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WO2001062810A1 - Copolymeres de sels de phosphonium allyle - Google Patents

Copolymeres de sels de phosphonium allyle Download PDF

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Publication number
WO2001062810A1
WO2001062810A1 PCT/EP2001/000444 EP0100444W WO0162810A1 WO 2001062810 A1 WO2001062810 A1 WO 2001062810A1 EP 0100444 W EP0100444 W EP 0100444W WO 0162810 A1 WO0162810 A1 WO 0162810A1
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WO
WIPO (PCT)
Prior art keywords
antimicrobial
substrate
polymers according
antimicrobial polymers
branched
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.)
Ceased
Application number
PCT/EP2001/000444
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German (de)
English (en)
Inventor
Gesellschaft Für Technologie Und Innovation Mbh Creavis
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Creavis Gesellschaft fuer Technologie und Innovation mbH
Original Assignee
Creavis Gesellschaft fuer Technologie und Innovation mbH
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Application filed by Creavis Gesellschaft fuer Technologie und Innovation mbH filed Critical Creavis Gesellschaft fuer Technologie und Innovation mbH
Priority to AU50298/01A priority Critical patent/AU5029801A/en
Publication of WO2001062810A1 publication Critical patent/WO2001062810A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/16—Chemical modification with polymerisable compounds
    • C08J7/18—Chemical modification with polymerisable compounds using wave energy or particle radiation
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/34—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-halogen bonds; Phosphonium salts
    • 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
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/10—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of amides or imides
    • 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
    • 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
    • C08F291/185—The monomer(s) not being present during the irradiation or the oxidation of the macromolecule

Definitions

  • the invention relates to antimicrobial polymers which are obtained by copolymerizing allylphosphonium salts with other 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 allylphosphonium salts with further monomers on a substrate, to a process for their preparation 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 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
  • 4,532,269 discloses a terpolymer of butyl methacrylate, tributyltin methacrylate and tert - butylaminoethyl methacrylate This polymer is used as an antimicrobial marine paint, whereby the hydrophilic tert - butylaminoethyl methacrylate requires the slow erosion of the polymer and thus releases the highly toxic tributyltin methacrylate as an antimicrobial agent
  • 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, antimicrobially active polymers which, if necessary, are intended as a coating to prevent the settlement and spread of bacteria on surfaces. It has now surprisingly been found that by copolymerizing allylphosphonium salts, in particular allyltriphenylphosphonium salts with ahphatically unsaturated monomers or by Graft copolymerization of these components on a substrate gives polymers with a surface that is permanently microbicidal, is not attacked by solvents and physical stresses and shows no migration. It is not necessary to use further biocidal active substances.
  • the present invention therefore relates to antimicrobial polymers which by copolymerization of a monomer of formula I.
  • Ri -H, branched or unbranched aliphatic hydrocarbon radical with 1 to 5 carbon atoms
  • R 2 -H, branched or unbranched aliphatic hydrocarbon radical with 1 to 5
  • R t , R 5 , R ⁇ substituted or unsubstituted, branched or unbranched aliphatic or aromatic hydrocarbon radical having 1 to 50 carbon atoms, where
  • allylphosphonium salts are of interest in other technical fields, such as the production of antimicrobial polymers.
  • European application 0 615 853 describes the use of compounds containing phosphonium as additives in formulations for paper coatings
  • German application 0 42 11 140 also describes the use of phosphonium salts as additives for the production of brighteners for aqueous-acidic galvanic nickel baths
  • a use as an ingredient of adhesive polymers is described in European application 0 581 532, the phosphonium salt being added here in a concentration of up to 1.5% by weight
  • the proportion of monomers of the formula I in the copolymer according to the invention should be between 5 and 99 mol%, in particular between 40 and 98 mol%, in order to obtain a sufficient antimicrobial action of the polymer
  • All monomers which undergo copolymerization with allyltriphenylphosphonium salts can be used as ahphatically unsaturated monomers.
  • suitable acrylates or methacrylates eg acrylic acid, tert-butyl methacrylate or methyl methacrylate, styrene, vinyl chloride, vinyl ether, acrylamides, acrylonitriles, olefins (ethylene, propylene, Butylene, isobutylene), allyl compounds, vinyl ketones, vinyl acetic acid, vinyl acetate or vinyl esters, in particular for example methyl methacrylate, ethyl methacrylate, butyl methacrylate, tert-butyl methacrylate, methyl acrylate, tert-acrylate, tert-acrylate, acrylate, butyl acrylate, Methacrylic acid 3-dimethylaminopropylamide, 2-diethylaminoethyl vinyl ether, me
  • the aliphatic unsaturated monomers are preferably acrylic acid or methacrylic acid compounds
  • the allyltriphenylphosphonium bromide and the allyltriphenylphosphonium chloride are preferably used as the monomer according to formula I.
  • the antimicrobial copolymers according to the invention can also be obtained by copolymerizing monomers of the formula I with at least one aliphatic unsaturated monomer.
  • the polymerization is expediently carried out radically by means of a free-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 monomers of the formula I with at least one aliphatic unsaturated monomer on a substrate. A physisorbed coating of the antimicrobial copolymer is obtained on the substrate
  • All polymeric plastics such as polyurethanes, polyamides, polyesters and ethers, polyether block amides, polystyrene, polyvinyl chloride, polycarbonates, polyorganosiloxanes, polyolefins, polysulfones, polyisoprene, polychloroprene, polytetrafluoroethylene (PTFE), and corresponding copolymers are particularly suitable as substrate materials 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 copolymers can be obtained by graft polymerization of a substrate with monomers of the formula I and at least one aliphatic unsaturated monomer.
  • the grafting of the substrate enables the antimicrobial copolymer to be covalently bonded to the substrate. All polymeric materials, such as already mentioned plastics are 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.
  • the substrate is activated before the graft polymerization by UV radiation, plasma treatment, corona treatment , Flame treatment, ozonization, electrical discharge, ⁇ -radiation around established methods
  • 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 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 photosensitizer such as Benzophenone
  • the photosensitizer 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 usually 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 enables 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 surface of the substrate facing away from the flame side.Activation by flame is accordingly limited to relatively thin, flat substrates.
  • the exposure times generally amount to 0 1 second to 1 minute, preferably 0 5 to 2 seconds, all of which are non-luminous flames and the distances between the substrate surfaces and the outer flame front are 0 2 to 5 cm, preferably 0 5 to 2 cm
  • Substrate surfaces are made using known methods, such as dipping,
  • 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 monomers according to formula I (component I) and at least one further aliphatic unsaturated monomer (component II) according to the invention exhibit a microbicidal or antimicrobial behavior even without grafting onto a substrate surface
  • a further embodiment of the present invention is that the copolymerization of components I and II is carried out on a substrate.
  • the components can be applied to the substrate in solution.
  • suitable solvents are water, ethanol, methanol, methyl ethyl ketone, diethyl ether and dioxane .
  • Component II can also serve as solvent
  • 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 that can be used include azonitriles, alkyl peroxides, hydroperoxides, acyl peroxides, peroxoketones, peresters, peroxocarbonates, peroxodisulfate, persulfate and all the usual photoinitiators such as acetophenones, ⁇ -hydroxyketones, dimethyl ketals and and benzophenone
  • the polymerization can also be initiated 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 furthermore relates to the use of the antimicrobial polymers according to the invention for the production of antimicrobially active products and the products thus produced as such.
  • the products can be modified 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 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
  • the present invention also relates to the use of the polymers or processes according to the invention according to the invention modified the surface Polymer substrates for the production of hygiene products or medical technology articles
  • hygiene products 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 2 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. After this time, the number of bacteria is 10 7 dropped to 10 2
  • Example lb 0.05 g of the product from Example 1 is 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. After this time, the number of bacteria is 10 7 dropped to 10
  • 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. After this time the number of bacteria is 10 7 dropped to 10 2
  • Example 2b 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 8.5 g of allyl triphenylphosphonium chloride (Aldrich), 3.5 ml of tert-butyl 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 are then dissolved in 4 ml of ethyl methyl ketone are slowly added dropwise with stirring. The mixture is heated to 70 ° C. and stirred at this temperature for 72 hours. After this time, the reaction mixture is stirred into 0.5 l of cyclohexane, the polymer product precipitating out. The polymer product is filtered off and the filter residue is filtered off rinsed with 100 ml of ethanol 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 is 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. After this time the number of bacteria is 10 7 dropped to 10 2
  • 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. After this time, the number of bacteria is 10 7 dropped to 10 3
  • Example 4 10 g of allyl triphenylphosphonium chloride (Aldrich), 2 ml of methyl methacrylate (Aldrich), and 60 ml of ethanol are placed in a three-necked flask and heated to 65 ° C. under a stream of argon. Then 0.15 g of azobisisobutyronitrile is dissolved in 4 ml of ethyl methyl ketone with stirring slowly added dropwise The mixture is heated to 70 ° C. and stirred at this temperature for 72 hours. After this time, the reaction mixture is stirred into 0.5 l of cyclohexane, the polymer product precipitating out. The polymer product is filtered off and the filter residue is rinsed with 100 ml of ethanol to still exist Removing residual monomers The product is then dried in vacuo at 50 ° C. for 24 hours
  • Example 4a 0.05 g of the product from Example 4 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 dropped to 10 3
  • 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 bacteria in the test mixture is determined. After this time, the number of bacteria is 10 7 dropped to 10 3
  • Example 5a 0.05 g of the product from Example 5 is 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 was removed, and the number of microbes in the test mixture determined
  • 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 15 g of allyltriphenylphosphonium bromide (Aldrich), 3 ml of methyl methacrylate (Aldrich) and 80 ml of ethanol are coated.
  • the radiation chamber is closed and placed at a distance of 10 cm under an Heraeus excimer radiation unit which has an emission of 308 nm.
  • the radiation 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 extracted 5 times for 6 hours at 30 ° C., then at 50 ° C
  • Example 6b 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 mixture is determined dropped from 10 7 to 10 4 Example 6b
  • a coated piece of film from Example 6 (5 by 4 cm) is in 30 ml

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des polymères antimicrobiens obtenus par copolymérisation d'un monomère de la formule (I) où R1 = -H, un reste d'hydrocarbure aliphatique ramifié ou non ramifié comprenant 1 à 5 atomes de carbone R2 = -H, un reste d'hydrocarbure aliphatique ramifié ou non ramifié comprenant 1 à 5 atomes de carbone R3 = -H, -CH3 R4, R5, R6 = un reste d'hydrocarbure aromatique ou aliphatique, ramifié ou non ramifié, substitué ou non substitué, comprenant 1 à 50 atomes de carbone, R4, R5 et R6 pouvant être identiques ou différents X<-> = CH3SO4<->, NO3<->, F<->, Cl<->, Br<->, I<->, CH3CO2<->, NO2<->, NO<->, CN<->, SCN<->, CNO<->, ClO<->, ClO2<->, ClO3<->, ClO4<-> avec d'autres monomères insaturés aliphatiques, ainsi qu'un procédé de production. Ces polymères peuvent être produits par copolymérisation par greffage d'un substrat, grâce à laquelle on obtient une couche liée covalente sur la surface du substrat. Lesdits polymères antimicrobiens peuvent être utilisés sous forme de revêtement microbicide, entre autres, sur des articles hygiéniques ou en médecine, ainsi que dans des vernis ou des peintures de protection.
PCT/EP2001/000444 2000-02-23 2001-01-17 Copolymeres de sels de phosphonium allyle Ceased WO2001062810A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU50298/01A AU5029801A (en) 2000-02-23 2001-01-17 Copolymers of allylphosphonium salts

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10008177.020000223 2000-02-23
DE2000108177 DE10008177A1 (de) 2000-02-23 2000-02-23 Copolymere von Allyltriphenylphosphoniumsalzen

Publications (1)

Publication Number Publication Date
WO2001062810A1 true WO2001062810A1 (fr) 2001-08-30

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DE (1) DE10008177A1 (fr)
WO (1) WO2001062810A1 (fr)

Cited By (4)

* 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
WO2004035666A3 (fr) * 2002-10-15 2004-05-27 Creavis Tech & Innovation Gmbh Elastomeres antimicrobiens
WO2017173294A1 (fr) * 2016-04-01 2017-10-05 Dentsply Sirona Inc. Compositions et procédés d'inhibition et d'interruption de formation de biofilm
US10138307B2 (en) 2013-01-31 2018-11-27 Fachhochschule Münster Antimicrobial polymer

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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
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
WO2014097309A1 (fr) 2012-12-17 2014-06-26 Asian Paints Ltd. Revêtement autonettoyant répondant à des stimuli

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DE2126221A1 (de) * 1970-05-26 1972-01-05 Imperial Chemical Industries of Australia and New Zealand Ltd., Melbourne (Australien) Pigmentdispersion sowie Verfahren zu deren Herstellung
EP0663409A1 (fr) * 1993-07-14 1995-07-19 Nippon Chemical Industrial Company Limited Polymere antimicrobien, lentille de contact et produits d'entretien de lentilles de contact
JPH0782511A (ja) * 1993-09-14 1995-03-28 Nippon Chem Ind Co Ltd 抗菌防汚塗料
JPH10157282A (ja) * 1996-12-04 1998-06-16 Mitsubishi Paper Mills Ltd インクジェット用被記録材

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WO2002080674A1 (fr) * 2001-04-06 2002-10-17 Creavis Gesellschaft Für Technologie Und Innovation Mbh Systemes de conservation antimicrobiens pour produits alimentaires
WO2004035666A3 (fr) * 2002-10-15 2004-05-27 Creavis Tech & Innovation Gmbh Elastomeres antimicrobiens
US10138307B2 (en) 2013-01-31 2018-11-27 Fachhochschule Münster Antimicrobial polymer
WO2017173294A1 (fr) * 2016-04-01 2017-10-05 Dentsply Sirona Inc. Compositions et procédés d'inhibition et d'interruption de formation de biofilm
JP2019518785A (ja) * 2016-04-01 2019-07-04 デンツプライシロナ インコーポレイテッド バイオフィルム形成を阻害および妨害するための組成物および方法

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