WO2001014435A1 - Copolymeres d'ether d'aminopropylvinyle - Google Patents

Copolymeres d'ether d'aminopropylvinyle Download PDF

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Publication number
WO2001014435A1
WO2001014435A1 PCT/EP2000/006506 EP0006506W WO0114435A1 WO 2001014435 A1 WO2001014435 A1 WO 2001014435A1 EP 0006506 W EP0006506 W EP 0006506W WO 0114435 A1 WO0114435 A1 WO 0114435A1
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WO
WIPO (PCT)
Prior art keywords
methyl
antimicrobial
substrate
vinyl ether
polymers according
Prior art date
Application number
PCT/EP2000/006506
Other languages
German (de)
English (en)
Inventor
Peter Ottersbach
Beate Kossmann
Original Assignee
Creavis Gesellschaft Für Technologie Und Innovation Mbh
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 Creavis Gesellschaft Für Technologie Und Innovation Mbh filed Critical Creavis Gesellschaft Für Technologie Und Innovation Mbh
Priority to CA002383030A priority Critical patent/CA2383030A1/fr
Priority to AU65625/00A priority patent/AU6562500A/en
Priority to JP2001518763A priority patent/JP2003507542A/ja
Priority to EP00953028A priority patent/EP1214366A1/fr
Publication of WO2001014435A1 publication Critical patent/WO2001014435A1/fr
Priority to NO20020767A priority patent/NO20020767L/no

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • 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
    • C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
    • C08F216/14—Monomers containing only one unsaturated aliphatic radical
    • C08F216/1458—Monomers containing nitrogen
    • 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
    • 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
    • C08F291/18—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00 on to irradiated or oxidised macromolecules
    • 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
    • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • 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

Definitions

  • the invention relates to antimicrobial polymers which are obtained by copolymerizing amino-functionalized vinyl ethers with further monomers.
  • the invention further relates to a process for the preparation and use of these antimicrobial polymers
  • the invention relates to antimicrobial polymers which are obtained by graft copolymerization of amino-functionalized vinyl ethers with further monomers on a substrate, a process for their preparation of the graft copolymers and their use
  • 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 intimate area and for nursing and elderly care. Bacteria must also be kept away from furniture and device surfaces in care stations, especially in the Area of intensive care and young child care, in hospitals, especially 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 object of the present invention is therefore to develop novel, antimicrobial polymers which prevent the settlement and spread of bacteria on surfaces
  • 3-aminopropyl vinyl ether is a commercially available product, the production of which can be found, for example, in European patent application 0 514 710. It is used, inter alia, as an additive for photoresist systems, described, for example, in US 5648194, or as a building block for adhesion promoters in special urethanesilanes, for example in US 5384342 The use of such compounds in antimicrobial polymers is not known
  • the present invention therefore relates to antimicrobial copolymers which are obtained by copolymerizing a vinyl ether of the general formula
  • the proportion of vinyl ether in the reaction mixture should, in order to obtain a sufficient antimicrobial effect of the polymer, between 5 and 98 mol%, preferably between 30-98 mol%, particularly preferably between 50-98 mol%, based on the sum the Monomers
  • All monomers which undergo copolymerization with vinyl ethers of the general formula can be used as aliphatic unsaturated monomers.
  • suitable acrylates or methacrylates such as acrylic acid, tert-butyl methacrylate or methyl methacrylate, styrene, vinyl chloride, vinyl ethers, acrylamides, acrylonitriles, olefins (ethylene, Propylene, butylene, isobutylene), allyl compounds, vinyl ketones, vinyl acetic acid, vinyl acetate or vinyl esters, in particular, for example, methacrylic acid methyl ester, methacrylic acid ethyl ester,
  • the aliphatic unsaturated monomers are preferably acrylic acid or methacrylic acid compounds and the vinyl ether of the general formula is 3-aminopropyl vinyl ether
  • the antimicrobial copolymers according to the invention can be obtained by copolymerization of vinyl ethers of the general formula, in particular with 3-aminopropyl vinyl ether, with one or more aliphatic unsaturated monomers.
  • the polymerization is expediently carried out radically by means of a radical initiator or radiation-induced. Typical procedures are described in the examples
  • the antimicrobial copolymers according to the invention can also be obtained by copolymerizing vinyl ethers of the general formula, in particular with 3-aminopropyl vinyl ether, and at least one aliphatic unsaturated monomer on a substrate. A physisorbed coating of the antimicrobial copolymer is obtained on the substrate
  • All polymeric plastics are particularly suitable as substrate materials. lyurethanes, 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 wooden bodies
  • the copolymers can be obtained by graft-polymerizing a substrate with vinyl ethers of the general formula, in particular with 3-aminopropyl vinyl ether, and at least one aliphatic unsaturated monomer.
  • the grafting of the substrate enables the antimicrobial copolymer to be covalently bound to the substrate as substrates
  • All polymeric materials, such as the plastics already mentioned, can be used
  • the surfaces of the substrates can be activated by a number of methods before the graft copolymerization.All standard methods for activating polymeric surfaces can be used here.For example, the activation of the substrate before the graft polymerization by UV radiation, plasma treatment, corona treatment, flame treatment , Ozonization, electrical discharge, ⁇ -radiation using established methods
  • the surfaces are expediently freed of oils, fats or other contaminants beforehand in a known manner by means of a solvent
  • the substrate 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 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 substrate before the graft polymerization with UV radiation can also be carried out with an additional photosensitizer.
  • the photosensitizer such as benzophenone
  • the photosensitizer is applied to the substrate surface and irradiated. This can also be done with a mercury vapor lamp with exposure times of 0 1 seconds to 20 minutes, preferably 1 second to 10 minutes
  • the activation can also be achieved by plasma treatment using 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 easily built or, for example, obtained from ARCOTEC, 71297 Monsheim, Germany. They can be operated with hydrocarbons or hydrogen as fuel gas In any case, damaging overheating of the substrate must be avoided, which is easily achieved by intimate contact with a cooled metal surface on the substrate surface facing away from the flame side.
  • the activation by flame is accordingly limited to relatively thin, flat substrates.
  • the exposure times are in the generally to 0 1 second to 1 minute, preferably 0 5 to 2 seconds, all of which are non-luminous flames and the distance from the substrate surfaces to the outer flame front is 0 2 to 5 cm, preferably 0 5 to 2 cm
  • the substrate surfaces activated in this way are produced using known methods, such as dipping, Spraying or brushing, coated with vinyl ethers of the general formula (component I), in particular with 3-aminopropyl vinyl ether, and one or more aliphatic unsaturated monomers (component II), optionally in solution, water, ethanol and water-ethanol mixtures have been used as solvents Preserved, but other solvents can also be used, provided they have sufficient bulk for the monomers and the substrate surfaces wet well. Solutions with monomer contents of 1 to 10% by weight, for example about 5% by weight, have been retained in practice and result in general coherent coats covering the 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 region or in the long-wave segment of the UV region of the electromagnetic radiation.
  • 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 of the comonomer compositions according to the invention 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.
  • the monomer used for swelling can be component II
  • the antimicrobial copolymers of vinyl ethers of the general formula (component I), in particular 3-aminopropyl vinyl ether, and at least one aliphatic unsaturated monomer (component II) according to the invention exhibit a microbicidal or antimicrobial behavior even without grafting onto a substrate surface.
  • Another embodiment of the present invention consists in this that the copolymerization of components I and II is carried out on a substrate
  • the components can be applied in solution to the substrate as a solvent
  • a solvent For example, water, ethanol, methanol, methyl ethyl ketone, diethyl ether, dioxane, hexane, heptane, benzene, toluene, chloroform, dichloromethane, tetrahydrofuran and acetonitrile are suitable as solvents for component I, component II can also be used
  • antimicrobial copolymers according to the invention can also be used directly, ie not by polymerizing the components on a substrate, but rather as an antimicrobial coating. Suitable coating methods are the application of the copolymers in solution or as a melt
  • the solution of the polymers according to the invention can be applied to the substrates, for example by dipping, spraying or painting
  • Initiators which can be used in the preparation of the copolymers according to the invention are, inter alia, azonitriles, alkyl peroxides, hydroperoxides, acyl peroxides, peroxoketones, peresters, peroxocarbonates, peroxodisulfate, persulfate and all customary photoinitiators such as acetophenones, ⁇ -hydroxyketones, dimethyl ketones and benzophenone.
  • Polymerization initiation can also be used also thermally or, as already stated, by electromagnetic radiation, such as UV light or ⁇ radiation
  • antimicrobial polymers according to the invention can also be used as components for the formulation of paints and varnishes
  • the present invention further relates to the use of the antimicrobial polymers or copolymers 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, polyolefms, silicones, polysiloxanes, polymethacrylate or polyterephthalates which have surfaces modified with polymers 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
  • copolymers or graft copolymers according to the invention can be used wherever bacteria-free, ie microbicidal surfaces or surfaces with non-stick properties are important.
  • examples of uses for the copolymers or graft polymers according to the invention are, in particular, paints, protective coatings or coatings in the following areas
  • Medical technology contact lenses, diapers, membranes, implants, everyday items, car seats, clothing (stockings, sportswear), hospital facilities, door handles, telephone receiver, public transport, animal cages, cash registers, carpets, wallpaper
  • the present invention furthermore relates to the use of the surface of the polymers or processes modified according to the invention, according to the invention
  • Polymer substrates for the production of hygiene products or medical technology articles are, for example, toothbrushes, toilet seats, combs and packaging materials.
  • hygiene articles also includes other objects that may come into contact with many people, such as telephone receivers, handrails of stairs, door and window handles as well as holding belts and handles in public transport.
  • Medical technology items include catheters, tubes, cover foils or surgical cutlery
  • Example 1 0.05 g of the product from Example 1 are placed in 20 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 Staphylococcus aureus more detectable
  • Example 2 0.05 g of the product from Example 1 are dissolved in 20 ml of a test germ suspension of pseudo- monas aeruginosa inserted and shaken After a contact time of 60 minutes, 1 ml of the test germ suspension is removed, and the number of bacteria in the test mixture is determined. After this time, the number of bacteria has dropped from 10 7 to 10 2
  • Example 2 0.05 g of the product from Example 2 are placed in 20 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 Staphylococcus aureus more detectable
  • Example 2 0.05 g of the product from Example 2 are placed in 20 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 10 7 dropped to 10 2
  • Example 3 6 g of 3-aminopropyl vinyl ether (Aldrich), 6 g of 2-diethylaminoethyl methacrylate (Aldrich) and 60 ml of ethanol are placed in a three-necked flask and heated to 65 ° C. under a stream of argon. 0.15 g of azobisisobutyronitrile is then dissolved in 4 ml of ethyl methyl ketone under Stirring slowly added dropwise The mixture is heated to 70 ° C. and stirred for 72 hours at this temperature. After this time, the reaction mixture is stirred into 0.5 l demineralized water, the polymer product precipitating. After filtering off the product, the filter residue becomes 100 ml of demineralized water rinsed to remove any remaining monomers. The product is then dried in vacuo at 50 ° C. for 24 hours
  • Example 3 0.05 g of the product from Example 3 are placed in 20 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 10 7 dropped to 10 2
  • Example 3 0.05 g of the product from Example 3 are placed in 20 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 10 7 dropped to 10 2
  • Example 4 0.05 g of the product from Example 4 are placed in 20 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 removed and the number of bacteria in the test batch determined. After this time, no bacteria from Staphylococcus aureus can be detected
  • Example 4b 0.05 g of the product from Example 4 are placed in 20 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 microbes in the test mixture is determined the bacterial count dropped from 10 7 to 10 2
  • 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 exposed to 20 ml of a mixture in a protective gas countercurrent 6 g of 3-aminopropyl vinyl ether (Aldrich), 6 g of butyl methacrylate (Aldrich) and 60 g of ethanol 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 irradiation is started, the exposure time is 15 minutes.
  • the film is then removed and rinsed with 30 ml of ethanol.
  • the film is then dried in vacuo at 50 ° C. for 12 hours.
  • the film is then extracted 5 times 6 hours at 30 ° C. in water. then dried at 50 ° C for 12 hours
  • Example 5b A coated piece of film from Example 5 (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. After this time there are no germs more detectable from Staphylococcus aureus Example 5b
  • a coated piece of film from Example 5 (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 to 10
  • Example 6 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 then counter-currented with 20 ml a mixture of 6 g of 3-aminopropyl vinyl ether (from Aldrich), 4 g of methacrylic acid tert-butyl ester (from Aldrich) and 60 g of ethanol.
  • 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 irradiation is started, the exposure time is 15 minutes.
  • the film is then removed and rinsed with 30 ml of ethanol.
  • the film is then dried in vacuo for 12 hours at 50 ° C.
  • the film is then 5 times 6 in water Extracted hours at 30 ° C, then dried at 50 ° C for 12 hours
  • a coated piece of film from Example 6 (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
  • Example 6b A coated piece of film from Example 6 (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

Abstract

L'invention concerne des copolymères antimicrobiens obtenus par copolymérisation de vinyléthers de la formule générale, notamment de 3-aminopropylvinyléthers avec d'autres monomères insaturés de manière aliphatique. L'invention concerne en outre un procédé permettant de les préparer. Ces polymères peuvent également s'obtenir par copolymérisation par greffage d'un substrat, un revêtement lié de manière covalente étant maintenu sur la surface du substrat. Ces polymères antimicrobiens s'utilisent comme revêtement microbicide, notamment sur des articles d'hygiène ou dans le domaine médical, ainsi que dans des peintures ou des enduits protecteurs.
PCT/EP2000/006506 1999-08-24 2000-07-08 Copolymeres d'ether d'aminopropylvinyle WO2001014435A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CA002383030A CA2383030A1 (fr) 1999-08-24 2000-07-08 Copolymeres d'ether d'aminopropylvinyle
AU65625/00A AU6562500A (en) 1999-08-24 2000-07-08 Copolymers of aminopropyl vinyl ether
JP2001518763A JP2003507542A (ja) 1999-08-24 2000-07-08 アミノプロピルビニルエーテルのコポリマー
EP00953028A EP1214366A1 (fr) 1999-08-24 2000-07-08 Copolymeres d'ether d'aminopropylvinyle
NO20020767A NO20020767L (no) 1999-08-24 2002-02-15 Kopolymer av aminopropylvinyleter

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19940023.7 1999-08-24
DE19940023A DE19940023A1 (de) 1999-08-24 1999-08-24 Copolymere des Aminopropylvinylethers

Publications (1)

Publication Number Publication Date
WO2001014435A1 true WO2001014435A1 (fr) 2001-03-01

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PCT/EP2000/006506 WO2001014435A1 (fr) 1999-08-24 2000-07-08 Copolymeres d'ether d'aminopropylvinyle

Country Status (8)

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EP (1) EP1214366A1 (fr)
JP (1) JP2003507542A (fr)
CN (1) CN1382164A (fr)
AU (1) AU6562500A (fr)
CA (1) CA2383030A1 (fr)
DE (1) DE19940023A1 (fr)
NO (1) NO20020767L (fr)
WO (1) WO2001014435A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002080674A1 (fr) * 2001-04-06 2002-10-17 Creavis Gesellschaft Für Technologie Und Innovation Mbh Systemes de conservation antimicrobiens pour produits alimentaires
WO2010077539A1 (fr) * 2008-12-29 2010-07-08 3M Innovative Properties Company Copolymère antimicrobien pour le revêtement de surfaces, obtenu par dérivation d'un copolymère vinylamine-alcool vinylique
WO2023033410A1 (fr) * 2021-08-30 2023-03-09 주식회사 엘지화학 Polymère antibactérien et film polymère antibactérien le comprenant

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JP5172067B2 (ja) * 2000-06-09 2013-03-27 ザ ルブリゾル コーポレイション 増粘剤
DE10110885A1 (de) * 2001-03-07 2002-09-12 Creavis Tech & Innovation Gmbh Mokrobizide Trennsysteme
DE10150741A1 (de) * 2001-10-13 2003-04-24 Creavis Tech & Innovation Gmbh Verfahren und Vorrichtung zur Durchflusssterilisation von Flüssigkeiten
DE10205923A1 (de) * 2002-02-12 2003-08-21 Creavis Tech & Innovation Gmbh Wasch- und Reinigungsformulierungen mit antimikrobiellen Polymeren
DE10211562B4 (de) * 2002-03-15 2006-09-28 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Antimikrobiell modifiziertes Substrat, Verfahren zu dessen Herstellung sowie dessen Verwendung
DE10246625A1 (de) 2002-10-07 2004-04-15 Basf Ag Verfahren zum Abtöten von Mikroorganismen
CN106310372B (zh) * 2015-06-23 2020-05-22 上海交通大学 可降解镁基骨内植物可载药高分子/钙磷复合涂层及制备

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Publication number Priority date Publication date Assignee Title
US2980634A (en) * 1954-10-08 1961-04-18 Rohm & Haas Quaternary ammonium compounds of polymers of aminoalkyl vinyl ethers
EP0862859A1 (fr) * 1997-03-06 1998-09-09 Hüls Aktiengesellschaft Procédé de préparation matières plastiques antimicrobiennes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2980634A (en) * 1954-10-08 1961-04-18 Rohm & Haas Quaternary ammonium compounds of polymers of aminoalkyl vinyl ethers
EP0862859A1 (fr) * 1997-03-06 1998-09-09 Hüls Aktiengesellschaft Procédé de préparation matières plastiques antimicrobiennes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002080674A1 (fr) * 2001-04-06 2002-10-17 Creavis Gesellschaft Für Technologie Und Innovation Mbh Systemes de conservation antimicrobiens pour produits alimentaires
WO2010077539A1 (fr) * 2008-12-29 2010-07-08 3M Innovative Properties Company Copolymère antimicrobien pour le revêtement de surfaces, obtenu par dérivation d'un copolymère vinylamine-alcool vinylique
WO2023033410A1 (fr) * 2021-08-30 2023-03-09 주식회사 엘지화학 Polymère antibactérien et film polymère antibactérien le comprenant

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DE19940023A1 (de) 2001-03-01
EP1214366A1 (fr) 2002-06-19
CN1382164A (zh) 2002-11-27
NO20020767L (no) 2002-04-24
CA2383030A1 (fr) 2001-03-01
NO20020767D0 (no) 2002-02-15
AU6562500A (en) 2001-03-19
JP2003507542A (ja) 2003-02-25

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