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WO1992018548A1 - Nouvelle composition pour lentilles de contact - Google Patents

Nouvelle composition pour lentilles de contact Download PDF

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Publication number
WO1992018548A1
WO1992018548A1 PCT/US1992/003128 US9203128W WO9218548A1 WO 1992018548 A1 WO1992018548 A1 WO 1992018548A1 US 9203128 W US9203128 W US 9203128W WO 9218548 A1 WO9218548 A1 WO 9218548A1
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WO
WIPO (PCT)
Prior art keywords
percent
weight
group
hydrogel
copolymer according
Prior art date
Application number
PCT/US1992/003128
Other languages
English (en)
Inventor
Richard Y. S. Chen
Original Assignee
Optical Research, Inc.
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 Optical Research, Inc. filed Critical Optical Research, Inc.
Publication of WO1992018548A1 publication Critical patent/WO1992018548A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers 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
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G02B1/043—Contact lenses

Definitions

  • This invention relates to contact lenses, and in particular to pliable or "soft" contact lens having an exceptional combination of oxygen permeability, strength, and resistance to protein and mucus deposits.
  • pliable or "soft" contact lens having an exceptional combination of oxygen permeability, strength, and resistance to protein and mucus deposits.
  • U.S. Patent No. 4,130,706 to Plambeck, Jr. proposes a methacrylate-type fluoropolymer ("FMA") for making contact lenses. While the lenses are described as hydrophilic and oxygen permeable, it is believed that they are not wettable enough to be truly comfortable to persons wearing the lenses and are not sufficiently permeable to oxygen to be worn safely and continuously for extended periods.
  • FMA methacrylate-type fluoropolymer
  • U.S. Patent No. 3,940,207 to Barkdoll proposes contact lenses constructed of fluorine- containing polymers that are soft and have a low refractive index. It is believed that these contact lenses are not sufficiently oxygen permeable to be worn safely for extended periods.
  • DMA N,N-dimethylacrylamide
  • hydrogel copolymer which can be used to form an easily fabricated pliable contact lens having the combination of oxygen permeability, wettability and resistance to protein and mucus deposits.
  • the present invention relates to a hydrogel copolymer for making contact lenses, the copolymer comprising, by weight, about 10 percent to about 85 percent of ⁇ -methylene-N-methylpyrrolidone or glycerdyl methacrylate and mixtures thereof, from about 5 to about 25 percent of N,N-dimethylacrylamide, about 5 percent to about 80 percent of a polymerizable fluoromonomer, and about 1 percent to about 15 percent of a polymerizable hydrophophic , non-hydrolyzable silicone monomer.
  • an initiator and a crosslinker are employed under circumstances disclosed below.
  • the copolymer comprises, by weight, from about 10 to 85 percent ⁇ -methylene-N-methylpyrrolidone, from about 5 to about 85 percent of glycerdyl methacrylate, from about 5 to about 60 percent of a polymerizable fluoromonomer, and from about 1 to about 15 percent of a polymerizable hydrophobic non-hydrolyzable silicone monomer.
  • the copolymer comprises, by weight, from about 40 to about 90 percent of ⁇ -methylene-N-methylpyrrolidone and from about 10 to about 60 percent of a polymerizable fluoromonomer such as fluoroacyrlates, styryl fluoro onomers and vinyl fluoromonomers.
  • a polymerizable fluoromonomer such as fluoroacyrlates, styryl fluoro onomers and vinyl fluoromonomers.
  • the present invention utilizes in various combinations, as described below ⁇ -methylene-N- methylpyrrolidone ("Q.-MMP") or glycerdyl methacrylate (“GMA”) and mixtures thereof, N,N-dimethyl methacrylamide, a polymerizable fluoromonomer, a polymerizable hydrophobic, non-hydrolyzable silicone monomer, an initiator, and a crosslinker.
  • Q.-MMP ⁇ -methylene-N- methylpyrrolidone
  • GMA glycerdyl methacrylate
  • the hydrogel copolymer comprises, by weight, from about 5 to about 85 percent of ⁇ - methylene-N-methylpyrrolidone or glycerdyl methacrylate and mixtures thereof, from about 10 to about 25 percent, and preferably from about 5 to about 20 percent of N,N-dimethylacrylamide, from about 5 to about 85 percent, and preferably from about 20 to about 40 percent by weight of a polymerizable fluoromonomer and from about 1 to about 15 percent, and preferably from about 2 to about 4 percent of a polymerizable hydrophobic non-hydrolyzable silicone monomer.
  • ⁇ -methylene-N-methylpyrrolidone Preferably, from about 20 to about 30 percent of ⁇ - methylene-N-methylpyrrolidone or from about 5 to about 30 percent of glycerdyl methacrylate is used. If a mixture of ⁇ -methylene-N-pyrrolidone and glyceridyl methacrylate is used, preferably from about 10 to about 85 percent of ⁇ -methylene-N-pyrrolidone and from about 5 to about 85 percent of glycerdyl methacrylate are used.
  • from about 50 to about 90 percent of ⁇ -methylene-N- pyrrolidone can be blended with from about 10 to about 50 percent of a polymerizable fluoromonomer to form the hydrogel copolymer.
  • the hydrogel copolymer can further include, by weight, from about 10 to about 25 percent of a polymerizable hydrophilic monomer selected from the group consisting of methacrylic acid (“MA”), 2-hydroxyethylmethacrylate (“HEMA”), N-vinyl-2-pyrrolidone (“NVP”) and N,N- ⁇ dimethylacrylamide (“DMA”) .
  • MA methacrylic acid
  • HEMA 2-hydroxyethylmethacrylate
  • NDP N-vinyl-2-pyrrolidone
  • DMA N,N- ⁇ dimethylacrylamide
  • the polymerizable fluoromonomer useful herein can vary.
  • An exemplary fluoromonomer is one based on a fluoroacrylate composition which includes the following fluorine-containing monomer:
  • R is H or CH 3
  • m is an integer from 0 to 9
  • n is an integer from 1 to 4.
  • Another exemplary fluoromonomer can be a fluoracrylate
  • a particularly preferred composition is 2,2,2-trifluoroethyl methacrylate (“FMA”) .
  • styryl fluoromonomer is pentafluorostyrene.
  • fluoromonomers are p-vinyl benzyl trifluoroacetate and p-vinyl benzyl hexafluoroisopropyl ether.
  • vinyl fluoromonomers can be used. They have the general formula
  • a particularly preferred vinyl fluoromonomer is 3 , 3 , 3 trifluorovinylpropane
  • R - H or CH 3 A particularly preferred pefluorocyclohexyl acrylate is perfluorocyclopentene. It is noted that only ⁇ -methylene-N-methylpyrrolidone and the polymerizable fluoromonomer can be used.
  • the polymerizable hydrophobic non- hydrolyzable silicone monomer useful herein can vary.
  • An exemplary silicone has the formula
  • A is selected from the group consisting of CPJ-CJ alkyl groups and phenyl groups
  • R is selected from the group consisting of a methyl group (CH 3 ) and hydrogen
  • X and Y are selected from the group consisting of C, to C 5 alkyl groups, phenyl groups and Z groups wherein Z is a group of the structure
  • alkanol ester co-monomers where a and A are as defined previously, and ⁇ is a phenyl group.
  • the alkyl group contains from 1 to 20 carbon atoms.
  • Exemplary silicon-containing monomers are disclosed in U.S. Patent Nos. 3,808,178 and 4,120,570 to Gaylord, the disclosures of which are incorporated herein by reference.
  • vinyl silicone monomers can be employed.
  • the general formula can be represented as
  • R 1 is selected from the class consisting of C, to C 6 alkyl groups and phenyl groups or a mixture of alkyl and phenyl groups.
  • Class (I) are particularly preferred.
  • any methyl group (CH 3 group) can be replaced by a benzene ring, as the preceding examples suggest.
  • vinyl silicone monomers are less reactive than acrylate silicone monomers.
  • cobalt-60 (“Co-60")
  • radiation may be used as a source of polymerization energy.
  • Co-60 may optionally be used as a source of polymerization energy even when vinyl silicone monomers are not employed.
  • non-hydrolyzable silicones include methyldi(trimethylsiloxy)silylpropylglycerol methacrylate, methylidi(trimethylsiloxy)silylpropyl- glycerolethyl methacrylate, m,p-styrlethyltrimethyl- silane, m,p-styrylethyltris(trimethylisiloxy)silane, methylacryloxypropyltris(trimethylsiloxy)silane and 4- (3-trimethylsilylpropyl)benzylstyrene sulfonate.
  • a crosslinker is used.
  • the crosslinker can constitute, by weight, about 0.01 percent to about 5 percent and more preferably about 0.5 percent to about 2 percent of the weight of the hydrogel copolymer.
  • the crosslinker is preferably one of a mixture of ethyleneglycoldimethacrylate (“EGDMA”) , a fluorine-containing compound, or a silicon-containing compound such as l,3-bis[(p-acryloxymethyl) phenethyl]tetramethyldisiloxane or bis(3- methacryloxypropyl)tetramethyldisiloxane.
  • a quantity of an initiator equal in weight to 0.05 percent to 2 about percent of the weight of the mixture of monomers is preferably added thereto, except when Co-60 is used as a source of polymerization energy.
  • the initiator may be selected from the group consisting essentially of 2,2•-azobis(2,4- di ethylvaleronitrile) ("VAZO 52"), azobisisobutyro- nitrile (“AIBN”), benzoinmethylether (“BME”) , di(sec- butyl)peroxydicarbonate (“SBC”), and isopropylperoxydicarbonate (“Ipp”) •
  • VAZO 52 2,2•-azobis(2,4- di ethylvaleronitrile)
  • AIBN azobisisobutyro- nitrile
  • BME benzoinmethylether
  • SBC sec- butyl)peroxydicarbonate
  • Ipp isopropylperoxydicarbonate
  • the initiator may also be
  • VAZO 52 or AIBN may be used as an initiator when polymerization is aided by ultraviolet or thermal radiation
  • BME may be used as the initiator when polymerization is aided by the ultraviolet radiation
  • SBC or Ipp may be used as the initiator when polymerization is aided by thermal radiation.
  • Co-60 or another radioactive source may also be used to promote polymerization, particularly when vinyl silicone monomers or other monomers that are not highly reactive are employed.
  • Co-60 or another radioactive source is not used, polymerization energy is supplied in the form of thermal energy or in the form of ultraviolet radiation, as may be appropriate in view of the initiator employed. When Co-60 radiation is employed, no initiators are needed.
  • the resulting polymer is formed in any conventional or otherwise suitable process into contact lenses.
  • the lenses have a shore hardness (D scale) within the range of 82 to 89.
  • Oxygen permeability in DK units (ml cm/cm 2 sec cmHg X 10 "10 ) at 35*C is within the range of 20 to 55.
  • the contact angle is within the range of 10 • -34*, light 5 transmission is greater than 95%, refractive index is close to that of HEMA, and the coefficient of expansion is within the range of 1.1 to 1.6.
  • the initiator is added to the mixture, and the mixture is poured into a test tube and polymerized by thermal polymerization (i.e., application of heat)
  • the polymerized material is a colorless, solid, transparent polymer.
  • the polymer is lathe-cut into buttons of conventional shape and size.
  • the buttons are ground to the shape of contact lenses having respective center thicknesses of 0.1mm to 0.2mm, and then polished.
  • the lenses are highly transparent (light transmission is greater than 95%) and have uniform optical properties. They have an oxygen permeability of 35 DK units at 35*C (normal eye temperature) , a contact angle of less than 18", and a refractive index of 1.405.
  • Example 1 The following examples are similar to Example 1 but illustrate variations of the materials and quantities thereof employed and of the method of polymerization.
  • Example 2 The shells are lathe-cut to form contact lenses in accordance therewith.
  • the mixture is molded in the form of shells and polymerized by UV polymerization in accordance with Example 2.
  • the shells are lathe-cut to form contact lenses in accordance therewith.
  • EGDMA VAZO-52 The mixture is molded in the form of shells and polymerized by thermal polymerization in accordance with Example 1.
  • the shells are lathe-cut to form contact lenses in accordance therewith.
  • the lenses are highly transparent (light transmission is greater than 95%) and have uniform optical properties. They have an oxygen permeability of 46.7 DK units at 35"C (normal eye temperature) , an expansion factor of 1.39, and a water content of about 54 percent.
  • VAZO-52 0.02 The mixture is molded in the form ' of shells and polymerized by UV polmerization in accordance with
  • Example 2 The shells are lathe-cut to form contact lenses in accordance therewith.
  • the lenses are highly transparent (light transmission is greater than 95%) and have uniform optical properties. They have an oxygen permeability of 47.4 DK units at 35"C, an expansion factor of 1.4, and a water content of about 65 percent.
  • the mixture is molded in the form of shells and polymerized by UV polymerization in accordance with Example 2.
  • the shells are lathe-cut to form contact lenses in accordance therewith.
  • the lenses are highly transparent (light transmission is greater than 95%) and have uniform optical properties. They have an oxygen permeability of 25 DK units at 35*C, an expansion factor of 1.32, and a water content of about 54.4 percent.
  • the mixture is molded in the form of shells and polymerized by UV polymerization in accordance with Example 2.
  • the shells are lathe-cut to form contact lenses in accordance therewith.
  • the lenses are highly transparent (light transmission is greater than 95%) and have uniform optical properties. They have an oxygen permeability of 62.7 DK units at 35°C, an expansion factor of 1.69, and a water content of 77.3 percent.
  • Example 9
  • VAZO-52 0.02 The mixture is molded in the form of shells and polymerized by UV polymerization in accordance with
  • Example 2 The shells are lathe-cut to form contact lenses in accordance therewith.
  • the lenses are highly transparent (light transmission is greater than 95%) and have uniform optical properties. They have an oxygen permeability of 45.5 DK units at 35*C, an expansion factor of 1.38, and a water content of 62.5 percent.
  • a novel and highly-effective contact lens that has an exceptional combination of oxygen permeability, wettability and resistance to protein and mucus deposits.
  • a novel material for manufacturing the lens is also provided, and it is noted that the material may be used for other medical articles needing the combination of oxygen permeability, wettability and resistance to protein and mucus deposits.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Eyeglasses (AREA)

Abstract

Un copolymère d'hydrogel permettant la production de lentilles de contact comprend, exprimé en poids, environ 5 à environ 85 pour cent de α-méthylène-N-méthylpyrrolidone ou de glycerdyle méthacrylate ainsi que des mélanges de ceux-ci, environ 5 à environ 35 pour cent de N,N-diméthylacrylamide, environ 5 à environ 60 pour cent d'un fluoromonomère polymérisable, et environ 1 à environ 15 pour cent d'un monomère de silicone polymérisable hydrophobe non hydrolysable. On utilise aussi habituellement de préférence une amorce et un agent de réticulation.
PCT/US1992/003128 1991-04-18 1992-04-16 Nouvelle composition pour lentilles de contact WO1992018548A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US68738591A 1991-04-18 1991-04-18
US687,385 1991-04-18
US78613091A 1991-10-31 1991-10-31
US786,130 1991-10-31

Publications (1)

Publication Number Publication Date
WO1992018548A1 true WO1992018548A1 (fr) 1992-10-29

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5741830A (en) * 1995-02-15 1998-04-21 Menicon Co., Ltd. Water-absorptive soft contact lens
WO2001071392A1 (fr) * 2000-03-24 2001-09-27 Novartis Ag Nouveaux polymeres
WO2003022321A3 (fr) * 2001-09-10 2003-07-10 Johnson & Johnson Vision Care Dispositifs biomedicaux contenant des agents humidifiants internes
US6822016B2 (en) 2001-09-10 2004-11-23 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US7461937B2 (en) 2001-09-10 2008-12-09 Johnson & Johnson Vision Care, Inc. Soft contact lenses displaying superior on-eye comfort
US8044111B2 (en) 2007-11-30 2011-10-25 Novartis Ag Actinically-crosslinkable silicone-containing block copolymers
US8071658B2 (en) 2007-03-22 2011-12-06 Novartis Ag Prepolymers with dangling polysiloxane-containing polymer chains
US8071703B2 (en) 2007-03-22 2011-12-06 Novartis Ag Silicone-containing prepolymers with dangling hydrophilic polymer chains
US8506856B2 (en) 2007-12-10 2013-08-13 Novartis Ag Method for making silicone hydrogel contact lenses
US8524800B2 (en) 2006-12-13 2013-09-03 Novartis Ag Actinically curable silicone hydrogel copolymers and uses thereof
US8557940B2 (en) 2010-07-30 2013-10-15 Novartis Ag Amphiphilic polysiloxane prepolymers and uses thereof
US8993651B2 (en) 2010-10-06 2015-03-31 Novartis Ag Polymerizable chain-extended polysiloxanes with pendant hydrophilic groups

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2256932A1 (en) * 1973-07-10 1975-08-01 Union Optics Corp Unsatd heterocyclic copolymers - form hydrogels suitable for contact lens
US4182822A (en) * 1976-11-08 1980-01-08 Chang Sing Hsiung Hydrophilic, soft and oxygen permeable copolymer composition
GB2152064A (en) * 1983-12-27 1985-07-31 Toyo Contact Lens Co Ltd Water-absorptive contact lenses
EP0253515A2 (fr) * 1986-07-18 1988-01-20 Optimers Inc. Lentille de contact souple à base d'un hydrogel fluoré
EP0295947A2 (fr) * 1987-06-18 1988-12-21 Ocular Technologies Inc. Lentille de contact perméable au gaz et procédé et matériaux pour sa préparation
WO1991004283A1 (fr) * 1989-09-14 1991-04-04 Chang Sing Hsiung Lentille de contact souple permeable au gaz presentant des performances cliniques ameliorees

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2256932A1 (en) * 1973-07-10 1975-08-01 Union Optics Corp Unsatd heterocyclic copolymers - form hydrogels suitable for contact lens
US4182822A (en) * 1976-11-08 1980-01-08 Chang Sing Hsiung Hydrophilic, soft and oxygen permeable copolymer composition
GB2152064A (en) * 1983-12-27 1985-07-31 Toyo Contact Lens Co Ltd Water-absorptive contact lenses
EP0253515A2 (fr) * 1986-07-18 1988-01-20 Optimers Inc. Lentille de contact souple à base d'un hydrogel fluoré
EP0295947A2 (fr) * 1987-06-18 1988-12-21 Ocular Technologies Inc. Lentille de contact perméable au gaz et procédé et matériaux pour sa préparation
WO1991004283A1 (fr) * 1989-09-14 1991-04-04 Chang Sing Hsiung Lentille de contact souple permeable au gaz presentant des performances cliniques ameliorees

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5741830A (en) * 1995-02-15 1998-04-21 Menicon Co., Ltd. Water-absorptive soft contact lens
US7091283B2 (en) 2000-03-24 2006-08-15 Novartis Ag Crosslinkable prepolymers from a hydrophilic monomer and a hydrophobic crosslinker
WO2001071392A1 (fr) * 2000-03-24 2001-09-27 Novartis Ag Nouveaux polymeres
US7566754B2 (en) 2000-03-24 2009-07-28 Novartis Ag Process for making contact lenses from prepolymers
US7268189B2 (en) 2000-03-24 2007-09-11 Novartis Ag Polymers
US7238750B2 (en) * 2000-03-24 2007-07-03 Novartis Ag Polymers
US8895687B2 (en) 2001-09-10 2014-11-25 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US8168720B2 (en) 2001-09-10 2012-05-01 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US6822016B2 (en) 2001-09-10 2004-11-23 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US7461937B2 (en) 2001-09-10 2008-12-09 Johnson & Johnson Vision Care, Inc. Soft contact lenses displaying superior on-eye comfort
WO2003022322A3 (fr) * 2001-09-10 2003-07-24 Johnson & Johnson Vision Care Dispositifs biomedicaux contenant des agents humidifiants internes
US10254443B2 (en) 2001-09-10 2019-04-09 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US9958577B2 (en) 2001-09-10 2018-05-01 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US10641926B2 (en) 2001-09-10 2020-05-05 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US9097914B2 (en) 2001-09-10 2015-08-04 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US8796353B2 (en) 2001-09-10 2014-08-05 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US10935696B2 (en) 2001-09-10 2021-03-02 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US11360241B2 (en) 2001-09-10 2022-06-14 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US8431669B2 (en) 2001-09-10 2013-04-30 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
WO2003022321A3 (fr) * 2001-09-10 2003-07-10 Johnson & Johnson Vision Care Dispositifs biomedicaux contenant des agents humidifiants internes
US7052131B2 (en) 2001-09-10 2006-05-30 J&J Vision Care, Inc. Biomedical devices containing internal wetting agents
US8524800B2 (en) 2006-12-13 2013-09-03 Novartis Ag Actinically curable silicone hydrogel copolymers and uses thereof
US8721945B2 (en) 2006-12-13 2014-05-13 Novartis Ag Actinically curable silicone hydrogel copolymers and uses thereof
US8071658B2 (en) 2007-03-22 2011-12-06 Novartis Ag Prepolymers with dangling polysiloxane-containing polymer chains
US8263679B2 (en) * 2007-03-22 2012-09-11 Novartis Ag Prepolymers with dangling polysiloxane-containing polymer chains
US20120046382A1 (en) * 2007-03-22 2012-02-23 Zhou Jian S Prepolymers with dangling polysiloxane-containing polymer chains
US8071703B2 (en) 2007-03-22 2011-12-06 Novartis Ag Silicone-containing prepolymers with dangling hydrophilic polymer chains
US8211955B2 (en) 2007-11-30 2012-07-03 Novartis Ag Actinically-crosslinkable silicone-containing block copolymers
US8044111B2 (en) 2007-11-30 2011-10-25 Novartis Ag Actinically-crosslinkable silicone-containing block copolymers
US8506856B2 (en) 2007-12-10 2013-08-13 Novartis Ag Method for making silicone hydrogel contact lenses
US8557940B2 (en) 2010-07-30 2013-10-15 Novartis Ag Amphiphilic polysiloxane prepolymers and uses thereof
US9341744B2 (en) 2010-07-30 2016-05-17 Novartis Ag Amphiphilic polysiloxane prepolymers and uses thereof
US8987403B2 (en) 2010-07-30 2015-03-24 Novartis Ag Amphiphilic polysiloxane prepolymers and uses thereof
US9109091B2 (en) 2010-10-06 2015-08-18 Novartis Ag Polymerizable chain-extended polysiloxanes with pendant hydrophilic groups
US8993651B2 (en) 2010-10-06 2015-03-31 Novartis Ag Polymerizable chain-extended polysiloxanes with pendant hydrophilic groups

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