Polysiloxane prepolymers for biomedical devices
First Claim
1. A prepolymer represented by the general formulae:
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M(*Dii*Diol*Dii*PS)x(*Dii*PS)y*Dii*M or
M(*Dii*Diol*Dii*PS)x(*Dii*PS)y*Dii*Diol*Dii*M wherein;
each M is independently a polymerizable ethylenically unsaturated radical;
each Dii is independently a diradical residue of a diisocyanate;
each Diol is independently a diradical residue of a diol having 1 to 10 carbon atoms;
each PS is independently a diradical residue of a polysiloxane-diol or a polysiloxane diamine;
each * is independently —
NH—
CO—
NH—
, —
NH—
COO—
or —
OCO—
NH—
;
x is at least 2, and y is at least 1.
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Accused Products
Abstract
A polysiloxane prepolymer that is useful for forming biomedical devices comprises blocks (I) and (II) and is terminated at each end with an ethylenically unsaturated radical:
(*Dii*Diol*Dii*PS)x (I)
(*Dii*PS)y (II) wherein: each Dii is independently a diradical residue of a diisocyanate; each Diol is independently a diradical residue of a diol having 1 to 10 carbon atoms; each PS is independently a diradical residue of a polysiloxane-containing diol or diamine; each * is independently —NH—CO—NH—, —NH—COO— or —OCO—NH—: x represents the number of blocks (I) and is at least 2, and y represents the number of blocks (II) and is at least 1.
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Citations
28 Claims
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1. A prepolymer represented by the general formulae:
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M(*Dii*Diol*Dii*PS)x(*Dii*PS)y*Dii*M or
M(*Dii*Diol*Dii*PS)x(*Dii*PS)y*Dii*Diol*Dii*Mwherein;
each M is independently a polymerizable ethylenically unsaturated radical;
each Dii is independently a diradical residue of a diisocyanate;
each Diol is independently a diradical residue of a diol having 1 to 10 carbon atoms;
each PS is independently a diradical residue of a polysiloxane-diol or a polysiloxane diamine;
each * is independently —
NH—
CO—
NH—
, —
NH—
COO—
or —
OCO—
NH—
;
x is at least 2, and y is at least 1. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28)
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7. The prepolymer of claim 6, wherein each R is alkylene, and each R′
- is independently alkyl or fluoroalkyl optionally including ether linkages.
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8. The prepolymer of claim 6, wherein Mn of PS ranges from 1000 to 8000.
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9. The prepolymer of claim 1, wherein the ratio of x to y is at least 0.6.
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10. The prepolymer of claim 1, wherein each M is independently a polymerizable ethylenically unsaturated radical of the formula:
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11. The prepolymer of claim 1, wherein:
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each M is methacryloxyethyl;
each Dii is the diradical residue of isophorone diisocyanate;
each Diol is the diradical residue of diethyleneglycol;
each PS is a diradical residue of a polydimethylsiloxane-diol having Mn of at least 2000; and
each * is —
NH—
COO—
or —
OCO—
NH—
.
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13. A copolymer that is the polymerization product of a monomeric mixture comprising a prepolymer of claim 1, and a comonomer.
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14. The copolymer of claim 13, wherein the monomeric mixture comprises a hydrophilic comonomer.
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15. The copolymer of claim 14, wherein the monomeric mixture comprises at least one hydrophilic monomer selected form the group consisting of:
- ethylenically unsaturated carboxylic acids;
(meth)acrylic substituted alcohols;
vinyl lactams; and
(meth)acrylamides.
- ethylenically unsaturated carboxylic acids;
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16. The copolymer of claim 15, wherein the monomeric mixture comprises at least one hydrophilic monomer selected form the group consisting of:
- methacrylic acid;
acrylic acid;
2-hydroxyethylmethacrylate;
glyceryl methacrylate;
N-vinyl pyrrolidone;
methacrylamide; and
N,N-dimethylacrylamide.
- methacrylic acid;
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17. The copolymer of claim 14, wherein the monomeric mixture further comprises a monofunctional silicone-containing monomer.
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18. The copolymer of claim 17, wherein the monomeric mixture further comprises methacryloxypropyl tris(trimethylsiloxy)silane.
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19. A hydrogel copolymer that is the hydrated polymerization product of a monomeric mixture comprising a prepolymer of claim 1, and a hydrophilic comonomer.
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20. The hydrogel copolymer of claim 19, having a water content of at least 20 weight percent.
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21. The hydrogel copolymer of claim 19, having a modulus no greater than 100 g/mm2.
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22. The hydrogel copolymer of claim 21, having a modulus between about 40 and 80 g/mm2.
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23. The hydrogel copolymer of claim 19, having an oxygen permeability of at least 100 barrers.
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24. The hydrogel copolymer of claim 23, having an oxygen permeability of at least 150 barrers.
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25. The hydrogel copolymer of claim 19, having a water content of at least 20 weight percent, a modulus between about 40 and 80 g/mm2, and an oxygen permeability of at least 150 barrers.
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26. A biomedical device comprising a copolymer of claim 19.
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27. An ophthalmic device comprising a copolymer of claim 19.
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28. The ophthalmic device of claim 27, that is a contact lens or an intraocular lens.
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12. A prepolymer comprising blocks (I) and (II) and terminated at each end with a polymerizable ethylenically unsaturated radical
(*Dii*Diol*Dii*PS)x-
(I)
(*Dii*PS)y
(II)wherein;
each Dii is independently a diradical residue of a diisocyanate;
each Diol is independently a diradical residue of a diol having 1 to 10 carbon atoms;
each PS is independently a diradical residue of a polysiloxane-diol;
each * is independently —
NH—
CO—
NH—
or —
OCO—
NH—
;
x represents the number of blocks (I) and is at least 2, and y represents the number of blocks (II) and is at least 1.
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Specification