Tinted contact lenses and a method for their preparation

• US 4,553,975 A
• Filed: 02/15/1984
• Issued: 11/19/1985
• Est. Priority Date: 08/12/1981
• Status: Expired due to Term

• Current Assignee: CIBA Vision Corporation (Bayer AG)
• Original Assignee: CIBA Vision Corporation (Bayer AG)
• Inventors: Su, Kai C.
• Primary Examiner(s): Clingman, A. Lionel
• Application Number:
  US06/580,398
• Time in Patent Office: 643 Days
• Field of Search: 8/507
• US Class Current: 8/507
• CPC Class Codes: D06P 3/008 using reactive dyes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/021 with pattern for identification or with cosmetic or therapeutic effects methods and processes take preference, e.g. printing, marking or copying processes B41M; identification in general G09F3/00; producing decorative effects in general B44C; surface treatment of glass C03C15/00 - C03C23/00; positioning or marking of lenses B24B13/0055

Abstract

Contact lenses comprising polymeric lens materials in which reactive dyestuffs have been covalently bonded to monomer units of the polymer backbone, said reactive dyestuffs being reactive dyes capable of forming either linkages with cellulose and reactive with hydroxyl, amino, amido or mercapto groups present in a hydrogel polymer to form the covalent bond therewith. The invention is of particular interest in the area of so-called hydrophilic or "soft" contact lenses, commonly referred to as hydrogel lenses.

Claims

1. A contact lens colored over at least a portion of its surface, comprising a copolymeric hydrogel material to which at least one reactive dyestuff of the formula ##STR12## or ##STR13## wherein D is the radical of an organic dyestuff radical;

R is a divalent organic electron attracting group capable of causing electron withdrawal of the C carbon atoms, thus activating the same;

X is hydrogen or halo; and

Y is leaving group;

or mixtures thereof, is covalently bonded external to the polymer backbone by reaction at temperatures up to 60°

C. with hydroxyl, amino, amido or mercapto groups present in said polymer, over the colored portion of the lens.

2. A contact lens according to claim 1, wherein said reactive dyestuff is covalently bonded by nucleophilic addition to said hydroxyl, amino, amido or mercapto groups.

3. A contact lens according to claim 1, wherein said hydrogel material contains hydroxy groups in the polymer.

4. A contact lens according to claim 1, wherein D is the radical of an azo, phthalocyanine, azomethine, nitro or anthraquinone dye.

5. A contact lens according to claim 1, comprising a colored central portion and a clear annular edge.

6. A contact lens according to claim 1, wherein the colored portion thereof has a light transmission of 90% or less in a segment of the visible light range.

7. A contact lens according to claim 1 wherein the reactive dyestuff is bonded to the polymer backbone by reaction at temperatures up to 50°

C.

8. A process for preparing a contact lens colored over at least a portion of its surface, comprising reacting at temperatures up to 60°

C. at least one reactive dyestuff of the formula ##STR14## or ##STR15## wherein D is the radical of an organic dyestuff radical;

R is a divalent organic electron attracting group capable of causing electron withdrawal of the C carbon atoms, thus activating the same;

X is hydrogen or halo; and

Y is a leaving group;

or mixtures thereof with hydroxyl, amino, amido or mercapto groups present in the polymeric hydrogel contact lens material, and removing unreacted dyestuff from said lens material.

9. A process according to claim 8, wherein said lens material is in the form of a contact lens.

10. A process according to claim 9, wherein the reaction is conducted in an aqueous medium having a pH of at least 9 and at a temperature of up to 40°

C.

11. A process according to claim 9, wherein the reactive dyestuff is applied to only a portion of said lens.

12. A process according to claim 8, wherein said dyestuff reacts by nucleophilic addition to said hydroxyl, amino, amido or mercapto groups in the hydrogel material.

13. A process according to claim 8, wherein said hydrogel material contains hydroxy groups in the polymer.

14. The process according to claim 8 wherein the reactive dyestuff and the polymeric hydrogel contact lens material is reacted at temperatures up to 50°

C.