MXPA99002859A - Cosmetic composition containing a new pigme - Google Patents

Abstract

The present invention relates to cosmetic compositions and mainly make-up, which contain a new red pigment of intense and saturated color, not generating free radicals. This novel pigment is a diketo-pyrrolo pyrrole DPP of the formula, in which R1 and R2 independently represent a hydrogen atom, an alkyl radical from 1 to 18 carbon atoms, alkenyl from 3 to 12 carbon atoms, alkoxycarbonyl from 2 to 5 atoms of carbon, phenyl optionally substituted by a halogen, R3 and R4 independently represent a hydrogen atom, an alkyl radical of 1 to 18 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen or phenyl, or a group -SO3M with M representing an atom of hydrogen, a metal atom or an ammonium group, the alkyl, alkenyl and alkoxy radicals which may be linear or branched. Thanks to this pigment it is possible to protect the skin, lips and keratin fibers from free radicals, without using antioxidants in the composition.

Description

COSMETIC COMPOSITION CONTAINING A NEW PLGMENT Description of the invention The present invention relates to cosmetic compositions containing a new red pigment of intense and saturated color, not generated from free radicals, and more especially to makeup compositions of the skin for both the skin and the human body, the fibers Keratin or like nails, eyelashes, eyebrows or hair and lips. Makeup compositions such as free or compacted powders, dye bases, cheek or eyelid make-up, lip carmines, anti-dark circles, blushes, mascaras, eyeliners, lipsticks or eye pencils , or even nail varnishes and make-up products for the body, are constituted of an appropriate vehicle and coloring agents of different natures, intended to confer a certain color to these compositions, before and / or after their application on skin, lips and / or keratin fibers. REF: 29448 These coloring agents can be lacquers, mineral or organic pigments and / or pearlescent pigments or even dyes. In the range of red pigments, those skilled in the cosmetic art have pigments of mineral origin such as red iron oxides or mixtures of brown iron oxide-yellow, and pigments of organic origin. The mineral pigments, and in particular the mineral oxides, have the advantage of being very stable, but they have the drawback of giving colors that are too faint and pale. Organic lacquers have the advantage of imparting bright colors to the compositions, but they are for the most part unstable to light, temperature or pH. Some of these lacquers also have the disadvantage of staining the skin unpleasantly after application, by spilling the dye. The pearlescent pigments allow by themselves to obtain varied colors, but never intense, with iridescent effects but more frequently very weak. On the other hand, certain coloring agents have the disadvantage of generating free radicals in makeup formulas, modifying the reflection of colors and the stability of the compositions, then on the skin after application, which favors cutaneous aging ( appearance of wrinkles, lines, yellowing of the skin). Coloring agents which present this disadvantage are, in particular, the brown-yellow iron hydroxide mixtures sold under the trade name "Sicomet Brun ZP 3569" by BASF, for example, the pigments of organic origin such as Rouge Flaming (Red D & amp;; C No. 36, Color Index 12.08-5) due to the commercial designation DC Red 36W 008 by WACKER, as well as the aluminum lacquer of floxin B on alumina Red D &C No.27 or Outside of Aluminum). Nowadays, to solve this problem, antioxidants are used, such as ethoxyquin. Unfortunately, it is often difficult to find an effective oxidizing agent 100%, taking into account the plurality of ingredients present in makeup compositions. In addition, antioxidant agents frequently generate degradation products (oxidation of the antioxidant agent) which can be troublesome. The present invention has exactly a cosmetic composition of a novel red pigment of intense and saturated color, stable, which has the advantage of generating much less free radicals than the pigments conventionally used, mainly to obtain a red color. Surprisingly, the applicant has found that diketopyrrolopyrroles (abbreviated DPP) could make it possible to limit the production of free radicals, since these have the property of generating very few free radicals, and thus avoid the use of antioxidants in the compositions. In addition, these pigments allow to obtain an intense coloration and in particular a red vermillon, very alive and intense, that does not spill on the skin, stable to the light, to the pH and to the temperature. * More precisely, the invention has for its object a composition for colored topical application, and more especially a cosmetic make-up composition containing a pigment of the formula (A): in which R; and R independently represent a hydrogen atom, an alkyl radical of 1 to 18 carbon atoms, alkenyl of 3 to 12 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, or a phenyl radical optionally substituted by a halogen, and R - and R independently represent a hydrogen atom, an alkyl radical of 1 to 18 carbon atoms, alkoxy of 1 to 4 carbon atoms, a halo radical, a phenyl radical, or a group -S03M with M representing a carbon atom. hydrogen, a metal atom or an ammonium group, the alkyl, alkenylp and alkoxy radicals which may be linear or branched. The radicals R- can be in the 2, 3, 4, 5 or 6 position and preferably in the 4 position. The metal M. can be sodium, potassium or lithium. The alkyl and alkoxy radicals can be linear or branched, and can be chosen mainly from the methyl, ethyl, n- and isopropyl, n-sec-, ter- or isobutyl, n-, sec-, ter- or isopentyl radicals, etc .; the alkenyl radicals can be linear or branched and can be chosen mainly from the radicals allyl, methallyl, 2-butenyl, 2-hexenyl, 3-hexenyl, 2-octenyl, etc. The halogen atom can be chlorine or fluorine. Preferably, Ri and R¿ independently represent a hydrogen atom, a methyl radical or 4-chlorophenyl. Advantageously, R; and R independently represent a hydrogen atom, 4-chloro or 4-tert-butyl. The pigment of the invention can be transparent or opaque and optionally - combined with other pigments to increase the stability of said pigment and of the composition of the invention to light and elements, as mentioned in WOA 98/56859 or improve the power of the color and / or the goniocro attic properties of the crystalline liquid of the multilayer pigments having goniochromatic properties. The manufacture of the diketoarylpyrrolo-pyrrole of the formula. { A) is described -mainly in the Ciba-Geigy documents, European patents EP-A-542669, EP-A-787730, EP-A-787731 and international patent WO 96/08537. Preferably, the "Irgazine red DPP-red BO" cataloged in the color index (abbreviated Cl) Pigment Red 254 No. Cl 56110 is used. It is the pyrrolo (3, 4-c) -pyrrol-1, -dione where the two benzene rings are dehydrogenated in 2.5 and chlorinated in position 4. This compound has the following formula (B): As another "DPP" pigment which can be used in the composition of the invention, mention may be made of: Cromophthalo BPP Roj.o BP P-Cl Pigmento Rojo 254 -No Cl 56110; Chromophthalo DPP Red .BP-C1 Pigment Red 254-No Cl 56110; -Rubber DPP Red 5G-C1 Pigment Red 25.5; -Irgazina DPP Rubina TR-C1 Pigment Red 254; -Rubber DPP Red 5049 B-Cl Pigment Red 270; -Irgazina Orange RA-C1 Pigment Orange 73; To show the property that DPP does not generate free radicals, the applicant has performed an ethylene test according to the procedure described in Article "Ethylene formation from ethionine as a method to evaluate oxygen free radical scavenging and metal inactivation by cosmetics" of J.B. Galey, F. Millecamps and Q.L. Nguyen, In t erna ti onal Journal of Cosme ti c Sci ence, 13, 65-78, 1991. The objective is to compare the behavior of the organic pigment according to the invention, in relation to that of the classic pigments in a photo-oxidation test using iron as a free radical generator.

In the ethylene test inhibition protocol, the FeCl3 used to activate the production of free metals has been replaced by each of the pigments to be tested. The results are given in the following table.

The Fe ^ Cls control at 0.005% is on average at 9000 (arbitrary unit - relative measurement). The higher the amount of ethylene, the greater the production of free radicals. The raw materials of brown iron oxide, yellow (Cl 77491 + Cl 77492) and Flaming red (Cl 12085), are not inert. At low dose, they activate until a certain concentration where the protective effect of pigment begins to take place, while for the DPP the rate of the product is very small in relation to the other two, and does not evolve as a function of the concentration. This pigment can then be sold for use in makeup compositions and solar colored compositions, mainly colors intended for the protection of the skin and / or mucous membranes such as labips, without generating free radicals, and thus limiting the degradation of the skin and / or mucous membranes. The pigment according to the invention can be incorporated into a cosmetic composition mainly of make-up, in an amount that can be easily determined by the person skilled in the art, based on its general knowledge, and which can mainly go from 0.01 to 50% by weight with relation to the weight of the composition, preferably in an amount ranging from 0.5 to 25%. This pigment can also be fixed on a polymer, in particular by grafting or encrusting. The composition of the invention can be presented in the form of a product to be applied on the lips, eyes, skin and / or keratin fibers. It therefore contains a cosmetically acceptable medium, that is to say a medium compatible with all keratin materials such as the skin of both the human body and the face, the nails, the hair, the eyelashes and the eyebrows. This medium can comprise or be present mainly in the form of suspension, dispersion or solution in aqueous solvent or hydroalcoholic medium, possibly thick or even gelled.; emulsion oil in water, water in oil, or multiple; .gel or foam; emulsified gel; dispersion of vesicles mainly of ionic lipids or not; biphasic or multiphasic lotion: spray; free, compacted or melted powder; anhydrous paste. The person skilled in the art will be able to choose the appropriate galenical form, as well as his method of preparation, based on his general knowledge, taking into account on the one hand the nature of the constituents used, mainly on their solubility in the support, and on the other hand part of the application considered for the composition. When the composition according to the invention is presented in the form of an emulsion, it may optionally also comprise a surfactant, preferably in an amount of 0.01 to 30% by weight relative to the total weight of the composition. According to the application considered, the composition may also comprise a film-forming polymer (such as nitrocellulose, hydrocarbon resin and / or silicone). This is mainly the case when it is desired to prepare a varnish-like composition for nails, mascara, eyeliner or. capillary composition of the lacquer type. The polymers can be dissolved or dispersed in the cosmetically acceptable medium, and optionally associated with coalescing agents and / or plasticizers. The composition according to the. invention can also comprise a fatty phase, mainly constituted of liquid fatty substances at room temperature (25 ° C in general) and / or of solid fatty substances at room temperature. such as waxes, pasty fatty substances, gums and their mixtures. As bodies, fatty liquids at ambient temperature, often referred to as oils, which can be used in the invention, there may be mentioned: hydrocarbon oils of animal origin such as perhydrosqualene; vegetable hydrocarbon oils such as liquid triglycerides of fatty acids of 4 to 10 carbon atoms, such as triglycerides of heptanoic or octanoic acids, or even oils of sunflower, corn, soybean, grape seed, sesame seed, apricot, macadamine, castor, avocado, triglycerides of capric / capric acids, jojoba oil, shea butter; linear or branched hydrocarbons of mineral or scientific origin such as paraffin oils and their derivatives, petrolatum, polydecenes, hydrogenated polyisobutene such as parleam; esters and synthesis ethers mainly of fatty acids such as, for example, Purcellin oil, isopropyl myristate, ethyl-2-hexyl palmitate, octyl-2-dadecyl stearate, octyl-2-dodecyl erucate, isostearate isostearyl; hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl alato, triisocetyl citrate, heptanoates, octanoates, decanoates of fatty alcohols; polyol esters such as propylene glycol dioctanoate, nepentyl glycol dieptanoate, diethylene glycol diisononanoate; and the pentaerythritol esters; fatty alcohols having from 12 to 26 carbon atoms such as oxtildodecanon, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol; the partially hydrocarbon and / or silicone fluorinated oils; silicone oils, such as volatile or non-volatile, linear or cyclic polymethylsiloxanes (PDMS), liquid or pasty at room temperature, such as cyclomethicones, dimethicones, which optionally include a phenyl group, such as phenyltrimethicones, phenyltrimethylsiloxydi phenyl siloxanes, di-phenylmethyldimethyl-trisiloxanes, and difzyldimethicones, phenyldimethicones, polymethylphenylsiloxanes; and its mixtures. These oils can be presented from 0 to 100% by weight in relation to their total weight of the fatty phase. The composition according to the invention can, in addition, comprise all the ingredients classically used in the related domains, and more especially in the cosmetic and dermatological domains. These ingredients are in particular chosen from preservatives, aqueous phase thickeners (polysaccharide biopolymers, synthetic polymers) or fat, perfumes, hydrophilic or lipophilic active agents and their mixtures. The amounts of these different ingredients are those conventionally used in the domains, in question, and for example from 0.01% to 20% of the total weight of the composition. The nature of these ingredients and their proportion must be compatible with obtaining the compositions according to the invention, stable, thick and shiny. The composition may also comprise water at a concentration ranging from 0 to 98% of the total weight of the composition. The composition of the invention can, furthermore, comprise a further particular phase, which can be present at a ratio of 0 to 35% by weight of the total composition, preferably from 0.05 to 20%, and which can comprise pigments and / or pearlescent materials and / or fillers used in cosmetic compositions. By pigments, it is to be understood the white or colored particles, mineral or organic, insoluble in the liquid fatty phase, intended to color and / or opaque the composition. By fillers, it should be understood the colorless or white, mineral or synthetic particles, laminar or non-laminar. By nacreous materials, iridescent particles, mainly produced by certain molluscs in their shell or synthesized, must be understood. These fillers and nacreous materials serve mainly to modify the texture of the composition. Pigments other than DPP may be present in the composition in a proportion of 0 to 25% by weight of the final composition, and preferably in a proportion of 2 to 15%. As mineral pigments which can be used in the invention, mention may be made of titanium, zirconium or cerium oxides, as well as zinc, iron or chromium oxides and ferric blue. Among the organic pigments which can be used in the invention, mention may be made of carbon black, and barium, strontium, cralcium and lu cium lacquers. The pearlescent materials may be present in the composition in a proportion of 0 to 20% of the total weight of the composition, preferably at a rate of the order of 1 to 15%. Among the nacreous materials which can be used in the invention, mention may be made of mica coated with titanium oxide, iron oxide, natural pigment or bismuth oxychloride, such as colored titanium mica. The fillers can be present in a proportion of 0 to 35% of the total weight of the composition, preferably from 0.5 to 15%, 3e can mainly mention talc, zinc extract, mica, and kaolin with the powders of Uailon (mainly Orgasol) and polyethylene, Teflon, starch, boron nitride, copolymer microefers such as Expancel (Nobel Industrie), polyrap (Dow Corning) and srystalone resin microspheres (Tospearl from Toshiba, for example) . The composition of the invention may advantageously comprise a solid or pasty fatty phase containing one or more gums and / or one or more waxes. The waxes may be hydrocarbon-based, fluorinated and / or silicone-containing, and of vegetable, mineral, animal and / or synthetic origin. In particular, the waxes have a melting temperature higher than 25 ° C and better still higher than 45 ° C. As the wax to be used in the composition of the invention, mention may be made of beeswax, Carnauba wax or Candelilla wax, paraffin, microcrystalline waxes, ceresin and ozokerite. Synthetic waxes such as polyethylene or Fischer Tropsch waxes, silicone waxes such as alkyl- or alkoxy-dimethicone having from 16 to 45 carbon atoms. The gums are in general of high molecular weight PDMS and the pasty bodies are in general hydrocarbon compounds co or the lanolins and their derivatives, or even the PDMS. The nature and quantity of solid bodies are a function of the mechanical properties and the textures sought. As an indicative, the composition may contain from 0 to 50% by weight of waxes, relative to the total weight of the composition, and better still from 5 to 30% by weight The composition according to the invention i can also comprise one or more organic solders cosmetically acceptable (tolerance, toxicology and tactile sensation acceptable). These organic solvents can represent from 0% to 98% of the total weight of the composition, and can be chosen from the group consisting of the solvents. hydrophilic organic, lipophilic organic solvents ,. the amphiphilic solvents or their mixtures Among the hydrophilic organic solvents, there may be mentioned, for example, the linear or branched lower monoalkols having from 1 to 8 carbon atoms, the polyols, the mono- or dialkyl isosorbide wherein the alkyl groups have 1 to 5 carbon atoms, glycol ethers and fatty esters This composition can have the appearance of a powder, cream, ointment ,. fluid lotion, flexible paste of dynamic viscosity at 25 ° C of the order of 1 to 40 Pa.s, ointment, molten or molded solid, and mainly in bar or in glass. The composition according to the invention can be advantageously used for the. make-up of - the. skin and / or lips and / or keratin fibers according to the nature of the constituents used. In particular, the composition of the invention can be a bar of lipstick or lipstick for lips, a lip gloss (gloss in anglosaxon terminology) usable as it is or to be applied on a film of lipstick for lips, mainly to increase its brilliance and / or color (top coat in Anglo-Saxon terminology). This can also be a basis for solid dye, an anti-wrinkle or eye contouring product, a eyeliner, a mask, a shadow for eyelids, a powder, a blush. These compositions may also contain cosmetic or dermatological active ingredients * with a view to mainly providing a clean or characteristic aspect to the composition. In this way, the composition may contain vitamins and other active agents lipophilic (lanolin, UVA filter) or hydrophilic (moisturizers such as glycerin).

The invention also has as its objective a cosmetic use of the above composition to care for and / or make up and / or protect the skin and / or the lips and / or the keratin fibers as well as using this composition for the preparation of an ointment intended for to treat and / or protect the skin and / or the lips. Another object of the invention is a method of cosmetic treatment of the skin and / or of the lips and / or of the keratin fibers, which consists in applying the defined composition to the skin and / or to the lips and / or the keratin fibers. previously. More specifically, the invention has a lip product or a flush. The composition of the invention can be obtained by heating the different constituents to the melting temperature of the highest waxes, and then casting the molten mixture in a mold (cup or glove finger). This can also be obtained by extrusion as described in the application EP-A-667 146.

The invention also has as its object the use, in a colored cosmetic composition, of a coloring agent as described above, in order to protect the skin and / or the lips and / or the keratin fibers against the damage of the radicals. free and / or to fight against the signs, cutaneous mainly photoinduced aging. These signs of aging are in particular wrinkles, fine lines, loose and / or yellowish skin. The object of the invention is also to provide a method for the cosmetic protection of the skin and / or of the lips and / or of the keratin fibers, against the damage of free radicals and / or to fight against the cutaneous signs of photoinduced aging, which it consists in applying the composition as defined above to the skin and / or the lips and / or the keratin fibers. The examples of compositions are given below illustratively and without limitation.

Example 1; Carmine for Lips Polyethylene Wax 14 g Sesame Oil 78 g DPP Pigment (Formula B) 5 g Titanium Dioxide 3 g Operation mode -Homogenization of the mixture oil + pigment for 45 minutes in an oil bath, -3 successive passes to a three-cylinder shredder, -Homogenization of the mixture oil + pigment for 30 minutes in a bathroom. of oil,-mold in mold at 42 ° C and 30 minutes in the freezer. A carmine is obtained, for lips of an intense vermilion red, high coverage, bright, stable to light, which leaves no trace or scratch (or mark) after the make-up removal.

Example 2: Blush; Talc 38 g Mica 20 g Bismuth oxychloride 8 g Zinc stearate 3 g Nylon powder 20 g DPP pigment (Formula B) 5 g Binder grease (*) as long as it is sufficient for lOOg (*) Mixture of carbon oils containing: -3.6 g triglycerides of capric / caprylic acid -2.0 g of hydrogenated isoparaffin. (non-volatile) -1.0 g of jojoba oil.

Operation mode -Maze all the charges and pigments, -5 minutes in a Lodige device (homogenizer mixer for dust). -Addition of the organic binder, -5 minutes in Lodige appliance, -Pase a. air jet (CHRISPRO), -Fitted to-160 microns.

Example 3: Lip gloss Aqueous dispersion of acrylic polymer / is tyrolean (Neocryl a-105 2 of Zeneca. '20% (Active matter) Acetyltributylate 2.5% Pigment DPP .1.5% Flaming red (CI12085 1.5% Glycerin 1.25% Water cbp 100% . It is noted that . in relation to this date, the best method known by the applicant to carry out the aforementioned invention is that which is clear from the present description of the invention.

Claims (15)

CLAIMS Having described the invention as above, property is claimed as contained in the following:

1. A colored composition for topical application, characterized in that it comprises; a pigment of the formula (A) in which Ri and R? independently represent a hydrogen atom, an alkyl radical of 1 to 18 carbon atoms, alkenyl of 3 to 12 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, phenyl optionally substituted by a halogen, R3 and R4 independently represent an atom of hydrogen / an alkyl radical of 1 to 18 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen or phenyl, or a group -SO3M with M representing a hydrogen atom, a metal atom or an ammonium group, alkyl, alkenyl and alkoxy radicals which may be linear or branched.

2. The composition according to claim 1, characterized in that Ri and R2 independently represent a hydrogen atom, a methyl radical or 4-chlorophenyl.

3. The composition according to claim 1 or 2, characterized in that R3 and R independently represent a hydrogen atom, 4-chloro or 4-tert-butyl.

4. The composition according to any of the preceding claims, characterized in that the coloring agent is pyrrolo- (3, 4-c) -pyrrol-1,4-dione where the two benzene rings are dihydrogenated in positions 2.5 and chlorinated in position 4.

5. The composition according to any of the preceding claims, characterized in that the coloring agent is present at a ratio of 0.01 to 50% by weight relative to the total weight of the composition.

6. The composition according to any of the preceding claims, characterized in that the coloring agent is present at a ratio of 1 to 25% in. weight in relation to the total weight of the composition.

7. The composition according to any of the preceding claims, characterized in that it is presented in the form of a makeup product of the skin, lips and / or keratin fibers of the human being.

8. The composition according to any of the preceding claims, characterized in that it is presented in the form of a nail varnish, mask, eyeliner or hair type composition, lipstick for lips, lip gloss, dye base, anti-wrinkle product , makeup for eyes or eyelids, powder, blush, makeup for body.

9. The composition according to any of the preceding claims, characterized in that it also comprises at least one fatty phase chosen from oils, waxes, gums, pasty fatty substances and their mixtures.

10. The composition according to any of the preceding claims, characterized in that it also contains a further particular phase, which can be presented at a ratio of 0 to 355 of the total weight of the composition.

11. The composition according to any of the preceding claims, characterized in that it is presented in the anhydrous form.

12. The cosmetic use of the composition according to any of the preceding claims, to care for and / or make up and / or protect the skin and / or the lips and / or the keratin fibers.

13. The use of the composition according to any of claims 1 to 11, for the preparation of an ointment intended to treat and / or protect the skin and / or the lips.

14. The use in or for the manufacture of the colored cosmetic composition of a coloring agent of the formula (A), as defined in claims 1 to 4, with a view to protecting the skin and / or the lips and / or keratin fibers against the damages of free radicals and / or to fight against cutaneous signs of aging.

15. The protection procedure. cosmetic of the skin and / or of the lips and / or of the keratin fibers, against the damages of the free radicals and / or to fight against the cutaneous signs of the photoinduced aging, characterized the procedure because it consists of applying on the skin and / or the lips and / or the keratinous fibers the composition according to any of claims 1 to 11. SUMMARY OF THE INVENTION The present invention relates to cosmetic compositions and mainly make-up compositions, which contain a new red pigment of intense and saturated color, not generating free radicals. - This novel pigment is a diketo-pyrrolo pyrrole DPP of the formula: wherein R: and R ^ independently represent a hydrogen atom, an alkyl radical of 1 to 18 carbon atoms, alkenyl of 3 to 12 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, phenyl optionally substituted by a halogen , R3 and R independently represent a hydrogen atom, an alkyl radical of 1 to 18 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen or phenyl, or a group -SO3M with M representing a hydrogen atom, an metal atom or an ammonium group, the alkyl, alkenyl and alkoxy radicals which may be linear or branched. Thanks to this pigment it is possible to protect the skin, lips and keratin fibers from free radicals, without using antioxidants in the composition.