Hydroswellable, Segmented, Aliphatic Polyurethanes and Polyurethane Ureas

a polyurethane urea and water-welling technology, applied in the direction of impression caps, prostheses, drug compositions, etc., can solve the problems of chemical degradation, prior art is virtually silent on self-standing peu and peu liquid solventless compositions, etc., and achieve the effect of restoring the function of diseased or defective articulating joints and increasing volum

a polyurethane urea and water-welling technology, applied in the direction of impression caps, prostheses, drug compositions, etc., can solve the problems of chemical degradation, prior art is virtually silent on self-standing peu and peu liquid solventless compositions, etc., and achieve the effect of restoring the function of diseased or defective articulating joints and increasing volum

US20090233887A1Inactive Publication Date: 2009-09-17POLY MED

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis and Characterization of a Typical Polyether-carbonate-urethane, P-1

[0023]For an initial charge, poly(ethylene glycol) (Mn=400 Da) (0.15 moles) and tin(II) 2-ethyl hexanoate (3.53×10−4 moles) were added to a 500 mL, 3-neck, round-bottom flask equipped with a PTFE coated magnetic stir bar. The contents were heated to 70° C. and allowed to stir for 10 minutes. For a second charge, trimethylene carbonate (0.882 moles) was added and the contents were heated to 135° C. Conditions were maintained until practically complete monomer conversion was achieved. The magnetic stir bar was removed and replaced by a stainless steel mechanical stirrer. The polymer was cooled to room temperature. For a third charge, 1,6-diisocyanatohexane (0.12 moles) was added and the contents were stirred until complete mixing was achieved. The contents were stirred and heated to 100° C. Conditions were maintained for 1.25 hours. The polymer was allowed to cool to room temperature and then dissolved in an ...

example 2

Synthesis and Characterization of Liquid Polyether-ester-urethane: General Method

[0024]For an initial charge, poly(ethylene glycol) (Mn=400 Da) and tin(II) 2-ethyl hexanoate were added to a 500 mL, 3-neck, round-bottom flask equipped with a PTFE coated magnetic stir bar. The contents were heated to 70° C. and allowed to stir for 10 minutes. For a second charge, dl-lactide and glycolide were added and the contents were heated to 135° C. Conditions were maintained until practically complete monomer conversion was achieved. The magnetic stir bar was removed and replaced with a stainless steel mechanical stirrer. The polymer was cooled to room temperature. For a third charge, 1,6-diisocyanatohexane was added and the contents were stirred until complete mixing was achieved. The contents were stirred and heated to 100° C. Conditions were maintained for 1.25 hours. The polymer was allowed to cool to room temperature and then dissolved in an equal part of tetrahydrofuran. The polymer soluti...

example 3

Synthesis and Characterization of Typical Polyether-ester-urethanes Using the General Method of Example 2, P-2, P-3, and P-4

[0025]Polyether-ester-urethanes P-2, P-3, and P-4 were prepared using the method of Example 2 with 0.15, 2.225, 0.15 moles of polyethylene glycol (M, =400 Da), 2.60×10−4, 3.18×10−4, 2.60×10−4 moles of tin(II) 2-ethyl hexanoate, 0.52, 0.64, 0.52 moles of dl-lactide, 0.13, 0.16, 0.13 moles of glycolide, and 0.18, 0.18, 0.12 moles of 1,6-diisocyanatohexane, respectively. Polymers P-2, P-3, and P-4 were characterized for molecular weight by GPC using tetrahydrofuran as the mobile phase which resulted in Mn of 11, 9, and 9 kDa, Mw of 20, 14, and 15 kDa, Mp of 20, 12, 14, kDa, and PDI of 1.9, 1.6, and 1.6, respectively. Identity and composition were confirmed by FT-IR and NMR, respectively.

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PUM

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Abstract

Hydroswellable, absorbable and non-absorbable, aliphatic, segmented polyurethanes and polyurethane-urea capable of swelling in the biological environment with associated increase in volume of at least 3 percent have more than one type of segments, including those derived from polyethylene glycol and the molecular chains are structurally tailored to allow the use of corresponding formulations and medical devices as carriers for bioactive agents, rheological modifiers of cyanoacrylate-based tissue adhesives, as protective devices for repairing defective or diseased components of articulating joints and their cartilage, and scaffolds for cartilage tissue engineering.

Description

[0001]The present application claims the benefit of prior provisional application, U.S. Ser. No. 61 / 069,046, filed Mar. 12, 2008.FIELD OF THE INVENTION[0002]The present invention is directed to hydroswellable (or water-swellable) absorbable and non-absorbable aliphatic, segmented polyurethanes and polyurethane-ureas, which can undergo swelling when placed in the biological environment manifested through an at least 3 percent increase in volume by virtue of having a highly hydrophilic polyalkylene oxide as an inherent part of their segmented chain molecules. By varying the type and fraction of the different segments constituting the copolymers, their pharmaceutical and biomedical applications as non-absorbable and absorbable materials entail their use in carriers for the controlled release of bioactive agents, rheological modifiers of absorbable and non-absorbable cyanoacrylate tissue adhesives, synthetic cartilage-like materials, and scaffolds for tissue engineering cartilage tissue...

Claims

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Application Information

Patent Timeline
17 Sep 2009
Publication
US20090233887A1
IPC
A61K31/65; C08G18/00; A61K47/34; A61L24/04; C08G77/04
CPC
A61L24/0021; C08G64/0241; A61L27/52; A61L2430/06; C08G18/12; C08G18/4244; C08G18/428; C08G18/4283
Inventors
SHALABY, SHALABY W.; CORBETT, JOEL T.