Rhamnolipide derivatives as emulsifiers and dispersing agents

Description

Field of invention

[0001] The invention relates to a dispersion, in particular an emulsion, containing at least one rhamnolipid derivative, and the use of the rhamnolipid derivatives as an emulsifier or dispersing agent. State of the art

[0002] Rhamnolipids are surfactants that can be produced by fermentation. They consist of one to two rhamnose units and one to three, usually β-hydroxy fatty acids. The fatty acids can be saturated or unsaturated.

[0003] The variation in chain length and quantity (congeners) of the fatty acid moieties has been described in several publications (Howe et al., FEBS J. 2006; 273(22):5101-12; Abdel-Mawgoud et al., Appl Microbiol Biotechnol, 86, 2010; pp. 1323-1336). Few covalent derivatives of the fatty acid moieties of rhamnolipids are known.

[0004] Miao et al., Journal of Surfactants and Detergents, 17 (6), 2014; 1069-1080, describes the synthesis of di-rhamnolipid ethyl ester by esterification with ethanol and the suitability of the esters as a non-ionic surfactant.

[0005] WO2001010447 and EP1889623 disclose the pharmaceutical and cosmetic uses of rhamnolipids and short-chain rhamnolipid esters (C1-C6; methyl to hexyl esters, linear or branched), especially in wound healing.

[0006] The object of the invention was to provide excellent emulsifiers or dispersing agents. Description of the invention

[0007] Surprisingly, it was found that the rhamnolipid derivatives described below, which are derivatized by a relatively long carbon chain or by substituents with a relatively large number of carbon atoms in total, exhibit excellent emulsifying and dispersing properties.

[0008] The subject matter of the present invention is therefore a dispersion containing at least one rhamnolipid derivative as described in claim 1. Field of invention

[0009] The invention relates to a dispersion, in particular an emulsion, containing at least one rhamnolipid derivative, and the use of the rhamnolipid derivatives as an emulsifier or dispersing agent. State of the art

[0010] Rhamnolipids are surfactants that can be produced by fermentation. They consist of one to two rhamnose units and one to three, usually β-hydroxy fatty acids. The fatty acids can be saturated or unsaturated.

[0011] The variation in chain length and quantity (congeners) of the fatty acid moieties has been described in several publications (Howe et al., FEBS J. 2006; 273(22):5101-12; Abdel-Mawgoud et al., Appl Microbiol Biotechnol, 86, 2010; pp. 1323-1336). Few covalent derivatives of the fatty acid moieties of rhamnolipids are known.

[0012] Miao et al., Journal of Surfactants and Detergents, 17 (6), 2014; 1069-1080, describes the synthesis of di-rhamnolipid ethyl ester by esterification with ethanol and the suitability of the esters as a non-ionic surfactant.

[0013] WO2001010447 and EP1889623 disclose the pharmaceutical and cosmetic uses of rhamnolipids and short-chain rhamnolipid esters (C1-C6; methyl to hexyl esters, linear or branched), especially in wound healing.

[0014] Abdel-Mawgoud et al. reveal the diversity of rhamnolipid structures and their microbial origin and role in Appl Microbiol Biotechnol. 2010 May, 86(5):1323-36. .

[0015] Miao et al. reveal the ethylation of di-rhamnolipids in Journal of Surfactants and Detergents, 2010 November, 17(6):1069-1080. .

[0016] The object of the invention was to provide excellent emulsifiers or dispersing agents. Description of the invention

[0017] Surprisingly, it was found that the rhamnolipid derivatives described below, which are derivatized by a relatively long carbon chain or by substituents with a relatively large number of carbon atoms in total, exhibit excellent emulsifying and dispersing properties.

[0018] The subject matter of the present invention is therefore a dispersion containing at least one rhamnolipid derivative as described in claim 1.

[0019] Another aspect of the invention is the use of these rhamnolipid derivatives as an emulsifier or dispersing agent.

[0020] One advantage of the rhamnolipid derivatives used in the present invention is their good biodegradability.

[0021] Another advantage of the present invention is that the rhamnolipid derivatives can be incorporated into the emulsion via the aqueous phase.

[0022] Another advantage of the present invention lies in the low skin-irritating effect of the rhamnolipid derivatives used.

[0023] Another advantage of the present invention lies in the low eye-irritating effect of the rhamnolipid derivatives used.

[0024] Another advantage of the present invention lies in the good dispersing effect of the rhamnolipid derivatives used towards decorative pigments and the resulting high color fastness of, for example, make-up products.

[0025] Another advantage of the present invention lies in its good emulsifying effect compared to organic UV filters and its good dispersing effect compared to inorganic UV filters.

[0026] Another advantage of the present invention is that after application of the emulsions according to the invention, the skin is less degreased.

[0027] Another advantage of the present invention is that the emulsions according to the invention can eliminate unwanted odors from the skin.

[0028] Another advantage of the present invention is that the emulsions according to the invention can improve skin elasticity.

[0029] Another advantage of the present invention is that the emulsions according to the invention are quickly absorbed into the skin and leave a light and pleasant feeling on the skin.

[0030] Another advantage of the present invention is that emulsions with low viscosities can be produced.

[0031] Another advantage of the present invention is that the emulsions according to the invention improve skin moisture.

[0032] Another advantage of the present invention is that the emulsions according to the invention exhibit good foamability in combination with other surfactants or non-derivatized mono- or di-rhamnolipid.

[0033] Another advantage of the present invention is that the rhamnolipid derivatives can also be used as co-emulsifiers in water-in-oil emulsions.

[0034] The terms "rhamnolipid" and "rhamnolipid ester" in connection with the present invention always also include their corresponding salts.

[0035] The terms "rhamnolipid" and "rhamnolipidamide" in connection with the present invention always also include their corresponding salts.

[0036] The term "mono-rhamnolipid" in connection with the present invention means compounds of the general formula (I) shown below with R 3< = H or their salts, in which n =0.

[0037] Distinct rhamnolipids are abbreviated according to the following nomenclature: "diRL-CXCY" refers to di-rhamnolipids of the general formula (I) with R 3< = H or their salts, in which one of the residues R 1< and R 2< = (CH 2 ) o -CH 3 with o = X-4 and the remaining residue R 1< or R 2< = (CH 2 ) o -CH 3 with o = Y-4.

[0038] The term "monoRL-CXCY" refers to mono-rhamnolipids of the general formula (I) with R 3< = H or their salts, in which one of the residues R 1< and R 2< = (CH 2 ) o -CH 3 with o = X-4 and the remaining residue R 1< or R 2< = (CH 2 ) o -CH 3 with o = Y-4.

[0039] The nomenclature used therefore does not distinguish between "CXCY" and "CYCX".

[0040] For rhamnolipids with m=0, monoRL-CX or diRL-CX is used accordingly.

[0041] If one of the above-mentioned indices X and / or Y is marked with ":Z", this means that the respective residue R 1< and / or R 2< = represents an unbranched, unsubstituted hydrocarbon residue with X-3 or Y-3 carbon atoms and Z double bonds.

[0042] Analogous nomenclature is used for rhamnolipid esters in the form di / monoRL-CXCY:Z-ester.

[0043] The "pH value" in connection with the present invention is defined as the value which is measured for the corresponding substance at 25 °C after five minutes of stirring with a pH electrode calibrated according to ISO 4319 (1977).

[0044] All percentages (%) are mass percentages unless otherwise stated.

[0045] The present invention relates to a dispersion containing at least A) a rhamnolipid derivative selected from the group consisting of rhamnolipid esters of general formula (I) and rhamnolipid amides of general formula (II) general formula (I), where m = 2, 1 or 0, in particular 1 or 0, n = 1 or 0, in particular 1, R 1< = organic residue with 2 to 24, preferably 5 to 13 carbon atoms, in particular optionally branched, optionally substituted, in particular hydroxy-substituted, optionally unsaturated, in particular optionally singly, doubly or triply unsaturated, alkyl residue, preferably one selected from the group consisting of pentenyl, heptenyl, nonenyl, undekenyl and tridekenyl and (CH 2 ) o-CH 3 with o = 1 to 23, preferably 4 to 12, R 2< = independent of each other identical or different organic residue with 2 to 24, preferably 5 to 13 carbon atoms, in particular optionally branched, optionally substituted, in particular hydroxy-substituted, optionally unsaturated, in particular optionally singly, doubly or triply unsaturated, alkyl residue, preferably such selected from the group consisting of pentenyl, heptenyl, nonenyl,Undekenyl and tridekenyl and (CH₂)₂o-CH₃ with o = 1 to 23, preferably 4 to 12, and R₃< = aliphatic residue with 7 to 32 carbon atoms, preferably 8 to 24 carbon atoms, particularly preferably 10 to 22 carbon atoms, , which is selected from the group of residues R 3< directly derived from R 3< OH = natural fatty alcohol, general formula (II), where m = 2, 1 or 0, in particular 1 or 0, n = 1 or 0, in particular 1, R 1< = organic residue with 2 to 24, preferably 5 to 13 carbon atoms, in particular optionally branched, optionally substituted, in particular hydroxy-substituted, optionally unsaturated, in particular optionally singly, doubly or triply unsaturated, alkyl residue, preferably one selected from the group consisting of pentenyl, heptenyl, nonenyl, undekenyl and tridekenyl and (CH 2 ) o-CH 3 with o = 1 to 23, preferably 4 to 12, R 2< = independent of each other identical or different organic residue with 2 to 24, preferably 5 to 13 carbon atoms, in particular optionally branched, optionally substituted, in particular hydroxy-substituted, optionally unsaturated, in particular optionally singly, doubly or triply unsaturated, alkyl residue, preferably such selected from the group consisting of pentenyl, heptenyl, nonenyl,Undekenyl and tridekenyl and (CH₂)₂o-CH₃ with o = 1 to 23, preferably 4 to 12, R₃a< = organic residue with 1 to 32, preferably 8 to 24, particularly preferably 10 to 22, carbon atoms, and R₃b< = organic residue with 1 to 32, preferably 8 to 24, particularly preferably 10 to 22, carbon atoms or H, preferably H, , with the proviso that the sum of the in R 3a and R 3b The number of carbon atoms contained is 7 to 44, preferably 8 to 24, particularly preferably 10 to 22.

[0046] According to the invention, the rhamnolipid derivative is preferably contained in the continuous phase of the dispersion according to the invention.

[0047] Particularly preferably, the rhamnolipid esters contained according to the invention are selected from diRLC10C10 ester, diRLC8C10 ester, diRLC10C12 ester, diRLC10C12:1 ester and monoRLC10C10 ester with R 3< = aliphatic residue with 7 to 32 carbon atoms, preferably 8 to 24 carbon atoms, particularly preferably 10 to 22 carbon atoms.

[0048] The rhamnolipid esters contained are characterized by the fact that R 3< is selected from the group of residues R 3< directly derived from R 3< OH = natural fatty alcohol.

[0049] In this context, rhamnolipid esters are particularly preferably selected according to the invention from diRLC10C10 ester, diRLC8C10 ester, diRLC10C12 ester, diRLC10C12:1 ester and monoRLC10C10 ester.

[0050] In connection with the present invention, the term "natural fatty alcohol" refers to alcohols obtainable by reduction of natural triacylglycerols, fatty acids or fatty acid methyl esters; these include in particular linear, saturated or unsaturated primary alkan-1-ols with 8-32 carbon atoms.

[0051] Particularly preferably, the rhamnolipid esters contained according to the invention are characterized in that R3 is selected from branched or linear alkyl groups, preferably with 8 to 24, and in particular 10 to 22, carbon atoms. In this context, rhamnolipid esters are particularly preferably selected from diRLC10C10 esters, diRLC8C10 esters, diRLC10C12 esters, diRLC10C12:1 esters, and monoRLC10C10 esters.

[0052] Particularly preferably, the rhamnolipid esters contained according to the invention are characterized in that R< 3< is selected from the group comprising, preferably consisting of, lauryl, myristyl, palmityl, stearyl, arachidyl, and behenyl residues. In this context, rhamnolipid esters are particularly preferably selected according to the invention from diRLC10C10 esters, diRLC8C10 esters, diRLC10C12 esters, diRLC10C12:1 esters, and monoRLC10C10 esters. The rhamnolipid esters contained according to the invention are preferably mixtures of rhamnolipid esters, which are particularly characterized in that they contain mono- and di-rhamnolipid esters.

[0053] Depending on the application, it may be preferred that the mixture compositions according to the invention contain more weight percent mono-rhamnolipid esters than di-rhamnolipid esters or more weight percent di-rhamnolipid esters than mono-rhamnolipid esters, wherein the weight percent refers to all mono- and di-rhamnolipid esters contained in the mixture composition.

[0054] For example, the mixture compositions according to the invention can contain, for example, more than 60 wt.%, in particular more than 80 wt.%, or even more than 95 wt.%, di-rhamnolipid esters, or, for example, more than 60 wt.%, in particular more than 80 wt.%, or even more than 95 wt.%, mono-rhamnolipid esters, wherein the wt. percent refer to all mono- and di-rhamnolipid esters contained in the mixture composition.

[0055] The rhamnolipid esters contained in the invention can be produced by a process comprising the process steps A) Providing at least one rhamnolipid, B) Reacting the rhamnolipid with at least one coupling reagent, C) Reacting the rhamnolipid activated by process step B) with an alcohol having 1 to 32, in particular 3 to 32, carbon atoms, and optionally D) Purifying the rhamnolipid ester, be manufactured.

[0056] Process step A) is carried out according to generally known prior art methods, in particular using genetically modified microorganisms that preferentially overexpress rhamnolipid synthesis genes, wherein these genes are preferably selected from rhlA, rhlB and rhlC. The person skilled in the art can find corresponding instructions in, for example, US2014296168 and WO2012013554.

[0057] In process step B), for example, dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N-cyclohexyl-N'-(2'-morpholinoethyl)carbodiimide metho-p-toluenesulfonate, N-benzyl-N'-3' dimethylaminopropylcarbodiimide hydrochloride, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, N-ethylcarbodiimide hydrochloride, or carbonyldiimidazole can be used as coupling reagents.

[0058] Preferably, the rhamnolipidamides contained according to the invention are selected from such compounds of general formula (II) in which organic residues R 3a< and R 3b< are selected from optionally mono- or polyunsaturated alkyl residues, which optionally have at least one amine group.

[0059] Preferred rhamnolipidamides included are selected from compounds of general formula (II), wherein m = 2, 1 or 0, in particular 1 or 0, n = 1 or 0, in particular 1, R 1< = optionally branched, optionally substituted, in particular hydroxy-substituted, optionally unsaturated, in particular optionally singly, doubly or triply unsaturated, alkyl group, with 2 to 24, preferably 5 to 13 carbon atoms, preferably one selected from the group consisting of pentenyl, heptenyl, nonenyl, undekenyl and tridekenyl and (CH 2 ) o -CH 3 with o = 1 to 23, preferably 4 to 12, R 2< = optionally branched, optionally substituted, in particular hydroxy-substituted, optionally unsaturated, in particular optionally singly, doubly or triply unsaturated, alkyl group with 2 to 24, preferably 5 to 13 carbon atoms, preferably one selected from the group consisting of pentenyl, Heptenyl, nonenyl, undekenyl and tridekenyl and (CH 2 ) o -CH 3 with o = 1 to 23, preferably 4 to 12.

[0060] Preferred rhamnolipidamides are selected from compounds of general formula (II), wherein R 3a< is selected from the group of alkyl groups which may optionally have an amine group, and R 3b< = organic group with 1 to 8 carbon atoms, in particular alkyl group, or H, particularly preferably H.

[0061] Particularly preferred rhamnolipidamides are selected from diRLC10C10 amides, diC8C10 amides, diRLC10C12 amides, diRLC10C12:1 amides and monoRLC10C10 amides with R 3a< = organic residue with 8 to 24, preferably 10 to 22, carbon atoms, in particular alkyl residue, and preferably R 3b< = H.

[0062] In an alternative preferred embodiment, the rhamnolipidamides contained are selected from compounds of general formula (II), wherein R 3a< = organic residue with 10 to 32 carbon atoms, in particular alkyl residue, and R 3b< = organic residue with 10 to 32 carbon atoms, in particular alkyl residue, wherein it is particularly preferred that R 3a< and R 3b< are selected independently of each other from alkyl residues with 10 to 22 carbon atoms.

[0063] In this context, rhamnolipid amides are particularly preferred from diRLC10C10 amides, diC8C10 amides, diRLC10C12 amides, diRLC10C12:1 amides and monoRLC10C10 amides.

[0064] Particularly preferred rhamnolipid amides are characterized in that R 3a< is selected from the group comprising, preferably consisting of, where R4< and R5< = independent identical or different alkyl groups with 1 to 6, preferably 1 to 3, particularly preferably 1, carbon atoms, R6< = an alkylene group with 1 to 6, preferably 2 to 3 carbon atoms, and where R 7< = an alkylene group with 1 to 22, preferably 2 to 18, in particular 3 to 8 carbon atoms, Z = H, OH, OR 8< with R 8< = alkyl group with 1 to 6, preferably 1 to 3, particularly preferably 1, carbon atoms, and preferably R 3b< = H.

[0065] In this context, rhamnolipid amides are particularly preferred from diRLC10C10 amides, diC8C10 amides, diRLC10C12 amides, diRLC10C12:1 amides and monoRLC10C10 amides.

[0066] In an alternative, preferred embodiment, the rhamnolipidamides contained according to the invention are characterized in that the residue -NR 3a< R 3b< is derived from an amine NHR 3a< R 3b< selected from amino acids and peptides. In this context, preferred amino acids are selected from the proteinogenic amino acids. Furthermore, preferred peptides in this context are selected from peptides consisting of proteinogenic amino acids, in particular peptides comprising 2 to 20, in particular 4 to 16, and most preferably 4 to 8 amino acids.

[0067] The rhamnolipidamides contained according to the invention are preferably mixtures of rhamnolipidamides, characterized in particular by the fact that they contain mono- and di-rhamnolipidamides. Depending on the application, it may be preferred that the mixtures contained according to the invention contain a higher weight percentage of mono-rhamnolipidamides than di-rhamnolipidamides or a higher weight percentage of di-rhamnolipidamides than mono-rhamnolipidamides, wherein the weight percentages refer to all mono- and di-rhamnolipidamides contained in the mixture. For example, the mixtures contained according to the invention may contain, for example, more than 60 wt.%, in particular more than 80 wt.%, or even more than 95 wt.%, di-rhamnolipidamides, or, for example, more than 60 wt.%, in particular more than 80 wt.%, or even more than 95 wt.%.-%, Mono-Rhamnolipidamides, where the weight percent refers to all mono- and di-rhamnolipidamides contained in the mixture composition.

[0068] The rhamnolipidamides contained in the invention can be produced by a process comprising the process steps A) Providing at least one rhamnolipid, B) Reacting the rhamnolipid with at least one coupling reagent, C) Reacting the rhamnolipid activated by process step B) with an amine, and optionally D) Purifying the rhamnolipid amide will be obtained.

[0069] Process step A) is carried out according to generally known prior art methods, in particular using genetically modified microorganisms that preferentially overexpress rhamnolipid synthesis genes, wherein these genes are preferably selected from rhlA, rhlB and rhlC. The person skilled in the art can find corresponding instructions in, for example, US2014296168 and WO2012013554.

[0070] In process step B), suitable coupling reagents include, for example, dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N-cyclohexyl-N'-(2'-morpholinoethyl)carbodiimide metho-p-toluenesulfonate, N-benzyl-N'-3'-dimethylaminopropylcarbodiimide hydrochloride, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, N-ethylcarbodiimide hydrochloride, and carbonyldiimidazole. In process step C), a catalyst such as N-ethyldiisopropylamine, trialkylamines, pyridine, 4-dimethylaminopyridine, and hydroxybenzotriazole can be used.

[0071] According to the invention, preferred dispersions are characterized in that they constitute an emulsion, in particular an oil-in-water emulsion.

[0072] According to the invention, preferred dispersions are characterized in that they A) the rhamnolipid derivative, B) at least one cosmetic oil and C) water. Component B) is a cosmetic oil.

[0073] In the context of the present invention, the term "cosmetic oil" refers to water-immiscible liquids suitable for the production of cosmetic formulations. Water-immiscible, in the context of the present invention, means that aqueous mixtures of cosmetic oils at room temperature, with oil concentrations of 0.5–99.5 vol.% based on the total mixture, result in a turbidity perceptible to the human eye or in the formation of two or more phases. Furthermore, in the context of the present invention, cosmetic oils are preferably characterized by having an interfacial tension with water of > 5 mN / m. Cosmetic oils can, for example, be based on oleochemistry or silicone chemistry.

[0074] Preferably, the dispersion according to the invention contains cosmetic oils selected from the group consisting of fatty alcohols, esters of linear fatty acids with linear or branched fatty alcohols, esters of branched fatty acids with linear or branched fatty alcohols, esters of linear fatty acids with unbranched or branched polyhydric alcohols, esters of branched fatty acids with unbranched or branched polyhydric alcohols, esters of linear fatty acids with unbranched or branched alcohols, esters of branched fatty acids with unbranched or branched alcohols, and esters of alkylhydroxycarboxylic acids with linear or branched fatty alcohols. Furthermore, mono-, di-, or triglycerides in liquid or solid form are included.Furthermore, esters of carboxylic acids, aromatic carboxylic acids, or dicarboxylic acids with linear or branched fatty alcohols, unbranched or branched polyhydric alcohols, or unbranched or branched alcohols. Furthermore, linear, cyclic, or branched hydrocarbons, with or without substituents, with or without double bonds. Furthermore, vegetable oils, carbonates with unbranched or branched alcohols, carbonates with unbranched or branched polyhydric alcohols, and carbonates with linear or branched fatty alcohols. Furthermore, ethers, with or without alkoxy groups, or silicone oils, with or without organic modification. Furthermore, mixtures of these oils in any proportions.Preferably esters of linear fatty acids with linear or branched fatty alcohols, esters of branched fatty acids with linear or branched fatty alcohols, esters of linear fatty acids with unbranched or branched polyhydric alcohols, esters of branched fatty acids with unbranched or branched polyhydric alcohols, esters of linear fatty acids with unbranched or branched alcohols, esters of branched fatty acids with unbranched or branched alcohols. Furthermore, mono-, di-, or triglycerides in liquid or solid form. Furthermore, esters of carboxylic acids, aromatic carboxylic acids, or dicarboxylic acids with linear or branched fatty alcohols, unbranched or branched polyhydric alcohols, or unbranched or branched alcohols. Furthermore, linear, cyclic, or branched hydrocarbons, with or without substituents, with or without double bonds.Furthermore, vegetable oils, carbonates with unbranched or branched alcohols, carbonates with unbranched or branched polyhydric alcohols, carbonates with linear or branched fatty alcohols, particularly preferably linear, cyclic, or branched hydrocarbons, with or without substituents, with or without double bonds. Also included are carbonates with unbranched or branched alcohols, carbonates with unbranched or branched polyhydric alcohols, and carbonates with linear or branched fatty alcohols. Esters of branched fatty acids with unbranched or branched polyhydric alcohols are also included.

[0075] Emulsions preferred according to the invention are characterized in that A) at least one rhamnolipid derivative in an amount of 0.1 wt.% to 10.0 wt.%, preferably in an amount of 0.5 wt.% to 7.0 wt.%, particularly preferably in an amount of 1.0 wt.% to 5.0 wt.%, B) the oil phase in an amount of 5.0 wt.% to 79.9 wt.%, preferably in an amount of 10.0 wt.% to 50.0 wt.%, particularly preferably in an amount of 12.0 wt.% to 35.0 wt.%, C) the aqueous phase in an amount of 20.0 wt.% to 94.9 wt.%, preferably in an amount of 50.0 wt.% to 90.0 wt.%, particularly preferably in an amount of 65.0 wt.% to 88.0 wt.%, is included, where the wt% refers to the total emulsion.

[0076] A further aspect of the present invention is the use of the rhamnolipid derivatives contained in the dispersions according to the invention as an emulsifier or dispersing agent. The rhamnolipid derivatives preferably contained in the dispersions according to the invention are preferably used as an emulsifier or dispersing agent within the scope of the present invention.

[0077] The following examples describe the present invention by way of example, without limiting the invention, the scope of which is evident from the entire description and the claims, to the embodiments mentioned in the examples. Examples: Example 1: Production of di-rhamnolipids

[0078] A fermentation with a recombinant strain Pseudomonas putida KT2440S pBBR1MCS2-Plac-rhlABC-T-Ptac-rhlC-TThe preparation of the strain is described in US2014296168. The pre-culture in shake flasks was carried out as described in WO2012013554. A mineral medium (M9) was also used for the main culture. Fermentation took place in a glucose-limited fed-batch process in a 2-liter fermenter. Glucose feeding was regulated based on the dissolved oxygen signal. The oxygen partial pressure of the fermentation broth was regulated at 20% saturation via the stirrer speed. The pH was adjusted to 7 using a pH electrode and the addition of 2M sulfuric acid or a 20 wt% ammonia solution. To prevent foaming of the fermentation broth, the defoamer DOW Corning 1500 was added as needed. Fermentation was carried out for 4 days until a biomass dry matter of 15 g / L was reached. The rhamnolipid concentration was determined by HPLC and was 9.8 g / l. After separating the cells by centrifugation at 10.At 10,000 g, the fermentation broth was adjusted to a pH of 3.1 by adding concentrated H₂SO₄. A pasty solid concentrate with a RL content of 45 wt% and a viscosity > 10,000 mPas was obtained by centrifugation at 10,000 g. A 50 wt% aqueous KOH solution was added to the pasty suspension of the concentrated rhamnolipid precipitate while stirring continuously, and the pH was adjusted to 6. This caused the pasty mass to liquefy, accompanied by a significant drop in viscosity. The suspension became a clear solution. The solution was adjusted to an active content of 35 wt% by adding water. The rhamnolipid purity was > 90 wt% based on the dry mass.

[0079] Rhamnolipid species detected by HPLC were: Total RL [%] (HPLC) 91 diRL-C8C10 13,9 monoRL-C8C10 0,51 diRL-C10C10 61,4 monoRL -C10C10 1,4 diRL-C10C12:1 5,9 diRL-C10C12 5,5 other RL 2,2 Example 2: Production of mono-rhamnolipids

[0080] The 35 wt% rhamnolipid solution prepared as described above was diluted to 1% by adding water. Two liters of this solution were heated to 50 °C. With gentle stirring, 200 units of a thermostable rhamnosidase (ThermoActive™ Rhamnosidase A, Prokazyme) were added, and the reaction was carried out overnight. After 20 h, a sample of the solution was analyzed by HPLC. The di-rhamnolipid had been completely converted to mono-rhamnolipid and rhamnose. The enzyme was then inactivated at 80 °C for one hour. The entire mixture was then freeze-dried. The freeze-dried product was adjusted to a mono-rhamnolipid active content of 35 wt% by adding water. Example 3a: Synthesis of di-rhamnolipid behenylamide

[0081] To activate the acid function, 25 g of di-rhamnolipid (40 mmol) are dissolved in THF with 6.25 ml of diisopropylcarbodiimide (40 mmol) at 55°C. Once an acid number of < 2 is reached, 15.6 g of behenylamine (48 mmol) and 1 wt% of 4-dimethylaminopyridine are added for catalysis. The resulting water of reaction promotes the formation of N,N'-diisopropylurea as a by-product. After a reaction time of 5 hours, the reaction mixture is dried on a rotary evaporator (45°C, < 300 mbar). Purification is carried out by extraction with ethyl acetate (1) : water (1) (2 x 20 ml each) to separate the urea formed. The ethyl acetate phase is evaporated (rotary evaporator, 45°C, < 300 mbar), and the rhamnolipid-behenylamide remains as a solid.

[0082] Further purification of the product can be carried out by column chromatography. Silica 60 gel (SIGMA Aldrich) serves as the stationary phase and ethyl acetate (99) : water (1) with 1% acetic acid as the mobile phase. Behenylamine residues, polar by-products, or any degradation products are removed from a 5% solution of the crude product. For thorough separation, a fraction comprises 10 ml at a drop rate of 15 ml / min and a total volume of 200 ml of starting solution. Example 3b: Synthesis of mono-rhamnolipid dioctylamide

[0083] To activate the acid function, 20.2 g of mono-rhamnolipid (40 mmol) are dissolved in toluene with 6.25 ml of diisopropylcarbodiimide at 55°C. Once the mixture reaches an acid number of < 2, 9.66 g of dioctylamine (40 mmol) are added, along with 1 wt% of 4-dimethylaminopyridine for catalysis. Any unreacted coupling reagent should be inactivated beforehand by adding 2 ml of water. After a reaction time of 10 h, the mixture is worked up. The reaction mixture is dried on a rotary evaporator (45°C, < 300 mbar).

[0084] For purification, the crude product is dissolved in ethyl acetate (2 parts) and extracted with water (1 part) at pH 5.8. The rhamnolipidamide remains in the ethyl acetate phase (filter off insoluble components). This phase is then dried on a rotary evaporator (45°C, <100 mbar) to obtain the rhamnolipidamide. Example 3c: Synthesis of mono-rhamnolipid stearylamide

[0085] To activate the acid function, 20.2 g of mono-rhamnolipid (40 mmol) are dissolved in THF with 6.25 ml of diisopropylcarbodiimide at 55°C. Once the mixture reaches an acid number of < 2, 10.8 g of octadecylamine (40 mmol) are added, along with 1 wt% of 4-dimethylaminopyridine for catalysis. Any unreacted coupling reagent should be inactivated beforehand by adding 2 ml of water. After a reaction time of 10 h, the mixture is worked up. The reaction mixture is dried on a rotary evaporator (45°C, < 300 mbar).

[0086] For purification, the crude product is dissolved in ethyl acetate (2 parts) and extracted with water (1 part) at pH 5.8. The rhamnolipid ester remains in the ethyl acetate phase (filter off insoluble fractions). This phase is also dried on a rotary evaporator (45°C, <100 mbar) to obtain the rhamnolipidamide. Example 4a: Synthesis of di-rhamnolipid stearyl ester

[0087] To activate the acid function, 25 g of di-rhamnolipid (40 mmol) from Example 1 are dissolved in THF with 6.25 ml of diisopropylcarbodiimide at 55°C. Once the mixture reaches an acid number of < 2, 10.8 g of stearyl alcohol (40 mmol) are added, along with 1 wt% of 4-dimethylaminopyridine for catalysis. Any unreacted coupling reagent should be inactivated beforehand by adding 2 ml of water. After a reaction time of 10 h, the mixture is worked up. The reaction mixture is dried on a rotary evaporator (45°C, < 300 mbar), and purification is carried out by extraction with ethyl acetate (1) and water (1) in two steps of 250 ml each. The rhamnolipid ester remains in the ethyl acetate phase. This is also dried on a rotary evaporator (45°C, <100mbar), leaving the viscous rhamnolipid ester.

[0088] Further purification of the product can be carried out by column chromatography. Silica 60 Gel (SIGMA Aldrich) serves as the stationary phase and ethyl acetate (99) : water (1) with 1% acetic acid as the mobile phase. Polar by-products or any degradation products are removed from a 5% solution of the rhamnolipid ester crude product. For careful separation, a fraction comprises 10 ml at a drop rate of 15 ml / min and a total volume of 200 ml of starting solution.

[0089] Analytical determination by HPLC was performed on a 50*3.0 mm column Poroshell 120 C18 (2.7µm) in 20mM NH 4 formats in H 2 O and MeCN at 30°C for 35 min. Example 4b: Synthesis of mono-rhamnolipid stearyl esters

[0090] To activate the acid function, 20.2 g of mono-rhamnolipid (40 mmol) are dissolved in THF with 6.25 ml of diisopropylcarbodiimide at 55°C. Once the mixture reaches an acid number of < 2, 10.8 g of stearyl alcohol (40 mmol) are added, along with 1 wt% of 4-dimethylaminopyridine for catalysis. Any unreacted coupling reagent should be inactivated beforehand by adding 2 ml of water. After a reaction time of 10 h, the mixture is worked up. The reaction mixture is dried on a rotary evaporator (45°C, < 300 mbar).

[0091] For purification, the crude product is dissolved in ethyl acetate (2 parts) and extracted with water (1 part) at pH 5.8. The rhamnolipid ester remains in the ethyl acetate phase (filter off insoluble fractions). This phase is also dried on a rotary evaporator (45°C, <100 mbar) to obtain the viscous rhamnolipid ester. Example 5a: non-inventive synthesis of di-rhamnolipid ethyl esters

[0092] The synthesis was carried out according to the procedure from the publication Miao et al. European Journal of Lipid Science and Technology, 117, 2015; 156-1609.

[0093] For this purpose, di-rhamnolipid from Example 1 was reacted with ethanol and sulfuric acid at 0 °C as described in the literature. The yield obtained was less than 5%.

[0094] This is due, among other things, in particular to the lack of coupling reagent. Example 5b: non-inventive synthesis of mono-rhamnolipid ethyl esters

[0095] The synthesis was carried out according to the procedure from the publication Miao et al. European Journal of Lipid Science and Technology, 117, 2015; 156-1609.

[0096] For this purpose, mono-RL from Example 2 is stirred into ethanol at 0°C and the esterification is catalyzed with sulfuric acid. The yield obtained was again less than 5%. Example 6: Emulsifying performance

[0097] All concentrations in the application examples are given in weight percent. Conventional homogenization processes known to those skilled in the art were used to produce the emulsions.

[0098] The emulsions were therefore typically prepared by heating the oil and water phases to 70–75°C. Then, either the oil phase was stirred into the water, or the oil and water phases were combined without stirring. Finally, homogenization was carried out for approximately 1–2 minutes using a suitable homogenizer (e.g., Ultrathurrax).

[0099] Stabilizing polymers (e.g., carbomers) are preferably stirred into the emulsion as an oil dispersion at temperatures of 50–60°C. A brief homogenization then follows.

[0100] The addition of further ingredients (e.g., preservatives, active ingredients) was preferably carried out at 40°C. If the formulations were preserved with organic acids, the pH value of the emulsions was adjusted to approximately 5.

[0101] These experiments are intended to show that the rhamnolipid derivatives according to the invention have advantages in terms of emulsion stability compared to unmodified mono- or di-rhamnolipids as well as to short-chain mono- or di-rhamnolipid esters.

[0102] To verify the storage stability of the emulsions, they were stored for three months at room temperature, 40°C, and 45°C. To verify cold stability, they were also stored for one month at -5°C and subjected to three freeze-thaw cycles of 25°C / -15°C / 25°C. Significant changes in appearance or consistency, and especially oil or water separation, were considered criteria for instability.

[0103] Comparison of the rhamnolipid derivatives according to the invention as emulsifiers 3a - c and 4a and b against the non-derivatized rhamnolipids according to example 1 and 2 and the non-derivatized examples 5a and b in two lotions with different composition and polarity of the oil phase. Recipe 1 1-1 1-2 1-3 1-4 1-5 Rhamnolipid derivative according to the invention as shown in Example 3a 3,00% - - - - Rhamnolipid derivative according to the invention as shown in Example 3b - 3,00% - - - Rhamnolipid derivative according to the invention as shown in Example 3c - - 3,00% - - Rhamnolipid derivative according to the invention as shown in Example 4a - - - 3,00% - Rhamnolipid derivative according to the invention as shown in Example 4b - - - - 3,00% Glyceryl Stearate 0,50% 0,50% 0,50% 0,50% 0,50% Stearic Acid 0,50% 0,50% 0,50% 0,50% 0,50% Caprylic / Capric Triglyceride 5,50% 5,50% 5,50% 5,50% 5,50% Ethylhexyl Palmitate 6,30% 6,30% 6,30% 6,30% 6,30% Water ad 100% ad 100% ad 100% ad 100% ad 100% Glycerin 3,00% 3,00% 3,00% 3,00% 3,00% Carbomer 1< 0,20% 0,20% 0,20% 0,20% 0,20% Sodium hydroxide (10% in water) 0,60% 0,60% 0,60% 0,60% 0,60% phenoxyethanol; Ethylhexylglycerol 2< 0,70% 0,70% 0,70% 0,70% 0,70% Consistency after production thick liquid thin liquid thick liquid thick liquid thick liquid stability Stable Stable Stable Stable Stable Recipe 1 1-6 1-7 1-8 1-9 Non-inventive, non-derivatized mono-rhamnolipid according to Example 2 3,00% - - - Non-inventive, non-derivatized di-rhamnolipid according to Example 1 - 3,00% - - Non-inventional mono-rhamnolipid derivative according to Example 5b - - 3,00% - 1< TEGO ®< Carbomer 141 (Evonik Nutrition & Care GmbH) 2< Euxyl PE 9010 (Schülke & Mayr GmbH) Non-inventional di-rhamnolipid derivative according to Example 5a - - - 3,00% Glyceryl Stearate 0,50% 0,50% 0,50% 0,50% Stearic Acid 0,50% 0,50% 0,50% 0,50% Caprylic / Capric Triglyceride 5,50% 5,50% 5,50% 5,50% Ethylhexyl Palmitate 6,30% 6,30% 6,30% 6,30% Water ad 100% ad 100% ad 100% ad 100% Glycerin 3,00% 3,00% 3,00% 3,00% Carbomer 3< 0,20% 0,20% 0,20% 0,20% Sodium hydroxide (10% in water) 0,60% 0,60% 0,60% 0,60% phenoxyethanol; Ethylhexylglycerol 4< 0,70% 0,70% 0,70% 0,70% Consistency after production pasty pasty pasty pasty stability Phase separation after 1 day at RT Phase separation after 1 day at RT Phase separation after 3 days at RT Phase separation after 3 days at RT 3< TEGO ®< Carbomer 141 (Evonik Nutrition & Care GmbH) 4< Euxyl PE 9010 (Schülke & Mayr GmbH) Recipe 2 2-1 2-2 2-3 2-4 2-5 Rhamnolipid derivative according to the invention as shown in Example 3a 3,00% - - - - Rhamnolipid derivative according to the invention as shown in Example 3b - 3,00% - - - Rhamnolipid derivative according to the invention as shown in Example 3c - - 3,00% - - Rhamnolipid derivative according to the invention as shown in Example 4a - - - 3,00% - Rhamnolipid derivative according to the invention as shown in Example 4b - - - - 3,00% Glyceryl Stearate 0,50% 0,50% 0,50% 0,50% 0,50% Stearic Acid 0,50% 0,50% 0,50% 0,50% 0,50% Ethylhexyl Palmitate 6,30% 6,30% 6,30% 6,30% 6,30% Paraffinum Perliquidum 5,50% 5,50% 5,50% 5,50% 5,50% Water ad 100% ad 100% ad 100% ad 100% ad 100% Glycerin 3,00% 3,00% 3,00% 3,00% 3,00% Carbomer 1< 0,20% 0,20% 0,20% 0,20% 0,20% Sodium hydroxide (10% in water) 0,60% 0,60% 0,60% 0,60% 0,60% phenoxyethanol; Ethylhexylglycerol 2< 0,70% 0,70% 0,70% 0,70% 0,70% Consistency after production thick liquid thin liquid thick liquid thick liquid thick liquid stability Stable Stable Stable Stable Stable Recipe 2 2-6 2-7 2-8 2-9 Non-inventive, non-derivatized mono-rhamnolipid according to Example 2 3,00% - - - Non-inventive, non-derivatized di-rhamnolipid according to Example 1 - 3,00% - - Non-inventional mono-rhamnolipid derivative according to Example 5b - - 3,00% - Non-inventional di-rhamnolipid derivative according to Example 5a - - - 3,00% Glyceryl Stearate 0,50% 0,50% 0,50% 0,50% Stearic Acid 0,50% 0,50% 0,50% 0,50% Ethylhexyl Palmitate 6,30% 6,30% 6,30% 6,30% Paraffinum Perliquidum 5,50% 5,50% 5,50% 5,50% Water ad 100% ad 100% ad 100% ad 100% Glycerin 3,00% 3,00% 3,00% 3,00% Carbomer 1< 0,20% 0,20% 0,20% 0,20% Sodium hydroxide (10% in water) 0,60% 0,60% 0,60% 0,60% phenoxyethanol; Ethylhexylglycerol 2< 0,70% 0,70% 0,70% 0,70% Consistency after production pasty pasty pasty pasty stability Phase separation after 1 day at RT Phase separation after 1 day at RT Phase separation after 5 days at RT Phase separation after 5 days at RT

[0104] While the formulations with the emulsifiers 3a according to the invention - c as well as 4a and bWhile each of the following results in a storage-stable lotion, those with the non-inventive comparison emulsifiers from Examples 1, 2, 5a and 5b show an initially excessively high viscosity and significant weaknesses in the storage stability of the emulsion. Examples of wording

[0105] These examples are intended to show that the rhamnolipid derivatives according to the invention can be used as emulsifiers in a variety of cosmetic formulations.

[0106] Furthermore, with the help of the rhamnolipid derivatives according to the invention, it is possible to stably incorporate pigments or solids into emulsion preparations.

[0107] Furthermore, the examples demonstrate the good compatibility with typical co-emulsifiers, oils, thickeners and stabilizers, as well as the good compatibility with emulsion-polluting ingredients such as UV filters, antimicrobial agents or cosmetic active ingredients. Lotions with low emulsifier content

[0108] Recipe 3-1 3-2 4-1 4-2 Rhamnolipid derivative according to the invention as shown in Example 4a 1,00% 0,50% 1,00% 0,50% Cetearyl Glucoside 5< - 0,50% - - Polyglyceryl-6 Stearates; Polyglyceryl-6 Behenate 6< - - - 1,00% Glyceryl Stearate 0,50% 0,50% 0,50% 0,50% Stearic Acid 0,50% 0,50% 0,50% 0,50% Caprylic / Capric Triglyceride 6,50% 6,50% Ethylhexyl Palmitate 8,10% 8,10% 8,10% 8,10% Paraffinum Perliquidum 6,50% 6,50% Water ad 100% ad 100% ad 100% ad 100% Glycerin 3,00% 3,00% 3,00% 3,00% Carbomer 1< 0,20% 0,20% 0,20% 0,20% Sodium Hydroxide (10% ig in Wasser) 0,60% 0,60% 0,60% 0,60% Phenoxyethanol; Ethylhexylglycerin 2< 0,70% 0,70% 0,70% 0,70% serum

[0109] Rezeptur 5-1 5-2 5-3 5-4 Erfindungsgemäßes Rhamnolipidderivat nach Bsp. 3a 2,00% 1,00% - - Erfindungsgemäßes Rhamnolipidderivat nach Bsp. 3c - - 2,00% 1,00% Sorbitan Laurate; Polyglyceryl-4 Laurate; Dilauryl Citrate 7< - 1,00% - 1,00% Ethylhexyl Stearate 7,00% 7,00% 7,00% 7,00% Octyldodecanol 4,00% 4,00% 4,00% 4,00% Caprylic / Capric Triglyceride 2,00% 2,00% 2,00% 2,00% Carbomer 8< 0,15% 0,15% 0,15% 0,15% Carbomer 1< 0,15% 0,15% 0,15% 0,15% Xanthan Gum 9< 0,10% 0,10% 0,10% 0,10% Hydrolyzed Hyaluronic Acid 10< 0,10% 0,10% 0,10% 0,10% 5< TEGO ®< Care CG 90 (Evonik Nutrition & Care GmbH) 6< TEGO ®< Care PBS 6 (Evonik Nutrition & Care GmbH) 7< TEGO ®< Care LTP (Evonik Nutrition & Care GmbH) 8< TEGO ®< Carbomer 140 (Evonik Nutrition & Care GmbH) 9< Keltrol CG-SFT (CP Kelco) 10< HyaCare ®< 50 (Evonik Nutrition & Care GmbH) Ceteareth-25; Glycerin; Cetyl Alcohol; Behenic Acid; Cholesterol; Ceramide EOS; Ceramide NP; Ceramide NS; Ceramide AP; Caprooyl Phytosphingosine; Caprooyl Sphingosine) 11< 1,00% 1,00% 1,00% 1,00% Glycerin 3,00% 3,00% 3,00% 3,00% Wasser ad 100% ad 100% ad 100% ad 100% Sodium Hydroxide (10% ig in Wasser) 0,90% 0,90% 0,90% 0,90% Caprooyl Phytosphingosine 12< 0,10% 0,10% 0,10% 0,10% Pentylene Glycol 1,40% 1,40% 1,40% 1,40% Phenoxyethanol; Caprylyl Glycol 13< 1,00% 1,00% 1,00% 1,00% O / W sunscreen lotion SPF 30

[0110] Rezeptur 6-1 6-2 6-3 6-4 Rhamnolipid derivative according to the invention as shown in Example 4a 3,00% 1,00% - - Rhamnolipid derivative according to the invention as shown in Example 4b - - 3,00% 1,00% Cetearyl Glucoside 3< - 1,00% - 1,00% Phenoxyethyl Caprylate 14< 6,10% 6,10% 6,10% 6,10% Cetearyl Alcohol 1,00% 1,00% 1,00% 1,00% Octocrylene 4,80% 4,80% 4,80% 4,80% Ethylhexyl Triazone 4,50% 4,50% 4,50% 4,50% Butyl methoxydibenzoylmethane 2,50% 2,50% 2,50% 2,50% Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine 15< 5,50% 5,50% 5,50% 5,50% Tocopheryl Acetate 0,50% 0,50% 0,50% 0,50% Glycerin 2,00% 2,00% 2,00% 2,00% Water ad 100% ad 100% ad 100% ad 100% Acrylates / C10-30 Alkyl Acrylates Crosspolymer 16< 0,10% 0,10% 0,10% 0,10% 11< SKINMIMICS ®< (Evonik Nutrition & Care GmbH) 12< SPHINGOKINE ®< NP (Evonik Nutrition & Care GmbH) 13< Verstatil ®< PC (Dr. Straetmans GmbH) 14< TEGOSOFT ®< XC (Evonik Nutrition & Care GmbH) 15< Tinosorb S (BASF) 16< TEGO ®< Carbomer 341 ER (Evonik Nutrition & Care GmbH) Sodium Hydroxide (10% in water) 0,30% 0,30% 0,30% 0,30% dipropylene glycol; methylparaben; ethylparaben; Aqua; Methylisothiazolinone 17< 0,80% 0,80% 0,80% 0,80% Lotion based on natural ingredients

[0111] Recipe 7-1 7-2 7-3 7-4 Rhamnolipid derivative according to the invention as shown in Example 4a 2,50% 1,50% - - Rhamnolipid derivative according to the invention as shown in Example 4b - - 2,50% 1,50% Polyglyceryl-3 Dicitrate / Stearate 18< - 1,00% - 1,00% Isopropyl Palmitate 5,00% 5,00% 5,00% 5,00% Prunus Amygdalus Dulcis (Sweet Almond) Oil 5,00% 5,00% 5,00% 5,00% Water ad 100% ad 100% ad 100% ad 100% Glycerin 3,00% 3,00% 3,00% 3,00% Xanthan Gum 7< 0,50% 0,50% 0,50% 0,50% Sodium Hydroxide (10%ig in Wasser) 0,20% 0,20% 0,20% 0,20% Benzyl Alcohol; Glycerin; Benzoic Acid; Sorbic Acid 19< 0,80% 0,80% 0,80% 0,80% 17< Microcare MEM (Thor) 18< TEGO ®< Care PSC 3 (Evonik Nutrition & Care GmbH) 19< Rokonsal BSB-N (Ashland) Light O / W lotion produced by cold manufacturing

[0112] Rezeptur 8-1 8-2 Erfindungsgemäßes Rhamnolipidderivat nach Bsp. 3a 2,50% 1,50% Sorbitan Laurate; Polyglyceryl-4 Laurate; Dilauryl Citrate 5< - 1,00% Ethylhexyl Palmitate 1,10% 1,10% Isohexadecane 5,50% 5,50% Cyclopentasiloxane 5,00% 5,00% Cellulose 20< 1,00% 1,00% Carbomer 6< 0,15% 0,15% Carbomer 1< 0,15% 0,15% Xanthan Gum 0,10% 0,10% Glycerin 3,00% 3,00% Wasser ad 100% ad 100% Sodium Hydroxide (10%ig in Wasser) 0,90% 0,90% Phenoxyethanol; Ethylhexylglycerin 2< 0,70% 0,70% O / W Baby Lotion

[0113] Rezeptur 9-1 9-2 Erfindungsgemäßes Rhamnolipidderivat nach Bsp. 3a 3,00% 2,00% Polyglyceryl-3 Methylglucose Distearate 21< - 0,50 % Stearyl Alcohol 1,00% 1,00% Isopropyl Palmitate 7,30 % 7,30 % Triisostearin 4,00% 4,00% Squalane 1,00% 1,00% Dimethicone 22< 0,50% 0,50% Wasser ad 100% ad 100% Glycerin 3,00% 3,00% Carbomer 1< 0,20% 0,20% Sodium Hydroxide (10%ig in Wasser) 0,60% 0,60% Sodium Lactate; Sodium PCA; Glycine; Fructose; Urea; Niacinamide; Inositol; Sodium Benzoate; Lactic Acid 23< 3,00% 3,00% Phenoxyethanol; Caprylyl Glycol 11< 1,00% 1,00% 20< TEGO ®< Feel C 10 (Evonik Nutrition & Care GmbH) 21< TEGO ®< Care 450 (Evonik Nutrition & Care GmbH) 22< ABIL ®< 350 (Evonik Nutrition & Care GmbH) Waterproofing lotion for baby wipes

[0114] Rezeptur 10-1 10-2 10-3 10-4 Erfindungsgemäßes 1,50% 1,00% - - Rhamnolipidderivat nach Bsp. 4a Erfindungsgemäßes - - 2,50% 1,50% Rhamnolipidderivat nach Bsp. 3b Cetearyl Glucoside 3< - 0,50 % - 0,50 % Polyglyceryl-3 Caprate 24< 0,50% 0,50% 0,50% 0,50% C12-15 Alkyl Benzoate 5,00% 5,00% 5,00% 5,00% Mineral Oil 5,00% 5,00% 5,00% 5,00% Gellan Gum 25< 0,03% 0,03% 0,03% 0,03% Wasser ad 100% ad 100% ad 100% ad 100% Glycerin 2,00% 2,00% 2,00% 2,00% Acrylates / C10-30 Alkyl Acrylate Crosspolymer 14< 0,05% 0,05% 0,05% 0,05% Sodium Hydroxide (10%ig in Wasser) 0,15% 0,15% 0,15% 0,15% Phenoxyethanol; Ethylhexylglycerin 2< 0,70% 0,70% 0,70% 0,70% O / W foundation for a natural skin feel

[0115] Rezeptur 11-1 11-2 11-3 11-4 Erfindungsgemäßes 5,00% 3,00% 5,00% 3,00% Rhamnolipidderivat nach Bsp. 3a Polyglyceryl-6 Stearate (and) Polyglyceryl-6 Behenate 4< - 1,50% - 1,50% Cetearyl Alcohol 1,50% 1,50% 1,50% 1,50% Glyceryl Stearate 1,00% 1,00% 1,00% 1,00% 23< LACTIL ®< (Evonik Nutrition & Care GmbH) 24< TEGOSOFT ®< PC 31 (Evonik Nutrition & Care GmbH) 25< Kelcogel CG-HA (CP Kelco) Myristyl Myristate 26< 1,00% 1,00% 1,00% 1,00% C12-15 Alkyl Benzoate 3,00% 3,00% 3,00% 3,00% Diethylhexyl Carbonate 27< 2,00% 2,00% 2,00% 2,00% Cyclopentasiloxane (and) Dimethicone Crosspolymer 28< 2,00% 2,00% 2,00% 2,00% Ethylhexyl Methoxycinnamate 8,00% 8,00% 8,00% 8,00% Ethylhexyl Salicylate 5,00% 5,00% 5,00% 5,00% Diethylamino Hydroxybenzoayl Hexyl Benzoate 29< 3,00% 3,00% 3,00% 3,00% Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine 13< 3,00% 3,00% 3,00% 3,00% Wasser ad 100% ad 100% ad 100% ad 100% Glycerin 1,00% 1,00% 1,00% 1,00% Xanthan Gum 0,15% 0,15% 0,15% 0,15% Titanium Dioxide; CI 77891 8,00% 8,00% 8,00% 8,00% CI 77492; Aqua; Glycerin; Xanthan Gum; Sodium Citrate 30< 1,70% 1,70% 1,70% 1,70% CI 77491; Aqua; Glycerin; Xanthan Gum; Sodium Citrate 31< 0,40% 0,40% 0,40% 0,40% CI 77499; Aqua; Glycerin; Xanthan Gum; Sodium Citrate 32< 0,10% 0,10% 0,10% 0,10% Glycerin 2,00% 2,00% 2,00% 2,00% Propylene Glycol 3,00% 3,00% 3,00% 3,00% Nylon-12 2,00% 2,00% - - Cellulose 18< - - 2,00% 2,00% Phenoxyethanol; Ethylhexylglycerin 2< 0,70% 0,70% 0,70% 0,70% Oil-in-water lotion for makeup removal with a silky skin feel

[0116] Rezeptur 12-1 12-2 Erfindungsgemäßes 3,00% 2,00% Rhamnolipidderivat nach Bsp. 3a 26< TEGOSOFT ®< MM (Evonik Nutrition & Care GmbH) 27< TEGOSOFT ®< DEC (Evonik Nutrition & Care GmbH) 28< 9045 Silicone Elastomer Blend (Dow Corning) 29< Uvinul A plus Granular (BASF) 30< Covarine Yellow WN 1792 GZ (Sensient Cosmetic Technologies) 31< Covarine Red WN 3798 GZ (Sensient Cosmetic Technologies) 32< Covarine Black WN 9798 GZ (Sensient Cosmetic Technologies) Bis-PEG / PPG-20 / 5 PEG / PPG-20 / 5 - 1,00% Dimethicone: Methoxy PEG / PPG-25 / 4 Dimethicone; Caprylic / Capric Triglyceride 33< Decyl Cocoate 34< 7,00% 7,00% Paraffinum Perliquidum 7,00% 7,00% Acrylates / C10-30 Alkyl Acrylate Crosspolymer 14< 0,15% 0,15% Glycerin 3,00% 3,00% Wasser ad 100% ad 100% Sodium Hydroxide (10%ig in Wasser) 0,45% 0,45% Alcohol 3,00% 3,00% Phenoxyethanol; Caprylyl Glycol 11< 1,00% 1,00% Natural oil-releasing cream

[0117] Rezeptur 13-1 13-2 14-1 14-2 Erfindungsgemäßes 4,00% 2,00% 4,00% 2,00% Rhamnolipidderivat nach Bsp. 4a Polyglyceryl-3 Distearate; Glyceryl Stearate Citrate 35< - 1,00% - - Polyglyceryl-6 Stearate; Polyglyceryl-6 Behenate - - - 1,00% Decyl Cocoate 32< 72,00% 72,00% - - Helianthus Annuus (Sunflower) Seed Oil 70,0% 70,0% Glycerin 2,00% 2,00% 2,00% 2,00% Wasser ad 100% ad 100% ad 100% ad 100% Benzyl Alcohol; Glycerin; Benzoic Acid; Sorbic Acid 17< 1,00% 1,00% 1,00% 1,00% Citric Acid (10% aq.) q.s. q.s. q.s. q.s. 33< ABIL ®< Care XL 80 (Evonik Nutrition & Care GmbH) 34< TEGOSOFT ®< DC (Evonik Nutrition & Care GmbH) 35< TEGO ®< Care NC (Evonik Nutrition & Care GmbH) Low viscosity W / O lotion

[0118] Rezeptur 15-1 15-2 16-1 16-2 Polyglyceryl-4 2,50% 2,50% - - Diisostearate / Polyhyd roxystearate / Sebacate 36< PEG / PPG-10 / 1 Dimethicone 37< - - 1,50% 1,50% Erfindungsgemäßes Rhamnolipidderivat nach Bsp. 4a 0,50% 0,20% 0,50% 0,20% Di-Rhamnolipid - 0,20% - 0,20% Hydrogenated Castor Oil 0,20% 0,20% 0,20% 0,20% Isopropyl Palmitate 10,00% 10,00% - - Prunus Amygdalus Dulcis (Sweet Almond) Oil 8,00% 8,00% - - Diethylhexyl Carbonate 25< 7,00% 7,00% 10,00% 10,00% Ethylhexyl Palmitate - - 8,00% 8,00% Dimethicone (5 mPas) - - 5,00% 5,00% Glycerin 3,00% 3,00% 2,00% 2,00% Wasser ad 100% ad 100% ad 100% ad 100% Magnesium Sulfate Heptahydrate 1,50% 1,50% - - Sodium Chloride - - 0,80% 0,80% Benzyl Alcohol; Glycerin; Benzoic Acid; Sorbic Acid 17< 1,00% 1,00% 1,00% 1,00% Citric Acid (10% aq.) q.s. q.s. q.s. q.s. 36< ISOLAN ®< GPS (Evonik Nutrition & Care GmbH) 37< ABIL ®< EM 90 (Evonik Nutrition & Care GmbH)

Claims

1. Dispersion containing at least A) one rhamnolipid derivative selected from the group consisting of rhamnolipid ester of the general formula (I) and rhamnolipid amide of the general formula (II): where m = 2, 1 or 0, in particular 1 or 0, n = 1 or 0, in particular 1, R1 = organic radical having 2 to 24, preferably 5 to 13, carbon atoms, in particular optionally branched, optionally substituted, in particular hydroxy-substituted, optionally unsaturated, in particular optionally mono-, bi- or tri-unsaturated, alkyl radical, preferably one selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH2)o-CH3 where o = 1 to 23, preferably 4 to 12, R2 = independently of one another, identical or different, organic radical having 2 to 24, preferably 5 to 13, carbon atoms, in particular optionally branched, optionally substituted, in particular hydroxy-substituted, optionally unsaturated, in particular optionally mono-, bi- or tri-unsaturated, alkyl radical, preferably one selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH2)o-CH3 where o = 1 to 23, preferably 4 to 12, and R3 = aliphatic radical having 7 to 32 carbon atoms, preferably 8 to 24 carbon atoms, more preferably 10 to 22 carbon atoms, which is selected from the group of R3 radicals derived directly from R3OH = natural fatty alcohol, where m = 2, 1 or 0, in particular 1 or 0, n = 1 or 0, in particular 1, R1 = organic radical having 2 to 24, preferably 5 to 13, carbon atoms, in particular optionally branched, optionally substituted, in particular hydroxy-substituted, optionally unsaturated, in particular optionally mono-, bi- or tri-unsaturated, alkyl radical, preferably one selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH2)o-CH3 where o = 1 to 23, preferably 4 to 12, R2 = independently of one another, identical or different, organic radical having 2 to 24, preferably 5 to 13, carbon atoms, in particular optionally branched, optionally substituted, in particular hydroxy-substituted, optionally unsaturated, in particular optionally mono-, bi- or tri-unsaturated, alkyl radical, preferably one selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH2)o-CH3 where o = 1 to 23, preferably 4 to 12, R3a = organic radical having 1 to 32, preferably 8 to 24, particularly preferably 10 to 22, carbon atoms, and R3b = organic radical having 1 to 32, preferably 8 to 24, particularly preferably 10 to 22, carbon atoms or H, preferably H, with the proviso that the sum of the carbon atoms contained in R3a and R3b is 7 to 44, preferably 8 to 24, particularly preferably 10 to 22.

2. Dispersion according to Claim 1, characterized in that it is an emulsion.

3. Dispersion according to Claim 1 or 2, characterized in that it contains A) the rhamnolipid derivative, B) at least one cosmetic oil, and C) water.

4. Dispersion according to Claim 3, characterized in that it contains A) in an amount of 0.1 wt% to 10.0 wt%, preferably in an amount of 0.5 wt% to 7.0 wt%, more preferably in an amount of 1.0 wt% to 5.0 wt%, B) in an amount of 5.0 wt% to 79.9 wt%, preferably in an amount of 10.0 wt% to 50.0 wt%, more preferably in an amount of 12.0 wt% to 35.0 wt%, C) in an amount of 20.0 wt% to 94.9 wt%, preferably in an amount of 50.0 wt% to 90.0 wt%, more preferably in an amount of 65.0 wt% to 88.0 wt%, where the percentages by weight refer to the total dispersion.

5. Dispersion according to at least one of the preceding claims, characterized in that, in the rhamnolipid ester present, R3 is selected from branched or linear alkyl radicals, preferably with 8 to 24, in particular 10 to 22, carbon atoms.

6. Dispersion according to at least one of the preceding claims, characterized in that, in the rhamnolipid ester present, R3 is selected from the group comprising, preferably consisting of, lauryl, myristyl, palmityl, stearyl, arachidyl and behenyl radicals.

7. Dispersion according to at least one of the preceding claims, characterized in that, in the rhamnolipid amide present, R3a is selected from the group of the alkyl radicals which optionally have amine groups, and R3b = alkyl radical with 1 to 8 carbon atoms or H, preferably H.

8. Dispersion according to at least one of the preceding claims, characterized in that, in the rhamnolipid amide present, R3a is selected from the group comprising where R4 and R5 = independently of one another, identical or different alkyl radical with 1 to 6, preferably 1 to 3, particularly preferably 1, carbon atom(s), R6 = an alkylene group with 1 to 6, preferably 2 to 3, carbon atoms, and where R7 = an alkylene group with 1 to 22, preferably 2 to 18, in particular 3 to 8, carbon atoms, Z = H, OH, OR8, where R8 = alkyl radical with 1 to 6, preferably 1 to 3, particularly preferably 1, carbon atom(s), and preferably R3b = H.

9. Dispersion according to at least one of the preceding claims, characterized in that, in the rhamnolipid amide present, the radical -NR3aR3b is derived from an amine NHR3aR3b, selected from amino acids and peptides.

10. Use of the rhamnolipid derivatives mentioned in one of the preceding claims, as emulsifier or dispersing aid.