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EP1747045A1 - Procede et composition pour restructurer des fibres de keratine - Google Patents

Procede et composition pour restructurer des fibres de keratine

Info

Publication number
EP1747045A1
EP1747045A1 EP05731059A EP05731059A EP1747045A1 EP 1747045 A1 EP1747045 A1 EP 1747045A1 EP 05731059 A EP05731059 A EP 05731059A EP 05731059 A EP05731059 A EP 05731059A EP 1747045 A1 EP1747045 A1 EP 1747045A1
Authority
EP
European Patent Office
Prior art keywords
acid
hair
preparation
formula
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05731059A
Other languages
German (de)
English (en)
Inventor
Sabine Kainz
Ursula Huchel
Olaf Lammerschop
Burkhard Müller
Thorsten Knappe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1747045A1 publication Critical patent/EP1747045A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/22—Peroxides; Oxygen; Ozone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • 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
    • A61Q5/12—Preparations containing hair conditioners
    • 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
    • A61Q5/004—Preparations used to protect coloured hair

Definitions

  • the invention relates to a process for restructuring keratin fibers, in which a keratin fiber is brought into contact with an aqueous preparation of at least one polysulfide and a reducing agent simultaneously or in succession, and is subsequently brought into contact with an oxidizing agent.
  • the invention further relates to preparations for use in this method.
  • Keratin fibers, especially hair are an important part of everyday life as an integral part of the human body and as an essential part of human clothing and home textiles.
  • the treatment with washing, cleaning, styling and coloring products for cleaning and design purposes, as well as their exposure to environmental influences such as ozone, salt and chlorine water, IR, UV and heat radiation (blow-drying) lead to over time cumulative damage to the fibers and thus to a reduction in their quality.
  • both cleaning hair with shampoos and decorating the hairstyle by dyeing or perming are interventions that influence the natural structure and properties of the hair. Consequently, after such a treatment, for example, the wet and dry combability, hold, fullness, shine and tactility of the hair can be unsatisfactory.
  • the hold of the color on the hair can continue to be unsatisfactory, particularly with frequent hair washing, so that there is a gradual bleeding of the color.
  • Care products of this type influence the natural structure and properties of the hair. After such treatments, for example, the wet and dry combability of the hair, the hold and the fullness of the hair can be improved or the hair can be protected against an increased split rate.
  • the hair is treated with special active ingredients, for example quaternary ammonium salts or special polymers.
  • special active ingredients for example quaternary ammonium salts or special polymers.
  • this treatment improves the combability, hold and fullness of the hair and reduces the split rate.
  • the active substances available both for separate aftertreatment agents and for combination preparations generally act preferentially on the hair surface.
  • Hair care products are known which give the hair shine, hold, fullness or better wet or dry combability or prevent the split ends.
  • the internal structural cohesion of the hair fibers can be greatly influenced in particular in oxidative and reductive processes such as coloring and perms.
  • Keratinic fibers are particularly exposed to deformation processes such as hair perms.
  • the permanent deformation of keratin fibers is usually carried out in such a way that the fiber is mechanically deformed and the deformation is determined by suitable aids.
  • the fiber Before and / or after this deformation, the fiber is treated with an aqueous preparation of a keratin-reducing substance and rinsed with water or an aqueous solution after an exposure time.
  • the fiber is then treated with the aqueous preparation of an oxidizing agent. After an exposure time, this is also rinsed out and the fiber is freed from the mechanical deformation aids (curlers, papillots).
  • the aqueous preparation of the keratin reducing agent is usually made alkaline, so that on the one hand a sufficient proportion of the thiol functions are deprotonated and on the other hand the fiber swells and in this way a deep penetration of the keratin-reducing substance into the fiber is made possible.
  • the keratin-reducing substance cleaves some of the disulfide bonds of keratin to -SH groups, so that the peptide crosslinking is loosened and the keratin structure is reoriented due to the tension in the fiber due to the mechanical deformation. 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 is often embrittlement and dulling of the hair.
  • other properties such as wet and dry combability, grip, smoothness, softness, gloss and tear resistance are also influenced in an undesirable manner.
  • Nourishing additives and film formers are often added to the permanent waving agent without, however, significantly improving the hair structure.
  • high-molecular polymers are used, for example, which attach to the top layer of skin and hair and there produce an external, subjectively perceptibly improved grip on the hair.
  • the structural damage to the interior of the hair which is caused by the reduction process in the case of perms, cannot be reduced, however, because the substances cannot penetrate the hair due to their size.
  • EP 723 772 describes that alkalizing agents such as basic amino acids together with cationic polymers in the waving agent cause the hair to swell more. On the one hand it leads to stronger shaping and longer durability of the perm, but on the other hand it also leads to hair damage.
  • the published patent application GB 216 041 9 describes a method in which hair is first treated with a reducing agent which is then rinsed out. Then an aqueous protein hydrolyzate, preferably with a molecular weight greater than 50,000 daltons, is applied to the areas to be treated, after which the neutralization is carried out. Subjectively, the area treated in this way felt better, but there was no reduction in hair damage inside.
  • the object of the present invention was to provide an improved method for restructuring keratin fibers, which has advantages over the prior art and enables adequate effectiveness and duration of action.
  • the process should also be able to be carried out under conditions which are gentle on the fibers and should be able to be carried out, for example, as part of a conventional permanent wave treatment or a customary hair straightening process.
  • the object of the invention is achieved by a method in which keratin fibers are brought into contact with certain polysulfides and simultaneously or subsequently with a reducing agent and in a further step with an oxidizing agent.
  • a first subject of the invention is therefore a process for restructuring keratin fibers, in which a keratin fiber
  • R is hydrogen or the rest
  • A represents a bond or a divalent saturated or mono- or polyunsaturated aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms, which may be substituted by one or more halogen, hydroxyl or carboxy groups and the shortest connection between the two of group A adjacent carbonyl groups consists of up to 12 carbon atoms, and wherein
  • R 1 and R 2 may be the same or different and are selected from R 5 0- and H 2 N - CH - CH 2 - S - S - CH 2 - CH - NH
  • R 5 is hydrogen or an alkyl group having 1 to 6 carbon atoms
  • n is an integer from 1 to 100 and where one or more carboxyl group (s) may be in the form of one or more of their salt (s), and a reducing agent is brought into contact simultaneously or successively, and then
  • (b) is contacted with an oxidizing agent.
  • all animal hair such as e.g. Wool, horsehair, angora hair, furs, feathers and silk and products or textiles made from them can be used.
  • the method according to the invention is preferably suitable for shaping human hair and wigs made therefrom. Because of the gentle process conditions, it is particularly suitable for deforming the hair on the living body, e.g. in connection with the production of permed hair or the straightening of curly hair.
  • Restructuring in the sense of the present invention means in particular a fiber reinforcement, an increase in tear strength and / or a reduction in the damage to keratin fibers caused by the most varied of influences.
  • the restoration of natural strength plays an important role.
  • Restructured fibers can, for example, have an increased tensile strength, an increased strength, an increased Characterize elasticity and / or an increased volume, which can be shown in a larger abundance, for example, in a hairstyle. Furthermore, they can have an improved gloss, an improved grip and / or easier combability.
  • the method according to the invention serves to strengthen, protect and repair keratin fibers and is particularly suitable for improving the hair structure and / or strengthening human hair.
  • fiber properties such as strength, elasticity or volume are positively influenced in the sense of an increase in these properties.
  • the method is suitable for styling purposes, such as shaping and shape retention, and for increasing the color fastness, in particular the wash fastness of colored keratin fibers, in particular colored human hair. Wash fastness is to be understood as the preservation of the color of a dyed keratin fiber with regard to color nuance and / or color intensity if the dyed fiber is exposed to the influence of aqueous agents, in particular surfactant-containing agents such as shampoos.
  • the method according to the invention is also suitable for protecting fibers from the damaging influence of light.
  • the method according to the invention does not require any toxicologically questionable substances, e.g. Radical formers or radicals occurring as intermediates.
  • polysulfides are used in which in formula (I) A denotes a divalent saturated aliphatic hydrocarbon radical having 2 to 6 carbon atoms, in particular the ethane-1,2-diyl radical.
  • n in formula (I) is an integer from 1 to 10.
  • Ways of producing polysulfides of the formula (I) which are suitable according to the invention are described in US Pat. No. 5,646,239 (in particular Examples 1 to 3), to which reference is hereby expressly made.
  • the polysulfides of the formula (I) used in the process according to the invention can preferably be prepared by polycondensing cystine or a cystine derivative in which the carboxyl groups have been esterified or otherwise derivatized with a dicarbonyl compound.
  • a dicarboxylic acid derivative in which the carboxyl groups are present in activated form is particularly suitable as the dicarbonyl compound, such as e.g. a dicarboxylic acid chloride.
  • the polysulfide of the formula (I) is used in the process according to the invention in the form of a condensation product which can be obtained by reacting cystine with a dicarboxylic acid derivative in which the carboxyl groups are present in activated form, e.g. a dicarboxylic acid dichloride.
  • this implementation can be carried out as interface condensation in a two-phase system.
  • the reducing agents which can be used in step (a) of the process according to the invention are preferably selected from keratin-reducing compounds, in particular compounds with at least one thiol group and their derivatives, and from sulfites, hydrogen sulfites and disulfites.
  • Compounds with at least one thiol group and their derivatives are, for example, thioglycolic acid, thiolactic acid, thio malic acid,
  • the monoethanolammonium salts or ammonium salts of thioglycolic acid and / or are particularly suitable of thiolactic acid and the respective free acids. In the process according to the invention, these are preferably used in the form of compositions which contain concentrations of 0.5 to 2.0 mol / kg of these compounds and have a pH of 5 to 12, in particular 7 to 9.5.
  • Alkalizing agents such as ammonia, alkali and ammonium carbonates and hydrogen carbonates or organic amines such as monoethanolamine are preferably used to adjust these pH values.
  • Examples of keratin-reducing compounds of the disulfite type are alkali disulfites, such as sodium disulfite (Na 2 S 2 0 5 ) and potassium disulfite (K 2 S 2 O 5 ), as well as magnesium disulfite and ammonium disulfite ((NH 4 ) 2 S 2 0 5 ).
  • Ammonium disulfite can be preferred according to the invention.
  • Examples of keratin-reducing compounds of the hydrogen sulfite type are hydrogen sulfites as alkali, magnesium, ammonium or alkanolammonium salt based on a C 2 -C - mono-, di- or trialkanolamine.
  • Ammonium bisulfite can be a particularly preferred bisulfite.
  • Examples of keratin-reducing compounds of the sulfite type are sulfites as alkali, ammonium or alkanolammonium salts based on a C 2 -C 4 -mono-, di- or trialkanolamine. Ammonium sulfite is preferred.
  • the use of sulfite and / or disulfite and / or hydrogen sulfate in the process according to the invention is preferably carried out at pH 5 to 8, in particular from pH 6 to 7.5.
  • Preferred C 2 -C 4 alkanolamines according to the invention are 2-aminoethanol (monoethanolamine) and N, N, N-tris (2-hydroxyethyl) amine (triethanolamine).
  • Monoethanolamine is a particularly preferred C 2 -C -alkanolamine, which is preferably used in the process according to the invention in the form of compositions which have a concentration of from 0.2 to 6% by weight of this amine, based on the overall composition.
  • Reducing agents which are particularly preferred according to the invention are thioglycolic acid and thiolactic acid and salts thereof.
  • the reducing agent is preferably used in the form of a composition which contains the reducing agent in an amount of 5 to 20% by weight, based on the overall composition.
  • the temperature when the reducing agent is brought into contact with the fiber is preferably in a range from about 10 to about 60 ° C.
  • Suitable oxidizing agents which can be used in step (b) of the process according to the invention are preferably substances which are selected from oxygen, air, H 2 O 2 , disulfides, sodium perborate and its hydrates, sodium and potassium bromate, sodium chlorite, sodium or potassium persulfate , Sodium iodate, calcium or magnesium bromate, tetrathionates, glyoxal, glutaraldehyde and mixtures of these substances.
  • oxygen or air it can be advantageous if catalytic amounts of manganese or cobalt sulfate or terpene derivatives are also present.
  • Air and / or H 0 are particularly preferred as oxidizing agents.
  • the oxidizing agents are preferably used in the form of aqueous preparations.
  • thioglycolic acid and / or thiolactic acid or one of their salts is used as reducing agent in step (a) of the process according to the invention and H 2 0 2 as oxidizing agent in step (b) of the process according to the invention.
  • the at least one polysulfide of the formula (I) according to the invention is present in the preparation used in step (a) of the process according to the invention in a total amount of 0.01 to 5, in particular 0.1 to 2,% by weight, based on the Total weight of the preparation.
  • the preparation used in step (a) of the process according to the invention preferably has a pH between 6 and 10, in particular between 7 and 9.5.
  • the preparations according to the invention can contain alkalizing agents such as ammonia, alkali and ammonium carbonates and hydrogen carbonates or organic amines such as monoethanolamine.
  • cystine in addition to the aqueous preparation of the polysulfide, cystine is also present in step (a) of the process according to the invention. It is preferred if the cystine, based on the weight of the at least one polysulfide of the formula (I), is present in an amount of 5 to 1000, in particular 50 to 500,% by weight.
  • step (a) of the process according to the invention it may be advantageous if, in addition to the aqueous preparation of the polysulfide and optionally cystine, succinic acid is also present.
  • the keratin fiber is brought into contact with the polysulfide and a reducing agent simultaneously or in succession.
  • step (a) of the process the fiber is brought into contact simultaneously with the polysulfide of the formula (I) and the reducing agent.
  • polysulfide and reducing agent are mixed with one another before being applied to the hair, for example 15 seconds to 12 hours before application to the hair.
  • it may be preferred to mix both components together shortly before application to the hair for example 15 seconds to 15 minutes before application to the hair.
  • the two components are mixed with one another for a long time before application to the hair, for example 1 to 12 hours beforehand.
  • step (a) of the process the fiber remains in contact with the polysulfide of the formula (I) and / or the reducing agent, preferably for an exposure time of 1 to 60, but in particular 5 to 30 minutes.
  • the fiber can be brought into contact with the polysulfide of the formula (I) and / or with the reducing agent in step (a) of the process according to the invention in such a way that other substances are present in addition to the aqueous preparation of the polysulfide and / or the reducing agent , These substances are preferably selected so that they form a suitable carrier for the treatment of the fiber for the polysulfide and / or for the reducing agent.
  • step (a) of the process according to the invention is carried out in such a way that a fiber is brought into contact with a preparation (R) which contains a polysulfide of the formula (I) and a reducing agent.
  • the substances present in the preparation (R) in addition to the polysulfide of the formula (I) preferably form a composition of the type familiar to the person skilled in the hair cosmetics industry as a "waving agent".
  • the fiber in step (a) of the process according to the invention is first of all prepared (V), which contains a polysulfide of formula (I), and then contacted with a reducing agent.
  • the preparation (V) contains a subset of the reducing agent used overall in the process according to the invention.
  • the fiber in step (a) of the process according to the invention is first brought into contact with a reducing agent and then with a preparation (Z) which contains a polysulfide of the formula (I).
  • the preparation (Z) contains a subset of the reducing agent used overall in the process according to the invention.
  • Bringing the fiber into contact with the oxidizing agent in step (b) of the process according to the invention can be carried out in such a way that other substances are present in addition to the oxidizing agent. These substances are preferably selected so that they form a carrier for the oxidizing agent suitable for treating the fiber.
  • step (b) of the method according to the invention is thus carried out in such a way that a fiber is brought into contact with a preparation (O) which contains the oxidizing agent.
  • the preparation (O) preferably forms a composition of the type which is familiar to the person skilled in the hair cosmetics industry as a "fixing agent".
  • step (c) there can additionally be at least one intermediate step (c), in which the fiber is treated with water or an aqueous preparation (C) and in particular rinsed which, in a preferred embodiment of the invention, is a composition of the type familiar to the person skilled in the hair cosmetics industry as an “intermediate rinse” suitable for use in a permanent wave method.
  • an intermediate rinse can contain, for example, a care substance, for example a protein hydrolyzate, in a carrier.
  • the fiber is preferably rinsed out with water.
  • the method according to the invention serves to permanently deform keratin fibers, in particular human hair.
  • the preparations used in the process according to the invention can be solid, liquid, gel-like or pasty. They are preferably selected from aqueous systems, natural or synthetic oils, water-in-oil or oil-in-water emulsions. Such systems and methods for their production are known in the prior art, to which reference is hereby made.
  • the preparations can be formulated as a cream, gel or liquid.
  • foam aerosols which are mixed with a liquefied gas such.
  • propane-butane mixtures, nitrogen, CO 2 , air, NO 2 , dimethyl ether, chlorofluorocarbon blowing agents or mixtures thereof are filled in aerosol containers with a foam valve.
  • the individual components of the method according to the invention are preferably used as a cream, gel or liquid.
  • the preparations used according to the invention can be in two or more phases.
  • Two-phase and multi-phase systems are systems in which there are at least two separate, continuous phases.
  • an aqueous phase and one or more, for example two, non-miscible, non-aqueous phases can be present separately from one another.
  • a water-in-oil emulsion and one separated from it are also possible, for example present aqueous phase or a water-in-oil emulsion and a separate aqueous phase present.
  • the invention also relates to an aqueous preparation for use in the process according to the invention which contains at least one polysulfide of the formula (I).
  • the aqueous preparation preferably contains 0.01 to 5, in particular 0.1 to 2% by weight of one or more polysulfides of the formula (I), based on the total weight of the preparation.
  • the preparation further contains buffer substances, for example a combination of ammonia and ammonium hydrogen carbonate, which keep the pH of the preparation in a range from 7 to 9.5.
  • buffer substances for example a combination of ammonia and ammonium hydrogen carbonate, which keep the pH of the preparation in a range from 7 to 9.5.
  • the preparation furthermore contains cystine, for example 0.001 to 10, but in particular 0.05 to 5% by weight of cystine, based on the total weight of the preparation.
  • the preparation furthermore contains a keratin-reducing compound, in particular thioglycolic acid and / or thiolactic acid or a salt thereof.
  • Active ingredients such as surfactants, complexing agents, polyols, fatty substances, oil substances, polymers, protein hydrolyzates, amino acids, vitamins, plant extracts, hydroxycarboxylic acids, emulsifiers, penetration aids and silicone oils can advantageously be used as further constituents of the preparations used in the process according to the invention.
  • Surfactants from the group of anionic, amphoteric, zwitterionic and nonionic surfactants are suitable as surfactants.
  • the surfactants have the task of promoting the wetting of the keratin surface by the treatment solution.
  • anionic surface-active substances are suitable as anionic surfactants, in particular those 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 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.
  • glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups can be contained in the molecule.
  • suitable 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,
  • 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 1 (OCH 2 CH 2 ) n - O - P -OR 2 (E1-I) I ox in R 1 preferably for an aliphatic hydrocarbon radical with 8 to 30 carbon atoms, R 2 for hydrogen, a radical (CH 2 CH2 ⁇ ) n R 1 or X, n for numbers from 1 to 10 and X for hydrogen, an alkali or alkaline earth metal or NR 3 R 4 R 5 R 6 , with R 3 to R 6 independently of one another representing hydrogen or a C1 to C4 - Hydrocarbon residue, stands,
  • 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 monoalkyl polyoxyethyl esters with 8 to 18 C atoms in the alkyl group and 1 to 6 oxyethyl groups, monoglycer disulfates, alkyl and alkenyl ether phosphates and protein fatty acid condensates.
  • cationic surface-active substances are suitable as cationic surfactants, in particular surfactants of the type of the quaternary ammonium compounds, the esterquats and the amidoamines.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides,
  • Dialkyldimethylammoniumchloride and Trialkylmethylammoniumchloride e.g. B. cetyltrimethylammonium chloride and bromide, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, as well as the compounds known under the INCI names quaternium-27 and quaternium-83 compounds.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Ester quats 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 ® .
  • the 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 are preferably present in the preparations used according to the invention in amounts of 0.05 to 10% by weight, based on the preparation as a whole. Amounts of 0.1 to 5% by weight are particularly preferred.
  • Zwitterionic surfactants are surface-active compounds that contain 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 amide
  • Ampholytic surfactants are surface-active compounds which, in addition to a C ⁇ -C 24 -alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -S0 3 H group in the molecule and are capable of forming internal salts.
  • suitable 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 acids and alkylaminoacetic acids each with about 8 to 24 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C12-Ci ⁇ -acylsarcosine.
  • Nonionic surfactants 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
  • Sorbitan fatty acid esters and addition products of ethylene oxide with sorbitan fatty acid esters such as, for example, the polysorbates
  • R 4 represents an alkyl or alkenyl radical having 4 to 22 carbon atoms
  • G represents a sugar radical having 5 or 6 carbon atoms
  • p represents numbers from 1 to 10. They can be obtained according to the relevant procedures in preparative organic chemistry. Representative of the extensive literature here is the review by Biermann et al. in Starch /force 45, 281 (1993), B. Salka in Cosm.Toil. 108, 89 (1993) and J. Kahre et al. in S ⁇ FW-Journal issue 8, 598 (1995).
  • 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.
  • Alkyl and / or alkenyl oligoglycosides are preferred an average degree of oligomerization p of 1.1 to 3.0 is used. From an application point of view, those alkyl and / or alkenyl oligoglycosides are preferred whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
  • the alkyl or alkenyl radical R 4 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,
  • Alkyl oligoglucosides based on hydrogenated Ci2 / ⁇ coco alcohol with a DP of 1 to 3 are preferred.
  • R 5 CO is an aliphatic acyl radical having 6 to 22 carbon atoms
  • R 6 is hydrogen, an alkyl or hydroxyalkyl radical having 1 to 4 Carbon atoms
  • [Z] represents a linear or branched polyhydroxyalkyl radical having 3 to 12 carbon atoms and 3 to 10 hydroxyl groups.
  • 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. With regard to the processes for their production, reference is made to US Pat. Nos.
  • 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 (E4-IV):
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides used are glucamides of the formula (E4-IV) in which R 8 is hydrogen or an alkyl group and R 7 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 8 is hydrogen or an alkyl group
  • R 7 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, petroselini
  • Fatty acid N-alkylglucamides of the formula (E4-IV) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C12 / 14 coconut fatty acid or a corresponding derivative are particularly preferred.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • the alkylene oxide addition products to saturated linear fatty alcohols and fatty acids, each with 2 to 30 moles of ethylene oxide per mole of fatty alcohol or fatty acid, and fatty acid esters of ethoxylated glycerol have proven to be preferred 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.
  • 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. Protein-fatty acid condensates, cocoamphodiacetates and fatty acid sulfates and their ethylene oxide and / or propylene oxide adducts are particularly preferred as surfactants.
  • Suitable complexing agents are, for example, EDTA, NTA, HEDP, organophosphonic acids, ß-alaninediacetic acid, and dipicolinic acid or mixtures of these substances.
  • polyols examples include glycerol and partial glycerol ether, 2-ethyl-1,3-hexanediol, 1,3-butanediol, 1,4-butanediol, 1,2-propanediol, 1,3-propanediol, pentanediols, for example 1,2- Pentanediol, hexanediols, for example 1,2-hexanediol or 1,6-hexanediol, dodecanediol, in particular 1,2-dodecanediol, neopentyl glycol and ethylene glycol.
  • 2-ethyl-1,3-hexanediol, 1,2-propanediol, 1,3-propanediol and 1,3-butanediol have proven to be particularly suitable.
  • polyols are preferably present in the preparations used according to the invention in amounts of 1-10, in particular 2-10,% by weight, based on the entire preparation.
  • Fat with water is understood to mean those alcohols which are not more than 10% by weight, based on the water mass, soluble in water at 20 ° C. Fat substances can be used as further active substances. Fats 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 with 6 to 30 carbon atoms in amounts of 0.1 can be used as fatty acids
  • Saturated, mono- or polyunsaturated, branched or unbranched fatty alcohols with C 6 -C 3 carbon atoms in amounts of 0.1-30% by weight, based on the entire preparation, can be used as fatty alcohols.
  • Natural and synthetic cosmetic oil bodies which can be used as active substances according to the invention are in particular:
  • 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.
  • Other triglyceride oils such as the liquid portions of beef tallow and synthetic triglyceride oils are also suitable.
  • the compounds are available as commercial products 1, 3-di- (2-ethyl-hexyl) - cyclohexane (Cetiol ® S), and di-n-octyl ether (Cetiol ® OE) may be preferred.
  • the amount of natural and synthetic cosmetic oil bodies used in the preparations used according to the invention is usually 0.1-30 % By weight, based on the entire preparation, preferably 0.1-20% by weight, and in particular 0.1-15% by weight.
  • the total amount of oil and fat components in the preparations according to the invention is usually 0.1-75% by weight, based on the entire preparation. Quantities of 0.1-35% by weight are preferred according to the invention.
  • polymers are advantageously used in the process according to the invention.
  • polymers are therefore added to the preparations used according to the invention, with both cationic, anionic, amphoteric and nonionic polymers having proven to be effective.
  • Cationic polymers are understood to mean polymers which have a group in the main and / or side chain which can be “temporary” or “permanent” cationic.
  • polymers which have a cationic group irrespective of the pH of the preparation are referred to as "permanently cationic".
  • These are usually polymers that contain a quaternary nitrogen atom, for example in the form of an ammonium group.
  • Preferred cationic groups are quaternary ammonium groups.
  • those polymers in which the quaternary ammonium group is linked via a C1-4 hydrocarbon group to a polymer main chain composed of acrylic acid, methacrylic acid or their derivatives have proven to be particularly suitable.
  • R 1 -H or -CH 3
  • R 2 , R 3 and R 4 are independently selected from C1-4 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 1 represents a methyl group
  • R 2 , R 3 and R 4 represent methyl groups m has the value 2.
  • Suitable physiologically acceptable 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 (methacryloyloxyethyltrimethylammonium chloride) with the INCI name Polyquatemium-37.
  • the crosslinking can take place with the aid of polyolefinically unsaturated compounds, for example divinylbenzene, tetraallyloxyethane, methylenebisacrylamide, diallyl ether, polyallylpolyglyceryl 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.
  • polymers are polyquaternium-6, -7, -22 and -39 and quaternium-52.
  • 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.
  • 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 of the formula (IX) preferably contain, as nonionic monomer units, acrylamide, methacrylamide, C 1 -C 8 -alkyl acrylate and C- M 2-methacrylic acid alkyl ester.
  • nonionic monomers acrylamide is particularly preferred.
  • these copolymers can also be crosslinked.
  • a preferred copolymer according to the invention is the crosslinked acrylamide-methacryloyloxyethyltrimethylammonium chloride copolymer.
  • 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 sold under the trade names Cosmedia ® Guar and Jaguar ® , Polysiloxanes with quaternary groups, such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Corning® 929 emulsion (containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. Goldschmidt), diquaternary polydimethylsiloxanes, Quatemium-80),
  • Vinylpyrrolidone-vinylimidazolium methochloride copolymers as are offered under the names Luviquat ® FC 370, FC 550, FC 905 and HM 552,
  • Polyquaternium 2 Polyquaternium 17, Polyquaternium 18 and Polyquaternium 27 polymers with quaternary nitrogen atoms in the main polymer chain.
  • cationic polymers can be used as cationic polymers (. B. commercial product, Quatrisoft ® LM 200) under the designations Polyquaternium-24, known polymers.
  • copolymers of vinyl pyrrolidone such as those available as commercial products Copolymer 845 (manufacturer: ISP), Gaffix ® VC 713 (manufacturer: ISP), Gafquat ® ASCP 1011, Gafquat ® HS 110, Luviquat ® 8155 and Luviquat ® MS 370 are.
  • Further cationic polymers that can be used according to the invention are the so-called “temporarily cationic” polymers.
  • polymers usually contain an amino group which is present as a quaternary ammonium group at certain pH values and is therefore cationic.
  • chitosan and its derivatives such as 101 are freely available commercially, for example under the trade names Hydagen CMF ®, Hydagen HCMF ®, Kytamer ® PC and Chitolam ® NB /.
  • 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 Alkylpolyglycodside according to DE-PS 44 13 686 and polymers of the type Polyquaternium-37.
  • anionic polymers which can be used in the preparations of the process 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, it being possible for the sulfonic acid group to be present in whole or in part as a sodium, potassium, ammonium, mono- or triethanolammonium salt ,
  • a homopolymer of 2-acrylamido-2 methylpropansulfon acid sold under the name Rheothik ® 11-80 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, with polyolefinically unsaturated compounds such as tetraallyloxyethane, allyl sucrose, allylpentaerythritol and methylene-bisacrylamide preferably being used as crosslinking agents.
  • 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 very suitable polymers.
  • a cross-linked with 1, 9-Decadiene-maleic acid methyl vinyl ether copolymer is available under the name Stabileze® ® QM.
  • amphoteric polymers can be used as polymers in all aqueous preparations of the process 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 in the molecule " - or -S0 3 ' groups, and summarized such polymers that contain -COOH or S0 3 H groups and quaternary ammonium groups.
  • amphopolymer suitable is that available under the name Amphomer ® acrylic resin which is a copolymer of tert-butylaminoethyl methacrylate, N- (1, 1, 3,3-tetramethylbutyl) -acrylamide and two or more monomers from the group of acrylic acid, Methacrylic acid and its simple esters.
  • Amphomer ® acrylic resin which is a copolymer of tert-butylaminoethyl methacrylate, N- (1, 1, 3,3-tetramethylbutyl) -acrylamide and two or more monomers from the group of acrylic acid, Methacrylic acid and its simple esters.
  • Amphoteric polymers which are preferably used are those polymers which essentially consist of one another
  • 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 carbonate, sodium sulfate, sodium bicarbonate, sodium sulfate, sodium sulfate, sodium bicarbonate, sodium sulfate, sodium bicarbonate, sodium sulfate, 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 bicarbonate, sodium bicarbonate, sodium sulfate, sodium bicarbonate
  • nonionic polymers can be contained in all aqueous preparations of the process according to the invention.
  • Suitable nonionic polymers are for example:
  • 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 methyl hydroxypropylcellulose, as they are for example sold under the trademark Culminal® ® and Benecel ® (AQUALON).
  • Culminal® ® and Benecel ® AQUALON.
  • 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 is above 200 ° C. at normal pressure.
  • Preferred siloxanes are polydialkylsiloxanes, such as, for example, polydimethylsiloxane, polyalkylarylsiloxanes, such as, for example, polyphenylmethylsiloxane, ethoxylated polydialkylsiloxanes and also polydialkylsiloxanes which contain amine and / or hydroxyl groups, and cyclomethicones.
  • 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 are preferably present in the preparations used according to the invention in amounts of 0.05 to 10% by weight, based on the entire preparation. 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 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 is also understood to mean total hydrolyzates and individual amino acids and their derivatives as well as mixtures of different amino acids.
  • Polymers constructed from amino acids and amino acid derivatives are understood by the term protein hydrolyzates. The latter include, for example, polyalanine, polyasparagine, polyserine, etc.
  • L-alanyl-L-proline polyglycine, glycyl-L-glutamine or D / L-methionine-S-methylsulfonium chloride.
  • ß-amino acids and their derivatives such as ß-alanine, anthranilic acid or hippuric acid can also be used according to the invention.
  • the molecular weight of the protein hydrolyzates which can be used according to the invention is between 75, the molecular weight for glycine, and 200,000, preferably the molecular weight is 75 to 50,000 and very particularly preferably 75 to 20,000 daltons.
  • protein hydrolyzates of plant, animal, marine or synthetic 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, for example, under the trademarks Gluadin ® (Cognis), DiaMin ® (Diamalt), Lexein ® (Inolex), Hydrosoy ® (Croda), Hydrolupin ® (Croda), Hydrosesame ® (Croda), Hydrotritium ® (Croda) and Crotein ® (Croda) available.
  • protein hydrolyzates amino acid mixtures obtained in some other way can also be used instead be used. 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 preferably present in the preparations used according to the invention in amounts of 0.1 to 10% by weight, based on the entire preparation. Amounts of 0.1 to 5% by weight are particularly preferred.
  • 2-pyrrolidinone-5-carboxylic acid and / or their derivatives can be used in the preparations of the process according to the invention.
  • the sodium, potassium, calcium, magnesium or ammonium salts are preferred, in which the ammonium ion carries one to three C 1 -C 4 -alkyl groups in addition to hydrogen.
  • the sodium salt is very particularly preferred.
  • the amounts used in the preparations according to the invention are 0.05 to 10% by weight, based on the preparation as a whole, particularly preferably 0.1 to 5 and in particular 0.1 to 3% by weight.
  • vitamins, provitamins and vitamin precursors and their derivatives has also proven to be advantageous.
  • 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.
  • the group of substances called vitamin A includes retinol (vitamin Ai) and 3,4-didehydroretinol (vitamin A 2 ).
  • the ß-carotene is the provitamin of retinol.
  • vitamin A acid and its esters, vitamin A aldehyde and vitamin are used as vitamin A components A alcohol and its esters such as the palmitate and the acetate into consideration.
  • 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. According to the invention, preference is given to nicotinamide, which is preferably present in the preparations used according to the invention in amounts of 0.05 to 1% by weight, based on the preparation as a whole.
  • 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 panthenol 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 Bs type mentioned are preferably present in the preparations used according to the invention in amounts of 0.05-10% by weight, based on the preparation as a whole. 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 preferably used in the preparations used according to the invention in amounts of 0.1 to 3% by weight, based on the entire preparation. 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 preparations used according to the invention in amounts of 0.05-1% by weight, based on the preparation as a whole ,
  • vitamin F usually means essential fatty acids, in particular linoleic acid, linolenic acid and arachidonic acid.
  • Vitamin H is the compound (3aS, 4S, 6aR) -2-oxohexa- hydrothienol [3,4-d] imidazole-4-valeric acid, for which the trivial name biotin has now become established.
  • Biotin is contained in the preparations 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 preparations used according to the invention preferably contain vitamins, provitamins and vitamin precursors from groups A, B, E and H.
  • Panthenol, pantolactone, pyridoxine and its derivatives as well as nicotinamide and biotin are particularly preferred.
  • plant extracts can be used in the preparations of the method according to the invention.
  • 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.
  • 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 diluted form, they usually contain about 2 to 80% by weight of active substance and, as a solvent, the extractant or extractant mixture used in their extraction.
  • hydroxycarboxylic acids and in particular the dihydroxy, trihydroxy and
  • polyhydroxycarboxylic acids as well as the dihydroxy, trihydroxy and polyhydroxy di, tri and polycarboxylic acids. It has been shown here that, in addition to the hydroxycarboxylic acids, the hydroxycarboxylic acid esters and the mixtures of hydroxycarboxylic acids and their esters as well as polymeric hydroxycarboxylic acids and their esters can be very particularly preferred.
  • Preferred hydroxycarboxylic acid esters are, for example, 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.
  • esters are primary, linear or branched aliphatic alcohols with 8-22 carbon atoms, for example fatty alcohols or synthetic fatty alcohols.
  • the esters of C12-C15 fatty alcohols are particularly preferred. Esters of this type are commercially available, eg under the trademark Cosmacol® ® EniChem, Augusta Industriale.
  • Particularly preferred polyhydroxy polycarboxylic acids are polylactic acid and poly-tartaric acid and their esters.
  • emulsifiers are used in the preparations of the process according to the invention.
  • 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.
  • An emulsion is to be understood as a droplet-like distribution (dispersion) of a liquid in another liquid with the use of energy to create stabilizing phase interfaces 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,
  • Sterols are understood to be a group of steroids which carry a hydroxyl group on the C atom 3 of the steroid structure and are isolated both from animal tissue (zoosterols) and from vegetable fats (phytosterols). Examples of zoosterols are cholesterol and lanosterol. Examples of suitable phytosterols are ergosterol, stigmasterol and sitosterol. Sterols, the so-called mycosterols, are also isolated from mushrooms and yeasts.
  • glucose phospholipids include primarily the glucose phospholipids, e.g. as lecithins or phosphididylcholines 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)
  • the preparations according to the invention preferably contain the emulsifiers in amounts of 0.1-25% by weight, in particular 0.1-3% by weight, based on the entire preparation.
  • the preparations 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 York, in the Römpp-Lexikon Chemie (Ed. J. Falbe, M. Regitz) (1997), page 1764, contain the definitions listed.
  • Nonionic emulsifiers with an HLB value of 10-15 can be particularly preferred according to the invention.
  • Heterocyclic compounds such as derivatives of imidazole, pyrrolidine, piperidine, dioxolane, dioxane, morpholine and piperazine can be used as further active substances.
  • Derivatives of these compounds are also suitable, for example the C 1-4 alkyl derivatives, Derivatives and C- aminoalkyl derivatives.
  • Preferred substituents which can be positioned both on carbon atoms and on nitrogen atoms of the heterocyclic ring systems are methyl, ethyl, ⁇ -hydroxyethyl and ⁇ -aminoethyl groups. These derivatives preferably contain 1 or 2 of these substituents.
  • heterocyclic compounds preferred according to the invention are, for example, 1-methylimidazole, 2-methylimidazole, 4 (5) -methylimidazole, 1,2-dimethylimidazole, 2-ethylimidazole, 2-isopropylimidazole, N-methylpyrrolidone, 1-methylpiperidine, 4-methylpiperidine, 2- Ethyl piperidine, 4-methylmorpholine, 4- (2-hydroxyethyl) morpholine, 1-ethylpiperazine, 1- (2-hydroxyethyl) piperazine, 1- (2-aminoethyl) piperazine.
  • Imidazole derivatives preferred according to the invention are biotin, hydantoin and benzimidazole.
  • the mono- and dialkylimidazoles, biotin and hydantoin are particularly preferred.
  • heterocyclic compounds are present in the preparations according to the invention in amounts of 0.5 to 10% by weight, based on the total preparation. Amounts of 2 to 6% by weight have proven to be particularly suitable.
  • amino acids and amino acid derivatives according to the invention are amino acids and amino acid derivatives according to the invention. From the group of amino acids, arginine, citrulline, histidine, ornithine and lysine in particular have proven to be suitable according to the invention.
  • the amino acids can be used both as free amino acids and as salts, e.g. B. can be used as hydrochloride.
  • oligopeptides consisting of an average of 2-3 amino acids, which have a high proportion (> 50%, in particular> 70%) of the amino acids mentioned, have also proven to be usable according to the invention.
  • Arginine and its salts and arginine-rich oligopeptides are particularly preferred according to the invention.
  • amino acids or derivatives are contained in the preparations according to the invention in amounts of 0.5 to 10% by weight, based on the total preparation. Amounts of 2 to 6% by weight have proven to be particularly suitable.
  • the preparations according to the invention contain penetration aids and / or swelling agents.
  • penetration aids and / or swelling agents include, for example, urea and urea derivatives, guanidine and its derivatives, arginine and its derivatives, water glass, imidazole and its derivatives, histidine and its derivatives, benzyl alcohol, glycerol, glycol and glycol ethers, propylene glycol and propylene glycol ethers, for example propylene glycol monoethyl ether, carbonates, hydrogen carbonates, Diols and triols, and in particular 1,2-diols and 1,3-diols such as, for example, 1,2-propanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-dodecanediol, 1,3-propanediol, 1st , 6-hexanediol, 1,5-pentanediol
  • the preparations according to the invention can contain waving power-boosting components, in particular urea, imidazole and the diols mentioned above.
  • waving power-boosting components in particular urea, imidazole and the diols mentioned above.
  • the waving-strengthening compounds can be present in the preparations according to the invention in amounts of 0.5 to 5% by weight, based on the entire preparation. Amounts of 1 to 4% by weight have proven to be sufficient, which is why these amounts are particularly preferred.
  • a stabilizer which is customary for stabilizing aqueous hydrogen peroxide preparations is preferably also used.
  • the pH of such aqueous H 2 O 2 preparations which usually contain about 0.5 to 15% by weight, usually about 0.5 to 3% by weight, H 2 0, ready for use, is preferably 2 to 6, especially 2 to 4; it is adjusted by acids, preferably phosphoric acid, phosphonic acids and / or dipicolinic acid.
  • Bromate-based fixatives usually contain the bromates in concentrations of 1 to 10% by weight and the pH of the solutions is adjusted to 4 to 7.
  • fixative concentrates which are diluted with water before use can be particularly preferred.
  • Fixing agents for permanent deformation of keratin fibers are often formulated as solids. They then contain the oxidizing agent in the form of a solid, for example sodium perborate. Only shortly before use, these agents are then mixed with water to form the aqueous preparations.
  • Oxidases such as tyrosinase, ascorbate oxidase and laccase are preferred, but also glucose oxidase, uricase or pyru- vatoxidase. 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 fixing agents according to the invention can also be formulated as solids. They then contain the oxidizing agent in the form of a solid, e.g. Potassium or sodium bromate. It is also possible and preferred to formulate the oxidizing agent as a two-component system. The two components, one of which is preferably a hydrogen peroxide solution or an aqueous solution of another oxidizing agent and the other of which contains the other constituents, in particular caring substances and / or reducing agents, are likewise only mixed shortly before use.
  • Silicones are also suitable as conditioning active substances.
  • Silicones which can be used according to the invention are preferably linear, cyclic or branched silicones selected from the types of cyclomethicones, dimethiconols, dimethiconcopolyols, amodimethicones,
  • Trimethylsilylamodimethicone and Phenyltrimethicone are known to the person skilled in the art under the nomenclature of the Cosmetic, Toiletry and Fragrance Association (CTFA) and in: M.D. Berthiaume, Society of the Cosmetic Chemists Monograph Series, "Silicones in Hair Care", Ed .: L. D. Rhein, ed .: Society of the Cosmetic Chemists, 1997, Chapter 2, which is explicitly referred to here.
  • CTFA Cosmetic, Toiletry and Fragrance Association
  • Polysiloxanes such as dialkyl and alkylarylsiloxanes, for example dimethylpolysiloxane and methylphenylpolysiloxane, and their alkoxylated analogs, analogs terminated with hydroxyl groups and quaternized analogues, and cyclic siloxanes.
  • silicones with the INCI names Dimethicone, PEG-12 Dimethicone, PEG / PPG-18/18 Dimethicone, Cyclomethicone, Dimethiconol, Quatemium-80 and Amodimethicone as well as their mixtures are particularly preferred silicones.
  • silicones examples include those from Dow Corning under the names DC 190 (INCI name: PEG / PPG-18/18 Dimethicone), DC 193 (INCI- Name: PEG-12 Dimethicone), DC 200, DC1401 (INCI name: Cyclomethicone, Dimethiconol) and DC 1403 (INCI name: Dimethicone, Dimethiconol) and the commercial products DC 244 (INCI name: Cyclomethicone), DC 344 (INCI name: Cyclomethicone) and DC 345 (INCI name: Cyclomethicone) from Dow Corning, Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone, Dow Corning 929 emulsion (containing a hydroxylamino-modified silicone, which also is called Amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker), Abil Quat 3270
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such. B. bentonite or fully synthetic hydrocolloids such.
  • hair-conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins, and silicone oils,
  • Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol,
  • active ingredients which improve fiber structure in particular mono-, di- and oligosaccharides, such as, for example, glucose, galactose, fructose, fructose and lactose,
  • - conditioning agents such as paraffin oils, vegetable oils, e.g. B. sunflower oil, orange oil, almond oil, wheat germ oil and peach seed oil as well quaternized amines such as methyl 1-alkylamidoethyl-2-alkylimidazolinium methosulfate,
  • anti-dandruff agents such as piroctone olamine, zinc omadine and climbazol
  • - opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers
  • Pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate,
  • Blowing agents such as propane-butane mixtures, N 2 O, dimethyl ether, C0 2 and air,
  • the preparations according to the invention can be used in hair care products such as shampoos, conditioners, rinses, aerosols and gels, or else in textile or fiber treatment products in the form of detergents, fabric softeners, impregnations and finishes.
  • the polysulfide (I) and the reducing agent can be applied successively to the fiber to be treated in any order or after prior mixing of the polysulfide (I) and reducing agent.
  • the polysulfide (I) and the reducing agent, and possibly also the oxidizing agent and, if appropriate, further constituents of the preparations used are provided separately from one another in a kit-of-parts.
  • the individual components can be mixed, dissolved, dispersed or emulsified in a suitable carrier.
  • the kit-of-parts preferably consists of a preparation containing the polysulfide (I) and / or at least one preparation as described in the preceding text as preparations V, Z, R or O, at least one of which is contained in the kit-of preparations containing a polysulfide of formula (I).
  • the invention thus furthermore relates to a kit for use in a process according to the invention, comprising at least (a) one of the preparations described above, comprising at least one polysulfide of the formula (I), and (b) a preparation comprising a reducing agent, in particular a keratin-reducing agent Connection, the preparations being packaged separately.
  • the invention also relates to a kit for use in a method according to the invention, which additionally comprises a preparation comprising an oxidizing agent.
  • the present invention further relates to a fiber, in particular a keratinic fiber, which is obtainable by the process described above.
  • Another object of the invention is the use of a polysulfide of the formula (I) for the restructuring of keratin fibers, in particular hair, the restructuring in particular comprising fiber reinforcement.
  • Synthesis example 1 Preparation of a polysulfide of formula (I) from cystine and succinic acid dichloride by interfacial condensation
  • Synthesis example 2 Preparation of a polysulfide of formula (I) from cystine and succinic acid dichloride by interfacial condensation
  • Synthesis example 3 Preparation of a polysulfide of formula (I) from cystine and succinic acid dichloride by interfacial condensation
  • Succinic dichloride (0.05 mol) was dissolved in 50 ml dichloromethane.
  • Cystine (0.05 mol) was dissolved in 100 ml of 2N NaOH, placed in the reaction vessel and cooled with ice water. The two solutions were given together and under dispersed vigorous stirring. The formation of a solid was observed at the interface. After the reaction was complete, the solid was isolated and the organic phase was separated from the aqueous phase. The aqueous phase was then combined with the solid and freeze-dried. Yield: 15.3 g of beige-yellow powder. The product obtained contained cystine and succinic acid.
  • Synthesis example 4 Preparation of a polysulfide of formula (I) from cystine dimethyl ester and succinic acid dichloride
  • the synthesis was carried out in accordance with US 5646239.
  • the polysulfide polymethyl ester “stage I” was first obtained (corresponding to US 5646239, example 2), which was then saponified to give the polysulfide “stage II” (corresponding to US 5646239, example 3).
  • tension values, gradients, elastic modulus, elongation at break and tensile strength at break of the wet hair were determined with the aid of a tension-stretching device from Dia-Stron (MTT 670).
  • the hair cross-sectional area of the wet individual hair was determined by means of contactless projection measurement using laser technology known in the prior art.
  • a universal dimension meter of the type UMD5000A from Zimmer was used for this.
  • the hair is then rinsed with water for 5 minutes.
  • Reference example untreated, i.e. healthy and undamaged hair.
  • the damage to the hair by the permanent wave method is clearly evident in the increase in the hair cross-sectional area, the reduction in the modulus of elasticity, the gradient, the tension values and the work values. An increase in the elongation at break can also be observed.
  • composition according to the invention The influence of the composition according to the invention on hair was investigated by means of tensile strain measurement in the wet state.
  • Example according to the invention double-crimped with addition of 2% product from synthesis example 1
  • Example according to the invention double-permed hair with 1% product from synthesis example 1 in the cold wave, as described under 3.2: steps a) with 1% product from synthesis example 1, b), c); Repetition of steps a) with 1% product from synthesis example 1, b), c); then d) and e).
  • composition according to the invention The influence of the composition according to the invention on hair was investigated by means of tensile strain measurement in the wet state.
  • Example according to the invention double-crimped with addition of 1% product from synthesis example 1
  • Example according to the invention double-crimped with addition of 1% product from synthesis example 1
  • Example according to the invention double-permed hair with 1% product
  • composition according to the invention The influence of the composition according to the invention on hair was investigated by means of tensile strain measurement in the wet state.
  • Example according to the invention double-permed hair with 1% succinic acid in the cold wave, as described under 3.2: steps f) with 1% succinic acid, g), c); Repetition of steps f) with 1% succinic acid, g), c); then d) and e).
  • Example 3.9 the cold well formulation described under 3.2 f) was replaced by the following cold well formulation: 17% ammonium thioglycolate (71%), 0.3% Turpinal SL, 2.5% ammonia (25%), 5% ammonium hydrogen carbonate, 1% Cremophor RH 40, 1% Lamepon S, 0.5% perfume, 0.1% Gluadin WQ (Laurdimonium hydroxypropyl hydrolyzed wheat protein) , 0.1% Merquat 100 (polydimethyldiallylammonium chloride), water ad 100.
  • Example according to the invention twice with a cold wave with the addition of 1% product from synthesis example 3 t-test, two-sided, in pairs
  • Example according to the invention twice with cold wave with addition of 1% product from synthesis example 3 3.64E-05 8.83E-04 1.27E-04 4.11 E-03 t-test, two-sided, in pairs
  • stage I shows a clear hair strengthening compared to the reference.
  • the tension and work values as well as the gradient and the modulus of elasticity are significantly increased.
  • the hair cross-sectional area and the elongation at break are significantly smaller.
  • stage II shows a positive effect, since the tension and work values, as well as the gradient and the modulus of elasticity increase significantly.
  • 1% product from synthesis example 1 was formulated into a cold wave pH 8.4 and the hair was treated with it.
  • a cold wave pH 8.4 was used for comparison. The cold wave was applied to dry hair.
  • Rinse time 10 min with 38 ° C warm water using a hand shower
  • Rinse time 10 min with 38 ° C warm water using a hand shower
  • test strands were tested in the same way by all panelists in pairs in a sensorial comparison.
  • the panelists assess the individual parameters on a quantitative
  • the attributes differ in the direction of the expression that is underlined in the tables.
  • Example recipe 1 waving agent
  • Example recipe 2 waving agent
  • Example formulation 3 2-phase 2-component perm a) basic well lotion aa) aqueous phase ammonia 25% 0.9 inventive polysulfide 1) 1 Merquat 100 4) 0.1 ammonium hydrogen carbonate 5.5 water ad 100 bb) oil phase Perfume 10 CI. 61565 0.002 Dow Corning 345 5) ad 100 b) activator ammonium thiolactate 70% 21 Ammonium thioglycolate 71% 57 Turpinal SL 1 Eumulgin L 6) 4 water ad 100
  • 57.5 mL basic well lotion consisting of 52 mL aqueous phase and 5.5 mL oil phase, and 22.5 mL activator are mixed before use to give 80 mL ready-to-use perm.
  • Example formulation 4 Alkaline pretreatment and / or intermediate treatment Dow Corning 939 7) 2 ethanol 96% 32 phytantriol 0.1 Merquat 100 0.1 monoethanolamine 0.5 polysulfide 1) 1 water ad 100
  • Example formulation 5 Alkaline, reductive pretreatment and / or intermediate treatment Dow Corning 939 2 ethanol 96% DEP denatures 32 phytantriol 0.1 Merquat 100 0.1 ammonia 25% 0.5 ammonium thioglycolate 71% 3 polysulfide 1) 1 according to the invention Water ad 100
  • Example recipe 6 Ready-to-use perm for normal hair Ammonium thioglycolate 71% 18 Turpinal SL 0.3 Ammonia 25% 2 Ammonium bicarbonate 8 Cremophor RH 40 1 Lamepon S 1 Perfume 0.5 Gluadin WQ 8) 0.1 Merquat 100 0.1 Polysulfide 1) 0.5 water ad 100
  • Example recipe 7 Ready-to-use perm for colored hair Ammonium thioglycolate 71% 11 Turpinal SL 0.3 Ammonia 25% 2 Ammonium hydrogen carbonate 4 Cremophor RH 40 1 Lamepon S 1 Perfume 0.5 Gluadin WQ 0.2 Merquat 100 0.2 Polysulfide 1) 1 according to the invention Water ad 100
  • polysulfide according to the invention for example product from one of synthesis examples 1 to 3
  • poly (dimethyldiallylammonium chloride) (40% active substance, INCI name Polyquaternium-6, CHEMVIRON)

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Abstract

La présente invention concerne un procédé pour restructurer des fibres de kératine. Ce procédé consiste à mettre en contact une fibre de kératine de manière simultanée ou consécutive avec (a) un agent de réduction et une préparation aqueuse d'au moins un polysulfure de formule (I) dans laquelle R3 représente hydroxy ou le radical (II) R4 représente hydrogène ou le radical (III), A représente une liaison ou un radical hydrocarbure bivalent saturé ou mono- ou poly-insaturé, aliphatique ou aromatique, avec de 1 à 20 atomes de carbone, qui peut être substitué avec un ou plusieurs groupes halogène, hydroxy ou carboxy, la liaison la plus courte entre les deux groupes carbonyle voisins du groupe A étant constituée d'au maximum 12 atomes de carbone et R1 et R2 peuvent être identiques ou différents et sont sélectionnés parmi R5O- et (IV), R5 représentant hydrogène ou un groupe alkyle avec de 1 à 6 atomes de carbone, n étant un nombre entier qui va de 1 à 100 et un ou plusieurs groupes carboxyle pouvant se présenter sous forme d'un ou de plusieurs de ses sels, puis (b) avec un agent d'oxydation. La présente invention concerne également des préparations à utiliser dans le cadre de ce procédé.
EP05731059A 2004-05-18 2005-04-08 Procede et composition pour restructurer des fibres de keratine Withdrawn EP1747045A1 (fr)

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DE102004024509A DE102004024509B4 (de) 2004-05-18 2004-05-18 Verfahren und Zubereitungen zur Restrukturierung von Haaren
PCT/EP2005/003697 WO2005115315A1 (fr) 2004-05-18 2005-04-08 Procede et composition pour restructurer des fibres de keratine

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EP1797861A1 (fr) * 2005-12-16 2007-06-20 KPSS-Kao Professional Salon Services GmbH Composition pour la mise en forme permanente des cheveux humains
EP2011543A1 (fr) * 2007-06-26 2009-01-07 KPSS-Kao Professional Salon Services GmbH Composition de mise en forme permanente de cheveux humains
EP2011478A1 (fr) * 2007-06-26 2009-01-07 KPSS-Kao Professional Salon Services GmbH Composition de mise en forme permanente de cheveux humains
EP2011479A1 (fr) * 2007-06-26 2009-01-07 KPSS-Kao Professional Salon Services GmbH Composition de mise en forme permanente de cheveux humains
CN110302085A (zh) * 2008-02-08 2019-10-08 高露洁-棕榄公司 精氨酸盐及其治疗口腔疾病的用途
ES2749198T3 (es) * 2008-12-05 2020-03-19 SWISS KRONO Tec AG Procedimiento para fabricar materiales a base de madera de productos de la trituración que contienen lignocelulosa y tales materiales a base de madera
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DE102004024509B4 (de) 2006-06-08
DE102004024509A1 (de) 2005-12-15
WO2005115315A1 (fr) 2005-12-08
AU2005247069A1 (en) 2005-12-08
RU2006144711A (ru) 2008-06-27
WO2005115315A8 (fr) 2007-02-01

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