EP1366086A1 - Formulations reactives comportant des polymeres antimicrobiens - Google Patents

Formulations reactives comportant des polymeres antimicrobiens

Info

Publication number
EP1366086A1
EP1366086A1 EP01984836A EP01984836A EP1366086A1 EP 1366086 A1 EP1366086 A1 EP 1366086A1 EP 01984836 A EP01984836 A EP 01984836A EP 01984836 A EP01984836 A EP 01984836A EP 1366086 A1 EP1366086 A1 EP 1366086A1
Authority
EP
European Patent Office
Prior art keywords
antimicrobial
phosphonium
formulations according
methacrylate
reactive formulations
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01984836A
Other languages
German (de)
English (en)
Inventor
Peter Ottersbach
Friedrich Sosna
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
CREAVIS GESELLSCHAFT fur TECHNOLOGIEUND INNOVATION MBH
CREAVIS GES fur TECHNOLOGIEUN
Creavis Gesellschaft fuer 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 fur TECHNOLOGIEUND INNOVATION MBH, CREAVIS GES fur TECHNOLOGIEUN, Creavis Gesellschaft fuer Technologie und Innovation mbH filed Critical CREAVIS GESELLSCHAFT fur TECHNOLOGIEUND INNOVATION MBH
Publication of EP1366086A1 publication Critical patent/EP1366086A1/fr
Withdrawn legal-status Critical Current

Links

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
    • 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
    • A01N37/12—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 the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
    • 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
    • A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/20—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
    • 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
    • C08F8/00—Chemical modification by after-treatment

Definitions

  • the invention relates to the use and use of antimicrobial polymers in reactive formulations.
  • Mucus layers often form, which cause microbial populations to rise extremely, which have a lasting impact on the quality of water, beverages and food, and can even lead to product spoilage and consumer health damage.
  • Bacteria must be kept away from all areas of life where hygiene is important. This affects textiles for direct body contact, especially 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, in particular 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 infections and in toilets.
  • Plastic cladding are equipped, which are particularly easy to handle. Next to the Undesired visual impression can also be reduced under certain circumstances, the function of appropriate components. In this context, for example, algae growth of photovoltaic functional areas should be considered.
  • the copolymer produced with aminomethacrylates is only a matrix or carrier substance for added microbicidal active substances which can diffuse or migrate from the carrier substance. Polymers of this type lose their effect more or less quickly when the necessary “minimal inhibitory concentration” (MIC) is no longer achieved. From European patent applications 0 862 858 it is also known that copolymers of tert-butylaminoethyl methacrylate, a methacrylic acid ester with a secondary amino function, have inherent microbicidal properties.
  • This terpolymer exhibits so-called contact microbicidity without the addition of a microbicidal active ingredient.
  • a large number of contact microbicidal polymers are known from the following patent applications: DE 100 24 270, DE 100 22 406, PCT / EP00 / 06501, DE 100 14 726, DE 100 08 177, PCT / EP00 / 06812, PCT / EP00 / 06487 , PCT / EP00 / 06506, PCT / EP00 / 02813, PCT / EP00 / 02819, PCT / EP00 / 02818, PCT / EP00 / 02780, PCT / EP00 / 02781, PCT / EP00 / 02783, PCT / EP00 / 02782, PCT / EP00 / 02799, PCT / EP00 / 02798, PCT / EP00 / 00545, PCT / EP00 / 00544.
  • These polymers do not contain any low molecular weight components; the antimicrobial properties are due to the contact of bacteria with the surface.
  • the present invention therefore relates to antimicrobial reactive formulations comprising one or more polymerizable monomers and one or more antimicrobial polymers.
  • the polymerizable monomers can be free-radically polymerizable, olefinically unsaturated monomers, but also polycondensable monomers. Examples of these monomers are given below.
  • the reactive formulations can already contain appropriate initiators such as thermal or UV starters; it is also possible to add a prepared mixture with these initiators before using the formulation.
  • Nitrogen and phosphorus functionalized monomers are preferably used to prepare the antimicrobial polymers, in particular the antimicrobial polymers are prepared from at least one of the following monomers:
  • Methacryloyloxyethyltrimethylammonium chloride 3-Methacryloylaminopropyltrime- thylammonium chloride, 2-methacryloyloxyethyltrimethylammonium chloride, 2-acryloyloxyethyl 4-benzoyldimethylammoniumbromid, 2-methacryloyloxyethyl-4- benzoyldimethylammoniumbromid, 2- acrylamido-2-methyl-1-propanesulfonic acid, 2-
  • the proportion of the antimicrobial polymers in the reactive formulations can be 0.01 to 25% by weight, preferably 0.01 to 10% by weight, particularly preferably 0.1 to 5% by weight.
  • the process of the invention is such that the reactive mixture, which in addition to optionally admixed initiators and additives such.
  • B. light and heat stabilizers preferably made of olefinically unsaturated monomers, such as. B. vinyl derivatives, styrene compounds, allyl derivatives, olefins, acrylic acid or methacrylic acid compounds, here in particular methyl methacrylate, methyl acrylate, methacrylic acid tert. -butyl ester, acrylic acid-tert.
  • This reaction mixture is then reacted according to the respective underlying hardening process of the reactive mixture, e.g. B. by supplying heat, light or moisture.
  • the result is a cured semifinished product or resin that has antimicrobial properties.
  • This antimicrobial product can now either be used directly, such as B. in a form hardened polymethyl methacrylate plates, or by a subsequent physical treatment, such as. B. grinding, prepare for further treatment steps.
  • the products thus obtained can e.g. B. as an aqueous solution or in powder form directly, for. B. for the disinfection of cooling water circuits or indirectly z. B. be used by working in paints or other coatings.
  • the formulations are preferably used in the form of powders or polymer particles, but can also be in dissolved form, e.g. B. can be used together with a suitable solvent.
  • the grain sizes of the polymer particles are preferably less than 1 mm, particularly preferably less than 500 ⁇ m.
  • these coatings can contain any polymer, preferably polyamides, polyurethanes, polyether block amides, polyester amides, polyester imides, PVC, polyolefins, silicones, polysiloxanes, polymethacrylate and / or polyterephthalates, or can be applied to these polymers.
  • Such products are preferably based on polyamides, polyurethanes, polyether block amides, polyester amides, polyester imides, PVC, polyolefins, silicones, polysiloxanes, polymethacrylate or polyterephthalates, metals, glasses, woods and ceramics which have surfaces coated with compounds or polymer formulations 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, coated pipes, semi-finished products, roofing, bathroom and toilet articles, kitchen articles, components of sanitary facilities, components of animal cages and dwellings, toys, components in water systems, Food packaging, controls (touch panel) of devices and contact lenses.
  • the formulations can be used wherever bacteria-free, algae and fungus-free, ie microbicidal surfaces or surfaces with non-stick properties are important. Examples of use for the compounds or polymer formulations according to the invention can be found in the following areas:
  • Marine hulls, port facilities, buoys, drilling platforms, ballast water tanks House: roofing, cellars, walls, facades, greenhouses, sun protection, garden fences, wood protection
  • Machine parts air conditioners, ion exchangers, process water, solar systems, heat exchangers, bioreactors, membranes, cooling water treatment - medical technology: contact lenses, diapers, membranes, implants
  • Articles of daily use car seats, clothing (stockings, sportswear), hospital equipment, door handles, telephone receivers, public transport, animal cages, cash registers, carpeting, wallpaper
  • objects of the present invention are the use with formulations, hygiene products or medical technology articles produced according to the invention.
  • Such hygiene products include toothbrushes, toilet seats, combs and packaging materials.
  • hygiene articles also includes other objects that may U. 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 articles are e.g. B. catheters, tubes, cover sheets or surgical cutlery.
  • the reactive formulations according to the invention are used as a biofouling inhibitor, in particular in cooling circuits.
  • a biofouling inhibitor in particular in cooling circuits.
  • the addition of microbicidal substances such as formalin is not possible with open cooling systems, as are common in power plants or chemical plants.
  • microbicidal substances are often highly corrosive or foam-forming, which prevents use in such systems.
  • reactive formulations according to the invention can be fed into the process water as pure substance, blend or as a coating of further polymers in finely dispersed form.
  • the bacteria are killed on the antimicrobial compounds or the polymer formulations and, if necessary, removed from the system by filtering off the dispersed polymer / blend. A deposit of bacteria or algae on system parts can be effectively prevented.
  • the present invention therefore furthermore relates to processes for the disinfection of cooling water streams, in which cooling water antimicrobial reactive formulations in dispersed form or antimicrobial compounds in dissolved form are added.
  • reactive formulation always means the polymerized form of the antimicrobial polymer in the formulations according to the invention.
  • the dispersed form of the reactive formulations can itself, for. B. by emulsion polymerization, precipitation or suspension polymerization or subsequently by grinding the antimicrobial polymer z. B. can be obtained in a jet mill.
  • the particles obtained in this way are preferably used in a size distribution of 0.001 to 3 mm (as ball diameter), so that on the one hand a large surface is available for killing the bacteria or algae, and on the other hand where necessary, the separation from the cooling water, for. B. is easily possible by filtration.
  • the method can e.g. B. be exercised in such a way that part (5-10%) of the reactive formulations used are continuously removed from the system and replaced by a corresponding amount of fresh material becomes.
  • further antimicrobial reactive formulations can be added, if necessary, while checking the bacterial count of the water. Depending on the water quality, 0.1-100 g of antimicrobial reactive formulation per m 3 of cooling water are sufficient.
  • a 3 by 3 cm piece of the plastic plate from Example 1a is placed on the bottom of a Beaker placed containing 10 mL of a test microbial suspension of Pseudomonas aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 3 germs per mL.
  • tert-butylaminoethyl methacrylate (Aldrich) and 250 ml of ethanol are placed in a three-necked flask and heated to 65 ° C. under a stream of argon. Then 0.5 g of azobisisobutyronitrile dissolved in 20 ml of ethanol are slowly added dropwise with stirring. The mixture is heated to 70 ° C. and stirred at this temperature for 6 hours. After this time, the solvent is removed from the reaction mixture by distillation. The product is then dried in vacuo at 50 ° C. for 24 hours. The product is then dissolved in 200 ml of acetone, after which the solvent is removed from the reaction mixture by distillation and dried in vacuo at 50 ° C. for 24 hours.
  • Example 2c A 3 x 3 cm piece of the plastic plate from Example 2a is placed on the bottom of a beaker containing 10 mL of a test microbial suspension of Pseudomonas aeruginosa. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs dropped from 10 7 to 10 2 germs per mL.
  • Example 2c A 3 x 3 cm piece of the plastic plate from Example 2a is placed on the bottom of a beaker containing 10 mL of a test microbial suspension of Pseudomonas aeruginosa. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs dropped from 10 7 to 10 2 germs per mL.
  • a 3 x 3 cm piece of the plastic plate from Example 2c is placed on the bottom of a beaker containing 10 mL of a test microbial suspension of Pseudomonas aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs dropped from 10 7 to 10 2 germs per mL.
  • 3g of the product from Example 2 are mixed and placed in a polyethylene bag, which is closed and locked between two metal plates spaced 3 cm apart. This assembly is now immersed in a water bath at 60 ° C for 14 hours. After the time has elapsed, the structure is removed from the water bath and the hardened plastic sheet is separated from the polyethylene film after cooling to room temperature.
  • Example 2g A 3 x 3 cm piece of the plastic plate from Example 2e is placed on the bottom of a beaker containing 10 mL of a test germ suspension from Pseudomonas aeruginosa. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs dropped from 10 7 to 10 2 germs per mL.
  • Example 2g A 3 x 3 cm piece of the plastic plate from Example 2e is placed on the bottom of a beaker containing 10 mL of a test germ suspension from Pseudomonas aeruginosa. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs dropped from 10 7 to 10 2 germs per mL.
  • Example 2g A 3 x 3 cm piece of the plastic plate from Example 2e is placed on the
  • Example 2 g The product from Example 2 g is comminuted in a centrifugal mill and separated into fractions of different grain sizes by means of a sieving machine. 0.1 g of the grain size fraction smaller than 80 micrometers are added to 20 ml of a test microbial suspension of Pseudomonas aeruginosa. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time no more Pseudomonas aeruginosa germs can be detected.
  • Example 2i 16 g of adipic acid (from Aldrich), 42 g of oleic acid (from Aldrich), 44 g of phthalic acid anhydride (from Aldrich), 105 g of anhydrous 1.1 are placed in a 500 ml three-necked flask with stirrer and descending condenser with vacuum. Weighed in 1-trihydroxymethylpropane (Aldrich) and 2 g of the product from Example 2 and displaced the air by evacuation and filling with argon. The mixture is then slowly heated under a gentle stream of argon until the contents of the flask begin to melt at approximately 124 ° C., so that stirring can begin. The inside temperature is now brought to 175 ° C within 2.5 hours.
  • Example 2j As soon as the temperature at the top of the column falls below 70 ° C, a pump is connected and slowly evacuated to 30 Torr over the course of two hours. At this pressure and an internal temperature of 175 ° C, the mixture is stirred for a further 7 hours. Then the pump is switched off and allowed to cool under argon. A highly branched polyester remains as the product.
  • Example 2j
  • Example 2 i The product from Example 2 i is mortared. 0.2 g of this ground product is added to 20 ml of a test germ suspension of Pseudomonas aeruginosa. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time no more Pseudomonas aeruginosa germs can be detected.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Water Supply & Treatment (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Hydrology & Water Resources (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Polymerisation Methods In General (AREA)
  • Graft Or Block Polymers (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne l'utilisation de polymères antimicrobiens dans des formulations réactives et l'utilisation de ces dernières.
EP01984836A 2001-01-23 2001-12-13 Formulations reactives comportant des polymeres antimicrobiens Withdrawn EP1366086A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10102900 2001-01-23
DE10102900A DE10102900A1 (de) 2001-01-23 2001-01-23 Antimikrobielle Polymere in Reaktivformulierungen
PCT/EP2001/014683 WO2002059163A1 (fr) 2001-01-23 2001-12-13 Formulations reactives comportant des polymeres antimicrobiens

Publications (1)

Publication Number Publication Date
EP1366086A1 true EP1366086A1 (fr) 2003-12-03

Family

ID=7671456

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01984836A Withdrawn EP1366086A1 (fr) 2001-01-23 2001-12-13 Formulations reactives comportant des polymeres antimicrobiens

Country Status (5)

Country Link
US (1) US20040072944A1 (fr)
EP (1) EP1366086A1 (fr)
JP (1) JP2004517201A (fr)
DE (1) DE10102900A1 (fr)
WO (1) WO2002059163A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10351004A1 (de) * 2003-10-30 2005-05-25 Basf Ag Nanopartikuläre Wirkstoffformulierungen
US20070166344A1 (en) * 2006-01-18 2007-07-19 Xin Qu Non-leaching surface-active film compositions for microbial adhesion prevention
US11284994B2 (en) 2017-11-01 2022-03-29 Alcon Inc. Bernoulli gripper for intraocular and contact lenses

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4172177A (en) * 1975-06-17 1979-10-23 Kyowa Gas Chemical Industry Co., Ltd. Water insoluble hydrophilic polymer composition
DE2548801A1 (de) * 1975-10-31 1977-05-12 Ilhelm Hans Prof Dipl Chem Dr Olymerisatzubereitungen aus polymerisaten bzw. copolymerisaten von estern ungesaettigter carbonsaeuren und di- bzw. polyisocyanaten
JP2501373B2 (ja) * 1991-03-18 1996-05-29 悦子 須郷 活魚用抗菌飼育材料およびその製造方法
US5242684A (en) * 1991-10-25 1993-09-07 Isp Investments Inc. Antimicrobial, low toxicity, non-irritating composition comprising a blend of bis-quaternary ammonium compounds coprecipitated with a copolymer of vinylpyrrolidone and an acrylamido or vinyl quaternary ammonium monomer
EP0606762B1 (fr) * 1992-12-25 1998-08-05 Japan Synthetic Rubber Co., Ltd. Composition résineuse antibacterielle
DE19709075A1 (de) * 1997-03-06 1998-09-10 Huels Chemische Werke Ag Verfahren zur Herstellung antimikrobieller Kunststoffe
GB9318170D0 (en) * 1993-09-02 1993-10-20 Kodak Ltd Antimicrobial polymers and compositions containing them
US6300395B1 (en) * 1994-12-07 2001-10-09 Nikon Parkerizing, Co., Ltd. Aqueous hydrophilization treatment composition and method for aluminum-containing metal material
DE19709076A1 (de) * 1997-03-06 1998-09-10 Huels Chemische Werke Ag Verfahren zur Herstellung antimikrobieller Kunststoffe
JPH10306239A (ja) * 1997-05-06 1998-11-17 Mitsubishi Rayon Co Ltd 抗菌性塗料
US5859136A (en) * 1997-11-03 1999-01-12 E. I. Du Pont De Nemours And Company Coating composition containing an amine functional dispersed polymer and an isocyanate curing agent

Non-Patent Citations (1)

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Title
See references of WO02059163A1 *

Also Published As

Publication number Publication date
JP2004517201A (ja) 2004-06-10
US20040072944A1 (en) 2004-04-15
DE10102900A1 (de) 2002-07-25
WO2002059163A1 (fr) 2002-08-01

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