Novel vinyl carbonate and vinyl carbamate contact lens material monomers

Claim 2

A copolymer formed by polymerizing a prepolymer mixture comprising: (a) a base monomer described by the general chemical formula: wherein X denotes an -0-, -S- or -NR 3- divalent radical; R' denotes an organic radical; R 2 denotes -H or -CH 3 ; R 3 denotes -H, or a monovalent alkyl radical; b equals 0 or 1; and (b) a crosslinking agent.

Claim 3

The copolymer of Claim 1 wherein the base monomer is 2-hydroxyethyl vinyl carbonate, 2-hydroxyethyl vinyl carbamate, 3-(2-pyrrolidinone-1-yl)propyl vinyl carbonate, 2-(2-pyrrolidinone-1-yl) ethyl vinyl carbonate, 2,2,2-trifluoroethyl vinyl carbonate, 2,2,2-trifluoroethyl vinyl carbamate, 1,1,1,3,3,3-hexafluoroprop-2-yl vinyl carbonate, 2,2,2-trifluoro-1-phenylethyl vinyl carbonate, trimethylsilylmethyl vinyl carbonate, trimethylsilyethyl vinyl carbonate, 3-(trimethylsilyl)propyl vinyl carbonate, t-butyldimethylsiloxyethyl vinyl carbonate, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate, 3-(vinyloxycarbonylthio)propyl-[tris(trimethylsiloxy)silane], 3-[tris(trimethylsiloxy)silyl]propyl allyl carbamate, 1,3-bis[4-vinyloxycarbonyloxy)but-1-yl] tetramethyl disiloxane, N-[tris(trimethylsiloxy)-silylpropyl]-N-methyl vinyl carbamate, N-Vinyloxycarbonyl-N -[tris(trimethylsiloxy)silylpropyl] piperazine, 3-[Tris(trimethylsiloxy)silyl]propylaminoethyl vinyl carbonate, N-(vinyloxycarbonyloxy)-pyrrolidin-2,5-dione, N-(vinyloxycarbonyloxyethyl)-pyrrolidin-2,5-dione, 4-sec-butylphenyl vinyl carbonate, 4-t-butylphenyl vinyl carbamate, 4(t-butyl)cyclohexyl vinyl carbamate, 1-adamantane vinyl carbonate, 1-adamantanemethyl vinyl carbonate, 1-adamantaneethyl vinyl carbonate, or 1-adamantane vinyl carbamate.

Claim 4

The copolymer of Claim 1 or Claim 2, wherein said crosslinking agent is described by the general formula: wherein X denotes an -0-, -S-, or -NR 3- divalent radical; R' denotes an organic radical; R 2 denotes -H or -CH 3 ; R 3 denotes -H or a monovalent alkyl radical; a equals 2, 3 or 4; and b equals 0 or 1.

Claim 5

The copolymer of Claim 3 wherein the crosslinking agent is propargyl vinyl carbamate of 1,3-bis[4- vinyloxycarbonyloxy)but-1-yl]-tetramethyl disiloxane.

Claim 6

The copolymer of Claim 3 wherein the crosslinking agent is of the formula:

Claim 7

The copolymer of Claim 3 wherein the crosslinking agent is 1,2-bis-(vinyloxycarbonyloxy)ethane, α-ω-bis-(vinyloxycarbonyl)triethyleneglycol, a-w-bis-(vinyloxycarbonyl)polyethylene glycol, α-ω-bis-(Vinyloxycarbonyl) polypropylene glycol, 2,2-dimethyl-1,3-bis-(vinyloxycarbonyloxy)propane, N,O-bis-(vinyloxycarbonyl)-ethanolamine, 2,2-dimethyl-N,N-bis(vinyloxycarbonyl)-1,3-propanediamine, or 1,5-bis-(vinyloxycarbonyloxy)-2,2,3,3,4,4-hexafluoropentane.

Claim 8

The copolymer of Claim 3 where a equals 2 and R 1 is of the general formula: where x and z are 1 to 6, y is on the average between 2 and 200 and R 1 denotes an alkyl radical or fluorinated alkyl radical with 1 to 6 carbon atoms.

Claim 9

A hydrogel copolymer formed by polymerizing a prepolymer mixture comprising a non-hydrophilic monomer of the general formula: wherein X denotes -0-, -S-, -NR 3- divalent radical; R NH denotes a non-hydrophilic organic radical; R 3 denotes -H or a monovalent alkyl radical; a is 1, 2, 3 or 4; b is 0 or 1; R 2 is hydrogen or methyl; and a hydrophilic monomer; and a crosslinking agent.

Claim 10

A hydrogel copolymer formed by polymerizing a prepolymer mixture comprising a non-hydrophilic monomer of the general formula: wherein X denotes -0-, -S-, -NR 3- divalent radical; R NH denotes a non-hydrophilic organic radical; R 3 denotes -H or a monovalent alkyl radical; a is 1, 2, 3 or 4; b is 0 or 1; R 2 is hydrogen or methyl; and a hydrophilic monomer; and a crosslinking agent.

Claim 11

The hydrogel material of Claim 8 wherein the hydrophilic monomer is N-vinyl-2-pyrrolidinone.

Claim 12

The novel hydrogel material of Claim 8 or Claim 9 wherein the non-hydrophilic monomer is 3-[tris-(trimethylsiloxy)silyl]propyl vinyl carbonate, t-butyl vinyl carbonate, t-butyldimethylsiloxyethyl vinyl carbonate, or 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate.

Claim 13

A soft, non-hydrogel, copolymer formed by polymerizing a mixture comprising: a non-hydrophilic monomer of the general chemical formula: wherein R 1 denotes -H or -CH 3 ; R NH is a largely non-hydrophilic organic radical; a is 1 or 2; and b is 0 or 1; a hydrophilic monomer chosen from the group consisting of N-vinyl-2-pyrrolidinone and 2-hydroxyethylmethacrylate, and a crosslinking monomer.

Claim 14

A soft, non-hydrogel, copolymer formed by polymerizing a mixture comprising: a non-hydrophilic monomer of the general chemical formula: wherein R 1 denotes -H or -CH 3 ; R NH is a largely non-hydrophilic organic radical; a is 1 or 2; and b is 0 or 1; a hydrophilic monomer chosen from the group consisting of N-vinyl-2-pyrrolidinone and 2-hydroxyethylmethacrylate, and a crosslinking monomer.

Claim 15

The copolymer of Claim 11 wherein the non-hydrophilic monomer is 3[tris(trimethylsiloxy)silyl] propyl vinyl carbonate, 1,3-bis(4-vinylbutylcarbonate) tetramethyldisiloxane, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate, 3-(Vinyloxycarbonylthio)propyl [tri(trimethylsiloxy)silane], 3-(trimethylsilyl)propyl vinyl carbonate, t-butyldimethylsiloxyethyl vinyl carbamate, trimethylsilylmethyl vinyl carbonate, trimethylsilylethyl vinyl carbonate, trifluoroethyl vinyl carbonate, t-butyl vinyl carbonate, 3[tris(trimethylsiloxy)silyl] propyl vinyl carbonate, 2,2,2-trifluoroethyl vinyl carbamate, 1,1,1,3,3,3-hexafluoro-2-propyl vinyl carbonate, 2,2,2-trifluoroethyl allyl carbonate, or 2,2,2-trifluoro-1-phenylethyl vinyl carbonate.

Claim 16

The copolymer of Claim 11 wherein the non-hydrophilic monomer is of the general formula:

Claim 17

A rigid gas permeable contact lens material comprising: a non-hydrophilic monomer of the general formula: wherein b is 0 or 1; a is 1, 2, 3 or 4; X denotes -0-, -NH- or -S-; and R NH denotes a non-hydrophilic moiety; R 1 is H or methyl; a crosslinking agent; and 1 to 20 wt % of a wetting monomer.

Claim 18

A rigid gas permeable contact lens material comprising: a non-hydrophilic monomer of the general formula: wherein b is 0 or 1; a is 1, 2, 3 or 4; X denotes -0-, -NH- or -S-; and R NH denotes a non-hydrophilic moiety; R 1 is H or methyl; a crosslinking agent; and 1 to 20 wt % of a wetting monomer.

Claim 19

A compound selected from: 3-(2-pyrrolidinone-1-yl)propyl vinyl carbonate; 2-(2-pyrrolidinone-1-yl)ethyl vinyl carbonate; 2,2,2-trifluoroethyl vinyl carbamate; 1,1,1,3,3,3-hexafluoroprop-2-yl vinyl carbonate; and 2,2,2-trifluorO-1-phenylethyl vinyl carbonate.

Claim 20

A compound selected from: 3-(2-pyrrolidinone-1-yl)propyl vinyl carbonate; 2-(2-pyrrolidinone-1-yl)ethyl vinyl carbonate; 2,2,2-trifluoroethyl vinyl carbamate; 1,1,1,3,3,3-hexafluoroprop-2-yl vinyl carbonate; and 2,2,2-trifluorO-1-phenylethyl vinyl carbonate.

Claim 21

A compound of the general formula: wherein R 2 denotes -H or -CH c ; b is O or 1 ; a is 1, 2, 3 or 4; and R is an organosilicon radical.

Claim 22

A compound of the general formula: wherein R 2 denotes -H or -CH c ; b is O or 1 ; a is 1, 2, 3 or 4; and R is an organosilicon radical.

Claim 23

A compound of Claim 16 selected from trimethylsilylmethyl vinyl carbonate, trimethylsilylethyl vinyl carbonate, 3-(trimethylsilyl)propyl vinyl carbonate, t-butyldimethylsiloxyethyl vinyl carbonate, 3-[tris-(trimethylsiloxy)silyl]propyl vinyl carbonate, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate, 3-(vinyloxycarbonylthio) propyl-[tris(trimethylsiloxy)silane], 3-[tris(trimethylsiloxy)silyl]propyl allyl carbamate, 1,3-bis[4-(vinyloxycarbonyloxy)but-1-yl]tetramethyl disiloxane, N-[tris(trimethylsiloxy)silylpropyl]-N-methyl vinyl carbamate, N-vinyloxycarbonyl-N'- [tris(trimethylsiloxy)silylpropyl] piperazine, and 3-[tris(trimethylsiloxy)-silyl]propylaminoethyl vinyl carbonate.

Claim 24

A compound of the general formula: wherein a is 1, 2, 3 or 4; X denotes -0-, -S- or -NR-; R 2 denotes -H or -CH 3 ; R 3 is -H or -CH 3 ; and R denotes a cycloalkyl, cycloaryl or heterocyclic radical.

Claim 25

A compound of the general formula: wherein a is 1, 2, 3 or 4; X denotes -0-, -S- or -NR-; R 2 denotes -H or -CH 3 ; R 3 is -H or -CH 3 ; and R denotes a cycloalkyl, cycloaryl or heterocyclic radical.

Claim 26

A compound of Claim 18 selected from N-(vinyloxycarbonyloxy)-pyrrolidin-2,5-dione, N-(vinyloxycarbonyloxyethyl-pyrrolidin-2.5-dione, 4-s-butylphenyl vinyl carbonate, 4-t-butylphenyl vinyl carbamate, 4(t-butyl)cyclohexyl vinyl carbonate, 1-adamantane vinyl carbonate, 1-adamantane methyl vinyl carbonate, 1-adamantane ethyl vinyl carbonate, and 1-adamantane vinyl carbamate.

Claim 27

A compound of the general formula: wherein a is 1, 2, 3 or 4; R 2 denotes -H or -CH 3 ; X denotes -S-; b is 0 or 1; and R is an organic radical.

Claim 28

A compound of the general formula: wherein a is 1, 2, 3 or 4; R 2 denotes -H or -CH 3 ; X denotes -S-; b is 0 or 1; and R is an organic radical.

Claim 29

Propargyl vinyl carbamate.

Claim 30

Propargyl vinyl carbamate.

Claim 31

1,3-bis[4-vinyloxycarbonyloxy)but-1-yl]tetramethyl disiloxane.

Claim 32

1,3-bis[4-vinyloxycarbonyloxy)but-1-yl]tetramethyl disiloxane.

Claim 33

1,2-bis-(vinyloxycarbonyloxy)ethane.

Claim 34

1,2-bis-(vinyloxycarbonyloxy)ethane.

Claim 35

α-ω-bis-(vinyloxycarbonyl)triethyleneglycol.

Claim 36

α-ω-bis-(vinyloxycarbonyl)triethyleneglycol.

Claim 37

α-ω-bis-(vinyloxycarbonyl)polyethylene glycol.

Claim 38

α-ω-bis-(vinyloxycarbonyl)polyethylene glycol.

Claim 39

a,w-bis-(vinyloxycarbonyl) polypropylene glycol.

Claim 40

a,w-bis-(vinyloxycarbonyl) polypropylene glycol.

Claim 41

2,2-dimethyl-1,3-bis-(vinyloxycarbonyloxy)propane.

Claim 42

2,2-dimethyl-1,3-bis-(vinyloxycarbonyloxy)propane.

Claim 43

N,0-bis-(vinyloxycarbonyl)-ethanolamine.

Claim 44

N,0-bis-(vinyloxycarbonyl)-ethanolamine.

Claim 45

2,2-dimethyl-N,N-bis(vinyloxycarbonyl-1,3-propanediamine.

Claim 46

2,2-dimethyl-N,N-bis(vinyloxycarbonyl-1,3-propanediamine.

Claim 47

1,5-bis-(vinyloxycarbonyloxy)-2,2,3,3,4,4-hexafluoropentane.

Claim 48

1,5-bis-(vinyloxycarbonyloxy)-2,2,3,3,4,4-hexafluoropentane.