Silicone-containing contact lens material and contact lenses made thereof

Claim 2

A contact lens comprised substantially of a polymer formed by free radical polymerization of an unsaturated, multifunctional, organosiloxane having the formula ##STR5## wherein: Y' is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl and allyl, X' is a divalent hydrocarbon having from 0 to 10 carbons, Y is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl, allyl and hydrogen, X is a divalent hydrocarbon having from 1 to 10 carbon atoms, or phenylene, A is selected from the group consisting of straight chain alkyl groups having 1 to 5 carbon atoms, branched chain, or cyclic alkyl groups having 3 to 5 carbon atoms, phenyl group and "Z" groups, Z is a group selected from the following: trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, nonamethyl tetrasiloxanyl, bis(trimethylsiloxy)methyl siloxanyl, or tris(trimethylsiloxy)siloxanyl "a" is an integer from 0 to 10, the total of "a" values is at least 2, "n" is an integer from 0 to about 10, and each of said X, X', Y, Y', a, A and Z groups each individually being the same or different.

Claim 3

A contact lens in accordance with claim 1 wherein said organosiloxane is 1,3-bis(γ-methacyloxypropyl)-1,1,3,3 tetra(trimethylsiloxy)disiloxane.

Claim 4

A contact lens in accordance with claim 1 wherein said organosiloxane is 1,3-bis(γ-methacryloxypropyl)-1,1,3,3 tetra(trimethylsiloxy)disiloxane.

Claim 5

A contact lens in accordance with claim 1 wherein said organosiloxane is tetra silane.

Claim 6

A contact lens in accordance with claim 1 wherein said organosiloxane is 1,3-bis(γ-methacryloxypropyl)-1,1,3,3 tetra(pentamethyl disiloxanyl)disiloxane.

Claim 7

A contact lens in accordance with claim 1 wherein said organosiloxane is 1,3-bis(γ-methacryloxypropyl)-1,1,3,3 tetra disiloxane.

Claim 8

A contact lens in accordance with claim 1 wherein said organosiloxane is 1,7-bis(γ-methacryloxypropyl)-1,1,3,3,5,5,7,7-octa(trimethylsiloxy)tetra siloxane.

Claim 9

A contact lens in accordance with claim 1 wherein said organosiloxane is tris(γ-methacryloxypropyl tetramethyl disiloxanyl)trimethylsiloxy silane.

Claim 10

A contact lens in accordance with claim 1 wherein said organosiloxane is 1,7-bis(γ-methacryloxypropyl)-1,1,7,7-tetra(pentamethyl disiloxanyl)-3,3,5,5-tetra(trimethylsiloxy)tetrasiloxane.

Claim 11

A contact lens in accordance with claim 1 wherein said organosiloxane is tris(γ-methacryloxypropyl tetramethyl disiloxanyl)methyl silane.

Claim 12

A contact lens material comprising a polymeric material formed from free radical polymerization of a monomeric mixture comprising a significant amount of a multifunctional, unsaturated, organosiloxane having the formula: ##STR6## wherein: Y' is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl and allyl, X' is a divalent hydrocarbon having from 0 to 10 carbons, Y is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl, allyl and hydrogen, X is a divalent hydrocarbon having from 1 to 10 carbon atoms, or phenylene, A is selected from the group consisting of straight chain alkyl groups having 1 to 5 carbon atoms, branched chain, or cyclic alkyl groups having 3 to 5 carbon atoms, phenyl group and "Z" groups, Z is a group selected from the following: trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, nonamethyl tetrasiloxanyl, bis(trimethylsiloxy)methyl siloxanyl or tris(trimethylsiloxy)siloxanyl "a" is an integer from 0 to 10, the total of "a" values is at least 2, "n" is an integer from 0 to about 10, and each of said X, X', Y, Y', a, A and Z groups each individually being the same or different and a monofunctional, unsaturated organosiloxane monomer having the formula: ##STR7## wherein: R is selected from the group consisting of methyl groups and hydrogen, "a" is an integer from 1 to 4, A is selected from the group consisting of straight chain alkyl groups having 1 to 5 carbon atoms, branched chain alkyl groups of from 3 to 5 carbon atoms, cyclohexyl group, phenyl group and Z groups, Z is a group selected from trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, nonamethyl tetrasiloxanyl, bis(trimethylsiloxy)methyl siloxanyl or tris(trimethylsiloxy)siloxanyl, "b" is an integer from 0 to 10, each "b", "A" and Z may be the same or different, and the total of "b" values being at least 1.

Claim 13

A contact lens material comprising a polymeric material formed from free radical polymerization of a monomeric mixture comprising a significant amount of a multifunctional, unsaturated, organosiloxane having the formula: ##STR6## wherein: Y' is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl and allyl, X' is a divalent hydrocarbon having from 0 to 10 carbons, Y is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl, allyl and hydrogen, X is a divalent hydrocarbon having from 1 to 10 carbon atoms, or phenylene, A is selected from the group consisting of straight chain alkyl groups having 1 to 5 carbon atoms, branched chain, or cyclic alkyl groups having 3 to 5 carbon atoms, phenyl group and "Z" groups, Z is a group selected from the following: trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, nonamethyl tetrasiloxanyl, bis(trimethylsiloxy)methyl siloxanyl or tris(trimethylsiloxy)siloxanyl "a" is an integer from 0 to 10, the total of "a" values is at least 2, "n" is an integer from 0 to about 10, and each of said X, X', Y, Y', a, A and Z groups each individually being the same or different and a monofunctional, unsaturated organosiloxane monomer having the formula: ##STR7## wherein: R is selected from the group consisting of methyl groups and hydrogen, "a" is an integer from 1 to 4, A is selected from the group consisting of straight chain alkyl groups having 1 to 5 carbon atoms, branched chain alkyl groups of from 3 to 5 carbon atoms, cyclohexyl group, phenyl group and Z groups, Z is a group selected from trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, nonamethyl tetrasiloxanyl, bis(trimethylsiloxy)methyl siloxanyl or tris(trimethylsiloxy)siloxanyl, "b" is an integer from 0 to 10, each "b", "A" and Z may be the same or different, and the total of "b" values being at least 1.

Claim 14

A contact lens material in accordance with claim 11 wherein said unsaturated polymerizable group Y and Y' is selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl and allyl and the divalent hydrocarbon of X and X' is selected from the group consisting of methylene, ethylene, propylene and butylene.

Claim 15

A contact lens material in accordance with claim 12 wherein A is selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, alkaryl, haloaryl and halo substituted lower alkyl radicals.

Claim 16

A contact lens material in accordance with claim 11 wherein said multifunctional organosiloxane is 1,3-bis(γ-methacryloxypropyl)-1,1,3,3tetra(trimethylsiloxy)disiloxane.

Claim 17

A contact lens material in accordance with claim 11 wherein said multifunctional organosiloxane is 1,3-bis(γ-methacryloxypropyl)-1,1,3,3tetra(trimethylsiloxy)disiloxane.

Claim 18

A contact lens material in accordance with claim 11 wherein said multifunctional organosiloxane is tetra γ-methacryloxypropyl dimethyl siloxy!silane.

Claim 19

A contact lens material in accordance with claim 11 wherein said multifunctional organosiloxane is 1,3-bis (γ-methacryloxypropyl)-1,1,3,3tetra(pentamethyl disiloxanyl)disiloxane.

Claim 20

A contact lens material in accordance with claim 11 wherein said multifunctional organosiloxane is 1,3-bis(γ-methacryloxypropyl)-1,1,3,3tetra bis(trimethylsiloxy)methyl siloxanyl!disiloxane.

Claim 21

A contact lens material in accordance with claim 11 wherein said multifunctional organosiloxane is 1,7-bis(γ-methacryloxypropyl)-1,1,3,3,5,5,7,7-octa(trimethylsiloxy)tetrasiloxane.

Claim 22

A contact lens material in accordance with claim 11 wherein said multifunctional organosiloxane is tris(γ-methacryloxypropyl tetramethyl disiloxanyl)trimethylsiloxy silane.

Claim 23

A contact lens material in accordance with claim 11 wherein said multifunctional organosiloxane is 1,7-bis(γ-methacryloxypropyl)-1,1,7,7-tetra(pentamethyl disiloxanyl)-3,3,5,5-tetra(trimethylsiloxy)tetrasiloxane.

Claim 24

A contact lens material in accordance with claim 11 wherein said multifunctional organosiloxane is tris(γmethacryloxypropyl tetramethyl disiloxanyl)methyl silane.

Claim 25

The contact lens material of claim 11 wherein said mixture comprises: (1) the multifunctional organosiloxane, (2) the monofunctional organosiloxane, and (3) a wetting agent wherein: the combination of (1) and (2) comprises 99 to 80% by weight of said mixture (1) being from about 30 to about 100% by weight of said combination and (2) being from 0 to 70% by weight of said combination, and (3) comprises 1 to 20% of said mixture, said wetting agent being an ethylenically unsaturated hydrophilic monomer.

Claim 26

A contact lens material in accordance with claim 23 wherein said mixture further comprises a hardening agent, said agent being an ester of a C 1 -C 20 monohydric or polyhydric alkanol or phenol and an acid selected from the group consisting of acrylic and methacrylic acid.

Claim 27

A contact lens material in accordance with claim 24 wherein said hardening agent comprises an itaconate mono or di ester.

Claim 28

An oxygen permeable, dimensionally stable, wettable contact lens of high trannsparency comprised substantially of a polymer formed by free radical polymerization of the following monomeric mixture comprising: (1) multifunctional organosiloxane, (2) monofunctional organosiloxane, (3) ester, (4) hydrophilic monomer and (5) itaconate wherein: the combination of (1) and (2) comprises from 3 to 65% by weight of said mixture, (1) being from about 30 to about 100% by weight of said combination and (2) being from about 0 to 70% by weight of said combination, (3) being from 1 to 45% by weight of said mixture, and (4) being from 1 to 20% by weight of said mixture and (5) being from 1 to 20% by weight of said mixture, said multifunctional organosiloxane (1) being: ##STR8## wherein: Y' is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl and allyl, X' is a divalent hydrocarbon having from 0 to 10 carbons, Y is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl, allyl and hydrogen, X is a divalent hydrocarbon having from 1 to 10 carbon atoms, or phenylene, A is selected from the group consisting of straight chain alkyl groups having 1 to 5 carbon atoms, branched chain, or cyclic alkyl groups having 3 to 5 carbon atoms, phenyl group and "Z" groups, Z is a group selected from the following: trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, nonamethyl tetrasiloxanyl, bis(trimethylsiloxy)methyl siloxanyl or tris(trimethylsiloxy) siloxanyl "a" is an integer from 0 to 10 the total of "a" values is at least 2, "n" is an integer from 0 to about 10, and each of said X, X', Y, Y', a, A and Z groups each individually being the same or different, (2) said monofunctional organosiloxane (2) being ##STR9## wherein: R is selected from the class consisting of methyl groups and hydrogen, "a" is an integer from 1 to 4, A is selected from the group consisting of straight chain alkyl groups having from 1 to 5 carbon atoms or branched alkyl groups of from 3 to 5 carbon atoms, cyclohexyl group, phenyl group and Z groups, Z is a group selected from trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, monamethyl tetrasiloxanyl, bis(trimethylsiloxy) methyl siloxanyl or tris(trimethylsiloxy) siloxanyl, "b" is an integer from 0 to 10, each "b", "A" and Z may be the same or different, and the total of "b" values being at least 1, said ester (3) being an ester of a C 1 -C 20 monohydric or polyhydric alkanol or phenol at an acid selected from the class consisting of acrylic and methacrylic acid, said hydrophilic monomer being an ethylenically unsaturated hydrophilic monomer to impart hydrophilic properties to the surface of the contact lens material, and said itaconate (5) being an itaconate mono or di ester.

Claim 29

An oxygen permeable, dimensionally stable, wettable contact lens of high trannsparency comprised substantially of a polymer formed by free radical polymerization of the following monomeric mixture comprising: (1) multifunctional organosiloxane, (2) monofunctional organosiloxane, (3) ester, (4) hydrophilic monomer and (5) itaconate wherein: the combination of (1) and (2) comprises from 3 to 65% by weight of said mixture, (1) being from about 30 to about 100% by weight of said combination and (2) being from about 0 to 70% by weight of said combination, (3) being from 1 to 45% by weight of said mixture, and (4) being from 1 to 20% by weight of said mixture and (5) being from 1 to 20% by weight of said mixture, said multifunctional organosiloxane (1) being: ##STR8## wherein: Y' is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl and allyl, X' is a divalent hydrocarbon having from 0 to 10 carbons, Y is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl, allyl and hydrogen, X is a divalent hydrocarbon having from 1 to 10 carbon atoms, or phenylene, A is selected from the group consisting of straight chain alkyl groups having 1 to 5 carbon atoms, branched chain, or cyclic alkyl groups having 3 to 5 carbon atoms, phenyl group and "Z" groups, Z is a group selected from the following: trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, nonamethyl tetrasiloxanyl, bis(trimethylsiloxy)methyl siloxanyl or tris(trimethylsiloxy) siloxanyl "a" is an integer from 0 to 10 the total of "a" values is at least 2, "n" is an integer from 0 to about 10, and each of said X, X', Y, Y', a, A and Z groups each individually being the same or different, (2) said monofunctional organosiloxane (2) being ##STR9## wherein: R is selected from the class consisting of methyl groups and hydrogen, "a" is an integer from 1 to 4, A is selected from the group consisting of straight chain alkyl groups having from 1 to 5 carbon atoms or branched alkyl groups of from 3 to 5 carbon atoms, cyclohexyl group, phenyl group and Z groups, Z is a group selected from trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, monamethyl tetrasiloxanyl, bis(trimethylsiloxy) methyl siloxanyl or tris(trimethylsiloxy) siloxanyl, "b" is an integer from 0 to 10, each "b", "A" and Z may be the same or different, and the total of "b" values being at least 1, said ester (3) being an ester of a C 1 -C 20 monohydric or polyhydric alkanol or phenol at an acid selected from the class consisting of acrylic and methacrylic acid, said hydrophilic monomer being an ethylenically unsaturated hydrophilic monomer to impart hydrophilic properties to the surface of the contact lens material, and said itaconate (5) being an itaconate mono or di ester.

Claim 30

An oxygen permeable, dimensionally stable, wettable contact lens of high transparency comprising substantially a polymer formed by free radical polymerization from a monomeric mixture of (1) multifunctional organosiloxane and (2) monofunctional organosiloxane polymerized in the presence of a wetting agent wherein (1) is present in an amount of above about 30% by weight of said mixture and (2) is present in an amount of up to about 70% by weight of said mixture said multifunctional organosiloxane (1) having the formula: ##STR10## wherein: Y' is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamino, acrylamido, styryl and allyl, X' is a divalent hydrocarbon having from 0 to 10 carbons, Y is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl, allyl and hydrogen, X is a divalent hydrocarbon having from 1 to 10 carbon atoms, or phenylene, A is selected from the group consisting of straight chain alkyl groups having 1 to 5 carbon atoms, branched chain, or cyclic alkyl groups having 3 to 5 carbon atoms, phenyl group and "Z" groups, Z is a group selected from the following: trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, nonamethyl tetrasiloxanyl, bis(trimethylsiloxy)methyl siloxanyl or tris(trimethylsiloxy) siloxanyl "a" is an integer from 0 to 10, the total of "a" values is at least 2, "n" is an integer from 0 to about 10, and each of said X, X', Y, Y', a, A and Z groups each individually being the same or different, said monofunctional organosiloxane (2) having the formula: ##STR11## wherein: R is selected from the group consisting of methyl groups and hydrogen, "a" is an integer from 1 to 4, A is selected from the group consisting of straight chain alkyl groups of from 1 to 5 carbon atoms and branched chain alkyl groups of from 3 to 5 carbon atoms, cyclohexyl group, phenyl group and Z groups, Z is a group selected from trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, monamethyl tetrasiloxanyl, bis(trimethylsiloxy) methyl siloxanyl or tris(trimethylsiloxy) siloxanyl, "b" is an integer from 0 to 10, each "b", "A" and Z may be the same or different, and the total of "b" values being at least 1, and said wetting agent being ethylenically unsaturated and admixed with said monomeric mixture.

Claim 31

An oxygen permeable, dimensionally stable, wettable contact lens of high transparency comprising substantially a polymer formed by free radical polymerization from a monomeric mixture of (1) multifunctional organosiloxane and (2) monofunctional organosiloxane polymerized in the presence of a wetting agent wherein (1) is present in an amount of above about 30% by weight of said mixture and (2) is present in an amount of up to about 70% by weight of said mixture said multifunctional organosiloxane (1) having the formula: ##STR10## wherein: Y' is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamino, acrylamido, styryl and allyl, X' is a divalent hydrocarbon having from 0 to 10 carbons, Y is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl, allyl and hydrogen, X is a divalent hydrocarbon having from 1 to 10 carbon atoms, or phenylene, A is selected from the group consisting of straight chain alkyl groups having 1 to 5 carbon atoms, branched chain, or cyclic alkyl groups having 3 to 5 carbon atoms, phenyl group and "Z" groups, Z is a group selected from the following: trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, nonamethyl tetrasiloxanyl, bis(trimethylsiloxy)methyl siloxanyl or tris(trimethylsiloxy) siloxanyl "a" is an integer from 0 to 10, the total of "a" values is at least 2, "n" is an integer from 0 to about 10, and each of said X, X', Y, Y', a, A and Z groups each individually being the same or different, said monofunctional organosiloxane (2) having the formula: ##STR11## wherein: R is selected from the group consisting of methyl groups and hydrogen, "a" is an integer from 1 to 4, A is selected from the group consisting of straight chain alkyl groups of from 1 to 5 carbon atoms and branched chain alkyl groups of from 3 to 5 carbon atoms, cyclohexyl group, phenyl group and Z groups, Z is a group selected from trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, monamethyl tetrasiloxanyl, bis(trimethylsiloxy) methyl siloxanyl or tris(trimethylsiloxy) siloxanyl, "b" is an integer from 0 to 10, each "b", "A" and Z may be the same or different, and the total of "b" values being at least 1, and said wetting agent being ethylenically unsaturated and admixed with said monomeric mixture.

Claim 32

An oxygen permeable, hard, machinable, dimensionally stable, contact lens in accordance with claim 27 wherein said mixture further comprises a hardening or softening agent.

Claim 33

An oxygen permeable, hard, machinable, dimensionally stable, contact lens in accordance, with claim 28 wherein said agent is a hydrophilic hardening agent.

Claim 34

A contact lens in accordance with claim 26 wherein said multifunctional organosiloxane is 1,3-bis (γmethacryloxypropyl)-1,1,3,3tetra(trimethylsiloxy) disiloxane and said monofunctional organosiloxane is methacryloxypropyl tris (trimethylsilyl)siloxane.

Claim 35

A contact lens in accordance with claim 30 wherein said ester is methylmethacrylate.

Claim 36

A contact lens in accordance with claim 23 wherein said multifunctional organosiloxane is 1,3-bis (γmethacryloxypropyl)-1,1,3,3tetra(trimethylsiloxy) disiloxane and said monofunctional organosiloxane is methacryloxypropyl tris (trimethylsilyl)siloxane.

Claim 37

A contact lens in accordance with claim 32 wherein said ester is methylmethacrylate.