EP2170045A2 - Polymères particulaires contenant une substance active biocide - Google Patents

Polymères particulaires contenant une substance active biocide

Info

Publication number
EP2170045A2
EP2170045A2 EP08760849A EP08760849A EP2170045A2 EP 2170045 A2 EP2170045 A2 EP 2170045A2 EP 08760849 A EP08760849 A EP 08760849A EP 08760849 A EP08760849 A EP 08760849A EP 2170045 A2 EP2170045 A2 EP 2170045A2
Authority
EP
European Patent Office
Prior art keywords
polymer matrix
polymer
matrix according
particulate
weight
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Withdrawn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
EP08760849A
Other languages
German (de)
English (en)
Inventor
Hermann Uhr
Frank Sauer
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.)
Lanxess Deutschland GmbH
Original Assignee
Lanxess Deutschland GmbH
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 Lanxess Deutschland GmbH filed Critical Lanxess Deutschland GmbH
Publication of EP2170045A2 publication Critical patent/EP2170045A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N25/08—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 containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds

Definitions

  • the present invention relates to particulate polymer matrix containing a biocidic agent homogeneously distributed in the polymeric matrix, to processes for their preparation, dispersions containing this particulate polymer matrix, and their use as microbiocidal agent for the protection of engineering materials
  • Biocides especially fungicides and algicides, are used in paint systems and plasters to prevent these systems from infesting with fungi and / or algae and the associated visual alteration and destruction of the paint itself or the substrate.
  • the active ingredients are incorporated directly or as formulations, such as solutions and dispersions of the active ingredients in the systems in question.
  • the long-term effect in the active media such as paints is not sufficiently good because the fungicidal and / or algicidal active substances are leached out of the paint film or the plaster with rainwater or condensation (so-called "leaching effect"), resulting in a decrease in concentration
  • the active ingredients in the dried, sometimes highly alkaline plasters and paints can be rapidly degraded (hydrolyzed) .
  • the unprotected active ingredients are even already present in the color packs and starting materials for the Plasters decompose and thereby lose their intended effectiveness.
  • EP-A-0758633 describes porous granules containing chemical substances, e.g. also contain biocides that release them slowly in the application.
  • microcapsules have become known, which preferably contain zinc pyrithione or irgarol and which are prepared by the fact that aqueous dispersions of a polymer, one or more active ingredients and a low-boiling solvent are freed from the solvent with vigorous stirring and the resulting microcapsules by filtration be isolated - -
  • microcapsules used are either too easily destroyed or in turn are prepared using solvents whose excessively high residual contents in the microcapsules limit their use.
  • a particulate polymer matrix was now found containing a biocidal active substance distributed homogeneously in the polymeric matrix, characterized in that
  • the polymer is a thermoplastic polymer
  • the polymer matrix has an active substance content of 2 to 80% by weight.
  • the polymer matrix is preferably monolithic particles in which the active ingredient is homogeneously distributed in the matrix.
  • the term "homogeneously distributed” is also understood to mean the distribution of an active ingredient introduced into the matrix after mixing and extrusion, for the sole purpose of clarification, microcapsules having a drug core surrounded by a thin polymer wall are not covered by the term polymer matrix ,
  • thermoplastic polymers that can be used according to the invention may be a multiplicity of different polymers. Preference is given to using polyacrylates, polyalkylene glycols, in particular polyethylene glycols or polyethylene-polypropylene glycol copolymers
  • the glass transition temperature T g of the thermoplastic polymers is generally from 30 to 250 ° C., preferably from 50 to 200 ° C. - -
  • thermoplastic polyacrylates are, in principle, all known polyacrylates which are solid at 40 ° C., preferably those of the general formula (1),
  • the polyurethanes may be all conventional, preferably solid polyurethanes.
  • the polyurethanes have repeat units of the general formula (III),
  • dihydroxy compounds are preferably formed by polycondensation of the dihydroxy compounds with phosgene or carbonic acid diesters. It is also possible to use mixtures of different dihydroxy compounds. If, for example, different bisphenols are used in multistage polycondensations, block polymers are obtained. If dicarboxylic acid dichlorides are used in addition to the carbonic acid esters, polyester polycarbonates are obtained which can likewise be used in the process according to the invention.
  • polyester it is possible to use preferably all polyesters which are solid at 40 ° C. and are in principle held together by ester bonds (-O-CO-).
  • the so-called homopolyesters may be both hydroxycarboxylic acid types (AB) and dihydroxy-dicarboxylic acid types (AA-BB).
  • AB types are preferably polyglycolic acids, polylactic acids, poly ( ⁇ -hydroxybutyric acid) s, poly ( ⁇ -caprolactone) s or polyhydroxybenzoic acids.
  • Aliphatic AA-BB types are aliphatic diols with aliphatic dicarboxylic acid esters which also contain hydroxy groups as end groups, which can then be used, for example, for the preparation of polyesterurethanes, for example polytetramethylene adipates.
  • AA-BB types of aliphatic diols and aromatic dicarboxylic acids it is preferred to use polyalkylene terephthalates such as polyethylene terephthalate, polybutylene terephthalate or poly (1,4-cyclohexanedimethylene terephthalate), in each case also mixtures of the dihydroxy compounds and dihydroxycarboxylic acids.
  • Purely aromatic polyesters are preferably composed of poly (4-hydroxybenzoic acid) or polycondensates of bisphenol A and phthalic acids.
  • polyesters of unsaturated dicarboxylic acids which are referred to as UP resins.
  • the preferred polyureas are formally polymers which have repeating units of the general formula (V)
  • the usable polyureas are not limited to "pure" polyureas, but it is also co-polymers with other structural units in the main chain can be used, for example urethane (polyurethane polyureas), amide (Polyamidpolyharnstoffe), imide (Polyimidpolyharnscher) or carbonate groups (Polycarbonatpolyharnscher).
  • mixtures of two or more of the above-mentioned can also be used.
  • Polymers are used.
  • auxiliaries may be added to polymers which favorably influence the properties and the stability of the polymers.
  • plasticizers and stabilizers such as antioxidants, radical scavengers or UV stabilizers.
  • the preferred polymers are from the groups of polyacrylates, polyalkylene glycols, polyurethanes and polyamides.
  • the biocidal active ingredients are preferably fungicides, algicides, bactericides and / or insecticides.
  • the algicides are preferably:
  • MCPA MCPA hydrazide, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron, metam, metamifop, metamitron, metazachlor, methabenzthiazuron, methazole, methopyrone, methyldymrone, methylisothiocyanate, metobromuron, metoxuron, metribuzin, metsulfuron, Molinate, Monalid, Monolinuron, MSMA, Metolachlor, Metosulam, Metobenzuron,
  • the algicides are triazine compounds such as terbutryn, cybutryn, propazine or terbutone, urea compounds such as diuron, benzthiazuron, methabenzthiazuron, tebuthiuron, and isoproturon, or uracils such as terbacil.
  • the fungicides are preferably
  • Triazoles such as:
  • Succinate dehydrogenase inhibitors such as:
  • Naphthalene derivatives such as:
  • Dichlorofluidide tolylfluanid, folpet, fluorfolpet; Captan, Captofol;
  • Benzimidazoles such as:
  • Morpholine derivatives such as:
  • Benzothiazoles such as:
  • Benzothiophene dioxides such as:
  • Isothiazolinones such as: - -
  • iodine derivatives such as:
  • Methoxyacrylates or similar such as:
  • Azoxystrobin Dimoxystrobin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Trifloxystrobin, 2,4-dihydro-5-methoxy-2-methyl-4- [2 - [[[[l- [3- (trifluoromethyl ) phenyl] ethylidenes] amino] oxy] methyl] phenyl] -3H-l, 2,4-triazol-3-ones (CAS No. 185336-79-2);
  • the fungicides are azaconazole, bromuconazole, cyproconazole, dichlobutrazole, diniconazole, hexaconazole, metaconazole, penconazole, propiconazole,
  • the bactericides are preferably:
  • Formaldehyde and formaldehyde compounds such as: benzyl alcohol (poly) -hemiformal, n-butanol-hemiformal, dazomet, ethylene glycol hemiformal, hexa-hydro-S-triazines, hexamethylenetetramine, N-hydroxymethyl-N '- methylthiourea, N-methylolchloroacetamide, oxazolidines , Paraformaldehyde, taurolin,
  • Isothiazolinones such as:
  • Aldehydes such as:
  • Cinnamaldehyde formaldehyde, glutardialdehyde, ⁇ -bromocinnamaldehyde, o-phthaldialdehyde;
  • Benzalkonium chloride benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dichlorobenzyldimethyl-alkylammonium chloride,
  • Microbicides with activated halogen group such as:
  • the particular fungicide and / or algaecide-containing polymer matrix and their application media for example the plasters and paints produced therewith, have a broad biological activity against fungi and algae.
  • microorganisms of the following genus are mentioned:
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium such as Chaetomium globosum
  • Coniophora like Coniophora puetana,
  • Lentinus like Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila, - -
  • Trichoderma like Trichoderma viride
  • the algae to be controlled are preferably prokaryotic algae (cyanophyta / blue-green algae), e.g. Representatives from the subclass Coccogoneae and the subclass Hormogoneae, such as eukaryotic representatives from the departments Heteromonyphyta, Rhodophyta, Chlorophyta, Euglenophyta, Cryptophyta, Dinophyta and Haptophyta.
  • prokaryotic algae cyanophyta / blue-green algae
  • Representatives from the subclass Coccogoneae and the subclass Hormogoneae such as eukaryotic representatives from the departments Heteromonyphyta, Rhodophyta, Chlorophyta, Euglenophyta, Cryptophyta, Dinophyta and Haptophyta.
  • active ingredients are, in particular, the following fungicides and algicides: azaconazole, bromuconazole, cyproconazole, dichlobutrazole, diniconazole, hexaconazole, metaconazole, penconazole, propiconazole, tebuconazole, dichlofluanid, tolylfluanid, fluorolipet, methfuroxam, carboxin, benzo [b] thiophene-S , S-dioxide-carbonic acid cyclohexylamide, fenpiclonil, butenafine, imazalil, N-octylisothiazolin-3-one, dichloro-N-octylisothiazolinone, mercaptobenzothiazole, thiocyanatomethylthiobenzothiazole, thiabendazole, N-butylbenzisothiazolinone "1-hydroxy-2-
  • the preferred active ingredient content of the polymer matrix according to the invention is preferably from 5 to 80% by weight, in particular from 5 to 70% by weight and particularly preferably from 15 to 70% by weight.
  • the particles of the matrix according to the invention are characterized by an irregular shape, in particular with grooves and / or furrows, whereby the distribution of the active substance in the polymer matrix is largely uniform due to the extrusion.
  • the polymer matrix according to the invention particularly preferably has a VOC (volatile organic content) content of less than 1 wt .-%, in particular less than 100 ppm, particularly preferably of 10 ppm.
  • VOC volatile organic content
  • VOC volatile organic content
  • the polymer matrix according to the invention is characterized in that its content of polymer and biocidal active ingredient together is greater than 90% by weight, in particular greater than 95% by weight.
  • the invention further relates to a process for the preparation of the particulate polymer matrix according to the invention, which comprises
  • thermoplastic polymer a thermoplastic polymer and a biocidic agent
  • the mixing of polymer and biocidal active ingredient is preferably carried out by mixing active ingredient, the polymer preferably in granulated or powdered form and optionally other auxiliaries such as inorganic extenders, such as natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or Diatomaceous earth and ground synthetic minerals such as fumed silica, alumina and silicates, plasticizers and stabilizers.
  • auxiliaries such as inorganic extenders, such as natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or Diatomaceous earth and ground synthetic minerals such as fumed silica, alumina and silicates, plasticizers and stabilizers.
  • the extrusion in step b) preferably takes place in that, kneading the mixture of the thermoplastic polymer and the active substance at an elevated temperature, preferably 30 to 200 C brings 0 intimately contact each other and thus homogenized.
  • extruders are used which are usually designed as screw extruders but can also be piston extruders.
  • the screw extruders can be equipped with only one shaft or with a double shaft. They are fed through a hopper or other feeder with the mixture obtained in a). As the screw transports the solid mixture through the extruder, it is first heated and then homogenized and plasticized in the screw at elevated temperature. Subsequently, the extrudate is extruded through a nozzle in general as a strand from the extruder. Both single-screw and multi-screw extruders can be used for the extrusion.
  • the various temperatures occurring in the extruder can vary over a wide temperature range, generally the homogenization takes place in a range from 20 to 250 ° C. Depending on the polymer and active substance used, preference is given to working at a temperature of 30 to 200 ° C.
  • the contact times in the extruder, or the actual kneading times in the heated part of the extruder can vary within a very wide range. In general, the contact times are from 5 seconds to 5 minutes, preferably 10 seconds to 2 minutes.
  • one or more extruder passes are run.
  • the extrudate is usually obtained as strands, which are then comminuted by suitable means to the size of less than 100 microns.
  • suitable means to the size of less than 100 microns.
  • all mills can be used which are capable of sufficiently chopping the corresponding extrudate.
  • Shock, impact, pressure, friction or shear can be used here as the principles of comminution, in which case the grinding elements carry out rotating, oscillating, tumbling or reciprocating movements.
  • Mentioned here are, for example, ball mills, granulators, hammer mills and also jet mills, such as e.g. Fine impact mills, counter-jet mills, cross-flow mills or spiral jet mills.
  • Further mills are, for example, roller, tube, disc, toothed disk, oscillating bell spring-loaded, centrifugal-controlled or cross-beater mills.
  • the milling can also be carried out at reduced temperatures in order to achieve sufficient brittleness of the ground material.
  • a coolant here carbon dioxide, ice or liquid nitrogen can be used, or the mills are cooled by appropriate cooling units to the appropriate temperature.
  • the invention further relates to dispersions containing at least the particulate polymer matrix according to the invention.
  • dispersions and pastes are mentioned.
  • the dispersions are preferably aqueous dispersions.
  • the dispersions optionally contain surfactants, wetting agents, thickeners, defoamers, preservatives and stabilizers.
  • Optionally usable surfactants may be any surfactants or mixtures of surfactants normally used to prepare suspensions. Examples which may be mentioned here are: nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates.
  • the wetting agents used are preferably oligo- or polyalkylene glycols or triols, or ethers of the abovementioned compounds.
  • ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, glycerol or mono or di-methyl, ethyl, propyl or butyl ether of the abovementioned compounds are used.
  • defoamers surface-active compounds are generally used which are only slightly soluble in the surfactant solution. Preference is given to defoamers which are derived from natural fats and oils, petroleum derivatives or silicone oils.
  • the optionally usable stabilizers may be antioxidants, radical scavengers or UV absorbers. Optionally, one or more of these substances can be used.
  • novel dispersions can be prepared, for example, by grinding together the particulate polymer matrix and the other substances contained in the dispersion or intimately mixing them together by means of a dissolver.
  • the dispersions generally contain from 2 to 95% by weight of the particulate polymer matrix according to the invention, preferably from 5 to 75% by weight.
  • the invention further relates to solid formulations comprising, in addition to the particulate polymer matrix, solid extrudates such as e.g. ground natural minerals, such as kaolins, clays, talc, marble, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates.
  • solid extrudates such as e.g. ground natural minerals, such as kaolins, clays, talc, marble, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • ground synthetic minerals such as finely divided silica, alumina and silicates.
  • the formulations can be obtained by intimately mixing the particulate polymer matrix with the solid extenders or by co-grinding. You can also be obtained by drying, for example spray drying, a liquid solid mixture.
  • the solid formulations generally contain from 10 to 98% by weight of the particulate polymer matrix according to the invention, preferably from 15 to 85% by weight.
  • the formulations may additionally contain other substances such as stabilizers, container preservatives and other non-extruded fungicides or algicides.
  • the invention furthermore relates to the use of the particulate polymer matrix according to the invention or of the liquid or solid formulations according to the invention as microbiocidal agent for the protection of technical materials.
  • the technical materials are adhesives, glues, paper, cardboard, leather, wood, wood-based materials, wood-plastic composites, paints, coolants or heat transfer fluids.
  • the particulate polymer matrix can be incorporated directly or in the form of the dispersion or solid formulation according to the invention.
  • Emulsion paints are understood as meaning aqueous, alkali-based paints based on polymer dispersions which serve as binders.
  • the polymer dispersions used for the preparation of emulsion paints contain, by way of example and by way of preference, polyacrylates, styrene acrylates, polyvinyl acetate, polyvinyl propionate and the like. Polymers.
  • the application concentrations of the inventive particulate polymer matrix or dispersions or fetsen formulations to be used depend on the type and occurrence of the microorganisms to be controlled, and on the composition of the material to be protected. The optimum amount used can be determined by test series.
  • the finished inks in particular emulsion paints or plasters, generally contain from 0.001% by weight to 20% by weight, preferably from 0.01% by weight to 10% by weight, of the particulate polymer matrix according to the invention.
  • the mixture thus obtained was passed three times through an extruder (Buss, equipment type PLK 46 L), wherein the extrudate was cooled in each case on a cooling roller and mechanically comminuted for the next pass.
  • an extruder Buss, equipment type PLK 46 L
  • T1 50 ° C
  • T2 91 ° C
  • T3 88 ° C
  • Tl is the temperature at the end of the plasticization zone and at the beginning of the extrusion and homogenization zone
  • T2 is the temperature in the middle of the extrusion and homogenization zone
  • T3 is the temperature at the end of the extrusion and homogenization zone
  • the extrudates obtained were coarsely pre-crushed.
  • Example 2 The material was pre-shredded twice on a Bexmill (grated mill), ground with a LSM 100 (spiral jet mill) and the ground material was sieved through a Rhewum LPK 400 air-jet sieve with 45 ⁇ m mesh size.
  • the mixture thus obtained was added twice via an extruder (Buss, type PLK 46 L plant), wherein the extrudate was cooled in each case on a cooling roller and mechanically comminuted for the next pass.
  • an extruder Buss, type PLK 46 L plant
  • T1 48 ° C
  • T2 88 ° C
  • T3 84 ° C
  • T1 48 ° C
  • T2 88 ° C
  • T3 84 ° C
  • Tl is the temperature at the end of the plasticization zone and at the beginning of the extrusion and homogenization zone
  • T2 is the temperature in the middle of the extrusion and homogenization zone
  • T3 is the temperature at the end of the extrusion and homogenization zone
  • the extrudates obtained were coarsely pre-crushed.
  • the material was pre-shredded twice on a Bexmill (grated mill), ground with a LSM 100 (spiral jet mill) and the ground material was sieved through a Rhewum LPK 400 air-jet sieve with 45 ⁇ m mesh size.
  • the mixture thus obtained was added twice via an extruder (Buss, type PLK 46 L plant), wherein the extrudate was cooled in each case on a cooling roller and mechanically comminuted for the next pass.
  • an extruder Buss, type PLK 46 L plant
  • T3 88 ° C
  • T3 88 ° C
  • Tl is the temperature at the end of the plasticization zone and at the beginning of the extrusion and homogenization zone
  • T2 is the temperature in the middle of the extrusion and homogenization zone
  • T3 is the temperature at the end of the extrusion and homogenization zone
  • the extrudates obtained were coarsely pre-crushed.
  • the material was pre-shredded twice on a Bexmill (grated mill), ground with a LSM 100 (spiral jet mill) and the ground material was sieved through a Rhewum LPK 400 air-jet sieve with 45 ⁇ m mesh size.
  • Eudragid RS 100 copolymer of acrylic acid and methacrylic acid with a low proportion of quaternary ammonium groups, average molecular weight 150000
  • 256 g of thiabendazoles were weighed into a 2 1 glass bottle and mixed on a roller mixer.
  • the mixture thus obtained was added twice via an extruder (Buss, type PLK 46 L plant), wherein the extrudate was cooled in each case on a cooling roller and mechanically comminuted for the next pass.
  • an extruder Buss, type PLK 46 L plant
  • T1 111 0 C
  • T2 121 0 C
  • T3 128 0 C
  • T1 111 0 C
  • T2 121 0 C
  • T3 128 0 C
  • Tl is the temperature at the end of the plasticization zone and at the beginning of the extrusion and homogenization zone
  • T2 is the temperature in the middle of the extrusion and homogenization zone
  • T3 is the temperature at the end of the extrusion and homogenization zone

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne une matrice polymère particulaire qui contient une substance active biocide répartie de manière homogène dans la matrice polymère, caractérisée en ce que le polymère est un polymère thermoplastique. Selon l'invention, plus de 90 % de toutes les particules présentent une taille de particule inférieure à 100 µm, de préférence de 1 à 50 µm et la matrice polymère a une teneur en substance active de 2 à 80 % en poids.
EP08760849A 2007-06-22 2008-06-11 Polymères particulaires contenant une substance active biocide Withdrawn EP2170045A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007028923A DE102007028923A1 (de) 2007-06-22 2007-06-22 Biozodwirkstoff haltige partikuläre Polymere
PCT/EP2008/057298 WO2009000650A2 (fr) 2007-06-22 2008-06-11 Polymères particulaires contenant une substance active biocide

Publications (1)

Publication Number Publication Date
EP2170045A2 true EP2170045A2 (fr) 2010-04-07

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EP08760849A Withdrawn EP2170045A2 (fr) 2007-06-22 2008-06-11 Polymères particulaires contenant une substance active biocide

Country Status (7)

Country Link
US (1) US20100297204A1 (fr)
EP (1) EP2170045A2 (fr)
JP (1) JP5520821B2 (fr)
CN (1) CN101784187A (fr)
AU (1) AU2008267882B2 (fr)
DE (1) DE102007028923A1 (fr)
WO (1) WO2009000650A2 (fr)

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CN101784187A (zh) 2010-07-21
WO2009000650A2 (fr) 2008-12-31
US20100297204A1 (en) 2010-11-25
JP2010530860A (ja) 2010-09-16
AU2008267882A1 (en) 2008-12-31
AU2008267882B2 (en) 2015-01-15
JP5520821B2 (ja) 2014-06-11
DE102007028923A1 (de) 2008-12-24
WO2009000650A3 (fr) 2009-06-04

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