Crosslinked siloxane-urethane polymer contact lens

• US 5,426,158 A
• Filed: 04/14/1994
• Issued: 06/20/1995
• Est. Priority Date: 09/28/1988
• Status: Expired due to Fees

• Current Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Harisiades, Paul, Mueller, Karl F.
• Primary Examiner(s): DEAN JR, RALPH H
• Application Number:
  US08/227,481
• Time in Patent Office: 432 Days
• Field of Search: 525/455, 525/479, 525/903, 528/26, 528/28
• US Class Current: 525/455
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 2270/00 Compositions for creating interpenetrating networks
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: Y10S 525/903 Interpenetrating network

Abstract

A contact lens is described which is synthesized by reaction in a mold of a isocyanate capped poly(dialkylsiloxane) prepolymer with a poly(dialkylsiloxane) di- or polyalkanol. The clear polyurethane rubber contact lens is readily made completely wettable by a transfer-grafting process or post-treatment and has a high oxygen permeability.

Claims

1. A compatible, interpenetrating-polymer-network composition which comprises

(I) 95-50% by weight of the total composition of a siloxane-urethane polymer formed by the reaction of;

(A) a di- or poly-hydroxyalkyl substituted alkyl polysiloxane having a number average molecular weight between about 200 and about 10,000 and

(B) a substantially compatible, aliphatic, cycloaliphatic or aromatic di- or tri-isocyanate,

wherein the total number of hydroxyl groups in component (A) is substantially stoichiometrically equivalent to the total number of isocyanate groups in component (B), and with the proviso that an effective crosslinking amount of (A) or (B) or both (A) and (B) is present and possesses a functionality greater than two, and

(II) 5-50% by weight of the total composition of a vinyl polymer or copolymer obtained by the free-radical polymerization of a vinyl monomer or mixture of vinyl monomers;

wherein said siloxane-urethane polymer (I) is formed by a polymerization which occurs prior to the polymerization reaction which forms said vinyl polymer (II).

2. A composition according to claim 1 wherein component (I) is 95-75% by weight and component (II) is 5-25% by weight of the total composition.

3. A composition according to claim 1 where in component (I) (A) is a di- or poly-hydroxy substituted polysiloxane of formula A₁, A₂ or A₃, with the structures:

##STR5## wherein;

R₁ is an alkyl group of 1 to 4 carbon atoms or phenyl,

R₂ is a linear or branched alkylene group with 2 to 6 carbon atoms a polyoxyalkylene group of structure;

##STR6## wherein R₃ is hydrogen or methyl and n is an integer from 1 to 50;

x₁, x₂ are integers from 1 to 500;

y₁ is 0 to 4, y₂ is 2 to 5 with the proviso that the ratios of;

##EQU3## are not greater than 70.

4. A composition according to claim 3 where in component (I)

(A) contains 40-60 hydroxyl equivalent percent of polysiloxane tetrols A₃,

wherein

x₁ is 10-50 and

R₁ is methyl, and

40-60 hydroxyl equivalent percent A₁, where

y₁ is zero,

x₁ is 15-60,

R₁ is methyl,

R₂ is propylene, 1-methylpropylene,

or ##STR7## (B) is isophorone diisocyanate or 2,2,4(2,4,4)-trimethylhexane-1,6-diisocyanate.

5. A composition according to claim 3 where in component (I)

(A) is of structure A₁, where

y₁ is zero, x₁ is 5-50,

R₁ is methyl,

R₂ is propylene, butylene, 1-methylpropylene or ##STR8## the diisocyanate (B) is isophorone diisocyanate or 2,2,4 (2,4,4) trimethylhexane-1,6-diisocyanate.

6. A composition according to claim 3 where in component (I)

(A) contains 40-60 hydroxyl equivalent percent of polysiloxane-tetrols of structure A₃, and diisocyanate (B) is isophorone diisocyanate or 2,4,4(2,4,4)-trimethylhexane-1,6-diisocyanate.

7. A composition according to claim 3 where in component (I)

(A) contains 40-60 hydroxyl equivalent percent of polysiloxane diols of structure A₁, where

y₁ is zero or 1

x₁ is 1-5,

R₁ is methyl,

R₂ is propylene, or butylene, and the diisocyanate (B) is isophorone diisocyanate or 2,2,4(2,4,4) trimethylhexane-1,6-diisocyanate.

8. A composition according to claim 1 where in component (I)

(B) is isophorone diisocyanate, 2,2,4(2,4,4)-trimethylhexane-1,6-diisocyanate or 1,2- or 1,4- toluene diisocyanate.

9. A composition according to claim 1 where in component (II) the vinyl polymer is prepared from a fluoroalkyl acrylate or methacrylate with 3 to 21 F atoms in the fluoroalkyl group, from an oligosiloxanyl-silylalkyl acrylate or methacrylate with 2 to 10 Si atoms in the oligosiloxanyl group, from a hydroxyalkyl acrylate or methacrylate, N-vinylpyrrolidone, N,N-dimethylacrylamide or methyl methacrylate.

10. A composition according to claim 1 where in component (II) the vinyl polymer is prepared from N,N-dimethylacrylamide, methyl methacrylate, 2-hydroxyethyl methacrylate, methacryloxypropyl-tris (trimethylsiloxy)silane or tridecylfluorohexyl-ethyl methacrylate.

11. An ophthalmic device prepared from the composition according to claim 1.

12. An ophthalmic device according to claim 11 which is a contact lens.

13. A composition according to claim 1, wherein component (I) (B) is a diisocyanate, triisocyanate or mixture thereof selected from the group consisting of ethylene diisocyanate, 1,2-diisocyanatopropane, 1,3,-diisocyanatopropane, 1,6-diisocyanatohexane, 1,2-diisocyanatocyclohexane, 1,3-diisocyanatocyclohexane, 1,4-diisocyanatobenzene;

bis(4-isocyanatocyclohexyl)methane, bis-4(isocyanatocyclohexenyl)methane, bis(4-1isocyanatophenyl)methane, 1,2- and 1,4-toluenediisocyanate;

3,3-dichloro-4,4'"'"'-diisocyanatobiphenyl;

tris(4-isocyanatophenyl)methane,1,5-diisocyanatonaphthalene, hydrogenated toluene diisocyanate;

1,isocyanatomethyl-5-isocyanato-1,3-3-trimethylcyclohexane (=isophorone diisocyanate);

1,3,5-tris(6-isocyanatohexyl)biuret, 1,6-diisocyanato-2,2-4-(2,4,4)-trimethylhexane, 2,2'"'"'diisocyanatodiethyl fumarate;

1,5-diisocyanato 1-carboxypentane;

1,2-, 1,3-, 1,6-, 1,7-, 1,8-, 2,7- and 2,3-diisocyanatonaphthalene;

2,4- and 2,7-diisocyanato 1-methylnaphthalene;

1,4-diisocyanatomethylcyclo-hexane;

1,3-diisocyanato-6(7)-methylnaphthalene;

4,4'"'"'-diisocyanatobiphenyl;

4,4'"'"'-diisocyanato-3,3'"'"'-dimethoxybisphenyl;

3,3'"'"'- and 4,4'"'"'-diisocyanato-2,2'"'"'-dimethyl biphenyl;

bis-(4-isocyanatophenyl)ethane and bis(4-isocyanatophenylether).