Adhesive systems containing polyisocyanate prepolymers and aspartate-ester curing agents, processes for preparing the same, medical uses therefor and dispensing systems for the same

a technology of aspartate and curing agent, applied in the direction of adhesive types, polyurea/polyurethane adhesives, applications, etc., can solve the problems of cyanoacrylates only suitable for external surgical sutures, limited use, high cost, etc., and achieve the effect of simplifying application

Inactive Publication Date: 2009-07-30
BAYER MATERIALSCIENCE AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented new type of material has been developed that combines two types of materials - one being made up mostly by polymethylene diphenol (PMDI) resin and another containing an amine group like urethane groups or similar chemicals called alkaloids. These compositions can be used for making strong bonds between different parts of skin when applied directly onto it's surface during medical procedures such as laser surgery or dental treatment. They are easier to apply than traditional methods involving PMDI alone because they only require adding certain substances beforehand.

Problems solved by technology

Technically speaking, there exist technical problem addressed in these patented documents relating to improving the performance and durability of medical devices made of polymer material called soft contact adherants. Current methods involve adding chemicals like formaldehydes, gluteron ammonia resists, urethanesulfonic acid monoazones, acroleimides, triphenols, etc.; while other compounds may improve upon certain aspects including faster setting times without causing unwanted side effects.

Method used

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  • Adhesive systems containing polyisocyanate prepolymers and aspartate-ester curing agents, processes for preparing the same, medical uses therefor and dispensing systems for the same
  • Adhesive systems containing polyisocyanate prepolymers and aspartate-ester curing agents, processes for preparing the same, medical uses therefor and dispensing systems for the same
  • Adhesive systems containing polyisocyanate prepolymers and aspartate-ester curing agents, processes for preparing the same, medical uses therefor and dispensing systems for the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

Prepolymer A

[0090]465 g of HDI and 2.35 g of benzoyl chloride were placed in a 11 four-necked flask. 931.8 g of a polyether with an ethylene oxide content of 63% and a propylene oxide content of 37% (each based on the total alkylene oxide content) started with TMP (3-functional) were added within 2 hrs at 80° C. and then stirred for a further hour. Next, the excess HDI was distilled off by thin film distillation at 130° C. and 0.1 mm Hg. 980 g (71%) of the prepolymer with an NCO content of 2.53% were obtained. The residual monomer content was <0.03% HDI.

example 2

Aspartate B

[0091]1 mol of 2-methyl-1,5-diaminopentane was slowly added dropwise to 2 mols of diethyl maleate under a nitrogen atmosphere, so that the reaction temperature did not exceed 60° C. The mixture was then heated at 60° C. until diethyl maleate was no longer detectable in the reaction mixture, The product was purified by distillation.

example 2a

Aspartate Component Partially Pre-Extended with Isocyanate Group-Containing Prepolymer

[0092]1000 g of HDI (hexamethylene diisocyanate), 1 g of benzoyl chloride and 1 g of methyl para-toluenesulphonate were placed with stirring in a 41 four-necked flask. 1000 g of a bifunctional polypropylene glycol polyether with an average molecular weight of 2000 g / mol were added within 3 hours at 80° C. and then stirred for a further hour. The excess HDI was then distilled off by thin film distillation at 130° C. and 0.1 torr. The prepolymer obtained has an NCO content of 3.7%.

[0093]200 g of the prepolymer were fed with stirring at room temperature into 291 g of the aspartate B) from 2-methyl-1,5-diaminopentane in a 11 four-necked flask. This was stirred for a further two hours, until isocyanate groups were no longer detectable by IR spectroscopy. The product obtained had a viscosity of 3740 mPas and an NH equivalent weight of 460 g / eq.

Tissue Bonding Examples:

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Abstract

Adhesive systems comprising: (A) an isocyanate group-containing prepolymer prepared by reacting: (A1) an aliphatic isocyante; and (A2) a polyol having a number average molecular weight of ≧400 g/mol and 2 to 6 OH groups; and (B) a curing component comprising: (B1) an amino group-containing aspartate ester of the general formula (I);
wherein X represents an n-valent organic radical derived from a corresponding n-functional primary amine X(NH2)n, R1 and R2 each independently represent an organic radical having no Zerevitinov active hydrogens and n represents a whole number of at least 2; and (B2) an organic filler having a viscosity of 10 to 6000 mPas at 23° C. measured according to DIN 53019; their use in wound and tissue incision closure, adhesive films comprising the same and dispensing systems therefor.

Description

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Claims

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Application Information

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Owner BAYER MATERIALSCIENCE AG
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