Biocompatible polyurethanes modified with lower alkyl sulfonate and lower alkyl carboxylate
AssigneeWisconsin Alumni Research Foundation
InventorsTimothy G. Grasel, Stuart L. Cooper
Life of this patent
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Abstract
Modified-polyurethane block copolymers and devices formed therefrom demonstrate excellent biocompatibility and improved physical and mechanical properties. In a preferred embodiment, from about 5 to about 25 percent of urethane hydrogen atoms are replaced with propyl sulfonate and propyl carboxylate groups to provide the modified copolymer.
Claims25
A biocompatible, substantially solid polyurethane composition comprising a polyether-polyurethane copolymer based on a mole ratio of about 1.5/0.5/1.0 to about 10/9/1 of (a) an organic diisocyanate, (b) a C.sub.2 -C.sub.14 alkyl or aryl diol or diamine or hydroxy-functional amine and (c) a polyol having a number average molecular weight from about 500 to about 3000, respectively, the copolymer being modified wherein about 5 to about 25 percent of the urethane hydrogen atoms of the copolymer are replaced with a combination of lower alkyl (C.sub.1 -C.sub.6) sulfonate groups and lower alkyl (C.sub.1 -C.sub.6) carboxylate groups.
A biocompatible substantially solid poly(tetramethylene oxide)-based polyurethane composition comprising a polyether-polyurethane copolymer based on a mole ratio of about 1.5/1.0/1.0 to about 10/9/1 of an organic diisocyanate, a C.sub.2 -C.sub.14 alkyl or aryl diol or diamine and polytetramethylene oxide having a number average molecular weight of from about 500 to about 3000, respectively, the copolymer being modified wherein about 5 to about 25 percent of the urethane hydrogen atoms of the copolymer are replaced with a combination of propyl sulfonate groups and propyl carboxylate groups.
A biocompatible poly(tetramethylene oxide)-based polyurethane composition comprising a polyetherpolyurethane copolymer based on a 3/2/1 mole ratio of about 1.5/0.5/1.0 to about 10/9/1 of methylene bis(p-phenyl isocyanate), 1,4-butanediol, and polytetramethylene oxide having a number average molecular weight from about 500 to about 3000, wherein about 5 to about 25 percent of the urethane hydrogen atoms of the copolymer are replaced with a combination of propyl sulfonate groups and propyl carboxylate groups.
A method for the production of a modified and substantially solid polyether-polyurethane copolymer composition which is biocompatible and which provides improved physical and mechanical properties, said method comprising the steps of:
- (a) providing a polyether-polyurethane copolymer based on a 3/2/1 mole ratio of an organic diisocyanate, a C.sub.2 -C.sub.14 alkyl or aryl diol or diamine and a polyol;
- (b) modifying the copolymer by replacing up to about 25 percent of the urethane hydrogen atoms thereof with a combination of propyl sulfonate groups and propyl carboxylate groups in the presence of a solvent;
- and
- (c) removing the solvent by drying the modified copolymer.
A method for the production of a modified and substantially solid poly(tetramethylene oxide)-based polyurethane composition comprising a polyether-polyurethane copolymer which is biocompatible and which demonstrates improved physical and mechanical properties, said method comprising the steps of:
- (a) providing a polyether-polyurethane copolymer based on a 3/2/1 mole ratio of an organic diisocyanate, a C.sub.2 -C.sub.14 alkyl or aryl diol or diamine and polytetramethylene oxide having a number average molecular weight of about 1000;
- (b) modifying the copolymer by replacing from about 5 to about 25 percent of the urethane hydrogen atoms thereof with a combination of propyl sulfonate groups and propyl carboxylate groups in the presence of a solvent;
- and
- (c) removing the solvent by drying the modified copolymer.
Dependencies are inferred from the claim text.