EP1635886A1 - Biocidal medical product containing branched amphiphilic macromolecules and metal nanoparticles, method for the production thereof and its use - Google Patents
Biocidal medical product containing branched amphiphilic macromolecules and metal nanoparticles, method for the production thereof and its useInfo
- 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- Withdrawn
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)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Composite Materials (AREA)
- Materials Engineering (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Materials For Medical Uses (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10323597A DE10323597A1 (en) | 2003-05-19 | 2003-05-19 | Medical device, process for its manufacture and use |
PCT/EP2004/005325 WO2004101011A1 (en) | 2003-05-19 | 2004-05-18 | Biocidal medical product containing branched amphiphilic macromolecules and metal nanoparticles, method for the production thereof and its use |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1635886A1 true EP1635886A1 (en) | 2006-03-22 |
Family
ID=33441252
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP04733559A Withdrawn EP1635886A1 (en) | 2003-05-19 | 2004-05-18 | Biocidal medical product containing branched amphiphilic macromolecules and metal nanoparticles, method for the production thereof and its use |
Country Status (4)
Country | Link |
---|---|
US (1) | US20040234604A1 (en) |
EP (1) | EP1635886A1 (en) |
DE (1) | DE10323597A1 (en) |
WO (1) | WO2004101011A1 (en) |
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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 (en) * | 2004-10-20 | 2006-05-04 | Aesculap Ag & Co. Kg | Reabsorbable carrier material, useful e.g. in medicinal-technical product and in the human or animal body, comprises silver particles |
ITTO20040854A1 (en) * | 2004-12-02 | 2005-03-02 | Torino Politecnico | WORKING PROCEDURE FOR GLASS, CERAMIC AND GLASS SURFACES FOR THE IMPLEMENTATION OF IMPLANTABLE DEVICES WITH ANTIBACTERIAL ACTION |
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DE102005044361A1 (en) * | 2005-09-09 | 2007-03-15 | Aesculap Ag & Co. Kg | Antimicrobial medical device product, process for its preparation and use |
DE102006011217A1 (en) * | 2006-03-03 | 2007-09-06 | Aesculap Ag & Co. Kg | Medicinal product with an anti-microbial coating, useful as a biocide, comprises a complex material of metal nanoparticles and macromolecules, where the macromolecule is partly formed from a polyamino acid |
DE102005044360A1 (en) * | 2005-09-09 | 2007-03-15 | Aesculap Ag & Co. Kg | Medicinal technical-product, useful as e.g. temporary or durable implant and as biocides, comprises anti-microbial equipment from a complex material from metal-nanoparticle and macromolecules |
WO2007028607A2 (en) * | 2005-09-09 | 2007-03-15 | Aesculap Ag & Co. Kg | Antimicrobial medical product, method for the production thereof and use thereof |
EP1959740A2 (en) | 2005-11-15 | 2008-08-27 | LG Electronics Inc. | Antimicrobial coating based on kimchi lactic acid bacteria |
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EP2316499B1 (en) * | 2006-06-12 | 2013-05-01 | Accentus Medical PLC | Metal implants |
CN100999432B (en) * | 2006-12-25 | 2010-08-11 | 大连大学 | Method of preparing C2 hydrocarbon by ion liquid catalyzed plasma methane conversion |
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DE102007003538A1 (en) * | 2007-01-24 | 2008-07-31 | Raumedic Ag | Method for producing a medical work equipment, medical work equipment produced by such a method and use of such a medical work equipment |
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AR009439A1 (en) * | 1996-12-23 | 2000-04-12 | Novartis Ag | AN ARTICLE THAT INCLUDES A SUBSTRATE WITH A PRIMARY POLYMERIC COATING THAT CARRIES REACTIVE GROUPS PREDOMINANTLY ON ITS SURFACE, A METHOD FOR PREPARING SUCH AN ARTICLE, AN ARTICLE THAT HAS A HYBRID-TYPE COATING AND A CONTACT LENS |
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 (en) * | 1999-07-30 | 2001-02-01 | J Peter Guggenbichler | Production of antimicrobial plastic articles, especially catheters, involves pretreatment with colloidal metal, especially colloidal silver, before the final moulding process |
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2003
- 2003-05-19 DE DE10323597A patent/DE10323597A1/en not_active Withdrawn
- 2003-11-17 US US10/714,552 patent/US20040234604A1/en not_active Abandoned
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2004
- 2004-05-18 WO PCT/EP2004/005325 patent/WO2004101011A1/en active Application Filing
- 2004-05-18 EP EP04733559A patent/EP1635886A1/en not_active Withdrawn
Non-Patent Citations (1)
Title |
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Also Published As
Publication number | Publication date |
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WO2004101011A1 (en) | 2004-11-25 |
US20040234604A1 (en) | 2004-11-25 |
DE10323597A1 (en) | 2004-12-09 |
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