FR2466492A1 - Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid - Google Patents

Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid Download PDF

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FR2466492A1
FR2466492A1 FR7924627A FR7924627A FR2466492A1 FR 2466492 A1 FR2466492 A1 FR 2466492A1 FR 7924627 A FR7924627 A FR 7924627A FR 7924627 A FR7924627 A FR 7924627A FR 2466492 A1 FR2466492 A1 FR 2466492A1
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Prior art keywords
coloring
amino acid
ketone
aldehyde
agent
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FR2466492B1 (en
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Societe National Elf Aquitaine
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Societe National Elf Aquitaine
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Priority to FR7924627A priority Critical patent/FR2466492A1/en
Priority to GB8031407A priority patent/GB2062016B/en
Priority to IT25076/80A priority patent/IT1133801B/en
Priority to US06/193,397 priority patent/US4293543A/en
Priority to DE19803037497 priority patent/DE3037497A1/en
Publication of FR2466492A1 publication Critical patent/FR2466492A1/en
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated

Abstract

In dyeing keratin-contg. substances or tissues with a dyestuff or co-reagent having a ketone- or aldehyde function, colour formation is intensified by also applying a sulphoxy gp.-contg. aminoacid, (I), before, during or after treatment with the dye or co-reagent. The materials can be used (1) in cosmetics, for skin-tanning and for dyeing nails and hair, (2) for dyeing furs and feathers and (3) for colouring horn, scale or tortoise-shell articles. A uniform shade is obtd. The colour resists washing and is developed more quickly. (I) are more soluble in water than thioaminoacids, whereby more solns. can be used. The sulphoxide function allows penetration and fixation of (I), and derived dye complex, in horn layer. (I)-derived compsns. are odourless.

Description

L'invention concerne un procédé et une composition pour la coloration de substances contenant de la kératine, notamment de tissus tels que peau et substances comme cheveux, poils, ongles, plumes, écailles, sabots, cornes, etc. Elle apporte un perfectionnement à la coloration de telles matières. The invention relates to a method and a composition for coloring substances containing keratin, in particular tissues such as skin and substances such as hair, hair, nails, feathers, scales, hooves, horns, etc. It brings an improvement to the coloring of such materials.

Des produits pour le développement de la coloration de la peau humaine, appelée couramment bronzage, par réaction de ces produits avec les acides aminés naturels constituant le tissu humain, sont bien connus dans l'art ; aussi ont-ils donné lieu à un certain nombre de travaux qui ont conduit à l'utilisation de produits non nocifs, permettant de développer sur la peau une coloration d'aspect naturel. Parmi les produits les plus employés à l'heure actuelle, ce sont des composés à fonction cétone ou aldéhyde, renfermant le plus souvent des fonctions alcool. Ainsi utiliset-on, dans les différentes compositions de bronzage, des substances telles que dihydroacétone, glycéraldéhyde, érythrulose, alloxane, aldéhyde tartrique, aldéhy- de-diméthoxy-succinique ou benzyl-amino-hydroxy-succinique.Ces diverses substances donnent une coloration brun par combinaison avec les amino-acides présents dans le sebum ou dans la première couche cornée de l'épiderme, selon un mécanisme connu, à savoir la réaction de Maillard. Cependant, la répartition et la nature des amino-acides de l'organisme ne sont pas uniformes à la surface de la peau : l'intensité et la nuance de la teinte obtenue varient donc beaucoup d'un endroit à l'autre de la peau traitée. Products for the development of human skin coloring, commonly called tanning, by reaction of these products with the natural amino acids constituting human tissue, are well known in the art; therefore they have given rise to a certain number of studies which have led to the use of non-harmful products, making it possible to develop a natural-looking coloration on the skin. Among the most widely used products at the present time, they are compounds with a ketone or aldehyde function, most often containing alcohol functions. Thus, in the various tanning compositions, substances such as dihydroacetone, glyceraldehyde, erythrulose, alloxane, tartaric aldehyde, aldehyde-dimethoxy-succinic or benzyl-amino-hydroxy-succinic are used. These various substances give a brown coloring by combination with the amino acids present in the sebum or in the first horny layer of the epidermis, according to a known mechanism, namely the Maillard reaction. However, the distribution and the nature of the amino acids of the organism are not uniform on the surface of the skin: the intensity and the shade of the shade obtained thus vary much from one place to another of the skin. processed.

D'autre part, les colorations, obtenues suivant l'art connu, ne résistent pas bien au lavage et s'atténuent assez rapidement avec le temps. I1 y a également lieu de noter l'inconvénient de la durée souvent trop longue du développement de la teinte, durée pendant laquelle la substance active peut s'éliminer par simple immersion dans l'eau ou par sudation ; elle peut également tacher des vêtements imprégnés de sebum.On the other hand, the colorings obtained according to the known art do not resist washing well and fade relatively quickly over time. There is also reason to note the disadvantage of the often too long duration of the development of the color, duration during which the active substance can be eliminated by simple immersion in water or by sweating; it can also stain clothing impregnated with sebum.

La présente invention apporte un perfectionnement qui permet d'éviter les inconvénients sus-indiqués : elle rend possible en effet l'obtention d'une coloration uniforme sur toute la surface traitée, résistant mieux au lavage et se développant plus rapidement que dans les cas de compositions classiques. De plus, le procédé et la composition, suivant l'invention, s'appliquent non seulement à la peau humaine, mais aux differents phanères humains et animaux. L'invention est ainsi utilisable en pelleterie, dans le traitement de plumes, aussi bien que pour les ongles et la coiffure. The present invention provides an improvement which makes it possible to avoid the abovementioned drawbacks: it in fact makes it possible to obtain a uniform coloring over the entire treated surface, better resistant to washing and developing more rapidly than in the case of classic compositions. In addition, the method and composition according to the invention apply not only to human skin, but to the various human and animal dander. The invention can thus be used in furs, in the treatment of feathers, as well as for nails and hairdressing.

La présente invention résulte de la constatation inattendue que la coloration des substances kératiniques ou tissus, par des composes à fonctions cétone ou aldéhyde, peut être in tensifiée par l'apport d'un acide aminé à la substance ou au tissu traité. Cet apport peut avoir lieu peu avant le traitement avec l'agent de coloration lui-même, peu après ce traitement ou bien simultanément avec lui. On constate alors les améliorations de la tenue de la coloration, indiquées plus haut. The present invention results from the unexpected observation that the coloring of keratinous substances or tissues, by compounds having ketone or aldehyde functions, can be increased by the addition of an amino acid to the substance or to the treated tissue. This contribution can take place shortly before the treatment with the coloring agent itself, shortly after this treatment or else simultaneously with it. We then observe the improvements in the behavior of the coloration, indicated above.

Le procédé suivant l'invention consiste à traiter la substance ou le tissu renfermant de la kératine avec une so- lution d'acide aminé avant, pendant ou après l'application d1 un composé aldéhydique ou cétonique, agent de coloration appelé également co-réactif. The process according to the invention consists in treating the substance or the tissue containing keratin with an amino acid solution before, during or after the application of an aldehyde or ketonic compound, a coloring agent also called a co-reactive agent. .

Suivant un trait préféré de l'invention, l'acide aminé est choisi parmi ceux dont la molécule contient du soufre, comme c'est le cas de la cysteine de la cystine ou de la méthionine libres ou combinées ; des résultats particulièrement favorables sont obtenus avec les sulfoxydes correspondants de ces produits, sulfoxyde de cysteine, mono et disulfoxyde de cystine et particulièrementtavec le sulfoxyde de méthionine. According to a preferred feature of the invention, the amino acid is chosen from those in which the molecule contains sulfur, as in the case of free or combined cysteine or cystine or methionine; particularly favorable results are obtained with the corresponding sulfoxides of these products, cysteine sulfoxide, mono and cystine disulfoxide and particularly with methionine sulfoxide.

La composition, pour la réalisation du procédé, suivant l'invention, est constituée par un ensemble de deux solutions ou dispersions dont une renferme l'agent de coloration classique ou coréactif, tandis que la seconde contient un ou plusieurs acides aminés dissous dans l'eau. La solution ou dispersion de l'agent de coloration lui-même peut comprendre les différents adjuvants habituels, tels que corps gras, alcools supérieurs, tensio-actif, etc., dont la nature et les proportions varient d'ailleurs avec la nature du tissu ou de la substance à traiter, autrement dit, qutil s'agisse de colorer la peau, les cheveux, des plumes, de la corne, etc. les adjuvants de l'agent du co-réactif de coloration choisis selon la technique connue en soi, qutil n'est pas utile de décrire ici. The composition for carrying out the process according to the invention consists of a set of two solutions or dispersions, one of which contains the conventional or co-reactive coloring agent, while the second contains one or more amino acids dissolved in the water. The solution or dispersion of the coloring agent itself can comprise the various usual adjuvants, such as fatty substances, higher alcohols, surfactant, etc., the nature and proportions of which also vary with the nature of the fabric. or the substance to be treated, in other words, whether it is coloring the skin, hair, feathers, horn, etc. the adjuvants of the coloring co-reagent agent chosen according to the technique known per se, which it is not useful to describe here.

En ce qui concerne l'acide aminé, il peut être formulé, seul, sous forme de solution ou d'émulsion, notamment comme lait ou crème, mais il peut être utile de lui adjoindre également des agents tensio-actifs, des émollients, des substances filtrant les rayons U.V., des composés facilitant la pénétra tion dans les tissus organiques. As regards the amino acid, it can be formulated, alone, in the form of a solution or emulsion, in particular as milk or cream, but it may be useful to also add to it surface-active agents, emollients, UV-filtering substances, compounds that facilitate penetration into organic tissue.

Les deux solutions ou dispersions sont destinées à titre mélangées au moment de l'emploi ou bien à être appliquées, sur la matière à traiter, successivement l'une après l'autre. The two solutions or dispersions are intended as a mixture at the time of use or else to be applied, on the material to be treated, successively one after the other.

Bien que les proportions des produits à employer puissent être très variées, 1 à 10 moles du co-réactif cétonique ou aldéhyde dique pour l à 10 moles d'amino-acide, une forme d'exécution préférée de l'invention consiste à employer 1 mole du co-réac tif cétonique ou aldéhydique pour 1 mole d'amino-acide.Although the proportions of the products to be used can be very varied, 1 to 10 moles of the ketone or aldehyde co-reactant for 1 to 10 moles of amino acid, a preferred embodiment of the invention consists in using 1 mole of the keto or aldehyde co-reagent per 1 mole of amino acid.

Comme déjà indiqué plus haut, l'invention peut entre pratiquée avec les différentes cétones et aldéhydes renfermant des groupes hydroxyle ou -NH, en particulier la di-hydroxy-1,3propanone-2

Figure img00030001

la tri-hydroxy-1,3,4-butanone-2 HOCH2
Figure img00030002

(erythrulose), di-hydroxy-2,3 propanal-l (gycéraldéhyde)
Figure img00030003

alloxane
Figure img00030004

di-hydroxy-2,3-dibutanal-1,4
Figure img00030005

aldéhyde tartre que) et d'autres corps à fonctions aldéhyde ou cétone, connus pour présenter des propriétés de "bronzage" de la peau.As already indicated above, the invention can be practiced with the various ketones and aldehydes containing hydroxyl or -NH groups, in particular di-hydroxy-1,3propanone-2
Figure img00030001

tri-hydroxy-1,3,4-butanone-2 HOCH2
Figure img00030002

(erythrulose), di-hydroxy-2,3 propanal-l (gycéraléhéhyde)
Figure img00030003

alloxane
Figure img00030004

di-hydroxy-2,3-dibutanal-1,4
Figure img00030005

aldehyde tartar as) and other bodies with aldehyde or ketone functions, known to exhibit "tanning" properties of the skin.

En ce qui concerne les acides aminés convenant à la réalisation de l'invention, ils peuvent être choisis parmi les différents amino-acides, surtout basiques, notamment arginine ou lysine ; peuvent être également employés des amino-acides tels que glycine, histidine, tyrosine, glutamine, sérine, etc. As regards the amino acids suitable for carrying out the invention, they can be chosen from the various amino acids, especially basic ones, in particular arginine or lysine; amino acids such as glycine, histidine, tyrosine, glutamine, serine, etc. can also be used.

Conviennent particulièrement bien les thio-amino-acides à sa voir cystéine, cystine, méthionine et leurs sulfoxydes corresw pondants, sulfoxyde de cystéine, mono et disulfoxyde de cystine, et tout particulièrement le sulfoxyde de méthionine

Figure img00030006

en ettet, cet amlno-aclue est non toxique, si bien qu'- il est utilisé dans l'alimentation au même titre que la méthionine. Sa solubilité dans l'eau est très grande, ce qui facilite sa mise en oeuvre et favorise la réaction avec les substances carbonylées elles-mtmes hydrosolubles. La présence de la fonction sulfoxyde permet la pénétration et la fixation de l'aminoacide et du complexe coloré qui en dérive, dans la couche cornée.Particularly suitable are thio-amino acids, see cysteine, cystine, methionine and their corresponding sulfoxides, cysteine sulfoxide, cystine mono and disulfoxide, and especially methionine sulfoxide
Figure img00030006

in fact, this amlno-aclue is non-toxic, so that it is used in food in the same way as methionine. Its solubility in water is very high, which facilitates its implementation and promotes the reaction with the carbonyl substances themselves water-soluble. The presence of the sulfoxide function allows the penetration and fixation of the amino acid and of the colored complex which is derived therefrom, in the stratum corneum.

Enfin les préparations faites à partir de cet amino-acide sont exemptes d'odeur.Finally the preparations made from this amino acid are free of odor.

L'invention est illustrée par les exemples non limitatifs qui suivent. The invention is illustrated by the following nonlimiting examples.

EXEMPLE I
On prépare deux solutions aqueuses, tamponnées à pN 7 avec du phosphate à 0,5 M : la première de ces solutions contient 0,1 mole d'amino-acide par litre, tandis que la seconde est à 2 moles de dihydroxy-acétone,

Figure img00040001

appelée DHA dans la suite de la présente description.EXAMPLE I
Two aqueous solutions are prepared, buffered to pN 7 with 0.5 M phosphate: the first of these solutions contains 0.1 mole of amino acid per liter, while the second is 2 moles of dihydroxyacetone,
Figure img00040001

called DHA in the remainder of this description.

Les deux solutions sont mélangées à raison de 3,6 volumes de so- lution d'amino-acide pour 0,4 volume de solution cétonique, ce qui représente 2,22 moles de cétone par mole d'acide aminé. Le mélange est maintenu à 320C et l'évolution de sa teinte est suivie par la mesure de la densité optique après des temps s'éChelon- nant entre 24 et96 heures. Comme le complexe coloré ne présente pas de maximum dans le domaine visible, les mesures sont effectuées dans l'ultraviolet très proche, à 420 nm, sur le mélange sus-indiqué, dilué au 1/10. The two solutions are mixed in an amount of 3.6 volumes of amino acid solution per 0.4 volume of ketone solution, which represents 2.22 moles of ketone per mole of amino acid. The mixture is maintained at 320C and the evolution of its color is followed by the measurement of the optical density after times ranging from 24 to 96 hours. As the colored complex does not have a maximum in the visible range, the measurements are carried out in very close ultraviolet, at 420 nm, on the above-mentioned mixture, diluted to 1/10.

Le tableau ci-après donne les densités optiques trouvées pour les différents mélanges ; ce sont les moyennes de 3 ou 4 mesures. Dans la colonne verticale des résultats après 3 h, on a porté les densités optiques mesurées sur le mélange non dilué, tandis que les autres colonnes concernent les liquides dilués au 1/10. M désigne le mélange dans lequel I' amino-acide est de la méthionine.The table below gives the optical densities found for the various mixtures; these are the means of 3 or 4 measurements. In the vertical column of the results after 3 h, the optical densities measured are plotted on the undiluted mixture, while the other columns relate to liquids diluted to 1/10. M denotes the mixture in which the amino acid is methionine.

S correspond au mélange dont l'amino-acide est le sulfoxyde de méthionine.S corresponds to the mixture of which the amino acid is methionine sulfoxide.

Ak désigne le mélange des 16 amino-acides présents dans la couche conjonctive du derme, c'est-à-dire-un-ensemble d'acides aminés, dans lequel prédominent la sérine et la citrulline (composition déterminée par Spier et Pascher).  Ak denotes the mixture of the 16 amino acids present in the connective layer of the dermis, that is to say, a set of amino acids, in which serine and citrulline predominate (composition determined by Spier and Pascher).

Pur Dilué au 1/10
3h 24h 48h 72h 96h
M 0,035 0,14 0,24 0,34 0,30
S 0,065 0,20 0,37 0,45 0,45
AA 0,065 0,16 0,27 0,37 0,37
On voit que le sulfoxyde de méthionine (ligne S) ajouté à de la dihydroxy-acétone fait évoluer la coloration du mélange plus rapidement que ne le font les acides aminés naturels (AA), et il conduit à une intensité finale grandement plus élevée :densité optique 0,45 après 72 h au lieu de 0,37.Pure Diluted 1/10
3h 24h 48h 72h 96h
M 0.035 0.14 0.24 0.34 0.30
S 0.065 0.20 0.37 0.45 0.45
AA 0.065 0.16 0.27 0.37 0.37
We see that the methionine sulfoxide (line S) added to dihydroxy-acetone changes the color of the mixture more quickly than do the natural amino acids (AA), and it leads to a much higher final intensity: density optical 0.45 after 72 h instead of 0.37.

EXEMPLE 2
Des essais d'application surpeau de sujets volontaires ont été effectués avec les deux crèmes suivantes, dont les compositions sont indiquées en poids.EXAMPLE 2
Application tests on the skin of voluntary subjects were carried out with the following two creams, the compositions of which are indicated by weight.

Crème 1
1 Mondodipalmito stéarate de polyoxyéthylène glycol .. 6
Acide stéarique ......................................... 1
Alcool cétylique ........................................ 2
Glycérides oléiques polyoxyéthylènes .................... 5 Myristate d'isopropyle ......................... 5
19
Conservateur : ester de l'acide parahydroxy
II benzoïque ............................................ 0,15
Sulfoxyde de méthionine ............................... 4,3
Eawu................................................... 65,5
69,95
La solution aqueuse II est introduite dans la dispersion grasse
I sous agitation modérée, après avoir été portées toutes deux à 700C. Cream 1
1 Mondodipalmito polyoxyethylene glycol stearate. 6
Stearic acid ......................................... 1
Cetyl alcohol ........................................ 2
Polyoxyethylene oleic glycerides .................... 5 Isopropyl myristate ...................... ... 5
19
Preservative: ester of parahydroxy acid
II benzoic ............................................ 0.15
Methionine sulfoxide ............................... 4.3
Eawu ................................................. .. 65.5
69.95
The aqueous solution II is introduced into the fatty dispersion
I with moderate agitation, after having both been brought to 700C.

Crème 2
t Monodipalmitostéarate de polyéthylène glycol ............ 8
I Alcool cétylique .............................................. 1
Huile de vaseline ............................................. 6
Lanoline 2 .2
17
Glycérine e 3,2
Il @ Conservateur : ester de l'acide parahydroxy
benzoïque ......................................... 0,15
Eau ................................................ 6,3
9,65
Les deux mélanges I et II sont chauffés à 700C, après quoi, on verse la solution II dans la dispersion grasse I sous agitation modérée ; dans le mélange ainsi obtenu, on introduit 0,56 partie en poids d'agent de coloration, la dihydroxy-acétone (DHA).La crème 1 puis la crème 2 sont appliquées successivement sur certai- nes parties de la peau de 10 patients bénévoles, à raison de 7,5 mg par cm2. Sur des zones témoins, on étend seulement de la crème 2 qui contient de l'agent développant la coloration.Cream 2
t Polyethylene glycol monodipalmitostearate ............ 8
I Cetyl alcohol .............................................. 1
Vaseline oil ............................................. 6
Lanolin 2 .2
17
Glycerin 3.2
Il @ Conservative: ester of parahydroxy acid
benzoic ......................................... 0.15
Water ................................................ 6 , 3
9.65
The two mixtures I and II are heated to 700C, after which solution II is poured into the fatty dispersion I with moderate stirring; 0.56 part by weight of coloring agent, dihydroxy acetone (DHA) is introduced into the mixture thus obtained. Cream 1 and then cream 2 are applied successively to certain parts of the skin of 10 volunteer patients , at a rate of 7.5 mg per cm2. On control zones, only cream 2 which contains coloring developing agent is spread.

Les résultats de ces essais sont résumés dans le tableau qui suit.The results of these tests are summarized in the following table.

On peut observer que, sur 10 patients, la cétone seule donne une coloration moyenne après 3 heures, par contre, par l'application préalable de la crème 1,qui contient du sulfoxyde de méthionine, on obtient, après 3 heures, une coloration très forte sur deux patients, forte sur 6 et moyenne sur 2. Les mesures après 2 et 5 jours montrent une bien meilleure tenue au lavage des zones qui ont reçu l'application de sulfoxyde de méthionine. It can be observed that, out of 10 patients, the ketone alone gives an average coloration after 3 hours, on the other hand, by the prior application of the cream 1, which contains methionine sulfoxide, a very discolouration is obtained after 3 hours strong in two patients, strong in 6 and medium in 2. Measurements after 2 and 5 days show a much better resistance to washing in the areas which have received the application of methionine sulfoxide.

(Voir le tableau à la page 8 ). (See table on page 8).

EXEMPLE 3
Deux zones de 9 carrés de 2 x 2 cm sont repérées sur la cuisse.EXAMPLE 3
Two areas of 9 squares of 2 x 2 cm are identified on the thigh.

L'une sert de témoin et reçoit la crème 2 à la DHA de l'exemple 2, l'autre est la zone d'essais et reçoit la crème 1 au sulfoxyde de méthionine, puis la crème 2 à la DHA. One serves as a control and receives cream 2 with DHA from Example 2, the other is the test zone and receives cream 1 with methionine sulfoxide, then cream 2 with DHA.

On enduit un carré de chaque zone toutes les heures pendant 9 heures avec 30 mg de crème et on photographie l'ensemble 9 heures après la première application.A square of each zone is coated every hour for 9 hours with 30 mg of cream and the whole is photographed 9 hours after the first application.

Conditions opératoires pour la photographie :
Film pour diapositives 160 ASA (lumière artificielle).Operating conditions for photography:
Film for slides 160 ASA (artificial light).

Eclairage par 4 lampes de 250 W chacune, situées à 50 cm environ de la surface à photographier.Lighting by 4 lamps of 250 W each, located approximately 50 cm from the surface to be photographed.

Appareil CANON FTP monté sur pied et situé à 60cm du sujet.CANON FTP device mounted on a stand and located 60cm from the subject.

Vitesse d'obturation : 1/250
Diaphragme 6,6
La surface de la peau est recouverte dtun cache en tissu blanc ne laissant apparattre que les zones traitées.Shutter speed: 1/250
Diaphragm 6.6
The surface of the skin is covered with a white cloth cover, leaving only the treated areas to appear.

Mesures : l'intensité de la coloration de chaque carré est mesurée par la mesure de densité optique sur les diapositives, à l'aide d'un photodensitomètre. Measurements: the intensity of the coloring of each square is measured by measuring the optical density on the slides, using a photodensitometer.

Le diagramme ci-joint met en évidence le développement plus rapide de la coloration et l'intensité beaucoup plus forte de celle-ci lorsque l'on fait une application préalable de la crème contenant le sulfoxyde de méthionine.The attached diagram highlights the faster development of the coloration and the much stronger intensity when the cream containing methionine sulfoxide is applied beforehand.

EXEMPLE 4
Deux sujets exempts de bronzage, l'un blond, l'autre brun, ont été intégralement traités avec la crème 1 de l'exemple 2 contenant du sulfoxyde de méthionine, puis avec la crème 2 à la DHA.EXAMPLE 4
Two subjects without tanning, one blond, the other brown, were treated in full with cream 1 of Example 2 containing methionine sulfoxide, then with cream 2 with DHA.

Après 3 heures, la coloration avait atteint son maximum dans les deux cas et présentait une excellente uniformité d'intensité et de nuance, à l'exception de quelques rares zones particulièrement cornées,telles que les coudes, les genoux et les talons.After 3 hours, the coloring had reached its maximum in both cases and exhibited excellent uniformity of intensity and nuance, with the exception of a few particularly horny areas, such as the elbows, knees and heels.

EXEMPLE 5
Un sujet atteint de vitiligo a étê traité sur les zones de dépigmentation avec la crème 1 au sulfoxyde de méthionine, puis avec la crème 2 contenant la DHA.EXAMPLE 5
A subject with vitiligo was treated on the depigmentation zones with methionine sulfoxide cream 1, then with cream 2 containing DHA.

Après 3 heures, une teinte voisine de celle des zones périphériques s'est développée, atténuant l'effet disgracieux de la maladie.After 3 hours, a shade close to that of the peripheral zones has developed, reducing the unsightly effect of the disease.

EXEMPLE 6
Une mèche de teinte blond clair a été immergée dans une solution aqueuse à 5% de sulfoxyde de méthionine, puis dans une solution aqueuse à 2% de DHA.EXAMPLE 6
A lock of light blond color was immersed in a 5% aqueous solution of methionine sulfoxide, then in a 2% aqueous solution of DHA.

Après 5 heures, une teinte brun foncé s'est développée ; elle résiste à l'application d'un shampooing. After 5 hours, a dark brown hue developed; it resists the application of a shampoo.

Sujet Temps apparition coloration Intensité aprés 3 h. Intensité après 48 h. Intensité après 5
jours, lavage
chaque jour
Zone I Zone II Zone I Zone II Zone I Zone II Zone I Zone II 1 1 h 1/2 h ++ ++++ ++ ++++ + +++ 2 1h30 1h ++ ++++ ++ ++++ + +++ 3 2h 1h30 ++ +++ ++ +++ + ++ 4 " " ++ +++ ++ +++ + ++ 5 " " ++ +++ ++ +++ + ++ 6 " " ++ +++ ++ +++ + ++ 7 " " ++ +++ ++ +++ + ++ 8 " " ++ +++ ++ +++ + ++ 9 3h 3h ++ ++ 0 0 0 0 10 " " ++ ++ 0 0 0 0 Subject Color appearance time Intensity after 3 h. Intensity after 48 h. Intensity after 5
washing days
every day
Zone I Zone II Zone I Zone II Zone I Zone II Zone I Zone II 1 1 1/2 hrs ++ ++++ ++ ++++ + +++ 2 1h30 1h ++ ++++ ++ ++++ + +++ 3 2h 1.5 hrs ++ +++ ++ +++ + ++ 4 "" ++ +++ ++ +++ + ++ 5 "" ++ +++ ++ +++ + ++ 6 "" ++ +++ ++ +++ + ++ 7 "" ++ +++ ++ +++ + ++ 8 "" ++ +++ ++ ++ + + ++ 9 3h 3h ++ ++ 0 0 0 0 10 "" ++ ++ 0 0 0 0

Claims (10)

ration. ration. avant, pendant, ou après le traitement avec l'agent de colo before, during, or after treatment with the colo agent caractérisé en ce qu'un acide aminé est apporté à ces derniers characterized in that an amino acid is provided to them veloppement de la coloration de cette substance ou du tissu, development of the coloring of this substance or of the tissue, co-réactif à fonction cétone ou aldéhyde, favorisant le dé co-reagent with ketone or aldehyde function, promoting de fermant de la kératine au moyen d'un agent de coloration ou closing keratin with a coloring agent or REVENDICATION5 1. Procédé pour la coloration dtune substance ou d'un tissu renCLAIMS5 1. Method for coloring a substance or a renown tissue 2. Procédé suivant la revendication 1, dans lequel l'agent de co2. The method of claim 1, wherein the co-agent loration ou co-réactif est une cétone ou aldéhyde portant des loration or co-reactant is a ketone or aldehyde carrying hydroxyles ou/et des groupes -NH, caractérisé en ce que 1'aci-  hydroxyls and / or -NH groups, characterized in that the acid de aminé contient du soufre dans sa molécule et est constitué of amino contains sulfur in its molecule and is made up par de la méthionine, de la cystéine ou de la cystine, libres with methionine, cysteine or cystine, free ou combinées. or combined. 3. Procédé suivant la revendication 1 ou 2, caractérisé e6e que3. Method according to claim 1 or 2, characterized e6e that l'acide aminé est le sulfoxyde de cystéine, le mono et le di the amino acid is cysteine sulfoxide, mono and di sulfoxyde de cystine ou le sulfoxyde de méthionine. cystine sulfoxide or methionine sulfoxide. 4. Procédé suivant une des revendications 1 à 3, caractérisé en4. Method according to one of claims 1 to 3, characterized in ce que les proportions d'agent de coloration et d'acide aminé what the proportions of coloring agent and amino acid sont telles qu'il se retrouve sur la substance ou tissu à are such that it is found on the substance or tissue to be traiter 1 à 10 moles de cet agent pour 1 à 10 moles d'acide treat 1 to 10 moles of this agent for 1 to 10 moles of acid aminé et de préférence I mole de co-réactif pour 1 mole d' amine and preferably I mole of co-reagent for 1 mole of acide aminé. amino acid. 5. Composition pour la réalisation du procédé suivant une des5. Composition for carrying out the process according to one of the revendications 1 à 4, caractérisée en ce qu'elle comprend deux Claims 1 to 4, characterized in that it comprises two dissolutions ou dispersions, dont la première contient l'agent dissolutions or dispersions, the first of which contains the agent de coloration ou co-réactif, notamment un composé cétonique coloring or co-reactive, in particular a ketone compound ou aldéhydique, et la seconde un acide aminé, plus particuliè or aldehyde, and the second an amino acid, more specifically rement thio-amino-acide. thio-amino acid. 6. COmposition suivant la revendication 5, caractérisée en ce6. Composition according to claim 5, characterized in that que l'acide aminé est du sulfoxyde de méthionine. that the amino acid is methionine sulfoxide. 7. Composition suivant la revendication 5 ou 6, caracténsée en7. Composition according to claim 5 or 6, characterized in ce qu'elle renferme 1 à 10 moles d'un composé cétonique ou what it contains 1 to 10 moles of a ketone compound or aldéhydique susceptible de colorer la peau, pour 1 à 10 moles aldehyde capable of coloring the skin, for 1 to 10 moles d'acide aminé et de préférence 1 mole de co-réactif pour t amino acid and preferably 1 mole of co-reactant for t mole d'acide aminé. mole of amino acid. 8. Application du procédé suivant uredes revendications 1 à 48. Application of the method according to claims 1 to 4 et de la composition, suivant une des revendications 5 à 7, and of the composition according to one of claims 5 to 7, au bronzage de la peau humaine, à la coloration des cheveux tanning of human skin, coloring of hair et à celle des ongles. and that of the nails. 9. Application du procédé suivant une des revendications 1 à9. Application of the method according to one of claims 1 to 4 et de la composition suivant une des revendications 5 à 7, 4 and of the composition according to one of claims 5 to 7, en pelleterie et à la coloration des plumes. in furskin and feather coloring. à la coloration d'articles en corne ou en écaille.  the coloring of horn or tortoiseshell articles. 4 et de la composition suivant une des revendications 5 à 7, 4 and of the composition according to one of claims 5 to 7, 10.Application du procédé suivant une des revendications 1 à 10.Application of the method according to one of claims 1 to
FR7924627A 1979-10-03 1979-10-03 Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid Granted FR2466492A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
FR7924627A FR2466492A1 (en) 1979-10-03 1979-10-03 Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid
GB8031407A GB2062016B (en) 1979-10-03 1980-09-29 Process and composition for the colouration of keratin-containing substances
IT25076/80A IT1133801B (en) 1979-10-03 1980-10-02 PROCEDURE AND COMPOSITION FOR THE COLORING OF SUBSTANCES CONTAINING KERATIN
US06/193,397 US4293543A (en) 1979-10-03 1980-10-02 Process and composition for the coloration of keratin-containing substances
DE19803037497 DE3037497A1 (en) 1979-10-03 1980-10-03 METHOD AND COMPOSITION FOR COLORING SUBSTANCES CONTAINING KERATIN, AND USE THEREOF

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FR7924627A FR2466492A1 (en) 1979-10-03 1979-10-03 Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid

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FR2466492B1 FR2466492B1 (en) 1983-04-22

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