Coopervision International Holding Company, LP

Charles A Francis

Arthur Back

Charlie Chen

Yuwen Liu

Li Yao

Ye Hong

Ying Zheng

Junhao Ge

Yuan Xu

David Robert Morsley

Xinfeng Shi

Ronghua Liu

Sarah L Almond

Hong Xue

Richard C Rogers

Yuan Ji

Hongjin Qiu

Yuan Sun

Shane Mao

Xining Zhang

Richard Rogers

Silicone hydrogel contact lenses having a high water content are described. The lenses are derived from a polymerizable composition including a first siloxane monomer represented by formula (1): wherein m of formula (1) represents one integer from 3 to 10, n of formula (1) represents one integer from 1 to 10, Rof formula (1) is an alkyl group having from 1 to 4 carbon atoms, and each Rof formula (1) is independently either a hydrogen atom or a methyl group; the lenses also include units derived from a second siloxane monomer having a number average molecular weight of at least 7,000 daltons, and at least one vinyl-containing cross-linking agent. The lenses have average equilibrium water contents from about 30% wt/wt to about 70% wt/wt when fully hydrated. Batches of silicone hydrogel contact lenses and methods of making silicone hydrogel contact lenses are also described.

High water content silicone hydrogel contact lenses

Silicone hydrogel contact lenses that are derived from a polymerizable composition including at least one siloxane monomer and at least one hydrophobic ethylene glycol methyl ether methacrylate-containing monomer, or at least one hydrophilic vinyl ether-containing monomer, or both, wherein, when the at least one hydrophobic ethylene glycol methyl ether methacrylate-containing monomer is present in the polymerizable composition, it is present in an amount of from 1 to 20 unit parts by weight, and when the at least one hydrophilic vinyl ether-containing monomer is present in the polymerizable composition, it is present in an amount of from 1 to 20 unit parts by weight, are described. Batches of silicone hydrogel contact lenses and methods of making silicone hydrogel contact lenses are also described.

Silicone hydrogel contact lenses

Silicone hydrogel contact lenses are formed from the reaction product of a polymerizable composition comprising at least one acrylate-containing siloxane monomer, at least one hydrophilic vinyl-containing monomer, and at least one vinyl-containing cross-linking agent. The contact lenses have ophthalmically-acceptable ionoflux values and surface wettability, and can be manufactured without the use of volatile organic solvents.

Silicone hydrogel contact lenses that are derived from a polymerizable composition including a first siloxane monomer represented by formula (3): 

A method for preparing a polymerizable monomer-dye compound is provided in which a monomer, a reactive dye, and base are combined under substantially anhydrous reaction conditions to form the polymerizable monomer-dye compound, wherein the monomer comprises a pendant reactive group that covalently links to the reactive dye to form the monomer-dye compound.

Reactive dyes for contact lenses

Silicone hydrogel contact lenses that have good dimensional stability, are ophthalmically-acceptable, and can be manufactured without the use of alcohol solvents are formed from the reaction product of a polymerizable composition comprising at least one mono-functional acrylate-containing siloxane monomer having a molecular weight of less than 2,000; at least one bi-functional acrylate-containing siloxane monomer having a molecular weight of at least 3,000; and at least one hydrophilic vinyl-containing monomer, wherein the polymerizable composition has a molar ratio of total amount of mono-functional acrylate-containing siloxane monomer to total amount of bi-functional acrylate-containing siloxane monomer of at least 30:1, respectively.

Silicone hydrogel contact lenses are produced without using volatile organic solvents to extract materials from the polymerized contact lens bodies, and instead are washed with aqueous liquids. The silicone hydrogel contact lenses so produced have ophthalmically wettable lens surfaces such that less than five percent of a batch of twenty or more such silicone hydrogel contact lenses have visually identifiable non-wetting spots when the contact lenses are located on eyes of subjects.

Silicone hydrogel contact lenses, when hydrated, have a plurality of depressions on one or more of the lens surfaces. The depressions have a depth less than 1 micrometer, or less than 100 nanometers. The silicone hydrogel contact lenses have not been subject to treatment with plasma. Methods of manufacturing the silicone hydrogel contact lenses are also disclosed.

Silicone hydrogel contact lenses and methods of making silicone hydrogel contact lenses

Silicone hydrogel contact lenses having ophthalmically acceptable levels of energy loss are described. The lenses are derived from a polymerizable composition including a first siloxane monomer represented by formula (1): wherein m of formula (1) represents one integer from 3 to 10, n of formula (1) represents one integer from 1 to 10, Rof formula (1) is an alkyl group having from 1 to 4 carbon atoms, and each Rof formula (1) is independently either a hydrogen atom or a methyl group; the lenses also include units derived from a second siloxane monomer which is a dual-end methacrylate end-capped polydimethylsiloxane having a number average molecular weight of at least 7,000 daltons. The average energy loss of the silicone hydrogel contact lenses is from about 30% to about 45% when the lenses are fully hydrated. Batches of silicone hydrogel contact lenses and methods of making silicone hydrogel contact lenses are also described.

Silicone hydrogel contact lenses having acceptable levels of energy loss

Ophthalmically acceptably wettable silicone hydrogel contact lenses are described. The lenses are derived from a polymerizable composition including a first siloxane monomer represented by formula (1): 

Wettable silicone hydrogel contact lenses

Silicone hydrogel contact lenses are produced without using volatile organic solvents to extract materials from the polymerized contact lens bodies, and instead are washed with aqueous liquids. The silicone hydrogel contact lenses so produced have ophthalmically wettable lens surfaces. The hydrated silicone hydrogel contact lenses have diameters that are at least 24% larger than the diameters of the silicone hydrogel contact lenses prior to hydration or washing.

Silicone hydrogel contact lenses and related compositions and methods

Ophthalmically acceptably wettable silicone hydrogel contact lenses are described. The lenses are derived from a polymerizable composition including a first siloxane monomer. The lenses have ophthalmically acceptably wettable lens surfaces when fully hydrated. Batches of silicone hydrogel contact lenses and methods of making silicone hydrogel contact lenses are also described.

Silicone hydrogel contact lenses having ophthalmically acceptable levels of energy loss are described. The lenses are derived from a polymerizable composition including a first siloxane monomer represented by formula (1): wherein m of formula (1) represents one integer from 3 to 10, n of formula (1) represents one integer from 1 to 10, Rof formula (1) is an alkyl group having from 1 to 4 carbon atoms, and each Rof formula (1) is independently either a hydrogen atom or a methyl group; the lenses also include units derived from a second siloxane monomer which is a dual-end methacrylate end-capped polydimethylsiloxane having a number average molecular weight of at least 7,000 daltons. Batches of silicone hydrogel contact lenses and methods of making silicone hydrogel contact lenses are also described.

Dimensionally stable silicone hydrogel contact lenses are described. The lenses are derived from a polymerizable composition including a first siloxane monomer represented by formula (1):  

Dimensionally stable silicone hydrogel contact lenses

Compositions and methods for improving demolding polar resin molds used in the production of silicone hydrogel materials are described. The present compositions and methods include the use of one or more reactive demolding agents. The reactive demolding agents react with components of a polymerization mixture to produce a polymerized silicone hydrogel device containing a reactant product of the demolding agent and the other components of the polymerization mixture. Polar resin molds used during the polymerization of the polymerization mixture are more easily separated than substantially identical molds used in the polymerization of a substantially identical material without a reactive demolding agent. The present compositions and methods may be used in the manufacture of silicone hydrogel lenses, such as contact lenses. The demolding aids may also be useful as delensing aids.

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Union City, CA, United States of America

Charles A Francis