High refractive index thermoplastic polyphosphonates
AssigneeJohnson & Johnson Vision Products, Inc., and Virginia Tech Intellectual Properties, Inc.
InventorsHosadurga K. Shobha, Venkat Sekharipuram, James E. McGrath, Atul Bhatnagar
Life of this patent
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Abstract
High refractive index, melt processable polyphosphonates and methods for preparing the same are provided. These polymers are particularly useful for optical and ophthalmic parts, such as lenses. A method of preparing optical and ophthalmic lenses by injection molding the polymers of the present invention into the form of the optical or ophthalmic lenses is also provided.
Claims24
A phosphonate homopolymer or copolymer having units of the formula:
- 18
- wherein R1, R2, and R3 are independently O or S;
- at least one of R1, R2, and R3 is S;
- R4 is a linear or branched C1-C4 alkyl or C1-C4 haloalkyl, phenyl, chlorophenyl, p-tolyl, benzyl, biphenyl, or cyclohexyl;
- and R5 is
- 19
- or any combination of any of the foregoing.
A phosphonate homopolymer or copolymer having units of the formula:
- 21
- wherein R6, R7, and R8 are independently O or S;
- R9 is a linear or branched C1-C4 alkyl or C1-C4 haloalkyl, phenyl, chlorophenyl, p-tolyl, benzyl, biphenyl, or cyclohexyl;
- and R10 is
- 22
A phosphonate copolymer comprising
- (a) a first unit having the formula
- 23
- wherein R16, R17, and R18 are independently O or S;
- R19 is phenyl;
- and R20 is
- 24
- (b) a second unit having the formula
- 25
- wherein R21, R22, and R23 are independently O or S;
- R24 is phenyl;
- and R25 is
- 26
An optical or ophthalmic lens, said lens comprising a melt-processable phosphonate homopolymer or copolymer having units of the formula:
- 27
- wherein R11, R12, and R13 independently are O or S;
- R14 is a linear or branched C1-C4 alkyl or C1-C4 haloalkyl, phenyl, chlorophenyl, p-tolyl, benzyl, biphenyl, or cyclohexyl;
- and R15 is
- 28
- or any combination of any of the foregoing.
A method for preparing a phosphonate homopolymer or copolymer, said method comprising reacting
- (a) at least one phosphonic acid halide having the formula
- 34
- wherein R26 and R28 are independently halogens;
- R27 is S;
- and R29 is a linear or branched C1-C4 alkyl or C1-C4 haloalkyl, phenyl, chlorophenyl, p-tolyl, benzyl, biphenyl, or cyclohexyl;
- with
- (b) a bisphenol selected from the group consisting of hydroquinone, resorcinol, 4,4′-dihydroxybiphenyl, 4,4′-cyclohexylidene diphenol, bisphenol A, bis(4-hydroxyphenyl)methane, 2,2-bis(2-hydroxyphenyl)propane, bis P, 4,4′-bis-S, 2,2′-bis-S, 2-hydroxyphenyl-4′-hydroxyphenyl sulfone, dihydroxydiphenyl ether, bis(4-hydroxyphenyl) sulfide, bis(2-hydroxyphenyl) sulfide, dihydroxybenzophenone, 1,5-dihydroxynaphthalene, 2,5-dihydroxynaphthalene, 2,2-bis(3,5-dimethyl-4-hydroxyphenyl) propane, thiodithiophenol, phenolphthalein, 4,4′-bis(hydroxyphenyl)phenylphosphine oxide, α,α′-bis(4-hydroxy-3-methylphenyl)-1,4-diisopropylbenzene, bis E, 2,2-bis(4-hydroxy-3-methylphenyl) propane, bis(4-hydroxy-3-methylphenyl) sulfide, dihydroxydiphenylether, 1,3-bis(4-hydroxyphenoxy) benzene, phenyl HC, t-butyl HQ, 4,4′-thiobis(t-butyl cresol), 2,2′-thiobis(4-t-octylphenol), and any combination of any of the foregoing to yield said homopolymer or copolymer.
A method for preparing a phosphonate homopolymer or copolymer, said method comprising reacting
- (a) at least one phosphonic acid halide having the formula
- 35
- wherein R26 and R28 are independently halogens;
- R27 is O;
- and R29 is a linear or branched C1-C4 alkyl or C1-C4 haloalkyl, phenyl, chlorophenyl, p-tolyl, benzyl, biphenyl, or cyclohexyl;
- with
- (b) phenolphthalein or 4,4′-bis(hydroxyphenyl)phenyl phosphine oxide to yield said homopolymer or copolymer.
A method for preparing an optical or opthalmic lens, said method comprising injection molding into the form of said lens, a melt-processable phosphonate homopolymer or copolymer having units of the formula:
- 36
- wherein R11, R12, and R13 independently are O or S;
- R14 is a linear or branched C1-C4 alkyl or C1-C4 haloalkyl, phenyl, chlorophenyl, p-tolyl, benzyl, biphenyl, or cyclohexyl;
- and R15 is
- 37
- or any combination of any of the foregoing.
Dependencies are inferred from the claim text.