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WO2025125110A1 - Compositions contenant de la guanidine et du carbonate - Google Patents

Compositions contenant de la guanidine et du carbonate Download PDF

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Publication number
WO2025125110A1
WO2025125110A1 PCT/EP2024/085074 EP2024085074W WO2025125110A1 WO 2025125110 A1 WO2025125110 A1 WO 2025125110A1 EP 2024085074 W EP2024085074 W EP 2024085074W WO 2025125110 A1 WO2025125110 A1 WO 2025125110A1
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Prior art keywords
zinc
carbonate
guanidine
range
composition
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German (de)
English (en)
Inventor
Stefan APENBERG
Roman Grabbe
Thomas Wunder
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Thor GmbH
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Thor GmbH
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    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof

Definitions

  • the present invention relates to compositions, in particular aqueous compositions, which contain the components: (a) guanidine and/or at least one salt of unsubstituted guanidine and (b) one or more carbonate compounds selected from the group consisting of sodium bicarbonate, sodium carbonate, potassium bicarbonate, potassium carbonate, ammonium bicarbonate and ammonium carbonate.
  • the compositions are characterized in that the weight ratio of component (a) to component (b) is in the range from 1:14 to 54:1, the content of guanidine and carbonate in the total composition being used as the basis for determining the weight ratio.
  • the invention further relates to technical products which contain the compositions according to the invention, and to the use of the compositions for stabilizing aqueous technical products against microbial attack.
  • biocides are usually added to the products or even to their components.
  • This class of substances includes highly antimicrobially effective compounds with sometimes differing activity profiles. Synergistic combinations of different 3-isothiazolin-3-ones are often used to reduce the amount of biocide needed.
  • WO 99/08530 A1 proposes the combined use of methylisothiazolin-3-one and 1,2-benzisothiazolin-3-one.
  • biocides are the so-called alkylguanidinium salts and polyguanidinium salts.
  • medium- and long-chain guanidines and biguanidines such as cocospropylenediamine-1,5-bis-guanidinium acetate, bis(guanidinooctyl)amine triacetate, poly(hexamethylenebiguanidine) hydrochloride, di(4'-chlorophenyldiguanido)hexane, chlorhexidine digluconate, and chlorhexidine diacetate, exhibit antimicrobial activity.
  • OMYA INTERNATIONAL AG promotes a buffer system called Omyasmart Next Generation (OSNG) technology, which is intended to enable the long-term stability of water-based systems and biocide-free formulations against microbial attack.
  • This buffer system is the subject of International Patent Application WO 2022/223804 AL.
  • This discloses a buffer composition comprising a first and a second buffer component, wherein a) the first buffer component is at least one water-soluble or water-dispersible source of magnesium ions and/or zinc ions, and b) the second buffer component is at least one alkali carbonate and/or at least one alkali bicarbonate.
  • compositions or stabilized products that stabilize against microbial infestation, preferably without or with a reduced content of classic preservatives or biocides, such as isothiazolinones, bronopol and pyrithiones.
  • composition preferably an aqueous composition, containing the components:
  • NaHCCE
  • the composition is further characterized in that it contains component (a) in an amount in the range of 100 to 7,500 ppm, preferably in the range of 250 to 5,000 ppm, based on the amount of guanidine in the composition and component (b) in an amount in the range of 250 to 25,000 ppm, preferably in the range of 500 to 10,000 ppm, based on the amount of carbonate.
  • compositions according to the invention require significantly fewer, and in some cases even no, preservatives, as are conventionally included for preservation. Nevertheless, these compositions, or the products containing these compositions, are characterized by excellent resistance to microbial attack due to the surprisingly effective interaction of the guanidine or guanidine salt, component (a), and the at least one carbonate compound, component (b).
  • the compositions are characterized in that the weight ratio of components (a) to (b) is in the range from 1:14 to 54:1, preferably in the range from 1:8.6 to 21:1, particularly preferably in the range from 1:8 to 8:1 and very particularly preferably in the range from 1:3.4 to 1.6:1, wherein in determining the weight ratio, the content in relation to the guanidine and carbonate in the It has proven particularly advantageous within the scope of the invention if the weight ratio of (a) to (b) in the compositions according to the invention lies within the ranges specified above, since a synergistic interaction of the guanidine and the carbonate has been demonstrated within this range.
  • composition according to the invention contains, as component (a), guanidine and/or at least one salt of unsubstituted guanidine.
  • At least one salt in the context of the present invention means that the composition contains a single salt of guanidine or several, i.e., two, three, four, five, or more, salts of guanidine.
  • guanidine and/or a salt of unsubstituted guanidine means that the composition contains, as component (a), guanidine and/or optionally also one or more salts of unsubstituted guanidine.
  • the guanidine is the compound according to the following formula:
  • the composition according to the invention contains as component (a) guanidine hydrochloride and/or guanidine carbonate and/or guanidine hydrogen carbonate, according to a particularly preferred embodiment of the invention, the composition contains as component (a) guanidine carbonate.
  • the composition according to the invention contains one or more carbonate compounds selected from the group consisting of sodium hydrogen carbonate (NaHCCL), sodium carbonate (TSfeCCL), and
  • KHCO3 Potassium hydrogen carbonate
  • K2CO3 potassium carbonate
  • Ammonium bicarbonate (NH4HCO3) and ammonium carbonate ((NH ⁇ CCh). Multiple means that the composition can contain two, three, four, five or six of the carbonate compounds mentioned.
  • the composition contains sodium carbonate (Na2CO3) and/or sodium bicarbonate (NaHCCE) as component (b).
  • Na2CO3 sodium carbonate
  • NaHCCE sodium bicarbonate
  • both the amounts of components (a) and (b) and the weight ratios of components (a) and (b) to one another are stated. Unless otherwise stated, the amounts relate in each case to the lead structures, guanidine (CN3H5) as component (a), or to the lead structure of component (b), carbonate ( CO32 ). Likewise, when determining the stated weight ratios, the content in relation to guanidine, without taking into account any counterion, as component (a), and the content of carbonate, without taking into account any counterion, as component (b), in the composition are used as the basis.
  • the amount of component (a), guanidine and/or its salt contained in the composition according to the invention can vary over wide ranges and is generally in the range from 100 ppm to 10,000 ppm, preferably in the range from 250 ppm to 7,500 ppm and particularly preferably in the range from 250 ppm to 5,000 ppm, based on the amount of guanidine in the total composition.
  • the amount of component (b), the one or more carbonate compound(s), contained in the composition according to the invention can vary over wide ranges and is generally in the range from 100 ppm to 50,000 ppm, preferably in the range from 500 ppm to 25,000 ppm, particularly preferably in the range from 1,000 ppm to 10,000 ppm, based on the amount of carbonate.
  • the invention therefore relates, according to one embodiment, to a composition which is characterized in that it comprises the components:
  • component (b) in an amount in the range from 100 ppm to 50,000 ppm, preferably in the range from 500 to 25,000 ppm, particularly preferably in the range from 1,000 to 10,000 ppm, based on the amount of carbonate, wherein the weight ratio of component (a) to component (b) is in the range from 1:14 to 54:1, preferably in the range from 1:8.6 to 21:1, particularly preferably in the range from 1:8 to 8:1 and very particularly preferably in the range from 1:3.4 to 1.6:1, wherein the content in relation to the guanidine and carbonate in the entire composition is used as the basis for determining the weight ratio.
  • the pH of the composition according to the invention can vary over a wide range.
  • the composition is characterized in that it has a pH in the range of pH 8 to pH 12, preferably a pH in the range of pH 8.5 to 11.5, particularly preferably a pH in the Range of pH 9.0 to 11.0.
  • the pH value can be adjusted to the claimed range using methods familiar to the person skilled in the art.
  • the composition according to the invention is preferably an aqueous composition whose water content can vary widely. This is generally between 10 and 90% by weight, based on the total composition. According to one embodiment of the invention, the composition is characterized by having a water content of greater than 1% by weight, preferably greater than 10% by weight, particularly preferably greater than 20% by weight, based on the total composition.
  • the composition, in particular the aqueous composition, according to the present invention is generally a technical, in particular an aqueous technical product, selected from the group consisting of: paints, varnishes, glazes and plasters, fillers and fillers, primers, emulsions, latices, polymer dispersions, chalk slurries, mineral slurries, titanium dioxide slurries, ceramic masses, modeling clays, adhesives, glues, case-containing products, starch- and cellulose-containing products, concrete admixtures, lignin sulfonates, bitumen emulsions, surfactant solutions, fuels, detergents, cleaning agents, pigment pastes and pigment dispersions, wax emulsions, silicone emulsions, impregnating agents, release agents and lubricants, inks, lithographic fluids, thickeners and thickener preparations, rheology aids, cosmetic products, fragrances, toiletries, cooling water, water in circuits, water for humid
  • the composition according to the invention is an aqueous technical product selected from the group consisting of paints, varnishes, glazes, plasters, fillers and putties, pigment pastes and pigment dispersions, starch- and cellulose-containing products, thickeners and thickener preparations, mineral slurries, titanium dioxide slurries, ceramic masses, detergents and cleaning agents.
  • the composition is characterized in that it:
  • component (c) one or more zinc compounds selected from the group consisting of zinc oxide, zinc chloride, zinc sulfate, zinc phosphate, zinc carbonate, zinc hydroxycarbonate ([ZnCO3]2'[Zn(OH)2]3), zinc ascorbate, zinc hydroxide, zinc dehydroacetate and zinc carboxylate, wherein the weight ratio of component (a) to component (b) is in the range from 1:14 to 54:1, preferably in the range from 1:8.6 to 21:1, particularly preferably in the range from 1:8 to 8:1 and very particularly preferably in the range from 1:3.4 to 1.6:1, wherein the content in relation to the guanidine and carbonate in the entire composition is used as the basis for determining the weight ratio.
  • Component (c) is generally selected from the group consisting of zinc oxide, zinc chloride, zinc sulfate, zinc phosphate, zinc carbonate, zinc hydroxycarbonate ([ZnCO3]2' [Zn(OH)2]3), zinc ascorbate, zinc hydroxide, zinc dehydroacetate, and zinc carboxylate.
  • component (c) is selected from the group consisting of zinc oxide and zinc carbonate; according to a particularly preferred embodiment, component (c) is zinc oxide.
  • composition according to the invention according to this embodiment which further contains component (c), has the advantage that the at least one zinc compound, component (c), interacts synergistically with components (a) and (b), whereby the content of components (a), (b) and (c) in the composition can be further reduced while maintaining the stabilizing activity against microorganisms.
  • the weight ratio of components (a) to (c) can vary widely.
  • the composition according to the invention is characterized in that the weight ratio of (a) to (c) is in the range from 0.77:1 to 12:1, preferably in the range from 1:1 to 10:1, wherein the content of guanidine and zinc is used as the basis for determining the weight ratio.
  • the amount of component (c), the at least one zinc compound, contained in the composition according to the invention can vary over wide ranges and is in the range from 10 to 5,000 ppm, preferably in the range from 25 to 2,500 ppm, particularly preferably in the range from 50 to 1,000 ppm, in each case based on the content of zinc in the composition.
  • the composition is characterized in that it:
  • component (a) to component (b) Contains dichlorooctylisothiazolinone, bronopol, dibromonitrilopropionamide, iodopropynyl butylcarbamate, phenoxyethanol, dibromodicyanobutane and quaternary ammonium compounds, wherein the weight ratio of component (a) to component (b) is in the range from 1:14 to 54:1, preferably in the range from 1:8.6 to 21:1, particularly preferably in the range from 1:8 to 8:1 and very particularly preferably in the range from 1:3.4 to 1.6:1, wherein the content in relation to the guanidine and carbonate in the entire composition is used as the basis for determining the weight ratio.
  • the inventive composition according to this embodiment which further comprises component (d), has the advantage that the at least one compound selected from the group consisting of sodium pyrithione, zinc pyrithione, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, N-methyl-1,2-benzisothiazolin-3-one, benzisothiazolin-3-one, N-butyl-1,2-benzisothiazolin-3-one, octylisothiazolinone, dichlorooctylisothiazolinone, bronopol, dibromonitrilopropionamide, iodopropynyl butylcarbamate, phenoxyethanol, dibromodicyanobutane and quaternary ammonium compounds, interacts synergistically with component (a), whereby the content of components (a), (b), optionally (c) and (d), while maintaining the antimicrobial Effectiveness, in
  • the invention therefore relates to a particularly aqueous composition containing:
  • component (b) one or more carbonate compounds selected from the group consisting of sodium bicarbonate (NaHCCE), sodium carbonate (TS ⁇ CCh), potassium bicarbonate (KHCO3), potassium carbonate (K2CO3), ammonium bicarbonate (NH4HCO3) and ammonium carbonate ((NEL ⁇ CCh), characterized in that the weight ratio of component (a) to component (b) is in the range from 1:14 to 54:1, preferably in the range from 1:8.6 to 21:1, particularly preferably in the range from 1:8 to 8:1 and very particularly preferably in the range from 1:3.4 to 1.6:1, wherein the content in relation to the guanidine and carbonate in the entire composition is used as the basis for determining the weight ratio, and optionally:
  • component (d) contained in the composition according to the invention can vary widely. According to a preferred embodiment of the invention, the composition is characterized in that it contains, as component (d):
  • (dl) phenoxyethanol in an amount in the range of 100 to 10,000 ppm, preferably in an amount in the range of 250 to 7,500 ppm, particularly preferably in an amount in the range of 500 to 5,000 ppm and/or
  • (d2) one or more compounds selected from sodium pyrithione, zinc pyrithione, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, N-methyl-1,2-benzisothiazolin-3-one, l,2-benzisothiazolin-3-one, N-butyl-l,2-benzisothiazolin-3-one, octylisothiazolinone, dichlorooctylisothiazolinone, bronopol, dibromonitrilopropionamide, iodopropynyl butylcarbamate, dibromodicyanobutane and quaternary ammonium compounds in a total amount in the range of 1 to 2000 ppm, preferably in a total amount in the range of 1 to 1000 ppm and particularly preferably in a total amount in the range of 1 to 750 ppm.
  • the present invention further provides a process for preparing the preferably aqueous compositions according to the invention, comprising mixing the above-defined components (a), (b), optionally (c) and optionally (d).
  • the present invention relates to a concentrate containing components (a) and (b).
  • This concentrate is suitable for stabilizing technical products against microbial attack by incorporating a certain amount of the concentrate into the technical product to be stabilized against microbial attack.
  • the concentrate according to the invention is the composition defined above, which is characterized in that it contains components (a) and (b) in an amount in the range from 1 to 100% by weight, preferably in the range from 10 to 60% by weight, particularly preferably in the range from 20 to 40% by weight.
  • this embodiment relates to a concentrate for stabilizing technical compositions against microbial attack, containing:
  • component (b) one or more carbonate compounds selected from the group consisting of sodium bicarbonate (NaHCCE), sodium carbonate (TS ⁇ CCE), potassium bicarbonate (KHCO3), potassium carbonate (K2CO3), ammonium bicarbonate (NH4HCO3) and ammonium carbonate ((NH ⁇ CCE), characterized in that the weight ratio of component (a) to component (b) is in the range from 1:14 to 54:1, preferably in the range from 1:8.6 to 21:1, particularly preferably in the range from 1:8 to 8:1 and very particularly preferably in the range from 1:3.4 to 1.6:1, wherein in determining the weight ratio the content in Reference to the guanidine and carbonate in the entire composition, further characterized in that the concentrate contains components (a) and (b) in an amount in the range of 1 to 100 wt.%, preferably in the range of 10 to 60 wt.%, particularly preferably in the range of 20 to 40 wt.%.
  • NaHCCE sodium bicarbonate
  • the concentrate can be in the form of a powder mixture or as a liquid concentrate, for example as an aqueous concentrate.
  • the concentrate according to the invention comprises the following components:
  • aqueous concentrates (A) to (D) have proven to be particularly advantageous, having the following composition:
  • the concentrate according to the invention comprises the following components:
  • the concentrate according to the invention comprises the following components or consists of:
  • the concentrate according to the invention consists of the following components: 20.00 wt.% guanidinium carbonate, 2.05 wt.% sodium hydrogen carbonate and 100% water.
  • the composition is an aqueous technical product stabilized against microbial attack, which is selected from a paint, a plaster and a filler, comprising:
  • component (b) one or more carbonate compounds selected from the group consisting of sodium bicarbonate (NaHCCh), sodium carbonate (TS ⁇ CCh), potassium bicarbonate (KHCO3), potassium carbonate (K2CO3), ammonium bicarbonate (NH4HCO3) and ammonium carbonate ((NFL ⁇ CCh), characterized in that the weight ratio of component (a) to component (b) is in the range from 1:14 to 54:1, preferably in the range from 1:8.6 to 21:1, particularly preferably in the range from 1:8 to 8:1 and very particularly preferably in the range from 1:3.4 to 1.6:1, wherein the content in relation to the guanidine and carbonate in the entire composition is used as the basis for determining the weight ratio,
  • the aqueous technical product stabilized against microbial attack according to the invention which is a paint, plaster, or filler, requires significantly less, in some cases even none, of the preservatives typically contained in such products for in-container preservation due to its composition. Nevertheless, due to the surprisingly effective interaction of the guanidine or the guanidine salt and the carbonate compound(s), these products are characterized by excellent resistance to microbial attack, particularly during storage. As a result, the aforementioned technical products are significantly improved in terms of their environmental compatibility and furthermore exhibit all known properties related to good and safe processing characteristics.
  • the aqueous technical product which is a paint, a plaster or a filler, contains as component (a) guanidine hydrochloride and/or guanidine carbonate.
  • the aqueous technical product which is a paint, a plaster or a filler, contains sodium carbonate and/or sodium bicarbonate as component (b).
  • the pigments used can be the usual pigment admixtures of emulsion paints, such as titanium dioxide, iron oxide, chromium oxide, cobalt blue, phthalocyanine pigments, spinel pigments, as well as nickel and chromium titanates. Silicates, carbonates, fluorspar, sulfates, and oxides are preferred fillers in the composition.
  • the aqueous technical product which is a paint, plaster, or filler, generally contains 1 to 35% by weight, preferably 2 to 20% by weight, particularly preferably 3 to 12% by weight of polymer dispersion, calculated in each case as the solids content of the polymer dispersion.
  • the polymer dispersions contained in the coating composition can be any polymer dispersions known per se from the prior art in the field of coating or paint systems. The properties of the dispersion, as well as of the finished products produced from it, are predominantly determined by the respective polymer.
  • the polymer is composed of various building blocks, the so-called monomers, which can also be combined with one another depending on the desired property profile.
  • Suitable monomers are, for example, vinyl carboxylates having 3 to 20 carbon atoms, N-vinylpyrrolidone, vinyl aromatics, vinyl halides, ethylenically unsaturated carboxylic acids, their esters, their amides or their anhydrides, nanohybrid dispersions, water glass, silicone resin emulsions, aqueous polyurethane dispersions, styrene acrylates, a-olefins and/or 1,3-dienes in the form of aqueous polymer dispersions or water-redispersible polymer powders.
  • ethylenically unsaturated carboxylic acids is particularly preferred, in particular Acrylic and methacrylic acid, furthermore ethylenically unsaturated carboxylic acid esters, especially acrylic and methacrylic acid esters with 1 to 12 carbon atoms in the alcohol moiety.
  • the alcohol moiety of the esters can consist of linear or branched alkyl chains, cycloaliphatics, or aromatics, which can additionally be modified with hydroxyl groups, halogen atoms, or epoxy groups.
  • styrene and styrene derivatives is also particularly preferred.
  • the aqueous technical product which is a paint, plaster or filler, may contain additional additives such as dispersants, thickeners, stabilizers, defoamers and/or hydrophobic agents.
  • the aqueous technical product which is a paint, plaster, or filler, contains 100% water.
  • the water content can generally vary over a wide range and is at least 10% by weight, preferably at least 15% by weight, particularly preferably at least 20% by weight.
  • the aqueous technical product which is a paint, a plaster or a filler, is substantially free, preferably completely free, of preservatives selected from the group consisting of 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 1,2-benzisothiazolin-3-one, N-butyl-1,2-benzisothiazolin-3-one, N-methyl-1,2-benzisothiazolin-3-one, octylisothiazolinone, Diehl oroctylisothiazolinone,
  • the present invention also relates to the use of the compositions defined above, comprising the components:
  • component (b) one or more carbonate compounds selected from the group consisting of sodium bicarbonate, sodium carbonate, potassium bicarbonate, potassium carbonate, ammonium bicarbonate and ammonium carbonate, characterized in that the weight ratio of component (a) to component (b) is in the range from 1:14 to 54:1, preferably in the range from 1:8.6 to 21:1, particularly preferably in the range from 1:8 to 8:1 and very particularly preferably in the range from 1:3.4 to 1.6:1, the content in relation to the guanidine and carbonate in the entire composition being used as the basis for determining the weight ratio, for stabilizing aqueous technical products against microbial attack.
  • the weight ratio of component (a) to component (b) is in the range from 1:14 to 54:1, preferably in the range from 1:8.6 to 21:1, particularly preferably in the range from 1:8 to 8:1 and very particularly preferably in the range from 1:3.4 to 1.6:1, the content in relation to the guanidine and carbonate in the entire
  • aqueous products i.e., water-based products
  • these products are characterized by excellent resistance to microbial attack, especially during storage.
  • components (a) and (b) used during use can vary widely. According to one embodiment of the invention, components (a) and (b) are used or added to the total aqueous technical product in a total amount in the range from 0.05 wt.% to 10 wt.%, preferably in the range from 0.1 wt.% to 5 wt.%, particularly preferably in the range from 0.2 wt.% to 2.5 wt.%.
  • microtiter plates were incubated for 48 hours at 30 °C. After 48 hours, the samples were evaluated for turbidity due to growth, and the optical density was also determined photometrically. This allowed the minimum inhibitory concentrations (MICs) of the two substances to be determined individually and in combination.
  • MICs minimum inhibitory concentrations
  • the resulting synergism was numerically expressed by calculating the synergy index (SI). The calculation was carried out according to the standard method of F.C. Kull et al., Applied Microbiology, Vol. 9 (1961), p. 538.
  • QB Concentration of component B as sole agent If the synergy index is above 1, this means that antagonism exists. If the synergy index is above 1, this means that the effects of the two compounds are additive. If the synergy index is below 1, this means that the two compounds are synergistic.
  • Example 1 Investigation of the synergistic interaction between guanidine and sodium carbonate (IS ⁇ CCh). Calculation of the synergistic index of guanidine and sodium carbonate with respect to Pseudomonas spec. DSM 115322 during an incubation period of 48 hours at 30 °C.
  • QB Concentration of sodium carbonate as the sole agent showing an endpoint Table 1 shows that the optimal synergism, i.e., the lowest synergy index (0.57) of a composition of guanidine and sodium carbonate, is at a ratio of 1545 ppm guanidine to 2000 ppm sodium carbonate. Synergism can be demonstrated when the weight ratio of guanidine to sodium carbonate is in the range of 1:25 to 30:1, or, converted to the lead structures, the weight ratio of guanidine to carbonate is in the range of 1:14 to 54:1.
  • Qb Concentration of sodium bicarbonate in the mixture showing an endpoint
  • QB Concentration of sodium bicarbonate as the sole agent showing an endpoint
  • Table 2 shows that the optimal synergism, i.e., the lowest synergy index (0.82) of a composition of guanidine and sodium bicarbonate, is at a ratio of 618 ppm guanidine to 7500 ppm sodium bicarbonate. Synergism can be demonstrated when the weight ratio of guanidine to sodium bicarbonate is in the range of 1:12 to 15:1, or, converted to the lead structures, the weight ratio of guanidine to carbonate is in the range of 1:8.6 to 21:1.
  • Bacteria mixture 2 is Bacteria mixture 2:
  • the cell suspensions of the bacterial mixtures were prepared by culturing the individual bacteria for 24 hours at 30°C in liquid culture on a shaker.
  • a Müller-Hinton liquid medium served as the medium for the cultivation of bacteria from bacterial mixture 1.
  • Bacteria from bacterial mixture 2 were cultivated in a Müller-Hinton liquid medium, which had previously been adjusted to pH 9.5-9.7 with an alkaline buffer solution. After cultivation, the individual liquid cultures were centrifuged, and the cells resuspended in physiological saline. To adjust the mixture to a total cell count of 10 9 /ml, the individual bacterial suspensions were, if necessary, mixed with saline before combining. diluted. The cell count of the vaccine suspension was determined using the chamber counting method.
  • Example 3 a so-called repetitive challenge test was conducted by repeatedly inoculating the samples at specific intervals with a bacterial suspension containing a cell count of 10 9 /ml (2% v/w), and monitoring the development of the bacteria using a semi-quantitative assessment method. After each inoculation, the samples were incubated at 30°C for 6 days (bacterial mixture 1) or 7 and 14 days (bacterial mixture 2), and the bacterial contamination was semi-quantitatively assessed after these periods.
  • the resulting synergism was numerically represented by calculating the synergy index (SI). The calculation was also carried out in the following examples according to the standard method of F.C. Kull et al., Applied Microbiology, Vol. 9 (1961), p. 538.

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Abstract

La présente invention concerne des compositions, en particulier des compositions aqueuses, contenant les composants suivants : (a) de la guanidine et/ou au moins un sel de guanidine non substituée et (b) un ou plusieurs composés carbonates choisis dans le groupe constitué par hydrogénocarbonate de sodium, carbonate de sodium, hydrogénocarbonate de potassium, carbonate de potassium, hydrogénocarbonate d'ammonium et carbonate d'ammonium. Les compositions sont caractérisées en ce que le rapport en poids du composant (a) au composant (b) se trouve dans la plage allant de 1:14 à 54:1, la détermination du rapport en poids étant basée dans chaque cas sur la teneur relative à la guanidine et au carbonate dans la composition globale. L'invention concerne en outre des produits industriels contenant les compositions de l'invention, et l'utilisation des compositions pour la stabilisation de produits industriels aqueux contre une contamination microbienne.
PCT/EP2024/085074 2023-12-12 2024-12-06 Compositions contenant de la guanidine et du carbonate Pending WO2025125110A1 (fr)

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