# US 2013/0158150 A1 · Multistep uv process to create surface modified contact lenses

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- Number: US 2013/0158150 A1
- Document ID: US20130158150A1
- Status: Published application
- Kind: A1
- Application number: 13/715,832
- Filed: 2012-12-14
- Published: 2013-06-20
- Earliest claimed: 2011-12-14
- Assignees: Semprus Biosciences Corp.
- Inventors: Zheng ZHANG; Alonzo COOK; Karen Ann SCHULTZ; Jun LI; Christopher R. LOOSE; Arthur COURY
- Web page: https://patentgrep.com/patent/US20130158150A1

## CPC

- C08G 77/00: Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08F 265/00: Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F 290/068: {Polysiloxanes}
- C08F 290/148: {Polysiloxanes}
- C08G 77/06: Preparatory processes
- C08G 77/442: containing vinyl polymer sequences
- C08K 5/0025: {Crosslinking or vulcanising agents; including accelerators}
- B29D 11/00038: {Production of contact lenses}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- B29D: PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE (making granules B29B9/00; making preforms B29B11/00)

## 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:
forming a silicon-containing polymer containing a photo-initiator in a first polymerization reaction mixture, in which the photo-initiator initiates the polymerization and/or crosslinking of the silicon-containing polymer;
forming a second polymerization reaction mixture comprising the silicon-containing polymer, a polymerization monomer, a free radical initiator system and a solvent system, the polymerization monomer comprising a zwitterionic monomer, wherein no more than 25% of the photo-initiator contained by the silicon-containing polymer is removed from the silicon-containing polymer before the silicon-containing polymer is combined with the solvent system of the second polymerization reaction mixture; and
polymerizing the monomer in the second polymerization reaction mixture to form a surface modification on the surface of the silicon-containing polymer.

### Claim 2 (depends on 1)

The process of claim 1 wherein no more than 20% of the photo-initiator contained by the silicon-containing polymer is removed from the silicon-containing polymer before the silicon-containing polymer is combined with the solvent system of the second polymerization reaction mixture

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

The process of claim 1 wherein the surface modification polymer comprises a zwitterionic polymer.

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

The process of claim 1 wherein the surface modification 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 8 (depends on 7)

The process of claim 7 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 9 (depends on 8)

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

### Claim 10 (depends on 7)

The process of claim 7 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 11 (depends on 7)

The process of claim 7 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 12

A process for modifying the surface of a silicon-containing polymer, the process comprising the steps of:
forming a silicon-containing polymer in a first polymerization reaction mixture, the first polymerization reaction mixture comprising a photo-initiator whereby the photo-initiator initiates the polymerization and/or crosslinking of the silicon-containing polymer;
forming a second polymerization reaction mixture comprising the silicon-containing polymer, a polymerization monomer, a free radical initiator system and a solvent system, the polymerization monomer comprising a zwitterionic monomer, wherein no additional photo-initiator is added to the silicon-containing polymer before the silicon-containing polymer is combined with the solvent system of the second polymerization reaction mixture; and
polymerizing the monomer in the second polymerization reaction mixture to form a surface modification polymer on the surface of the silicon-containing polymer.

### Claim 13

A process for modifying the surface of a silicon-containing polymer, the process comprising the steps of:
forming a silicon-containing polymer in a first polymerization reaction mixture, the first polymerization reaction mixture comprising a photo-initiator whereby the photo-initiator initiates the polymerization and/or crosslinking of the silicon-containing polymer;
forming a second polymerization reaction mixture comprising the silicon-containing polymer, a polymerization monomer, a free radical initiator system and a solvent system, the polymerization monomer comprising a zwitterionic monomer, wherein a residual amount of the photo-initiator that initiated the formation of the silicon-containing polymer in the first reaction mixture is present in the silicon-containing polymer when the silicon-containing polymer is combined with the solvent system of the second polymerization reaction mixture; and
polymerizing the monomer in the second polymerization reaction mixture to form a surface modification polymer on the surface of the silicon-containing polymer.

### Claim 14 (depends on 13)

The process of claim 13 wherein the silicon-containing polymer contains more than 10 ppm of the photo-initiator that initiated the formation of the silicon-containing polymer in the first reaction mixture when the silicon-containing polymer is combined with the solvent system of the second polymerization reaction mixture.

### Claim 15 (depends on 13)

The process of claim 13 wherein the silicon-containing polymer contains more than 1,000 ppm of the photo-initiator that initiated the formation of the silicon-containing polymer in the first reaction mixture when the silicon-containing polymer is combined with the solvent system of the second polymerization reaction mixture.

### Claim 16

A process for modifying the surface of a silicon-containing polymer, the process comprising the steps of:
forming a silicon-containing polymer in a first polymerization reaction mixture, the first polymerization reaction mixture comprising two or more unique photo-initiators whereby a first photo-initiator initiates the polymerization and/or crosslinking of the silicon-containing polymer;
forming a second polymerization reaction mixture comprising the silicon-containing polymer, a polymerization monomer, a free radical initiator system and a solvent system, the polymerization monomer comprising a zwitterionic monomer, wherein a second photo-initiator is present in the silicon-containing polymer when the silicon-containing polymer is combined with the solvent system of the second polymerization reaction mixture; and
polymerizing the monomer in the second polymerization reaction mixture to form a surface modification polymer on the surface of the silicon-containing polymer.

### Claim 17 (depends on 16)

The process of claim 16 wherein the first and second initiators are capable of being initiated at different wavelengths.

### Claim 18 (depends on 1)

An article formed by the process of claim 1.

### Claim 19 (depends on 18)

The article of claim 18 wherein the article is a contact lens.