Method of making a contact lens material with increased oxygen permeability

• US 4,306,042 A
• Filed: 09/08/1980
• Issued: 12/15/1981
• Est. Priority Date: 09/02/1980
• Status: Expired due to Term

• Current Assignee: Dome Patent LP
• Original Assignee: Neefe Optical Laboratory
• Inventors: Neefe, Russell A.
• Primary Examiner(s): Lilling, Herbert J.
• Application Number:
  US06/185,000
• Time in Patent Office: 463 Days
• Field of Search: 526/279, 526/75, 264/1, 556/433, 204/159.13
• US Class Current: 522/99
• 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 (a) siloxanyl alkylester, an ester derivative of acrylic or methacrylic acid, surface wetting agent and an oxygen permeable crosslinking agent. The copolymer can be made either hard, soft or elasticmeric with improved oxygen permeability.

Claims

1. A method of making an oxygen permeable material for the manufacture of contact lens by the synthesization of the monomer 1,1,1-tris(methylsiloxy)methacryloxypropylsilane (a siloxanyl alkyl ester) by the following procedures:

(a) a mixture is prepared having the relationship of one mole of methacryloxypropyltrimethoxysilane with three to forty moles of trimethylchlorosilane;

(b) the mixture is then added to water whose volume is from 3 to 10 times that of the mixture;

(c) agitation is maintained for 30 minutes to 48 hours;

(d) then allow the mixture to separate into layers, remove and filter the upper organic layer;

(e) the unwanted by-product (hexamethyldisilane) is then removed by vacuum distillation;

(f) forming an oxygen permeable contact lens material by copolymerizing from 5% to 90% by weight of the 1,1,1-tris(trimethylsiloxy)methacryloxypropylsilane prepared above;

3% to 90% by weight of an ester of acrylic or methacrylic acid;

from 0.05% to 90% by weight of a surface wetting agent, from 0.01% to 90% by weight of an oxygen permeable crosslinking agent selected from the class of multifunctional siloxanyl alkyl esters in the presence of a free radical or a photo initiator.

2. A method of making an oxygen permeable material for the manufacture of contact lens by utilizing the synthesization of 1,5 bis(methacryloxypropyl) 1,1,5,5-tetrakis(trimethylsiloxy)dimethyltrisiloxane (an oxygen permeable crosslinking agent that is a dimer of siloxanyl alkyl ester) by the following procedure:

(a) a mixture is prepared with the relationship of;

(1) 2 moles methacryloxypropyltrimethoxysilane;

(2) 1 mole dimethyldiacetoxysilane; and

(3) 4 moles trimethylacetoxysilane;

the mixture is placed in a container that is equipped with a method of cooling and agitating;

(b) start agitation and cooling and in a dropwise manner add 65g of ethanol/sulfuric acid solution (the catalyst solution consists of 34.2% by weight of concentrated sulfuric acid, 39.5% by weight of medical grade ethanol and 26.3% by weight of distilled water) to one mole of methacryloxypropyltrimethoxysilane;

(c) after entirety of ethanol/sulfuric acid solution is added, continue the agitation for 24 to 72 hours;

(d) discontinue agitation and allow the mixture to separate into two layers, remove the upper layer;

(e) the unwanted by-products are then removed by vacuum distillation;

(f) forming an oxygen permeable contact lens material by copolymerizing from 5% to 90% by weight of a siloxyl alkyl ester, from 3% to 90% by weight of an ester of acrylic or methacrylic acid;

from 0.5% to 90% by weight of surface wetting agent, from 0.01% to 90% by weight of the 1,1,5,5-tetrakis(trimethylsiloxy) 1,3-bis(methacryloxypropyl)dimethyltrisiloxane prepared above, and in the presence of a free radical or photo initiator.

3. A method of making an oxygen permeable contact lens material utilizing the synthesization of 1,5,9 tris(methacryloxypropyl)-1,1,5,9,9-pentakis(trimethylsiloxy)tetramethylpentasiloxane (an oxygen permeable crosslinking agent that is a trimer of a siloxanyl alkyl ester) by the following procedures:

(a) a mixture is prepared with the relationship of;

(1) 3 moles methacryloxypropyltrimethyoxysilane;

(2) 2 moles dimethyldiacetoxysilane; and

(3) 5 moles trimethylacetoxysilane;

the mixture is placed in a container that is equipped with a method of cooling and agitating;

(b) start agitation and cooling and in a dropwise manner add 65 g of ethanol/sulfuric acid solution (the catalyst consists of 34.2% by weight of concentrated sulfuric acid, 39.5% by weight of medical grade ethanol, and 26.3% by weight of distilled water) to one mole of methacryloxypropyltrimethoxysilane;

(c) after entirety of ethanol/sulfuric acid solution is added, continue agitation for 24 to 72 hours;

(d) discontinue agitation and allow the two layers to separate, remove the upper layer;

(e) the unwanted by-products are then removed by vacuum distillation;

(f) forming an oxygen permeable contact lens material by copolymerizing from 5% to 90% by weight of a siloxanyl alkyl ester, from 3% to 90% by weight of an ester of acrylic or methacrylic acid, from 0.5% to 90% by weight of a surface wetting agent, from 0.01% to 90% by weight of the 1,5,9-tris(methacryloxypropyl) 1,1,5,9,9-pentakis(trimethylsiloxy)tetramethylpentasiloxane prepared above, and in the presence of a free radical or photo initiator.

4. A method of making an oxygen permeable contact lens material by utilizing the synthesization of 1,5,9,13 tetrakis(methacryloxypropyl) 1,1,5,9,13,13-hexakis(trimethylsiloxy)hexamethylheptasiloxane (an oxygen permeable crosslinking agent that is a tetramer of a siloxanyl alkyl ester) by the following procedures:

(a) a mixture is prepared with the relationship of;

(1) 4 moles methacryloxypropyltrimethoxysilane;

(2) 3 moles dimethyldiacetoxysilane, and (3) 6 moles trimethylacetoxysilane;

this mixture is placed in a container that is equipped with a method of cooling and agitating;

(b) start agitation and cooling and in a dropwise manner add 65 g of ethanol/sulfuric acid solution (the catalyst solution consists of 34.2% by weight of concentrated sulfuric acid, 39.5% by weight of medical grade ethanol, and 26.3% by weight of distilled water) to one mole of methacryloxypropyltrimethoxysilane;

(c) after entirety of ethanol/sulfuric acid solution is added, continue agitation for 24 to 72 hours;

(d) discontinue agitation and allow the two layers to separate, remove the upper layer;

(f) forming an oxygen permeable contact lens material by copolymerizing from 5% to 90% by weight of a siloxanyl alkyl ester from 3% to 90% by weight of an ester of acrylic or methacrylic acid, from 0.5% to 90% by weight of a surface wetting agent, from 0.01% to 90% by weight of the 1,5,9,13-tetrakis(methacryloxypropyl) 1,1,5,9,13,13-hexakis(trimethylsiloxy)hexamethylheptasiloxane prepared above, and in the presence of a free radical or photo initiator.