Antimicrobial synergies
Patent Information
- Authority / Receiving Office
- EP · EP
- Patent Type
- Applications
- Current Assignee / Owner
- SYMRISE GMBH & CO KG
- Filing Date
- 2024-07-09
- Publication Date
- 2026-05-20
AI Technical Summary
Current antimicrobial agents in personal care, pharmaceutical, and household products may induce undesirable side effects and require high concentrations to be effective, while also facing challenges in providing synergistic antimicrobial activity against a range of pathogens.
A mixture comprising compounds of formula (I) or (II) in combination with further antimicrobial agents, where the compounds synergistically enhance or improve the antimicrobial effect, reducing the need for high concentrations and minimizing side effects.
The combination of compounds of formula (I) or (II) with other antimicrobial agents demonstrates enhanced antimicrobial activity against common pathogens, ensuring product safety and shelf-life without increasing concentrations, thereby reducing potential side effects and improving antimicrobial efficacy.
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Abstract
Description
[0001] Antimicrobial synergies
[0002] The present invention primarily relates to a mixture comprising or consisting of one or more compound(s) of formula (I) or (II) as defined herein and one or more further antimicrobial agent(s) and it relates to a product comprising a mixture as defined herein. Moreover, the present invention relates to the use of one or more compound(s) of formula (I) or (II) as defined herein to improve the antimicrobial effect of one or more further antimicrobial agent(s) and to the use of one or more further antimicrobial agent(s) to improve the antimicrobial effect of one or more compound(s) of formula (I) or (II) as defined herein. The present invention further relates to the use of a mixture as defined herein as an antimicrobial agent and to a process as defined herein for improving the antimicrobial effect of one or more compound(s) as defined in step (a) and / or of one or more compound(s) as defined in step (b) of the process. Moreover, the present invention relates to a process for inhibiting or preventing the growth of one or more microorganisms in a product or semifinished product and to a process for inhibiting or preventing the growth of one or more microorganisms on a mammal’s skin or mucosa and / or for inhibiting or preventing the growth of one or more microorganisms on / in a surface. Moreover, the present invention relates to a mixture or compound as defined herein for use as an antimicrobial agent for inhibiting or preventing the growth of one or more microorganisms on a mammal’s skin or mucosa. Finally, the present invention relates to the use of one or more compound(s) as defined herein as antimicrobial agent(s) and to a process as defined herein for inhibiting or preventing the growth of one or more microorganisms on a mammal’s skin or mucosa, and / or for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, and / or for inhibiting or preventing the growth of one or more microorganisms on / in a surface.
[0003] The present invention is one of a series of inventions related to 3-hydroxypropylesters and structurally related compounds co-filed by the same applicant and on the same date as PCT patent applications, which are titled “3-Hydroxypropylesters as antioxidants and tocopherol boosters”, “3-Hydroxypropylesters as solubility enhancers for lipophilic ingredients”, “3-Hydroxypropylesters as foam and viscosity modulating agents in surfactant containing formulations”, “3-Hydroxypropylesters as emulsifying agents”, and “3- Hydroxypropylesters as antimicrobial agents”, whose content is incorporated herein by way of reference.
[0004] Further aspects of the present invention will arise from the description below, in particular from the examples, as well as from the attached patent claims.
[0005] Personal care, pharmaceutical, and household products usually contain antimicrobial agents to increase their shelf-life and to guarantee safety for the consumer’s health. The aim is to protect consumers of said products from potentially pathogenic microorganisms that might otherwise grow inside the products, and to stop or delay the biological and / or physicochemical deterioration of the product. The same rationale applies to semi-finished products that are used in the production of said personal care, pharmaceutical, and household products.
[0006] The preservation of said products can be achieved by chemical, physical or physicochemical methods. The most common strategy is the incorporation of antimicrobial agents into said products. Common antimicrobial agents are, for example, parabens, formaldehyde releasers, isothiazolinones, organic acids, triclosan, phenoxyethanol and benzyl alcohol. Some antimicrobial agents, however, have the drawback that they might induce undesirable side effects in consumers. These effects might range from mild skin irritation to allergic reactions to the chemicals used.
[0007] Hence, it was an object of the present invention to provide new combinations of antimicrobial agents that are highly active against a range of common pathogens and, preferably, enable the reduction of the concentration of the antimicrobial agents in personal care, pharmaceutical, and household products to a minimum while still ensuring the protection of said products against the growth of pathogenic microorganisms. It was a further object of the present invention to provide new combinations of antimicrobial agents that lead to a synergistic improvement of the antimicrobial activity of the resulting mixture. Further objects underlying the present invention follow from the description and the patent claims below. According to a first aspect of the present invention, the stated objects are achieved by a mixture comprising or consisting of
[0008] (i) one or more compound(s) of formula (I) wherein X is selected from the group consisting of and wherein R1is selected from the group consisting of -H and -OH, and R2is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), preferably R2is selected from the group consisting of -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), or wherein R1is -OH and R2and the -OH group shown in formula (I) are joined together to form the following compound of formula (l-a): or wherein R1and R2are joined together to form the following compound of formula (l-b):
[0009] (l-b) and
[0010] (ii) one or more further antimicrobial agent(s) (that are different from the compound(s) of formula (I) as defined in constituent (i)), preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0011] In the context of the studies underlying the present invention, it was surprisingly found that mixtures as defined herein display particularly advantageous antimicrobial properties against various bacteria and fungi commonly found in personal care, pharmaceutical, and household products. Said products often are in direct contact with the skin, mucosa, or hair of the consumer of the product or with other surfaces used by humans, such as, for instance, kitchen and bathroom surfaces. Hence, it is particularly advantageous to ensure that said products are protected against the growth of potentially pathogenic microorganisms. This ensures that the products are safe to use for the consumer and can be stored for a sufficient amount of time without degrading.
[0012] Another aspect of the present invention relates to a mixture comprising or consisting of (i) one or more compound(s) of formula (II) wherein X is selected from the group consisting of and wherein n = 1 , R1is selected from the group consisting of -H and -OH, and R2is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), preferably R2is selected from the group consisting of -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), or wherein n = 1 , R1is -OH, and R2and the -OH group shown in formula (II) are joined together to form the following compound of formula (l-a): or wherein n = 1 and R1and R2are joined together to form the following compound of formula (l-b):
[0013] (l-b) or wherein n = 2-10, preferably 3-10, more preferably 4-10, R1is -OH, and R2= -H, and
[0014] (ii) one or more further antimicrobial agent(s) (that are different from the compound(s) of formula (II) (and (l-a) and (l-b)) as defined in constituent (i)), preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0015] According to a preferred embodiment, the one or more compound(s) of formula (II) of constituent (i) is / are selected from the group consisting of
[0016] According to a preferred embodiment, the one or more compound(s) of formula (I) or (II) of 5 constituent (i) is / are selected from the group consisting of
[0017] Particularly preferably, the one or more compound(s) of formula (I) or (II) of constituent (i) is / are selected from the group consisting of
[0018]
[0019]
[0020] According to another preferred embodiment, constituent (i) comprises a mixture of the following two compounds of formula (I) or (II): According to another preferred embodiment, constituent (i) comprises a mixture of the following two compounds of formula (I) or (II):
[0021] Preferably, the one or more further antimicrobial agent(s) of constituent (ii) of the mixture is / are
[0022] (ii-1) selected from the group consisting of 1 ,2-decanediol (decylene glycol), 1 ,2- heptanediol, 1 ,2-hexanediol, 1 ,2-nonanediol, 1 ,2-octanediol, 1 ,2-pentanediol, 1 ,2- propanediol, 1 ,3-propanediol, 2,3-decanediol, 2,3-heptanediol, 2,3-hexanediol, 2,3- nonanediol, 2,3-octanediol, 2,3-pentanediol, 2-benzylheptanol, 2- hydroxyacetophenone, 2-methyl 5-cyclohexylpentanol, 3-hydroxypropyl 2- hydroxybenzoate, 4-hydroxyacetophenone, alkyl (C 12-22) trimethyl ammonium bromide and chloride, anisic acid and salts thereof, anisic acid 3-hydroxypropylester, ascorbic acid and salts thereof, ascorbyl palmitate, azelaic acid, azeloyl diglycinate, benzalkonium bromide, benzalkonium chloride, benzalkonium saccharinate, benzethonium chloride, benzoic acid, benzoic acid 3-hydroxypropylester, benzyl alcohol, benzyl salicylate, benzysothiazolinone, bisabolol, bronopol (2-bromo-2- nitropropane-1 ,3-diol), butylene glycol, butylparaben, camphor, caprylhydroxamic acid, capryloyl glycine, capryloyl / caproyl anhydro methyl glucamide, caprylyl glyceryl ether, caprylyl / capric triglyceride, cetylpyridinium chloride, chlorhexidine, chlorhexidine diacetate, chlorhexidine digluconate, chlorhexidine dihydrochloride, chlorocresol, chloroxylenol, chlorphenesin, citronellyl methylcrotonate, climbazole, cyclohexylglycerin, dehydroacetic acid, diazolidinyl urea, dimethyl phenylbutanol, dimethyl phenylpropanol, dipropylene glycol, disodium EDTA, DMDM hydantoin, ethanol, ethyl lauroyl arginate HCI, ethyl lauroyl arginate laurate, ethylhexylglycerin, ethylparaben, eucalyptol, farnesol, garcinia mangostana peel extract, gluconic acid and salts thereof, glycerine, glyceryl caprate, glyceryl caprylate, glyceryl heptanoate, glyceryl laurate, glyceryl undecylenate, glycolipids, heptylglycerin, hexamidine, hexamidine diisethionate, hexylene glycol, hexylglycerin, hydroxyethoxyphenyl butanol, hydroxyethoxyphenyl butanone, imidazolidinyl urea, iodopropynyl butylcarbamate, isoamyl laurate, isobutylparaben, isopropylparaben, itaconic acid and salts thereof, jasmol, lactic acid, lauryl alcohol, levulinic acid, mandelic acid, mannitol, menthol, methyl salicylate, methyl undecylenate, methylbenzyl alcohol, methylchloroisothiazolinone, methylheptylglycerin, methylisothiazolinone, methylparaben and salts thereof, methylpropanediol, morinda citrifolia callus culture lysate, octenidine HCI, octylisothiazolinone, o-cymen-5-ol , panthenol, PCA ethyl cocoyl arginate, phenethyl alcohol, phenoxyethanol, phenylpropanol, piroctone olamine, polyarginine, polyglyceryl-10 laurate, polyglyceryl-2 caprate, polyglyceryl-3 caprylate, polyglyceryl-4 caprylate / caprate, polyglyceryl-4 laurate / sebacate, polylysine, potassium sorbate, propanediol caprate, propanediol caprylate, propanediol laurate, propanediol undecylenate, propylene glycol, propylene glycol caprylate, propylparaben, raspberry ketone, saccharide isomerate, salicylic acid, salvia officinalis (sage) oil, silver chloride, silver citrate, sodium anisate, sodium benzoate, sodium caproyl lactylate, sodium caproyl / lauroyl lactylate, sodium ethylparaben, sodium lactate, sodium lauroyl lactylate, sodium levulinate, levulinic acid, sodium methylparaben, sodium phytate, phytic acid, sodium propylparaben, sorbic acid, sorbitan caprylate, sorbitol, TEA-salicylate, tetraselmis extract, tetrasodium glutamate diacetate, thymol, triclocarban, triclosan, triethyl citrate, trisodium dicarboxymethyl alaninate, trisodium ethylenediamine disuccinate, tropolone, undecylenic acid, undecylenoyl glycine, xylityl caprylate, xylityl sesquicaprylate, zinc citrate, zinc lactate, zinc neodecanoate, zinc pyrithione, zinc ricinoleate, and capryloyl / caproyl anhydro methyl glucamide (and) water.
[0023] According to another preferred embodiment, the one or more further antimicrobial agent(s) of constituent (ii) of the mixture is / are
[0024] (ii-2) selected from the group consisting of 1 ,2-decanediol (decylene glycol), 1 ,2- heptanediol, 1 ,2-hexanediol, 1 ,2-nonanediol, 1 ,2-octanediol, 1 ,2-pentanediol, 1 ,3- propanediol, 2,3-heptanediol, 2,3-hexanediol, 2,3-nonanediol, 2,3-octanediol, 2,3- pentanediol, 2-benzylheptanol, 2-methyl 5-cyclohexylpentanol, 4- hydroxyacetophenone, anisic acid and salts thereof, anisic acid 3- hydroxypropylester, ascorbic acid and salts thereof, benzalkonium chloride, benzethonium chloride, benzoic acid, benzoic acid 3-hydroxypropylester, benzyl alcohol, benzyl salicylate, bisabolol, butylene glycol, caprylhydroxamic acid, capryloyl glycine, capryloyl / caproyl anhydro methyl glucamide, caprylyl glyceryl ether, cetylpyridinium chloride, chlorphenesin, citronellyl methylcrotonate, climbazole, cyclohexylglycerin, dehydroacetic acid, dimethyl phenylbutanol, dimethyl phenylpropanol, dipropylene glycol, disodium EDTA, ethanol, ethyl lauroyl arginate HCI, ethyl lauroyl arginate laurate, ethylhexylglycerin, ethylparaben, farnesol, garcinia mangostana peel extract, gluconic acid and salts thereof, glycerine, glyceryl caprate, glyceryl caprylate, glyceryl laurate, glyceryl undecylenate, heptylglycerin, hexamidine diisethionate, hexylene glycol, hexylglycerin, hydroxyethoxyphenyl butanol, hydroxyethoxyphenyl butanone, imidazolidinyl urea, isobutylparaben, itaconic acid and salts thereof, jasmol, lactic acid, lauryl alcohol, levulinic acid, mandelic acid, methylbenzyl alcohol, methylheptylglycerin, methylparaben and salts thereof, morinda citrifolia callus culture lysate, octenidine HCI, o-cymen-5-ol, panthenol, PCA ethyl cocoyl arginate, phenethyl alcohol, phenoxyethanol, phenylpropanol, piroctone olamine, polyglyceryl-10 laurate, polyglyceryl-2 caprate, polyglyceryl-3 caprylate, polylysine, potassium sorbate, propanediol caprate, propanediol caprylate, propanediol laurate, propanediol undecylenate, propylene glycol, propylene glycol caprylate, propylparaben, raspberry ketone, salicylic acid, salvia officinalis (sage) oil, sodium benzoate, sodium caproyl lactylate, sodium caproyl / lauroyl lactylate, sodium lactate, sodium lauroyl lactylate, sodium levulinate, levulinic acid, sodium phytate, phytic acid, sorbic acid, sorbitan caprylate, sorbitol, tetraselmis extract, tetrasodium glutamate diacetate, thymol, triethyl citrate, trisodium dicarboxymethyl alaninate, trisodium ethylenediamine disuccinate, tropolone, undecylenoyl glycine, xylityl caprylate, xylityl sesquicaprylate, zinc citrate, zinc lactate, zinc neodecanoate, and zinc ricinoleate, more preferably is / are
[0025] (ii-3) selected from the group consisting of 1 ,2-decanediol (decylene glycol), 1 ,2- heptanediol, 1 ,2-hexanediol, 1 ,2-nonanediol, 1 ,2-octanediol, 1 ,2-pentanediol, 1 ,3- propanediol, 2,3-heptanediol, 2,3-hexanediol, 2,3-nonanediol, 2,3-octanediol, 2,3- pentanediol, 2-methyl 5-cyclohexylpentanol, 4-hydroxyacetophenone, anisic acid and salts thereof, anisic acid 3-hydroxypropylester, benzoic acid, benzoic acid 3- hydroxypropylester, benzyl alcohol, benzyl salicylate, bisabolol, butylene glycol, caprylhydroxamic acid, capryloyl glycine, capryloyl / caproyl anhydro methyl glucamide, caprylyl glyceryl ether, chlorphenesin, citronellyl methylcrotonate, climbazole, cyclohexylglycerin, dehydroacetic acid, dimethyl phenylbutanol, dimethyl phenylpropanol, dipropylene glycol, ethanol, ethyl lauroyl arginate HCI, ethyl lauroyl arginate laurate, ethylhexylglycerin, ethylparaben, farnesol, garcinia mangostana peel extract, glycerine, glyceryl caprate, glyceryl caprylate, glyceryl laurate, glyceryl undecylenate, heptylglycerin, hexylene glycol, hydroxyethoxyphenyl butanol, hydroxyethoxyphenyl butanone, itaconic acid and salts thereof, lactic acid, lauryl alcohol, levulinic acid, methylhepthylglycerin, methylparaben and salts thereof, morinda citrifolia callus culture lysate, octenidine HCI, o-cymen-5-ol, panthenol, phenoxyethanol, phenylpropanol, piroctone olamine, polyglyceryl-2 caprate, polyglyceryl-3 caprylate, potassium sorbate, propanediol caprate, propanediol caprylate, propanediol laurate, propanediol undecylenate, propylene glycol, propylene glycol caprylate, raspberry ketone, salvia officinalis (sage) oil, sodium benzoate, sodium caproyl / lauroyl lactylate, sodium levulinate, levulinic acid, sorbic acid, sorbitan caprylate, sorbitol, tetraselmis extract, tetrasodium glutamate diacetate, triethyl citrate, trisodium ethylenediamine disuccinate, tropolone, undecylenoyl glycine, xylityl caprylate, xylityl sesquicaprylate, zinc citrate, zinc lactate, zinc neodecanoate, and zinc ricinoleate, more preferably is / are
[0026] (ii-4) selected from the group consisting of 1 ,2-decanediol (decylene glycol), 1 ,2- heptanediol, 1 ,2-hexanediol, 1 ,2-nonanediol, 1 ,2-octanediol, 1 ,2-pentanediol (pentylene glycol), 1 ,3-propanediol, 2-methyl 5-cyclohexylpentanol, 4- hydroxyacetophenone, benzoic acid 3-hyroxypropylester, anisic acid 3- hydroxypropylester, benzyl alcohol, benzyl salicylate, bisabolol, butylene glycol, caprylhydroxamic acid, capryloyl glycine, capryloyl / caproyl anhydro methyl glucamide, caprylyl glyceryl ether, chlorphenesin, citronellyl methylcrotonate, dimethyl phenylbutanol, dimethyl phenylpropanol, dipropylene glycol, ethylhexylglycerin, ethylparaben, farnesol, garcinia mangostana peel extract, glyceryl caprylate, glyceryl laurate, glyceryl undecylenate, heptylglycerin, hexylene glycol, hydroxyethoxyphenyl butanol, hydroxyethoxyphenyl butanone, itaconic acid and salts thereof, lauryl alcohol, methylhepthylglycerin, methylparaben and salts thereof, morinda citrifolia callus culture lysate, octenidine HCI, o-cymen-5-ol, panthenol, phenoxyethanol, phenylpropanol, piroctone olamine, polyglyceryl-2 caprate, polyglyceryl-3 caprylate, potassium sorbate, propanediol caprylate, propanediol undecylenate, propylene glycol, propylene glycol caprylate, raspberry ketone, salvia officinalis (sage) oil, sodium benzoate, sodium caproyl / lauroyl lactylate, triethyl citrate, undecylenoyl glycine, xylityl caprylate, xylityl sesquicaprylate, zinc citrate, zinc lactate, zinc neodecanoate, and zinc ricinoleate, more preferably is / are
[0027] (ii-5) selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2- heptanediol, 1 ,2-nonanediol, 1 ,3-propanediol, 2-methyl-5-cyclohexylpentanol, benzyl salicylate, bisabolol, caprylhydroxamic acid, capryloyl / caproyl anhydro methyl glucamide, chlorphenesin, ethylparaben, glyceryl caprylate, heptylglycerin, hydroxyethoxyphenyl butanol, hydroxyethoxyphenyl butanone, itaconic acid, methylheptylglycerin, methylparaben, potassium sorbate, propanediol caprate, propanediol laurate, propylene glycol caprylate, raspberry ketone, sodium benzoate, and sodium methylparaben, more preferably is / are
[0028] (ii-6) selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2- heptanediol, 1 ,3-propanediol, caprylhydroxamic acid, chlorphenesin, glyceryl caprylate, hydroxyethoxyphenyl butanone, and methylheptylglycerin, most preferably is / are
[0029] (ii-7) selected from the group consisting of 1 ,2-heptanediol, caprylhydroxamic acid, chlorphenesin, glyceryl caprylate, hydroxyethoxyphenyl butanone, and methylheptylglycerin.
[0030] According to a preferred embodiment of the mixture according to the invention, the one or more compound(s) of formula (I) of constituent (i) is / are selected from the group consisting of and the one or more further antimicrobial agent(s) of constituent (ii) is / are selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,3-propanediol, caprylhydroxamic acid, chlorphenesin, glyceryl caprylate, hydroxyethoxyphenyl butanone, and methylheptylglycerin.
[0031] According to another preferred embodiment of the mixture according to the invention, the compound of formula (I) of constituent (i) is and the one or more further antimicrobial agent(s) of constituent (ii) is / are selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,3-propanediol, caprylhydroxamic acid, chlorphenesin, glyceryl caprylate, hydroxyethoxyphenyl butanone, and methylheptylglycerin.
[0032] According to another preferred embodiment of the mixture according to the invention, the compound of formula (I) of constituent (i) is and the one or more further antimicrobial agent(s) of constituent (ii) is / are selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,3-propanediol, caprylhydroxamic acid, chlorphenesin, glyceryl caprylate, hydroxyethoxyphenyl butanone, and methylheptylglycerin.
[0033] According to a preferred embodiment, the mixture according to the invention comprises or consists of
[0034] (benzoic acid 3-hydroxypropylester) and
[0035] (ii) 1 ,2-pentanediol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0036] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0037] (ii) 1 ,2-hexanediol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0038] According to another preferred embodiment, the mixture according to the invention comprises or consists of
[0039] (ii) 1 ,2-heptanediol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0040] According to another preferred embodiment, the mixture according to the invention comprises or consists of and (ii) 1 ,2-nonanediol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0041] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0042] (ii) 1 ,3-propanediol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0043] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0044] (ii) 2-methyl-5-cyclohexylpentanol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i). According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0045] (ii) benzyl salicylate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0046] According to another preferred embodiment, the mixture according to the invention comprises or consists of
[0047] (ii) bisabolol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0048] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0049] (ii) caprylhydroxamic acid, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0050] According to another preferred embodiment, the mixture according to the invention comprises or consists of
[0051] (ii) capryloyl / caproyl anhydro methyl glucamide, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0052] According to another preferred embodiment, the mixture according to the invention comprises or consists of and (ii) chlorphenesin, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0053] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0054] (ii) ethylparaben, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0055] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0056] (ii) glyceryl caprylate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i). According to another preferred embodiment, the mixture according to the invention comprises or consists of
[0057] (ii) heptylglycerin, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0058] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0059] (ii) hydroxyethoxyphenyl butanol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0060] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0061] (ii) hydroxyethoxyphenyl butanone, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0062] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0063] (ii) itaconic acid, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0064] According to another preferred embodiment, the mixture according to the invention comprises or consists of and (ii) methylheptylglycerin, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0065] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0066] (ii) methylparaben, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0067] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0068] (ii) potassium sorbate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i). According to another preferred embodiment, the mixture according to the invention comprises or consists of
[0069] (ii) propanediol caprate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0070] According to another preferred embodiment, the mixture according to the invention comprises or consists of
[0071] (ii) propanediol laurate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0072] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0073] (ii) propylene glycol caprylate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0074] According to another preferred embodiment, the mixture according to the invention comprises or consists of
[0075] (ii) raspberry ketone, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0076] According to another preferred embodiment, the mixture according to the invention comprises or consists of and (ii) sodium benzoate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0077] According to another preferred embodiment, the mixture according to the invention comprises or consists of
[0078] (ii) sodium methylparaben, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0079] According to another preferred embodiment, the mixture according to the invention comprises or consists of
[0080] (anisic acid 3-hydroxypropylester) and
[0081] (ii) 1 ,2-pentanediol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0082] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0083] (ii) 1 ,2-hexanediol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0084] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0085] (ii) 1 ,2-heptanediol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i). According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0086] (ii) 1 ,2-nonanediol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0087] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0088] (ii) 1 ,3-propanediol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0089] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0090] (ii) 2-methyl-5-cyclohexylpentanol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0091] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0092] (ii) benzyl salicylate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0093] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0094] (ii) bisabolol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0095] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0096] (ii) caprylhydroxamic acid, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0097] According to another preferred embodiment, the mixture according to the invention comprises or consists of and (ii) capryloyl / caproyl anhydro methyl glucamide, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0098] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0099] (ii) chlorphenesin, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0100] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0101] (ii) ethylparaben, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i). According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0102] (ii) glyceryl caprylate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0103] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0104] (ii) heptylglycerin, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0105] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0106] (ii) hydroxyethoxyphenyl butanol, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0107] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0108] (ii) hydroxyethoxyphenyl butanone, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i). According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0109] (ii) itaconic acid, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0110] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0111] (ii) methylheptylglycerin, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0112] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0113] (ii) methylparaben, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0114] According to another preferred embodiment, the mixture according to the invention comprises or consists of
[0115] (ii) potassium sorbate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0116] According to another preferred embodiment, the mixture according to the invention comprises or consists of (ii) propanediol caprate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0117] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0118] (ii) propanediol laurate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0119] According to another preferred embodiment, the mixture according to the invention comprises or consists of (ii) propylene glycol caprylate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0120] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0121] (ii) raspberry ketone, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0122] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0123] (ii) sodium benzoate, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0124] According to another preferred embodiment, the mixture according to the invention comprises or consists of and
[0125] (ii) sodium methylparaben, preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
[0126] According to another preferred embodiment, the mixture according to the invention comprises or consists of [2-(3,4-dihydroxytetrahydrofuran-2-yl)-2-hydroxy-ethyl] benzoate, preferably of the following structure
[0127] (constituent (i); compound of formula (I) or (II) as defined herein; cf. column “Constituent
[0128] (i)” in Table 1 below) and constituent (ii) (further antimicrobial agent; cf. column “Constituent
[0129] (ii)” in Table 1 below, respectively), preferably wherein the total amounts of [2-(3,4- dihydroxytetrahydrofuran-2-yl)-2-hydroxy-ethyl] benzoate and of constituent (ii), respectively, contained in the mixture are such that [2-(3,4-dihydroxytetrahydrofuran-2-yl)- 2-hydroxy-ethyl] benzoate synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of [2-(3,4- dihydroxytetrahydrofuran-2-yl)-2-hydroxy-ethyl] benzoate.
[0130] Table 1 : Specific mixtures of [2-(3,4-dihydroxytetrahydrofuran-2-yl)-2-hydroxy-ethyl benzoate (constituent (i); compound of formula (I) or (II) as defined herein) with a further antimicrobial agent (constituent (ii)), respectively According to another preferred embodiment, the mixture according to the invention comprises or consists of [2-(3,4-dihydroxytetrahydrofuran-2-yl)-2-hydroxy-ethyl] 4- methoxybenzoate, preferably of the following structure (constituent (i); compound of formula (I) or (II) as defined herein; cf. column “Constituent
[0131] (i)” in Table 2 below) and constituent (ii) (further antimicrobial agent; cf. column “Constituent
[0132] (ii)” in Table 2 below, respectively), preferably wherein the total amounts of [2-(3,4- dihydroxytetrahydrofuran-2-yl)-2-hydroxy-ethyl] 4-methoxybenzoate and of constituent (ii), respectively, contained in the mixture are such that [2-(3,4-dihydroxytetrahydrofuran-2-yl)- 2-hydroxy-ethyl] 4-methoxybenzoate synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of [2-(3,4-dihydroxytetrahydrofuran-2-yl)-2-hydroxy-ethyl] 4-methoxybenzoate.
[0133] Table 2: Specific mixtures of [2-(3,4-dihydroxytetrahydrofuran-2-yl)-2-hydroxy-ethyl] 4- methoxybenzoate (constituent (i); compound of formula (I) or (II) as defined herein) with a further antimicrobial agent (constituent (ii)), respectively According to another preferred embodiment, the mixture according to the invention comprises or consists of 1 ,4-anhydroarabinitol-5-benzoate, preferably of the following structure
[0134] (constituent (i); compound of formula (I) or (II) as defined herein; cf. column “Constituent (i)” in Table 3 below) and constituent (ii) (further antimicrobial agent; cf. column “Constituent
[0135] (ii)” in Table 3 below, respectively), preferably wherein the total amounts of 1 ,4- anhydroarabinitol-5-benzoate and of constituent (ii), respectively, contained in the mixture are such that 1 ,4-anhydroarabinitol-5-benzoate synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of 1 ,4-anhydroarabinitol-5-benzoate.
[0136] Table 3: Specific mixtures of 1 ,4-anhydroarabinitol-5-benzoate (constituent (i); compound of formula (I) or (II) as defined herein) with a further antimicrobial agent (constituent (ii)), respectively According to another preferred embodiment, the mixture according to the invention comprises or consists of 1 ,4-anhydroarabinitol-5-(4-methoxybenzoate), preferably of the following structure
[0137] (constituent (i); compound of formula (I) or (II) as defined herein; cf. column “Constituent (i)” in Table 4 below) and constituent (ii) (further antimicrobial agent; cf. column “Constituent
[0138] (ii)” in Table 4 below, respectively), preferably wherein the total amounts of 1 ,4- anhydroarabinitol-5-(4-methoxybenzoate) and of constituent (ii), respectively, contained in the mixture are such that 1 ,4-anhydroarabinitol-5-(4-methoxybenzoate) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of 1 ,4-anhydroarabinitol-5-(4-methoxybenzoate).
[0139]
[0140]
[0141] Table 4: Specific mixtures of 1 ,4-anhydroarabinitol-5-(4-methoxybenzoate) (constituent (i); compound of formula (I) or (II) as defined herein) with a further antimicrobial agent (constituent (ii)), respectively
[0142] According to another preferred embodiment, the mixture according to the invention comprises or consists of 2,3,4-trihydroxybutyl (4-methoxybenzoate), preferably of the following structures
[0143] (a mixture of [(2S,3R)-2,3,4-trihydroxybutyl] anisate and [(2R,3S)-2,3,4-trihydroxybutyl] anisate, in the following: erytritol anisate),
[0144] (constituent (i); compound(s) of formula (I) or (II) as defined herein; cf. column “Constituent
[0145] (i)” in Table 5 below) and constituent (ii) (further antimicrobial agent; cf. column “Constituent
[0146] (ii)” in Table 5 below, respectively), preferably wherein the total amounts of 2,3,4- trihydroxybutyl (4-methoxybenzoate), more preferably of erytritol anisate, and of constituent (ii), respectively, contained in the mixture are such that 2,3,4-trihydroxybutyl (4- methoxybenzoate), preferably erytritol anisate, synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of 2,3,4-trihydroxybutyl (4-methoxybenzoate), preferably of erytritol anisate.
[0147] Table 5: Specific mixtures of 2,3,4-trihydroxybutyl (4-methoxybenzoate), preferably erytritol anisate (constituent (i); compound(s) of formula (I) or (II) as defined herein), with a further antimicrobial agent (constituent (ii)), respectively
[0148] According to another preferred embodiment, the mixture according to the invention comprises or consists of 2,3,4,5-tetrahydroxypentyl benzoate, preferably of the following structures
[0149] (a mixture of [(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl] benzoate and [(2R, 3R,4S)-2, 3,4,5- tetrahydroxypentyl] benzoate, in the following: xylitol benzoate),
[0150] (constituent (i); compound(s) of formula (I) or (II) as defined herein; cf. column “Constituent (i)” in Table 6 below) and constituent (ii) (further antimicrobial agent; cf. column “Constituent
[0151] (ii)” in Table 6 below, respectively), preferably wherein the total amounts of 2, 3,4,5- tetrahydroxypentyl benzoate, more preferably of xylitol benzoate, and of constituent (ii), respectively, contained in the mixture are such that 2,3,4,5-tetrahydroxypentyl benzoate, preferably xylitol benzoate, synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of 2, 3,4,5- tetrahydroxypentyl benzoate, preferably of xylitol benzoate.
[0152] Table 6: Specific mixtures of 2,3,4,5-tetrahydroxypentyl benzoate, preferably of xylitol benzoate (constituent (i); compound(s) of formula (I) or (II) as defined herein), with a further antimicrobial agent (constituent (ii)), respectively
[0153] According to another preferred embodiment, the mixture according to the invention comprises or consists of 2,3,4,5,6-pentahydroxyhexyl benzoate, preferably of the following structure ([(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl] benzoate, in the following: mannitol-1- benzoate),
[0154] (constituent (i); compound of formula (I) or (II) as defined herein; cf. column “Constituent
[0155] (i)” in Table 7 below) and constituent (ii) (further antimicrobial agent; cf. column “Constituent
[0156] (ii)” in Table 7 below, respectively), preferably wherein the total amounts of 2, 3, 4,5,6- pentahydroxyhexyl benzoate, more preferably of mannitol-1 -benzoate, and of constituent (ii), respectively, contained in the mixture are such that 2,3,4,5,6-pentahydroxyhexyl benzoate, preferably mannitol-1 -benzoate, synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of 2,3,4,5,6-pentahydroxyhexyl benzoate, preferably of mannitol-1 -benzoate.
[0157] Table 7: Specific mixtures of 2,3,4,5,6-pentahydroxyhexyl benzoate, preferably mannitol- 1 -benzoate (constituent (i); compound of formula (I) or (II) as defined herein), with a further antimicrobial agent (constituent (ii)), respectively
[0158] According to another preferred embodiment, the mixture according to the invention comprises or consists of 2,3,4,5,6-pentahydroxyhexyl (4-methoxybenzoate), preferably of the following structure ([(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl] anisate, in the following: mannitol-1- anisate),
[0159] (constituent (i); compound of formula (I) or (II) as defined herein; cf. column “Constituent (i)” in Table 8 below) and constituent (ii) (further antimicrobial agent; cf. column “Constituent (ii)” in Table 8 below, respectively), preferably wherein the total amounts of 2, 3, 4,5,6- pentahydroxyhexyl (4-methoxybenzoate), more preferably of mannitol-1-anisate, and of constituent (ii), respectively, contained in the mixture are such that 2, 3, 4,5,6- pentahydroxyhexyl (4-methoxybenzoate), preferably mannitol-1-anisate, synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of 2,3,4,5,6-pentahydroxyhexyl (4-methoxybenzoate), preferably of mannitol-1-anisate.
[0160] Table 8: Specific mixtures of 2,3,4,5,6-pentahydroxyhexyl (4-methoxybenzoate), preferably mannitol-1-anisate (constituent (i); compound of formula (I) or (II) as defined herein), with a further antimicrobial agent (constituent (ii)), respectively
[0161] According to another preferred embodiment, the mixture according to the invention comprises or consists of 2,3,4,5,6-pentahydroxyhexyl benzoate, preferably of the following structures
[0162] (a mixture of [(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl] benzoate and [(2R,3R,4R,5S)- 2,3,4,5,6-pentahydroxyhexyl] benzoate, in the following: sorbitol benzoate),
[0163] (constituent (i); compound(s) of formula (I) or (II) as defined herein; cf. column “Constituent
[0164] (i)” in Table 9 below) and constituent (ii) (further antimicrobial agent; cf. column “Constituent
[0165] (ii)” in Table 9 below, respectively), preferably wherein the total amounts of 2,3,4,5,6- pentahydroxyhexyl benzoate, more preferably of sorbitol benzoate, and of constituent (ii), respectively, contained in the mixture are such that 2,3,4,5,6-pentahydroxyhexyl benzoate, preferably sorbitol benzoate, synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of 2,3,4,5,6- pentahydroxyhexyl benzoate, preferably of sorbitol benzoate.
[0166] Table 9: Specific mixtures of 2,3,4,5,6-pentahydroxyhexyl benzoate, preferably sorbitol benzoate (constituent (i); compound(s) of formula (I) or (II) as defined herein), with a further antimicrobial agent (constituent (ii)), respectively
[0167] According to another preferred embodiment, the mixture according to the invention comprises or consists of 2,3,4,5,6-pentahydroxyhexyl (4-methoxybenzoate), preferably of the following structures (a mixture of [(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl] anisate and [(2R,3R,4R,5S)- 2,3,4,5,6-pentahydroxyhexyl] anisate, in the following: sorbitol anisate),
[0168] (constituent (i); compound(s) of formula (I) or (II) as defined herein; cf. column “Constituent (i)” in Table 10 below) and constituent (ii) (further antimicrobial agent; cf. column “Constituent (ii)” in Table 10 below, respectively), preferably wherein the total amounts of 2,3,4,5,6-pentahydroxyhexyl (4-methoxybenzoate), more preferably of sorbitol anisate, and of constituent (ii), respectively, contained in the mixture are such that 2,3,4,5,6- pentahydroxyhexyl (4-methoxybenzoate), preferably sorbitol anisate, synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of 2,3,4,5,6-pentahydroxyhexyl (4-methoxybenzoate), preferably of sorbitol anisate.
[0169] Table 10: Specific mixtures of 2,3,4,5,6-pentahydroxyhexyl (4-methoxybenzoate), preferably sorbitol anisate (constituent (i); compound(s) of formula (I) or (II) as defined herein), with a further antimicrobial agent (constituent (ii)), respectively
[0170] According to a preferred embodiment, the mixture according to the invention comprises a total amount of from 10 to 90 wt.%, preferably from 30 to 70 wt.%, more preferably from 40 to 60 wt.%, of the compounds of formula (I) and (II) of constituent (i), based on the total weight of the mixture, and / or the mixture comprises a total amount of from 10 to 90 wt.%, preferably from 30 to 70 wt.%, more preferably from 40 to 60 wt.%, of the one or more further antimicrobial agent(s) of constituent (ii), based on the total weight of the mixture.
[0171] Another aspect of the present invention relates to a product comprising a mixture as defined herein, preferably wherein the product is selected from the group consisting of personal care products, pharmaceutical products, and household products, more preferably wherein the product is i. in the form of a dispersion comprising an oil component in an amount of > 1 wt.%, preferably in an amount of > 3 wt.%, preferably in the form of an emulsion, more preferably an O / W emulsion, a W / O emulsion, a multiple emulsion, a hydrodispersion gel, a balm, a multiple emulsion of the water-in-oil type (W / O / W) or of the oil-in-water type (O / W / O), a PIT emulsion, a Pickering emulsion, a micro-emulsion, a liquid, a lotion, a suspension, a milk, an ointment, a paste, a gel, a cream-based, an oil-based or a liposome-based formulation; ii. in the form of a liquid surfactant formulation;
[0172] Hi. in the form of a solid surfactant formulation; or iv. in the form of an aqueous or aqueous / alcoholic, preferably aqueous / ethanolic solution or aqueous / glycolic, solution. Preferably, the oil component corresponds to one or more oil body / bodies or wax(es), more preferably selected from the group consisting of natural fats and oils, more preferably selected from the group consisting of prunus amygdalus dulcis (sweet almond) oil, caprylic / capric triglyceride, argania spinosa kernel oil, butyrospermum parkii (shea) butter, cannabis sativa seed oil, olea europaea (olive) fruit oil, persea gratissima (avocado) oil, vitis vinifera (grape) seed oil, ricinus communis (castor) seed oil, sesamum indicum (sesame) seed oil, heliantus annuus (sunflower) seed oil, crambe abyssinica seed oil, cocos nucifera (coconut) oil, and triheptanoin castoryl maleate, fatty alcohols and alcohols, more preferably selected from the group consisting of octyldodecanol, isocetyl alcohol, cetyl alcohol, stearyl alcohol, and cetearyl alcohol, glyceryl esters and derivatives thereof, more preferably selected from the group consisting of PEG-7 glyceryl cocoate, PEG-6 caprylic / capric glycerides, polyglyceryl-3-caprate, polyglyceryl-4-caprate, PEG-5 bertholletia excelsa seed oily glyceryl esters, PEG-7 carapa guianensis glyceryl esters, PEG-7 caprylic / capric glycerides, PEG-7 theobroma grandiflorum seed butter glyceryl esters, cocoglycerides, glyceryl caprylate / caprate, glyceryl oleate, polyglyceryl-2 caprate, polyglyceryl-4 cocoate, polyglyceryl-3 diisostearate, and PEG-10 olive glycerides, esters, more preferably selected from the group consisting of cetearyl nonanoate, propanediol dicaprylate / caprate, ethylhexyl isononanoate, PPG3 benzyl ether myristate, cetyl palmitate, myristyl myristate, myristyl stearate, myristyl oleate, myristyl behenate, ethylhexyl hydroxystearate, DI-PPG-3 myristyl ether adipate, DI-PPG-2 myreth-10 adipate, PPG-15 stearyl ether, diethylhexyl succinate, propylene glycol isostearate, diethylhexyl adipate, butyl stearate, ethylhexyl cocoate, ethylhexyl stearate, pentaerythrityl tetracaprylate / tetracaprate, tridecyl neopentanonate, myristyl lactate, PPG-10 cetyl ether, PPG-15 stearyl ether, pentaerythrityl stearate / caprate / caprylate adipate, diisopropyl dimer dilinoleate, isopropyl isostearate, pentaerythrityl tetraisostearate, C12-15 alkyl benzoate, triisononanoin, isostearyl isostearate, triisostearin, trimethylolpropane triisostearate, diisopropyl adipate, isocetyl stearate, propylene glycol dicaprlyate / dicaprate, PPG 2 myristyl ether propionate, isostearyl neopentanoate, isopropyl palmitate, isopropyl myristate, cetyl esters, bis-diglyceryl polyacyladipate-2, isoamyl cocoate, cetyl ethylhexanoate, cetyl ricinoleate, decyl cocoate, diethylhexyl carbonate, decyl oleate, cetearyl ethylhexanoate, lauryl oleate, oleyl erucate, ethylhexyl palmitate, ethylhexyl stearate, stearyl heptanoate, phenoxyethyl caprylate, hexyl laurate, dibutyl adipate, coco- caprlyate, dicaprylyl carbonate, coco-caprylate / caprate, caprylyl capylate / caprate, propylheptyl caprylate, decyltetradecyl ethylhexanoate, cetearyl isononanoate, neopentyl glycol diheptanoate, diheptyl succinate, heptyl undecylenate, propylene glycol dibenzoate, isopropyl laurate, propylene glycol diethylhexanoate, cetyl lactate, lauryl lactate, C12-15 alkyl lactate, diethylhexyl malate, isocetyl stearoyl stearate, isodecyl neopentanoate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl erucate, erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenate, dipropylheptyl carbonate, and erucyl erucate, ethers, more preferably selected from the group consisting of PPG-3 myristyl ether, PPG- 11 stearyl ether, PPG-15 stearyl ether, PPG-14 butyl ether, and dicaprylyl ether, siloxanes and silanes, more preferably selected from the group consisting of dimethicone, PEG-14 dimethicone, PEG / PPG-14 / 4 dimethicone, and PEG / PPG-4 / 12 dimethicone, waxes, more preferably selected from the group consisting of cera alba (beeswax), copernicia cerifera (carnauba) wax, glyceryl rosinate, rhus verniciflua peel cera, euphorbia cerifera (candelilla) wax, hydrolyzed sunflower seed wax, jasminum officinale (jasmine) flower wax, acacia decurrens flower wax, myrica cerifera (bayberry) fruit wax, citrus aurantium dulcis (orange) peel wax, hydrogenated rapeseed oil, oryza sative (rice) bran wax, camellia sinensis leaf wax, vitis vinifera (grape) leaf wax, saccharum officinarum (sugarcane) wax, microcrystalline wax, lanolin (wool) wax, paraffin, synthetic wax, ozocerite, and hydrogenated jojoba wax(es), and naphtenic hydrocarbons, more preferably selected from the group consisting of squalene, dialkylcyclohexanes, and mineral oils.
[0173] Preferably, the personal care product is selected from the group consisting of deodorant products, body care and cleansing products, intimate care and cleansing products, foot care and cleansing products, oral care and cleansing products, scalp care and cleansing products, and face care and cleansing products, more preferably wherein the personal care product is selected from the group consisting of deodorant sprays, deodorant roll-ons, deodorant sticks, deodorant creams, foot creams, body washes, mouth washes, toothpastes, shampoos, hair conditioner, styling wax, styling gels, styling foams, styling creams, styling mousses, styling serums, styling pomades, micellar waters, intimate washes, cleansers, toners, serums, moisturizers, eye creams, balms, soaps, facial masks, sunscreens, liquids for wet wipes, primers, concealers, foundations, rouges, bronzers, highlighters, eyebrow pencils, eyebrow creams, eyebrow waxes, eyebrow gels, eyebrow powders, eyeshadows, eyeliners, mascara, lipsticks, lip glosses, lip liners, lip balms, face powders, setting powders, setting sprays, and nail polishes, and / or the household product is selected from the group consisting of alcohol free glass cleaners, glass cleaners, all-purpose cleaners, all-purpose sprays, degreasers, carpet cleaners, wood cleaners, floor cleaners, laminate cleaners, vinyl cleaners, ceramic cleaners, cork cleaners, linoleum cleaners, porcelain cleaners, stone cleaners, concrete cleaners, parquet cleaners, high gloss floor cleaners, kitchen cleaners, fat solver cleaners, bathroom cleaners, toilet cleaners, chalk cleaners, automatic dish washes, hand dish wash fluids, antibacterial hand dish wash fluids, fabric softeners, fabric care, liquid laundry detergents, powder laundry detergents, and hygiene wash detergents, and / or the pharmaceutical product is selected from the group consisting of deodorant sprays, deodorant roll-ons, deodorant sticks, deodorant creams, foot creams, body washes, mouth washes, toothpastes, shampoos, intimate washes, cleansers, serums, moisturizers, eye creams, balms, soaps, facial masks, sunscreens, and liquids for wet wipes.
[0174] According to a preferred embodiment, the product according to the invention comprises from 0.001 to 15 wt.%, preferably from 0.01 to 10 wt.%, more preferably from 0.05 to 2.5 wt.%, most preferably from 0.1 to 1 wt.%, of the mixture according to the invention, based on the total weight of the product.
[0175] Another aspect of the present invention relates to the use of
[0176] (i) one or more compound(s) of formula (I) wherein X is selected from the group consisting of an and wherein R1is selected from the group consisting of -H and -OH and R2is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), preferably R2is selected from the group consisting of -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), wherein R1is -OH and R2and the -OH group shown in formula (I) are joined together to form the following compound of formula (l-a): wherein R1and R2are joined together to form the following compound of formula (l-b): and / or of one or more compound(s) of formula (II) as defined herein to, preferably synergistically, improve the antimicrobial effect of
[0177] (ii) one or more further antimicrobial agent(s) (that are different from the compound(s) of formula (I) and (II) as defined in constituent (i)), and / or use of (ii) one or more further antimicrobial agent(s) to, preferably synergistically, improve the antimicrobial effect of (i) one or more compound(s) of formula (I), and / or use of (ii) one or more further antimicrobial agent(s) to, preferably synergistically, improve the antimicrobial effect of (i) one or more compound(s) of formula (II).
[0178] According to a preferred embodiment of the use according to the invention, the, preferably synergistically, improved antimicrobial effect is one or more effect(s) selected from the group consisting of an antibacterial effect, an antiviral effect, an antifungal effect, preferably an anti-yeast and / or anti-mold effect.
[0179] Preferably, the antimicrobial effect is achieved against one or more microorganism(s) selected from the group consisting of bacteria and fungi, preferably gram positive and gram negative bacteria, yeasts and filamentous fungi, more preferably selected from the group consisting of Staphylococcus aureus, Candida albicans, Aspergillus brasiliensis, Pseudomonas aeruginosa and Escherichia coli.
[0180] Another aspect of the present invention relates to the use of a mixture according to the invention as an antimicrobial agent.
[0181] According to a preferred embodiment of the use of a mixture according to the invention as an antimicrobial agent, the use is
[0182] (a) for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and / or
[0183] (b) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, and / or (c) for inhibiting or preventing the growth of one or more microorganisms on a surface.
[0184] Another preferred embodiment relates to the use of a mixture according to the invention as an antimicrobial agent
[0185] (a) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, and / or
[0186] (b) for inhibiting or preventing the growth of one or more microorganisms on a surface.
[0187] Another aspect of the present invention relates to a mixture according to the invention for use as an antimicrobial agent, preferably for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin.
[0188] Another aspect of the present invention relates to a process for, preferably synergistically, improving the antimicrobial effect of one or more compound(s) as defined in step (a) and / or of one or more compound(s) as defined in step (b) comprising or consisting of the following steps:
[0189] (a) Providing one or more compound(s) of formula (I) wherein X is selected from the group consisting of and wherein R1is selected from the group consisting of -H and -OH and R2is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)- CH(OH)-CH2(OH), preferably R2is selected from the group consisting of -CH2(OH),
[0190] -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), wherein R1is -OH and R2and the -OH group shown in formula (I) are joined together to form the following compound of formula (l-a): wherein R1and R2are joined together to form the following compound of formula (l-b): and / or providing one or more compound(s) of formula (II) as defined herein, and
[0191] (b) providing one or more further antimicrobial agent(s) (that are different from the compound(s) of formula (I) and (II) as defined in step (a)), and
[0192] (c) mixing the compounds provided in steps (a) and (b).
[0193] Another aspect of the present invention relates to a process for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, comprising or consisting of the following steps:
[0194] (a) Providing (i) one or more compound(s) of formula (I) wherein X is selected from the group consisting of and wherein R1is selected from the group consisting of -H and -OH and R2is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), preferably R2is selected from the group consisting of -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), or wherein R1is -OH and R2and the -OH group shown in formula (I) are joined together to form the following compound of formula (l-a): or wherein R1and R2are joined together to form the following compound of formula (l-b):
[0195] (l-b) and / or providing one or more compound(s) of formula (II) as defined herein, and
[0196] (ii) one or more further antimicrobial agent(s) (that are different from the compound(s) of formula (I) and (II) as defined in constituent (i)), or providing a mixture of constituents (i) and (ii), and
[0197] (b) providing the remaining ingredients of the product or semi-finished product, and
[0198] (c) mixing the compounds provided in steps (a) and (b).
[0199] According to a preferred embodiment of the process, the one or more compound(s) of constituent (i) as provided in step (a) synergistically improve(s) the antimicrobial effect of the one or more compound(s) of constituent (ii) as provided in step (a) and / or the one or more compound(s) of constituent (ii) as provided in step (a) synergistically improve(s) the antimicrobial effect of the one or more compound(s) of constituent (i) as provided in step (a).
[0200] Another aspect of the present invention relates to a process for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and / or for inhibiting or preventing the growth of one or more microorganisms on / in a surface comprising or consisting of the following steps:
[0201] (a) Providing a mixture as defined herein or the constituents (i) and (ii) as defined herein or a product as defined herein, and
[0202] (b) bringing the mixture or constituents or product provided in step (a) in contact with a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, on which the growth of one or more microorganisms is to be inhibited or prevented and / or in contact with a surface on / in which the growth of one or more microorganisms is to be inhibited or prevented.
[0203] A preferred embodiment relates to a process for inhibiting or preventing the growth of one or more microorganisms on / in a surface comprising or consisting of the following steps:
[0204] (a) Providing a mixture as defined herein or the constituents (i) and (ii) as defined herein or a product as defined herein, and
[0205] (b) bringing the mixture or constituents or product provided in step (a) in contact with a surface on / in which the growth of one or more microorganisms is to be inhibited or prevented.
[0206] Another aspect of the present invention relates to the use of a compound of formula (II) or of a mixture of two or more compounds of formula (II) or of a composition or product (preferably as defined herein) comprising one or more compound(s) of formula (II) wherein X is selected from the group consisting of and wherein n = 1 , R1is selected from the group consisting of -H and -OH, and R2is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and
[0207] -CH(OH)-CH(OH)-CH2(OH), preferably R2is selected from the group consisting of -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), or wherein n = 1 , R1is -OH, and R2and the -OH group shown in formula (II) are joined together to form the following compound of formula (l-a): wherein n = 1 , R1and R2are joined together to form the following compound of formula (I- b):
[0208] (l-b) or wherein n = 2-10, preferably 3-10, more preferably 4-10, R1is -OH, and R2= -H, as an antimicrobial agent, preferably
[0209] (i) for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and / or
[0210] (ii) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, and / or
[0211] (iii) for inhibiting or preventing the growth of one or more microorganisms on a surface.
[0212] According to a preferred embodiment, the compound of formula (II) or mixture or composition or product as defined herein is used is as an antimicrobial agent, preferably (i) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, and / or
[0213] (ii) for inhibiting or preventing the growth of one or more microorganisms on a surface. Another aspect of the present invention relates to use of one or more compound(s) selected from the group consisting of and / or of one or more compound(s) of formula (II) wherein X is selected from the group consisting of and n = 2-10, preferably 3-10, more preferably 4-10, R1is -OH, and R2= -H, as antimicrobial agent(s), preferably
[0214] (i) for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and / or
[0215] (ii) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, and / or
[0216] (iii) for inhibiting or preventing the growth of one or more microorganisms on a surface. Preferred is the use of one or more compound(s) selected from the group consisting of
[0217] as antimicrobial agent(s), preferably
[0218] (i) for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and / or
[0219] (ii) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, and / or
[0220] (iii) for inhibiting or preventing the growth of one or more microorganisms on a surface.
[0221] Another aspect of the present invention relates to a compound as defined herein for use as an antimicrobial agent, preferably for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin.
[0222] Another aspect of the present invention relates to a process (i) for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and / or (ii) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, and / or (iii) for inhibiting or preventing the growth of one or more microorganisms on / in a surface, comprising or consisting of the following steps:
[0223] (a) Providing a compound of formula (II) or a mixture of two or more compounds of formula (II) or a composition or product (preferably as defined herein) comprising one or more compound(s) of formula (II) wherein X is selected from the group consisting of and wherein n = 1 , R1is selected from the group consisting of -H and -OH, and R2is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), preferably R2is selected from the group consisting of -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH), or wherein n = 1 , R1is -OH, and R2and the -OH group shown in formula (II) are joined together to form the following compound of formula (l-a): or wherein n = 1 , R1and R2are joined together to form the following compound of formula (l-b):
[0224] (l-b) or wherein n = 2-10, preferably 3-10, more preferably 4-10, R1is -OH, and R2=
[0225] -H,
[0226] (b) bringing the compound or mixture or composition or product provided in step (a) in contact with (i) a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, on which the growth of one or more microorganisms is to be inhibited or prevented and / or in contact with (ii) the other ingredients of the product or semi-finished product in which the growth of one or more microorganisms is to be inhibited or prevented and / or in contact with (iii) a surface on / in which the growth of one or more microorganisms is to be inhibited or prevented.
[0227] Another aspect of the present invention relates to a process (i) for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and / or (ii) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined herein, and / or (iii) for inhibiting or preventing the growth of one or more microorganisms on / in a surface, comprising or consisting of the following steps:
[0228] (a) Providing one or more compound(s) selected from the group consisting of:
[0229]
[0230] 10 wherein X is selected from the group consisting of and n = 2-10, preferably 3-10, more preferably 4-10, R1is -OH, and R2= -H,
[0231] (b) bringing the compound(s) provided in step (a) in contact with (i) a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, on which the growth of one or more microorganisms is to be inhibited or prevented and / or in contact with (ii) the other ingredients of the product or semifinished product in which the growth of one or more microorganisms is to be inhibited or prevented and / or in contact with (iii) a surface, on / in which the growth of one or more microorganisms is to be inhibited or prevented.
[0232] According to a preferred embodiment, one or more compounds selected from the group consisting of
[0233] are provided in step (a) of the process. (Preferred) embodiments of the mixtures according to the invention correspond to or can be derived from the (preferred) embodiments of the products according to the invention which are explained above or vice versa. (Preferred) embodiments of the mixtures according to the invention correspond to or can be derived from the (preferred) embodiments of the uses according to the invention which are explained above or vice versa. (Preferred) embodiments of the mixtures according to the invention correspond to or can be derived from the (preferred) embodiments of the processes according to the invention which are explained above or vice versa. (Preferred) embodiments of the uses according to the invention correspond to or can be derived from the (preferred) embodiments of the processes according to the invention which are explained above or vice versa. Moreover, the (preferred) embodiments described herein can be arbitrarily combined with each other as long as technically sensible.
[0234] The invention will now be described in more detail hereinafter with references to the examples. Further aspects of the present invention are disclosed in the accompanying claims. Unless otherwise stated, all values refer to weight-% (wt.%).
[0235] Examples:
[0236] 1. Compounds
[0237] The compounds of formulae (I) and (II) can be obtained, for instance, by following the synthetic approaches described in Synthesis, 2003, (15), 2373-2377; Journal of the Korean Chemical Society, 2002, 46(5); Tetrahedron Letters, 2015, 56(15), 1973-1975; and JP2011207990A.
[0238] The compounds of formulae (I) and (II) are accessible not only via precursors of petrochemical origin, but advantageously also in a sustainable and / or cost-efficient way from biobased starting materials comprising only non-fossil fuel-based carbon. Assessment of the biobased carbon in a material can be performed through standard test methods. Using radiocarbon and isotope ratio mass spectrometry analysis, the biobased content of materials can be determined. ASTM International, formally known as the American Society for Testing and Materials, has established a standard test method for assessing the biobased content of materials. The ASTM method is designated ASTM D6866. According to a preferred embodiment of the present invention, more than 50% of the carbon atoms contained in a compound of formula (I) are biobased, based on the total number of carbon atoms contained in said compound of formula (I). More preferably, more than 60%, 70%, 75%, 80%, 85%, or 90% of the carbon atoms contained in a compound of formula (I) are biobased, based on the total number of carbon atoms contained in said compound of formula (I). According to another preferred embodiment of the present invention, more than 50% of the carbon atoms contained in a compound of formula (II) are biobased, based on the total number of carbon atoms contained in said compound of formula (II). More preferably, more than 60%, 70%, 75%, 80%, 85%, or 90% of the carbon atoms contained in a compound of formula (II) are biobased, based on the total number of carbon atoms contained in said compound of formula (II).
[0239] 2. Testing of Minimum Inhibitory Concentration
[0240] The Minimum Inhibitory Concentration (MIC) test is a test on growth inhibition. The estimation of MICs is executed in 96 well plates. Through the comparison of bacterial growth with positive and negative controls via optical density (OD), different concentrations of given test substances are evaluated.
[0241] Bacteria were cultivated under adjusted conditions based on information of the German Collection of Microorganisms and Cell Cultures (DSMZ) and stored in 10 % or 50 % glycerol prior to use. Afterwards, the following method was applied: Growth medium (according to microorganism) was added to each well of the microplate. Then, the test-substances, dissolved in DMSO, were added in different concentrations, positive controls (water controls only with medium), solvent controls (DMSO controls only with medium), and negative controls (benchmarks according to organism). Finally, the microorganisms were added in a concentration of 1 to 6 x 106CFU I ml (CFU = colony forming units). The incubation of the microplates was carried out at appropriate conditions.
[0242] According to the resulting growth, substance concentrations are labelled either as inhibiting or not and MIC is defined as the lowest concentration where a complete growth inhibition is visible. Experiments are performed at least twice.
[0243] The synergistic activity of the compounds of formula (I) or (II) in combination with different further antimicrobial agents was determined by measuring the Minimum Inhibitory Concentrations (MIC) according to the method as described above.
[0244] To verify that the tested combinations act synergistically against microorganisms, corresponding experiments were conducted with selected organisms from the list of Staphylococcus aureus, Candida albicans, Aspergillus brasiliensis, Pseudomonas aeruginosa and Escherichia coll. The synergistic activities of the compounds of formula (I) or (II) and different further antimicrobial agents in a mixture of 1 :1 were determined by measuring the MIC of the mixtures and compare the determined MICs of the mixtures with the MICs of the pure substances, respectively. The calculation of a synergy index gave a quantitative indication of the synergistic effects.
[0245] To calculate the synergy index with MIC values, the Kull equation was used as follows:
[0246] Table 12
[0247] Table 13
[0248] Table 14
[0249] Table 15
[0250] Table 16
[0251] Table 17 Table 18: *The MIC value of 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone (hydroxyethoxyphenyl butanone) was determined as being larger than 10000. For the calculation, a MIC value of 10000 was used. The respective SI value is calculated as 0.75. The actual SI value will be lower.
[0252] Table 19
[0253] Table 20
[0254] Table 21: *The MIC value of hydroxyethoxyphenyl butanol was determined as being larger than 30000. For the calculation, a MIC value of 30000 was used. The respective SI value is calculated as 0.58. The actual SI value will be lower.
[0255] Table 22
[0256] Table 23 Table 24
[0257] Table 25
[0258] Table 26: *The MIC value of hydroxyethoxyphenyl butanol was determined as being larger than 30000. For the calculation, a MIC value of 30000 was used. The respective SI value is calculated as 0.88. The actual SI value will be lower.
[0259] Table 27
[0260] Table 28
[0261] 3. Formulation examples
[0262] Cosmetic formulations (compositions) - amounts are indicated as % by weight for all formulations.
[0263] DEODORANTS Table 29: Deodorant Spray with ACH Table 30: Sport Fit Deo
[0264] Table 31 : Deodorant Aerosol Table 32: Antiperspirant stick
[0265] Table 33: Deodorant Roll-on GELS
[0266] Table 34: Cold & Hot Firming Gel with Thermolat & Frescolat
[0267] Table 35: After Sun Refreshing Gel
[0268] Table 36: Anti-wrinkle gel
[0269] Table 37: Cleansing Micellar Gel
[0270] HAIR CARE Table 38: Sprayable hair conditioner with zinc pyrithrione, leave-on
[0271] Table 39: Detox Refreshing Spray for Hair
[0272] Table 40: Hair Refresher Mist
[0273] EMULSIONS
[0274] Table 41 : Cream o / w
[0275] Table 42: Hand and body cream
[0276] Table 43: Body lotion
[0277] Table 44: Antibacterial body lotion, sprayable
[0278] Table 45: Barrier repair cream
[0279] Table 46: Detox Face Primer
[0280] Table 47: Emulsion with low emulsifier content
[0281] Leave on w / o
[0282] Table 48: Baby Erythema Cotton Cream Table 49: Weather Protection Cream
[0283] Table 50: Natural Night Cream Aloe SUN CARE
[0284] Table 51 : Sun protection milk (w / o)
[0285] Table 52: Sunscreen lotion (o / w. broadband protection)
[0286] Table 53: Anti-Wrinkle Day Emulsion exp. SPF 15
[0287] Table 54: Daily face cream SPF 20
[0288] Table 55: Refreshing Gel Sunscreen, with exp. SPF 30, UVA / UVB balanced
[0289] Table 56: Sun protection soft cream (w / o), SPF 40 Table 57: Light Sunscreen Fluid, exp. SPF 50
[0290] Table 58: Tinted Sunscreen cream against hyperpigmentation exp. SPF 50*
[0291] Table 59: Glow Brightener, expected SPF 50plus*
[0292] WIPES
[0293] Table 60: PEG-free Wet Wipe
[0294] Table 61 : Baby Soft Wet Wipes Table 62: After-Shave Wipes
[0295] Table 63: Cool Sebum Control Cleanser MASKS
[0296] Table 64: Glow Dream Mask
[0297] Table 65: Sheet mask - New Skin
[0298] Table 66: Detox Mask
[0299] Table 67: Sheet mask - Ultra Calming
[0300] Table 68: Watermelon Face Mask & Scrub
[0301] Table 69: Illuminating Snow MASK with Glacier Water
[0302] Concentrates & Solid formulations: Table 70: Natural Beauty Enhancer (Solid concentrate)
[0303] Table 71 : Solid Body Oil
[0304] Table 72: Night SERUM Table 73: Eye contour serum
[0305] Table 74: Advanced Lifting serum
[0306] Table 75: Illumination effect serum
[0307] Table 76: All in one bar- Shampoo-body-beard HAND CARE
[0308] Table 77: Hygiene & Care Hand Cream
[0309] GLASSCLEANER
[0310] Table 78: Alcohol free glass cleaner
[0311] Table 79: Glass cleaner
[0312] Table 80: Refill concentrate
[0313] Table 81 : Effective glass cleaner ALL PURPOSE AND FLOOR CLEANERS
[0314] Table 82: All purpose cleaner
[0315]
[0316] Table 83: All Purpose Cleaner Test formulation pH 6.5
[0317] Table 84: Floor Cleaner
[0318] Table 85: Floor Cleaner with gloss
[0319] Table 86: Simple floor cleaner
[0320] KITCHEN CLEANERS
[0321] Table 87: Power fat solvent
[0322] HAND DISH WASH LIQUID (HDWL)
[0323] Table 88: Simple hand dish wash liquid Table 89: Antibacterial HDWL Table 90: High performance HDWL with enzymes
[0324] Table 91 : HDWL
[0325] Table 92: HDWL
[0326] LIQUID DETERGENTS Table 93: Color detergent Nature liquid
[0327] Table 94: Compact liquid detergent
Claims
Claims:1 . Mixture comprising or consisting of(i) one or more compound(s) of formula (I)wherein X is selected from the group consisting ofan and wherein R1is selected from the group consisting of -H and -OH, and R2is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and H(OH)-CH(OH)-CH2(OH)wherein R1is -OH and R2and the -OH group shown in formula (I) are joined together to form the following compound of formula (l-a):wherein R1and R2are joined together to form the following compound of formula (l-b):(l-b) and (ii) one or more further antimicrobial agent(s), preferably wherein the total amounts of constituents (i) and (ii), respectively, contained in the mixture are such that constituent (i) synergistically improves the antimicrobial effect of constituent (ii) and / or that constituent (ii) synergistically improve(s) the antimicrobial effect of constituent (i).
2. Mixture according to claim 1 , wherein the one or more compound(s) of formula (I) of constituent (i) is / are selected from the group consisting of3. Mixture according to claim 1 or 2, wherein the one or more further antimicrobial agent(s) of constituent (ii) is / are(ii-1) selected from the group consisting of 1 ,2-decanediol (Decylene Glycol), 1 ,2- heptanediol, 1 ,2-hexanediol, 1 ,2-nonanediol, 1 ,2-octanediol, 1 ,2-pentanediol, 1 ,2-propanediol, 1 ,3-propanediol, 2,3-decanediol, 2,3-heptanediol, 2,3- hexanediol, 2,3-nonanediol, 2,3-octanediol, 2,3-pentanediol, 2- benzylheptanol, 2-hydroxyacetophenone, 2-methyl 5-cyclohexylpentanol, 3- hydroxypropyl 2-hydroxybenzoate, 4-hydroxyacetophenone, alkyl (C 12-22) trimethyl ammonium bromide and chloride, anisic acid and salts thereof, anisic acid 3-hydroxypropylester, ascorbic acid and salts thereof, ascorbyl palmitate, azelaic acid, azeloyl diglycinate, benzalkonium bromide,benzalkonium chloride, benzalkonium saccharinate, benzethonium chloride, benzoic acid, benzoic acid 3-hydroxypropylester, benzyl alcohol, benzyl salicylate, benzysothiazolinone, bisabolol, bronopol (2-bromo-2-nitropropane- 1 ,3-diol), butylene glycol, butylparaben, camphor, caprylhydroxamic acid, capryloyl glycine, capryloyl / caproyl anhydro methyl glucamide, caprylyl glyceryl ether, caprylyl / capric triglyceride, cetylpyridinium chloride, chlorhexidine, chlorhexidine diacetate, chlorhexidine digluconate, chlorhexidine dihydrochloride, chlorocresol, chloroxylenol, chlorphenesin, citronellyl methylcrotonate, climbazole, cyclohexylglycerin, dehydroacetic acid, diazolidinyl urea, dimethyl phenylbutanol, dimethyl phenylpropanol, dipropylene glycol, disodium EDTA, DMDM hydantoin, ethanol, ethyl lauroyl arginate HCI, ethyl lauroyl arginate laurate, ethylhexylglycerin, ethylparaben, eucalyptol, farnesol, garcinia mangostana peel extract, gluconic acid and salts thereof, glycerine, glyceryl caprate, glyceryl caprylate, glyceryl heptanoate, glyceryl laurate, glyceryl undecylenate, glycolipids, heptylglycerin, hexamidine, hexamidine diisethionate, hexylene glycol, hexylglycerin, hydroxyethoxyphenyl butanol, hydroxyethoxyphenyl butanone, imidazolidinyl urea, iodopropynyl butylcarbamate, isoamyl laurate, isobutylparaben, isopropylparaben, itaconic acid and salts thereof, jasmol, lactic acid, lauryl alcohol, levulinic acid, mandelic acid, mannitol, menthol, methyl salicylate, methyl undecylenate, methylbenzyl alcohol, methylchloroisothiazolinone, methylheptylglycerin, methylisothiazolinone, methylparaben and salts thereof, methylpropanediol, morinda citrifolia callus culture lysate, octenidine HCI, octylisothiazolinone, o-cymen-5-ol , panthenol, PCA ethyl cocoyl arginate, phenethyl alcohol, phenoxyethanol, phenylpropanol, piroctone olamine, polyarginine, polyglyceryl-10 laurate, polyglyceryl-2 caprate, polyglyceryl-3 caprylate, polyglyceryl-4 caprylate / caprate, polyglyceryl-4 laurate / sebacate, polylysine, potassium sorbate, propanediol caprate, propanediol caprylate, propanediol laurate, propanediol undecylenate, propylene glycol, propylene glycol caprylate, propylparaben, raspberry ketone, saccharide isomerate, salicylic acid, salvia officinalis (sage) oil, silver chloride, silver citrate, sodium anisate, sodium benzoate, sodium caproyl lactylate, sodium caproyl / lauroyl lactylate, sodium ethylparaben, sodium lactate, sodium lauroyl lactylate, sodium levulinate, levulinic acid, sodium methylparaben, sodium phytate, phytic acid, sodium propylparaben, sorbic acid, sorbitan caprylate, sorbitol, TEA-salicylate, tetraselmis extract, tetrasodium glutamate diacetate, thymol, triclocarban, triclosan, triethyl citrate, trisodium dicarboxy methyl alaninate, trisodium ethylenediamine disuccinate, tropolone, undecylenic acid, undecylenoyl glycine, xylityl caprylate, xylityl sesquicaprylate, zinc citrate, zinclactate, zinc neodecanoate, zinc pyrithione, zinc ricinoleate, and capryloyl / caproyl anhydro methyl glucamide (and) water.
4. Mixture according to any of the preceding claims, wherein the one or more compound(s) of formula (I) of constituent (i) is / are selected from the group consisting ofand wherein the one or more further antimicrobial agent(s) of constituent (ii) is / are(ii-6) selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2- heptanediol, 1 ,3-propanediol, caprylhydroxamic acid, chlorphenesin, glyceryl caprylate, hydroxyethoxyphenyl butanone, and methylheptylglycerin.
5. Product comprising a mixture according to any of the claims 1 to 4, preferably wherein the product is selected from the group consisting of personal care products, pharmaceutical products, and household products, more preferably wherein the product is i. in the form of a dispersion comprising an oil component in an amount of > 1 wt.%, preferably in an amount of > 3 wt.%, preferably in the form of an emulsion, more preferably an O / W emulsion, a W / O emulsion, a multiple emulsion, a hydrodispersion gel, a balm, a multiple emulsion of the water-in- oil type (W / O / W) or of the oil-in-water type (O / W / O), a PIT emulsion, a Pickering emulsion, a micro-emulsion, a liquid, a lotion, a suspension, a milk, an ointment, a paste, a gel, a cream-based, an oil-based or a liposome-based formulation; ii. in the form of a liquid surfactant formulation;Hi. in the form of a solid surfactant formulation; oriv. in the form of an aqueous or aqueous / alcoholic, preferably aqueous / ethanolic solution or aqueous / glycolic, solution.
6. Product according to claim 5, wherein the personal care product is selected from the group consisting of deodorant products, body care and cleansing products, intimate care and cleansing products, foot care and cleansing products, oral care and cleansing products, scalp care and cleansing products, and face care and cleansing products, more preferably wherein the personal care product is selected from the group consisting of deodorant sprays, deodorant roll-ons, deodorant sticks, deodorant creams, foot creams, body washes, mouth washes, toothpastes, shampoos, hair conditioner, styling wax, styling gels, styling foams, styling creams, styling mousses, styling serums, styling pomades, micellar waters, intimate washes, cleansers, toners, serums, moisturizers, eye creams, balms, soaps, facial masks, sunscreens, liquids for wet wipes, primers, concealers, foundations, rouges, bronzers, highlighters, eyebrow pencils, eyebrow creams, eyebrow waxes, eyebrow gels, eyebrow powders, eyeshadows, eyeliners, mascara, lipsticks, lip glosses, lip liners, lip balms, face powders, setting powders, setting sprays, and nail polishes, and / or wherein the household product is selected from the group consisting of alcohol free glass cleaners, glass cleaners, all-purpose cleaners, all-purpose sprays, degreasers, carpet cleaners, wood cleaners, floor cleaners, laminate cleaners, vinyl cleaners, ceramic cleaners, cork cleaners, linoleum cleaners, porcelain cleaners, stone cleaners, concrete cleaners, parquet cleaners, high gloss floor cleaners, kitchen cleaners, fat solver cleaners, bathroom cleaners, toilet cleaners, chalk cleaners, automatic dish washes, hand dish wash fluids, antibacterial hand dish wash fluids, fabric softeners, fabric care, liquid laundry detergents, powder laundry detergents, and hygiene wash detergents, and / or wherein the pharmaceutical product is selected from the group consisting of deodorant sprays, deodorant roll-ons, deodorant sticks, deodorant creams, foot creams, body washes, mouth washes, toothpastes, shampoos, intimate washes, cleansers, serums, moisturizers, eye creams, balms, soaps, facial masks, sunscreens, and liquids for wet wipes.
7. Product according to claim 5 or 6 comprising from 0.001 to 15 wt.%, preferably from 0.01 to 10 wt.%, more preferably from 0.05 to 2.5 wt.%, most preferably from 0.1 to 1 wt.%, of the mixture according to any of the claims 1 to 4, based on the total weight of the product.
8. Use of(i) one or more compound(s) of formula (I)wherein X is selected from the group consisting ofan and wherein R1is selected from the group consisting of -H and -OH and R2is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and - CH(OH)-CH(OH)-CH2(OH)wherein R1is -OH and R2and the -OH group shown in formula (I) are joined together to form the following compound of formula (l-a):or wherein R1and R2are joined together to form the following compound of formula (l-b):(l-b) to, preferably synergistically, improve the antimicrobial effect of(ii) one or more further antimicrobial agent(s), and / or use of (ii) one or more further antimicrobial agent(s) to, preferably synergistically, improve the antimicrobial effect of (i) one or more compound(s) of formula (I).
9. Use according to claim 8, wherein the, preferably synergistically, improved antimicrobial effect is one or more effect(s) selected from the group consisting of an antibacterial effect, an antiviral effect, an antifungal effect, preferably an anti-yeast and / or anti-mold effect.
10. Use according to claim 8 or 9, wherein the antimicrobial effect is achieved against one or more microorganism(s) selected from the group consisting of bacteria and fungi, preferably gram positive and gram negative bacteria, yeasts and filamentous fungi, more preferably selected from the group consisting of Staphylococcus aureus, Candida albicans, Aspergillus brasiliensis, Pseudomonas aeruginosa and Escherichia coli.
11. Use of a mixture as defined in any of the claims 1 to 4 as an antimicrobial agent, preferably(a) for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, and / or(b) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined in any of the claims 5 to 7, and / or(c) for inhibiting or preventing the growth of one or more microorganisms on a surface.
12. Process for, preferably synergistically, improving the antimicrobial effect of one or more compound(s) as defined in step (a) and / or of one or more compound(s) as defined in step (b) comprising or consisting of the following steps:(a) Providing one or more compound(s) of formula (I)wherein X is selected from the group consisting ofand wherein R1is selected from the group consisting of -H and -OH and R2is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH) or wherein R1is -OH and R2and the -OH group shown in formula (I) are joined together to form the following compound of formula (l-a):or wherein R1and R2are joined together to form the following compound of formula (l-b):(b) providing one or more further antimicrobial agent(s), and(c) mixing the compounds provided in steps (a) and (b).
13. Process for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined in any of the claims 5 to 7, comprising or consisting of the following steps:(a) Providing(i) one or more compound(s) of formula (I)wherein X is selected from the group consisting ofwherein R1is selected from the group consisting of -H and -OH and R2is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH)wherein R1is -OH and R2and the -OH group shown in formula (I) are joined together to form the following compound of formula (l-a):wherein R1and R2are joined together to form the following compound of formula (l-b):(ii) one or more further antimicrobial agent(s), or providing a mixture of constituents (i) and (ii), and(b) providing the remaining ingredients of the product or semi-finished product, and(c) mixing the compounds provided in steps (a) and (b).
14. Process for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, and / or for inhibiting or preventing the growth of one or more microorganisms on / in a surface comprising or consisting of the following steps:(a) Providing a mixture as defined in any of claims 1 to 4 or the constituents (i) and (ii) as defined in any of the claims 1 to 4 or a product as defined in any of the claims 5 to 7, and(b) bringing the mixture or constituents or product provided in step (a) in contact with a mammal’s, preferably human’s, skin or mucosa, preferably skin, on which the growth of one or more microorganisms is to be inhibited or prevented and / or in contact with a surface on / in which the growth of one or more microorganisms is to be inhibited or prevented.
15. Use of one or more compound(s) selected from the group consisting ofand / or of one or more compound(s) of formula (II)wherein X is selected from the group consisting ofand n = 3-10, preferably 4-10, R1is -OH, and R2= -H, as antimicrobial agent(s), preferably(i) for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and / or(ii) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined in any of the claims 5 to 7, and / or(iii) for inhibiting or preventing the growth of one or more microorganisms on a surface.
16. Process (i) for inhibiting or preventing the growth of one or more microorganisms on a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, and / or (ii) for inhibiting or preventing the growth of one or more microorganisms in a product or semi-finished product, preferably in a product as defined in any of the claims 5 to 7, and / or (iii) for inhibiting or preventing the growth of one or more microorganisms on / in a surface, comprising or consisting of the following steps:(a) Providing one or more compound(s) selected from the group consisting of:wherein X is selected from the group consisting ofand n = 3-10, preferably 4-10, R1is -OH, and R2= -H,(b) bringing the compound(s) provided in step (a) in contact with (i) a mammal’s, preferably human’s, skin or mucosa, preferably skin, more preferably human axillary skin, on which the growth of one or more microorganisms is to be inhibited or prevented and / or in contact with (ii) the other ingredients of the product or semi- finished product in which the growth of one or more microorganisms is to be inhibited or prevented and / or in contact with (iii) a surface, on / in which the growth of one or more microorganisms is to be inhibited or prevented.