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EP0094153A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Inherently wettable silicone resin optical devices

Assignee: Dow Silicones Corp
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Filing: 1983-04-13
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Granted: —
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Expires: 2003-04-13
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Abstract

Abstract This invention provides oxygen permeable, inherently wettable optical devices useful as corneal, scleral or intraocular lenses. The lenses are composed of a cured polysiloxane resin having a water-in-air contact angle no greater than 80°. The polysiloxane resin is prepared from an acrylate-functional polysiloxane composition containing at least 30 mole percent of H 2 C=CRCOOR'SiO 1.5 units and any remaining siloxane units present in the composition are R"SiO 1.5 R" 2 SiO and/or R" 3 SiO O . 5 where each R is -H or -Ch 3 , each R' is a divalent alkylene radical of 1 to 4 carbon atoms and each R" is an alkyl or haloalkyl radical of from 1 to 3 carbon atoms, a phenyl radical or hydrogen. The inherent wettability results from the level of the specific type of acrylate-functional siloxane units present. In an alternative embodiment, the physical properties of the device are improved by the inclusion of up to 30 weight percent of compatible aliphatically unsaturated organic compound such as methyl methacrylate.

Inventors

  • 👤 Darrel Duane Mitchell

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-30 23:21
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043; C; C08; C08F; C08F283/00; C08F283/12; C08F283/124; C08G; C08G77/00; C08G77/04; C08G77/20; C08L; C08L83/00; C08L83/04; C08L83/06

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 262 words
As an optical device, a lens to be worn against or inside the eye which is inherently wettable by human tear fluid and possesses an oxygen gas permeability coefficient of at least 2 x 10-10 (cm 3 · cm)/(cm 2 · sec · cm Hg) which results in a calculated open eye Equivalent Oxygen Performance of at least 3 percent at 0.1 mm thickness at 21°±2°C, said lens consisting essentially of an optically clear biocompatible cured polysiloxane resin having a flexural strength value of at least 3,500 p.s.i. and durometer value of at least 60 on the Shore D scale in the unhydrated state at 21°±2°C and having an advancing water-in-air contact angle value not greater than 80° at 21°±2°C in the unhydrated state, said resin having been prepared by curing an acrylate-functionai polysiloxane composition containing at least 30 mole percent of acrylate-functional siloxane units of the unit formula H 2 C=CRCOOR'SiO 1.5 , where said mole percentage is based upon the total moles of siloxane units present in said polysiloxane composition, essentially any remaining siloxane units present in said composition being selected from the group consisting of siloxane units of the unit formula R"SiO 1.5 ' R" 2 SiO and R" 3 SiO 0.5 , wherein R is a methyl radical or hydrogen, R' is a divalent alkylene radical of from 1 to 4 inclusive carbon atoms, and each R" is selected from the group consisting of alkyl radicals of from 1 to 3 inclusive carbon atoms, haloalkyl radicals of from 1 to 3 inclusive carbon atoms, phenyl radicals and hydrogen.
Claim 2
Dependent Claim 262 words
As an optical device, a lens to be worn against or inside the eye which is inherently wettable by human tear fluid and possesses an oxygen gas permeability coefficient of at least 2 x 10-10 (cm 3 · cm)/(cm 2 · sec · cm Hg) which results in a calculated open eye Equivalent Oxygen Performance of at least 3 percent at 0.1 mm thickness at 21°±2°C, said lens consisting essentially of an optically clear biocompatible cured polysiloxane resin having a flexural strength value of at least 3,500 p.s.i. and durometer value of at least 60 on the Shore D scale in the unhydrated state at 21°±2°C and having an advancing water-in-air contact angle value not greater than 80° at 21°±2°C in the unhydrated state, said resin having been prepared by curing an acrylate-functionai polysiloxane composition containing at least 30 mole percent of acrylate-functional siloxane units of the unit formula H 2 C=CRCOOR'SiO 1.5 , where said mole percentage is based upon the total moles of siloxane units present in said polysiloxane composition, essentially any remaining siloxane units present in said composition being selected from the group consisting of siloxane units of the unit formula R"SiO 1.5 ' R" 2 SiO and R" 3 SiO 0.5 , wherein R is a methyl radical or hydrogen, R' is a divalent alkylene radical of from 1 to 4 inclusive carbon atoms, and each R" is selected from the group consisting of alkyl radicals of from 1 to 3 inclusive carbon atoms, haloalkyl radicals of from 1 to 3 inclusive carbon atoms, phenyl radicals and hydrogen.
Claim 3
Dependent Claim 334 words
As an optical device, a lens to be worn against or inside the eye which is inherently wettable by human tear fluid and possesses an oxygen gas permeability coefficient (DK) value of at least 2 x 10 -10 (cm 3 · cm) / (cm 2 · sec ·cm Hg) which results in a calculated open eye Equivalent Oxygen Performance of at least 3 percent at 0.1 mm thickness at 21°+2°C, said lens consisting essentially of an optically clear biocompatible cured polysiloxane/organic copolymer resin having a flexural strength value of at least 3,500 p.s.i. and a durometer value of at least 60 on the Shore D scale in the unhydrated state at 21°±2°C and having an advancing water-in-air contact angle value not greater than 80° at 21°±2°C in the unhydrated state, said resin having been prepared by curing a compatible mixture consisting essentially of (A) an acrylate-functional polysiloxane composition containing at least 30 mole percent of acrylate-functional siloxane units of the unit formula H 2 C=CRCOOR'SiO 1.5 , where said mole percentage is based upon the total moles of siloxane units present in said polysiloxane composition, essentially any remaining siloxane units present in said composition being selected from the group consisting of siloxane units of the unit formula R" 2 SiO and R" 3 SiO 0.5 , wherein R is a methyl radical or hydrogen, R' is a divalent alkylene radical of from 1 to 4 inclusive carbon atoms, and each R" is selected from the group consisting of alkyl radicals of from 1 to 3 inclusive carbon atoms, haloalkyl radicals of from 1 to 3 inclusive carbon atoms, phenyl radicals and hydrogen and (B) up to 60 weight percent, based upon the total weight of the mixture, of at least one aliphatically unsaturated organic compound that is free of silicon atoms and has a molecular weight of less than 200, there being no = SiH siloxane units present in said mixture when a compound capable of providing -OH radicals is included in the mixture.
Claim 4
Dependent Claim 334 words
As an optical device, a lens to be worn against or inside the eye which is inherently wettable by human tear fluid and possesses an oxygen gas permeability coefficient (DK) value of at least 2 x 10 -10 (cm 3 · cm) / (cm 2 · sec ·cm Hg) which results in a calculated open eye Equivalent Oxygen Performance of at least 3 percent at 0.1 mm thickness at 21°+2°C, said lens consisting essentially of an optically clear biocompatible cured polysiloxane/organic copolymer resin having a flexural strength value of at least 3,500 p.s.i. and a durometer value of at least 60 on the Shore D scale in the unhydrated state at 21°±2°C and having an advancing water-in-air contact angle value not greater than 80° at 21°±2°C in the unhydrated state, said resin having been prepared by curing a compatible mixture consisting essentially of (A) an acrylate-functional polysiloxane composition containing at least 30 mole percent of acrylate-functional siloxane units of the unit formula H 2 C=CRCOOR'SiO 1.5 , where said mole percentage is based upon the total moles of siloxane units present in said polysiloxane composition, essentially any remaining siloxane units present in said composition being selected from the group consisting of siloxane units of the unit formula R" 2 SiO and R" 3 SiO 0.5 , wherein R is a methyl radical or hydrogen, R' is a divalent alkylene radical of from 1 to 4 inclusive carbon atoms, and each R" is selected from the group consisting of alkyl radicals of from 1 to 3 inclusive carbon atoms, haloalkyl radicals of from 1 to 3 inclusive carbon atoms, phenyl radicals and hydrogen and (B) up to 60 weight percent, based upon the total weight of the mixture, of at least one aliphatically unsaturated organic compound that is free of silicon atoms and has a molecular weight of less than 200, there being no = SiH siloxane units present in said mixture when a compound capable of providing -OH radicals is included in the mixture.
Claim 5
Dependent Claim 230 words
A composition of matter consisting essentially of an acrylate-functional polysiloxane composition containing at least 30 mole percent of acrylate-functional siloxane units of the unit formula H 2 C=CRCOOR'SiO 1.5 , where said mole percentage is based upon the total moles of siloxane units present in said polysiloxane composition, essentially any remaining siloxane units present in said composition being selected from the group consisting of siloxane units of the unit formula R"SiO 1.5 , R" 2 SiO, and R' 3 SiO 0.5 ' wherein R is a methyl radical or hydrogen, R' is a divalent alkylene radical of from 1 to 4 inclusive carbon atoms, and each R" is selected from the group consisting of alkyl radicals of from 1 to 3 inclusive. carbon atoms, haloalkyl radicals of from 1 to 3 inclusive carbon atoms, phenyl radicals and hydrogen, said composition being curable to an optically clear polysiloxane resin having a flexural strength of at least 3,500 p.s.i., a durometer value of at least 60 on the Shore D scale at 21°±2°C, and advancing water-in-air contact angle no greater than 80°C at 21°±2°C in the unhydrated state and an oxygen gas permeability coefficient (DK) value of at least 2 x 10 -10 (cm 3 ·cm)/(cm 2 · sec ·cm Hg) which results in a calculated open eye Equivalent Oxygen Performance of at least 3 percent at 0.1 mm thickness at 21°±2°C.
Claim 6
Dependent Claim 230 words
A composition of matter consisting essentially of an acrylate-functional polysiloxane composition containing at least 30 mole percent of acrylate-functional siloxane units of the unit formula H 2 C=CRCOOR'SiO 1.5 , where said mole percentage is based upon the total moles of siloxane units present in said polysiloxane composition, essentially any remaining siloxane units present in said composition being selected from the group consisting of siloxane units of the unit formula R"SiO 1.5 , R" 2 SiO, and R' 3 SiO 0.5 ' wherein R is a methyl radical or hydrogen, R' is a divalent alkylene radical of from 1 to 4 inclusive carbon atoms, and each R" is selected from the group consisting of alkyl radicals of from 1 to 3 inclusive. carbon atoms, haloalkyl radicals of from 1 to 3 inclusive carbon atoms, phenyl radicals and hydrogen, said composition being curable to an optically clear polysiloxane resin having a flexural strength of at least 3,500 p.s.i., a durometer value of at least 60 on the Shore D scale at 21°±2°C, and advancing water-in-air contact angle no greater than 80°C at 21°±2°C in the unhydrated state and an oxygen gas permeability coefficient (DK) value of at least 2 x 10 -10 (cm 3 ·cm)/(cm 2 · sec ·cm Hg) which results in a calculated open eye Equivalent Oxygen Performance of at least 3 percent at 0.1 mm thickness at 21°±2°C.
Claim 7
Dependent Claim 302 words
A composition of matter consisting essentially of a compatible mixture of (A) an acrylate-functional polysiloxane composition containing at least 30 mole percent of acrylate-functional siloxane units of the unit formula H 2 C=CRCOOR'SiO 1.5 , where said mole percentage is based upon the total moles of siloxane units present in said polysiloxane composition, essentially any remaining siloxane units present in said composition being selected from the group consisting of siloxane units of the unit formula R"SiO 1.5 , R" 2 SiO, and R" 3 SiO 0.5 , wherein R is a methyl radical or hydrogen, R' is a divalent alkylene radical of from 1 to 4 inclusive carbon atoms, and each R" is selected from the group consisting of alkyl radicals of from 1 to 3 inclusive carbon atoms, haloalkyl radicals of from 1 to 3 inclusive carbon atoms, phenyl radicals and hydrogen and (B) up to 60 weight percent, based upon the total weight of the mixture, of at least one aliphatically unsaturated organic compound that is free of silicon atoms and has a molecular weight of less than 200, there being no = SiH siloxane units present in said mixture when a compound capable of providing -OH radicals is included in the mixture, said mixture being curable to an optically clear polysiloxane/organic copolymer resin having a flexural strength of at least 3,500 p.s.i., a durometer value of at least 60 on the Shore D scale at 21°±2°C, an advancing water-in-air contact angle no greater than 80°C at 21°±2°C in the unhydrated state and an oxygen gas permeability coefficient (DK) value of at least 2 x 10 -10 (cm 3 · cm) / (cm 2 · sec · cm Hg) which results in a calculated open eye Equivalent Oxygen Performance of at least 3 percent at 0.1 mm thickness at 21°±2°C.
Claim 8
Dependent Claim 302 words
A composition of matter consisting essentially of a compatible mixture of (A) an acrylate-functional polysiloxane composition containing at least 30 mole percent of acrylate-functional siloxane units of the unit formula H 2 C=CRCOOR'SiO 1.5 , where said mole percentage is based upon the total moles of siloxane units present in said polysiloxane composition, essentially any remaining siloxane units present in said composition being selected from the group consisting of siloxane units of the unit formula R"SiO 1.5 , R" 2 SiO, and R" 3 SiO 0.5 , wherein R is a methyl radical or hydrogen, R' is a divalent alkylene radical of from 1 to 4 inclusive carbon atoms, and each R" is selected from the group consisting of alkyl radicals of from 1 to 3 inclusive carbon atoms, haloalkyl radicals of from 1 to 3 inclusive carbon atoms, phenyl radicals and hydrogen and (B) up to 60 weight percent, based upon the total weight of the mixture, of at least one aliphatically unsaturated organic compound that is free of silicon atoms and has a molecular weight of less than 200, there being no = SiH siloxane units present in said mixture when a compound capable of providing -OH radicals is included in the mixture, said mixture being curable to an optically clear polysiloxane/organic copolymer resin having a flexural strength of at least 3,500 p.s.i., a durometer value of at least 60 on the Shore D scale at 21°±2°C, an advancing water-in-air contact angle no greater than 80°C at 21°±2°C in the unhydrated state and an oxygen gas permeability coefficient (DK) value of at least 2 x 10 -10 (cm 3 · cm) / (cm 2 · sec · cm Hg) which results in a calculated open eye Equivalent Oxygen Performance of at least 3 percent at 0.1 mm thickness at 21°±2°C.

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