Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
• • 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
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
• • 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
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
• • 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
  • A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
  • C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
• • 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
  • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
  • A61L2300/204—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with nitrogen-containing functional groups, e.g. aminoxides, nitriles, guanidines
• • 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 a process for the preparation of antimicrobial polymers by polymerizing amino-functionalized monomers and the use of the antimicrobial polymers thus produced
• the invention relates to a process for the preparation of antimicrobial polymers by graft polymerization of amino-functionalized monomers on a substrate and the use of the antimicrobial substrates thus produced
• Bacteria must be kept away from all areas of life in which hygiene is important.This affects textiles for direct body contact, in particular for the genital area and for nursing and elderly care.In addition, bacteria must be kept away from furniture and device surfaces in care stations, particularly in the area of Intensive care and the care of small children, in hospitals, in particular in rooms for medical interventions and in isolation stations for critical infection cases and in toilets
• Tert-butylaminoethyl methacrylate is a commercially available monomer in methacrylate chemistry and is used in particular as a hydrophilic component in copolymerizations.
• EP-PS 0 290 676 describes the use of various polyacrylates and polymethacrylates as a matrix for the immobilization of bactericidal quaternary ammonium compounds
• US Pat. No. 4,532,269 discloses a terpolymer of butyl methacrylate, tributyltin methacrylate and tert-butylaminoethyl methacrylate.
• This polymer is used as an antimicrobial marine paint, the hydrophilic tert-butylaminoethyl methacrylate requiring the slow erosion of the polymer and thus the highly toxic tributyltin microbial methacrylate releases
• the copolymer made with aminomethacrylates is only a matrix or carrier substance for added microbicidal active ingredients that can diffuse or migrate from the carrier substance.
• Polymers of this type lose their effect more or less quickly if the necessary "minimal inhibitory concentration" on the surface ( MIK) is no longer achieved
• the present invention is therefore based on the object of developing novel, antimicrobial polymers which, if necessary, are intended as a coating to prevent the settling and spreading of bacteria on surfaces
• the present invention relates to a process for the preparation of antimicrobial polymers, characterized in that aliphatic unsaturated monomers which are functionalized at least simply by a secondary amino group are polymerized
• the aliphatic unsaturated monomers functionalized at least simply by a secondary amino group in the process according to the invention can have a hydrocarbon radical of up to 50, preferably up to 30, particularly preferably up to 22 carbon atoms.
• the substituents of the amino group can have aliphatic or vinyl hydrocarbon radicals such as methyl, Have ethyl, propyl or acrylic radicals or cyclic hydrocarbon radicals such as substituted or unsubstituted phenyl or cyclohexyl radicals having up to 25 carbon atoms.
• the amino group can also be substituted by keto or aldehyde groups such as acryloyl or oxo groups
• the monomers used according to the invention should have a molar mass of less than 900, preferably less than 550 g / mol
• aliphatic unsaturated monomers of the general formula which are functionalized simply by a secondary amino group are functionalized simply by a secondary amino group
• R Branched, unbranched or cyclic, saturated or unsaturated hydrocarbon radical with up to 50 C atoms, which can be substituted by O, N or S atoms and R 2 branched, unbranched or cyclic, saturated or unsaturated hydrocarbon radical with up to 25 C. Atoms which can be substituted by O, N or S atoms, be used
• all aliphatic unsaturated monomers which have at least one secondary amino function are suitable as monomer units - ethyl butenate, 3-methylamino-2-butenoate, 3-methylamino-1-phenyl-2-propen-1-one, 2-methyl-N-4-methylamino-1-anthraquinoyl-acrylamide, N-9, 10-dihydro -4- (4-methylphenylamino) -9,10-dioxo-l-anthrachinyl-2-methyl-propenamide, 2-hydroxy-3- (3-triethoxysilylpropylamino) -2-propenoic acid propyl ester, l- (l-methylethylamino) -3 - (2
• the method according to the invention can also be carried out by polymerizing the monomers functionalized at least simply by a secondary amino group on a substrate. A physisorbed coating of the antimicrobial copolymer is obtained on the substrate
• Suitable substrate materials are above all all all polymeric plastics, such as polyurethanes, polyamides, polyesters and ethers, polyether block amides, polystyrene, polyvinyl chloride, polycarbonates, polyorganosiloxanes, polyolefins, polysulfones, polyisoprene, polychloroprene, polytetrafluoroethylene (PTFE), corresponding copolymers and Blends as well as natural and synthetic rubbers, with or without radiation-sensitive groups.
• the method according to the invention can also be applied to surfaces of lacquered or otherwise plastic, metal, glass or wood bodies
• the antimicrobial polymers can be obtained by graft-polymerizing a substrate with an aliphatically unsaturated monomer functionalized at least simply by a secondary amino group.
• the grafting of the substrate enables covalent attachment of the antimicrobial polymers on the substrate All polymeric materials, such as the plastics already mentioned, can be used as substrates
• the surfaces of the substrates can be activated before the graft copolymerization using a number of methods. All standard methods for activating polymeric surfaces can be used here.
• the activation of the substrate before the graft polymerization is carried out by UV radiation, plasma treatment, corona treatment, flame treatment, ozonization, electrical discharge of ⁇ -radiation, methods used
• the surfaces are expediently freed of oils, fats or other contaminants beforehand in a known manner by means of a solvent
• the substrates can be activated by UV radiation in the wavelength range 170-400 nm, preferably 170-250 nm.
• a suitable radiation source is, for example, a UV excimer device HERAEUS Noblelight, Hanau, Germany.
• mercury vapor lamps are also suitable for substrate activation if they are emit significant amounts of radiation in the areas mentioned
• the exposure time is generally 0 1 seconds to 20 minutes, preferably 1 second to 10 minutes
• the activation of the standard polymers with UV radiation can also be carried out with an additional photosensitizer.
• the activation can also be achieved by plasma treatment by means of an RF or microwave plasma (Hexagon, Fa Technics Plasma, 85551 Kirchheim, Germany) in air, nitrogen or argon atmosphere.
• the exposure times are generally 2 seconds to 30 minutes, preferably 5 seconds up to 10 minutes
• the energy input for laboratory devices is between 100 and 500 W, preferably between 200 and 300 W.
• Corona devices SOFTAL, Hamburg, Germany
• the exposure times in this case are generally 1 to 10 minutes, preferably 1 to 60 seconds
• Activation by electrical discharge, electron or ⁇ -rays (e.g. from a cobalt 60 source) and ozonization enable short exposure times, which are generally 0 1 to 60 seconds
• Flaming substrate surfaces also leads to their activation.
• Suitable devices in particular those with a barrier flame front, can be built in a simple manner or, for example, can be obtained from ARCOTEC, 71297 Monsheim, Germany
• Exposure times generally range from 0.1 seconds to 1 minute, preferably
• the substrate surfaces activated in this way are coated by known methods, such as dipping, spraying or brushing, with aliphatic unsaturated monomers which are at least simply functionalized by a secondary amino group, if appropriate in solution.
• Water and water / ethanol mixtures have retained as solvents, however other solvents can also be used, provided they have sufficient bulk for the monomers and wet the substrate surfaces well.
• Other solvents are, for example, ethanol, methanol, methyl ethyl ketone, diethyl ether, dioxane, hexane, heptane, benzene, toluene, chloroform, dichloromethane, tetrahydrofuran and acetonitrile solutions with monomer contents of 1 to 10% by weight, for example approximately 5% by weight, have been found to be effective in practice and generally give, in one pass, Coatings covering substrate surface with layer thicknesses that can be more than 0 1 ⁇ m
• the graft copolymerization of the monomers applied to the activated surfaces can expediently be initiated by radiation in the short-wave segment of the visible range or in the long-wave segment of the UV range of the electromagnetic radiation.
• the radiation from a UV excimer of the wavelengths 250 to 500 nm is very suitable. preferably from 290 to 320 nm
• mercury vapor lamps are suitable, provided they emit considerable amounts of radiation in the areas mentioned.
• the exposure times are generally 10 seconds to 30 minutes, preferably 2 to 15 minutes
• graft copolymerization can also be achieved by a process which is described in European patent application 0 872 512 and is based on a graft polymerization of swollen monomer and initiator molecules
• further aliphatic unsaturated monomers can be used, in addition to the monomers functionalized by a secondary amino group.
• An aliphatic unsaturated monomer functionalized at least simply by a secondary amine group with acrylates or methacrylates, for example acrylic acid, tert-butyl methacrylate or methyl methacrylate, can be used as the monomer mixture.
• Styrene, vinyl chloride, vinyl ether, acrylamides, acrylonitriles, olefins (ethylene, propylene, butylene, isobutylene), allyl compounds, vinyl ketones, vinyl acetic acid, vinyl acetate or vinyl esters can be used
• the antimicrobial polymers made from aliphatic unsaturated monomers, which are functionalized at least simply by a secondary amino group, produced by the process according to the invention show a microbicidal or antimicrobial behavior even without grafting onto a substrate surface
• customary radical initiators can be added.
• the initiators are azonitriles, alkyl peroxides, hydroperoxides, acyl peroxides, peroxoketones, peresters, peroxocarbonates, peroxodisulfate, persulfate and all customary photoinitiators such as, for example Use acetophenones, ⁇ -hydroxy ketones, dimethyl ketals and benzophenone.
• the polymerization can also be initiated thermally or, as already stated, by electromagnetic radiation, such as UV light or ⁇ radiation
• the present invention furthermore relates to the use of the antimicrobial polymers produced according to the invention for the production of antimicrobially active products and the products thus produced as such.
• the products can contain or consist of modified polymer substrates according to the invention.
• Such products are preferably based on polyamides, polyurethanes, polyether block amides, polyester amides or -imides, PVC, polyolefins, silicones, polysiloxanes, polymethacrylate or polyterephthalates, which have surfaces modified with the polymers produced according to the invention
• Antimicrobial products of this type are, for example, and in particular machine parts for food processing, components of air conditioning systems, roofing, bathroom and toilet articles, cake articles, components of sanitary facilities, components of animal cages and dwellings, toys, components in water systems, food packaging, operating elements (touch panel ) of devices and contact lenses
• the present invention also relates to the use of the polymer substrates modified on the surface with the antimicrobial polymers produced according to the invention for the production of hygiene products or medical articles.
• hygiene products are, for example, toothbrushes, toilet seats, combs and packaging materials also other objects that may come into contact with many people, such as a telephone handset, handrails of stairs, door and window handles, and holding straps and handles in public transport.
• Medical technology items include catheters, tubes, cover foils or surgical cutlery
• the polymers, copolymers or graft polymers produced by the process according to the invention can be used wherever bacterial-free, ie microbicidal surfaces or surfaces with non-stick properties are important. Examples of uses for microbicidal polymers or graft polymers produced by the process according to the invention are, in particular, paints, protective coatings or coatings in the following Areas
• Heat exchangers bioreactors, membranes, medical technology, contact lenses, diapers, membranes, implants, utensils, car seats, clothing (stockings, sportswear), hospital equipment, door handles, telephone receivers, public transport, animal cages, cash registers, carpets, wallpapers
• a polyamide 12 film is exposed for 2 minutes at a pressure of 1 mbar to 172 nm radiation from an excimer radiation source from Heraeus.
• the film activated in this way is placed in an irradiation reactor under protective gas and fixed thereupon the film is countercurrently flowed with 20 ml of a mixture of 3 g of 2-acrylamido-2-methoxyacetic acid methyl ester (Fa Aldrich) and 97 g of methanol are coated.
• the radiation chamber is closed and placed 10 cm below one another Excimer irradiation unit made by Heraeus, which has an emission of the wavelength 308 nm.
• the irradiation is started, the exposure time is 15 minutes.
• the film is then removed and rinsed with 30 ml of methanol.
• the film is then dried in a vacuum at 50 ° C. for 12 hours the film is extracted in water 5 times 6 hours at 30 ° C, then dried at 50 ° C for 12 hours
• a coated piece of film from Example 1 (5 ⁇ 4 cm) is placed in 30 ml of a test microbial suspension of Staphylococcus aureus and shaken. After a contact time of 15 minutes, 1 ml of the test microbial suspension is removed, and the number of bacteria in the test batch is determined more detectable from Staphylococcus aureus
• a coated piece of film from Example 1 (5 ⁇ 4 cm) is placed in 30 ml of a test microbial suspension of Pseudomonas aeruginosa and shaken. After a contact time of 60 minutes, 1 ml of the test microbial suspension is removed, and the number of bacteria in the test mixture is determined dropped from 10 7 to 10 4
• a polyamide 12 film is exposed for 2 minutes at a pressure of 1 mbar to 172 nm radiation from an excimer radiation source from Heraeus.
• the film activated in this way is placed in an irradiation reactor under protective gas and fixed thereupon the film is countercurrently flowed with 20 ml of a mixture of 3 g of 2-acetamidoacrylic acid methyl ester (from Aldrich) and 97 g of methanol are coated.
• the radiation chamber is closed and placed at a distance of 10 cm under an excimer radiation unit from Heraeus, which has an emission of the wavelength 308 nm.
• the radiation is started, the Exposure time is 15 minutes.
• the film is then removed and unwound with 30 ml of methanol.
• the film is then dried in vacuo at 50 ° C. for 12 hours.
• the film is then extracted 5 times for 6 hours at 30 ° C., then at 50 ° C. 12 Hours dried
• Example 2a A coated piece of film from Example 2 (5 ⁇ 4 cm) is placed in 30 ml of a test microbial suspension of Staphylococcus aureus and shaken. After a contact time of 15 minutes, 1 ml of the test microbial suspension is removed, and the number of bacteria in the test batch is determined the bacterial count decreased from 10 7 to 10 4
• a coated piece of film from Example 2 (5 ⁇ 4 cm) is placed in 30 ml of a test microbial suspension of Pseudomonas aeruginosa and shaken. After a contact time of 60 minutes, 1 ml of the test microbial suspension is removed, and the number of bacteria in the test mixture is determined dropped from 10 7 to 10 4
• EXAMPLE 3 A polyamide 12 film is exposed to 172 nm radiation from an excimer radiation source from Heraeus for 2 minutes at a pressure of 1 mbar.
• the film activated in this way is placed in a radiation reactor under a protective gas and fixed thereupon Mixture of 3 g of acrylic acid-tert-butylamide (from Aldrich) and 97 g of methanol are coated.
• the radiation chamber is closed and placed at a distance of 10 cm under an excimer radiation unit from Heraeus, which has an emission of the wavelength 308 nm.
• the radiation is started, the Exposure time is 15 minutes.
• the film is then removed and 30 ml Methanol is unwound.
• the film is then dried under vacuum at 50 ° C. for 12 hours.
• the film is then extracted 5 times for 6 hours at 30 ° C. in water, then dried at 50 ° C. for 12 hours
• a coated piece of film from Example 3 (5 ⁇ 4 cm) is placed in 30 ml of a test microbial suspension of Staphylococcus aureus and shaken. After a contact time of 15 minutes, 1 ml of the test microbial suspension is removed, and the number of bacteria in the test mixture is determined more detectable from Staphylococcus aureus
• a coated piece of film from Example 3 (5 ⁇ 4 cm) is placed in 30 ml of a test microbial suspension of Pseudomonas aeruginosa and shaken. After a contact time of 60 minutes, 1 ml of the test microbial suspension is removed, and the number of bacteria in the test mixture is determined dropped from 10 7 to 10 4
• a polyamide 12 film is exposed for 2 minutes at a pressure of 1 mbar to 172 nm radiation from an excimer radiation source from Heraeus.
• the film activated in this way is placed in an irradiation reactor under protective gas and fixed thereupon the film is countercurrently flowed with 20 ml of a mixture of 3 g of 2-acrylamido-2-methoxyacetic acid methyl ester (from Aldrich), 2 g of methyl methacrylate (from Aldrich) and 95 g of methanol are coated.
• the radiation chamber is closed and placed at a distance of 10 cm under an excimer radiation unit from Heraeus, which emits the The wavelength is 308 nm.
• the irradiation is started, the exposure time is 15 minutes.
• the film is then removed and rinsed with 30 ml of methanol.
• the film is then dried in vacuo for 12 hours at 50 ° C.
• the film is then extracted in water 5 times 6 hours at 30 ° C., then dried at 50 ° C. for 12 hours
• a coated piece of film from example 4 (5 ⁇ 4 cm) is placed in 30 ml of a test germ suspension of Staphylococcus aureus and shaken. After a contact time of 15 minutes, 1 ml of the test germ suspension is removed, and the number of germs in the test mixture is determined. After this time there are no germs more detectable from Staphylococcus aureus
• Example 4b A coated piece of film from example 4 (5 ⁇ 4 cm) is placed in 30 ml of a test microbial suspension of Pseudomonas aeruginosa and shaken. After a contact time of 60 minutes, 1 ml of the test microbial suspension is removed, and the number of bacteria in the test batch is determined the bacterial count decreased from 10 7 to 10 4
• a polyamide 12 film is exposed for 2 minutes at a pressure of 1 mbar to 172 nm radiation from an excimer radiation source from Heraeus.
• the film activated in this way is placed in an irradiation reactor under protective gas and fixed thereupon the film is countercurrently flowed with 20 ml of a mixture of 3 g of 2-acetamidoacrylic acid methyl ester (from Aldrich), 2 g of methyl methacrylate (from Aldrich) and 95 g of methanol are coated.
• the radiation chamber is closed and placed at a distance of 10 cm under an excimer radiation unit from Heraeus, which has an emission of the wavelength 308 nm.
• the radiation is started, the exposure time is 15 minutes.
• the film is then removed and rinsed with 30 ml of methanol.
• the film is then 12 Dried in vacuo at 50 ° C for hours.
• the film is then extracted in water 5 times 6 hours at 30 ° C., then dried at 50 ° C. for 12 hours.
• the back of the film is then treated in the same way, so that a polyamide film coated on both sides with grafted polymer is finally obtained.
• a coated piece of film from Example 5 (5 ⁇ 4 cm) is placed in 30 ml of a test germ suspension of Staphylococcus aureus and shaken. After a contact time of 15 minutes, 1 ml of the test microbial suspension is removed and the number of microbes in the test mixture is determined. After this time, no Staphylococcus aureus germs can be detected.
• Example 5b A coated piece of film from Example 5 (5 ⁇ 4 cm) is placed in 30 ml of a test germ suspension of Pseudomonas aeruginosa and shaken. After a contact time of 60 minutes, 1 ml of the test microbial suspension is removed, and the number of microbes in the test mixture is determined. After this time the number of germs has dropped from 10 7 to 10 4 .

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• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• General Health & Medical Sciences (AREA)
• Plant Pathology (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Medicinal Chemistry (AREA)
• Materials Engineering (AREA)
• Zoology (AREA)
• Public Health (AREA)
• Polymers & Plastics (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Dentistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Environmental Sciences (AREA)
• Veterinary Medicine (AREA)
• Epidemiology (AREA)
• Animal Behavior & Ethology (AREA)
• Biomedical Technology (AREA)
• Hematology (AREA)
• Toxicology (AREA)
• Molecular Biology (AREA)
• Dermatology (AREA)
• Oral & Maxillofacial Surgery (AREA)
• Transplantation (AREA)
• Treatments Of Macromolecular Shaped Articles (AREA)
• Paints Or Removers (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Graft Or Block Polymers (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Materials For Medical Uses (AREA)
• Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)

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• 1999
  • 1999-05-12 DE DE19921900A patent/DE19921900A1/de not_active Withdrawn
• 2000
  • 2000-03-30 EP EP00920619A patent/EP1183289A1/de not_active Withdrawn
  • 2000-03-30 WO PCT/EP2000/002780 patent/WO2000069933A1/de not_active Application Discontinuation
  • 2000-03-30 JP JP2000618348A patent/JP2002544346A/ja active Pending
  • 2000-03-30 CN CN00810325A patent/CN1361796A/zh active Pending
  • 2000-03-30 AU AU37901/00A patent/AU3790100A/en not_active Abandoned
• 2001
  • 2001-11-12 NO NO20015530A patent/NO20015530L/no unknown

Non-Patent Citations (1)

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