# US 10,371,864 B2 · (Meth)acrylamide polymers for contact lens and intraocular lens

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- Number: US 10,371,864 B2
- Document ID: US10371864B2
- Status: Granted
- Kind: B2
- Application number: 15/304,648
- Filed: 2015-04-17
- Published: 2017-02-09
- Granted: 2019-08-06
- Earliest claimed: 2014-04-18
- Assignees: Benz Research and Development Corporation
- Applicants: Benz Research and Development Corp.
- Inventors: Patrick H. Benz; Adam Reboul
- Web page: https://patentgrep.com/patent/US10371864B2

## CPC

- G02B 1/043: {Contact lenses}
- A61L 27/16: obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 27/52: Hydrogels or hydrocolloids
- C08F 20/54: Amides {, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide}
- C08F 20/56: Acrylamide; Methacrylamide
- C08F 20/58: containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-acryloylmorpholine}
- C08F 220/58: containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine}
- G02B 1/041: {Lenses}
- G02C 7/049: {Contact lenses having special fitting or structural features achieved by special materials or material structures}
- A61L 2430/16: for reconstruction of eye parts, e.g. intraocular lens, cornea
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- G02C: SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES (trial frames for testing the eyes A61B3/04; goggles or eyeshields not having the same features as spectacles A61F9/00)

## Abstract

An contact lens or intraocular lens (IOL) with very high water content polymers that have increased hydrolytic stability to withstand high temperatures such as autoclave temperatures, 123 C or even higher temperatures while in an aqueous environment comprising at least one polymer comprising one or more monomeric subunits comprising a polymerized acrylamide or methacrylamide group, at least one side group comprising an aliphatic carbon moiety substituted by at least one hydroxyl moiety, wherein the one or more monomeric subunits comprising a polymerized acrylamide or methacrylamide group, at least one side group comprising an aliphatic carbon moiety substituted by at least one hydroxyl moiety, comprise at least 50 wt. % of the polymer.

## Claims

### Claim 1

A contact lens or IOL comprising at least one polymer comprising
a first monomeric subunit comprising a polymerized acrylamide or methacrylamide group, at least one side group comprising an aliphatic carbon moiety substituted by at least two hydroxyl moieties,
a second monomeric subunit comprising a polymerized acrylate or methacrylate group, and
a cross-linking monomeric subunit comprising a polymerized di(meth)acrylamide monomer,
wherein the first monomeric subunit constitutes at least 50 wt. % of the polymer, and
the polymer does not comprise an ionic moiety.

### Claim 2 (depends on 1)

The contact lens of claim 1, wherein the side group of the first monomeric subunit comprises a branched or unbranched C3-5 aliphatic carbon moiety substituted by two hydroxyl moieties.

### Claim 3 (depends on 1)

The contact lens of claim 1, wherein the cross-linking monomeric subunit constitutes greater than zero, but less than 5% of the polymer.

### Claim 4 (depends on 1)

The contact lens of claim 1, wherein the side group of the first monomeric subunit is a 2,3-dihydroxylpropyl moiety.

### Claim 5 (depends on 1)

The contact lens according to claim 1, wherein at least one polymer further comprises a polymerized UV absorbing monomer.

### Claim 6

A contact lens blank, comprising a polymer formed from a mixture of monomers comprising a crosslinking monomer, a monomer comprising a polymerized acrylate or methacrylate group, and greater than about 50 wt. % of 2,3-dihydroxylpropyl (meth)acrylamide.

### Claim 7 (depends on 6)

The contact lens blank according to claim 6, wherein the crosslinking monomer is a PEG di(meth)acrylamide.

### Claim 8 (depends on 6)

The contact lens blank according to claim 6, wherein the contact lens further comprises water.

### Claim 9 (depends on 6)

The contact lens blank according to claim 6, wherein the contact lens blank has an equilibrium water content of about 70 percent to about 75 percent.

### Claim 10 (depends on 9)

The contact lens blank according to claim 9, wherein the contact lens blank is capable of being machined.

### Claim 11 (depends on 6)

The contact lens blank according to claim 6, wherein the mixture of monomers further comprises a UV absorbing monomer.

### Claim 12

A composition comprising a polymer formed from a mixture of monomers constitutes greater than 50 wt. % dihydroxylpropyl (meth)acrylamide and a second monomer comprising a polymerized acrylate or methacrylate group, wherein the mixture of monomers comprises greater than zero, but less than 5 wt. % of a di-functional (meth)acrylamide monomer and the polymer does not comprise an ionic moiety.

### Claim 13 (depends on 12)

The composition of claim 12, wherein the mixture of monomers further comprises a UV absorbing monomer.

### Claim 14 (depends on 13)

The composition of claim 13, wherein the polymer further comprises water.

### Claim 15 (depends on 13)

The composition of claim 13, wherein the polymer is suitable for use in a contact lens or IOL.

### Claim 16 (depends on 13)

The composition of claim 13, wherein the composition is suitable for use in a contact lens.

### Claim 17

A lens comprising at least one polymer comprising, a first monomeric subunit comprising polymerized 2,3-dihydroxypropyl (meth)acrylamide and a second monomeric subunit comprising 2-hydroxyethylmethacrylate and optionally a crosslinking monomeric subunit.

### Claim 18 (depends on 17)

The lens of claim 17, wherein the first monomeric subunit constitutes at least 50 wt. % of the polymer.

### Claim 19 (depends on 17)

The lens of claim 17, wherein the crosslinking monomeric subunit is present, and is a PEG di(meth)acrylamide.

### Claim 20 (depends on 17)

The lens of claim 17, wherein the 2,3-dihydroxypropyl(meth)acrylamide monomer subunits constitutes 50 wt. % to 60 wt. % of the polymer.

### Claim 21

A polymer consisting of a first monomeric subunit comprising polymerized 2,3-dihydroxypropyl (meth)acrylamide, a second monomeric subunit comprising 2-hydroxyethylmethacrylate, and optionally one or more selected from the group consisting of a cross-linking monomeric subunit, a UV absorbing monomer, and a polymer initiator.

### Claim 22 (depends on 21)

The polymer of claim 21, wherein the cross-linking monomeric subunit is present, and is a PEG di(meth)acrylamide.

### Claim 23 (depends on 21)

The polymer of claim 21, wherein the polymerized 2,3-dihydroxypropyl (meth)acrylamide constitutes at least 50 wt. % of the polymer.

### Claim 24 (depends on 21)

The polymer of claim 21, wherein the polymerized 2,3-dihydroxypropyl (meth)acrylamide constitutes 50 wt. % to 60 wt. % of the polymer.

### Claim 25 (depends on 21)

The polymer of claim 21, wherein the cross-linking monomeric subunit constitutes greater than zero, but less than 5% of the polymer.

### Claim 26 (depends on 21)

The polymer of claim 21, wherein the polymer has an equilibrium water content of about 70 percent to about 75 percent.

### Claim 27 (depends on 1)

The contact lens of claim 1, wherein the contact lens further comprises water.

### Claim 28 (depends on 27)

The contact lens of claim 27, wherein the contact lens has an equilibrium water content of about 70 percent to about 75 percent.

### Claim 29 (depends on 1)

The contact lens of claim 1, wherein the first monomeric subunit constitutes 50 wt. % to 60 wt. % of the polymer.