Hydroxy-substituted polymeric shaped hydrogel article
First Claim
1. An ophthalmic device prepared by a process comprising the steps:
- a. thermoforming an uncrosslinked polymer having a softening temperature of at least 100°
C. comprising the product of at least 95 weight percent of an ethylenically-unsaturated monomer bearing at least one trihaloacetoxy-substituent group, said ethylenically unsaturated monomer being(1) a compound having a formula ##STR2## wherein R is hydrogen or methyl, X is fluoro, chloro, bromo, iodo, perhaloacetoxy or perfluoroalkylsulfonoxy of one to three carbon atoms, and Y is trichloroacetyl or trifluoroacetyl, or(2) vinyl trihaloacetate, by heating said uncrosslinked polymer in a mold or pressing into sheets or films at a temperature in the range of 150°
to 400°
C. for 5 seconds to 15 minutes, and then cooling the resulting thermoformed polymer, to provide a thermoplastic, hydrogel precursor ophthalmic device.b. solvolyzing the hydrogel precursor ophthalmic device by reacting with a nucleophile which causes displacement of said trihaloacetoxy group to provide a hyroxy-substituted polymeric ophthalmic device, said solvolyzing step taking place in the presence of a diluent which is not a solvent for said thermoformed polymer, wherein when said polymer is derived from vinyl trihaloacetate it has a syndiotactic stereochemical configuration.
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Abstract
Articles including ophthalmic devices prepared by a process comprising the steps of thermoforming a polymer comprising units derived from an ethylenically-unsaturated monomer bearing at least one trihaloacetoxy-substituent group, by heating the polymer in a mold or in sheet-form at a temperature in the range of 100° to 400° C. for about 5 seconds to 15 minutes, and then cooling said polymer, to provide a shaped article, solvolyzing the resulting shaped article to provide a hydroxy-substituted polymeric shaped article, and optionally hydrating said hydroxy-substituted polymeric shaped article to provide a shaped hydrogel article. When the polymer is derived from vinyl trihaloacetate it has a syndiotactic stereochemical configuration.
33 Citations
21 Claims
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1. An ophthalmic device prepared by a process comprising the steps:
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a. thermoforming an uncrosslinked polymer having a softening temperature of at least 100°
C. comprising the product of at least 95 weight percent of an ethylenically-unsaturated monomer bearing at least one trihaloacetoxy-substituent group, said ethylenically unsaturated monomer being(1) a compound having a formula ##STR2## wherein R is hydrogen or methyl, X is fluoro, chloro, bromo, iodo, perhaloacetoxy or perfluoroalkylsulfonoxy of one to three carbon atoms, and Y is trichloroacetyl or trifluoroacetyl, or (2) vinyl trihaloacetate, by heating said uncrosslinked polymer in a mold or pressing into sheets or films at a temperature in the range of 150°
to 400°
C. for 5 seconds to 15 minutes, and then cooling the resulting thermoformed polymer, to provide a thermoplastic, hydrogel precursor ophthalmic device.b. solvolyzing the hydrogel precursor ophthalmic device by reacting with a nucleophile which causes displacement of said trihaloacetoxy group to provide a hyroxy-substituted polymeric ophthalmic device, said solvolyzing step taking place in the presence of a diluent which is not a solvent for said thermoformed polymer, wherein when said polymer is derived from vinyl trihaloacetate it has a syndiotactic stereochemical configuration. - View Dependent Claims (2, 3, 4, 5, 6)
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7. An ophthalmic device prepared by a process comprising the steps:
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a. thermoforming an uncrosslinked polymer having a softening temperature of at least 100°
C. comprising the product of at least 95 weight percent of an ethylenically-unsaturated monomer bearing at least one trihaloacetoxy-substituent group, said ethylenically unsaturated monomer being(1) a compound having a formula ##STR3## wherein R is hydrogen or methyl, X is fluoro, chloro, bromo, iodo, perhaloacetoxy or perfluoroalkylsulfonoxy of one to three carbon atoms, and Y is trichloroacetyl or trifluoroacetyl, or (2) vinyl trihaloacetate, by heating said uncrosslinked polymer in a mold or pressing into sheets or films at a temperature in the range of 150°
to 400°
C. for 5 seconds to 15 minutes, and then cooling the resulting thermoformed polymer, to provide a thermoplastic, hydrogel precursor ophthalmic device.b. solvolyzing the hydrogel precursor ophthalmic device by reacting with a nucleophile which causes displacement of said trihaloacetoxy group to provide a hyroxy-substituted polymeric ophthalmic device, said solvolyzing step taking place in the presence of a diluent which is not a solvent for said thermoformed polymer, c. hydrating said hydroxy-substituted polymeric article to provide a shaped hydrogel ophthalmic device, wherein when said polymer is derived from vinyl trihaloacetate it has a syndiotactic stereochemical configuration. - View Dependent Claims (8, 9, 10, 11, 12, 13)
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14. A shaped article prepared by a process comprising the steps:
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a. thermoforming an uncrosslinked polymer having a softening temperature of at least 100°
C. comprising the product of at least 95 weight percent of an ethylenically-unsaturated monomer bearing at least one trihaloacetoxy-substituent group, said ethylenically unsaturated monomer being(1) a compound having a formula ##STR4## wherein R is hydrogen or methyl, X is fluoro, chloro, bromo, iodo, perhaloacetoxy or perfluoroalkylsulfonoxy of one to three carbon atoms, and Y is trichloroacetyl or trifluoroacetyl, or (2) vinyl trihaloacetate, by heating said uncrosslinked polymer in a mold or pressing into sheets or films at a temperature in the range of 150°
to 400°
C. for 5 seconds to 15 minutes, and then cooling the resulting thermoformed polymer, to provide a thermoplastic, hydrogel precursor shaped article,b. solvolyzing the hydrogel precursor shaped article by reacting with a nucleophile which causes displacement of said trihaloacetoxy group to provide a hydroxy-substituted polymeric shaped article, said solvolyzing step taking place in the presence of a diluent which is not a solvent for said thermoformed polymer, wherein when said polymer is derived from vinyl trihaloactate it has a syndiotactic stereochemical configuration. - View Dependent Claims (15, 16, 17, 18, 19)
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20. An article bearing a hydrogel precursor coating prepared by a method comprising the steps:
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a. providing an article bearing a coating of an uncrosslinked polymer having a softening temperature of at least 100°
C. comprising the product of at least 95 weight percent of an ethylenically-unsaturated monomer bearing at least one trihaloacetoxy-substituent group, said ethylenically unsaturated monomer being(1) a compound having a formula ##STR5## wherein R is a hydrogen or methyl, X is fluoro, chloro, bromo, iodo, prehaloacetoxy or perfluoroalkylsulfonoxy of one to three carbon atoms, and Y is trichloroacetyl or trifluoroacetyl, or (2) vinyl trihaloacetate, b. heating said coated article at a temperature in the range of 150°
to 400°
C. for 5 seconds to 15 minutes to provide an article bearing a coating of a thermoformed polymer, andc. cooling said coated article to provide an article bearing a thermoplastic, hydrogel precursor coating solvolyzing said resulting coated article with a nucleophile capable of displacing said trihaloacetoxy group to provide a hydroxy-substituted-polymer coated article, wherein when said polymer is derived from vinyl trihaloactate it has a syndiotactic stereochemical configuration. - View Dependent Claims (21)
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Specification