WO2002030373A2 - Nouvelle utilisation d'aldehydes a chaine courte et de composes separant le formaldehyde - Google Patents

Nouvelle utilisation d'aldehydes a chaine courte et de composes separant le formaldehyde Download PDF

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Publication number
WO2002030373A2
WO2002030373A2 PCT/EP2001/011056 EP0111056W WO0230373A2 WO 2002030373 A2 WO2002030373 A2 WO 2002030373A2 EP 0111056 W EP0111056 W EP 0111056W WO 0230373 A2 WO0230373 A2 WO 0230373A2
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Prior art keywords
acid
compounds
preferred
alcohol
hair
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PCT/EP2001/011056
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German (de)
English (en)
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WO2002030373A3 (fr
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Astrid Kleen
Horst Höffkes
Doris Oberkobusch
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Henkel Kommanditgesellschaft Auf Aktien
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Priority to EP01986594A priority Critical patent/EP1322281A2/fr
Priority to AU2002223557A priority patent/AU2002223557A1/en
Publication of WO2002030373A2 publication Critical patent/WO2002030373A2/fr
Publication of WO2002030373A3 publication Critical patent/WO2002030373A3/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen

Definitions

  • the invention relates to the use of short-chain aldehydes and or formaldehyde-releasing compounds for the color stabilization of dyeings of keratin fibers, corresponding preparations and methods for the care and dyeing and care of colored fibers.
  • oxidation dyes are used for permanent, intensive dyeings with appropriate fastness properties.
  • Such colorants usually contain oxidation dye products, so-called developer components and coupler components.
  • the developer components form the actual dyes under the influence of oxidizing agents or atmospheric oxygen with one another or under coupling with one or more coupler components.
  • the oxidation coloring agents are characterized by excellent, long-lasting coloring results.
  • a mixture of a large number of oxidation dye precursors usually has to be used; in many cases direct dyes are still used for shading. Do the in the course of color dyes that are formed or used directly have different fastness properties (e.g.
  • Coloring agents or tinting agents which contain so-called direct draws as the coloring component are usually used for temporary dyeings. These are dye molecules that attach directly to the hair and do not require an oxidative process to form the color. These dyes include, for example, henna, which is known from antiquity for coloring body and hair. These dyeings are generally significantly more sensitive to shampooing than the oxidative dyeings, so that a much undesired shift in nuances or even a visible "discoloration" occurs much more quickly.
  • Color stability in the sense of the invention is to be understood to mean the preservation of the original coloring with regard to nuance and / or intensity when the keratinic fiber is exposed to the repeated influence of aqueous agents, in particular surfactant-containing agents such as shampoos.
  • the present invention therefore firstly relates to cosmetic compositions containing short-chain aldehydes and / or formaldehyde-releasing compounds (A) as active ingredients for color stabilization of the dyeing of fibers.
  • keratin fibers are understood to mean furs, wool, feathers and in particular human hair.
  • short-chain aldehydes are understood to mean aldehydes which can be saturated or unsaturated and / or straight-chain or branched or cyclic and / or aromatic and / or heterocyclic and have a molecular weight of less than 500.
  • the short-chain aldehydes for the purposes of the invention can have one, two or three formyl groups. All or part of the formyl groups can be present as hemiacetals, acetals, oximes, hydrazones, semicarbazones or imines.
  • the active compounds according to the invention also include all compounds which Can release formaldehyde so that it is available as an active ingredient in a cosmetic agent for color stabilization.
  • Aldehydes in general and compounds which release formaldehyde and formaldehyde have been known for a long time and are widely used in cosmetic compositions for preservation, ie for stabilizing the compositions against microbial attack. It is also known that formaldehyde and formaldehyde-releasing substances can stabilize the hair structure by crosslinking.
  • active substances according to the invention include formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, acrolein, crotonaldehyde, benzaldehyde, cinnamaldehyde, o-, m- and p-anisaldehyde, nicotinaldehyde, furfural, glyceraldehyde, glycolaldehyde, citral , Piperonal, glyoxal, methylglyoxal, malonaldehyde, succinaldehyde, glutaraldehyde, adipaldehyde, phthalaldehyde, isophthalaldehyde, terephthalaldehyde, 5-bromo-5-nitro-l, 3-dioxane, 2-bromo-2-nitropropane-l, 3-di
  • the active compounds according to the invention are in the compositions in concentrations of 0.01% by weight to 10% by weight, preferably from 0.05% by weight to 7.5% by weight and very particularly preferably in amounts of 0.1% by weight .% contain up to 5% by weight.
  • the color-retaining active ingredient (A) directly into the coloring or tinting agent, which means that the active ingredient (A) according to the invention in combination with Use oxidation dye precursors (B). It may be advantageous to add the active ingredient (A) to the coloring or tinting agent immediately before use.
  • Oxidation dye precursors of developer (B1) and coupler type (B2), natural and synthetic direct dyes (C) and precursors of nature-analogous dyes, such as indole and indoline derivatives, and mixtures of representatives of one or more of these groups can be used as dye precursors ,
  • Oxidation dye precursors of the developer type (B1) are usually primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazole derivatives and 2,4, 5,6-tetraaminopyrimidine and its derivatives used.
  • Suitable developer components are, for example, p-phenylenediamine, p-toluenediamine, p-aminophenol, o-aminophenol, 1- (2'-hydroxyethyl) -2,5-diaminobenzene, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2- (2,5-diamino-phenoxy) -ethanol, 4-amino-3-methylphenol, 2,4,5,6-tetraaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 4 -Hydroxy-2,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2-hydroxymethylamino-4-aminophenol, bis- (4- aminophenyl) amine, 4-amino-3-fluorophenol, 2-aminomethyl-4-a
  • B. 4,5-diamino-l- (2'-hydroxyethyl) pyrazole Particularly advantageous developer components are p-phenylenediamine, p-toluenediamine, p-aminophenol, l- (2'-hydroxyethyl) -2,5-diaminobenzene, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2 , 4,5,6-tetraaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives are generally used as oxidation dye precursors of the coupler type (B2).
  • coupler components are m-aminophenol and its derivatives such as 5-amino-2-methylphenol, 5- (3-hydroxypropylamino) -2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 2 , 6-Dimethyl-3-aminophenol, 3-trifluoroacetylamino-2-chloro-6-methylphenol, 5 - amino-4-chloro-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5- (2nd '-Hydroxyethyl) amino-2-methylphenol, 3 - (diethylamino) phenol, N-cyclopentyl-3-aminophenol, 1, 3-dihydroxy-5- (methylamino) benzene, 3- (ethylamino) -4- methylphenol and 2,4-dichloro-3-aminophenol, o-aminophenol and its derivatives, m-diaminobenzene and
  • Pyridine derivatives such as 2,6-dihydroxypyridine, 2-amino-3-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3 , 4-dimethylpyridine, 2,6-dihydroxy-4-methylpyridine, 2,6-diaminopyridine, 2,3-diamino-6-methoxypyridine and 3,5-diamino-2,6-dimethoxypyridine, naphthalene derivatives such as 1-naphthol, 2-methyl-l-naphthol, 2-hydroxymethyl-1-naphthol, 2-hydroxyethyl-l-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxy-naphthalene, 1,7-dihydroxynaphthalene, 1,8- Dihydroxynaphthalene, 2,7-dihydroxynaphthalene and 2,3-di
  • coupler components are 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxy-naphthalene, 3-aminophenol, 5-amino-2-methylphenol, 2-amino-3-hydroxypyridine, re- sorcin, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol and 2,6-dihydroxy-3,4-dimethylpyridine.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Particularly suitable direct dyes are those with the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, HC Blue 12, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16 and Basic Brown 17 known compounds as well as 1,4-bis- (ß- hydroxyethyl) amino-2-nitrobenzene, 4-amino-2-nitrodiphenylamine-2'-carboxylic acid, 6-nitro-l, 2,3,4-tetrahydroquinoxaline, hydroxyethyl-2-nitro-toluidine, picramic acid, 2- Amino-6-chloro-4-nitrophenol, 4-ethylamino-3-nitro
  • Directly occurring dyes found in nature include, for example, henna red, henna neutral, chamomile flowers, sandalwood, black tea, sapwood, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • the hair colorants according to the invention may contain minor components in minor amounts, provided that these do not adversely affect the coloring result or for other reasons, e.g. B. toxicological, must be excluded.
  • the dyes which can be used in the hair dyeing and tinting agents according to the invention reference is also expressly made to the monograph Ch. Zviak, The Science of Hair Care, chapter 7 (pages 248-250; direct dyes) and chapter 8, pages 264-267; Oxidation dye precursors), published as Volume 7 of the "Dermatology" series (ed .: Ch., Culnan and H.
  • indoles and indolines and their physiologically tolerable salts are used as precursors of nature-analogous dyes.
  • Those indoles and indolines are preferably used which have at least one hydroxyl or amino group, preferably as a substituent on the six-membered ring.
  • These groups can carry further substituents, e.g. B. in the form of etherification or esterification of the hydroxy group or an alkylation of the amino group.
  • N-methyl-5,6-dihydroxyindoline N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and especially that 5,6-dihydroxyindoline and N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole and in particular the 5 6-dihydroxyindole.
  • indoline and indole derivatives in the colorants used in the process according to the invention both as free bases and in the form of their physiologically salts in question with inorganic or organic acids, e.g. B. the hydrochlorides, sulfates and hydrobromides, are used.
  • amino acids are aminocarboxylic acids, in particular aminocarboxylic acids and ⁇ -aminocarboxylic acids.
  • Arginine, lysine, ornithine and histidine are again particularly preferred among the ⁇ -aminocarboxylic acids.
  • a very particularly preferred amino acid is arginine, in particular in free form, but also used as the hydrochloride.
  • Both the oxidation dye precursors and the substantive dyes are contained in the agents according to the invention preferably in amounts of 0.01 to 20% by weight, preferably 0.1 to 5% by weight, in each case based on the total agent.
  • Hair dyes especially if the coloring is oxidative, be it with atmospheric oxygen or other oxidizing agents such as hydrogen peroxide, are usually weakly acidic to alkaline, i.e. H. adjusted to pH values in the range from about 5 to 11.
  • the colorants contain alkalizing agents, usually alkali or alkaline earth metal hydroxides, ammonia or organic amines.
  • Preferred alkalizing agents are monoethanolamine, monoisopropanolamine, 2-amino-2-methyl-propanol, 2-amino-2-methyl-l, 3-propanediol, 2-amino-2-ethyl-l, 3-propanediol, 2-amino-2 -methylbutanol and triethanolamine as well as alkali and alkaline earth metal hydroxides.
  • Monoethanolamine, triethanolamine and 2-amino-2-methyl-propanol and 2-amino-2-methyl-1,3-propanediol are particularly preferred in this group.
  • the use of ⁇ -amino acids such as ⁇ -aminocaproic acid as an alkalizing agent is also possible.
  • customary oxidizing agents such as in particular hydrogen peroxide or its adducts with urea, melamine or sodium borate, can be used.
  • oxidation with atmospheric oxygen as the only oxidizing agent can be preferred.
  • enzymes where the enzymes are used both to produce oxidizing per compounds and to enhance the effect of a small amount of oxidizing agents present, or also enzymes are used which transfer electrons from suitable developer components (reducing agents) to atmospheric oxygen.
  • Oxidases such as tyrosinase, ascorbate oxidase and laccase are preferred, but also glucose oxidase, uricase or pyruvate oxidase. Furthermore, the procedure should be mentioned to increase the effect of small amounts (e.g. 1% and less, based on the total agent) of hydrogen peroxide by peroxidases.
  • the preparation of the oxidizing agent is then expediently mixed with the preparation with the dye precursors immediately before dyeing the hair.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 10. It is particularly preferred to use the hair dye in a weakly alkaline environment.
  • the application temperatures can be in a range between 15 and 40 ° C., preferably at the temperature of the scalp. After an exposure time of approximately 5 to 45, in particular 15 to 30, minutes, the hair dye is rinsed off the hair to be colored. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. B. a coloring shampoo was used.
  • the preparation with the dye precursors can be applied to the hair without prior mixing with the oxidation component. After an exposure time of 20 to 30 minutes, the oxidation component is then applied, if necessary after an intermediate rinse. After a further exposure time of 10 to 20 minutes, rinsing is carried out and, if desired, re-shampooed.
  • the corresponding agent is adjusted to a pH of about 4 to 7.
  • air oxidation is initially aimed for, the agent applied preferably having a pH of 7 to 10.
  • the use of acidic peroxidisulfate solutions as the oxidizing agent can be preferred.
  • the formation of the color can be supported and increased by adding certain metal ions to the agent.
  • metal ions are, for example, Zn + , Cu 2+ , Fe 2+ , Fe 3+ , Mn 2+ , Mn 4+ , Li + , Mg 2+ , Ca 2+ and Al 3+ .
  • Zn 2+ , Cu 2+ and Mn 2+ are particularly suitable.
  • the metal ions can be used in the form of any physiologically acceptable salt.
  • Preferred salts are the acetates, sulfates, halides, lactates and tartrates.
  • the action of the active ingredient (A) according to the invention can be further improved by fatty substances (D).
  • Fat substances are to be understood as meaning fatty acids, fatty alcohols, natural and synthetic waxes, which can be present both in solid form and in liquid form in aqueous dispersion, and natural and synthetic cosmetic oil components.
  • Linear and / or branched, saturated and / or unsaturated fatty acids having 6 to 30 carbon atoms can be used as fatty acids.
  • Fatty acids with 10-22 carbon atoms are preferred.
  • isostearic as the commercial products Emersol ® 871 and Emersol ® 875
  • isopalmitic acids such as the commercial product Edenor ® IP 95, and all other products sold under the trade names Edenor ® (Cognis) fatty acids.
  • fatty acids are 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, aelaeoleinic acid , Behenic acid and erucic acid and their technical mixtures, which are obtained, for example, in the pressure splitting of natural fats and oils, in the oxidation of aldehydes from Roelen's oxosynthesis or in the dimerization of unsaturated fatty acids.
  • the fatty acid cuts which are obtainable from coconut oil or palm oil are usually particularly preferred; the use of stearic acid is generally particularly preferred.
  • the amount used is 0.1-15% by weight, based on the total agent. In a preferred embodiment, the amount is 0.5-10% by weight, with amounts of 1-5% by weight being very particularly advantageous.
  • Saturated, mono- or polyunsaturated, branched or unbranched fatty alcohols with C 6 -C 30 , preferably C 10 -C 22 and very particularly preferably C 12 -C 22 carbon atoms can be used as fatty alcohols.
  • the fatty alcohols are derived from preferably natural fatty acids, and it can usually be assumed that they are obtained from the esters of the 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.
  • Such substances are, for example, under the names Stenol ® , for example Stenol ® 1618 or Lanette ® , for example Lanette ® O or Lorol ® , for example Lorol ® C8, Lorol ® C14, Lorol ® Cl 8, Lorol ® C8-18, HD-Ocenol ® , Crodacol ® , for example Crodacol ® CS, Novol ® , Eutanol ® G, Guerbitol ® 16, Guerbitol ® 18, Guerbitol ® 20, Isofol ® 12, Isofol ® 16, Isofol ® 24, Isofol ® 36, Isocarb ® 12, Isocarb ® 16 or Isocarb ® 24 are available for purchase.
  • the invention also wool wax alcohols, as are commercially available, for example under the names of Corona ®, White Swan ®, Coronet ® or Fluilan ® can be used.
  • the fatty alcohols are used in amounts of 0.1-30% by weight, based on the entire preparation, preferably in amounts of 0.1-20% by weight.
  • Solid paraffins or isoparaffins, carnauba waxes, beeswaxes, candelilla waxes, ozokerites, ceresine, walnut, sunflower wax, fruit waxes such as apple wax or, for example, can be used according to the invention as natural or synthetic waxes Citrus wax, micro waxes made of PE or PP.
  • Such waxes are available, for example, from Kahl & Co., Trittau.
  • the amount used is 0.1-50% by weight, based on the total agent, preferably 0.1
  • the natural and synthetic cosmetic oil bodies which can increase the effect of the active ingredient according to the invention include, for example:
  • oils examples include sunflower oil, olive oil, soybean oil, rapeseed oil, almond oil, jojoba oil, orange oil, wheat germ oil, peach seed oil and the liquid components of coconut oil.
  • triglyceride oils such as the liquid portions of beef tallow and synthetic triglyceride oils are also suitable.
  • the compounds are available as commercial products l, 3-di- (2-ethyl-hexyl) -cyclohexane (Cetiol ® S), and di-n-octyl ether (Cetiol ® OE) may be preferred.
  • Ester oils are understood to be the esters of C 6 -C 30 fatty acids with C 2 -C 30 fatty alcohols.
  • the monoesters of fatty acids with alcohols having 2 to 24 carbon atoms are preferred.
  • Examples of fatty acid constituents used in the esters are 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, arenoleic acid, elaoleic acid, elaoleic acid, elaoleic acid Gadoleic acid, behenic acid and erucic acid as well as their technical mixtures which occur, for example, in the pressure splitting of natural fats and oils, in the oxidation of aldehydes from Roele
  • fatty alcohol components in the ester oils are isopropyl alcohol, capron alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol alcohol, palmoleyl, stearyl, isostearyl, oleyl, Elaidylalko- hol, petroselinyl, linolyl alcohol, linolenyl, elaeostearyl, arachyl, gadoleyl, behenyl alcohol, erucyl alcohol and brassidyl alcohol and technical mixtures thereof, for example, in the high-pressure hydrogenation of technical Methylestern based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols.
  • iso-propyl myristate IPM Rilanit ®
  • isononanoic acid C16-18 alkyl ester Cetiol ® SN
  • 2-ethylhexyl palmitate Cegesoft ® 24
  • stearic acid-2-ethylhexyl ester Cetiol ® 868
  • Ce tyloleat glycerol tricaprylate
  • cocofatty alcohol-caprinatV caprylate Cetiol ® LC
  • n-butyl tylstearat oleyl erucate
  • isopropyl palmitate Rosanit ® IPP
  • oleyl Oleate Cetiol ®
  • hexyl laurate Cetiol ® A
  • di- n-butyl adipate Cetiol ® B
  • Dicarboxylic acid esters such as di-n-butyl adipate, di- (2-ethylhexyl) adipate, di- (2-ethylhexyl) succinate and di-isotridecylacelate as well as diol esters such as ethylene glycol dioleate, ethylene glycol di-isotridecanoate, propylene glycol di (2 -ethylhexanoate), propylene glycol di-isostearate, propylene glycol di-pelargonate, butanediol di-isostearate, neopentyl glycol dicaprylate,
  • Partialglyceri.de preferably follow formula (I), CH ⁇ CH.CH.O ⁇ R 1
  • R 1 , R 2 and R 3 independently of one another represent hydrogen or a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22, preferably 12 to 18, carbon atoms, with the proviso that at least one of these groups represents a Acyl radical and at least one of these groups represents hydrogen.
  • the sum (m + n + q) represents 0 or numbers from 1 to 100, preferably 0 or 5 to 25.
  • R 1 preferably represents an acyl radical and R 2 and R 3 represents hydrogen and the sum (m + n + q) is 0.
  • Typical examples are mono- and / or diglycerides based on caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linoleic acid , Elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures. Oleic acid monoglycerides are preferably used.
  • the amount of natural and synthetic cosmetic oil bodies used in the agents used according to the invention is usually 0.1-30% by weight, based on the total agent, preferably 0.1-20% by weight, and in particular 0.1-15% by weight. -%.
  • the total amount of oil and fat components in the agents according to the invention is usually 0.5-75% by weight, based on the total agent. Quantities of 0.5-35% by weight are preferred according to the invention.
  • hydroxycarboxylic acid esters are full esters of glycolic acid, lactic acid, malic acid, tartaric acid or citric acid.
  • Other basically suitable hydroxycarboxylic acid esters are esters of ⁇ -hydroxypropionic acid, tartronic acid, D-gluconic acid, sugar acid, Mucic acid or glucuronic acid.
  • Suitable alcohol components of these esters are primary, linear or branched aliphatic alcohols with 8-22 carbon atoms, for example fatty alcohols or synthetic fatty alcohols.
  • the esters of C ⁇ -C 15 fatty alcohols are particularly preferred.
  • Esters of this type are commercially available, eg under the trademark Cosmacol® ® EniChem, Augusta Industriale.
  • the amount of hydroxycarboxylic acid esters used is 0.1-15% by weight, based on the composition, preferably 0.1-10% by weight and very particularly preferably 0.1-5% by weight.
  • the agents used according to the invention therefore contain surfactants.
  • surfactants is understood to mean surface-active substances that form adsorption layers on surfaces and interfaces or that can aggregate in volume phases to form micelloidal or lyotropic mesophases.
  • anionic surfactants consisting of a hydrophobic residue and a negatively charged hydrophilic head group
  • amphoteric surfactants which carry both a negative and a compensating positive charge
  • cationic surfactants which in addition to a hydrophobic residue have a positively charged hydrophilic group
  • nonionic surfactants which have no charges but strong dipole moments and are highly hydrated in aqueous solution.
  • anionic surfactants suitable for use on the human body are suitable as anionic surfactants (E1) in preparations according to the invention. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 8 to 30 carbon atoms.
  • anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 8 to 30 carbon atoms.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts with 2 to 4 carbon atoms in the alkanol group, - linear and branched fatty acids with 8 to 30 carbon atoms (soaps),
  • Alkyl group with 8 to 30 carbon atoms and x 0 or 1 to 16,
  • Alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO (CH 2 -CH 2 O) X -OSO 3 H, in which R is a preferably linear alkyl group with 8 to 30 C atoms and x 0 or 1 to 12,
  • Esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols having 8 to 22 carbon atoms,
  • R 4 is preferably an aliphatic hydrocarbon radical having 8 to 30 carbon atoms
  • R 5 is hydrogen, a radical (CH 2 CH 2 O) n R 18 or X
  • n is a number of 1 to 10
  • X is hydrogen, an alkali or alkaline earth metal or NR 6 R 7 R 8 R 9 , with R 6 to R 9 independently of one another being hydrogen or a C to C 4 hydrocarbon radical
  • Alk stands for CH 2 CH 2 , CHCH 3 CH 2 and / or CH 2 CHCH 3
  • n stands for numbers from 0.5 to 5
  • M stands for a cation as described in DE-OS 197 36 906.5
  • R n CO stands for a linear or branched acyl radical with 6 to 22 carbon atoms, x, y and z in total for 0 or for numbers from 1 to 30, preferably 2 to 10, and X stands for an alkali or alkaline earth metal
  • Typical examples of monoglyceride (ether) sulfates which are suitable for the purposes of the invention are the reaction products of lauric acid monoglyceride, coconut fatty acid monoglyceride, palmitic acid monoglyceride, stearic acid monoglyceride, oleic acid monoglyceride and tallow fatty acid monoglyceride and their ethylene oxide adducts or their form of sulfuric acid with sulfuric acid trioxide.
  • Monoglyceride sulfates of the formula (IV) are preferably used, in which R 25 CO represents a linear acyl radical having 8 to 18 carbon atoms, as described, for example, in EP-Bl 0 561 825, EP-Bl 0 561 999, DE-Al '42 04 700 or from AKBiswas et al. in J.Am.Oil.Chem.Soc. 37, 171 (1960) and FUAhmed in J.Am.Oil.Chem.Soc. 67, 8 (1990),
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, sulfosuccinic acid and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid mono-alkyl polyoxyethyl ester with 8 up to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, monoglycer disulfates, alkyl and alkenyl ether phosphates as well as protein fatty acid condensates.
  • Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one - COO _) - or -SO group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyl-dimethylammonium glycinate, and 2-alkyl -3-carboxymethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid
  • Ampholytic surfactants (E3) are understood to mean those surface-active compounds which, in addition to a C s - C 24 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and for the formation of internal ones Salts are capable.
  • ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid each with about 8 to 24 C. Atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethyl aminopropionate and C 12 _ C lg - sarcosine.
  • Nonionic surfactants (E4) contain, for example, a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether groups as the hydrophilic group.
  • Such connections are, for example - Adducts of 2 to 50 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear and branched fatty alcohols with 8 to 30 C atoms, with fatty acids with 8 to 30 C atoms and with alkylphenols with 8 to 15 C atoms in the alkyl group,
  • Adducts of 5 to 60 moles of ethylene oxide with castor oil and hardened castor oil Adducts of 5 to 60 moles of ethylene oxide with castor oil and hardened castor oil
  • Sorbitan fatty acid esters and addition products of ethylene oxide with sorbitan fatty acid esters such as, for example, the polysorbates
  • the alkyl and alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably from glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • the index number p in the general formula (VI) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
  • the value p for a certain alkyl oligoglycoside is an analytically determined arithmetic parameter, which usually represents a fractional number.
  • Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, preference is given to those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
  • the alkyl or alkenyl radical R 1 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capronic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 15 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms.
  • Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol, and the like technical mixtures which can be obtained as described above.
  • Alkyl oligoglucosides based on hardened C 12/14 coco alcohol with a DP of 1 to 3 are preferred.
  • R ! 6 CO for an aliphatic acyl radical with 6 to 22 carbon atoms
  • R for hydrogen, an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms
  • [Z] for a linear or branched polyhydroxyalkyl radical with 3 to 12 carbon atoms and 3 to 10 hydroxyl groups stands.
  • the fatty acid N-alkyl polyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • a reducing sugar with ammonia, an alkylamine or an alkanolamine
  • subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride With regard to the processes for their production, reference is made to US Pat. Nos. 1,985,424, 2,016,962 and 2,703,798 and international patent application WO 92/06984. An overview of this topic by H. Kelkenberg can be found in Tens. Surf. Det. 25, 8 (1988).
  • the fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars having 5 or 6 carbon atoms, in particular from glucose.
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (III):
  • the fatty acid N-alkylpolyhydroxyalkylamides used are preferably glucamides of the formula (VIII) in which R 17 is hydrogen or an alkyl group and R 16 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, Isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures.
  • R 17 is hydrogen or an alkyl group
  • R 16 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, Isostearic acid, oleic acid, elaidic acid,
  • Fatty acid N-alkylglucamides of the formula (III) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C 12/14 coconut fatty acid or a corresponding derivative are particularly preferred.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • alkylene oxide adducts with saturated linear fatty alcohols and fatty acids, each with 2 to 30 moles of ethylene oxide per mole of fatty alcohol or fatty acid, have proven to be preferred nonionic surfactants. Preparations with excellent properties are also obtained if they contain fatty acid esters of ethoxylated glycerol as nonionic surfactants.
  • the alkyl radical R contains 6 to 22 carbon atoms and can be either linear or branched. Primary linear and methyl-branched aliphatic radicals in the 2-position are preferred. Such alkyl radicals are, for example, 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. 1-Octyl, 1-decyl, 1-lauryl, 1-myristyl are particularly preferred. When using so-called "oxo alcohols" as starting materials, compounds with an odd number of carbon atoms in the alkyl chain predominate.
  • nonionic surfactants are the sugar surfactants. These can be contained in the agents used according to the invention preferably in amounts of 0.1-20% by weight, based on the total agent. Amounts of 0.5-15% by weight are preferred, and amounts of 0.5-7.5% by weight are very particularly preferred.
  • the compounds with alkyl groups used as surfactant can each be uniform substances. However, it is generally preferred to start from natural vegetable or animal raw materials in the production of these substances, so that substance mixtures with different alkyl chain lengths depending on the respective raw material are obtained.
  • both products with a "normal” homolog distribution and those with a narrowed homolog distribution can be used.
  • “Normal” homolog distribution is understood to mean mixtures of homologs which are obtained as catalysts from the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates.
  • narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.
  • the surfactants (E) are used in amounts of 0.1-45% by weight, preferably 0.5-30% by weight and very particularly preferably 0.5-25% by weight, based on the total agent used according to the invention ,
  • Cationic surfactants (E6) of the quaternary ammonium compound type, the esterquat type and the amidoamine type can also be used according to the invention.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B.
  • cetyltrimemylammonium chloride stearyltrimethylammomum chloride, distearyldimemylammonium chloride, lauryldimethylammonium chloride, lauiyldimethylbenzylammonium chloride and tricetylmethylammonium chloride, as well as the compounds known under the INCI names Quate ⁇ ium-27 and Quateridazium-83 compounds.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Esterquats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
  • Preferred ester quats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines.
  • Such products are sold, for example, under the trademarks Stepantex ® , Dehyquart ® and Armocare ® .
  • alkylamidoamines are usually produced by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • An inventively particularly suitable compound from this group is that available under the name Tegoamid ® S 18 commercially stearamidopropyl dimethylamine.
  • the cationic surfactants (E6) are preferably present in the agents used according to the invention in amounts of 0.05 to 10% by weight, based on the total agent. Amounts of 0.1 to 5% by weight are particularly preferred.
  • Anionic, nonionic, zwitterionic and / or amphoteric surfactants and mixtures thereof can be preferred according to the invention.
  • the action of the active ingredient according to the invention can be increased by emulsifiers (F).
  • Emulsifiers cause water or oil-stable adsorption layers to form at the phase interface, which protect the dispersed droplets against coalescence and thus stabilize the emulsion.
  • emulsifiers are therefore made up of a hydrophobic and a hydrophilic part of the molecule. Hydrophilic emulsifiers preferably form O / W emulsions and hydrophobic emulsifiers preferably form W / O emulsions.
  • emulsifiers Under an emulsion is a droplet-like distribution (dispersion) of a liquid in another liquid with the expenditure of energy to create stabilizing phase boundary to understand surfaces by means of surfactants.
  • the selection of these emulsifying surfactants or emulsifiers is based on the substances to be dispersed and the particular external phase as well as the fine particle size of the emulsion. Further definitions and properties of emulsifiers can be found in "H.-D. Dörfler, interfacial and colloid chemistry, VCH Verlagsgesellschaft mbH. Weinheim, 1994 ".
  • Emulsifiers which can be used according to the invention are, for example
  • alkyl (oligo) glucosides for example the commercially available product Montanov ® 68,
  • Adducts of 5 to 60 moles of ethylene oxide with castor oil and hardened castor oil Adducts of 5 to 60 moles of ethylene oxide with castor oil and hardened castor oil
  • Sterols are understood to be a group of steroids which carry a hydroxyl group on the C atom 3 of the steroid structure and which 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. Sterols, the so-called mycosterols, are also isolated from fungi and yeasts.
  • glucose phospholipids include primarily the glucose phospholipids, e.g. as lecithins or phosphatidylcholines from e.g. Egg yolks or plant seeds (e.g. soybeans) are understood.
  • Fatty acid esters of sugars and sugar alcohols such as sorbitol, - polyglycerols and polyglycerol such as polyglycerol poly-12-hydroxystearate (commercial product Dehymuls® ® PGPH)
  • compositions according to the invention preferably contain the emulsifiers in amounts of 0.1-25% by weight, in particular 0.5-15% by weight, based on the total composition.
  • compositions according to the invention can preferably contain at least one nonionic emulsifier with an HLB value of 8 to 18, according to the 10th edition, Georg Thieme Verlag Stuttgart, New in the Rompp-Lexikon Chemie (Ed. J. Falbe, M. Regitz) York, (1997), page 1764.
  • Nonionic emulsifiers with an HLB value of 10-15 can be particularly preferred according to the invention.
  • polymers (G) can support the color-preserving action of the active ingredient according to the invention.
  • polymers are therefore added to the agents used according to the invention, both cationic, anionic, amphoteric and nonionic polymers having proven effective.
  • Cationic polymers (G1) are understood to mean polymers which have a group in the main and / or side chain which can be “temporary” or “permanent” cationic.
  • “permanently cationic” refers to those polymers which have a cationic group regardless of the pH of the agent. These are generally polymers which contain a quaternary nitrogen atom, for example in the form of an ammonium group.
  • Preferred cationic groups are quaternary ammo
  • those polymers in which the quaternary ammonium group is bonded via a C 1-4 hydrocarbon group to a polymer main chain composed of acrylic acid, methacrylic acid or their derivatives have proven to be particularly suitable.
  • R 18 -H or -CH 3
  • R 19 , R 20 and R 21 are independently selected from C 1-4 - alkyl, alkenyl or hydroxyalkyl groups
  • m 1, 2, 3 or 4 "n is a natural number
  • X is a physiologically compatible organic or inorganic anion
  • copolymers consisting essentially of the monomer units listed in formula (IX) and nonionic monomer units are particularly preferred cationic polymers.
  • those are preferred according to the invention , for which at least one of the following conditions applies:
  • R 18 stands for a methyl group
  • R 20 and R 21 stand for methyl groups
  • m has the value 2.
  • Suitable physiologically compatible counterions X " are, for example, halide ions, sulfate ions, phosphate ions, methosulfate ions and organic ions such as lactate, citrate, tartrate and acetate ions.
  • halide ions in particular chloride, are preferred.
  • a particularly suitable homopolymer is, if desired crosslinked, poly (methacryloyloxyemylfrimemylammonium chloride) with the INCI name Polyquaternium-37.
  • the crosslinking can be carried out with the aid of polyolefinically unsaturated compounds, for example divinylbenzene, tetraallyloxyethane, methylene bisacrylamide, diallyl ether, polyallyl polyglyceryl ether, or allyl ethers of sugars or sugar derivatives such as erythritol, pentaerythritol, arabitol, mannitol, sorbitol, sucrose or glucose.
  • Methylene bisacrylamide is a preferred crosslinking agent.
  • the homopolymer is preferably used in the form of a non-aqueous polymer dispersion which should not have a polymer content below 30% by weight.
  • a non-aqueous polymer dispersion which should not have a polymer content below 30% by weight.
  • Such polymer dispersions are available under the names Salcare ® SC 95 (approx. 50% polymer content, further components: mineral oil (INCI name: Mineral Oil) and tridecyl-polyoxypropylene-polyoxyethylene ether (INCI name: PPG-1-Trideceth- 6)) and Salcare ® SC 96 (approx.
  • Copolymers with monomer units according to formula (IX) preferably contain acrylamide, methacrylamide, acrylic acid-C, as non-ionic monomer units. 4- alkyl esters and methacrylic acid-Cj- 4- alkyl esters. Among these nonionic monomers, acrylamide is particularly preferred. As in the case of the homopolymers described above, these copolymers can also be crosslinked. A preferred copolymer according to the invention is the crosslinked acrylamide-memacryloyloxyethyltrimethylammomum chloride copolymer. Such copolymers in which the monomers are present in a weight ratio of about 20:80, commercially available as about 50% non-aqueous polymer dispersion under the name Salcare ® SC 92nd
  • Celquat ® and Polymer JR ® Quaternized cellulose derivatives, as are commercially available under the names Celquat ® and Polymer JR ® .
  • the compounds Celquat ® H 100, Celquat ® L 200 and Polymer JR ® 400 are preferred quaternized cellulose derivatives,
  • honey for example the commercial product Honeyquat ® 50,
  • cationic guar derivatives such as, in particular, the products marketed under the trade names Cosmedia ® Guar and Jaguar ® ,
  • - polysiloxanes with quaternary groups such as the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethyl silylamodimethicon), Dow Corning ® 929 Emulsion (containing a hydroxylamino-modified silicone which is also known as amodimethicone ), SM-2059 (Manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. G ⁇ ldschmidt), diquaternary polydimethylsiloxanes, quaterium-80),
  • Vinylpyrrolidone-vinylimidazolium methochloride copolymers as are offered under the names Luviquat ® FC 370, FC 550, FC 905 and HM 552,
  • cationic polymers of the invention are the "temporarily cationic" polymers. These polymers usually contain an amino group present at certain pH values as a quaternary ammonium group and thus cationic are preferred, for example, chitosan and its derivatives, such as, for example, under the trade designations Hydagen ®. CMF, Hydagen ® HCMF, Kytamer ® PC and Chitolam ® NB / 101 are commercially available.
  • preferred cationic polymers are cationic cellulose derivatives and chitosan and its derivatives, in particular the commercial products Polymer ® JR 400, Hydagen ® HCMF and Kytamer ® PC, cationic guar derivatives, cationic honey derivatives, in particular the commercial product Honeyquat ® 50, cationic alkyl polyglycosides according to DE-PS 44 13 686 and polymers of the type Polyquaternium-37.
  • cationized protein hydrolyzates are to be counted among the cationic polymers, the underlying protein hydrolyzate being derived from animals, for example from collagen, milk or keratin, from plants, for example from wheat, corn, rice, potatoes, soy or almonds, from marine life forms, for example from fish collagen or algae, or biotechnologically obtained protein hydrolyzates.
  • the protein hydrolysates on which the cationic derivatives according to the invention are based can be obtained from the corresponding proteins by chemical, in particular alkaline or acidic hydrolysis, by enzymatic hydrolysis and / or a combination of both types of hydrolysis.
  • the hydrolysis of proteins usually results in a protein hydrolyzate with a molecular weight distribution of approximately 100 daltons up to several thousand daltons.
  • Preferred cationic protein hydrolyzates are those whose underlying protein content has a molecular weight of 100 to 25,000 Daltons, preferably 250 to 5000 Daltons.
  • Cationic protein hydrolyzates also include quaternized amino acids and their mixtures. The quaternization of the protein hydrolyzates or the amino acids is frequently carried out using quaternary ammonium salts such as, for example, N, N-dimethyl-N- (n-alkyl) -N- (2-hydroxy-3-chloro-n-propyl) ammonium halides.
  • the cationic protein hydrolyzates can also be further derivatized.
  • Typical examples of the cationic protein hydrolyzates and derivatives according to the invention are those under the INCI names in the "International Cosmetic Ingredient Dictionary and Handbook" (seventh edition 1997, The Cosmetic, Toiletry, and Fragrance Association 1101 17 * Street, NW, Suite 300 , Washington, DC 20036-4702) and commercially available products: Cocodimonium Hydroxypropyl Hydrolyzed Collagen, Cocodimopnium Hydroxypropyl Hydrolyzed Casein, Cocodimonium Hydroxypropyl Hydrolyzed Collagen, Cocodimonium Hydroxypropyl Hydrolyzed Hair Keratin, Cocodimonium Hydroxypropyl Hydrolyzed Keratin, Cocodimonium Hydroxypropy Hydrolyzed - propyl hydrolyzed silk, cocodimonium hydroxypropyl hydrolyzed soy protein, cocodimonium hydroxypropyl hydrolyzed wheat protein, cocodimonium
  • the plant-based cationic protein hydrolyzates and derivatives are very particularly preferred.
  • the anionic polymers (G2) which can support the color-preserving action of the active ingredient according to the invention, are anionic polymers which have carboxylate and / or sulfonate groups.
  • anionic monomers from which such polymers can consist are acrylic acid, methacrylic acid, Crotonic acid, maleic anhydride and 2-acrylamido-2-methylpropanesulfonic acid.
  • the acidic groups can be present in whole or in part as sodium, potassium, ammonium, mono- or triethanolammonium salt.
  • Preferred monomers are 2-acrylamido-2-methylpropanesulfonic acid and acrylic acid.
  • Anionic polymers which contain 2-acrylamido-2-methylpropanesulfonic acid as the sole or co-monomer have proven to be very particularly effective, the sulfonic acid group being able to be present in whole or in part as the sodium, potassium, ammonium, mono- or triethanolammonium salt ,
  • the homopolymer of 2-acrylamido-2-methyl propane sulfonic acid which is available for example under the name Rheothik ® l 1-80 is commercially.
  • copolymers of at least one anionic monomer and at least one nonionic monomer are preferred.
  • anionic monomers reference is made to the substances listed above.
  • Preferred nonionic monomers are acrylamide, methacrylamide, acrylic acid ester, methacrylic acid ester, vinyl pyrrolidone, vinyl ether and vinyl ester.
  • Preferred anionic copolymers are acrylic acid-acrylamide copolymers and in particular polyacrylamide copolymers with monomers containing sulfonic acid groups.
  • a particularly preferred anionic copolymer consists of 70 to 55 mol% of acrylamide and 30 to 45 mol% of 2-acrylamido-2-methylpropanesulfonic acid, the sulfonic acid group being wholly or partly as sodium, potassium, ammonium, mono- or triethanolammonium Salt is present.
  • This copolymer can also be crosslinked, the crosslinking agents used preferably being polyolefinically unsaturated compounds such as tetraallyloxyethane, allyl sucrose, allylpentaerythritol and methylene bisacrylamide.
  • Such a polymer is contained in the commercial product Sepigel ® 305 from SEPPIC.
  • the use of this compound, which in addition to the polymer component contains a hydrocarbon mixture (C, 3 -C 4 -isoparaffin) and a nonionic emulsifier (Laureth-7), has proven to be particularly advantageous in the context of the teaching according to the invention.
  • Also known as compound with isohexadecane and poly sold under the name Simulgel® ® 600 sorbate-80 sodium acryloyldimethyltaurate copolymers have proven effective as inventively particularly.
  • anionic homopolymers are uncrosslinked and crosslinked polyacrylic acids. Allyl ethers of pentaerythritol, sucrose and propylene can be preferred crosslinking agents. Such compounds are for example available under the trademark Carbopol ® commercially.
  • Copolymers of maleic anhydride and methyl vinyl ether are also color-preserving polymers.
  • a cross-linked with 1,9-decadiene painting einklare-methyl vinyl ether copolymer is available under the name Stabileze® ® QM.
  • amphoteric polymers can be used as polymers to increase the effect of the active ingredient combination according to the invention.
  • amphoteric polymers includes both those polymers which contain both free amino groups and free -COOH or SO 3 H groups in the molecule and are capable of forming internal salts, and also zwitterionic polymers which contain quaternary ammonium groups and -COO " - or -SO 3 " groups, and summarized those polymers which contain -COOH or SO 3 H groups and quaternary ammonium groups.
  • amphopolymer suitable is that available under the name Amphomer ® acrylic resin which is a copolymer of ethyl methacrylate tert-butylamino, N- (1J, 3,3-tetramethylbutyl) -acrylamide and two or more monomers from the group of acrylic acid, Methacrylic acid and its simple esters.
  • Amphomer ® acrylic resin which is a copolymer of ethyl methacrylate tert-butylamino, N- (1J, 3,3-tetramethylbutyl) -acrylamide and two or more monomers from the group of acrylic acid, Methacrylic acid and its simple esters.
  • Amphoteric polymers which are preferably used are those polymers which essentially consist of one another
  • A is the anion of an organic or inorganic acid
  • these compounds can be used both directly and in salt form, which is obtained by neutralizing the polymers, for example with an alkali metal hydroxide.
  • an alkali metal hydroxide for example, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium sulfate, sodium sulfate, sodium sulfate ion ;
  • Acrylamido-propyl-trimethyl-a-ammonium chloride is a particularly preferred monomer (a).
  • Acrylic acid is preferably used as monomer (b) for the polymers mentioned.
  • the agents according to the invention can contain nonionic polymers (G4).
  • Suitable nonionic polymers are, for example:
  • Vinylpyrrolidone / Vinylester copolymers as are marketed, for example under the trademark Luviskol ® (BASF). Luviskol ® VA 64 and Luviskol ® VA 73, each vinylpyrrolidone / vinyl acetate copolymers are also preferred nonionic polymers.
  • Cellulose ethers such as hydroxypropyl cellulose, hydroxyethyl cellulose and hydroxypropylcellulose Methylhy- as they are for example sold under the trademark Culminal® ® and Benecel ® (AQUALON).
  • Siloxanes These siloxanes can be both water-soluble and water-insoluble. Both volatile and non-volatile siloxanes are suitable, non-volatile siloxanes being understood to mean those compounds whose boiling point at normal pressure is above 200 ° C.
  • Preferred siloxanes are polydialkylsiloxanes, such as, for example, polydimethylsiloxane, polyalkylarylsiloxanes, such as, for example, polyphenylmethylsiloxane, ethoxylated polydialkylsiloxanes and polydialkylsiloxanes which contain amine and / or hydroxyl groups.
  • the preparations used contain several, in particular two different polymers of the same charge and / or each contain an ionic and an amphoteric and / or non-ionic polymer.
  • the polymers (G) are preferably present in the agents used according to the invention in amounts of 0.05 to 10% by weight, based on the total agent. Amounts from 0.1 to 5, in particular from 0.1 to 3% by weight are particularly preferred.
  • Protein hydrolyzates and / or amino acids and their derivatives (H) may also be present in the preparations used according to the invention.
  • Protein hydrolyzates are product mixtures that are obtained by acidic, basic or enzymatically catalyzed breakdown of proteins (proteins).
  • protein hydrolyzates of both vegetable and animal origin can be used.
  • Animal protein hydrolyzates are, for example, elastin, collagen, keratin, silk and milk protein protein hydrolyzates, which can also be in the form of salts.
  • Such products are, for example, under the trademarks Dehylan ® (Cognis), Promois ® (Interorgana), Collapuron ® (Cognis), Nutrilan ® (Cognis), Gelita-Sol ® (Deutsche Gelatine Fabriken Stoess & Co), Lexein ® (Inolex) and Kerasol ® (Croda) sold.
  • protein hydrolysates of plant origin e.g. B. soy, almond, pea, potato and wheat protein hydrolyzates.
  • Such products are available, for example, under the trademarks Gluadin ® (Cognis), DiaMin ® (Diamalt), Lexein ® (Inolex) and Crotein ® (Croda).
  • amino acid mixtures obtained in some other way can optionally be used in their place. It is also possible to use derivatives of the protein hydrolyzates, for example in the form of their fatty acid condensation products. Such products are sold for example under the names Lamepon® ® (Cognis), Lexein ® (Inolex), Crolastin ® (Croda) or crotein ® (Croda).
  • the protein hydrolyzates or their derivatives are contained in the agents used according to the invention preferably in amounts of 0.1 to 10% by weight, based on the total agent. Amounts of 0.1 to 5% by weight are particularly preferred.
  • the action of the active ingredients (A) can be increased by UV filters (I).
  • the structure and physical properties of the UV filters to be used according to the invention are not subject to any general restrictions. Rather, all UV filters that can be used in the cosmetics sector are suitable, the absorption maximum of which lies in the UV A (315-400 nm), in the UVB (280-315 nm or in the UVC ( ⁇ 280 nm) range. UV filters with an absorption maximum in the UVB Range, especially in the range from about 280 to about 300 nm, are particularly preferred.
  • the UV filters used according to the invention can be selected, for example, from substituted benzophenones, p-aminobenzoic acid esters, diphenylacrylic acid esters, cinnamic acid esters, salicylic acid esters, benzimidazoles and o-aminobenzoic acid esters.
  • UV filters which can be used according to the invention are 4-amino-benzoic acid, N, N, N-trimethyl-4- (2-oxobom-3-ylidenemethyl) aniline-methylsulfate, 3,3,5-trimethyl-cyclohexyl-salicylate (homosalates ), 2-Hydroxy-4-methoxy-benzophenone (Benzophenone-3; UvinuI ® M 40, Uvasorb ® MET, Neo Heliopan ® BB, Eusolex ® 4360), 2-phenylbenzimidazole-5-sulfonic acid and its potassium, sodium - and triethanolamine salts (phenylbenzimidazole sulfonic acid; Parsol ® HS; Neo Helio ⁇ an ® Hydro), 3,3 '- (1,4-phenylenedimethylene) -bis (7,7-dimethyl-2-oxo-bicyclo- [2.2J] hept -l-yl-methane
  • 4-Amino-benzoic acid, N, N, N-trimethyl-4- (2-oxobom-3-ylidene methyl) aniline methyl sulfate are preferred, 3,3,5-trimethyl-cyclohexyisalicylate, 2-hydroxy-4-methoxy-benzophenone, 2-phenylbenzimidazole-5-sulfonic acid and its potassium, sodium and triethanolamine salts, 3,3 '- (1,4-phenylenedimethylene ) -bis (7,7-dimethyl-2-oxobicyclo- [2.2.1] hept-1-yl-methanesulfonic acid) and their salts, l- (4-tert-butylphenyl) -3- (4-methoxyphenyl) propane-1,3-dione, ⁇ - (2-oxobom-3-ylidene) toluene-4-sulfonic acid and its salts, ethyl ethoxylated 4-amino
  • 2-hydroxy-4-methoxy-benzophenone, 2-phenylbenzimidazole-5-sulfonic acid and their potassium, sodium and triethanolamine salts, l- (4-tert-butylphenyl) -3- (4-methoxyphenyl) are very particularly preferred -propan-l, 3-dione, 4-methoxycinnamic acid-2-ethylhexyl ester and 3- (4'-methylbenzylidene) -D, L-camphor.
  • Preferred UV filters are those whose molar extinction coefficient at the absorption maximum is above 15,000, in particular above 20,000.
  • the water-insoluble compound has, in the context of the teaching according to the invention, the higher activity than those water-soluble compounds which differ from it by one or more additional ionic grapples.
  • water-insoluble are UV filters which do not dissolve in water at 20 ° C. by more than 1% by weight, in particular not more than 0.1% by weight.
  • these compounds should be at least 0.1, in particular at least 1% by weight soluble in conventional cosmetic oil components at room temperature). The use of water-insoluble UV filters can therefore be preferred according to the invention.
  • those UV filters are preferred which have a cationic group, in particular a quaternary ammonium group.
  • These UV filters have the general structure U - Q.
  • the structural part U stands for a group that absorbs UV rays.
  • this group can be derived from the known UV filters mentioned above, which can be used in the cosmetics sector, in which a group, usually a hydrogen atom, of the UV filter is replaced by a cationic group Q, in particular with a quaternary amino function , Connections from which the structural part U can be derived are, for example
  • Structural parts U which are derived from cinnamic acid amide or from N, N-dimethylamino-benzoic acid amide are preferred according to the invention.
  • the component parts U can be selected so that the absorption maximum of the UV filter can be both in the UVA (315-400 nm) and in the UVB (280-315 nm) or in the UVC ( ⁇ 280 nm) range.
  • UV filters with an absorption maximum in the UVB range in particular in the range from approximately 280 to approximately 300 nm, are particularly preferred.
  • the structural part U is preferably chosen such that the molar extinction coefficient of the UV filter at the absorption maximum is above 15,000, in particular above 20,000.
  • the structural part Q preferably contains a quaternary ammonium group as the cationic group.
  • this quaternary ammonium group can be directly connected to the structural part U, so that the structural part U represents one of the four substituents of the positively charged nitrogen atom.
  • one of the four substituents is preferred on positively charged nitrogen atom is a group, in particular an alkylene group having 2 to 6 carbon atoms, which functions as a connection between the structural part U and the positively charged nitrogen atom.
  • the Grappe Q advantageously has the general structure - (CH 2 ) X -N + R 1 R 2 R 3 X " , in which x stands for an integer from 1 to 4, R 1 and R 2 independently of one another stand for C M - Alkylgrappen, R 3 stands for a C,. 22 -Alkylrarappe or a Benzylgrappe and X " for a physiologically compatible anion.
  • x preferably represents the number 3, R 1 and R 2 each for a methyl group and R 3 either for a methyl group or a saturated or unsaturated, linear or branched hydrocarbon chain with 8 to 22, in particular 10 to 18, carbon atoms.
  • Physiologically acceptable anions are, for example, inorganic anions such as halides, in particular chloride, bromide and fluoride, sulfate ions and phosphate ions, and organic anions such as lactate, citrate, acetate, tartrate, methosulfate and tosylate.
  • inorganic anions such as halides, in particular chloride, bromide and fluoride, sulfate ions and phosphate ions
  • organic anions such as lactate, citrate, acetate, tartrate, methosulfate and tosylate.
  • Two preferred UV filters with cationic groups are the commercially available compounds cinnamic acid-trimethylammonium chloride (quat Incro- ® UV-283), and dodecyl-dimethylammobenzamidopropyl dimemylammoniumtosylat (Escalol ® HP 610).
  • the teaching of the invention also includes the use of a combination of several UV filters.
  • the combination of at least one water-insoluble UV filter with at least one UV filter with a cationic group is preferred.
  • the UV filters (I) are usually contained in the agents used according to the invention in amounts of 0.1-5% by weight, based on the total agent. Amounts of 0.4-2.5% by weight are preferred.
  • the color-preserving action of the active ingredient according to the invention can be further increased by a 2-pyrrolidinone-5-carboxylic acid and its derivatives (J).
  • Another The object of the invention is therefore the use of the color-retaining active ingredient in combination with derivatives of 2-pyrrolidinone-5-carboxylic acid.
  • Preferred are the sodium, potassium, calcium, magnesium or ammonium salts in which the ammonium ion carries one to three C r to C 4 alkyl groups in addition to hydrogen.
  • the sodium salt is very particularly preferred.
  • the amounts used in the agents according to the invention are 0.05 to 10% by weight, based on the total agent, particularly preferably 0.1 to 5 and in particular 0.1 to 3% by weight.
  • Vitamins, pro-vitamins and vitamin precursors which are usually assigned to groups A, B, C, E, F and H are preferred according to the invention.
  • vitamin A and 3,4-didehydroretinol belong to the group of substances referred to as vitamin A.
  • ⁇ -carotene is the provitamin of retinol.
  • vitamin A contains, for example, vitamin A component Acid and its esters, vitamin A aldehyde and vitamin A alcohol as well as its esters such as palmitate and acetate.
  • the preparations used according to the invention preferably contain the vitamin A component in amounts of 0.05-1% by weight, based on the entire preparation.
  • the vitamin B group or the vitamin B complex include u. a.
  • Vitamin B 2 (riboflavin)
  • nicotinic acid and nicotinamide are often listed under this name.
  • Preferred according to the invention is the nicotinic acid amide, which is contained in the agents used according to the invention preferably in amounts of 0.05 to 1% by weight, based on the total agent.
  • panthenol and / or pantolactone is preferably used.
  • Derivatives of panthenol which can be used according to the invention are in particular the esters and ethers of Panthenols and cationically derivatized panthenols. Individual representatives are, for example, panthenol triacetate, panthenol monoethyl ether and its monoacetate and the cationic panthenol derivatives disclosed in WO 92/13829.
  • the compounds of the vitamin B 5 type mentioned are preferably present in the agents used according to the invention in amounts of 0.05-10% by weight, based on the total agent. Amounts of 0.1-5% by weight are particularly preferred.
  • - Vitamin B 6 pyridoxine as well as pyridoxamine and pyridoxal).
  • Vitamin C (ascorbic acid). Vitamin C is used in the agents used according to the invention preferably in amounts of 0.1 to 3% by weight, based on the total agent. Use in the form of the palmitic acid ester, the glucosides or phosphates can be preferred. Use in combination with tocopherols may also be preferred.
  • Vitamin E tocopherols, especially ⁇ -tocopherol.
  • Tocopherol and its derivatives which include in particular the esters such as acetate, nicotinate, phosphate and succinate, are preferably present in the agents used according to the invention in amounts of 0.05-1% by weight, based on the total agent ,
  • Vitamin F usually means essential fatty acids, in particular linoleic acid, linolenic acid and arachidonic acid.
  • Vitamin H is the compound (3aS, 4S, 6ai?) - 2-oxohexahydrotMenol [3,4-d] -imidazole-4-valeric acid, for which the trivial name biotin has now become established.
  • Biotin is contained in the agents used according to the invention preferably in amounts of 0.0001 to 1.0% by weight, in particular in amounts of 0.001 to 0.01% by weight.
  • the agents used according to the invention preferably contain vitamins, provitamins and vitamin precursors from grappa A, B, E and H. Panthenol, pantolactone, pyridoxine and its derivatives as well as nicotinamide and biotin are particularly preferred.
  • extracts are usually produced by extracting the entire plant. In individual cases, however, it may also be preferred to produce the extracts exclusively from flowers and / or leaves of the plant.
  • the extracts from green tea, almond, aloe vera, coconut, mango, apricot, lime, wheat, kiwi and melon are particularly suitable for the use according to the invention.
  • Water, alcohols and mixtures thereof can be used as extractants for the production of the plant extracts mentioned.
  • the alcohols lower alcohols such as ethanol and isopropanol, but in particular polyhydric alcohols such as ethylene glycol and propylene glycol, are preferred, both as the sole extracting agent and in a mixture with water.
  • Plant extracts based on water / propylene glycol in a ratio of 1:10 to 10: 1 have proven to be particularly suitable.
  • the plant extracts can be used both in pure and in diluted form. If they are used in dilute form, they usually contain about 2 to 80% by weight of active substance and, as a solvent, the extractant or mixture of extractants used in their extraction.
  • mixtures of several, in particular two, different plant extracts in the agents according to the invention may be preferred.
  • the color-preserving active ingredient according to the invention can in principle be added directly to the colorant.
  • the application of the color-preserving active ingredient to the dyed ceramic fiber can, however, also take place in a separate step, either before or after the actual dyeing process. Separate treatments, possibly also days or weeks before or after the dyeing process, are encompassed by the teaching according to the invention. However, it is preferred to use the active ingredient according to the invention after coloring and in particular in the colorant.
  • the term dyeing process includes all processes known to the person skilled in the art, in which a dye is applied to the optionally moistened hair and either left on the hair for a time between a few minutes and about 45 minutes and then with water or a surfactant-containing agent is rinsed out or left entirely on the hair.
  • a dye is applied to the optionally moistened hair and either left on the hair for a time between a few minutes and about 45 minutes and then with water or a surfactant-containing agent is rinsed out or left entirely on the hair.
  • monographs e.g. BKH Schrader, Fundamentals and Recipes of Cosmetics, 2nd edition, Hüthig Buch Verlag, Heidelberg, 1989, referring to the corresponding knowledge of the expert.
  • the color-preserving active ingredient combination according to the invention is applied to the keratin fiber, in particular human hair.
  • the formulations of these preparations include, for example, creams, lotions, solutions, water, emulsions such as W / O, O / W, PIT emulsions (emulsions based on the teaching of phase inversion, PIT), microemulsions and multiple emulsions, gels, Sprays, aerosols and foam aerosols are suitable.
  • the pH of these preparations can in principle be between 2 and 11. It is preferably between 5 and 11, values from 6 to 10 being particularly preferred. Virtually any acid or base that can be used for cosmetic purposes can be used to adjust this pH.
  • Food acids are usually used as acids.
  • Edible acids are those acids that are ingested as part of normal food intake and have positive effects on the human organism.
  • Edible acids are, for example, acetic acid, lactic acid, tartaric acid, citric acid, malic acid, ascorbic acid and gluconic acid.
  • citric acid and lactic acid is particularly preferred.
  • Preferred bases are ammonia, alkali metal hydroxides, monoethanolamine, triethanolamine and N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine.
  • Preparations remaining on the hair have proven to be particularly effective and can therefore represent preferred embodiments of the teaching according to the invention.
  • “remaining on the hair” is understood to mean those preparations which are not rinsed out of the hair again after a period of a few seconds to an hour using water or an aqueous solution. Rather, the preparations remain until the next hair wash, i.e. usually more than 12 hours on the hair.
  • these preparations are formulated as a hair treatment or hair conditioner.
  • the preparations according to the invention in accordance with this embodiment can be rinsed out with water or an at least predominantly water-containing agent after this exposure time has expired; however, as stated above, they can be left on the hair. It may be preferred to prepare the preparation according to the invention before using a cleaning agent, one Apply waving or other hair treatment agents to the hair. In this case, the preparation according to the invention serves as color protection for the subsequent applications.
  • the agents according to the invention can also be, for example, cleaning agents such as shampoos, conditioning agents such as rinses, setting agents such as hair setting agents, foam setting agents, styling gels and hair dryer shafts, permanent shaping agents such as permanent waving and fixing agents, and in particular as part of a permanent waving process pretreatment agents or rinses used in the dyeing process.
  • cleaning agents such as shampoos
  • conditioning agents such as rinses
  • setting agents such as hair setting agents, foam setting agents, styling gels and hair dryer shafts
  • permanent shaping agents such as permanent waving and fixing agents, and in particular as part of a permanent waving process pretreatment agents or rinses used in the dyeing process.
  • these preparations can in principle contain all further components known to the person skilled in the art for such cosmetic compositions.
  • non-ionic polymers such as, for example, vinyl pyrrolidone / vinyl acrylate copolymers, polyvinyl pyrrolidone and vinyl pyrrolidone / vinyl acetate copolymers and polysiloxanes,
  • - Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, for.
  • methyl cellulose, hydroxyalkyl cellulose and carboxy methyl cellulose starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as.
  • B. bentonite or fully synthetic hydrocolloids such.
  • Structurants such as maleic acid and lactic acid
  • hair-conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins, and silicone oils,
  • Solvents and intermediates such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, - Symmetrical and asymmetrical, linear and branched dialkyl ethers with a total of between 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 and 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 Di tert-butyl ether
  • Fatty alcohols especially linear and / or saturated fatty alcohols with 8 to 30 carbon atoms,
  • active ingredients which improve the fiber tract in particular mono-, di- and oligosaccharides such as, for example, glucose, galactose, fractose, fructose and lactose,
  • paraffin oils such as paraffin oils, vegetable oils, e.g. B. sunflower oil, orange oil, almond oil, wheat germ oil and peach seed oil as well
  • Phospholipids for example soy lecithin, egg lecithin and cephalins,
  • quaternized amines such as memyl-l-alkylamidoethyl-2-alkylimidazolinium methosulfate,
  • anti-dandruff agents such as piroctone olamine, zinc omadine and climbazol
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates,
  • opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers
  • Pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate
  • Propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air,
  • the invention also relates to agents for improving the fastness to washing of colored fibers and for intensifying the coloring, in particular keratin fibers, which comprise a combination of a. the active ingredient (A) and b. contain a dye precursor (B) and / or a substantive dye (C).
  • a particularly preferred embodiment here is one in which the active ingredient (A) and dye precursors (B) and / or substantive dyes (C) are packaged separately and only added together immediately before use.
  • a third object of the invention is an agent for improving the fastness to washing of dyed fibers and for intensifying the dyeing, in particular keratinic fibers, which comprises an active ingredient combination of a. a compound (A) according to claim 1 and b. contains a polymer (G), with the proviso that the compound (A) is not formaldehyde or a compound which releases formaldehyde.
  • a particularly preferred embodiment is that in which the composition comprising the active ingredient (A) and the polymer (G) as an active ingredient combination after dyeing on the dyed fiber is applied.
  • surfactants (E) and / or fatty substances (D) are also present.
  • a fourth object of the invention is a process for improving the wash-fastness of dyeings of fibers, in particular keratin fibers, in which a coloring agent with the active ingredient according to the invention, as used in one of claims 1 to 9, is applied to the fibers, the agent if desired after an exposure time of 1 to 45 minutes.
  • Strands of Kerling (0.5 g Kerling, natural white) were tied in the middle and half bleached. The other half was bleached twice and subjected to two conventional perm treatments with the commercial product Poly Lock-Normal Perm.
  • the fibers were each exposed in a first step for 30 minutes at room temperature to the reducing solution (containing 7.9% by weight of thioglycolic acid), rinsed with pure water and then fixed at room temperature for 10 minutes (oxidation solution containing 2 6 wt .-% hydrogen peroxide). After the oxidative treatment, the fibers were rinsed and dried again.
  • a mixture of 1 g of a coloring cream (commercial product Poly Diadem skin care cream coloring 718 hazelnut) and 1 ml of an aqueous 6% hydrogen peroxide solution was applied to the strands and left there at 32 ° C. for 30 minutes. The hair was then rinsed with water.
  • a coloring cream commercial product Poly Diadem skin care cream coloring 718 hazelnut
  • an aqueous 6% hydrogen peroxide solution was applied to the strands and left there at 32 ° C. for 30 minutes. The hair was then rinsed with water.
  • the hair was treated for 5 minutes with 1 g of a conditioning agent from Table 1 at 32 ° C., rinsed, dried and measured by colorimetry. Value 6 - - subsequently thereto the strands of hair with an aqueous solution% Texapon ® NSO, pH was consisting of 1.0 wt. 7, washed 6 times, and dried in turn colorimetrically measured. d. Colorimetric measurement
  • each strand of hair was measured at eight points using the Text Flash color measurement system from Datacolor.
  • the sample to be measured was fixed in a clamping device on the spectrophotometer, the reflectance values over the range of visible light from 390 - 700 nm measured at a distance of 10 nm and processed by a computer.
  • the computer program determined the standard color values according to the CIELAB system in accordance with DIN 5033.
  • the measurement results of the total color difference ⁇ E were evaluated with the Data Color Tools QC software according to formula (I) and summarized in the following table.
  • the composition marked with “V” served as the standard
  • Methylparaben (and) propylparaben) (COGNIS) 13- INCI name: Imidazolidinyl Urea (Sutton Laboratories)
  • Glucoside (COGNIS) 3 Liquid dispersion of pearlescent substances and amphoteric surfactant (approx. 62%
  • CTFA name Glycol Distearate (and) Glycerin (and) Laureth-4
  • the formaldehyde is added immediately before use.
  • Etidronic Acid (COGNIS) 48- acrylic ester-methacrylic acid copolymer (25% active substance) (BASF)
  • BASF active substance
  • the glutardialdehyde is added immediately before use.

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Abstract

Selon la présente invention, l'utilisation d'aldéhydes à chaîne courte et/ou de formaldéhyde et/ou de composés séparant le formaldéhyde permet d'améliorer sensiblement la tenue de la couleur de fibres colorées, notamment de fibres de kératine.
PCT/EP2001/011056 2000-10-04 2001-09-25 Nouvelle utilisation d'aldehydes a chaine courte et de composes separant le formaldehyde WO2002030373A2 (fr)

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EP01986594A EP1322281A2 (fr) 2000-10-04 2001-09-25 Nouvelle utilisation d'aldehydes a chaine courte et de composes separant le formaldehyde
AU2002223557A AU2002223557A1 (en) 2000-10-04 2001-09-25 Novel use of short-chained aldehydes and compoundsseparating formaldehyde

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DE2000148922 DE10048922A1 (de) 2000-10-04 2000-10-04 Neue Verwendung von kurzkettigen Aldehyden und Formaldehyd abspaltenden Verbindungen
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WO2003030848A1 (fr) * 2001-10-02 2003-04-17 Henkel Kommanditgesellschaft Auf Aktien Procede pour teindre des fibres de keratine en utilisant des composes carbonyles pour ameliorer la stabilite chromatique des colorations de cheveux
WO2003035018A1 (fr) * 2001-10-23 2003-05-01 Henkel Kommanditgesellschaft Auf Aktien Nouvelle utilisation de tensioactifs derives du sucre et de glycerides partiels d'acides gras dans des colorants
WO2017182822A1 (fr) * 2016-04-22 2017-10-26 Innospec Limited Procédés, compositions et utilisations associées
WO2017182819A1 (fr) * 2016-04-22 2017-10-26 Innospec Limited Procédés, compositions et utilisations associées
WO2017182821A1 (fr) * 2016-04-22 2017-10-26 Innospec Limited Procédés, compositions et utilisations associées
WO2017182820A1 (fr) * 2016-04-22 2017-10-26 Innospec Limited Procédés, compositions et utilisations associées
WO2018060720A1 (fr) * 2016-09-30 2018-04-05 Innospec Limited Réduction de perte de couleur d'une matière colorée à l'aide d'un sel aminique d'un acide carboxylique
WO2018060728A3 (fr) * 2016-09-30 2018-05-17 Innospec Limited Compositions et procédés
US11234917B2 (en) * 2016-09-30 2022-02-01 Innospec Limited Methods, compositions and uses relating thereto
US11311471B2 (en) * 2016-09-30 2022-04-26 Innospec Limited Methods, compositions and uses relating thereto

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ATE328570T1 (de) * 2002-04-25 2006-06-15 Oreal Verwendung von alpha-dialdehyden in anwesenheit eines ammoniumsalzes einer brönsted säure zum färben von keratinfasern
DE10218588A1 (de) * 2002-04-26 2003-11-06 Wella Ag Mittel zum oxidativen Färben von Keratinfasern
DE10260832A1 (de) * 2002-12-23 2004-07-01 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern
DE102006038343A1 (de) * 2006-08-15 2008-02-21 Henkel Kgaa Aufhell- und/oder Färbemittel mit Aldehyd(en)
FR2915376B1 (fr) * 2007-04-30 2011-06-24 Oreal Utilisation d'un agent de couplage multi-carbo sites multi-groupements pour proteger la couleur vis-a-vis du lavage de fibres keratiniques teintes artificiellement; procedes de coloration
DE102016219007A1 (de) * 2016-09-30 2018-04-05 Henkel Ag & Co. Kgaa Verbessert konditionierende Haarbehandlungsmittel mit Auswaschschutz
DE102016218997A1 (de) * 2016-09-30 2018-04-05 Henkel Ag & Co. Kgaa Verbessert konditionierende Haarbehandlungsmittel mit Auswaschschutz
DE102016218999A1 (de) * 2016-09-30 2018-04-05 Henkel Ag & Co. Kgaa Verbessert konditionierende Haarbehandlungsmittel mit Auswaschschutz
FR3118708B1 (fr) * 2021-01-11 2023-08-25 Oreal Composition pour fibres kératineuses
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See also references of EP1322281A2 *

Cited By (51)

* Cited by examiner, † Cited by third party
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WO2003030848A1 (fr) * 2001-10-02 2003-04-17 Henkel Kommanditgesellschaft Auf Aktien Procede pour teindre des fibres de keratine en utilisant des composes carbonyles pour ameliorer la stabilite chromatique des colorations de cheveux
WO2003035018A1 (fr) * 2001-10-23 2003-05-01 Henkel Kommanditgesellschaft Auf Aktien Nouvelle utilisation de tensioactifs derives du sucre et de glycerides partiels d'acides gras dans des colorants
JP2019518000A (ja) * 2016-04-22 2019-06-27 インノスペック リミテッドＩｎｎｏｓｐｅｃ Ｌｉｍｉｔｅｄ 方法、組成物、及びそれらに関する使用
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WO2017182821A1 (fr) * 2016-04-22 2017-10-26 Innospec Limited Procédés, compositions et utilisations associées
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KR20180132907A (ko) * 2016-04-22 2018-12-12 이노스펙 리미티드 방법, 조성물 및 그에 관한 용도
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KR20180133915A (ko) * 2016-04-22 2018-12-17 이노스펙 리미티드 방법, 조성물 및 그에 관한 용도
KR20180135019A (ko) * 2016-04-22 2018-12-19 이노스펙 리미티드 방법, 조성물 및 그에 관한 용도
CN109069372A (zh) * 2016-04-22 2018-12-21 因诺斯佩克有限公司 方法、组合物和与其相关的用途
CN109069371A (zh) * 2016-04-22 2018-12-21 因诺斯佩克有限公司 方法、组合物和与其相关的用途
CN109152710A (zh) * 2016-04-22 2019-01-04 因诺斯佩克有限公司 方法、组合物及其相关用途
CN109310594A (zh) * 2016-04-22 2019-02-05 因诺斯佩克有限公司 方法、组合物及其相关用途
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JP2019515898A (ja) * 2016-04-22 2019-06-13 インノスペック リミテッドＩｎｎｏｓｐｅｃ Ｌｉｍｉｔｅｄ 方法、組成物、及びそれらに関する使用
WO2017182822A1 (fr) * 2016-04-22 2017-10-26 Innospec Limited Procédés, compositions et utilisations associées
GB2554485B (en) * 2016-04-22 2020-01-01 Innospec Ltd Methods, compositions and uses relating thereto
GB2552571B (en) * 2016-04-22 2019-04-17 Innospec Ltd A method of treating hair with a composition comprising a hydroxy-substituted aldehyde
WO2017182819A1 (fr) * 2016-04-22 2017-10-26 Innospec Limited Procédés, compositions et utilisations associées
KR20180132906A (ko) * 2016-04-22 2018-12-12 이노스펙 리미티드 방법, 조성물 및 그에 관한 용도
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GB2552569B (en) * 2016-04-22 2020-12-16 Innospec Ltd Composition comprising alpha-substituted aldehyde and use thereof with dyed hair
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RU2748840C2 (ru) * 2016-04-22 2021-05-31 Инноспек Лимитед Способы, композиции и относящиеся к ним применения
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RU2756099C2 (ru) * 2016-04-22 2021-09-28 Инноспек Лимитед Способы, композиции и относящиеся к ним применения
RU2763495C2 (ru) * 2016-04-22 2021-12-29 Инноспек Лимитед Способы, композиции и относящиеся к ним применения
RU2763928C1 (ru) * 2016-04-22 2022-01-11 Инноспек Лимитед Способы, композиции и относящиеся к ним применения
KR102351479B1 (ko) * 2016-04-22 2022-01-17 이노스펙 리미티드 방법, 조성물 및 그에 관한 용도
KR102351475B1 (ko) * 2016-04-22 2022-01-17 이노스펙 리미티드 방법, 조성물 및 그에 관한 용도
KR102407551B1 (ko) * 2016-04-22 2022-06-10 이노스펙 리미티드 방법, 조성물 및 그에 관한 용도
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US11253453B2 (en) 2016-09-30 2022-02-22 Innospec Limited Reducing colour loss from a dyed material by using an amine salt of a carboxylic acid
US11311471B2 (en) * 2016-09-30 2022-04-26 Innospec Limited Methods, compositions and uses relating thereto
US11234917B2 (en) * 2016-09-30 2022-02-01 Innospec Limited Methods, compositions and uses relating thereto
WO2018060728A3 (fr) * 2016-09-30 2018-05-17 Innospec Limited Compositions et procédés
WO2018060720A1 (fr) * 2016-09-30 2018-04-05 Innospec Limited Réduction de perte de couleur d'une matière colorée à l'aide d'un sel aminique d'un acide carboxylique
AU2017334287B2 (en) * 2016-09-30 2023-06-08 Innospec Limited Cosmetic compositions for combatting colour loss from a dyed material

Also Published As

Publication number Publication date
WO2002030373A3 (fr) 2002-08-22
DE10048922A1 (de) 2002-04-11
AU2002223557A1 (en) 2002-04-22
EP1322281A2 (fr) 2003-07-02

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