Product comprising sophorolipids

The synergistic effect of Poloxamer 184 and sophorolipids in a micellar structure addresses the inefficiency of pigment removal in cosmetic cleansers, enhancing solubilization and skin cleansing efficacy.

WO2026046592A1PCT designated stage Publication Date: 2026-03-05BEIERSDORF AG
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Patent Information

Application Number
PCT/EP2025/071031
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-09-02
Filing Date
2025-07-22
Publication Date
2026-03-05

AI Technical Summary

Technical Problem

Existing cosmetic cleansing products often fail to effectively solubilize inorganic pigments, particularly CI 77491, leading to insufficient removal from the skin.

Method used

Aqueous cosmetic cleansing preparations containing Poloxamer 184 and sophorolipids, specifically lactonic or acidic sophorolipids, form a synergistic micellar structure that enhances the solubilization of inorganic pigments like CI 77491.

Benefits of technology

The combination of Poloxamer 184 and sophorolipids significantly improves the solubilization of CI 77491, ensuring effective removal without skin irritation.

✦ Generated by Eureka AI based on patent content.

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Abstract

A cosmetic product.
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Description

[0001] Product containing sophorolipids

[0002] The present invention relates to a cosmetic product comprising sophorolipids and poloxamer.

[0003] Cosmetic products generally serve not only to make one look beautiful and attractive, but also contribute significantly to increased self-esteem and well-being. Consumers often apply decorative cosmetics to improve their appearance. However, these products are removed from the skin in the evening before going to bed. Cosmetic cleansing products are used for this removal; these products offer particularly effective cleansing without causing skin irritation.

[0004] A typical category of these cleansing products are thin, water-based cosmetic preparations used to remove makeup. Well-known products, such as Nivea Micellar Water (GNPD registration number 11509114), contain micelles made of surfactants dissolved in the aqueous solution. The advantage of these products is that, due to their high water content, they are particularly gentle yet still allow for the removal of makeup from the skin without excessive friction.

[0005] Crucial to the product's success is the ability to effectively solubilize and remove the pigments typically found in makeup products from the skin. A well-known pigment often found in makeup products is the red dye CI 77491.

[0006] Well-known products often contain poloxamers to solubilize these pigments. Poloxamers are block copolymers of ethylene oxide and propylene oxide. They are low-foaming and foam-reducing nonionic surfactants used for dispersion and emulsification in the chemical and technical industries.

[0007] The problem is that often insufficient solubilization of these pigments is achieved.

[0008] Accordingly, one object of the present invention was to improve the solubilizability of pigments, in particular inorganic pigments, especially iron oxides, in particular CI 77491. This is intended to enable improved removal of these pigments from the skin.

[0009] Two-phase makeup removers are described, among other places, in WO 2016146360 A1. However, this document did not provide any reference to the present invention. Surprisingly, these problems have been solved by the present invention.

[0010] The present invention relates to an aqueous cosmetic cleansing preparation, advantageously having a micellar structure, comprising a) Poloxamer 184, and b) Sophorolipid.

[0011] Micellar structures, also known as association colloids, are aggregated molecular complexes of amphiphilic molecules or surfactants. Such micelles can be detected using a reverse CMC method. An undiluted sample is used for this purpose. The sample is diluted stepwise with water, and the surface tension is measured after each dilution step. By examining the recorded surface tension curve as a function of the cleaning agent concentration in water, a micellar structure can be identified if the surface tension no longer changes with increasing concentration of the cleaning agent. The measurement must be performed at 20°C sample temperature and ambient temperature. The CMC measurement can be performed using a Krüss K100 tensiometer.

[0012] Equipment:

[0013] Measuring body: Krüss standard ring

[0014] Radius: 9.545 mm

[0015] Wire diameter: 0.37 mm

[0016] Parameter:

[0017] Surface sensing speed: 10 mm / min

[0018] Surface detection sensitivity: 0.001 g

[0019] Immersion depth: 3.00 mm

[0020] Number of values: 30 (maximum)

[0021] Dilution: exponential

[0022] Flow rate: 34ml / min

[0023] After each dilution step, the sample was stirred for 180 seconds before the surface tension was measured. Surprisingly, it was found that the specific combination of the invention synergistically increases the solubilizability of pigments, particularly inorganic pigments, especially iron oxides, and in particular CI 77491.

[0024] The invention also relates to the use of the cleaning preparation according to the invention for removing make-up from human skin.

[0025] The invention also relates to the use of Poloxamer 184 and sophorolipid in a cosmetic aqueous cleansing preparation for the solubilization of pigments, in particular inorganic pigments, in particular iron oxides, in particular CI 77491, from human skin.

[0026] When the term preparation is used below, the statement always refers to the cleaning preparation according to the invention.

[0027] Unless otherwise stated, all tests and measurements were performed under "normal conditions". "Normal conditions" refers to 20°C, 1013 hPa, and 50% relative humidity.

[0028] The term "skin" refers exclusively to human skin.

[0029] Where weight percentages (wt%) are given below without reference to a specific composition or mixture, these percentages always refer to the total weight of the preparation. Where ratios of components / substances / groups of substances are disclosed below, these ratios refer to the weight ratios of the components / substances / groups of substances mentioned.

[0030] Where weight percentage ranges for the components of the preparation are specified below, the disclosure of the present application also includes all individual values ​​in steps of 0.1 wt.% within these weight percentage ranges.

[0031] The terms “according to the invention”, “advantageous according to the invention”, “advantageous in the sense of the present invention”, etc., always refer, within the scope of the present disclosure, to the preparation according to the invention as well as the use according to the invention and the method.

[0032] The term "free from" within the meaning of this disclosure means that the proportion of the substance in question does not exceed 0.1% by weight and, in particular, is 0% by weight based on the total weight of the preparation. Thus, accidental introduction through impurities should not lead to exclusion from the scope of protection. Emulsifiers are defined as all substances listed under the term "emulsifying agent" in the International Cosmetic Ingredient Dictionary and Handbook, Thirteenth Edition 2010 (ISBN 1-882621-47-6). Surfactants are defined as all substances listed under the term "surfactant" in the International Cosmetic Ingredient Dictionary and Handbook, Thirteenth Edition 2010 (ISBN 1-882621-47-6).

[0033] Any viscosity values ​​given in this disclosure refer to measurements taken at 25°C in a 150 ml wide-mouth bottle (VWR No.: 807-0001) using the Rheomat R 123 from proRheo. The Rheomat R 123 from proRheo GmbH is a rotational viscometer, meaning that a measuring element rotates within the substance being measured. The force required to rotate the measuring element within the sample at a predetermined speed is measured. The viscosity is then calculated from this torque, the rotational speed of the measuring element, and the geometric dimensions of the measuring system. The measuring element used is No. 1 (article no. 200 0191), suitable for a viscosity range up to 10,000 mPa·s and a rotational speed of 62.5 min⁻¹.

[0034] When this disclosure refers to an average, that average always refers to arithmetic means.

[0035] Any information regarding the molecular weight of polymers given in this disclosure refers to a measurement by means of light scattering.

[0036] Advantageously, the sophorolipid is used in a proportion of 0.0001 to 1 wt.%, preferably 0.05 to 0.5 wt.% and particularly preferably 0.075 to 0.3 wt.%, based on the total mass of the preparation.

[0037] Furthermore, it has been shown according to the invention that certain sophorolipids are particularly suitable for the application, as they form an even more effective synergism with poloxamer 184 in the solubilization of CI 77491. This is evident from the measurement data shown. It is particularly preferred if the invention is characterized in that the lactonic sophorolipid is included as the sophorolipid. The lactonic sophorolipid has CAS number 148409-20-5 and the chemical name 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoic acid 1',4"-lactone-6',6"-diacetate. When the term lactonic sophorolipid is used in the following disclosure, it describes the substance 17-L-[(2'-0-β-D-Glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoic acid 1',4"-lactone-6',6"-diacetate.A preferred object of the invention is therefore an aqueous cosmetic cleansing preparation, advantageously having a micellar structure comprising a) Poloxamer 184, and b) Lactonic sophorolipid.

[0038] Advantageously, the lactonic sophorolipid is used in a proportion of 0.0001 to 1 wt.%, preferably 0.05 to 0.5 wt.% and particularly preferably 0.075 to 0.3 wt.%, based on the total mass of the preparation.

[0039] Furthermore, it has been shown according to the invention that certain sophorolipids are particularly suitable for the application, as they form an even more effective synergism with poloxamer 184 in the solubilization of CI 77491. This is evident from the measurement data shown. It is particularly preferred if the invention is characterized in that the acidic sophorolipid is included. The acidic sophorolipid has the chemical name (E)-17-[(2R,3R,4S,5S',6R)-6-(acetyloxymethyl)-3-[(2S,3R,4S,5S,6R')-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxyoctadec-9-enoic acid. When the term acidic sophorolipid is used in the following disclosure, it refers to the substance (E)-17- [(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3-[(2S,3R',4S,5S,6 / : ? l )-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxyoctadec-9-enoic acid.

[0040] A preferred object of the invention is therefore an aqueous cosmetic cleansing preparation, advantageously having a micellar structure comprising a) Poloxamer 184, and b) an acidic sophorolipid.

[0041] Advantageously, the acidic sophorolipid is used in a proportion of 0.0001 to 1 wt.%, preferably 0.05 to 0.5 wt.% and particularly preferably 0.075 to 0.3 wt.%, based on the total mass of the preparation.

[0042] Advantageously, Poloxamer 184 is used in a proportion of 0.01 to 3.0 wt.%, preferably 0.05 to 2.5 wt.% and particularly preferably 0.2 to 1.3 wt.%, based on the total mass of the preparation.

[0043] It is further advantageous if the weight ratio of the sophorolipid to the poloxamer 184 is from 12:1 to 1:200, preferably from 10:1 to 1:20, preferably from 2:1 to 10:1, and particularly preferably from 1:3 to 1:7. It is further advantageous if the weight ratio of the lactonic sophorolipid to the poloxamer 184 is from 10:1 to 1:20, preferably from 2:1 to 10:1, and particularly preferably from 1:3 to 1:7.

[0044] Advantageously, the preparation according to the invention has only a small oil phase or no oil phase at all. If an oil phase is advantageously included, it is preferred that the oil phase constitutes less than 2 wt.%, preferably less than 1.0 wt.%, preferably less than 0.8 wt.%, preferably less than 0.6 wt.%, preferably less than 0.4 wt.%, preferably less than 0.2 wt.%, and particularly preferably less than 0.1 wt.%. It is particularly preferred if the proportion of the oil phase is 0.0 wt.%. Consequently, it is advantageous if no oil phase is included. By definition, emulsifiers and surfactants are not included in the quantity of the oil phase.

[0045] Furthermore, it is advantageous if the preparation is characterized by the fact that it comprises sodium chloride. If sodium chloride is included, it is preferred if the proportion of sodium chloride is 0.01 to 0.1 wt.%, preferably 0.02 to 0.05 wt.%, based on the total weight of the preparation.

[0046] Furthermore, it is advantageous in the context of the present invention if the preparation is characterized by comprising glycerin. If glycerin is included, it is advantageous if it is present in a proportion of 0.1 to 5 wt.%, preferably 0.8 to 2.5 wt.%, and particularly preferably 0.9 to 1.2 wt.%, based on the total weight.

[0047] Furthermore, it is advantageous in the context of the present invention if the preparation is characterized in that it comprises 1,2-hexanediol. If 1,2-hexanediol is included, it is advantageous if it is present in a proportion of 0.1 to 5 wt.%, preferably 0.2 to 1.5 wt.%, and particularly preferably 0.3 to 0.8 wt.%, based on the total weight.

[0048] Furthermore, it is advantageous in the context of the present invention if the preparation is characterized by comprising phenoxyethanol. If phenoxyethanol is included, it is advantageous if it is present in a proportion of 0.1 to 5 wt.%, preferably 0.2 to 1.5 wt.%, and particularly preferably 0.3 to 0.8 wt.%, based on the total weight.

[0049] It is further advantageous within the meaning of the present invention if the preparation is characterized in that it has a pH value in the range of 4.0 to 8.5, preferably in the range of 6.0 to 8.0, more preferably in the range of 6.5 to 7.5, and particularly preferably in the range of 6.8 to 7.2. To adjust the pH value, it is advantageous to use sodium hydroxide or citric acid or their salts.

[0050] According to the invention, it is still possible and also preferred if the preparation comprises one or more further surfactants.

[0051] For example, it is advantageous if at least one cationic surfactant is included. Quaternary surfactants with a positive charge are advantageously chosen as cationic surfactants. Quaternary surfactants contain at least one nitrogen atom covalently bonded to four alkyl and / or aryl groups. This results in a positive charge, regardless of the pH value. Advantageous quaternary surfactants include alkyl betaine, alkylamidopropyl betaine, and alkylamidopropyl hydroxysulfaine.Cationic surfactants can further preferably be selected, in accordance with the present invention, from the group of quaternary ammonium compounds, in particular benzyltrialkylammonium chlorides or bromides, such as benzyldimethylstearylammonium chloride, furthermore alkyltrialkylammonium salts, for example, cetyltrimethylammonium chloride or bromide, alkyldimethylhydroxyethylammonium chlorides or bromides, dialkyldimethylammonium chlorides or bromides, alkylamidethyltrimethylammonium ether sulfates, alkylpyridinium salts, for example, laurylpyrimidinium or cetylpyrimidinium chloride, imidazoline derivatives and compounds with cationic character such as amine oxides, for example, alkyldimethylamine oxides or alkylaminoethyldimethylamine oxides. The use of cetyltrimethylammonium salts is particularly advantageous. The inclusion of cetyltrimethylammonium chloride is especially preferred.

[0052] If a cationic surfactant is included, it is preferred that the proportion of cationic surfactants is 0.01 to 0.4 wt.%, preferably 0.015 to 0.2 wt.% and particularly preferably 0.02 to 0.1 wt.%, based on the total weight of the preparation.

[0053] If cetyltrimethylammonium chloride is included, it is preferred that the proportion of cetyltrimethylammonium chloride is from 0.01 to 0.4 wt.%, preferably from 0.015 to 0.2 wt.% and particularly preferably from 0.02 to 0.1 wt.%, based on the total weight of the preparation.

[0054] Furthermore, it is preferred if at least one anionic surfactant is included. If at least one anionic surfactant is included, it is preferred if the total proportion of anionic surfactants is 0.01 to 0.5 wt.%, preferably 0.03 to 0.3 wt.%, and particularly 0.06 to 0.2 wt.%, based on the total weight of the preparation. In general, it is preferred if the proportion of the other surfactants is less than 1.5 wt.%, preferably less than 1.1 wt.%, and particularly preferably less than 0.9 wt.%, based on the total weight of the preparation.

[0055] Furthermore, it is advantageous if the preparation is characterized in that it contains water in a proportion of at least 85 wt.%, preferably at least 90 wt.% and particularly preferably at least 95 wt.%, the figures referring to the total weight of the preparation.

[0056] Furthermore, the preparation according to the invention can comprise additional ingredients which are commonly contained in such formulations. Such ingredients are colorants, active ingredients, moisturizing agents, complexing agents, and / or preservatives.

[0057] Examples

[0058] The following example recipes are intended to illustrate the present invention. Numerical values ​​refer to weight percentages based on the total mass of the preparation.

[0059] Example formulations 2 and 4 are examples according to the invention. The remaining examples listed in the first table are comparative examples not according to the invention. The example formulations already contain the pigment CI 77491 for the follow-up test. According to the invention, the examples are provided without the aforementioned pigment, with the amount being compensated for by water.

[0060] 20 g of sample, as described in the examples in the table above, were prepared and stirred using a magnetic stirrer until an optically homogeneous liquid was obtained. 3 ml of sample were then immediately transferred to a LUMiFuge cuvette. The transmission from the bottom of the cuvette was measured at 200 l / min, approximately 4.7 g at a temperature of 25 °C, for up to 180 min. The integral transmission in % is shown in the table. The measurements were performed using a LUMiFuge 116 instrument. The measurement wavelength was set to 880 nm.

[0061] The transmission values ​​indicate how long the pigments remain solubilized in the sample. That is, the lower the transmission, the more pigment is solubilized and the better the solution properties of the formula.

[0062] Figure 1 shows the transmission of the samples in % on the Y-axis and the time in seconds on the X-axis. Example 1 shows the highest transmission over the entire time period. This means that this sample provides the poorest solubilization of CI 77491. Examples 3 and 5 show the samples containing only a sophorolipid. When combinations of poloxamer and sophorolipid are used, a synergistic improvement in the solubilization of CI 77491 is observed. The combination with the acidic sophorolipid is particularly effective.

[0063] Further example recipes:

Claims

Claims 1. Aqueous cleaning preparation, advantageously having a micellar structure, comprising a) Poloxamer 184, and b) Sophorolipid.

2. Preparation according to claim 1 characterized in that an acidic sophorolipid is included as the sophorolipid.

3. Preparation according to claim 1 characterized in that the sophorolipid is contained in a proportion of 0.0001 to 1 wt.%, preferably 0.05 to 0.5 wt.% and particularly preferably 0.075 to 0.3 wt.%, based on the total mass of the preparation.

4. Preparation according to one of the preceding claims characterized in that an acidic sophorolipid is included as the sophorolipid, wherein the proportion of the acidic sophorolipid is from 0.0001 to 1 wt.%, preferably from 0.05 to 0.5 wt.% and particularly preferably from 0.075 to 0.3 wt.%, based on the total mass of the preparation.

5. Preparation according to one of the preceding claims characterized in that the poloxamer 184 is contained in a proportion of 0.01 to 3.0 wt.%, preferably 0.05 to 2.5 wt.% and particularly preferably 0.2 to 1.3 wt.%, based on the total mass of the preparation.

6. Preparation according to one of the preceding claims characterized in that the weight ratio of the sophorolipid to the poloxamer 184 is from 12:1 to 1:200, preferably from 10:1 to 1:20, preferably from 2:1 to 10:1 and particularly preferably from 1:3 to 1:

7.

7. Preparation according to one of the preceding claims characterized in that the preparation does not contain an oil phase.

8. Preparation according to one of claims 1 to 6 characterized in that an oil phase is included in the preparation, wherein it is preferred if the oil phase constitutes less than 2 wt.%, preferably less than 1.0 wt.%, preferably less than 0.8 wt.%, preferably less than 0.6 wt.%, preferably less than 0.4 wt.%, preferably less than 0.2 wt.% and particularly preferably less than 0.1 wt.%.

9. Preparation according to one of the preceding claims characterized in that the preparation comprises sodium chloride.

10. Preparation according to claim 9 characterized in that the proportion of sodium chloride is 0.01 to 0.1 wt.%, preferably 0.02 to 0.05 wt.%, based on the total weight of the preparation.

11. Preparation according to one of the preceding claims characterized in that the preparation comprises at least one cationic surfactant, preferably containing cetyltrimethylammonium chloride.

12. Preparation according to claim 11 characterized in that the proportion of cationic surfactants is 0.01 to 0.4 wt.%, preferably 0.015 to 0.2 wt.% and particularly preferably 0.02 to 0.1 wt.%, based on the total weight of the preparation.

13. Preparation according to one of the preceding claims characterized in that it further contains at least one anionic surfactant, wherein it is preferred that the total proportion of these anionic surfactants is 0.01 to 0.5 wt.%, preferably 0.03 to 0.3 wt.% and in particular 0.06 to 0.2 wt.%, based on the total weight of the preparation.

14. Preparation according to one of the preceding claims characterized in that water is contained in a proportion of at least 85 wt.%, preferably at least 90 wt.% and particularly preferably at least 95 wt.%, wherein the values ​​refer to the total weight of the preparation.

15. Use of the preparation according to any of the preceding claims for removing make-up from human skin.

16. Use of Poloxamer 184 and sophorolipid, in particular an acidic sophorolipid, in a cosmetic aqueous cleansing preparation for the solubilization of pigments, in particular inorganic pigment, in particular iron oxides, in particular CI 77491, from human skin.

Citation Information

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