MXPA99008948A - Compositions comprising santalins, santarubins for artificially coloring the skin - Google Patents

Abstract

The invention relates to cosmetic and/or dermopharmaceutical compositions comprising at least one extract of red wood as a skin-coloring agent;said compositions may further comprise dihydroxyacetone. The invention also relates to cosmetic and/or dermopharaceutic compositions comprising at least one compound of the following formula:(I) wherein:R1, R2, R3, R6, and R9, identical or different, independently represent a hydrogen atom or an alkyl radical in C1-C4, R4, R5, R7, and R8, identical or different, independently represent a hydrogen atom, a hydroxyl radical, or an alcoxy radical in C1-C4. The invention also relates to the applications of said compositions to coloring the skin.

Description

"COMPOSITIONS COMPRISING SANTALI AS, SANTARRUBINS FOR THE ARTIFICIAL COLORING OF THE SKIN DESCRIPTION OF THE INVENTION The present invention relates to new cosmetic and / or dermatological compositions comprising at least one specific compound, namely a red wood extract, for To give the skin an artifi-cial coloration similar to natural tanning and to its uses in the aforementioned cosmetic field.Today, it is important to have a good appearance and a tanned skin -it is always a sign of good health.However, natural tanning it is not always desirable insofar as it requires prolonged exposures - to UV rays, in particular to UV-A radiation that causes tanning of the skin but in contrast they are liable to induce an alteration of this, particularly in case of sensitive skin or a skin continually exposed to solar radiation. It is therefore desirable to find an alternative to natural tan that is compatible with the demands of such skins. Most of the cosmetic products destined for the artificial tanning of the skin are based on carbonic derivatives that allow, by interaction with the amino acids of the skin, the formation of colored products. In this regard, it is known that dihydroxyacetone, or DHA, is a particularly interesting product that is commonly used in cosmetics as an artificial tanning agent for the skin; applied on the latter, particularly on the face, allows to obtain a tanning effect or REF .: 31359 toasting, similar in appearance to that which may result from prolonged exposure to the sun (natural tanning) or under a UV lamp. However, the use of DHA may present some inconvenient results. Thus, the DHA presents an annoying tendency, more or less pronounced according to the nature of the medium in which it is formulated, to be degraded over time, this degradation being translated generally over time by an undesirable yellowing. of the compositions that contain it. A phenomenon of this kind means that the activity of DHA, and in particular its behavior in coloring the skin, can be diminished at the moment of the application of these compositions on the skin. Thus, the intensity of the coloration obtained on the skin may appear as still insufficient. Another drawback of DHA is the slowness with which the coloring develops: it is necessary to count several hours (3 to 5 hours in general), so that the coloring is revealed. In addition, the coloration produced on the skin by DHA is often judged too yellow - by the users. There is therefore a growing demand for autobobjí ceaptes products that act quickly and confer a color more similar to natural tanning. In order to respond to this need, it has been proposed to associate DHA with various compounds: thus, WO 95/15742 describes the -ssociation of DHA with amino acids. However, the use of such associations is very impractical insofar as it requires either an application in two times or separate conditioning -complexes. Document FR-2,726,761 describes the association of the same DHA with lawsone and / or juglone: this association is still not very satisfactory, due this time to the sensitization risks that it presents. Thus, new compounds and new compositions are being investigated that allow the skin to artificially confer a coloration to the natural tan in a simple, effective, fast and risk-free manner. Now, as a consequence of important investigations carried out in the field of artificial coloring of the skin, the Applicant Firm has now discovered that the use of particular compounds, on the other hand known in the state of the art as dyes, it allowed a lasting artificial coloration similar to the natural bronzing, and this, immediately after the application on the skin. The subject of the present invention is therefore a new composition - cosmetics and / or dermatology, characterized in that it comprises, on a cosmetically acceptable support, at least one extract of red wood as a skin coloring agent. For the purposes of the present invention, the term "skin coloring agent" means a compound which has a particular affinity for the skin which allows it to impart artificial coloring to the skin. By "durable coloring", a coloring is understood that it is not eliminated neither with water nor with the help of a solvent, and that it resists the friction and washing by a solution containing tensio-active agents. A coloration of this durable kind is thus distinguished from the superficial and momentary coloring provided by, for example, a product of - makeup or a ritual mask. The subject of the present invention is also the novel use of at least one extract as defined above in, or for the manufacture of, cosmetic and / or dermatological compositions intended to confer on the skin an artificial coloration similar to natural tanning. . The subject of the present invention is also a method for the cosmetic treatment of the skin intended to give it an artificial coloration similar to natural tanning, characterized in that it consists of applying an effective amount of an extract or a composition thereof cosmetics thereon, such as have defined previously. The compositions and uses according to the invention have an artificial coloration similar to natural tanning in an exceptionally short time lapse. Thus, an inme-diata coloration is obtained which allows a visualization of the application and, consequently, a better homogeneity in the spread of the composition on the skin and, by following cushion, of the resulting coloration. Furthermore, the artificial coloration obtained on the skin according to the invention is extremely similar to the natural braze and also very resistant to water and time (it can persist on the skin for several days). Other features, aspects and advantages of the present invention will appear on reading the detailed description that follows. The compounds used in the present invention are extracts of red wood: among these red woods, the so-called "soluble" red woods and the so-called "insoluble" red woods are distinguished. Under the name of "soluble" redwoods, gene- very different species of the genus "Cesalpinia" such as Cesalpinia sappan, more commonly called Sapan Wood, Cesalpinia brasil ie, also called Wood of Brazil, Cesalpinia crista or also Ce salpinia echipata. Under the name of "insoluble" red woods are usually grouped the species of Asian and West African red woods of the genus "Pterocarpus" and the genus "Baphia": these woods are for example the Pterocarpus santalinus, the Pterocarpus osun, the Pterocarpus soyauxii , the Pterocarpus erinaceus, the Pterocarpus indicus or also the sharp Baphia. - These woods can also be called padauk, sandalwood (Sandalwood), narrawood, ca wood or also barwood. Thus, extracts that can be used in the present invention can, for example, be obtained from Red Santal Wood (Pterocar pus santal inus), by aqueous basic extraction, as the product sold under the trade name "Santal Concentrado SL 709C "by the Company -COPIAA or also by means of solvent extraction of the Santal powder as the product sold under the trade name" Santal Poudre SL PP "by the same COPIAA Company. It is also possible to mention the hydroalcoholic extract of Red Santal Wood powder from the ALBAN MULLER Company. Extracts that are equally suitable for the present invention can be obtained from reddish woods such as Camwood (Baphia crisp) or also Barwood (Pterocarpus soyauxii, Pterocarpus erinaceus): the latter is thus fractionated and then crushed: an alcoholic extraction classical or by percolation is done next on this - crushed in order to collect a powdery extract particularly adapted for the embodiment of the present invention.

Preferably, these extracts are obtained from the corresponding red wood core.

Preferably, red wood extracts called "insoluble" red woods will be used in the present invention.

The compounds extracted from such woods and which are particularly suitable for the embodiment of the present invention are, for example, santalins A, B and C and santarrubins A. B and C.

Some of these compounds are known as food product colorants or also as dyes of leather or wool. They are described for example in "Santalin-A peerless natural colourant", Cosmetics & Toiletries, vol. 101, April 1986, page 69.

However, its use as a skin coloring agent as defined above has never been described.

Preferably, the redwood extracts used in the present invention comprise at least one molecule corresponding to the following formula (I): (l) in which: - R., R, 3, g and g, identical or different independently represent a hydrogen atom or an alkyl radical of C ^ -C ^ - R4, R5, R-, and Rg. identical or different independently represent a hydrogen atom, a hydroxyl radical or an alkoxy radical of - Preferably, the compounds used in the present invention are those corresponding to formula (I) indicated above for which R and Rg each represent a hydrogen atom. A particularly preferred family of compounds which are suitable for the present invention is that of the compounds which respond to the formula (I) indicated above for which R2, Rg, Rg, R7 and Rg each represents a hydroquinone atom. A preferred compound of - this family is the one for which, in addition, R1 and R3 each represent a methyl radical, R. represents a methoxy radical and Rg represents hydrogeny, Another preferred compound of this family is that for which, in addition, R. and R , each represents a methyl radical and R4 and Rg represent each a methoxy radical. A third preferred compound of this family is that for which, in addition, R1 and Rg each represents hydrogen and.

Rg each represents a hydroxyl radical. Another particularly preferred family of compounds which are suitable for the present invention is that of the compounds which respond to the formula (I) indicated above for which: "R2 R4 and R6 each represent hydrogen, - R, and R represent each one a methyl radical, - R 7 represents the methoxy radical A preferred compound of this second family is that for which, in addition, R 5 represents a methoxy radical, R g represents hydrogen and R g represents a methyl radical. second family is that for which, in addition, Rg represents a hydroxyl radical, Rg represents hydrogen and Rg represents a methyl radical.A third preferred compound of this second family is that for which, in addition, R5 and Rg represent each a hydroxyl radical and Rg represents hydrogen, preferably the red wood extract is present in the compositions according to the present invention in proportions sufficient for ferr to the skin, after application, a coloration similar to the coloration obtained as a result of a natural tan. It is thus generally present in proportions comprised between - 0.05 and 10% by weight relative to the total weight of the composition, and preferably comprised between 09.1 and 5% by weight relative to the total weight of the composition. The cosmetic and / or dermatological compositions considered by the present invention may well contain one or more other skin coloring agents such as, for example, mono- or polycarbonylated derivatives such as isatin, alloxan, ninhydrin, glyceraldehyde The mesothartic aldehyde, the 4,5-pyrazoline dione derivatives, may be those skin coloring agents which may or may not be associated with straight dyes or indole derivatives. In a preferred embodiment of the invention, the compositions further comprise dihydroxyacetone (DHA). Thus, the subject of the present invention is also a cosmetic and / or dermatological composition, characterized in that I comprise, in a cosmetically acceptable support, a red wood extract as defined above and dihydroxyacetone. Indeed, the dihydroxyacetone and redwood extracts previously defined have an excellent chemical compatibility in the composition of the compositions that contain them, as well as a very good completeness of the colorations that confer to the skin, which allows them to be associated in Proper proportions, reach an artificial coloring of the skin remarkably close to the coloring conferred by natural brojí ceado. The dihydroxyacetone or DHA is present in the compositions according to the invention in proportions that allow the association of the two skin coloring agents, namely the red wood extract and the dihydroxyacetone itself, confer to the skin, after application, a coloration as close as possible to that obtained as a result of a natural tan. DHA is thus generally present in a proportion between 0.5 and 10% by weight relative to the total weight of the emulsion, and preferably between 1 and 7% by weight relative to the total weight of the composition. The dihydroxyacetone can also be applied to the skin in f? of an independent composition, separately from the composition comprising the red wood extract, for example before or after the application of the latter. In a preferred embodiment of the cosmetic treatment according to the invention, a composition comprising dihydroxyacetone is applied in a first step, then, in a second step, the composition comprising the red wood extract, with you look at shading, according to the will -of the user, the coloration judged sometimes a little yellow contributed by dihydroxyacetone alone. The compositions according to the invention can also contain one or more sunscreens active to UVA and / or UVB (absorbers), diophiles or lipophiles, or also pigments of metal oxides coated or not. The compositions according to the present invention may also comprise conventional cosmetic adjuvants particularly chosen from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, antioxidants, free anti-free radicals, opacifiers, stabilizers, emollients, silicones, -, tt-hydroxy acids, anti-foam agents, moisturizing agents, vitamins, perfumes preservatives, surfactants, fillers, sequestrants, polymers , propellants, alkalizing agents or acidulants, dyes, or any other ingredient customarily used in the cosmetic and / or dermatological field, in particular for the manufacture of sunscreen compositions in the form of emulsions. The fatty substances may be constituted by an oil or a cement or their mixtures. By oil, a liquid compound is understood at room temperature. By wax, it is meant a solid or substantially solid compound at room temperature, and whose melting point is generally higher than 35 ° C. As oils, mineral oils (petroleum jelly) can be mentioned; vegetables (sweet almond oil, macadamia oil, currant nuggets, jojoba oil); synthetics such as perhydrosqualene, alcohols, acids or fatty esters (such as the benzoate of C.-Cc alcohols sold under the trade name "Finsolv TN" by the Finetex Company, octyl palmitate, isopropyl lanolate , the triglycerides of which the capric / caprylic acids), the oxyethylenated or oxypropylenated fatty esters and ethers; silicone compounds (cyclomethicone, polydimethylsiloxanes or (PDMS) or fluorinated ones, polyalkylenes) Waxy compounds include paraffin wax, carnauba wax, beeswax, hydrogenated castor oil, organic solvents, among others. the lower alcohols and polyols.

Thickeners can be chosen in particular from crosslinked polyacrylic acids, guar gums and modified or non-modified celluloses such as hydroxypropylated guar gum, methylhydroxyethylcellulose and hydroxypropylmethylcellulose. Of course, the person skilled in the art will try to choose the one or more complementary compounds mentioned above and / or their amounts in such a way that the advantageous properties intrinsically related to the use of the compounds of formula (I) indicated above in accordance with the invention are not, or substantially, altered by the o-additions considered. The compositions according to the invention can be prepared according to techniques well known to the person skilled in the art., in particular those intended for the preparation of oil-in-water or water-in-oil type emulsions. This composition can be present in particular in the form of an emulsion, simple or complex (H / E, E / H, H / E / H or E / H / E) such as a cream, a milk, or in the form of a gel or of a cream gel, in the form of a lotion, of powder, of solid stick and possibly be conditioned in aerosol and presented in the form of foam or spray. Preferably, the compositions according to the invention are in the form of an oil-in-water emulsion. When it is an emulsion, the aqueous phase of this can comprise a nonionic vesicular dispersion prepared according to known methods (Banham, Stanriish and Watkins, J. Mol. Biol. 13. 238 (1965), FR 2.315.991. and FR 2,416,008).

Concrete, but by no means limiting, examples illustrating the invention will be given below. EXAMPLE 1: This example tries to show, in a first phase, the intensity -of the coloration obtained with a red wood extract according to the present invention as well as the speed with which this coloration develops. In a second phase, the improvement will be shown, in terms of coloring tonality, provided by a composition according to the invention (composition A containing a DHA association-red wood extract according to the invention) in relation to a classical composition that only contains DHA (composition B).

The Applicant firm has made the following composition A (the amounts are expressed as a percentage of weight in relation to the total weight of the composition): Composition A: = Blend c € tilestearil glucoside / cetilestearilico alcohol sold under the trade name "Montanov 68"by Seppic 7.5% - dimethicone 0.5% - benzoate of alcohols of C1? / C15 sold under the trade name "Finsolv TN" by Finetex 15% - Propylene glycol 10% - dihydroxyacetone 5% - Santal wood extract sold in powder form under the trade name "Santal Poudre'SL PP" by the COPIAA Society 0.3% - preservatives cs - water csp 100% The applicant firm has also made a B identical to A but does not contain any Bois de Santal extract. Evaluation protocol: 2 Compositions A and B were applied at a rate of 1 mg / cm on a 2 zone of 7 x 7 cm delimited on the back of four volunteers. The following three series of colorimetric measurements have been made - with the help of a Minolta CM-1000 colorimeter: - 1s) before application of the composition (to), - 25) 30 minutes after the application (T3Q,), - 3Q) 5 hours after the application and after washing (- ,,) - The results are expressed in the system (L *, a *, b *) in which L * represents the luminance, a * represents the axis red-green (-a * = green, + a * = red) and b * represents the yellow axis blue-l, (-b * * blue, + b * = yellow) Thus, a * and b * express the hue of the to skin. For the evaluation of the intensity of the coloration, the following is taken into account: - a? L * which translates the darkening of the color: the more IL * is negative, the more the color becomes darker. - to the relation? a * /? b * which translates the red / yellow balance and therefore the tonality. The results obtained are grouped in the following table (I): 25 Table (I) It is thus observed that 30 minutes after application, composition B, which only contains DHA, has conferred practically no color to the skin, since DHA has not had time to act (? L * = 0.13 ). On the contrary, the composition according to the invention has already given the skin a significant coloration (? L * = -1.74) and this maintaining a good red-yellow balance (? A * /? B * = 1.05 ). Thus, the wood extract from Santal according to the invention confers on itself an intense and similar color to the natural tanning of the skin. It is further observed that, 5 hours after the application of the compositions and after washing, the two compositions A and B have conferred to the skin a darkening of similar intensity (AL * = -0.86 and AL * = -0.94) due to the action of the DHA but the composition A according to the invention gives the skin a much less yellow coloration than the DHA and much -more like the red-yellow balance (? A * /? B * = 0.81 contra? A * /? B * = 0.63 for composition B). Thus, the composition according to the invention gives the skin a coloration particularly similar to natural tanning, and this very quickly. EXAMPLE 2: The applicant has made the two compositions C (according to the invention) and D (composition containing only the DHA) below (the quantities are expressed as a percentage by weight with respect to the total weight of the -composition): COMPOSITION C : - cetylstearyl glucoside / cetyl stearyl alcohol mixture sold under the trade name "Montanov 68" by Seppic 7.5% - dimethicone 0.5% - C12 / C15 alcohol benzoate sold under the trade name "Finsolv TN" by Finetex 15% - Propylene glycol 10% - dihydroxyacetone 5% - alcoholic extract of Pterocarpus soyauxii in powder form * 0.3% - preservatives cs - water csp 100% * The alcoholic extract of Pterocarpus soyauxii in powder form was obtained according to the following extraction method: the reddish wood of -Pterocarpus soyauxi was fractioned into small pieces of wood that will be passed through the Thermomix 3300 mixer ( VORWECK). This first coarse shred was then subjected to the RETSCH shredder provided with a -0.5 mm grid. 50 g of powder were placed in a column overheated by a separating funnel filled with alcohol (EtOH 60 ° - 500 ml). The percolation was performed under a flow rate of 30 to 50 ml / hour. The collected eluent was evaporated and then dried in vacuo over P-The composition D is identical to composition C but does not contain any Pterocarpus soyauxii. Evaluation protocol: Compositions C and D were applied twice, with 24 hours of 2 2 terval, at a rate of 1 mg (cm over a 7 X 7 c area delimited on the back of four volunteers. were performed with the help of a Minolta CM-1000 colorimeter before application of the composition (T0) then 5 hours after the second application (T? .C) - As in Example 1, the results were expressed in the L system *, a *, b *.? a * = a * T24 + 5 - a * T0? b * = b * T24 + 5 - b * T0 The results are grouped in the table (II) given below Table (II) In the same way as in the previous example, the value of? A * /? B * is higher for the composition of the invention: it is therefore when the coloration conferred by this composition on the skin has a redder hue than the conferred by the composition that only contains DHA that is too yellow. Thus, the coloration conferred by the composition according to the invention on the skin is much more similar to the red / yellow balance and therefore more similar to the coloring provided by natural tanning. A composition such as composition C makes it possible to quickly achieve a first coloration, then, after the development of DHA, obtain a lasting coloration very similar to that conferred by a natural tan. It is noted that in relation to this date, the best method known by the applicant to carry out the said invention, is that which is clear from the present description of the invention.

Claims (5)

1. REVINDI CAC I ON ES Having described the invention as above, the content of the following claims is claimed as property: 1.- Cosmetic and / or dermatological composition, characterized by the he / she comprising, in a cosmetically acceptable support, at least one red wood extract as a skin coloring agent.
2. 2. Composition according to claim 1, characterized by the fact that the red wood is chosen among the red woods called "inso lubles".
3. 3. Composition according to claim 2, characterized by the fact that the red wood is of the genus "Pterocarpus" or of the genus "Baphia".
4. 4. Composition according to claim 3, characterized by the fact that the red wood is of the genus "Pterocarpus".
5. 5. Composition according to claim 4, characterized by the fact that the extract is obtained by aqueous basic extraction of Pteroca pus santalinus. 6, - Composition according to claim 4, characterized in that the extract is obtained by hydroalcoholic extraction of Pterocarpus soyauxii. 7. Composition according to any one of the preceding claims, characterized in that the extract is present in the final composition in a content ranging between 0.05 and 10%, preferably between 0.1 and 5% in weight, in relation to the total weight of the composition. 8. Composition according to any one of the preceding claims, characterized in that the extract comprises at least one compound of formula (I) below (0 in which: -R1, R2, R, Rg and Rg, identical or different represent a hydrogen atom or an alkyl radical of C, -C4. -R ^, Rg, R7, and Rg, identical or different they represent a hydrogen atom, a hydroxyl radical or an alkoxy radical of C> -C4 9.- Cosmetic and / or dermatological composition, characterized in that it comprises, on a cosmetically acceptable support, at least one compound of formula (I) (I) wherein: - R R > Rq »Rg» and Rq > identical or different represent a hydrogen atom or an alkyl radical of C, - C4, - R., Rg, R7 and Rg, identical or different represent a hydrogen atom, a hydroxyl radical or a C1-C4 alkoxy radical . as a skin coloring agent. 10. The composition according to claim 8 or 9, characterized in that the radicals R2 and g each represent a hydrogen atom. II.- Composition according to any one of claims 8 to 10, characterized in that the compound of formula (I) is a -santaline. 12. Composition according to any one of claims 8 to 10, characterized in that the compound of formula (I) is a -santarrubin. 13. Composition according to any one of the preceding claims, characterized in that it also comprises another agent of -coloring the skin, preferably dihydroxyacetone. 14. Composition according to claim 13, characterized in that the dihydroxyacetone is present in the composition in a cushion ranging between 0.5 and 10%, preferably between 1 and 7% by weight, in relation to the total weight of the composition. 15.- Cosmetic and / or dermatological composition, characterized in that it comprises, in a cosmetically acceptable support, a red-wood extract or a compound of formula (I) such as has been defined in any one of claims 1 to 6 and 8 to 12 and dihydroxyacetone. 16. Process for the cosmetic treatment of the skin intended to confer an artificial coloration similar to natural tanning, characterized in that it consists in applying an effective amount of a red wood extract, a compound of formula (I) or a composition thereon. as defined in any one of the preceding claims. 17. Process according to claim 16, characterized in that - the fact that it comprises the following two steps: - 1) a composition comprising dihydroxyacetone-ii) is applied to the skin when the coloring provided by the dihydroxyacetone is revealed -on the skin, any of the compositions defined in any one of claims 1 to 15 is applied to the skin in order to qualify this coloration. 18. Use of at least one extract of red wood or of at least one compound of formula (I) as defined in any one of claims 1 to 6 and 8 to 12 in, or for the manufacture of, -cosmetic and / or dermatological compositions designed to give the skin an artificial coloration similar to natural tanning.