Polysiloxane prepolymers for biomedical devices
First Claim
Patent Images
1. A prepolymer represented by the general formula:
-
M(*Dii*PS)x*Dii*M
(I) wherein;
each M is independently a polymerizable ethylenically unsaturated radical;
each Dii is independently a diradical residue of a diisocyanate;
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—
; and
x is at least 2.
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Accused Products
Abstract
A polysiloxane prepolymer that is useful for forming biomedical devices has the formula:
M(*Dii*PS)x*Dii*M (I) wherein: each M is independently a polymerizable ethylenically unsaturated radical; each Dii is independently a diradical residue of a diisocyanate; 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—; and x is at least 2.
65 Citations
25 Claims
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1. A prepolymer represented by the general formula:
-
M(*Dii*PS)x*Dii*M
(I)wherein;
each M is independently a polymerizable ethylenically unsaturated radical;
each Dii is independently a diradical residue of a diisocyanate;
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—
; and
x is at least 2. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25)
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5. The prepolymer of claim 4, wherein each R is alkylene, and each R′
- is independently alkyl or fluoroalkyl optionally including ether linkages.
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6. The prepolymer of claim 5, wherein Mn of PS ranges from 1000 to 8000.
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7. The prepolymer of claim 1, wherein x is at least 3.
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8. The prepolymer of claim 1, wherein each M is independently a polymerizable ethylenically unsaturated radical of the formula:
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9. The prepolymer of claim 1, wherein:
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each M is 2-ethylenemethacrylate;
each Dii is the diradical residue of isophorone diisocyanate;
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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10. A copolymer that is the polymerization product of a monomeric mixture comprising a prepolymer of claim 1, and a comonomer.
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11. The copolymer of claim 10, wherein the monomeric mixture comprises a hydrophilic comonomer.
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12. The copolymer of claim 11, wherein the monomeric mixture comprises at least one hydrophilic monomer selected form the group consisting of:
- unsaturated carboxylic acids;
(meth)acrylic substituted alcohols;
vinyl lactams; and
(meth)acrylamides.
- unsaturated carboxylic acids;
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13. The copolymer of claim 12, 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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14. The copolymer of claim 11, wherein the monomeric mixture further comprises a monofunctional silicone-containing monomer.
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15. The copolymer of claim 14, wherein the monomeric mixture further comprises methacryloxypropyl tris(trimethylsiloxy)silane.
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16. 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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17. The hydrogel copolymer of claim 16, having a water content of at least 20 weight percent.
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18. The hydrogel copolymer of claim 16, having a modulus no greater than 100 g/mm2.
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19. The hydrogel copolymer of claim 18, having an oxygen permeability of at least 100 barrers.
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20. The hydrogel copolymer of claim 16, having an oxygen permeability of at least 100 barrers.
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21. The hydrogel copolymer of claim 20, having an oxygen permeability of at least 150 barrers.
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22. The hydrogel copolymer of claim 16, having a water content of at least 20 weight percent, a modulus no greater than 100 g/mm2, and an oxygen permeability of at least 150 barrers.
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23. A biomedical device comprising a hydrogel copolymer of claim 16.
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24. An ophthalmic device comprising a copolymer of claim 16.
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25. The ophthalmic device of claim 24, that is a contact lens or an intraocular lens.
Specification