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WO2019180041A1 - Stérilisant organique - Google Patents

Stérilisant organique Download PDF

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Publication number
WO2019180041A1
WO2019180041A1 PCT/EP2019/056880 EP2019056880W WO2019180041A1 WO 2019180041 A1 WO2019180041 A1 WO 2019180041A1 EP 2019056880 W EP2019056880 W EP 2019056880W WO 2019180041 A1 WO2019180041 A1 WO 2019180041A1
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WIPO (PCT)
Prior art keywords
amino acid
disinfecting agent
agent
polyglucosamine
disinfecting
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/EP2019/056880
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English (en)
Inventor
Sanjeev SWAMY
René GÄLLI
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.)
Livinguard AG
Original Assignee
Livinguard AG
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Filing date
Publication date
Application filed by Livinguard AG filed Critical Livinguard AG
Publication of WO2019180041A1 publication Critical patent/WO2019180041A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/227—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin with nitrogen-containing groups
    • 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
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • 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
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/33—Amino carboxylic acids
    • 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
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/12—Soft surfaces, e.g. textile
    • 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
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces

Definitions

  • the present invention relates to an organic disinfecting agent comprising at least one amino acid, at least one amino acid derivative and/or at least one iminosugar, and polyglucosamine.
  • the disinfecting agent can be used for sanitizing surfaces or can be applied in combination with cleaning agents, such as detergents.
  • Disinfectants are extensively used in everyday life to prevent microbial spread and microbial infections, such as in the health care sector, the food industry, agriculture, or in common household products.
  • disinfectants are provided in solution and applied directly onto contaminated surfaces, such as in hospitals or of laboratoiy equipment, or skin wounds. In case these disinfectants are not neutralized, such as by autoclaving, or cannot be easily
  • an antimicrobial agent which comprises environmentally friendly chemical agents.
  • the agents are preferably natural, organic compounds. Such compounds are usually biodegradable, thereby reducing the risk of accumulation and contamination of the environment.
  • the agents should be well tolerated by living tissues and could be used, for example, for sensitive applications such as preservative for food, as wound sanitizing agent or in combination with cleaning agents, for example detergents used in laundry machines.
  • the production of such antimicrobial agents should be cost-efficient, in particular in terms of the costs for the chemical agents used.
  • the present invention solves the shortcomings of the state of the art by providing in a 1 st embodiment of the invention a disinfecting agent comprising
  • At least one amino acid at least one amino acid derivative, and/or at least one iminosugar, or
  • the inventors have found that common amino acids, peptides and quaternaiy ammonium comprising amino acid derivatives, or iminosugars can be combined with polyglucosamine (chitosan) to achieve a high antimicrobial activity.
  • the at least one amino acid, amino acid derivative, iminosugar and/or polyglucosamine each carries at least one positive charge. Such positive charges are believed to adhere to the negatively charged membranes of microorganisms and to disrupt the membrane integrity, thereby acting biocidal.
  • At most 1%, preferably at most 0.8%, more preferably at most 0.1% of the amine groups of polyglucosamine are functionalized with the at least one amino acid, and/or amino acid derivative.
  • the polyglucosamine is non-animal derived.
  • non-animal derived polyglucosamine can be isolated from fungi, such as mucorales.
  • the at least one amino acid is selected from the group consisting of natural amino acid, unnatural amino acid, non-proteinogenic amino acid, and/or wherein the at least one amino acid derivative is selected from the group consisting of peptide and quatemaiy ammonium comprising amino acid derivative.
  • the amino acid and/or amino acid derivative has an isoelectric point equal to or above 7, preferably equal to or above 8, more preferably equal to or above 8.5, and/or has a pH- independent positive charge.
  • amino acids and/or amino acid derivatives with an isoelectric point above 7 allows that the acids and/or amino acid derivatives carry a positive net charge at any pH value below the isoelectric point. Thus, the higher the isoelectric point, the larger is the range of pH values suitable for providing a positive net charge.
  • amino acids or amino acid derivatives such as quatemaiy ammonium comprising amino acid derivatives, may have a constant positive charge, which is pH independent. It has been found that a positive charge of the amino acid and/or amino acid derivative applied to the textile enhances the overall antimicrobial activity, in particular against gram-positive and gram-negative bacteria. Positive charges are believed to adhere to the negatively charged membranes of microorganisms and to disrupt the membrane integrity, thereby acting biocidal.
  • the natural, unnatural or non-proteinogenic amino acid is in L configuration, and/or wherein the peptide is an L-peptide.
  • the L-enantiomers of amino acids and peptides can be easily obtained from cultures, e.g. of E. coli, L. lactis or S. cerevisiae, rendering a complicated, cost-inefficient chemical synthesis unnecüy.
  • the amino acid is lysine, arginine, or histidine, preferably arginine.
  • amino acids lysine, arginine, or histidine are environmentally friendly, as they can be obtained from common biological cultures. Moreover, these amino acids can be used as food additives or preservatives in the food industry, as they are non-toxic to living tissues. Arginine is one of the preferred amino acids because it is available at comparatively low costs.
  • the peptide is a dipeptide or a polypeptide, preferably wherein the polypeptide contains 3 to 50 amino acids.
  • the amino acid derivative is a lantibiotic, preferably wherein the amino acid derivative is nisin.
  • Nisin is commonly used as a food preservative, and, thus, can be also used for sanitizing packages or other products in the food industry.
  • the iminosugar is D-fagomine.
  • the amino acid derivative is carnitine or betaine.
  • Carnitine in particular L-carnitine
  • betaine are naturally occurring amino acid derivatives, which comprise quaternary ammonium groups that are positively charged in a pH-independent manner.
  • carnitine has proven to have an adequate antimicrobial activity in combination with polyglucosamine.
  • the disinfecting agent comprises arginine and carnitine.
  • arginine and carnitine confers a particularly high antimicrobial activity, e.g. against both gram-negative and gram-positive bacteria.
  • polyglucosamine is essentially free of thiol groups.
  • Essentially free of certain groups or compounds in the context of the present invention means that the respective groups or compounds are comprised only as usual impurities, i.e. they are not added to the formulations of the present invention and/or the formulations of the present invention are not derivatized with the groups.
  • the disinfecting agent comprises at most 1.8%, preferably at most 1%, more preferably at most 0.5% of trehalose, most preferably at most 0.1% trehalose. In a most preferred embodiment, the disinfecting agent is essentially free of trehalose.
  • the disinfecting agent is a solution or suspension.
  • the disinfecting agent of any one of the preceding embodiments comprises at most 10%, preferably at most 5%, more preferably at most 2%, more preferably at most 1%, most preferably at most 0.5% of an organic solvent, based on the total amount of solvent.
  • the organic solvents ethanol or isopropanol can be comprised in very low amounts, or the disinfecting solution can be essentially free of organic solvents, such as ethanol or isopropanol. Thereby, the disinfecting solution can be well tolerated during use, e.g. for cleaning the human skin.
  • the disinfecting agent comprises water as a solvent.
  • the water is the main solvent of the disinfecting agent.
  • the disinfecting agent can be prepared using mainly water as solvent, i.e. more than 50% of the solvent can be water. Preferably water is the only solvent in the disinfecting agent.
  • the disinfecting agent has a pH between pH 4 and pH 12, more preferably to between pH 6 and pH 11.5, even further preferably between pH 8 and pH 11, most preferably between pH 9 and pH
  • a basic pH of the disinfecting agent improves the overall antimicrobial activity.
  • the disinfecting agent is in particular effective in its anti- microbial activity when the pH is adjusted to the indicated pH range and in particular to the indicated basic pH range.
  • the disinfecting agent is a powder.
  • the disinfecting agent comprises at most 10%, preferably at most 5%, more preferably at most 2%, further preferably at most 1%, most preferably at most 0.5% of a lyophilisate of polyglucosamine, based on the total weight of chitosan comprised in the disinfection agent.
  • the disinfecting agent is essentially free of a lyophilisate of polyglucosamine.
  • the polyglucosamine is provided in water-soluble form.
  • a water-soluble form of polyglucosamine can be provided by dissolving a powder or flakes comprising polyglucosamine in an acidic medium. By using a water-soluble form in the liquor, polyglucosamine can be well dispersed.
  • the mass ratio between the amino acid or the amino acid derivative and polyglucosamine is between 0.25:1 and 5:1, preferably between 0.5:1 and 3:1, more preferably between 1:1 and 2:1.
  • polyglucosamine is between 2:1 and 5:1, preferably between 3:1 and 4:1.
  • the disinfecting agent further comprises one, two, three, or all four antimicrobial agents selected from the group consisting of propiconazole, silver ions, polyhexamethylene biguanide, quaternary ammonium organosilane.
  • antimicrobial agents are not biodegradable. In certain applications it may nevertheless be desirable to add them because they increase the overall antimicrobial activity of the disinfecting agent.
  • the inventors found that these antimicrobial agents can be well combined with amino acids and/or amino acid derivatives, and
  • quatemaiy ammonium organosilane is a hydrophilic quaternary ammonium organosilane, preferably an organomethoxysilane compound, more preferably N- trimethoxysilylpropyl-n,n,n-trimethylammonium chloride.
  • the disinfecting agent comprises at least one organic acid, preferably selected from the group consisting of acetic acid, citric acid, lactic acid, formic acid and p-toluenesulfonic acid.
  • the disinfecting agent comprises:
  • the disinfecting agent comprises the polyglucosamine or a salt thereof in an amount of 0,5% to 10%, preferably, 1% to 8%, more preferably 2,5% to 7%, most preferably 5%.
  • the disinfecting comprises the organic acid or a salt thereof in an amount of 0,5% to 20%, preferably,
  • the organic acid is citric acid
  • At least 90%, preferably at least 95%, more preferably at least 98%, even more preferably at least 99%, further preferably at most 99.9%, and most preferably about 100% of the disinfecting agent is made from a renewable raw material, and/or is biodegradable and/or natural and organic.
  • the present invention is directed to a cleaning agent, such as a detergent, dish-washing detergent, or rinsing agent, comprising the agent of any one of the 1 st to 32 nd embodiment.
  • a cleaning agent such as a detergent, dish-washing detergent, or rinsing agent
  • the cleaning agent comprises linear alkyl benzene sulphonate, linear alkyl benzene, a non-ionic tenside and/or an anionic tenside.
  • the cleaning agent comprises soap, glycerine, fats, and other components generally added to soaps.
  • the present invention is directed to a method for the preparation of a disinfecting agent according to any one of embodiments 1 to 32, comprising mixing the at least one amino acid, the at least one amino acid derivative and/or the at least one iminosugar in powder or liquid form and polyglucosamine in powder or liquid form.
  • At most 3%, preferably at most 2%, more preferably at most 1%, most preferably at most 0.5% of the at least one amino acid, amino acid derivative and/or polyglucosamine are activated with a cross- linking reagent, in particular with a carbodiimide and/or a N-hydroxysuccinimide.
  • a cross- linking reagent in particular with a carbodiimide and/or a N-hydroxysuccinimide.
  • polyglucosamine are essentially free of a crosslinking reagent, in particular with a carbodiimide and/or a N-hydroxysuccinimide.
  • the at least one amino acid, amino acid derivative and/or imino sugar and polyglucosamine are mixed in a solvent, preferably water, to form a solution or suspension, preferably wherein the pH of the solution of suspension is adjusted to between pH 4 and pH 12, more preferably to between pH 6 and pH 11.5, even further preferably between pH 8 and pH 11, most preferably between pH 9 and pH 10.5.
  • the solution or suspension is stirred for at least 10 minutes, preferably at least 20 minutes, more preferably at least 30 minutes, at a temperature of at least 30 °C, preferably at least 40 °C, more preferably at least 50°C, and/or at a temperature of at most 70 °C, preferably at most 60 °C, more preferably at most 55°C.
  • the stirring/incubation step allows for a further increase in antimicrobial activity.
  • the inventors believe that during incubation, polyglucosamine molecules react with the amino acid and/or amino acid derivate, such that an ester bond is formed.
  • a temperature of the reaction mixture of at least 30 °C, more preferably at least 40 °C, even more preferably at least 50 °C, was found to foster the reaction in the incubation step.
  • the present invention is directed to a method for the reduction of microbial contamination in a liquid, comprising applying to the liquid the disinfecting agent according to any one of embodiments 1 to 32 or the cleaning agent according to any one of embodiments 33 to 35.
  • the disinfecting agent or the cleaning agent is added into a washing machine in the course of a laundry cycle for washing one or more textile products.
  • the disinfecting agent or the cleaning agent is added together with a washing detergent into the washing machine, preferably wherein the disinfecting solution is comprised in the washing detergent.
  • the disinfecting agent or the cleaning agent is added into the washing machine at a rinsing step, such that the disinfecting solution remains partially adhered to the one or more textile products at the end of the laundry cycle.
  • the disinfecting agent or the cleaning agent is applied to the liquid, such that the liquid comprises 0.001 to 1% by weight, preferably 0.002 to 0.5% by weight polyglucosamine,
  • O.001 to 1% by weight preferably 0.01 to 0.5% by weight the amino acid, 0.001 to 1% by weight, preferably 0.01 to 0.5% by weight the amino acid derivative, and/or 0.001 to 1% by weight, preferably 0.002 to 0.5% by weight the iminosugar.
  • the reduction of antimicrobial contamination in the liquid is at least 90%, preferably at least 99%, more preferably at least 99.9%, most preferably at least 99.99%, when measured in accordance with the ASTME-2149 test method against
  • P. aeruginosa Staphylococcus aureus and/or E. coli.
  • the present invention is directed to a method of sanitizing a surface, in particular a surface contaminated with microbes, comprising applying to the surface a disinfecting agent according to any one of embodiments l to 32 or a cleaning agent according to any one of embodiments 33 to 35.
  • the disinfecting agent or cleaning agent is applied to the surface in the course of cleaning the surface, in particular by wiping, rinsing, or mopping and/or with the help of a wipe, towel, or mop.
  • the surface is living human or animal skin, preferably skin of the human hand or face, or the surface is a floor, a kitchen top, a table, a medical device, furniture, in particular in an operating theater or emergency room, a door handle, a dish, cutlery, a steering wheel, a keyboard, bathroom surface, vehicle surface, a surface in a restaurant or hotel, a wall, or an electrical consumer product.
  • the disinfecting agent is applied such that 0.001 to 1% by weight, preferably 0.01 to 0.5% by weight polyglucosamine, 0.0002 to 1% by weight, preferably 0.01 to 0.5% by weight the amino acid, 0.001 to 1% by weight, preferably 0.01 to 0.5% by weight the amino acid derivative, and/or 0.001 to 1% by weight, preferably 0.002 to 0.5% by weight the iminosugar are applied to the surface.
  • the reduction of antimicrobial contamination on the surface is at least 90%, preferably at least 99%, more preferably at least 99.9%, when measured in accordance with the ASTME-2149 test method against P. aeruginosa, Staphylococcus aureus and/or E. coli.
  • antimicrobial as used in the context of the present invention relates to the ability to kill at least some types of microorganisms, or to inhibit the growth or reproduction of at least some types of microorganisms. Said term relates to any compound, agent, product or process that is harmful to one or more "microorganism” as used in the context of the present invention. Preferably, the one or more "microorganism” gets killed by the "antimicrobial” product or process.
  • antimicrobial agent means any chemical compound that acts antimicrobial against at least some types of microorganisms.
  • Exemplaiy antimicrobial agents are chitosan, quaternaiy ammonium organosilane, silver cations, polyhexamethylene biguanide (PHMB), propiconazole, amino acids, amino acid derivatives, and iminosugars.
  • microorganism and“microbe”, which are used interchangeably in the context of the present invention, are defined to comprise any organism too small to be seen by the unaided eye, such as, especially, single-celled organisms.
  • microorganism and microbe cover prokaryotes including bacteria and archaea, eukaiyotes including protists, animals like dust mites or spider mites, fungi, and plants like green algae, as well as viruses.
  • biodegradable refers to any form of textile, amino acid, amino acid derivative, chitosan, antimicrobial agent or other chemical compounds, which can be decomposed by living cells, such as bacteria.
  • natural and organic refers to organic compounds that may by produced by living organisms.
  • all amino acids that are synthesized by biological cells or chitosan are natural and organic compounds.
  • the present invention relates to a natural and organic disinfecting agent.
  • the agent comprises naturally occurring functional agents, such as amino acids or peptides, in combination with chitosan.
  • the disinfecting agent is environmentally friendly, as the antimicrobial agents, such as natural amino acids, are biodegradable.
  • the use of amino acids and/or amino acid derivatives as antimicrobial agents lowers the production costs for the production of the antimicrobial agent, e.g. in comparison to antimicrobial agents comprising chitosan only.
  • the antimicrobial agent comprises at least one amino acid, amino acid derivative and/or iminosugar, and chitosan.
  • Both the amino acid and the amino acid derivative contain at least two functional groups, one of them being a carboxy group, and the other one being an amine group or quaternary amine group. Unless otherwise indicated, the carboxy group and the amino group are not derivatized, e.g. with crosslinking agents.
  • the amino acid may be an alpha- amino acid, as represented by the following structural formula:
  • the amino acid may be a beta-, gamma- or delta-amino acid.
  • the exemplaiy proteinogenic amino acid L-arginine is represented by the following structural formula:
  • the exemplaiy non-proteinogenic amino acid derivative L-camitine is represented by the following structural formula:
  • Chitosan has a structure as shown hereinafter, wherein n indicates the number of monomer units as known in the art:
  • Nisin is a lantibiotic with the following structure:
  • D-fagomine is a iminosugar with the following structure:
  • R’-COOH groups of amino acids and/or amino acid derivatives may react with R”-OH groups of chitosan by forming an ester bond R’-COO-R’.
  • Antimicrobial performance of disinfecting agents according to the invention were performed following the ASTME-2149 test method.
  • test bacteria E . coli, S. aureus, P. aeruginosa
  • the buffer further comprised a detergent as indicated.
  • 5 m ⁇ to 2.5 ml of the antimicrobial agent were added to obtain the total test volume, and the flasks were shaken for 1 hour.
  • 0.3% bovine serum albumin (BSA) was added to the flasks, as indicated in the examples. After incubation, the log reduction over the initial time point was determined.
  • BSA bovine serum albumin
  • the Log Reduction (R) of bacteria was calculated by:
  • L-arginine is known in the art and commercially available, e.g. by Sciencelab. In the following examples, L-arginine is provided as a powder with 100% by weight.
  • L-carnitine was provided by Lonza Specialty Chemicals Switzerland as a powder with > 98% by weight.
  • Propiconazole is known in the art and commercially available, e.g. Utconazol
  • Propiconazole can be bound to the textile material using a crosslinking agent, in particular a preferably blocked isocyanate compound, which results in urethane bonds, or an acrylate based-product.
  • a crosslinking agent in particular a preferably blocked isocyanate compound, which results in urethane bonds, or an acrylate based-product.
  • propiconazole it is preferred to use a crosslinking agent in the liquor, in particular the exhaust liquor. It is even more preferred that the formulation of propiconazole contains the cross linking agent or the cross-linking agent is part of the propiconazole formulation.
  • propiconazol Utpan Chempro
  • the quaternary ammonium organosilane can comprise an organomethoxysilane, preferably N-trimethoxysilylpropyl-N,N,N-trimethylammonium chloride, as provided by Gelest Inc. as a 50% stock solution.
  • Polyhexamethylene biguanide is known in the art and commercially available. In the following examples, polyhexamethylene biguanide (PHMB, Thor GmbH) was provided as a 20% stock solution.
  • PHMB polyhexamethylene biguanide
  • An antimicrobial agent can comprise silver cations.
  • the silver cations are trapped in an inorganic or organic matrix.
  • the inorganic matrix is an aluminosilicate.
  • the organic matrix is a polymeric matrix.
  • Such silver- containing microbial agents are known in the art and available on the market.
  • Silvadur 930 Flex (0.1% silver cations trapped in a polymeric matrix) was provided by Dow Chemical Company.
  • As a cross-linker blocked polyisocyanate, e.g. oxime- blocked polyisocyanate, can be used. Oxime-blocked polyisocyanate is, for example, provided by Schoeller Technologies AG.
  • a disinfecting agent according to the invention was prepared by mixing
  • the disinfecting agent was added to 51 ml cell culture in PBS and tested according to ASTME-2149, as described above, with test parameters as compiled in Table 1.
  • concentrations of the antimicrobial agent of at least 0.5% confer high antimicrobial activity of at least log 4, i.e. > 99.99% bacterial reduction.
  • concentrations of the disinfecting agent in a concentration of between 0.5% and 1% is also of economic interest, as the costs for the production and application are reasonable.
  • the disinfecting agent can be combined with a nonionic detergent, such as Triton X-ioo (Octoxynol 9), e.g. in a cleaning agent.
  • a nonionic detergent such as Triton X-ioo (Octoxynol 9)
  • a disinfecting agent according to the invention was prepared by mixing
  • the pH of the mixture was adjusted, as specified in the following table 2.
  • the mixture was stirred for 10 minutes at room temperature or 50 °C, as indicated below, to obtain the disinfecting agents.
  • Each disinfecting agent was added to 101 ml cell culture in PBS and tested according to the ASTME 2149 test method as described above.
  • the total test volume further comprised 0.3% BSA and 0.15% of the detergent“Surf Excel Quickwash powder”.
  • Surf Excel comprises anionic detergents.
  • the disinfecting agents 1 to 7 applied in a concentration of about 0.5% have a particularly high antimicrobial activity of more than log 5 (>99-999 reduction) against the gram-positive bacterium S. aureus, even in combination with the anionic washing detergent Surf Excel.
  • the antimicrobial activity of the disinfecting agent was tested with respect to the pH of the disinfecting agent.
  • the ASTME 2149 test was conducted as described in the following table 4.
  • the antimicrobial performance was increased, in particular against E. coli, if the pH of the disinfecting agent was basic, cf. Sample ID 8.
  • the improved activity of the disinfecting agent at basic pH values even outcompetes a increases concentration of the disinfecting agent at a lower pH value.
  • antimicrobial agents were also tested according to the ASTME 2149 test method as described above, using no detergent in the test flasks, as summarized in Table 5.
  • the disinfecting agents 1 to 7 confer a high protection against gram-positive and gram-negative bacteria.
  • a disinfecting agent according to the invention was prepared by mixing
  • antimicrobial agents were also tested according to the ASTME 2149 test method as described above, using Triton X-100 in the test flasks, as summarized in Table 7.
  • the improved activity of the disinfecting agent at basic pH values was confirmed also when used in combination with the nonionic detergent Triton X-100.
  • the disinfecting agent of Sample ID 9 of table 6 at a pH of 10.44 was compared to the same agent but at a pH of 4.87 (Sample ID 10).
  • the activity of the disinfecting agent at a pH 10.44 increased for E. coli from log 1.78 to 6.02 and for S. aureus still from 3.14 to 5.34.
  • Disinfecting agents according to the invention comprising chitosan and an organic acid such as citric acid, lactic acid or acetic acid were prepared and tested according to the ASTM-E2149 test method as described above, as summarized in Table 8.
  • Table 8 Antimicrobial performance of samples l to 4 comprising chitosan and an organic acid.

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Abstract

L'invention concerne un stérilisant comprenant : au moins un acide aminé; au moins un dérivé d'acide aminé et/ou au moins un iminosucre ou un sel de celui-ci; ou un polyglucosamine ou un sel de celui-ci. Elle concerne un agent nettoyant, un détergent, un détergent pour la vaisselle, ou un agent de rinçage, comprenant le stérilisant. L'invention concerne un procédé de préparation d'un stérilisant, qui consiste à mélanger le ou les acides aminés, le ou les dérivés d'acides aminés et/ou le ou les iminosucres sous forme de poudre ou de liquide et le polyglucosamine sous forme de poudre ou de liquide. L'invention concerne également un procédé de réduction de la contamination microbienne dans un liquide, qui consiste à appliquer sur le liquide le stérilisant ou l'agent nettoyant. L'invention concerne en outre un procédé de désinfection d'une surface, en particulier une surface contaminée par des microbes, qui consiste à appliquer sur la surface un stérilisant ou un agent nettoyant.
PCT/EP2019/056880 2018-03-19 2019-03-19 Stérilisant organique Ceased WO2019180041A1 (fr)

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EP18162645.8A EP3543325A1 (fr) 2018-03-19 2018-03-19 Agent de désinfection organique
EP18162645.8 2018-03-19

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WO2019180041A1 true WO2019180041A1 (fr) 2019-09-26

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WO2023012809A1 (fr) * 2021-08-05 2023-02-09 Prerna Goradia Formulation désinfectante de surface

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