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Diisocyanate terminated macromer and formulation thereof for use as an internal adhesive or sealant

A macromonomer, polyisocyanate technology, applied in polyurea/polyurethane adhesives, adhesive types, adhesives, etc., can solve the problem of not providing enough operation and repositioning opportunities

Inactive Publication Date: 2008-03-05
ETHICON INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these copolymers are not suitable for use as surgical adhesives or sealants because the copolymers are already polymerized, i.e. already cured, and do not provide sufficient opportunities for manipulation and repositioning
In addition, it is not believed that such copolymers closely resemble the mechanical properties of undamaged tissue

Method used

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  • Diisocyanate terminated macromer and formulation thereof for use as an internal adhesive or sealant
  • Diisocyanate terminated macromer and formulation thereof for use as an internal adhesive or sealant
  • Diisocyanate terminated macromer and formulation thereof for use as an internal adhesive or sealant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102] Embodiment 1. Preparation of Polymer

[0103] Compare Prepolymer A1

[0104] Polyethylene glycol Mw900g / mol (50g, 0.056mol) was dried under vacuum at 120°C for 4 hours. The polymer was then cooled to room temperature under nitrogen and glycolide (12.90 g, 0.11 mol) was added. The catalyst stannous octoate was added in the amount of 1 mol catalyst: 30,000 mol glycolide. The mixture was continuously stirred under nitrogen and heated to 150 °C for 3 hours. Next, the polymer was cooled to 70°C and p-phenylene diisocyanate (19.57 g, 0.122 mol) was added. The reaction was continued for 4 hours under nitrogen with stirring. The theoretical structure of the resulting prepolymer is:

[0105]

[0106] The polymer is a white waxy resin at room temperature.

[0107] Prepolymer B1

[0108] A 10% ethyl acetate solution was prepared with 1 mol of tetraethylene glycol, 2.75 mol of 4-nitrobenzoyl chloride and 6 equivalents of sodium carbonate. The reaction was performed under...

Embodiment 2

[0124] Example 2: Degradation studies

[0125] The test polymers were cast on glass and allowed to moisture cure for several hours at ambient humidity until a rubbery film formed. The films were then subjected to the following accelerated hydrolysis conditions. This method consists of hydrolytically degrading the sample while maintaining a constant pH by titration with a standard base and measuring the amount of base used over time. Measurements and titrations were performed automatically by a pH stainstrument (718STAT Titrator Complete, MetroOhm, using SoftwareTiNet2.4). The samples were placed in a stirred, sealed 70 ml bath of deionized water maintained at a pH of 7.27 at 75°C + / - 0.2°C. The pH change (pH drop) of each sample bath was continuously monitored from the 7.27 set point. If any drop in pH was detected, sodium hydroxide solution was added to bring the pH back to 7.27 (NaOH 0.05N). Hydrolysis was continued until titrating base was no longer required to maintain...

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Abstract

A novel macromer is described herein, comprising benzoyl isocyanate terminal moieties and at least two residues of a water-soluble polymer having a molecular weight ranging from 80 to 10,000 adjacent to the carbonyl group of the benzoyl isocyanate moieties, thereby forming at least two ester linkages in the macromer.

Description

field of invention [0001] The present invention describes a novel polyisocyanate macromer and its use to form an in vivo adhesive or sealant for cardiovascular, peripheral vascular, cardiothoracic, gynecological, neurological and general abdominal surgery. More specifically, the macromer or formulation thereof polymerizes in the human body to form an elastic gel that is biocompatible and degrades to non-toxic, biocompatible products. Furthermore, the degradation products are water soluble, thus allowing the degradation products to be eliminated from the human body as waste products. Background of the invention [0002] In general, the key needs for tissue adhesives are: [0003] (1) When used, the adhesive must closely resemble the mechanical properties of undamaged tissue; [0004] (2) The adhesive should provide sufficient tack for "basic" fixation and an opportunity to manipulate and reposition before force-setting; [0005] (3) Any exothermic process involved in the c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/10C08G18/42C08G18/76A61L24/04C08G18/30
CPCC08G18/4252C08G18/771C09J175/06C08G2230/00A61L24/046C08L75/04C08G18/76C08G18/42C08G18/80
Inventor B·D·费茨
Owner ETHICON INC