Hydrophilic contact lens made from polysiloxanes containing hydrophilic sidechains

A hydrophilic, hydrolytically stable, biologically inert contact lens with the capability of transporting oxygen sufficiently to meet the requirements of the human cornea, comprising a polysiloxane monomer having the following formula:

• ##STR91## wherein Y.sub.1 and Y.sub.2 equal the same or different and are selected from the group consisting of a monovalent hydrocarbon having from 1 to 20 carbon atoms and a halogenated monovalent hydrocarbon having from 1 to 20 carbon atoms,
• X is selected from the group consisting of a hydroxyl radical, a monovalent hydrocarbon having from 1 to 20 carbon atoms, halogenated monovalent hydrocarbon having from 1 to 20 carbon atoms, ##STR92## wherein R is a monovalent hydrocarbon having from 1 to 20 carbon atoms, R.sub.1 is a monovalent hydrocarbon having from 1 to 20 carbon atoms, n.sub.1 is an integer from zero to 1 and n.sub.2 is an integer from 1 to 3, ##STR93## wherein R.sub.2 and R.sub.3 are the same or different and are monovalent hydrocarbons having from 1 to 20 carbon atoms and n.sub.3 is an integer from zero to 1,
• --R.sub.4 --A
• wherein R.sub.4 is a divalent hydrocarbon having from 1 to about 22 carbon atoms and A is a free radical polymerizably activated monovalent unsaturated group,
• a is at least 1, b is zero or at least 2, c is 1 if b is zero and c is zero if b is at least 2, d is at least 1, except when b is zero and a is 1 then d is zero or greater, e is at least 1 and f is zero or greater,
• Z.sub.1 through Z.sub.7 are the same or different and at least one of Z.sub.1 through Z.sub.7 is equal to a hydrophilic sidechain, said Z.sub.1 through Z.sub.7 are selected from the group consisting of a monovalent hydrocarbon having from 1 to 20 carbon atoms, a halogenated monovalent hydrocarbon having from 1 to 20 carbon atoms and a hydrophilic sidechain with the following formulas selected from the group consisting of ##STR94## wherein R.sub.5 is a divalent hydrocarbon having from 1 to 10 carbon atoms, R.sub.6 is selected from the group consisting of methyl and hydrogen, R.sub.7 is selected from the group consisting of hydrogen, a monovalent hydrocarbon having from 1 to 10 carbon atoms, ##STR95## wherein R.sub.8 is selected from the group consisting of a monovalent hydrocarbon having from 1 to 10 carbon atoms and hydrogen, and n.sub.4 is at least 1,
• --R.sub.9 --OH).sub.n.sbsb.5
• wherein R.sub.9 is a hydrocarbon having from 1 to 20 carbon atoms and a valence of n.sub.5 +1, n.sub.5 is at least 1, there cannot be an --OH group on an aliphatic carbon atom beta to the Si atom, and there cannot be more than one OH group on any one carbon atom, ##STR96## wherein R.sub.10 is a divalent hydrocarbon having from 1 to 10 carbon atoms, R.sub.11 is selected from the group consisting of hydrogen and methyl and R.sub.12 is a hydrocarbon having from 2 to 20 carbon atoms and a valance of n.sub.8 +1 and can have no more than one oxygen atom attached to any one carbon atom, n.sub.6 is zero or greater, n.sub.7 is an integer from zero to 1 and n.sub.8 is at least 1, ##STR97## wherein R.sub.13 is a divalent hydrocarbon having from 2 to 10 carbon atoms and the ##STR98## group is not attached to a carbon atom of R.sub.13 which is alpha to the Si atom, R.sub.14 and R.sub.15 can be the same or different and are selected from the group consisting of a monovalent hydrocarbon having from 1 to 10 carbon atoms, hydrogen, --CH.sub.2 --CH.sub.2).sub.n.sbsb.9 OH wherein n.sub.9 is an integer from 1 to 3 and ##STR99## wherein R.sub.16 and R.sub.17 are the same or different and are selected from the group consisting of hydrogen and a monovalent hydrocarbon having from 1 to 10 carbon atoms and n.sub.10 is an integer from 1 to 5, ##STR100## wherein R.sub.18 is a divalent hydrocarbon having from 1 to 20 carbon atoms and R.sub.19 and R.sub.20 are the same or different and are selected from the group consisting of hydrogen and a monovalent hydrocarbon having from 1 to 10 carbon atoms, ##STR101## wherein R.sub.21 is a divalent or trivalent hydrocarbon having from 1 to 10 carbon atoms and the S atom is not attached to R.sub.21 by an aliphatic carbon atom beta to the Si atom, R.sub.21 may or may not be attached to R.sub.22 to form a ring which contains more than 3 carbon atoms and R.sub.22 is selected from the group consisting of a hydrocarbon having from 1 to 10 carbon atoms and --O.sup..crclbar. M.sup..sym. where M is selected from the group consisting of a monovalent metal ion and a quaternery ammonium ion, and n.sub.11 is an integer from 1 to 2, ##STR102## wherein R.sub.23 is a divalent hydrocarbon having from 3 to 10 carbon atoms and the N.sup..sym. must be attached to a carbon atom of R.sub.23 which is at least 2 carbon atoms away from the Si atom, R.sub.24, R.sub.25 and R.sub.26 are the same or different and are monovalent hydrocarbons having from 1 to 10 carbon atoms, X.sub.1.sup..crclbar. is a monovalent anion selected from the group consisting of halides, R.sub.27 --COO.sup..crclbar. wherein R.sub.27 is selected from the group consisting of hydrogen, a monovalent hydrocarbon having from 1 to 10 carbon atoms and a halogenated monovalent hydrocarbon having from 1 to 10 carbon atoms and R.sub.28 --SO.sub.3.sup..crclbar. wherein R.sub.28 is selected from the group consisting of a monovalent hydrocarbon having from 1 to 10 carbon atoms and a halogenated monovalent hydrocarbon having from 1 to 10 carbon atoms, ##STR103## wherein R.sub.29 is a divalent hydrocarbon having from 1 to 10 carbon atoms and n.sub.12 is an integer from 0 to 1 and when n.sub.12 is 1 the oxygen cannot be attached to an aliphatic carbon atom in R.sub.29 which is beta to the Si atom, R.sub.30 is a divalent hydrocarbon having from 1 to 10 carbon atoms, R.sub.31 is a hydrocarbon having from 2 to 20 carbon atoms and a valence of n.sub.13 +1 and can have no more than one oxygen atom attached to any one carbon atom and n.sub.13 is at least 1, ##STR104## wherein R.sub.32 is a divalent hydrocarbon having from 1 to 10 carbon atoms and the ester oxygen atom bonded to R.sub.32 cannot be attached to an aliphatic carbon atom in R.sub.32 which is beta to the Si atom, R.sub.33 is a hydrocarbon having from 2 to 20 carbon atoms and a valence of n.sub.14 +1 and can have no more than one oxygen atom attached to any one carbon atom and n.sub.14 is an integer of at least 1, ##STR105## wherein R.sub.34 is a divalent hydrocarbon having from 1 to 10 carbon atoms, ##STR106## wherein R.sub.35 is a divalent hydrocarbon having from 2 to 10 carbon atoms and n.sub.15 is an integer from 1 to 10, ##STR107## wherein R.sub.36 is a divalent hydrocarbon having from 2 to 10 carbon atoms and the carbonyl group is not attached to a carbon atom alpha to the Si atom, R.sub.37 is selected from the group consisting of methyl and hydrogen, R.sub.38 is selected from the group consisting of hydrogen, a monovalent hydrocarbon having from 1 to 10 carbon atoms and ##STR108## wherein R.sub.39 is a monovalent hydrocarbon having from 1 to 10 carbon atoms and n.sub.16 is at least 1, ##STR109## wherein R.sub.40 is a divalent hydrocarbon having from 1 to 10 carbon atoms, R.sub.41 and R.sub.42 can be the same or different and are selected from the group consisting of hydrogen, a monovalent hydrocarbon having from 1 to 10 carbon atoms and --CH.sub.2).sub.n.sbsb.17 OH wherein n.sub.17 is an integer from 2 to 4, ##STR110## wherein R.sub.43 is a divalent hydrocarbon having from 2 to 10 carbon atoms and the S atom cannot be attached to a carbon atom of R.sub.43 which is alpha to the Si atom, R.sub.44 and R.sub.45 can be the same or different and are selected from the group consisting of hydrogen and a monovalent hydrocarbon having from 1 to 10 carbon atoms, ##STR111## wherein R.sub.46 is a divalent hydrocarbon having from 1 to 10 carbon atoms and n.sub.18 is an integer from zero to 3, ##STR112## wherein R.sub.47 and R.sub.48 are selected from the group consisting of hydrogen, divalent or monovalent hydrocarbon having from 0 to 10 carbon atoms and R.sub.49 is selected from the group consisting of hydrogen, divalent or monovalent hydrocarbon having from 1 to 10 carbon atoms and only one of R.sub.47, R.sub.48 and R.sub.49 must be a divalent hydrocarbon and attached to the Si atom, R.sub.50 is selected from the group consisting of hydrogen, a monovalent hydrocarbon having from 1 to 10 carbon atoms and --CH.sub.2).sub.n.sbsb.20 OH where n.sub.20 is an integer from 2 to 4, and n.sub.19 is an integer from zero to 3, ##STR113## wherein R.sub.51 is a divalent hydrocarbon having from 2 to 10 carbon atoms and the carbonyl group cannot be attached to a carbon atom of R.sub.51 alpha to the Si atom and X.sub.2.sup..sym. is a monovalent cation selected from the group consisting of monovalent metal cations and ##STR114## wherein R.sub.52, R.sub.53, R.sub.54 and R.sub.55 can be the same or different and selected from the group consisting of hydrogen and a monovalent hydrocarbon having from 1 to 10 carbon atoms, and ##STR115## wherein R.sub.56 is a divalent hydrocarbon having from 2 to 10 carbon atoms and the carbonyl group cannot be attached to a carbon atom of R.sub.56 which is alpha to the Si atom, R.sub.57 is a divalent hydrocarbon having from one to 10 carbon atoms, R.sub.58 is selected from the group consisting of hydrogen and a monovalent hydrocarbon having from 1 to 10 carbon atoms and n.sub.21 is an integer from zero to 10, polymerized to form a polymer in a crosslinked network.