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WO1993006817A1 - Cysteamine-based process for perming hair without generating unpleasant odours - Google Patents

Cysteamine-based process for perming hair without generating unpleasant odours Download PDF

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Publication number
WO1993006817A1
WO1993006817A1 PCT/FR1992/000916 FR9200916W WO9306817A1 WO 1993006817 A1 WO1993006817 A1 WO 1993006817A1 FR 9200916 W FR9200916 W FR 9200916W WO 9306817 A1 WO9306817 A1 WO 9306817A1
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WO
WIPO (PCT)
Prior art keywords
hair
compound
composition
mercaptan type
aqueous composition
Prior art date
Application number
PCT/FR1992/000916
Other languages
French (fr)
Inventor
Henri Samain
Claude Dubief
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by L'oreal filed Critical L'oreal
Publication of WO1993006817A1 publication Critical patent/WO1993006817A1/en

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Classifications

    • 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
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures

Definitions

  • cysteamine does not generate an unpleasant odor.
  • the subject of the present invention is a new process for permanent deformation of the hair using, as reducing agent for cysteamine, this process comprising, between the reduction step and the oxidation step, a particular treatment making it possible to combat the residual unpleasant odor permeating the hair.
  • the conventional technique for achieving permanent hair deformation consists in firstly opening the disulfide bridges of the keratin using a composition containing a reducing agent (reduction step), then, after having preferably rinsed the hair, to reconstitute in a second time said disulfide bonds by applying to the hair under tension, an oxidizing composition (oxidation step also called fixing) so as to give the hair the desired final shape.
  • a composition containing a reducing agent reduction step
  • an oxidizing composition oxidation step also called fixing
  • This technique of permanent deformation of the hair makes it possible indifferently to carry out either a waving of the hair or a straightening or straightening.
  • compositions for carrying out the first stage of a perming operation are generally in the form of lotions, creams, gels or powders to be diluted in a liquid support, and contain, as reducing agent, preferably a thiol .
  • cysteamine or 2-amino ethanethiol has proved to be particularly favorable for obtaining good curling of the hair, but it has been found that the hair thus treated developed sometimes, after a week to a month, a very unpleasant smell.
  • This bad odor is more particularly perceptible when the treated hair is in the wet state or in a humid environment.
  • the appearance of bad smells is particularly favored by a hot and humid climate or by a tendency of the subject to secrete a lot of sebum.
  • cysteamine and also its salts are generally not used as a reducing agent in a process of permanent deformation of the hair.
  • the present invention therefore relates to a process for permanent deformation of the hair comprising a reduction step using cysteamine or one of its salts and an oxidation step, this process being characterized in that between the reduction step and the step
  • an aqueous composition is applied to the hair of a compound of mercaptan type other than cysteamine having a good curling efficiency, to combat the unpleasant residual odor permeating the hair.
  • tbioglycolic acid and its salts can be used according to the invention, tbioglycolic acid and its salts, cysteine,
  • -N- (2-mercapto-ethyl) propionamide p-mercaptopropionic acid and its derivatives, homocysteamine, thiolactic acid, thioglycerol, 2-amino hydrochloride N- (2-mercapto-ethyl) acetamide.
  • thioglycolic acid and its salts, cysteine, acid are used.
  • the compound of the mercaptan type is used at a concentration of between 2 and 20% and preferably between 4 and 15% relative to the total weight of the aqueous composition.
  • the pH of the composition should preferably be between 7.5 and 9.5 and preferably between 8.5 and 9.5.
  • the aqueous composition of the mercaptan type compound must have a crimping efficiency, expressed in radius of curvature, of less than 12 mm for a curler with a diameter of 9 mm.
  • the crimping efficiency is determined according to the following protocol:
  • the hair is rolled out, left to act for another 5 min and then rinsed with water.
  • the mean radius of curvature of the undulations obtained is measured.
  • the effectiveness of the mercaptan tested is greater the smaller the radius of curvature.
  • the hair is rinsed with water before the application of the composition containing the compound of the mercaptan type.
  • the aqueous composition containing the mercaptan-type compound can of course contain various cosmetic ingredients such as for example an anionic, nonionic or amphoteric or zwitterionic or cationic surfactant, an alkalizing agent, a preservative, a stabilizer, a treatment agent such as cations and polymers, a dye, a sunscreen, a thickening agent or a pearlescent agent.
  • various cosmetic ingredients such as for example an anionic, nonionic or amphoteric or zwitterionic or cationic surfactant, an alkalizing agent, a preservative, a stabilizer, a treatment agent such as cations and polymers, a dye, a sunscreen, a thickening agent or a pearlescent agent.
  • the composition containing the compound of mercaptan type is preferably applied for 5 to 30 minutes to the hair, which is then rinsed with water before the application of the oxidizing composition.
  • cysteamine or one of its salts is present in the reducing composition at a concentration of between 2 and 12% by weight of cysteamine base relative to the total weight of the reducing composition.
  • the pH of the reducing composition is between 6 and 10 and is obtained using an alkaline agent such as, for example, ammonia, monoethanolamine, diethanolamine, triethanolamine, an alkali carbonate or bicarbonate or of ammonium, an alkali hydroxide or using an acidifying agent such as for example hydrochloric acid, acetic acid, lactic acid, oxalic acid, boric acid, citric acid or phosphoric acid or also by means of a buffer such as for example mono and dipotasic phosphate and 3rd ammonium acid carbonate.
  • an alkaline agent such as, for example, ammonia, monoethanolamine, diethanolamine, triethanolamine, an alkali carbonate or bicarbonate or of ammonium, an alkali hydroxide or using an acidifying agent such as for example hydrochloric acid, acetic acid, lactic acid, oxalic acid, boric acid, citric acid or phosphoric acid or also by means of a buffer such as for example mono and di
  • the reducing composition may also contain a surfactant of the nonionic, anionic, cationic or amphoteric type.
  • the reducing composition may also contain treating agents, active substances such as panthotenic acid, fall arrest agents, dandruff agents, thickeners, suspending agents, sequestering agents, opacifying agents, dyes, sun filters as well as perfumes and preservatives.
  • the oxidizing composition is of the type commonly used and contains, as oxidizing agent, hydrogen peroxide, an alkali bromate, a persalt, a polythionate or a mixture of alkali bromate and parsley.
  • the concentration of hydrogen peroxide can vary from 1 to 20 volumes and preferably from 1 to 10, the concentration of alkali bromate from 2 to 12% and that of parsley from 0.1 to 15% by weight relative to the total weight of the oxidizing composition.
  • the pH of the oxidizing composition is generally between 2 and 8 but preferably between 3 and 6.
  • the following reducing composition (A) is applied to wet hair previously wound on curlers with a diameter of 14 mm:
  • composition (B) is then applied to the hair:
  • composition (B) By way of comparison, the same process was carried out by omitting the treatment using composition (B) and it was found that after a certain period of time, the hair gave off an unpleasant odor.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

Process for perming hair consisting in, after the reduction stage, using cysteamine or one of its salts, and before oxidation, in applying onto the hair an aqueous composition of a compound of the mercaptan type other than cysteamine. The process prevents the formation of unpleasant residual odour.

Description

Procédé de déformation permanente des cheveux à base de  Permanent hair deformation process based on
cystéamine ne générant pas d'odeur désagréable.  cysteamine does not generate an unpleasant odor.
La présente invention a pour objet un nouveau procédé de déformation permanente des cheveux utilisant en tant qu'agent réducteur de la cysteamine, ce procédé comportant, entre l'étape de réduction et l'étape d'oxydation, un traitement particulier permettant de combattre l'odeur désagréable résiduelle imprégnant les cheveux. The subject of the present invention is a new process for permanent deformation of the hair using, as reducing agent for cysteamine, this process comprising, between the reduction step and the oxidation step, a particular treatment making it possible to combat the residual unpleasant odor permeating the hair.
La technique classique pour réaliser la déformation permanente des cheveux consiste à réaliser, dans un premier temps, l'ouverture des ponts disulfures de la kératine à l'aide d'une composition contenant un agent réducteur (étape de réduction), puis, après avoir de préférence rincé la chevelure, à reconstituer dans un second temps lesdites liaisons disulfures en appliquant, sur les cheveux sous tension, une composition oxydante (étape d'oxydation dite aussi de fixation) de façon à donner aux cheveux la forme définitive recherchée. L'application de la composition réductrice peut être effectuée avant ou après l'enroulement des cheveux sur les bigoudis.  The conventional technique for achieving permanent hair deformation consists in firstly opening the disulfide bridges of the keratin using a composition containing a reducing agent (reduction step), then, after having preferably rinsed the hair, to reconstitute in a second time said disulfide bonds by applying to the hair under tension, an oxidizing composition (oxidation step also called fixing) so as to give the hair the desired final shape. The application of the reducing composition can be carried out before or after winding the hair on the curlers.
Cette technique de déformation permanente des cheveux permet indifféremment de réaliser soit une ondulation des cheveux soit un défrisage ou décrêpage.  This technique of permanent deformation of the hair makes it possible indifferently to carry out either a waving of the hair or a straightening or straightening.
Les compositions pour réaliser le premier temps d'une opération de permanente se présentent généralement sous forme de lotions, de crèmes, de gels ou de poudres à diluer dans un support liquide, et contiennent, en tant qu'agent réducteur, de préférence un thiol.  The compositions for carrying out the first stage of a perming operation are generally in the form of lotions, creams, gels or powders to be diluted in a liquid support, and contain, as reducing agent, preferably a thiol .
Parmi les thiols préconisés pour réaliser le premier temps d'une opération de permanente, la cysteamine ou amino-2 ethanethiol s'est révélée particulièrement favorable pour l'obtention de bonnes frisures des cheveux mais l'on a constaté que les cheveux ainsi traités développaient parfois, après une semaine à un mois, une odeur très désagréable.  Among the thiols recommended for carrying out the first phase of a perming operation, cysteamine or 2-amino ethanethiol has proved to be particularly favorable for obtaining good curling of the hair, but it has been found that the hair thus treated developed sometimes, after a week to a month, a very unpleasant smell.
Cette mauvaise odeur est plus particulièrement perceptible lorsque les cheveux traités sont à l'état mouillé ou dans un environnement humide. Ainsi, l'apparition de mauvaises odeurs est tout particulièrement favorisée par un climat chaud et humide ou encore par une tendance du sujet à sécréter beaucoup de sébum.  This bad odor is more particularly perceptible when the treated hair is in the wet state or in a humid environment. Thus, the appearance of bad smells is particularly favored by a hot and humid climate or by a tendency of the subject to secrete a lot of sebum.
Du fait de cet inconvénient, la cysteamine ainsi d'ailleurs que ses sels, même à de faibles concentrations, n'est généralement pas utilisée en tant qu'agent réducteur dans un procédé de déformation permanente des cheveux. Because of this drawback, cysteamine and also its salts, even at low concentrations, are generally not used as a reducing agent in a process of permanent deformation of the hair.
Après diverses recherches, on a constaté de façon surprenante et inattendue qu'il était possible de prévenir l'apparition des mauvaises odeurs dues à l'emploi de la cysteamine ou de l'un de ses sels, en procédant après l'étape de réduction et avant l'étape de fixation, à l'application d'une composition aqueuse contenant un composé de type mercaptan.  After various researches, it was surprisingly and unexpectedly found that it was possible to prevent the appearance of bad odors due to the use of cysteamine or one of its salts, by proceeding after the reduction step. and before the fixing step, to the application of an aqueous composition containing a compound of mercaptan type.
La présente invention a donc pour objet un procédé de déformation permanente des cheveux comprenant une étape de réduction à l'aide de cysteamine ou de l'un de ses sels et une étape d'oxydation, ce procédé étant caractérisé par le fait qu'entre l'étape de réduction et l'étape  The present invention therefore relates to a process for permanent deformation of the hair comprising a reduction step using cysteamine or one of its salts and an oxidation step, this process being characterized in that between the reduction step and the step
d'oxydation, on applique sur les cheveux une composition aqueuse d'un composé de type mercaptan autre que la cysteamine ayant une Donne efficacité de frisure, pour combattre l'odeur désagréable résiduelle imprégnant les cheveux.  oxidation, an aqueous composition is applied to the hair of a compound of mercaptan type other than cysteamine having a good curling efficiency, to combat the unpleasant residual odor permeating the hair.
Comme composé de type mercaptan, on peut utiliser selon l'invention, l'acide tbioglycolique et ses sels, la cystéine, le  As a compound of mercaptan type, there can be used according to the invention, tbioglycolic acid and its salts, cysteine,
monothioglycolate de glycérol ou de glycol, le chlorhydrate d'amino-2  glycerol or glycol monothioglycolate, amino-2 hydrochloride
-N-(mercapto-2 éthyl) propionamide, l'acide p-mercaptopropionique et ses dérivés, l'homocysteamine, l'acide thiolactique, le thioglycérol, le chlorhydrate d'amino-2 N-(mercapto-2 éthyl) acétamide. De préférence, on utilise l'acide thioglycolique et ses sels, la cystéine, l'acide  -N- (2-mercapto-ethyl) propionamide, p-mercaptopropionic acid and its derivatives, homocysteamine, thiolactic acid, thioglycerol, 2-amino hydrochloride N- (2-mercapto-ethyl) acetamide. Preferably, thioglycolic acid and its salts, cysteine, acid are used.
p-mercaptopropionique ou le chlorhydrate d'amino-2 N-(mercapto-2 éthyl) propionamide. p-mercaptopropionic or 2-amino hydrochloride N- (2-mercapto-ethyl) propionamide.
De préférence, le composé du type mercaptan est utilisé à une concentration comprise entre 2 et 20 % et de préférence entre 4 et 15 % par rapport au poids total de la composition aqueuse.  Preferably, the compound of the mercaptan type is used at a concentration of between 2 and 20% and preferably between 4 and 15% relative to the total weight of the aqueous composition.
Le pH de la composition doit de préférence être compris entre 7,5 et 9,5 et de préférence entre 8,5 et 9,5.  The pH of the composition should preferably be between 7.5 and 9.5 and preferably between 8.5 and 9.5.
Selon l'invention la composition aqueuse du composé de type mercaptan doit avoir une efficacité de frisure, exprimée en rayon de courbure, inférieure à 12 mm pour un bigoudi de 9 mm de diamètre.  According to the invention, the aqueous composition of the mercaptan type compound must have a crimping efficiency, expressed in radius of curvature, of less than 12 mm for a curler with a diameter of 9 mm.
L'efficacité de frisure est déterminée selon le protocole suivant : The crimping efficiency is determined according to the following protocol:
On utilise ces perruques de cheveux humains dont les mèches ont une longueur égale à 15 cm. Les mèches de cheveux normalisées sont enroulées sur des bigoudis d'un diamètre de 9 mm. On applique la solution aqueuse de mercaptan, on laisse agir 15 min et on rince à l'eau, puis on applique une solution oxydante d'eau oxygénée à 8 volumes et on laisse agir pendant 5 min. We use these human hair wigs whose strands have a length equal to 15 cm. Standardized locks of hair are rolled up on curlers with a diameter of 9 mm. The aqueous mercaptan solution is applied, left to act for 15 min and rinsed with water, then an oxidizing solution of hydrogen peroxide is applied to 8 volumes and it is left to act for 5 min.
On déroule les cheveux, on laisse agir encore 5 min puis on rince à l'eau.  The hair is rolled out, left to act for another 5 min and then rinsed with water.
A mi-longueur des mèches humides, on mesure le rayon de courbure moyen des ondulations obtenues. L'efficacité du mercaptan testé est d'autant plus grande que le rayon de courbure est plus faible.  At mid-length of the wet strands, the mean radius of curvature of the undulations obtained is measured. The effectiveness of the mercaptan tested is greater the smaller the radius of curvature.
Selon une forme de réalisation préférée du procédé selon l'invention, les cheveux sont rincés à l'eau préalablement à l'application de la composition contenant le composé du type mercaptan.  According to a preferred embodiment of the method according to the invention, the hair is rinsed with water before the application of the composition containing the compound of the mercaptan type.
La composition aqueuse contenant le composé de type mercaptan peut bien entendu contenir divers ingrédients cosmétiques tels que par exemple un agent tensioactif anionique, nonionique ou amphotère ou zwitterionique ou cationique, un agent alcalinisant, un agent conservateur, un stabilisant, un agent de traitement tel que des cations et des polymères, un colorant, un filtre solaire, un agent épaississant ou un agent nacrant.  The aqueous composition containing the mercaptan-type compound can of course contain various cosmetic ingredients such as for example an anionic, nonionic or amphoteric or zwitterionic or cationic surfactant, an alkalizing agent, a preservative, a stabilizer, a treatment agent such as cations and polymers, a dye, a sunscreen, a thickening agent or a pearlescent agent.
Selon le procédé de l'invention, la composition contenant le composé de type mercaptan est appliquée de préférence pendant 5 à 30 minutes sur les cheveux, qui sont ensuite rincés à l'eau avant l'application de la composition oxydante.  According to the process of the invention, the composition containing the compound of mercaptan type is preferably applied for 5 to 30 minutes to the hair, which is then rinsed with water before the application of the oxidizing composition.
Selon l'invention, la cysteamine ou l'un de ses sels est présent dans la composition réductrice à une concentration comprise entre 2 et 12 % en poids en cysteamine base par rapport au poids total de la composition réductrice.  According to the invention, cysteamine or one of its salts is present in the reducing composition at a concentration of between 2 and 12% by weight of cysteamine base relative to the total weight of the reducing composition.
De préférence, le pH de la composition réductrice est compris entre 6 et 10 et est obtenu à l'aide d'un agent alcalin tel que par exemple l'ammoniaque, la monoethanolamine, la diethanolamine, la triethanolamine, un carbonate ou bicarbonate alcalin ou d'ammonium, un hydroxyde alcalin ou à l'aide d'un agent acidifiant tel que par exemple l'acide chlorhydrique, l'acide acétique, l'acide lactique, l'acide oxalique, l'acide borique, l'acide citrique ou l'acide phosphorique ou encore au moyen d'un tampon tel que par exemple le phosphate mono et dipotasεique et 3e carbonate acide d'ammonium.  Preferably, the pH of the reducing composition is between 6 and 10 and is obtained using an alkaline agent such as, for example, ammonia, monoethanolamine, diethanolamine, triethanolamine, an alkali carbonate or bicarbonate or of ammonium, an alkali hydroxide or using an acidifying agent such as for example hydrochloric acid, acetic acid, lactic acid, oxalic acid, boric acid, citric acid or phosphoric acid or also by means of a buffer such as for example mono and dipotasic phosphate and 3rd ammonium acid carbonate.
Selon une forme de réalisation préférée, la composition réductrice peut contenir également un agent tensioactif de type non ionique, anionique, cationique ou amphotère. La composition réductrice peut également contenir des agents traitants, des substances actives tels que l'acide panthotenique, des agents antichutes, des agents antipelliculaires, des épaississants, des agents de suspension, des agents séquestrants, des agents opacifiants, des colorants, des filtres solaires ainsi que des parfums et conservateurs. According to a preferred embodiment, the reducing composition may also contain a surfactant of the nonionic, anionic, cationic or amphoteric type. The reducing composition may also contain treating agents, active substances such as panthotenic acid, fall arrest agents, dandruff agents, thickeners, suspending agents, sequestering agents, opacifying agents, dyes, sun filters as well as perfumes and preservatives.
La composition oxydante est du type couramment utilisée et contient comme agent oxydant de l'eau oxygénée, un bromate alcalin, un persel, un polythionate ou un mélange de bromate alcalin et de persel. La concentration en eau oxygénée peut varier de 1 à 20 volumes et de préférence de 1 à 10, la concentration en bromate alcalin de 2 à 12 % et celle en persel de 0,1 à 15 % en poids par rapport au poids total de la composition oxydante. Le pH de la composition oxydante est généralement compris entre 2 et 8 mais de préférence entre 3 et 6.  The oxidizing composition is of the type commonly used and contains, as oxidizing agent, hydrogen peroxide, an alkali bromate, a persalt, a polythionate or a mixture of alkali bromate and parsley. The concentration of hydrogen peroxide can vary from 1 to 20 volumes and preferably from 1 to 10, the concentration of alkali bromate from 2 to 12% and that of parsley from 0.1 to 15% by weight relative to the total weight of the oxidizing composition. The pH of the oxidizing composition is generally between 2 and 8 but preferably between 3 and 6.
On va maintenant donner à titre d'illustration et sans aucun caractère limitatif, plusieurs exemples du procédé de déformation permanente des cheveux selon l'invention. We will now give by way of illustration and without any limiting character, several examples of the process for permanent deformation of the hair according to the invention.
EXEMPLES EXEMPLE 1 : EXAMPLES EXAMPLE 1:
Sur des cheveux mouillés, préalablement enroulés sur des bigoudis d'un diamètre de 14 mm, on applique la composition réductrice (A) suivante : The following reducing composition (A) is applied to wet hair previously wound on curlers with a diameter of 14 mm:
Composition (A) : Composition (A):
- Chlorhydrate de cysteamine ....................................... 11,3 g - Cysteamine hydrochloride ....................................... 11.3 g
- Chlorure d'oléocétyldiméthylhydroxyéthylammonium  - Oleocetyldimethylhydroxyethylammonium chloride
en solution aqueuse à 30 % en matière active............... 0,39 g (MA) in aqueous solution at 30% active ingredient ............... 0.39 g (MA)
- Ammoniaque.........................qs pH = 8,5 - Ammonia ......................... qs pH = 8.5
- Eau ............................................................ qsp 100 g Après avoir laissé agir la composition pendant 15 minutes, on rince les cheveux à l'eau courante et on applique ensuite sur les cheveux la composition (B) suivante :  - Water ................................................ ............ qs 100 g After leaving the composition to act for 15 minutes, the hair is rinsed with running water and the following composition (B) is then applied to the hair:
Composition (B) : Composition (B):
- Acide thioglycolique ............................................... 9,2 g- Thioglycolic acid ............................................... 9.2g
- Chlorure d'oléocétyldiméthylhydroxyéthylammonium - Oleocetyldimethylhydroxyethylammonium chloride
en solution aqueuse à 30 % en matière active 0,39 g (MA) in aqueous solution at 30% active ingredient 0.39 g (MA)
- Ammoniaque ........................qs pH = 8,5 - Ammonia ........................ qs pH = 8.5
- Eau..............................................................qsp 100 g  - Water ................................................ .............. qs 100 g
On laisse agir la composition pendant 15 minutes, puis on rince à nouveau à l'eau courante avant d'appliquer la composition oxydante (C) suivante : The composition is left to act for 15 minutes, then rinsed again with running water before applying the following oxidizing composition (C):
Composition (C) : Composition (C):
- Peroxyde d'hydrogène en solution aqueuse à 200 Volumes.... 4,8 g - Hydrogen peroxide in aqueous solution at 200 Volumes .... 4.8 g
- Acide citrique..................... qs pH = 3  - Citric acid ..................... qs pH = 3
- Eau................................................................qsp 100 g Après avoir laissé agir la composition oxydante pendant 10 minutes, on rince à l'eau puis enlève les bigoudis et sèche les cheveux. - Water ................................................ ................ qs 100 g After allowing the oxidizing composition to act for 10 minutes, rinse with water and then remove the curlers and dry the hair.
On ne constate pas la formation de mauvaises odeurs dans le temps même après humidification des cheveux.  We do not see the formation of bad odors over time even after hair moistening.
A titre de comparaison, le même procédé a été réalisé en omettant le traitement à l'aide de la composition (B) et l'on a constaté qu'après une certaine période de temps, les cheveux dégageaient une odeur désagréable.  By way of comparison, the same process was carried out by omitting the treatment using composition (B) and it was found that after a certain period of time, the hair gave off an unpleasant odor.
En utilisant le même mode opératoire que décrit ci-dessus à l'exemple 1, on a procédé à une déformation permanente des cheveux à l'aide des compositions des exemples 2 à 8 suivants : Using the same procedure as described above in Example 1, the hair was permanently deformed using the compositions of Examples 2 to 8 below:
EXEMPLE 2 EXAMPLE 2
Composition (A) : Composition (A):
- Chlorhydrate de cystéamine ......................................... 11,3 g- Cysteamine hydrochloride ......................................... 11.3 g
- Chlorure d'oléocétyldiméthylhydroxyéthylammonium - Oleocetyldimethylhydroxyethylammonium chloride
en solution aqueuse à 30 % en matière active................ 0,39 g (MA)e n aqueous solution containing 30% active material ................ 0.39 g (MA)
- Ammoniaque.........................qs pH = 8,5 - Ammonia ......................... qs pH = 8.5
- Eau.........................................................qsp 100 g  - Water ................................................ ......... qs 100 g
Composition (B) : Composition (B):
- cystéine.............................................................. 12,2 g - cysteine ................................................ .............. 12.2 g
- Chlorure d'oléocêtyldiméthylhydroxyêthylammonium  - Oleocetyldimethylhydroxyethylammonium chloride
en solution aqueuse à 30 % en matière active............... 0 ,39 g (MA) in aqueous solution at 30% active ingredient ............... 0.39 g (MA)
- Ammoniaque.........................qs pH = 9,3 - Ammonia ......................... qs pH = 9.3
- Eau................................................................ qsp 100 g - Water ................................................ ................ qs 100 g
Composition (C) : Composition (C):
- Peroxyde d'hydrogène en solution aqueuse a 200 Volumes.... 4,8 g - Hydrogen peroxide in aqueous solution at 200 Volumes .... 4.8 g
- Acide citrique.....................qs pF = 3 - Citric acid ..................... qs pF = 3
- Eau ...............................................................qsp 100 g On ne constate pas l a formation de mauvaises odeurs dans le temps même après humidification des cheveux. - Water ................................................ ............... qs 100 g We do not see the formation of bad odors over time even after moistening the hair.
EXEMPLE 3 : EXAMPLE 3:
Composition (A) : Composition (A):
- Chlorhydrate de cysteamine ....................................... 7 g- Cysteamine hydrochloride ....................................... 7 g
- Monoethanolamine .................. qs pH = 8 - Monoethanolamine .................. qs pH = 8
- Eau pure .......................................................... qs 100 g  - Pure water ............................................... ........... qs 100 g
Composition (B) Composition (B)
- Thioglycolate de glycérol ....................................... 16 g - Glycérol ............................................................ 6 g- Glycerol thioglycolate ....................................... 16 g - Glycerol ... .................................................. ....... 6 g
- Ammoniaque ........................ qs pH = 8.5 - Ammonia ........................ qs pH = 8.5
- Eau pure ......................................................... qs 100 g  - Pure water ............................................... .......... qs 100 g
Composition (C) Composition (C)
- Eau oxygénée ......................................... qs 8 volumes- Hydrogen peroxide ......................................... qs 8 volumes
- Acide citrique qs pH = 3 - Citric acid qs pH = 3
- Stannate de sodium ............................................. 0,1 g - Sodium stannate ............................................. 0 , 1 g
- Eau pure ............................ qs ..................... 100 g - Pure water ............................ qs .................. ... 100 g
Aucune odeur ne se développe sur les cheveux ainsi traités. A l'inverse, une odeur se développe sur les mèches de cheveux n'ayant pas subi l'application de la composition (B). EXEMPLE 4 : No odor develops on the hair thus treated. Conversely, an odor develops on locks of hair which has not undergone the application of composition (B). EXAMPLE 4:
Composition (A) Composition (A)
- Chlorhydrate de cysteamine....................................... 8,45 g - Monoethanolamine ................. qs pH = 9 - Cysteamine hydrochloride ....................................... 8.45 g - Monoethanolamine. ................ qs pH = 9
- Eau pure ........................................................... qs 100 g Composition (B) - Pure water ............................................... ............ qs 100 g Composition (B)
- Acide mercaptopropionique ...................................... 16 g- Mercaptopropionic acid ...................................... 16 g
- Ammoniaque .......................... qs pH = 9,35 - Ammonia .......................... qs pH = 9.35
- Eau pure .......................................................... qs 100 g  - Pure water ............................................... ........... qs 100 g
Composition (C) Composition (C)
- Eau oxygénée ......................................... qs 8 volumes - Acide citrique ................... qs pH = 3 - Hydrogen peroxide ......................................... qs 8 volumes - Citric acid ................... qs pH = 3
- Stannate de sodium ............................................. 0,1 g - Sodium stannate ............................................. 0 , 1 g
- Eau pure ......................... qs ...................... 100 g - Pure water ......................... qs ..................... 100 g
EXEMPLE 5 : EXAMPLE 5:
Composition (A) : Composition (A):
- Cysteamine ........................................................ 5 g- Cysteamine ................................................ ........ 5 g
- Acide chlorhydrique ............... qs pH = 8 - Hydrochloric acid ............... qs pH = 8
- Eau pure .......................................................... ςs 100 g  - Pure water ............................................... ........... ςs 100 g
Composition (B) Composition (B)
- Chlorydrate d'amino-2-N(mercapto-2 éthyl) propionamide ... 16 g - Ammoniaque ........................ qs pH = 8,5 - Amino-2-N hydrochloride (2-mercapto-ethyl) propionamide ... 16 g - Ammonia ........................ qs pH = 8.5
- Eau pure ...................................................... qs 100 g  - Pure water ............................................... ....... qs 100 g
Composition (C) Composition (C)
- Eau oxygénée ......................................... qs 6 volumes- Hydrogen peroxide ......................................... qs 6 volumes
- Acide citrique ................... qs pH = 3 - Citric acid ................... qs pH = 3
- Eau pure ......................... qs ...................... 100 g EXEMPLE 6 : Composition (A) - Chlorhydrate de cysteamine ...................................... 7 g- Pure water ......................... qs ..................... 100 g EXAMPLE 6 Composition (A) - Cysteamine hydrochloride ...................................... 7 g
- Monoethanolamine .................. qs pH = 8 - Monoethanolamine .................. qs pH = 8
- Eau pure ........................................................... qs 100 g  - Pure water ............................................... ............ qs 100 g
Composition (B) Composition (B)
- Thioglycolate de glycol ......................................... 16 g- Glycol thioglycolate ......................................... 16 g
- Glycol ............................................................ 6 g- Glycol ................................................ ............ 6 g
- Ammoniaque ........................ qs pH = 8,6 - Ammonia ........................ qs pH = 8.6
- Eau pure .......................................................... qs 100 g  - Pure water ............................................... ........... qs 100 g
Composition (C) Composition (C)
- Eau oxygénée ......................................... qs 8 volumes- Hydrogen peroxide ......................................... qs 8 volumes
- Acide citrique ................... qs pH = 3 - Citric acid ................... qs pH = 3
- Stannate de sodium ........................................... 0,1 g- Sodium stannate ........................................... 0.1 g
- Eau pure ......................... qs ...................... 100 g - Pure water ......................... qs ..................... 100 g
EXEMPLE 7 : Composition (A) EXAMPLE 7: Composition (A)
- Chlorhydrate de cysteamine ................................... 7 g- Cysteamine hydrochloride ................................... 7 g
- Monoethanolamine .................. qs pH = 8 - Monoethanolamine .................. qs pH = 8
- Eau pure .......................................................... qs 100 g  - Pure water ............................................... ........... qs 100 g
Composition (B) Composition (B)
- Cystéine .......................................................... 14 g- Cysteine ................................................ .......... 14 g
- Acide tbioglycolique ......................................... 6 g - Ammoniaque ........................ qs pH = 9,5 - Tbioglycolic acid ......................................... 6 g - Ammonia .. ...................... qs pH = 9.5
- Eau pure .......................................................... qs 100 g Composition (C) - Pure water ............................................... ........... qs 100 g Composition (C)
- Eau oxygénée ......................................... qs 8 volumes- Hydrogen peroxide ......................................... qs 8 volumes
- Acide citrique ................... qs pH = 3 - Citric acid ................... qs pH = 3
- Eau pure ......................... qs ...................... 100 g  - Pure water ......................... qs ..................... 100 g
EXEMPLE 8 : EXAMPLE 8:
Composition (A) Composition (A)
- Chlorhydrate de cysteamine ...................................... 7 g- Cysteamine hydrochloride ...................................... 7 g
- Monoethanolamine .................. qs pH = 8 - Monoethanolamine .................. qs pH = 8
- Eau pure .............................................................. qs 100 g. Composition (B)  - Pure water ............................................... ............... qs 100 g. Composition (B)
- Chlorhydrate d'homocysteamine ................................... 12 g- Homocysteamine hydrochloride ................................... 12 g
- Ammoniaque ........................ qs pH = 8,5 - Ammonia ........................ qs pH = 8.5
- Eau pure ..................................................... qs 100 g  - Pure water ............................................... ...... qs 100 g
Composition (C) Composition (C)
- Eau oxygénée ......................................... qs 7,5 volumes- Hydrogen peroxide ......................................... qs 7,5 volumes
- Acide phosphorique .............. qs pH = 3 - Phosphoric acid .............. qs pH = 3
- Eau pure ......................... qs ...................... 100 g - Pure water ......................... qs ..................... 100 g

Claims

R E V E N D I C A T I O N S
1. Procédé de déformation permanente des cheveux comprenant une étape de réduction à l'aide de cysteamine ou de l'un de ses sels et une étape d'oxydation, caractérisé par le fait qu'entre l'étape de réduction et l'étape d'oxydation, on applique sur les cheveux une composition aqueuse d'un composé de type mercaptan autre que la cysteamine ayant une bonne efficacité de frisure. 1. A method for permanent deformation of the hair comprising a reduction step using cysteamine or one of its salts and an oxidation step, characterized in that between the reduction step and the step oxidation, an aqueous composition is applied to the hair of a compound of mercaptan type other than cysteamine having good curling efficiency.
2. Frocédé, selon la revendication 1, caractérisé par le fait que le composé de type mercaptan est choisi parmi l'acide thioglycolique et ses sels, la cystéine, le monothioglycolate de glycérol ou de glycol, le chlorhydrate d'amino-2-N-(mercapto-2 éthyl) propionamide,  2. Method, according to claim 1, characterized in that the compound of mercaptan type is chosen from thioglycolic acid and its salts, cysteine, glycerol or glycol monothioglycolate, amino-2-N hydrochloride - (2-mercapto-ethyl) propionamide,
l'acide β-mercaptopropionique et ses dérivés, l'homocystéine, l'acide thiolactique, le thioglycérol, le chlorhydrate d'amino-2 N-(mercapto-2 éthyl) acétamide.  β-mercaptopropionic acid and its derivatives, homocysteine, thiolactic acid, thioglycerol, 2-amino-hydrochloride N- (2-mercapto-ethyl) acetamide.
3. Procédé, selon la revendication. 2, caractérisé par le fait que le composé de type mercaptan est de préférence l'acide thioglycolique et ses sels, la cystéine, l'acide β-mercaptopropionique et le chlorhydrate d'amino-2 N(mercapto-2 éthyl) propionamide.  3. Method according to claim. 2, characterized in that the compound of mercaptan type is preferably thioglycolic acid and its salts, cysteine, β-mercaptopropionic acid and 2-amino hydrochloride (2-mercapto-ethyl) propionamide.
4. Procédé selon l'une des revendications 1 à 3, caractérisé par le fait que le composé de type mercaptan est présent à une concentration comprise entre 2 et 20 % par rapport au poids total de la composition aqueuse.  4. Method according to one of claims 1 to 3, characterized in that the compound of mercaptan type is present at a concentration of between 2 and 20% relative to the total weight of the aqueous composition.
5. Procédé selon les revendications 1 à 4, caractérisé par le fait que le pH de la composition aqueuse du composé de type mercaptan est compris entre 7,5 et 9,5.  5. Method according to claims 1 to 4, characterized in that the pH of the aqueous composition of the compound of mercaptan type is between 7.5 and 9.5.
6. Procédé selon l'une des revendications 1 à 5, caractérisé par le fait que les cheveux sont rincés à l'eau préalablement à l'application de la composition aqueuse du composé de type mercaptan.  6. Method according to one of claims 1 to 5, characterized in that the hair is rinsed with water before the application of the aqueous composition of the compound of mercaptan type.
7. Procédé selon l'une quelconque des revendications précédentes, caractérisé par le fait que la composition aqueuse du composé de type mercaptan contient en outre au moins un ingrédient cosmétique choisi parmi un agent tensioactif anionique, n-onionique ou amphotère ou zwitterioniqυe ou cationique, un agent alcalinisant, un agent conservateur, un stabilisant, un agent de traitement, un colorant, un filtre solaire, un agent épaississant ou un agent nacrant. 7. Method according to any one of the preceding claims, characterized in that the aqueous composition of the compound of mercaptan type also contains at least one cosmetic ingredient chosen from an anionic, n-onionic or amphoteric or zwitterionic or cationic surfactant, an alkalizing agent, a preservative, a stabilizer, a treatment agent, a dye, a sunscreen, a thickening agent or a pearling agent.
8. Procédé selon l'une quelconque des revendications précédentes, caractérisé par le fait que la composition aqueuse du composé de type mercaptan est appliquée sur les cheveux pendant un temps de 5 à 20 minutes. 8. Method according to any one of the preceding claims, characterized in that the aqueous composition of the compound of mercaptan type is applied to the hair for a time of 5 to 20 minutes.
9. Procédé selon l'une quelconque des revendications précédentes, caractérisé par le fait qu'après application sur les cheveux de la composition aqueuse du composé de type mercaptan, on procède à un rinçage des cheveux à l'eau.  9. Method according to any one of the preceding claims, characterized in that after application to the hair of the aqueous composition of the compound of mercaptan type, the hair is rinsed with water.
PCT/FR1992/000916 1991-10-04 1992-10-02 Cysteamine-based process for perming hair without generating unpleasant odours WO1993006817A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9112230A FR2682017B1 (en) 1991-10-04 1991-10-04 PROCESS FOR PERMANENT DEFORMATION OF CYSTEAMINE-BASED HAIR THAT DOES NOT GENERATE AN UNpleasant Odor.
FR91/12230 1991-10-04

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5601813A (en) * 1992-01-10 1997-02-11 Helene Curtis, Inc. Cysteamine permanent wave composition and method
EP0893118A1 (en) * 1997-07-25 1999-01-27 Wella Aktiengesellschaft Saturated alkylsubstituted N-mercaptoacetyl-heterocycles, agent and method for permanently shaping hair based thereon and processes for their preparation
US6302119B1 (en) 1999-12-06 2001-10-16 Bristol-Myers Squibb Company Low odor permanent waving compositions containing a disulfide

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989007435A2 (en) * 1988-02-19 1989-08-24 Amethyst Investment Group, Inc. Permanent wave process and compositions
EP0362663A1 (en) * 1988-10-04 1990-04-11 Henkel Kommanditgesellschaft auf Aktien Permanent wave composition
EP0261387B1 (en) * 1986-09-20 1991-05-08 Wella Aktiengesellschaft Composition and process for lastingly reshaping the hair

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0261387B1 (en) * 1986-09-20 1991-05-08 Wella Aktiengesellschaft Composition and process for lastingly reshaping the hair
WO1989007435A2 (en) * 1988-02-19 1989-08-24 Amethyst Investment Group, Inc. Permanent wave process and compositions
EP0362663A1 (en) * 1988-10-04 1990-04-11 Henkel Kommanditgesellschaft auf Aktien Permanent wave composition

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5601813A (en) * 1992-01-10 1997-02-11 Helene Curtis, Inc. Cysteamine permanent wave composition and method
EP0893118A1 (en) * 1997-07-25 1999-01-27 Wella Aktiengesellschaft Saturated alkylsubstituted N-mercaptoacetyl-heterocycles, agent and method for permanently shaping hair based thereon and processes for their preparation
US6302119B1 (en) 1999-12-06 2001-10-16 Bristol-Myers Squibb Company Low odor permanent waving compositions containing a disulfide

Also Published As

Publication number Publication date
FR2682017B1 (en) 1993-11-19
FR2682017A1 (en) 1993-04-09

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