Stabilization of poly(oxyalkylene) containing polymeric materials
First Claim
1. A medical device comprising:
- a poly(oxyalkylene)-containing polymeric material and a biocompatible organic multi-acid or biocompatible salt thereof, wherein the poly(oxyalkylene)-containing polymeric material has a polymer network having at least one unit of formula (I) —
O—
(R1—
O)n—
(R2—
O)m—
(R3—
O)p—
(I) wherein R1, R2, and R3, independently of one other, are each linear or branched C2-C4-alkylene, and n, m and p, independently of one another, are each a number from 0 to 100, wherein the sum of (n+m+p) is 5 to 1000;
wherein the biocompatible organic multi-acid or biocompatible salt thereof is distributed within the poly(oxyalkylene)-containing polymeric material but not crosslinked to the polymer network, and wherein the biocompatible organic multi-acid or biocompatible salt thereof is present in an amount effective to improve the stability of the medical device so that the medical device has a decreased susceptibility to oxidative degradation, characterized by having at least an 1.5-fold reduction of the amount of detectable formic acid and optionally other degradation by-products.
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Abstract
The present invention provides a method for producing a medical device, preferably an ophthalmic device, more preferably a contact lens, made of a stabilized poly(oxyalkylene)-containing polymeric material. The method of the invention comprises the steps of: curing, in a mold, a composition comprising (a) a prepolymer having at least one poly(oxyalkylene) unit, (b) a biocompatible organic multi-acid or biocompatible salt thereof in an amount sufficient to improve the stability of the poly(oxyalkylene)-containing polymer made from the composition, (c) optionally a photoinitiator or a thermal initiator, and (d) optionally one or more vinylic monomers, to form the medical device being less susceptible to oxidative degradation; and removing the medical device from the mold.
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Citations
41 Claims
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1. A medical device comprising:
- a poly(oxyalkylene)-containing polymeric material and a biocompatible organic multi-acid or biocompatible salt thereof, wherein the poly(oxyalkylene)-containing polymeric material has a polymer network having at least one unit of formula (I)
—
O—
(R1—
O)n—
(R2—
O)m—
(R3—
O)p—
(I)wherein R1, R2, and R3, independently of one other, are each linear or branched C2-C4-alkylene, and n, m and p, independently of one another, are each a number from 0 to 100, wherein the sum of (n+m+p) is 5 to 1000;
wherein the biocompatible organic multi-acid or biocompatible salt thereof is distributed within the poly(oxyalkylene)-containing polymeric material but not crosslinked to the polymer network, and wherein the biocompatible organic multi-acid or biocompatible salt thereof is present in an amount effective to improve the stability of the medical device so that the medical device has a decreased susceptibility to oxidative degradation, characterized by having at least an 1.5-fold reduction of the amount of detectable formic acid and optionally other degradation by-products.- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)
- a poly(oxyalkylene)-containing polymeric material and a biocompatible organic multi-acid or biocompatible salt thereof, wherein the poly(oxyalkylene)-containing polymeric material has a polymer network having at least one unit of formula (I)
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12. A method for producing a medical device, comprising the steps of:
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(1) obtaining a polymerizable fluid composition comprising (a) a prepolymer having ethylenically unsaturated groups and at least one poly(oxyalkylene) unit of formula (I) —
O—
(R1—
O)n—
(R2—
O)m—
(R3—
O)p—
(I)wherein R1, R2, and R3, independently of one other, are each linear or branched C2-C4-alkylene, and n, m and p, independently of one another, are each a number from 0 to 100, wherein the sum of (n+m+p) is 5 to 1000, (b) a biocompatible organic multi-acid or biocompatible salt thereof, (c) optionally a photoinitiator or a thermal initiator, and (d) optionally one or more vinylic monomers;
(2) introducing an amount of the polymerizable fluid composition in a mold for making the medical device; and
(3) actinically or thermally polymerizing the polymerizable fluid composition in the mold to form the medical device having a polymer network having at least one unit of formula (I) and the biocompatible organic multi-acid or biocompatible salt thereof which is not crosslinked to the polymer network, wherein the biocompatible organic multi-acid or biocompatible salt thereof is present in an amount effective to improve the stability of the medical device so that the medical device has a decreased susceptibility to oxidative degradation characterized by having at least an 1.5-fold reduction of the amount of detectable formic acid and optionally other degradation by-products. - View Dependent Claims (13, 14, 15, 16, 17, 18, 19, 20, 21, 22)
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23. A method for producing a medical device, comprising the steps of:
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(1) introducing a reactive mixture into a mold by using a Reaction Injection Molding (RIM) process to form the medical device, wherein the reactive mixture comprises (a) a monomer or prepolymer having functional groups and at least one poly(oxyalkylene) unit of formula (I) —
O—
(R1—
O)n—
(R2—
O)m—
(R3—
O)p—
(I)in which R1, R2, and R3, independently of one other, are each linear or branched C2-C4-alkylene, and n, m and p, independently of one another, are each a number from 0 to 100, wherein the sum of (n+m+p) is 5 to 1000, wherein the functional groups are amino, carboxy, hydroxy or isocyanato groups, and (b) an organic diamine, an organic polyamine, an organic diacid, an organic polyacid, an organic diol, an organic polyol, an organic diisocyante, or organic polyisocyanate, provided that components (a) and (b) react with each other to form a polyurea and/or polyurethane network;
(2) removing the medical device from the mold; and
(3) impregnating the medical device with a biocompatible organic multi-acid or biocompatible salt thereof in an amount effective to improve the stability of the medical device so that the medical device has a decreased susceptibility to oxidative degradation characterized by having at least an 1.5-fold reduction of the amount of detectable formic acid and optionally other degradation by-products. - View Dependent Claims (24, 25, 26, 27)
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28. A stabilized poly(oxyalkylene)-containing polymeric material, comprising:
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(a) a polymer network having at least one unit of formula (I) —
O—
(R1—
O)n—
(R2—
O)m—
(R3—
O)p—
(I)wherein R1, R2, and R3, independently of one other, are each linear or branched C2-C6-alkylene, and n, m and p, independently of one another, are each a number from 0 to 100, wherein the sum of (n+m+p) is 5 to 1000; and
(b) a biocompatible organic multi-acid or biocompatible salt thereof present in an amount sufficient to improve the stability of the poly(oxyalkylene)-containing polymeric material, which is distributed within the polymeric material but not crosslinked to the polymer network. - View Dependent Claims (29, 30, 31, 32, 33, 34)
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35. A method for sterilizing a medical device having a core material and/or a coating, wherein the core material and the coating, independently of each other, are made of a poly(oxyalkylene)-containing polymeric material, the method comprising:
- autoclaving the medical device in a solution containing a water-soluble and biocompatible organic multi-acid or biocompatible salt thereof in an amount sufficient to improve the stability of the poly(oxyalkylene)-containing polymeric material, so that the poly(oxyalkylene)-containing polymeric material has a decreased susceptibility to oxidative degradation characterized by having at least an 1.5-fold reduction of the amount of detectable formic acid and optionally other degradation by-products.
- View Dependent Claims (36, 37, 38, 39)
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40. An aqueous solution for sterilizing and/or storing an ophthalmic device, wherein the ophthalmic device is made of a poly(oxyalkylene)-containing polymeric material, the aqueous solution having:
- a biocompatible organic multi-acid or biocompatible salt thereof in an amount sufficient to improve the stability of the poly(oxyalkylene)-containing polymeric material;
an osmolarity of about 200 to 450 milli-osmole in 1000 ml (unit;
mOsm/ml), wherein the aqueous solution is capable of improving the stability of the poly(oxyalkylene)-containing polymeric material, so that the poly(oxyalkylene)-containing polymeric material has a reduced susceptibility to oxidative degradation characterized by having at least an 1.5-fold reduction of the amount of detectable formic acid and optionally other degradation by-products. - View Dependent Claims (41)
- a biocompatible organic multi-acid or biocompatible salt thereof in an amount sufficient to improve the stability of the poly(oxyalkylene)-containing polymeric material;
Specification