# US 2013/0158211 A1 · Imbibing process for contact lens surface modification

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- Number: US 2013/0158211 A1
- Document ID: US20130158211A1
- Status: Published application
- Kind: A1
- Application number: 13/715,790
- Filed: 2012-12-14
- Published: 2013-06-20
- Earliest claimed: 2011-12-14
- Assignees: Semprus Biosciences Corp.
- Inventors: Zheng ZHANG; Karen Ann SCHULTZ; Matt SKINNER; Christopher R. LOOSE
- Web page: https://patentgrep.com/patent/US20130158211A1

## CPC

- C08G 77/388: containing nitrogen
- G02B 1/043: {Contact lenses}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS

## Abstract

Medical devices having a wettable, biocompatible surface are described herein. Processes for producing such devices are also described.

## Claims

### Claim 1

A process for modifying the surface of a silicon-containing polymer, the process comprising the steps of:
imbibing a zwitterionic monomer or a free radical initiator into a silicon-containing polymer in an imbibing mixture comprising the silicon-containing polymer, at least one of the zwitterionic monomer and the free radical initiator, and a solvent system; and
polymerizing the zwitterionic monomer to modify the surface of the silicon-containing polymer with a zwitterionic polymer in a polymerization reaction mixture, the polymerization reaction mixture comprising the imbibed silicon-containing polymer, a solvent system and the zwitterionic monomer or the free radical initiator, the polymerization reaction mixture having a composition that differs from the composition of the imbibing mixture.

### Claim 2 (depends on 1)

The process of claim 1 wherein the imbibing mixture comprises the zwitterionic monomer but not the free radical initiator.

### Claim 3 (depends on 1)

The process of claim 1 wherein the imbibing mixture comprises the free radical initiator and the zwitterionic monomer, and the imbibing mixture and polymerization reaction comprise different solvent systems.

### Claim 4 (depends on 1)

The process of claim 1 wherein the silicon-containing polymer contains at least 1 wt. % silicon.

### Claim 5 (depends on 1)

The process of claim 1 wherein the silicon-containing polymer contains at least 20 wt. % silicon.

### Claim 6 (depends on 1)

The process of claim 1 wherein the zwitterionic polymer comprises a carboxyammonium polymer or a sulfoammonium polymer.

### Claim 7 (depends on 1)

The process of claim 1 wherein the zwitterionic polymer comprises a carboxybetaine polymer or a sulfobetaine polymer.

### Claim 8 (depends on 1)

The process of claim 1 wherein the zwitterionic polymer comprises at least one repeat unit corresponding to Formula 2:
wherein
X3 is hydrogen, alkyl or substituted alkyl, and
X4 is a pendant group comprising an oxylated alkylene moiety, a zwitterionic moiety, an anionic moiety, or a cationic moiety.

### Claim 9 (depends on 8)

The process of claim 8 wherein X3 is hydrogen or alkyl.

### Claim 10 (depends on 8)

The process of claim 8 wherein the repeat unit of Formula 2 is a zwitterionic repeat unit comprising a zwitterionic moiety corresponding to Formula ZI-1, ZI-2, ZI-3, ZI-4, ZI-5, ZI-6A, ZI-6B, or ZI-7.

### Claim 11 (depends on 1)

The process of claim 1 wherein the zwitterionic polymer comprises repeat units corresponding to Formula 3:
wherein X44 comprises an oxylated alkylene moiety, a zwitterionic moiety, an anionic moiety, or a cationic moiety.

### Claim 12 (depends on 11)

The process of claim 11 wherein X44 is —OX45, —NHX45, or —SX45, and X45 is a substituted hydrocarbyl or heterocyclo moiety comprising an oxylated alkylene moiety, a zwitterionic moiety, an anionic moiety, or a cationic moiety.

### Claim 13 (depends on 11)

The process of claim 11 wherein X44 is —O(CH2)2N+(CH3)2(CH2)nSO3−, —O(CH2)2N+(CH3)2(CH2)nCO2−, NH(CH2)3N+(CH3)2(CH2)nCO2−, or —NH(CH2)3N+(CH3)2(CH2)nSO3−, and n is 1-8.

### Claim 14 (depends on 11)

The process of claim 11 wherein X44 is —NH(CH2)mN(CH2)nCH3(CH2)pSO3, —NH(CH2)mN(CH2)nCH3(CH2)pCO2, —NH(CH2)mN+[(CH2)nCH3]2(CH2)pSO3, —NH(CH2)N+[(CH2)nCH3]2 (CH2)pCO2, —NH(CH2)mNcyclo-(CH2)pCO2, or —NH(CH2)mNcyclo-(CH2)pSO3, Ncyclo- is a heterocyclic structure or a heterocyclic derivative containing at least one nitrogen atom, m is 1-8; n is 0-5; and p is 1-8.

### Claim 15 (depends on 11)

The process of claim 11 wherein X44 is —O(CH2)mN(CH2)nCH3(CH2)pSO3, —O(CH2)mN(CH2)nCH3(CH2)pCO2, —O(CH2)mN+[(CH2)nCH3]2(CH2)pSO3, —O(CH2)N+[(CH2)nCH3]2 (CH2)pCO2, —O(CH2)mNcyclo-(CH2)pCO2, or —O(CH2)mNcyclo-(CH2)pSO3, Ncyclo- is a heterocyclic structure or a heterocyclic derivative containing at least one nitrogen atom, m is 1-8; n is 0-5; and p is 1-8.

### Claim 16 (depends on 30)

The process of claim 30 wherein X44 is —O(CH2)2N+(CH3)2(CH2)3SO3, —O(CH2)2N+(CH3)2(CH2)2CO2, —NH(CH2)2N+(CH3)2(CH2)3SO3, —NH(CH2)2N+(CH3)2(CH2)2CO2, —NH(CH2)3N+(CH3)2(CH2)3SO3, —NH(CH2)3N+(CH3)2(CH2)2CO2, —O(CH2)2N+(CH2CH3)2(CH2)3SO3, —O(CH2)2N+(CH2CH3)2(CH2)2CO2, —O(CH2)2N+(CH2CH2CH2CH3)2 (CH2)3SO3, —O(CH2)2N+(CH2CH2CH2CH3)2(CH2)2CO2 or —NH(CH2)3Ncyclo-(CH2)3SO3 and Ncyclo- is a heterocyclic structure or a heterocyclic derivative containing at least one nitrogen atom

### Claim 17

A process for modifying the surface of a silicon-containing polymer, the process comprising the steps of:
imbibing a zwitterionic monomer into a silicon-containing polymer in an imbibing mixture comprising the silicon-containing polymer, the zwitterionic monomer, and a solvent system; and
polymerizing the zwitterionic monomer to modify the surface of the silicon-containing polymer with a zwitterionic polymer in a polymerization reaction mixture comprising the imbibed silicon-containing polymer, a free radical initiator and a solvent system wherein the polymerization reaction mixture has a composition that differs from the composition of the imbibing mixture.

### Claim 18 (depends on 17)

The process of claim 17 wherein the silicon-containing polymer contains at least 1 wt. % silicon.

### Claim 19 (depends on 17)

The process of claim 17 wherein the silicon-containing polymer contains at least 20 wt. % silicon.

### Claim 20 (depends on 17)

The process of claim 17 wherein the zwitterionic polymer comprises a carboxyammonium polymer or a sulfoammonium polymer.

### Claim 21 (depends on 17)

The process of claim 17 wherein the zwitterionic polymer comprises a carboxybetaine polymer or a sulfobetaine polymer

### Claim 22 (depends on 1)

An article formed by the process of claim 1.

### Claim 23 (depends on 22)

The article of claim 22 wherein the article is a contact lens.