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Hydrophilic contact lens made from polysiloxanes containing hydrophilic sidechains

  • US 4,259,467 A
  • Filed: 12/10/1979
  • Issued: 03/31/1981
  • Est. Priority Date: 12/10/1979
  • Status: Expired due to Term
First Claim
Patent Images

1. 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 Y1 and Y2 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, R1 is a monovalent hydrocarbon having from 1 to 20 carbon atoms, n1 is an integer from zero to 1 and n2 is an integer from 1 to 3, ##STR93## wherein R2 and R3 are the same or different and are monovalent hydrocarbons having from 1 to 20 carbon atoms and n3 is an integer from zero to 1,
    
    
    space="preserve" listing-type="equation">--R.sub.4 --Awherein R4 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,Z1 through Z7 are the same or different and at least one of Z1 through Z7 is equal to a hydrophilic sidechain, said Z1 through Z7 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 R5 is a divalent hydrocarbon having from 1 to 10 carbon atoms, R6 is selected from the group consisting of methyl and hydrogen, R7 is selected from the group consisting of hydrogen, a monovalent hydrocarbon having from 1 to 10 carbon atoms, ##STR95## wherein R8 is selected from the group consisting of a monovalent hydrocarbon having from 1 to 10 carbon atoms and hydrogen, and n4 is at least 1,
    
    
    space="preserve" listing-type="equation">--R.sub.9 --OH).sub.n.sbsb.5 wherein R9 is a hydrocarbon having from 1 to 20 carbon atoms and a valence of n5 +1, n5 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 R10 is a divalent hydrocarbon having from 1 to 10 carbon atoms, R11 is selected from the group consisting of hydrogen and methyl and R12 is a hydrocarbon having from 2 to 20 carbon atoms and a valance of n8 +1 and can have no more than one oxygen atom attached to any one carbon atom, n6 is zero or greater, n7 is an integer from zero to 1 and n8 is at least 1, ##STR97## wherein R13 is a divalent hydrocarbon having from 2 to 10 carbon atoms and the ##STR98## group is not attached to a carbon atom of R13 which is alpha to the Si atom, R14 and R15 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, --CH2 --CH2)n.sbsb.9 OH wherein n9 is an integer from 1 to 3 and ##STR99## wherein R16 and R17 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 n10 is an integer from 1 to 5, ##STR100## wherein R18 is a divalent hydrocarbon having from 1 to 20 carbon atoms and R19 and R20 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 R21 is a divalent or trivalent hydrocarbon having from 1 to 10 carbon atoms and the S atom is not attached to R21 by an aliphatic carbon atom beta to the Si atom, R21 may or may not be attached to R22 to form a ring which contains more than 3 carbon atoms and R22 is selected from the group consisting of a hydrocarbon having from 1 to 10 carbon atoms and --O.sup.⊖

    M.sup.⊕

    where M is selected from the group consisting of a monovalent metal ion and a quaternery ammonium ion, and n11 is an integer from 1 to 2, ##STR102## wherein R23 is a divalent hydrocarbon having from 3 to 10 carbon atoms and the N.sup.⊕

    must be attached to a carbon atom of R23 which is at least 2 carbon atoms away from the Si atom, R24, R25 and R26 are the same or different and are monovalent hydrocarbons having from 1 to 10 carbon atoms, X1.sup.⊖

    is a monovalent anion selected from the group consisting of halides, R27 --COO.sup.⊖

    wherein R27 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 R28 --SO3.sup.⊖

    wherein R28 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 R29 is a divalent hydrocarbon having from 1 to 10 carbon atoms and n12 is an integer from 0 to 1 and when n12 is 1 the oxygen cannot be attached to an aliphatic carbon atom in R29 which is beta to the Si atom, R30 is a divalent hydrocarbon having from 1 to 10 carbon atoms, R31 is a hydrocarbon having from 2 to 20 carbon atoms and a valence of n13 +1 and can have no more than one oxygen atom attached to any one carbon atom and n13 is at least 1, ##STR104## wherein R32 is a divalent hydrocarbon having from 1 to 10 carbon atoms and the ester oxygen atom bonded to R32 cannot be attached to an aliphatic carbon atom in R32 which is beta to the Si atom, R33 is a hydrocarbon having from 2 to 20 carbon atoms and a valence of n14 +1 and can have no more than one oxygen atom attached to any one carbon atom and n14 is an integer of at least 1, ##STR105## wherein R34 is a divalent hydrocarbon having from 1 to 10 carbon atoms, ##STR106## wherein R35 is a divalent hydrocarbon having from 2 to 10 carbon atoms and n15 is an integer from 1 to 10, ##STR107## wherein R36 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, R37 is selected from the group consisting of methyl and hydrogen, R38 is selected from the group consisting of hydrogen, a monovalent hydrocarbon having from 1 to 10 carbon atoms and ##STR108## wherein R39 is a monovalent hydrocarbon having from 1 to 10 carbon atoms and n16 is at least 1, ##STR109## wherein R40 is a divalent hydrocarbon having from 1 to 10 carbon atoms, R41 and R42 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 --CH2)n.sbsb.17 OH wherein n17 is an integer from 2 to 4, ##STR110## wherein R43 is a divalent hydrocarbon having from 2 to 10 carbon atoms and the S atom cannot be attached to a carbon atom of R43 which is alpha to the Si atom, R44 and R45 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 R46 is a divalent hydrocarbon having from 1 to 10 carbon atoms and n18 is an integer from zero to 3, ##STR112## wherein R47 and R48 are selected from the group consisting of hydrogen, divalent or monovalent hydrocarbon having from 0 to 10 carbon atoms and R49 is selected from the group consisting of hydrogen, divalent or monovalent hydrocarbon having from 1 to 10 carbon atoms and only one of R47, R48 and R49 must be a divalent hydrocarbon and attached to the Si atom, R50 is selected from the group consisting of hydrogen, a monovalent hydrocarbon having from 1 to 10 carbon atoms and --CH2)n.sbsb.20 OH where n20 is an integer from 2 to 4, and n19 is an integer from zero to 3, ##STR113## wherein R51 is a divalent hydrocarbon having from 2 to 10 carbon atoms and the carbonyl group cannot be attached to a carbon atom of R51 alpha to the Si atom and X2.sup.⊕

    is a monovalent cation selected from the group consisting of monovalent metal cations and ##STR114## wherein R52, R53, R54 and R55 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 R56 is a divalent hydrocarbon having from 2 to 10 carbon atoms and the carbonyl group cannot be attached to a carbon atom of R56 which is alpha to the Si atom, R57 is a divalent hydrocarbon having from one to 10 carbon atoms, R58 is selected from the group consisting of hydrogen and a monovalent hydrocarbon having from 1 to 10 carbon atoms and n21 is an integer from zero to 10, polymerized to form a polymer in a crosslinked network.

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