EP3052075A1 - Agents de soins capillaires contenant des oligopeptides et des esters d'acide hyaluronique - Google Patents

Agents de soins capillaires contenant des oligopeptides et des esters d'acide hyaluronique

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Publication number
EP3052075A1
EP3052075A1 EP14799663.1A EP14799663A EP3052075A1 EP 3052075 A1 EP3052075 A1 EP 3052075A1 EP 14799663 A EP14799663 A EP 14799663A EP 3052075 A1 EP3052075 A1 EP 3052075A1
Authority
EP
European Patent Office
Prior art keywords
glu
weight
hair treatment
hair
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.)
Withdrawn
Application number
EP14799663.1A
Other languages
German (de)
English (en)
Inventor
Volker Scheunemann
Erik Schulze Zur Wiesche
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 EP3052075A1 publication Critical patent/EP3052075A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8135—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers, e.g. vinyl esters (polyvinylacetate)
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • 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
    • A61Q5/002—Preparations for repairing the hair, e.g. hair cure
    • 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
    • A61Q5/02—Preparations for cleaning 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/591—Mixtures of compounds not provided for by any of the codes A61K2800/592 - A61K2800/596
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions

Definitions

  • the invention relates to hair treatment compositions, in particular so-called conditioners, with a combination of active ingredients for gentle and effective hair care.
  • the hair is treated with special active ingredients, for example quaternary ammonium salts or special polymers, usually in the form of a rinse.
  • special active ingredients for example quaternary ammonium salts or special polymers, usually in the form of a rinse.
  • this treatment improves the combability, the hold and the fullness of the hair and reduces the split rate.
  • oligopeptides for the care of keratinic fibers is known, for example, from WO2010 / 026010 A1.
  • oligopeptides with the sequence Tyr-Glu-Glu-Glu-Ile-Arg-Val-Leu are disclosed as particularly suitable for hair care.
  • Hyaluronic acid and its derivatives are popular ingredients in skin cosmetics. They are also being used increasingly in hair cosmetics.
  • WO2009 / 080220 A1 discloses polysaccharides esterified at the hydroxyl function with glucosamine or galactoamine residues, which are e.g. selected from lipoic acid esterified hyaluronic acid. These substances have film-forming properties that strengthen the hair follicles and protect the hair against splitting and external influences from free radicals. In tests, improved softness, lightness, curl retention, and a reduction in brittleness have been demonstrated.
  • a first subject of the present invention are hair treatment compositions containing - in each case based on their weight - a) 0.0001 to 10 wt .-% of at least one oligopeptide, the at least one Amino Acid Sequence Glu-Glu-Glu
  • amino group may be free or protonated and the carboxy groups may be free or deprotonated
  • the parenthesized hydrogen atom of the amino group, as well as the bracketed hydroxy group of the acid function means that the respective groups can be present as such (then it is an oligopeptide with the relevant number of amino acids as shown (see above) Formula 3) or that the amino acid sequence is present in an oligopeptide, which comprises even more amino acids - depending on where the other amino acid (s) is / are bound, the parenthetical components of the above formula by the / are the other Replaced amino acid residue (s).
  • Hair treatment compositions for the purposes of the present invention are, for example, hair shampoos, hair conditioners, conditioning shampoos, hairsprays, hair conditioners, hair treatments, hair wraps, hair tonics, perming solutions, hair dye shampoos, hair dyes, hair fixatives, hair dressings, hairstyling preparations, hair lotions, mousses, hair gels , Hair waxes or their combinations.
  • agents according to the invention are preferably those agents which the man uses anyway.
  • Preferred agents according to the invention are therefore shampoos, conditioners or hair tonics.
  • the hair treatment compositions according to the invention contain, by weight, 0.0001 to 10% by weight of at least one oligopeptide containing at least one amino acid residue Glu-Glu-Glu, i. has at least three consecutive glutamic acids.
  • Oligopeptides in the sense of the present application are acid amide-like linked by peptide bonds condensation products of amino acids comprising at least 3 and a maximum of 25 amino acids
  • the oligopeptide comprises 5 to 15 Amino acids, preferably 6 to 13 amino acids, particularly preferably 7 to 12 amino acids and in particular 8, 9 or 10 amino acids.
  • the molecular weight of the oligopeptide contained in the agents of the invention may vary.
  • Hair treatment compositions preferred according to the invention are characterized in that the oligopeptide has a molecular weight of from 650 to 3000 Da, preferably from 750 to 2500 Da, particularly preferably from 850 to 2000 Da and in particular from 1000 to 1600 Da.
  • preferred hair treatment compositions according to the invention are characterized in that the oligopeptide comprises 5 to 15 amino acids, preferably 6 to 13 amino acids, more preferably 7 to 12 amino acids and especially 8, 9 or 10 amino acids and a molecular weight of 650 to 3000 Da, preferably 750 to 2500 Da, more preferably from 850 to 2000 Da and in particular from 1000 to 1600 Da.
  • oligopeptides which do not consist solely of the three glutamic acids but have further amino acids bound to this sequence.
  • These other amino acids are preferably selected from certain amino acids, while certain other representatives are less preferred in the present invention.
  • oligopeptides used in the agents according to the invention contain no methionine.
  • oligopeptides used in the agents according to the invention contain no cysteine and / or cystine.
  • oligopeptides used in the agents according to the invention contain no aspartic acid and / or asparagine.
  • oligopeptides used in the agents according to the invention contain no serine and / or threonine.
  • oligopeptides used in the agents according to the invention contain tyrosine.
  • oligopeptides used in the agents according to the invention contain leucine.
  • oligopeptides used in the agents according to the invention contain isoleucine.
  • oligopeptides used in the agents according to the invention contain arginine.
  • oligopeptides used in the agents according to the invention contain valine.
  • a particularly preferred oligopeptide additionally contains tyrosine, which is preferably linked via its acid function to the Glu-Glu-Glu sequence.
  • Hair treatment agents which are preferred according to the invention are therefore characterized in that the oligopeptide contained in them has at least one amino acid sequence Tyr-Glu-Glu-Glu, where the amino group can be free or protonated and the carboxy groups can be free or deprotonated.
  • Another particularly preferred oligopeptide additionally contains isoleucine, which is preferably linked to the Glu-Glu-Glu sequence via its amino function.
  • Hair-treatment compositions which are preferred according to the invention are therefore characterized in that the oligopeptide contained in them has at least one amino acid sequence Glu-Glu-Glu-Ile, wherein the amino group can be free or protonated and the carboxy groups can be free or deprotonated.
  • Oligopeptides which have both the abovementioned amino acids (tyrosine and isoleucine) are preferred according to the invention.
  • oligopeptides additionally contain arginine, which is preferably bound to isoleucine
  • Still further preferred oligopeptides additionally contain valine, which is preferably bound to the arginine.
  • Hair-treatment agents which are further preferred according to the invention are therefore characterized in that the oligopeptide contained in them has at least one amino acid sequence Tyr-Glu-Glu-Glu-Ile-Arg-Val, the amino groups being free or protonated and the carboxy groups being free or deprotonated can.
  • Still further preferred oligopeptides additionally contain leucine, which is preferably bound to the valine.
  • Further preferred hair treatment compositions according to the invention are characterized in that the oligopeptide contained in them has at least one amino acid sequence Tyr-Glu-Glu-Glu-Ile-Arg-Val-Leu, wherein the amino groups are free or protonated and the carboxy groups are free or deprotonated may be present.
  • Particularly preferred oligopeptides additionally contain leucine, which is preferably bound to the tyrosine.
  • Further preferred hair treatment compositions according to the invention are characterized in that the oligopeptide contained in them has at least one amino acid sequence Leu-Tyr-Glu-Glu-Glu-Ile-Arg-Val-Leu, wherein the amino groups are free or protonated and the Carboxy groups may be present freely or deprotonated.
  • compositions according to the invention containing at least two oligopeptides which satisfy the abovementioned criteria but differ from one another.
  • hair treatment agents containing at least two mutually different oligopetides A and B, both containing the amino acid sequence Glu-Glu-Glu are preferred.
  • Such mutually different oligopeptides A and B correspond to each other in that they carry three consecutive Glu amino acids in their amino acid sequence, but have differences in the upstream or downstream amino acids. Preference is given to mutually different peptides with partial agreement, which may well be greater than in the above-mentioned three amino acids.
  • compositions are characterized in that they contain at least two mutually different oligopeptides A and B, both of which contain the amino acid sequence Glu-Glu-Glu-Ile.
  • hair treatment agents containing at least two mutually different oligopeptides A and B, both containing the amino acid sequence Tyr-Glu-Glu-Glu.
  • Still further preferred hair treatment agents are characterized by containing at least two mutually different oligopetides A and B, both containing the amino acid sequence Glu-Glu-Glu-Ile-Arg.
  • Even more preferred hair treatment agents contain at least two mutually different oligopetides A and B, both containing the amino acid sequence Tyr-Glu-Glu-Glu-Ile.
  • Very particularly preferred hair treatment compositions are characterized in that they contain at least two mutually different oligopeptides A and B, both of which contain the amino acid sequence Glu-Glu-Glu-Ile-Arg.
  • most particularly preferred hair treatment agents contain at least two mutually different oligopetides A and B, both containing the amino acid sequence Tyr-Glu-Glu-Glu-Ile-Arg.
  • hair treatment compositions containing at least two distinct oligopetides A and B, both of which contain the amino acid sequence Glu-Glu-Glu-Ile-Arg-Val are further preferred embodiments of the present invention.
  • hair treatment compositions containing at least two mutually different oligopeptides A and B, both of which contain the amino acid sequence Tyr-Glu-Glu-Glu-Ile-Arg-Val.
  • Still further preferred hair treatment compositions according to the invention contain at least two mutually different oligopetides A and B, both of which contain the amino acid sequence Glu-Glu-Glu-Ile-Arg-Val-Leu. Also, even more preferred hair treatment agents contain at least two mutually different oligopetides A and B, both containing the amino acid sequence Tyr-Glu-Glu-Glu-Ile-Arg-Val-Leu.
  • Particularly preferred hair treatment agents are characterized in that they contain at least two mutually different oligopetides A and B, wherein the oligopeptide A has the amino acid sequence Leu-Tyr-Glu-Glu-Glu-Ile-Arg-Val-Leu, wherein the amino groups are free or protonated and the carboxy groups may be free or deprotonated and the oligopeptide B has the amino acid sequence Tyr-Glu-Glu-Glu-Ile-Arg-Val-Leu, wherein the amino groups are free or protonated and the carboxy groups are free or may be present deprotonated.
  • Very particularly preferred agents of this last-mentioned embodiment contain, based on the weight of the composition, 0.00001 to 1% by weight of oligopeptide A and 0.00001 to 1% by weight of oligopeptide B.
  • Further preferred agents of this last-mentioned embodiment contain -0.00005 to 0.1% by weight of oligopeptide A and 0.00005 to 0.1% by weight of oligopeptide B, based on the weight of the agent.
  • Still further preferred agents of this latter embodiment contain, based on the weight of the agent, from 0.0001 to 0.01% by weight of oligopeptide A and from 0.0001 to 0.001% by weight of oligopeptide B.
  • the use of the abovementioned oligopeptides imparts outstanding properties to the hair treatment compositions according to the invention.
  • the compositions of the invention impart more resilience to the hairs treated with them, resulting in higher tensile strengths of the keratin fibers and a reduction in elasticity loss, e.g. when damaged by atmospheric agents.
  • the particularly preferred oligopeptides also stabilize the moisture balance of the keratinic fibers, so that the combability improves and the aging process is delayed.
  • compositions of the invention are that the moldability and restructurability of keratinic fibers treated with them is improved.
  • oligopeptides used in the context of the present invention which satisfy the abovementioned conditions, can advantageously be obtained from keratinic materials. It is preferred according to the invention that these oligopeptides are used in high proportions, based on the total keratinic peptide content of the agents.
  • Preferred hair treatment agents according to the invention are characterized in that at least 0.1% by weight, preferably at least 0.5% by weight, particularly preferably at least 1% by weight, more preferably at least 2.5% by weight, even more preferred at least 5% by weight and in particular at least 10% by weight of all the keratinic peptides contained in the composition Have amino acid sequence Glu-Glu-Glu.
  • compositions according to the invention are characterized in that at least 0.1 wt .-%, preferably at least 0.5 wt .-%, particularly preferably at least 1 wt .-%, more preferably at least 2.5 wt .-%, even further preferably at least 5% by weight and in particular at least 10% by weight of all the keratinic peptides contained in the middle have the amino acid sequence Glu-Glu-Glu-Ile.
  • Still further preferred hair treatment compositions according to the invention are characterized in that at least 0.1 wt .-%, preferably at least 0.5 wt .-%, particularly preferably at least 1 wt .-%, more preferably at least 2.5 wt .-%, still more preferably at least 5% by weight and in particular at least 10% by weight of all the keratinic peptides contained in the middle have the amino acid sequence Tyr-Glu-Glu-Glu.
  • Particularly preferred hair treatment compositions according to the invention are characterized in that at least 0.1% by weight, preferably at least 0.5% by weight, more preferably at least 1% by weight, more preferably at least 2.5% by weight, still further preferably at least 5% by weight and in particular at least 10% by weight of all the keratinic peptides contained in the middle have the amino acid sequence Tyr-Glu-Glu-Glu-Ile.
  • Very particularly preferred hair treatment compositions according to the invention are characterized in that at least 0.1% by weight, preferably at least 0.5% by weight, more preferably at least 1% by weight, more preferably at least 2.5% by weight, still more preferably at least 5% by weight and in particular at least 10% by weight of all the keratinic peptides contained in the middle have the amino acid sequence Tyr-Glu-Glu-Glu-Ile-Arg.
  • Still further preferred hair treatment compositions according to the invention are characterized in that at least 0.1 wt .-%, preferably at least 0.5 wt .-%, particularly preferably at least 1 wt .-%, more preferably at least 2.5 wt .-%, still more preferably at least 5% by weight and in particular at least 10% by weight of all the keratinic peptides contained in the middle have the amino acid sequence Tyr-Glu-Glu-Glu-Ile-Arg-Val.
  • Particularly preferred hair treatment compositions according to the invention are characterized in that at least 0.1% by weight, preferably at least 0.5% by weight, more preferably at least 1% by weight, more preferably at least 2.5% by weight, still further preferably at least 5% by weight and in particular at least 10% by weight of all the keratinic peptides contained in the middle have the amino acid sequence Tyr-Glu-Glu-Glu-Ile-Arg-Val-Leu.
  • the abovementioned conditions relate to the total content of the agents according to the invention to peptides which originate from keratinic materials.
  • oligopeptides of keratinic origin in addition to the oligopeptides of keratinic origin, of course, other peptides and / or protenihydrolysates can be used, for example from other native sources.
  • wheat protein hydrolysates in addition to the additional use of wheat protein hydrolysates is preferred, see below.
  • the hair treatment compositions according to the invention contain as the second essential ingredient - based on their weight - 0.0001 to 10 wt .-% of at least one ester of hyaluronic acid with lipoic acid, formic acid or mixtures thereof.
  • the agents according to the invention may accordingly contain esters of hyaluronic acid with lipoic acid, esters of hyaluronic acid with formic acid or mixed esters of hyaluronic acid with lipoic acid and formic acid.
  • esters of hyaluronic acid with lipoic acid esters of hyaluronic acid with formic acid or mixed esters of hyaluronic acid with lipoic acid and formic acid.
  • esters of hyaluronic acid with lipoic acid esters of hyaluronic acid with formic acid or mixed esters of hyaluronic acid with lipoic acid and formic acid.
  • esters of hyaluronic acid with lipoic acid esters of hyaluronic acid with formic acid
  • mixed esters of hyaluronic acid with lipoic acid and formic acid are particularly preferred in view of their effectiveness in the combination according to the invention.
  • Hair treatment agents preferred according to the invention are characterized in that they contain 0.0005 to 7.5% by weight, preferably 0.001 to 6% by weight, more preferably 0.005 to 5% by weight, more preferably 0.01 to 4% by weight. % and in particular 0.1 to 3 wt .-% of at least one ester of hyaluronic acid with lipoic acid, formic acid or mixtures thereof of the formula (I)
  • X is selected from H, Na and K
  • R1, R2, R3 and R4 are independently selected from -H, -C (0) -H and
  • the hyaluronic acid has 4 esterifiable hydroxyl groups, so that, based on the individual repeating unit, the following hyaluronic acid esters can be used according to the invention:
  • Hyaluronic acid esters in which an OH group is esterified with lipoic acid in which an OH group is esterified with lipoic acid
  • Hyaluronic acid esters in which two OH groups are esterified with lipoic acid in which two OH groups are esterified with lipoic acid
  • Hyaluronic acid esters in which three OH groups are esterified with lipoic acid
  • Hyaluronic acid esters in which four OH groups are esterified with lipoic acid in which four OH groups are esterified with lipoic acid
  • Hyaluronic acid esters in which an OH group is esterified with formic acid in which an OH group is esterified with formic acid
  • Hyaluronic acid esters in which two OH groups are esterified with formic acid
  • Hyaluronic acid esters in which three OH groups are esterified with formic acid Hyaluronic acid esters in which four OH groups are esterified with formic acid
  • Hyaluronic acid esters in which an OH group is esterified with lipoic acid and an OH group with formic acid,
  • Hyaluronic acid esters in which one OH group is esterified with lipoic acid and two OH groups with formic acid,
  • Hyaluronic acid esters in which one OH group is esterified with lipoic acid and three OH groups with formic acid,
  • Hyaluronic acid esters in which two OH groups are esterified with lipoic acid and one OH group with formic acid,
  • Hyaluronic acid esters in which two OH groups are esterified with lipoic acid and two OH groups with formic acid,
  • Hyaluronic acid esters in which three OH groups with lipoic acid and one OH group with
  • Formic acid are esterified.
  • esterification takes place statistically, so that individual monomer units can remain completely unesterified. It is inventively preferred if a certain part of the esterifiable OH groups is esterified with lipoic acid, regardless of how they are distributed to the hyaluronic acid molecule.
  • Hair treatment agents preferred according to the invention are characterized in that the degree of esterification of the OH groups with lipoic acid is 0.1 to 0.5 mol / mol, preferably 0.125 to 0.45 mol / mol, more preferably 0.2 to 0.4 mol / mol, even more preferably 0.25 to 0.35 mol / mol and in particular 0.27 to 0.33 mol / mol.
  • most preferably 27 to 33 OH groups are esterified with lipoic acid on 25 repetition units (with 100 OH groups).
  • esterifiable OH groups is esterified with formic acid, likewise irrespective of how they are distributed over the hyaluronic acid molecule.
  • Hair treatment agents which are preferred according to the invention are characterized in that the degree of esterification of the OH groups with formic acid is 0.001 to 0.5 mol / mol, preferably 0.002 to 0.4 mol / mol, more preferably 0.005 to 0.3 mol / mol, even more preferably 0 , 0075 to 0.25 mol / mol and in particular 0.01 to 0.2 mol / mol.
  • most preferably one to 20 OH groups are esterified with formic acid to 25 repeating units (having 100 OH groups).
  • Particularly preferred hair treatment compositions according to the invention are characterized in that the degree of esterification of the OH groups with lipoic acid is 0.1 to 0.5 mol / mol, preferably 0.125 to 0.45 mol / mol, more preferably 0.2 to 0.4 mol / mol , even more preferably 0.25 to 0.35 mol / mol and in particular 0.27 to 0.33 mol / mol and the degree of esterification of the OH groups with formic acid 0.001 to 0.5 mol / mol, preferably 0.002 to 0.4 mol / mol, more preferably 0.005 to 0.3 mol / mol, even more preferably 0.0075 to 0.25 mol / mol and in particular 0.01 to 0.2 mol / mol.
  • most preferably 27 to 33 OH groups are esterified with lipoic acid and one to 20 OH groups are esterified with formic acid over 25 repetition units (with 100
  • preferred hair treatment compositions contain from 0.0005 to 7.5% by weight, preferably from 0.001 to 6% by weight, more preferably from 0.005 to 5% by weight, more preferably from 0.01 to 4% by weight and in particular 0, 1 to 3 wt .-% of at least one ester of hyaluronic acid with lipoic acid having at least one recurring unit of the formula (II)
  • X is selected from H, Na and K
  • n stands for numbers from 1 to 10000
  • R1, R2 and R3 are independently selected from -H, -C (0) -H and
  • compositions according to the invention contain 0.0005 to 7.5 wt .-%, preferably 0.001 to 6 wt .-%, more preferably 0.005 to 5 wt .-%, more preferably 0.01 to 4 wt .-% and in particular 0 , 1 to 3% by weight of at least one ester of hyaluronic acid with lipoic acid of the formula (IIa)
  • X is selected from H, Na and K
  • n and m are numbers from 100 to 10000, and
  • R1, R2, R3 and R4 are independently selected from -H, -C (0) -H and
  • the recurring units with the indices n and m need not necessarily be bound together as a block, but rather they may be present in a statically distributed manner over the entire molecule.
  • Still further preferred hair treatment compositions according to the invention contain from 0.0005 to 7.5 wt .-%, preferably 0.001 to 6 wt .-%, more preferably 0.005 to 5 wt .-%, more preferably 0.01 to 4 wt .-% and in particular 0.1 to 3% by weight of at least one ester of hyaluronic acid with lipoic acid of the formula (IIb)
  • n, m and o stand for numbers from 100 to 10000
  • R1, R2, R3 and R4 are independently selected from -H, -C (0) -H and
  • the recurring units with the indices n, m and o need not necessarily be bound together as a block, but rather they can be present in a statically distributed manner over the entire molecule.
  • compositions according to the invention contain 0.0005 to 7.5 wt .-%, preferably 0.001 to 6 wt .-%, more preferably 0.005 to 5 wt .-%, more preferably 0.01 to 4 wt .-% and in particular 0 , 1 to 3 wt .-% of at least one ester of hyaluronic acid with lipoic acid having at least one recurring unit of the formula (III)
  • X is selected from H, Na and K
  • n stands for numbers from 1 to 10000
  • R1, R2 and R4 are independently selected from -H, -C (O) -H and
  • compositions according to the invention contain 0.0005 to 7.5 wt .-%, preferably 0.001 to 6 wt .-%, more preferably 0.005 to 5 wt .-%, more preferably 0.01 to 4 wt .-% and in particular 0 , 1 to 3% by weight of at least one ester of hyaluronic acid with lipoic acid of the formula (IIIa)
  • X is selected from H, Na and K
  • n and m are numbers from 100 to 10000, and
  • R1, R2, R3 and R4 are independently selected from -H, -C (0) -H and
  • the repeating units with the indices n and m do not necessarily have to be bound together as a block; rather, they can be statically distributed over the entire molecule.
  • Still further preferred hair treatment compositions according to the invention contain from 0.0005 to 7.5 wt .-%, preferably 0.001 to 6 wt .-%, more preferably 0.005 to 5 wt .-%, more preferably 0.01 to 4 wt .-% and in particular 0.1 to 3% by weight of at least one ester of hyaluronic acid with lipoic acid of the formula (IIIb)
  • X is selected from H, Na and K
  • n, m and o stand for numbers from 100 to 10000
  • R1, R2, R3 and R4 are independently selected from -H, -C (0) -H and
  • the repeating units with the indices n, m and o do not necessarily have to be bound together as a block, but rather they can be present in a statically distributed manner over the entire molecule.
  • compositions according to the invention contain 0.0005 to 7.5 wt .-%, preferably 0.001 to 6 wt .-%, more preferably 0.005 to 5 wt .-%, more preferably 0.01 to 4 wt .-% and in particular 0 , 1 to 3 wt .-% of at least one ester of hyaluronic acid with lipoic acid having at least one recurring unit of the formula (IV)
  • X is selected from H, Na and K
  • n stands for numbers from 1 to 10000
  • R1, R3 and R4 are independently selected from -H, -C (0) -H and
  • compositions according to the invention contain 0.0005 to 7.5 wt .-%, preferably 0.001 to 6 wt .-%, more preferably 0.005 to 5 wt .-%, more preferably 0.01 to 4 wt .-% and in particular 0 , 1 to 3% by weight of at least one ester of hyaluronic acid with lipoic acid of the formula (IVa)
  • X is selected from H, Na and K
  • n and m are numbers from 100 to 10000, and
  • R1, R2, R3 and R4 are independently selected from -H, -C (0) -H and
  • the repeating units with the indices n and m do not necessarily have to be bound together as a block, but rather they can be present in a statically distributed manner over the entire molecule.
  • Still further preferred hair treatment compositions according to the invention contain from 0.0005 to 7.5 wt .-%, preferably 0.001 to 6 wt .-%, more preferably 0.005 to 5 wt .-%, more preferably 0.01 to 4 wt .-% and in particular 0.1 to 3% by weight of at least one ester of hyaluronic acid with lipoic acid of the formula (IVb)
  • n, m and o stand for numbers from 100 to 10000
  • R1, R2, R3 and R4 are independently selected from -H, -C (0) -H and
  • the repeating units with the indices n, m and o need not necessarily be bound as a block to each other, but they may be statically distributed over the entire molecule.
  • compositions according to the invention contain 0.0005 to 7.5 wt .-%, preferably 0.001 to 6 wt .-%, more preferably 0.005 to 5 wt .-%, more preferably 0.01 to 4 wt .-% and in particular 0 , 1 to 3 wt .-% of at least one ester of hyaluronic acid with lipoic acid having at least one recurring unit of the formula (V)
  • X is selected from H, Na and K
  • n stands for numbers from 1 to 10000
  • R2, R3 and R4 are independently selected from -H, -C (0) -H and
  • compositions according to the invention contain 0.0005 to 7.5 wt .-%, preferably 0.001 to 6 wt .-%, more preferably 0.005 to 5 wt .-%, more preferably 0.01 to 4 wt .-% and in particular 0 , 1 to 3 wt .-% of at least one ester of hyaluronic acid with Ionic acid of formula (Va)
  • X is selected from H, Na and K
  • n and m are numbers from 100 to 10000, and
  • R1, R2, R3 and R4 are independently selected from -H, -C (0) -H and
  • the recurring units with the indices n and m need not necessarily be bound together as a block, but rather they may be present in a statically distributed manner over the entire molecule.
  • Still further preferred hair treatment compositions according to the invention contain from 0.0005 to 7.5 wt .-%, preferably 0.001 to 6 wt .-%, more preferably 0.005 to 5 wt .-%, more preferably 0.01 to 4 wt .-% and in particular 0.1 to 3% by weight of at least one ester of hyaluronic acid with lipoic acid of the formula (Vb)
  • (Vb), in the X is selected from H, Na and K,
  • n, m and o stand for numbers from 100 to 10000
  • R1, R2, R3 and R4 are independently selected from -H, -C (0) -H and
  • the recurring units with the indices n, m and o do not necessarily have to be bound together as a block; rather, they can be present in a statically distributed manner over the entire molecule.
  • preferred hair treatment compositions contain from 0.0005 to 7.5% by weight, preferably from 0.001 to 6% by weight, more preferably from 0.005 to 5% by weight, more preferably from 0.01 to 4% by weight and in particular 0, 1 to 3 wt .-% of at least one ester of hyaluronic acid with formic acid having at least one recurring unit of the formula (VI)
  • X is selected from H, Na and K
  • R1, R2 and R3 are independently selected from -H, -C (0) -H and
  • the agents according to the invention may contain further active ingredients and adjuvants. These are described below.
  • the inventive compositions additionally contain at least one emulsifier or a surfactant, wherein surface-active substances depending on the field of application as surfactants or as Emulsifiers are selected and selected from anionic, cationic, zwitterionic, ampholytic and nonionic surfactants and emulsifiers.
  • preferred hair treatment compositions are characterized in that they - based on its weight - 0.5 to 70 wt .-%, preferably 1 to 60 wt .-% and in particular 5 to 25 wt .-% of anionic (s) and / or nonionic (s) and / or cationic and / or amphoteric surfactant (s).
  • Suitable anionic surfactants and emulsifiers for the compositions according to the invention are all anionic surfactants suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. As a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having about 8 to 30 carbon atoms. In addition, glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups may be present in the molecule.
  • Zwitterionic surfactants and emulsifiers are surface-active compounds which carry in the molecule at least one quaternary ammonium group and at least one -COO ⁇ ) or -SO 3 () group.
  • Particularly suitable zwitterionic surfactants and emulsifiers are the so-called betaines, such as N-alkyl-N, N-dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinates, for example cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3 carboxymethyl-3-hydroxyethyl imidazolines having in each case 8 to 18 carbon atoms in the alkyl or acyl group and the coco acylaminoethylhydroxyethyl carboxymethyl glycinate.
  • Ampholytic surfactants and emulsifiers are understood as meaning those surface-active compounds which, apart from a Cs-C24-alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H-group and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylaminopropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 24 C Atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 -C 18 acyl sarcosine.
  • Nonionic surfactants and emulsifiers contain as hydrophilic group z.
  • compositions according to the invention which additionally contain fatty alcohol (s) and / or fatty alcohol alkoxylate (s), preferably C 12-22 fatty alcohol (s) and / or C 12-22 fatty alcohol ethoxylate (s) having 10 to 30 EO units, especially preferably C 16-18 fatty alcohol (s) and / or C 16-18 fatty alcohol ethoxylate (s) having 12 to 20 EO units, preferably in amounts of from 5 to 20% by weight, preferably from 7.5 to 17.5% by weight and in particular from 10 to 15% by weight, based in each case on the weight of the composition.
  • fatty alcohol (s) and / or fatty alcohol alkoxylate (s) preferably C 12-22 fatty alcohol (s) and / or C 12-22 fatty alcohol ethoxylate (s) having 10 to 30 EO units, especially preferably C 16-18 fatty alcohol (s) and / or C 16-18 fatty alcohol ethoxylate (s) having 12 to 20 EO units, preferably in amounts of from 5 to 20%
  • hair-treatment compositions according to the invention contain, by weight, from 0.1 to 20% by weight, preferably from 0.25 to 17.5% by weight and in particular from 5 to 15% by weight of anionic surfactant ( e), particularly preferably fatty alcohol ether sulfates of the formula
  • n represents values of from 5 to 21, preferably from 7 to 19, more preferably from 9 to 17 and in particular from 11 to 13 and k for values of 1, 2, 3, 4, 5, 6, 7, 8 , 9 or 10, preferably 1, 2 or 3 and especially 2
  • M is a cation from the group Na + , K + NHV, Vi Mg 2+ , Vi Zn 2+ , preferably Na + .
  • the agents according to the invention may contain from 0.01 to 10% by weight of at least one polymer from the group of cationic and / or amphoteric polymers.
  • Cationic or amphoteric polymers are to be understood as meaning polymers which have a group in the main and / or side chain which may be “temporary” or “permanent” cationic.
  • "permanently cationic” refers to those polymers which have a cationic group, irrespective of the pH of the agent. These are usually polymers containing 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 bonded via a C1-C4 hydrocarbon group to a polymer main chain constructed from acrylic acid, methacrylic acid or derivatives thereof have proven to be particularly suitable.
  • the agents according to the invention can also contain amphoteric polymers. These additionally have at least one negatively charged group in the molecule and are also referred to as zwitterionic polymers.
  • agents according to the invention are preferred which, based on their weight, are from 0.05 to 7.5% by weight, preferably from 0.1 to 5% by weight, more preferably from 0.2 to 3.5% by weight and in particular from 0.25 to 2.5% by weight of amphoteric polymer (s).
  • agents contain amphoteric polymers or not
  • further preferred agents according to the invention are characterized in that they contain, based on their weight, from 0.05 to 7.5% by weight, preferably from 0.1 to 5% by weight. -%, particularly preferably 0.2 to 3.5 wt .-% and in particular 0.25 to 2.5 wt .-% cationic (s) polymer (s) included.
  • the agents of the invention may contain amphoteric polymers.
  • the agents according to the invention may with particular preference contain one or more amino acids.
  • Particularly preferred amino acids which can be used according to the invention are from the group glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrosine, tryptophan, proline, aspartic acid, glutamic acid, asparagine, glutamine, serine, threonine, cysteine, methionine, lysine, arginine, histidine, ⁇ Alanine, 4-aminobutyric acid (GABA), betaine, L-cystine (L-Cyss), L-carnitine, L-citrulline, L-theanine, 3 ', 4'-dihydroxy-L-phenylalanine (L-dopa), 5'-hydroxy-L-tryptophan, L-
  • Preferred agents according to the invention contain one or more amino acids in narrower quantitative ranges.
  • preferred hair treatment compositions according to the invention are characterized in that they contain as care substance - based on their weight - 0.01 to 5 wt .-%, preferably 0.02 to 2.5 wt .-%, particularly preferably 0.05 to 1, 5 Wt .-%, more preferably 0.075 to 1 wt .-% and in particular 0.1 to 0.25 wt .-% amino acid (s), preferably from the group of glycine and / or alanine and / or valine and / or lysine and / or leucine and / or threonine.
  • compositions according to the invention may furthermore contain all active substances, additives and auxiliaries known for such preparations.
  • the agents contain at least one surfactant, wherein in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable.
  • anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable.
  • the agents according to the invention may contain emulsifiers (F).
  • Emulsifiers effect at the phase interface the formation of water- or oil-stable adsorption layers, which protect the dispersed droplets against coalescence and thus stabilize the emulsion.
  • Emulsifiers are therefore constructed like surfactants from a hydrophobic and a hydrophilic part of the molecule. Hydrophilic emulsifiers preferably form O / W emulsions and hydrophobic emulsifiers preferably form W / O emulsions.
  • compositions according to the invention may also contain plant extracts (L).
  • extracts are produced by extraction of the whole plant. However, in individual cases it may also be preferred to prepare the extracts exclusively from flowers and / or leaves of the plant.
  • compositions according to the invention comprise the silicone (s) preferably in amounts of from 0.1 to 10% by weight, preferably from 0.25 to 7% by weight and in particular from 0.5 to 5% by weight. , in each case based on the total mean.
  • x is a number from 0 to 100, preferably from 0 to 50, more preferably from 0 to 20 and in particular 0 to 10.
  • Preferred silicones which can be used according to the invention have viscosities of from 0.2 to 2 mm 2 s at 20 ° C., silicones having viscosities of from 0.5 to 1 mm 2 s being particularly preferred.
  • agents according to the invention contain one or more amino-functionality
  • Silicones Such silicones may e.g. through the formula
  • R in the above formula is a hydrocarbon or a hydrocarbon radical having 1 to about 6 carbon atoms
  • Q is a polar radical of the general formula -R HZ, wherein R is a divalent linking group attached to hydrogen and the radical Z.
  • Z is an organic, amino-functional radical containing at least one amino-functional group; "a” assumes values in the range of about 0 to about 2, “b” assumes values in the range of about 1 to about 3, “a” + “b” is less than or equal to 3, and “c” is a number in the range from about 1 to about 3, and x is a number ranging from 1 to about 2,000, preferably from about 3 to about 50, and most preferably from about 3 to about 25, and y is a number ranging from about 20 to about 10,000 , preferably from about 125 to about 10,000, and most preferably from about 150 to about 1,000, and M is a suitable silicone end group as known in the art, preferably trimethylsiloxy.
  • Non-limiting examples of the groups represented by R include alkyl groups such as methyl, ethyl, propyl, isopropyl, isopropyl, butyl, isobutyl, amyl, isoamyl, hexyl, isohexyl and the like; Alkenyl radicals such as vinyl, halovinyl, alkylvinyl, allyl, haloallyl, alkylallyl; Cycloalkyl radicals such as cyclobutyl, cyclopentyl, cyclohexyl and the like; Phenyl radicals, benzyl radicals, halohydrocarbon radicals such as 3-chloropropyl, 4-bromobutyl, 3,3,3-trifluoropropyl, chlorocyclohexyl, bromophenyl, chlorophenyl and the like, and sulfur containing radicals such as mercaptoethyl, mercaptopropyl,
  • R examples include methylene, ethylene, propylene, hexamethylene, decamethylene, -CH 2 CH (CH 3) CH 2 -, phenylene, Naphthylene, -CH 2 CH 2 SCH 2 CH 2 , -CH 2 CH 2 OCH 2 -, -OCH 2 CH 2 -, -OCH 2 CH 2 CH 2 -, -CH 2 CH (CH 3) C (O) 2 -, - (CH 2 ) 3 CC (O) 2 CH 2 - , -C 6 H 4 C 6 H4, -C 6 H 4CH2C6H4-; and - (CH (CH 3)
  • Z is an organic, amino-functional radical containing at least one functional amino group.
  • a possible formula for Z is NH (CH 2) z NH 2, wherein z is 1 or more.
  • Another possible formula for Z is -NH (CH 2) z (CH 2) zzNH, wherein both z and zz are independently 1 or more, this structure comprising diamino ring structures, such as piperazinyl.
  • Z is most preferably a -NHCH 2 CH 2 NH 2 radical.
  • Another possible formula for Z is --N (CH 2) z (CH 2) zzNX 2 or --NX 2, wherein each X of X 2 is independently selected from the group consisting of hydrogen and alkyl groups of 1 to 12 carbon atoms, and zz is 0.
  • Q is most preferably a polar amine-functional radical of the formula -CH 2 CH 2 CH 2 NHCH 2 CH 2 NH 2.
  • "a” assumes values in the range of about 0 to about 2
  • "b” assumes values in the range of about 2 to about 3
  • "a "+” b is less than or equal to 3
  • " c is a number in the range of about 1 to about 3.
  • the molar ratio of R a Q b SiO (4-a-b) / 2 units to R c SiO (4- C ) / 2 units range from about 1: 2 to 1:65, preferably from about 1: 5 to about 1:65, and most preferably from about 1:15 to about 1:20
  • One or more silicones of the above formula may be used, then the various variable substituents in the above formula may be different for the various silicone components present in the silicone blend.
  • Preferred agents according to the invention are characterized in that they contain an amino-functional silicone of the formula (Si-II)
  • G is -H, a phenyl group, -OH, -O-CH 3 , -CH 3 , -O-CH 2 CH 3 , -CH 2 CH 3 , -O-CH 2 CH 2 CH 3 , -
  • CH 2 CH 2 CH 3 -O-CH (CH 3 ) 2, -CH (CH 3 ) 2 , -O-CH 2 CH 2 CH 2 CH 3 , -CH 2 CH 2 CH 2 CH 3 , -O- CH 2 CH (CH 3 ) 2, -CH 2 CH (CH 3 ) 2, -0-CH (CH 3) CH 2 CH 3, -CH (CH 3) CH 2 CH 3, -0-C (CH 3) 3, - C (CH 3) 3;
  • a is a number between 0 and 3, in particular 0;
  • b is a number between 0 and 1, in particular 1,
  • n and n are numbers whose sum (m + n) is between 1 and 2000, preferably between 50 and 150, where n is preferably values from 0 to 1999 and in particular from 49 to 149 and m preferably values from 1 to 2000, in particular from 1 to 10,
  • R - R ' is a monovalent radical selected from
  • each Q is a chemical bond, -CH 2 -, -CH 2 -CH 2 -, -CH 2 CH 2 CH 2 -, -C (CH 3 ) 2, - CH 2 CH 2 CH 2 CH 2 -, -CH 2 C (CH 3 ) 2, -CH ( CH 3 ) CH 2 CH 2 -,
  • R " is identical or different radicals from the group -H, -phenyl, -benzyl, -CH 2 -CH (CH 3 ) Ph, the Ci-20-alkyl radicals, preferably -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CH (CH 3 ) 2 , -CH 2 CH 2 CH 2 H 3 , -CH 2 CH (CH 3 ) 2 , -CH (CH 3 ) CH 2 CH 3 , -C (CH 3 ) 3 , and A represents an anion, which is preferably selected from chloride, bromide, iodide or methosulfate.
  • Particularly preferred agents according to the invention are characterized in that they contain at least one amino-functional silicone of the formula (Si-IIa)
  • n and n are numbers whose sum (m + n) is between 1 and 2000, preferably between 50 and 150, where n preferably values of 0 to 1999 and in particular of 49 to 149 and m preferably values of 1 to 2000 , in particular from 1 to 10 assumes.
  • silicones are referred to as trimethylsilylamodimethicones according to the INCI declaration.
  • compositions according to the invention which are an amino-functional silicone of the formula (Si-IIb)
  • R is -OH, -O-CH 3 or a -CH 3 group and m, n1 and n2 are numbers whose
  • Sum (n1 + n2) preferably values from 0 to 1999 and in particular from 49 to 149 and m preferably values from 1 to 2000, in particular from 1 to 10 assumes.
  • silicones are referred to as amodimethicones according to the INCI declaration.
  • Amine number stands for the milliequivalents of amine per gram of aminofunktioinelen silicone. It can be determined by titration and also expressed in mg KOH / g.
  • Agents preferred according to the invention are characterized in that, based on their weight, they contain 0.01 to 10% by weight, preferably 0.1 to 8% by weight, particularly preferably 0.25 to 7.5% by weight and in particular 0, 5 to 5 wt.% Amino-functional silicone (s) included.
  • agents according to the invention which contain at least one silicone of the formula Si-III
  • the silicones described above have a backbone composed of -Si-O-Si units.
  • these Si-O-Si units may also be interrupted by carbon chains.
  • Appropriate molecules are accessible by chain extension reactions and are preferably used in the form of silicone-in-water emulsions.
  • R is identical or different radicals from the group -H, -phenyl, -benzyl, -CH 2 -CH (CH 3 ) Ph, the Ci-20-alkyl radicals, preferably -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CH (CH 3 ) 2, -CH 2 CH 2 CH 2 H 3, -CH 2 CH (CH 3 ) 2, -CH (CH 3 ) CH 2 CH 3 , -C (CH 3 ) 3 , x and y represent a number of 0 to 200, preferably from 0 to 10, more preferably from 0 to 7 and in particular 0, 1, 2, 3, 4, 5 or 6, and n is a number from 0 to 10, preferably from 1 to 8 and in particular stands for 2, 3, 4, 5, 6.
  • the silicones are preferably water-soluble. Agents preferred according to the invention are characterized in that they contain at least one water-soluble silicone.
  • the NTU value Nephelometrie Turbidity Unit
  • the compositions according to the invention have advantageous properties and also confer advantageous properties on the hair treated with them. In particular, in hair and scalp treatment benefits have been observed bvzw the advantages of the oligopeptides. Hyaluronic acid ester go out alone.
  • hair treatment compositions according to the invention increase the elasticity of the hair treated with them and lead to an inner-structural strengthening of the hair fibers, which is reflected, for example, in higher melting temperatures in differential thermal analysis.
  • compositions according to the invention cause an increase in the elasticity and, surprisingly, sebum-regulating effects. The visual impression of "greasy" skin or hair is thus avoided or weakened.
  • Another object of the present invention is a method for improving at least one of the properties

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Abstract

Agents de soins capillaires contenant chacun, rapporté à leur poids total, 0,0001 à 10 % en poids d'au moins un oligopeptide qui contient au moins une séquence d'acides aminés Glu-Glu-Glu (formule (I)), les groupes amino pouvant être libres ou protonés, et les groupes carboxy pouvant être libres ou déprotonés, et 0,0001 à 10 % en poids d'au moins un ester d'acide hyaluronique estérifié avec de l'acide liponique, de l'acide formique ou leur mélange. Dans ces agents, l'ester d'acide hyaluronique et certains oligopeptides renforcent de manière synergique leur effet positif sur les cheveux et les follicules pileux.
EP14799663.1A 2013-10-02 2014-09-24 Agents de soins capillaires contenant des oligopeptides et des esters d'acide hyaluronique Withdrawn EP3052075A1 (fr)

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DE102013220061.7A DE102013220061A1 (de) 2013-10-02 2013-10-02 Leistungsgesteigerte Haarbehandlungsmittel
PCT/DE2014/200502 WO2015048965A1 (fr) 2013-10-02 2014-09-24 Agents de soins capillaires contenant des oligopeptides et des esters d'acide hyaluronique

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US5136093A (en) 1991-02-06 1992-08-04 Smith Ronald J Quaternized panthenol compounds and their use
DE4413686C2 (de) 1994-04-20 1996-10-24 Henkel Kgaa Kationische Zuckertenside, Verfahren zu ihrer Herstellung und deren Verwendung
JP2004269430A (ja) * 2003-03-10 2004-09-30 Ichimaru Pharcos Co Ltd 毛髪処理用組成物及び損傷毛用毛髪化粧料
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ITMI20072416A1 (it) 2007-12-21 2009-06-22 Sigea Srl Derivati polisaccaridici dell'acido lipoico, loro preparazione ed uso come dermocosmetici e presidi medicali
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