Hydrophilic silicone rubber article and process for its preparation

• US 4,920,184 A
• Filed: 08/05/1988
• Issued: 04/24/1990
• Est. Priority Date: 05/15/1985
• Status: Expired due to Fees

• Current Assignee: CIBA Vision Corporation (Novartis Ag)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Neumann, Walter, Schafer, Horst, Kossmehl, Gerhard
• Primary Examiner(s): Jacobs, Lewis T.
• Assistant Examiner(s): NOT, DEFINED
• Application Number:
  US07/228,867
• Time in Patent Office: 627 Days
• Field of Search: 525/477, 525/478
• US Class Current: 525/477
• CPC Class Codes: C08G 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence
• CPC Class Codes: C08J 2383/04 Polysiloxanes
• CPC Class Codes: C08J 7/12 Chemical modification
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Hydrophilic silicone rubber article, the surface of which is hydrophilized partly or completely by reaction (equilibration reaction) with organosiloxanes, the organosiloxanes being synthesized by the reaction of SiH-group-containing siloxanes with allyl compounds which contain protected OH groups. These articles are particularly useful as contact lenses and intraocular lenses.

Claims

1. An improved process for hydrophilizing the surface of a molded silicone rubber article in which the silicone rubber at its surface is reacted in a catalyzed equilibration reaction with an organosiloxane, wherein the improvement comprises

using as the organosiloxane a preformed organosiloxane containing hydroxyalkyl or protected hydroxyalkyl moieties, synthesized by reacting a siloxane containing a Si--H group with an allyloxy compound in the presence of a catalyst.

2. A process according to claim 1 which additionally comprises hydrolyzing the equilibrated reaction product formed by the process of claim 1.

3. A process according to claim 1 wherein the silicone rubber article is a contact lens.

4. A process according to claim 1 in which the organosiloxane is selected from the group consisting of linear α

,ω

-organodimethylsiloxane, linear trimethysilyl-terminated organomethylsiloxanes, cyclic organomethylsiloxanes, cyclic diorganosiloxanes and mixtures thereof.

5. A process according to claim 4, in which the organosiloxane is an α

,ω

-organodimethylsiloxane selected from the group consisting of 1,3-bis(3-trimethylsilyloxypropyl)-1,1,3,3,-tetramethyl-disoloxane, 1,3-bis-(3-hydroxypropyl)-1,1,3,3-tetramethyldisiloxane, 3,5-bis(3-trimethylsilyloxypropyl)-1,1,1,3,5,7,7,7-octamethyltetrasiloxane, 3,5-bis(3-hydroxypropyl)-1,1,1,3,5,7,7,7-octamethyltetrasiloxane, 1,3-bis-(6,7-epoxy-4-oxaheptyl)-1,1,3,3-tetramethyldisiloxane, 1,3-bis(6,7-dihydroxy-5-oxaheptyl)-1,1,3,3-tetramethyldisiloxane, and mixtures thereof.

6. A process according to claim 4 in which the organosiloxane is a silyl-terminated organomethylsiloxane addition product of the general formula ##STR8## wherein R is --O--Si(CH₃)₃ or ##STR9## obtained from allyloxytrimethylsilane or allyl glycidyl ether and polymethylhydrogensiloxanes of different chain length and having the formula ##STR10## wherein n=2 or from about 10 to about 50, or their hydrolysis products in which R is --OH or --O--CH₂ --CH(OH)--CH₂ --OH.

7. A process according to claim 4 in which the organosiloxane is a cyclic organomethylsiloxane or cyclic diorganosiloxane selected from the group consisting of 2,4,6,8-tetrakis(3-trimethylsilyloxypropyl)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,4,6,8-tetrakis-(6,7-epoxy-4-oxaheptyl)-2,4,6,8-tetramethylcylcotetrasiloxane, 2,4,6,8-tetrakis(3-acetoxypropyl)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,4,6,8-tetrakis(3-hydroxypropyl)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,4,6,8-tetrakis(6,7-dihydroxy-4-oxaheptyl)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,2,4,4,6,6,8,8-octakis-(3-acetoxypropyl)cyclotetrasiloxane, 2,2,4,4,6,6,8,8-octakis(3-hydroxypropyl)cyclotetrasiloxane and mixtures thereof.

8. A process according to claim 1, wherein a Lewis acid or concentrated sulfuric acid is used as equilibration catalyst.

9. A process according to claim 8, wherein hexachlorocyclotriphosphazene is used as Lewis acid.

10. A process according to claim 8 wherein the equilibration reaction is carried out in an ether as solvent.

11. A process according to claim 1, wherein the SiH-group-containing siloxane is reacted with the allyl compound in the presence of hexachloroplatinic acid as catalyst.

12. A process according to claim 1 wherein polydimethylsiloxane is used as the silicone rubber.