AQUEOUS COMPOSITIONS COMPRISING 6-UNDECANOL-ESTERS

Abstract

Aqueous compositions containing 6-undecanol-esters are useful in cosmetic aplications. Methods for producing 6-undecanol-esters are also provided.

Claims

1. An aqueous composition, containing: at least one 6-undecanol-ester, obtainable by esterification of undecart-6-ol with one selected from the group consisting of A) a monocarboxylic acid with 6 to 32, carbon atoms, and B) a polyfunctional carboxylic acid with 2 to 44 carbon atoms.

2. The aqueous composition according to claim 1, wherein the monocarboxylic acid is a fatty acid.

3. The aqueous composition according to claim 1, wherein the polyfunctional carboxylic acid is an aliphatic, linear dicarboxylic acid.

4. The aqueous composition according to claim 1, wherein the aqueous composition is a formulation.

5. The aqueous composition according to claim 1, wherein the aqueous composition contains at least one humectant.

6. A method for preparing 6-undecanol-esters, the method containing: (a) providing ethanol and/or a lower alkanoic acid or any salts thereof, and contacting the ethanol and/or the lower alkanoic acid or any salts thereof with at least one microorganism capable of carrying out two-carbon chain elongation, to produce hexanoic acid and/or a salt thereof and/or an ester thereof; (b) contacting the hexanoic acid and/or the salt thereof andlor the ester thereof from (a) with at least one ketonization catalyst under suitable reaction conditions for chemical ketonization of the hexanoic acid and/or the salt thereof and/or the ester thereof to 6-undecanone; (c) contacting the 6-undecanone with at least one hydrogenation metal catalyst for catalytic hydrogenation of the 6-undecanone to 6-undecanol; and (d) esterifying the 6-undecanol with at least one selected from the group consisting of A) acyl group donors providing acyl groups of a monocarboxylic acid with 6 to 32 carbon atoms, and B) acyl group donors providing acyl groups of a polyfunctional carboxylic acid with 2 to 44 carbon atoms.

7. The method according to claim 6, wherein the at least one microorganism in (a) is selected from the group consisting of Clostridium corboxidivorans and Clostridium kluyveri.

8. The method according to claim 6, wherein the at least one ketonization catalyst of (b) is a metal oxide catalyst ora mixture thereof.

9. The method according to claim 6, wherein (b) is carried out at a temperature between 150? C. and 350? C.

10. The method according to claim 6, wherein the at least one hydrogenation metal catalyst of (c) is selected from the group consisting of ruthenium (Ru) catalysts, rhenium (Re) catalysts, nickel (Ni) catalysts, iron (Fe) catalysts, cobalt (Co) catalysts, palladium (Pd) catalysts, and platinum (Pt) catalysts.

11. The method according to claim 6, wherein the lower alkanoic acid in (a) is selected from the group consisting of acetic acid and butanoic acid.

12. The method according to claim 6, wherein the provision of the ethanol and/or the lower alkanoic acid or any salts thereof in (a) comprises synthesis of the ethanol and/or the lower alkanoic acid or any salts thereof from synthesis gas.

13. A method of preparing a cosmetic formulation, the method comprising: mixing the aqueous composition according to claim 1 with at least one further component selected from the group consisting of humectants, UV light protection filters, and pigments.

14. A method of avoiding skin dryness, the method comprising: spreading the aqueous composition according to claim 1 on skin.

15. The aqueous composition according to claim 1, wherein the monocarboxylic acid has 8 to 22 carbon atoms, and wherein the polyfunctional carboxylic acid is a dicarboxylic acid with 2 to 18 carbon atoms.

16. The aqueous composition according to claim 3, wherein the polyfunctional carboxylic acid is selected from the group consisting of oxalic acid, malonic acid, tartronic acid, succinic acid, maleic acid, tartaric acid, maleic acid, fumaric acid, sorbic acid, alpha-ketoglutaric acid, glutaric acid, adipic acid, pimelic acid, cork acid, azelaic acid, sebacic acid, undecane dicarboxylic acid, dodecane dicarboxylic acid, and brassylic acid.

17. The aqueous composition according to claim 4, wherein the aqueous composition is a cosmetic formulation and comprises at least one further component selected from the group consisting of humectants, UV light protection filters, and pigments.

18. The method according to claim 6, wherein in (d), the monocarboxylic acid has 8 to 22 carbon atoms, and the polyfunctional carboxylic acid is a dicarboxylic acid with 2 to 18 carbon atoms.

19. The method according to claim 8, wherein the at least one ketonization catalyst of (b) is selected from the group consisting of heteropoly acid (H.sub.3PW.sub.12O.sub.40) catalysts, niobium oxide (Nb.sub.2O.sub.5) catalysts, titanium oxide (TiO.sub.2) catalysts, cerium oxide (CeO.sub.2) catalysts, zinc-chromium (ZnCr) mixed oxide catalysts, manganese oxide (MnO.sub.x) catalysts, lanthanumoxide (La.sub.2O.sub.3) catalysts, magnesium oxide (MgO) catalysts, iron oxide (FeO, FeO.sub.2, Fe.sub.2O.sub.3, Fe.sub.3O.sub.4Fe.sub.4O.sub.5, Fe.sub.5O.sub.6, Fe.sub.5O.sub.7), silicon-aluminium (Si.sub.yAl.sub.zO) mixed oxide catalysts, aluminium oxide (Al.sub.2O.sub.3) catalysts, zirconia (ZrO.sub.2) catalysts, and mixtures thereof.

20. The method according to claim 12, wherein the synthesis is by at least one acetogenic microorganism.

Description

[0155] The following figures are part of the examples:

[0156] FIG. 1 shows emulsions after repeated freezing/thawing.

EXAMPLES

Example 1: Synthesis of 6-dodecanol from Ethanol and Acetate

Cultivation of Clostridium kluyveri and Extraction of Hexanoic Acid

[0157] The bacterium Clostridium kluyveri was cultivated for the biotransformation of ethanol and acetate to hexanoic acid. For the inSitu extraction of the produced hexanoic acid a mixture of tetradecane with trioctylphosphineoxide (TOPO) was continuously passed through the cultivation. All cultivation steps were carried out under anaerobic conditions in pressure-resistant glass bottles that can be closed airtight with a butyl rubber stopper.

[0158] The precultivation of Clostridium kluyveri was carried out in a 1000 mL pressure-resistant glass bottle in 250 ml of EvoDM45 medium (pH 5.5; 0.004 g/L Mg-acetate, 0.164 g/l Na-acetate, 0.016 g/L Ca-acetate, 0.25 g/l K-acetate, 0.107 mL/L H.sub.3Pat (8.5%), 2.92 g/l Na-acetate, 0.35 mg/L Co-acetate, 1.245 mg/L Ni-acetate, 20 pg/L d-biotin, 20 ?g/L folic acid,10 ?g/L pyridoxine-HCl, 50 ?g/L thiamine-HC, 50 pg/L Riboflavin, 50 pg/L nicotinic acid, 50 ?g/L Ca-pantothenate, 50 ?g/L Vitamin B12, 50 ?g/L p-aminobenzoate, 50 ?g/L lipoic acid, 0.702 mg/L (NH.sub.4).sub.2Fe(SO.sub.4).sub.2?4 H.sub.2O, 1 ml/L KS-acetate (93,5 mM), 20 mL/L ethanol, 0.37 g/L acetic acid) at 37? C., 150 rpm and a ventilation rate of 1 L/h with a mixture of 25% CO.sub.2 and 75% N.sub.2 in an open water bath shaker. The gas was discharged into the headspace of the reactor. The pH was hold at 5.5 by automatic addition of 2.5 M NH.sub.3 solution. Fresh medium was continuously fed to the reactor with a dilution rate of 2.0 d.sup.?1 and fermentation broth continuously removed from the reactor through a KrosFlo? hollow fiber polyethersulfone membrane with a pore size of 0.2 ?m (Spectrumlabs, Rancho Dominguez, USA) to retain the cells in the reactor and hold an OD.sub.600nm of ?1.5.

[0159] For the main culture 150 ml of EvoDM39 medium (pH 5.8; 0.429 g/L Mg-acetate, 0.164 g/l Na-acetate, 0.016 g/L Ca-acetate, 2.454 g/l K-acetate, 0.107 mL/L H.sub.3PO.sub.4 (8.5%), 1.01 mL/L acetic acid, 0.35 mg/L Co-acetate, 1.245 mg/L Ni-acetate, 20 ?g/L d-biotin, 20 ?g/L folic acid, 10 ?g/L pyridoxine-HCl, 50 ?g/L thiamine-HCl, 50 ?g/L Riboflavin, 50 ?g/L nicotinic acid, 50 ?g/L Ca-pantothenate, 50 ?g/L Vitamin B12, 50 ?g/L p-aminobenzoate, 50 ?g/L lipoic acid, 0.702 mg/L (NH.sub.4).sub.2Fe(SO.sub.4).sub.2?4 H.sub.2O, 1 ml/L KS-acetate (93,5 mM), 20 mL/L ethanol, 8.8 mL NH.sub.3 solution (2,5 mol/L), 27.75 ml/L acetic acid (144 g/L)) were inoculated in a 1000 ml bottle with 100 ml cell broth from the preculture to an OD.sub.600nm of 0.71.

[0160] The cultivation was carried out at 37? C., 150 rpm and a ventilation rate of 1 L/h with a mixture of 25% CO.sub.2 and 75% N.sub.2 in an open water bath shaker for 65 h. The gas was discharged into the headspace of the reactor. The pH was held at 5.8 by automatic addition of 2.5 M NH.sub.3 solution. Fresh medium was continuously fed to the reactor with a dilution rate of 0.5 d.sup.?1 and fermentation broth continuously removed from the reactor by holding an OD.sub.600nm of ?0.5. Additional 120 g of a mixture of 6% (w/w) TOPO in tetradecane was added to the fermentation broth. Then this organic mixture was continuously fed to the reactor and the organic phase also continuously removed from the reactor with a dilution rate of 1 d.sup.?1.

[0161] During cultivation several 5 mL samples from both, the aqueous and the organic phase, were taken to determinate OD.sub.600nm, pH and product formation. The determination of the product concentrations was performed by semiquantitative 1H-NMR spectroscopy. As an internal quantification standard sodium trimethylsilylpropionate (T(M)SP) was used.

[0162] During the main cultivation in the aqueous phase a steady state concentration of 8.18 g/L ethanol, 3.20 g/L acetate, 1.81 g/L butyrate and 0.81 g/L hexanoate was reached. The OD.sub.600nm remained stable at 0.5. In the organic phase a steady state concentration of 0.43 g/kg ethanol, 0.08 g/kg acetate, 1.13 g/kg butyrate and 8.09 g/kg hexanoate was reached. After the experiment the cells remained viable while transferred to further cultivations.

[0163] The distribution coefficient K.sub.D of the substrates and products in the system aqueous medium and 6% TOPO in tetradecane was calculated from the concentrations in both phases.

[00001]$K\left(D\right)=\frac{c\left(\mathrm{organic}\mathrm{phase}\right)}{c\left(\mathrm{aqueous}\mathrm{phase}\right)}$

[0164] The K.sub.D in the steady state was 0.05 for ethanol, 0.03 for acetic acid, 0.62 for butyric acid and 9.99 for hexanoic acid.

Ketonization of Hexanoic Acid to 6-undecanone

[0165] The ketonization was conducted in a heated continuous flow-bed reactor. At first, the reactor was charged with magnesium oxide on silica (50 wt. %, 14.00 g) and heated under an argon flow (54 mL/min) at 330? C. for one hour. The temperature was raised to 360? C. Than a mixture of hexanoic acid in tetradecane (v/v: 3/1) was continuously fed to the reactor with a rate of 3.3 mL/h. The gaseous out stream was collected by two cooling traps, which were cooled with water and a mixture of dry ice and isopropanol. The collected fractions were weighted and analyzed by gas chromatography (GC) for their composition. In total, 370.65 g of hexanoic acid was fed to the reactor, which equals to a maximum theoretical yield of 271.70 g of 6-undecanone and 28.75 g of water and 70.21 g of carbon dioxide as by-products. The obtained amount of 6-undecanone was 267.67 g and the amount of water was 28.32 g. This corresponds to a 99% mass recovery at full conversion. The high productivity and selectivity were confirmed by regular GC measurements, as only traces of hexanoic acid and no side-products were detected.

Hydrogenation of 6-undecanone to 6-undecanol

[0166] The hydrogenation reaction for 6-undecanone to 6-undecanol was performed in a 300 ml autoclave reactor (PARR Instrument Company). The reactor was placed in an aluminum block and the temperature was controlled by a thermocouple placed inside the reactor. Typically, 30 mg of solid catalyst, 170.3 mg, 1.0 mmol of substrate was added to a 4 ml glass vial having an oven dried magnetic stirrer. 2.0 ml of dry Toluene was used as solvent, vial was fitted with a screw cap and a needle was inserted through the septum. The vial was placed in the reactor. The reactor was purged three times with 10 bar of H.sub.2 and then the pressure was increased to 20 bar. The reactor was heated to the desired temperature of 120? C. for 20 h. After the reaction, the reactor was cooled down to 5? C. using an ice bath, the gas phase was slowly released, and the remaining liquid was carefully separated from the solid catalyst and was analyzed separately using an internal standard (100 ?L n-hexadecane).

[0167] The catalyst 3.0 Co@?-Al.sub.2O.sub.3 showed 99% ketone conversion and an alcohol yield of 98%. The catalyst preparation method was as follows:

[0168] 3wt % Co@?-Al.sub.2O.sub.3, using Ascorbic acid as reductant and glucose as capping agent in H.sub.2O,

[0169] Pyrolysis at 800? C. for 2 h, Co salt is Cobalt(II) nitrate hexahydrate. In a typical synthesis, 149 mg, 0.51 mmol of Co(NO.sub.3).sub.2. 6H.sub.2O was dissolved in 20 ml D.I H.sub.2O followed by the stepwise addition of aqueous solutions of 265 mg, 3.0 mmol ascorbic acid and 92 mg, 1 mmol of D-(+)-glucose. The contents were stirred at 90? C. for 2-3 h. Next, 1.0 g of ?-Al.sub.2O.sub.3 support was added and the slurry was stirred overnight at R.T. Excess water was removed through centrifugation and the solids were dried in oven at 120? C. for 10 h and then pyrolyzed at 800? C. for 2 h under argon atmosphere.

Example 2: Undec-6-yl Hexanoate

[0170] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and hexanoic acid (min. 98% (purified ntermediate from Example 1), 116.2 g/mol, 70.9 g, 0.61 mol) was heated under catalytic addition of 0.17 g para-toluene sulfonic acid and stirred at 160? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity of less than 20 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered, washed with water and distilled in vacuum. A colorless to slightly yellow oil was obtained. Saponification value: 207 mg KOH/g. Purity (GC): >98%.

Example 3: Undec-6-yl Laurate

[0171] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and lauric acid (min. 99% (from Sigma-Aldrich), 200.3 g/mol, 116.2 g, 0.58 mol) was heated under catalytic addition of 1.1 g para-toluene sulfonic acid and stirred to 150? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity of less than 20 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered, washed with water and distilled in vacuum. A colorless to slightly yellow oil was obtained.

[0172] Saponification value: 158 mg KOH/g. Purity (GC): >98%.

Example 4: Undec-6-yl Stearate

[0173] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and stearic acid (min. 92%, Palmac 90-18 (from IOI), acid value 199 mg KOH/g, 284 g/mol, 156.2 g, 0.55 mol) was heated under catalytic addition of 0.26 g of tin(II)oxide and stirred at 180? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity of less than 20 mg KOH/g was reached.

[0174] The product was neutralized with potassium hydroxide solution and subsequently filtered, bleached with H.sub.2O.sub.2 solution and washed with water. After drying a slightly yellowish wax was obtained. Acid value: <1 mg KOH/g; Saponification value: 129 mg KOH/g. Purity (GC): >95%.

Example 5: Undec-6-yl Caprylate/Caprate

[0175] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and caprylic/capric acid (Kortacid 0810 (from Oleon), acid value 360 mg KOH/g, 156 g/mol, 95.2 g, 0.61 mol) was heated under catalytic addition of 0.2 g para-toluene sulfonic acid and stirred at 160? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity of less than 20 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered, washed with water and distilled in vacuum. A slightly yellowish oil was obtained.

[0176] Saponification value: 181 mg KOH/g. Purity (GC): >97%.

Example 6: Undec-6-yl Cocoate

[0177] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and distilled coconut fatty acid (Wilfarin DC-0818 (from Wilmar), acid value 270 mg KOH/g, 208 g/mol, 114.4 g, 0.55 mol) was heated under catalytic addition of 0.43 g of tin(I1)oxide and stirred at 160? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity of less than 20 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered, bleached with H.sub.2O.sub.2 solution and washed with water. After drying a yellowish oil was obtained.

[0178] Acid value: 1 mg KOH/g; Saponification value: 156 mg KOH/g. Purity (GC): >95%.

Example 7: Undec-6-yl 12-Hydroxystearate

[0179] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and 12-hydroxystearic acid (H.C.O. Fatty Acid (from Jayant), acid value 182 mg KOH/g, 308 g/mol, 169.4 g, 0.55 mol) was heated under catalytic addition of 0.27 g of tin(I1)oxide and stirred at 180? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity of less than 20 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered, bleached with H.sub.2O.sub.2 solution and washed with water. After drying a yellowish wax was obtained.

[0180] Acid value: 1 mg KOH/g; Saponification value: 122 mg KOH/g. Purity (GC): >92%.

Example 8: Undec-6-yl lsostearate

[0181] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and isostearic acid (PRISORINE 3503 (from Croda), acid value 190 mg KOH/g, 295 g/mol, 162.3 g, 0.55 mol) was heated under catalytic addition of 0.13 g of tin(II)oxide and stirred at 180? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity of less than 20 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered, bleached with H.sub.2O.sub.2 solution and washed with water. After drying a yellowish oil was obtained. Acid value: 2 mg KOH/g; Saponification value: 125 mg KOH/g. Purity (GC): >90%.

Example 9: Undec-6-yl Oleate

[0182] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and oleic acid (Wilfarin OA 7075 (from Wilmar), acid value 200 mg KOH/g, 281 g/mol, 154.6 g, 0.55 mol) was heated under catalytic addition of 0.25 g of tin(II)oxide and stirred at 180? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity of less than 20 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered, bleached with H.sub.2O.sub.2 solution and washed with water. After drying a yellow oil was obtained.

[0183] Acid value: 1 mg KOH/g; Saponification value: 128 mg KOH/g. Purity (GC): >92%.

Example 10: Bis(undec-6-yl)malate

[0184] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and D,L-malic acid (min. 98% (from Sigma-Aldrich), 134.1 g/mol, 37.5 g, 0.28 mol) was heated under catalytic addition of 0.14 g para-toluene sulfonic acid and stirred at 160? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity below 30 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered and washed with water. After drying a yellowish oil was obtained.

[0185] Acid value: 2 mg KOH/g; Saponification value: 255 mg KOH/g. Purity (GC): >90%.

Example 11: Bis(undec-6-yl)succinate

[0186] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and succinic acid (min. 99% (from Sigma-Aldrich), 118.9 g/mol, 33.3 g, 0.28 mol) was heated under catalytic addition of 0.13 g para-toluene sulfonic acid and stirred at 180? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity below 30 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered and washed with water. After drying a slightly yellowish wax was obtained.

[0187] Acid value: 2 mg KOH/g; Saponification value: 262 mg KOH/g. Purity (GC): >90%.

Example 12: Bis(undec-6-yl)sebacate

[0188] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and sebacic acid (min. 99% (from Sigma-Aldrich), 202.3 g/mol, 56.6 g, 0.28 mol) was heated under catalytic addition of 0.8 g para-toluene sulfonic acid and stirred at 180? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity below 30 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered and washed with water. After drying a yellowish wax was obtained.

[0189] Acid value: 1 mg KOH/g; Saponification value: 223 mg KOH/g. Purity (GC): >90%.

Example 13: Furan-2, 5-dicarboxylic acid bis(undec-6-yl)ester

[0190] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and dimethyl furan-2,5-dicarboxylate (min. 99% (from Sigma-Aldrich), 184.1 g/mol, 53.4 g, 0.29 mol) was heated under catalytic addition of 0.15 g para-toluene sulfonic acid and stirred at 150? C. The resulting methanol was continuously distilled off in vacuum until an acidity of approx. 20 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered and washed with water. After drying a yellowish oil was obtained.

[0191] Acid value: 2 mg KOH/g; Saponification value: 260 mg KOH/g. Purity (GC): >85%.

Example 14: Tris(undec-6-yl)citrate

[0192] A mixture of undecan-6-ol (172.3 g/mol, 100.0 g, 0.58 mol) and citric acid (min. 99% (from Sigma-Aldrich), 192.1 g/mol, 34.6 g, 0.18 mol) was heated under catalytic addition of 0.13 g para-toluene sulfonic acid and stirred at 180? C. The resulting water was continuously distilled off in vacuum and under a flow of nitrogen until an acidity of approx. 30 mg KOH/g was reached. The product was neutralized with potassium hydroxide solution and subsequently filtered and washed with water. After drying a yellowish wax was obtained.

[0193] Acid value: 2 mg KOH/g; Saponification value: 260 mg KOH/g. Purity (GC): >85%.

Example 15: Application Testings

[0194] In order to show the advantageous property of aqueous compositions comprising 6-undecanol-esters, the following W/O emulsions have been prepared using common methods. The water phase was added slowly and incorporated into the oil phase. The mixture was subsequently homogenized. As reference substrate TEGOSOFT DC (Decyl Cocoate) was used in the comparative example which is not in the scope of this invention.

[0195] To evaluate the freeze stability the following formulations for a body lotion were subjected to two freeze thaw cycles from room temperature to ?15? C. and back to room temperature. The freeze stability of the aqueous compositions was determined by visual inspection after the samples reached room temperature again. The following terminology was used to describe the freeze stability:

TABLE-US-00001 Freeze stability Very good (++) No or minimal water separation Good (+) Very weak water separation Medium (0) Weak water separation Weak (?) Strong water separation Very weak (??) Very strong oil separation

[0196] The sensory of the cosmetic emulsions are evaluated by a trained sensory panel. At least 5 persons are evaluating the sensory profile of the formulations without knowing the composition of the evaluated samples. The properties the majority of the panellists have described is reported in the table below; given numbers are weight percentages.

Body Lotion

[0197]

TABLE-US-00002 Phase Ingredient A B* C* A ISOLAN? GPS 2.5 2.5 2.5 TEGOSOFT? DC (Decyl 21.0 Cocoate) Example 3 21.0 Example 11 21.0 Bees wax 0.2 0.2 0.2 Castor wax 0.3 0.3 0.3 Dermofeel? Toco 70 non GMO 0.2 0.2 0.2 B Verstatil PC (Phenoxyethanol; 0.8 0.8 0.8 Carpylyl Glycol) C Glycerin 3.0 3.0 3.0 Water 70.5 70.5 70.5 Zink sulphate*7 H.sub.2O 1.5 1.5 1.5 Freeze stability (?) (++) (++) Sensory characterization During During During distribution: distribution: distribution: easy to typical typical distribute, distribution distribution light, non- behaviour, behaviour, tacky very light, very light, 5 minutes non-waxy non-tacky after 5 minutes 5 minutes absorption: after after non-tacky, absorption: absorption: medium level high high of residue, not absorption, absorption, slippery smooth, light, slippery slippery *According to the invention

[0198] In FIG. 1 formulation B containing example 3 is shown on the left in comparison to formulation A containing Decyl Cocoate on the right after freeze-thaw-cycles.

[0199] The sensory results surprisingly show lower distribution ability for the systems containing the inventive examples compared to the reference sample while showing high absorption as well as slippery properties 5 minutes after absorption. After the freeze stability test the inventive systems show no signs of instability whereas the comparative sample shows strong water separation which is not acceptable for cosmetic formulations.

Example 16: Further Exemplary Aqueous Compositions Comprising 6-undecanol-esters According to the Invention

[0200] The following examples demonstrate the versatile applicability of 6-undecanol-esters in different cosmetic formulations and their compatibility with various other ingredients such as emulsifiers, stabilizers, preservatives or active compounds like UV-filters or antimicrobial drugs which are usually challenging to formulate. The application of the invention is not limited to the formulations shown. The preparation of the examples has been done according to common standard methods.

Natural Body Spray

[0201]

TABLE-US-00003 w/w- w/w- w/w- w/w- Phase Ingredient % % % % A TEGO? Care LTP (Sorbitan 2.50 3.00 Laurate; Polyglyceryl-4 Laurate; Dilauryl Citrate) TEGO? Care PBS 6 3.00 3.00 (Polyglyceryl-6 Stearate; Polyglyceryl-6 Behenate) Example 2 12.50 12.00 Example 10 14.00 9.50 B Water Ad Ad Ad Ad 100 100 100 100 Glycerin 3.00 3.00 3.00 4.00 Gellan Gum (Kelcogel 0.10 0.10 0.10 0.15 CG-HA, CP Kelco) C dermsosoft? OMP 2.50 2.50 2.50 2.50 (Methylpropandiol; Caprylyl Glycol; Penylpropanol)

W/O Cream

[0202]

TABLE-US-00004 Phase Ingredient w/w-% w/w-% w/w-% A ISOLAN? PDI (Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate) 3.00 ISOLAN? 17 (Polyglyceryl-4 Diisostearate/Polyhydroxystearate/ 3.00 3.00 Sebacate (and) Caprylic/Capric Triglyceride (and) Polyglyceryl-3 Oleate (and) Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate) Hydrogenated Castor Oil 0.40 0.40 0.40 Beeswax 0.60 0.60 0.60 TEGOSOFT? CT (Caprylic/Capric Triglyceride) 5.00 5.00 5.00 TEGOSOFT? P (Isopropyl Palmitate) 5.00 5.00 5.00 TEGOSOFT? OER (Oleyl Erucate) 3.00 3.00 3.00 Prunus Amygdalus Dulcis (Sweet Almond) Oil 3.00 3.00 3.00 Example 3 6.00 7.00 3.00 Example 11 4.00 B Water ad ad ad 100 100 100 Glycerin 5.00 5.00 3.00 C Magnesium Sulfate Heptahydrate 1.00 1.50 0.90 Sodium Benzoate, Potassium Sorbate, Water (Euxyl K 712, 0.50 0.50 0.50 Sch?lke & Mayr) Citric Acid (10% in water) q.s. q.s. q.s.

Anti-Aging Day Cream

[0203]

TABLE-US-00005 Phase Ingredient w/w-% w/w-% w/w-% A ABIL? EM 90 (Cetyl PEG/PPG-10/1 Dimethicone Triglyceride) 3.00 ABIL? EM 180 (Cetyl PEG/PPG-10/1 Dimethicone Triglyceride) 2.00 ABIL? WE 09 (Polyglyceryl-4 Isostearate; Cetyl PEG/PPG-10/1 4.00 Dimethicone; Hexyl Laurate) TEGOSOFT? AC (Isoamyl Cocoate) 5.00 4.00 5.00 TEGOSOFT? DEC (Diethylhexyl Carbonate) 6.00 5.00 5.00 Example 4 7.00 6.00 Example 12 10.00 2.00 HyaCare? Filler CL (Aqua, Ethylhexyl Stearate, Sodium 2.50 2.50 2.50 Hyaluronate Crosspolymer, Polyglyceryl-4 Diisostearate/Polyhydroxystearate/Sebacate, Sodium Isostearate) Tocopherol 0.50 0.50 0.50 Methyl Methacrylate Crosspolymer (Covabead LH 85, Sensient) 2.00 2.00 2.00 B Water ad ad ad 100 100 100 Sodium Chloride 0.80 0.80 0.80 Glycerin 4.00 4.00 4.00 Butylene Glycol 4.00 4.00 4.00 TEGO? Pep 4-Even (Tetrapeptide-30; Glycerin) 2.50 2.50 2.50 Sodium Ascorbyl Palmitate 1.50 1.50 1.50 Urea 2.50 2.50 2.50 Sodium Bisulfite 0.10 0.10 0.10 Z Preservative, Perfume q.s. q.s. q.s.

Light & Caring Cream

[0204]

TABLE-US-00006 Phase Ingredient w/w-% w/w-% A ABIL? EM 90 (Cetyl PEG/PPG-10/1 2.00 1.50 Dimethicone) ABIL? EM 97 S (Bis-PEG/PPG-14/14 1.00 Dimethicone (and) Dimethicone) TEGOSOFT? OP (Ethylhexyl Palmitate) 5.00 5.00 TEGOSOFT? CT (Caprylic/Capric 5.00 5.00 Triglyceride) TEGOSOFT? DEC (Diethylhexyl Carbonate) 10.00 10.00 Example 5 6.00 6.00 dermofeel? viscolid (Hydrogenated Vegetable 0.50 0.50 Oil) B Water ad ad 100 100 Sodium Chloride 0.50 0.50 C Phenoxyethanol, Ethylhexylglycerin (euxyl? 0.80 0.80 PE 9010, Sch?lke & Mayr)

Serum

[0205]

TABLE-US-00007 w/w- Phase Ingredient % A TEGO? Care 165 (Glyceryl Stearate; 3.00 PEG-100 Stearate) TEGO? Alkanol 18 (Stearyl Alcohol) 0.50 Isononyl Isononanoate 4.00 Hydrogenated Polyisobutene 3.00 TEGOSOFT? APM (PPG-3 Myristyl Ether) 3.00 Example 6 0.50 Tocopherol 0.50 B Aqua ad 100 Butylene Glycol 5.00 SKINMIMICS? (Ceteareth-25; Glycerin; 2.50 Cetyl Alcohol; Behenic Acid; Cholesterol; Ceramide NP; Ceramide NS; Ceramide EOS; Ceramide EOP; Ceramide AP; Caprooyl Phytosphingosine; Caprooyl Sphingosine) C Polyacrylamide; C13-14 Isoparaffin; 0.75 Laureth-7 (Sepigel 305, Seppic) Z Preservative, Perfume q.s.

Rich Natural Cream

[0206]

TABLE-US-00008 Phase Ingredient w/w-% w/w-% w/w-% w/w-% A TEGO? Care PSC 3 (Polyglyceryl-3 3.00 Dicitrate/Stearate) Symbiomuls GC (Glyceryl Stearate Citrate; Cetearyl 3.50 Alcohol; Glyceryl Caprylate) Dermofeel NC (Polyglyceryl-3 Distearate (and) 2.50 3.00 Glyceryl Stearate Citrate) TEGIN? M Pellets (Glyceryl Stearate) 0.90 0.30 0.90 0.50 TEGO? Alkanol 1618 (Cetearyl Alcohol) 0.60 0.30 0.60 0.60 TEGOSOFT? P (Isopropyl Palmitate) 3.00 3.00 3.00 3.00 Prunus Amygdalus Dulcis Oil 5.00 5.00 5.00 5.00 TEGOSOFT? CT (Caprylic/Capric Triglyceride) 4.50 4.50 4.50 4.50 Triisostearin 3.50 3.50 3.50 3.50 Example 7 6.00 4.00 2.50 Example 13 6.00 2.00 5.00 B Water ad ad ad ad 100 100 100 100 Glycerin 3.00 4.00 3.00 5.00 Xanthan Gum (Keltrol CG-SFT, CP Kelco) 0.30 0.30 0.30 0.30 C Sodium hydroxide (10% in water) q.s. q.s. q.s. q.s. Z Preservative, Perfume q.s. q.s. q.s. q.s.

After Shave Lotion

[0207]

TABLE-US-00009 w/w- w/w- Phase Ingredient % % A ABIL? Care 85 (Bis-PEG/PPG-16/16 1.50 PEG/PPG-16/16 Dimethicone; Caprylic/Capric Triglyceride) ABIL? Care XL 80 (Bis-PEG/PPG-20/5 1.50 PEG/PPG-20/5 Dimethicone (and) Methoxy PEG/PPG-25/4 Dimethicone (and) Caprylic/Capric Triglyceride) TEGOSOFT? CT (Caprylic/Capric 3.00 3.00 Triglyceride) Example 8 3.50 3.50 Tocopheryl Acetate 0.50 0.50 Menthyl Lactate (Frescolat ML) 0.50 0.50 B TEGO? SMO 80 V (Polysorbate 80) 0.50 0.50 Aqua ad ad 100 100 Glycerin 2.00 2.00 Alcohol 15.00 15.00 C TEGO? Carbomer 141 (Carbomer) 0.20 0.20 Xanthan Gum 0.10 0.10 Mineral Oil (30 mPas) 1.60 1.60 D Sodium hydroxide (10% in water) q.s. q.s. Z Preservative, Perfume q.s. q.s.

Light W/O Emulsion

[0208]

TABLE-US-00010 w/w- Phase Ingredient % A ISOLAN? GPS (Polyglyceryl-4 Diisostearate/ 3.00 Polyhydroxystearate/Sebacate) Example 9 6.40 TEGOSOFT? DEC (Diethylhexyl Carbonate) 6.40 Dicaprylyl Carbonate, Stearalkonium Hectorite, 3.00 Propylene Carbonate (Cosmedia? Gel CC, Cognis) B Water ad 100 Glycerin 2.00 Magnesium Sulfate Heptahydrate 1.50 C Phenoxyethanol, Ethylhexylglycerin (euxyl? 0.70 PE 9010, Sch?lke & Mayr)

Anti-Aging Hydration Cream

[0209]

TABLE-US-00011 Phase Ingredient w/w-% A TEGO? Care 450 (Polyglyceryl-3 Methylglucose 3.00 Distearate) TEGIN? M Pellets (Glyceryl Stearate) 2.00 TEGO? Alkanol 18 (Stearyl Alcohol) 1.00 TEGOSOFT? MM (Myristyl Myristate) 1.00 TEGOSOFT? DO (Decyl Oleate) 8.00 Example 14 11.50 Phytosphingosine SLC (Salicyloyl Phytosphingosine) 0.10 B Glycerin 3.00 Aqua ad 100 C TEGO? Carbomer 134 (Carbomer) 0.20 TEGOSOFT? P (Isopropyl Palmitate) 0.80 D Sodium hydroxide (10% in water) q.s. Z Preservative, Perfume q.s.

Light O/W Sun Care Lotion

[0210]

TABLE-US-00012 Phase Ingredient w/w-% A AXOL? C 62 Pellets (Glyceryl Stearate Citrate) 2.50 TEGO? Alkanol 1618 (Cetearyl Alcohol) 1.00 Example 5 6.00 Isoadipate (Diisopropyl Adipate) 3.00 Butyloctyl Salicylate (HallBrite BHB, The 2.00 HallStar Company) Tocopheryl Acetate 0.20 Dimethicone (5 mPas) 1.00 Butyl Methoxydibenzoylmethane 1.50 Diethylamino Hydroxybenzoyl Hexyl Benzoate 4.00 (Uvinul A Plus, BASF) Ethylhexyl Triazone 2.00 Ethylhexyl Salicylate 5.00 Octocrylene 8.00 Ethylhexyl methoxycrylene 1.50 B Titanium Dioxide; Trimethoxycaprylylsilane 1.00 C Glycerin 3.20 EDTA 0.02 Water ad 100 D Acrylates/C10-30 Alkyl Acrylate Crosspolymer 0.10 Example 9 0.90 E Sodium Hydroxide (10% in water) q.s Z Preservative, Perfume q.s

Sun Care Spray SPF 30

[0211]

TABLE-US-00013 Phase Ingredient w/w-% A TEGO? Care PBS 6 MB (Polyglyceryl-6 Stearate, 3.00 Polyglyceryl-6 Behenate) Example 2 3.00 Bis-ethylhexyloxyphenol Methoxyphenyl Triazine 3.00 (Tinosorb S, BASF) Butyl Methoxydibenzoylmethane 2.00 Homosalate 4.00 Ethylhexyl Salicylate 4.00 Octocrylene 4.00 TEGO? Feel C 10 (Cellulose) 1.00 B Water ad 100 Gellan Gum (Kelcogel CG-HA, CP Kelco) 0.03 EDTA 0.05 Glycerin 3.00 Acrylates/C10-30 Alkyl Acrylate Crosspolymer 0.20 C Phenylbenzimidazole Sulfonic Acid 2.00 Tromethamine 0.88 Water 7.12 E Tromethamine (Trisaminomethane, 30% in water) q.s. F dermofeel? OMP (Methylpropanediol, Caprylyl 3.00 Glycol, Phenylpropanol)

Cationic Hand Cream

[0212]

TABLE-US-00014 Phase Ingredient w/w-% A VARISOFT? TA 100 (Distearyldimonium Chloride) 3.50 TEGIN? M Pellets (Glyceryl Stearate) 1.50 TEGO? Alkanol 18 (Stearyl Alcohol) 1.00 Example 12 13.00 TEGOSOFT? DEC (Diethylhexyl Carbonate) 8.00 TEGOSOFT? CR (Cetyl Ricinoleate) 1.00 Triisostearin 1.00 B TEGO? Cosmo C 100 (Creatine) 0.50 Glycerin 3.00 Water ad 100 Z Preservative, Parfum q.s.

AP/Deo Roll-On, PEG- and ACH-Free

[0213]

TABLE-US-00015 Phase Ingredient w/w-% A TEGO? Care APD 18 (Polyglyceryl-6 Stearate; 5.00 Polyglyceryl-6 Behenate; C18-22 Hydroxyalkyl Hydroxypropyl Guar) Example 3 5.00 B Water ad 100 Glycerin 3.00 Potassium Alum 5.00 C Preservative, Perfume q.s.

Oil Release Lotion

[0214]

TABLE-US-00016 Phase Ingredient w/w-% A TEGO? Care PBS 6 (Polyglyceryl-6 Stearate, 3.00 Polyglyceryl-6 Behenate) TEGOSOFT? DEC (Diethylhexyl Carbonate) 10.00 Example 8 26.00 TEGOSOFT? OER (Oleyl Erucate) 10.00 TEGOSOFT? CT (Caprylic/Capric Triglyceride) 15.00 TEGOSOFT? AC (Isoamyl Cocoate) 10.00 TEGO? Feel C 10 (Cellulose) 1.00 B Aqua ad 100 Glycerin 3.00 C Phenoxyethanol, Ethylhexylglycerin (Euxyl PE 0.70 9010, Schulke & Mayr GmbH) D Citric Acid (10% in water) q.s.

W/O Make-Up Foundation:

[0215]

TABLE-US-00017 w/w- w/w- w/w- w/w- w/w- w/w- Nomenclature according to INCI % % % % % % A ISOLAN? 17 (Polyglyceryl-4 4.00 3.00 2.00 3.00 2.00 Diisostearate/Polyhydroxystearate/ Sebacate (and) Caprylic/Capric Triglyceride (and) Polyglyceryl-3 Oleate (and) Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate) ISOLAN? GPS (Polyglyceryl-4 1.00 Diisostearate/Polyhydroxystearate/Sebacate Dehymuls PGPH (Polyglyceryl-2 1.50 Dipolyhydroxystearate) Cithrol PG3PR (Polyglyceryl-3 Polyricinoleate) 2.00 ABIL? EM 90 (Cetyl PEG/PPG-10/1 Dimethicone) 1.50 3.00 Dermofeel sensolv (Isoamyl Laurate) 7.00 6.00 5.00 7.00 2.50 6.00 Decyl Cocoate 4.00 4.00 4.00 3.00 Isopropyl Myristate 6.00 6.00 4.50 Caprylic/Capric Triglyceride 4.00 3.00 4.00 Diethylhexyl Carbonate 4.00 5.00 Dimethicone 15.00 Example 4 3.00 2.00 6.00 4.00 Example 11 2.00 5.00 5.00 2.00 0.50 CI 77891 (and) Hydrogenated Lecithin 5.00 5.00 5.00 5.00 5.00 CI 77492 (and) Hydrogenated Lecithin 0.60 0.60 0.60 0.60 0.60 CI 77491 (and) Hydrogenated Lecithin 0.35 0.35 0.35 0.35 0.35 CI 77499 (and) Hydrogenated Lecithin 0.10 0.10 0.10 0.10 0.10 Disteardimonium Hectorite dimethicone, propylencarbonat 2.00 2.00 2.00 2.00 2.00 B Water ad ad ad ad ad 100 100 100 100 100 Sodium chloride 1.00 1.00 1.50 Magnesium Sulfate Heptahydrate 1.50 2.00 Glycerin 3.00 3.00 3.00 5.00 5.00 C Phenoxyethanol, Caprylyl Glycol 1.00 1.00 1.00 1.00 1.00

Clear Conditioning Shampoo

[0216]

TABLE-US-00018 Ingredient w/w-% Example 7 0.1 TEXAPON? NSO, BASF, 28%-ig 32.00 (INCI: Sodium Laureth Sulfate) REWODERM? LI S 80, Evonik Nutrition & Care GmbH 2.00 (INCI: (PEG-200 Hydrogenated Glyceryl Palmate; PEG-7 Glyceryl Cocoate) Perfume 0.25 Water ad 100.00 TEGO? Cosmo C 100, Evonik Nutrition & Care GmbH, 1.50 (INCI: Creatine) Jaguar C-162, Solvay, (INCI: Hydroxypropyl Guar 0.20 Hydroxypropyltrimonium Chloride) TEGO? Betain F 50, Evonik Nutrition & Care GmbH, 8.00 38%-ig (INCI: Cocamidopropyl Betaine) NaCl 2.50 Citric Acid, 30%-ig q.s. (pH 5.0) Preservative q.s.

Pearlizing Shampoo

[0217]

TABLE-US-00019 Ingredient w/w-% TEXAPON? NSO, BASF, 28%-ig 32.00 (INCI: Sodium Laureth Sulfate) Example 6 0.20 Perfume 0.15 Water ad 100.00 TEGO? Betain F 50, Evonik Nutrition & Care GmbH, 38%-ig 8.00 (INCI: Cocamidopropyl Betaine) TEGO? Pearl N 300, Evonik Nutrition & Care GmbH, 2.00 (INCI: Glycol Distearate; Laureth-4; Cocamidopropyl Betaine) ANTIL? 171 Evonik Nutrition & Care GmbH, 2.50 (INCI: PEG-18 Glyceryl Oleate/Cocoate) NaCl 0.90 Citric Acid, 30%-ig q.s. (pH 5.5) Preservative q.s.

Conditioning Shampoo

[0218]

TABLE-US-00020 Ingredient w/w-% TEXAPON? NSO, BASF, 28%-ig (INCI: Sodium 32.00 Laureth Sulfate) ANTIL? 200, Evonik Nutrition & Care GmbH, 2.00 (INCI: PEG-200 Hydrogenated Glyceryl Palmate; PEG-7 Glyceryl Cocoate) Perfume 0.25 Water ad 100.00 Polymer JR 400, Amerchol, (INCI: Polyquaternium-10) 0.40 TEGO? Betain F 50, Evonik Nutrition & Care GmbH, 8.00 38%-ig (INCI: Cocamidopropyl Betaine) Example 10 0.50 TEGO? Pearl N 300, Evonik Nutrition & Care GmbH, 2.00 (INCI: Glycol Distearate; Laureth-4; Cocamidopropyl Betaine) NaCl 0.30 Citric Acid, 30%-ig q.s. (pH 5.5) Preservative q.s.

Anti-Dandruff Shampoo

[0219]

TABLE-US-00021 Ingredient w/w-% TEXAPON? LS 35, BASF, 30%-ig 24.00 (INCI: Sodium Lauryl Sulfate) TAGAT? CH 40, Evonik Nutrition & Care GmbH, 2.00 (INCI: PEG-40 Hydrogenated Castor Oil) TEGOSOFT? GC, Evonik Nutrition & Care GmbH, 1.00 (INCI: PEG-7 Glyceryl Cocoate) Example 13 0.15 Perfume 0.20 Water ad 100.00 Polymer JR 400, Amerchol, (INCI: Polyquaternium-10) 0.20 TEGO? Betain F 50, Evonik Nutrition & Care GmbH, 16.00 38%-ig (INCI: Cocamidopropyl Betaine) Hostapon SG, Clariant, (INCI: Sodium Cocoyl Glycinate) 5.00 Microcare ZP, Thor, (INCI: Zinc Pyrithione) 0.200 Octopirox, Clariant, (INCI: Octopirox) 0.10 ABIL? Quat 3272, Evonik Nutrition & Care GmbH, 0.80 (INCI: Quaternium-80) REWOMID? D 212, Evonik Nutrition & Care GmbH, 0.80 (INCI: Cocamide MEA) ANTIL? 500, Evonik Nutrition & Care GmbH, 0.80 (INCI: PEG-200 Glyceryl Stearate) Glycerin 1.50 NaCl 0.90 Citric Acid, 30%-ig q.s. (pH 5.5) Preservative q.s.

Shampoo, PEG-Free

[0220]

TABLE-US-00022 Ingredient w/w-% TEXAPON? LS 35, BASF, 30% (INCI: Sodium Lauryl 28.00 Sulfate) Water ad 100.00 UCARE Polymer JR-400, Dow Chemicals, 0.10 (INCI: Polyquaternium-10) Jaguar C-162, Solvay, (INCI: Hydroxypropyl 0.10 Guar Hydroxypropyltrimonium Chloride) ANTIL? CM 90, Evonik Nutrition & Care GmbH, 0.50 (INCI: Cocamide MEA) ANTIL? SPA 80, Evonik Nutrition & Care GmbH, 1.00 (INCI: Isostearamide MIPA; Glyceryl Laurate) Xanthan Gum 0.50 Example 14 0.10 Dehyton AB 30, BASF, 31%, (INCI: Coco-Betaine) 8.00 Prifrac 2920, Croda, (INCI: Lauric Acid) 0.50 TEGOSOFT? PC 41, Evonik Nutrition & Care GmbH, 1.00 (INCI: Polyglyceryl-4 Caprate) Glycerin 1.00 Uvinul MS 40, BASF, (INCI: Benzophenon-4) 0.10 Versene 100, The Dow Chemical Company, (INCI: 0.10 Tetrasodium EDTA) Sodium Chloride 1.00 Perfume, preservative q.s. Citric Acid, 30%-ig q.s. (pH 5.0)

Shampoo, Sulfate-Free

[0221]

TABLE-US-00023 Ingredient w/w-% Bioterge AS-40 AOS, Stepan, (INCI: Sodium C14-16 30.00 Olefin Sulfonate) Water ad 100.00 Jaguar C-162, Solvay, (INCI: Hydroxypropyl 0.15 Guar Hydroxypropyltrimonium Chloride) ANTIL? 500 Pellets, Evonik Nutrition & Care GmbH, 0.20 (INCI: PEG-200 Glyceryl Stearate) ANTIL? SPA 80, Evonik Nutrition & Care GmbH, 0.50 (INCI: Isostearamide MIPA; Glyceryl Laurate) Example 2 0.10 Dehyton AB 30, BASF, 31%, (INCI: Coco-Betaine) 8.00 TAGAT? CH 40, Evonik Nutrition & Care GmbH, 1.00 (INCI: PEG-40 Hydrogenated Castor Oil) Glycerin 1.00 Uvinul MS 40, BASF, (INCI: Benzophenon-4) 0.10 Sodium Chloride 1.50 Perfume, preservative q.s. Citric Acid, 30%-ig q.s. (pH 5.5)

Shampoo, Sulfat-Free

[0222]

TABLE-US-00024 Ingredient w/w-% TEGO? Betain F 50, Evonik Nutrition & Care GmbH, 22.00 38%-ig, (INCI: Cocamidopropyl Betaine) Water ad 100.00 Jaguar C-162, Solvay, (INCI: Hydroxypropyl 0.10 Guar Hydroxypropyltrimonium Chloride) ANTIL? 500 Pellets, Evonik Nutrition & Care GmbH, 0.30 (INCI: PEG-200 Glyceryl Stearate) REWOPAL? PEG 6000 DS A, Evonik Nutrition & 0.50 Care GmbH, (INCI: PEG-150 Distearate) Example 11 0.10 Hostapon SG, Clariant, (INCI: Sodium Cocoyl Glycinate) 10.00 TEGO? Solve 61, Evonik Nutrition & Care GmbH, 1.00 (INCI: Polyglyceryl-6 Caprylate; Polyglyceryl-3 Cocoate; Polyglyceryl-4 Caprate; Polyglyceryl-6 Ricinoleate) Glycerin 0.50 Sodium Chloride 1.00 Perfume, preservative q.s. Citric Acid, 30%-ig q.s. (pH 4.8)

Rinse-Off Conditioner

[0223]

TABLE-US-00025 Ingredient w/w-% Water ad 100.00 VARISOFT? EQ 65, Evonik Nutrition & Care GmbH, 2.00 (INCI: Distearoylethyl Dimonium Chloride; Cetearyl Alcohol) VARISOFT? BT 85, Evonik Nutrition & Care GmbH, 1.00 (INCI: Behentrimonium Chloride) Example 14 0.20 TEGO? Alkanol 1618, Evonik Nutrition & Care GmbH, 5.00 (INCI: Cetearyl Alcohol) Citric Acid, 30%-ig q.s. (pH 4.0) Preservative, Perfume q.s.

Rinse-Off Conditioner

[0224]

TABLE-US-00026 Ingredient w/w-% Water ad 100.00 TEGIN? M Pellets, Evonik Nutrition & Care GmbH, 1.00 (INCI: Glyceryl Stearate) TEGO? Care PSC 3, Evonik Nutrition & Care GmbH, 0.50 (INCI: Polyglyceryl-3 Dicitrate/Stearate) Jaguar C-162, Solvay, (INCI: Hydroxypropyl Guar 0.10 Hydroxypropyltrimonium Chloride) Example 6 1.00 TEGO? Alkanol 1618, Evonik Nutrition & Care GmbH, 6.00 (INCI: Cetearyl Alcohol) Citric Acid, 30%-ig q.s. (pH 4.5) Preservative, Perfume q.s.

Wet Wipes Impregnation Fluid

[0225]

TABLE-US-00027 Ingredient w/w-% Pentylene Glycol 2.0 Glycerin 1.0 TEGO? Solve 61 (Polyglyceryl-6 Caprylate; 2.0 Polyglyceryl-3 Cocoate; Polyglyceryl-4 Caprate; Polyglyceryl-6 Ricinoleate) Example 3 0.5 Allantoin 0.2 Maltodextrin 0.5 Chamomilla extract 0.1 Preservative q.s. Perfume q.s. Water ad 100.0 Citric Acid, 30% ad pH 5.5

Wet Wipes Impregnation Fluid

[0226]

TABLE-US-00028 Ingredient w/w-% TEGO? Solve 61 (Polyglyceryl-6 Caprylate; 1.5 Polyglyceryl-3 Cocoate; Polyglyceryl-4 Caprate; Polyglyceryl-6 Ricinoleate) TEGO? Solve 55 (Polyglyceryl-6 Caprylate; 1.0 Polyglyceryl-4 Caprate; Propylene Glycol) Example 2 0.2 Example 11 0.1 Preservative q.s. Perfume 0.1 Propanediol 3.0 Water ad 100.0

Cleansing Micellar Water

[0227]

TABLE-US-00029 Ingredient w/w-% Water ad 100.0 TEGOSOFT? PC 41 (Polyglyceryl-4 Caprate) 5.5 Preservative q.s. Example 6 0.3 Glycerin 1.0 Disodium EDTA 0.2 Citric Acid, 30% ad pH 5.5

Micellar Water

[0228]

TABLE-US-00030 Ingredient w/w-% REWOTERIC? AM C (Sodium Cocoamphopropionate) 3.0 Example 14 0.6 TEGOSOFT? GMC 6 (PEG-6 Caprylic/Capric Glycerides) 5.0 Water ad 100.0 Glycerin 8.0 Citric Acid ad pH 5.5 Preservative q.s.