Fluorine containing polymeric compositions useful in contact lenses

• US 4,996,275 A
• Filed: 12/12/1989
• Issued: 02/26/1991
• Est. Priority Date: 10/11/1985
• Status: Expired due to Term

• Current Assignee: B&L International Holdings Corp.
• Original Assignee: Polymer Technology Group, Inc. (DSM-Firmenich AG)
• Inventors: Ellis, Jeanne Y., Ellis, Edward J.
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): Mulcahy, Peter D.
• Application Number:
  US07/449,565
• Time in Patent Office: 441 Days
• Field of Search: 526/245, 526/246, 351/160 R, 351/160 H
• US Class Current: 526/245
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 290/062 Polyethers
• CPC Class Codes: C08F 290/068 Polysiloxanes
• 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

Improved contact lens compositions are achieved through incorporation of a fluorine containing mono or diester of itaconic acid in siloxane polymeric contact lens compositions. Copolymers include components which modify contact lens mechanical, optical and transport properties as well as surface characteristics to achieve at least some compositions having an oxygen permeability of at least DK35 with a refractive index of from 1.35 to 1.5 and a percent hydration below 2 percent of total weight. Contact lenses made of materials of this invention are highly permeable to oxygen and resistant to the deposition of tear components providing extended wear capability through improved biocompatibility.

Claims

1. A contact lens formed from polymerization of a monomeric mixture of bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate, bis(methacryloxypropyl)1,1,3,3-tetrakis (trimethyl siloxy) disiloxane, tris(trimethylsiloxy) silylpropyl methacrylate, n-vinyl pryyolidone, methacrylic acid and a cross linking agent.

2. A contact lens in accordance with claim 1, wherein said cross linking agent is tetraethylene glycol dimethacrylate.

3. A contact lens formed from polymerization of a monomeric mixture of bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate, bis(methacryloxypropyl)1,1,3,3-tetrakis (trimethyl siloxy) disiloxane, tris(trimethylsiloxy) silylpropyl methacrylate, n-vinyl pyrrolidone, a cross linking agent, and a material selected from the class consisting of methylmethacrylate, methacrylic acid and mixture thereof.

4. A contact lens formed from polymerization of a monomeric mixture of bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate, bis(methacryloxypropyl)1,1,3,3-tetrakis (trimethyl siloxy) disiloxane, tris(trimethylsiloxy) silylpropyl methacrylate, methylmethacrylate, methacrylic acid and a cross linking agent.

5. A contact lens in accordance with claim 4 wherein tetraethylene glycol dimethacrylate is said cross linking agent.

6. A contact lens in accordance with claim 4 and further comprising a neutral nomomer to increase hydrophilic properties.

7. An oxygen permeable dimensionally stable hydrophilic, contact lens of high transparency, comprising a polymer formed by free radical polymerization from

(A) 5 to 60% by weight of a fluorine containing itaconate mono or diester having the structure:

##STR3## wherein;

Z₁ and Z₂ can be the same or different and are each of a group selected from among the following with at least one of Z₁ or Z₂ containing fluorine;

Hydrogen,

straight chain alkyl groups or fluoro substituted alkyl groups containing from 1 to 18 carbon atoms,

branched chain alkyl groups or fluoro substituted alkyl groups containing from 4 to 18 carbon atoms

cyclic alkyl groups or fluoro substituted cyclic alkyl groups containing from 5 to 18 carbon atoms,

phenyl groups and fluoro substituted phenyl groups, or

benzyl and fluoro substituted benzyl groups, phenethyl and fluoro substituted phenethyl groups,

ethers and polyethers of the general structure

space="preserve" listing-type="equation">(C.sub.x P.sub.2x O).sub.e --(C.sub.y P.sub.2y+1)

WHEREIN;

"P" is hydrogen or fluorine

"x" is an integer from 1 to 4

"y" is an integer from 1 to 10

"e" is an integer from 1 to 10,

(B) from up to 95% by weight of at least one ethylenically unsaturated organosiloxane having the following formula;

##EQU6## WHEREIN;

"X" is an ethylenically unsaturated group selected from the group consisting of vinyl, acryloxy, methacryloxy, vinyloxy, and carbovinyloxy,

"Y" represents no group or is selected from the group consisting of a divalent alkane radical having from 1 to 10 carbon atoms, a divalent alkane radical having 2 to 10 carbon atoms, and a phenylene radical,

"a" is an integer from 1 to 10,

"n" is an integer from 2 to 30,

"b" is an integer from 0 to 3 and may be the same or different within each "i" moiety,

"R" is selected from the class consisting of hydrogen, hydroxy, alkoxy, carboalkoxy, alkyl and substituted alkyl groups containing from 1 to 20 carbon atoms, cyclic alkyl or substituted cyclic alkyl groups containing from 5 to 10 carbon atoms, phenyl and substituted phenyl groups, benzyl and substituted benzyl groups and phenethyl and substituted phenethyl groups, "R" and "b" may be the same or different within each "i" moiety,

(C) 0 to 55% by weight of the entire composition of a vinyl monomer hardness modifying agent,

(D) 0 to 55% by weight of the entire composition of a hydrophilic organic monomer,

(E) 0 to 20% by weight of the entire composition of a non-siloxane containing cross-linking monomer.