Polymeric compositions useful in oxygen permeable contact lenses

• US 5,177,168 A
• Filed: 03/16/1992
• Issued: 01/05/1993
• Est. Priority Date: 10/17/1989
• Status: Expired due to Term

• Current Assignee: B&L International Holdings Corp.
• Original Assignee: Polymer Technology Group, Inc. (DSM-Firmenich AG)
• Inventors: Rothenberger, Scott D., Baron, Richard C.
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): SAROFIM, NABIL F
• Application Number:
  US07/851,873
• Time in Patent Office: 295 Days
• Field of Search: 526/318, 526/321, 526/325, 526/328.5, 526/245, 526/279
• US Class Current: 526/321
• CPC Class Codes: C08L 33/06 of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
• 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: G02B 1/043 Contact lenses

Abstract

Carboxylic acid esters devoid of beta hydrogens are homopolymerized or copolymerized with contact lens organic materials to form desirable contact lens materials and contact lenses. These materials have good contact lens properties, including desirable DK values, hardness, machineability and a desirable refractive index of at least 1.

Claims

1. A method of modifying the hardness and DK value of a contact lens material comprising copolymerizing a carboxylic acid ester derived from at least one alcohol having no beta hydrogens with a contact lens material to obtain desirable hardness and oxygen permeability, said copolymerization being carried out by intermixing said material and ester and then polymerizing under free radical conditions, said ester having the following formula:

##STR14## WHEREIN;

A is selected from the group consisting of mesaconic acid, itaconic acid, citraconic acid, methylene malonate, maleic acid, fumaric acid, ethylene tricarboxylic acid, acrylic acid, and methacrylic acid,

n=1, 2, or 3

R₁, R₂ and R₃ are the same or different and each are alky, cycloalkyl or aryl groups having from 1 to 10 carbon atoms or ether groups having from 2 to 10 carbon atoms,

where when A is derived from a dibasic or tribasic acid, the ester can be a full ester, half ester, partial ester or a mixed ester, said ester being derived from at least one alcohol which is devoid of beta hydrogens,

said lens having a Shore D hardness of at least 70 and a DK of at least 10.

2. A method of modifying the hardness and DK value of a contact lens material comprising copolymerizing a carboxylic acid ester derived from at least one alcohol having no beta hydrogens with a contact lens material to obtain desirable hardness and oxygen permeability, said copolymerization being carried out by intermixing said material and ester and then polymerizing under free radical conditions, wherein said ester is dineopentyl itaconate.

3. A method of modifying the hardness and DK value of a contact lens material comprising copolymerizing a carboxylic acid ester derived from at least one alcohol having no beta hydrogens with a contact lens material to obtain desirable hardness and oxygen permeability, said copolymerization being carried out by intermixing said material and ester and then polymerizing under free radical conditions, wherein said ester is a neopentyl ester.

4. A method of modifying the hardness and DK value of a contact lens material comprising copolymerizing a carboxylic acid ester derived from at least one alcohol having no beta hydrogens with a contact lens material to obtain desirable hardness and oxygen permeability, said copolymerization being carried out by intermixing said material and ester and then polymerizing under free radical conditions, wherein said ester is neopentyl fumarate.

5. A method of modifying the hardness and DK value of a contact lens material comprising copolymerizing a carboxylic acid ester derived from at least one alcohol having no beta hydrogens with a contact lens material to obtain desirable hardness and oxygen permeability, said copolymerization being carried out by intermixing said material and ester and then polymerizing under free radical conditions, wherein said ester is a neopentyl maleate.