Highly concentrated monorhamnolipid solutions

Abstract

This invention relates to compositions comprising at least one dissolved monorhamnolipid at a very high concentration at a specific acidic pH, and to methods of its preparation and its uses.

Description

[0001] Field of invention This invention relates to compositions containing at least one monorhamnolipid in a dissolved state at a very high concentration at a specific acidic pH, and to its preparation method and its use.

[0002] Existing technology Rhamnolipids are surfactant glycolipids and metabolic products of certain microorganisms. They possess excellent properties as surfactants, such as strong foam formation, and are of great interest for a wide variety of technological applications.

[0003] Surfactants, primarily used in cosmetic formulations (such as shampoos and liquid soaps), household detergents, and dishwashing liquids, must be liquid at the product manufacturers' typical processing temperatures to sustain and enable their use in the manufacturers' respective piping systems and pumps. Therefore, the viscosity of the raw material should be relatively low to maintain simple and continuous delivery. Simultaneously, the highest possible surfactant concentration is required to allow for the preparation of environmentally friendly formulations with low water content.

[0004] EP3023431 discloses a composition comprising 30% to 70% by weight of at least one rhamnolipid and 30% to 70% by weight of water, wherein the weight percentages are based on the total composition, and wherein the composition has a pH of 5.5 to 7.0 at 25°C.

[0005] EP4155371 discloses the use of a composition comprising at least 92% by weight of monorhamnolipids for the preparation of non-cosmetic cleansing formulations, wherein the weight percentage is based on all rhamnolipids contained in the composition.

[0006] WO2015091294 discloses an antibacterial composition comprising rhamnolipin, wherein the rhamnolipin comprises at least 50% by weight of monorhamnolipin.

[0007] EP0597358 discloses a method for the quantitative purification of glycolipids, characterized by purifying the glycolipids by acidifying a glycolipid-containing solution to pH ≤ 5.0, subsequently heating the batch to 60°C-130°C, then cooling the batch to ≤ 50°C, and centrifuging the batch to precipitate the glycolipid-containing phase. Using this method, a solid suspension or paste with a high rhamnose glycolipid solid content between 30% and 40% by weight and very high viscosity is obtained.

[0008] EP2735605A1 discloses a method for separating rhamnolipids, the method comprising: A) providing an aqueous medium containing at least one rhamnolipid and having a pH less than 6; B) contacting the aqueous medium with at least one organic solvent to provide a multiphase system and separate the aqueous phase; C) increasing the pH to 6 or higher to provide a multiphase organic system; and D) separating the rhamnolipid-rich organic phase.

[0009] One drawback of this product form is the undesirable and relatively high viscosity decrease upon dilution. Another drawback is the reduced microbial stability at neutral pH.

[0010] To date, there is no available method that allows very high concentrations of rhamnolipids to be used, for example, as stock solutions for the preparation of end-consumer formulations.

[0011] One object of the present invention is to provide a rhamnolipin solution having an exceptionally high concentration of rhamnolipin.

[0012] Description of the invention Surprisingly, it has been found that a particularly highly concentrated monorhamnolipid solution can be obtained by the method according to the invention.

[0013] Therefore, the present invention provides a composition comprising at least one monorhamnolipid in a dissolved state, wherein the total content of the monorhamnolipid in a dissolved state is from 71.0% to 98.0% by weight, characterized in that the pH of the composition at 25°C is in the range of 2.5 to 4.2.

[0014] The present invention further provides a method for preparing a composition comprising at least one monorhamnolipid in a dissolved state.

[0015] One advantage of this invention is that, in the case of highly active ingredients, a smaller amount is required in the final formulation.

[0016] Another advantage of this invention is that the ionic strength of the rhamnolipid-based compositions can be kept very low. Therefore, the formulation personnel have high flexibility in adjusting the pH and salt content of the final formulation.

[0017] Another advantage of the present invention is that the composition has increased microbial stability.

[0018] Another advantage of the present invention is that the composition can be easily diluted because the rhamnolipin, as the active ingredient, is already in its dissolved state.

[0019] Another advantage of the present invention is that the composition can be thoroughly mixed with other surfactants.

[0020] Another advantage of the present invention is that the composition can be formulated into a concentrated final formulation (“concentrate”).

[0021] Another advantage of the present invention is that, due to its high concentration, the composition has a reduced tendency to foam, thus simplifying transportation and delivery.

[0022] Another advantage of the present invention is that the composition allows for the simple addition of, for example, hydrophobic components (e.g., oils).

[0023] Another advantage of the present invention is that the composition has high storage stability.

[0024] Another advantage of this invention is that no significant change in viscosity is observed when diluted with water.

[0025] Another advantage of the present invention is that the composition causes less contamination in the pipeline during its preparation and transportation, and therefore can be cleaned more easily.

[0026] Another advantage of the present invention is that the composition results in much lower energy consumption for its transport, and thus a lower CO2 footprint.

[0027] Another advantage of the present invention is that the composition exhibits a lower water content, thus making it easier to solubilize and / or add hydrophobic ingredients such as essential oils.

[0028] Another advantage of the present invention is that the composition can more effectively solubilize ceramide-based active ingredients (if not at all).

[0029] Another advantage of the present invention is that, compared to dirhamnolipids, the composition exhibits a lower foaming volume in water-based solutions.

[0030] Another advantage of the present invention is that the composition exhibits higher color stability compared to dirhamnolipids.

[0031] Another advantage of the present invention is that the composition exhibits a reduced odor compared to dirhamnolipids.

[0032] Another advantage of the present invention is that adding the composition to the formulation reduces the need for acid or the amount required for corresponding pH adjustment.

[0033] Another advantage of the present invention is that the composition can have a very low viscosity, and therefore can be easily handled, for example, by a pump.

[0034] Another advantage of the present invention is that the compositions of the present invention can be used to formulate formulations with low foaming properties, which can be used, for example, in dishwashing applications, eye makeup removers, and micellar water formulations.

[0035] The composition according to the invention comprises at least one monorhamnolipid in a dissolved state, wherein the total content of the monorhamnolipid in a dissolved state is 71.0% to 98.0% by weight, preferably 73.0% to 95.0% by weight, more preferably 75.0% to 85.0% by weight, wherein the weight percentage is based on the total composition, characterized in that the pH of the composition at 25°C is in the range of 2.5 to 4.2, preferably in the range of 3.0 to 3.9, more preferably in the range of 3.2 to 3.8, and most preferably in the range of 3.2 to 3.4.

[0036] Then, in the context of the description of the average below, unless otherwise stated, the average is the mean of multiples.

[0037] Unless otherwise stated, percentages are weight percentages. The same applies to parts per million (ppm).

[0038] In the cases described below, unless otherwise stated, the measurements were determined at a temperature of 25°C and a pressure of 1013 mbar.

[0039] When determining the content of rhamnolipids in the context of this invention, the mass of the non-salt form is taken into account; therefore, the weight of the corresponding cation is not considered.

[0040] In the context of this invention, the term "rhamnolipid" should preferably be understood specifically to compounds of general formula (I) and their salts. General Formula (I) in mRL = 2, 1, or 0. nRL = 1 or 0, R 1RL and R 2RL = Independent, identical or different organic residues, said organic residues having 2 to 24, preferably 5 to 13 carbon atoms, said organic residues being particularly optionally branched, optionally substituted, particularly hydroxylated, optionally unsaturated, particularly optionally mono-, di- or tri-unsaturated alkyl residues, preferably selected from pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH2). oThose with -CH, where o = 1 to 23, preferably 4 to 12. If nRL = 1, the glycosidic bond between the two rhamnose units is preferably in the α-configuration. The optically active carbon atom of the fatty acid is preferably present as an R-enantiomer (e.g., (R)-3-{(R)-3-[2-O-(α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxodecanoyl}oxodecanoate).

[0041] In the context of this invention, the term "dirhamnolipid" should be understood to mean a compound of general formula (I) or a salt thereof, where nRL=1.

[0042] In the context of this invention, the term "monorhamnetin" should be understood to mean a compound of general formula (I) or a salt thereof, where nRL=0.

[0043] Different rhamnolipides are abbreviated according to the following nomenclature: “BiRL-CXCY” is understood to refer to a dirhamnolipid of general formula (I), where mRL=1 and residues R 1RL and residue R 2RL One of them is (CH2) o -CH3, where o=X-4, and the remaining residues R 1RL or R 2RL =(CH2) o -CH3, where o=Y-4.

[0044] “monorol-CXCY” is understood to refer to a monorhamnolipid of general formula (I), where mRL=1 and residues R 1RL and residue R 2RL One of them is (CH2) o -CH3, where o=X-4, and the remaining residues R 1RL or R 2RL =(CH2) o -CH3, where o=Y-4.

[0045] Therefore, the naming convention used does not distinguish between "CXCY" and "CYCX".

[0046] For rhamnolipids where mRL=0, either single RL-CX or double RL-CX is used accordingly.

[0047] If one of the above indices X and / or Y carries a ":Z", then this means the corresponding residue R 1RL and / or R 2RL It is equivalent to an unbranched, unsubstituted hydrocarbon residue with X-3 or Y-3 carbon atoms and Z double bonds.

[0048] Methods for preparing the relevant rhamnolipids are disclosed, for example, in EP2786743 and EP2787065; if a mixture of dirhamnolipids and monorhamnolipids is obtained, they can be converted into monorhamnolipids using rhamnosidase.

[0049] Rhamnolipids available in the context of this invention can also be obtained from Pseudomonas ( ). Pseudomonas Fermentation of ), especially Pseudomonas aeruginosa ( Pseudomonas aeruginosa The product is produced by fermentation of the bacteria, preferably non-genetically modified cells, i.e., techniques disclosed in the 1980s, such as those described in EP0282942 and DE4127908. Rhamnolipids produced in Pseudomonas aeruginosa cells can also be used in the context of this invention, cells that have been genetically modified to produce higher rhamnolipid titers; such cells have been disclosed, for example, by Lei et al. in Biotechnol. Lett. 2020 Jun;42(6):997-1002.

[0050] Rhamnolipids produced by Pseudomonas aeruginosa are commercially available from Jeneil Biotech Inc., for example under the trademark Zonix; from Logos Technologies (the technology was acquired by Stepan), for example under the trademark NatSurFact; from Biotensidion GmbH, for example under the trademark Rhapynal; from AGAEtechnologies, for example under the names R90, R95, R95Md, R95Dd; from Locus Bio-EnergySolutions; and from Shanghai Yusheng Industry Co. Ltd., for example under the trademark Bio-201 Glycolipids.

[0051] Most of the products mentioned above are mixtures of dirhamnolipids and monorhamnolipids, which need to be converted into monorhamnolipids, for example, using rhamnosidase.

[0052] The compositions according to the invention comprise at least one monorhamnolipid in a dissolved state. In the context of this invention, the term "monorhamnolipid in a dissolved state" means that the compositions according to the invention comprise a specified amount of monorhamnolipid in liquid form such that the monorhamnolipid does not precipitate when centrifuged at 500g for 10 minutes.

[0053] However, of course, additional rhamnolipids exceeding the specified concentration range can be included in a sedimentable form.

[0054] Preferably, the monorhamnolipid in the dissolved state contained in the composition according to the invention is in an aqueous solution.

[0055] The preferred composition according to the invention is characterized in that the content of monorhamnolipid in the composition is from 85.0% to 100.0% by weight, preferably from 95% to 100.0% by weight, more preferably from 98.0% to 100.0% by weight, wherein the weight percentage is based on all rhamnolipids contained in the total composition.

[0056] The preferred composition according to the invention is characterized in that the monorhamnolipid comprises: 12% to 32% by weight of single RL-C8C10, 51% to 81% by weight of single RL-C10C10, 1% to 9% by weight of single RL-C10C12, 1% to 9% by weight of single RL-C10C12:1, The weight percentages are based on all monorhamnolipids contained in the composition.

[0057] The preferred composition according to the invention is characterized in that the composition has a viscosity of 0.3 to 5 Pas, preferably 0.5 to 3 Pas, particularly preferably 0.6 to 2 Pas, said viscosity being measured in a rheometer at 10 s. -1 The shear rate was measured.

[0058] The viscosity was measured using a rheometer (MCR 302, Anton Paar Germany) in a parallel plate measurement system. The upper plate had a diameter of 40 mm, the gap distance was 0.5 mm, and the measurement temperature was 25°C. The measurement ranged from 0.1 to 100 s. -1 It is carried out within the range of shear rates.

[0059] The composition according to the invention preferably contains at least one cosmetic active ingredient, said cosmetic active ingredient being preferably selected from ceramide and sphingosine bases.

[0060] The sphingosine bases are preferably selected from sphingosine, dihydrosphingosine, 6-hydroxysphingosine, and phytosphingosine.

[0061] The preferred composition according to the invention is characterized in that the cosmetic active ingredient is selected from the group consisting of, preferably, ceramide NP, ceramide AP, ceramide EOP, ceramide NDS, ceramide ADS, ceramide EODS, ceramide NS, ceramide AS, ceramide EOS, ceramide NH, ceramide AH and ceramide EOH, and preferably selected from the group consisting of, preferably, ceramide NP, ceramide AP, ceramide NS, ceramide EOP and ceramide EOS.

[0062] The preferred composition according to the invention is characterized in that the content of the cosmetic active ingredient (in particular at least one ceramide) is from 0.5% by weight to 10.0% by weight, preferably from 0.8% by weight to 7.0% by weight, more preferably from 1.2% by weight to 4.0% by weight, wherein the weight percentage is based on the total composition.

[0063] The composition according to the invention preferably contains at least one preservative.

[0064] Preferably, the composition according to the invention is characterized in that the preservative is selected from the group consisting of, and preferably from, the group consisting of: For anisic acid, benzoic acid, levulinic acid, sorbic acid, lactic acid, mandelic acid, salicylic acid, dehydroacetic acid, capryloyl hydroxamic acid, cinnamic acid, geraniic acid, nonanoic acid, and salts of the above acids. Methylparaben, ethylparaben Phenylacetol, benzyl alcohol, phenethyl alcohol, phenoxyethanol Propylene glycol, pentanediol, 1,2-hexanediol, octyl glycol, undecyl alcohol, methylpropanediol, Ethylhexylglycerol, n-octylglycerol, n-heptylglycerol, n-hexylglycerol, methylheptylglycerol Undecylaminopropyltrimethylammonium methyl sulfate, Isothiazolinones, preferably selected from chloromethylisothiazolinone (CIT), methylisothiazolinone (MIT), benzisothiazolinone (BIT), and butylbenzisothiazolinone (BBIT). Triethyl citrate, Citral Hydroxymethylglycine salt, glyceryl caprylate, Iodopropynyl butylcarbamate (IPBC), and Sodium hexanoyl / lauroyl lactylate.

[0065] Furthermore, the present invention provides a method for preparing a composition comprising at least one monorhamnolipid in a dissolved state, the method comprising the following steps: A) Provide a source composition comprising at least one monorhamnolipid, preferably wherein the content of said monorhamnolipid is from 0.5% to 15.0% by weight, more preferably from 5% to 14.0% by weight, and more preferably from 8.0% to 12.0% by weight, wherein said weight percentage is based on the total source composition. B) The pH of the source composition is reduced to a range of 1.8 to 3.5, preferably to a range of 2.2 to 3.4, more preferably to a range of 2.5 to 3.2, and most preferably to a range of 2.6 to 3.1, while obtaining a multiphase system. C) Remove the water-rich phase from the multiphase system, and The pH of the remaining fraction is increased, preferably to the range of 2.5 to 4.2, more preferably to the range of 3.0 to 3.9, more preferably to the range of 3.2 to 3.8, and most preferably to the range of 3.2 to 3.4.

[0066] Preferably, the composition according to the invention is prepared by the method according to the invention.

[0067] The preferred method according to the invention is characterized in that the content of monorhamnolipids in the source composition is 85.0% to 100.0% by weight, preferably 95% to 100.0% by weight, more preferably 98.0% to 100.0% by weight, wherein the weight percentage is based on all rhamnolipids contained in the total source composition.

[0068] Monorhamnolipids can be produced by fermentation methods using microorganisms known in the art. A preferred method according to the invention is characterized in that the source composition provided in step A) is a cell-free fermentation broth.

[0069] In the context of this invention, the term "cell-free" means that the cells of an organism producing monorhamnolipids have been removed, for example by centrifugation.

[0070] The preferred method according to the invention is characterized in that the pH value in step B) is reduced using an acid, particularly an inorganic acid, which is particularly preferably selected from HCl, H2SO4, nitric acid, phosphoric acid, and carbonic acid, especially HCl or H2SO4.

[0071] The preferred method according to the invention is characterized in that, in step C), the pH value is increased by an inorganic base or ammonia, wherein the inorganic base is particularly an alkaline earth metal base or an alkali metal base, preferably an aqueous solution, wherein NaOH and KOH are particularly preferred.

[0072] The inorganic base is preferably in the form of an aqueous solution with a concentration of 0.01M to 15M, more preferably 0.1M to 5M.

[0073] Furthermore, the present invention provides a composition comprising at least one monorhamnolipid in a dissolved state, said composition being obtainable by a method according to the invention. The composition according to the invention is preferably obtained by a method of the invention comprising steps A) to D).

[0074] Furthermore, the present invention provides a method for producing cosmetic or pharmaceutical formulations comprising monorhamnolipids and ceramides, the method comprising the following steps: I) Providing a composition according to the invention, wherein the composition comprises at least one ceramide and preferably at least one sphingosine base, II) The composition is formulated with at least one additional component selected from: emollients, emulsifiers, co-emulsifiers, thickeners, viscosity modifiers, stabilizers, water-soluble growth promoters, solids, fillers, pearlescent additives, opacifiers, insect repellents, self-tanning agents, surfactants, preservatives, conditioning agents, fragrances, colorants, cosmetic active ingredients, care additives, refatting agents, electrolytes, UV filters, and solvents.

[0075] The preferred method according to the invention is characterized in that the ceramide is selected from the group consisting of, preferably, ceramide NP, ceramide AP, ceramide EOP, ceramide NDS, ceramide ADS, ceramide EODS, ceramide NS, ceramide AS, ceramide EOS, ceramide NH, ceramide AH and ceramide EOH, and preferably selected from the group consisting of, preferably, ceramide NP, ceramide AP, ceramide NS, ceramide EOP and ceramide EOS.

[0076] The sphingosine base, preferably selected from sphingosine, dihydrosphingosine, 6-hydroxysphingosine, and phytosphingosine, is commonly included in the provided composition.

[0077] In method step II) of the method of the present invention, exemplary representatives of the various groups of the additional components are known to those skilled in the art and can be obtained, for example, from German application DE102008001788.4. This patent application is incorporated herein by reference and is therefore considered part of this disclosure.

[0078] Regarding the additional components and the amounts of the additional components used, reference is made explicitly to relevant manuals known to those skilled in the art, such as K. Schrader, “Grundlagen und Rezepturen der Kosmetika” [Cosmetic Fundamentals and Formulation], 2nd edition, pp. 329-341, Hüthig Buch Verlag, Heidelberg.

[0079] The amount of each additive depends on its intended use.

[0080] Typical starting formulations for relevant applications are known in the art and are, for example, included in the brochures of manufacturers of the relevant base materials and active substances. These existing formulations can generally be used as is. However, any necessary modifications for adjustment and optimization can be made directly through simple testing.

[0081] The preferred additional component in step II) of the method comprises water and preferably cholesterol.

[0082] In a preferred method according to the invention, a composition according to the invention is provided in step I), the composition comprising ceramide NP and phytosphingosine, preferably additionally comprising ceramide AP and ceramide EOP, and the additional component in step II) comprises water and preferably cholesterol.

[0083] Furthermore, the present invention provides the use of the compositions according to the invention in the preparation of end-user products, which are preferably formulations, particularly cleaning or care formulations, more preferably household care or cosmetic formulations. The cleaning formulations are preferably laundry formulations, dishwashing formulations, automotive cleaning formulations, hard floor cleaning formulations, glass cleaners, bathroom cleaners, kitchen cleaners, oven cleaners, general-purpose cleaners, wipes, metal cleaners, membrane cleaners for food and beverage applications, CIP (clean in place) cleaners, large kitchen cleaners, traffic film removers, carpet cleaners, alkaline cleaners, pre-stain removers, mild cleaners, or neutral cleaners.

[0084] Brief description of the attached figures Figure 1 : The foam volume of different test solutions over time.

[0085] The embodiments listed below describe the invention by way of example, but are not intended to limit the invention (the scope of which is obvious from the entire specification and claims) to the embodiments specified in the examples.

[0086] Example: Example 1: Preparation of highly concentrated monorhamnolipid Through *Pseudomonas putida* ( Pseudomonas putida Fermentation of strain pBBR1MCS2-Plac-rhIAB was performed to produce monorhamnolipids, similar to the *Pseudomonas putida* strain pBBR1MCS2-Plac-rhIABC-T-Ptac-rhIC-T described in EP2786743, but with the Bsu36I restriction site inserted directly after the stop codon of the rhlB gene, thus omitting rhlC. Pre-culture in shake flasks was performed as described in EP2598646. For the master culture, mineral medium (M9) was used. Fermentation was carried out in a 2-liter fermenter with a carbon-limited glucose feed. The glucose feed was controlled by dissolved oxygen (DO) signals. DO was adjusted to 20% saturation via a stirrer. The pH was adjusted to 7 via a pH electrode and the addition of 2M sulfuric acid or 20% by weight ammonia. To prevent excessive foaming of the fermentation broth, Dow Corning 1500 antifoaming agent was added as needed. The fermentation lasted for 4 days, reaching a dry biomass of 16 g / L. The concentration of monorhamnolipids was determined by HPLC and was 8.5 g / L.

[0087] After separating the cells by centrifugation at 10,000g, the pH of the fermentation broth was adjusted to 3.1 by adding concentrated H2SO4.

[0088] A multiphase composition was obtained, which was separated by centrifugation at 10,000 g, and the upper aqueous phase was discarded.

[0089] The remaining material was further processed.

[0090] The compositions listed in Table 1 were obtained by raising the pH using KOH (aqueous solution) and diluting with water to a given monorhamnolipid concentration; weight percentages are based on the total composition.

[0091] Viscosity was measured using a rheometer (MCR 302, Anton Paar Germany) in a parallel plate measurement system. The upper plate had a diameter of 40 mm, the gap distance was 0.5 mm, and the measurement temperature was 25 °C. The measurement range was from 0.1 to 100 s. -1 It is carried out within the range of shear rates.

[0092] Table 1: Viscosity (Pas, shear rate 10s) of monorhamnolipin compositions as a function of rhamnolipin concentration (wt%) and pH -1 )

[0093] Table 1 shows the viscosity of monorhamnolipid solutions based on pH and concentration.

[0094] At a concentration of 50% and a pH below 4, all samples exhibited phase separation, even leading to multiphase flow. In cases of phase separation (multiphase flow), viscosity could not be measured.

[0095] The sample is homogeneous at pH 4.0 or higher, and the viscosity decreases as pH increases.

[0096] At concentrations of 60% and 70%, phase separation is dominant.

[0097] At a concentration of 75.5%, the mixture did not exhibit phase separation at any of the listed pH values. Surprisingly, low viscosity was observed at pH 3.3. At this pH, a highly concentrated, low-viscosity rhamnolipid solution was provided.

[0098] A minimum viscosity was detected at pH 3.3, which was the lowest for all compositions, even when the mRL concentration was significantly reduced.

[0099] Example 2: Solubilization of ceramide 3B (i.e., NP) The solubility of monorhamnolipids was investigated by mixing them with ceramides.

[0100] The maximum amount of ceramide solubilized in monorhamnolipid was determined by adding ceramide to the mixture according to the invention and heating to 70°C. The maximum amount was determined by producing a mixture of clear formulations. The samples were evaluated by visual observation and additionally by microscopic analysis using polarized light. When no luminescence was observed in the sample, the solution was free of crystals and, by definition, clear.

[0101] In addition, turbidity values ​​were determined by turbidity measurement (HACH 2100AN IS Turbidimeter) in an 11 mm glass cuvette. All samples showing turbidity values ​​<30 NTU were assessed as non-turbid. After cooling to 20°C, the "clear mixture" must not become turbid again within a 2-day period.

[0102] Table 2 shows the dosage used for the combination.

[0103] Table 2: Examples of combinations of monorhamnolipids, dirhamnolipids, sophorolipids, and ceramides

[0104] According to the present invention Examples 2D and 2E did not yield clear solutions at pH 3.3.

[0105] Example 3: Preparation of cosmetic formulations containing ceramides and monorhamnolipids Composition 2C from Example 2 was used to prepare micelle gels and shampoo formulations based on a stock solution.

[0106] As described in Example 2, stock solutions of monorhamnolipids, ceramides, and other lipids were prepared. Additional components, such as the ceramides described above, were added: Table 3: Stock solutions of monorhamnolipids, ceramides, and other lipids

[0107] According to the present invention Micellar gels are prepared by using the aforementioned stock solution: Dilute xanthan gum in water. Use Ultra-Turrax. ® Mix phase A for 10 minutes (8000 rpm). Add all components of phase B, including the stock solution, in the given order, while stirring with a spatula. Adjust the pH to 6 with citric acid.

[0108] Table 4: Micellar Gels

[0109] Use the aforementioned stock solution to prepare a shampoo: Dissolve cationic guar gum in water. Add the ingredients, including the stock solution, in the given order and adjust the pH to 5.5.

[0110] Example 4: Evaluation of foaming properties using the SITA foam tester The foaming properties of surfactants and surfactant-based cleaning products are important attributes perceived by consumers. This parameter can be determined using the SITA Foam Tester R-2000 from SITA Messtechnik GmbH. In this device, air is introduced into a defined volume of surfactant solution via a special rotor to generate foam. Computer-controlled sensing technology measures the total volume of the liquid and the generated foam over time.

[0111] Compositions were prepared containing 0.5% by weight of total monorhamnolipid concentration, with a total hardness of 10°dH (German hardness), and pH values ​​of 6 and 7, respectively.

[0112] Two different monorhamnolipid concentrates from Table 1 above were used to prepare the compositions: 75%@pH3.3 and 50%@pH7.0.

[0113] According to the present invention To evaluate foaming performance, the foaming properties of 300 mL of each test solution were tested at a constant stirring speed of 1500 rpm for 10 seconds at 30°C. A total of eight such measurements were performed for each test solution. All samples were tested twice.

[0114] Figure 1 The foam volume for each test solution changes over time: Measurement parameters: Temperature: 30℃±0.5℃; Sample volume / measurement: 300mL; Concentration of test sample: 0.5% by weight (10°dH (German hardness)) in water, pH adjusted with NaOH; Stirring speed: 1500rpm; Stirring time: 10 seconds; Interval: 8; Number of repetitions: 2.

[0115] like Figure 1 As shown, compositions containing monorhamnolipin from a 75% @ pH 3.3 concentrate exhibit significantly lower foam volumes compared to monorhamnolipin from a 40% @ pH 7.0 concentrate. For the monorhamnolipin from the 40% @ pH 7.0 concentrate, the highest foam volume was observed at pH 7, and in stark contrast, for the monorhamnolipin from the 75% @ pH 3.3 concentrate, no foam volume was observed at the same pH value.

[0116] At pH 6, a similarly low foam volume was observed for monorhamnolipids from a 75%@pH 3.3 concentrate.

[0117] This result is desirable because low foam volume is preferred in many applications, such as eye makeup removers and micellar water formulations.

Claims

1. A composition comprising at least one monorhamnolipid in a dissolved state, wherein the total content of the monorhamnolipid in the dissolved state is 71.0% to 98.0% by weight, preferably 73.0% to 95.0% by weight, more preferably 75.0% to 85.0% by weight, wherein the weight percentage is based on the total composition, characterized in that... The composition has a pH in the range of 2.5 to 4.2 at 25°C, preferably in the range of 3.0 to 3.9, more preferably in the range of 3.2 to 3.8, and most preferably in the range of 3.2 to 3.

4.

2. The composition according to claim 1, characterized in that... The composition contains 85.0% to 100.0% by weight, preferably 95% to 100.0% by weight, and more preferably 98.0% to 100.0% by weight, wherein the weight percentage is based on all rhamnolipids contained in the total composition.

3. The composition according to claim 1 or 2, characterized in that... The monorhamnolipid comprises: 12% to 32% by weight of single RL-C8C10, 51% to 81% by weight of single RL-C10C10, 1% to 9% by weight of single RL-C10C12, 1% to 9% by weight of single RL-C10C12:1, The weight percentages are based on all monorhamnolipids contained in the composition.

4. The composition according to at least one of the preceding claims, characterized in that... The composition has a viscosity of 0.3 to 5 Pas, preferably 0.5 to 3 Pas, and particularly preferably 0.6 to 2 Pas, which is measured in a rheometer over 10 s. -1 The measurements were taken at the shear rate.

5. The composition according to at least one of the preceding claims, characterized in that... The composition contains at least one cosmetic active ingredient, which is preferably selected from ceramide and sphingosine bases.

6. The composition according to claim 5, characterized in that... The active ingredient in the cosmetic is selected from ceramide NP, ceramide AP, ceramide EOP, ceramide NDS, ceramide ADS, ceramide EODS, ceramide NS, ceramide AS, ceramide EOS, ceramide NH, ceramide AH and ceramide EOH, preferably selected from ceramide NP, ceramide AP, ceramide NS, ceramide EOP and ceramide EOS.

7. The composition according to claim 5 or 6, characterized in that... The content of the cosmetic active ingredient is from 0.5% to 10.0% by weight, wherein the weight percentage is based on the total composition.

8. The composition according to at least one of the preceding claims, characterized in that... The composition contains at least one preservative.

9. The composition according to claim 8, characterized in that... The preservative is selected from the following: For anisic acid, benzoic acid, levulinic acid, sorbic acid, lactic acid, mandelic acid, salicylic acid, dehydroacetic acid, capryloyl hydroxamic acid, cinnamic acid, geraniic acid, nonanoic acid, and salts of the above acids. Methylparaben, ethylparaben Phenylacetol, benzyl alcohol, phenethyl alcohol, phenoxyethanol Propylene glycol, pentanediol, 1,2-hexanediol, octyl glycol, undecyl alcohol, methylpropanediol, Ethylhexylglycerol, n-octylglycerol, n-heptylglycerol, n-hexylglycerol, methylheptylglycerol Undecylaminopropyltrimethylammonium methyl sulfate, Isothiazolinones, Triethyl citrate, Citral Hydroxymethylglycine salt, glyceryl caprylate, Iodopropynyl butylcarbamate, and Sodium hexanoyl / lauroyl lactylate.

10. A method for preparing a composition comprising at least one monorhamnolipid in a dissolved state, the method comprising the following steps: A) Provide a source composition comprising at least one monorhamnolipid, preferably wherein the content of said monorhamnolipid is from 0.5% to 15.0% by weight, more preferably from 5% to 14.0% by weight, and more preferably from 8.0% to 12.0% by weight, wherein said weight percentage is based on the total source composition. B) The pH of the source composition is reduced to a range of 1.8 to 3.5, preferably to a range of 2.2 to 3.4, more preferably to a range of 2.5 to 3.2, and most preferably to a range of 2.6 to 3.1, while obtaining a multiphase system. C) Remove the water-rich phase from the multiphase system, and D) Increase the pH of the remaining fraction, preferably to the range of 2.5 to 4.2, more preferably to the range of 3.0 to 3.9, more preferably to the range of 3.2 to 3.8, and most preferably to the range of 3.2 to 3.

4.

11. The method according to claim 10, characterized in that... The source composition provided in step A) is a cell-free fermentation broth.

12. The method according to claim 10 or 11, characterized in that... In step B), the pH value is lowered using an acid, particularly an inorganic acid, which is especially preferably selected from HCl, H2SO4, nitric acid, phosphoric acid, and carbonic acid, particularly HCl or H2SO4.

13. A composition comprising at least one monorhamnolipid in a dissolved state, said composition being obtainable by the method according to at least one of claims 10 to 12.

14. A method for preparing a cosmetic or pharmaceutical formulation, said formulation comprising a monorhamnolipid and a ceramide, said method comprising the following steps: I) Providing a composition according to any one of claims 1 to 9 and 13, wherein the composition comprises at least one ceramide and preferably at least one sphingosine base, II) Formulating the composition with at least one additional component selected from: Emollients, emulsifiers, co-emulsifiers, thickeners, viscosity modifiers, stabilizers, water-soluble growth promoters, solids, fillers, pearlescent additives, opacifiers, insect repellents, self-tanning agents, preservatives, conditioning agents, fragrances, colorants, cosmetic active ingredients, care additives, fatliquoring agents, electrolytes, UV filters, and solvents.

15. Use of the composition according to at least one of claims 1 to 9 or 13 for the preparation of an end-user product, wherein the end-user product is preferably a formulation, particularly a cleaning formulation or a care formulation, more preferably a home care formulation or a cosmetic formulation.

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