EP3077054A1 - Agents de traitement capillaire contenant un ou plusieurs silicones substitués - Google Patents

Agents de traitement capillaire contenant un ou plusieurs silicones substitués

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Publication number
EP3077054A1
EP3077054A1 EP14795836.7A EP14795836A EP3077054A1 EP 3077054 A1 EP3077054 A1 EP 3077054A1 EP 14795836 A EP14795836 A EP 14795836A EP 3077054 A1 EP3077054 A1 EP 3077054A1
Authority
EP
European Patent Office
Prior art keywords
copolymers
sty
styrene
acrylic acid
methacrylic 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Withdrawn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
EP14795836.7A
Other languages
German (de)
English (en)
Inventor
Erik Schulze Zur Wiesche
René KROHN
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 EP3077054A1 publication Critical patent/EP3077054A1/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Withdrawn legal-status Critical Current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
    • A61K8/72—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
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—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
    • A61K8/8141—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • 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
    • A61Q5/004—Preparations used to protect coloured 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
    • A61K2800/594—Mixtures of polymers

Definitions

  • the invention relates to hair treatment compositions containing specifically substituted silicone (s) and the use of these agents for the cleaning and / or care of hair.
  • Keratin fiber care products affect the natural structure and properties of hair.
  • the wet and dry combability of the hair, the hold and the fullness of the hair can be optimized or the hair can be protected from increased splits following such treatments. It has therefore long been customary to subject the hair to a special aftertreatment.
  • the hair is treated with 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 splitting rate.
  • Another problem is colored hair. If the dyes formed or used directly in the course of color formation have significantly different fastnesses (eg UV stability, perspiration fastness, wash fastness, etc.), a noticeable and therefore undesirable color shift can occur over time. This phenomenon occurs more frequently when the hairstyle has hair or hair zones of different degrees of damage. An example of this is long hair, in which the hair tips exposed for a long time to all sorts of environmental influences are usually much more damaged than the relatively newly regrown hair zones.
  • fastnesses eg UV stability, perspiration fastness, wash fastness, etc.
  • UV filters are defined by their purpose. They are therefore “substances which are exclusively or predominantly intended to protect the skin by absorption, reflection or scattering of certain UV radiation against certain UV radiation.” Regardless of whether they are organic or inorganic, so-called chemical or physical all UV filters are assigned to this definition and only the UV filters listed in the Cosmetics Regulation may be used, as the individual substances are generally not protected over the entire UV spectrum offer many substances are usually combined. In addition, synergistic effects usually result from the combination of UV filters.
  • UV protection in skincare products is widely elaborated in terms of formulation, less complex systems are used in hair care products for "dead” matter, and the quantities in which filter substances can be incorporated are usually lower for technical reasons, partly for cost reasons.
  • octocrylene-containing agents can be significantly improved with respect to the above-mentioned task complex, if certain acrylate polymers and substituted silicones are used.
  • a first subject of the present invention is a hair treatment composition containing - in each case based on its weight - a) 0, 1 to 20 wt .-% of at least one silicone, which groups of the formula (I)
  • n is from 1 to 1000
  • R1 is -H or -CH3 and R is a straight-chain or branched alkyl radical having 8 to 24 C atoms and a is an integer from 1 to 20;
  • R 2 is -H or -Ch and X is -H, an alkali metal cation or a straight-chain or branched alkyl radical having 1 to 24 C atoms;
  • 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.
  • means according to the invention are preferably agents which the man applies anyway.
  • Preferred agents according to the invention are therefore shampoos, conditioners or hair tonics.
  • compositions of the invention impart improved properties to the keratinic fibers treated with them which persist even under intense UV irradiation (e.g., lightness, softness, entangleability, natural feel and airy hairstyle, brightness), and the effects are more persistent and persistent. In particular, these effects are resistant to many shampoos.
  • compositions of the invention contain as the first essential ingredient 0, 1 to 20 wt .-% of at least one silicone having moieties of the formula (I).
  • n stands for values of 1 to 1000, preferred values being 1 to 40, preferably 1 to 30, more preferably 1 to 20 and especially for the values 2, 3, 4, 5, 6, 7, 8 , 9 or 10 stand.
  • A represents a grouping in which R1 is -H or -CH3 and R is a straight-chain or branched alkyl radical having 8 to 24 C atoms and a is an integer from 1 to 20;
  • R1 -H.
  • Hair treatment agents which are particularly preferred according to the invention are characterized in that they contain from 0.1 to 20% by weight, preferably from 0.25 to 15% by weight, more preferably from 0.5 to 10% by weight, even more preferably from 0.75 to 7.5 wt .-% and in particular 1 to 5 wt .-% of at least one Silicones containing groupings of the formula (la)
  • a is an integer from 1 to 20.
  • the silicones used according to the invention may consist entirely of groupings of the formula (I) or (Ia), preference being given to end groups -Ch, -O-CH 3 or -OH.
  • silicones used in the invention further groups, especially those of the formula
  • Such co-silicones of units of the above-mentioned formula and units of the formula (I) or (Ia) can also have as end groups -CH 3, -O-CH 3 or -OH.
  • the units can be present in blocks or statistically distributed in such co-silicones.
  • Particularly preferred hair treatment compositions according to the invention are characterized in that they contain from 0.1 to 20% by weight, preferably from 0.25 to 15% by weight, more preferably from 0.5 to 10% by weight, even more preferably from 0.75 to 7.5% by weight and in particular 1 to 5% by weight of at least one silicone of the formula (II):
  • R 1 is -H or -CH 3 and R is a straight-chain or branched alkyl radical having 8 to 24 C atoms and a is an integer from 1 to 20;
  • Q is -OH or -CH 3 or -OCH 3 ;
  • indices k, n, m, o, p, q are integers from 0 to 1000, with the proviso that n + p> 0 and k + m + o + q> 0,
  • A is a grouping in which R 1 is -H or -CH 3 and R is a straight-chain or branched alkyl radical having 8 to 24 C atoms and a is an integer from 1 to 20;
  • R1 -H.
  • compositions according to the invention are therefore characterized in that they contain 0.1 to 20% by weight, preferably 0.25 to 15% by weight, more preferably 0.5 to 10% by weight, even more preferably 0.75 to 7.5% by weight and in particular 1 to 5% by weight of at least one silicone of the formula (III):
  • R is selected off
  • --CH (CH 2 CH 3 ) - (CH 2 ) 5 a is an integer from 1 to 20;
  • Q is -OH or -CH 3 or -OCH 3 ;
  • indices k, n, m, o, p, q are integers from 0 to 1000, with the proviso that n + p> 0 and k + m + o + q> 0
  • Particularly preferred hair treatment agents are therefore characterized by being 0.1 to 20% by weight, preferably 0.25 to 15% by weight, more preferably 0.5 to 10% by weight, still more preferably 0.75 to 7.5% by weight and in particular 1 to 5% by weight of at least one silicone of the formula (IV):
  • R is - (CH 2) i2-CH 3 and Q is -OH or -OCH 3;
  • Q is -OH or -CH 3 or -OCH 3 ;
  • indices k, n, m, o, p, q are integers from 0 to 1000, with the proviso that n + p> 0 and k + m + o + q> 0
  • Q is -OH or -CH 3 or -OCH 3 .
  • the two Q's do not have to be identical, but the termination at one end may be different than at the other end, with the following combinations being preferred:
  • the two groups are identical at the respective chain end. More preferably, Q is -OH or -OCh.
  • the silicones of the formulas (IIa), (IIb), (IIIa), (IIIb), (IVa) and (IVb) represent particularly preferred embodiments:
  • the average molecular weight of the silicones a) contained in the agents according to the invention is preferably from 2,000 to 300,000 and more preferably from 5,000 to 200,000, in particular from 10,000 to 150,000 daltons.
  • the average molecular weights of amino-substituted silicones can be measured, for example, by gel permeation chromatography (GPC) at room temperature in polystyrene.
  • GPC gel permeation chromatography
  • columns Styragel columns ⁇ , as eluent THF and as flow rate 1 ml / min can be selected.
  • the detection preferably takes place by means of refractometry and UV meter.
  • compositions according to the invention contain from 0.1 to 20% by weight of at least one copolymer which has monomer units of the formulas (V) and (VI)
  • R 2 is -H or -Ch and X is -H, an alkali metal cation or a straight-chain or branched alkyl radical having 1 to 24 C atoms.
  • the copolymers can only consist of monomers of the formulas (V) and (VI), but they can also contain further monomer building blocks. It has proved to be preferred in view of the protective action against the damage of the hair structure, if at least 50 wt .-%, preferably at least 60 wt .-%, more preferably at least 70 wt .-%, still more preferably at least 80 wt .-%, particularly preferably at least 90 wt .-% and in particular at least 99 wt .-% of the copolymers of monomers of the formulas (V) and (VI) consist.
  • the structural unit (V) attributable monomer is styrene
  • the copolymers may contain a single type of monomer units (VI) or several different monomer units (VI, VI ' , VI " , etc.) Examples of the first embodiment would be copolymers of styrene and acrylic acid, an example of the second embodiment would be copolymers of styrene, acrylic acid and methacrylate.
  • Particularly preferred hair treatment agents are therefore characterized by being 0.5 to 17.5% by weight, preferably 1 to 15% by weight, more preferably 1.5 to 12.5, particularly preferably 2 to 10 and in particular 3 to 8 wt .-% of at least one copolymer containing monomer units of the formulas (V) and (Via)
  • compositions according to the invention contain from 0.1 to 10% by weight of (RS) -2-cyano
  • Hair treatment compositions are characterized by having 0.25 to 9 wt%, preferably 0.5 to 8 wt%, more preferably 0.75 to 7 wt%, most preferably 1 to 6 wt%, and especially 2.5 to 5 wt .-% (RS) -2-cyano-3,3-diphenylacrylic acid-2-ethylhexylester included. It has proved to be preferred if the ingredients a), b) and c) are used in certain proportions to each other. In this way, the UV protection effect is optimally reinforced.
  • Hair treatment agents which are preferred according to the invention are characterized in that the weight ratio of ingredients b) to a) is in the range from 1:50 to 50: 1, preferably in the range from 1:10 to 25: 1, more preferably in the range from 1: 1 to 5 : 1, more preferably in the range of 1, 5: 1 to 4: 1 and in particular in the range of 1, 75: 1 to 2.5: 1.
  • Further preferred hair treatment compositions according to the invention are characterized in that the weight ratio of the ingredients a) to c) in the range from 1:50 to 50: 1, preferably in the range from 1:10 to 25: 1, more preferably in the range from 1: 5 to 5: 1, more preferably in the range of 1, 5: 1 to 4: 1 and in particular in the range of 1, 1: 1 to 1: 1, 1.
  • compositions of the invention contain depending on the application further essential ingredients.
  • Cleansing or conditioning compositions such as shampoos or conditioners contain at least one surfactant, surfactants depending on the field of application being referred to as surfactants or as emulsifiers and being selected from anionic, cationic, zwitterionic, ampholytic and nonionic surfactants and emulsifiers.
  • Hair treatment compositions which are preferred according to the invention are characterized in that they contain, based on their weight, from 0.5 to 70% by weight, preferably from 1 to 60% by weight and in particular from 5 to 25% by weight of anionic 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 as well as hydroxyl groups may be present in the molecule.
  • Zwitterionic surfactants and emulsifiers are those 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 each having 8 to 18 carbon atoms in the alkyl or acyl group, and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • Zwitterionic surfactants and emulsifiers are those 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 each having 8 to 18 carbon atoms in the alkyl or acyl group, and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • 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 -SCbH 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 C12-C18 acylsarcosine.
  • Cationic surfactants of the quaternary ammonium compound type, the esterquats and the amidoamines can be used according to the invention.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides.
  • the long alkyl chains of these surfactants preferably have 10 to 18 carbon atoms, such as.
  • cetyl trimethyl ammonium chloride stearyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, lauryl dimethyl ammonium chloride, lauryl dimethyl benzyl ammonium chloride and tricetylmethyl ammonium chloride.
  • Further preferred cationic surfactants are the imidazolium compounds known under the INCI names Quaternium-27 and Quaternium-83.
  • 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-homocysteine, S-methyl-L-methionine, S-allyl-L-cysteine, S
  • Preferred agents according to the invention contain one or more amino acids in narrower quantitative ranges.
  • preferred cosmetic compositions according to the invention are characterized in that they contain, as a care substance, based on their weight, from 0.01 to 5% by weight, preferably from 0.02 to 2.5% by weight, particularly preferably from 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 glycine and / or alanine and / or valine and / or lysine and / or leucine and / or threonine.
  • the silicones having structural units of the formula (I) used according to the invention can of course be used together with further conventional silicones.
  • Preferred agents according to the invention are characterized in that they contain at least one further silicone.
  • Preferred silicones which can be used according to the invention have viscosities of 0.2 to 2 mm 2 s -1 at 20 ° C., with silicones having viscosities of 0.5 to 1 mm 2 s being particularly preferred.
  • Particularly preferred agents according to the invention contain one or more amino-functional silicones.
  • 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-
  • 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 ) 2 3 ) CH 2 CH 2 - is,
  • R represents 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)
  • compositions according to the invention which are an amino-functional silicone of the formula (Si-IIb)
  • R is -OH, -O-Ch or a -Ch group and m
  • n1 and n2 are numbers whose sum (m + n1 + n2) is between 1 and 2,000, preferably between 50 and 150, wherein the sum (n1 + n2) preferably assumes 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.
  • silicones are referred to as amodimethicones according to the INCI declaration.
  • agents according to the invention which contain an amino-functional silicone whose amine number is above 0.25 meq / g, preferably above 0.3 meq / g and in particular above 0.4 meq / g, are preferred ,
  • the amine number stands for the milliequivalents of amine per gram of the amino-functional 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, more preferably 0.25 to 7.5% by weight and in particular 0, 5 to 5 wt.% Amino-functional silicone (s) included.
  • 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 from 0 to 200, preferably from 0 to 10, more preferably from 0 to 7 and especially 0, 1, 2, 3, 4, 5 or 6, and n is a number from 0 to 10, preferably from 1 to 8 and especially 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 agents according to the invention may contain at least one proteolipid of the formula (P-1)
  • R ' is a straight-chain or branched, saturated or unsaturated hydrocarbon radical having 1 to 24 carbon atoms
  • R means a protein, a peptide or a protein hydrolyzate
  • X is -C (O) O- or -N + (R '" 2 ) R' V - or -N (R"')R' V - or -C (O) -N (R V ) R VI - stands,
  • the proteolipids are used in the agents according to the invention
  • Preferred cosmetic agents according to the invention contain, by weight, 0.01 to 10% by weight, preferably 0.02 to 5% by weight, particularly preferably 0.05 to 2.5% by weight, more preferably 0, 1 to 1% by weight and in particular 0, 15 to 0.5% by weight of proteolipid (s)
  • the radical R " in formula (P1) represents a peptide or a protein or a protein hydrolyzate.
  • Preferred radicals R " are oligopetides which have 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 parenthetized hydrogen atom of the amino group, as well as the parenthetical group of the acid function means that the respective groups may be present as such (then it is an oligopeptide with the relevant number of amino acids as shown (in the above formula 3) or that the amino acid sequence is present in an oligopeptide which comprises further amino acids - depending on where the other amino acid (s) is / are bound, the parenthetized components of the above formula are replaced by the other amino acid residue (s).
  • 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 molecular weight of the proteolipid contained in the inventive compositions vary.
  • Cosmetic agents preferred according to the invention are characterized in that the proteolipid has a molar mass of from 1000 to 30,000 Da, preferably from 1250 to 25,000 Da, more preferably from 1,500 to 20,000 Da and in particular from 2,000 to 15,000 Da.
  • R "oligopeptides are preferably used, which not only consist of the three glutamic acids, but contain further bound to this sequence amino acids. These additional amino acids are preferably selected from certain amino acids are while certain other agents according to the invention are less preferred.
  • radical R "of the proteolipids used in the agents according to the invention contains no methionine It is further preferred if the radical R " of the proteolipids used in the agents according to the invention contains no cysteine and / or cystine.
  • radical R "of the proteolipids used in the agents according to the invention does not contain aspartic acid and / or asparagine It is further preferred if the radical R " of the proteolipids used in the agents according to the invention contains no serine and / or threonine.
  • the radical R " contains the proteolipids used in the agents according to the invention tyrosine It is further preferred if the radical R " contains the proteolipids used in the agents according to the invention leucine. It is further preferred if the radical R ' ' of the proteolipids used in the agents according to the invention comprises isoleucine.It is further preferred if the radical R '' of the proteolipids used in the agents according to the invention contains arginine. It is further preferred if the radical R " contains the proteolipids used in the agents according to the invention valine.
  • radicals R "which are particularly preferred oligopeptides or amino acid sequences contained in the preferred oligopeptides are described below:
  • a particularly preferred oligopeptide additionally contains tyrosine, which is preferably linked via its acid function to the Glu-Glu-Glu sequence.
  • Cosmetic agents which are preferred according to the invention are therefore characterized in that the oligopeptide contained in the proteolipids of the formula (I) as the radical R "has at least one amino acid sequence Tyr-Glu-Glu-Glu, where the amino group is free or protonated and the carboxy groups may 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.
  • Cosmetic agents which are preferred according to the invention are therefore characterized in that the oligopeptide contained in the proteolipids of the formula (I) as the radical R "has at least one amino acid sequence Glu-Glu-Glu-Ile, where the amino group is free or protonated and the carboxy groups may be free or deprotonated.
  • Oligopeptides which have both the abovementioned amino acids (tyrosine and isoleucine) are preferred according to the invention.
  • Hair treatment agents according to the invention are particularly preferred in which the oligopeptide contained in the proteolipids of the formula (I) as the radical R "has at least one amino acid sequence Tyr-Glu-Glu-Glu-Ile, where the amino group is free or protonated and the carboxy- groups may be free or deprotonated form.
  • further preferred oligopeptides additionally contain arginine, which is preferably bound to isoleucine.
  • the in the proteolipids of formula (I) oligopeptide contained as the radical R "represents at least one amino acid sequence Tyr -Glu-Glu-Glu-Ile-Arg, wherein the amino groups may be free or protonated and the carboxy groups may be free or deprotonated.
  • Still further preferred oligopeptides additionally contain valine, which is preferably bound to the arginine.
  • further preferred cosmetic product is therefore characterized in that the in the proteolipids of formula (I) having oligopeptide contained as the radical R "represents at least one amino acid sequence Tyr-Glu-Glu-Glu-Ile-Arg-Val, wherein the amino groups free
  • Even more preferred oligopeptides additionally contain leucine, which is preferably bound to valine.
  • Cosmetic agents which are further preferred according to the invention are characterized in that in the proteolipids of the formula (I) as radical R " Oligopeptide contained 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 may be present freely or deprotonated. Particularly preferred oligopeptides additionally contain leucine, which is preferably bound to the tyrosine.
  • oligopeptide contained in the proteolipids of the formula (I) as the radical R has at least one amino acid sequence Leu-Tyr-Glu-Glu-Glu-Ile-Arg-Val-Leu, where the amino Groups are free or protonated and the carboxy groups may be free or deprotonated.
  • cosmetic agents according to the invention are preferred which at least one proteolipd of formula (I), in which R "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 free or may be present deprotonated.
  • the radical R " in formula (P1) may be a peptide or a protein or a protein hydrolyzate, protein hydrolysates being preferred Protein hydrolysates are product mixtures which are obtained by acid, base or enzymatically catalyzed degradation of proteins (proteins) According to the invention, protein hydrolysates of both vegetable and animal origin can be used.
  • Animal protein hydrolysates are, for example, elastin, collagen, keratin, silk and milk protein hydrolysates, which may also be present in the form of salts.
  • Such products are, for example, under the trademarks Dehylan ® (Cognis), Promois® ® (Interorgana) Collapuron ® (Cognis), Nutrilan® ® (Cognis), Gelita-Sol ® (German Gelatinefabriken Stoess & Co), Lexein ® (Inolex) and kerasol tm ® (Croda) sold.
  • Preferred according to the invention is the use of protein hydrolysates of plant origin, eg. Soybean, almond, rice, pea, potato and wheat protein hydrolysates.
  • Such products are, for example, under the trademarks Gluadin ® (Cognis), diamine ® (Diamalt) ® (Inolex) and Crotein ® (Croda) available.
  • the radical R " is selected from keratin or keratin hydrolysates
  • Preferred cosmetic agents according to the invention are characterized in that they contain at least one proteolipid of formula (P1) in which R " for keratin or a keratin hydrolyzate is.
  • particularly preferred cosmetic agents according to the invention are characterized in that they contain at least one proteolipd of the formula (I) in which X is -N + (CH 3) 2 -CH 2 -CH (OH) -CH 2 - and R 'is (- CH 2 ) i7-CH 3 .
  • preferred cosmetic agents according to the invention are characterized in that they contain at least one proteolipd of the formula (P1) in which X is -C (O) -O- and R 'is - (CH 2) 7 -CH 3 .
  • protein hydrolysates in addition to the proteolipids. These enhance the effect of the proteolipids and in turn are amplified in their effects.
  • the protein hydrolyzates have been described above as R "detailed summary are preferred cosmetic composition of the invention which additionally -. Based on its weight - 0.01 to 10 wt .-%, preferably 0.05 to 7 wt .-%, particularly preferably 0, 1 to 5 wt .-%, more preferably 0.25 to 2.5 wt .-% and in particular 0.5 to 2.0 Wt% protein hydrolyzate (s), preferably keratin hydrolyzate (s).
  • cosmetic agents which are preferred according to the invention are therefore characterized by being transparent or translucent.
  • NTU Nephelometrie Turbidity Unit
  • n is from 1 to 1000
  • R1 is -H or -Chta and R is a straight-chain or branched alkyl radical having 8 to 24 C atoms and a is an integer from 1 to 20, for reducing the damage to the hair structure by external influences, in particular by

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Abstract

Agents de traitement capillaire contenant respectivement par rapport à leurs poids, de 0,1 à 20 % en poids d'au moins un silicone qui présente des groupes de formule (I) (I), dans laquelle n représente des valeurs de 1 à 1000, A représente un groupe [formule] dans lequel R1 représente -H ou -CH3, et R représente un résidu alkyle linéaire ou ramifié comprenant de 8 à 24 atomes de C, et a représente un entier entre 1 et 20 ; de 0,1 à 20% en poids d'au moins un copolymère comprenant des unités monomères de formule (V) et (VI), (VI) où R2 représente -H ou -CH3 et X représente -H, un cation de métal alcalin ou un résidu alkyle linéaire ou ramifié comprenant de 1 à 24 atomes de C ; de 0,1 à 10 % en poids de 2-éthylhexylester d'acide (RS)-2-cyano-3,3-diphénylacrylique, présentant un effet protecteur amélioré contre le rayonnement UV et donnant aux cheveux traités des propriétés améliorées en matière de facilité de coiffage, de brillance, d'élasticité, de fragilité et de ténacité de rupture.
EP14795836.7A 2013-12-05 2014-11-11 Agents de traitement capillaire contenant un ou plusieurs silicones substitués Withdrawn EP3077054A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102013224993.4A DE102013224993A1 (de) 2013-12-05 2013-12-05 Haarbehandlungsmittel mit substituierten Silikon(en)
PCT/EP2014/074232 WO2015082174A1 (fr) 2013-12-05 2014-11-11 Agents de traitement capillaire contenant un ou plusieurs silicones substitués

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EP3077054A1 true EP3077054A1 (fr) 2016-10-12

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CA3039514C (fr) * 2016-10-04 2022-01-25 University Of Florida Research Foundation, Incorporated Compositions d'acides amines et utilisations associees
EP3773922A1 (fr) * 2018-04-03 2021-02-17 HFC Prestige International Holding Switzerland S.a.r.l. Composition à deux composants
WO2020008074A1 (fr) 2018-07-06 2020-01-09 Hfc Prestige International Holding Switzerland S.A.R.L Composition de coloration capillaire et procédés pour son application et son élimination
JP2021529832A (ja) 2018-07-06 2021-11-04 エイチエフシー・プレステージ・インターナショナル・ホールディング・スウィッツァーランド・エスアーエールエル 多成分組成物

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DE3725030A1 (de) 1987-07-29 1989-02-09 Henkel Kgaa Oberflaechenaktive hydroxysulfonate
DE102004030885A1 (de) * 2004-06-25 2006-02-09 Henkel Kgaa Haarreinigungsmittel mit aminofunktionellen Siliconen
WO2006040286A1 (fr) * 2004-10-15 2006-04-20 Ciba Specialty Chemicals Holding Inc. Formulations de soins capillaires comprenant un poly-organo-siloxane amino-fonctionnel
JP2006117606A (ja) * 2004-10-22 2006-05-11 Shiseido Co Ltd 毛髪化粧料

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DE102013224993A1 (de) 2015-06-11
WO2015082174A1 (fr) 2015-06-11

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