Oxygen permeable contact lens material comprising copolymers of multifunctional siloxanyl alkylesters

• US 4,414,375 A
• Filed: 09/08/1981
• Issued: 11/08/1983
• Est. Priority Date: 09/02/1980
• Status: Expired due to Fees

• Current Assignee: Dome Patent LP
• Original Assignee: Russell A. Neefe
• Inventors: Neefe, Russell A.
• Primary Examiner(s): Marquis, Melvyn I.
• Assistant Examiner(s): Lilling, Herbert J.
• Application Number:
  US06/300,189
• Time in Patent Office: 791 Days
• Field of Search: 526/279, 526/79, 526/273, 526/260, 526/264, 526/265
• US Class Current: 526/260
• 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

Abstract

An oxygen permeable contact lens fabricated from a copolymer of a multifunctional siloxanyl alkylester a monomer selected from the group consisting of, an ester of acrylic or methacrylic acid and from an ester of itaconic acid or mixture thereof. The copolymer can be made either hard, soft, or elasticmeric with improved oxygen permeability.

Claims

1. An oxygen permeable material for the manufacture of contact lenses formed by copolymerizing (a) from 5 to 90% by weight of a multifunctional siloxanyl alkyl ester, monomer having two or more α

, ω

terminally bonded through divalent hydrocarbon groups to an activated unsaturated group, (b) an effective amount of a copolymerizable monomer up to 90% by weight of an ester of acrylic or methacrylic acid or mixture thereof, or from (c) an effective amount of a copolymerizable monomer up an ester of itaconic acid, (d) from 0.5 to 40% by weight of a hydrophilic monomer for a surface wetting agent, and (e) from 0 to 20% by weight of an ester crosslinking agent in the presence of a free radical or a photo initiator.

2. A composition as defined in claim 1 wherein said multifunctional siloxanyl alkyl ester monomer having two or more α

, ω

terminally bonded through divalent hydrocarbon groups to an activated unsaturated groups;

includes at least one of the following group;

tetrakis-(trimethylsiloxy)bis(methacryloxypropyl)disiloxane

tetrakis-(trimethylsiloxy)bis(methacryloxypropyl)dimethyltrisiloxane

pentakis-(trimethylsiloxy)tris(methacryoxypropyl)tetramethyl-pentasiloxane

hexakis-(trimethylsiloxy)tetrakis-(methacryloxpropyl)-hexamethyl heptasiloxane

tris-(methacryloxymethyldimethylsiloxy)methacryloxypropylsiloxane

tetrakis-(methacryloxymethyldimethylsiloxy)tetramethylcyclotetra-siloxane

tetrakis-(methacryloxymethyldimethylsiloxy)siloxane.

3. A composition as defined in claim 1 wherein said ester of acrylic or methacrylic acid include at least one of the following group:

butyl acrylate, butyl methacrylate

cyclohexyl acrylate, cyclohexyl methacrylate

2-ethylacrylate, 2-ethylmethacrylate

glycidyl acrylate, glycidyl methacrylate

hexyl acrylate, hexyl methacrylate

lauryl acrylate, lauryl methacrylate

methyl acrylate, methyl methacrylate

stearyl acrylate, stearyl methacrylate.

4. A composition as defined in claim 1 wherein said ester of itaconic acid include at least one of the following group:

butyl itaconate

dibutyl itaconate

methyl itaconate

dimethyl itaconate

phenyl itaconate

diphenyl itaconate.

5. A composition as defined in claim 1 wherein said a hydrophiliomonomer for a surface wetting agent include at least one of the following group:

acrylamide

2-acrylamido-2 methyl propane sulfonic acid

t-butylaminoethyl methacrylate

dimethylaminoethylacrylate, dimethylaminoethylmethacrylate

N-(1,1-dimethyl-3-oxobutyl)acrylamide

glacial acrylic acid, glacial methacrylic acid

glyceryl acrylate, glyceryl methacrylate

itaconic acid

propylene glycolmonoacrylate, propylene glycol monomethacrylate

ethylene glycol monoacrylate, ethylene glycol monomethacrylate methacrylamide

morpholinoethyl acrylate, morphilinoethyl methacrylate

piperidinoethyl acrylate, piperidinoethyl methacrylate

triethylene glycol methacrylate

N-vinyl pyrrolidone

dihydroxypropyl acrylate, dihydroxypropyl methacrylate.

6. A composition as defined in claim 1 wherein said an ester crosslinking agent include at least one of the following group:

bis(methacryloxypropyl)tetramethyldisiloxane

1,3 bis(glycidoxypropyl)tetramethyldisiloxane

divinyl diphenyl silane

ethylene glycol diacrylate, ethylene glycol dimethacrylate diethylene glycol dicacrylate, diethylene glycol dimethacrylate trimethylpropane triacrylate, trimethylpropane trimethacrylate triethylene glycol diacrylate, triethylene glycol dimethacrylate tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate.