WO2002058757A1 - Antimicrobial incision films - Google Patents

Antimicrobial incision films Download PDF

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Publication number
WO2002058757A1
WO2002058757A1 PCT/EP2001/014657 EP0114657W WO02058757A1 WO 2002058757 A1 WO2002058757 A1 WO 2002058757A1 EP 0114657 W EP0114657 W EP 0114657W WO 02058757 A1 WO02058757 A1 WO 02058757A1
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Prior art keywords
incision
films
film
antimicrobial polymers
films according
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PCT/EP2001/014657
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German (de)
French (fr)
Inventor
Peter Ottersbach
Markus Oles
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Creavis Gesellschaft Für Technologie Und Innovation Mbh
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Publication of WO2002058757A1 publication Critical patent/WO2002058757A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/44—Medicaments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/58—Adhesives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/04—Macromolecular materials
    • A61L31/041—Mixtures of macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/16—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents

Definitions

  • the invention relates to the production and use of antimicrobial incision films.
  • a newer method to minimize problems is the use of antimicrobial coated incision foils, which are supposed to suppress the spread of skin germs of the patient in surgical wounds more efficiently than can be achieved by skin disinfection with antiseptics alone. Wound infections are often considered inevitable precisely because many of the germs involved come from the patient's skin itself. So it can e.g. B. in orthopedic interventions come to considerable complications when germs from the patient's skin enter the operating area and germs are carried away.
  • the patient's skin is preoperatively treated with various disinfectants such as B. disinfected chlorhexidine or alcohol-containing antiseptics and thus reduces the germ infestation.
  • an incision film is applied to the surgical area. To do this, the incise film is unfolded and the cover paper is peeled off parallel to the holder edges. The incise film is gently applied to the skin, which has meanwhile dried, by pressing it on from the center with a sterile cloth. This avoids air pockets. The surgical incision is then made in the foil area. The film adheres / sticks firmly to the skin, even at the cut edge, even when stretched. After long interventions, the film can then be removed again easily. The incision film is used to cover the surgical field and is intended to prevent intraoperative wound contamination Prevent skin.
  • the present invention is therefore based on the object of developing novel incision films which avoid the described disadvantages of the incision films coated with low molecular weight antiseptics.
  • the invention therefore relates to incision films containing antimicrobial polymers.
  • the proportion of the antimicrobial polymer in the Incision film fluctuate within wide limits without the antimicrobial effect becoming too small, for example from 0.5 to 95% by weight, preferably 1 to 70% by weight, particularly preferably 1 to 20% by weight.
  • the antimicrobial polymer can either be used directly in the manufacture of the films, e.g. in the extrusion or blow molding, with incorporated or subsequently in the form of a coating, for. B. as part of a varnish or resin.
  • the result is a surface of the film impregnated with an antimicrobial polymer.
  • the incision films consist of a polymer blend, of antimicrobial polymers with at least one further polymer or of a copolymer of the respective monomers.
  • metal foils in addition to polymer foils, metal foils, e.g. possible for burns.
  • the incision film according to the invention can apply a skin pressure sensitive adhesive (e.g. EUDRAGIT from Röhm) to iron.
  • a skin pressure sensitive adhesive e.g. EUDRAGIT from Röhm
  • This can either have no antimicrobial properties or contain antimicrobial polymers. If the skin pressure sensitive adhesive contains antimicrobial polymers, the film and the applied adhesive are to be understood as incision films.
  • the addition of antimicrobial polymers to the skin pressure sensitive adhesive can also be carried out in addition to the previously mentioned possibilities for coating, glare formation or copolymerization with antimicrobial polymers.
  • Nitrogen and phosphorus functionalized monomers are preferably used for the preparation of the antimicrobial polymers, in particular one or more of the following Monomer e:
  • 2-diethylaminoethyl methacrylic acid 2-methacryloyloxyethyltrimethylammonium chloride, 3 - methacryloylaminopropyltrimethylammonium chloride, 2-methacryloyloxyethyltrimethylammonium bromide, 2-methacryloyloxyethyl-4-benzoyldimethylammonium bromide, 2-methacryloyloxyethylidylphomidylphosphonium triflammonium bromide
  • the incision film consists or contains polymers
  • these can be polypropylene, polyamides, polysulfoxides, polysiloxanes, polyurethanes, polystyrene, polyvinyl chloride, polymethyl methacrylate, polyacrylic acid, polysilicones or polyurethanes, their blends or copolymers.
  • the film from Example 1 with its coated side facing the skin, is placed on the left forearm of a test subject and attached to the edge of the film by means of conventional skin patches.
  • an uncoated polyethylene film (reference film) of the same size is attached in an analogous manner. After three hours, both foils are removed and a skin wipe is carried out to determine the microbial contamination of the previously covered areas of the skin. It can be seen here that the skin surface treated with the film from Example 1 has a significantly lower germ load than that treated with the reference film.
  • Example 2a After filtering off the product, the filter residue is rinsed with 100 ml of a mixture of ethanol / demineralized water in a ratio of 1: 1 in order to remove any remaining monomers. The product is then dried in vacuo at 50 ° C for 24 hours. 2 g of the product are dissolved in 10 g of ethanol and applied to a 4 by 6 cm polyethylene film using a 100 micrometer doctor blade. The film is then dried at 50 ° C for 24 hours.
  • Example 2a Example 2a:
  • Example 2 2 g of the product from Example 2 are dissolved in 10 g of ethanol and applied to a 4 by 6 cm polyethylene film using a 100 micrometer doctor blade. The film is then dried at 50 ° C for 24 hours.
  • This film with its coated side facing the skin, is placed on the left forearm of a test subject and attached to the skin by means of conventional skin patches on the edge of the film.
  • an uncoated polyethylene film (reference film) of the same size is attached in an analogous manner. After three hours, both foils are removed and a skin wipe is carried out to determine the microbial contamination of the previously covered areas of the skin. This shows that the surface of the skin treated with the coated film has a significantly lower germ load than that treated with the reference film.
  • Example 2 2 g of the product from Example 2 are dissolved in 10 g of ethanol and applied to a 4 by 6 cm silicone film using a 100 micrometer doctor blade. The film is then dried at 50 ° C for 24 hours.
  • This film with its coated side facing the skin, is placed on the left forearm of a test subject and attached to the skin by means of conventional skin patches on the edge of the film.
  • An uncoated silicone film (reference film) of the same size is attached to the right forearm of the test subject in an analogous manner. After three hours, both foils are removed and a skin wipe is carried out to determine the microbial contamination of the previously covered areas of the skin. This shows that the surface of the skin treated with the coated film has a significantly lower germ load than that treated with the reference film.
  • Example 3 90 ml of 2-tert-methacrylic acid. butylaminoethyl ester (from Aldrich) and 180 ml of ethanol are placed in a three-necked flask and heated to 65 ° C. under a stream of argon. After that 0.745 g of azobisisobutyronitrile dissolved in 20 ml of ethyl methyl ketone was slowly added dropwise with stirring. The mixture is heated to 70 ° C. and stirred at this temperature for 72 hours. After this time, the reaction mixture is stirred into 1 liter of demineralized water, the polymeric product precipitating.
  • the filter residue is rinsed with 100 ml of a 10% solution of ethanol in water in order to remove any remaining monomers.
  • the product is then dried in vacuo at 50 ° C for 24 hours. 4 g of the product are dissolved in 32 g of di-isononyl phthalate. Then 64 g of polyvinyl chloride granules are added to this mixture, the mixture being stirred intimately until it becomes pasty. 20 g of the paste obtained are spread onto a metal plate using a doctor blade in such a way that a layer thickness of 0.7 mm is obtained. The plate with the paste on it is then heated to 200 ° C. for 2 minutes, during which the paste gels and a soft PVC film is formed.
  • Example 3a A 4 x 6 cm piece of film from Example 3 is placed on the left forearm of a test subject and attached to the skin on the edge of the film by means of conventional skin plasters.
  • An uncoated PVC film (reference film) of the same size is attached in an analogous manner to the right forearm of the test subject. After three hours, both foils are removed and a skin wipe is carried out to determine the microbial contamination of the previously covered areas of the skin. It can be seen here that the skin surface treated with the film from Example 3 has a significantly lower germ load than that treated with the reference film.
  • Example 4 50 ml tert. -Butylaminoethyl methacrylate (Aldrich) and 250 ml of ethanol are placed in a three-necked flask and heated to 65 ° C. under a stream of argon. Then 0.6 g of azobisisobutyronitrile dissolved in 20 ml of ethyl methyl ketone are slowly added dropwise with stirring. The mixture is heated to 70 ° C. and stirred at this temperature for 72 hours. After this time, the reaction mixture is stirred into 1.5 l of deionized water, the polymeric product precipitating.
  • the filter residue is rinsed with 100 ml of a mixture of ethanol / demineralized water in a ratio of 1: 1 in order to remove any remaining remove monomers.
  • the product is then dried in vacuo at 50 ° C for 24 hours. 30 g of the product are compounded together with 1000 g of PVC granulate. The compound is then extruded into a 4 cm wide film using a laboratory extruder.
  • a 4 by 6 cm piece of film from Example 4 is placed on the left forearm of a test subject and attached to the skin on the edge of the film using conventional skin patches.
  • An equally large PVC film without antimil ⁇ obial additives (reference film) is attached in an analogous manner to the subject's right forearm. After three hours, both foils are removed and a skin wipe is carried out to determine the microbial contamination of the previously covered areas of the skin. It can be seen here that the skin surface treated with the film from Example 3 has a significantly lower germ load than that treated with the reference film.

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Abstract

The invention relates to a method for producing antimicrobially effective incision films.

Description

Antimikrobielle InzisionsfolienAntimicrobial incision films
Die Erfindung betrifft die Herstellung und die Verwendung antimikrobieller Inzisionsfolien.The invention relates to the production and use of antimicrobial incision films.
Allein in Deutschland gibt es nach einer Studie der Deutschen Krankenhausgesellschaft jedes Jahr ca. 1 Mio. mosokomiale Infektionen. Jede fünfte davon ist eine Wundinfektion. Viele dieser Wundinfektionen könnten vermieden werden, wenn konsequent antiseptische Maßnahmen angewandt würden.According to a study by the German Hospital Society, there are approximately 1 million mosocomial infections in Germany alone. Every fifth of them is a wound infection. Many of these wound infections could be avoided if consistent antiseptic measures were used.
Eine neuere Methode zur Problemminimierung ist der Einsatz antimikrobiell beschichteter Inzisionsfolien, welche die Verschleppung von Hautkeimen des Patienten in Operationswunden effizienter unterdrücken sollen, als es durch eine Hautdesinfektion mit Antiseptika alleine erreicht werden kann. Wundinfektionen werden gerade deshalb oft als unvermeidbar angesehen, da viele der beteiligten Keime von der Haut des Patienten selber stammen. So kann es z. B. bei orthopädischen Eingriffen zu erheblichen Komplikationen kommen, wenn Keime von der Haut des Patienten in den Operationsbereich gelangen und eine Keimverschleppung stattfindet.A newer method to minimize problems is the use of antimicrobial coated incision foils, which are supposed to suppress the spread of skin germs of the patient in surgical wounds more efficiently than can be achieved by skin disinfection with antiseptics alone. Wound infections are often considered inevitable precisely because many of the germs involved come from the patient's skin itself. So it can e.g. B. in orthopedic interventions come to considerable complications when germs from the patient's skin enter the operating area and germs are carried away.
Dass eine Hautdesinfektion im Vorfeld einer Operation alleine Keime nicht in ausreichendem Maße abtötet, wird durch zahlreiche Studien hinlänglich gezeigt. Eine gängige Maßnahme zur Reduzierung der Keimbelastung bei operativen Eingriffen ist deshalb das folgende Verfahren.Numerous studies have sufficiently shown that skin disinfection alone does not sufficiently kill germs prior to surgery. The following procedure is therefore a common measure for reducing the bacterial load during surgical interventions.
Die Haut des Patienten wird präoperativ durch verschiedene Desinfektionsmittel wie z. B. Chlorhexidin oder alkoholhaltigen Antiseptika desinfiziert und so der Keimbefall reduziert. Zusätzlich wird eine Inzisionsfolie auf den Operationsbereich aufgebracht. Dazu wird die Inzisionsfolie entfaltet und das Abdeckpapier parallel zu den Halterändern abgezogen. Unter leichter Spannung wird die Inzisionsfolie auf die inzwischen abgetrocknete Haut geldebt, indem die Folie vom Zentrum beginnend mit einem sterilen Tuch aufgedrückt wird. Hierdurch werden Lufteinschlüsse vermieden. Im Folienbereich wird dann der OP-Schnitt gesetzt. Die Folie haftet/klebt fest auf der Haut, auch am Schnittrand selbst bei starker Dehnung. Nach langen Eingriffen lässt sich die Folie anschließend wieder gut entfernen. Die Inzisionsfolie dient damit zur Abdeckung des Operationsfeldes und soll intraoperative Wundkontanimationen aus der Haut verhindern.The patient's skin is preoperatively treated with various disinfectants such as B. disinfected chlorhexidine or alcohol-containing antiseptics and thus reduces the germ infestation. In addition, an incision film is applied to the surgical area. To do this, the incise film is unfolded and the cover paper is peeled off parallel to the holder edges. The incise film is gently applied to the skin, which has meanwhile dried, by pressing it on from the center with a sterile cloth. This avoids air pockets. The surgical incision is then made in the foil area. The film adheres / sticks firmly to the skin, even at the cut edge, even when stretched. After long interventions, the film can then be removed again easily. The incision film is used to cover the surgical field and is intended to prevent intraoperative wound contamination Prevent skin.
In der Literatur ist der Einsatz von Inzisionsfolien noch sehr umstritten. Viele klinische Studien aus dem Jahre 1986 und 1987 bezweifeln den Nutzen solcher Folien. Breitner, S., Ogdeschel, G. beschrieben in Unfallchirurgie 12 (1986), 301-304, den Einsatz einer Inzisionsfolie unter klinisch kontrollierten Bedingungen an 123 Patienten mit orthopädischen Operationen. Die Autoren kamen zu dem Ergebnis, dass Bakterien der normalen Hautflora nur in seltenen Fällen Infektionserreger nach orthopädischen Operationen sind und kommen damit zu dem Schluss, dass eine Profilaxe von Wundinfektionen nicht notwendig ist. Ähnlich sehen es die Autoren Diwan, P.A. et al. in Aust.N.Z.J. Surg., 57 (1987), 859-863. Auch sie sahen in einer Idinisch randomisierten Studie keinen Unterschied hinsichtlich der Infektionsrate bei Verwendung von Inzisionsfolien. All diesen Untersuchungen ist gemeinsam, dass die Inzisionsfolien nicht antimikrobiell beschichtet waren.The use of incision foils is still very controversial in the literature. Many clinical studies from 1986 and 1987 question the usefulness of such films. Breitner, S., Ogdeschel, G. described in Unfallchirurgie 12 (1986), 301-304, the use of an incision film under clinically controlled conditions in 123 patients with orthopedic operations. The authors came to the conclusion that bacteria of the normal skin flora are only rarely infectious agents after orthopedic surgery and thus come to the conclusion that a profiling of wound infections is not necessary. The authors Diwan, P.A. et al. in Aust.N.Z.J. Surg., 57: 859-863 (1987). They also saw no difference in the infection rate when using incision foils in an Idinically randomized study. All of these investigations have in common that the incision films were not coated with an antimicrobial agent.
Der vorliegenden Erfindung liegt daher die Aufgabe zugrunde neuartige Inzisionsfolien zu entwickeln, welche die beschriebenen Nachteile der mit niedermolekularen Antiseptika beschichteten Inzisionsfolien vermeiden.The present invention is therefore based on the object of developing novel incision films which avoid the described disadvantages of the incision films coated with low molecular weight antiseptics.
Aus der europäischen Patentanmeldungen 0 862 858 ist bekannt, dass Copolymere von tert.- Butylaminoethylmethacrylat, einem Methacrylsäureester mit sekundärer Aminofunktion, inhärent mikrobizide Eigenschaften besitzen. Die antimikrobielle Wirksamkeit dieser polymeren Systeme ist eng mit ihrer dreidimensionalen Struktur, Konformation und verfügbaren Oberfläche verbunden. Sie eignen sich vor allem in Anwendungsbereichen, in denen es auf einen langanhaltenden, oberflächenaktiven Schutz vor mikrobiellem Angriff ankommt.From European patent applications 0 862 858 it is known that copolymers of tert-butylaminoethyl methacrylate, a methacrylic acid ester with a secondary amino function, have inherent microbicidal properties. The antimicrobial effectiveness of these polymeric systems is closely related to their three-dimensional structure, conformation and available surface. They are particularly suitable in areas of application where long-lasting, surface-active protection against microbial attack is important.
Es wurde nun überraschend gefunden, dass sich die beschriebene Aufgabe durch Einsatz antimikrobieller Polymere zur Herstellung von Inzisionsfolien lösen lässt.It has now surprisingly been found that the object described can be achieved by using antimicrobial polymers for the production of incision films.
Gegenstand der Erfindung sind daher Inzisionsfolien, enthaltend antimikrobielle Polymere.The invention therefore relates to incision films containing antimicrobial polymers.
Durch den engen Hautkontakt kann der Anteil des antimikrobiellen Polymeren in der Inzisionsfolie in weiten Grenzen schwanken, ohne das der antimikrobielle Effekt zu gering wird, so z.B. von 0,5 bis 95 Gew.-%, bevorzugt 1 bis 70 Gew.-%, besonders bevorzugt 1 bis 20 Gew.-%.Due to the close skin contact, the proportion of the antimicrobial polymer in the Incision film fluctuate within wide limits without the antimicrobial effect becoming too small, for example from 0.5 to 95% by weight, preferably 1 to 70% by weight, particularly preferably 1 to 20% by weight.
Hierbei kann das antimikrobielle Polymer entweder unmittelbar bei der Herstellung der Folien, z.B. bei der Extrusion bzw. der Blasformung, mit eingearbeitet oder aber nachträglich in Form einer Beschichtung, z. B. als Teil eines Lackes oder Harzes, auf diese aufgebracht werden. Hierdurch erhält man als Ergebnis eine mit antimikrobiellem Polymer imprägnierte Oberfläche der Folie.The antimicrobial polymer can either be used directly in the manufacture of the films, e.g. in the extrusion or blow molding, with incorporated or subsequently in the form of a coating, for. B. as part of a varnish or resin. The result is a surface of the film impregnated with an antimicrobial polymer.
Es ist auch möglich, das die Inzisionsfolien aus einem Polymerblend, von antimikrobiellen Polymeren mit mindestens einem weiteren Polymeren oder aus einem Copolymerisat der jeweiligen Monomeren besteht.It is also possible for the incision films to consist of a polymer blend, of antimicrobial polymers with at least one further polymer or of a copolymer of the respective monomers.
Im Falle der Beschichtung sind neben Polymerfolien auch Metallfolien, z.B. für Verbrennungen denkbar.In the case of coating, in addition to polymer foils, metal foils, e.g. possible for burns.
Weiterhin kann die erfindungsgemäße Inzisionsfolie einen Hauthaftkleber (z.B: EUDRAGIT der Fa. Röhm) auf eisen. Dieser kann entweder keine antimikrobiellen Eigenschaften besitzen oder antimikrobielle Polymere enthalten. Enthält der Hauthaftkleber antimikrobielle Polymere so ist die Folie und der aufgebrachte Kleber als Inzisionsfolie zu verstehen. Der Zusatz von antimikrobiellen Polymeren in den Hauthaftkleber kann auch zusätzlich zu den bereits genannten Möglichkeiten der Beschichtung, Blendbildung oder Copolymerisation mit antimikrobiellen Polymeren erfolgen.Furthermore, the incision film according to the invention can apply a skin pressure sensitive adhesive (e.g. EUDRAGIT from Röhm) to iron. This can either have no antimicrobial properties or contain antimicrobial polymers. If the skin pressure sensitive adhesive contains antimicrobial polymers, the film and the applied adhesive are to be understood as incision films. The addition of antimicrobial polymers to the skin pressure sensitive adhesive can also be carried out in addition to the previously mentioned possibilities for coating, glare formation or copolymerization with antimicrobial polymers.
Die so behandelten Oberflächen zeigen eine antimikrobielle Wirksamkeit die dauerhaft, und gegen physikalische Beanspruchungen widerstandsfähig ist. Diese Beschichtungen enthalten keine niedermolekularen Biozide, was eine Migration toxikologisch problematischer Stoffe über den gesamten Nutzungszeitraum hinweg effektiv ausschließt. Bevorzugt werden zur Herstellung der antimikrobiellen Polymere Stickstoff- und Phosphorfünktionalisierte Monomere eingesetzt, insbesondere eines oder mehrere der folgenden Monomer e:The surfaces treated in this way show an antimicrobial effectiveness that is permanent and resistant to physical stress. These coatings do not contain any low molecular weight biocides, which effectively rules out the migration of toxicologically problematic substances over the entire period of use. Nitrogen and phosphorus functionalized monomers are preferably used for the preparation of the antimicrobial polymers, in particular one or more of the following Monomer e:
Methacrylsäure-2-tert. -butylaminoethylester, Methacrylsäure-2-diethylaminoethylester, Meth- acrylsäure-2-diethylaminomethylester, Acrylsäure-2-tert. -butylaminoethylester, Acrylsäure-3- dimethylaminopropylester, Acrylsäure-2-diethylaminoethylester, Acrylsäure-2-dimethylamino- ethylester, Dimethylaminopropylmethacrylamid, Diethylaminopropylmethacrylamid, Acrylsäure- 3-dimethylaminopropylamid, 2-Methacryloyloxyethyltrimethylammoniummethosulfat,Methacrylic acid-2-tert. -butylaminoethyl ester, methacrylic acid-2-diethylaminoethyl ester, methacrylic acid-2-diethylaminomethyl ester, acrylic acid-2-tert. -butylaminoethyl ester, acrylic acid 3-dimethylaminopropyl ester, acrylic acid 2-diethylaminoethyl ester, acrylic acid 2-dimethylamino ethyl ester, dimethylaminopropyl methacrylamide, diethylaminopropyl methacrylamide, acrylic acid 3-dimethylaminopropylamide, 2-methacryloyloxyethyltrimethylammonium methosulfate,
Methacrylsäure-2-diethylaminoethylester, 2-Methacryloyloxyethyltrimethylammoniumchlorid, 3 - Methacryloylaminopropyltrimethylammonium-chlorid, 2-Methacryloyloxyethyltrimethyl- ammoniumchlorid, 2- Acryloyloxyethyl-4-benzoyldimethylammoniumbromid, 2- Meth- acryloyloxyethyl-4-benzoyldimethylammoniumbromid, Allyltriphenylphosphoniumbromid,2-diethylaminoethyl methacrylic acid, 2-methacryloyloxyethyltrimethylammonium chloride, 3 - methacryloylaminopropyltrimethylammonium chloride, 2-methacryloyloxyethyltrimethylammonium bromide, 2-methacryloyloxyethyl-4-benzoyldimethylammonium bromide, 2-methacryloyloxyethylidylphomidylphosphonium triflammonium bromide
Allyltriphenylphosphoniumchlorid, 2- Acrylamido-2-methyl- 1 -propansulfonsäure, 2-Diethylami- noethylvinylether und/oder 3-Aminopropylvinylether.Allyl triphenylphosphonium chloride, 2-acrylamido-2-methyl-1-propanesulfonic acid, 2-diethylaminoethyl vinyl ether and / or 3-aminopropyl vinyl ether.
Sofern die Inzisionsfolie aus Polymeren besteht oder enthält, können dies Polypropylen, Polyamide, Polysulfoxide, Polysiloxane, Polyurethane, Polystyrol, Polyvinylchlorid, Polymethylmethacrylat, Polyacrylsäure, Polysilikone oder Polyurethane deren Blends oder Copolymere sein.If the incision film consists or contains polymers, these can be polypropylene, polyamides, polysulfoxides, polysiloxanes, polyurethanes, polystyrene, polyvinyl chloride, polymethyl methacrylate, polyacrylic acid, polysilicones or polyurethanes, their blends or copolymers.
Wird als Inzisionsfolie ein Copolymerisat aus den Monomeren der antimikrobiellen Polymeren und Monomeren von einem oder mehreren weiteren Polymeren eingesetzt, so werden bevorzugt Monomere oder Oligomere der o. g. Polymeren verwendet.If a copolymer made from the monomers of the antimicrobial polymers and monomers of one or more other polymers is used as the incision film, monomers or oligomers of the abovementioned are preferred. Polymers used.
Zur weiteren Beschreibung der vorliegenden Erfindung werden die folgenden Beispiele gegeben, die die Erfindung weiter erläutern, nicht aber ihren Umfang begrenzen sollen, wie er in den Patentansprüchen dargelegt ist.To further describe the present invention, the following examples are given, which further illustrate the invention but are not intended to limit its scope as set out in the claims.
Beispiel 1:Example 1:
50 ml Dimethylaminopropylmethacrylamid (Fa. Aldrich) und 250 ml Ethanol werden in einem Dreihalskolben vorgelegt und unter Argonzustrom auf 65° C erhitzt. Danach werden 0,6 g50 ml of dimethylaminopropyl methacrylamide (Aldrich) and 250 ml of ethanol are placed in a three-necked flask and heated to 65 ° C. under a stream of argon. After that, 0.6 g
Azobisisobutyronitril gelöst in 20 ml Ethylmethylketon unter Rühren langsam zugetropft. Das Gemisch wird auf 70 °C erhitzt und 72 h Stunden bei dieser Temperatur gerührt. Nach Ablauf dieser Zeit wird die Reaktionsmischung in 1,5 1 VE- Wasser eingerührt, wobei das polymere Produkt ausfällt. Nach Abfiltrieren des Produktes wird der Filterrückstand mit 100 ml einer Mischung aus Ethanol/VE-Wasser im Verhältnis 1 : 1 gespült, um noch vorhandene Rest- monomere zu entfernen. Im Anschluss wird das Produkt für 24 Stunden bei 50 °C im Vakuum getrocknet. 2 g des Produktes werden in 10 g Ethanol gelöst und mit einem 100 Mikrometer Rakel auf eine 4 mal 6 cm große Polyethylenfolie aufgetragen. Die Folie wird im Anschluss bei 50 °C für 24 Stunden getrocknet.Azobisisobutyronitrile dissolved in 20 ml of ethyl methyl ketone was slowly added dropwise with stirring. The The mixture is heated to 70 ° C. and stirred at this temperature for 72 hours. After this time, the reaction mixture is stirred into 1.5 l of demineralized water, the polymeric product precipitating. After filtering off the product, the filter residue is rinsed with 100 ml of a mixture of ethanol / demineralized water in a ratio of 1: 1 in order to remove any remaining monomers. The product is then dried in vacuo at 50 ° C for 24 hours. 2 g of the product are dissolved in 10 g of ethanol and applied to a 4 by 6 cm polyethylene film using a 100 micrometer doctor blade. The film is then dried at 50 ° C for 24 hours.
Beispiel la:Example la:
Die Folie aus Beispiel 1 wird mit ihrer beschichteten Seite zur Haut gewandt auf den linken Unterarm einer Versuchsperson gelegt und mittels konventioneller Hautpflaster am Rand der Folie auf der Haut befestigt. Auf dem rechten Unterarm der Versuchsperson wird eine gleich große unbeschichtete Polyethylenfolie (Referenzfolie) in analoger Weise befestigt. Nach Ablauf von drei Stunden werden beide Folien entfernt, und es wird jeweils ein Hautabklatsch zur Feststellung der mikrobiellen Keimbelastung der vormals abgedeckten Hautpartien durchgeführt. Hierbei zeigt sich, das die mit der Folie aus Beispiel 1 behandelte Hautoberfläche eine signifikant geringere Keimbelastung aufweist als die mit der Referenzfolie behandelte.The film from Example 1, with its coated side facing the skin, is placed on the left forearm of a test subject and attached to the edge of the film by means of conventional skin patches. On the right forearm of the test person, an uncoated polyethylene film (reference film) of the same size is attached in an analogous manner. After three hours, both foils are removed and a skin wipe is carried out to determine the microbial contamination of the previously covered areas of the skin. It can be seen here that the skin surface treated with the film from Example 1 has a significantly lower germ load than that treated with the reference film.
Beispiel 2:Example 2:
50 ml tert. -Butylaminoethylmethacrylat (Fa. Aldrich) und 250 ml Ethanol werden in einem Dreihalskolben vorgelegt und unter Argonzustrom auf 65 °C erhitzt. Danach werden 0,6 g Azobisisobutyronitril gelöst in 20 ml Ethylmethylketon unter Rühren langsam zugetropft. Das Gemisch wird auf 70 °C erhitzt und 72 h Stunden bei dieser Temperatur gerührt. Nach Ablauf dieser Zeit wird die Reaktionsmischung in 1,5 1 VE- Wasser eingerührt, wobei das polymere Produkt ausfällt. Nach Abfiltrieren des Produktes wird der Filterrückstand mit 100 ml einer Mischung aus Ethanol/VE-Wasser im Verhältnis 1 : 1 gespült, um noch vorhandene Rest- monomere zu entfernen. Im Anschluss wird das Produkt für 24 Stunden bei 50 °C im Vakuum getrocknet. 2 g des Produktes werden in 10 g Ethanol gelöst und mit einem 100 Mikrometer Rakel auf eine 4 mal 6 cm große Polyethylenfolie aufgetragen. Die Folie wird im Anschluss bei 50 °C für 24 Stunden getrocknet. Beispiel 2a:50 ml tert. -Butylaminoethyl methacrylate (Aldrich) and 250 ml of ethanol are placed in a three-necked flask and heated to 65 ° C. under a stream of argon. Then 0.6 g of azobisisobutyronitrile dissolved in 20 ml of ethyl methyl ketone are slowly added dropwise with stirring. The mixture is heated to 70 ° C. and stirred at this temperature for 72 hours. After this time, the reaction mixture is stirred into 1.5 l of demineralized water, the polymeric product precipitating. After filtering off the product, the filter residue is rinsed with 100 ml of a mixture of ethanol / demineralized water in a ratio of 1: 1 in order to remove any remaining monomers. The product is then dried in vacuo at 50 ° C for 24 hours. 2 g of the product are dissolved in 10 g of ethanol and applied to a 4 by 6 cm polyethylene film using a 100 micrometer doctor blade. The film is then dried at 50 ° C for 24 hours. Example 2a:
2 g des Produktes aus Beispiel 2 werden in 10 g Ethanol gelöst und mit einem 100 Mikrometer Rakel auf eine 4 mal 6 cm große Polyethylenfolie aufgetragen. Die Folie wird im Anschluss bei 50 °C für 24 Stunden getrocknet.2 g of the product from Example 2 are dissolved in 10 g of ethanol and applied to a 4 by 6 cm polyethylene film using a 100 micrometer doctor blade. The film is then dried at 50 ° C for 24 hours.
Diese Folie wird mit ihrer beschichteten Seite zur Haut gewandt auf den linken Unterarm einer Versuchsperson gelegt und mittels konventioneller Hautpflaster am Rand der Folie auf der Haut befestigt. Auf dem rechten Unterarm der Versuchsperson wird eine gleich große unbeschichtete Polyethylenfolie (Referenzfolie) in analoger Weise befestigt. Nach Ablauf von drei Stunden werden beide Folien entfernt, und es wird jeweils ein Hautabklatsch zur Feststellung der mikrobiellen Keimbelastung der vormals abgedeckten Hautpartien durchgeführt. Hierbei zeigt sich, das die mit der beschichteten Folie behandelte Hautoberfläche eine signifikant geringere Keimbelastung aufweist als die mit der Referenzfolie behandelte.This film, with its coated side facing the skin, is placed on the left forearm of a test subject and attached to the skin by means of conventional skin patches on the edge of the film. On the right forearm of the test person, an uncoated polyethylene film (reference film) of the same size is attached in an analogous manner. After three hours, both foils are removed and a skin wipe is carried out to determine the microbial contamination of the previously covered areas of the skin. This shows that the surface of the skin treated with the coated film has a significantly lower germ load than that treated with the reference film.
Beispiel 2b:Example 2b
2 g des Produktes aus Beispiel 2 werden in 10 g Ethanol gelöst und mit einem 100 Mikrometer Rakel auf eine 4 mal 6 cm große Silikonfolie aufgetragen. Die Folie wird im Anschluss bei 50 °C für 24 Stunden getrocknet.2 g of the product from Example 2 are dissolved in 10 g of ethanol and applied to a 4 by 6 cm silicone film using a 100 micrometer doctor blade. The film is then dried at 50 ° C for 24 hours.
Diese Folie wird mit ihrer beschichteten Seite zur Haut gewandt auf den linken Unterarm einer Versuchsperson gelegt und mittels konventioneller Hautpflaster am Rand der Folie auf der Haut befestigt. Auf dem rechten Unterarm der Versuchsperson wird eine gleich große unbeschichtete Silikonfolie (Referenzfolie) in analoger Weise befestigt. Nach Ablauf von drei Stunden werden beide Folien entfernt, und es wird jeweils ein Hautabklatsch zur Feststellung der mikrobiellen Keimbelastung der vormals abgedeckten Hautpartien durchgeführt. Hierbei zeigt sich, das die mit der beschichteten Folie behandelte Hautoberfläche eine signifikant geringere Keimbelastung aufweist als die mit der Referenzfolie behandelte.This film, with its coated side facing the skin, is placed on the left forearm of a test subject and attached to the skin by means of conventional skin patches on the edge of the film. An uncoated silicone film (reference film) of the same size is attached to the right forearm of the test subject in an analogous manner. After three hours, both foils are removed and a skin wipe is carried out to determine the microbial contamination of the previously covered areas of the skin. This shows that the surface of the skin treated with the coated film has a significantly lower germ load than that treated with the reference film.
Beispiel 3: 90 ml Methacrylsäure-2-tert. -butylaminoethylester (Fa. Aldrich) und 180 ml Ethanol werden in einem Dreihalskolben vorgelegt und unter Argonzustrom auf 65 °C erhitzt. Danach werden 0,745 g Azobisisobutyronitril gelöst in 20 ml Ethylmethylketon unter Rühren langsam zugetropft. Das Gemisch wird auf 70 °C erhitzt und 72 h Stunden bei dieser Temperatur gerührt. Nach Ablauf dieser Zeit wird die Reaktionsmischung in 1 1 entmineralisiertes Wasser eingerührt, wobei das polymere Produkt ausfällt. Nach Abfiltrieren des Produktes wird der Filterrückstand mit 100 ml einer 10 %igen Lösung von Ethanol in Wasser gespült, um noch vorhandene Restmonomere zu entfernen. Im Anschluss wird das Produkt für 24 Stunden bei 50 °C im Vakuum getrocknet. 4 g des Produktes werden in 32 g Di-isononylphthalat gelöst. Anschließend werden dieser Mischung 64 g Polyvinylchloridgranulat zugegeben, wobei die Mischung innig verrührt bis sie pastös wird. 20 g der erhaltenen Paste werden mit einem Rakel so auf eine Metallplatte aufgestrichen, dass sich eine Schichtdicke von 0,7 mm Dicke einstellt. Die Platte mit der daraufliegenden Paste wird dann für 2 Minuten auf 200 °C erhitzt, wobei die Paste geliert und eine Weich-PVC-Folie entsteht.Example 3: 90 ml of 2-tert-methacrylic acid. butylaminoethyl ester (from Aldrich) and 180 ml of ethanol are placed in a three-necked flask and heated to 65 ° C. under a stream of argon. After that 0.745 g of azobisisobutyronitrile dissolved in 20 ml of ethyl methyl ketone was slowly added dropwise with stirring. The mixture is heated to 70 ° C. and stirred at this temperature for 72 hours. After this time, the reaction mixture is stirred into 1 liter of demineralized water, the polymeric product precipitating. After filtering off the product, the filter residue is rinsed with 100 ml of a 10% solution of ethanol in water in order to remove any remaining monomers. The product is then dried in vacuo at 50 ° C for 24 hours. 4 g of the product are dissolved in 32 g of di-isononyl phthalate. Then 64 g of polyvinyl chloride granules are added to this mixture, the mixture being stirred intimately until it becomes pasty. 20 g of the paste obtained are spread onto a metal plate using a doctor blade in such a way that a layer thickness of 0.7 mm is obtained. The plate with the paste on it is then heated to 200 ° C. for 2 minutes, during which the paste gels and a soft PVC film is formed.
Beispiel 3a: Ein 4 mal 6 cm großes Folienstück aus Beispiel 3 wird auf den linken Unterarm einer Versuchsperson gelegt und mittels konventioneller Hautpflaster am Rand der Folie auf der Haut befestigt. Auf dem rechten Unterarm der Versuchsperson wird eine gleich große unbeschichtete PVC-Folie (Referenzfolie) in analoger Weise befestigt. Nach Ablauf von drei Stunden werden beide Folien entfernt, und es wird jeweils ein Hautabklatsch zur Feststellung der mikrobiellen Keimbelastung der vormals abgedeckten Hautpartien durchgeführt. Hierbei zeigt sich, das die mit der Folie aus Beispiel 3 behandelte Hautoberfläche eine signifikant geringere Keimbelastung aufweist als die mit der Referenzfolie behandelte.Example 3a: A 4 x 6 cm piece of film from Example 3 is placed on the left forearm of a test subject and attached to the skin on the edge of the film by means of conventional skin plasters. An uncoated PVC film (reference film) of the same size is attached in an analogous manner to the right forearm of the test subject. After three hours, both foils are removed and a skin wipe is carried out to determine the microbial contamination of the previously covered areas of the skin. It can be seen here that the skin surface treated with the film from Example 3 has a significantly lower germ load than that treated with the reference film.
Beispiel 4: 50 ml tert. -Butylaminoethylmethacrylat (Fa. Aldrich) und 250 ml Ethanol werden in einem Dreihalskolben vorgelegt und unter Argonzustrom auf 65 °C erhitzt. Danach werden 0,6 g Azobisisobutyronitril gelöst in 20 ml Ethylmethylketon unter Rühren langsam zugetropft. Das Gemisch wird auf 70 °C erhitzt und 72 h Stunden bei dieser Temperatur gerührt. Nach Ablauf dieser Zeit wird die Reaktionsmischung in 1,5 1 VE-Wasser eingerührt, wobei das polymere Produkt ausfällt. Nach Abfiltrieren des Produktes wird der Filterrückstand mit 100 ml einer Mischung aus Ethanol/VE-Wasser im Verhältnis 1 : 1 gespült, um noch vorhandene Rest- monomere zu entfernen. Im Anschluss wird das Produkt für 24 Stunden bei 50 °C im Vakuum getrocknet. 30 g des Produktes werden zusammen mit 1000 g PVC-Granulat compundiert. Im Anschluss wird das Compound mittels eines Laborextruders zu einer 4 cm breiten Folie extrudiert.Example 4: 50 ml tert. -Butylaminoethyl methacrylate (Aldrich) and 250 ml of ethanol are placed in a three-necked flask and heated to 65 ° C. under a stream of argon. Then 0.6 g of azobisisobutyronitrile dissolved in 20 ml of ethyl methyl ketone are slowly added dropwise with stirring. The mixture is heated to 70 ° C. and stirred at this temperature for 72 hours. After this time, the reaction mixture is stirred into 1.5 l of deionized water, the polymeric product precipitating. After filtering off the product, the filter residue is rinsed with 100 ml of a mixture of ethanol / demineralized water in a ratio of 1: 1 in order to remove any remaining remove monomers. The product is then dried in vacuo at 50 ° C for 24 hours. 30 g of the product are compounded together with 1000 g of PVC granulate. The compound is then extruded into a 4 cm wide film using a laboratory extruder.
Beispiel 4a:Example 4a
Ein 4 mal 6 cm großes Folienstück aus Beispiel 4 wird auf den linken Unterarm einer Versuchsperson gelegt und mittels konventioneller Hautpflaster am Rand der Folie auf der Haut befestigt. Auf dem rechten Unterarm der Versuchsperson wird eine gleich große PVC-Folie ohne antimilαobielle Additive (Referenzfolie) in analoger Weise befestigt. Nach Ablauf von drei Stunden werden beide Folien entfernt, und es wird jeweils ein Hautabklatsch zur Feststellung der mikrobiellen Keimbelastung der vormals abgedeckten Hautpartien durchgeführt. Hierbei zeigt sich, das die mit der Folie aus Beispiel 3 behandelte Hautoberfläche eine signifikant geringere Keimbelastung aufweist als die mit der Referenzfolie behandelte. A 4 by 6 cm piece of film from Example 4 is placed on the left forearm of a test subject and attached to the skin on the edge of the film using conventional skin patches. An equally large PVC film without antimilαobial additives (reference film) is attached in an analogous manner to the subject's right forearm. After three hours, both foils are removed and a skin wipe is carried out to determine the microbial contamination of the previously covered areas of the skin. It can be seen here that the skin surface treated with the film from Example 3 has a significantly lower germ load than that treated with the reference film.

Claims

Patentansprüche: claims:
1. Inzisionsfolien, enthaltend antimikrobielle Polymere.1. Incision films containing antimicrobial polymers.
2. Inzisionsfolien nach Anspruch 1, dadurch gekennzeichnet, dass die Inzisionsfolien zu 0,5 bis 95 Gew.-% aus antimikrobiellen Polymeren bestehen.2. incision films according to claim 1, characterized in that the incision films consist of 0.5 to 95 wt .-% of antimicrobial polymers.
3. Inzisionsfolien nach Anspruch 1 und 2, dadurch gekennzeichnet, dass die Inzisionsfolien mit den antimikrobiellen Polymeren beschichtet sind.3. incision films according to claim 1 and 2, characterized in that the incision films are coated with the antimicrobial polymers.
4. Inzisionsfolien nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass die Inzisionsfolien aus einem Polymerblend aus den antimikrobiellen Polymeren und mindestens einem weiteren Polymeren bestehen.4. incise films according to claim 1 or 2, characterized in that the incise films consist of a polymer blend of the antimicrobial polymers and at least one other polymer.
5. Inzisionsfolien nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass die Inzisionsfolien aus einem Copolymerisat der Monomeren der antimikrobiellen5. incision films according to claim 1 or 2, characterized in that the incision films from a copolymer of the monomers of the antimicrobial
Polymeren und den Monomeren mindestens eines weiteren Polymeren, bestehen.Polymers and the monomers of at least one other polymer.
6. Inzisionsfolien nach den Ansprüchen 1 bis 5, dadurch gekennzeichnet, dass die Inzisionsfolien einen Hauthaftkleber aufweisen, der die antimikrobiellen Polymere enthält.6. incision films according to claims 1 to 5, characterized in that the incision films have a skin pressure sensitive adhesive which contains the antimicrobial polymers.
7. Inzisionsfolien nach den Ansprüchen 1 bis 6, dadurch gekennzeichnet, dass die antimikrobiellen Polymere aus Stickstoff- und phosphorfunktionalisierten7. incise films according to claims 1 to 6, characterized in that the antimicrobial polymers from nitrogen and phosphorus functionalized
Monomeren hergestellt werden. Monomers are produced.
8. Inzisionsfolien nach den Ansprüchen 1 bis 7, dadurch gekennzeichnet, dass die antimikrobiellen Polymere aus einem oder mehreren Monomeren aus der Gruppe: Methacrylsäure-2-tert.-butylaminoethylester, Methacrylsäure-2-diethylaminoethylester, Methacrylsäure-2-diethylaminomethylester, Acrylsäure-2-tert. -butylaminoethylester, Acryl- säure-3 -dimethylaminopropylester, Acrylsäure-2-diethylaminoethylester, Acrylsäure-2- dimethylaminoethylester, Dimethylaminopropylmethacrylamid, Diethylaminopropyl- methacrylamid, Acrylsäure-3 -dimethylaminopropylamid, 2-Methacryloyloxyethyltrimethyl- ammoniummethosulfat, Methacrylsäure-2-diethylaminoethylester, 2-Methacryloyloxyethyl- trimethylammoniumchlorid, 3-Methacryloylaminopropyltrimethylammonium-chlorid, 2-8. incise films according to claims 1 to 7, characterized in that the antimicrobial polymers from one or more monomers from the group: 2-tert-butylaminoethyl methacrylate, 2-diethylaminoethyl methacrylate, 2-diethylaminomethyl methacrylate, 2-acrylate tert. -butylaminoethyl ester, acrylic acid-3-dimethylaminopropyl ester, acrylic acid-2-diethylaminoethyl ester, acrylic acid-2-dimethylaminoethyl ester, dimethylaminopropyl methacrylamide, diethylaminopropyl methacrylamide, acrylic acid-3-dimethylaminopropylamide, 2-methacryloyloxyethyltrimethyl-methylethylamethylethylamethylethylamethylamethylethylamethylethylamethylethylaminoethylamethylethylamethylethylamethylethylamethylethylamethylethylamethylethylamethylethylamethylamethylethylamethylethylamethylamethylethylamethylethylamethylethylamethylethylamethylethylamethylethylamethylethylamethylethylamethylamethylethylamethylethylamethylethylamethylethylamethylamethylethylamethylethylamethylethylamethylamethylethylamethylethylamino - trimethylammonium chloride, 3-methacryloylaminopropyltrimethylammonium chloride, 2-
Methacryloyloxyethyltrimethylammoniumchlorid, 2- Acryloyloxyethyl-4-benzoyldimethyl- ammoniumbromid, 2- Methacryloyloxyethyl-4-benzoyldimethylammoniumbromid, Allyltri- phenylphosphoniumbromid, Allyltriphenylphosphoniumchlorid, 2-Acrylamido-2-methyl- 1- propansulfonsäure, 2-Diethylaminoethylvinylether und/oder 3-Aminopropylvinylether hergestellt wurden.Methacryloyloxyethyltrimethylammonium chloride, 2-acryloyloxyethyl 4-benzoyldimethylammoniumbromid, 2-methacryloyloxyethyl 4-benzoyldimethylammoniumbromid, Allyltri- phenylphosphoniumbromid, Allyltriphenylphosphoniumchlorid, 2-acrylamido-2-methyl-1-propanesulfonic acid, 2-diethylaminoethyl vinyl ether and / or 3-aminopropyl were prepared.
9. Inzisionsfolien nach den Ansprüchen 1 bis 8, dadurch gekennzeichnet, dass die weiteren Polymere aus der Gruppe Polypropylen, Polyamide, Polysulfoxide, Polysiloxane, Polyurethane, Polystyrol, Polyvinylchlorid, Polymethylmethacrylat,9. incise films according to claims 1 to 8, characterized in that the further polymers from the group polypropylene, polyamides, polysulfoxides, polysiloxanes, polyurethanes, polystyrene, polyvinyl chloride, polymethyl methacrylate,
Polyacrylsäure, Polysilikone oder Polyurethane deren Blends oder Copolymere ausgewählt sind. Polyacrylic acid, polysilicones or polyurethanes whose blends or copolymers are selected.
PCT/EP2001/014657 2001-01-23 2001-12-13 Antimicrobial incision films WO2002058757A1 (en)

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