Ultraviolet radiation absorbing agent for bonding to an ocular lens

• US 5,098,445 A
• Filed: 01/22/1990
• Issued: 03/24/1992
• Est. Priority Date: 03/14/1989
• Status: Expired due to Term

• Current Assignee: CIBA Vision Corporation (Novartis Ag)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Su, Kai C., Hung, William M.
• Primary Examiner(s): Clingman, A. Lionel
• Application Number:
  US07/468,386
• Time in Patent Office: 792 Days
• Field of Search: 8/507
• US Class Current: 8/507
• CPC Class Codes: C07D 251/50 with a halogen atom attached to the third ring carbon atom
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: D06P 1/6426 Heterocyclic compounds

Abstract

An ultraviolet radiation absorbing contact lens and method ofl 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;

E,A=an ultraviolet radiation absorbing component; and

E¹ =an aqueous soluble moiety.

Claims

1. An ultraviolet radiation absorbing agent for bonding to an ocular lens, wherein said agent has the formula:

##STR9## wherein A and E are ultraviolet radiation absorbing components which are either identical to or dissimilar to each other, or of the formula ##STR10## where X=Cl or F;

A=an ultraviolet radiation absorbing component selected from the group consisting of p-benzoic acid, p-salicyclic acid, substituted benzophenone, substitued benzotriazoles, benzoic acid esters, acrylates, oxalic acid diamides, and hydroxy phenyltriazines;

E=an ultraviolet radiation absorbing component selected from the group consisting of p-aminobenzoic acid, p-aminosalicylic acid, substituted benzophenone and substituted benzotriazoles, benzoic acid esters, acrylates, oxalic acid diamides, and hydroxy phenyltriazines;

E¹ =an aqueous soluble moiety of the formula ##STR11## where Y is an amine salt or an alkali metal salt; and

R₅ -R₆ are selected from the group consisting of hydrogen, alkyl chains varying from C₁ to C₁₈, C₁ -C₁₈ alkoxy, halogen, nitro, hydroxy, carboxy, sulfonic acid or a salt thereof.

2. The compounds in claim 1 wherein at least one of A and E is selected from the group consisting of ##STR12## where R₁ -R₂ are independently selected from the group consisting of hydrogen, alkyl chains varying from C₁ to C₁₈, C₁ -C₁₈ alkoxy, halogen, nitro, hydroxy, carboxy, sulfonic acid, or sulfonic acid alkali metal salts and R₃ and R₄ are independently selected from hydrogen and C₁ -C₁₈ alkyl.

3. The compound of claim 2 wherein said R₁, R₂, R₃ and R₄ C₁ -C₁₈ alkyl is C₁ -C₄ alkyl, and said R₁ and R₂ C₁ -C₁₈ alkoxy is C₁ -C₄ alkoxy.

4. The ultraviolet radiation absorbing agent of claim 1, wherein said agent is selected from the group consisting of 2-chloro-4-[(4-carboxy)phenylamino]-6-{2-sulfo-4-[(2-hydroxy-4-methoxy-5-sulfo)benzoyl]phenylamino}-s-triazine;

2-chloro-4-[(3-hydroxy-4-carboxy)phenylamino]-6-{4-[(2-hydroxy-4-methoxy-5-sulfo)benzoyl]phenylamino}-s-triazine;

2-chloro-4-[(3-hydroxy-4-carboxy)phenylamino]-6-{2-sulfo-4-[(2-hydroxy-4-methoxy-5-sulfo)benzoly]phenylamino}-s-triazine;

2-chloro-4-[(4-carboxy)phenylamino]-6-{4-[(2-hydroxy-4-methoxy-5-sulfo)benzoyl]phenylamino}-s-triazine; and

sodium salts thereof.

5. The compound of claim 1 wherein said R₅ and R₆ C₁ -C₁₈ alkyl and C₁ -C₁₈ alkoxy are selected from C₁ -C₄ alkyl and C₁ -C₄ alkoxy.

6. The compound in claim 1, wherein said compound is selected from the group consisting of;

2-chloro-4-[7-(1,3-disulfo)naphthylamino]-6-[(3-hydroxy-4-carboxy)phenylamino]-s-triazine;

2-chloro-4-[3-(2,7-disulfo)naphthylamino]-6-[(3-hydroxy-4-carboxy)phenylamino]-s-triazine;

2-chloro-4-[(3-hydroxy-4-benzotriazo-2-yl)phenylamino]-6-[7-(1,3-disulfo)naphthylamino]-s-triazine;

2-chloro-4-[4-(2-hydroxy-4-methoxybenzoyl)phenylamino]-6-[7-(1,3-disulfo)naphthylamino]-s-triazine.

7. The compound of claim 1 wherein A and E are different components.

8. The compound of claim 1 wherein A and E are identical components.