SILICONE HYDROGEL CONTACT LENS MODIFIED USING LANTHANIDE OR TRANSITION METAL OXIDANTS

• US 20130176529A1
• Filed: 12/14/2012
• Published: 07/11/2013
• Est. Priority Date: 12/14/2011
• Status: Active Grant

• Current Assignee: Arrow International Incorporated (Teleflex Incorporated)
• Original Assignee: Semprus BioSciences Corp. (Teleflex Incorporated)
• Inventors: LI, Jun, ZHANG, Zheng, LOOSE, Christopher R., COURY, Arthur
• Granted Patent: US 8,870,372 B2
• Time in Patent Office: Days
• US Class Current: 351/159.33
• CPC Class Codes: C08F 20/10 Esters
• CPC Class Codes: C08G 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence
• CPC Class Codes: C08J 2383/04 Polysiloxanes
• CPC Class Codes: C08J 7/16 with polymerisable compounds
• 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 7/04 Contact lenses for the eyes disinfection or sterilisation of contact lenses A61L12/00

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 reaction mixture comprising the silicon-containing polymer, a polymerization monomer, a free radical redox initiator system and a solvent system, the polymerization monomer comprising a zwitterionic monomer and the free radical redox initiator system comprising a Lanthanide or Transition metal oxidant; and

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

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

3. The process of claim 1 wherein the silicon-containing polymer contains at least 25 wt. % silicon.

4. The process of claim 1 wherein the Lanthanide or Transition metal oxidant is a cerium (IV) salt.

5. The process of claim 1 wherein the Lanthanide or Transition metal oxidant is selected from the following:

Fe²⁺, Cr²⁺, V²⁺, Ti³⁺, Co²⁺, and Cu⁺.

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

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

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

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

10. The process of claim 1 wherein the surface modification polymer comprises at least one repeat unit corresponding to Formula 2:

11. The process of claim 1 wherein the surface modification polymer 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 methyl and X⁴⁴ comprises an oxylated alkylene moiety corresponding to Formula POA-1 or a zwitterionic moiety corresponding to Formula ZI-1, ZI-2, ZI-3, ZI-4, ZI-5, ZI-6A, ZI-6B, or ZI-7.

14. 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.

15. 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.

16. 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.

17. The process of claim 11 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.

18. The process of claim 1 wherein the surface modification polymer comprises repeat units corresponding to Formula 4:

19. The process of claim 1 wherein the surface modification polymer comprises repeat units corresponding to Formula 5, Formula 6, Formula 7, Formula 8, or Formula 9:

20. The process of claim 1 wherein the silicon-containing polymer is comprised by a contact lens.

21. A contact lens formed by the process of claim 1.