HIGH IONIC STRENGTH PROCESS FOR CONTACT LENS MODIFICATION

• US 20130188124A1
• Filed: 12/14/2012
• Published: 07/25/2013
• Est. Priority Date: 12/14/2011
• Status: Abandoned Application

• Current Assignee: Arrow International Incorporated (Teleflex Incorporated)
• Original Assignee: Semprus BioSciences Corp. (Teleflex Incorporated)
• Inventors: LI, Jun, ZHANG, Zheng, LOOSE, Christopher R.
• Application Number:
  US13/715,819
• Publication Number:
  US 20130188124A1
• Time in Patent Office: Days
• US Class Current: 351/159.33
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00865 Applying coatings; tinting; colouring printing, marking or copying processes B41M; identification in general G09F3/00; producing decorative effects in general B44C; positioning or marking of lenses B24B13/0055
• CPC Class Codes: C08J 2383/04 Polysiloxanes
• CPC Class Codes: C08J 2433/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/049 Contact lenses having special fitting or structural features achieved by special materials or material structures

Abstract

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

Claims

1. A process for modifying the surface of a silicon-containing polymer, the process comprising the steps of:

forming a polymerization reaction mixture comprising the silicon-containing polymer, a polymerization monomer, a free radical initiator system, a salt, and a solvent system, the polymerization monomer comprising a zwitterionic monomer; and

polymerizing the monomer in the polymerization reaction mixture to form a surface modification polymer on the surface of the silicon-containing polymer.

2. The process of claim 1 wherein the salt is a monovalent salt.

3. The process of claim 1 wherein the salt is selected from sodium chloride, potassium chloride, potassium iodide, sodium bromide, ammonium bromide, alkali metal nitrates, and ammonium nitrates.

4. The process of claim 3 wherein the salt is present in the polymerization reaction mixture at a concentration of from about 10 mM to about 10 M.

5. The process of claim 1 wherein the salt is present in the polymerization reaction mixture at a concentration of from about 100 mM to about 5 M.

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

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

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

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

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

11. The process of claim 1 wherein the surface modification polymer comprises repeat units corresponding to Formula 3:

12. 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.

13. The process of claim 11 wherein X³ is hydrogen or alkyl.

14. The process of claim 11 wherein the repeat units corresponding to Formula 3 comprise cationic repeat units and/or an anionic repeat units.

15. 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.

16. 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.

17. 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.

18. The process of claim 11 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.

19. An article formed by the process of claim 1.

20. The article of claim 19 wherein the article is a contact lens.