Dimethylacrylamide-copolymer hydrogels with high oxygen permeability

• US 4,954,587 A
• Filed: 05/23/1989
• Issued: 09/04/1990
• Est. Priority Date: 07/05/1988
• Status: Expired due to Fees

• Current Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Mueller, Karl F.
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): SAROFIM, NABIL F
• Application Number:
  US07/356,801
• Time in Patent Office: 469 Days
• Field of Search: 526/245, 526/279, 526/286
• US Class Current: 526/245
• CPC Class Codes: A61L 26/0014 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 26/008 Hydrogels or hydrocolloids
• CPC Class Codes: A61L 27/16 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/52 Hydrogels or hydrocolloids
• CPC Class Codes: C08F 220/22 Esters containing halogen
• CPC Class Codes: C08F 220/54 Amides , e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

This invention describes polymers which are obtained by copolymerization of 15-85 wt % N,N-dimethylacrylamide with about 15-85% of a fluorinated monomer such as perfluoroalkyl-alkylene acrylate or methacrylate with from 3 to 25 fluorine atoms and optionally, 0-50 wt % other acrylates or methacrylates and 0-20 wt %, but not more than 5 mol % of a polyvinyl functional crosslinking agent. These polymers are machinable in the dry state and form clear hydrogels with about 25-75 wt % water content and which possess oxygen-permeabilities 3-7 times higher than conventional hydrogels of similar water content. In the absence of crosslinking, the novel polymers are plasticized by water, forming clear hydroplastics with 30-70 wt % water content. The crosslinked polymers are especially useful for fabricating contact lenses for extended wear by either cutting and polishing a xerogel button, or by spin casting or direct molding in bulk or in solution.

Claims

1. A copolymer, having the characteristics of high clarity, high hydrophilicity, and high oxygen permeability and which is, in the water swollen hydrated state, soft and flexible, which copolymer comprises the polymerization product of, with weight percent based on the total weight of monomers (a), (b), (c) and (d), of

(a) 24.9 to 70 percent by weight of N,N-dimethylacrylamide,

(b) 65 to 19.9 percent by weight of a vinyl monomer selected from the group consisting of the acrylate or methacrylate esters of formula B1 ##STR5## wherein R₁ is hydrogen or methyl,

n is an integer from 1-4,

m is an integer from 0-11,

X is hydrogen or fluorine, with the proviso that, when m is 0, X is fluorine;

and hexafluoroisopropyl methacrylate,

(c) 10 to 40 percent by weight of a C₂ -C₄ -hydroxyalkyl acrylate or methacrylate, a C₂ -C₄ -alkoxy-alkyl acrylate or methacrylate or an oligosiloxanyl-silylalkyl acrylate or methacrylate containing 2 to 10 silicon atoms, or mixture thereof, and

(d) 0.1 to 3 percent by weight of a crosslinking agent having at least two copolymerizable vinyl groups.

2. A copolymer according to claim 1 wherein based on the total weight of copolymer, component (a) is 34.99 to 55 percent by weight, component (b) is 14.9 to 55 percent by weight, component (c) is 10 to 40 percent by weight, and component (d) is 0.1 to 2 percent by weight.

3. A copolymer according to claim 1 wherein component (b) is hexafluoroisopropyl methacrylate, undecafluorocyclohexyl-methyl methacrylate or a fluorinated acrylate or methacrylate of formula B1 where X is fluorine.

4. A copolymer according to claim 1 wherein component (b) is a fluorinated methacrylate of formula B1where X is fluorine, n is 1 or 2, and m is 1 to 7, and component (c) is 10 to 40 percent by weight.

5. A copolymer according to claim 4 wherein in component (b) R₁ is methyl.

6. A copolymer according to claim 4 wherein component (c) is methoxy-ethyl acrylate, ethoxy-ethyl methacrylate, methoxy-ethyl methacrylate, 2-hydroxyethyl methacrylate or a mixture thereof.

7. A copolymer according to claim 4 wherein component (c) is methoxyethyl methacrylate or a mixture of methoxyethyl methacrylate and 2-hydroxyethyl methacrylate.

8. A copolymer according to claim 1 wherein component (c) is 5 to 30 percent by weight of an oligosiloxanyl-silylalkyl methacrylate having 3 to 7 silicon atoms.

9. A copolymer according to claim 8 wherein component (c) is tris(trimethylsiloxanyl-silyl)propyl methacrylate.

10. A copolymer according to claim 1 wherein component (c) is 0.1 to 10 percent by weight of an ethylenically unsaturated carboxylic acid, an ethylenically unsaturated sulfonic acid, a tertiary di-C₁ -C₂ -alkylaminoalkyl acrylate or methacrylate or a hydroxy-C₂ -C₄ -alkyl acrylate or methacrylate.

11. A copolymer according to claim 1 wherein component (c) is methoxy-ethyl methacrylate, methoxy-ethyl acrylate or ethoxy-ethyl methacrylate.

12. A copolymer according to claim 1, wherein component (d) is a poly(vinyl alcohol-co-ethylene) reacted with 0.1-10 mol % of a vinyl unsaturated isocyanate.