WO2012163594A2 - Agents d'ondulation sensiblement sans ammoniac, contenant de la cystéine - Google Patents

Agents d'ondulation sensiblement sans ammoniac, contenant de la cystéine Download PDF

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Publication number
WO2012163594A2
WO2012163594A2 PCT/EP2012/057146 EP2012057146W WO2012163594A2 WO 2012163594 A2 WO2012163594 A2 WO 2012163594A2 EP 2012057146 W EP2012057146 W EP 2012057146W WO 2012163594 A2 WO2012163594 A2 WO 2012163594A2
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Prior art keywords
agent
mmol
cysteine
fibers
acid
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PCT/EP2012/057146
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German (de)
English (en)
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WO2012163594A3 (fr
Inventor
Yvonne Lissner
Wolfgang Wolff
Birgit Rautenberg-Groth
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Henkel Ag & Co. Kgaa
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Publication of WO2012163594A2 publication Critical patent/WO2012163594A2/fr
Publication of WO2012163594A3 publication Critical patent/WO2012163594A3/fr

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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
    • A61K8/40—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 of 8.0 to 8.5, containing cysteine 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.
  • Ammonia-free or low-inertity wave agents containing carboxylate-containing thiol compounds and at least one (C 2 to C 6 ) alkanolamine as alkalizing agent are described in the earlier German patent application DE 10 2010 029 976.
  • 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 8.0 to 8.5 and containing not more than 0, 1 mmol of ammonia per 100 g of the agent containing
  • 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.
  • compositions according to the invention 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.
  • the agents according to the invention preferably are substantially free of (NH 4 ) ions and may contain only 0 to 0, 1 mmol (NH 4 ) ions per 100 g of the inventive composition.
  • 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 value is pH 8, 1 to pH 8.5, preferably pH 8.1 to 8.4 and in particular pH 8.1 to pH 8.3, is.
  • the agents according to the invention contain cysteine as the first essential ingredient.
  • agents according to the invention contain, based on their weight, from 1.0 to 15.0% by weight, preferably from 1.5 to 10, more preferably from 2.0 to 7.5 and in particular from 2.25 to 5% by weight. cysteine.
  • cysteine in the form of the hydrocyanic hydrochloride leads to particularly storage-stable products.
  • Preferred agents according to the invention therefore contain cysteine hydrochloride monohydrate.
  • the preferred concentration of cysteine in the compositions according to the invention is from 40 mmol to 130 mmol, in particular from 50 mmol to 120 mmol, of cysteine, in each case based on 100 g of the agent.
  • 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.
  • 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).
  • 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,
  • Further preferred imidazole derivatives according to the invention are biotin, hydantoin and benzimidazole. Most preferably, the imidazole.
  • 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, for example, 2-ethyl-1,3-hexanediol, 1,3-butanediol, 1,4-butanediol, 1,2-propanediol,
  • 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 liquid at room temperature, ie 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.
  • triglyceride oils such as the liquid portions of beef tallow as well as synthetic triglyceride oils.
  • 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 their technical mixtures, the z. B.
  • dicarboxylic acid esters such as di-n-butyl adipate, di (2-ethylhexyl) adipate, di (2-ethylhexyl) succinate and diisotridecyl acelate
  • 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.
  • 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.
  • 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 become.
  • 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 reduction of 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 choice of these emulsifying surfactants or Emulsifiers depend 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.
  • the 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. Consequently, in this way, the power achieved with an agent formulated according to the invention can be achieved with a marked reduction in 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.
  • Suitable protein hydrolysates are in particular 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 SOgH 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, Represents methacrylic acid and its 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, if appropriate, 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
  • 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
  • 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) in 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 derivatives thereof,
  • 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.
  • kit-of-parts comprising
  • At least one container containing a means of the first subject of the invention and (Ii) at least one container containing at least one fixing agent having a pH of at most pH 7, comprising at least one oxidizing agent.
  • 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 the H202 "containing fixing agent is preferably from 2 to 6, in particular 2 to 4.
  • the H202" preparations preferably contain 0.5 to 15 wt .-%, in particular 0.5 to 3 wt .-%, ⁇ 2 ⁇
  • 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 may be preferred by spraying the fibers with a liquid with water, happen.
  • 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.
  • 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.
  • the formulations E1 and E2 provided an improved compatibility with reduced skin redness and irritation as well as significantly reduced odor nuisance.

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  • Health & Medical Sciences (AREA)
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  • Public Health (AREA)
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  • Epidemiology (AREA)
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Abstract

Agents aqueux destinés à l'ondulation permanente de fibres de kératine, notamment de cheveux humains, présentant un pH de 8,0 à 8,5 et ne contenant pas plus de 0,1 mmol d'ammoniac pour 100 g d'agent, comprenant (a) 0,5 à 20% en poids de cystéine (b) 0,5 à 10% en poids d'au moins une alcanolamine (C2 à C6) en tant qu'agent basifiant, ces agents ayant un effet ondulant remarquable, étant doux pour la peau et dégageant moins d'odeur.
PCT/EP2012/057146 2011-06-01 2012-04-19 Agents d'ondulation sensiblement sans ammoniac, contenant de la cystéine WO2012163594A2 (fr)

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DE201110076852 DE102011076852A1 (de) 2011-06-01 2011-06-01 Im wesentlichen Ammoniak freie Wellmittel mit Cystein
DE102011076852.1 2011-06-01

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WO2016182087A1 (fr) * 2015-05-12 2016-11-17 L'oreal Composition pour fibres de kératine

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DE102015200139B4 (de) 2015-01-08 2021-07-08 Schaeffler Technologies AG & Co. KG Nockenwellenverstelleranbindung an eine Doppelnockenwelle
CN105411881A (zh) * 2015-12-17 2016-03-23 玉兰生物科技发展（天津）有限公司 一种烫发剂及其制备方法

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EP0363057B1 (fr) 1988-10-04 1994-04-06 L'oreal, S.A. Solution pour onduler les cheveux
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WO2016182087A1 (fr) * 2015-05-12 2016-11-17 L'oreal Composition pour fibres de kératine
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