en) Foldable ophthalmic and otorhinolaryngological device materials
US4985559A (en) UV Absorbing vinyl monomers
US5693095A (en) High refractive index ophthalmic lens materials
US20060106458A1 (en) Biomedical compositions
US6018001A (en) Process for producing contact lens with hydrophilic surface and contact lens obtained thereby
US6313187B2 (en) High refractive index ophthalmic device materials prepared using a post-polymerization cross-linking method
US7033391B2 (en) High refractive index silicone-containing prepolymers with blue light absorption capability
US20060252850A1 (en) Radiation-absorbing polymeric materials and ophthalmic devices comprising same
US20070092830A1 (en) Polymeric radiation-absorbing materials and ophthalmic devices comprising same
US20060036022A1 (en) Covalently-bound, hydrophilic coating compositions for surgical implants
US6727336B1 (en) Ocular lens materials and process for producing the same
US20050055090A1 (en) Process for manufacturing intraocular lenses with blue light absorption characteristics
WO2001071392A1 (en) Crosslinkable or polymerizable prepolymers
US6036891A (en) Polymerizable hydrophilic ultraviolet light absorbing monomers