Fumarate and fumaramide siloxane hydrogel compositions

• US 5,496,871 A
• Filed: 03/01/1995
• Issued: 03/05/1996
• Est. Priority Date: 03/15/1993
• Status: Expired due to Term

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Lai, Yu-Chin, Bambury, Ronald E.
• Primary Examiner(s): Nagumo, Mark
• Application Number:
  US08/397,300
• Time in Patent Office: 370 Days
• Field of Search: 523/106, 523/107, 523/108, 526/245, 526/279
• US Class Current: 523/107
• CPC Class Codes: C07F 7/081 comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C08F 290/064 Polymers containing more than one epoxy group per molecule
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08F 30/08 containing silicon
• CPC Class Codes: C08L 35/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Novel fumarate- and fumaramide-containing monomers are disclosed which are especially useful in the preparation of biocompatible devices, especially contact lenses.

Claims

1. A contact lens produced from a monomer mix comprising

a) at least one fumarate-containing or fumaramide-containing monomer having the following schematic representations:

##STR9## wherein ##STR10## X₁, X₂, Y₁ and Y₂ are independently O or NR₄, except that when G is siloxane-containing, X₁ and X₂ must be NR₄ ;

Z₁ and Z₂ are independently OR₃ or NR₄ R₅ ;

R₁, R₂, R₃, R₄ and R₅ are independently H or an alkyl group having 1 to 10 C atoms;

R₆, R₇, R₈, R₉, R₁₀ and R₁₁ are independently hydrogen or an alkyl-containing group having 1 to 10 C atoms, or fluoroalkyl-containing group having 1 to 10 C atoms;

R₁₂, R₁₃ and R₁₄ are independently methyl, trimethylsiloxy or pentamethyldisiloxanyloxy;

m is 1 to 10;

n is 5 to 100;

b) at least one hydrophilic monomer.

2. The contact lens of claim 1 wherein said hydrophilic monomer is selected from the group consisting of N-vinyl pyrrolidone, N-vinyl-N-methyl acetamide, N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide, N,N-dimethyl acrylamide, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, methacrylic acid and acrylic acid.

3. The contact lens of claim 1 wherein said hydrophilic monomer is N,N-dimethylacrylamide.

4. The contact lens of claim 1 wherein said hydrophilic monomer is N-vinyl pyrrolidone.

5. The contact lens of claim 1 wherein said monomer mix further comprises a hydrophilic monomers.

6. The contact lens of claim 1 wherein said monomer mix further comprises at least one polyorganosiloxane-containing monomer.

7. The contact lens of claim 1 wherein said monomer mix further comprises a bulky polysiloxanylalkyl monomer.

8. The contact lens of claim 1 wherein said monomer mix is a hydrogel.

9. The contact lens of claim 1 wherein said monomer mix is cured using a combination of thermal and UV energy.

10. The contact lens of claim 1 wherein said monomer mix is cured using UV energy.

11. A monomer mix comprising

a) at least one fumarate-containing or fumaramide-containing monomer having the following schematic representations:

##STR11## wherein ##STR12## X₁, X₂, Y₁ and Y₂ are independently O or NR₄, except that when G is siloxane-containing, X₁ and X₂ must be NR₄ ;

Z₁ and Z₂ are independently OR₃ or NR₄ R₅ ;

R₁, R₂, R₃, R₄ and R₅ are independently H or an alkyl group having 1 to 10 C atoms;

R₆, R₇, R₈, R₉, R₁₀ and R₁₁ are independently hydrogen or an alkyl-containing group having 1 to 10 C atoms, or fluoroalkyl-containing group having 1 to 10 C atoms;

R₁₂, R₁₃ and R₁₄ are independently methyl, trimethylsiloxy or pentamethyldisiloxanyloxy;

m is 1 to 10;

n is 5 to 100;

b) at least one hydrophilic monomer;

c) at least one initiator;

wherein said mix is cured using a combination of thermal and UV energy.

12. The monomer mix of claim 11 wherein said mix is cured using UV energy.