Composition comprising ceramide and triglyceride

Abstract

The invention relates to a composition comprising at least one ceramide and at least one triglyceride at specific concentrations, a process for producing a formulation comprising at least one ceramide and the use of at least one triglyceride at high concentrations for stabilization of a ceramide-containing composition.

Description

[0001] Composition comprising ceramide and triglyceride

[0002] Field of the invention

[0003] The invention relates to a composition comprising at least one ceramide and at least one triglyceride at specific concentrations, a process for producing a formulation comprising at least one ceramide and the use of at least one triglyceride at high concentrations for stabilization of a ceramide-containing composition.

[0004] Prior art

[0005] Ceramides are used in many cosmetic formulations. However, their low solubility and strong tendency to recrystallization complicate the stable incorporation into cosmetic formulations. Especially at temperatures just above freezing, formulations often suffer from inhomogeneities. In addition, microbial stabilization of ceramide-containing formulations is challenging since preservatives regularly adversely affect the physical stability of formulations.

[0006] The prior art addresses this problem by various delivery forms.

[0007] For instance, WO1998053797 describes encapsulated water-insoluble active ingredients having amphiphilic character, with a content of water and at least one surfactant from the group of esters of long-chain carboxylic acids with carboxylic acids comprising hydroxyl groups or salts thereof and esters of long-chain carboxylic acids with polyalcohols, in which ceramides may be the waterinsoluble active ingredients.

[0008] WO1999029293 describes a composition for topical application, comprising a combination of a free sphingoid base and a ceramide.

[0009] JP2008297301 describes ceramides and phytosterol derivatives in triglyceride-containing oil solutions in liquid form for incorporation into dermatological preparations.

[0010] The object of the invention was to provide compositions comprising ceramides which have excellent physical stability.

[0011] Description of the invention

[0012] It has been found that, surprisingly, the compositions described below are able to solve the problem addressed by the invention.

[0013] The present invention therefore relates to a composition comprising at least one ceramide and triglyceride as described in claim 1 . The invention further relates to a process for producing a cosmetic or pharmaceutical formulation and to the use of a triglyceride for stabilization of a ceramide-containing composition.

[0014] An advantage of the present invention is that the compositions according to the invention have increased storage stability and are thus slower to change in their nature over time, particularly with regard to their viscosity, compared to ceramide-containing compositions according to the prior art.

[0015] One advantage of the composition according to the invention is that the composition in formulations has superior sensory properties which lead to an improved skin feel and / or hair feel.

[0016] It is a further advantage of the composition according to the invention that the composition in formulations has improved distributability compared to the individual components.

[0017] It is a further advantage of the composition according to the invention that the composition in formulations has improved absorption compared to the individual components.

[0018] It is a further advantage of the composition according to the invention that the composition in formulations has reduced oiliness compared to the individual components.

[0019] It is a further advantage of the composition according to the invention that the composition in formulations has reduced waxiness compared to the individual components.

[0020] It is a further advantage of the composition according to the invention that the composition in formulations has improved glidability compared to the individual components.

[0021] It is a further advantage of the composition according to the invention that the composition in formulations has reduced tackiness compared to the individual components.

[0022] It is a further advantage of the composition according to the invention that the composition in formulations has improved silkiness / velvetiness compared to the individual components.

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

[0024] It is a further advantage of the composition according to the invention that the composition in reduces brittle hair stronger compared to the individual components.

[0025] It is a further advantage of the composition according to the invention that the composition supports the penetration of Ceramides and lipids into the hair fibre stronger compared to the individual components.

[0026] It is a further advantage of the composition according to the invention that the composition increases the hydrophobicity of hair stronger compared to the individual components.

[0027] It is a further advantage of the composition according to the invention that the composition prevents the damage of hair caused by daily grooming activities stronger compared to the individual components.

[0028] It is a further advantage of the composition according to the invention that the composition prevents hair breakage.

[0029] It is a further advantage of the composition according to the invention that the composition increases the hydrophobicity of hair. It is a further advantage of the composition according to the invention that the composition prevents wash out of lipids from hair fibres.

[0030] The present invention therefore relates to a composition comprising

[0031] A) at least on ceramide,

[0032] B) at least one triglyceride, characterised in that component B) is comprised in an amount of from 60.0 wt-% to 99.0 wt-%, preferably from 80.0 wt-% to 98.5 wt-%, more preferably from 90.0 wt-% to 98.5 wt-%, where the percentages by weight refer to the total composition.

[0033] In the context of the present invention, the term “ceramide” is understood to mean acylated sphingoid bases, where the sphingoid bases are preferably selected from sphingosine, sphinganine, 6-hydroxysphingosine and phytosphingosine.

[0034] The “pH” in connection with the present invention is defined as the value which is measured for the relevant composition at 22°C after stirring for five minutes using a pH electrode calibrated in accordance with ISO 4319 (1977).

[0035] Unless stated otherwise, all percentages (%) given are percentages by mass.

[0036] It is preferred in accordance with the invention that the composition according to the invention is characterized in that said at least one ceramide is selected from the group comprising ceramide NP, ceramide AP, ceramide EOP, ceramide NG (also known as ceramide NDS and ceramide 2), ceramide ADS, ceramide EODS, ceramide NS, ceramide AS, ceramide EOS, ceramide NH, ceramide AH and ceramide EOH, preferably selected from the group comprising ceramide NG, ceramide NP, ceramide AP, ceramide NS, most preferably ceramide NG.

[0037] Preferred compositions according to the invention are characterized in that component A) is comprised in an amount of from 0.1 wt-% to 12.5 wt-%, preferably from 0.2 wt-% to 6.0 wt-%, more preferably from 0.3 wt-% to 2.0 wt-%, where the percentages by weight refer to the total composition.

[0038] A preferred composition according to the invention is characterized in that said composition comprises at least two ceramides, preferably at least three ceramides, particularly preferably precisely three ceramides.

[0039] Any type of triglyceride is suited to be comprised in component B) of the composition of the instant invention.

[0040] Especially suited are natural oils, which preferably are isolated from plants. Preferred compositions according to the invention are characterized in that said component B) comprises of from 50.0 wt-% to 90.0 wt-%, preferably from 60.0 wt-% to 87 wt-%, more preferably from 65.0 wt-% to 85 wt-%, triglycerides in which at least one fatty acid acyl residue comprises at least one hydroxy group, where the percentages by weight refer to the total component B).

[0041] Preferably compositions according to the invention are characterized in that said component B) comprises of from 50.0 wt-% to 85.0 wt-%, preferably from 60.0 wt-% to 80.0 wt-%, more preferably from 65.0 wt-% to 75.0 wt-%, triricinolein, where the percentages by weight refer to the total component B).

[0042] A preferred composition according to the invention is characterized in that said component B) comprises of from 0.3 wt-% to 2.0 wt-%, preferably from 0.4 wt-% to 1.5 wt-%, more preferably from 0.5 wt-% to 1.2 wt-%, triglycerides comprising at least one palmitoleic acid acyl group, where the percentages by weight refer to the total component B).

[0043] Compositions according to the invention are especially preferred which are characterized in that said component B) comprises a mixture of castor oil, preferably castor seed oil, and macadamia nut oil, preferably in a weight ratio of from 10:1 to 30:1 , more preferably from 15:1 to 25:1.

[0044] Any macadamia nut oil is suited to be used in said mixture. Macadamia Integrifolia seed oil; Macadamia I ntegrifolia / Tetraphy Ila and / or Macadamia Ternifolia seed oil are preferably comprised in said mixture, with Macadamia Integrifolia seed oil being especially preferred.

[0045] Preferably said mixture makes up 80 wt.-% to 100 wt.-% of said component B).

[0046] A composition according to the invention is preferably characterized in that it comprises

[0047] C) cholesterol and / or at least one cholesterol derivative selected from the group comprising, preferably consisting of, cholesterol sulfate, cholesterol hydrogen succinate and 7- dehydrocholesterol, most preferably cholesterol.

[0048] Preferably component C) is comprised in an amount of from 0.05 wt-% to 3.0 wt-%, preferably from 0.1 wt-% to 2.0 wt-%, more preferably from 0.2 wt-% to 1.0 wt-%, where the percentages by weight refer to the total composition.

[0049] A preferred composition according to the invention is characterized in that said component B) comprises

[0050] D) at least one fatty acid. Fatty acids preferably comprised in component D) of the composition according to the invention are selected from the group comprising, preferably consisting of, caproic acid, caprylic 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, petroselinic acid, elaidic acid, arachic acid, behenic acid, erucic acid, gadoleic acid, linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, arachidonic acid, with palmitic acid and palmitoleic acid being preferred and with palmitic acid being especially preferred.

[0051] Preferably component D) is comprised in an amount of from 0. 5 wt-% to 8.0 wt-%, preferably from 1.0 wt-% to 5.0 wt-%, more preferably from 1.5 wt-% to 3.0 wt-%, where the percentages by weight refer to the total composition.

[0052] The present invention further relates to a process for producing a cosmetic or pharmaceutical formulation comprising at least one ceramide, comprising the process steps of: a) providing a composition according to the instant invention; b) adding a cosmetic or pharmaceutical acceptable carrier, preferable water or a natural oil, and preferably one further cosmetical and pharmaceutical formulation ingredient.

[0053] Preferred compositions according to the instant invention are preferably used in the context of the process according to the instant invention.

[0054] Said further cosmetical and pharmaceutical formulation ingredient preferably added in step b) of the process of the instant invention is preferably selected from the group of surfactants, emollients, emulsifiers, thickeners, UV light protection filters, antioxidants, hydrotropes, solids and fillers, film formers, pearlescence additives, opacifiers, deodorant and antiperspirant active ingredients, insect repellents, self-tanning agents, preservatives, conditioning agents, perfumes, dyes, odour absorbers, superfatting agents and solvents, preferably perfumes, conditioning agents and thickeners, with emuslifiers being especially preferred.

[0055] As the composition according to the instant invention due to its comprised components is especially suited for the preparation of hair care formulations, the process according to the instant invention preferably is for producing a hair care formulation.

[0056] The at least one further cosmetical and pharmaceutical formulation preferably added according to the instant invention in step b) preferably is selected from the group comprising, preferably consisting of, creatine, creatinine, caffeine, carnitine, biotin, arjunolic acid, xymenynic acid, minoxidil, arginine and derivatives thereof, wherein said derivative preferably is selected from the group comprising, preferably consisting of, creatine hydrates, disodium phosphocreatine, caffeine benzide, caffeine carboxylic acid, caffeine hydrates, carnitine HCI, acetyl carnitine, acetyl carnitine HCI, carnitine fumarate, carnitine hydroxycitrate, carnitine linoleate, carnitine pyroglutamate, carnitine tartrate, palmitoyl carnitine, D / L-carnitine, D / L-carnitine HCI, hexadecanoyl carnitine, levo carnitine, allantoin biotin, biotinoyl hexapeptide-2 amide, biotinoyl pentapeptide-4, biotinoyl tripeptide-1 , biotinoyl tripeptide-35, ethyl biotinate, monoethanolamine biotinate, biotin ethyl ester, biotinum, acetyl arginine, arginine HCI, keratin hydrolysate, wheat protein hydrolysate, silk protein hydrolysate, Cetrimonium Chloride, Dicetyldimonium Chloride, Distearoyldimonium Chloride, Behentrimonium Chloride, Behentrimonium Methosulfate, Bis-(lsostearoyl / Oleoyl Isopropyl) Dimonium Methosulfate, Dioleoylethyl Hydroxyethlmonium Methosulfate, Distearoyl Dimonium Chloride, Quaternium 87, Quaternium-80, Guarhydroxypropyltrimonium Chloride, cationic celluloses, copolymers of vinylpyrrolidone and quaternized acrylates

[0057] A preferred process according to the instant invention is characterized in that said process comprises c) emulsification of the formulation.

[0058] In consequence, cosmetic or pharmaceutical formulation produced by the process according to the instant invention preferably is an emulsion, in particular an oil-in-water emulsion.

[0059] To facilitate the emulsification step c) of the process according to the instant invention it is preferred in accordance with the invention that the at least one emulsifier is present in process step c).

[0060] Emulsifiers preferably present are selected from the group of acyl lactylates (especially sodium lauroyl lactylate), ethoxylated fatty alcohols (especially ceteareth-25), ethoxylated fatty acids (especially PEG_100 stearates), polyglycerol esters (especially polyglyceryl-3 methylglucose distearate, polyglyceryl-6 stearate, polyglyceryl-6 behenate, polyglyceryl-10 stearate, polyglyceryl- 10 behenate), glycerol esters, (especially glyceryl stearate citrate), ethoxylated sorbitan esters, lecithin, hydrogenated lecithin, phosphatidylcholin and hydrogenated phosphatidylcholin, alkyl trimethyl ammonium salts, dialkyl dimethyl ammonium salts,

[0061] The term "acyl lactylate" in the context of the present invention is understood to mean salt-form reaction products of fatty acid with lactic acid and / or polylactic acid.

[0062] A preferred process according to the instant invention is characterized in that said process comprises d) adjusting the pH of the formulation to a range of 3.0 to 8.0, preferably 3.5 to 6.0 particularly preferably 4.0 to 5.0.

[0063] The formulations prepared by the process according to the invention are in particular physically stable formulations. In the context of the present invention, the term "physically stable formulations containing at least one ceramide" is understood in particular to mean formulations which in particular do not exhibit any crystallization of the ceramide and no separation or inhomogeneity after six months of storage at 25°C.

[0064] The present invention further relates to the use of of at least one triglyceride in a total amount of from 60.0 wt-% to 99.0 wt-%, preferably from 80.0 wt-% to 98.5 wt-%, more preferably from 95.0 wt-% to 98.5 wt-%, wherein the percentages refer to the total composition, for physical stabilization of a ceramide-containing composition, in particular with regard to homogeneity, and / or for preventing crystallization of at least one ceramide in a composition

[0065] Preferably the ceramide-containing composition in the use of the instant invention comprises at least one fatty acid.

[0066] In the context of the use according to the instant invention the ceramide-containing composition are preferably equal to the preferred compositions according to the instant invention, especially regarding components A), and the triglyceride preferably used is preferably equal to the preferred component B) of the preferred compositions according to the instant invention.

[0067] Brief description of the figures

[0068] Figure 1 : Survival probability of 15000 resp. 20000 cycles

[0069] Figure 2: Survival probability of Caucasian brown hair and ethnic hair as well as of ethnic hair treated with a leave in conditioner containing 1% example 1 E or a combination of 0.005% Ceramide NP + 0.005% Ceramide NG.

[0070] The examples adduced hereinafter describe the present invention by way of example, without any intention that the invention, the scope of application of which is apparent from the entirety of the description and the claims, be restricted to the embodiments specified in the examples.

[0071] Examples:

[0072] Example 1: Formulation composition

[0073] Castor seed oil in general comprises 80 wt.-% to 85 wt.-% tririconlein referring to all triglycerides in the oil; the castor seed oil used in the examples has a triricinolein content of 81 wt.-%.

[0074] Table 1 : Examples 1A-1 E are in accordance with the present invention, example 1F is not according to the present invention.

[0075] Example 2: Stability against recrystallization of Ceramides

[0076] The examples 1A-1G were prepared by heating all ingredients to 85-90 °C until the solution was completely clear. Then the formulations were cooled to 30 °C under simple stirring and a stability test was initiated. The formulations are stored at room temperature for 3 months and after 1 week, 1, 2 and 3 months they are controlled visually regarding recrystallized Ceramides. The following table shows the results.

[0077] Table 2: Stability test of examples 1A-1G regarding recrystallization.

[0078] The results of the stability test show that a sufficient amount of triglycerides is necessary to get a clear, stable formulation of Ceramides. Example 1 F contains mostly Isopropylmyristate, a well- known cosmetic emollient. However, this is not sufficient to stabilize ceramides against recrystallization. Example 3: Reduction of brittle hair

[0079] Due to repeated shampooing hair fibres are loosing lipids. Especially Ceramide NG is reduced. (Simultaneous HPLC Analysis of Ceramide and Dihydroceramide in Human Hairs, Y. Lee et al, Arch Pharm Res Vol 32, No 12, 1795-1801, 2009). The loss of Ceramide NG and other hair lipids reduce the natural hydrophobicity of the hair so that surfactants can penetrate into the hair shaft more easily. Thus, the extraction of lipids by shampooing increases with increasing length of the hair. This leads to brittle hair, especially at the hair tips.

[0080] For the following experiment hair tips taken from 20cm long hair tress of a 27 year old Caucasian woman were used. It was known that the hair only underwent normal grooming activities like washing with a shampoo, application of a conditioner and drying with a hair blower. The hair has never been bleached, permed, colored, straightened with a flat iron or with a specific straightening formulation. For the determination of hair breakage the hair tips were fixed with specific crimps. For every experiment 50 single hair fibers were used. The single hair fibers were treated with the test formulations, that means they were soaked into the test formulation for 30 min and afterwards each single hair fiber was rinsed for 6s using tap water. After at least 4 h drying at 22 °C and 50% relative humidity hair breakage was determined using an automatic cyclic tester (CYC800, Diastron, UK). By this device single hair fibers are repeatedly stretched until a specific stress is reached and the number of cycles until the hair fiber breaks is recorded. Using this number of cycles a specific software (Weibull analysis) calculates the survival probability for a different number of cycles. The lower the survival probability is the more brittle the hair will be.

[0081] As test formulations a simple standard conditioner was used (example A, vehicle). To this standard conditioner 1% of example 1 D, representing a formulation in accordance with the present invention (example B), or 0.01% Ceramide NG (representing the concentration of Ceramide NG added by 1% of example 1 D) (example C) were added. For comparison reason untreated hair was also measured.

[0082] Testformulation

[0083] Table 2: Composition of test formulation for the determination of hair breakage

[0084] Figure 1 shows the survival probability for different number of stretching cycles.

[0085] The untreated hair represents the status of the hair tips before treatment with a test formulation. The treatment with the vehicle was able to increase the survival probability from approx. 20 to 25% (15000 cycles) resp. 11% to 19% (20000 cycles). The treatment with example 1 D leads to the highest survival probabilities of 35% (15000 cycles) resp 30% (20000 cycles). The treatment with Ceramide NG was also able to increase the survival probability in comparison with the untreated hair and the vehicle but the increase was lower compared to example 1 D. This demonstrates in a very clear way that the high oil content Ceramide solution was more effective compared to the single Ceramide.

[0086] Example 4 Improvement of the mechanical resistance of ethnic hair

[0087] Ethnic hair is known to have a significantly lower mechanical resistance compared to Caucasian or Asian hair due to its highly curly structure so that hair breakage is a main concern for ethnic hair. For the following experiment a leave in conditioner containing either 1 % of example 1 E or 0.005% of Ceramide NP + 0.005% Ceramide NG (representing the concentration which was added by 1% of example 1 E) was sprayed on ethnic hair tresses. After drying for at least 4 h at 22 °C and 50 % relative humidity single hair fibres were taken from the tresses and fixed with crimps. Then hair breakage was measured. For demonstrating the lower mechanical resistance of ethnic hair compared to other hair ethnicities the results for Caucasian hair is also shown in Figure 2.

[0088] In table 3 the composition of the leave in conditioner is shown.

[0089] Table 3: composition of the test formulations

[0090] The results of the hair breakage measurement show that ethnic hair is much more sensitive to hair breakage compared to Caucasian hair. After application of a leave in conditioner containing 1% of example 1E the survival probability was increased significantly meaning that the ethnic hair has a stronger mechanical resistance. The leave in conditioner which contains the equivalent concentration of Ceramides also increased the survival probability but not as strong as the leave in conditioner containing example 1 E. The results of this example show that the high oil containing Ceramide solution is more effective in improving the mechanical resistance of ethnic hair compared to the single Ceramides.

Claims

Claims1 . A composition comprisingA) at least on ceramide,B) at least one triglyceride, characterised in that component B) is comprised in an amount of from 60.0 wt-% to 99.0 wt- %, preferably from 80.0 wt-% to 98.5 wt-%, more preferably from 90wt-% to 98.5 wt-%, where the percentages by weight refer to the total composition.

2. Composition according to claim 1 , characterized in that said at least one ceramide is selected from the group comprising ceramide NP, ceramide AP, ceramide EOP, ceramideNG, ceramide ADS, ceramide EODS, ceramide NS, ceramide AS, ceramide EOS, ceramideNH, ceramide AH and ceramide EOH, preferably selected from the group comprising ceramide NG, ceramide NP ceramide NS, ceramide AP, most preferably ceramide NG.

3. Composition according to Claim 1 or 2, characterized in that component A) is comprised in an amount of from 0.1 wt-% to 12.5 wt-%, preferably from 0.2 wt-% to 6.0 wt-%, more preferably from 0.3 wt-% to 2.0 wt-%, where the percentages by weight refer to the total composition.

4. Composition according to at least one of the preceding claims, characterized in that said component B) comprises of from 50.0 wt-% to 90.0 wt-%, preferably from 60.0 wt-% to 87 wt-%, more preferably from 65.0 wt-% to 85 wt-%, triglycerides in which at least one fatty acid acyl residue comprises at least one hydroxy group, where the percentages by weight refer to the total component B).

5. Composition according to at least one of the preceding claims, characterized in that said component B) comprises of from 50.0 wt-% to 85.0 wt-%, preferably from 60.0 wt-% to 80.0 wt-%, more preferably from 65.0 wt-% to 75.0 wt-%, triricinolein, where the percentages by weight refer to the total component B).

6. Composition according to at least one of the preceding claims, characterized in that said component B) comprises of from 0.3 wt-% to 2.0 wt-%, preferably from 0.4 wt-% to 1 .5 wt-%, more preferably from 0.5 wt-% to 1.2 wt-%, triglycerides comprising at least one palmitoleic acid acyl group, where the percentages by weight refer to the total component B).

7. Composition according to at least one of the preceding claims, characterized in that said component B) comprises a mixture of castor oil, preferably castor seed oil, and macadamia nut oil, preferably in a weight ratio of from 10:1 to 30:1 , more preferably from 15:1 to 25:1.

8. Composition according to at least one of the preceding claims, characterized in that it comprisesC) cholesterol and / or at least one cholesterol derivative selected from the group comprising cholesterol sulfate, cholesterol hydrogen succinate and 7- dehydrocholesterol, wherein preferably component C) is comprised in an amount of from 0.05 wt-% to 3.0 wt-%, preferably from 0.1 wt-% to 2.0 wt-%, more preferably from 0.2 wt-% to 1.0 wt-%, where the percentages by weight refer to the total composition.

9. Composition according to at least one of the preceding claims, characterized in that it comprisesD) at least one fatty acid, wherein preferably component D) is comprised in an amount of from 0. 5 wt-% to 8.0 wt-%, preferably from 1.0 wt-% to 5.0 wt-%, more preferably from 1.5 wt-% to 3.0 wt-%, where the percentages by weight refer to the total composition.

10. Process for producing a cosmetic or pharmaceutical formulation comprising at least one ceramide, comprising the process steps of: a) providing a composition according to at least one of the claims 1 to 9; b) adding a cosmetic or pharmaceutical acceptable carrier, and preferably one further cosmetical and pharmaceutical formulation ingredient.

11. Process according to claim 10, characterized in that process comprises c) emulsification of the formulation.

12. Process according to claim 10 or 11 , characterized in that process comprises d) adjusting the pH of the formulation to a range of 3.0 to 8.0, preferably 3.5 to 6.0 particularly preferably 4.0 to 5.0.

13. Use of at least one triglyceride in a total amount of from 60.0 wt-% to 99.0 wt-%, preferably from 80.0 wt-% to 98.5 wt-%, more preferably from 95.0 wt-% to 98.5 wt-%, wherein the percentages refer to the total composition, for physical stabilization of a ceramide-containing composition, in particular with regard to homogeneity, and / or for preventing crystallization of at least one ceramide in a composition.

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