Silicone-containing contact lens material and contact lenses made thereof

• US 4,826,936 A
• Filed: 10/04/1985
• Issued: 05/02/1989
• Est. Priority Date: 12/04/1981
• Status: Expired due to Term

• Current Assignee: B&L International Holdings Corp.
• Original Assignee: Polymer Technology Group, Inc. (DSM-Firmenich AG)
• Inventors: Ellis, Edward J.
• Primary Examiner(s): Briggs, Sr., Wilbert J.
• Application Number:
  US06/784,958
• Time in Patent Office: 1,306 Days
• Field of Search: 526/279, 526/258
• US Class Current: 526/258
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08F 30/08 containing silicon
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: G02B 1/04 made of organic materials, e.g. plastics G02B1/08 takes precedence
• CPC Class Codes: G02C 7/04 Contact lenses for the eyes disinfection or sterilisation of contact lenses A61L12/00

Abstract

According to the invention contact lenses are formed of unsaturated, multifunctional, organosiloxanes alone or mixed with monofunctional organosilanes and in some cases a hardening agent such as methyl methacrylate, hydrophilic monomer wetting agents, and itaconate hydrophilic and hardening agents. In the preferred embodiment, an additional hydrophilic cross-linking agent is used and the multifunctional organosiloxane is less than 50% of the organosiloxane used. The multifunctional organosiloxane adds higher impact strength and reduces brittleness, probably due to greater cross-linking density in the final product and retains the desirable properties of silicone-containing materials for use in contact lenses.

Claims

1. A contact lens material comprising a polymer formed from polymerization of a mixture of from 20 to 50% by weight of a multifunctional, unsaturated, organosiloxane having the formula:

##STR5## WHEREIN;

Y'"'"' is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl and allyl,

X'"'"' is a divalent hydrocarbon having from 0 to 10 carbons,

Y is an unsaturated polymerizable group selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl and allyl, or hydrogen,

X is a divalent hydrocarbon having from 1 to 10 carbon atoms, or phenylene,

A is selected from the group consisting of straight chain, branched chain, or cyclic alkyl groups having 1 to 5 carbon atoms, phenyl groups and "Z" groups,

Z is a group selected from the following;

trimethyl siloxy

pentamethyl disiloxanyl

heptamethyl trisiloxanyl

nonamethyl tetrasiloxanyl

bis(trimethylsiloxy)methyl siloxanyl

Tris(trimethylsiloxy) siloxanyl

"a" is an integer from 0 to 10;

the total of "a" values is at least 2,

"n" is an integer from 0 to about 10, and each of said X, X'"'"', Y, Y'"'"' a, A and Z groups being the same or different,

combined with from 30 to 50% by weight of a monofunctional, unsaturated organosiloxane monomer having the formula;

##STR6## WHEREIN;

R is selected from the group consisting of methyl groups and hydrogen,

"a" is an integer from 1 to 4,

A is selected from the group consisting of straight chain, branched chain, or alkyl groups of from 1 to 5 carbon atoms, cyclohexyl groups, phenyl groups and Z groups,

Z is a group selected from trimethyl siloxy, pentamethyl disiloxanyl, heptamethyl trisiloxanyl, nonamethyl tetrasiloxanyl, bis(trimethylsiloxy) methyl siloxanyl, tris(trimethylsiloxy) siloxanyl,

"b" is an integer from 0 to 10, each "b", "A" and Z may be the same or different, and the total of "b" values being at least 1,

and a hydrophilic cross-linking agent.

2. A contact lens material in accordance with claim 1 wherein said unsaturated polymerizable group Y and Y'"'"' is selected from the group consisting of vinyl, methacryloxy, acryloxy, methacrylamido, acrylamido, styryl, allyl and the alkylene radical of X and X'"'"' is selected from the class consisting of methylene, ethylene, propylene, butylene.

3. A contact lens material in accordance with claim 2 wherein A is chosen from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, alkaryl, haloaryl and halo substituted lower alkyl radicals.

4. A contact lens material in accordance with claim 1 wherein said multifunctional organosiloxane is 1,3-Bis(γ

-methacryloxymethyl)-1,1,3,3 tetra(trimethylsiloxy)disiloxane.

5. A contact lens material in accordance with claim 1 wherein said multifunctional organosiloxane is 1,3-Bis(γ

-methaoryloxypropyl)-1,1,3,3 tetra(trimethylsiloxy)disiloxane.

6. A contact lens material in accordance with claim 1 wherein said multifunctional organosiloxane is tetra[γ

-methacryloxypropyl dimethyl siloxy]silane.

7. A contact lens material in accordance with claim 1 wherein said multifunctional organosiloxane is 1,3-Bis(γ

-methacryloxypropyl)-1,1,3,3 tetra(pentamethyl disiloxanyl) disiloxane.

8. A contact lens material in accordance with claim 1 wherein said multifunctional organosiloxane is 1,3-Bis(γ

-methacryloxypropyl)-1,1,3,3 tetra[Bis(trimethylsiloxy)methyl siloxanyl]disiloxane.

9. A contact lens material in accordance with claim 1 wherein said multifunctional organosiloxane is 1,7-Bis (γ

-methacryloxypropyl)-1,1,3,3,5,5,7,7-octa(trimethylsiloxy)tetrasiloxane.

10. A contact lens material in accordance with claim 1 wherein said multifunctional organosiloxane is Tris(γ

-methacryloxypropyl tetramethyl disiloxanyl)trimethylsiloxy silane.

11. A contact lens material in accordance with claim 1 wherein said multifunctional organosiloxane is 1,7-Bis(γ

-methacryloxypropyl)-1,1,7,7-tetra(pentamethyl disiloxanyl)-3,3,5,5-tetra (trimethylsiloxy)tetrasiloxane.

12. A contact lens material in accordance with claim 1 wherein said multifunctional organosiloxane is Tris(γ

-methacryloxypropyl tetramethyl disiloxanyl)methyl silane.

13. The contact lens composition of claim 1 wherein said multifunctional siloxane and said monofunctional unsaturated organosiloxane monomer are present in combination,

said combination being present in an amount of 35 to 75% by weight admixed with from 1 to 20% by weight of the entire combination of a wetting agent and from 1 to 10% by weight of the entire combination of said hydrophilic cross-linking agent,

said wetting agent being a hydrophilic monomer.

14. A contact lens composition in accordance with claim 13 and further comprising from 1 to 45% by weight of a hardening agent which is an ester of a C₁ -C₂ monohydric or polyhydric alkanol or phenol and an acid selected from the group consisting of acrylic and methacrylic acid.

15. A contact lens material in accordance with claim 14 and further comprising an itaconate mono or di ester adding hardening and hydrophilic properties to said material.

16. A contact lens material in accordance with claim 1 and further comprising said itaconate being present in an amount of from 1 to 20% by weight of the entire material.

17. A contact lens material for use in forming contact lenses, said material comprising a polymer formed from polymerization of a mixture of dimethyl itaconate, methylmethacrylate, methacrylic acid, N-vinyl-2-pyrrolidone, tetraethylene glycol dimethacrylate, and a mixture of 20 to 50% 1,3-Bis(-methacryloxypropyl)-1,1,3,3 tetra(trimethylsiloxy)disiloxane and 50 to 80% by weight of a monomer of methacryloxypropyltris (trimethylsilyl) siloxane.

18. A contact lens material in accordance with claim 17 wherein said monomer is present in an amount of 80% by weight.