Ultraviolet absorbing lenses and method of making the same

• US 4,929,250 A
• Filed: 03/14/1989
• Issued: 05/29/1990
• Est. Priority Date: 03/14/1989
• Status: Expired due to Term

• Current Assignee: CIBA Vision Corporation (Bayer AG)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Su, Kai C., Hung, William M.
• Primary Examiner(s): CLINGMAN, A
• Application Number:
  US07/323,354
• Time in Patent Office: 441 Days
• Field of Search: 8/507, 8/549, 8/648
• US Class Current: 8/507
• CPC Class Codes: D06P 1/6426 Heterocyclic compounds
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

An ultraviolet radiation absorbing contact lens and method of making the same, comprising a copolymeric hydrogel material to which is covalently bonded at least one halotriazine reactive ultraviolet radiation absorbing agent of the formula: ##STR1## where X=Cl or F;

A=an ultraviolet radiation absorbing component; and

B=an aqueous soluble moiety.

Claims

1. A process for preparing an ultraviolet radiation absorbing contact or intraocular lens material, comprising the steps of preparing an aqueous solution of effective amounts of a halotriazine reactive ultraviolet radiation absorbing agent and a base, wherein said reactive ultraviolet radiation absorbing agent is of the formula:

##STR8## where X=Cl or F;

A=an ultraviolet radiation absorbing component selected from the group consisting of ##STR9## where R₁ -R₃ are selected from the group consisting of hydrogen, alkyl chains varying from C₁ to C₁₈, alkoxy, halogen, nitro, hydroxy, carboxy, sulfonic acid, or sulfonic acid salt substituents; and

B=an aqueous soluble moiety of the formula ##STR10## where Y is an amine salt or an alkali salt; and

R₁ -R₂ are selected from the group consisting of hydrogen, alkyl chains varying from C₁ to C₁₈, alkoxy, halogen, nitro, hydroxy, carboxy, sulfonic acid, or sulfonic acid salt substituents,

maintaining said solution for a preselected period of time at a temperature up to at least 30°

C.;

adding a polymeric contact or intraocular lens material to said solution;

said polymeric lens material having an exoskeletal functional group selected from the group consisting of hydroxyl, amino, amide and mercapto groups and removing said polymeric lens material from the solution after a preselected time.

2. A process according to claim 1, and further comprising the step of adding an effective amount of an ammonium quaternary salt to said solution prior to said maintaining step.

3. A process according to claim 2, wherein said ammonium quaternary salt is selected from the group consisting of triethylbenzylammonium chloride, tetrabutylammonium hydrogen sulfate, phenyltrimethylammonium chloride, benzyltributylammonium chloride, tetrabutylammonium bromide, and tetramethylammonium chloride.

4. A process according to claim 1, and further comprising the step of shaping said polymeric material into a contact lens.

5. A process according to claim 1, wherein said solution has a pH of at least 10.

6. A process according to claim 1, wherein said absorbing agent is fluorotriazine reactive.

7. A process according to claim 1, wherein said absorbing agent is chlorotriazine reactive.

8. A process to claim 1, and further comprising the step of shaping said polymeric material into an intraocular lens.

9. An ultraviolet radiation absorbing contact or intraocular lens, comprising a polymeric contact or intraocular lens material said polymeric lens material having an exoskeletal functional group selected from the group consisting of hydroxyl, amino, amide and mercapto groups to which is covalently bonded at least one halotriazine reactive ultraviolet radiation absorbing agent of the formula:

##STR11## where X=Cl or F;

A=an ultraviolet radiation absorbing component; and

B=an aqueous soluble moiety

or mixtures thereof, wherein said ultraviolet radiation absorbing component is selected from the group consisting of;

##STR12## where R₁ -R₃ are selected from the group consisting of hydrogen, alkyl chains varying from C₁ to C₁₈, alkoxy, halogen, nitro, hydroxy, carboxy, sulfonic acid, or sulfonic acid salt substituents; and

wherein said aqueous soluble moiety has the formula;

##STR13## where;

Y is an amine salt or an alkali salt; and

R₁ -R₂ are selected from the group consisting of H, alkyl chains varying from C₁ to C₁₈, alkoxy, halogen, nitro, hydroxy, carboxy, sulfonic acid, or sulfonic acid salt substituents.