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WO1993021897A1 - Permanent waving process - Google Patents

Permanent waving process Download PDF

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Publication number
WO1993021897A1
WO1993021897A1 PCT/EP1993/000931 EP9300931W WO9321897A1 WO 1993021897 A1 WO1993021897 A1 WO 1993021897A1 EP 9300931 W EP9300931 W EP 9300931W WO 9321897 A1 WO9321897 A1 WO 9321897A1
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WO
WIPO (PCT)
Prior art keywords
hair
alkyl
aqueous preparation
carbon atoms
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1993/000931
Other languages
German (de)
French (fr)
Inventor
Jörg KAHRE
Reinhard Müller
Doris Oberkobusch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Filing date
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Publication of WO1993021897A1 publication Critical patent/WO1993021897A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/604Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/04Preparations for permanent waving or straightening the hair

Definitions

  • the invention relates to a method for permanent hair shaping by reductive splitting and renewed oxidative knotting of disulfide bonds in hair keratin.
  • the permanent hair shaping is carried out according to the known Mamawe11 method in such a way that the hair is mechanically deformed and the deformation z.
  • the hair is treated with the aqueous preparation of a keratin-reducing substance and rinsed with water or an aqueous solution after an exposure time.
  • the hair is then treated with the aqueous preparation of an oxidizing agent. After an exposure time, this is also rinsed out of the hair and the hair is freed from the mechanical deformation aids (curlers, papillots).
  • the aqueous preparation of the keratin-reducing agent is usually made alkaline, so that the hair swells and in this way a deep penetration of the keratin-reducing substance into the hair is made possible.
  • the keratin-reducing substance cleaves a part of the disulfide bonds of the keratin to -SH groups, so that the peptide cross-linking is loosened and, due to the tension in the hair due to the mechanical deformation, the keratin structure is reoriented. Under the influence of the oxidizing agent, disulfide bonds are again formed, and in this way the keratin structure is re-fixed in the predetermined deformation.
  • a negative side effect of the permanent waving of the hair that is carried out in this way is, however, regularly embrittlement and dulling of the hair. Furthermore, in many cases, other properties such as wet and dry combability, grip, smoothness, softness, gloss and tear resistance are also undesirably influenced. Finally, the application permanent wave preparations, especially in people with sensitive scalp, lead to an undesirable, increased skin stress.
  • a corresponding modification of the reducing solution generally leads to unsatisfactory wave outputs.
  • additives such as structurants, polymers, film formers and crosslinking resins can indeed reduce the damage to the hair; however, the structure of the hair remains more or less weakened.
  • DE-OS 41 07 313 describes the use of alkyl polyglycosides in preparations for shaping human hair.
  • the invention therefore relates to a process for permanent shaping of hair, in which the hair is treated with the aqueous preparation of a keratin-reducing substance before and / or after a mechanical shaping, rinsed after an exposure time, then with an aqueous one Preparation of an oxidizing agent fixed and also rinsed after an exposure time, characterized in that in the aqueous Preparation of the oxidizing agent an alkyl glycoside of the general formula (I),
  • R stands for an alkyl radical with 6 to 22 carbon atoms
  • Z for a mono- or oligosaccharide and its degree of oligomerization x for a number from 1.1 to 5, or its adduct with 1 to 10 molecules of ethylene oxide and / or propylene oxide in combination with a surface-active compound A, selected from the non-ionic, zwitterionic and amphoteric surfactants, and / or a polymeric compound B, where in the event that the polymeric compound B is a cation polymer, this is selected from
  • the aqueous preparation of the keratin-reducing substance is referred to below as the waving agent and the aqueous preparation of the oxidizing agent is referred to as the fixing agent.
  • alkyl glycosides of the formula (I) which can be used according to the invention are characterized by the following parameters.
  • 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.
  • the alkyl glycosides which can be used according to the invention can contain only one specific alkyl radical R. Usually, however, these compounds are produced starting from natural fats and oils or mineral oils. In this case, the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the particular workup of these compounds. Starting from natural fats and oils, the alkyl residues predominantly have an even number of carbon atoms. Such alkyl residues 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', compounds with an odd number of carbon atoms in the alkyl chain predom
  • Alkyl glycosides in which R consists either essentially of CQ and Cio-alkyl groups or essentially of C12 and (4-ATkyl groups) are particularly preferred.
  • Any mono- or oligosaccharides can be used as sugar building block Z.
  • Sugar with 5 or 6 carbon atoms and the corresponding oligosaccharides are usually used.
  • sugars are glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allos, altrose, mannose, gulose, idose, talose and sucrose.
  • Preferred sugar components are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkyl glycosides according to the invention contain an average of 1.1 to 5 sugar units. Alkyl glycosides with x values from 1.3 to 2 are preferred. Alkyl glycosides in which x is 1.4 to 1.6 are very particularly preferred.
  • alkoxylated homologs of the alkyl glycosides mentioned can also be used according to the invention.
  • These homologues can contain an average of up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
  • These products also usually do not represent uniform compounds, but instead have a corresponding homolog distribution depending on the selected ethoxylation process.
  • Such alkoxylated compounds can be obtained, for example, by using ethoxylated fatty alcohols for the synthesis of the alkyl glycosides.
  • the alkyl glycoside is preferably contained in the fixing agent in an amount of 0.1 to 40% by weight, based in each case on the total fixing agent. Amounts of 0.5 to 20% by weight are particularly preferred.
  • Another active ingredient component according to the invention are the surface-active compounds A, which are selected from the group of nonionic, zwitterionic and amphoteric surfactants.
  • Non-ionic surfactants contain z.
  • B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
  • Such connections are, for example
  • Ci2-C22 ⁇ ' EttLiteremono- and diesters of adducts of 1 to 30 moles of ethylene oxide with glycerol,
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one -CO ⁇ (") - or -S ⁇ 3 (") - 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 coconut alkyl-dimethylammonium glycinate, N-acylaminopropyl-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 cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate.
  • a preferred zwitterionic surfactant is the fatty acid
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a C 6 -C 16 -alkyl or acyl group, contain at least one free amino group and at least one -C00H or -SO3H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-Al ytaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the ATkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2-i8-AcyTsarcosine.
  • the compounds with ATkyT groups used in the aTs surfactants can each be uniform substances. However, it is generally preferred to use native 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 narrow homolog distribution can be used.
  • “Normal” homolog distribution means mixtures of HomoTogen which are obtained in the implementation of FettaTkohoT and ATkyTenoxid using ATkaTimetaTTen, ATkaTi etaTThydroxiden or ATkali metal alcoholate as Catalytic converters.
  • narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alkaline carbonates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.
  • the fixing agents according to the invention preferably contain the surface-active compounds A in amounts of 0.5 to 10% by weight, based on the total fixing agent.
  • polymeric compounds B Another component in active ingredient combinations according to the invention are polymeric compounds B.
  • the cationic polymers used according to the invention are selected from the group comprising quaternized cellulose ethers, polysiloxanes with quaternary groups,
  • Dimethyldiallylammonium chloride polymers and copolymers such as. B.
  • Copolymers of acrylamide and dimethyldiallylammonium chloride which are commercially available under the name Merquat R 550, are particularly preferred cationic polymers.
  • zwitterionic polymers are understood to mean those polymers which contain both cationic and anionic groups or groups which can easily be converted into them.
  • Cationic groups are, for example, groups which contain at least one ammonium or phosphonium unit; Examples of a unit which can easily be converted into a cationic group are primary, secondary and in particular tertiary amino groups. Ammonium groups are preferred cationic groups.
  • Suitable anionic groups are, for example, carbon, sulfone and phosphoric acid groups in free form or in salt form.
  • the carboxylic acid groups and their alkali, alkaline earth, aluminum and ammonium salts are preferred anionic groups.
  • the zwitterionic polymers used according to the invention can be constructed from monomers which contain both cationic and anionic groups.
  • the polymers can consist of a single type of monomer.
  • copolymers of the monomers mentioned and other nonionic monomers can be, for example, vinyl-based esters and vinyls, such as methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, hydroxypropyl methacrylate, acrylamide, vinyl pyrrolidone and Be ethanol.
  • These copolymers preferably contain at least 20%, in particular at least 50%, of ionic monomers.
  • Polymers preferred in the context of the invention are built up from at least 2 ionic monomers, a cationic and an anionic monomer.
  • Cationic and anionic monomers can be present in a 1: 1 molar ratio. However, it is preferred to use an excess of one type of monomer, in particular the cationic monomers. As a rule, cationic and anionic monomers are used in a ratio of 95: 5 to 60:40.
  • the polymers can furthermore contain nonionic monomers of the type mentioned above in amounts of up to 50 mol%, in particular up to 20 mol%.
  • preferred zwitterionic polymers are the zwitterionic polymers described in DE-A-39 29 973, which essentially consist of one another
  • Rl-CH CR 2 -C0-Z- (C n H 2n ) -N ( + )
  • AcryTamidopropyltrimethyTammoniumchTorid is a very particularly preferred monomer of FormeT (II).
  • Monomeric carboxylic acids of the general form (III) are acrylic acid, methacrylic acid, crotonic acid and 2-methyl-crotonic acid. Acrylic or methacrylic acid, in particular acrylic acid, are preferably used.
  • Prefers Salts of these carboxylic acids used are the lithium, sodium, potassium, magnesium, calcium and aluminum salts. The sodium salt is particularly preferred.
  • the ammonium salts can be used in which the ammonium ion can have one to three alkyl groups with 1-4 carbon atoms or hydroxyalkyl groups with 2-4 carbon atoms as substituents. Salts with unsubstituted ammonium ions and triethanolammonium ions are preferred.
  • Polysiloxane-polyorganobetaine copolymers are also preferred zwitterionic polymers.
  • Suitable amphoteric polymers are, for example, octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers.
  • Anionic polymers suitable according to the invention are, for example, vinyl acetate / crotonic acid copolymers, vinyl pyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and their esters as well as uncrosslinked and polyols crosslinked polyacrylic acids.
  • Suitable nonionic polymers are, for example, polyvinyl pyrrolidone
  • the polymeric compounds are cationic, zwitterionic or amphoteric polymers.
  • the use of the zwitterionic and a photomeric polymers is very particularly preferred.
  • the polymeric compounds B are contained in the fixing agents according to the invention preferably in amounts of 0.01 to 5% by weight, based on the total fixing agent. Concentrations of 0.01 to 2% by weight are particularly preferred.
  • the preparations according to the invention can contain all the constituents customary in hair treatment compositions. It depends on the type of agent, which of the components mentioned in the following are included in the agent.
  • oxidizing agents e.g. B. hydrogen peroxide and the usual stabilizers for stabilizing aqueous hydrogen peroxide preparations.
  • the pH of such aqueous H2O2 preparations which contain about 0.5 to 3.0% by weight of H2O2 is preferably 2 to 4; it is admitted by inorganic acids, preferably phosphoric acid.
  • Other preferred oxidizing agents are sodium and potassium bromate. Such bromates are used in concentrations of 1 to 10% by weight and the pH of the solutions is adjusted to 4 to 7.
  • Anionic and cationic surfactants may also be present.
  • Suitable anionic surfactants in hair treatment agents according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a TipophiTe ATkyTrios with about 10 to 22 carbon atoms.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • suitable anionic surfactants are in the form of the sodium, potassium and ammonium salts as well as the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group,
  • Esters of tartaric acid and citric acid with alcohols which are addition products of about 2-15 molecules of ethylene oxide and / or propylene oxide onto fatty alcohols with 8 to 22 carbon atoms.
  • 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, and sulfosuccinic acid and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid ono -ATkyTpolyoxyethylester with 8 to 18 carbon atoms in the ATkyT ⁇ group and 1 to 6 oxyethyl groups.
  • quaternary ammonium compounds such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg. B. cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetyl methylammonium chloride may be included.
  • the quaternized protein hydrolyzates are further cationic surfactants which can be used according to the invention.
  • Thickeners such as agar agar, guar gum, alginates and xanthan gum, structurants such as glucose and maleic acid,
  • Protein hydrolyzates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, as well as their condensation products with fatty acids, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, GTycerin and DiethyTengTykoT, dyes,
  • Anti-dandruff agents such as Piroctone OTamine and zinc Omadine, substances for adjusting the pH such as citric acid / sodium citrate buffer,
  • Active ingredients such as PanthenoT, ATTantoin, PyrroTidoncarboxylic acids, plant extracts and vitamins, light protection itteT,
  • Consistency enhancers such as sugar esters, PoTyolester or PolyolaTkylether, fats and waxes such as walrus, beeswax, montan wax, paraffins and fatty alcohols
  • Superfatting agents such as polyethoxylated lanolin derivatives, lecithin derivatives and fatty acid alkanolamides, complexing agents such as EDTA, NTA and phosphonic acids,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and also primary, secondary and tertiary phosphates, opacifiers such as latex,
  • Pearlescent agents such as ethylene glycol mono- and distearate, blowing agents such as propane-butane mixtures, N2O, dimethyl ether and air, and antioxidants.
  • the fixing agents according to the invention can be formulated as a cream, gel or liquid. It may be preferred to prepare the preparations in the form of Foam aerosols to assemble, which with a liquefied gas such.
  • the corrugating agents contain the usual mercaptans for this as a compulsory component as keratin-reducing substances.
  • Such compounds are, for example, thioglycolic acid, thiolic acid, 3-mercaptopropionic acid and their salts and esters, cysteamine, cysteine, multicolored salts and alkali salts of sulfurous acid.
  • the alkali metal or ammonium salts of thioglycolic acid and / or thiolic acid and the free acids are particularly suitable. These can be used in the keratin-reducing preparations of the first stage of the hair shaping process according to the invention in a concentration of 0.5 to 1.0 mol / kg at a pH of 6.5 to 10.
  • the exposure time for the keratin-reducing preparation is generally 20 to 40 minutes, the thickness of the hair to be treated, the desired degree of deformation, the size of the mechanical shaping aid used (hair curler) and the type of keratin reducing agent being further influencing variables .
  • the active substance combinations according to the invention are contained in the fixative.
  • the fixative contains the active compound combinations according to the invention and the corrugating agent likewise contains an alkyl glycoside according to formula (I).
  • Alkyl glycoside 1 2.0%
  • Fatty amine derivative with betaine structure (approx. 30% active substance
  • CTFA name Coco-Betaine (HENKEL) 2) Cream permanent wave:
  • alkyl glycoside 1 1.5% thioglycolic acid 8.0% cocoamidobetaine 1.0% ammonia (25%) 6.4% ammonium carbonate 3.0%
  • Alkyl glycoside 2 2.0%
  • Alkyl glycoside 1 2.0%
  • Gafquat R 755 2.5%
  • N-coconut alkyl aminopropionate 1.0%

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Abstract

The patent relates to a permanent waving process for hair in which the hair is treated before and/or after mechanical waving with an aqueous preparation of a keratin-reducing substance, rinsed after a period during which it is left to act, fixed with a second aqueous preparation of an oxiding agent and again rinsed after a period of action. The aqueous preparation of oxiding agent keratin reducing substance contains an alkyl glycoside of general formula (I): RO-(Z)x in which R is an alkyl residue with 6 to 22 carbon atoms, Z is a mono or oligosaccharide and its degree of oligomerisation x for a number from 1.1 to 5, or its addition compound with 1 to 10 molecules of ethylene oxide and/or propylene oxide, in combination with a surface-active compound A selected from among the non-ionogenic, hybrid ionic and amphoteric tensides and/or a polymeric compound B, with the provisio that when the polymeric compound B is a cationic polymer, it is selected from among quaternised cellulose ethers, polysiloxanes with quaternary groups, dimethyl diallyl ammonium chloride polymers and copolymers, dimethyl amino-ethyl methacrylate vinyl pyrrolidone copolymers quaternised with diethyl sulphate and vinyl pyrrolidone-methoimidazolineium chloride copolymers. The use of this combination of agents improved the properties of the permanently waved hair while reducing the stress on the scalp.

Description

"Verfahren zur dauerhaften Verformung von Haaren" "Process for permanent shaping of hair"

Die Erfindung betrifft ein Verfahren zur dauerhaften Haarverformung durch reduktive Spaltung und erneute oxidative Knüpfung von Disulfidbindungen des Haarkeratins.The invention relates to a method for permanent hair shaping by reductive splitting and renewed oxidative knotting of disulfide bonds in hair keratin.

Die dauerhafte Haarverformung wird nach den bekannten Dauerwe11-Verfahren in der Weise durchgeführt, daß man das Haar mechanisch verformt und die Verformung z. B. durch Aufwickeln auf Haarwickler oder Papilloten fest¬ legt. Vor und/oder nach dieser Verformung behandelt man das Haar mit der wäßrigen Zubereitung einer keratinreduzierenden Substanz und spült nach einer Einwirkungszeit mit Wasser oder einer wäßrigen Lösung. In einem zweiten Schritt behandelt man dann das Haar mit der wäßrigen Zubereitung eines Oxidationsmittels. Nach einer Einwirkungszeit wird auch dieses aus dem Haar ausgespült und das Haar von den mechanischen Verformungshilfs¬ mitteln (Wickler, Papilloten) befreit.The permanent hair shaping is carried out according to the known Dauerwe11 method in such a way that the hair is mechanically deformed and the deformation z. B. fix¬ by winding on hair rollers or papillots. Before and / or after this shaping, the hair is treated with the aqueous preparation of a keratin-reducing substance and rinsed with water or an aqueous solution after an exposure time. In a second step, the hair is then treated with the aqueous preparation of an oxidizing agent. After an exposure time, this is also rinsed out of the hair and the hair is freed from the mechanical deformation aids (curlers, papillots).

Die wäßrige Zubereitung des Keratinreduktionsmittels ist üblicherweise alkalisch eingestellt, damit das Haar quillt und auf diese Weise ein tie¬ fes Eindringen der keratinreduzierenden Substanz in das Haar ermöglicht wird. Die keratinreduzierende Substanz spaltet einen Teil der Disulfid- Bindungen des Keratins zu -SH-Gruppen, so daß es zu einer Lockerung der PeptidVernetzung und infolge der Spannung des Haares durch die mechanische Verformung zu einer Neuorientierung des Keratingefüges kommt. Unter dem Einfluß des Oxidationsmittels werden erneut Disulfid-Bindungen geknüpft, und auf diese Weise wird das Keratingefüge in der vorgegebenen Verformung neu fixiert.The aqueous preparation of the keratin-reducing agent is usually made alkaline, so that the hair swells and in this way a deep penetration of the keratin-reducing substance into the hair is made possible. The keratin-reducing substance cleaves a part of the disulfide bonds of the keratin to -SH groups, so that the peptide cross-linking is loosened and, due to the tension in the hair due to the mechanical deformation, the keratin structure is reoriented. Under the influence of the oxidizing agent, disulfide bonds are again formed, and in this way the keratin structure is re-fixed in the predetermined deformation.

Eine negative Begleiterscheinung der so durchgeführten Dauerwellung des Haares ist aber regelmäßig ein Verspröden und Stumpfwerden der Haare. Weiterhin werden in vielen Fällen auch andere Eigenschaften wie Naß- und Trockenkämmbarkeit, Griff, Geschmeidigkeit, Weichheit, Glanz und Reißfe¬ stigkeit in ungewünschter Weise beeinflußt. Schließlich kann die Anwendung von Dauerwellpräparaten insbesondere bei Personen mit empfindlicher Kopf¬ haut zu einer unerwünschten, erhöhten Hautbelastung führen.A negative side effect of the permanent waving of the hair that is carried out in this way is, however, regularly embrittlement and dulling of the hair. Furthermore, in many cases, other properties such as wet and dry combability, grip, smoothness, softness, gloss and tear resistance are also undesirably influenced. Finally, the application permanent wave preparations, especially in people with sensitive scalp, lead to an undesirable, increased skin stress.

Es hat daher in der Vergangenheit nicht an Versuchen gefehlt, hier für Abh lfe zu sorgen.There has been no shortage of attempts to remedy this in the past.

Eine entsprechende Modifizierung der reduzierenden Lösung führt zu in der Regel nicht befriedigenden Welleistungen. Die Zugabe bekannter Zusätze wie Strukturanten, Polymere, Filmbildner und vernetzende Harze kann die Schä¬ digung des Haares zwar verringern; jedoch bleibt das Haar in seiner Struktur mehr oder weniger geschwächt.A corresponding modification of the reducing solution generally leads to unsatisfactory wave outputs. The addition of known additives such as structurants, polymers, film formers and crosslinking resins can indeed reduce the damage to the hair; however, the structure of the hair remains more or less weakened.

Weiterhin ist aus der DE-PS 4109365 bekannt, für Dauerwe11verfahren Zu¬ bereitungen mit Alkylpolyglykosiden zu verwenden. Der Druckschrift ist jedoch keinerlei Hinweis auf bestimmte Wirkungen dieser Komponente zu entnehmen.Furthermore, it is known from DE-PS 4109365 to use preparations with alkyl polyglycosides for long-term processes. However, there is no indication in the publication of certain effects of this component.

Schließlich wird auch in der DE-OS 41 07 313 die Verwendung von Alkylpolyglykosiden in Zubereitungen zur Verformung von menschlichen Haaren beschrieben.Finally, DE-OS 41 07 313 describes the use of alkyl polyglycosides in preparations for shaping human hair.

Es bestand daher weiterhin die Aufgabe, ein Verfahren der dauerhaften Haarverformung zu finden, bei welchem die genannten unerwünschten Neben¬ wirkungen weiter reduziert oder ganz ausgeschlossen werden.There was therefore still the task of finding a method of permanent hair shaping in which the undesired side effects mentioned are further reduced or eliminated entirely.

Es wurde nun überraschenderweise gefunden, daß eine wesentliche Verbesse¬ rung der Eigenschaften dauergewellter Haare bei geringerer Belastung der Kopfhaut dadurch erreicht wird, daß den während des WellVerfahrens einge¬ setzten Mitteln Kombinationen spezieller Verbindungen zugesetzt werden.It has now surprisingly been found that a significant improvement in the properties of permed hair with less stress on the scalp is achieved by adding combinations of special compounds to the agents used during the waving process.

Gegenstand der Erfindung ist daher ein Verfahren zur dauerhaften Verfor¬ mung von Haaren, bei welchem man das Haar vor und/oder nach einer mecha¬ nischen Verformung mit der wäßrigen Zubereitung einer keratinreduzierenden Substanz behandelt, nach einer Einwirkungszeit spült, dann mit einer wä߬ rigen Zubereitung eines Oxidationsmittels fixiert und ebenfalls nach einer Einwirkungszeit spült, dadurch gekennzeichnet, daß in der wäßrigen Zubereitung des Oxidationsmittels ein Alkylglykosid der allgemeinen Formel (I),The invention therefore relates to a process for permanent shaping of hair, in which the hair is treated with the aqueous preparation of a keratin-reducing substance before and / or after a mechanical shaping, rinsed after an exposure time, then with an aqueous one Preparation of an oxidizing agent fixed and also rinsed after an exposure time, characterized in that in the aqueous Preparation of the oxidizing agent an alkyl glycoside of the general formula (I),

0-(Z)x (I)0- (Z) x (I)

in der R steht für einen Alkylrest mit 6 bis 22 Kohlenstoffatomen, Z für ein Mono- oder Oligosaccharid und dessen Oligomerisationsgrad x für eine Zahl von 1,1 bis 5, oder dessen Anlagerungsprodukt mit 1 bis 10 Molekülen Ethylenoxid und/oder Propylenoxid in Kombination mit einer oberflächen¬ aktiven Verbindung A, ausgewählt unter den nichtionogenen, zwitterio¬ nischen und amphoteren Tensiden, und/oder einer polymeren Verbindung B, wobei für den Fall, daß die polymere Verbindung B ein Kationpolymer ist, diese ausgewählt ist ausin which R stands for an alkyl radical with 6 to 22 carbon atoms, Z for a mono- or oligosaccharide and its degree of oligomerization x for a number from 1.1 to 5, or its adduct with 1 to 10 molecules of ethylene oxide and / or propylene oxide in combination with a surface-active compound A, selected from the non-ionic, zwitterionic and amphoteric surfactants, and / or a polymeric compound B, where in the event that the polymeric compound B is a cation polymer, this is selected from

- quaternierten Celluloseethern, Polysiloxanen mit quaternären Gruppen,quaternized cellulose ethers, polysiloxanes with quaternary groups,

- Dimethyldiallylammoniumchlorid-Polymeren und -Copolymeren,- dimethyldiallylammonium chloride polymers and copolymers,

- mit Diethylsulfat quaternierten Dimethylaminoethylmethacrylat-Vinyl- pyrrolidon-Copolymeren, und- Dimethylaminoethyl methacrylate-vinyl pyrrolidone copolymers quaternized with diethyl sulfate, and

- Vinylpyrrolidon-Methoimidazoliniumchlorid-Copolymeren.- Vinyl pyrrolidone-methoimidazolinium chloride copolymers.

Im weiteren wird die wäßrige Zubereitung der keratinreduzierenden Substanz als Wellmittel und die wäßrige Zubereitung des Oxidationsmittels als Fi¬ xiermittel bezeichnet.The aqueous preparation of the keratin-reducing substance is referred to below as the waving agent and the aqueous preparation of the oxidizing agent is referred to as the fixing agent.

Die erfindungsgemäß verwendbaren Alkylglykoside der Formel (I) sind durch die folgenden Parameter gekennzeichnet.The alkyl glycosides of the formula (I) which can be used according to the invention are characterized by the following parameters.

Der Alkylrest R enthält 6 bis 22 Kohlenstoffatome und kann sowohl linear als auch verzweigt sein. Bevorzugt sind primäre lineare und in 2-Stellung methylverzweigte aliphatische Reste. Die erfindungsgemäß verwendbaren Al¬ kylglykoside können lediglich einen bestimmten Alkylrest R enthalten. Üb¬ licherweise werden diese Verbindungen aber ausgehend von natürlichen Fetten und Ölen oder Mineralölen hergestellt. In diesem Fall liegen als Alkylreste R Mischungen entsprechend den Ausgangsverbindungen bzw. ent¬ sprechend der jeweiligen Aufarbeitung dieser Verbindungen vor. Ausgehend von natürlichen Fetten und Ölen weisen die Alkylreste ganz überwiegend eine geradzahlige Anzahl von Kohlenstoffatomen auf. Solche Alkylreste sind beispielsweise 1-Octyl, 1-Decyl, 1-Lauryl, 1-Myristyl, 1-Cetyl und 1- Stearyl. Besonders bevorzugt sind 1-Octyl, 1-Decyl, 1-Lauryl, 1-Myristyl. Bei Verwendung sogenannter 'Oxo-Alkohole" überwiegen Verbindungen mit ei¬ ner ungeraden Anzahl von Kohlenstoffatomen in der Alkyl ette.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. The alkyl glycosides which can be used according to the invention can contain only one specific alkyl radical R. Usually, however, these compounds are produced starting from natural fats and oils or mineral oils. In this case, the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the particular workup of these compounds. Starting from natural fats and oils, the alkyl residues predominantly have an even number of carbon atoms. Such alkyl residues 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', compounds with an odd number of carbon atoms in the alkyl chain predominate.

Besonders bevorzugt sind solche Alkylglykoside, bei denen R entweder im wesentlichen aus CQ- und Cio-Alkylgruppen oder im wesentlichen aus C12- und ( 4-ATkylgruppen besteht.Alkyl glycosides in which R consists either essentially of CQ and Cio-alkyl groups or essentially of C12 and (4-ATkyl groups) are particularly preferred.

Als Zuckerbaustein Z können beliebige Mono- oder Oligosaccharide einge¬ setzt werden. Üblicherweise werden Zucker mit 5 bzw. 6 Kohlenstoffatomen sowie die entsprechenden Oligosaccharide eingesetzt. Solche Zucker sind beispielsweise Glucose, Fructose, Galactose, Arabinose, Ribose, Xylose, Lyxose, AIlose, Altrose, Mannose, Gulose, Idose, Talose und Sucrose. Be¬ vorzugte Zuckerbausteine sind Glucose, Fructose, Galactose, Arabinose und Sucrose; Glucose ist besonders bevorzugt.Any mono- or oligosaccharides can be used as sugar building block Z. Sugar with 5 or 6 carbon atoms and the corresponding oligosaccharides are usually used. Examples of such sugars are glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allos, altrose, mannose, gulose, idose, talose and sucrose. Preferred sugar components are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.

Die erfindungsgemäßen Alkylglykoside enthalten im Schnitt 1,1 bis 5 Zuk- kereinheiten. Alkylglykoside mit x-Werten von 1,3 bis 2 sind bevorzugt. Ganz besonders bevorzugt sind Alkylglykoside, bei denen x 1,4 bis 1,6 be¬ trägt.The alkyl glycosides according to the invention contain an average of 1.1 to 5 sugar units. Alkyl glycosides with x values from 1.3 to 2 are preferred. Alkyl glycosides in which x is 1.4 to 1.6 are very particularly preferred.

Auch die alkoxylierten Homologen der genannten Alkylglykoside können er¬ findungsgemäß eingesetzt werden. Diese Homologen können durchschnittlich bis zu 10 Ethylenoxid- und/oder Propylenoxideinheiten pro Alkylglykosid- einheit enthalten. Auch diese Produkte stellen üblicherweise keine ein¬ heitlichen Verbindungen dar, sondern weisen in Abhängigkeit von dem ge¬ wählten Ethoxylierungsverfahren eine_ entsprechende Homologenverteilung auf. Solche alkoxylierten Verbindungen können beispielsweise dadurch er¬ halten werden, daß zur Synthese der Alkylglykoside ethoxylierte Fettal¬ kohole verwendet werden.The alkoxylated homologs of the alkyl glycosides mentioned can also be used according to the invention. These homologues can contain an average of up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit. These products also usually do not represent uniform compounds, but instead have a corresponding homolog distribution depending on the selected ethoxylation process. Such alkoxylated compounds can be obtained, for example, by using ethoxylated fatty alcohols for the synthesis of the alkyl glycosides.

Das Alkylglykosid ist im Fixiermittel bevorzugt in einer Menge von 0,1 bis 40 Gew.-%, jeweils bezogen auf das gesamte Fixiermittel, enthalten. Mengen von 0,5 bis 20 Gew.-% sind besonders bevorzugt. Eine weitere erfindungsgemäße Wirkstoffkomponente sind die oberflächen¬ aktiven Verbindungen A, die ausgewählt sind aus der Gruppe der nichtiono- genen, zwitterionischen und amphoteren Tenside.The alkyl glycoside is preferably contained in the fixing agent in an amount of 0.1 to 40% by weight, based in each case on the total fixing agent. Amounts of 0.5 to 20% by weight are particularly preferred. Another active ingredient component according to the invention are the surface-active compounds A, which are selected from the group of nonionic, zwitterionic and amphoteric surfactants.

Nichtionogene Tenside enthalten als hydrophile Gruppe z. B. eine Polyol- gruppe, eine Polyalkylenglykolethergruppe oder eine Kombination aus Poly- ol- und Polyglykolethergruppe. Solche Verbindungen sind beispielsweiseNon-ionic surfactants contain z. B. a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group. Such connections are, for example

Anlagerungsprodukte von 2 bis 30 Mol Ethylenoxid und/oder 0 bis 5 Mol Propylenoxid an lineare Fettalkohole mit 8 bis 22 C-Atomen, an Fett¬ säuren mit 12 bis 22 C-Atomen und an Alkylphenole mit 8 bis 15 C-Ato¬ men in der Alkylgruppe,Addition products of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 carbon atoms, with fatty acids with 12 to 22 carbon atoms and with alkylphenols with 8 to 15 carbon atoms in the alkyl group,

Ci2-C22~':ettsäuremono- und -diester von Anlagerungsprodukten von 1 bis 30 Mol Ethylenoxid an Glycerin,Ci2-C22 ~ ' : Ettsäuremono- and diesters of adducts of 1 to 30 moles of ethylene oxide with glycerol,

Glycerinmono- und -diester und Sorbitanmono- und -diester von gesät¬ tigten und ungesättigten C8-C22-fre't'tsäuren und deren Ethylenoxidan- lagerungsprodukte undGlycerol monoesters and diesters and sorbitan monoesters and diesters of saturated and unsaturated C8-C22 free acids and their ethylene oxide addition products and

Anlagerungsprodukte von 5 bis 60 Mol Ethylenoxid an Rizinusöl und ge¬ härtetes Rizinusöl.Addition products of 5 to 60 moles of ethylene oxide with castor oil and hardened castor oil.

Als zwitterionische Tenside werden solche oberflächenaktiven Verbindungen bezeichnet, die im Molekül mindestens eine quartäre Ammoniumgruppe und mindestens eine -COθ(")- oder -Sθ3(")-Gruppe tragen. Besonders geeignete zwitterionische Tenside sind die sogenannten Betaine wie die N-Alkyl-N,N- dimethylam onium-glycinate, beispielsweise das KokosaIkyl-dimethylarnmo- niumglycinat, N-Acyl-aminopropyl-N,N-dimethylammoniumglycinate, bei¬ spielsweise das Kokosacylaminopropyl-dimethylammoniumglycinat, und 2- Alkyl-3-carboxymethyl-3-hydroxyethyl-imidazoline mit jeweils 8 bis 18 C- Atomen in der Alkyl- oder Acylgruppe sowie das Kokosacylaminoethylhy- droxyethylcarboxymethylglycinat. Ein bevorzugtes zwitterionisches Tensid ist das unter der CTFA-Bezeichnung Cocamidopropyl Betaine bekannte Fett- säureamid-Derivat.Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one -COθ (") - or -Sθ3 (") - 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 coconut alkyl-dimethylammonium glycinate, N-acylaminopropyl-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 cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate. A preferred zwitterionic surfactant is the fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine.

Unter ampholytisehen Tensiden werden solche oberflächenaktiven Verbindun¬ gen verstanden, die außer einer Cß-Ciß-Alkyl- oder -Acylgruppe im Molekül mindestens eine freie Aminogruppe und mindestens eine -C00H- oder -SO3H- Gruppe enthalten und zur Ausbildung innerer Salze befähigt sind. Beispiele für geeignete ampholytische Tenside sind N-Alkylglycine, N-Alkylpropion- säuren, N-Alkylaminobuttersäuren, N-Alkyliminodipropionsäuren, N-Hydroxy- ethyl-N-alkylamidopropylglycine, N-Alkyltaurine, N-Alkylsarcosine, 2- Al yTaminopropionsäuren und Alkylaminoessigsäuren mit jeweils etwa 8 bis 18 C-Atomen in der ATkylgruppe. Besonders bevorzugte ampholytische Tenside sind das N-Kokosalkylaminopropionat, das Kokosacylaminoethylaminopropionat und das Ci2-i8-AcyTsarcosin.Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a C 6 -C 16 -alkyl or acyl group, contain at least one free amino group and at least one -C00H or -SO3H group in the molecule and are capable of forming internal salts. Examples suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-Al ytaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the ATkyl group. Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2-i8-AcyTsarcosine.

Bei den aTs Tenside eingesetzten Verbindungen mit ATkyTgruppen kann es sich jeweils um einheitliche Substanzen handeln. Es ist jedoch in der Re¬ gel bevorzugt, bei der Herstellung dieser Stoffe von nativen pflanzlichen oder tierischen Rohstoffen auszugehen, so daß man Substanzgemische mit unterschiedlichen, vom jeweiligen Rohstoff abhängigen Alkylkettenlängen erhält.The compounds with ATkyT groups used in the aTs surfactants can each be uniform substances. However, it is generally preferred to use native 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.

Bei den Tensiden, die Anlagerungsprodukte von Ethylen- und/oder Propylen- oxid an FettaTkohoTe oder Derivate dieser AnTagerungsprodukte darsteTlen, können sowohl Produkte mit einer "normalen" Homologenverteilung als auch solche mit einer eingeengten HomologenverteiTung verwendet werden. Unter "normaler" Homologenverte lung werden dabei Mischungen von HomoTogen ver¬ standen, die man bei der Umsetzung von FettaTkohoT und ATkyTenoxid unter Verwendung von ATkaTimetaTTen, ATkaTi etaTThydroxiden oder ATkali etallalkohoTaten aTs KataTysatoren erhält. Eingeengte Homologenverteilungen werden dagegen erhalten, wenn beispielsweise Hydrotalcite, Erdalkalimetallsalze von Ethercarbonsäuren, ErdaTkaTi e- talloxide, -hydroxide oder -aTkohoTate als Katalysatoren verwendet werden. Die Verwendung von Produkten mit eingeengter Homologenverteilung kann be¬ vorzugt sein.In the case of the surfactants, which are addition products of ethylene and / or propylene oxide onto fatty acids or derivatives of these addition products, both products with a "normal" homolog distribution and those with a narrow homolog distribution can be used. “Normal” homolog distribution means mixtures of HomoTogen which are obtained in the implementation of FettaTkohoT and ATkyTenoxid using ATkaTimetaTTen, ATkaTi etaTThydroxiden or ATkali metal alcoholate as Catalytic converters. By contrast, narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alkaline carbonates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.

Vorzugsweise enthalten die erfindungsgemäßen FixiermitteT die ober- fTächenaktiven Verbindungen A in Mengen von 0,5 bis 10 Gew.-%, bezogen auf das gesamte FixiermitteT.The fixing agents according to the invention preferably contain the surface-active compounds A in amounts of 0.5 to 10% by weight, based on the total fixing agent.

Eine weitere Komponente in erfindungsgemäßen Wirkstoffkombinationen sind polymere Verbindungen B. Die erfindungsgemäß verwendeten kationischen Polymeren sind ausgewählt aus der Gruppe, umfassend quaternisierte Celluloseether, Polysiloxane mit quaternären Gruppen,Another component in active ingredient combinations according to the invention are polymeric compounds B. The cationic polymers used according to the invention are selected from the group comprising quaternized cellulose ethers, polysiloxanes with quaternary groups,

Dimethyldiallylammoniumchlorid-Polymere und -Copolymere, wie z. B.Dimethyldiallylammonium chloride polymers and copolymers, such as. B.

Acrylamid-Dimethyldiallylammoniumchlorid-Copolymere, mit Diethylsulfat quatemierte Dimethylaminoethylmethacrylat-Vinyl- pyrrolidon-Copoly ere, undAcrylamide-dimethyldiallylammonium chloride copolymers, dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate, and

Vinylpyrrolidon-Methoimidazoliniumchlorid-Copolymere.Vinyl pyrrolidone-methoimidazolinium chloride copolymers.

Copolymere von Acrylamid und Dimethyldiallylammoniumchlorid, die unter der Bezeichnung MerquatR550 im Handel erhältlich sind, sind besonders bevor¬ zugte kationische Polymere.Copolymers of acrylamide and dimethyldiallylammonium chloride, which are commercially available under the name Merquat R 550, are particularly preferred cationic polymers.

Unter zwitterionischen Polymerisaten im Sinne der Erfindung werden solche Polymerisate verstanden, die sowohl kationische als auch anionische Grup¬ pen oder leicht in diese überführbare Gruppen enthalten.In the context of the invention, zwitterionic polymers are understood to mean those polymers which contain both cationic and anionic groups or groups which can easily be converted into them.

Kationische Gruppen sind beispielsweise Gruppen, die mindestens eine Am¬ monium- oder Phosphonium-Einheit enthalten; Beispiele für eine leicht in eine kationische Gruppe überführbare Einheit sind primäre, sekundäre und insbesondere tertiäre Amino-Gruppen. Ammoniumgruppen sind bevorzugte kat¬ ionische Gruppen.Cationic groups are, for example, groups which contain at least one ammonium or phosphonium unit; Examples of a unit which can easily be converted into a cationic group are primary, secondary and in particular tertiary amino groups. Ammonium groups are preferred cationic groups.

Als anionische Gruppen kommen beispielsweise Carbon-, Sulfon- und Phos¬ phorsäuregruppen in freier Form oder in Salzform in Betracht. Die Carbon¬ säuregruppen und ihre Alkali-, Erdalkali-, Aluminium- und Ammoniumsalze sind bevorzugte anionische Gruppen.Suitable anionic groups are, for example, carbon, sulfone and phosphoric acid groups in free form or in salt form. The carboxylic acid groups and their alkali, alkaline earth, aluminum and ammonium salts are preferred anionic groups.

Die erfindungsgemäß eingesetzten zwitterionischen Polymerisate können aus Monomeren aufgebaut sein, die sowohl kationische als auch anionische Gruppen enthalten. Die Polymerisate können in diesem Fall aus einem ein¬ zigen Monomertyp bestehen. Es ist aber auch möglich, Copolymere aus den genannten Monomeren und weiteren nichtionischen Monomeren einzusetzen. Solche nichtionischen Monomere können beispielsweise Ester und A ide auf Vinylbasis, wie Methylacrylat, Ethylacrylat, Methylmethacrylat, Ethylmethacrylat, Hydroxypropylmethacrylat, Acrylamid, Vinylpyrrolidon und Vinylalkohol sein. Bevorzugt enthalten diese Copoly erisate mindestens 20 %, insbesondere mindestens 50 %, an ionischen Monomeren.The zwitterionic polymers used according to the invention can be constructed from monomers which contain both cationic and anionic groups. In this case, the polymers can consist of a single type of monomer. However, it is also possible to use copolymers of the monomers mentioned and other nonionic monomers. Such nonionic monomers can be, for example, vinyl-based esters and vinyls, such as methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, hydroxypropyl methacrylate, acrylamide, vinyl pyrrolidone and Be ethanol. These copolymers preferably contain at least 20%, in particular at least 50%, of ionic monomers.

Im Rahmen der Erfindung bevorzugte Polymerisate sind aus mindestens 2 io¬ nischen Monomeren, einem kationischen und einem anionischen Monomer, auf¬ gebaut. Kationische und anionische Monomere können dabei in einem Molver¬ hältnis 1:1 vorliegen. Es ist jedoch bevorzugt, einen Monomertyp, insbe¬ sondere die kationischen Monomeren, im Überschuß einzusetzen. In der Regel werden kationische und anionische Monomere im Verhältnis 95:5 bis 60:40 eingesetzt. Weiterhin können die Polymeren nichtionische Monomere der oben genannten Art in Mengen bis zu 50 Mol-%, insbesondere bis zu 20 Mol-% enthalten.Polymers preferred in the context of the invention are built up from at least 2 ionic monomers, a cationic and an anionic monomer. Cationic and anionic monomers can be present in a 1: 1 molar ratio. However, it is preferred to use an excess of one type of monomer, in particular the cationic monomers. As a rule, cationic and anionic monomers are used in a ratio of 95: 5 to 60:40. The polymers can furthermore contain nonionic monomers of the type mentioned above in amounts of up to 50 mol%, in particular up to 20 mol%.

Unter den zwitterionischen Polymeren sind erfindungsgemäß bevorzugt die in der DE-A-39 29 973 beschriebenen zwitterionischen Polymerisate, die sich im wesentlichen zusammensetzen ausAccording to the invention, preferred zwitterionic polymers are the zwitterionic polymers described in DE-A-39 29 973, which essentially consist of one another

Monomeren mit quartären Ammoniumgruppen der allgemeinen Formel (II), Rl-CH=CR2-C0-Z-(CnH2n)-N(+)R3R4R5 Ä(") (II) in der R* und R2 unabhängig voneinander stehen für Wasserstoff oder eine Methylgruppe und R3, 4 und R^ unabhängig voneinander für Alkylgruppen mit 1 bis 4 Kohlenstoff-Atomen, Z eine NH-Gruppe oder ein Sauerstoffatom, n eine ganze Zahl von 2 bis 5 und Ä(~) das Anion einer organischen oder an¬ organischen Säure ist und monomeren Carbonsäuren der aTTge einen Formel (III), R6-CH=CR7-C00H (III) in denen R*> und R? unabhängig voneinander Wasserstoff oder MethyTgruppen sind, oder ATkaTi-, ErdaTkali-, Aluminium- oder AmmoniumsaTzen dieser Säuren.Monomers with quaternary ammonium groups of the general formula (II), Rl-CH = CR 2 -C0-Z- (C n H 2n ) -N ( + ) R 3 R 4 R 5 Ä ( " ) (II) in the R * and R 2 independently represent hydrogen or a methyl group and R 3 , 4 and R ^ independently of one another alkyl groups having 1 to 4 carbon atoms, Z an NH group or an oxygen atom, n an integer from 2 to 5 and Ä (~) is the anion of an organic or inorganic acid and monomeric carboxylic acids of aTTge have a formula (III), R6-CH = CR 7 -C00H (III) in which R *> and R? are independently of one another hydrogen or methyl groups, or ATkaTi, ErdaTkali, aluminum or ammonium etching of these acids.

Das AcryTamidopropyl-trimethyTammoniumchTorid ist ein ganz besonders be¬ vorzugtes Monomer der FormeT (II).AcryTamidopropyltrimethyTammoniumchTorid is a very particularly preferred monomer of FormeT (II).

Monomere Carbonsäuren der aTlgemeinen FormeT (III) sind AcryTsäure, Meth¬ acryTsäure, Crotonsäure und 2-MethyT-crotonsäure. Bevorzugt werden Acryl- oder MethacryTsäure, insbesondere Acrylsäure, eingesetzt. Bevorzugt eingesetzte Salze dieser Carbonsäuren sind das Lithium-, Natrium-, Kali¬ um-, Magnesium-, Calcium- und Aluminiumsalz. Besonders bevorzugt ist das Natriumsalz. Weiterhin können die Ammoniumsalze eingesetzt werden, bei denen das Ammoniumion ein bis drei Alkylgruppen mit 1-4 Kohlenstoffatomen oder Hydroxyalkylgruppen mit 2-4 Kohlenstoffatomen als Substituenten haben kann. Salze mit unsubstituierten Ammoniumionen und Triethanolammoniumionen sind bevorzugt.Monomeric carboxylic acids of the general form (III) are acrylic acid, methacrylic acid, crotonic acid and 2-methyl-crotonic acid. Acrylic or methacrylic acid, in particular acrylic acid, are preferably used. Prefers Salts of these carboxylic acids used are the lithium, sodium, potassium, magnesium, calcium and aluminum salts. The sodium salt is particularly preferred. Furthermore, the ammonium salts can be used in which the ammonium ion can have one to three alkyl groups with 1-4 carbon atoms or hydroxyalkyl groups with 2-4 carbon atoms as substituents. Salts with unsubstituted ammonium ions and triethanolammonium ions are preferred.

Bezüglich der Herstellung dieser zwitterionischen Polymere wird ausdrück¬ lich auf die Offenbarung der DE-A-3929973 Bezug genommen.With regard to the production of these zwitterionic polymers, reference is expressly made to the disclosure of DE-A-3929973.

Ebenfalls bevorzugte zwitterionische Polymerisate sind Polysiloxan-Poly- organobetain-Copolymere.Polysiloxane-polyorganobetaine copolymers are also preferred zwitterionic polymers.

Geeignete amphotere Polymere sind beispielsweise Octylacrylamid/Methyl- methacrylat/tert.Butylaminoethylmethacrylat/2-Hydroxypropylmethacrylat- Copolymere.Suitable amphoteric polymers are, for example, octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers.

Erfindungsgemäß geeignete anionische Polymere sind beispielsweise Vinylacetat/Crotonsäure-Copolymere, Vinylpyrrolidon/Vinylacrylat-Copolymere, Vinylacetat/Butylmaleat/Isobornylacrylat-Copolymere, Methylvinylether/Maleinsäureanhydrid-Copolymere und deren Ester sowie unvernetzte und mit Polyolen vernetzte Polyacrylsäuren.Anionic polymers suitable according to the invention are, for example, vinyl acetate / crotonic acid copolymers, vinyl pyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and their esters as well as uncrosslinked and polyols crosslinked polyacrylic acids.

Geeignete nichtionogene Polymere sind beispielsweise PolyvinylpyrrolidonSuitable nonionic polymers are, for example, polyvinyl pyrrolidone

Vinylpyrrolidon/Vinylacetat-Copolymere,Vinyl pyrrolidone / vinyl acetate copolymers,

Vinylpyrrolidon/Dimethylaminoethylmethacrylat/Vinylcaprolactam-Ter- polymere sowie gegebenfalls derivatisierte Celluloseether.Vinyl pyrrolidone / dimethylaminoethyl methacrylate / vinyl caprolactam terpolymers and, if necessary, derivatized cellulose ethers.

Besonders gute Ergebnisse wurden gefunden, wenn es sich bei den polymeren Verbindungen um kationische, zwitterionische oder amphotere Polymere han¬ delt. Die Verwendung der zwitterionischen und a photeren Polymeren ist ganz besonders bevorzugt. Die poly eren Verbindungen B sind in den erfindungsgemäßen Fixiermitteln vorzugsweise in Mengen von 0,01 bis 5 Gew.-%, bezogen auf das gesamte FixiermitteT, enthaTten. Konzentrationen von 0,01 bis 2 Gew.-% sind be¬ sonders bevorzugt.Particularly good results have been found when the polymeric compounds are cationic, zwitterionic or amphoteric polymers. The use of the zwitterionic and a photomeric polymers is very particularly preferred. The polymeric compounds B are contained in the fixing agents according to the invention preferably in amounts of 0.01 to 5% by weight, based on the total fixing agent. Concentrations of 0.01 to 2% by weight are particularly preferred.

Neben den ATkyTgTykosiden, den oberflächenaktiven Verbindungen A und den polymeren Verbindungen B können die erfindungsgemäßen Zubereitungen alle in Haarbehandlungsmitteln üblichen Bestandteile enthalten. Dabei hängt es von der Art des Mittels ab, weTche der im foTgenden genannten Bestandteile im Mittel enthaTten sind.In addition to the ATkyTg tycosides, the surface-active compounds A and the polymeric compounds B, the preparations according to the invention can contain all the constituents customary in hair treatment compositions. It depends on the type of agent, which of the components mentioned in the following are included in the agent.

Zwingender Bestandteil des Fixiermittels sind Oxidationsmittel, z. B. Wasserstoffperoxid und die zur Stabilisierung wäßriger Wasserstoffper- oxidzubereitungen üblichen Stabilisatoren. Der pH-Wert solcher wäßriger H2θ2-Zubereitungen, die etwa 0,5 bis 3,0 Gew.-% H2O2 enthalten, liegt be¬ vorzugt bei 2 bis 4; er wird durch anorganische Säuren, bevorzugt Phos¬ phorsäure eingesteht. Weitere bevorzugte OxidationsmitteT sind Natrium- und KaTiumbromat. SoTche Bromate werden in Konzentrationen von 1 bis 10 Gew.-% eingesetzt und der pH-Wert der Lösungen wird auf 4 bis 7 einge¬ stellt.Mandatory component of the fixative are oxidizing agents, e.g. B. hydrogen peroxide and the usual stabilizers for stabilizing aqueous hydrogen peroxide preparations. The pH of such aqueous H2O2 preparations which contain about 0.5 to 3.0% by weight of H2O2 is preferably 2 to 4; it is admitted by inorganic acids, preferably phosphoric acid. Other preferred oxidizing agents are sodium and potassium bromate. Such bromates are used in concentrations of 1 to 10% by weight and the pH of the solutions is adjusted to 4 to 7.

Weiterhin können anionische und kationische Tenside enthalten sein.Anionic and cationic surfactants may also be present.

Als anionische Tenside eignen sich in erfindungsgemäßen Haarbehandlungs- mitteTn alle für die Verwendung am menschlichen Körper geeigneten anioni¬ schen oberflächenaktiven Stoffe. Diese sind gekennzeichnet durch eine wasserlöslich machende, anionische Gruppe wie z. B. eine Carboxylat-, Sulfat-, Sulfonat- oder Phosphat-Gruppe und eine TipophiTe ATkyTgruppe mit etwa 10 bis 22 C-Atomen. Zusätzlich können im Molekül Glykol- oder Poly- glykolether-Gruppen, Ester-, Ether- und Amidgruppen sowie Hydroxylgruppen enthalten sein. Beispiele für geeignete anionische Tenside sind jeweils in Form der Natrium-, KaTium- und Ammonium- sowie der Mono-, Di- und Trialkanolammoniumsalze mit 2 oder 3 C-Atomen in der Alkanolgruppe,Suitable anionic surfactants in hair treatment agents according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a TipophiTe ATkyTgruppe with about 10 to 22 carbon atoms. In addition, the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups. Examples of suitable anionic surfactants are in the form of the sodium, potassium and ammonium salts as well as the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group,

lineare Fettsäure mit 10 bis 22 C-Atomen (Seifen), Ethercarbonsäuren der Formel R-0-(CH2-CH2θ)x-CH2-COOH, in der R eine lineare Alkylgruppe mit 10 bis 22 C-Atomen und x = 0 oder 1 bis 10 ist,linear fatty acid with 10 to 22 carbon atoms (soaps), Ether carboxylic acids of the formula R-0- (CH2-CH2θ) x -CH2-COOH, in which R is a linear alkyl group with 10 to 22 C atoms and x = 0 or 1 to 10,

Acylsarcoside mit 10 bis 18 C-Atomen in der Acylgruppe, Acyltauride mit 10 bis 18 C-Atomen in der Acylgruppe, Acylisethionate mit 10 bis 18 C-Atomen in der Acylgruppe, Sulfobernsteinsäuremono- und dialkylester mit 8 bis 18 C-Atomen in der Alkylgruppe und Sulfobernsteinsäuremono-alkylpolyoxyethylester mit 8 bis 18 C-Atomen in der Alkylgruppe und 1 bis 6 Oxyethylgruppen, lineare Alkansulfonate mit 12 bis 18 C-Atomen, lineare Alpha-Olefinsulfonate mit 12 bis 18 C-Atomen, Alpha-Sulfofettsäuremethylester von Fettsäuren mit 12 bis 18 C-Atomen, Alkylsulfate und Alkylpolyglykolethersulfate der Formel R-0(CH2-CH2θ)x-OSÖ3H, in der R eine bevorzugt lineare Alkylgruppe mit 10 bis 18 C-Atomen und x = 0 oder 1 bis 12 ist, Gemische oberflächenaktiver Hydroxysulfonate gemäß DE-A-3725030, sulfatierten Hydroxyalkylpolyethylen- und/oder Hydroxyalkylen- propylenglykolether gemäß DE-A-3723354Acyl sarcosides with 10 to 18 carbon atoms in the acyl group, acyl taurides with 10 to 18 carbon atoms in the acyl group, acyl isethionates with 10 to 18 carbon atoms in the acyl group, monosulfonic acid and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid mono-alkyl polyoxyethyl esters with 8 to 18 C atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkanesulfonates with 12 to 18 C atoms, linear alpha-olefin sulfonates with 12 to 18 C atoms, alpha-sulfofatty acid methyl esters of fatty acids with 12 to 18 carbon atoms, alkyl sulfates and alkyl polyglycol ether sulfates of the formula R-0 (CH2-CH2θ) x -OSÖ3H, in which R is a preferably linear alkyl group with 10 to 18 carbon atoms and x = 0 or 1 to 12, mixtures of surface-active hydroxysulfonates according to DE-A-3725030, sulfated hydroxyalkyl polyethylene and / or hydroxyalkylene propylene glycol ether according to DE-A-3723354

Sulfonate ungesättigter Fettsäuren mit 12 bis 24 C-Atomen und 1 bis 6 Doppelbindungen gemäß DE-A-3926344,Sulfonates of unsaturated fatty acids with 12 to 24 carbon atoms and 1 to 6 double bonds according to DE-A-3926344,

Ester der Weinsäure und Zitronensäure mit Alkoholen, die Anlagerungs¬ produkte von etwa 2-15 Molekülen Ethylenoxid und/oder Propylenoxid an Fettalkohole mit 8 bis 22 C-Atomen darstellen.Esters of tartaric acid and citric acid with alcohols, which are addition products of about 2-15 molecules of ethylene oxide and / or propylene oxide onto fatty alcohols with 8 to 22 carbon atoms.

Bevorzugte anionische Tenside sind Alkylsulfate, Alkylpolyglykolethersul¬ fate und Ethercarbonsäuren mit 10 bis 18 C-Atomen in der Alkylgruppe und bis zu 12 Glykolethergruppen im Molekül, sowie Sulfobernsteinsäuremono- und -dialkylester mit 8 bis 18 C-Atomen in der Alkylgruppe und Sulfobern- steinsäure ono-aTkyTpolyoxyethylester mit 8 bis 18 C-Atomen in der ATkyT¬ gruppe und 1 bis 6 Oxyethylgruppen.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, and sulfosuccinic acid and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid ono -ATkyTpolyoxyethylester with 8 to 18 carbon atoms in the ATkyT¬ group and 1 to 6 oxyethyl groups.

Als kationische Tenside können in den erfindungsgemäßen Haarbehandlungs¬ mitteln schließlich insbesondere quartäre Ammoniumverbindungen wie Alkyl- trimethylammoniumchloride, Dialkyldimethylammoniumchloride und Trialkyl- methylammoniumchloride, z. B. Cetyltrimethylammoniumchlorid, Stearyltri- methylammoniumchlorid, Distearyldimethylammoniumchlorid, Lauryldimethyl- ammoniumchlorid, Lauryldimethylbenzylammoniumchlorid und Tricetyl- methylammoniumchlorid enthalten sein. Weitere erfindungsgemäß verwendbare kationische Tenside stellen die quaternisierten Proteinhydrolysate dar.Finally, quaternary ammonium compounds such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg. B. cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetyl methylammonium chloride may be included. The quaternized protein hydrolyzates are further cationic surfactants which can be used according to the invention.

Weitere übliche Bestandteile der erfindungsgemäßen wäßrigen Lösungen sind:Other common constituents of the aqueous solutions according to the invention are:

Verdickungsmittel wie Agar-Agar, Guar-Gum, Alginate und Xanthan-Gum, Strukturanten wie Glucose und Maleinsäure,Thickeners such as agar agar, guar gum, alginates and xanthan gum, structurants such as glucose and maleic acid,

Proteinhydrolysate, insbesondere Elastin-, Kollagen-, Keratin-, Milcheiweiß-, Sojaprotein- und WeizenproteinhydroTysate, sowie deren Kondensationsprodukte mit Fettsäuren, ParfümöTe, Dimethylisosorbid und Cyclodextrine,Protein hydrolyzates, in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, as well as their condensation products with fatty acids, perfume oils, dimethyl isosorbide and cyclodextrins,

LösungsVermittler, wie Ethanol, Isopropanol, Ethylenglykol, Propylen- glykol, GTycerin und DiethyTengTykoT, Farbstoffe,Solubilizers, such as ethanol, isopropanol, ethylene glycol, propylene glycol, GTycerin and DiethyTengTykoT, dyes,

Antischuppenwirkstoffe wie Piroctone OTamine und Zink Omadine, Substanzen zur EinsteTTung des pH-Wertes wie Citronensäure/Natrium- citrat-Puffer,Anti-dandruff agents such as Piroctone OTamine and zinc Omadine, substances for adjusting the pH such as citric acid / sodium citrate buffer,

Wirkstoffe wie PanthenoT, ATTantoin, PyrroTidoncarbonsäuren, PfTan- zenextrakte und Vitamine, Lichtschutz itteT,Active ingredients such as PanthenoT, ATTantoin, PyrroTidoncarboxylic acids, plant extracts and vitamins, light protection itteT,

Konsistenzgeber wie Zuckerester, PoTyolester oder PolyolaTkylether, Fette und Wachse, wie Walrat, Bienenwachs, Montanwachs, Paraffine und Fettalkohole,Consistency enhancers such as sugar esters, PoTyolester or PolyolaTkylether, fats and waxes such as walrus, beeswax, montan wax, paraffins and fatty alcohols

Überfettungsmittel wie polyethoxylierte Lanolinderivate, Lecithinderivate und Fettsäurealkanolamide, Komplexb ldner wie EDTA, NTA und Phosphonsäuren,Superfatting agents such as polyethoxylated lanolin derivatives, lecithin derivatives and fatty acid alkanolamides, complexing agents such as EDTA, NTA and phosphonic acids,

Quell- und Penetrationsstoffe wie Glycerin, Propylenglykolmonoethyl- ether, Carbonate, Hydrogencarbonate, Guanidine, Harnstoffe sowie pri¬ märe, sekundäre und tertiäre Phosphate, Trübungsmittel wie Latex,Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and also primary, secondary and tertiary phosphates, opacifiers such as latex,

Perlglanzmittel wie EthylenglykoTmono- und -distearat, TreibmitteT wie Propan-Butan-Gemische, N2O, DimethyTether und Luft sowie Antioxidantien.Pearlescent agents such as ethylene glycol mono- and distearate, blowing agents such as propane-butane mixtures, N2O, dimethyl ether and air, and antioxidants.

Die erfindungsgemäßen Fixiermittel können als Creme, Gel oder Flüssigkeit formuliert sein. Es kann bevorzugt sein, die Zubereitungen in Form von Schaumaerosolen zu konfektionieren, die mit einem verflüssigten Gas wie z. B. Propan-Butan-Gemisehen, Stickstoff, CO2, Luft, N2O, Dimethylether, Fluorchlorkohlenwasserstofftreibmitteln oder Gemischen davon in Aerosol¬ behältern mit Schaumventil abgefüllt werden.The fixing agents according to the invention can be formulated as a cream, gel or liquid. It may be preferred to prepare the preparations in the form of Foam aerosols to assemble, which with a liquefied gas such. B. propane-butane mixtures, nitrogen, CO2, air, N2O, dimethyl ether, chlorofluorocarbon blowing agents or mixtures thereof in aerosol containers with a foam valve.

Die Wellmittel enthalten als zwingenden Bestandteil als keratinreduzie¬ rende Substanzen die dafür üblichen Mercaptane. Solche Verbindungen sind beispielsweise Thioglykolsäure, ThiomiIchsäure, 3-Mercaptopropionsäure sowie deren Salze und Ester, Cysteamin, Cystein, Bunte Salze und Alkali¬ salze der schwefligen Säure. Bevorzugt geeignet sind die Alkali- oder Am¬ moniumsalze der Thioglykolsäure und/oder der ThiomiIchsäure sowie die freien Säuren. Diese können in den keratinreduzierenden Zubereitungen der ersten Stufe des erfindungsgemäßen Haarverformungsverfahrens in einer Konzentration von 0,5 bis 1,0 Mol/kg bei einem pH-Wert von 6,5 bis 10 eingesetzt werden. Die Einwirkungszeit für die keratinreduzierende Zube¬ reitung beträgt in der Regel 20 bis 40 Minuten, wobei die Dicke des zu behandelnden Haares, der gewünschte Verformungsgrad, die Größe der ver¬ wendeten mechanischen Verformungshilfe (Haarwickler) und die Art des Ke- ratinreduktionsmittels weitere Einflußgrößen sind.The corrugating agents contain the usual mercaptans for this as a compulsory component as keratin-reducing substances. Such compounds are, for example, thioglycolic acid, thiolic acid, 3-mercaptopropionic acid and their salts and esters, cysteamine, cysteine, multicolored salts and alkali salts of sulfurous acid. The alkali metal or ammonium salts of thioglycolic acid and / or thiolic acid and the free acids are particularly suitable. These can be used in the keratin-reducing preparations of the first stage of the hair shaping process according to the invention in a concentration of 0.5 to 1.0 mol / kg at a pH of 6.5 to 10. The exposure time for the keratin-reducing preparation is generally 20 to 40 minutes, the thickness of the hair to be treated, the desired degree of deformation, the size of the mechanical shaping aid used (hair curler) and the type of keratin reducing agent being further influencing variables .

Zu einer deutlichen Verbesserung der Eigenschaften dauergewellter Haare genügt es, wenn die erfindungsgemäßen Wirkstoffkombinationen im Fixier¬ mittel enthalten sind. Besonders groß ist der Effekt jedoch, wenn das Fixiermittel die erfindungsgemäßen Wirkstoffkombinationen und das Well¬ mittel ebenfalls ein Alkylglykosid gemäß Formel (I) enthält. To significantly improve the properties of permed hair, it is sufficient if the active substance combinations according to the invention are contained in the fixative. However, the effect is particularly great if the fixative contains the active compound combinations according to the invention and the corrugating agent likewise contains an alkyl glycoside according to formula (I).

B e i s p i e l e:Example:

Die Angaben in den folgenden Formulierungsbeispielen sind jeweils in Ge¬ wichtsprozent.The details in the following formulation examples are in percent by weight.

1) Geldauerwelle:1) Geldauerwelle:

Figure imgf000016_0001
Figure imgf000016_0001

AlkyTgTykosid mit R=Ci2/i , Z=GTucose und x=l,4AlkyTgTykosid with R = Ci2 / i, Z = GTucose and x = 1,4

Fixierlösung:Fixing solution:

Alkylglykosid 1 2,0 %Alkyl glycoside 1 2.0%

Wasserstoffperoxid (50%ig) 6,0 %Hydrogen peroxide (50%) 6.0%

Natriu TauryTethersuTfat 1,0 %Natriu TauryTethersuTfat 1.0%

DehytonR AB 302 1,0 %Dehyton R AB 30 2 1.0%

Hydroxyethandiphosphonsäure 0,4 %Hydroxyethane diphosphonic acid 0.4%

Panthenol 1,0 %Panthenol 1.0%

2-PyrroTidon-5-carbonsäure 2,0 %2-pyrroidone-5-carboxylic acid 2.0%

Xanthan-Gum 0,1 %Xanthan gum 0.1%

Natronlauge (45 %ig) 0,8 %Sodium hydroxide solution (45%) 0.8%

Parfümöl q.s.Perfume oil q.s.

Wasser ad 100,0 %Water ad 100.0%

Fettaminderivat mit Betainstruktur (ca. 30 % Aktivsubstanz;Fatty amine derivative with betaine structure (approx. 30% active substance;

CTFA-Bezeichnung: Coco-Betaine) (HENKEL) 2) Cremedauerwelle:CTFA name: Coco-Betaine) (HENKEL) 2) Cream permanent wave:

Wellcreme:Corrugated cream:

Alkylglykosid 23 2,0 %Alkyl glycoside 23 2.0%

Thioglykolsäure 8,0 %Thioglycolic acid 8.0%

Hydroxyethandiphosphonsäure 0,3 %Hydroxyethane diphosphonic acid 0.3%

Ammoniak (25 %) 7,3 %Ammonia (25%) 7.3%

A moniumcarbonat 3,0 %A monium carbonate 3.0%

Cetyl/Stearyl-Alkohol 5,0 %Cetyl / stearyl alcohol 5.0%

Guerbet-Alkohol 4,0 %Guerbet alcohol 4.0%

Parfümöl q.s.Perfume oil q.s.

Wasser ad 100,0 %Water ad 100.0%

Alkylglykosid mit

Figure imgf000017_0001
Z=Glucose und x=l,6Alkylglycoside with
Figure imgf000017_0001
Z = glucose and x = 1.6

Fixierlösung:Fixing solution:

Alkylglykosid 2Alkyl glycoside 2

Gehärtetes RizinusölHardened castor oil

KaliumbromatPotassium bromate

NitrilotriessigsäureNitrilotriacetic acid

CitronensäureCitric acid

MerquatR5504 MerquatR550 4

ParfümölPerfume oil

Wasser

Figure imgf000017_0002
water
Figure imgf000017_0002

Dimethyldiallylammoniumchlorid-Acrylamid-Copolymer (8% in Wasser) (MOBIL 0IL)Dimethyldiallylammonium chloride-acrylamide copolymer (8% in water) (MOBIL 0IL)

3) Flüssigdauerwelle:3) Liquid perm:

Wellotion: Alkylglykosid 1 1,5 % Thioglykolsäure 8,0 % Cocoamidobetain 1,0 % Ammoniak (25 %) 6,4 % Ammoniumcarbonat 3,0 %

Figure imgf000018_0001
Wellotion: alkyl glycoside 1 1.5% thioglycolic acid 8.0% cocoamidobetaine 1.0% ammonia (25%) 6.4% ammonium carbonate 3.0%
Figure imgf000018_0001

4) Flüssigdauerwelle:4) Liquid perm:

Wellotion:Wellotion:

Alkylglykosid 2 2,0 %Alkyl glycoside 2 2.0%

ThioglykoTsäure 10,0 %Thioglycotic acid 10.0%

Hydroxyethandiphosphonsäure 0,3 -6Hydroxyethane diphosphonic acid 0.3 -6

Ammoniak (25 %) 2,5Ammonia (25%) 2.5

A moniumcarbonat 4,5 %A monium carbonate 4.5%

AbiTRß99505 2,5 %AbiTRß9950 5 2.5%

ParfümöT q.s.Perfumery q.s.

Wasser ad 100,0 %Water ad 100.0%

5 PolysiToxan-PoTyorganobetain-CopoTymer (30 % Aktivsubstanz) (GoTd- schmidt) Fixierlösung: 5 PolysiToxan-PoTyorganobetain-CopoTymer (30% active substance) (GoTd-schmidt) Fixing solution:

Alkylglykosid 1 2,0 %Alkyl glycoside 1 2.0%

Fettalkoholethersulfat 4,5 %Fatty alcohol ether sulfate 4.5%

Wasserstoffperoxid (50%) 5,0 %Hydrogen peroxide (50%) 5.0%

GafquatR7556 1,0 %Gafquat R 755 6 1.0%

Xanthan-Gum 0,1 %Xanthan gum 0.1%

Hydroxyethandiphosphonsäure 1,0 %Hydroxyethane diphosphonic acid 1.0%

Ethylendiamintetraessigsäure 0,1 %Ethylenediaminetetraacetic acid 0.1%

Natronlauge (45 %) 0,8 %Sodium hydroxide solution (45%) 0.8%

Parfümöl q.s.Perfume oil q.s.

Wasser ad 100,0 %Water ad 100.0%

quaternisiertes Poly(vinylpyrrolidon-dimethyla inoethylmethacrylat) (19 % Aktivsubstanz in Wasser) (GAF)quaternized poly (vinylpyrrolidone-dimethyla inoethyl methacrylate) (19% active substance in water) (GAF)

5) Flüssigdauerwelle:5) Liquid perm:

Figure imgf000019_0001
Parfümöl q.s.
Figure imgf000019_0001
Perfume oil qs

Wasser ad 100,0 %Water ad 100.0%

7 Copolymer aus HydroxyethyTceTTuTose und Dianyldimethylammoniumchlorid (CTFA-Bezeichnung: Polyquaternium-4) (National Starch)7 Copolymer of HydroxyethyTceTTuTose and Dianyldimethylammonium Chloride (CTFA name: Polyquaternium-4) (National Starch)

6) Flüssigdauerwelle:6) Liquid perm:

Wellotion:Wellotion:

ATkyTgTykosid 2 1,5 %ATkyTgTykosid 2 1.5%

ThiogTykoTsäure 10,0 % Kokosacylaminopropyl-dimethylammoniumglycinat 1,5 %ThiogTykoTäure 10.0% cocoacylaminopropyl-dimethylammonium glycinate 1.5%

Hydroxyethandiphosphonsäure 0,3 %Hydroxyethane diphosphonic acid 0.3%

Ammoniak (25 %) 2,5 %Ammonia (25%) 2.5%

Ammoniumcarbonat 4,5 %Ammonium carbonate 4.5%

GafquatR755 2,5 %Gafquat R 755 2.5%

Parfümöl q.s. Wasser ad 100,0 -Perfume oil q.s. Water ad 100.0 -

FixierTösung:Fixing solution:

ATkyTgTykosid 2 2,0 %ATkyTgTykosid 2 2.0%

FettaTkohoTethersuTfat 4,5 %Fatty cohesion suated 4.5%

Wasserstoffperoxid (50 %) 5,0 %Hydrogen peroxide (50%) 5.0%

Xanthan-Gu 0,1 %Xanthan Gu 0.1%

LuviquatR FC-5508 1,0 %Luviquat R FC-550 8 1.0%

Hydroxyethandiphosphonsäure 1,0 %Hydroxyethane diphosphonic acid 1.0%

Ethylenamintetraessigsäure 0,1 %Ethylene amine tetraacetic acid 0.1%

Natronlauge (45 %) 0,8 %Sodium hydroxide solution (45%) 0.8%

ParfümöT q.s.Perfumery q.s.

Wasser ad 100,0 %Water ad 100.0%

VinylimidazoTiniu methochlorid-Vinylpyrrolidon-Copolymerisat (50:50) (40 % Aktivsubstanz) (BASF)" 7) Flüssigdauerwelle:VinylimidazoTiniu methochloride-vinylpyrrolidone copolymer (50:50) (40% active substance) (BASF) " 7) Liquid perm:

Wellotion:Wellotion:

Alkylglykosid 2Alkyl glycoside 2

ThioglykolsäureThioglycolic acid

Cχ2-i8-AcylsarcosinCχ2-i8 acyl sarcosine

HydroxyethandiphosphonsäureHydroxyethane diphosphonic acid

Ammoniak (25 %)Ammonia (25%)

AmmoniumcarbonatAmmonium carbonate

Harnstoffurea

MerquatR550Merquat R 550

ParfümölPerfume oil

Wasserwater

Fixierlösung:Fixing solution:

Alkylglykosid 2Alkyl glycoside 2

FettalkoholethersulfatFatty alcohol ether sulfate

KaliumbromatPotassium bromate

Xanthan-GumXanthan gum

CitronensäureCitric acid

MerquatR550Merquat R 550

ParfümölPerfume oil

Wasser

Figure imgf000021_0001
water
Figure imgf000021_0001

8) Flüssigdauerwelle:8) Liquid perm:

Wellotion:Wellotion:

Alkylglykosid 2 1,5 %Alkyl glycoside 2 1.5%

Thioglykolsäure 8,0 %Thioglycolic acid 8.0%

N-Kokosalkylaminopropionat 1,0 %N-coconut alkyl aminopropionate 1.0%

Hydroxyethandiphosphonsäure 0,2 %Hydroxyethane diphosphonic acid 0.2%

Ammoniak (25 %) 1,7 %Ammonia (25%) 1.7%

Ammoniumcarbonat 5,0 %Ammonium carbonate 5.0%

Harnstoff 2,0 %Urea 2.0%

Parfümöl q.s. Wasser ad 100,0 # Fixierlösung:Perfume oil qs water ad 100.0 # Fixing solution:

Alkylglykosid 2 2,5 %Alkyl glycoside 2 2.5%

Fetta1koholethersu1fat 2,0 %Fatty alcohol alcohol 2.0%

KaTiumbromat 3,5 %Potassium bromate 3.5%

Xanthan-Gum 0,3 %Xanthan gum 0.3%

Citronensäure 0,1 %Citric acid 0.1%

MerquatR550 0,4 %Merquat R 550 0.4%

ParfümöT q.s.Perfumery q.s.

Wasser ad 100,0 %Water ad 100.0%

9) Flüssigdauerwelle:9) Liquid perm:

Figure imgf000022_0001
10) Schaumdauerwelle:
Figure imgf000022_0001
10) Foam perm:

Wellschäum:Corrugated foam:

Alkylglykosid 1 5,5Alkyl glycoside 1 5.5

Thioglykolsäure 8,0Thioglycolic acid 8.0

Natriumlaurylethersulfat 3,5Sodium lauryl ether sulfate 3.5

Ammoniak (25 %) 6,3Ammonia (25%) 6.3

Ammoniumcarbonat 3,0Ammonium carbonate 3.0

Nitrilotriessigsäure 0,3Nitrilotriacetic acid 0.3

Harnstoff 1,5Urea 1.5

Dimethylisosorbid 1,0Dimethyl isosorbide 1.0

Propan/Butan 3,5Propane / butane 3.5

Parfümöl q.s.Perfume oil q.s.

Wasser ad 100,0 %Water ad 100.0%

Fixierschaum:Fixing foam:

Alkylglykosid 1 3,5Alkyl glycoside 1 3.5

Natriumlaurylethersulfat 2,0 %Sodium lauryl ether sulfate 2.0%

Kaliumbromat 3,5 %Potassium bromate 3.5%

Fettalkoholethoxylat 3,0 %Fatty alcohol ethoxylate 3.0%

Propan/Butan 3,5 %Propane / butane 3.5%

Parfümöl q.s.Perfume oil q.s.

Wasser ad 100,0 hWater ad 100.0 h

11) Schau dauerwelle:11) Look perm:

Wellschäum:Corrugated foam:

Alkylglykosid 2 3,0 %Alkyl glycoside 2 3.0%

Thioglykolsäure 9,0 %Thioglycolic acid 9.0%

Nitrilotriessigsäure 0,3 %Nitrilotriacetic acid 0.3%

Ammoniak (25 %) 6,3 %Ammonia (25%) 6.3%

GafquatR 755 3,0 %Gafquat R 755 3.0%

Fettalkoholethoxylat 2,5 %Fatty alcohol ethoxylate 2.5%

Natriumlaurylethersulfat 3,5 %Sodium lauryl ether sulfate 3.5%

Harnstoff 1,5 %

Figure imgf000024_0001
Urea 1.5%
Figure imgf000024_0001

12) Schaumdauerwelle:12) Foam perm:

Figure imgf000024_0002
Figure imgf000025_0001
Figure imgf000024_0002
Figure imgf000025_0001

13) Dauerwellotion:13) Permanent wave lotion:

Figure imgf000025_0002
Figure imgf000025_0002

9 Poly(dimethyldiallylammoniumchlorid) (40 % Aktivsubstanz) (MOBIL OIL) 10 Poly(20)oxyethylensorbitanmonolaurat (ATLAS) 9 poly (dimethyldiallylammonium chloride) (40% active substance) (MOBIL OIL) 10 poly (20) oxyethylene sorbitan monolaurate (ATLAS)

Figure imgf000025_0003
Figure imgf000025_0003

Claims

P a t e n t a n s p r ü c h e Patent claims 1. Verfahren zur dauerhaften Verformung von Haaren, bei welchem man das Haar vor und/oder nach einer mechanischen Verformung mit einer wäßri¬ gen Zubereitung einer keratinreduzierenden Substanz behandelt, nach einer Einwirkungszeit spült, dann mit einer wäßrigen Zubereitung eines Oxidationsmittels fixiert und ebenfalls nach einer Einwirkungszeit spült, dadurch gekennzeichnet, daß in der wäßrigen Zubereitung des Oxidationsmittels ein Alkylglykosid der allgemeinen Formel (I),1. A process for permanent shaping of hair, in which the hair is treated with an aqueous preparation of a keratin-reducing substance before and / or after a mechanical shaping, rinsed after an exposure time, then fixed with an aqueous preparation of an oxidizing agent and likewise after a Exposure time rinses, characterized in that in the aqueous preparation of the oxidizing agent, an alkyl glycoside of the general formula (I), R0-(Z)X (I) R 0- (Z) X (I) in der R steht für einen AlkyTrest mit 6 bis 22 Kohlenstoffatomen, Z für ein Mono- oder OTigosaccharid und dessen Oligomerisationsgrad x für eine ZahT von 1,1 bis 5, oder dessen Anlagerungsprodukt mit 1 bisin which R stands for an alkyl radical with 6 to 22 carbon atoms, Z for a mono- or OTigosaccharide and its degree of oligomerization x for a ZahT of 1.1 to 5, or its adduct with 1 to 10 MoTeküTen EthyTenoxid und/oder PropyTenoxid in Kombination mit einer oberfTächenaktiven Verbindung Ar ausgewähTt unter den nichtionogenen, zwitterionischen und amphoteren Tensiden, und/oder einer poTymeren Verbindung B, wobei für den Fall, daß die poly ere10 MoTeküTen EthyTenoxid and / or PropyTenoxid in combination with a surface-active compound A r selected from the nonionic, zwitterionic and amphoteric surfactants, and / or a polymeric compound B, in the event that the poly ere Verbindung B ein Kationpolymer ist, diese ausgewählt ist ausCompound B is a cation polymer, this is selected from - quaternisierten CelTuToseethern, PoTysiToxanen mit quaternären Gruppen,quaternized CelTuTose ethers, PoTysiToxanes with quaternary groups, - DimethyTdiaTTyTammoniumchTorid-PoTymeren und -CopoTymeren,- DimethyTdiaTTyTammoniumchTorid-PoTymeren and -CopoTymeren, - mit DiethyTsuTfat quaternierten DimethylaminoethylmethacryTat- VinyT- pyrroTidon-CopoTymeren, und- DimethylaminoethylmethacryTat- VinyT- pyrroTidon-CopoTymeren quaternized with DiethyTsuTfat, and - VinyTpyrroTidon-MethoimidazoTiniumchTorid-CopoTymeren,- VinyTpyrroTidon-MethoimidazoTiniumchTorid-CopoTymeren, enthaTten ist.is included. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß das ATkyTgTy¬ kosid ausgewähTt ist aus den Verbindungen der Formel (I), bei denen R für einen Alkylrest mit 8 bis 14 Kohlenstoffatomen steht und Z ausge¬ wählt ist aus der Gruppe, die durch Glucose, Fructose, Galactose, Arabinose und Sucrose gebildet wird.2. The method according to claim 1, characterized in that the ATkyTgTy¬ kosid is selected from the compounds of formula (I) in which R represents an alkyl radical with 8 to 14 carbon atoms and Z is selected from the group formed by glucose, fructose, galactose, arabinose and sucrose. 3. Verfahren nach einem der Ansprüche 1 oder 2, dadurch gekennzeichnet, daß das Alkylglykosid ausgewählt ist aus den Verbindungen der Formel (I), bei denen R für Glucose und der mittlere Oligomerisationsgrad x für eine Zahl von 1,3 bis 2 steht.3. The method according to any one of claims 1 or 2, characterized in that the alkyl glycoside is selected from the compounds of formula (I) in which R is glucose and the average degree of oligomerization x is a number from 1.3 to 2. 4. Verfahren nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß das Alkylglykosid in der wäßrigen Zubereitung in einer Menge von 0,1 bis 40 Gew.-%, insbesondere von 0,5 bis 20 Gew.-%, jeweils bezogen auf die gesamte Zubereitung, enthalten ist.4. The method according to any one of claims 1 to 3, characterized in that the alkyl glycoside in the aqueous preparation in an amount of 0.1 to 40 wt .-%, in particular from 0.5 to 20 wt .-%, each based on the entire preparation is included. 5. Verfahren nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß die oberflächenaktive Verbindung aus der Gruppe der ampholytischen und zwitterionischen Tenside ausgewählt ist.5. The method according to any one of claims 1 to 4, characterized in that the surface-active compound is selected from the group of ampholytic and zwitterionic surfactants. 6. Verfahren nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß die oberflächenaktive Verbindung A in einer Menge von 0,5 bis 10 Gew.-%, bezogen auf die gesamte Zubereitung, enthalten ist.6. The method according to any one of claims 1 to 5, characterized in that the surface-active compound A is contained in an amount of 0.5 to 10 wt .-%, based on the entire preparation. 7. Verfahren nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, daß die polymere Verbindung B ausgewählt ist aus der Gruppe der zwitterionischen und amphoteren Polymere.7. The method according to any one of claims 1 to 6, characterized in that the polymeric compound B is selected from the group of zwitterionic and amphoteric polymers. 8. Verfahren nach einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, daß die polymere Verbindung B in einer Menge von 0,01 bis 5 Gew.-%, bezogen auf die gesamte Zubereitung, enthalten ist.8. The method according to any one of claims 1 to 7, characterized in that the polymeric compound B is contained in an amount of 0.01 to 5 wt .-%, based on the entire preparation. 9. Verfahren nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, daß auch in der wäßrigen Zubereitung des Reduktionsmittels ein Alkyl¬ glykosid der Formel (I) enthalten ist. 9. The method according to any one of claims 1 to 8, characterized in that an alkyl glycoside of the formula (I) is also contained in the aqueous preparation of the reducing agent.
PCT/EP1993/000931 1992-04-24 1993-04-16 Permanent waving process Ceased WO1993021897A1 (en)

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WO1995005158A1 (en) * 1993-08-19 1995-02-23 Henkel Kommanditgesellschaft Auf Aktien Aerosol-foam preparations
WO1996007394A1 (en) * 1994-09-05 1996-03-14 Henkel Kommanditgesellschaft Auf Aktien Process and agent for permanent shaping of keratin fibers
US6555100B1 (en) 1997-12-31 2003-04-29 L'ORéAL S.A. Compositions for treating keratinous materials containing a combination of a zwitterion polymer and a water insoluble non-volatile silicon

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US5494659A (en) 1993-08-20 1996-02-27 Henkel Kommanditgesellschaft Auf Aktien Hair treatment composition
BR9606543A (en) * 1995-07-28 1998-06-23 Wella Ag Process for permanent hair shaping
DE19815972C1 (en) * 1998-04-09 1999-09-30 Goldwell Gmbh Fast-acting permanent wave fixative with conditioning effect on hair
DE19904014A1 (en) * 1999-02-02 2000-08-10 Goldwell Gmbh Water-based aerosol mousse permanent waving composition that collapses quickly contains dimethyl ether as propellant
DE19919087C2 (en) * 1999-04-27 2003-02-27 Cognis Deutschland Gmbh Process for permanent deformation of keratin fibers
FR2814066B1 (en) * 2000-09-18 2004-05-07 Oreal PROCESS FOR PERMANENT DEFORMATION OF KERATINIC MATERIALS USING AN ORGANIC ABSORBENT AGENT
US20070267035A1 (en) 2004-09-07 2007-11-22 Henkel Kommanditgesellschaft Auf Aktien Composition and Method for the Smoothing of Fibres Containing Keratin

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995005158A1 (en) * 1993-08-19 1995-02-23 Henkel Kommanditgesellschaft Auf Aktien Aerosol-foam preparations
WO1996007394A1 (en) * 1994-09-05 1996-03-14 Henkel Kommanditgesellschaft Auf Aktien Process and agent for permanent shaping of keratin fibers
US6555100B1 (en) 1997-12-31 2003-04-29 L'ORéAL S.A. Compositions for treating keratinous materials containing a combination of a zwitterion polymer and a water insoluble non-volatile silicon

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