WO1991010421A1 - Utilisation de derives n-acyle d'homocysteine pour modifier la structure de la keratine et des compositions cosmetiques contenant ces derives - Google Patents

Utilisation de derives n-acyle d'homocysteine pour modifier la structure de la keratine et des compositions cosmetiques contenant ces derives Download PDF

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Publication number
WO1991010421A1
WO1991010421A1 PCT/EP1991/000128 EP9100128W WO9110421A1 WO 1991010421 A1 WO1991010421 A1 WO 1991010421A1 EP 9100128 W EP9100128 W EP 9100128W WO 9110421 A1 WO9110421 A1 WO 9110421A1
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Prior art keywords
homocysteine
derivatives
depilatory
composition
hair
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PCT/EP1991/000128
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English (en)
Inventor
Hervé Tournier
Hubert Delagneau
Philippe Bussat
Roland Hyacinthe
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Reckitt & Colman
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Publication of WO1991010421A1 publication Critical patent/WO1991010421A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/04—Depilatories
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair

Definitions

  • N-acyl derivatives of homocvsteine to modify the structure of keratin and cosmetic compositions containing these derivatives.
  • the present invention relates to the treatment of materials of organic origin based on keratin, in particular horn, bristles, nails, hair, wool, silk and other analogous biosubstances, in order permanently to modify their shape and structure.
  • This treatment consists in attacking the sulfur bonds constituting crosslinking bridges in their polypeptide skeleton.
  • the invention also relates to cosmetic compositions, for example for use on the hair to wave straight hair or to straighten curly hair, or depilatory compositions to remove superfluous hair.
  • the term "permanent modification” is here intended to refer to a treatment leading to a more or less pronounced restructuring, deformation or degradation of the keratin due to the more or less complete breakage of the thioether or disulfide (cysteine type) bonds of the polypeptide.
  • the invention relates in particular to the use of some N-acyl derivatives of homocysteine and its water- soluble salts, the formula of which derivatives will be specified below, to effect such a permanent modification.
  • the document US-A-4 121 904 also specifies that the sulfur- containing reagent is able to act either as free thiol or, if the pH is alkaline, as thiolate anion in accordance with the following equations, where A-SH denotes the active thiol and B denotes the non-sulfur-containing portion of the keratin chain.
  • sulfur-containing organic compounds having a keratolytic action which are commonly used to modify the structure of keratin, the following may be mentioned as examples : lower mercaptocarboxylic acids of formula HS-(CH 2 ) n -COOH, where n is an integer no higher than about 4 to 5, for example thioglycolic acid and thiolactic acid and their alkali metal, alkaline earth metal and ammonium salts.
  • the sulfur-containing glycols may also be mentioned, for example thioglycol, thioglycerol and aminothioglycol.
  • Cysteine, cysteamine and the glyceride esters of thioglycolic acid are also mentioned (see EP-A-302,265) .
  • the keratolytic action of homocysteine and some of its derivatives is also known.
  • the Japanese document JP 61-165.316 HADA KESHOHIN KAGAK
  • the document EP-A-236,533 (SUMITOMO) describes a preparation for permanent waving containing homocysteine or its esters with lower aliphatic alcohols ( C ⁇ to C 6 ) .
  • homocysteine is more effective than cysteine and its effect is longer lasting. Moreover, the proportion of homocystine (inactive) naturally present in homocysteine is well below the proportion of cystine present in cysteine.
  • This document also provides for the use of homocysteine in the form of its salts with inorganic or organic bases.
  • R denotes an alkanoyl C- ⁇ to C group, benzoyl, toluoyl and ethylbenzoyl.
  • N- acyl derivatives of homocysteine do not all have a keratolytic action.
  • N-(3,4,5-trimethoxy benzoyl)-homocysteine has hypnotic properties ; N -(carboxymethylacetyl)- homocysteine is said to be mucolytic and N,£3-diacetyl homocysteine has trophic properties for the skin and hair, whereas N-( (chromon-2-yl) carbonyl)-homocysteine is cicatrization accelerator and a hair protector. It however discloses in the family of aliphatic N-acyl derivatives of homocysteine only the N-propionyl (C 3 ) derivative. Knowing the above, it is all the more surpri ⁇ sing to have discovered that the N-acyl homocysteines of formula (II)
  • the present invention has therefore as its object the use of N-acyl-derivatives of homocysteine of formula HS-(CH 2 ) 2 -CH-COOH (II)
  • R is substituted or unsubstituted, saturated or unsaturated, straight-chain or branched CO-alkyl radical of more than 4 carbon atoms, for lasting modification of keratinous materials, in particular as agents for waving hair or as depilatory agents
  • R can be (a) an indepen ⁇ dent single radical or, (b) can constitute a recurring unit in a polymer as will be seen below.
  • the number of carbons in R is limited to 24 ; however, the C 5 to C 16 , particularly C 6 -C 12 , and more particularly the c 6 -c l ° compounds, are preferred because it is within this range that the effectiveness of the derivatives (II) is the most satisfactory.
  • the derivatives (II) are used in aqueous solution or dispersion, such solutions or disper ⁇ sions also being able to contain other ingredients customarily used in cosmetology for depilatory formulations or for formulations for permanent waving of the hair.
  • Such ingredients are well known to those skilled in the art and are widely mentioned in the prior art.
  • the derivatives (II) can be used individually or as mixtures or in combination with other known organic or inorganic sulfur-containing keratolytic compounds.
  • the aqueous phase can advantageoulsy comprise a lipophilic phase with which the derivative or derivatives (II) are combined ; this lipophilic phase can consist of vegetable or mineral oil or fatty matter, or of dispersion of liposomes, for example. It should be noted that, in this latter case, because of the lipophilic chain of the derivatives (II) the latter are incorporated easily in the liposome membrane, which increases their keratolytic activity.
  • the derivatives (II) When the derivatives (II) are used in composi- tions for permanent waving or for straightening curly hair, their concentration in the aqueous phase is generally of the order of 0,5 to 10 % by weight depending on wether they are or are not combined with other known keratolytic agents such as thioglycolate, thioglycerol, thioglycol, 3-mercaptopropionic acid, N-hydroxyethy1)-mercaptoacetami- de, N-methylmercaptoacetamide, ⁇ - mercaptoethylamine (cys- teamine) , mercaptopropionamide, 2-mercaptoethanesulfonic acid, dimercaptoadipic acid, dithiothreitol, homocysteine thiolactone and inorganic sulfides such as lithium, sodium, potassium, caesium, magnesium, calcium, strontium and barium sulfides (see for example
  • the pH of the aqueous phase is preferably between 7 and 8,5, but it is possible to go outside these limits for some special applications.
  • the rates of reactions are, in fact, lower at the lower power pHs, but pHs which are too high could cause too severe an attack on the hair if the action is prolonged. A compromise must therefore be achieved depending on the type of application intended.
  • compositions can also contain other ingredients, such as thickeners, agents for increasing the viscosity, surfactants, buffers, swelling agents, colour ⁇ ants, perfumes, opacifying agents, etc.
  • thickeners agents for increasing the viscosity
  • surfactants buffers
  • swelling agents swelling agents
  • colour ⁇ ants perfumes
  • opacifying agents etc.
  • the derivatives (II) When used in the aqueous depilatory compositions, their concentration is generally somewhat higher than in the compositions for use in treatment of the hair, in particular of the order of 1 to 15 % by weight, depending on whether they act on their own or in combination with other keratolytes. However, it is in particular on the increase in the pH that reliance is placed to lead to an effective disintegration rather than a simple deformation of the keratin.
  • the pH is generally of the order of 10 to 12, 5, but these values can be modified in certain cases. In general, it is sought to establish a compromise between the effectiveness of the depilatory (high pH) and its harmlessness to the skin (pH as low as possible, but adequate rate of treatment) .
  • the N-acyl derivatives of homocysteine are very active at pHs which are relatively not very high (of the order of 10 to 11) , which makes them particularly valuable for these applica ⁇ tions.
  • the depilatory compositions of the present invention generally comprise, in addition to the active depilatory agents, thickeners enabling "body” to be given to the composition during its application to the skin, wetting agents (surfactants) to improve the contact with the skin, and softening fillers such as clay, MgO, bentonite, talc, etc., as well as other adjuvants, in particular perfumes.
  • thickeners those which may be mentioned are the natural gums (guar, xanthan, tragacanth, karaya, etc.) and some hydrophilic polymers such as carboxymethylcellulose, hydroxyethy1cellulose, polyvinyl alcohol, swelling hydroxyacrylates and dextrins.
  • the surfactants can be anionic (soaps, alkyl- and alkyl- aryl-sulfonates and mixed sulfates of fatty alcohols and alkali metals) ; cationic (quaternary alkyl-arylalkyl- or aryl-ammonium compounds) ; nonionic (polyoxyethylenated fatty alcohols, polyoxyalkylenated alkylphenols, etc.) and amphoteric (sulfo- and phosphobetaines) .
  • the formulations comprise at least one polymer which, on drying, forms films at the surface of the skin onto which the depilatory composition has been applied.
  • the drying time is calculated to correspond to the time necessary for the depilatory to act on the keratin of the hairs to be epilated, the film thus formed can then simply be removed, this film then painless ⁇ ly bringing away the hairs degraded by the depilatory.
  • a film-forming polymer of this type can be, for example, PVA (polyvinyl alcohol) , PVP (polyvinylpyrrolidone) , polyacryl- a ide, polyacrylic acid and others in the form of polyacry- lic solutions, dispersions or latex and also the latexes of poly(1,4-cis-isoprene) having molecular weights which can reach and exceed 10 6 daltons (see for example, the document EP-A-196,896, which describes depilatory films containing such polymers and, as depilatory, thioglycolic acid) .
  • PVA polyvinyl alcohol
  • PVP polyvinylpyrrolidone
  • polyacryl- a ide polyacrylic acid and others in the form of polyacry- lic solutions, dispersions or latex and also the latexes of poly(1,4-cis-isoprene) having molecular weights which can reach and exceed 10 6 daltons
  • a polymer consisting of a succession of alkylene units, some of which comprise an acyl group linked to the amino group of homocysteine.
  • Such a polymer corresponds to the derivatives (II) (case b) in which the group R (also substituted by other appended hydrophilic functions) represents a monomer unit repeated n times. —[CH(COOH)-CH-CH 2 -CH(OCH 3 ) ] n
  • Such a polymer can be produced, for example, by reaction of homocysteine thiolactone with a polymer comprising anhydride or acylchloride functions.
  • a suitable polymer for this reaction is the polymer termed GANTREZ AN-
  • the present depilatory compositions can contain a variety of adjuvants, such as gelling agents, emollients, swelling agents, agents for increasing the viscosity, thickeners, surfactants, perfumes, softeners, etc. , all well known to those skilled in the art and being mentioned in the prior art mentioned below, as well as plasticizers, in particular, glycerol, polyglycerol, polyglycerides and polyols, such as polyethy ⁇ lene glycol (PEG) .
  • adjuvants such as gelling agents, emollients, swelling agents, agents for increasing the viscosity, thickeners, surfactants, perfumes, softeners, etc.
  • plasticizers in particular, glycerol, polyglycerol, polyglycerides and polyols, such as polyethy ⁇ lene glycol (PEG) .
  • plasticizers which are suitable, the following may be mentioned in particular : diethylene glycol, triethylene glycol, triethanolamine, butane-l,3-diol, Carbowax-2000, triethanolamine acetate and ethanol-acetamide.
  • the compositions can also contain epilation accelerators (see, for example, EP-A-96,521 (PROCTER & GAMBLE)), i.e. urea guanidine, thiourea and thiocyanate.
  • the portion by weight of these accelarators is preferably between 0.5 to 10 %.
  • the compounds of formula II are obtained easily by reaction of homocysteine in the lactone form with an acyl halide or anhydride RCOX or RCO-O-OCR in accordance with the known techniques (for example described in detail in the document FR-A-2,265,355), followed by opening of the lactone ring in in an alkaline medium.
  • the present invention has at least as its object the N-acyl derivatives of homocysteine as well as their salts characterized in that they correspond to the general formula HS-(CH 2 ) 2 -CH-COOH (II)
  • R represents an aliphatic acyl group containing from 5 to 24 carbon atoms, notably the derivatives of formula II wherein R is a Cg-Cn ⁇ O radical, and particularly the derivatives described as examples and more particularly the examples which follow and illustrate the invention in more detail.
  • 2-thiopyridine formed by reaction of 2.2*-dithiopyridine with the free thiol functions of a standard sample of keratin (lock of hair) treated beforehand (under standard conditions) with a compound for which it is desired to test the activity.
  • TRIS-EDTA buffer at pH 8.5 prepared from 24.2 g of TRIS diluted in 100 ml of a 0.2 M solution of EDTA (tetrasodium salt) and then made up to 1 liter and then adjusted to a pH of 8.2
  • the hair is allowed to react for exactly l hour in the vessel, which is closed or preferably under a blanket of nitrogen, and the optical density* is measured at 353 nm against a blank sample obtained after the hair has been attacked in a sodium hydroxide solution at pH 12,5 without depilatory agent.
  • the optical density values obtained are used directly for comparison (comparison with 3 - 5 % calcium thioglycolate or thioglycerol solutions at pH 12,5) to assess the degree of attack associated specifically with the depilatory agents concerned.
  • optical densities exceed a values of 2 it is preferable to carry out a dilution by a factor of 5 or 10.
  • the product can optionally be recrystallized from ethanol.
  • ethyl heptanoate takes place, the chloroform being stabilized with 1 % of ethanol. This prevents immediate crystalliza ⁇ tion of the product in ethanol.
  • the cylic compound was then opened by dissol ⁇ ving in aqueous 2N NaOH.
  • the keratolytic activity of these derivatives was measured in aqueous solution (1 - 4% ; pH 12.5) using the abovementioned test. It was found that the activity of the C ⁇ and C 8 compounds was about 30 - 40 % higher than that of of the C ⁇ derivative ; the reactivity then decreases progressively when the chain length increases above C 9 to C 0
  • the results, in terms of comparative activity are given in the table below.
  • the first line corresponds to the activity of thioglycerol on its own.
  • the second line corresponds to the addition of 1 % of homocysteine only.
  • a polymer of formula (III) containing grafted homocysteine groups was prepared by reaction stoichiome- trie amounts (molecular equivalents) of GANTREZ AN -119 polymer (manufactured by GAF Corp.) and of homocysteine thiolactone (free base) in THF. The THF was evaporated, the residue dissolved in ethanol and the desired polymer precipitated by adding ether (yield 85 %) .
  • Aqueous film-forming compositions were prepared containing concentrations by weight of 2 to 10 % of the abovementioned polymer to which 2 to 10 % of polyvinyl alcohol (PVA, MW 100 000) had been added.
  • Variable amounts from 1 to 4 %) of derivatives (II) (C 7 to C 12 ) were also added to some samples. These compositions were used as depilatory in thin layers and it was found that after a drying time of about 15 - 20 minutes it was possible easily to pull off the films thus formed, the hairs to be removed being removed simultaneously with the film.
  • N-heptanoylhomocysteine then incorporates into the liposome membrane to a large extent by virtue of its heptanoyl chain.
  • a depilatory cream was prepared by mixing the following ingredients (parts by weight) at 75° C (mixture A) :
  • a depilatory composition was thus obtained which was in form of a gel having thixotropic properties during its application to the skin to be epilated. After a few minutes 1 application (3 to 5 minutes) , the depilatory effect being obtained, the gel was removed by simple washing with water.
  • Example 11 2 parts by weight of hydroxyethylcellulose (NATROSOL 250 HHR from Hercules Co.) were intimately mixed at ambient temperature into 60 parts by weight of water and the following were added (all in parts by weight) : 5 of sorbitol, 10 of potassium thioglycolate (30 % aqueous solution) and 1 part of N-octanoylhomocysteine. The pH was then adjusted to 12 - 12.5 using a
  • the above composition formed a stable hydrophilic gel having improved depilatory properties and a weak sulfur odour and capable of being rinsed off easily with water after use.
  • An active concentrate for aerosols was prepared by intimatly mixing the following ingredients :
  • a composition for permanent waving was prepared by intimately mixing 60 parts by weight of water, 5 parts of ammonium thioglycolate (60 % solution of thioglycolic acid neutralized with ammonia) , 2 parts by weight of 28 % aqueous solution of ammonium lauryl sulphate and 2 parts by weight of N-heptanoylhomocysteine and then adjusting the pH to 8.5 - 9.5 using 28 % aqueous NH 4 0H.
  • This composition was successivefully used for waving hair using the techniques customary in hairdressing salons.
  • a gel for permanent waving was prepared in the following way (parts by weight) : 0.5 part of carboxyme- thylcellulose (CMC-7M from Hercules and Co.) was dispersed in 60 parts of water and, at 75° C, a mixture, brought to 75° C, comprising 1 part of liquid paraffin oil (viscosity at 20° C, 70 mPa s) , 0.2 part of cetyl alcohol and 5 parts of ethoxylated (by 10 molecules of ethylene oxide) cetyl alcohol was added to this dispersion, with stirring.
  • CMC-7M carboxyme- thylcellulose
  • the mixture was then cooled to 45 - 50° C and 4 parts of a ⁇ - monothioglycerol and 4 parts of N-decanoyl- homocysteine were added thereto and the pH was adjusted to 8.5 - 9.5 by adding monoethanolamine.
  • the composition was then made up with 0.5 part of a perfume product and with water to give a total of 100 parts by weight. A composition for permanent waving was thus obtained which is effective and releases only a slight odour during its use in a hairdressing salon.

Abstract

L'utilisation de dérivés N-acyle d'homocystéine de formule (II) où R est un radical CO-alkyle à chaîne linéaire ou ramifiée ayant plus de quatre atomes de carbone, substitué ou non substitué, saturé ou non saturé, ainsi que les dérivés de formule (II), permet de modifier de manière durable les matières kératineuses, en particulier sous forme d'agents d'ondulation des cheveux ou d'agents dépilatoires, ou de compositions kératolytiques.
PCT/EP1991/000128 1990-01-16 1991-01-12 Utilisation de derives n-acyle d'homocysteine pour modifier la structure de la keratine et des compositions cosmetiques contenant ces derives WO1991010421A1 (fr)

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CH13090 1990-01-16
CH130/90-9 1990-01-16

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IE (1) IE910124A1 (fr)
PT (1) PT96499A (fr)
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994014428A1 (fr) * 1992-12-22 1994-07-07 Handelman, Joseph, H. Reduction de la pousse des poils a l'aide de composes reactifs de sulfhydryle
EP0713694A1 (fr) * 1994-11-24 1996-05-29 Wella Aktiengesellschaft Composition pour la déformation permanente des cheveux
US5645825A (en) * 1995-06-07 1997-07-08 The Procter & Gamble Company Depilatory compositions comprising sulfhydryl compounds
WO1998030197A1 (fr) * 1997-01-11 1998-07-16 Wella Aktiengesellschaft Procede et agent pour permanentes a base de mercaptoacetamides substitues par alkyle a chaine n-ramifiee et procede permettant de preparer ledit agent
WO1999002125A1 (fr) * 1997-07-09 1999-01-21 Reckitt & Colman France Compositions depilatoires, procedes pour leur preparation et leur utilisation
WO1999006013A2 (fr) * 1997-07-31 1999-02-11 Wella Aktiengesellschaft Agent et procede pour le permanentage des cheveux et procede pour la production de l-alkylmercaptoacetamides
WO1999007330A2 (fr) * 1997-08-06 1999-02-18 Wella Aktiengesellschaft Procedes et agents appropries pour permanenter des cheveux, a base de mercaptoacetamides n,n-disubstitues et procede permettant de preparer lesdits mercaptoacetamides
US5985253A (en) * 1997-03-14 1999-11-16 Wella Ag Hair shaping compositions containing mercaptoethylamines and methods for the permanent shaping of hair using same
US6162425A (en) * 1997-07-25 2000-12-19 Wella Aktiengesellschaft Saturated, alkyl-substituted n-mercaptoacetyl heterocyclic compounds and compositions and methods for permanent shaping of hair based on same and processes for making same
WO2001006998A1 (fr) * 1999-07-23 2001-02-01 Unilever Plc Traitement capillaire utilisant des composes amino organiques
WO2001074318A2 (fr) * 2000-04-01 2001-10-11 Wella Aktiengesellschaft Agent et procede pour le permanentage durable des cheveux a base d'amides de l'acide 2-mercaptopropionique et procede pour leur production
US6743419B1 (en) * 1992-12-22 2004-06-01 The Gillette Company Method of reducing hair growth employing sulfhydryl active compounds
JP2013177384A (ja) * 2012-02-09 2013-09-09 Kracie Seiyaku Kk 角質剥離組成物
US8557229B2 (en) 2010-03-26 2013-10-15 The Procter & Gamble Company Hair removal method and hair removal kit
US9216304B2 (en) 2010-03-26 2015-12-22 The Gillette Company Method of depilation and depilatory kit

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WO1985004880A1 (fr) * 1984-04-19 1985-11-07 University Of Tennessee Research Corporation Liposome fusionne et procede induit par un acide pour la fusion des liposomes
JPS61165316A (ja) * 1985-01-17 1986-07-26 Kishiyouhin Kagaku Kaihou Kenkyusho:Kk 脱毛剤

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Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5411991A (en) * 1992-12-22 1995-05-02 Shander; Douglas Method of reducing hair growth employing sulfhydryl active compounds
AU687778B2 (en) * 1992-12-22 1998-03-05 Gillette Company, The Reduction of hair growth employing sulfhydryl reactive compounds
WO1994014428A1 (fr) * 1992-12-22 1994-07-07 Handelman, Joseph, H. Reduction de la pousse des poils a l'aide de composes reactifs de sulfhydryle
US6743419B1 (en) * 1992-12-22 2004-06-01 The Gillette Company Method of reducing hair growth employing sulfhydryl active compounds
EP0713694A1 (fr) * 1994-11-24 1996-05-29 Wella Aktiengesellschaft Composition pour la déformation permanente des cheveux
US5635170A (en) * 1994-11-24 1997-06-03 Wella Aktiengesellchaft Composition and method for permanent shaping of hair
US5897857A (en) * 1995-06-07 1999-04-27 The Procter & Gamble Company Depilatory compositions comprising sulfhydryl compounds
US5645825A (en) * 1995-06-07 1997-07-08 The Procter & Gamble Company Depilatory compositions comprising sulfhydryl compounds
WO1998030197A1 (fr) * 1997-01-11 1998-07-16 Wella Aktiengesellschaft Procede et agent pour permanentes a base de mercaptoacetamides substitues par alkyle a chaine n-ramifiee et procede permettant de preparer ledit agent
US6153180A (en) * 1997-01-11 2000-11-28 Wella Aktiengesellschaft Agent and method for permanently shaping the hair, based on n-branched-chain alkyl-substituted mercapto acetamides and process for their preparation
US5985253A (en) * 1997-03-14 1999-11-16 Wella Ag Hair shaping compositions containing mercaptoethylamines and methods for the permanent shaping of hair using same
WO1999002125A1 (fr) * 1997-07-09 1999-01-21 Reckitt & Colman France Compositions depilatoires, procedes pour leur preparation et leur utilisation
AU755351B2 (en) * 1997-07-09 2002-12-12 Reckitt Benckiser France Depilatory compositions, methods for their preparation and their use
US6306380B1 (en) 1997-07-09 2001-10-23 Reckitt & Colman France Cosmetic depilatory compositions comprising a continuous aqueous phase and an oil phase
US6162425A (en) * 1997-07-25 2000-12-19 Wella Aktiengesellschaft Saturated, alkyl-substituted n-mercaptoacetyl heterocyclic compounds and compositions and methods for permanent shaping of hair based on same and processes for making same
WO1999006013A3 (fr) * 1997-07-31 1999-08-19 Wella Ag Agent et procede pour le permanentage des cheveux et procede pour la production de l-alkylmercaptoacetamides
WO1999006013A2 (fr) * 1997-07-31 1999-02-11 Wella Aktiengesellschaft Agent et procede pour le permanentage des cheveux et procede pour la production de l-alkylmercaptoacetamides
WO1999007330A2 (fr) * 1997-08-06 1999-02-18 Wella Aktiengesellschaft Procedes et agents appropries pour permanenter des cheveux, a base de mercaptoacetamides n,n-disubstitues et procede permettant de preparer lesdits mercaptoacetamides
WO1999007330A3 (fr) * 1997-08-06 1999-08-19 Wella Ag Procedes et agents appropries pour permanenter des cheveux, a base de mercaptoacetamides n,n-disubstitues et procede permettant de preparer lesdits mercaptoacetamides
US6399051B2 (en) 1997-08-06 2002-06-04 Wella Aktiengesellschaft Method and agents for permanently styling hair, with a base consisting of N,N-disubstituted mercaptoacetamides
DE19733952C2 (de) * 1997-08-06 1999-12-23 Wella Ag Mittel zur dauerhaften Haarverformung auf Basis von N,N-disubstituierten Mercaptoacetamiden sowie Verfahren zur Herstellung dieser Mercaptoacetamide
DE19733952A1 (de) * 1997-08-06 1999-02-18 Wella Ag Mittel und Verfahren zur dauerhaften Haarverformung auf Basis von N,N-disubstituierten Mercaptoacetamiden sowie Verfahren zur Herstellung dieser Mercaptoacetamide
WO2001006998A1 (fr) * 1999-07-23 2001-02-01 Unilever Plc Traitement capillaire utilisant des composes amino organiques
US6509011B1 (en) 1999-07-23 2003-01-21 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method of hair treatment using organic amino compounds
WO2001074318A2 (fr) * 2000-04-01 2001-10-11 Wella Aktiengesellschaft Agent et procede pour le permanentage durable des cheveux a base d'amides de l'acide 2-mercaptopropionique et procede pour leur production
WO2001074318A3 (fr) * 2000-04-01 2002-02-14 Wella Ag Agent et procede pour le permanentage durable des cheveux a base d'amides de l'acide 2-mercaptopropionique et procede pour leur production
US7341715B2 (en) 2000-04-01 2008-03-11 Wella Ag Method and agents on the basis of 2-mercaptopropionic acid amides for durable hair forming and a method for producing same
US8557229B2 (en) 2010-03-26 2013-10-15 The Procter & Gamble Company Hair removal method and hair removal kit
US9216304B2 (en) 2010-03-26 2015-12-22 The Gillette Company Method of depilation and depilatory kit
JP2013177384A (ja) * 2012-02-09 2013-09-09 Kracie Seiyaku Kk 角質剥離組成物

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AU7055391A (en) 1991-08-05
PT96499A (pt) 1991-10-15
IE910124A1 (en) 1991-07-17

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