Compositions comprising ceramides, polyglycerol carboxylates, and cholesterol

Abstract

This invention relates to compositions comprising at least one ceramide, at least one polyglycerol carboxylate, and cholesterol in a specific weight ratio.

Description

Invention Field

[0001] This invention relates to compositions comprising at least one ceramide, at least one polyglycerol carboxylate, and cholesterol in a specific weight ratio. Existing technology

[0002] EP3117821 discloses a method for preparing a ceramide dispersion composition, wherein a mixture of ceramide, nonionic surfactant and polyol is heated to a temperature equal to or higher than 100°C.

[0003] EP2295032 discloses a ceramide dispersion comprising a natural ceramide and at least one surfactant, wherein the ceramide dispersion in the at least one surfactant comprises at least one polyglycerol fatty acid ester having an HLB of 10 to 16.

[0004] EP975325 discloses a composition for topical application comprising a combination of a free sphingoid base and a ceramide.

[0005] US8710034 discloses a composition comprising ceramides and cholesterol for improving the skin barrier function.

[0006] US2006198800A1 discloses a skin care composition comprising: a safe and effective amount of at least one anti-wrinkle agent and a safe and effective amount of a natural peeling complex.

[0007] The object of this invention is to provide a ceramide-containing composition that further improves the cosmetic properties of the ceramide present.

[0008] Invention Description

[0009] It has been surprisingly found that the composition described in claim 1 is able to solve the problems that this invention aims to address.

[0010] Therefore, the present invention relates to a composition comprising at least one ceramide, at least one polyglycerol carboxylate, and cholesterol in a specific weight ratio.

[0011] The present invention also relates to the use of the compositions according to the invention for increasing the barrier function of the skin.

[0012] One advantage of the present invention is that, compared with ceramide-containing compositions according to the prior art, the compositions according to the present invention have improved storage stability, and therefore their properties change more slowly over time, especially in terms of viscosity.

[0013] Another advantage of the present invention is that, compared with ceramide-containing compositions according to the prior art, the compositions according to the present invention can withstand a greater number of freeze-thaw steps without significant viscosity loss.

[0014] One advantage of the compositions according to the invention is that the compositions in the formulation have excellent sensory properties, which result in improved skin sensation and / or hair sensation.

[0015] Another advantage of the composition according to the invention is that the composition in the formulation stimulates the proliferation of human follicular dermal papillary cells (HFDPC) in vitro, which is equivalent to stimulating hair growth in vivo.

[0016] Another advantage of the compositions according to the invention is that the compositions in the formulation have improved dispersibility compared to individual components.

[0017] Another advantage of the compositions according to the invention is that the composition in the formulation has improved absorption compared to the individual components.

[0018] Another advantage of the compositions according to the invention is that the composition in the formulation has reduced oiliness compared to the individual components.

[0019] Another advantage of the composition according to the invention is that the composition in the formulation has reduced wax content compared to the individual components.

[0020] Another advantage of the compositions according to the invention is that the compositions in the formulation have improved glidability compared to the individual components.

[0021] Another advantage of the composition according to the invention is that the composition in the formulation has reduced tackiness compared to the individual components.

[0022] Another advantage of the composition according to the invention is that the composition in the formulation has improved silkiness / velvetiness compared to the individual components.

[0023] Another advantage of the composition according to the invention is that it improves skin roughness and skin smoothness more effectively than ceramide-containing compositions according to the prior art.

[0024] Another advantage of the compositions according to the invention is that they regenerate the barrier damaged by SDS more effectively than ceramide-containing compositions according to the prior art.

[0025] In the context of this invention, the term "ceramide" should be understood to mean an acylated sphingosine base, wherein the sphingosine base is preferably selected from sphingosine, dihydrosphingosine, 6-hydroxysphingosine, and phytosphingosine.

[0026] In connection with this invention, “pH” is defined as the value of the relevant composition measured at 22°C after stirring for five minutes using a pH electrode calibrated according to ISO 4319 (1977).

[0027] The polyglycerol carboxylate present according to the present invention is a mixture of different substances; therefore, it will be clear to those skilled in the art that the specified values ​​are average values ​​for the mixture.

[0028] In the context of this invention, the term "polyglycerol" should be understood to mean polyglycerol that may also contain glycerol. Therefore, any glycerol fraction should also be considered for the purposes of calculation, mass, etc. Due to its polymerization properties, polyglycerol is a statistical mixture of many compounds. Polyglycerol can have ether bonds formed between two primary sites, one primary site and one secondary site, or two secondary sites of the glycerol monomer. For this reason, the basic framework of polyglycerol is generally not composed solely of linearly linked glycerol units, but may also contain branches and rings. For details, see, for example, "Original synthesis of linear, branched and cyclic oligoglycerol standards", Cassel et al., J. Org. Chem. 2001, 875-896.

[0029] This also applies to the term "polyglycerol carboxylate" in connection with this invention.

[0030] Unless otherwise stated, all percentages (%) given are mass percentages.

[0031] Therefore, the present invention relates to a composition comprising

[0032] A) At least one ceramide,

[0033] B) at least one polyglycerol carboxylate, and

[0034] C) Cholesterol and / or at least one cholesterol derivative selected from cholesterol sulfate, particularly potassium salts of cholesterol sulfate (potassium cholesteryl sulfate), cholesterol hydrogen succinate, and 7-dehydrocholesterol, preferably in a total amount of 0.1% to 3.0% by weight, more preferably 0.1% to 2.0% by weight, particularly preferably 0.2% to 1.0% by weight, wherein the weight percentages are relative to the total composition.

[0035] Its features

[0036] The weight ratio of all present ceramides to the sum of present cholesterol and / or at least one cholesterol derivative is 1:0.1 to 1:0.9, preferably 1:0.1 to 1:0.8, and particularly preferably 1:0.2 to 1:0.7.

[0037] The preferred composition according to the invention is characterized in that

[0038] The weight ratio of all present ceramides to all present polyglycerol carboxylates is 1:1 to 1:30, preferably 1:1 to 1:25, and particularly preferably 1:2 to 1:20.

[0039] According to a preferred embodiment of the invention, the composition according to the invention is characterized in that it comprises

[0040] D) At least one sphingosine base, preferably selected from sphingosine, dihydrosphingosine, 6-hydroxysphingosine, N-acetylphytosphingosine, and phytosphingosine, especially phytosphingosine.

[0041] According to the invention, component D) is preferably present in an amount of 0.01% to 2.0% by weight, preferably 0.02% to 1% by weight, and particularly preferably 0.02% to 0.8% by weight, based on the total composition according to the invention.

[0042] According to the present invention, in the composition according to the present invention, the weight ratio of component A) to component D) is preferably 1:1 to 1:0.01, more preferably 1:0.8 to 1:0.02, and particularly preferably 1:0.7 to 1:0.05.

[0043] According to a preferred embodiment of the invention, the composition according to the invention is characterized in that it comprises

[0044] E) At least one free fatty acid, preferably selected from fatty acids with a chain length of 12 to 40, more preferably 14 to 24, and particularly preferably 16 to 22 carbon atoms.

[0045] According to the invention, component E) is preferably present in an amount of 0.01% to 3.0% by weight, preferably 0.05% to 2.0% by weight, and particularly preferably 0.1% to 1.0% by weight, based on the total composition according to the invention.

[0046] According to the present invention, in the composition according to the present invention, the weight ratio of component B) to component E) is preferably 1:0.001 to 1:1, more preferably 1:0.01 to 1:0.5, and particularly preferably 1:0.02 to 1:0.1.

[0047] According to the present invention, the composition is characterized in that it comprises 20% to 99% by weight, preferably 40% to 97% by weight, and particularly preferably 50% to 95% by weight of water based on the total composition.

[0048] The preferred composition according to the invention is an active ingredient concentrate with a high content of active ingredients; such a preferred composition according to the invention is characterized in that the composition contains components A), B) and C) in a total amount of 1.0% to 25% by weight, preferably 2.0% to 20% by weight, particularly preferably 4.0% to 15% by weight, based on the total composition.

[0049] The preferred composition according to the present invention contains at least two ceramides, preferably at least three ceramides, and particularly preferably exactly three ceramides.

[0050] The ceramides preferably present in the compositions according to the invention are selected from ceramide NP, ceramide AP, ceramide EOP, ceramide NDS, ceramide ADS, ceramide EODS, ceramide NS, ceramide AS, ceramide EOS, ceramide NH, ceramide AH and ceramide EOH, and more preferably from ceramide NP, ceramide AP, ceramide NS, ceramide EOP and ceramide EOS.

[0051] The preferred composition according to the invention is characterized in that the polyglycerol carboxylate of component B is composed of polyglycerol with a degree of polymerization of 2.0 to 25, preferably 2.5 to 20, and particularly preferably 3.0 to 15.

[0052] The degree of polymerization N of polyglycerol is calculated using the following formula based on its hydroxyl value (OHN, expressed as mg KOH / g):

[0053]

[0054] Appropriate methods for determining hydroxyl values ​​are particularly those according to DGF CV 17a(53), Ph.Eur.2.5.3Method A and DIN53240.

[0055] A preferred feature of the composition of the present invention is that the polyglycerol carboxylate of component B) is composed of at least one carboxylic acid selected from fatty acids, wherein the fatty acid has 12 to 26, preferably 14 to 24, and particularly preferably 16 to 22 carbon atoms.

[0056] A preferred feature of the composition of the present invention is that the polyglycerol carboxylate of component B) does not contain any dicarboxylic acid (preferably any polycarboxylic acid) esterified into the polyglycerol carboxylate.

[0057] Fatty acids are typically unbranched and contain an even number of carbon atoms. Any double bond has a cis configuration. Examples of fatty acids are: hexanoic acid, octanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, isostearic acid, stearic acid, 12-hydroxystearic acid, dihydroxystearic acid, oleic acid, linoleic acid, linolenic acid, phellandral acid, leucine, arachidic acid, benzyl acid, erucic acid, codoleic acid, linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, and arachidonic acid.

[0058] According to the present invention, at least one carboxylic acid of the polyglycerol carboxylate constituting component B) is particularly preferably selected from palmitic acid, stearic acid and benzyl acid.

[0059] According to the invention, the polyglycerol carboxylate of component B) is particularly preferred to be composed of a mixture of fatty acids, especially a mixture of at least two selected from palmitic acid, stearic acid and betaine acid, wherein the sum of these comprises at least 60% by weight, preferably at least 75% by weight, and even more preferably at least 85% by weight, based on all fatty acids present in the mixture. In this respect, according to the invention, the weight ratio of palmitic acid to stearic acid to betaine acid is particularly preferred to be 1.0:3.0 to 1.0:3.0 to 1.0, preferably 1.2:2.1 to 1.4:2.4 to 1.0.

[0060] According to the invention, the polyglycerol carboxylates present in component B) can be provided by mixing different separately obtained polyglycerol carboxylates. Thus, for example, by mixing polyglycerol palmitate with polyglycerol betaine.

[0061] According to the present invention, the polyglycerol carboxylate present in component B) is preferably characterized by having a saponification value of 20 to 199 mg KOH / g, preferably 30 to 100 mg KOH / g, and particularly preferably 40 to 70 mg KOH / g.

[0062] This ensures excellent dispersion stability.

[0063] The saponification value was determined by a person skilled in the art according to DGF CV 3 or DIN EN ISO 3681.

[0064] Preferred compositions according to the invention, particularly formulations, especially in the form of cosmetic formulations, pharmaceutical formulations or dermatological formulations.

[0065] Formulations can be prepared by mixing the above-mentioned active ingredient concentrate, wherein the concentration of the active ingredient is reduced compared to the above-mentioned concentrate; the preferred alternative composition according to the invention is characterized in that it contains components A), B) and C) in a total amount of 0.01% to 1.25% by weight, preferably 0.01% to 1.00% by weight, particularly preferably 0.02% to 1.00% by weight based on the total composition, and is particularly preferred as a cosmetic formulation, pharmaceutical formulation or dermatological formulation.

[0066] The formulations according to the invention may further comprise at least one additional component selected from the following:

[0067] Moisturizer

[0068] Emulsifier,

[0069] Thickener / viscosity modifier / stabilizer

[0070] UV light protection filters

[0071] Antioxidants

[0072] Water-soluble growth promoters (or polyols),

[0073] Solids and fillers

[0074] Film-forming agent,

[0075] Pearlescent additives

[0076] Deodorant and antiperspirant active ingredients,

[0077] Insect repellent,

[0078] Self-tanning agent

[0079] preservative,

[0080] Conditioner,

[0081] Spices,

[0082] dye,

[0083] Odor absorbent

[0084] Cosmetic active ingredients

[0085] Nursing additives

[0086] Superfatting agent

[0087] Solvent.

[0088] Substances that can be used as exemplary representatives of each group are known to those skilled in the art and can be found, for example, in German application DE 102008001788.4. This patent application is hereby incorporated by reference and thus forms part of this disclosure.

[0089] For information on other optional components and their amounts, please refer in particular to relevant manuals known to those skilled in the art, such as K. Schrader, "Grundlagen und Rezepturen der Kosmetika [Cosmetics-fundamentals and formulations]", 2nd edition, pp. 329-341, Hüthig Buch VerlagHeidelberg.

[0090] The specific amount of additives is determined by the intended use.

[0091] Typical boundary formulations for various applications are known existing technologies and are included in manufacturers' manuals, such as those for specific base materials and active ingredients. These existing formulations can generally be used without modification. However, if necessary, modifications can be made for adjustment and optimization without complicating the process through simple testing.

[0092] The preferred composition of the present invention is an emulsion, particularly an oil-in-water emulsion.

[0093] The composition particularly preferred according to the invention is characterized in that the pH of the composition is 4.0 to 8.0, preferably 4.5 to 7.4, and particularly preferably 5.0 to 7.2.

[0094] The present invention also relates to the use of the compositions according to the invention for increasing the barrier function of the skin.

[0095] The embodiments listed below illustrate the invention by way of example, and are not intended to limit the invention to the implementations specified in the embodiments. The scope of the invention is obvious from the description and claims as a whole.

[0096] The following figures form part of the embodiments:

[0097] Figure 1 The concentration of LDH in the skin model supernatant was measured 24 hours after the test formulation was applied to a skin model previously damaged by SDS.

[0098] Figure 2Interleukin-1α concentration in the supernatant of the skin model was measured 24 hours after the test formulation was applied to a skin model previously damaged by SDS.

[0099] Figure 3 This figure shows the difference in the SEsm parameter relative to the initial value T0. A decrease in SEsm corresponds to an improvement in skin smoothness.

[0100] Figure 4 The figure shows the difference in roughness parameter relative to the initial value T0 one week after the application of the test formulation.

[0101] Figure 5 The figure shows the difference in roughness parameter relative to the initial value T0 two weeks after the application of the test formulation. Example

[0102] The embodiments of this invention are marked with *.

[0103] Example 1: Synthesis of the polyglycerol carboxylates used (polyglycerol-6 esterified with C16-, C18- and C22-carboxylates)

[0104] A mixture of commercially available polyglycerol-6 (Spiga Nord SpA; 245.0 g, hydroxyl value = 980 mg KOH / g), an industrial-grade mixture of stearic acid and palmitic acid (79.0 g, acid value = 207 mg KOH / g, C16 / C18: 0~47:53), benzalkonium chloride (28.3 g, acid value = 165.5 mg KOH / g), and Na2CO3 (2.0 g) was heated to 240°C for 3 hours under nitrogen atmosphere. The mixture was then stirred at this temperature, and the generated water was continuously removed until an acid value ≤1.0 was achieved. The saponification value of the resulting product was 61 mg KOH / g.

[0105] Example 1b: Synthesis of the polyglycerol carboxylates used (polyglycerol-6 esterified with C16- and C18-carboxylates)

[0106] A mixture of commercially available polyglycerol-6 (Spiga Nord SpA; 223.7 g, hydroxyl value = 980 mg KOH / g), an industrial-grade mixture of stearic acid and palmitic acid (79.0 g, acid value = 207 mg KOH / g, C16 / C18: 0~47:53), and Ca(OH)2 (15 mg) was heated to 240°C for 3 hours under nitrogen atmosphere. The mixture was then stirred at this temperature, and the generated water was continuously removed until an acid value ≤1.0 was achieved. The saponification value of the resulting product was 69 mg KOH / g.

[0107] Example 1c: Synthesis of the polyglycerol carboxylates used (polyglycerol-10 esterified with C16- and C18-carboxylates)

[0108] A mixture of commercially available polyglycerol-10 (Spiga Nord SpA; 283.9 g, hydroxyl value = 898 mg KOH / g), an industrial-grade mixture of stearic acid and palmitic acid (79.0 g, acid value = 207 mg KOH / g, C16 / C18: 0~47:53), benzalkonium chloride (28.3 g, acid value = 165.5 mg KOH / g), and Na2CO3 (2.7 g) was heated to 240°C for 3 hours under nitrogen atmosphere. The mixture was then stirred at this temperature, and the generated water was continuously removed until an acid value ≤1.0 was achieved. The saponification value of the resulting product was 58 mg KOH / g.

[0109] Example 1d: Synthesis of the polyglycerol carboxylates used (polyglycerol-10 esterified with C8-, C10-, C16- and C18-carboxylates)

[0110] A mixture of commercially available polyglycerol-10 (Spiga Nord SpA; 310.0 g, hydroxyl value = 898 mg KOH / g), an industrial-grade mixture of stearic acid and palmitic acid (79.0 g, acid value = 207 mg KOH / g, C16 / C18: 0~47:53), benzalkonium chloride (28.3 g, acid value = 165.5 mg KOH / g), an industrial-grade mixture of octanoic acid and capric acid (5.00 g, acid value = 362 mg KOH / g, C8 / C10~58:42), and Na2CO3 (32.0 g) was heated to 240°C for 3 hours under nitrogen atmosphere. The mixture was then stirred at this temperature, and the generated water was continuously removed until an acid value ≤1.0 was achieved. The saponification value of the resulting product was 57 mg KOH / g.

[0111] Example 2: Regeneration of damaged skin barrier

[0112] The following formulations are used; Example A is an embodiment of the present invention, and Example B corresponds to the prior art described in Example 9 of US2006198800.

[0113] Example A (w / w%)* Example B (w / w%) Polyglycerol from Example 1 6.0 Sodium lauroyl lactyl lactate 10 Ceramide EOP 0.001 0.001 Ceramide NP 1 1 Ceramide AP 0.5 0.5 cholesterol 0.5 0.5 Phytosphingosine 0.5 0.5 Saccharin 0.5 preservative qs qs water Up to 100.0 Up to 100.0

[0114] The following tests were performed on epidermal skin models (EpiCS, SkinInVitro, Troisdorf). These three-dimensional skin models consisted of the epidermis, proliferating keratinocytes, and stratum corneum, possessing intact barrier function. To investigate the regenerative effect of the test formulation on the damaged skin barrier, the skin models were damaged with a 0.325% sodium dodecyl sulfate aqueous solution (SDS) for 40 minutes. The test formulation was then applied. The test formulations used were Examples A* and B, at concentrations of 0.1%, 0.3%, and 0.5% in water. The medium was also tested. This was ultrapure water. The application duration was 1 hour.

[0115] The medium changes after administration. The supernatant is removed the next day. This supernatant is used to quantify lactate dehydrogenase (LDH) and interleukin-1α. LDH is released, especially when cell membranes are damaged. Interleukin-1α is a protein expressed by cells during inflammation.

[0116] Figure 1 The results show LDH concentrations 24 hours after application of the test formulation to a skin model previously damaged by SDS. Damage to the skin barrier caused by sodium lauryl sulfate (SLS) dramatically increased LDH enzyme concentrations. This increase was reduced by both test formulations. The mediator (SDS + mediator) did not show this effect. It is quite clear that the reduction induced by Example A of the present invention is more significant than the reduction induced by Example B of the prior art.

[0117] Figure 2 The concentration of interleukin-1α (IL-1α) is shown 24 hours after application of the test formulation to a skin model previously damaged by SDS. Damage to the skin barrier by SDS initiates an inflammatory process, as evidenced by a sharp increase in IL-1α concentration. The mediator (ultrapure water) cannot terminate this inflammatory process (SDS + mediator), and the expression of the inflammatory marker IL-1α was significantly reduced in skin models treated with both test formulations after SDS damage. In Example A, this returned to the level of the undamaged skin model (mediator); in Test Formulation B, IL-1α expression was also significantly reduced, but significantly higher than in Example A.

[0118] The skin model tests described above show that both test formulations can repair the damage to the skin barrier caused by sodium lauryl sulfate, but Embodiment A of the present invention shows a significant advantage over the prior art Embodiment B.

[0119] Example 3: In vivo study of dry skin

[0120] In this study, 40 volunteers with dry skin participated. Volunteers either received two test formulations, which were applied to the left and right inner forearms, or they received one test formulation, which was applied to one forearm while the other forearm remained untreated (control). Test formulations and controls were assigned randomly, but all test formulations and controls were tested on 20 volunteers each.

[0121] Volunteers were instructed to use only the test formulation during the study. However, normal cleaning / showering was permitted.

[0122] The test formulation was applied twice daily over a two-week period. Images of the inner forearm were recorded before application, one week later, and two weeks later. A Visioscan VC 98 camera from CK electronic GmbH was used for this purpose. This is a specific camera that records magnified black-and-white images of the skin surface. The roughness parameters R1, R2, R3, R4, and R5, as well as the SEsm parameter (skin smoothness), were then determined using integrated software based on the grayscale distribution in the images. This parameter is proportional to the width and shape of the wrinkles. A more detailed description of how to calculate this parameter can be found in the Visioscan VC 98 camera manual, version "VC 98english FireWire04 / 2005DK".

[0123] If skin smoothness improves, the SEsm parameter will inevitably decrease.

[0124] The roughness parameters R1, R2, R3, R4, and R5 are initially derived from the metal industry and defined as Ra-Rz in DIN 4762-4768. In Visioscan software, these results are expressed as exponents (in grayscale) and correlated with the initial Ra-Rz value. The parameters have the following meanings:

[0125] parameter name DIN name R1 Roughness depth Rt R2 Maximum roughness depth Rmax R3 Average roughness depth Rz R4 Smoothness depth Rp R5 Arithmetic mean roughness Ra

[0126] To determine the effectiveness of the test formulation, for each volunteer, the difference between the parameter and the initial value after one and two weeks (T1-T0, T2-T0) was determined, and the average value of the 20 volunteers was calculated.

[0127] The table below shows the composition of the test formulation. This is an O / W emulsion based on commercially available cosmetic raw materials. The preparation of the formulation requires the following steps:

[0128] 1. Heat phase A and phase B to 70°C.

[0129] 2. Add phase B to phase A without stirring.

[0130] 3. Then homogenize the mixture.

[0131] 4. Cool the emulsion to 60°C with stirring and add phase C.

[0132] 5. Briefly homogenize the mixture again.

[0133] 6. Cool the emulsion further to 30°C with stirring. Below 40°C, add phases D, E, and F.

[0134] Table 1: Test formulations used in in vivo studies

[0135] Figure 3 The results for skin smoothness are presented. The medium, i.e., the formulation base without active ingredients, does not improve skin smoothness; on the contrary, it worsens it. Only the test formulation containing Example A of the present invention improved skin smoothness, while the test formulation containing Example B had almost no effect on skin smoothness.

[0136] Under the given roughness parameters, both test formulations reduced skin roughness, while the medium showed no effect. After one and two weeks of continuous application, formulation A according to the invention improved skin roughness more significantly than formulation B of the prior art.

[0137] Summary of findings: In conclusion, the results of the in vivo study indicate that Example A of the present invention shows improved efficacy compared to Example B of the prior art in improving skin smoothness and reducing skin roughness in volunteers with dry skin.

[0138] Other formulations according to the present invention are as follows:

[0139]

[0140]

[0141] The formulation is prepared as follows:

[0142] Phase A and phase C are heated to 90°C. Phase A is then added to phase C with stirring. The preemulsion is then homogenized, for example, using Ultra Turrax. The emulsion is cooled to 40°C with gentle stirring and a preservative is added. The mixture is then further cooled to 30°C with stirring.

[0143] Example 4: Emulsion stability

[0144] Prepare the following formulations as follows:

[0145] Polyglycerol ester, ceramide, phytosphoside, benzyl acid, glyceryl monostearate, cetearyl alcohol, and triethyl citrate were heated to 85°C (phase A). Water was also heated to 85°C. Phase A was then added to the water with stirring. The pre-emulsion was then homogenized using a rotor-stator homogenizer. The emulsion was cooled to 30°C with gentle stirring, and sodium levulinate and potassium sorbate were added.

[0146] Example A (w / w%)* Example B (w / w%) Polyglycerol from Example 1 6.0 Sodium lauroyl lactyl lactate 10 Ceramide EOP 0.001 0.001 Ceramide NP 1 1 Ceramide AP 0.5 0.5 cholesterol 0.5 0.5 Phytosphingosine 0.5 0.5 Saccharin 0.5 preservative qs qs water Up to 100.0 Up to 100.0

[0147]

[0148]

[0149] 1) Acid value = 1.7 mg KOH / g; Saponification value = 160 mg KOH / g.

[0150] 2) 17 (Evonik)

[0151] 3) W(Evonik)

[0152] 4) Acid value = 1.3 mg KOH / g; Saponification value = 141 mg KOH / g.

[0153] 5) PDI (Evonik)

[0154] 6) GPS (Evonik)

[0155] Formulations 18 to 21 formed a uniform and stable layered dispersion. It was found that formulations 22 to 27 exhibited non-uniformity and immediate phase separation when using a rotor-stator homogenizer.

Claims

1. A composition comprising A) At least one ceramide, B) At least one polyglycerol carboxylate, free from any dicarboxylic acid esterified into the polyglycerol carboxylate, wherein the polyglycerol carboxylate of component B) comprises polyglycerol with a degree of polymerization of 3.0 to 15 and at least one carboxylic acid selected from fatty acids having 12 to 26 carbon atoms, and the polyglycerol carboxylate of component B) comprises a mixture of at least two selected from palmitic acid, stearic acid, and betaine acid, wherein the sum of these is based on all fatty acids present in the mixture comprising at least 60% by weight. C) Cholesterol and / or at least one cholesterol derivative selected from cholesterol sulfate, cholesterol monosuccinate, and 7-dehydrocholesterol, wherein the cholesterol and / or at least one cholesterol derivative are present in a total amount of 0.1% to 3.0% by weight, wherein the weight percentage is relative to the total composition. Its features are, The weight ratio of all present ceramides to the sum of present cholesterol and / or at least one cholesterol derivative is from 1:0.1 to 1:0.

9. The weight ratio of all present ceramides to all present polyglycerol carboxylates is 1:1 to 1:30, and The composition has a saponification value of 30 to 100 mg KOH / g.

2. The composition according to claim 1, characterized in that, The at least one polyglycerol carboxylate does not contain any polycarboxylic acids that have been esterified into the polyglycerol carboxylate.

3. The composition according to claim 1, characterized in that, The weight ratio of all present ceramides to the sum of present cholesterol and / or at least one cholesterol derivative is 1:0.1 to 1:0.

8.

4. The composition according to claim 1, characterized in that, The weight ratio of all present ceramides to the sum of present cholesterol and / or at least one cholesterol derivative is 1:0.2 to 1:0.

7.

5. The composition according to claim 1, characterized in that, The weight ratio of all present ceramides to all present polyglycerol carboxylates is 1:1 to 1:

25.

6. The composition according to claim 1, characterized in that, The weight ratio of all present ceramides to all present polyglycerol carboxylates is 1:2 to 1:

20.

7. The composition according to claim 1, characterized in that, The cholesterol and / or at least one cholesterol derivative are present in a total amount of 0.1% to 2.0% by weight, wherein the weight percentage is relative to the total composition.

8. The composition according to claim 1, characterized in that, The cholesterol and / or at least one cholesterol derivative are present in a total amount of 0.2% to 1.0% by weight, wherein the weight percentage is relative to the total composition.

9. The composition according to claim 1, characterized in that, The composition contains 20% to 99% by weight of water based on the total composition.

10. The composition according to claim 1, characterized in that, The composition contains 40% to 97% by weight of water based on the total composition.

11. The composition according to claim 1, characterized in that, The composition contains 50% to 95% by weight of water based on the total composition.

12. The composition according to claim 1, characterized in that, The composition comprises components A), B) and C in a total amount of 1.0% to 25% by weight based on the total composition.

13. The composition according to claim 1, characterized in that, The composition comprises components A), B) and C in a total amount of 2.0% to 20% by weight based on the total composition.

14. The composition according to claim 1, characterized in that, The composition comprises components A), B) and C in a total amount of 4.0% to 15% by weight based on the total composition.

15. The composition according to claim 1, characterized in that, The composition contains at least two types of ceramides.

16. The composition according to claim 1, characterized in that, The composition contains at least three types of ceramides.

17. The composition according to claim 1, characterized in that, The composition contains exactly three ceramides.

18. The composition according to claim 1, characterized in that, The at least one ceramide is selected from ceramide NP, ceramide AP, ceramide EOP, ceramide NDS, ceramide ADS, ceramide EODS, ceramide NS, ceramide AS, ceramide EOS, ceramide NH, ceramide AH and ceramide EOH.

19. The composition according to claim 18, characterized in that, The at least one ceramide is selected from ceramide NP, ceramide AP, ceramide NS, ceramide EOP, and ceramide EOS.

20. The composition according to claim 1, characterized in that, The polyglycerol carboxylate of component B) is composed of a mixture of at least two selected from palmitic acid, stearic acid and benzyl acid, wherein the sum of these is based on all fatty acids present in the mixture comprising at least 75% by weight.

21. The composition according to claim 1, characterized in that, The polyglycerol carboxylate of component B) is composed of a mixture of at least two selected from palmitic acid, stearic acid and benzolic acid, wherein the sum of these is based on all fatty acids present in the mixture comprising at least 85% by weight.

22. The composition according to claim 1, characterized in that, The composition has a saponification value of 40 to 70 mg KOH / g.

23. The composition according to claim 1, wherein it is in the form of a cosmetic formulation, a pharmaceutical formulation or a dermatological formulation.

24. The composition according to claim 1, characterized in that, The composition comprises components A), B) and C in a total amount of 0.01% to 1.25% by weight based on the total composition.

25. The composition according to claim 1, characterized in that, The composition comprises components A), B) and C in total amounts of 0.01% to 1.00% by weight based on the total composition.

26. The composition according to claim 1, characterized in that, The composition comprises components A), B) and C in a total amount of 0.02% to 1.00% by weight based on the total composition.

27. The composition according to claim 1, characterized in that, The pH of the composition is from 4.0 to 8.

0.

28. The composition according to claim 1, characterized in that, The pH of the composition is 4.5 to 7.

4.

29. The composition according to claim 1, characterized in that, The pH of the composition is 5.0 to 7.

2.

30. Use of the composition according to at least one of the preceding claims for increasing the barrier function of the skin.

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