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EP0579503A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Radiation-curable, urethane-acrylate prepolymers and crosslinked polymers

Assignee: Ethicon Inc
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Filing: 1993-07-16
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Granted: —
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Expires: 2013-07-16
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Abstract

Abstract A radiation-curable prepolymer of a polyurethane endtipped with an hydroxy (acrylate or methacrylate) is disclosed. The polyurethane is derived from the reaction of a polyfunctional isocyanate with a hydrolyzable oligomer of an anhydrous cyclic ester of an hydroxy acid. Crosslinked polymers prepared by irradiating the prepolymers are also disclosed. The crosslinked polymers are bioabsorbable and biocompatible with bodily tissue, yet still maintain the outstanding mechanical properties one would expect from a polyurethane. The prepolymers and crosslinked polymers are especially well-suited for the fabrication of surgical devices, particularly wound closure devices such as surgical staples and clips, in a stereolithography apparatus.

Inventors

  • 👤 Donald W. Regula
  • 👤 Michael F. Bregen
  • 👤 Stuart L. Cooper
  • 👤 Dennis D. Jamiolkowski
  • 👤 Rao S. Bezwada

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-31 11:24
CPC Classifications
A; A61; A61L; A61L31/00; A61L31/04; A61L31/06; A61L31/14; A61L31/148; B; B33; B33Y; B33Y70/00; B33Y80/00; C; C08; C08F; C08F290/00; C08F290/08; C08F290/14; C08F290/147; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/671; C08G18/672; C08G2230/00

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 43 words
A radiation-curable, urethane-acrylate prepolymer comprising the reaction product of the following: a) a urethane prepolymer of a polyfunctional isocyanate and a hydrolyzable oligomer of an anhydrous cyclic ester of an hydroxy acid, and b) an endtipping amount of an hydroxy (acrylate or methacrylate).
Claim 2
Dependent Claim 28 words
The urethane-acrylate prepolymer of claim 1 wherein the anhydrous cyclic ester of an hydroxy acid is lactide, glycolide, para-dioxanone, trimethylene carbonate, or a mixture of any of these.
Claim 3
Dependent Claim 31 words
The urethane-acrylate prepolymer of claim 1 wherein the anhydrous cyclic ester of an hydroxy acid is a mixture of ε-caprolactone and any of the following: lactide, glycolide, para-dioxanone, or trimethylene carbonate.
Claim 4
Dependent Claim 33 words
The urethane-acrylate prepolymer of any one of claims 1 to 3 wherein the polyfunctional isocyanate is toluene diisocyanate, isophorone diisocyanate, (meta) tetramethyl xylene diisocyanate, 4,4' methylene diphenylene diisocyanate, lysine triisocyanate, or isocyanatoethyl methacrylate.
Claim 5
Dependent Claim 21 words
The urethane-acrylate prepolymer of any one of claims 1 to 4 wherein the hydroxy (acrylate or methacrylate) is HEMA or HEA.
Claim 6
Dependent Claim 40 words
The urethane-acrylate prepolymer of claim 5 wherein the hydroxy (acrylate or methacrylate) is HEMA and wherein the endtipping amount of HEMA is defined by a mole ratio of the urethane prepolymer to HEMA of between about 2:1 to about 1:2.
Claim 7
Dependent Claim 26 words
A crosslinked polymer prepared by irradiating the urethane-acrylate prepolymer of any one of claims 1 to 6 under conditions sufficient to induce curing of said prepolymer.
Claim 8
Dependent Claim 19 words
The crosslinked polymer of claim 7 wherein the urethane-acrylate prepolymer is irradiated in the presence of a reactive diluent.
Claim 9
Dependent Claim 23 words
The crosslinked polymer of claim 7 or claim 8 wherein the urethane-acrylate prepolymer is irradiated by photopolymerization in the presence of a photoinitiator.
Claim 10
Dependent Claim 29 words
The crosslinked polymer of any one of claims 7 to 9 wherein the crosslinked polymer is shaped to form a surgical device such as a surgical staple or clip.

References Cited (Backward Citations)

USRE29131E Cited
JPS61190519A Cited

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