FR2679448A1 - AZETROPIC MIXTURE OF 2-HYDROXY PROPYL THIOGLYCOLATE AND 2-HYDROXY METHYL-ETHYL THIOGLYCOLATE, PROCESS FOR OBTAINING THE SAME, AND USE THEREOF IN A PROCESS FOR PERMANENTLY DEFORMING HAIR. - Google Patents
AZETROPIC MIXTURE OF 2-HYDROXY PROPYL THIOGLYCOLATE AND 2-HYDROXY METHYL-ETHYL THIOGLYCOLATE, PROCESS FOR OBTAINING THE SAME, AND USE THEREOF IN A PROCESS FOR PERMANENTLY DEFORMING HAIR. Download PDFInfo
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- FR2679448A1 FR2679448A1 FR9109280A FR9109280A FR2679448A1 FR 2679448 A1 FR2679448 A1 FR 2679448A1 FR 9109280 A FR9109280 A FR 9109280A FR 9109280 A FR9109280 A FR 9109280A FR 2679448 A1 FR2679448 A1 FR 2679448A1
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- 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
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Abstract
Description
La présente invention a pour objet un mélange azétrope d'esters de propanediol-1,2 de 11 acide thioglycolique, son procédé d'obtention et son utilisation, en tant qutagent réducteur, dans un procédé de déformation permanente des cheveux. The subject of the present invention is an azetropic mixture of 1,2-propanediol esters of thioglycolic acid, its process for obtaining and its use, as a reducing agent, in a process of permanent hair deformation.
ta technique classique pour réaliser une déformation permanente des cheveux consiste, dans un premier temps, à réaliser ltouverture des liaisons disulfures de la kératine (cystine) à itaide 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 recherchée. Cette technique permet indifféremment de réaliser soit 11 ondulation des cheveux soit leur défrisage ou leur décrêpage. The conventional technique for producing a permanent deformation of the hair consists, first of all, in opening the disulfide bonds of the keratin (cystine) with the aid of 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, on the undervoltage hair, an oxidizing composition (oxidation stage also called fixation) so as to give the hair the desired shape. This technique allows indifferently to achieve either 11 hair waving or straightening or curing.
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 time of a permanent operation are generally in the form of lotions, creams, gels or powders for dilution in a liquid carrier, and preferably contain a reducing agent. thiol.
Parmi ces derniers, ceux couramment utilisés sont l'acide thioglycolique et l'acide thiolactique ou un mélange de ces acides, ainsi que leurs esters tels que par exemple le monothioglycolate de glycérol, ou de glycol. Among these, those commonly used are thioglycolic acid and thiolactic acid or a mixture of these acids, as well as their esters such as, for example, glycerol monothioglycolate, or glycol.
Ces agents réducteurs sont particulièrement efficaces pour réduire les liaisons disulfures de la kératine, en particulier l'acide thioglycolique qui est généralement considéré comme le produit de référence en permanente. These reducing agents are particularly effective in reducing the disulfide bonds of keratin, in particular thioglycolic acid which is generally considered as the permanent reference product.
On a toutefois constaté que l'acide thioglycolique devait être utilisé en milieu suffisamment basique (pH a 8,5) si l'on voulait obtenir une frisure satisfaisante. However, it has been found that thioglycolic acid should be used in a sufficiently basic medium (pH 8.5) in order to obtain a satisfactory crimp.
Le monothioglycolate de glycérol permet en partie de remédier à cet inconvénient dans la mesure où lton peut obtenir une frisure optimum à pH 4 8,5, de préférence à un pH compris entre 6 et 8. Toutefois, dans cette zone de pH, la frisure obtenue avec le monothioglycolate de glycérol reste notablement inférieure à celle obtenue avec 1V acide thioglycolique notamment sous forme de thioglycolate dtammonium, à un pH beaucoup plus basique. In part, the glycerol monothioglycolate makes it possible to overcome this disadvantage insofar as it is possible to obtain an optimum crimp at pH 4,85, preferably at a pH of between 6 and 8. However, in this pH zone, the crimp obtained with the glycerol monothioglycolate remains significantly lower than that obtained with 1V thioglycolic acid, especially in the form of ammonium thioglycolate, at a much more basic pH.
Après différentes études, on vient maintenant de constater qu il était possible de remédier aux inconvénients des agents réducteurs connus en utilisant un mélange azéotrope bien défini de monoesters de propanediol-1,2 de l'acide thioglycolique. After various studies, it has now been found that the disadvantages of the known reducing agents can be overcome by using a well-defined azeotropic mixture of 1,2-propanediol monoesters of thioglycolic acid.
En effet, ce mélange azéotrope permet, à la même concentration molaire, d'obtenir non seulement une frisure supérieure à celle obtenue avec le monothioglycolate de glycérol mais également une frisure pratiquement équivalente à celle obtenue à pH alcalin avec l'acide thioglycolique. Indeed, this azeotropic mixture allows, at the same molar concentration, to obtain not only a curl greater than that obtained with the glycerol monothioglycolate, but also a crimp substantially equivalent to that obtained at alkaline pH with thioglycolic acid.
On a par ailleurs constaté que l'état des cheveux traités avec le mélange azéotrope selon l'invention était très satisfaisant sur le plan cosmétique. It has also been found that the condition of the hair treated with the azeotropic mixture according to the invention was very satisfactory from the cosmetic point of view.
La présente invention a donc pour objet, à titre de produit industriel nouveau, un mélange azéotrope d'esters de propanediol-1,2 de l'acide thioglycolique, celui-ci étant constitué de 2/3 de thioglycolate d'hydroxy-2 propyle de formule
HS-CH2-COO-CH2-CHOH-CH3 (I) et de 1/3 de thioglycolate d'hydroxy-2 méthyl-l éthyle de formule
HS-CH2-COO-CH(CH3)-CH20H (II)
Ces proportions sont indifféremment molaires ou pondérales dans la mesure où ces deux esters (I) et (II) ont la même masse moléculaire.The subject of the present invention is therefore, as a new industrial product, an azeotropic mixture of propanediol-1,2 esters of thioglycolic acid, this latter consisting of 2/3 of 2-hydroxypropyl thioglycolate Formula
HS-CH 2 -COO-CH 2 -CHOH-CH 3 (I) and 1/3 of 2-hydroxyethyl-1-methylethyl thioglycolate of formula
HS-CH2-COO-CH (CH3) -CH2OH (II)
These proportions are indifferently molar or weight to the extent that these two esters (I) and (II) have the same molecular weight.
La présente invention a également pour objet le procédé de préparation du mélange azéotrope tel que défini ci-dessus. The present invention also relates to the process for preparing the azeotropic mixture as defined above.
Ce procédé consiste à faire réagir l'acide thioglycolique avec le propanediol-1,2, sans catalyseur, en distillant l'eau formée au fur et à mesure de l'avancement de la réaction. This process consists of reacting thioglycolic acid with 1,2-propanediol, without catalyst, by distilling the water formed as the progress of the reaction.
La réaction est de préférence conduite sous atmosphère inerte en présence d'un excès de propanediol-1,2 afin d'éviter la formation du diester qui présente l'inconvénient majeur d'être insoluble dans lteau. The reaction is preferably conducted under an inert atmosphere in the presence of an excess of 1,2-propanediol to avoid the formation of the diester which has the major disadvantage of being insoluble in water.
En pratique, deux équivalents de propanediol-1,2 se sont avérés suffisants. La température de réaction est généralement comprise entre 80 et 1700C, et de préférence entre 100 et 1500C pour permettre l'élimination par distillation, de l'eau formée, sous pression normale, sans dégradation. On peut également faciliter l'élimination de l'eau par azéotropie, et dans ce cas, on utilise un solvant classique tel que par exemple du toluène ou du xylène ou encore du dichloroéthane. In practice, two equivalents of 1,2-propanediol were found to be sufficient. The reaction temperature is generally between 80 and 1700C, and preferably between 100 and 1500C to allow the removal by distillation of the water formed, under normal pressure, without degradation. It is also possible to facilitate the removal of water by azeotropy, and in this case, a conventional solvent such as for example toluene or xylene or dichloroethane is used.
Lorsque la réaction est terminée, on procède à une distillation sous pression réduite de façon à obtenir le mélange azéotrope selon l'invention. Le vide est de préférence compris entre 2 et 30 hPa car dans ces conditions, la composition du mélange azéotrope selon l'invention (proportion de 2/3 de (I) pour 1/3 de (II)) reste constante. When the reaction is complete, distillation is carried out under reduced pressure so as to obtain the azeotropic mixture according to the invention. The vacuum is preferably between 2 and 30 hPa because under these conditions, the composition of the azeotropic mixture according to the invention (proportion of 2/3 of (I) for 1/3 of (II)) remains constant.
La température d'ébullition du mélange azéotrope est fonction du vide appliqué. A titre exemple, la température d'ébullition est d'environ 137-143"C sous 26,6 hPa et d'environ 106-1150C sous 5,32 hPa. The boiling temperature of the azeotropic mixture is a function of the applied vacuum. For example, the boiling temperature is about 137-143 ° C at 26.6 hPa and about 106-1150 ° C at 5.32 hPa.
Le mélange azéotrope selon l'invention forme également un azéotrope avec le propanediol-1,2, ce qui permet de 11 obtenir indifféremment pur ou éventuellement en solution dans le propanediol-1,2. The azeotropic mixture according to the invention also forms an azeotrope with 1,2-propanediol, which makes it possible to obtain indifferently pure or optionally in solution in 1,2-propanediol.
On doit également noter que de facon tout à fait inattendue et surprenante, la proportion des esters (I) et (II) du mélange azéotrope selon l'invention reste constante ctest-à-dire 2/3 de (I) et 1/3 de (II) quelle que soit la teneur en propanediol-1,2. It should also be noted that, quite unexpectedly and surprisingly, the proportion of esters (I) and (II) of the azeotropic mixture according to the invention remains constant, that is to say 2/3 of (I) and 1/3 of (II) regardless of the content of 1,2-propanediol.
Le mélange azéotrope selon 11 invention peut également être préparé par transesterification d'un ester de l'acide thioglycolique avec un équivalent de propanediol-1,2, sans catalyseur acide. The azeotropic mixture according to the invention can also be prepared by transesterification of a thioglycolic acid ester with an equivalent of 1,2-propanediol, without an acid catalyst.
Les esters de l'acide thioglycolique particulièrement préférés sont le thioglycolate d'éthyle et le thioglycolate de méthyle. La réaction de transesterification est de préférence conduite sous atmosphère inerte et à une température supérieure au point d'ébullition de méthanol ou du méthanol libéré, de façon à faciliter leur élimination sous pression normale. Particularly preferred thioglycolic acid esters are ethyl thioglycolate and methyl thioglycolate. The transesterification reaction is preferably conducted under an inert atmosphere and at a temperature above the boiling point of methanol or methanol released, so as to facilitate their removal under normal pressure.
On peut également utiliser un co-solvant en formant un azéotrope avec le méthanol ou méthanol de facon à faciliter leur élimination. Parmi les solvants préférés, on peut citer notamment le dichloro-1,2 éthane, le
N,N-diméthyl formamide ou le toluène. Dans la pratique, un équivalent de propanediol-1,2 est suffisant mais on peut bien entendu l'utiliser en excès si l'on souhaite augmenter la vitesse de réaction.A co-solvent can also be used by forming an azeotrope with methanol or methanol so as to facilitate their removal. Among the preferred solvents, mention may in particular be made of 1,2-dichloroethane,
N, N-dimethylformamide or toluene. In practice, an equivalent of 1,2-propanediol is sufficient but it can of course be used in excess if it is desired to increase the reaction rate.
Après la fin de la réaction, on procède à une distillation de facon à obtenir le mélange azéotrope selon l'invention dans les proportions de 2/3 de (I) et 1/3 de (II). After the end of the reaction, distillation is carried out so as to obtain the azeotropic mixture according to the invention in the proportions of 2/3 of (I) and 1/3 of (II).
La présente invention a également pour objet une composition réductrice pour le premier temps d'une opération de déformation permanente des cheveux contenant, dans un véhicule cosmétique approprié, en tant qu agent réducteur, le mélange azéotrope selon l'invention. The present invention also relates to a reducing composition for the first time of a permanent hair deformation operation containing, in a suitable cosmetic vehicle, as reducing agent, the azeotropic mixture according to the invention.
Dans les compositions selon I1 invention, le mélange azéotrope est généralement présent à une concentration comprise entre 2 et 30 Z et de préférence entre 5 et 20 Z en poids par rapport au poids total de la composition réductrice. In the compositions according to the invention, the azeotropic mixture is generally present at a concentration of between 2 and 30% and preferably between 5 and 20% by weight relative to the total weight of the reducing composition.
Le pH de la composition est de préférence compris entre 4 et 8 et plus particulièrement entre 6 et 8 et est obtenu à l'aide d'un agent alcalin tel que par exemple l'ammoniaque, la monoéthanolamine, la diéthanolamine, la triéthanolamine, 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 de tampons tels que par exemple le phosphate mono et dipotassique et le carbonate acide d'ammonium. The pH of the composition is preferably between 4 and 8 and more particularly between 6 and 8 and is obtained using an alkaline agent such as, for example, ammonia, monoethanolamine, diethanolamine or triethanolamine. alkali metal or ammonium carbonate or bicarbonate, an alkaline hydroxide or with the aid of an acidifying agent such as, for example, hydrochloric acid, acetic acid, lactic acid, oxalic acid or boric acid citric acid or phosphoric acid, or by means of buffers such as, for example, mono and dipotassium phosphate and ammonium hydrogen carbonate.
La composition réductrice peut également contenir d'autres agents réducteurs connus tels que par exemple l'acide thioglycolique, le monothioglycolate de glycérol ou de glycol, la cystéamine et ses dérivés acylés C -C tels que la N-acétylcystéamine ou la N-propionylcystéamine, la cystéine, la N-acétylcystéine, les N-mercaptoalkylamides de sucres tels que le N-(mercapto-2-éthyl)gluconamide, l'acide (3-mercaptopropionique et ses dérivés, l'acide thiolactique, l'acide thiomalique, la pantéthéine, le thioglycérol, les sulfites et les bisulfites d'un métal-alcalin ou alcalino-terreux, les N-(mercaptoalkyl)ù > -hydroxyalkylamides décrits dans la demande de brevet EP 354 835, les N-mono ou N,N-dialkylmercapto 4-butyramides décrits dans la demande de brevet EP 368 763, et les aminomercaptoalkylamides décrits dans la demande de brevet EP 403 267. The reducing composition may also contain other known reducing agents such as, for example, thioglycolic acid, glycerol or glycol monothioglycolate, cysteamine and its acyl derivatives C -C such as N-acetylcysteamine or N-propionylcysteamine, cysteine, N-acetylcysteine, N-mercaptoalkylamides of sugars such as N- (mercapto-2-ethyl) gluconamide, (3-mercaptopropionic acid and its derivatives, thiolactic acid, thiomalic acid, pantothin, thioglycerol, sulphites and bisulphites of a metal-alkali or alkaline earth metal, N- (mercaptoalkyl) ù -hydroxyalkylamides described in patent application EP 354 835, N-mono or N, N- dialkylmercapto 4-butyramides described in the patent application EP 368 763, and the aminomercaptoalkylamides described in the patent application EP 403 267.
Selon un mode de réalisation préféré, la composition réductrice contient également un agent tensio-actif de type non ionique, anionique, cationique ou amphotère et parmi ceux-ci on peut citer les alkylsulfates, les alkylbenzènesulfates, les alkyléthersulfates, les alkylsulfonates, les sels d'ammonium quaternaire, les alkylbétaines, les alkylphénols oxyéthylénés, les alcanolamides diacides gras, les esters d'acides gras oxyéthylénés ainsi que d'autres agents tensio-actifs non ioniques du type hydroxypropyléther. According to a preferred embodiment, the reducing composition also contains a surfactant of nonionic, anionic, cationic or amphoteric type and among these there may be mentioned alkyl sulphates, alkyl benzene sulphates, alkyl ether sulphates, alkyl sulphonates, quaternary ammonium, alkylbetaines, oxyethylenated alkylphenols, fatty acid alkanolamides, oxyethylenated fatty acid esters and other hydroxypropyl ether type nonionic surfactants.
Lorsque la composition réductrice contient au moins un agent tensio-actif, celui-ci est généralement présent à une concentration maximale de 30% en poids, mais de préférence comprise entre 0,5 et 10% par rapport au poids total de la composition réductrice. When the reducing composition contains at least one surfactant, it is generally present at a maximum concentration of 30% by weight, but preferably between 0.5 and 10% relative to the total weight of the reducing composition.
Dans le but d'améliorer les propriétés cosmétiques des cheveux ou encore d'en atténuer ou d'éviter leur dégradation, la composition réductrice peut également contenir un agent traitant de nature cationique, anionique, non -ionique ou amphotère. In order to improve the cosmetic properties of the hair or to reduce or prevent its degradation, the reducing composition may also contain a treating agent of cationic, anionic, nonionic or amphoteric nature.
Parmi les agents traitants particulièrement préférés, on peut notamment citer ceux décrits dans les brevets français nO 2.598.613, et n0 2.470.596. On peut également utiliser comme agents traitants des silicones volatiles ou non, linéaires ou cycliques et leurs mélanges, les polydiméthylsiloxanes, les polyorganosiloxanes quaternisés tels que ceux décrits dans la demande de brevet francais n" 2.535.730, les polyorganosiloxanes à groupements aminoalkyles modifiés par des groupements alkoxycarbonylalkyles tels que ceux décrits dans le brevet US n" 4.749.732, des polyorganosiloxanes tels que le copolymère polydiméthylsiloxanepolyoxyalkyle du type Diméthicone Copolyol, un polydiméthylsiloxane à groupements terminaux stéaroxy (stéaroxydiméthicone), un copolymère polydiméthylsiloxane-dialkylammonium acétate ou un copolymère polydiméthyl -siloxane polyalkylbétalne décrits dans le brevet Britannique n" 2.197.352, des polysiloxanes organo modifiés par des groupements mercapto ou mercaptoalkyles tels que ceux décrits dans le brevet Français nO 1.530.369 et dans la demande de brevet européen n" 295.780, ainsi que des silanes tels que le stéaroxytriméthylsilane. Particularly preferred treating agents include those described in French Patent Nos. 2,598,613 and 2,470,596. It is also possible to use volatile or non-volatile, linear or cyclic silicones and mixtures thereof, polydimethylsiloxanes, quaternized polyorganosiloxanes such as those described in French Patent Application No. 2,535,730, polyorganosiloxanes containing aminoalkyl groups modified with alkoxycarbonylalkyl groups such as those described in US Pat. No. 4,749,732, polyorganosiloxanes such as polydimethylsiloxanepolyoxyalkyl copolymer of Dimethicone Copolyol type, a polydimethylsiloxane containing stearoxyl end groups (stearoxydimethicone), a polydimethylsiloxane-dialkylammonium acetate copolymer or a polydimethylsiloxane copolymer; polyalkylbethanol described in British Patent No. 2,197,352, organo-modified polysiloxanes with mercapto or mercaptoalkyl groups such as those described in French Patent No. 1,530,369 and in European Patent Application No. 295,780, as well as silanes such as stearoxytrimethylsilane.
La composition réductrice peut également contenir d'autres ingrédients traitants tels que des aminoacides basiques (tels que la lysine, l'arginine) ou acides (tels que l'acide glutamique, l'acide aspartique), des peptides et leurs dérivés, des hydrolysats de protéines, des cires, des agents de gonflement et de pénétration ou permettant de renforcer l'efficacité du réducteur tels que le mélange SiO2/PDMS (polydiméthylsiloxane), le diméthylisosorbitol, l'urée et ses dérivés, la pyrrolidone, les N-alkyl-pyrrolidones, la thiamorpholinone, les alkyléthers d'alkylèneglycol ou de dialkylèneglycol tels que par exemple le monométhyléther de propylèneglycol, le monométhyléther de dipropylèneglycol, le monoéthyléther de l'éthylèneglycol et le monoéthyléther du diéthylèneglycol, des alcanediols en C -C tels que par exemple le propanediol-1,2 et le butanediol-1,2, l'imidazolidinone-2 ainsi que d'autres composés tels que des alcools gras, des dérivés de la lanoline, des ingrédients actifs tels que l'acide panthothénique, desagents 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. The reducing composition may also contain other treating ingredients such as basic amino acids (such as lysine, arginine) or acidic acids (such as glutamic acid, aspartic acid), peptides and their derivatives, hydrolysates proteins, waxes, swelling and penetration agents or to enhance the effectiveness of the reducing agent, such as SiO 2 / PDMS (polydimethylsiloxane), dimethylisosorbitol, urea and its derivatives, pyrrolidone, N-alkyl pyrrolidones, thiamorpholinone, alkylene glycol or dialkylene glycol alkyl ethers such as, for example, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, ethylene glycol monoethyl ether and diethylene glycol monoethyl ether, C -C alkanediols such as, for example 1,2-propanediol and 1,2-butanediol, imidazolidinone-2 and other compounds such as fatty alcohols, lanolin derivatives e, active ingredients such as pantothenic acid, anti-hair loss agents, anti-dandruff agents, thickeners, suspending agents, sequestering agents, opacifying agents, dyes, sunscreens as well as perfumes and preservatives.
La composition réductrice selon l'invention se présente essentiellement sous forme aqueuse notamment sous la forme d'une lotion épaissie ou non, d'une crème ou d'un gel. The reducing composition according to the invention is essentially in aqueous form, in particular in the form of a thickened lotion or not, a cream or a gel.
La composition réductrice selon 11 invention peut être également du type exothermique, c'est-à-dire provoquant un certain échauffement lors de l'application sur les cheveux, ce qui apporte un agrément à la personne qui subit le premier temps de la permanente ou du défrisage. The reducing composition according to the invention may also be of the exothermic type, that is to say, causing a certain heating during application to the hair, which is acceptable to the person who suffers the first stage of the perm or straightening.
La composition réductrice selon 11 invention peut également contenir un solvant tel que par exemple de méthanol, du propanol, ou de l'isopropanol ou encore du glycérol à une concentration maximale de 20% par rapport au poids total de la composition. The reducing composition according to the invention may also contain a solvent such as for example methanol, propanol or isopropanol or glycerol at a maximum concentration of 20% relative to the total weight of the composition.
Le mélange azéotrope selon l'invention n'étant pas très stable en milieu aqueux, il est préférable de réaliser la composition au moment de l'emploi par mélange des différents ingrédients. The azeotropic mixture according to the invention is not very stable in aqueous medium, it is preferable to make the composition at the time of use by mixing the various ingredients.
De façon à pouvoir réaliser la composition réductrice, les ingrédients se présentent donc conditionnés en plusieurs parties, le mélange azéotrope étant toujours en milieu anhydre. In order to achieve the reducing composition, the ingredients are therefore packaged in several parts, the azeotropic mixture being always in an anhydrous medium.
L'agent régulateur de pH est généralement présent dans la partie contenant le milieu aqueux. The pH regulating agent is generally present in the portion containing the aqueous medium.
Les adjuvants cosmétiques peuvent être présents soit dans la phase aqueuse, soit dans la phase anhydre à condition-bien entendu que le mélange azéotrope reste en milieu totalement anhydre et que les composés soient compatibles entre eux. The cosmetic adjuvants may be present either in the aqueous phase or in the anhydrous phase provided, of course, that the azeotropic mixture remains in a completely anhydrous medium and that the compounds are compatible with one another.
Le véhicule des compositions selon l'invention est de préférence de l'eau ou une solution hydroalcoolique d'un alcool inférieur tel que méthanol, l'isopropanol ou le butanol. The vehicle of the compositions according to the invention is preferably water or a hydroalcoholic solution of a lower alcohol such as methanol, isopropanol or butanol.
Lorsque les compositions sont destinées à une opération de défrisage ou de décrêpage des cheveux, la composition réductrice est de préférence sous forme d'une crème de façon à maintenir les cheveux aussi raides que possible. On réalise ces crèmes sous forme d'émulsions "lourdes" > par exemple à base de stéarate de glycéryle, de stéarate de glycol, de cires auto-émulsionnables, d'alcools gras, etc... When the compositions are intended for hair straightening or straightening operation, the reducing composition is preferably in the form of a cream so as to keep the hair as straight as possible. These creams are produced in the form of "heavy" emulsions, for example based on glyceryl stearate, glycol stearate, self-emulsifiable waxes, fatty alcohols, etc.
On peut également utiliser des liquides ou des gels contenant des agents épaississants tels que des polymères ou des copolymères carboxyvinyliques qui "collent" les cheveux et les maintiennent dans la position lisse pendant le temps de pose. It is also possible to use liquids or gels containing thickeners such as carboxyvinyl polymers or copolymers which "stick" the hair and keep it in the smooth position during the exposure time.
Les compositions selon l'invention peuvent etre également sous forme dite 'tauto-neutralisante" ou encore "auto-régulée" et dans ce cas, le mélange azéotrope selon l'invention est associé à au moins un disulfure soit connu pour son utilisation dans une composition réductrice pour permanente auto-neutralisante soit dérivant du mélange azéotrope selon l'invention et correspondant donc aux trois composés suivants de formule (III), (IV) et (V)::
<tb> +S-CH2-COO-CH2-CHOH-CH3 <SEP> i <SEP> 2 <SEP> (I <SEP> Il) <SEP>
<tb> [2 <SEP> 3 <SEP> 2] <SEP> 2
<tb>
<tb> [2 <SEP> 3 <SEP> 2] <SEP> 2
<Tb>
Parmi les disulfures connus, on peut notamment mentionner l'acide dithioglycolique, le dithioglycérol, la N,N'-diacétyl-cystamine, la cystine, la pantéthine, les disulfures des N-(mercaptoalkyl) oe-hydroxyalkylamides décrits dans la demande de brevet EP 354 835, les disulfures des N-mono ou
N,N-dialkylmercapto 4-butyramides décrits dans la demande de brevet
EP 368 763 et les disulfures des aminomercaptoalkylamides décrits dans la demande de brevet EP 403 267.Among the known disulfides, mention may in particular be made of dithioglycolic acid, dithioglycerol, N, N'-diacetyl-cystamine, cystine, pantethine, disulphides of the N- (mercaptoalkyl) oe-hydroxyalkylamides described in the patent application. EP 354 835, disulphides of N-mono or
N, N-dialkylmercapto 4-butyramides described in the patent application
EP 368 763 and disulphides of aminomercaptoalkylamides described in patent application EP 403 267.
Dans les compositions auto-neutralisantes, le disulfure est généralement présent en un rapport molaire de 0,-5 à 2,5 et de préférence de 1 à 2 par rapport au mélange azéotrope des composés (I) et (Il). In the self-neutralizing compositions, the disulfide is generally present in a molar ratio of from 0.5 to 2.5 and preferably from 1 to 2 relative to the azeotropic mixture of the compounds (I) and (II).
Les disulfures de formule (III), (IV) et (V) sont obtenus par oxydation du mélange azéotrope des composés (I) et (II)j soit à l'air, soit en utilisant des oxydants connus comme par exemple l'eau oxygénée en présence éventuellement de sels métalliques tels que par exemple les sels ferreux. The disulfides of formula (III), (IV) and (V) are obtained by oxidation of the azeotropic mixture of compounds (I) and (II) either in air or by using known oxidants, for example water oxygenated optionally in the presence of metal salts such as, for example, ferrous salts.
La présente invention a également pour objet un procédé de déformation permanente des cheveux consistant, dans une première étape, à réduire les liaisons disulfures de la kératine par application, pendant environ 5 à 60 minutes, d'une composition réductrice telle que définie ci-dessus puis dans une seconde étape à reformer lesdites liaisons par application d'une composition oxydante ou éventuellement en laissant agir l'oxygène de l'air. The present invention also relates to a permanent hair deformation process consisting, in a first step, of reducing the disulfide bonds of keratin by applying, for about 5 to 60 minutes, a reducing composition as defined above. then in a second step to reform the said bonds by application of an oxidizing composition or optionally leaving the oxygen in the air.
La présente invention a également pour objet un procédé d'ondulation des cheveux dans lequel on applique une composition réductrice telle que définie ci-dessus sur des cheveux mouillés préalablement roulés sur des rouleaux ayant de 4 à 20 mm de diamètre, la composition pouvant éventuellement être appliquée au fur et à mesure de ltenroulage des cheveux; on laisse ensuite agir la composition réductrice pendant un temps de 5 à 60 min. de préférence de 5 à 30 min. à une température pouvant être comprise entre 20 et 55"C, puis on rince ensuite abondamment et après quoi on applique sur les cheveux enroulés une composition 'oxydante, permettant de reformer les liaisons disulfures de la kératine, pendant un temps de pose de 2 à 10 minutes. Après avoir enlevé les rouleaux, on rince abondamment la chevelure. The subject of the present invention is also a method of waving the hair in which a reducing composition as defined above is applied to wet hair previously rolled on rolls having from 4 to 20 mm in diameter, the composition possibly being able to be applied as the hair is rolled up; the reducing composition is then allowed to act for a period of 5 to 60 minutes. preferably from 5 to 30 min. at a temperature which may be between 20 and 55 ° C, then rinsed thoroughly and then applied to the wound hair an oxidizing composition, to reform the disulfide bonds of keratin, for a laying time of 2 to 10 minutes After removing the rollers, the hair is thoroughly rinsed.
La composition d'oxydation ou oxydante est du type couramment utilisé 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. The oxidation or oxidizing composition is of the type commonly used and contains as oxidizing agent oxygenated water, an alkaline bromate, a persalt, a polythionate or a mixture of alkaline bromate and persalt.
La concentration en eau oxygénée peut varier de 1 à 20 volumes et de préférence de I à 10, la concentration en bromate alcalin de 2 à 12 Z et celle en persel de 0,1 à 15 Z 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. L'eau oxygénée peut être stabilisée par exemple par la phénacétine, l'acétanilide, les phosphates mono ou trisodiques ou par le sulfate d'hydroxy-8 quinoléine. The concentration of hydrogen peroxide can vary from 1 to 20 volumes and preferably from 1 to 10, the alkali bromate concentration from 2 to 12% and the persalt concentration from 0.1 to 15% by weight relative to the total weight of the product. oxidizing composition. The pH of the oxidizing composition is generally between 2 and 8 but preferably between 3 and 6. The hydrogen peroxide may be stabilized for example by phenacetine, acetanilide, mono or trisodium phosphates or by hydroxy sulfate -8 quinoline.
L'oxydation peut être immédiate ou différée.Oxidation can be immediate or delayed.
La présente invention a également pour objet un procédé de défrisage ou de décrêpage des cheveux dans lequel on applique sur les cheveux une composition réductrice selon l'invention, puis on soumet les cheveux à une déformation mécanique permettant de les fixer dans leur nouvelle forme, par une opération de lissage des cheveux avec un peigne à large dents, avec le dos d'un peigne ou à la main. Après un temps de pose de 5 à 60 min., en particulier de 5 à 30 min., on procède alors à un nouveau lissage puis on rince soigneusement et on applique la composition oxydante ou fixatrice que lton laisse agir pendant un temps de 2 à 10 min. environ puis on rince abondamment les cheveux. The subject of the present invention is also a hair straightening or decreping process in which a reducing composition according to the invention is applied to the hair, and then the hair is subjected to a mechanical deformation allowing them to be fixed in their new shape by an operation of smoothing the hair with a comb with large teeth, with the back of a comb or by hand. After a laying time of 5 to 60 min., In particular 5 to 30 min., A new smoothing is then carried out and then rinsed thoroughly and the oxidizing or fixing composition is applied which allows it to act for a period of 2 to 10 minutes. about then rinses the hair thoroughly.
On va maintenant donner à titre d'illustration et sans aucun caractère limitatif des exemples de préparation du mélange azéotrope selon l'invention ainsi que des exemples de compositions réductrices selon l'invention et leur utilisation dans un procédé de déformation permanente des cheveux. Examples of the preparation of the azeotropic mixture according to the invention, as well as examples of reducing compositions according to the invention and their use in a permanent hair deformation process, will now be given by way of non-limiting illustration.
EXEMPLES DE PREPARATION
EXEMPLE 1 : Préparation du mélange azéotrope constitué de 2/3 de thioglycolate d'hydroxy-2 propyle (I) et de 1/3 de thioglycolate d'hydroxy-2 méthyl-l éthyle (II) par esterification directe.EXAMPLES OF PREPARATION
EXAMPLE 1 Preparation of the azeotropic mixture consisting of 2/3 of 2-hydroxypropyl thioglycolate (I) and 1/3 of 2-hydroxyethyl-1-ethyl (II) thioglycolate by direct esterification.
a) Sans co-solvant
On chauffe 7 heures à 140-1500C, sous atmosphère d'argon, un mélange de 456,6 g (4,96 moles) d'acide thioglycolique et 754,4 g (9,92 moles) de propanediol-1,2 en distillant au fur et à mesure l'eau formée.a) Without co-solvent
A mixture of 456.6 g (4.96 mol) of thioglycolic acid and 754.4 g (9.92 mol) of 1,2-propanediol is heated under argon for 7 hours at 140 ° C. to 140 ° C. under argon. distilling as the water formed.
L'eau résiduelle et une partie du propanediol-1,2 en excès sont ensuite distillés sous le vide d'une trompe à eau (Eb 4 1100C). The residual water and part of the excess propanediol-1,2 are then distilled under the vacuum of a water pump (Eb 4 1100C).
On procède ensuite à la distillation proprement dite sous un vide d'environ 5,32 hPa en recueillant :
- la fraction 76-105"C (218,7 g) dont la composition pondérale déterminée par dosage de thiol et C.P.G. est la suivante ester (I) : 73 g ester (II) : 35,6 g
108,6 g propanediol-1,2 : 110,1 g
- la fraction 106-115"C (444,6 g de liquide incolore) contenant uniquement le mélange azéotrope des deux esters dans le rapport 2/1. Le dosage de thiol (I2 0,1N). L'analyse C.P.G. et le spectre RMN13C sont conformes.The actual distillation is then carried out under a vacuum of approximately 5.32 hPa, collecting:
the fraction 76 ° -105 ° C. (218.7 g) whose weight composition determined by thiol and CPG assay is the following ester (I): 73 g ester (II): 35.6 g
108.6 g 1,2-propanediol: 110.1 g
the fraction 106-115 ° C (444.6 g of colorless liquid) containing only the azeotropic mixture of the two esters in the ratio 2/1, the thiol assay (I2 0.1N), the GPC analysis and the spectrum; 13C NMR are compliant.
Analyse élémentaire : C10H2006S2
(Fraction : 106-115 C/5,32 hPa)
HZ H% O% S%
Calculé 39,98 6,71 31,96 21,35
Trouvé 40,09 6,67 32,12 21,60
b) Avec un co-solvant
On chauffe 6 heures au reflux et sous atmosphère d'argon, une solution de 92 g (1 mole) d'acide thioglycolique, 113 cm3 (1,5 moles) de propanediol-1,2 et 150 cm3 de dichloro-1,2 éthane en recueillant l'eau formée à l'aide d'un appareil Dean-Stark.Elemental analysis: C10H2006S2
(Fraction: 106-115 C / 5.32 hPa)
HZ H% O% S%
Calculated 39.98 6.71 31.96 21.35
Found 40.09 6.67 32.12 21.60
b) With a co-solvent
A solution of 92 g (1 mole) of thioglycolic acid, 113 cm 3 (1.5 moles) of 1,2-propanediol and 150 cm 3 of 1,2-dichloroethane is refluxed for 6 hours under an argon atmosphere. ethane by collecting the water formed using a Dean-Stark apparatus.
On distille ensuite sous le vide de la trompe à eau et on recueille 69,4 g de liquide incolore de point d'ébullition 137-143"C sous 26,6 hPa. It is then distilled under water-jet vacuum and 69.4 g of colorless liquid having a boiling point of 137 ° -143 ° C. is collected under 26.6 hPa.
Le spectre RMN 3C correspond au mélange (I)/(II) : 2/1. The 3C NMR spectrum corresponds to the mixture (I) / (II): 2/1.
EXEMPLE 2 : Préparation du mélange azéotrope constitué de 2/3 de thioglycolate d'hydroxy-2 propyle (I) et de 1/3 de thioglycolate d'hydroxy-2 méthyl-l éthyle par transesterification.EXAMPLE 2 Preparation of the azeotropic mixture consisting of 2/3 of 2-hydroxypropyl thioglycolate (I) and 1/3 of 2-hydroxyethyl-1-methylethyl thioglycolate by transesterification.
On chauffe 3 heures à 120 OC, sous atmosphère inerte, une solution de 60 g (0,5 mole) de thioglycolate d'éthyle et 76 g (0,5 mole) de propanediol-1,2 en distillant méthanol formé. A solution of 60 g (0.5 mole) of ethyl thioglycolate and 76 g (0.5 mole) of 1,2-propanediol while distilling the methanol formed is heated for 3 hours at 120 ° C. under an inert atmosphere.
On purifie ensuite par distillation sous le vide d'une trompe à eau pour recueillir 31,5 g de liquide incolore de point d'ébullition 140-143 C sous 27,9 hPa. It is then purified by vacuum distillation with a water pump to collect 31.5 g of colorless liquid with a boiling point of 140-143 ° C at 27.9 hPa.
Le spectre RMN C est conforme. The C NMR spectrum is consistent.
Analyse élémentaire : C10H20O6S2 HZ HZ OZ 5%
Calculé 39,98 6,71 31,96 21,35
Trouvé 40,02 6,71 32,12 21,53
EXEMPLE 3 : Préparation du mélange des disulfures (III), (IV) et (V).Elemental analysis: C10H20O6S2 HZ HZ OZ 5%
Calculated 39.98 6.71 31.96 21.35
Found 40.02 6.71 32.12 21.53
EXAMPLE 3 Preparation of the mixture of disulfides (III), (IV) and (V).
A une solution de 15 g (0,1 mole) du mélange azéotrope (I)/(II) obtenu selon l'exemple 1 ou 2 dans 100 cm3 de tétrahydrofuranne, on ajoute goutte à goutte 5,1 cm3 (0,05 mole) d'eau oxygénée à 30 % et agite à température ambiante. To a solution of 15 g (0.1 mole) of the azeotropic mixture (I) / (II) obtained according to Example 1 or 2 in 100 cm 3 of tetrahydrofuran, 5.1 cm 3 (0.05 mole) is added dropwise. ) 30% hydrogen peroxide and stirred at room temperature.
La transformation est complète après 1 h de réaction (C.C.M. et dosage de thiol). The transformation is complete after 1 hour of reaction (C.C.M. and thiol assay).
Après évaporation du solvant et séchage sous vide à 40 C, on obtient 14,1 g de liquide incolore à jaune très pâle. After evaporation of the solvent and drying under vacuum at 40 ° C., 14.1 g of colorless to very pale yellow liquid are obtained.
Par RMN13C DMSO d6, C C.P.G. capillaire DBI et couplage GC/MS, on met en évidence la présence des 2 disulfures symétriques (III) et (IV) et du disulfure mixte (V). By 13 C NMR DMSO d6, C.P.G. DBI capillary and GC / MS coupling, the presence of symmetrical (III) and (IV) disulfides and mixed disulfide (V) is demonstrated.
Analyse élémentaire : C10H1806S2 C% H% H% O% Si
Calculé 40,25 6,08 32,17 21,49
Trouvé 40,15 6,12 32,20 21,43
EXEMPLES DE COMPOSITION
EXEMPLE A
On prépare selon l'invention, une composition réductrice de 'déformation permanente des cheveux en procédant de la manière suivante
On prépare tout d'abord la solution (a) - Mélange azéotrope (I)/(II)................................. 15 g - Propylène glycol........................................... 7,8 g
On prépare ensuite la solution (b) - Tégobétaine HS vendue par la Société GOLDSCHMIDT............ 2,3 g - Triéthanolamine............................................. 2,4 g - Parfum qs - Eau déminéralisée qsp....................................... 77,2 g
Après mélange de la solution (a) avec la solution (b), on obtient 100 g de composition réductrice ayant un pH de 7,0.Elemental analysis: C10H1806S2 C% H% H% O% Si
Calculated 40.25 6.08 32.17 21.49
Found 40,15 6,12 32,20 21,43
EXAMPLES OF COMPOSITION
EXAMPLE A
According to the invention, a reducing composition for permanent deformation of the hair is prepared as follows:
The solution (a) - Azeotropic mixture (I) / (II) is first prepared ............................. .... 15 g - Propylene glycol ......................................... .. 7.8 g
Then the solution (b) - Tegobétaine HS sold by the company GOLDSCHMIDT ............ 2.3 g - Triethanolamine ................ ............................. 2,4 g - Perfume qs - Demineralised water qsp .......... ............................. 77.2 g
After mixing solution (a) with solution (b), 100 g of reducing composition having a pH of 7.0 are obtained.
On applique cette composition réductrice sur des cheveux mouillés, préalablement enroulés sur des bigoudis, et on laisse agir 20 minutes à température ambiante. On rince ensuite abondamment à Liteau et on applique alors la composition oxydante suivante : - Eau oxygénée à 200 volumes ; 4,8 g - Stabilisant................................................. 0,2 g - Alcool oléique à 20 moles d'oxyde d'éthylène 1,5 g - Acide citrique qs...................... pH 3 - Eau déminéralisée qsp........................................ 100 g
On laisse agir la composition oxydante pendant 10 minutes, rince abondamment à l'eau puis on enlève les bigoudis.This reducing composition is applied to wet hair, previously wound on curlers, and allowed to act for 20 minutes at room temperature. Then rinsed abundantly at Liteau and then applies the following oxidizing composition: - hydrogen peroxide 200 volumes; 4.8 g - Stabilizer ............................................ ..... 0.2 g - Oleic alcohol with 20 moles of ethylene oxide 1.5 g - Citric acid qs ..................... pH 3 - Demineralized water qs ........................................ 100 g
The oxidizing composition is allowed to act for 10 minutes, rinsed thoroughly with water and then the curlers are removed.
Après séchage sous casque, on constate que les cheveux présentent de belles boucles avec un bon degré de frisure. After drying under the helmet, we find that the hair has beautiful curls with a good degree of crimp.
: * *
*
En utilisant le même mode opératoire que décrit ci-dessus, on a procédé à une déformation permanente des cheveux à l'aide des compositions réductrices et oxydantes des exemples B à E suivantes
EXEMPLE B 1) COMPOSITION REDUCTRICE
Solution (a) - Mélange azéotrope (I)/(II).................................. 7,5 g - Monothioglycolate de glycérol 8,3 g - Glycérine 3,9 g
Solution (b) - Chlorure d'oléocétyl diméthylammonium 1,4 g - Carbonate acide d'ammonium.................................. 3,5 g - Parfum qs - Eau déminéralisée qsp....................................... 80,3 g
On obtient 100 g de solution ayant un pH de 7,1.
: * *
*
Using the same procedure as described above, the hair was permanently deformed using the reducing and oxidizing compositions of Examples B to E below.
EXAMPLE B 1) REDUCING COMPOSITION
Solution (a) - Azeotropic mixture (I) / (II) .................................. 7, 5 g - Glycerol Monothioglycolate 8.3 g - Glycerin 3.9 g
Solution (b) - oleocetyl dimethylammonium chloride 1.4 g - Ammonium acid carbonate .............................. .... 3.5 g - Perfume qs - Demineralized water qsp ................................... .... 80.3 g
100 g of solution having a pH of 7.1 are obtained.
2) COMPOSITION OXYDANTE -Eau oxygénée à 200 volumes..................................... 4,8 g - Stabilisants : sulfate d'hydroxy-8 quinoléine et phénacétine 0,06 g - Acide citrique qs................ pH 3 - Eau déminéralisée qsp..........................................100 g
EXEMPLE C 1) COMPOSITION REDUCTRICE
Solution (a) - Mélange azéotrope (I)/(II)..................................... 7,5 g - Propylène glycol............................................... 7,8 g
Solution (b) - Chlorhydrate de cystéamine..................................... 5,6 g - Tégobétaïne HS vendue par la Société GOLDSCHMIDT............... 1,3 g - Triéthanolamine................................................ 2,1 g - Parfum qs - Eau déminéralisée qsp.......................................... 84,7 g
On obtient 100 g de solution ayant un pH de 7,0.2) OXIDIZING COMPOSITION - Oxygenated water at 200 volumes ..................................... 4,8 g - Stabilizers: 8-hydroxyquinoline sulfate and phenacetin 0.06 g - Citric acid qs ................ pH 3 - Demineralised water qs ....... ................................... 100 g
EXAMPLE C 1) REDUCTIVE COMPOSITION
Solution (a) - Azeotropic mixture (I) / (II) .................................... 7.5 g - Propylene glycol .......................................... ..... 7.8 g
Solution (b) - Cysteamine Hydrochloride ..................................... 5.6 g - Tegobetaine HS sold by the company GOLDSCHMIDT ............... 1,3 g - Triethanolamine ...................... .......................... 2.1 g - Perfume qs - Demineralized water qsp ............. ............................. 84.7 g
100 g of solution having a pH of 7.0 are obtained.
2) COMPOSITION OXYDANTE - Bromate de sodium.............................................. 8 g - Triéthanolamine qs............... pH 7,5 - Phosphate monosodique monohydraté.............................. 0,3 g - Phosphate trisodique........................................... 0,5 g - Eau déminéralisée qsp..........................................100 g
EXEMPLE D 1) COMPOSITION REDUCTRICE
Solution (a) - Mélange azéotrope (I)/(II)..................................... 7,5 g - Propylène glycol............................................... 7,8 g
Solution (b) - N-acétylcystéamine............................................. 5,9 g - Tégobétaïne HS vendue par la Société GOLDSCHMIDT............... 1,3 g - Triéthanolamine 1,7 g - Parfum qs - Eau déminéralisée qsp.......................................... 84,7 g
On obtient 100 g de solution ayant un pH de 6,9.2) OXIDIZING COMPOSITION - Sodium bromate .......................................... .... 8 g - Triethanolamine qs ............... pH 7.5 - Sodium dihydrogen phosphate monohydrate .................. ............ 0.3 g - Trisodium phosphate ............................... ............ 0.5 g - demineralised water qs .............................. ............ 100 g
EXAMPLE D 1) REDUCING COMPOSITION
Solution (a) - Azeotropic mixture (I) / (II) .................................... 7.5 g - Propylene glycol .......................................... ..... 7.8 g
Solution (b) - N-acetylcysteamine .......................................... ... 5.9 g - Tegobetaine HS sold by GOLDSCHMIDT ............... 1.3 g - Triethanolamine 1.7 g - Perfume qs - Demineralized water qs ... ....................................... 84.7 g
100 g of solution having a pH of 6.9 are obtained.
2) COMPOSITION OXYDANTE
On utilise la même composition oxydante que celle décrite à l'exemple A.2) OXIDIZING COMPOSITION
The same oxidizing composition is used as that described in Example A.
EXEMPLE E 1) COMPOSITION REDUCTRICE
Solution (a) - Mélange azéotrope (I)/(II)..................................... 7,5 g - N-propionylcystéamine.......................................... 5,9 g - Propylène glycol 7,8 g
Solution (b) - Tégobétaïne HS vendue par la Société GOLDSCHMIDT............... 1,3 g - Triéthanolamine 1,7 g - Parfum qs - Eau déminéralisée qsp.......................................... 78,8 g
On obtient 100 g de solution ayant un pH de 6,9.EXAMPLE E 1) REDUCING COMPOSITION
Solution (a) - Azeotropic mixture (I) / (II) .................................... 7.5 g - N-propionylcysteamine ......................................... 5.9 g - Propylene glycol 7.8 g
Solution (b) - Tegobetaine HS sold by the company GOLDSCHMIDT ............... 1,3 g - Triethanolamine 1,7 g - Perfume qs - Demineralized water qsp ...... .................................... 78.8 g
100 g of solution having a pH of 6.9 are obtained.
2) COMPOSITION OXYDANTE
On utilise la même composition oxydante que celle décrite à l'exemple B. 2) OXIDIZING COMPOSITION
The same oxidizing composition is used as that described in Example B.
Claims (17)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9109280A FR2679448B1 (en) | 1991-07-23 | 1991-07-23 | AZETROPE MIXTURE OF 2-HYDROXY-2-PROPYL THIOGLYCOLATE AND 2-HYDROXY-2-METHYL-ETHYL THIOGLYCOLATE, PROCESS FOR THE PRODUCTION THEREOF, AND USE THEREOF IN A PERMANENT HAIR DEFORMATION PROCESS. |
| PCT/FR1992/000728 WO1993001791A1 (en) | 1991-07-23 | 1992-07-23 | Azeotropic blend of propyl 2-hydroxy thioglycolate and ethyl 1-methyl 2-hydroxy thioglycolate, process for its preparation and use thereof in a process for achieving a permanent change in hair waviness |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9109280A FR2679448B1 (en) | 1991-07-23 | 1991-07-23 | AZETROPE MIXTURE OF 2-HYDROXY-2-PROPYL THIOGLYCOLATE AND 2-HYDROXY-2-METHYL-ETHYL THIOGLYCOLATE, PROCESS FOR THE PRODUCTION THEREOF, AND USE THEREOF IN A PERMANENT HAIR DEFORMATION PROCESS. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2679448A1 true FR2679448A1 (en) | 1993-01-29 |
| FR2679448B1 FR2679448B1 (en) | 1993-10-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9109280A Expired - Fee Related FR2679448B1 (en) | 1991-07-23 | 1991-07-23 | AZETROPE MIXTURE OF 2-HYDROXY-2-PROPYL THIOGLYCOLATE AND 2-HYDROXY-2-METHYL-ETHYL THIOGLYCOLATE, PROCESS FOR THE PRODUCTION THEREOF, AND USE THEREOF IN A PERMANENT HAIR DEFORMATION PROCESS. |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2679448B1 (en) |
| WO (1) | WO1993001791A1 (en) |
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Also Published As
| Publication number | Publication date |
|---|---|
| FR2679448B1 (en) | 1993-10-15 |
| WO1993001791A1 (en) | 1993-02-04 |
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