EP1599568B1 - Hydrophile polyurethanschaumformkörper enthaltend einen antimikrobiellen wirkstoff - Google Patents

Hydrophile polyurethanschaumformkörper enthaltend einen antimikrobiellen wirkstoff Download PDF

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Publication number
EP1599568B1
EP1599568B1 EP04715941A EP04715941A EP1599568B1 EP 1599568 B1 EP1599568 B1 EP 1599568B1 EP 04715941 A EP04715941 A EP 04715941A EP 04715941 A EP04715941 A EP 04715941A EP 1599568 B1 EP1599568 B1 EP 1599568B1
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EP
European Patent Office
Prior art keywords
cleaning article
article
cleaning
quaternary ammonium
polyurethane composition
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.)
Expired - Lifetime
Application number
EP04715941A
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English (en)
French (fr)
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EP1599568A1 (de
Inventor
Farid Ahmad Reckitt Benckiser Inc. NEKMARD
Diane Joyce Burt
James Chi-Cheng Feng
Paul Hermann
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.)
Reckitt Benckiser LLC
HH Brown Shoe Technologies Inc
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Reckitt Benckiser LLC
HH Brown Shoe Technologies Inc
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Publication date
Priority claimed from GB0317198A external-priority patent/GB0317198D0/en
Priority claimed from GB0321869A external-priority patent/GB2406099A/en
Application filed by Reckitt Benckiser LLC, HH Brown Shoe Technologies Inc filed Critical Reckitt Benckiser LLC
Publication of EP1599568A1 publication Critical patent/EP1599568A1/de
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/04—Detergent materials or soaps characterised by their shape or physical properties combined with or containing other objects
    • C11D17/041—Compositions releasably affixed on a substrate or incorporated into a dispensing means
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/04—Detergent materials or soaps characterised by their shape or physical properties combined with or containing other objects
    • C11D17/049—Cleaning or scouring pads; Wipes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3726—Polyurethanes

Definitions

  • the present invention relates to articles having an antimicrobial benefit. More particularly the present invention relates to hydrophilic foam articles having an antimicrobial benefit.
  • cleaning articles which are used a number of times are used a breeding ground for undesirable bacteria and other microorganisms. Such include gram positive microorganisms as well as gram negative microorganisms.
  • the cleaning article indeed may be an incubator for such undesired microorganisms.
  • such cleaning articles are maintained in a moist state at a generally room temperature (approx. 20°C) environment, such typically are also suitable conditions for maintaining the viability of such microorganism.
  • room temperature approximately 20°C
  • the growth of the undesired micro-organisms increases the amount of these microorganisms which may come into contact with both the user, and with the surface to be treated upon the next use of the cleaning article.
  • US Patent 5091102 describes a substantially flexible dry matrix and the result and article capable of cleaning a surface by removing dust and/or organic film and rendering the surface substantially static-free, suitable for use as a garment, air filter or mat, wherein the dry matrix is uniformly coated with an amount of treatment solution sufficient to allow the matrix to retain its substantially dry characteristics, said treatment solution comprising between about 25% and 75% of at least one glycol compound, between about 0.2% and 60% of a cationic surfactant, an antimicrobial compound and optionally up to about 45% of a nonionic surfactant.
  • the foamed polyurethane composition may be used solely as hydrophilic foams providing an antimicrobial benefit, as well as in forming cleaning articles which may consist wholly of, or only partially of the foamed polyurethane composition which exhibits an antimicrobial benefit.
  • the polyurethane foam compositions of the invention is hydrophilic, and is capable of absorbing water, as well as containing and releasing a quaternary ammonium compound having germicidal properties.
  • the foamed polyurethane composition are advantageously formed of a polyurethane prepolymer composition which is used to form a foamed article, especially a foamed article having hydrophilic properties.
  • the selection of the polyurethane prepolymer is not critical and it is expected that any of a variety of known and commercially available polyurethane prepolymers may be used.
  • the hydrophilic polyurethane foam compositions of the present invention are prepared using an isocyanate-capped polyether prepolymer. Isocyanate-capped polyether prepolymers such as those disclosed in U.S. Pat. No. 4,137,200 are suitable for use in the present invention. These prepolymers have a defined average isocyanate functionality greater than 2.
  • the polyurethane prepolymer is foamed in the presence of an aqueous component, preferably water, in the conventional manner known in the art.
  • the aqueous component may also be a water slurry or suspension, a water emulsion, or a water solution having water soluble materials disposed therein.
  • the reaction mixture which contains at least the polyurethane prepolymer, and a quaternary ammonium compound having germicidal properties.
  • the reaction mixture typically contains further constituents which take part in reaction whereby the polyurethane foams which exhibit an antimicrobial benefit are formed.
  • the alkyl substituents may be long-chain alkyl, long-chain alkoxyaryl, long-chain alkylaryl, halogen-substituted long-chain alkylaryl, long-chain alkylphenoxyalkyl, arylalkyl, etc.
  • the remaining substituents on the nitrogen atoms other than the abovementioned alkyl substituents are hydrocarbons usually containing no more than 12 carbon atoms.
  • the substituents R 1 , R 2 , R 3 and R 4 may be straight-chained or may be branched, but are preferably straight-chained, and may include one or more amide, ether or ester linkages.
  • the counterion X may be any salt-forming anion which permits water solubility of the quaternary ammonium complex.
  • Exemplary quaternary ammonium salts within the above description include the alkyl ammonium halides such as cetyl trimethyl ammonium bromide, alkyl aryl ammonium halides such as octadecyl dimethyl benzyl ammonium bromide, N-alkyl pyridinium halides such as N-cetyl pyridinium bromide, and the like.
  • Particularly useful quaternary germicides include compositions which include a single quaternary compound, as well as mixtures of two or more different quaternary compounds.
  • Such useful quaternary compounds are available under the BARDAC®, BARQUAT®, HYAMINE®, LONZABAC®, and ONYXIDE® trademarks, which are more fully described in, for example, McCutcheon's Functional Materials (Vol. 2), North American Edition, 1998 , as well as the respective product literature from the suppliers identified below.
  • BTC® 65 is a commercially available preparation which is described to contain in 50%wt, of a C 12 -C 16 alkyl dimethyl benzyl ammonium chlorideprovided in an aqueous alcoholic carrier wherein water comprises 46%wt, of the commercial preparation, and ethanol comprises the remaining 4%wt, of the commercial preparation.
  • BTC® 2125M90 is a commercial available preparation which is described to contain 45%wt, of a C 12 -C 16 dimethyl benzyl ammonium chloride, 45%wt. of a C 12 -C 18 alkyldimethyl(ethylbenzyl) ammonium chloride, 4%wt. water, 3%wt. ethanol, and the remaining balance of 3%wt.
  • a further class of nonionic surfactants are primary and secondary linear and branched alcohol ethoxylates, such as those based on C 6 -C 18 alcohols which further include an average of from 2 to 80 moles of ethoxylation per mol of alcohol.
  • These examples include the Genapol® UD (ex.
  • nonionic surfactant constituent when present, may comprise two or more nonionic surfactants.
  • the nonionic surfactant is present in the compositions of the present invention in an amount of from about 0.1 % to about 10% by weight, more preferably is present in an amount of from about 1 -5%wt., and most preferably in an amount of from about 1-3.5%wt.
  • the lower alkanol of such alkanotammonium will normally be of 2 to 4 carbon atoms and is preferably ethanol.
  • R 1 is a C 12 - C 15 alkyl
  • n is from about 7 to about 13
  • M is an alkali metal counterion.
  • exemplary amphoteric surfactants include one or more water-soluble betaine surfactants which may be represented by the general formula: wherein: R 1 is an alkyl group containing from 8 to 18 carbon atoms, or the amido radical which may be represented by the following general formula: wherein R is an alkyl group having from 8 to 18 carbon atoms, a is an integer having a value of from 1 to 4 inclusive, and R 2 is a C 1 -C 4 alkylene group.
  • water-soluble betaine surfactants include dodecyl dimethyl betaine, as well as cocoamidopropylbetaine.
  • a further constituent which is optionally, but in certain cases desirably included in the foamed polyurethane compositions of the invention are one or more organic solvents which provides both a solvency function, as well as an anti-foaming function.
  • organic solvents can be virtually any organic solvent material.
  • silane compund also be included in the reaction mixture containing the polymer precursor.
  • the silanes are useful as coupling agents for the bulking agents, particularly where such bulking agents are minerals and thereby facilitate the incorporation of the bulking agents into the three dimensional structure of the polyurethane foams.
  • a cleaning article which exhibits an antimicrobial benefit
  • the foamed polyurethane article comprises at least one layer of a fibrous substrate bonded to a sponge formed from the foamed polyurethane composition, and preferably comprises a foamed polyurethane composition layer layered in register and between two fibrous substrate layers.
  • Nonwoven fibrous substrates may be a combination of wood pulp fibers and textile length synthetic fibers formed by well known dry-form or wet-lay processes. Synthetic fibers such as rayon, nylon, orlon and polyester as well as blends thereof can be employed, with or without fibers obtained from naturally occurring sources, e.g., wood pulp fibers, cellulose and the like. In certain embodiments, the wood pulp fibers should comprise about 30 to about 60 percent by weight of the nonwoven fabric, preferably about 55 to about 60 percent by weight, the remainder being synthetic fibers. The wood pulp fibers provide for absorbency, abrasion and soil retention whereas the synthetic fibers provide for substrate strength and resiliency.
  • Synthetic fibers such as rayon, nylon, orlon and polyester as well as blends thereof can be employed, with or without fibers obtained from naturally occurring sources, e.g., wood pulp fibers, cellulose and the like.
  • the wood pulp fibers should comprise about 30 to about 60 percent by weight of the nonwoven fabric, preferably about 55 to about 60 percent by weight
  • a particularly preferred embodiment of a cleaning article according to the invention is a multilayered cleaning article which comprises a layer of the foamed polyurethane composition providing an antimicrobial benefit layered in register and between two fibrous substrate layers, particularly where one of said fibrous substrate layers is constructed to provide an abrasive effect, while the other said fibrous substrate layer includes a quilted pattern.
  • Such an embodiment provides dual-function in that the abrasive layer may be used to improve the removal of soils or other materials on hard surfaces, while the opposite layer provides good water absorption and an attractive appearance. While any bonding means can be used, inter alia, stitching, adhesive, and the like, conveniently the two fibrous substrate layers are bonded to the intermediate polyurethane foam layer during the in-situ polymerization of the polyurethane foam.
  • the cleaning article would first be moistened with water or with any other cleaning composition and used to wipe the cutting board or cutting surface, thereafter it is contemplated that it would be rinsed in water, wrung to remove a majority of the water entrained within the sponge, and thereafter used to manually wash the dishes. Due to the rapid contact kill, most, if not all of the undesired micro-organisms which may come into contact from the cutting board or cutting surface and into the cleaning article would be destroyed or deactivated prior to coming into contact with the dishes to be manually washed particularly when the protocol of an intermediate rinsing step is practiced as outlined above.
  • a reaction mixture is formed from two components, the first component being the polyurethane prepolymer composition, e.g., HYPOL JT6000, and the second component being a premixture of the remaining constituents.
  • the second component was conveniently formed by combining its constituent in appropriate measured amounts in a standard laboratory glass beaker using conventional laboratory stirrer to ensure homogeneity of the second component.
  • test sponge was used to wipe the inoculated bottom of Plate I (Petri dish) for 2-3 seconds. This step represented a periodic challenge with a microbiological bioburden (viable test bacteria dried onto surfaces/carriers which are wiped.)
  • This sequence was repeated several times utilizing the same test sponge, so that the performance of a test sponge over a sequence of days, with 10 rinse/squeeze cycles performed on each assay day, could be evaluated.
  • the sequence was performed on sequential calendar days, as well as non-sequential calendar days where days were omitted, e.g., wherein the testing was not performed over two weekend days, but resumed during the following work week.
  • the number of survivors present on the plates were quantitated and the resulted recorded.
  • the results indicated below indicate the averaged results for the 3 replicates of the test sponges.
  • the sequence of the days is indicated in order of calendar days, which may not be sequential.
  • the results in the column indicated as "L” indicated the number of colonies of surviving Enterobacter aerogenes present on the plate (Plate 2) onto which the liquid was eluted from the test sponge
  • the results in the column indicated as "W” indicated the number of survivors present on the plate (Plate 3) which was wiped with the test sponge
  • the results in the column indicated as "R” indicated the number of survivors present on the plate (Plate R) which was wiped in order to assay the redeposition of Enterobacter aerogenes.
  • test sponges As can be seen from the foregoing, the tested cleaning articles (test sponges) produced according to the inventive teaching exhibited a good residual antimicrobial benefit is retained even after the cleaning article has been rinse/squeeze cycled a large number of times.
  • a multilayered cleaning article as depicted on Figures 2A and 2B comprising a layer of a foamed polyurethane composition according to the invention layered in register with a first abrasive fibrous substrate layer was produced.
  • the second component was conveniently formed by combining its constituents in appropriate measured amounts in a standard laboratory glass beaker using conventional laboratory stirrer to ensure homogeneity of the second component.
  • the second component is first formed by first providing the water to a suitable vessel, using a laboratory stirrer the Wollastonite 325 is added until a suspension is formed, followed by the Silquest 1120 which is allowed to mix approximately 10-20 minutes a homogenous mixture is attained, followed by the Tomadol 91-6, then Pluronic F88, then fragrance, then dye, followed by the Dowanol DPnB, and ultimately the BTC 65 and following the addition of the final constituent mixing is allowed to continue for further 20 minutes.
  • the quantity of eluted germicidal quaternary ammonium compounds were evaluated by a standard analytical technique via titration utilizing a tetraphenylborate solution. Of course other analytical techniques may be used and are expected to provide comparable results.
  • a sheet of a non-woven fibrous substrate material (Dexter® 10494 having a "quilted” surface) was applied to a flat laboratory benchtop. Subsequently a reaction mixture was formed from two components, the first component being the polyurethane prepolymer composition, e.g., HYPOL JT6000, and the second component being a premixture of the remaining constituents all of which are identified on Table 4, following.
  • the second component was conveniently formed by combining its constituents in appropriate measured amounts in a standard laboratory glass beaker using conventional laboratory stirrer to ensure homogeneity of the second component.
  • FIG. 3A , 3B and 3C A further embodiment of tri-layered cleaning article 30 is depicted on Figures 3A , 3B and 3C .
  • a foamed polyurethane layer 32 layered in register and between a first abrasive fibrous substrate layer 34 and a second fibrous substrate layer 36 comprising a quilted pattern having raised regions 38 bounded by recessed regions 40 which recessed regions are bonded to the foamed polyurethane layer 32 while the raised regions 38 are not.
  • Such a construction defines cavities 42 between the surface of the foamed polyurethane layer 32 and the raised regions 38, as bounded by the portion of the recessed regions 40 of the fibrous layer 36 not adhered to the foamed polyurethane layer.
  • the resultant tri-layered cleaning article formed was cut into a hexagonal shape measuring 5 inches in maximum width, and 6 inches in maximum height, and the ultimate thickness of the flexible wiping article was approximately 2-8 millimeter, as depicted on Figures 3A , 3B and 3C .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Detergent Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)
  • Materials For Medical Uses (AREA)

Claims (11)

  1. Hydrophile Polyurethanschaumzusammensetzung, umfassend:
    0,001-10 Gew.-% einer oder mehrerer quartärer Ammoniumverbindungen mit keimtötenden Eigenschaften, die im Allgemeinen in der gesamten Zusammensetzung verteilt sind,
    einen oberflächenaktiven Detergensbestandteil, bestehend aus einem oder mehreren nichtionischen, kationischen, zwitterionischen und amphoteren oberflächenaktiven Mitteln in einer Menge, die etwa 10 Gew.-% nicht übersteigt,
    wobei das nichtionische oberflächenaktive Mittel ausgewählt ist aus Polyalkylenoxidkondensaten von Alkylphenolen, Kondensationsprodukten von aliphatischen Alkohoolen mit 1 bis etwa 60 mol eines Alkylenoxids, primären und sekundären linearen und verzweigten Alkoholethoxylaten, Alkoxyblockcopolymeren, Alkylmonoglycosiden, Alkylpolyglycosiden und Aminoxiden,
    wobei die hydrophile Polyurethanschaumzusammensetzung eine Dichte von mindestens 0,25 g/cm3 aufweist,
    geformt durch ein Verfahren, das die folgenden Verfahrensschritte umfasst:
    Bereitstellen eines Reaktionsgemischs, umfassend mindestens ein Polyurethanpräpolymer, die quartäre Ammoniumverbindung mit keimtötenden Eigenschaften und den oberflächenaktiven Detergensbestandteil, bestehend aus einem oder mehreren nichtionischen, kationischen, zwitterionischen und amphoteren oberflächenaktiven Mitteln; und anschließend Formen der hydrophilen Polyurethanschaumzusammensetzung, die nach mindestens fünfundzwanzig (25) Spül-/Ausdrückzyklen eine Elution von mindestens etwa 100 parts per million, vorzugsweise mindestens etwa 150 parts per million an keimtötenden quartären Ammoniumverbindungen in dem aus dem Gegenstand ausgedrückten oder ausgewrungenen Fluid aufweist.
  2. Hydrophile Polyurethanschaumzusammensetzung nach Anspruch 1, die nach mindestens fünfzig (50) Spül-/Ausdrückzyklen eine Elution von mindestens etwa 200 parts per million an keimtötenden quartären Ammoniumverbindungen in dem aus dem Gegenstand ausgedrückten oder ausgewrungenen Fluid aufweist.
  3. Hydrophile Polyurethanschaumzusammensetzung nach Anspruch 1, die nach mindestens vierzig (40) Spül-/Ausdrückzyklen eine Elution von mindestens etwa 300 parts per million an keimtötenden quartären Ammoniumverbindungen in dem aus dem Gegenstand ausgedrückten oder ausgewrungenen Fluid aufweist.
  4. Reinigungsgegenstand, umfassend eine hydrophile Polyurethanschaumzusammensetzung nach einem der vorangehenden Ansprüche.
  5. Reinigungsgegenstand nach Anspruch 4, wobei der Reinigungsgegenstand mindestens eine Schicht aus einem faserartigen Substrat umfasst, das an einen aus der hydrophilen Polyurethanschaumzusammensetzung geformten Schwamm gebunden ist.
  6. Reinigungsgegenstand nach Anspruch 4, wobei der Reinigungsgegenstand mindestens zwei Schichten aus einem faserartigen Substrat umfasst, das an einen aus der hydrophilen Polyurethanschaumzusammensetzung geformten Schwamm gebunden ist.
  7. Reinigungsgegenstand nach einem der Ansprüche 4, 5 oder 6, der nach mindestens fünfzig (50) Spül-/Ausdrückzyklen eine Elution von mindestens etwa 200 parts per million der keimtötenden quartären Ammoniumverbindungen in dem aus dem Gegenstand ausgedrückten oder ausgewrungenen Fluid aufweist.
  8. Reinigungsgegenstand nach einem der Ansprüche 4 bis 7, wobei die maximale Dicke der in einem Reinigungsgegenstand vorliegenden Polyurethanschaumschicht ein Maß der maximalen Dicke nicht über 10 Millimeter aufweist, wobei der Reinigungsgegenstand nach mindestens zehn (10) Spül-/Ausdrückzyklen, vorzugsweise mindestens fünfundzwanzig (25) Spül-/Ausdrückzyklen eine Elution von mindestens etwa 200 parts per million an keimtötenden quartären Ammoniumverbindungen in dem aus dem Gegenstand ausgedrückten oder ausgewrungenen Fluid aufweist.
  9. Verfahren zum Reinigen und/oder Hygienisieren einer eine Behandlung benötigenden Oberfläche, wobei das Verfahren die folgenden Schritte einschließt:
    Bereitstellen eines Polyurethanschaumgegenstands nach einem der Ansprüche 1 bis 3 oder eines Reinigungsgegenstands nach einem der Ansprüche 4 bis 8 und Inkontaktbringen der Oberfläche mit dem hydrophilen Polyurethanschaumgegenstand derart, dass dafür eine reinigende und/oder hygienisierende Wirkung bereitgestellt wird.
  10. Verfahren zur Herstellung eines Reinigungsgegenstands nach einem der Ansprüche 4 bis 8, wobei das Verfahren die folgenden Schritte umfasst:
    Bereitstellen eines Reaktionsgemischs, umfassend mindestens ein Polyurethanpräpolymer, eine quartäre Ammoniumverbindung mit keimtötenden Eigenschaften und einen oberflächenaktiven Detergensbestandteil, und
    anschließend Formen der im Reinigungsgegenstand verwendeten hydrophilen Polyurethanschaumzusammensetzung
  11. Reinigungsgegenstand, hergestellt durch das Verfahren nach Anspruch 10.
EP04715941A 2003-03-05 2004-03-01 Hydrophile polyurethanschaumformkörper enthaltend einen antimikrobiellen wirkstoff Expired - Lifetime EP1599568B1 (de)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US45215003P 2003-03-05 2003-03-05
US452150P 2003-03-05
GB0317198 2003-07-23
GB0317198A GB0317198D0 (en) 2003-07-23 2003-07-23 Foam articles having an antimicrobial benefit
GB0321869A GB2406099A (en) 2003-09-18 2003-09-18 Foam articles having an antimicrobial benefit
GB0321869 2003-09-18
PCT/GB2004/000843 WO2004078900A1 (en) 2003-03-05 2004-03-01 Hydrophilic polyurethane foam articles comprising an antimicrobial compound

Publications (2)

Publication Number Publication Date
EP1599568A1 EP1599568A1 (de) 2005-11-30
EP1599568B1 true EP1599568B1 (de) 2009-01-21

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EP (1) EP1599568B1 (de)
AT (1) ATE421569T1 (de)
DE (1) DE602004019192D1 (de)
ES (1) ES2320766T3 (de)
WO (1) WO2004078900A1 (de)

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ES2320766T3 (es) 2009-05-28
EP1599568A1 (de) 2005-11-30
DE602004019192D1 (de) 2009-03-12
ATE421569T1 (de) 2009-02-15

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