Multistep UV process to create surface modified contact lenses
View Patent ↗Medical devices having a wettable, biocompatible surface are described herein. Processes for producing such devices are also described.
1. 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.
2. 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.
3. The process of claim 1 wherein the silicon-containing polymer contains at least 1 wt. % silicon.
4. The process of claim 1 wherein the silicon-containing polymer contains at least 20 wt. % silicon.
5. The process of claim 1 wherein the surface modification polymer comprises a carboxyammonium polymer or a sulfoammonium polymer.
6. The process of claim 1 wherein the surface modification polymer comprises a zwitterionic polymer.
7. The process of claim 1 wherein the surface modification polymer comprises a carboxybetaine polymer or a sulfobetaine polymer.
8. The process of claim 1 wherein the surface modification polymer comprises repeat units corresponding to Formula 3:
wherein X 44 comprises an oxylated alkylene moiety, a zwitterionic moiety, an anionic moiety, or a cationic moiety.
9. The process of claim 8 wherein X 44 is —OX 45 , —NHX 45 , or —SX 45 , and X 45 is a substituted hydrocarbyl or heterocyclo moiety comprising an oxylated alkylene moiety, a zwitterionic moiety, an anionic moiety, or a cationic moiety.
10. The process of claim 9 wherein X 3 is hydrogen or alkyl.
11. The process of claim 8 wherein X 44 is —O(CH 2 ) 2 N + (CH 3 ) 2 (CH 2 ) n SO 3 − , —O(CH 2 ) 2 N + (CH 3 ) 2 (CH 2 ) n CO 2 − , —NH(CH 2 ) 3 N + (CH 3 ) 2 (CH 2 ) n CO 2 − , or —NH(CH 2 ) 3 N + (CH 3 ) 2 (CH 2 ) n SO 3 − , and n is 1-8.
12. The process of claim 8 wherein X 44 is —NH(CH 2 ) m N(CH 2 ) n CH 3 (CH 2 ) p SO 3 , —NH(CH 2 ) m N(CH 2 ) m CH 3 (CH 2 ) p CO 2 , —NH(CH 2 ) m N + [(CH 2 ) n CH 3 ] 2 (CH 2 ) p SO 3 , —NH(CH 2 )N + [(CH 2 ) n CH 3 ] 2 (CH 2 ) p CO 2 , —NH(CH 2 ) m Ncyclo-(CH 2 ) p CO 2 , or —NH(CH 2 ) m Ncyclo-(CH 2 ) p SO 3 , 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.
13. The process of claim 1 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.
14. The process of claim 1 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.
15. The process of claim 1 wherein the free-radical initiator system comprises first and second initiator sand the first and second initiators are capable of being initiated at different wavelengths.
16. An article formed by the process of claim 1 .
17. The article of claim 16 wherein the article is a contact lens.