EP2579948A2 - Agent d'ondulation sensiblement dépourvu d'ammoniac - Google Patents

Agent d'ondulation sensiblement dépourvu d'ammoniac

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Publication number
EP2579948A2
EP2579948A2 EP11723433.6A EP11723433A EP2579948A2 EP 2579948 A2 EP2579948 A2 EP 2579948A2 EP 11723433 A EP11723433 A EP 11723433A EP 2579948 A2 EP2579948 A2 EP 2579948A2
Authority
EP
European Patent Office
Prior art keywords
mmol
agent
acid
fibers
group
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP11723433.6A
Other languages
German (de)
English (en)
Inventor
Birgit Rautenberg-Groth
Yvonne Lissner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP2579948A2 publication Critical patent/EP2579948A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/22—Peroxides; Oxygen; Ozone
    • A—HUMAN NECESSITIES
    • A45—HAND OR TRAVELLING ARTICLES
    • A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
    • A45D7/00—Processes of waving, straightening or curling hair
    • A45D7/04—Processes of waving, straightening or curling hair chemical
    • 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
    • A61K8/41—Amines
    • 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

  • the invention relates to substantially ammonia-free - preferably ammonia-free - Wellsch, with a pH greater than pH 7, containing 100 g of the agent 30 mmol to 165 mmol of at least one carboxyl-containing or carboxylate-containing thiol compound and at least one (C 2 to C 6 ) alkanolamine.
  • the permanent deformation of keratin fibers is usually carried out by mechanically deforming the fiber and defining the deformation by suitable means. Before and / or after this deformation, the fiber is treated with the aqueous preparation of a keratin-reducing substance and rinsed after a contact time with water or an aqueous solution. In a second step, the fiber is then treated with the aqueous preparation of an oxidizing agent. After a period of action, this is also rinsed and the fiber of the mechanical deformation aids (winder, Papilloten) freed.
  • the aqueous preparation of the keratin-reducing substance is usually adjusted to be alkaline so that a sufficient proportion of the thiol functions is deprotonated and, on the other hand, the fiber swells and in this way a deep penetration of the keratin-reducing substance into the fiber is made possible.
  • the keratin-reducing substance cleaves some of the disulfide bonds of the keratin to -SH groups, resulting in a loosening of the peptide cross-linking and, due to the tension of the fiber due to the mechanical deformation, a reorientation of the keratinous fugue.
  • the alkaline pH of the corrugating agent is effected by adding ammonia.
  • Ammonia promotes the hair swelling particularly and thus additionally supports the penetration of the keratin-reducing substance and the quality of the Well Sign.
  • the scalp especially in persons with sensitive skin, usually by the ammonia but also by the keratin-reducing substances are irritated.
  • a perceived unpleasant odor is the companion of corrugating agents with ammonia-based alkalizing agents. Both negative side effects should be minimized or optimally avoided altogether without compromising the well efficiency.
  • a first subject of the invention are water-containing agents for the permanent deformation of keratin-containing fibers, in particular human hair, which has a pH of greater than pH 7 and contains not more than 0.1 mmol of ammonia per 100 g of the composition
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or one equivalent of a mono- or polyvalent cation
  • compositions according to the invention have an ammonia content of not more than 0.1 mmol per 100 g of the composition according to the invention. This means that the agents according to the invention are substantially free of ammonia and may only contain 0 to 0.1 mmol of ammonia per 100 g of the agent according to the invention.
  • the agents according to the invention preferably have an ammonia content of not more than 0.01 mmol, very particularly preferably not more than 0.001 mmol, very particularly preferably not more than 0.0001 mmol, in each case based on 100 g of the agent according to the invention , Most preferably, the agents of the invention are free of ammonia. In alkaline systems, the addition of ammonium ion-containing compounds, ie (NH 4 + ) -containing compounds, may cause ammonia to form.
  • the compositions according to the invention therefore preferably have a content of (NH 4 + ) ions of not more than 0.1 mmol per 100 g of the agent according to the invention. This means that the agents according to the invention are preferably essentially free of (NH 4 + ) ions and may only contain 0 to 0.1 mmol (NH 4 + ) ions per 100 g of the agent according to the invention.
  • the agents according to the invention preferably have a content of (NH 4 + ) ions of not more than 0.01 mmol, very particularly preferably not more than 0.001 mmol, very particularly preferably not more than 0.0001 mmol, in each case to 100 g of the agent according to the invention.
  • the agents of the invention are free of (NH 4 + ) ions.
  • the agents according to the invention particularly well achieve the object if the pH is pH 7.5 to pH 10.0, in particular pH 8.0 to pH 9.5.
  • compositions according to the invention necessarily contain at least one carboxyl-containing or carboxylate-containing thiol compound of the formula (I).
  • the aliphatic hydrocarbon skeleton X of the formula (I) may be saturated or unsaturated, linear or branched.
  • X is methylene, ethane-1, 1-diyl, ethane-1, 2-diyl, propane-1, 1-diyl, propane-1,2-diyl, propane-1, 3-diyl stands,
  • each of these groups may optionally be additionally substituted with at least one of the following: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2 .
  • X is methylene or ethane-1, 1-diyl
  • each of these groups may optionally be additionally substituted with at least one of the following radicals: carboxyl group, carboxylate group, hydroxy group, -NH 2 .
  • M is one equivalent of a monovalent or polyvalent cation.
  • the monovalent or polyvalent cation M z + with a charge number z of one or higher serves merely to compensate for the singly negative charge of the saline-forming carboxylate fragment -COO " in formula (I), for which the equivalent cation of the corresponding cation is to be used 1 / z
  • the fragment - COOM of the formula (I) in the case of salt formation stands for the group: -COO " 1 / z (M z + ).
  • physiologically compatible cations are suitable as mono- or polyvalent cation M z + .
  • these are metal cations of the physiologically acceptable metals from the groups Ia, Ib, IIa, IIb, IIIb, Via or VIII of the Periodic Table of the Elements, as well as cationic organic compounds having a quaternized nitrogen atom.
  • the latter will for example, by protonation of primary, secondary or tertiary organic amines with an acid, such as formed with compounds of formula (I) in their acidic form, or by permanent quaternization of said organic amines.
  • (C 2 to C 6 ) alkanolammonium ions are preferred.
  • these cationic organic (C 2 to C 6 ) alkanolammonium ions are 2-ammonioethanol and 2-trimethylammonioethanol.
  • M in formula (I) preferably represents a hydrogen atom, a (C 2 to C 6 ) alkanolammonium ion, an alkali metal ion, half an equivalent of an alkaline earth metal ion or half an equivalent of a zinc ion, more preferably a hydrogen atom or a (C 2 to C 6 ) - alkanolammonium ion.
  • the term (C 2 to C 6 ) -alkanolammonium ion means organic ammonium compounds which have two to six carbon atoms which form a carbon skeleton to which at least one ammonio group (preferably exactly one ammonio group) and at least one hydroxy group (again preferably exactly one hydroxy group) binds.
  • Preferred (C 2 to C 6 ) alkanolammonium ions are 2-ammonioethane-1-ol, 3-ammoniopropan-1-ol, 4-aminobutan-1-ol, 5-ammoniopentan-1-ol, 1-ammononiopropane 2-ol, 1-ammoniobutan-2-ol, 1-ammononiopentan-2-ol, 1-ammoniopentan-3-ol, 1-ammoniopentan-4-ol, 3-ammonio-2-methylpropan-1-ol, 1 - Ammonio-2-methylpropan-2-ol, 3-ammoniopropane-1, 2-diol or 2-ammonio-2-methylpropane-1, 3-diol.
  • M in formula (I) for a hydrogen atom, 2-ammonioethane-1-ol or 2-ammonio-2-methylpropan-1-ol.
  • Preferred agents contain as compound of the formula (I) at least one compound of the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid and the salts of the abovementioned thioacids.
  • Preferred compounds of the formula (I) are selected from the salts of thioglycolic acid and / or the salts of thiolactic acid and / or thioglycolic acid and / or thiolactic acid.
  • the compounds of the formula (I) are preferably contained in the corrugating agents in an amount of from 40 mmol to 130 mmol, in particular from 50 mmol to 120 mmol, in each case based on 100 g of the composition.
  • the agents according to the invention additionally contain no further keratin-reducing compounds.
  • Keratin-reducing compounds are able to reductively cleave the disulfide bridges of keratin.
  • the term (C 2 to C 6 ) -alkanolamine means organic amine compounds which have a carbon skeleton of two to six carbon atoms, to which at least one amino group (preferably exactly one amino group) and at least one hydroxyl group (again preferably exactly one hydroxy group ) binds.
  • the (C 2 to C 6 ) alkanolamines of the alkalizing agent combination (b) according to the invention are preferably primary amines.
  • At least one (C 2 to C 6 ) alkanolamine having exactly one amino group is preferable to use.
  • this is preferably a primary amine.
  • composition according to the invention preferably contains at least one (C 2 to C 6 ) -alkanolamine selected from 2-aminoethane-1-ol (monoethanolamine), 3-aminopropan-1-ol, 4-aminobutan-1-ol, 5-aminopentane-1 -ol, 1-aminopropan-2-ol, 1-aminobutan-2-ol, 1-aminopentan-2-ol, 1-aminopentan-3-ol, 1-aminopentan-4-ol, 3-amino-2-methylpropane -1 -ol, 1-amino-2-methylpropan-2-ol, 3-aminopropane-1, 2-diol, 2-amino-2-methylpropane-1, 3-diol (especially 2-amino-1-ol , 2-amino-2-methylpropan-1-ol and 2-amino-2-methyl-propane-1,3-diol).
  • C 2 to C 6 alkano
  • Monoethanolamine has proven to be a particularly suitable (C 2 to C 6 ) alkanolamine as an alkalizing agent.
  • compositions of the invention contain the (C 2 to C 6 ) alkanolamines preferably in an amount of 0.5 wt .-% to 5.0 wt .-%, in particular from 0.7 wt .-% to 2.0 wt. -%, in each case based on the weight of the entire composition.
  • the agent of this embodiment of the invention comprises an alkalizing agent combination
  • (b2) at least one compound comprising at least one HCO 3 ⁇ ion and / or at least one C0 3 2 ⁇ ion.
  • the additional alkalizing agent (b2) is preferably selected from Na 2 C0 3 , NaHC0 3 , K 2 C0 3 , KHC0 3 , CaC0 3 or mixtures thereof (especially under Na 2 C0 3 , NaHC0 3 or mixtures thereof).
  • Containing agent for the permanent deformation keratin inconveniencer fibers, in particular human hair which has a pH greater than pH 7 and containing not more than 0.001 mmol of ammonia per 100 g of the agent containing
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or one equivalent of a mono- or polyvalent cation
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M represents a hydrogen atom or one equivalent of a mono- or polyvalent one cation
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or one equivalent of a mono- or polyvalent cation
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M represents a hydrogen atom or one equivalent of a mono- or polyvalent one cation
  • Containing agent for the permanent deformation keratin inconveniencer fibers, in particular human hair which has a pH greater than pH 7 and containing not more than 0.001 mmol of ammonia per 100 g of the agent containing
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the salts of the aforementioned thioacids.
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the salts of the aforementioned thioacids
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the salts of the aforementioned thioacids.
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the salts of the aforementioned thioacids.
  • Containing agent for the permanent deformation keratin inconveniencer fibers, in particular human hair which has a pH greater than pH 7 and containing not more than 0.001 mmol of ammonia per 100 g of the agent containing
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or a (C 2 to C 6 ) alkanolammonium ion
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or a (C 2 to C 6 ) alkanolammonium ion
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or a (C 2 to C 6 ) alkanolammonium ion
  • X represents an aliphatic hydrocarbon skeleton, which may additionally be at least one of the following groups is substituted: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or a (C 2 to C 6 ) alkanolammonium ion
  • Containing agent for the permanent deformation keratin inconveniencer fibers, in particular human hair which has a pH greater than pH 7 and containing not more than 0.001 mmol of ammonia per 100 g of the agent containing
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the (C 2 to C 6 ) -alkanolammonium salts of the aforementioned thioacids.
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the (C 2 to C 6 ) -alkanolammonium salts of the aforementioned thioacids
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the (C 2 to C 6 ) -alkanolammonium salts of the aforementioned thioacids.
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the (C 2 to C 6 ) -alkanolammonium salts of the aforementioned thioacids.
  • Containing agent for the permanent deformation keratin inconveniencer fibers, in particular human hair which has a pH greater than pH 7 and containing not more than 0.001 mmol of ammonia per 100 g of the agent containing
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or one equivalent of a mono- or polyvalent cation
  • (b2) at least one compound comprising at least one HCO 3 " ion and / or at least one C0 3 2" ion.
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or one equivalent of a mono- or polyvalent cation
  • (b2) at least one compound comprising at least one HCO 3 ⁇ ion and / or at least one C0 3 2 ⁇ ion.
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or one equivalent of a mono- or polyvalent cation
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or one equivalent of a mono- or polyvalent cation
  • (b2) at least one compound comprising at least one HCO 3 ⁇ ion and / or at least one C0 3 2 ⁇ ion.
  • Containing agent for the permanent deformation keratin inconveniencer fibers, in particular human hair which has a pH greater than pH 7 and containing not more than 0.001 mmol of ammonia per 100 g of the agent containing
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the salts of the aforementioned thioacids.
  • (b2) at least one compound comprising at least one HCO 3 ⁇ ion and / or at least one C0 3 2 ⁇ ion.
  • composition containing (A) to 100 g of the composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the salts of the aforementioned thioacids
  • (b2) at least one compound comprising at least one HCO 3 ⁇ ion and / or at least one C0 3 2 ⁇ ion.
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the salts of the aforementioned thioacids.
  • (b2) at least one compound comprising at least one HCO 3 ⁇ ion and / or at least one C0 3 2 ⁇ ion.
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the salts of the aforementioned thioacids.
  • Containing agent for the permanent deformation keratin inconveniencer fibers, in particular human hair which has a pH greater than pH 7 and containing not more than 0.001 mmol of ammonia per 100 g of the agent containing
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or a (C 2 to C 6 ) alkanolammonium ion
  • (b2) at least one compound comprising at least one HCO 3 ⁇ ion and / or at least one C0 3 2 ⁇ ion.
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or a (C 2 to C 6 ) alkanolammonium ion
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or a (C 2 to C 6 ) alkanolammonium ion
  • (b2) at least one compound comprising at least one HCO 3 " ion and / or at least one C0 3 2" ion.
  • X represents an aliphatic hydrocarbon skeleton optionally additionally substituted with at least one of the following groups: thiol group, carboxyl group, carboxylate group, hydroxy group, -NH 2
  • M is a hydrogen atom or a (C 2 to C 6 ) alkanolammonium ion
  • (b1) at least one (C 2 to C 6 ) alkanolamine and (b2) at least one compound comprising at least one HCO 3 ⁇ ion and / or at least one C0 3 2 ⁇ ion.
  • Containing agent for the permanent deformation keratin inconveniencer fibers, in particular human hair which has a pH greater than pH 7 and containing not more than 0.001 mmol of ammonia per 100 g of the agent containing
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the (C 2 to C 6 ) -alkanolammonium salts of the aforementioned thioacids.
  • (b2) at least one compound comprising at least one HCO 3 ⁇ ion and / or at least one C0 3 2 ⁇ ion.
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the (C 2 to C 6 ) -alkanolammonium salts of the aforementioned thioacids
  • (b2) at least one compound comprising at least one HCO 3 " ion and / or at least one C0 3 2" ion.
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the (C 2 to C 6 ) -alkanolammonium salts of the aforementioned thioacids.
  • (b2) at least one compound comprising at least one HCO 3 ⁇ ion and / or at least one C0 3 2 ⁇ ion.
  • composition 30 mmol to 165 mmol of one or more compounds from the group formed from thioglycolic acid, thiolactic acid, cysteine, thiomalic acid, and the (C 2 to C 6 ) -alkanolammonium salts of the aforementioned thioacids.
  • (b2) at least one compound comprising at least one HCO 3 ⁇ ion and / or at least one C0 3 2 ⁇ ion.
  • All of the aforementioned means of embodiments (A) to (FF) are preferably free of ammonia and free of (NH 4 + ) ions.
  • compositions according to the invention may contain reinforcing components such as, for example
  • Heterocyclic compounds such as imidazole, pyrrolidine, piperidine, dioxolane, dioxane, morpholine and piperazine as well as derivatives of these compounds such as, for example, the C 1-4 alkyl groups
  • Substituents which may be positioned on both carbon atoms and nitrogen atoms of the heterocyclic ring systems are methyl, ethyl, ⁇ -hydroxyethyl and ⁇ -aminoethyl groups.
  • Preferred derivatives of heterocyclic compounds according to the invention are, for example, 1-methylimidazole, 2-methylimidazole, 4 (5) -methylimidazole, 1, 2-dimethylimidazole, 2-ethylimidazole, 2-isopropylimidazole, N-methylpyrrolidone, 1-methylpiperidine, 4-methylpiperidine, 2 Ethyl piperidine, 4-methylmorpholine, 4- (2- Hydroxyethyl) morpholine, 1-ethylpiperazine, 1- (2-hydroxyethyl) piperazine, 1- (2-aminoethyl) piperazine.
  • Further preferred imidazole derivatives according to the invention are biotin, hydantoin and benzimi
  • Amino acids such as in particular arginine, citrulline, histidine, ornithine and lysine.
  • the amino acids can be used both as free amino acid and as salts, eg. B. as hydrochlorides used.
  • oligopeptides of on average 2-3 amino acids, which have a high proportion (> 50%, in particular> 70%) of the amino acids mentioned, have proven to be usable according to the invention.
  • Particularly preferred according to the invention are arginine and its salts and arginine-rich oligopeptides.
  • Diols such as 2-ethyl-1, 3-hexanediol, 1, 3-butanediol, 1, 4-butanediol, 1, 2-propanediol, 1, 3-propanediol, neopentyl glycol and ethylene glycol.
  • 1, 3-diols, especially 2-ethyl-1, 3-hexanediol and 1, 3-butanediol, have been found to be particularly suitable.
  • the well-enhancing compounds may be present in the compositions according to the invention in amounts of from 0.5 to 5% by weight, based on the total agent. Quantities of 1 to 4% by weight, in the case of the diols of 0.5 to 3 wt .-%, have been found to be sufficient, which is why these amounts are particularly preferred.
  • the agents according to the invention may additionally contain at least one oil component.
  • Oil components which are suitable according to the invention are, in principle, all oils and fatty substances and also mixtures thereof with solid paraffins and waxes. Preference is given to those oil components whose solubility in water at 20 ° C. is less than 1% by weight, in particular less than 0.1% by weight.
  • the melting point of the individual oil or fat components is preferably below about 40 ° C.
  • Oil components which are at room temperature, d. H. may be liquid below 25 ° C, may be particularly preferred according to the invention. When using several oil and fat components and possibly solid paraffins and waxes, it is usually sufficient, however, if the mixture of oil and fat components and possibly paraffins and waxes meets these conditions.
  • a preferred group of oil components are vegetable oils.
  • vegetable oils examples include apricot kernel oil, avocado oil, sunflower oil, olive oil, soybean oil, rapeseed oil, almond oil, jojoba oil, orange oil, wheat germ oil, peach kernel oil and the liquid portions of coconut oil.
  • other triglycerides such as the liquid portions of beef tallow and synthetic triglycerides, are also suitable.
  • liquid paraffin oils and synthetic hydrocarbons and also di-n-alkyl ethers having a total of from 12 to 36 carbon atoms, in particular 12 to 24 carbon atoms, such as, for example, di-n-octyl ether, di-n -decyl ether, di-n-nonyl ether, di-n-undecyl ether, di-n-dodecyl ether, n-hexyl n-octyl ether, n-octyl n-decyl ether, n-decyl n-undecyl ether, n-undecyl-n dodecyl ether and n-hexyl n-undecyl ether and di-tert-butyl ether, di-isopentyl ether, di-3-ethyl decyl ether,
  • the compounds are available as commercial products 1, 3-di- (2-ethyl-hexyl) -cyclohexane (Cetiol ® S), and di-n-octyl ether (Cetiol ® OE) may be preferred.
  • oil components are fatty acid and fatty alcohol esters.
  • the monoesters of the fatty acids with alcohols having 3 to 24 C atoms are preferred.
  • This group of substances are the products of the esterification of fatty acids having 8 to 24 carbon atoms such as caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, Petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures, the z.
  • alcohols such as isopropyl alcohol, glycerol, caproic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, for example in the pressure splitting of natural fats and oils.
  • Isotridecyl alcohol myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol, and technical mixtures thereof, which are described, for example, in US Pat. B.
  • dicarboxylic acid esters such as di-n-butyl adipate, di (2-ethylhexyl) adipate, di (2-ethylhexyl) succinate and di-isotridecyl acelate and diol esters such as ethylene glycol dioleate, ethylene glycol diisotridecanoate, propylene glycol di (2-ethylhexanoate), propylene glycol di-isostearate, propylene glycol di-pelargonat, butanediol di-isostearate and Neopentylglykoldi-capylate oil components used in the invention, as complex esters such.
  • dicarboxylic acid esters such as di-n-butyl adipate, di (2-ethylhexyl) adipate, di (2-ethylhexyl) succinate and di-isotridecyl acelate
  • diol esters such as
  • oil components which can preferably be used according to the invention are also silicone oils, in particular dialkyl and alkylaryl siloxanes, such as, for example, dimethylpolysiloxane and methylphenylpolysiloxane, and also their alkoxylated and quaternized analogs and also cyclic siloxanes.
  • silicones examples include the products marketed by Dow Corning under the names DC 190, DC 200 and DC 1401 and the commercial products DC 344 and DC 345 from Dow Corning, Q2-7224 (manufacturer: Dow Corning, a stabilized trimethylsilylamodimethicone), Dow Corning® 929 emulsion (containing a hydroxylamino-modified silicone, also referred to as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abif-Quat 3270 and 3272 (manufacturer : Th. Goldschmidt; diquaternary polydimethylsiloxanes, quaternium-80).
  • Dow Corning a stabilized trimethylsilylamodimethicone
  • Dow Corning® 929 emulsion containing a hydroxylamino-modified silicone, also referred to as amodimethicone
  • SM-2059 manufactured by General Electric
  • silicone oils having a kinematic viscosity of up to 50,000 cSt, measured at 25 ° C. may be preferred. Very particular preference is given to silicone oils having kinematic viscosities of up to 10,000 cSt, measured at 25.degree.
  • the determination of the viscosities is carried out according to the falling ball method according to the method "british standard 188". Comparable values are obtained with manufacturer's "British Standard 188" analog test specifications, for example "CTM 0577” from Dow Corning Corporation.
  • especially cyclic siloxanes such as the products of Dow Corning ® 344, Dow Corning ® 345, Dow Corning ® 244, Dow Corning ® 245 or Dow Corning ® 246 are used as oil component having kinematic viscosities of up to 10,000 cSt at 25 ° C determined according to the manufacturer's instructions.
  • oil components which can be used according to the invention are also dialkyl carbonates, as described in detail in DE-OS 197 101 54, to which reference is expressly made.
  • Dioctyl carbonates, especially the di-2-ethylhexyl carbonate, are preferred oil components within the scope of the present invention.
  • compositions according to the invention may additionally contain only limited water-miscible alcohols.
  • water-immiscible miscible are meant those alcohols which are soluble in water at 20 ° C to not more than 10 wt .-%, based on the mass of water.
  • triols and in particular diols have proven to be particularly suitable according to the invention.
  • Alcohols having 4 to 20, in particular 4 to 10, carbon atoms can be used according to the invention.
  • the alcohols used in the invention may be saturated or unsaturated and linear, branched or cyclic.
  • the fatty alcohols are derived from preferably natural fatty acids, which can usually be based on recovery from the esters of fatty acids by reduction.
  • those fatty alcohol cuts which are produced by reducing naturally occurring triglycerides such as beef tallow, palm oil, peanut oil, rapeseed oil, cottonseed oil, soybean oil, sunflower oil and linseed oil or fatty acid esters formed from their transesterification products with corresponding alcohols, and thus represent a mixture of different fatty alcohols.
  • alcohols are 2-ethyl-hexanediol-1, 3, butanol-1, cyclohexanol, pentanol-1 and 1, 2-butanediol.
  • 2-ethyl-hexanediol-1, 3, but also butanol-1 and cyclohexanol are particularly preferred.
  • emulsifiers can be used in the compositions according to the invention.
  • Emulsifiers effect at the phase interface the formation of water- or oil-stable adsorption layers, which protect the dispersed droplets against coalescence and thus stabilize the emulsion.
  • Emulsifiers are therefore constructed like surfactants from a hydrophobic and a hydrophilic part of the molecule.
  • Hydrophilic emulsifiers preferably form O / W emulsions and hydrophobic emulsifiers preferably form W / O emulsions.
  • An emulsion is to be understood as meaning a droplet-like distribution (dispersion) of a liquid in another liquid under the expense of energy in order to create stabilizing phase interfaces by means of surfactants.
  • the selection of these emulsifying surfactants or emulsifiers depends on the substances to be dispersed and the respective outer phase and the fineness of the emulsion. Further definitions and properties of emulsifiers can be found in "H.-D. Dörfler, Grenz perennial- and Kolloidchemie, VCH Verlagsgesellschaft mbH. Weinheim, 1994".
  • Emulsifiers which can be used according to the invention are, for example
  • Glucosides mixtures of alkyl (oligo) and fatty alcohols for example, the commercially available product ® Montanov 68,
  • Sterols are understood to mean a group of steroids which have a hydroxyl group on C-atom 3 of the steroid skeleton and are isolated both from animal tissue (zoosterols) and from vegetable fats (phytosterols). Examples of zoosterols are cholesterol and lanosterol. Examples of suitable phytosterols are ergosterol, stigmasterol and sitosterol. Mushrooms and yeasts are also used to isolate sterols, the so-called mycosterols.
  • glucose phospholipids e.g. as lecithins or phosphatidylcholines from e.g. Egg yolk or plant seeds (e.g., soybeans) are understood.
  • Fatty acid esters of sugars and sugar alcohols such as sorbitol
  • Polyglycerols and polyglycerol derivatives such as polyglycerol poly-12-hydroxystearate (commercial product Dehymuls ® PGPH),
  • Linear and branched fatty acids with 8 to 30 C atoms and their Na, K, Ca, Mg and Zn salts.
  • the agents according to the invention preferably contain the emulsifiers in amounts of from 0.1 to 25% by weight, in particular from 0.1 to 3% by weight, based on the respective total composition.
  • the agents according to the invention may preferably contain at least one nonionic emulsifier having an HLB value of 8 to 18, according to the methods described in the Römpp Lexikon Chemie (Hrg. J. Falbe, M. Regitz), 10th edition, Georg Thieme Verlag Stuttgart, New York, (1997), page 1764, listed definitions.
  • Nonionic emulsifiers having an HLB value of 10 to 15 may be particularly preferred according to the invention.
  • the agent according to the invention is present as a water-containing agent.
  • a water-containing agent in the context of the invention contains at least 40% by weight of water, based on the weight of the entire composition.
  • the hydrous agent according to the invention can be present in various forms, for example as a lotion, oil-in-water emulsion or water-in-oil emulsion.
  • teaching according to the invention also encompasses those embodiments of the agent according to the invention in which a multiphase agent is present, which can be prepared from two or more separately prepared starting preparations only immediately before use. This embodiment may be preferred for incompatible components. It has surprisingly been found that in this way formulated corrugation result in a significantly increased wave effect for the same amount of the respective keratin-reducing components.
  • the power achieved with a formulation formulated according to the invention can be achieved by significantly reducing the proportion of the keratin-reducing substance, and thus with additional protection of the hair and scalp.
  • Two- and multi-phase systems which can be used according to the invention are systems in which there are at least two separate, continuous phases.
  • Examples of such systems are preparations which have the following phases:
  • No two-phase systems in the context of the present invention are systems in which only a continuous phase is present, such.
  • pure oil-in-water or water-in-oil emulsions are systems in which only a continuous phase is present, such.
  • compositions according to the invention contain a care agent selected from protein hydrolysates and their derivatives.
  • Particularly suitable protein hydrolysates are elastin, collagen, keratin, milk protein, silk protein, soy protein, almond protein, pea protein, potato protein, oat protein, corn protein and wheat protein hydrolysates.
  • products based on plants can be preferred according to the invention.
  • Suitable derivatives are, in particular, quaternized protein hydrolysates.
  • Examples of this class of compounds are sold under the names Lamequat® ® L (CTFA name: lauryl ryldimonium hydroxypropylamino Hydrolyzed Animal Protein; Grunau), Croquat ® WKP and Gluadin® ® WQ on the market products. The latter plant-based product may be preferred.
  • the protein derivatives are contained in the agents according to the invention preferably in amounts of 0, 1 to 10 wt .-%, based on the total amount of the composition. Amounts of 0.1 to 5 wt .-% are preferred.
  • the agents according to the invention preferably also contain at least one conditioning agent.
  • Suitable conditioning agents are preferably cationic polymers. These are usually polymers containing a quaternary nitrogen atom, for example in the form of a
  • Preferred cationic polymers are, for example
  • quaternized cellulose derivatives such as are available under the names of Celquat ® and Polymer JR ® commercially.
  • the compounds Celquat ® H 100, Celquat L 200 and Polymer JR ® ® 400 are preferred quaternized cellulose derivatives.
  • Copolymers of vinylpyrrolidone with quaternized derivatives of dialkylaminoacrylate and - methacrylate such as diethyl sulfate quaternized vinylpyrrolidone dimethylaminomethacrylate copolymers.
  • Such compounds are sold under the names Gafquat ® 734 and Gafquat ® 755 commercially.
  • Vinylpyrrolidone-Vinylimidazoliniummethochlorid copolymers such as those sold under the name Luviquat ® ,
  • Suitable conditioning agents are also ampho-polymers.
  • ampho-polymers amphoteric polymers, i. H. Polymers containing in the molecule both free amino groups and free -COOH or SO H groups and to form internal
  • Salts are capable of zwitterionic polymers containing in the molecule quaternary ammonium groups and
  • amphopolymer suitable is the acrylic resin commercially available as Amphomer ®, which is a copolymer of tert-butylaminoethyl methacrylate, N- (1, 1, 3,3-tetramethylbutyl) -acrylamide and two or more monomers from the group of acrylic acid, Methacrylic acid and its represents simple esters.
  • amphopolymers are composed of unsaturated carboxylic acids (for example acrylic and methacrylic acid), cationically derivatized unsaturated carboxylic acids (for example acrylamidopropyltrimethylammonium chloride) and optionally further ionic or nonionic monomers, as described, for example, in German Publication 39 29 973 and the cited prior art can be found there.
  • unsaturated carboxylic acids for example acrylic and methacrylic acid
  • cationically derivatized unsaturated carboxylic acids for example acrylamidopropyltrimethylammonium chloride
  • optionally further ionic or nonionic monomers as described, for example, in German Publication 39 29 973 and the cited prior art can be found there.
  • Terpolymers of acrylic acid, methyl acrylate and Methacrylamidopropyltrimoniumchlorid as they are commercially available under the name Merquat ® 2001 N and the commercial product Merquat ® 280, according to the invention
  • the cationic or amphoteric polymers are contained in the preparations according to the invention preferably in amounts of 0.1 to 5 wt .-%, based on the total preparation.
  • Fancorsil ® LIM-1 silicone gums, such as, for example, the product of Dow Corning ® 1784th
  • cationic surfactants which can be used as conditioning agents in the compositions according to the invention are, in particular, quaternary ammonium compounds.
  • ammonium halides in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg. Cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride.
  • estersquats such as those marketed under the trademarks Dehyquart ® and Stepantex ® methyl hydroxyalkyl dialkoyloxyalkyl ammonium methosulfate be used.
  • Alkylamidoamines in particular fatty acid amidoamines, such as the stearylamidopropyldimethylamine obtainable under the name Tego Amid® S 18, are distinguished not only by a good conditioning action but also by their good biodegradability.
  • the individual phases may be dyed with dyes in order to achieve a particularly good visual appearance of the agent.
  • dyes are preferably soluble only in the aqueous or only in at least one non-aqueous phase in an amount that makes a corresponding coloring visible to the viewer. It is also possible to color both the non-aqueous and the aqueous phase with different dyes, preferably in different colors. However, the sole staining of a nonaqueous phase is preferred.
  • zwitterionic surfactants such as betaines and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines.
  • ampholytic surfactants such as N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids.
  • nonionic surfactants such as addition products of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide to linear fatty alcohols having 15 to 22 carbon atoms, to fatty acids having 12 to 22 carbon atoms and to alkylphenols having 8 to 15 carbon atoms in the alkyl group, C-
  • nonionic polymers such as vinyl pyrrolidone / vinyl acrylate copolymers, polyvinyl pyrrolidone and vinyl pyrrolidone / vinyl acetate copolymers,
  • anionic polymers such as polyacrylic and polymethacrylic acids, their salts, their copolymers with acrylic and methacrylic acid esters and amides and their derivatives, which are obtained by cross-linking with polyfunctional agents,
  • Polyoxycarboxylic acids such as polyketo- and polyaldehydocarboxylic acids and their salts, and also polymers and copolymers of crotonic acid with esters and amides of acrylic and methacrylic acid, such as vinyl acetate-crotonic acid and vinyl acetate-vinylpropionate-crotonic acid copolymers,
  • organic thickeners such as agar-agar, guar gum, alginates, cellulose ethers such as methyl and methyl hydroxypropyl cellulose, gelatin, pectins and / or xanthan gum.
  • Ethoxylated fatty alcohols especially those with limited homolog distribution, such as for example as a commercial product under the name Arlypon ® F (Henkel) on the market, alkoxylated methylglucoside esters, such as the commercial product Glucamate ® DOE 120 (Amerchol), and ethoxylated propylene glycol esters, such as the commercial product Antil ® 141 (Goldschmidt) may be preferred organic thickeners.
  • Structurants such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example soya lecithin, egg
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol, diethylene glycol and ethoxylated triglycerides, and fatty alcohol ethoxylates and their derivatives,
  • Anti-dandruff agents such as climbazole, piroctone olamine and zinc omadine,
  • Active ingredients such as bisabolol, allantoin, panthenol, niacinmide, tocopherol and plant extracts,
  • Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers,
  • Swelling and penetration substances such as PCA, glycerol, propylene glycol monoethyl ether, carbonates,
  • Opacifiers such as latex or styrene / acrylamide copolymers
  • Pearlescing agents such as ethylene glycol mono- and distearate or PEG-3-distearate,
  • Propellants such as propane-butane mixtures, N2O, dimethyl ether, CO2 and air.
  • a second subject of the invention is a kit-of-parts comprising
  • Oxidizing agents in the sense of the invention are capable of oxidatively forming a disulfide bond from two thiol groups.
  • suitable are sodium bromate or potassium bromate or hydrogen peroxide.
  • Hydrogen peroxide is a particularly preferred oxidizing agent.
  • the fixing agents preferably contain at least 50% by weight of water.
  • the pH of H202 "containing fixing agent is preferably from 2 to 6, especially 2 to 4.
  • the H202" preparations preferably contain 0.5 to 15 wt .-%, in particular 0.5 to 3 wt .-%, H2O2.
  • Bromate-based fixatives preferably contain the bromates in concentrations of 1 to 10% by weight and the pH of these solutions is again preferably adjusted to 4 to 7.
  • a third object of the invention is a process for the permanent transformation of keratin-containing fibers, in particular human hair, in which
  • step (iii) or mechanical smoothing means such as a comb or brush, a smoothing board or a heatable smoothing iron in the case of hair straightening.
  • the shaping aids for example winders
  • the keratin-containing fibers are moistened prior to step (i). This can be done by spraying the fibers with a liquid, preferably water.
  • a liquid preferably water.
  • the fibers are shampooed with a conventional shampoo, rinsed and then toweled with a towel. After completion of the terry step remains a noticeable residual moisture in the hair back.
  • Mechanical smoothing is understood according to the invention to mean stretching of the curly fiber along its longest spatial extent.
  • the reaction time Z1 is preferably 5-60 minutes, more preferably 10-30 minutes.
  • the reaction time Z2 is preferably 1-30 minutes, more preferably 5-20 minutes.
  • the fixing agents which can be used in the process according to the invention and preferably usable fixing agents are those of the second subject of the invention.
  • Table 1 comprises two formulations according to the invention, which are labeled E1 and E2, and a comparative composition, which is marked with a V.
  • Each example formulation was tested on 10 subjects in the half-page test using the following perming procedure:
  • the entire hair is moistened with water and toweled with a towel.
  • the head hair is parted with a comb in a left and a right half. Subsequently, the hair is wound on winder.
  • the left half is treated with 30 ml of preparation W according to the invention and the right half side with 30 ml of the corresponding comparative formulation V of the respective example.
  • the hair is rinsed with water and 25 mL of a fixative according to the following Table 2 applied to the entire hair area.
  • the obtained wave result and condition of the scalp are visually evaluated and data on the feel of the treated scalp are collected by questioning the sample.
  • Trimethylhexadecylammonium chloride (about 24-26% active ingredient, INCI name: Aqua (Water), Cetrimonium Chloride) (Cognis)
  • N-dimethyl-N-cocoalkylamine N-oxide about 30% active ingredient, INCI name: Cocamine Oxide (Akzo Nobel)
  • composition V1 was observed sporadic redness of the treated scalp area.
  • Formulations E1 and E2 provided improved tolerability with reduced skin redness and irritation and reduced odor nuisance.

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Abstract

La présente invention concerne un agent contenant de l'eau destiné à la mise en forme permanente de fibres de kératine, notamment de cheveux/poils humains, ledit agent ayant un pH de 8,0 à 8,5, ne contenant pas plus de 0,1 mmol d'ammoniac pour 100 g de l'agent, et contenant (a) 0,5 à 20 % en poids de cystéine, (b) 0,5 à 10 % en poids d'au moins une alcanolamine en C2 à C6 en tant qu'agent d'alcalinisation. Les agents selon l'invention présentent un effet d'ondulation accru, sont inoffensifs pour la peau et ont une odeur moins forte.
EP11723433.6A 2010-06-11 2011-05-31 Agent d'ondulation sensiblement dépourvu d'ammoniac Withdrawn EP2579948A2 (fr)

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DE102010029976A DE102010029976A1 (de) 2010-06-11 2010-06-11 Im wesentlichen Ammoniak freie Wellmittel
PCT/EP2011/058878 WO2011154278A2 (fr) 2010-06-11 2011-05-31 Agent d'ondulation sensiblement dépourvu d'ammoniac

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DE102011076852A1 (de) 2011-06-01 2012-12-06 Henkel Kgaa Im wesentlichen Ammoniak freie Wellmittel mit Cystein

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Publication number Priority date Publication date Assignee Title
US2631965A (en) * 1950-05-24 1953-03-17 Ernst O Schnell Permanent waving of hair
JPS5984810A (ja) * 1982-11-08 1984-05-16 Shiseido Co Ltd パ−マネントウエ−ブ用剤第１剤
JPS6038318A (ja) * 1983-08-10 1985-02-27 Mitsubishi Gas Chem Co Inc システイン系パ−マネントウエ−ブ用第１液
US4913900A (en) * 1988-05-31 1990-04-03 Helene Curtis, Inc. Conditioning permanent wave composition and method
US4963349A (en) 1988-10-04 1990-10-16 Redken Laboratories, Inc. Permanent wave solution
DE3929973A1 (de) 1989-09-08 1991-03-14 Henkel Kgaa Haarpflegemittel
JPH0745388B2 (ja) * 1990-11-28 1995-05-17 花王株式会社 毛髪処理剤組成物
DE4436065A1 (de) 1994-10-10 1996-04-11 Henkel Kgaa Mittel und Verfahren zur dauerhaften Verformung von Keratinfasern
DE19710154C2 (de) 1997-03-12 1999-04-01 Henkel Kgaa Verwendung von Dialkylcarbonaten
FR2795316B1 (fr) * 1999-06-28 2004-12-24 Oreal Procede de permanente comprenant l'application preliminaire d'une composition comprenant au moins un polymere anionique
US20070264218A1 (en) * 2004-07-08 2007-11-15 Yuji Hirano Reducing Composition for Permanent Wave or Straight Permanent
EP1880710A1 (fr) * 2006-07-21 2008-01-23 Wella Aktiengesellschaft Méthode et agent pour la déformation permanente de cheveux
KR100795588B1 (ko) * 2007-01-25 2008-01-21 임채성 이욕식 퍼머넌트 웨이브 및 스트레이트너 조성물
US20130189209A1 (en) * 2010-02-26 2013-07-25 Satoshi Yamaki Hair shape-controlling composition

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