Composition comprising glyceryl nonanoate esters

Abstract

The invention relates to compositions comprising glycerol and glyceryl esters of nonanoic acid, their preparation and use.

Description

[0001] Composition comprising glyceryl nonanoate esters

[0002] Field of the invention

[0003] The invention relates to compositions comprising glycerol and glyceryl ester of nonanoic acid, their preparation and use.

[0004] Prior art

[0005] Glyceryl monoesters of short chain fatty acids, especially Glyceryl Caprylate (INCI), are commonly used in cosmetic formulations as wetting agents, antimicrobials, thickening agents, co-emulsifiers and emollients with moisturizing properties. It’s a drawback of these ingredients that they are currently made from tropical oils, which are known to be a reason for deforestation. It’s another drawback of such substances, that these are typically solid pastes at common temperatures in production facilities of 15 to 25 °C. In addition, the glyceryl monoesters are exclusively obtained on industrial scale by a complex and quite energy consuming distillative purification out of the synthesis mixture containing glycerol, glyceryl monoesters, glyceryl diesters and glyceryl tri-esters. Therefore, certain by-products are being partly disposed.

[0006] It is an object of the instant invention to provide liquid and thus cold-processable compositions that bear excellent antimicrobial properties in cosmetic formulations, which can be obtained by using a more sustainable fatty acid source that is not based on petrochemicals or tropical oils, preferably by a simple and sustainable production process without the necessity of a distillation step to remove unwanted side-products.

[0007] Description of the invention

[0008] Surprisingly, it was found that the disadvantages of the prior art can be overcome by compositions comprising glycerol and glyceryl nonanoate esters. These compositions can be obtained by a simple manufacturing process, in which glycerol is reacted with nonanoic acid, preferably at elevated temperatures.

[0009] An advantage of the present invention is that it reduces whitening and soaping during the application of a formulation

[0010] An advantage of the present invention is that it provides compositions that are easily accessible via heating and mixing without a distillation. Another advantage of the present invention is that the compositions can be produced from fully biobased raw materials, which are not based on tropical oils, since sunflower oil based nonanoic acid is available.

[0011] Another advantage of the present invention is that the compositions are clear liquids at 25 °C, which makes them easily cold processable.

[0012] Another advantage of the present invention are the excellent antimicrobial properties of the compositions.

[0013] Another advantage of the present invention is the improved odor of the pelargonic acid based compositions compared to market standards that are typically based on caprylic acid.

[0014] Another advantage of the compositions of the present invention is that they accelerate the emulsion formation. Improved emulsification properties can lead to shorter production times or energy saving by lower stirring input.

[0015] Another advantage of the present invention is that the compositions resulted in emulsions with improved shine and gloss.

[0016] Another advantage of the compositions of the present invention is that they provide very good pigment wetting properties and are especially suitable for a use in color cosmetics.

[0017] Another advantage of the compositions of the present invention is the antimicrobial performance against deo germs.

[0018] A further advantage of the compositions of the present invention is the boosting of the antimicrobial performance against Athlete’s foot.

[0019] Another advantage of the present invention is the very good antimicrobial performance against Cutibacterium acnes.

[0020] A further advantage of the compositions of the present invention is that these can mask the undesired odors of other ingredients in the formulation or also in the pure mixtures. It leads to less perfume or flavor usage in the formulations.

[0021] Another advantage is that the compositions of the present invention provide a good thickening performance in cleansing formulations.

[0022] A further advantage of the compositions of the present invention is that these build stable W / O formulations whereas the non-inventive materials like Glyceryl Monocaprylate show instability under the same conditions.

[0023] The instant invention provides a composition comprising

[0024] A) glycerol and

[0025] B) glyceryl mono-nonanoate, glyceryl di-nonanoate and glyceryl tri-nonanoate.

[0026] Where average values are stated hereinbelow, then, unless stated otherwise, these are number- averaged average values.

[0027] Unless stated otherwise, percentages are data in per cent by weight. The same is true for parts per million (ppm). 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.

[0028] The “nonanoates” in the context of the instant invention preferably are “n-nonanoates”.

[0029] The quantification of the individual components of the inventive and non-inventive compositions (examples 1 to 7) is carried out by a GC / FID analysis according to the following description. The contents of glycerol and nonanoic acid are determined quantitatively as weight percent (wt.-%), while the content of diglycerol and all glyceryl and diglyceryl nonanoates as wt.-% are analyzed semi quantitatively by using suitable reference substances as listed below.

[0030] For the analysis, 40 mg glyceryl monolaurate, 30 mg of glyceryl dilaurate, 20 mg of glyceryl tricaprylate (as calibration reference standard for all the glyceryl nonanoates), 25 mg 1 ,3-propanediol (as internal standard for the glycerol quantification) and 100 mg of the respective composition (example 1 to 5) are dissolved in 5 ml of a mixture of pyridine / chloroform (4:1). Then, 0.25 ml of the clear solution are transferred into an autosampler vial. Subsequently, 0.5 ml of N-Methyl-N- (trimethylsilyl)trifluoroacetamide (MSTFA) are being added. The derivatization of the hydroxyl groups is completed by heating to 80°C for 30 min.

[0031] An aliquot of the final sample is analyzed by GC / FID using the following conditions.

[0032] Instrument: Gas chromatograph Agilent 7890

[0033] Column: Agilent HP-1 , 30 m * 0.32 mm, df 0.25 pm

[0034] Flow: 2 ml / min constant flow, hydrogen

[0035] Oven Temp. Prog.: 80°C; 8°C / min; 300°C, 15 min

[0036] Injector: 1 pl Split 1 :20

[0037] Detector: FID, 310°C

[0038] Glycerol and nonanoic acid (the latter one is typically not present) are quantified using 1 ,3- propanediol as internal standard, based on an internal standard calibration established from calibration reference mixtures. 1- and 2-glyceryl mono-nonanoate as well as diglyceryl monononanoate are quantified as wt.-% based on peak area comparison with glyceryl monolaurate. 1 ,2- and 1 ,3-glyceryl di-nonanoate as well as diglyceryl di-nonanoate (sum of isomers) are quantified as wt.-% based on peak area comparison with glyceryl dilaurate (e.g. pure 1 , 2-glyceryl dilaurate). Glyceryl tri-nonanoate is quantified as wt.-% based on peak area comparison with glyceryl tricaprylate. Diglycerol is quantified as wt.-% based on peak area comparison with glycerol.

[0039] Due to an obvious underrepresentation of the amounts of the semi quantitatively analyzed substances mentioned above, all the corresponding wt.-% are corrected with a factor of 1 .04, which is the average quotient of [100 wt.-% minus wt.-% of glycerol] and [the sum of all wt.-% of the not quantitatively analyzed components] in the respective composition (wt.-% result of first square bracket divided by wt.-% result of second square bracket). This means that all wt.-% of all glyceryl nonanoates have to be multiplied with 1 .04 for obtaining the correct wt.-%. A preferred composition according to the instant invention is characterised in that said glyceryl mono-nonanoate is comprised as a mixture of 1 -glyceryl mono-nonanoate and 2-glyceryl monononanoate.

[0040] The weight ratio of said 1 -glyceryl mono-nonanoate and said 2-glyceryl mono-nonanoate preferably is in the range of 50:1 to 2:1 , preferably 30:1 to 3:1 , more preferably 18:1 to 4:1 .

[0041] A preferred composition according to the instant invention is characterised in that said glyceryl dinonanoate is comprised as a mixture of 1 , 2-glyceryl di-nonanoate and 1 ,3-glyceryl di-nonanoate. The weight ratio of said 1 , 2-glyceryl di-nonanoate and said 1 ,3-glyceryl di-nonanoate preferably is in the range of 2:1 to 1 :4, preferably 3:2 to 1 :3, more preferably 1 :1 to 1 :2.

[0042] Preferably the composition according to the instant invention is characterised in that component A) is comprised in an amount of from 0.1 wt.-% - 32 wt.-%, preferably 5 wt.-% - 27 wt.-%, most preferably 10 wt.-% - 22 wt.-%, and component B) is comprised in an amount of from 50 wt.-% - 99.9 wt.-%, preferably 70 wt.-% - 95 wt.-%, most preferably 75 wt.-% - 90 wt.-%, wherein the percentages by weight refer to the total composition.

[0043] A preferred composition according to the instant invention is characterised in that it comprises 0.1 wt.-% - 32 wt.-%, preferably 5 wt.-% - 27 wt.-%, most preferably 10 wt.-% - 22 wt.-%, glycerol, 25 wt.-% - 60 wt.-%, preferably 30 wt.-% - 55 wt.-%, most preferably 35 wt.-% - 48 wt.-%, of 1- glyceryl mono-nonanoate,

[0044] 1 wt.-% - 15 wt.-%, preferably 2 wt.-% - 10 wt.-%, most preferably 3 wt.-% - 8 wt.-%, of 2-glyceryl mono-nonanoate,

[0045] 3 wt.-% - 25 wt.-%, preferably 5 wt.-% - 20 wt.-%, most preferably 7 wt.-% - 15 wt.-%, of 1 ,2- glyceryl di-nonanoate,

[0046] 7 wt.-% - 35 wt.-%, preferably 9 wt.-% - 25 wt.-%, most preferably 12 wt.-% - 21 wt.-%, of 1 ,3- glyceryl di-nonanoate, and

[0047] 0.1 wt.-% - 15 wt.-%, preferably 1 wt.-% - 10 wt.-%, most preferably 2 wt.-% - 8 wt.-%, of glyceryl tri-nonanoate, wherein the percentages by weight refer to the sum of glycerol and all glyceryl esters of nonanoic acid.

[0048] A more preferred composition according to the instant invention is characterised in that it comprises

[0049] 10 wt.-% - 22 wt.-% glycerol,

[0050] 35 wt.-% - 48 wt.-% of 1 -glyceryl mono-nonanoate,

[0051] 3 wt.-% - 8 wt.-% of 2-glyceryl mono-nonanoate,

[0052] 7 wt.-% - 15 wt.-% of 1 , 2-glyceryl di-nonanoate,

[0053] 12 wt.-% - 21 wt.-% of 1 ,3-glyceryl di-nonanoate and 2 wt.-% - 8 wt.-% of glyceryl tri-nonanoate, wherein the percentages by weight refer to the sum of glycerol and all glyceryl esters of nonanoic acid.

[0054] Preferably the composition according to the instant invention comprises diglycerol and at least one diglycerol ester of nonanoic acid.

[0055] Preferably the sum of said diglycerol and all said diglyceryl esters of nonanoic acid is comprised in the composition according to the instant invention in an amount from 0.01 wt.-% - 10 wt.-%, preferably 0.1 wt.-% - 8.0 wt.-%, most preferably 0.5 wt.-% - 6.0 wt.-%, wherein the percentages by weight refer to the total composition.

[0056] Alternatively preferable, the composition according to the instant invention does not comprise any diglycerol nor any diglycerol ester of nonanoic acid.

[0057] The instant invention further provides a process for the preparation of a glyceryl ester of nonanoic acid comprising the steps of

[0058] I) providing glycerol and a nonanoic acid acyl group donor,

[0059] II) keeping the temperature of the mixture in a range of 30 °C to 300 °C, preferably 35 °C to 280 °C, most preferably to 200 °C to 260 °C, for 1 hour to 100 hours, preferably 4 hours to 60 hours, most preferably 8 hours to 36 hours,

[0060] III) distilling off the reaction water.

[0061] The nonanoic acid acyl group donor provided in step I) of the process of the instant invention is preferably selected from nonanoic acid esters, for example methyl- and ethyl esters or glycerides, and nonanoic acid, wherein nonanoic acid is especially preferred.

[0062] The nonanoic acid acyl group donor provided in step I) of the process of the instant invention is preferably based on a non-tropical plant oil, like sunflower oil.

[0063] A preferred process according to the instant invention is characterised in that the molar ratio of said provided glycerol and nonanoic acid acyl groups provided by the donor is in the range of 1 .0:0.4 to 1 .0:1 .4, preferably 1 .0:0.5 to 1 .0:1 .2, more preferably 1 .0:0.6 to 1 .0:1 .0.

[0064] Preferably the process according to the instant invention is characterised in that said provided glycerol and said at least one nonanoic acid acyl group donor in sum account for at least 90 wt.-%, preferably 95 wt.-%, more preferably 98 wt.-%, of all components provided in the total process. In process step II) of the process according to the instant invention a catalyst can be present. Such might be, for example sulfuric acid, sulfonic acid, p-toluenesulfonic acid, and in general Lewis acids, or also simple zinc (II) salts. Also, an enzymatic catalyst, like for example a lipase, can be present in process step II) of the process according to the instant invention. A preferred enzymatic catalyst present in process step II) of the process according to the instant invention is the lipase B from Candida antarctica, knowns as CalB. A preferred enzymatic catalyst present in process step II) of the process according to the instant invention can be selected from the commercial products Lipozyme TL IM, Novozym 435, Lipozyme IM 20, Lipase SP382, Lipase SP525, Lipase SP523, (all commercial products from Novozymes A / S, Bagsvaerd, Denmark), Chirazyme L2, Chirazyme L5, Chirazyme L8, Chirazyme L9 (all commercial products from Roche Molecular Biochemicals, Mannheim, Germany), CALB Immo Plus TM from Purolite, and Lipase M “Amano”, Lipase F-AP 15 “Amano”, Lipase AY “Amano”, Lipase N “Amano”, Lipase R “Amano”, Lipase A “Amano”, Lipase D “Amano”, Lipase G “Amano” (all commercial products from Amano, Japan).

[0065] If an enzymatic catalyst is present in process step II) of the process according to the instant invention, the temperature is preferably kept between 35 °C to and 95 °C.

[0066] A preferred process according to the instant invention is characterised in that in process step II) a pressure within the range of 0.1 mbar to 3 bar, preferably 1 mbar to 2 bar, more preferably 5 mbar to 1 .1 bar, is applied.

[0067] Preferably the process according to the instant invention is characterised in that process step III) is conducted in a temperature range of 35 to 300 °C, preferably 45 to 280 °C, more preferably 90 to 260 °C, and a pressure range of 0.1 mbar to 1.5 bar, preferably 0.5 mbar to 1.2 bar, more preferably 1 mbar to 1.1 bar.

[0068] The instant invention further provides a composition comprising glycerol and glyceryl esters of nonanoic acid obtainable by the process according to the instant invention.

[0069] The composition according to the instant invention and obtainable by the process according to the instant invention have outstanding properties useful in a wide variety of formulations; thus, the instant invention provides the use of a composition according to the instant invention and / or obtainable by the process according to the instant invention for the preparation of a formulation, preferably a cosmetic formulation. The instant invention provides the use of a composition according to the instant invention and / or obtainable by the process according to the instant invention as antimicrobial agent, preferably in a cosmetic formulation.

[0070] The instant invention provides the use of a composition according to the instant invention and / or obtainable by the process according to the instant invention as wetting agent, preferably in a cosmetic formulation.

[0071] The composition according to the instant invention and / or obtainable by the process according to the instant invention in the above uses according to the instant invention preferably is used in a concentration of 0.01 wt.-% - 10 wt.-%, preferably 0.1 wt.-% - 5 wt.-%, most preferably 0.2 wt.-% - 3 wt.-%, wherein the percentages by weight refer to the sum of glycerol and all glyceryl esters of nonanoic acid in the total formulation.

[0072] The instant invention provides the use of a composition according to the instant invention and / or obtainable by the process according to the instant invention as anti-whitening and / or anti-soaping agent, preferably in a cosmetic formulation.

[0073] The composition according to the instant invention and / or obtainable by the process according to the instant invention in the use as anti-whitening and / or anti-soaping agent according to the instant invention preferably is used in a concentration of 0.1 wt.-% - 10 wt.-%, preferably 0.2 wt.-% - 5.0 wt.-%, most preferably 0.5 wt.-% - 3.5 wt.-%, wherein the percentages by weight refer to the sum of glycerol and all glyceryl esters of nonanoic acid in the total formulation.

[0074] The formulation in the context of the uses of the instant invention preferably has a pH in the range of 3.5 to 7.5, preferably 4.0 to 7.0, more preferably 4.5 to 6.5 and particularly preferably 4.8 to 6.2. The “pH” in connection with the present invention is defined as the value which is measured for the relevant composition at 25 °C after stirring for five minutes using a pH electrode calibrated in accordance with ISO 4319 (1977).

[0075] 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.

[0076] Examples: Example 1 (inventive):

[0077] 138 g (1 ,50 mol) of glycerol and 190 g (1 .20 mol) of n-nonanoic acid were heated to 220 °C while stirring and distilling off the reaction water. As soon as the acid value was below 2 mg KOH / g and the reaction mixture was a clear, homogeneous liquid, it was cooled down to 25 °C. The product was a yellowish clear liquid.

[0078] Example 2 (inventive):

[0079] 138 g (1 .50 mol) of glycerol and 166 g (1 .05 mol) of n-nonanoic acid were heated to 220 °C while stirring and distilling off the reaction water. As soon as the acid value was below 2 mg KOH / g and the reaction mixture was a clear, homogeneous liquid, it was cooled down to 25 °C. The product was a yellowish clear liquid.

[0080] Example 3 (inventive):

[0081] 138 g (1 .50 mol) of glycerol and 213 g (1 .35 mol) of n-nonanoic acid were heated to 220 °C while stirring and distilling off the reaction water. As soon as the acid value was below 2 mg KOH / g and the reaction mixture was a clear, homogeneous liquid, it was cooled down to 25 °C. The product was a yellowish clear liquid.

[0082] Example 4 (non-inventive):

[0083] 127 g (1.38 mol) of glycerol, 97 g (0.67 mol) of n-octanoic acid and 76 g (0.44 mol) of n-decanoic acid were heated to 220 °C while stirring and distilling off the reaction water. As soon as the acid value was below 2 mg KOH / g and the reaction mixture was a clear, homogeneous liquid, it was cooled down to 25 °C. The product was a yellowish clear liquid.

[0084] Example 5 (non-inventive):

[0085] Glyceryl Caprylate (INCI, tradename: Dermosoft® GMCY MB), contains more than 85 % Glyceryl Monocaprylate.

[0086] Example 6 (non-inventive): 138 g (1.50 mol) of glycerol and 151 g (1.05 mol) of n-octanoic acid were heated to 220 °C while stirring and distilling off the reaction water. As soon as the acid value was below 2 mg KOH / g and the reaction mixture was a clear, homogeneous liquid, it was cooled down to 25 °C. The product was a yellowish clear liquid.

[0087] Example 7 (non-inventive):

[0088] 138 g (1.50 mol) of glycerol and 195 g (1.35 mol) of n-octanoic acid were heated to 220 °C while stirring and distilling off the reaction water. As soon as the acid value was below 2 mg KOH / g and the reaction mixture was a clear, homogeneous liquid, it was cooled down to 25 °C. The product was a yellowish clear liquid.

[0089] Example 8: Determination of antimicrobial performance, basics

[0090] Formulations:

[0091] “Antimicrobial” is the composition to be tested. All given amounts in the formulation are usage percentages by weight.

[0092] Formulation 1 : An O / W emulsion has been prepared as following. The ingredients and the amounts are provided in the table below.

[0093] Processing:

[0094] 1 . Heat phase A and C separately up to 78 °C.

[0095] 2. Add phase B to A under stirring and wait until everything is dissolved. 3. Add phase C to A / B under stirring. Homogenize with the usage of an Ultra Turrax.

[0096] 4. Add phase D at 40 °C.

[0097] 5. Cool down to room temperature.

[0098] 6. Adjust the pH.

[0099] Formulation 2: Another O / W emulsion has been prepared as following. The ingredients and the amounts are provided in the table below. Processing: 1 . Heat phase A and B separately up to 78 °C.

[0100] 2. Add phase A1 to A under stirring and wait until everything is dissolved.

[0101] 3. Add phase B to A / A1 under stirring. Homogenize for 90 sec. with the usage of an Ultra

[0102] Turrax.

[0103] 4. Add phase C at 40 °C.

[0104] 5. Cool down to room temperature while stirring.

[0105] 6. Adjust the pH. Fomulation 3: A surfactant base has been prepared as following. The ingredients and the amounts are provided in the table below.

[0106]

[0107] Processing: 1. Mix the components of phase A and stir until clearly dissolved.

[0108] 2. Add phase B to phase A. Stir until homogenized.

[0109] 3. Adjust the pH value with phase C. Formulation 4: Another surfactant base has been prepared as following. The ingredients and the amounts are provided in the table below.

[0110] Processing:

[0111] 1 . Mix the components of phase A and stir until clearly dissolved.

[0112] 2. Add phase B to phase A. Stir until homogenized.

[0113] 3. Adjust the pH value with phase C. Formulation 5: Another surfactant base has been prepared as following. The ingredients and the amounts are provided in the table below.

[0114] Processing:

[0115] 1 . Mix the components of phase A and stir until clearly dissolved.

[0116] 2. Add phase B to phase A. Stir until homogenized.

[0117] 3. Adjust the pH value with phase C.

[0118] Formulation 6: A W / O emulsion has been prepared as following. The ingredients and the amounts are provided in the table below.

[0119] Processing:

[0120] 1 . Mix phase A and B separately and heat up to 78 °C

[0121] 2. Measure the pH of the water-phase. 3. Slowly and stepwise add phase A to phase B while stirring.

[0122] 4. Homogenize it with the usage of an Ultra Turrax.

[0123] 5. Add phase C at 40-45 °C.

[0124] 6. Cool down to room temperature while stirring.

[0125] Formulation 7: Another W / O emulsion has been prepared as following. The ingredients and the amounts are provided in the table below.

[0126] Processing:

[0127] 1 . Mix phase B at room temperature and adjust the pH to 5.3

[0128] 2. Heat phase A up to 78 °C.

[0129] 3. Add phase B slowly into phase A while stirring

[0130] 4. Homogenize for a short time.

[0131] 5. Add part C at 40-45 °C.

[0132] 6. Cool down with gentle stirring to 30°C.

[0133] Antimicrobial test method:

[0134] The antimicrobial activity against specific microorganisms was evaluated as follows.

[0135] Preparation of the inoculum:

[0136] Preparatory to the test, the surface of casein soya bean digest agar for bacteria or Saboraud- dextrose agar without the addition of antibiotics for fungi is inoculated with the recently grown stock culture of each of the specified microorganisms. The bacterial cultures are inoculated at 30-35°C for 18-24 hours, the culture of C. albicans at 20-25°C for 48 hours, and the culture of A. brasiliensis at 20-25°C for 1 week or until good sporulation is obtained.

[0137] Method:

[0138] To count the viable microorganisms in the inoculated products, the agar medium used for the initial cultivation of the respective microorganism is used. The test sample is inoculated with a suspension of the test organism to give an inoculum of 105to 106microorganisms per milliliter of the preparation. The volume of the suspension of inoculum does not exceed 1 per cent of the volume of the product. The suspension is mixed thoroughly to ensure homogeneous distribution. The inoculated product is maintained at 20-25°C, protected from light. At zero hour and at 7, 14 and 28 days 1 ml is removed from the sample and the number of viable microorganisms is determined by plate count.

[0139] Evaluation:

[0140] The criteria for the evaluation of the antimicrobial activity are given in tables below in terms of the log reduction in the number of viable microorganisms against the value obtained for the inoculum.

[0141] Result 1 : colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH: 4.5 in the formulation 1 .

[0142] ‘Here, 3% dermosoft 1388 (INCI: Glycerin, Aqua, Sodium Levulinate, Sodium Anisate) is combined with 0.2% example 5 and 1 . Result 2: colony forming units per g after incubation time for the germ E. coli at pH: 5 in the formulation 4.

[0143] ‘Usage concentration is 0.5% in both cases. Result 3: colony forming units per g after incubation time for the germ Candida albicans at pH: 5 in the formulation 4.

[0144] ‘Usage concentration is 0.5% in both cases. Result 4: colony forming units per g after incubation time for the germ Candida albicans at pH: 6 in the formulation 2.

[0145] ‘Usage concentration is 1 % in all cases. Result 5: colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH: 5 in the formulation 5.

[0146] ‘Here usage level is 1%.

[0147] Result 6: colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH: 5 in the formulation 3.

[0148] ‘Usage concentration is 1% in both cases.

[0149] Result 7: colony forming units per g after incubation time for the germ Pseudomonas aeruginosa at pH: 5 in the formulation 3.

[0150] ‘Usage concentration is 1% in both cases.

[0151] Result 8: colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH: 5 in the formulation 2. ‘Usage concentration are 0.2% example 1 or example 5 combined with 3% dermosoft 1388 (INCI: Glycerin, Aqua, Sodium Levulinate, Sodium Anisate). Result 9 : colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH: 5.3 in the formulation 1

[0152] ‘Here usage level is 0.5%.

[0153] Result 10: colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH: 5.5 in the formulation 1 .

[0154] ‘Here usage level is 1 %.

[0155] Result 11 : colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH:

[0156] 5.5 in the formulation 1 ‘Here usage level is 0.4 %.

[0157] Result 12: colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH:

[0158] 5.5 in the formulation 1 .

[0159] Here usage level is 0.8 %. Result 13: colony forming units per g after incubation time for the germ Staphylococcus aureus at pH:

[0160] 6 in the formulation 2.

[0161] ‘Usage concentration are 0.2% GPE or GMCY combined with 3% dermosoft 1388 (INCI: Glycerin, Aqua, Sodium Levulinate, Sodium Anisate).

[0162] Result 14: colony forming units per g after incubation time for the germ Aspergillus brasiliensis in the formulation 7.

[0163] ‘Here usage level is 1%.

[0164] Result 15: colony forming units per g after incubation time for the germ Aspergillus brasiliensis in the formulation 6.

[0165] ‘Here usage level is 0.5 %. Result 16: colony forming units per g after incubation time for the germ Staphylococcus aureus in the formulation 1 at pH: 5.

[0166] Here usage level is 0.5%. Result 17: colony forming units per g after incubation time for the germ Candida albicans in the formulation 1 at pH: 5.

[0167] ‘Here usage level is 0.5%. Result 18: colony forming units per g after incubation time for the germ Escherichia coli in the formulation 4 at pH: 5.

[0168] ‘Here usage level is 0.5%.

[0169] Result 19: colony forming units per g after incubation time for the germ Aspergillus brasiliensis in the formulation 4 at pH: 5.

[0170] ‘Here usage level is 0.5%.

[0171] Result 20: colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH: 5.3 in the formulation 1 .

[0172] ‘Usage concentration is 1 % Result 21 : colony forming units per g after incubation time for the germ Candida albicans at pH: 5.3 in the formulation 1 .

[0173] ‘Usage concentration is 1%

[0174] Result 22: colony forming units per g after incubation time for the germ Aspergillus brasiliensis in the formulation 6.

[0175] ‘Usage concentration is 1% Result 23: colony forming units per g after incubation time for the germ Candida albicans in the formulation 6.

[0176] ‘Usage concentration is 1%

[0177] Result 24: colony forming units per g after incubation time for the germ Aspergillus brasiliensis in the formulation 6.

[0178] ‘Usage concentration is 1%

[0179] Result 25: colony forming units per g after incubation time for the germ Candida albicans at pH: 5 in the formulation 1.

[0180] ‘Here usage level is 0.5 %.

[0181] Result 26: colony forming units per g after incubation time for the germ Staphylococcus aureus at pH:5 in the formulation 1 .

[0182] ‘Usage concentration is 0.5%

[0183] Result 27: colony forming units per g after incubation time for the germ Candida albicans at pH:5 in the formulation 1 . ‘Usage concentration is 0.5%

[0184] Result 28: colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH:5 in the formulation 1 .

[0185] ‘Usage concentration is 0.5%

[0186] Result 29: colony forming units per g after incubation time for the germ Staphylococcus aureus at pH:6 in the formulation 1 .

[0187] ‘Usage concentration is 0.5% Result 30: colony forming units per g after incubation time for the germ Candida albicans at pH:6 in the formulation 1 .

[0188] ‘Usage concentration is 0.5% Result 31 : colony forming units per g after incubation time for the germ Escherichia coli at pH:5 in the formulation 4.

[0189] ‘Usage concentration is 0.5%

[0190] Result 32: colony forming units per g after incubation time for the germ Candida albicans at pH:5 in the formulation 4.

[0191] ‘Usage concentration is 0.5%

[0192] Result 33: colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH:5 in the formulation 4. ‘Usage concentration is 0.5%

[0193] Result 34: colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH:5 in the formulation 4.

[0194] ‘Usage concentration is 0.5%

[0195] Result 35: colony forming units per g after incubation time for the germ Candida albicans at pH:6 in the formulation 2. ‘Usage concentration is 1%

[0196] Result 36: colony forming units per g after incubation time for the germ Aspergillus brasiliensis at pH:6 in the formulation 2.

[0197] ‘Usage concentration is 1%

[0198] Result 37: colony forming units per g after incubation time for the germ Candida albicans at pH:6 in the formulation 2.

[0199] ‘Usage concentration is 1% Result 38: colony forming units per g after incubation time for the germ Staphylococcus aureus at pH:5 in the formulation 1 .

[0200] ‘Usage concentration is 0.2% combined with 0.23% dermosoft anisate (INCI: Sodium Anisate). Result 39: colony forming units per g after incubation time for the germ Escherichia coli at pH:5 in the formulation 1 .

[0201] ‘Usage concentration is 0.2% combined with 0.23% dermosoft anisate (INCI: Sodium Anisate).

[0202] Result 40: colony forming units per g after incubation time for the germ Candida albicans at pH:5 in the formulation 1 .

[0203] ‘Usage concentration is 0.2% combined with 0.23% dermosoft anisate (INCI: Sodium Anisate).

[0204] Example 9: Determination of emulsion stability

[0205] Formulation 6 has been prepared with inventive examples 1 and 2 and non-inventive example 5. These formulations were stored at 4 °C, 25 °C and also at 40 °C during 1 month. The formulation with non-inventive example 5 showed phase-separation after 1 month storage which was not seen with both inventive examples.

[0206] Example 10: Thickening performance in a cosmetic formulation

[0207] The thickening effect of inventive example 1 was evaluated in comparison to non-inventive example 5 and vehicle. A cosmetic formulation is prepared with the ingredients as described in the table below. The viscosities were measured with the aid of a Brookfield viscosimeter (spindle 62, 30 rpm) at 22 °C. Inventive example shows superior thickening performance in cleansing formulations compared to non-inventive example 5 and vehicle.

[0208] Example 11: Odor masking test In order to evaluate odor masking properties, a test was performed with 13 test people. Prior to the test, the formulations and the mixtures were prepared as stated in the tables below. In the first part, testers smelled the formulations in the table 1 and judged the odor on a grading scale from 0 (no odor) to 3 (strong odor). In the second part, the same testers also smelled the mixtures in the table 2 and evaluated on a grading scale from 0 (no odor) to 3 (strong odor).

[0209] Table 1 :

[0210] Processing:

[0211] Heat phase A and C separately up to 78 °C.

[0212] 1 . Add phase B to A under stirring and wait until everything is dissolved.

[0213] 2. Add phase C to A / B under stirring. Homogenize with the usage of an Ultra Turrax. 3. Add phase D at 40 °C.

[0214] 4. Cool down to room temperature.

[0215] Table 2:

[0216] Example 12: Whitening of cosmetic formulations, given numbers are weight percentages, except for the whitening evaluation numbers at the bottom of the table:

[0217] * according to the instant invention

[0218] The natural o / w-emulsions which composition is shown in the table above was formulated according to the following procedure: 1 . Mix Xanthan Gum and Glycerin, add water (80 °C) in portions and homogenize

[0219] 2. Heat phase A and phase B separately to 80°C

[0220] 3. Add Phase B without stirring

[0221] 4. Homogenize

[0222] 5. Cool down to 30°C

[0223] 6. Add phase C and stir well

[0224] 7. Adjust pH to 5.2 with citric acid (10% aq. solution)

[0225] The whitening of the formulations was evaluated by a trained sensory panel. At least 10 persons assessed the whitening profile of the formulations without knowing the composition of the evaluated samples. Therefore, 50 mg of the respective formulation was put into a pre-marked 10 cm3circle on the forearm of each panellist. Then, the cream was evenly spread in the circle by circular movements with the index finger of the other arm. The whitening was evaluated within the period of 20 to 80 circular movements by applying a scoring from 0 (no whitening) to 10 (high whitening).

Claims

Claims1 . Composition comprisingA) glycerol andB) glyceryl mono-nonanoate, glyceryl di-nonanoate and glyceryl tri-nonanoate.

2. Composition according to claim 1 characterised in that said glyceryl mono-nonanoate is comprised as a mixture of 1 -glyceryl mono-nonanoate and 2-glyceryl mono-nonanoate.

3. Composition according to claim 1 or 2 characterised in that component A) is comprised in an amount of from 0.1 wt.-% - 32 wt.-%, preferably 5 wt.-% - 27 wt.-%, most preferably 10 wt.- % - 22 wt.-%, and component B) is comprised in an amount of from 50 wt.-% - 99.9 wt.-%, preferably 70 wt.-% - 95 wt.-%, most preferably 75 wt.-% - 90 wt.-%, wherein the percentages by weight refer to the total composition.

4. Composition according to any of the preceding claims characterised in that it comprises 0.1 wt.-% - 32 wt.-%, preferably 5 wt.-% - 27 wt.-%, most preferably 10 wt.-% - 22 wt.-%, glycerol,25 wt.-% - 60 wt.-%, preferably 30 wt.-% - 55 wt.-%, most preferably 35 wt.-% - 48 wt.-%, of 1- glyceryl mono-nonanoate,1 wt.-% - 15 wt.-%, preferably 2 wt.-% - 10 wt.-%, most preferably 3 wt.-% - 8 wt.-%, of 2-glyceryl mono-nonanoate,3 wt.-% - 25 wt.-%, preferably 5 wt.-% - 20 wt.-%, most preferably 7 wt.-% - 15 wt.-%, of 1 ,2- glyceryl di-nonanoate,7 wt.-% - 35 wt.-%, preferably 9 wt.-% - 25 wt.-%, most preferably 12 wt.-% - 21 wt.-%, of 1 ,3- glyceryl di-nonanoate, and0.1 wt.-% - 15 wt.-%, preferably 1 wt.-% - 10 wt.-%, most preferably 2 wt.-% - 8 wt.-%, of glyceryl tri-nonanoate, wherein the percentages by weight refer to the sum of glycerol and all glyceryl esters of nonanoic acid.

5. Composition according to any of the preceding claims characterised in that it comprises diglycerol and at least one diglyceryl ester of nonanoic acid, preferably in an amount from 0.01 wt.-% - 10 wt.-%, preferably 0.1 wt.-% - 8.0 wt.-%, most preferably 0.5 wt.-% - 6.0 wt.-%, wherein the percentages by weight refer to the total composition.

6. Process for the preparation of a glycerol ester of nonanoic acid comprising the steps of I) providing glycerol and at least one nonanoic acid acyl group donor, preferably selected from nonanoic acid esters and nonanoic acid,II) keeping the temperature of the mixture in a range of 35 °C to 300 °C for 1 hour to 100 hours,III) distilling off the reaction water.

7. Process according to claim 6, characterised in that the molar ratio of said provided glycerol and the amount of nonanoic acid acyl groups provided by the donor is in the range of 1 .0:0.4 to 1 .0:1 .4, preferably 1 .0:0.5 to 1 .0:1 .2, more preferably 1 .0:0.6 to 1 .0:1 .0.

8. Process according to claim 6 or 7, characterised in that said provided glycerol and said at least one nonanoic acid acyl group donor in sum account for at least 90 wt.-%, preferably 95 wt.-%, more preferably 98 wt.-%, of all components provided in the total process.

9. Process according to any of claims 6 to 8 characterised in that in process step II) a pressure within the range of 0.1 mbar to 3 bar, preferably 1 mbar to 2 bar, more preferably 5 mbar to1 .1 bar, is applied.

10. Process according to any of claims 6 to 9 characterised in that process step III) is conducted in a temperature range of 30 to 300 °C, preferably 45 to 280 °C, more preferably 90 to 260 °C, and a pressure range of 0.1 mbar to 1 .5 bar, preferably 0.5 mbar to 1 .2 bar, more preferably 1 mbar to 1.1 bar.11 Composition comprising glycerol and glyceryl esters of nonanoic acid obtainable by a process according to any of the claims 6 to 10.

12. Use of a composition according to any of the claims 1 to 5 or 11 for the preparation of a formulation, preferably a cosmetic formulation, preferably in a concentration of 0.01 wt.-% - 10 wt.-%, preferably 0.1 wt.-% - 5 wt.-%, most preferably 0.2 wt.-% - 3 wt.-%, wherein the percentages by weight refer to the sum of glycerol and all glyceryl esters of nonanoic acid in the total formulation.

13. Use of a composition according to any of the claims 1 to 5 or 11 as antimicrobial agent, preferably in a cosmetic formulation, preferably in a concentration of 0.01 wt.-% - 10 wt.-%, preferably 0.1 wt.-% - 5 wt.-%, most preferably 0.2 wt.-% - 3 wt.-%, wherein the percentages by weight refer to the sum of glycerol and all glyceryl esters of nonanoic acid in the total formulation.

14. Use of a composition according to any of the claims 1 to 5 or 11 as wetting agent, preferably in a cosmetic formulation, preferably in a concentration of 0.01 wt.-% - 10 wt.-%, preferably 0.1 wt.-% - 5 wt.-%, most preferably 0.2 wt.-% - 3 wt.-%, wherein the percentages by weight refer to the sum of glycerol and all glyceryl esters of nonanoic acid in the total formulation.

15. Use of a composition according to any of the claims 1 to 5 or 11 as anti-whitening-and- soaping agent, preferably in a cosmetic formulation, preferably in a concentration of 0.1 wt.- % - 10 wt.-%, preferably 0.2 wt.-% - 5.0 wt.-%, most preferably 0.5 wt.-% - 3.5 wt.-%, wherein the percentages by weight refer to the sum of glycerol and all glyceryl esters of nonanoic acid in the total formulation.

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