# US 10,117,963 B2 · Medical adhesives for stopping heavy bleeding and sealing leakages

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- Number: US 10,117,963 B2
- Document ID: US10117963B2
- Status: Granted
- Kind: B2
- Application number: 15/667,744
- Filed: 2017-08-03
- Published: 2017-11-16
- Granted: 2018-11-06
- Earliest claimed: 2008-07-17
- Assignees: Adhesys Medical GmbH
- Applicants: Adhesys Medical GmbH
- Inventors: Heike Heckroth; Burkhard Köhler; Sebastian Dörr
- Web page: https://patentgrep.com/patent/US10117963B2

## CPC

- A61L 24/0094: {containing macromolecular fillers}
- A61L 24/046: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds (A61L24/043 takes precedence)}
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 7/04: Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- C08G 18/089: {Reaction retarding agents}
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/4837: {and other oxyalkylene units}
- C08L 75/04: Polyurethanes
- C09J 175/12: from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
- A61L 2400/04: Materials for stopping bleeding
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)

## Abstract

The present invention relates to a method that includes providing a formulation having an isocyanate-functional prepolymer and a curing component comprising an amino-functional aspartic ester of the general formula (I) applying the formulation to a cell tissue; and curing the formulation such that the loss of blood (haemostatic) or tissue fluids is staunched or leaks in cell tissues are sealed.

## Claims

### Claim 1

A method of staunching the loss of blood (haemostatic) or tissue fluids comprising:
a. providing a formulation comprising
A) an isocyanate-functional prepolymer obtained from
A1) an aliphatic isocyanate and
A2) a polyol component having a number-average molecular weight of greater than or equal to 400 g/mol and an average OH functionality of 2 to 6,
B) a curing component comprising
B1) an amino-functional aspartic ester of the general formula (I)
where
X is an organic radical obtained by removing the primary amino groups from 1,3-diaminopentane, 1,5-diaminopentane, or 1, 13-diamino-4,7,10-trioxatridecane,
R1 and R2 are ethyl and
n is 2
b. applying the formulation to a cell tissue; wherein the cell tissue comprises human or animal tissue; and
c. curing the formulation such that the loss of blood (haemostatic) or tissue fluids is staunched,
wherein the formulation is applied in an in vivo application or an in vitro application.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the curing component further comprises organic fillers which have a viscosity as measured to DIN 53019 at 23° C. in the range of from 10 to 6000 mPas.

### Claim 3 (depends on 2)

The method according to claim 2, wherein the formulation further comprises reaction products of the isocyanate-functional prepolymer with the organic fillers.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the formulation further comprises reaction products of the isocyanate-functional prepolymer with the amino-functional aspartic ester.

### Claim 5 (depends on 4)

The method according to claim 4, wherein the formulation further comprises reaction products of the isocyanate-functional prepolymer with organic fillers.

### Claim 6 (depends on 1)

The method according to claim 1, wherein the curing component further comprises organic fillers which have a viscosity as measured to DIN 53019 at 23° C. in the range of from 10 to 6000 mPas and wherein the formulation further comprises reaction products of the isocyanate-functional prepolymer with the amino-functional aspartic ester and the organic fillers.

### Claim 7 (depends on 1)

The method according to claim 1, wherein the polyol component has a number-average molecular weight of 4000 to 8500 g/mol.

### Claim 8 (depends on 1)

The method according to claim 1, wherein the polyol component comprises a polyalkylene oxide polyether.

### Claim 9 (depends on 8)

The method according to claim 8, wherein the polyalkylene oxide polyether contain from 60% to 90% of ethylene oxide-based units, based on the total amount of alkylene oxide units.

### Claim 10 (depends on 2)

The method according to claim 2, wherein the organic fillers comprise polyether polyols.

### Claim 11 (depends on 1)

The method according to claim 1, wherein the formulation is cured for a period of time from 30 seconds to 10 minutes.

### Claim 12 (depends on 1)

The method according to claim 1, wherein the formulation is cured for a period of time from 30 seconds to 2 minutes.