Mixture compositions comprising lactylates, method for their production and use thereof

Abstract

The invention relates to mixture compositions comprising lactylates, a method for their production and their use.

Description

[0001] Mixture compositions comprising lactylates, method for their production and use thereof

[0002] Field of the invention

[0003] The invention relates to mixture compositions comprising lactylates, a method for their production and their use.

[0004] Prior art

[0005] (Poly)lactic acid esters of fatty acids, also known as acyl lactylic acid esters and lactylates can be obtained via different routes:

[0006] US3636017 discloses the process of producing a fatty acyl lactic acid product composed predominately of at least one fatty acid ester of lactic acid, whose fatty acid has from about 14 to about 24 carbons, comprising the steps:

[0007] (a) separately reacting lactic acid in an aqueous medium at a temperature from ambient to about 80 °C with from about three-quarters of (a), to about an equal, molar equivalent of an at least partly soluble in water basicly-acting agent selected from alkali metal, ammonium, alkaline earth metal, and magnesium oxides, hydroxides, carbonates, and bicarbonates, whose cation forms with it the corresponding water dispersible lactate, to form said corresponding lactate salt in said aqueous medium;

[0008] (b) then heating said lactic acid salt in said aqueous medium with at least one said fatty acid in the proportion of from about 1.5 to about 1 mole of said salt per mole of fatty acid to and at a temperature within the range of about 180 to about 220 °C. to drive off from about the major part to substantially all of the water and esterify and fatty acid with said lactic acid salt and form the corresponding salt of said fatty acid ester of lactic acid;

[0009] (c) thereafter treating said salt of said ester with an aqueous solution of a mineral acid member of the class consisting of sulfuric, hydrochloric and phosphoric acids, and heating their dispersion at a temperature of from about 60 °C to about 95 °C. for a time sufficient substantially completely to convert said salt of said ester to the corresponding acyl lactic acid, the amount of said mineral acid and its concentration in said dispersion being at least sufficient to convert said salt to said acyl lactic acid and below that which could produce any destructive products thereof under the reaction conditions; and

[0010] (d) separating said fatty acyl lactic acid from said aqueous dispersion.

[0011] US2789992 discloses a fatty acid lactylate composition selected from the group consisting of compositions of the general formula

[0012] RCO(OCHCO)nOH

[0013] CH3 and their salts, wherein RCO is the acyl radical of a fatty acid containing from 16 to 22 carbon atoms and n is the average number of lactylic groups present in such lactylate composition ranging from 1 to 8.5.

[0014] US2744825 discloses a method of retarding apparent staling in yeast leavened baked products which comprises incorporating in the dough prior to baking from 0.1 to 1.0%, based on the weight of flour, of a fatty acid lactylate composition of the general formula RCO(OCHCO)nOX

[0015] CH3in which RCO is the acyl radical of a fatty acid having from 16 to 22 carbon atoms, X is a cation, and n is the average number of lactylic groups present in such lactylate composition ranging from 1 to 8.5.

[0016] Usually, the manufacturing process does not produce chemically pure lactylates (e.g. lauroyl-2- lactylate) since lactic acid readily undergoes self-esterification producing a variety of polylactyls. The nomenclature is usually as exemplary described in the following:

[0017] Lauroyl-1 -Lactylate = Lauroyl-Monolactylate

[0018] Lauroyl-2-Lactylate = Lauroyl-Dilactylate = lauric acid ester of lactyl lactate (which is the acyclic lactic acid dimer)

[0019] Lauroyl-3-Lactylate = Lauroyl-Trilactylate

[0020] Lactylates are used in a variety of products including baked goods and mixes, pancakes, waffles, cereals, pastas, instant rice, liquid shortenings, egg whites, whipped toppings, icings, fillings, puddings, toppings, frozen desserts, creamers, cream liqueurs, sugar confectionaries, dehydrated fruits and vegetables, dehydrated potatoes, snack dips, chewing gum, dietetic foods, minced and diced canned meats, mostarda di frutta, sauces, gravies, pet food, food packaging such as paper, paperboard and cellophane, and pharmaceuticals.

[0021] Lactylates are also used in a variety of personal care products including shampoos, skin conditioners, lotions, barrier creams, makeup bases, lipsticks, deodorants, and shaving creams. In addition, lactylates are bio-friendly additives for use in polyolefins, flame retardants, pigments, and PVC.

[0022] It is well known that in ceramide blends crystallization of the ceramides must be avoided because otherwise the bioavailability of the ceramides is decreased, i.e. they become inert und unfunctional.

[0023] EP3733157 discloses a composition containing at least one ceramide, at least one sphingoid base and triethyl citrate, a method for preparing a formulation containing at least one ceramide and the use of triethyl citrate to stabilize a ceramide-containing formulation. WO1998053797 discloses encapsulated, water-insoluble active ingredients with an amphiphilic character, containing water and at least one surfactant from the group of esters of long-chain carboxylic acids with hydroxyl-containing carboxylic acids or their salts and the esters of long-chain carboxylic acids with polyalcohols. It is explicitly stated that the long-chain carboxylic acids belonging to the group of C8 to C12 fatty acids, especially C10 fatty acid, work best.

[0024] WO2018177730 discloses a method for producing a formulation containing ceramide, comprising the method steps: A) Melting a mixture containing at least one wax and at least one ceramide, B) Cooling the melted mixture to obtain a solidified melt containing the at least one wax and the at least one ceramide, C) Incorporating the solidified melt into a formulation containing oil.

[0025] The object of the invention was to provide a means that can physically stabilize compositions comprising ceramides.

[0026] Description of the invention

[0027] Surprisingly, it was found that mixture compositions comprising lactylates as described in claim 1 can solve the problem addressed by the invention.

[0028] The present invention therefore provides mixture compositions comprising lactylates as described in claim 1 and their use for the physical stabilization of a ceramide.

[0029] The invention further provides a process for the preparation of a mixture of lactylates.

[0030] An advantage of the present invention is that the dissolution temperature for the ceramides in oils is lowered. This makes it possible that ceramide-containing formulations can be prepared in an energy-saving manner since only a relatively small amount of substance has to be heated to high temperatures, and most of the formulation constituents can be formulated at relatively low temperatures.

[0031] This results in a further advantage, namely that temperature-sensitive ingredients may be incorporated into ceramide-containing formulations.

[0032] The high dissolution temperature of the ceramides in oils often presents a technical problem, since for example sufficiently high temperatures are not attained using steam heaters. This problem is also solved by the invention.

[0033] A further advantage of the present invention is that ceramides may also be introduced into formulations in a one-pot process due to the present invention. Another advantage of the present invention is that the formulations according to the invention have increased storage stability and are thus slower to change in their nature over time, particularly regarding their viscosity, compared to ceramide-containing formulations according to the prior art. Another advantage of the present invention is that the formulations according to the invention tolerate a higher number of freeze-thaw steps without significant loss of viscosity, compared to ceramide-containing formulations according to the prior art.

[0034] One advantage of the composition according to the invention is that the composition in formulations has superior sensory properties which lead to an improved skin feel and / or hair feel.

[0035] It is a further advantage of the composition according to the invention that the composition in formulations stimulates in vitro human follicular dermal papilla cells (HFDPCs) to proliferate, which in vivo equates to stimulation of hair growth.

[0036] It is a further advantage of the composition according to the invention that the composition in formulations has improved distributability compared to the individual components.

[0037] It is a further advantage of the composition according to the invention that the composition in formulations has improved absorption compared to the individual components.

[0038] It is a further advantage of the composition according to the invention that the composition in formulations has reduced oiliness compared to the individual components.

[0039] It is a further advantage of the composition according to the invention that the composition in formulations has reduced waxiness compared to the individual components.

[0040] It is a further advantage of the composition according to the invention that the composition in formulations has improved glidability compared to the individual components.

[0041] It is a further advantage of the composition according to the invention that the composition in formulations has reduced tackiness compared to the individual components.

[0042] It is a further advantage of the composition according to the invention that the composition in formulations has improved silkiness / velvetiness compared to the individual components.

[0043] The present invention provides a mixture composition comprising a monolactylate of at least one carboxylic acid with 12 carbon atoms and at least one oligolactylate of at least one carboxylic acid with 12 carbon atoms and a monolactylate of at least one carboxylic acid with 14 to 22 carbon atoms and at least one oligolactylate of at least one carboxylic acid with 14 to 22 carbon atoms.

[0044] The term “lactylate” in context with the instant invention are esters of carboxylic acids with lactic acid and / or with oligomers of lactic acid.

[0045] The structure is depicted in general formula (I) with RC(O) being an acyl radical of a carboxylic acid with 6 to 24 carbon atoms, X being a hydrogen atom or a cation and n = 1 to 10. general formula (I)

[0046] The term “oligolactylate” in context with the instant invention encompasses di-, tri-, tetra- and all higher lactylates.

[0047] The term “lactylate” in context with the instant invention encompasses mono- as well as oligolactylates.

[0048] Where average values are stated hereinbelow, then, unless stated otherwise, these are number- averaged average values.

[0049] Unless stated otherwise, percentages are data in per cent by weight. The same is true for parts per million (ppm).

[0050] Wherever measurement values are stated hereinbelow, then, unless stated otherwise, these have been determined at a temperature of 25°C and a pressure of 1013 mbar.

[0051] A preferred mixture composition according to the instant invention is characterized in that the molar ratio of the sum of all said at least one carboxylic acid with 12 carbon atoms and the sum of all said at least one carboxylic acid with 14 to 22 carbon atoms comprised in all lactylates is in the range of from 99:1 to 1 :99, preferred from 95:5 to 50:50, more preferred from 90:10 to 55:45, most preferred from 85:15 to 60:40.

[0052] GC Method M01

[0053] The molar ratio of said at least one carboxylic acid with 12 carbon atoms to the sum of all said at least one carboxylic acid with 14 to 22 carbon atoms can be determined via the method below after saponification of the lactylates and isolation of the fatty acids.

[0054] For this purpose, 0.05 g of the mixture composition is boiled under reflux in a mixture of 0.5 mL of 2N ethanolic KOH and 0.5 mL of toluene for 2 h. After cooling to room temperature, 1 mL of water are added, and the solution is adjusted to pH 2-3 with sulfuric acid. The fatty acids are isolated by extraction with three portions of the double volume of petroleum ether. The combined extracts are evaporated to a volume of approx. 0.5 mL and 1 mL of chloroform are added. A 0.25 mL aliquot is transferred to an autosampler vial and 0.5 mL MSTFA [A / -methyl-A / -(trimethylsilyl) trifluoroacetamide] and 0.03 mL trimethylchlorsilane as derivatization agent are added. The derivatization is finalized at 80°C within 30 minutes. An aliquot is analyzed by GC.

[0055] The fatty acid analysis by GC is carried out using a gas chromatograph equipped with a split / splitless injector, a capillary column and a flame ionization detector. Conditions:

[0056] Injector: 290°C, split 1 :20 mL

[0057] Injected volume: 1 pL

[0058] Column: 30 m * 0.32 mm HP1 0.25 pm

[0059] Carrier gas: Hydrogen, constant flow 2mL / min

[0060] Temp, program: 80°C to 300°C at 8°C / min;

[0061] Detector: FID at 310°C

[0062] Hydrogen30 mL / min

[0063] Air 400 mL / min

[0064] Make-up gas (purge gas) 12 mL / min

[0065] When using these conditions, the trimethylsilyl carboxylate esters are separated according to their chain length.

[0066] The relative mass content ratio of the individual carboxylic acids (chain-length distribution) is evaluated from the percentage of the peak area in the chromatogram. The corresponding molar ratio is calculated with respect to the individual molecular weights of the carboxylic acids.

[0067] A preferred mixture composition according to the instant invention has a content of

[0068] 50 wt.-% to 90 wt.-%, preferably 55 wt.-% to 85 wt.-%, more preferably 60 wt.-% to 80 wt.-%, of the sum of said monolactylate of at least one carboxylic acid with 12 carbon atoms and of said at least one oligolactylate of at least one carboxylic acid with 12 carbon atoms, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition.

[0069] The content of the individual lactylates in the mixture composition according to the instant invention is determined via the GC Method M02 described below.

[0070] GC Method M02

[0071] For analysis by GC, 10 mg of the sample are dissolved in 0.5 mL pyridine:chloroform (4:1) together with 1 .5 mg tridecanoic acid and 1 .5 mg 1 ,2-propanediol. This solution is then treated with 0.5 mL MSTFA [A / -methy l-A / -(trimethy Isily I) trifluoroacetamide] and 0.03 mL trimethylchlorosilane. The alcohol and acid groups are quantitatively converted to their trimethylsilyl ethers and esters by reaction at 80°C for 30 minutes and then analyzed by GC / FID.

[0072] The analysis is carried out in a gas chromatograph equipped with a split / splitless injector, a capillary column, and a flame ionization detector under the following conditions: Injector: 290 °C, Split 1 :20

[0073] Injection volume: 1 pl column: 30 m * 0.32 mm HP1 0.25 pm carrier gas: hydrogen, const, flow 2 mL / min temperature program: 80 °C - 300 °C with 8 °C / min,

[0074] 15 minutes hold-up at 300 °C.

[0075] Detector: FID at 310 °C

[0076] Hydrogen 30 mL / min

[0077] Air 400 mL / min

[0078] Make Up Gas 12 mL / min

[0079] The trimethylsilyl derivatives of lactic acid, of the lactic acid oligomers, of the fatty acids, of the monolactylates, of the dilactylates, of the trilacty lates, of tridecanoic acid, and of 1 ,2-propanediol are separated.

[0080] The mass fraction of fatty acids can be determined by evaluating the peak areas of the individual fatty acids compared to the peak area of the tridecanoic acid added as an internal standard with a known content.

[0081] The mass fraction of lactic acid as a sum can be determined by evaluating the sum of the peak areas of the lactic acid monomer and oligomers compared to the peak area of the 1 ,2-propanediol which is added as an internal standard with a known content. The GC system is calibrated for this purpose by measuring mixtures of lactic acid and the internal standard 1 ,2-propanediol with known compositions.

[0082] The contents of monolactylates, dilactylates, and tri lactylates are determined according to their area-% shares in the gas chromatogram. For this, the sum of all area percentage shares of the monolactylates, dilactylates, and trilactylates as well as of all unidentified peaks are normalized to the wt-% content of 100% minus the sodium content (as determined via ICP-OES; see below), minus the water content, minus the quantitatively determined contents of lactic acid and its oligomers and minus the quantitatively determined contents free fatty acids.

[0083] Suitable detection methods for determining the water content are in particular those according to DIN 51777, DGF E-lll 10 and DGF C-lll 13a.

[0084] An example for the determination of the overall composition of a mixture composition according to the instant invention is shown below:

[0085] A preferred mixture composition according to the instant invention has a content of

[0086] 10 wt.-% to 50 wt.-%, preferably 15 wt.-% to 45 wt.-%, more preferably 20 wt.-% to 40 wt.-%, of the sum of said monolactylate of at least one carboxylic acid with 14 to 22 carbon atoms and of said at least one oligolactylate of at least one carboxylic acid with 14 to 22 carbon atoms, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition.

[0087] A more preferred mixture composition according to the instant invention has a content of

[0088] 50 wt.-% to 90 wt.-%, preferably 55 wt.-% to 85 wt.-%, more preferably 60 wt.-% to 80 wt.-%, of the sum of said monolactylate of at least one carboxylic acid with 12 carbon atoms and of said at least one oligolactylate of at least one carboxylic acid with 12 carbon atoms, and 10 wt.-% to 50 wt.-%, preferably 15 wt.-% to 45 wt.-%, more preferably 20 wt.-% to 40 wt.-%, of the sum of said monolactylate of at least one carboxylic acid with 14 to 22 carbon atoms and of said at least one oligolactylate of at least one carboxylic acid with 14 to 22 carbon atoms, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition.

[0089] In a preferred mixture composition according to the instant invention the above-mentioned content of lactylates is due to lactylates of fatty acids with the appropriate number of carbon atoms.

[0090] Fatty acids can be produced for example based on naturally occurring vegetable or animal oils and have preferably 6 to 30 carbon atoms, especially 8 to 22 carbon atoms. Natural fatty acids are generally unbranched and usually consist of an even number of carbon atoms. Any double bonds have cis configuration.

[0091] Even more preferred fatty acids of the lactylates with the above-mentioned content in the mixture composition are selected from lauric acid, myristic acid, palmitic acid, palmitoleic acid, isostearic acid, stearic acid, 12-hydroxystearic acid, di hydroxy stearic acid, oleic acid, linoleic acid, linolenic acid, petroselinic acid, elaidic acid, arachic acid, behenic acid, erucic acid, gadoleic acid, eicosapentaenoic acid, docosahexaenoic acid and arachidonic acid.

[0092] A preferred mixture composition according to the instant invention has a content of at least 85 wt.-%, preferably 90 wt.-% to 100 wt.-%, of the sum of said monolactylate of at least one carboxylic acid with 12 carbon atoms and of said monolactylate of at least one carboxylic acid with 14 to 22 carbon atoms and of said at least one oligolactylate of at least one carboxylic acid with 12 carbon atoms, and of said at least one oligolactylate of at least one carboxylic acid with 14 to 22 carbon atoms, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition.

[0093] A preferred mixture composition according to the instant invention has a content of

[0094] 50 wt.-% to 90 wt.-%, preferably 55 wt.-% to 85 wt.-%, more preferably 60 wt.-% to 80 wt.-%, of the sum of monolactylate of lauric acid and of at least one oligolactylate, preferably dilactylate, of lauric acid, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition.

[0095] A preferred mixture composition according to the instant invention has a content of

[0096] 10 wt.-% to 50 wt.-%, preferably 15 wt.-% to 45 wt.-%, more preferably 20 wt.-% to 40 wt.-%, of the sum of monolactylate of myristic acid and of at least one oligolactylate, preferably dilactylate, of myristic acid, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition. A more preferred mixture composition according to the instant invention has a content of

[0097] 50 wt.-% to 90 wt.-%, preferably 55 wt.-% to 85 wt.-%, more preferably 60 wt.-% to 80 wt.-%, of the sum of monolactylate of lauric acid and of dilactylate of lauric acid, and

[0098] 10 wt.-% to 50 wt.-%, preferably 15 wt.-% to 45 wt.-%, more preferably 20 wt.-% to 40 wt.-%, of the sum of monolactylate of myristic acid and of dilactylate of myristic acid, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition.

[0099] A preferred mixture composition according to the instant invention has a content of

[0100] 25 wt.-% to 70 wt.-%, preferably 30 wt.-% to 60 wt.-%, more preferably 40 wt.-% to 56 wt.-%, of the sum of all monolactylates comprised in the mixture composition according to the instant invention, wherein the percentages by weight refer to the total mixture composition.

[0101] A preferred mixture composition according to the instant invention has a content of

[0102] 0.01 wt.-% to 15 wt.-%, preferably 1 .0 wt.-% to 12 wt.-%, more preferably 2.0 wt.-% to 10 wt.-%, of the sum of all dilactylates comprised in the mixture composition according to the instant invention, wherein the percentages by weight refer to the total mixture composition.

[0103] A preferred mixture composition according to the instant invention has a content of 0.02 wt.-% to 15.0 wt.-%, preferably 0.05 wt.-% to 10 wt.-%, more preferably 0.1 wt.-% to 5 wt.-%, of the sum of all trilactylates comprised in the mixture composition according to the instant invention, wherein the percentages by weight refer to the total mixture composition.

[0104] A preferred mixture composition according to the instant invention has a content of

[0105] 0.5 wt.-% to 30 wt.-%, preferably 2.0 wt.-% to 18.0 wt.-%, more preferably 4.0 wt.-% to 15.0 wt.-%, lactic acid monomers and / or oligomers, wherein the percentages by weight refer to the total mixture composition.

[0106] A preferred mixture composition according to the instant invention is characterized in that at least 90 wt.%, preferably 92 wt.% to 100 wt.%, preferably 95 wt.% to 98 wt.%, of all lactic acid residues within the lactylates comprised in the mixture composition according to the instant invention are L- lactic acid residues, wherein the percentages by weight refer to all lactic acid residues within all lactylates comprised in the mixture composition according to the instant invention. This is due to the preferred mixture composition according to the instant invention being characterized in that the lactic acid used in the preparation process of the lactylates comprised in the mixture composition according to the instant invention was prepared by fermentation of a microorganism, preferably with natural carbohydrates, for example glucose, sucrose and saccharose, as carbon source.

[0107] A preferred mixture composition according to the instant invention is characterized in that it has a specific rotation at 589 nm at 25 °C of from -15.0 deg mL g-1dnrr1to -0.1 deg mL g-1dnrr1, preferably -7.5 deg mL g-1dm-1to -2.5 deg mL g-1dm-1, more preferably -5.5 deg mL g-1dm-1to -4.5 deg mL g-1dnrr1.

[0108] A suitable method for measuring the specific rotation is described below:

[0109] The measurement of the optical rotation follows the principle of optical zero balancing. Monochromatic light passes from the polarizer through the sample room and the analyzer to a photomultiplier. In the zero-balancing position, the polarizer and analyzer are oriented perpendicular to each other. If the plane of the polarized light is rotated by an optically active substance in the sample room, the analyzer is moved with a servo system until the optical zero balancing is reached again. The optical rotation is measured with an optical encoder and displayed digitally. The specific rotation is calculated with the optical rotation and concentration of the measured solution.

[0110] Apparatus: Analytical Balance, Polarimeter Autopol V Plus, Volumetric flask 20 mL Chemicals: Ethanol, Merck Art Nr. 1.00983.1000 Charge: 11239083236

[0111] Reference Material: Sucrose, Merck Art Nr. 1 .07687.0250 Charge: K51117387 017 Parameters:

[0112] Temperature: 25 °C

[0113] Concentration: 0.5 g / 50 mL

[0114] Wavelength: 589 nm

[0115] Path length: 10 dm

[0116] Solvent: Ethanol

[0117] Approximately 0.5 g of the sample are weighed into a 50 mL graduated flask and solved in 35 mL ethanol at room temperature. Then the solution was tempered at 25 °C and filled up to the mark with ethanol. After homogenization the sample solution was measured.

[0118] A preferred mixture composition according to the instant invention has an acid value of 30 mg KOH / g to 80 mg KOH / g, preferably 40 mg KOH / g to 75 mg KOH / g, especially preferably from 50 mg KOH / g to 70 mg KOH / g.

[0119] Suitable methods for determining the acid value are in particular those according to DGF C-V 2, DIN EN ISO 2114, Ph. Eur. 2.5.1 , ISO 3682 and ASTM D 974. A preferred mixture composition according to the instant invention has a saponification value of 180 mg KOH / g to 225 mg KOH / g, preferably 185 mg KOH / g to 215 mg KOH / g, especially preferably from 190 mg KOH / g to 210 mg KOH / g.

[0120] Suitable detection methods for determining the saponification value are in particular those according to DGF C-V 3, DIN EN ISO 3681 and Ph. Eur. 2.5.6.

[0121] A preferred mixture composition according to the instant invention has an ester value of 105 KOH / g to 160 mg KOH / g, preferably 110 KOH / g to 155 mg KOH / g, especially preferably from 115 KOH / g to 150 mg KOH / g.

[0122] The ester value is calculated by “saponification value minus acid value”.

[0123] A preferred mixture composition according to the instant invention comprises at least one free fatty acid or its salt.

[0124] The free fatty acid as a salt is preferably comprised as sodium salt.

[0125] A preferred mixture composition according to the instant invention is characterized in that it has a content of

[0126] 5.0 wt.-% to 45 wt.-%, preferably 15 wt.-% to 40 wt.-%, more preferably 22 wt.-% to 36 wt.-%, of at least one free fatty acid and / or its salt, wherein the percentages by weight refer to the total composition.

[0127] In the above only the free fatty acid contributes to the weight percentages, the counter cation is disregarded. The content of free fatty acid is determined via the GC Method M02 described above.

[0128] A preferred mixture composition according to the instant invention is characterized in that it has a content of

[0129] 5.0 wt.-% to 40 wt.-%, preferably 8.0 wt.-% to 35 wt.-%, more preferably 10 wt.-% to 30 wt.-%, free lauric acid and / or its salt, wherein the percentages by weight refer to the total composition.

[0130] In the above only the free lauric acid contributes to the weight percentages, the counter cation is disregarded. The content of free lauric acid is determined via the GC Method M02 described above. A preferred mixture composition according to the instant invention comprises at least one selected from the group of lactic acid, lactic acid oligomers and their salts.

[0131] A preferred mixture composition according to the instant invention is characterized in that it has a content of

[0132] 0.1 wt.-% to 30 wt.-%, preferably 1 .0 wt.-% to 20 wt.-%, more preferably 3.0 wt.-% to 15 wt.-%, of all lactic acid, lactic acid oligomers and their salts, wherein the percentages by weight refer to the total composition.

[0133] In the above only the lactic acid and its oligomers contribute to the weight percentages, the counter cation is disregarded. The sum is being determined as content of lactic acid, lactic acid dimer and lactic acid trimer via the GC Method M02 described above.

[0134] A preferred mixture composition according to the instant invention is characterized in that it has a Na+content of 1 .0% to 15.0%, preferred 5.0% to 9.0%, more preferred 6.0% to 8.0%, wherein the percentages by weight refer to the total composition.

[0135] A suitable method for determining the sodium content is inductively coupled plasma mass spectroscopy (ICP-OES) as describes below:

[0136] To a sample, which may be homogenized, if necessary, concentrated HNO3 / H2O2 is added and the sample is digested in the microwave for 20 minutes. The sample is cooled down to room temperature and diluted with deionized water to a predefined volume. The sampled material is introduced in a high-energy argon plasma (ICP-OES) for excitation and atomization.

[0137] Concentrations are quantified using a calibration curve achieved by measuring external reference standards.

[0138] The present invention further provides a process for the preparation of a mixture of lactylates, preferably the mixture composition according of the instant invention comprising lactylates, comprising the steps of

[0139] A) providing lactic acid, at least one carboxylic acid with 12 carbon atoms and at least one carboxylic acid with 14 to 22 carbon atoms,

[0140] B) esterification of said acids provided in A) while obtaining a mixture of lactylates, and optionally

[0141] C) purification of said mixture of lactylates.

[0142] A preferred process according to the instant invention is characterized in that said lactic acid provided in process step A) is provided by a fermentation process. A preferred process according to the instant invention is characterized in that said carboxylic acids provided in process step A) are selected from fatty acids.

[0143] The fatty acids can be provided in many different ways, for example as free fatty acids, as their salts or as activated fatty acid species, for example as acyl chlorides.

[0144] However, in a preferred process according to the instant invention the fatty acids are provided in the form of free fatty acids; preferably no acyl chlorides are present in the process of the instant invention.

[0145] A preferred process according to the instant invention is characterized in that said at least one carboxylic acid with 12 carbon atoms provided in process step A) is lauric acid, and preferably said at least one carboxylic acid with 14 to 22 carbon atoms provided in process step A) is myristic acid.

[0146] A preferred process according to the instant invention is characterized in that the the molar ratio of the sum of all said at least one carboxylic acid with 12 carbon atoms and the sum of all said at least one carboxylic acid with 14 to 22 carbon atoms provided in process step A) is in the range of from 99:1 to 1 :99, preferred from 95:5 to 50:50, more preferred from 90:10 to 55:45, most preferred from 85:15 to 60:40.

[0147] A preferred process according to the instant invention is characterized in that in the esterification of process step B) the molar ratio of lactic acid and the sum of all carboxylic acids with 12 to 22 carbon atoms provided in process step A) is in the range from 0.80:1 .00 to 1 .50:1 .00, preferably 1 .00:1 .00 to 1 .30:1 .00, more preferably 1 .05:1 .00 to 1 .25:1 .00.

[0148] A preferred process according to the instant invention is characterized in that the esterification of process step B) is carried out in the presence of a base, preferably a sodium base, most preferably selected from NaOH and Na2CO3, preferably provided as aqueous solution.

[0149] A preferred process according to the instant invention is characterized in that the esterification of process step B) is carried out in the presence of a sodium base and that in the esterification of process step B) the molar ratio of Na+provided by the sodium base and lactic acid is in the range from 0.70:1.00 to 1.20:1.00, preferably 0.80:1.00 to 1.05:1.00, more preferably 0.85:1.00 to 1.02:1.00. A preferred process according to the instant invention is characterized in that in process step B) the sum of all lactic acid, all carboxylic acids, intermediates and lactylates account for at least 50 wt.- %, preferably 60 wt.-% to 98 wt.-%, more preferably 70 wt.-% to 95 wt.-%, of the reaction mixture.

[0150] In the above there is hardly any room for the addition of solvents; a preferred process according to the instant invention thus is characterized in that it is free of organic solvents.

[0151] The compositions according to the instant invention are useful for the preparation of cosmetic or pharmaceutical formulations.

[0152] Thus, the present invention further relates to a cosmetic or pharmaceutical formulation comprising a composition according to the instant invention, a cosmetic and / or pharmaceutical acceptable carrier, preferable water, and a cosmetical and / or pharmaceutical formulation ingredient.

[0153] Said one further cosmetical and pharmaceutical formulation ingredient is, of course, different from any component comprised in the composition of the instant invention.

[0154] Preferred compositions according to the instant invention are preferably comprised in the formulations according to the instant invention.

[0155] A preferred formulation according to the instant invention is characterized in that it has a content of 70.0 wt.-% to 95.0 wt.-%, preferably 73.0 wt.-% to 91 .0 wt.-%, more preferably 76.0 wt.-% to 88.0 wt.-%, of water, wherein the percentages by weight refer to the total formulation.

[0156] A preferred formulation according to the instant invention is characterized in that it has a content of 2.8 wt.-% to 8.8 wt.-%, preferably 3.3 wt.-% to 8.3 wt.-%, more preferably 3.8 wt.-% to 7.8 wt.-%, of the sum of all monolactylates and oligolactylates, wherein the percentages by weight refer to the total formulation.

[0157] Said cosmetical and pharmaceutical formulation ingredient is preferably selected from the group of actives, surfactants, emollients, emulsifiers, thickeners, UV light protection filters, antioxidants, hydrotropes, solids and fillers, film formers, pearlescence additives, opacifiers, deodorant and antiperspirant active ingredients, insect repellents, self-tanning agents, preservatives, conditioning agents, perfumes, dyes, odour absorbers, superfatting agents and solvents, preferably actives and thickeners. A preferred formulation according to the instant invention comprises as said cosmetical and pharmaceutical formulation ingredient at least one ceramide.

[0158] In the context of the present invention, the term “ceramide” is understood as acylated sphingoid bases, where the sphingoid bases are preferably selected from sphingosine, sphinganine, 6- hydroxysphingosine and phytosphingosine, also in glycosylated form, for example as glucosylceramides.

[0159] A preferred formulation according to the instant invention is characterized in that said at least one ceramide is selected from the group comprising, preferably consisting of, ceramide NP, ceramide AP, ceramide EOP, ceramide NG (also known as ceramide NDS and ceramide 2), ceramide ADS, ceramide EODS, ceramide NS, ceramide AS, ceramide EOS, ceramide NH, ceramide AH and ceramide EOH, preferably selected from the group comprising ceramide NP, ceramide NG, ceramide AP and ceramide EOP, most preferably ceramide NP.

[0160] A preferred formulation according to the instant invention is characterized in that it has a content of 2.8 wt.-% to 8.8 wt.-%, preferably 3.3 wt.-% to 8.3 wt.-%, more preferably 3.8 wt.-% to 7.8 wt.-%, of the sum of all monolactylates and oligolactylates and

[0161] 0.1 wt.-% to 5.0 wt.-%, preferably 0.5 wt.-% to 3.0 wt.-%, more preferably 1 .3 wt.-% to 2.3 wt.-%, of the sum of all ceramides, wherein the percentages by weight refer to the total formulation.

[0162] A preferred formulation according to the instant invention is characterized in that it has a content of ceramide NP of

[0163] 10 wt.-% to 100 wt.-%, preferably 20 wt.-% to 90 wt.-%, more preferably 25 wt.-% to 80 wt.-%, wherein the percentages by weight refer to the sum of all ceramides.

[0164] Preferably the mass ratio of all lactylates and all ceramides comprised in the formulation according to the instant invention is in the range of from 1 .10:1 .00 to 6.00:1 .00, preferably 1 .40:1 .00 to 5.50:1 .00, more preferably 1 .60:1 .00 to 5.30:1 .00.

[0165] A preferred formulation according to the instant invention comprises as said cosmetical and pharmaceutical formulation ingredient cholesterol.

[0166] A preferred formulation according to the instant invention is characterized in that it has a content of 2.8 wt.-% to 8.8 wt.-%, preferably 3.3 wt.-% to 8.3 wt.-%, more preferably 3.8 wt.-% to 7.8 wt.-%, of the sum of all monolactylates and oligolactylates and

[0167] 0.05 wt.-% to 1 .5 wt.-%, preferably 0.2 wt.-% to 0.9 wt.-%, more preferably 0.4 wt.-% to 0.7 wt.-%, of cholesterol, wherein the percentages by weight refer to the total formulation.

[0168] Preferably the mass ratio of all lactylates and cholesterol comprised in the formulation according to the instant invention is in the range of from 1 .00:1 .00 to 95.00:1 .00, preferably 2.00: 1 .00 to 40.00:1 .00, more preferably 5.00:1 .00 to 20.00:1 .00.

[0169] The cholesterol can be of vegetable, animal or synthetic origin.

[0170] A preferred formulation according to the instant invention comprises as said cosmetical and pharmaceutical formulation ingredient at least one carbomer.

[0171] A preferred formulation according to the instant invention is characterized in that it has a content of 2.8 wt.-% to 8.8 wt.-%, preferably 3.3 wt.-% to 8.3 wt.-%, more preferably 3.8 wt.-% to 7.8 wt.-%, of the sum of all monolactylates and oligolactylates and

[0172] 0.01 wt.-% to 1 .00 wt.-%, preferably 0.05 wt.-% to 0.80 wt.-%, more preferably 0.10 wt.-% to 0.60 wt.-%, of the sum of all carbomers, wherein the percentages by weight refer to the total formulation.

[0173] Preferably the mass ratio of all lactylates and all carbomers comprised in the formulation according to the instant invention is in the range of from 1 .00:1 .00 to 95.00:1 .00, preferably 3.00:1 .00 to 85.00:1 .00, more preferably 5.00:1 .00 to 80.00:1 .00.

[0174] A preferred formulation according to the instant invention comprises as said cosmetical and pharmaceutical formulation ingredient at least one xanthan gum.

[0175] A preferred formulation according to the instant invention is characterized in that it has a content of 2.8 wt.-% to 8.8 wt.-%, preferably 3.3 wt.-% to 8.3 wt.-%, more preferably 3.8 wt.-% to 7.8 wt.-%, of the sum of all monolactylates and oligolactylates and

[0176] 0.005 wt.-% to 1 .5 wt.-%, preferably 0.05 wt.-% to 1 .0 wt.-%, more preferably 0.1 wt.-% to 0.7 wt.-%, of the sum of all xanthan gums, wherein the percentages by weight refer to the total formulation.

[0177] Preferably the mass ratio of all lactylates and all xanthan gums comprised in the formulation according to the instant invention is in the range of from 1 .00:1 .00 to 95.00:1 .00, preferably 3.00:1 .00 to 85.00:1 .00, more preferably 5.00:1 .00 to 80.00:1 .00.

[0178] A preferred formulation according to the instant invention comprises as said cosmetical and pharmaceutical formulation ingredient at least one preservative selected from the group of triethy Icitrat, caprylyl glycol, methylparaben, propylparaben, phenoxyethanol, ethylhexylglycerin and benzoic acid.

[0179] A preferred formulation according to the instant invention is characterized in that it has a content of 2.8 wt.-% to 8.8 wt.-%, preferably 3.3 wt.-% to 8.3 wt.-%, more preferably 3.8 wt.-% to 7.8 wt.-%, of the sum of all monolactylates and oligolactylates and, preferably if the case,

[0180] 0.05 wt.-% to 3.0 wt.-%, preferably 0.1 wt.-% to 2.5 wt.-%, more preferably 0.4 wt.-% to 1 .9 wt.-%, of the sum of said at least one preservative, wherein the percentages by weight refer to the total formulation.

[0181] Preferably the mass ratio of all lactylates and all preservatives comprised in the formulation according to the instant invention is in the range of from 1 .00:1 .00 to 80.00:1 .00, preferably 1 .50:1 .00 to 40.00:1 .00, more preferably 1 .80: 1 .00 to 25.00:1 .00.

[0182] A preferred formulation according to the instant invention is characterized in that it has a viscosity of 10 to 200000 mPa s, preferably 100 to 100000 mPa s, most preferably 500 to 10000 mPa s, at 25 °C.

[0183] A suitable method for the determination of the viscosity is measuring the Brookfield viscosity (Brookfield RVT, Spindle 5, 50 rpm).

[0184] A preferred formulation according to the instant invention is characterized in that it does not comprise liposomes.

[0185] The present invention further relates to the use of a composition according to the instant invention for physical stabilization of a ceramide-containing formulation, in particular regarding homogeneity, and / or for preventing crystallization of at least one ceramide in a formulation.

[0186] In the context of the present invention, the term “physically stable” is understood to describe formulations which in particular do not exhibit any crystallization of the ceramide and no separation or inhomogeneity after six months of storage at 25° C.

[0187] The examples adduced hereinafter describe the present invention by way of example, without any intention that the invention, the scope of application of which is apparent from the entirety of the description and the claims, be restricted to the embodiments specified in the examples. Examples

[0188] Example 1 (inventive): Mixture of C12 and C14 fatty acids (n / n = 73:27), 0.80 equiv. of lactic acid

[0189] A mixture of lauric acid (99% C12, 130.0 g, 0.649 mol), myristic acid (98% C14, 55.7 g, 0.244 mol) and L-(+)-lactic acid (90% aq., 71.5 g, 0.714 mol) was heated to 50 °C and then NaOH (50% aq., 57.0 g, 0.713 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 175 °C, the pressure was reduced to 30 mbar and the resulting water was continuously distilled until an acid value of 65 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 63 mg KOH / g, SV = 201 mg KOH / g, EV = 138 mg KOH / g, Na = 6.8%).

[0190] Example 2 (inventive): Mixture of C12 and C14 fatty acids (n / n = 73:27), 0.90 equiv. of lactic acid

[0191] A mixture of lauric acid (99% C12, 95.0 g, 0.474 mol), myristic acid (98% C14, 40.7 g, 0.178 mol) and L-(+)-lactic acid (90% aq., 58.8 g, 0.587 mol) was heated to 50 °C and then NaOH (50% aq., 43.1 g, 0.539 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 180 °C, the pressure was reduced to 30 mbar and the resulting water was continuously distilled until an acid value of 61 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 58 mg KOH / g, SV = 209 mg KOH / g, EV = 151 mg KOH / g, Na = 6.8%).

[0192] Example 3 (inventive): Mixture of C12 and C14 fatty acids (n / n = 73:27), 1.00 equiv. of lactic acid

[0193] A mixture of lauric acid (99% C12, 125.0 g, 0.624 mol), myristic acid (98% C14, 53.6 g, 0.235 mol) and L-(+)-lactic acid (90% aq., 85.9 g, 0.858 mol) was heated to 50 °C and then NaOH (50% aq., 58.6 g, 0.733 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 180 °C, the pressure was reduced to 30 mbar and the resulting water was continuously distilled until an acid value of 67 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 67 mg KOH / g, SV = 218 mg KOH / g, EV = 151 mg KOH / g, Na = 6.8%).

[0194] Example 4 (inventive): Mixture of C12 and C14 fatty acids (n / n = 73:27), 1. 10 equiv. of lactic acid A mixture of lauric acid (99% C12, 140.0 g, 0.699 mol), myristic acid (98% C14, 60.0 g, 0.263 mol) and L-(+)-lactic acid (90% aq., 105.9 g, 1.06 mol) was heated to 50 °C and then NaOH (50% aq., 74.5 g, 0.931 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 175 °C, the pressure was reduced to 30 mbar and the resulting water was continuously distilled until an acid value of 70 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 66 mg KOH / g, SV = 204 mg KOH / g, EV = 138 mg KOH / g, Na = 7.0%).

[0195] Example 5 (inventive): Mixture of C12 and C14 fatty acids (n / n = 65:35), 1. 15 equiv. of lactic acid

[0196] A mixture of lauric acid (99% C12, 150.0 g, 0.749 mol), myristic acid (98% C14, 92.2 g, 0.404 mol) and L-(+)-lactic acid (90% aq., 132.6 g, 1.32 mol) was heated to 50 °C and then NaOH (50% aq.,

[0197] 94.8 g, 1.19 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 175 °C and the resulting water was continuously distilled until an acid value of 70 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 69 mg KOH / g, SV = 194 mg KOH / g, EV = 125 mg KOH / g, Na = 7.7%).

[0198] Example 6 (inventive): Mixture of C12 and C14 fatty acids (n / n = 80:20), 1. 15 equiv. of lactic acid

[0199] A mixture of lauric acid (99% C12, 150 g, 0.749 mol), myristic acid (98% C14, 42.8 g, 0.187 mol) and L-(+)-lactic acid (90% aq., 107.7 g, 1.08 mol) was heated to 50 °C and then NaOH (50% aq.,

[0200] 75.9 g, 0.949 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 175 °C and the resulting water was continuously distilled until an acid value of 70 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 66 mg KOH / g, SV = 200 mg KOH / g, EV = 134 mg KOH / g, Na = 7.5%).

[0201] Example 7 (inventive): Mixture of C12 and C14 fatty acids (n / n = 73:27), 1.20 equiv. of lactic acid

[0202] A mixture of lauric acid (99% C12, 130.0 g, 0.649 mol), myristic acid (98% C14, 55.7 g, 0.244 mol) and L-(+)-lactic acid (90% aq., 107.3 g, 1.07 mol) was heated to 50 °C and then NaOH (50% aq., 74.1 g, 0.926 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 200 °C, the pressure was reduced to 30 mbar and the resulting water was continuously distilled until an acid value of 68 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 61 mg KOH / g, SV = 204 mg KOH / g, EV = 143 mg KOH / g, Na = 7.7%).

[0203] Example 8 (inventive): Mixture of C12 and C16 fatty acids (n / n = 80:20), 1. 15 equiv. of lactic acid

[0204] A mixture of lauric acid (99% C12, 150 g, 0.749 mol), palmitic acid (99% C16, 48.1 g, 0.187 mol) and L-(+)-lactic acid (90% aq., 107.8 g, 1.08 mol) was heated to 50 °C and then NaOH (50% aq., 75.6 g, 0.946 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 175 °C and the resulting water was continuously distilled until an acid value of 65 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 60 mg KOH / g, SV = 195 mg KOH / g, EV = 135 mg KOH / g, Na = 7.6%).

[0205] Example 9 (inventive): Mixture of C12 and C18 fatty acids (n / n = 80:20), 1. 15 equiv. of lactic acid

[0206] A mixture of lauric acid (99% C12, 150 g, 0.749 mol), stearic acid (95% C18, 53.3 g, 0.187 mol) and L-(+)-lactic acid (90% aq., 107.8 g, 1.08 mol) was heated to 50 °C and then NaOH (50% aq., 75.6 g, 0.946 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 175 °C and the resulting water was continuously distilled until an acid value of 65 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 61 mg KOH / g, SV = 190 mg KOH / g, EV = 129 mg KOH / g, Na = 7.1%).

[0207] Example 10 (inventive): Mixture of C12 and C22 fatty acids (n / n = 80:20), 1. 15 equiv. of lactic acid

[0208] A mixture of lauric acid (99% C12, 150 g, 0.749 mol), behenic acid (95% C22, 63.8 g, 0.187 mol) and L-(+)-lactic acid (90% aq., 107.8 g, 1.08 mol) was heated to 50 °C and then NaOH (50% aq., 75.6 g, 0.946 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 175 °C and the resulting water was continuously distilled until an acid value of 60 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 55 mg KOH / g, SV = 172 mg KOH / g, EV = 117 mg KOH / g, Na = 7.5%).

[0209] Example 11 (inventive): Mixture of C12, C14, C16 and C18 fatty acids (hydrogenated coconut fatty acid), 1. 15 equiv. of lactic acid A mixture of hydrogenated coconut fatty acid (54% C12, 21% C14, 11% C16, 12% C18, 215.0 g, 0.980 mol) and L-(+)-lactic acid (90% aq., 112.8 g, 1.13 mol) was heated to 50 °C and then NaOH (50% aq., 79.2 g, 0.990 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 175 °C and the resulting water was continuously distilled until an acid value of 65 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 59 mg KOH / g, SV = 196 mg KOH / g, EV = 137 mg KOH / g, Na = 6.7%).

[0210] Example 12 (non-inventive): C12 fatty acid, 1. 15 equiv. of lactic acid

[0211] A mixture of lauric acid (99% C12, 151.3 g, 0.755 mol) and L-(+)-lactic acid (90% aq., 87.0 g, 0.869 mol) was heated to 50 °C and then NaOH (50% aq., 60.1 g, 0.752 mol) was carefully added. The pressure was reduced to 500 mbar and the mixture was heated to 120 °C. Once the water was almost completely removed from the reaction mixture, the temperature was increased to 175 °C and the resulting water was continuously distilled until an acid value of 30 mg KOH / g was reached. The mixture was allowed to cool to obtain the target product (AV = 29 mg KOH / g, SV = 204 mg KOH / g, EV = 175 mg KOH / g, Na = 7.5%).

[0212] Example 13 (non-inventive): Commercially available Koplactylate Na (Sodium Lauroyl Lactylate- SLL; Kumar Organic Products Limited)

[0213] This commercially available product is lauroyl lactylate (based only on C12 fatty acid) according to GC analysis.

[0214] Example 14 (non-inventive): Commercially available Capmul S12L (Sodium Lauroyl Lactylate; ABITEC Corporation)

[0215] This commercially available product is lauroyl lactylate (based only on C12 fatty acid) according to GC analysis.

[0216] Example 15 (non-inventive): Commercially available dermosoft® decalact MB (Sodium Caproyl / Lauroyl Lactylate; Evonik Industries AG)

[0217] This commercially available product is a mixture of caproyl lactylate and lauroyl lactylate (based on a mixture of C10 and C12 fatty acids) according to GC analysis. Application Example 16:

[0218] Ceramide containing formulations were produced using Example 9 (inventive), Example 8 (inventive), Example 5 (inventive), Example 12 (non-inventive) and Example 15 (non-inventive). The formulations had the compositions which are shown in Table 1 :

[0219] Table 1 :

[0220] For the preparation of the formulations, homogenization techniques known to the skilled person were used. All concentrations are given in weight percent.

[0221] To create Phase B, Carbomer was dispersed in water at room temperature using an Ultra Turrax. Then, Phenoxyethanol and Ethylhexylglycerin were added. Phase A and B were heated to 85- 90 °C and then Phase B was added to Phase A without stirring followed by homogenization of the mixture for 2 min using an Ultra Turrax. Afterwards the mixture was cooled down under stirring to 30 °C and Phase C was added.

[0222] The obtained formulations were stored for 6 months at room temperature. One day after production (“Start”) as well as after 1 , 3 and 6 months the viscosity (Brookfield RVT, Spindle 5, 50 rpm) was measured and a microscopic picture was taken using a polarization filter and 40x magnification to check if ceramide recrystallization occurred. Table 2 gives the results of the storage tests.

[0223] Table 2:

[0224] From the results of the storage tests in Table 2 it is obvious that only formulations which were based on inventive compositions do not show ceramide recrystallization after 6 months.

[0225] Application Example 17:

[0226] Ceramide containing formulations were produced using Example 7 (inventive), Example 13 (Koplactylate Na; non-inventive) and Example 14 (Capmul S12L; non-inventive). The formulations had the compositions shown in Table 3:

[0227] Table 3

[0228] The formulations were produced as follows: Xanthan Gum was dispersed in water at room temperature using an Ultra Turrax and then Methylparaben and Propylparaben were added. Phase A and B were heated to 85-90 °C and then, Phase B was added to Phase A without stirring and the blend was homogenized using an Ultra Turrax for 2 minutes. Afterwards the blends were cooled down to 30 °C under stirring.

[0229] The obtained blends were stored for 6 months at room temperature. One day after production (“Start”) as well as after 1 , 3 and 6 months the viscosity (Brookfield RVT, Spindle 5, 50 rpm) was measured and a microscopic picture was taken using a polarization filter and 40x magnification to check if ceramide recrystallization occurred. Table 4 gives the results of the storage tests.

[0230] Table 4

[0231] From the results of the storage tests in Table 4 it is obvious that only formulations which are based on inventive compositions do not show ceramide recrystallization after 6 months.

[0232] Formulation Examples:

[0233] Each of the formulations below was produced 4 times while incorporating formulations No. 16A, 16B, 16C and 17A into them, depicted as “No. X” below.

[0234] Face cream

[0235]

[0236] Preparation: Heat phase A and B to 85 °C. Add phase A to B with stirring. Homogenize. Cool down to 40 °C while stirring. Add phase C, D and E. Cool down to 30 °C while stirring.

[0237] Preparation: Heat phase A and B to 85 °C. Add phase A to B with stirring. Homogenize. Cool down to 40 °C while stirring. Add phase C, D and E. Cool down to 30 °C while stirring.

[0238] Face cream III

[0239] Preparation: Heat phase A and B to 85 °C. Add phase A to B with stirring. Homogenize. Cool down to 40 °C while stirring. Add phase C and D. Cool down to 30 °C while stirring.

[0240] O / W lotion, skin fluid

[0241]

[0242] Preparation:

[0243] Heat phase A and B to 85 °C. Add phase A to B with stirring. Homogenize. Cool to approx. 40 °C while stirring gently and then add phase C. Homogenize for a short time. Add phase D, E and F step by step.

[0244] Enjoy The Sun Lotion, SPF 50

[0245] Preparation:

[0246] Heat phase A and B separately to approx. 85 °C. Add phase A to B. Homogenize. Cool to approx.

[0247] 50 °C with gentle stirring, then add phase C. Homogenize. Cool to approx. 35 °C with gentle stirring, then add phase D, E, F and G.

[0248] Microemulsion Preparation:

[0249] Add phase B to phase A slowly while stirring. Add phase C, D, E and F step by step. Adjust pH with phase G to pH 5-5.5. Facial Cleanser

[0250] Preparation

[0251] Heat phase A to 85 °and stirr until it is clear. Add phase B to A slowly with gentle stirring. Cool down to 30 °C. Add phase C. Adjust pH with phase D between 5.0-5.5.

[0252] Shampoo

[0253] Preparation: Mix Sodium Laureth Sulfate, dermofeel sensolv MB, dermofeel G10 LW 70 MB until the solution is clear, heat if necessary. Add the other ingredients step by step in the given order. Cool down while stirring to 30 °C. Oral Care (Mouth Wash)

[0254] Preparation

[0255] Dissolve the flavor in RHEANCE One. Add the water slowly while stirring, then add the remaining ingredients in the given order.

[0256] Deo Formulation (Natural Milky Deo Roll-On) Preparation

[0257] Heat phase A to 80 °C and disperse phase B in A. Separately heat phase C to 85 °C and add phase C into phase A / B. Cool down to 35 °C and add phase D while stirring slowly. Add phase E to adjust the pH value.

[0258] Shower Gel

[0259] Preparation

[0260] Mix the ingredients slowly step by step in the given order while stirring.

[0261] Facial Masque

[0262] Preparation Heat phase A and B to 85 °C. Add phase A to B with stirring. Homogenize. Cool to 50 °C with gentle stirring. Add phase C at about 50 °C. Homogenize again for a short time. Cool to appr. 35 °C with gentle stirring. Prepare phase D. Add phase D with stirring. Add phase E. Adjust pH with phase F to 4.0-5.0.

[0263] Conditioner for Hair

[0264] Preparation Heat phase A and B to 85 °C. Add phase B to phase A without stirring. Homogenize. Cool down to 30 °C while stirring. Add phase C and D.

[0265] W / O Emulsion Preparation

[0266] Heat phase A to approx. 85 °C. Add phase B (80 °C or room temperature) slowly while stirring.

[0267] Homogenize for a short time. Cool to below 30 °C with gentle stirring and add phase C. Homogenize again for a short time.

Claims

1. Claims1 . Mixture composition comprising a monolactylate of at least one carboxylic acid with 12 carbon atoms and at least one oligolactylate of at least one carboxylic acid with 12 carbon atoms and a monolactylate of at least one carboxylic acid with 14 to 22 carbon atoms and at least one oligolactylate of at least one carboxylic acid with 14 to 22 carbon atoms.

2. Mixture composition according to claim 1 with a content of50 wt.-% to 90 wt.-%, preferably 55 wt.-% to 85 wt.-%, more preferably 60 wt.-% to 80 wt.-%, of the sum of said monolactylate of at least one carboxylic acid with 12 carbon atoms and of said at least one oligolactylate of at least one carboxylic acid with 12 carbon atoms, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition.

3. Mixture composition according to claim 1 or 2 with a content of10 wt.-% to 50 wt.-%, preferably 15 wt.-% to 45 wt.-%, more preferably 20 wt.-% to 40 wt.-%, of the sum of said monolactylate of at least one carboxylic acid with 14 to 22 carbon atoms and of said at least one oligolactylate of at least one carboxylic acid with 14 to 22 carbon atoms, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition.

4. Mixture composition according to any of the preceding claims with a content of50 wt.-% to 90 wt.-%, preferably 55 wt.-% to 85 wt.-%, more preferably 60 wt.-% to 80 wt.-%, of the sum of monolactylate of lauric acid and of at least one oligolactylate, preferably dilacty late, of lauric acid, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition.

5. Mixture composition according to any of the preceding claims with a content of10 wt.-% to 50 wt.-%, preferably 15 wt.-% to 45 wt.-%, more preferably 20 wt.-% to 40 wt.-%, of the sum of monolactylate of myristic acid and of at least one oligolactylate preferably dilacty late, of myristic acid, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition.

6. Mixture composition according to any of the preceding claims with a content of50 wt.-% to 90 wt.-%, preferably 55 wt.-% to 85 wt.-%, more preferably 60 wt.-% to 80 wt.-%, of the sum of monolactylate of lauric acid and of dilactylate of lauric acid, and10 wt.-% to 50 wt.-%, preferably 15 wt.-% to 45 wt.-%, more preferably 20 wt.-% to 40 wt.-%, of the sum of monolactylate of myristic acid and of dilactylate of myristic acid, wherein the percentages by weight refer to the sum of all monolactylates and oligolactylates comprised in the composition.

7. Process for the preparation of a mixture of lactylates comprising the steps ofA) providing lactic acid, at least one carboxylic acid with 12 carbon atoms and at least one carboxylic acid with 14 to 22 carbon atoms,B) esterification of said acids provided in A) while obtaining a mixture of lactylates, and optionallyC) purification of said mixture of lactylates.

8. Process according to claim 7 characterized in that said lactic acid provided in process stepA) is provided by a fermentation process.

9. Process according to claim 7 or 8 characterized in that said at least one carboxylic acid with 12 carbon atoms provided in process step A) is lauric acid, and preferably said at least one carboxylic acid with 14 to 22 carbon atoms provided in process step A) is myristic acid.

10. Process according to any of claim 7 to 9 characterized in that the the molar ratio of the sum of all said at least one carboxylic acid with 12 carbon atoms and the sum of all said at least one carboxylic acid with 14 to 22 carbon atoms provided in process step A) is in the range of from 99:1 to 1 :99, preferred from 95:5 to 50:50, more preferred from 90:10 to 55:45, most preferred from 85:15 to 60:40.

11. Process according to any of claim 7 to 10 characterized in that esterification of process stepB) is carried out in the presence of a base, preferably a sodium base, most preferably selected from NaOH and Na2CO3.

12. Cosmetic or pharmaceutical formulation comprising a composition according to any of the claims 1 to 6, a cosmetic and / or pharmaceutical acceptable carrier, preferable water, and a cosmetical and / or pharmaceutical formulation ingredient.

13. Formulation according to claim 12, characterized in that it comprises as said cosmetical and pharmaceutical formulation ingredient at least one ceramide, preferably selected from the group comprising ceramide NP, ceramide AP, ceramide EOP, ceramide NG, ceramide ADS, ceramide EODS, ceramide NS, ceramide AS, ceramide EOS, ceramide NH, ceramide AH and ceramide EOH, preferably selected from the group comprising ceramide NP, ceramide NG, ceramide AP, most preferably ceramide NP.

14. Formulation according to claim 12 or 13, characterized in that it has a content of2.8 wt.-% to 8.8 wt.-%, preferably 3.3 wt.-% to 8.3 wt.-%, more preferably 3.8 wt.-% to 7.8 wt.-%, of the sum of all monolactylates and oligolactylates and0.1 wt.-% to 5.0 wt.-%, preferably 0.5 wt.-% to 3.0 wt.-%, more preferably 1 .3 wt.-% to 2.3 wt.-%, of the sum of all ceramides, wherein the percentages by weight refer to the total formulation.

15. Use of a composition according to any of the claims 1 to 6 for the physical stabilization of a ceramide-containing formulation, in particular regarding homogeneity, and / or for preventing crystallization of at least one ceramide in a formulation.

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