# US 5,346,976 A · Itaconate copolymeric compositions for contact lenses

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- Number: US 5,346,976 A
- Document ID: US5346976A
- Status: Granted
- Kind: A
- Application number: 08/038,970
- Filed: 1993-03-29
- Granted: 1994-09-13
- Earliest claimed: 1993-03-29
- Assignees: Polymer Technology Corporation
- Inventors: Edward J. Ellis; Alfred P. Olson; James A. Bonafini, Jr.
- Web page: https://patentgrep.com/patent/US5346976A

## CPC

- G02B 1/043: {Contact lenses}
- C08F 230/08: containing silicon
- Y10S 525/937: Utility as body contact e.g. implant, contact lens or I.U.D.
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Copolymers useful as contact lens materials are the polymerization product of a mixture comprising: (a) an itaconate; (b) a compound represented by formula (I): ##STR1## wherein: each A is independently an activated unsaturated radical; each R is independently selected from the group consisting of a C.sub.1 -C.sub.12 monovalent hydrocarbon radical, a C.sub.1 -C.sub.12 monovalent hydrocarbon radical containing ether linkages, a halogen-substituted C.sub.1 -C.sub.12 monovalent hydrocarbon radical, and a halogen-substituted C.sub.1 -C.sub.12 monovalent hydrocarbon radical containing ether linkages; each R' is independently a C.sub.1 -C.sub.22 divalent hydrocarbon radical; and n averages about 15 to about 50; (c) an ethylenically unsaturated organosiloxane monomer; and (d) a hydrophilic monomer.

## Claims

### Claim 1

A copolymer useful as a contact lens material which is the polymerization product of a mixture comprising:
(a) an itaconate;
(b) a siloxane compound represented by formula (I): ##STR7## wherein: each A is independently an activated unsaturated radical;
each R is independently selected from the group consisting of a C.sub.1 -C.sub.12 monovalent hydrocarbon radical, a C.sub.1 -C.sub.12 monovalent hydrocarbon radical containing ether linkages, a halogen-substituted C.sub.1 -C.sub.12 monovalent hydrocarbon radical, and a halogen-substituted C.sub.1 -C.sub.12 monovalent hydrocarbon radical containing ether linkages;
each R' is independently a C.sub.1 -C.sub.22 divalent hydrocarbon radical; and
n averages about 15 to about 50;
(c) an ethylenically unsaturated, monofunctional organosiloxane monomer; and
(d) a hydrophilic monomer.

### Claim 2 (depends on 1)

The copolymer of claim 1, wherein compound (b) is ##STR8## wherein n averages about 25.

### Claim 3 (depends on 2)

The copolymer of claim 2, wherein itaconate (a) is bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate.

### Claim 4 (depends on 1)

The copolymer of claim 1, wherein said mixture comprises:
(a) the itaconate at about 5 to about 60 weight percent;
(b) the siloxane compound of formula (I) at about 3 to about 25 weight percent;
(c) the ethylenically unsaturated, monofunctional organosiloxane monomer at about 2 to about 60 weight percent;
(d) the hydrophilic monomer at about 1 to about 25 weight percent;
(e) a hardness modifying (meth)acrylate monomer at 0 to about 50 weight percent; and
(f) a non-silicone containing crosslinking agent at 0 to about 20 weight percent.

### Claim 5 (depends on 4)

The copolymer of claim 4, wherein said mixture comprises:
(a) the itaconate at about 20 to about 55 weight percent;
(b) the siloxane compound of formula (I) at about 9 to about 20 weight percent;
(c) the ethylenically unsaturated, monofunctional organosiloxane monomer at about 5 to about 50 weight percent;
(d) the hydrophilic monomer at about 5 to about 15 weight percent;
(e) the (meth)acrylate monomer at about 5 to about 35 weight percent; and
(f) the non-silicone containing crosslinking agent at about 1 to about 10 weight percent.

### Claim 6 (depends on 5)

The copolymer of claim 5, wherein the organosiloxane monomer (c) includes tris(trimethylsiloxy)silylpropyl methacrylate.

### Claim 7 (depends on 5)

The copolymer of claim 5, wherein the (meth)acrylate monomer (e) includes at least one alkyl (meth)acrylate.

### Claim 8 (depends on 7)

The copolymer of claim 7, wherein the alkyl (meth)acrylate is selected from the group consisting of methyl methacrylate, neopentyl methacrylate, and mixtures thereof.

### Claim 9 (depends on 5)

The copolymer of claim 5, wherein the hydrophilic monomer (d) is selected from the group consisting of methacrylic acid, N-vinylpyrrolidone, and mixtures thereof.

### Claim 10 (depends on 5)

The copolymer of claim 5, wherein the crosslinking agent (f) includes neopentyl glycol dimethacrylate.

### Claim 11 (depends on 4)

The copolymer of claim 4, wherein said mixture comprises:
(a) the itaconate at about 20 to about 55 weight percent;
(b) the siloxane compound of formula (I) at about 9 to about 20 weight percent;
(c) the ethylenically unsaturated, monofunctional organosiloxane monomer at about 5 to about 50 weight percent;
(d) the hydrophilic monomer at about 5 to about 15 weight percent; and
(e) the (meth)acrylate monomer at about 5 to about 35 weight percent.

### Claim 12 (depends on 4)

The copolymer of claim 4, wherein said mixture comprises:
(a) the itaconate at about 20 to about 55 weight percent;
(b) the siloxane compound of formula (I) at about 9 to about 20 weight percent;
(c) the ethylenically unsaturated, monofunctional organosiloxane monomer at about 5 to about 50 weight percent;
(d) the hydrophilic monomer at about 5 to about 15 weight percent; and
(f) the non-silicone containing crosslinking agent at about 1 to about 10 weight percent.

### Claim 13 (depends on 1)

A copolymer of claim 1, wherein said mixture consists essentially of: bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate; the compound ##STR9## wherein n averages about 25; tris(trimethylsiloxy)silylpropyl methacrylate; methacrylic acid; N-vinylpyrrolidone; at least one monomer selected from the group consisting of methyl methacrylate and neopentyl methacrylate; and at least one free radical initiator.

### Claim 14 (depends on 1)

A copolymer of claim 1, wherein said mixture consists essentially of: bis(1,1,1,3,3,3-hexafluoro-2propyl) itaconate; the compound ##STR10## wherein n averages about 25; tris(trimethylsiloxy)silylpropyl methacrylate; methacrylic acid; N-vinylpyrrolidone; neopentyl glycol dimethacrylate; neopentyl methacrylate; and at least one free radical initiator.

### Claim 15

A rigid, gas permeable contact lens formed of a copolymer which is the polymerization product of a mixture comprising:
(a) an itaconate;
(b) a siloxane compound represented by formula (I): ##STR11## wherein: each A is independently an activated unsaturated radical;
each R is independently selected from the group consisting of a C.sub.1 -C.sub.12 monovalent hydrocarbon radical, a C.sub.1 -C.sub.12 monovalent hydrocarbon radical containing ether linkages, a halogen-substituted C.sub.1 -C.sub.12 monovalent hydrocarbon radical, and a halogen-substituted C.sub.1 -C.sub.12 monovalent hydrocarbon radical containing ether linkages;
each R' is independently a C.sub.1 -C.sub.22 divalent hydrocarbon radical; and
n average about 15 to about 50; and
(c) an ethylenically unsaturated, monofunctional organosiloxane monomer; and
(d) a hydrophilic monomer.

### Claim 16 (depends on 15)

The contact lens of claim 15, wherein compound (b) has the formula ##STR12## wherein n averages about 25.

### Claim 17 (depends on 16)

The contact lens of claim 16, wherein the itaconate is bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate.

### Claim 18 (depends on 15)

The contact lens of claim 15, wherein the copolymer is the polymerization product of a mixture consisting essentially of: bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate; the compound ##STR13## wherein n averages about 25; tris(trimethylsiloxy)silylpropyl methacrylate; methacrylic acid; N-vinylpyrrolidone; at least one monomer selected from the group consisting of methyl methacrylate and neopentyl methacrylate; and at least one free radical initiator.

### Claim 19 (depends on 15)

The contact lens of claim 15, wherein the copolymer is the polymerization product of a mixture consisting essentially of: bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate; the compound ##STR14## wherein n averages about 25; tris(trimethylsiloxy)silylpropyl methacrylate; methacrylic acid; N-vinylpyrrolidone; neopentyl glycol dimethacrylate; neopentyl methacrylate; and at least one free radical initiator.