EP1635886A1 - Produit medical biocide contenant des macromolecules amphiphiles ramifiees et des nanoparticules de metal, procede de production correspondant et utilisation - Google Patents

Produit medical biocide contenant des macromolecules amphiphiles ramifiees et des nanoparticules de metal, procede de production correspondant et utilisation

Info

Publication number
EP1635886A1
EP1635886A1 EP04733559A EP04733559A EP1635886A1 EP 1635886 A1 EP1635886 A1 EP 1635886A1 EP 04733559 A EP04733559 A EP 04733559A EP 04733559 A EP04733559 A EP 04733559A EP 1635886 A1 EP1635886 A1 EP 1635886A1
Authority
EP
European Patent Office
Prior art keywords
medical
medical product
product
product according
hybrid complex
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04733559A
Other languages
German (de)
English (en)
Inventor
Stefan Mecking
Jörg C. TILLER
Erich Odermatt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aesculap AG
Albert Ludwigs Universitaet Freiburg
Original Assignee
Aesculap AG
Albert Ludwigs Universitaet Freiburg
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Aesculap AG, Albert Ludwigs Universitaet Freiburg filed Critical Aesculap AG
Publication of EP1635886A1 publication Critical patent/EP1635886A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • 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
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • 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
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/40—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
    • A61L27/44—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix
    • A61L27/446—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix with other specific inorganic fillers other than those covered by A61L27/443 or A61L27/46
    • 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
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/54—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
    • A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • 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
    • A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • A61L2300/104—Silver, e.g. silver sulfadiazine
    • 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
    • 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
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/62—Encapsulated active agents, e.g. emulsified droplets
    • A61L2300/624—Nanocapsules

Definitions

  • the invention relates to a medical-technical product with a layer of a hybrid complex material, the use of a hybrid complex material as a biocide in medical-technical products and a method for producing the hybrid complex material and a method for producing medical-technical products with the hybrid complex material.
  • Silver is known as one of the most toxic metals for microorganisms. Silver has an extremely broad antimicrobial spectrum, which includes both gram negative and gram positive bacteria. The microbial toxicity results from an interference of the silver ions in the transmembrane energy metabolism and, with a few exceptions, is highly toxic to the vast majority of microorganisms. The human body, on the other hand, can tolerate silver up to concentrations of up to approx. 1 mg per day and person and is not allergic to silver. Silver colloids have long been known to have antimicrobial properties and, at the same time, are relatively environmentally friendly and non-toxic (Biochemische Zeitschrift 1919, 94, 47). Various methods have therefore been used to apply or incorporate silver or silver ions onto products to be treated with biocides.
  • the invention has for its object to provide medical products with a long-term non-toxic biocidal coating that counteracts intra- or post-operative microbial contamination and enables a complication-free temporary or permanent use in the body.
  • the coating should be able to be applied in a simple manner at the desired locations.
  • a medical product with a layer of a hybrid complex material made of a branched amphiphilic macromolecule and a metal nanoparticle, the layer being provided at least on the surface and at least on part of the surface.
  • the advantage of the medical-technical product according to the invention is, in particular, that the biocidal finish, in particular the coating, forms a sufficiently stable adhesive bond through interaction forces with the surface of the product materials and therefore detachment, i.e. Prevents wiping or washing of the biocidal material.
  • the products equipped in this way always have effective protection against microbial colonization even after being introduced into the body or after a more or less long postoperative stay in the body.
  • Such coating materials are from the publication by Mecking et al. (Chem. Comm. 2002, 3018-3019 of November 19, 2002), the content of which is referred to here.
  • the organic chemical complexing agents on which these hybrid complexes are based are known from US Pat. No. 3,425,549 from 1969 and are of great importance as chelating reagents in the chemical industry.
  • the medical technology product according to the invention has a layer made of a hybrid complex material which consists of a different branched amphiphilic macromolecule and a metal nanoparticle.
  • This layer is provided at least on the surface of the product and on this surface at least on part of the total surface of the product.
  • the product can also contain the hybrid complex material within its material.
  • the metal nanoparticles are not ionic particles but elementary metallic nanoparticles.
  • each nanoparticle is surrounded by at least one branched amphiphilic macromolecule.
  • the at least one macromolecule encloses the metal nanoparticle like a shell from all sides. It is also possible for a large number of individual macromolecules to envelop the metal nanoparticle.
  • amphiphilic macromolecule is advantageously an amphiphilic polyalkyleneimine, in particular a polyethyleneimine or polypropyleneimine.
  • alkyleneimines are also conceivable which, in their branched basic structure, have a sufficient number of primary, secondary or tertiary nitrogen atoms in order to coat the metal nanoparticle located inside with sufficient stability.
  • the polyalkyleneimine has a degree of branching of 20 to 90%, preferably 40 to 80%, in particular approximately 60%.
  • the polyalkyleneimine has alkyl-substituted secondary or tertiary amino groups.
  • the secondary or tertiary amino groups preferably carry methyl or ethyl substituents.
  • the branched amphiphilic polyalkyleneimine advantageously has amide groups which are in particular oriented away from the metal nanoparticle in the interior of the polyalkyleneimine. In these amide groups, the N atoms derive from the polyalkyleneimine backbone and the C atoms from a carboxylic acid.
  • the amide groups carry an aliphatic fatty acid residue which is preferably oriented towards the outside.
  • the number of carbon atoms in this fatty acid residue is 6 to 22, preferably 12 to 18 and in particular 16 carbon atoms.
  • the aliphatic residue of the fatty acid can consist of branched or unbranched carbon chains. It can also originate from both saturated and at least partially unsaturated fatty acids. They are preferably linear, saturated with an even number of carbon atoms.
  • This preferred orientation of the acid residues which are bound to the polyalkylene skeleton via the amide group and the inward orientation of the amine groups of the polyalkyleneimine system result in the amphiphilic character of this macromolecule.
  • the amidation of the underlying polyalkyleneimine structure is possible using various reagents and is known from the publication by Rannard and Davies (Org. Lett. 2000, 2, 2177).
  • the production of the polyalkyleneimine basic structure has already been described in US Pat. No. 3,425,549 for special alkyleneimines and is known, for example, for polyethyleneimine from US Pat. No. 2,182,306.
  • the molecular weight of the macromolecule is 800 to 20,000, preferably 2,000 to 10,000 and in particular approximately 5,000.
  • the molecular weight depends in particular on the number of carbon atoms, both the fatty acid residues on the amide groups and the number of carbon atoms on the alkyl radicals of the polyalkyleneimine and the degree of branching of the polyalkyleneimine.
  • polyethyleneimines with relatively short fatty acid residues and without alkyl substituents have a relatively low molecular weight
  • molecules with long-chain alkyl residues and fatty acid residues have a high molecular weight.
  • the metal nanoparticle is advantageously a silver or a copper nanoparticle, in particular silver.
  • Silver and, to a lesser extent, copper represent the most toxic metals with regard to the microorganisms to be combated, such as gram-positive cocci, multi-resistant coagulase positive and negative staphylococci and enterococci gram-negative enterobacteria such as P. aeoroginosa and C. albicans these microorganisms.
  • the ratio of silver atoms to the nitrogen atoms which are in direct contact with them, preferably secondary or tertiary and which are oriented inwards in the macromolecule, is 1: 2 to 1:10, preferably 1: 3 to 1: 5 and in particular 1: 4th If the proportion of nitrogen atoms is too low, these are not sufficient to completely coat the silver atoms or silver nanoparticles and the amount of silver enclosed by the macromolecules is either very small or a complete coating of the silver atoms is no longer possible. In contrast, a high proportion of nitrogen atoms that are in direct contact with the silver atoms has no negative influence on the properties, in particular stability, of the hybrid complex.
  • the hybrid complex has a total diameter of 0.5 to 10 nm, preferably 1 to 5 nm and in particular approximately 2 nm.
  • the size of the amphiphilic hybrid complex is thus in the lower range of the currently known metal nanoparticles.
  • the product according to the invention is a temporary or permanent implant for the human or animal body.
  • the implants provided with the hybrid complex are preferably joint implants, stents, screws, nails and plates for repairing fractures made of metal and / or plastic and in particular hernia nets and vascular prostheses as well as membranes and foils, e.g. for adhesion prophylaxis, incontinence bands and in general around textile implants.
  • the biocidal coating of these implants makes it possible to incorporate them into acutely infected or infection-prone body regions, since the implants themselves have an antimicrobial effect due to the hybrid complex material and actively contribute to the reduction of an existing or potential infection.
  • the medical technology products are medical instruments, in particular surgical scissors, pliers and clamps, as well as catheters or probes and other instruments, in particular for minimally invasive microsurgical interventions.
  • these instruments exposed to mechanical stress, in particular by rubbing and wiping, the adhesive property of the hybrid complex material on the surfaces and the insolubility in an aqueous environment are of great importance.
  • the risk of infection due to use is also present in the case of longer surgical interventions or if the instruments to be used during an intervention are insufficient of instruments to be used multiple times, particularly with regard to the Creutzfeldt-Jakob or HIV problem.
  • the medical technology products can also be products such as drainage tubes or sutures, which represent an intermediate group of medical technology products between medical instruments and implants. This also includes products such as wound dressings.
  • the medical technology products are made of metal, preferably titanium or surgical steel.
  • the material of the products is non-resorbable or at least partially resorbable polymers.
  • the hybrid complex material can also be present in addition to a coating on the surface as an additional component to the polymer material in the interior of the product.
  • the material of the medical technology products can also be ceramic materials.
  • the product can advantageously be sterilized and is in particular in a sterilized form. All currently available methods which do not change the chemical structure or the properties of the hybrid complex can be considered as sterilization methods.
  • the medical technology product according to the invention is in sterile form in the state of use. Because of the biocidal coating, the medical technology products coated in this way can also be opened and made available before immediate use or implantation.
  • the invention further comprises the use of a hybrid complex material made from a branched amphiphilic macromolecule and a metal nanoparticle as a biocide in medical technology products. In the hybrid complex material according to the invention, in particular each metal nanoparticle is surrounded in a shell-like manner with at least one branched amphiphilic macromolecule.
  • the biocide is applied to at least part of the surface of the medical device product. Depending on the application and area of application of the product, it may make sense to only provide the biocide with the part of the product that comes into contact with the, preferably internal, part of the human body.
  • the hybrid complex material is incorporated directly into the interior of the medical product.
  • the hybrid complex material is applied or incorporated both on at least part of the surface and in the interior of the medical product.
  • the hybrid complex material can initially be present inside the product and, in the case of resorbable products, a constantly renewing surface of the product and thus an unused biocidal layer can be exposed, which permanently protects the implant from microbial colonization until it is is completely absorbed.
  • the invention also encompasses a method for producing a hybrid complex material from a branched amphiphilic macromolecule and a metal nanoparticle, in which in particular each metal nanoparticle is enveloped like a shell by at least one branched amphiphilic macromolecule.
  • a metal compound is dissolved in a solution of a complex amphiphilic polyalkyleneimine dissolved, especially in an organic solvent.
  • the metal compound is preferably a silver salt, in particular silver nitrate.
  • silver salts in particular silver acetate, or copper salts are also conceivable, the toxic effect of copper on undesirable microorganisms being weaker than the effect of silver.
  • the solvent of the amphiphilic polyalkyleneimine is advantageously an aprotic, preferably aromatic, solvent.
  • the solvent is toluene.
  • the metal compound can also be a MetaN complex, in particular a silver complex, which has a lower stability than the complex with the polyalkyleneimine.
  • an amphiphilic polyalkyleneimine is used, which is prepared by amidating a branched polyalkyleneimine with a fatty acid. This amidation is described in Rannard and Davies (Organic Letters 2002, 2, 2117) and in US 3,425,549.
  • the polyalkyleneimine is preferably polyethyleneimine or polypropyleneimine, in particular polyethyleneimine.
  • the hybrid complex material in particular in the form of a solution, is applied to the product from the outside.
  • the hybrid complex material can the finished medical product can be applied, in particular by spraying or by dipping.
  • the hybrid complex material is advantageous to process at room temperature and is dried after application to the product.
  • the hybrid complex material is particularly preferably applied to a suture material together with a lubricant on the suture material, in particular as a solution in an organic solvent such as ethyl acetate.
  • the hybrid complex material for the production of medical technology products is added directly into the polymer material during the production of the product, in particular in the form of a solution.
  • the material of the product By adding to the material of the product, an even distribution of the biocidal hybrid complex material is achieved within the medical product. This is of crucial importance in particular in the case of resorbable or partially resorbable products, so that after the absorption of the superficial layer of the product material, every further layer underneath has the same biocidal properties and thus the entire product material has the antimicrobial properties over the entire surface during its lifetime.
  • the hybrid complex material is mixed with the product material and then shaped to the desired product, in particular extruded, spun, pressed, rolled, cast or blown.
  • the mixture of polymer and hybrid complex is particularly preferably spun into a thread material which, depending on the type of polymer used, is either woven or forcibly into resorbable or non-resorbable suture material or into textile products.
  • amphiphilic amidated polyethyleneimine is produced by amidation according to Rannard and Davies (Org. Lei, 2000, 2, 2117).
  • the am-PEI is dissolved in dry toluene.
  • Silver nitrate in a ratio of 0.5 (Ag + / N atoms) is then dissolved in the toluene solution.
  • the reduction with Li [HBEt 3 ] produced a clear yellow colloidal silver solution.
  • a complete reduction of Ag + to Ag takes place by extracting the colloidal solution with an aqueous solution of sodium thiosulfate.
  • the reaction solution is then checked for any remaining Ag + with sodium sulfide.
  • Transmission electron microscopy (TEM) revealed silver manoparticles with a diameter of 1 to 2 nm.
  • am-PE ⁇ 7AgN0 3 , am-PEI / Li [HBEt 3 ] and am-PEI showed no antimicrobial activity under the same experimental conditions.
  • Figure 1 shows a hybrid complex (1, 2) absorbed on a surface (3).
  • FIG. 1 shows a hybrid complex (1, 2) consisting of a coated silver nanoparticle (2), coated by a branched polyethyleneimine macromolecule (1) amidated with palmitic acid.
  • the wavy lines here mean a palmitic acid residue, ie a saturated carbon hydrogen chain with 15 carbon atoms.
  • the silver nanoparticle (2) is immediately surrounded by primary, secondary or tertiary nitrogen atoms.
  • the palmitic acid residues are each bound to amide groups, the nitrogen atoms of which are each derived from the polyethylene lenimin backbone and formerly represented primary amines, ie terminal NH 2 groups.
  • these amide groups are bonded directly to a nitrogen atom which is in the immediate vicinity of the silver nanoparticle (2), or the amide groups are bonded to further secondary or tertiary nitrogen atoms which are not directly adjacent to the silver nanoparticle (2), so that the amide group with the associated hydrophobic fatty acid residue is arranged more or less far from the coated silver nanoparticle (2) by such amine group spacers.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Dermatology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Epidemiology (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Composite Materials (AREA)
  • Materials Engineering (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Materials For Medical Uses (AREA)

Abstract

L'invention concerne un produit médical comportant une couche de matériau à complexe hybride, à base d'une macromolécule amphiphile ramifiée et d'une nanoparticule de métal, l'utilisation d'un matériau à complexe hybride à base d'une macromolécule amphiphile ramifiée et d'une nanoparticule, comme biocide dans des produits médicaux, ainsi qu'un procédé permettant de produire un matériau à complexe hybride à base d'une macromolécule amphiphile ramifiée et d'une nanoparticule de métal, par dissolution d'un composé métal, de manière à effectuer un complexage, puis par réduction du composé métal. L'invention concerne également un procédé permettant de produire des produits médicaux, où le matériau à complexe hybride est appliqué depuis l'extérieur sur le produit ou est ajouté dans le matériau polymère du produit lors de sa production.
EP04733559A 2003-05-19 2004-05-18 Produit medical biocide contenant des macromolecules amphiphiles ramifiees et des nanoparticules de metal, procede de production correspondant et utilisation Withdrawn EP1635886A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10323597A DE10323597A1 (de) 2003-05-19 2003-05-19 Medizintechnisches Produkt, Verfahren zu seiner Herstellung und Verwendung
PCT/EP2004/005325 WO2004101011A1 (fr) 2003-05-19 2004-05-18 Produit medical biocide contenant des macromolecules amphiphiles ramifiees et des nanoparticules de metal, procede de production correspondant et utilisation

Publications (1)

Publication Number Publication Date
EP1635886A1 true EP1635886A1 (fr) 2006-03-22

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP04733559A Withdrawn EP1635886A1 (fr) 2003-05-19 2004-05-18 Produit medical biocide contenant des macromolecules amphiphiles ramifiees et des nanoparticules de metal, procede de production correspondant et utilisation

Country Status (4)

Country Link
US (1) US20040234604A1 (fr)
EP (1) EP1635886A1 (fr)
DE (1) DE10323597A1 (fr)
WO (1) WO2004101011A1 (fr)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0208642D0 (en) * 2002-04-16 2002-05-22 Accentus Plc Metal implants
GB0405680D0 (en) * 2004-03-13 2004-04-21 Accentus Plc Metal implants
DE102004052203A1 (de) * 2004-10-20 2006-05-04 Aesculap Ag & Co. Kg Trägermaterial mit Silberpartikeln, Bereitstellung des Trägermaterials, medizintechnisches Produkt enthaltend das erfindungsgemäße Material und Verfahren zur Detektion des Trägermaterials sowie von Adhäsionen
ITTO20040854A1 (it) * 2004-12-02 2005-03-02 Torino Politecnico Procedimento di funzionamento di superfici vetrose, vetroceramiche e ceramiche per la realizzazione di dispositivi impiantabili ad azione antibatterica
CA2600718A1 (fr) * 2005-03-21 2006-09-28 Regents Of The University Of California Formation controlable de nanostructures sur des surfaces microstructurees
DE102006011217A1 (de) * 2006-03-03 2007-09-06 Aesculap Ag & Co. Kg Antimikrobielles medizintechnisches Produkt, Verfahren zu seiner Herstellung und Verwendung
DE102005044361A1 (de) * 2005-09-09 2007-03-15 Aesculap Ag & Co. Kg Antimikrobielles medizintechnisches Produkt, Verfahren zu seiner Herstellung und Verwendung
DE502006007526D1 (de) 2005-09-09 2010-09-09 Aesculap Ag Antimikrobielles medizintechnisches produkt, verfahren zu seiner herstellung und verwendung
DE102005044360A1 (de) * 2005-09-09 2007-03-15 Aesculap Ag & Co. Kg Antimikrobielles medizintechnisches Produkt, Verfahren zu seiner Herstellung und Verwendung
EP1959740A2 (fr) 2005-11-15 2008-08-27 LG Electronics Inc. Revêtement antibactérien basé sur l'acide lactique produit par les bactéries du kimchi
DE102006013871A1 (de) * 2006-03-23 2007-09-27 Justus-Liebig-Universität Giessen Elektrochemisches Verfahren zur Abscheidung von nanoskaligen Metallen, Halbmetallen und Verbindungen dieser Metalle und/oder Halbmetalle an der Grenzfläche zwischen einer Niedertempereturentladung und einer ionischen Flüssigkeit
EP2316499B1 (fr) * 2006-06-12 2013-05-01 Accentus Medical PLC Implants métalliques
CN100999432B (zh) * 2006-12-25 2010-08-11 大连大学 离子液体催化等离子体甲烷转化制c2烃的方法
AU2008206819B2 (en) * 2007-01-15 2013-07-11 Accentus Medical Limited Metal implants
DE102007003538A1 (de) * 2007-01-24 2008-07-31 Raumedic Ag Verfahren zur Herstellung eines medizinischen Arbeitsmittels, nach einem derartigen Verfahren hergestelltes medizinisches Arbeitsmittel sowie Verwendung eines derartigen medizinischen Arbeitsmittels
DE102007012253A1 (de) 2007-03-09 2008-09-11 Aesculap Ag & Co. Kg Antimikrobielles medizintechnisches Produkt, Verfahren zu seiner Herstellung und Verwendung
EP2147733A4 (fr) * 2007-05-16 2012-12-12 Dainippon Ink & Chemicals Procédé de production de nanostructure contenant de l'argent, et nanostructure contenant de l'argent
US7987979B2 (en) * 2007-05-31 2011-08-02 Hand Held Products, Inc. Data collection device enclosure
AU2008306596B2 (en) 2007-10-03 2013-04-04 Accentus Plc Method of manufacturing metal with biocidal properties
US20110020170A1 (en) * 2008-03-19 2011-01-27 Basf Se Metal nanoparticles stabilized with derivatized polyethyleneimines or polyvinylamines
DE102008031310A1 (de) 2008-07-04 2010-01-07 Thüringisches Institut für Textil- und Kunststoff-Forschung e.V. Verfahren zur Herstellung von Metallnanopartikeldispersionen und Produkte daraus
DE102008052837A1 (de) * 2008-10-13 2010-04-15 Aesculap Ag Textiles Implantat mit Kern-Mantel-Aufbau und Verfahren zu seiner Herstellung
US8641418B2 (en) 2010-03-29 2014-02-04 Biomet 3I, Llc Titanium nano-scale etching on an implant surface
CZ2011549A3 (cs) * 2011-09-02 2012-10-24 Univerzita Palackého v Olomouci Zpusob imobilizace nanocástic stríbra na pevné substráty
WO2013142118A1 (fr) 2012-03-20 2013-09-26 Biomet 3I, Llc Traitement de surface pour une surface d'implant
GB2511528A (en) 2013-03-06 2014-09-10 Speciality Fibres And Materials Ltd Absorbent materials
US11039621B2 (en) 2014-02-19 2021-06-22 Corning Incorporated Antimicrobial glass compositions, glasses and polymeric articles incorporating the same
US9622483B2 (en) 2014-02-19 2017-04-18 Corning Incorporated Antimicrobial glass compositions, glasses and polymeric articles incorporating the same
US11039620B2 (en) 2014-02-19 2021-06-22 Corning Incorporated Antimicrobial glass compositions, glasses and polymeric articles incorporating the same
CN103893830B (zh) * 2014-03-31 2016-04-06 刘文博 纳米银抗感染疝修补片及其制备方法
DE102014215353A1 (de) * 2014-08-04 2016-02-04 Aesculap Ag Antimikrobieller Sterilcontainer
US11737970B1 (en) * 2015-11-23 2023-08-29 Nexgen Semi Holding, Inc. Drug delivery systems and methods for making and using the same
CZ307996B6 (cs) * 2016-01-27 2019-10-09 Univerzita PalackĂ©ho v Olomouci Polymerní substrát s imobilizovanými nanočásticemi stříbra a způsob jeho přípravy

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2182306A (en) * 1935-05-10 1939-12-05 Ig Farbenindustrie Ag Polymerization of ethylene imines
US3425549A (en) * 1966-03-04 1969-02-04 Petrolite Corp Flotation process
US5019096A (en) * 1988-02-11 1991-05-28 Trustees Of Columbia University In The City Of New York Infection-resistant compositions, medical devices and surfaces and methods for preparing and using same
US5399363A (en) * 1991-01-25 1995-03-21 Eastman Kodak Company Surface modified anticancer nanoparticles
US5874165A (en) * 1996-06-03 1999-02-23 Gore Enterprise Holdings, Inc. Materials and method for the immobilization of bioactive species onto polymeric subtrates
AR009439A1 (es) * 1996-12-23 2000-04-12 Novartis Ag Un articulo que comprende un sustrato con un recubrimiento polimerico primario que porta grupos reactivos predominantemente en su superficie, unmetodo para preparar dicho articulo, un articulo que posee un recubrimiento de tipo hibrido y una lente de contacto
IL122153A (en) * 1997-11-10 2005-03-20 Alomone Labs Ltd Biocompatible polymeric coating material
US6273875B1 (en) * 1998-08-17 2001-08-14 Edwards Lifesciences Corporation Medical devices having improved antimicrobial/antithrombogenic properties
DE19936059A1 (de) * 1999-07-30 2001-02-01 J Peter Guggenbichler Verfahren zur Herstellung von antimikrobiellen Kunststoffkörpern

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004101011A1 *

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