Wettable silicone hydrogel compositions and methods for their manufacture

Claim 5

The method of claim 2 wherein said bulky polysiloxanylalkyl (meth)acrylic monomer is selected from the group consisting of methacryloxypropyl tris(trimethylsiloxy)silane, pentamethyldisiloxanylmethylmethacrylate, tris(trimethylsiloxy)methacryloxy propylsilane, phenyltetramethyldisiloxanylethyl acetate, and methyldi(trimethylsiloxy)methacryloxymethyl silane.

Claim 8

The method of claim 4 wherein said silicone-containing prepolymer is a urethane-containing prepolymer having the following schematic representations: E(*D*A'*D*G).sub.a *D*A"*D*E'; or E(*D*G*D*A").sub.a *D*G*D*E'; where D denotes an alkyl diradical, an alkyl cycloalkyl diradical, a cycloalkyl diradical, an aryl diradical or an alkylaryl diradical having 6 to 30 carbon atoms; G denotes an alkyl diradical, a cycloalkyl diradical, an alkyl cycloalkyl diradical, an aryl diradical or an alkylaryl diradical having 1 to 40 carbon atoms and which may contain ether, thio or amine linkages in the main chain; *denotes a urethane or ureido linkage; a is at least 1; A" denotes a divalent polymeric radical of formula: ##STR8## wherein: R s and R s' independently denote an alkyl or fluoro-substituted alkyl group having 1 to 10 carbon atoms which may contain ether linkages between carbon atoms; m is at least 1; and p provides a moiety weight of 400 to 10,000; E and E' independently denote a polymerizable unsaturated organic radical represented by the formula: ##STR9## wherein: R 14 denotes a divalent alkylene radical having 1 to 10 carbon atoms; R 12 denotes H or CH 3 ; R 13 denotes H, a (C 1 -C 6 ) alkyl radical or a --CO--Y--R 15 group wherein Y is --O--, --S-- or --NH-- and R 15 is a alkyl radical having 1 to 12 carbon atoms; X is --CO-- or --OCO--; Z is --O-- or --NH--; Ar denotes an aromatic radical having 6 to 30 carbon atoms; w is 0 to 6; x is 0 or 1; y is 0 or 1; and z is 0 or 1.

Claim 9

The method of claim 5 wherein said urethane-containing prepolymer is represented by the formula: ##STR10## wherein: R 16 is a diradical of a diisocyanate after removal of the isocyanate group, and is most preferably the diradical of isophorone diisocyanate, and m, p and a are the same as previously defined.

Claim 11

The method of claim 1, 2 or 4 wherein said ring-containing oxazolone monomer is 2-vinyl-4,4-dimethyl-2-oxazolin-5-one.

Claim 13

A silicone-containing hydrogel composition prepared by polymerizing a monomer mix comprising 0.5 to 10 weight percent of a ring-containing oxazolone monomer able to be converted to a highly polar hydrophilic amino acid upon hydration, with an α, ω-bis(methacryloxyalkyl)polysiloxane monomer, and at least one additional hydrophilic monomer.

Claim 14

A silicone-containing hydrogel composition prepared by polymerizing a monomer mix comprising 0.5 to 10 weight percent of a ring-containing oxazolone monomer able to be converted to a highly polar hydrophilic amino acid upon hydration, with an α, ω-bis(methacryloxyalkyl)polysiloxane monomer, and at least one additional hydrophilic monomer.

Claim 15

A silicone-containing hydrogel composition prepared by polymerizing a monomer mix comprising from about 0.5 to about 10 weight percent of a ring-containing oxazolone monomer able to be converted to a highly polar hydrophilic amino acid upon hydration with a bulky polysiloxanylalkyl (meth)acrylic monomer having the following formula: ##STR11## wherein: X is O or NR; each R is independently hydrogen or methyl; and each R 1 is independently a lower alkyl or phenyl group; and f is 1 or 3 to 10; and at least one additional hydrophilic monomer into a monomer mix and b) curing the monomer mix resulting from step a) to form a silicone-containing hydrogel composition.

Claim 16

A silicone-containing hydrogel composition prepared by polymerizing a monomer mix comprising from about 0.5 to about 10 weight percent of a ring-containing oxazolone monomer able to be converted to a highly polar hydrophilic amino acid upon hydration with a bulky polysiloxanylalkyl (meth)acrylic monomer having the following formula: ##STR11## wherein: X is O or NR; each R is independently hydrogen or methyl; and each R 1 is independently a lower alkyl or phenyl group; and f is 1 or 3 to 10; and at least one additional hydrophilic monomer into a monomer mix and b) curing the monomer mix resulting from step a) to form a silicone-containing hydrogel composition.

Claim 17

The composition of claim 11 wherein said bulky polysiloxanylalkyl (meth)acrylic monomer is selected from the group consisting of methacryloxypropyl tris(trimethylsiloxy)silane, pentamethyldisiloxanylmethylmethacrylate, tris(trimethylsiloxy)methacryloxy propylsilane, phenyltetramethyldisiloxanylethyl acetate, and methyldi(trimethylsiloxy)methacryloxymethyl silane.

Claim 18

A silicone-containing hydrogel composition prepared by polymerizing a monomer mix comprising from about 0.5 to about 10 weight percent of a ring-containing oxazolone monomer able to be converted to a highly polar hydrophilic amino acid upon hydration with a urethane-containing prepolymer and at least one additional hydrophilic monomer into a monomer mix and b) curing the monomer mix resulting from step a) to form a silicone-containing hydrogel composition.

Claim 19

A silicone-containing hydrogel composition prepared by polymerizing a monomer mix comprising from about 0.5 to about 10 weight percent of a ring-containing oxazolone monomer able to be converted to a highly polar hydrophilic amino acid upon hydration with a urethane-containing prepolymer and at least one additional hydrophilic monomer into a monomer mix and b) curing the monomer mix resulting from step a) to form a silicone-containing hydrogel composition.

Claim 20

The composition of claim 13 wherein said silicone-containing prepolymer is urethane-containing prepolymer having the following schematic representations: E(*D*A"*D*G).sub.a *D*A"*D*E'; or E (*D*G*D*A").sub.a *D*G*D*E'; where D denotes an alkyl diradical, an alkyl cycloalkyl diradical, a cycloalkyl diradical, an aryl diradical or an alkylaryl diradical having 6 to 30 carbon atoms; G denotes an alkyl diradical, a cycloalkyl diradical, an alkyl cycloalkyl diradical, an aryl diradical or an alkylaryl diradical having 1 to 40 carbon atoms and which may contain ether, thio or amine linkages in the main chain; *denotes a urethane or ureido linkage; a is at least 1; A" denotes a divalent polymeric radical of formula: ##STR12## wherein: R s and R s' independently denote an alkyl or fluoro-substituted alkyl group having 1 to 10 carbon atoms which may contain ether linkages between carbon atoms; m is at least 1; and p provides a moiety weight of 400 to 10,000; E and E' independently denote a polymerizable unsaturated organic radical represented by the formula: ##STR13## wherein R 14 denotes a divalent alkylene radical having 1 to 10 carbon atoms; R 12 denotes H or CH 3 ; R 13 denotes H, a (C 1 -C 6 ) alkyl radical or a --CO--Y--R 15 group wherein Y is --O--, --S-- or --NH-- and R 15 is a alkyl radical having 1 to 12 carbon atoms; X is --CO-- or --OCO--; Z is --O-- or --NH--; Ar denotes an aromatic radical having 6 to 30 carbon atoms; w is 0 to 6; x is 0 or 1; y is 0 or 1; and z is 0 or 1.

Claim 21

The composition of claim 14 wherein said urethane-containing prepolymer is represented by the formula: ##STR14## wherein: R 16 is a diradical of a diisocyanate after removal of the isocyanate group, and is most preferably the diradical of isophorone diisocyanate, and m, p and a are the same as previously defined.

Claim 22

The composition of claims 10, 11 or 13 wherein said ring-containing oxazolone monomer is selected from the group consisting of 2-vinyl-4,4-dimethyl-2-oxazolin-5-one, 2-isopropenyl-4,4-dimethyl-2-oxazolin-5-one, cyclohexane-spiro-4'-(2'-isopropenyl-2'-oxazol-5'-one), cyclohexane-spiro-4'-(2'-vinyl-2'-oxazol-5'-one) and 2-(1-propenyl)-4,4-dimethyl-oxazol-5-one.

Claim 23

The composition of claims 10, 11 or 13 wherein said ring-containing oxazolone monomer is 2-vinyl-4,4-dimethyl-2-oxazolin-5-one.

Claim 24

The composition of claims 10, 11 or 13 wherein said additional hydrophilic monomer is selected from the group consisting of N,N-dimethylacrylamide and N-vinyl pyrrolidone.

Claim 27

A silicone-containing hydrogel composition prepared by polymerizing a monomer mix comprising a hydrophilic (meth)acrylamido alkanoic acid, at least one silicone-containing monomer, and at least one hydrophilic monomer in addition to and different from said hydrophilic monomer.

Claim 28

A silicone-containing hydrogel composition prepared by polymerizing a monomer mix comprising a hydrophilic (meth)acrylamido alkanoic acid, at least one silicone-containing monomer, and at least one hydrophilic monomer in addition to and different from said hydrophilic monomer.

Claim 29

An improved silicone-containing hydrogel formulation prepared by polymerizing a monomer mix comprising a silicone-containing monomer, and at least one hydrophilic monomer the improvement of which comprises the addition to said monomer mix of a hydrophilic ring-containing monomer able to be converted to a highly polar amino acid upon hydration in the amount of from about 0.5 to about 10 weight percent.

Claim 30

An improved silicone-containing hydrogel formulation prepared by polymerizing a monomer mix comprising a silicone-containing monomer, and at least one hydrophilic monomer the improvement of which comprises the addition to said monomer mix of a hydrophilic ring-containing monomer able to be converted to a highly polar amino acid upon hydration in the amount of from about 0.5 to about 10 weight percent.

Claim 31

A contact lens made from the composition of claim 20.

Claim 32

A contact lens made from the composition of claims 10, 11 or 13.