High refractive index ophthalmic device materials prepared using a post-polymerization cross-linking method

• US 6,313,187 B2
• Filed: 01/19/2001
• Issued: 11/06/2001
• Est. Priority Date: 04/15/1998
• Status: Expired due to Term

• Current Assignee: Novartis Ag
• Original Assignee: Alcon Manufacturing Limited (Alcon Incorporated)
• Inventors: Weinschenk, Joseph I. III, Schlueter, Douglas C., LeBoeuf, Albert R.
• Primary Examiner(s): Yoon, Tae H.
• Application Number:
  US09/766,493
• Publication Number:
  US 20010025086A1
• Time in Patent Office: 291 Days
• Field of Search: 522/13, 522/182, 522/183, 522/184, 523/106, 526/232
• US Class Current: 522/13
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/16 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 220/12 of monohydric alcohols or phenols
• CPC Class Codes: C08F 220/26 Esters containing oxygen in addition to the carboxy oxygen
• CPC Class Codes: C08L 33/04 Homopolymers or copolymers of esters C08L43/04 takes precedence
• CPC Class Codes: C08L 33/06 of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Acrylic, high refractive index ophthalmic device materials comprising an aryl acrylic monomer, a first stage polymerization initiator and a second stage cross-linking agent are prepared in a two-stage method. The monomers used to form the ophthalmic device materials do not contain cross-linking agents having more than one unsaturated bond. In the first stage of the method, the materials are polymerized. In the second stage, the materials are cross-linked by exposure to heat.

Claims

1. A two-stage method for preparing an acrylic, high refractive index ophthalmic device material, wherein the ophthalmic device material comprises

(i) at least two aryl acrylic hydrophobic monomers of the formula

 

wherein;

X is H or CH₃;

m is 0-10;

Y is nothing, O, S, or NR wherein R is H, CH₃, C_nH_2n+1 (n=1-10) iso OC₃H₇, C₆H₅, or CH₂C₆H₅;

Ar is any aromatic ring which can be unsubstituted or substituted with CH₃, C₂H₅, n-C₃H₇, iso-C₃H₇, OCH₃, C₆H₁₁, Cl, Br, C₆H₅, or CH₂C₆H₅;

and further wherein at least one of the aryl acrylic hydrophobic monomers is a methacrylate monomer and at least one of the aryl acrylic hydrophobic monomers is an acrylate monomer;

(ii) a first stage polymerization initiator selected from the group consisting of photoinitiators and thermal free radical initiators having a 10 hr t_½

of about 55°

C. or less; and

(iii) a second stage cross-linking agent where the second stage cross-linking agent is a thermal free radical initiator having a 10 hr t_½

of about 50°

C. or greater if the first stage polymerization initiator is a photoinitiator and the second stage cross-linking agent is a thermal free radical initiator having a 10 hr t_½

of about 65°

C. or greater if the first stage polymerization initiator is a thermal free radical initiator having a 10 hr t_½

of about 55°

C. or less, wherein the first stage of the method comprises polymerizing the ophthalmic device material by activating the first stage polymerization initiator without activating the second stage cross-linking agent; and

the second stage of the method comprises cross-linking the ophthalmic device material by activating the second stage cross-linking agent.

2. The method of claim 1 wherein the ophthalmic device materials comprise a total of at least 50% (w/w) of aryl acrylic hydrophobic monomers of Formula (I).

3. The method of claim 2 wherein the ophthalmic device materials comprise a total of at least 70% (w/w) of aryl acrylic hydrophobic monomers of Formula (I).