Strong, silicone containing polymers with high oxygen permeability
AssigneeCiba-Geigy Corporation
InventorsKarl F. Mueller, Sonia J. Heiber, Walter L. Plankl
Life of this patent
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Abstract
Clear, strong, crosslinked polymers are described, which are obtained by copolymerization of (A) 8-70% of a linear or branched polysiloxane of 400-100,000 molecular weight (MW) containing at least two terminal or pendant, polymerizable, vinyl groups per each 5000 MW unit of polysiloxane and which are attached to the polysiloxane through at least two urethane, thiourethane, urea or amide linkages and (B) 30-92% of a mono- or divinyl compound or a mixture of such monomers consisting of 85 to 100% of water insoluble monomers. These polymers are useful in the preparation of hard or soft contact lenses.
Claims28
A polymer, suitable for use in contact lenses, comprising the crosslinked copolymerization product of
- (A) from about 15 to about 60% by weight of said polymer of a linear or branched polysiloxane macromer having a molecular weight from about 400 to about 100,000, as measured by end group analysis or gel permeation chromatography, said macromer containing at least two terminal or pendant, polymerizable olefinic groups per each 5000 molecular weight unit of polysiloxane, said groups being attached to the polysiloxane through at least two urethane, thiourethane, urea or amide linkages, said macromer having the structure A.sub.1 or A.sub.2, ##STR16## wherein:
- R.sub.1 is a linear or branched alkylene group with 2-6 carbon atoms or a polyoxyalkylene group of structure G ##STR17## wherein R.sub.3 is hydrogen or methyl and n is an integer from 1-50 or R.sub.2, R.sub.a, R.sub.b, R.sub.c, R.sub.d, R.sub.e, F.sub.f, R.sub.g, R.sub.h, R.sub.i, R.sub.j, and R.sub.k are independently methyl or phenyl, x.sub.1 and X.sub.2 are integers from 1 to 500 with the provison that the sum of x.sub.1 +x.sub.2 is 7 to 1000, y.sub.1 is 0 to 14 and y.sub.2 is 1 to 13 with the proviso that the ratio of ##EQU3## is not greater than 70, E.sub.1, E.sub.2, E.sub.3, T.sub.1 and T.sub.2 are each a direct bond,
- m is 1 or 2,
- x is a di- or tri-radical:
- --Z.sub.1 --CO--NH--R.sub.4 --(NH--CO--).sub.v
- wherein v=1 or 2, Z.sub.1 is oxygen, sulfur or NR.sub.5, wherein R.sub.5 is hydrogen or lower (C.sub.1 -C.sub.4) alkyl, Z.sub.1 is connected to R.sub.1 ;
- and R.sub.4 is a di- or triradical obtained by removing the NCO-groups from an aliphatic, cycloaliphatic or aromatic di- or triisocyanate;
- Y is:
- ##STR18## wherein:
- R.sub.6 is:
- hydrogen, methyl, --COOR.sub.5 or --COOR.sub.7 OH with the proviso that if R.sub.6 is other than hydrogen,
- m and w.sub.1 are each 1;
- and R.sub.8 is a direct bond;
- Z.sub.2 =oxygen or --NR.sub.5 --
- R.sub.7 is a linear or branched alkylene of 2 to 10 carbon atoms, phenylene or phenylalkylene with 2 to 10 carbon atoms in the alkylene, or polyoxyalkylene of structure G,
- R.sub.8 is R.sub.7 or a tri- or tetra radical residue with 2-4 carbon atoms;
- w.sub.1 is 1 to 3;
- R.sub.9 is an alkylene group of from 2 to 4 carbon atoms or a direct bond with the proviso that if w.sub.1 =1, R.sub.9 is a direct bond, and it follows that R.sub.8 is a di-radical;
- R.sub.10 is hydrogen, methyl or --CH.sub.2 COOH, with the proviso that if R.sub.10 is --CH.sub.2 COOH, R.sub.6 is hydrogen;
- R.sub.11 is a direct bond or an aliphatic di-, tri- or tetra-radical with from 1-6 carbon atoms, and
- w.sub.2 is 1 to 3, with the proviso that if R.sub.11 is a direct bond, w.sub.2 is 1, and
- (B) about 85 to about 40% by weight of said polymer of a mixture of water-soluble and water-insoluble monomers or water-insoluble monomers, said monomers being monoolefinic, diolefinic or a mixture of monoolefinic and diolefinic monmers, with from 85 to 100% by weight of the total monomers being water-insoluble, and with from 25 to 0% by weight of the total monomers being diolefinic.
Dependencies are inferred from the claim text.