EP2323618A2 - Préparation pour fibres kératiniques, contenant au moins un polymère cationique amphiphile spécial et au moins un polymère additionnel filmogène et/ou fixant choisi parmi le chitosane et ses dérivés - Google Patents

Préparation pour fibres kératiniques, contenant au moins un polymère cationique amphiphile spécial et au moins un polymère additionnel filmogène et/ou fixant choisi parmi le chitosane et ses dérivés

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Publication number
EP2323618A2
EP2323618A2 EP09780872A EP09780872A EP2323618A2 EP 2323618 A2 EP2323618 A2 EP 2323618A2 EP 09780872 A EP09780872 A EP 09780872A EP 09780872 A EP09780872 A EP 09780872A EP 2323618 A2 EP2323618 A2 EP 2323618A2
Authority
EP
European Patent Office
Prior art keywords
formula
structural unit
group
composition according
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.)
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Application number
EP09780872A
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German (de)
English (en)
Inventor
Burkhard Müller
Pamela Kaftan
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
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Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP2323618A2 publication Critical patent/EP2323618A2/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Withdrawn legal-status Critical Current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
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; 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
    • A61K8/817—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)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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 present invention relates to hair treatment compositions containing a combination of at least one particular amphiphilic cationic polymer with at least one film-forming and / or setting polymer selected from chitosan and its derivatives, the use of these agents for temporary shaping and / or care of keratin-containing fibers and aerosol hair sprays foams based on these agents.
  • all animal hair e.g. Wool, horsehair, angora hair, furs, feathers and products or textiles made from them.
  • the keratinic fibers are human hairs.
  • Corresponding temporary shaping agents usually contain synthetic polymers as the shaping component.
  • Preparations containing a dissolved or dispersed polymer can be applied to the hair by means of propellant gases or by a pumping mechanism.
  • hair gels and hair waxes are generally not applied directly to the hair, but distributed by means of a comb or hands in the hair.
  • the most important property of a composition for the temporary deformation of keratinic fibers is to give the treated fibers in the produced form the strongest possible hold. If the keratin fibers are human hair, it is also referred to as a strong hairstyle or the high degree of retention of the styling agent.
  • the hairstyle hold is essentially determined by the type and amount of the synthetic polymer used, but also an influence of the other constituents of the styling agent may be given. In addition to a high degree of hold, styling agents must meet a whole range of other requirements.
  • properties on the hair may be broadly subdivided into properties on the hair, properties of the particular formulation, eg properties of the foam, of the gel or of the sprayed aerosol, and of properties which affect the handling of the styling agent, whereby the properties on the hair are of particular importance. Particularly noteworthy are moisture resistance, low tackiness and a balanced conditioning effect. Furthermore, a styling agent should be universally applicable as possible for all hair types.
  • the polymers can be subdivided into cationic, anionic, nonionic and amphoteric film-forming and / or setting polymers.
  • the polymers when applied to hair, the polymers give a polymer film which, on the one hand, gives the hairstyle strong hold but, on the other hand, is sufficiently flexible not to break under stress. If the polymer film is too brittle, it results in the formation of so-called Filmpiaken, that is residues that detach during the movement of the hair and give the impression that the user of the corresponding styling agent would dandruff.
  • Object of the present invention was therefore to provide a means for temporary deformation and / or care keratinic fibers available, which is characterized by a high degree of hold or by a high care effect and in particular excellent handling during application to the keratin fibers has.
  • compositions achieved with this combination even have, in addition, a transparency that is visible to the naked eye.
  • a first subject of the present invention is therefore an agent for treating keratin-containing fibers, especially human hair, contained in a cosmetically acceptable carrier
  • R 1 and R 4 independently of one another represent a hydrogen atom or a methyl group
  • X 1 and X 2 independently of one another represent an oxygen atom or a group NH
  • a 1 and A 2 independently of one another represent a group of ethane-1,2-diyl, Propane-1, 3-diyl or butane-1, 4-diyl,
  • R 2 , R 3 , R 5 and R 6 independently of one another are a (C 1 to C 4 ) -alkyl group, R 7 is a (C 8 to C 30 ) -alkyl group and
  • Film-forming polymers are polymers which leave a continuous film on the skin, the hair or the nails when drying.
  • Such film formers can be used in a wide variety of cosmetic products, such as for example face masks, make-up, hair fixatives, hair sprays, hair gels, hair waxes, hair treatments, shampoos or nail varnishes.
  • Particular preference is given to polymers which have a sufficient solubility in water or water / alcohol mixtures in order to be present in completely completely dissolved form in the agent according to the invention.
  • the film-forming polymers may be of synthetic or natural origin.
  • film-forming polymers are understood as meaning polymers which, when used in 0.01 to 20% strength by weight aqueous, alcoholic or aqueous-alcoholic solution, are capable of depositing a transparent polymer film on the hair.
  • Firming polymers contribute to the maintenance and / or build-up of the hair volume and hair fullness of the overall hairstyle. These polymers are at the same time also film-forming polymers and therefore generally typical substances for shaping hair treatment agents such as hair fixatives, hair foams, hair waxes, hair sprays.
  • the film formation can be quite selective and connect only a few fibers.
  • derivatives are meant, according to the invention, derivatives of a chemical compound (e.g., chitosan) which can be prepared from this chemical compound by structurally altering a functional group of said chemical compound.
  • a chemical compound e.g., chitosan
  • physiologically acceptable anions such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • Examples of (C 1 to C 4 ) -alkyl groups according to the invention are methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl.
  • Examples of (C 8 to C 30 ) -alkyl groups according to the invention are octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl), docosyl ( behenyl).
  • amphiphilic, cationic polymers according to the invention preferably have a molecular weight of from 10,000 g / mol to 50,000,000 g / mol, in particular from 50,000 g / mol to 5,000,000 g / mol, more preferably from 75,000 g / mol to 1,000,000 g / mol.
  • Preferred agents according to the invention comprise the amphiphilic, cationic polymers (a) in an amount of from 0.1% by weight to 20.0% by weight, particularly preferably from 0.2% by weight to 10.0% by weight .-%, most preferably from 0.5 to 7.0 wt.%, Each based on the weight of the composition.
  • the properties of the agent according to the invention prove to be particularly advantageous when it is formulated as an aerosol spray, aerosol foam, pump spray or pump foam. This preferred form of packaging will be described later in detail.
  • amphiphilic cationic polymers (a) are preferably used in the agents according to the invention if the amphiphilic, cationic polymers (a) with respect to the abovementioned formulas (I) to (IV) fulfill one or more of the following features:
  • R 1 and R 4 each represent a methyl group
  • X 1 stands for a group NH
  • X 2 stands for a group NH
  • a 1 and A 2 are each independently ethane-1, 2-diyl or propane-1, 3-diyl,
  • R 2 , R 3 , R 5 and R 6 independently of one another represent methyl or ethyl, (particularly preferably methyl),
  • R 7 is a (Ci 0 to C 24 ) alkyl group, in particular decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl ).
  • the structural unit of the formula (III) is according to the invention a very particularly preferred structural unit.
  • the structural unit of the formula (IV) is selected, to consist of at least one structural unit of the formulas (IV-1) to (IV-8)
  • particularly preferred structural unit of the formula (IV) are the structural units of the formula (IV-7) and / or the formula (IV-8), wherein in each case R 7 is octyl (capryl), decyl (caprinyl), dodecyl (lauryl ), Tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl).
  • the structural unit of the formula (IV-8) represents according to the invention a very particularly preferred structural unit of the formula (IV).
  • a very particularly preferred amphiphilic, cationic polymer contained in the agent according to the invention comprises at least one structural unit of the formula (I), at least one structural unit of the formula (II), at least one structural unit of the formula (III-8) and at least one structural unit of the formula (IV -8th),
  • R 7 is octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl).
  • a very particularly preferred amphiphilic, cationic polymer according to the invention is the copolymer of N-vinylpyrrolidone, N-vinylcaprolactam, N- (3-dimethylaminopropyl) methacrylamide and 3- (methacryloylamino) propyl-lauryl-dimethylammonium chloride (INCI name:
  • Polyquaternium-69 which is marketed for example under the trade name Aqua Style ® 300 (28-32 wt .-% of active substance in ethanol-water mixture, molecular weight 350,000) by the company ISP.
  • composition according to the invention necessarily contains at least one film-forming and / or setting polymer selected from chitosan and its derivatives.
  • Chitosans are biopolymers and are counted among the group of hydrocolloids. Chemically, these are partially deacetylated chitins of different molecular weight.
  • chitosans For the production of chitosans is based on chitin, preferably the shell remains of crustaceans, which are available as cheap raw materials in large quantities.
  • the chitin is usually first deproteinized by the addition of bases, demineralized by the addition of mineral acids and finally deacetylated by the addition of strong bases, wherein the molecular weights can be distributed over a broad spectrum.
  • bases Preferably used are those having an average molecular weight of 800,000 to 1,200,000 daltons, a Brookfield viscosity (1% by weight in glycolic acid) below 5000 mPas, a degree of deacetylation in the range of 80 to 88%, and a Have ash content of less than 0.3 wt .-%.
  • chitosans as typical cationic biopolymers
  • cationically derivatized chitosans such as, for example, quaternization products
  • alkoxylated chitosans are also suitable for the purposes of the invention.
  • Agents preferred according to the invention are characterized in that they contain neutralization products of chitosan with at least one acid as chitosan derivative (s) according to the invention.
  • the acid used for the neutralization is preferably selected from organic acids, in particular from formic acid, acetic acid, citric acid, lactic acid, pyrrolidonecarboxylic acid, nicotinic acid, hydroxyisobutyric acid,
  • Hydroxyisovalerianchure or mixtures of these acids It is very particularly preferred to select the acid (s) used for the neutralization from lactic acid, pyrrolidonecarboxylic acid, nicotinic acid, hydroxyisobutyric acid, hydroxyisovaleric acid or mixtures of these acids.
  • Suitable chitosan are, for example, under the trade names Hydagen ® CMF (1 wt .-% active ingredient in aqueous solution with 0.4 wt .-% glycolic acid, molecular weight 500000 to 5000000 g / mol Cognis), Hydagen ® HCMF (chitosan (80%) deacetylated), molecular weight 50,000 to 1,000,000 g / mol, Cognis), Kytamer ® PC (80 wt .-% of active substance of chitosan pyrolidoncarboxylat (INCI name: chitosan PCA), Amerchol) and Chitolam ® NB / commercially 101 freely available.
  • Hydagen ® CMF (1 wt .-% active ingredient in aqueous solution with 0.4 wt .-% glycolic acid, molecular weight 500000 to 5000000 g / mol Cognis)
  • the chitosan or its derivatives are preferred in the inventive compositions in an amount of 0.01 wt .-% to 20 wt .-%, particularly preferably from 0.01 wt .-% to 10.0 wt .-%, completely particularly preferably from 0.1% by weight to 1% by weight, based in each case on the weight of the composition according to the invention.
  • a preferred embodiment of the agent according to the invention is an agent for treating keratin-containing fibers, in particular human hair, contained in a cosmetically acceptable carrier (a) at least one amphiphilic, cationic polymer comprising at least one structural unit of the formula (I), at least one structural unit of the formula (II), at least one structural unit of the formula (III-8) and at least one structural unit of the formula (IV-
  • R 7 is octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl) and
  • the abovementioned polymer with the INCI name Polyquaternium 69 (vide supra) is particularly suitable as the amphiphilic cationic polymer.
  • the neutralization products of chitosan are again preferably selected from neutralization products of chitosan with at least one organic acid selected from lactic acid, pyrrolidonecarboxylic acid, nicotinic acid, hydroxyisobutyric acid, hydroxyisovaleric acid or mixtures of these acids.
  • the combinations of the above amphiphilic, cationic polymer (a) with at least one neutralization product of chitosan selected from Hydagen ® CMF (1 wt .-% of active substance in aqueous solution with 0.4 wt .-% glycolic acid, molecular weight 500000 to 5000000 g / mol Cognis), Hydagen ® HCMF (chitosan (80% deacetylated), molecular weight 50,000 to 1,000,000 g / mol, Cognis), Kytamer ® PC (80 wt .-% of active substance of chitosan pyrolidoncarboxylat (INCI name: chitosan PCA), Amerchol ) Chitolam ® NB / 101 or mixtures thereof.
  • Hydagen ® CMF (1 wt .-% of active substance in aqueous solution with 0.4 wt .-% glycolic acid, molecular weight 500000 to 5000000 g
  • the agents according to the invention may contain at least one further film-forming and / or setting polymer selected from nonionic polymers and / or from permanently cationic polymers and / or from amphoteric polymers.
  • the composition according to the invention can contain, in addition to the polymers (a) and (b), at least one film-forming nonionic and / or setting nonionic polymer (c1).
  • the film-forming nonionic and / or setting nonionic polymer (c1) from at least one film-forming nonionic and / or setting nonionic polymer containing at least one structural unit selected from the group of structural units of the formulas (M1) to (M3 )
  • R ' is a hydrogen atom or a (C 2 to C 18 ) acyl group.
  • such film-forming nonionic and / or reinforcing nonionic polymers (c1) with at least one structural element of the formula (M3) are preferably suitable which according to formula (M3) as R 'is a hydrogen atom, an acetyl group or a propanoyl group, in particular a hydrogen atom or a Acetyl group, wear.
  • the film-forming nonionic and / or setting nonionic polymers (c1) are preferably selected from at least one polymer of the group that is formed
  • Suitable polyvinylpyrrolidones are, for example, commercial products such as Luviskol ® K 90 or Luviskol ® K 85 from BASF SE.
  • Suitable polyvinyl alcohols are marketed under the trade names Elvanol.RTM ® from DuPont or Vinol ® 523/540 by Air Products.
  • Suitable polyvinyl acetate is marketed under the trade name Vinac ® as an emulsion from Air Products.
  • Means comprising as film-forming nonionic and / or setting nonionic polymer (c1) at least one polymer selected from the group formed from
  • Copolymers of N-vinylpyrrolidone and vinyl esters of carboxylic acids having 2 to 18 carbon atoms are very particularly preferred according to the invention.
  • a cosmetically acceptable carrier (a) at least one amphiphilic, cationic polymer comprising at least one structural unit of the formula (I), at least one structural unit of the formula (II) , at least one structural unit of the formula (III-8) and at least one structural unit of the formula (IV-8),
  • R 7 is octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl),
  • a cosmetically acceptable carrier (a) at least one amphiphilic, cationic polymer comprising at least one structural unit of the formula (I), at least one structural unit of the formula (II) , at least one structural unit of the formula (III-8) and at least one structural unit of the formula (IV-8),
  • R 7 is octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl),
  • the molar ratio of the structural units comprised of the monomer N-vinylpyrrolidone to the structural units of the polymer comprised of the monomer vinyl acetate is in the range from 20:80 to 80:20, in particular from 30:70 to 70:30 ,
  • Suitable copolymers of vinylpyrrolidone and vinyl acetate are available, for example under the trademark Luviskol ® VA 37, Luviskol ® VA 55, Luviskol ® VA 64 and Luviskol ® VA 73 from the firm BASF SE.
  • amphiphilic, cationic polymer (a) are preferred (vide supra).
  • all of the above-mentioned preferred quantities with respect to the polymer components (a) and (b) of the agent according to the invention are also mutatis mutandis preferred for these embodiments.
  • the composition according to the invention can contain, in addition to the polymers (a) and (b), at least one permanent cationic and / or permanent cationic polymer (c2) which has at least one structural unit containing at least one permanently cationized nitrogen atom ,
  • the polymers (c2) are different from the amphiphilic, cationic polymers (a).
  • Permanently cationized nitrogen atoms are to be understood as meaning those nitrogen atoms which carry a positive charge and thereby form a quaternary ammonium compound.
  • Quaternary ammonium compounds are most commonly prepared by reacting tertiary amines with alkylating agents, e.g. Methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also produced ethylene oxide.
  • alkylating agents e.g. Methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also produced ethylene oxide.
  • alkylating agents e.g. Methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also produced ethylene oxide.
  • alkylating agents e.g. Methyl chloride, benzyl chloride, dimethyl sulfate, dodec
  • Preferred agents according to the invention comprise the film-forming cationic and / or setting cationic polymers (c2) in an amount of from 0.1% by weight to 20.0% by weight, particularly preferably from 0.2% by weight to 10.0 wt .-%, most preferably from 0.5 wt .-% to 5.0 wt .-%, each based on the weight of the composition.
  • the cationic film-forming and / or cationic fixing polymers are particularly preferably selected according to the invention from cationic, quaternized cellulose derivatives.
  • those agents are particularly preferred containing in a cosmetically acceptable carrier
  • R 1 and R 4 independently of one another represent a hydrogen atom or a methyl group
  • X 1 and X 2 independently of one another represent an oxygen atom or a group NH
  • a 1 and A 2 independently of one another are a group of ethane-1, 2-diyl, propane-1, 3-diyl or butane-1, 4-diyl,
  • R 2 , R 3 , R 5 and R 6 independently of one another represent a (C 1 to C 4 ) -alkyl group
  • R 7 is a (C 8 to C 30 ) -alkyl group, (b) at least one film-forming and / or setting polymer selected from chitosan and its derivatives and (c2) at least one additional film-forming cationic and / or setting cationic
  • Polymer selected from the group of cationic, quaternized cellulose derivatives.
  • such agents in the context of this embodiment are particularly suitable, which contain in a cosmetically acceptable carrier
  • R 7 is octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl),
  • Hexadecyl cetyl
  • octadecyl stearyl
  • eicosyl arachyl
  • docosyl behenyl
  • Polymer selected from the group of cationic, quaternized cellulose derivatives.
  • such cationic, quaternized celluloses prove to be advantageous in the sense of the invention, which carry more than one permanent cationic charge in a side chain.
  • cationic cellulose derivatives those which are prepared from the reaction of hydroxyethylcellulose with a dimethyldiallylammonium reactant (in particular dimethyldiallylammonium chloride), if appropriate in the presence of further reactants.
  • a dimethyldiallylammonium reactant in particular dimethyldiallylammonium chloride
  • these cationic celluloses such cationic celluloses with the INCI name Polyquaternium-4 in turn, are particularly suitable, which are sold for example under the names of Celquat ® H 100, Celquat L 200 ® by the company National Starch.
  • agents according to the invention which are present in a cosmetically acceptable carrier are found to be particularly suitable
  • R 7 is octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl),
  • a dimethyldiallylammonium reactant especially dimethyldiallylammonium chloride
  • the abovementioned preferred embodiments of the amphiphilic, cationic polymer (a) are suitable (vide supra).
  • all of the above-mentioned preferred quantities with respect to the polymer components (a) and (b) of the agent according to the invention are also suitable mutatis mutandis for these embodiments as well.
  • At least one cationic film-forming and / or cationic setting polymer (c2) is particularly preferred which comprises at least one structural unit of the formula (I) and at least one structural unit of the formula (VI) and optionally at least one structural unit of the formula (V)
  • R 1 and R 4 independently of one another represent a hydrogen atom or a methyl group
  • a 1 and A 2 are each independently a group of ethane-1, 2-diyl, propane-1, 3-diyl or
  • R 2 , R 3 , R 5 and R 6 independently of one another represent a (C 1 to C 4 ) -alkyl group
  • R 7 is a (C 8 to C 30 ) alkyl group.
  • ком ⁇ онент (VI) To compensate for the positive charge of the monomer (VI) are all possible physiologically acceptable anions, such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • physiologically acceptable anions such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • agents which are particularly preferably suitable according to the invention are those agents which are contained in a cosmetically acceptable carrier
  • R 1 and R 4 independently of one another represent a hydrogen atom or a methyl group
  • X 1 and X 2 independently of one another represent an oxygen atom or a group NH
  • a 1 and A 2 independently of one another are a group of ethane-1, 2-diyl, propane-1, 3-diyl or butane-1, 4-diyl,
  • R 2 , R 3 , R 5 and R 6 independently of one another represent a (C 1 to C 4 ) -alkyl group
  • R 7 is a (C 8 to C 30 ) alkyl group
  • (c2) at least one additional film-forming cationic and / or setting cationic polymer which comprises at least one structural unit of the formula (I) and at least one structural unit of the formula (VI) and at least one structural unit of the formula (V)
  • R 1 and R 4 independently of one another represent a hydrogen atom or a methyl group
  • a 1 and A 2 independently of one another are a group of ethane-1, 2-diyl, propane-1, 3-diyl or butane-1, 4-diyl,
  • R 2 , R 3 , R 5 and R 6 independently of one another represent a (C 1 to C 4 ) -alkyl group
  • R 7 is a (C 8 to C 30 ) alkyl group.
  • agents which are particularly preferred according to the invention and which contain in a cosmetically acceptable carrier (a) at least one amphiphilic, cationic polymer comprising at least one structural unit of the formula (I), at least one structural unit of the formula (II), at least one structural unit of the formula (III-8) and at least one structural unit of the formula (IV-8)
  • R 7 is octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl),
  • (c2) at least one additional film-forming cationic and / or setting cationic polymer which comprises at least one structural unit of the formula (I) and at least one structural unit of the formula (VI) and at least one structural unit of the formula (V)
  • R 1 and R 4 independently of one another represent a hydrogen atom or a methyl group
  • a 1 and A 2 independently of one another are a group of ethane-1, 2-diyl, propane-1, 3-diyl or butane-1, 4-diyl,
  • R 2 , R 3 , R 5 and R 6 independently of one another represent a (C 1 to C 4 ) -alkyl group
  • R 7 is a (C 8 to C 30 ) alkyl group.
  • Suitable compounds (c2) are for example as
  • amphiphilic, cationic polymer (a) are preferred (vide supra).
  • all of the above-mentioned preferred quantities with respect to the polymer components (a) and (b) of the agent according to the invention are also mutatis mutandis preferred for these embodiments.
  • R is a (C 1 to C 4 ) -alkyl group, in particular a methyl group, and additionally has at least one further cationic and / or nonionic structural element.
  • R 1 and R 4 independently of one another represent a hydrogen atom or a methyl group
  • X 1 and X 2 independently of one another represent an oxygen atom or a group NH
  • a 1 and A 2 independently of one another are a group of ethane-1, 2-diyl, propane-1, 3-diyl or butane-1, 4-diyl,
  • R 2 , R 3 , R 5 and R 6 independently of one another represent a (C 1 to C 4 ) -alkyl group
  • R 7 is a (C 8 to C 30 ) -alkyl group, (b) at least one film-forming and / or setting polymer selected from chitosan and its derivatives and (c2) at least one additional film-forming cationic and / or setting cationic
  • Nitrogen atom contains at least one structural element of the formula (M4)
  • R is a (C 1 to C 4 ) -alkyl group, in particular a methyl group, and additionally has at least one further cationic and / or nonionic structural element.
  • Means that comply with this embodiment form transparent, i. unclouded compositions. A clouding is not visible to the naked eye.
  • the means of this embodiment additionally excellently satisfy the advantageous parameters with regard to the strong hairstyle hold or volume or hair care.
  • component (c2) To compensate for the positive polymer charge of component (c2) are all possible physiologically acceptable anions, such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • physiologically acceptable anions such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • (a) at least one amphiphilic, cationic polymer comprising at least one structural unit of the formula (I), at least one structural unit of the formula (II), at least one structural unit of the formula (III-8) and at least one structural unit of the formula (IV-8) wherein R 7 is octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl),
  • R is a (C 1 to C 4 ) -alkyl group, in particular a methyl group, and additionally has at least one further cationic and / or nonionic structural element.
  • the abovementioned polymer with the INCI name Polyquaternium 69 is particularly suitable as the amphiphilic cationic polymer (a).
  • At least one copolymer (c2-1) is present in the agent according to the invention, in addition to at least one structural element of the formula (M4) additionally comprises a structural element of the formula (I)
  • R is a (C 1 to C 4 ) -alkyl group, in particular a methyl group.
  • the copolymers (c2-1) To compensate for the positive polymer charge of the copolymers (c2-1) are all possible physiologically acceptable anions, such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • physiologically acceptable anions such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • Very particularly preferred cationic film-forming and / or cationic fixing polymers as copolymers (c2-1) contain 10 to 30 mol%, preferably 15 to 25 mol% and in particular 20 mol% of structural units of the formula (M4) and 70 to 90 mol .-%, preferably 75 to 85 mol .-% and in particular 80 mol .-% of structural units according to formula (I).
  • copolymers (c2-1) in addition to polymer units resulting from the incorporation of said structural units of the formula (M4) and (I) in the copolymer, a maximum of 5 wt .-%, preferably at most 1 wt. %, Contain polymer units due to incorporation of other monomers.
  • Polyquaternium-16 N-methylvinylimidazole / vinylpyrrolidone copolymers
  • BASF under the trade names Luviquat ® Style , Luviquat.RTM ® FC 370, Luviquat.RTM ® FC 550, FC 905 and Luviquat.RTM ® Luviquat.RTM ® HM 552
  • agents according to the invention comprise a copolymer (c2-1), in particular of the formula (poly), which has molar masses within a certain range.
  • a copolymer (c2-1) has a molecular weight of 50 to 400 kDa, preferably of 100 to 300 kDa, more preferably of 150 to 250 kDa and in particular of 190 to 210 kDa.
  • compositions according to the invention may also contain copolymers (c2-2) which, starting from the copolymer (c2-1), comprise structural units of the formula ## STR1 ## as additional structural units (II)
  • agents according to the invention are therefore characterized in that they comprise as cationic film-forming and / or cationic setting polymer (c2) at least one copolymer (c2-2) which has at least one structural unit of formula (M4-a) and at least one structural unit according to Formula (I) and at least one structural unit according to formula (II)
  • copolymers (c2-2) in addition to polymer units resulting from the incorporation of the structural units of the formula (M4-a), (I) and (II) in the copolymer, a maximum of 5 wt .-% , preferably at most 1 wt .-%, contain polymer units, which go back to the incorporation of other monomers.
  • the copolymers (c2-2) are preferably composed exclusively of structural units of the formulas (M4-a), (I) and (II) and can be represented by the general formula (Poly 2)
  • indices m, n and p vary depending on the molecular weight of the polymer and should not mean that they are block copolymers. Rather, structural units of said formulas can be present in the molecule in a statistically distributed manner.
  • physiologically acceptable anions such as chloride, bromide, hydrogen sulfate, Methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • a methosulfate be used refer to those N-methylvinylimidazole / vinylpyrrolidone / vinylcaprolactam copolymers, according to INCI nomenclature as Polyquaternium-46 and are for example available under the trade names Luviquat ® Hold by BASF ,
  • Very particularly preferred copolymers (c2-2) contain 1 to 20 mol%, preferably 5 to 15 mol% and in particular 10 mol% of structural units of the formula (M4-a) and 30 to 50 mol%, preferably 35 to 45 mol% and in particular 40 mol% of structural units of the formula (I) and 40 to 60 mol%, preferably 45 to 55 mol% and in particular 60 mol% of structural units of the formula (II) ,
  • agents according to the invention contain a copolymer (c2-2) which has molecular weights within a certain range.
  • agents according to the invention are preferred in which the copolymer (c2-2) has a molecular weight of from 100 to 1000 kDa, preferably from 250 to 900 kDa, more preferably from 500 to 850 kDa and in particular from 650 to 710 kDa.
  • the agents according to the invention may also be copolymers (c2) as film-forming cationic and / or setting cationic polymer (c2) -3), which have as structural units structural units of the formulas (M4-a) and (I), as well as further structural inhibitors from the group of the vinylimidazole units and further structural units from the group of the acrylamide and / or methacrylamide units.
  • agents according to the invention are characterized in that they comprise as cationic film-forming and / or cationic setting polymer (c2) at least one copolymer (c2-3) which has at least one structural unit of formula (M4-a) and at least one further structural unit of formula (I) and at least one structural unit of the formula (VI) and at least one structural unit of the formula (VII)
  • the copolymers (c2-3) in addition to polymer units resulting from the incorporation of said structural units of the formula (M4-a), (I), (VI) and (VII) in the copolymer, a maximum of 5 Wt .-%, preferably at most 1 wt .-%, polymer units, which go back to the incorporation of other monomers.
  • the Copolymers (c2-3) are built up exclusively from structural units of the formula (M4-a), (I), (VI) and (VII) and can be distinguished by the general formula (Poly3)
  • physiologically acceptable anions such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • a methosulfate be used refer to those N-Methylvinylimidazol ⁇ / inylpyrrolidon ⁇ / inylimidazol / methacrylamide copolymers, according to INCI nomenclature as Polyquaternium-68 and are, for example, from BASF under the tradename Luviquat ® Supreme available.
  • Very particularly preferred copolymers (c2-3) contain 1 to 12 mol%, preferably 3 to 9 mol% and in particular 6 mol% of structural units of the formula (M4-a) and 45 to 65 mol%, preferably 50 to 60 mol% and in particular 55 mol% of structural units of the formula (I) and 1 to 20 mol%, preferably 5 to 15 mol% and in particular 10 mol% of structural units of the formula (VI) and 20 to 40 mol%, preferably 25 to 35 mol% and in particular 29 mol% of structural units of the formula (VII).
  • agents according to the invention contain a copolymer (c2-3) which has molecular weights within a certain range.
  • agents according to the invention are preferred in which the copolymer (c2-3) has a molecular weight of 100 to 500 kDa, preferably from 150 to 400 kDa, more preferably from 250 to 350 kDa and in particular from 290 to 310 kDa.
  • Vinylpyrrolidone / i-vinyl-S-methyl-I H-imidazolium chloride copolymers (such as for example that with the INCI name Polyquaternium-16 under the trade names Luviquat ® Style, Luviquat ® FC 370, Luviquat ® FC 550, Luviquat ® FC 905 and Luviquat ® HM 552 (BASF SE)), vinyl pyrrolidone / i-vinyl-3-methyl-I H-imidazolium copolymers (such for example that with the INCI name Polyquaternium-44 under the trade names Luviquat ® Care (BASF SE)), vinylpyrrolidone / vinylcaprolactam / i-vinyl-3-methyl-I H- imidazolium Terpolynner (such as that with the INCI name Polyquaternium - 46 under the trade names Luviquat ® Care or Luviquat ® Hold (BASF SE)), vinylpyrroli
  • amphiphilic, cationic polymer (a) are preferred (vide supra).
  • all of the above-mentioned preferred quantities with respect to the polymer components (a) and (b) of the agent according to the invention are also mutatis mutandis preferred for these embodiments.
  • the agents according to the invention preferably additionally contain at least one surfactant, nonionic, anionic, cationic, ampholytic surfactants being suitable in principle.
  • the group of ampholytic or amphoteric surfactants includes zwitterionic surfactants and ampholytes.
  • the surfactants according to the invention may already have emulsifying activity.
  • the additional surfactants are in the inventive composition preferably in an amount of 0.01 wt .-% to 5 wt .-%, particularly preferably from 0.05 wt .-% to 0.5 wt .-%, each based on the Weight of the agent, included.
  • agents according to the invention additionally comprise at least one nonionic surfactant.
  • Nonionic surfactants contain as hydrophilic group e.g. a polyol group, one
  • Such compounds are, for example
  • alkylphenols having 8 to 15 carbon atoms in the alkyl group such as those available under the trade names Dehydol ® LS, Dehydol ® LT types (Cognis), C 2 -C 3 o-fatty acid mono- and diesters of addition products of 1 to 30 moles of ethylene oxide with glycerol, addition products of 5 to 60 moles of ethylene oxide with castor oil and hydrogenated castor oil, Polyol fatty acid esters, such as the commercial product Hydagen ® HSP (Cognis) or
  • alkylene oxide addition products of saturated linear fatty alcohols and fatty acids with in each case 2 to 100 mol of ethylene oxide per mole of fatty alcohol or fatty acid have proven to be very particularly preferred nonionic surfactants. Preparations with excellent properties are also obtained when they contain as nonionic surfactants C 12 -C 30 fatty acid mono- and diesters of addition products of 1 to 30 moles of ethylene oxide with glycerol and / or addition products of 5 to 60 moles of ethylene oxide with castor oil and hydrogenated castor oil ,
  • both products with a "normal” homolog distribution and those with a narrow homolog distribution can be used.
  • "normal” homolog distribution are meant mixtures of homologs obtained in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates as catalysts. Narrowed homolog distributions are obtained when, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alkoxides are used as catalysts. The use of products with narrow homolog distribution may be preferred.
  • the agents according to the invention as surfactant very particularly preferably contain at least one addition product of from 15 to 100 mol of ethylene oxide, in particular from 15 to 50 mol of ethylene oxide, to a linear or branched (in particular linear) fatty alcohol having from 8 to 22 carbon atoms.
  • ethylene oxide in particular from 15 to 50 mol of ethylene oxide
  • linear or branched (in particular linear) fatty alcohol having from 8 to 22 carbon atoms.
  • ceteareth-15, ceteareth-25 or ceteareth-50 which are marketed as Eumulgin ® CS 15 (Cognis), Cremophor A25 (BASF SE) or Eumulgin ® CS 50 (Cognis).
  • Suitable anionic surfactants are in principle 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.
  • anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts having 2 to 4 C atoms in the alkanol group, linear and branched fatty acids having 8 to 30 C atoms (Soap),
  • Ethercarbon Acid the formula RO- (CH2-CH2 ⁇ ) ⁇ -CH2-COOH, in which R is a linear
  • Alkyl group having 8 to 30 C atoms and x 0 or 1 to 16,
  • Sulfosuccinic acid mono-alkyl polyoxyethyl esters having 8 to 24 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkanesulfonates having 8 to 24 carbon atoms, linear alpha-olefin sulfonates having 8 to 24 carbon atoms,
  • Alpha sulfo fatty acid methyl esters of fatty acids having 8 to 30 carbon atoms, - alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO (CH 2 -CH 2 O) x -OSO 3 H, in which R is a preferably linear alkyl group having 8 to 30 carbon atoms and x 0 or 1 to 12,
  • OX in the R 1 is preferably an aliphatic hydrocarbon radical having 8 to 30 carbon atoms
  • R 2 is hydrogen, a radical (CH 2 CH 2 O) n R 1 or X, n is from 1 to 10 and X is hydrogen, an alkali or alkaline earth metal or NR 3 R 4 R 5 R 6 , where R 3 to R 6 independently of one another represent hydrogen or a C 1 to C 4 hydrocarbon radical, is a sulfated fatty acid alkylene glycol ester of the formula (E1-II) R 7 CO (AlkO ) n SO 3 M (E1-II) in which R 7 CO is a linear or branched, aliphatic, saturated and / or unsaturated acyl group containing 6 to 22 carbon atoms, Alk is CH 2 CH 2, CHCH 3 CH 2 and / or CH 2 CHCH 3 , n is from 0.5 to 5 and M is a cation as described in DE-OS 197 36 906,
  • Typical examples of monoglyceride (ether) sulfates suitable for the purposes of the invention are the reaction products of lauric acid monoglyceride, coconut fatty acid monoglyceride, palmitic acid monoglyceride, stearic acid monoglyceride, oleic acid monoglyceride and tallow fatty acid monoglyceride and their ethylene oxide adducts with sulfur trioxide or chlorosulfonic acid in the form of their sodium salts.
  • monoglyceride sulfates of the formula (E1-III) are used in which R 8 CO is a linear acyl radical having 8 to 18 carbon atoms, amide-ether carboxylic acids,
  • Condensation products of C 8 - C 30 - fatty alcohols with protein hydrolysates and / or amino acids and their derivatives which are known to the skilled person as protein fatty acid condensates, such as Lamepon ® - types Gluadin ® - types Hostapon ® KCG or Amisoft ® - types.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 C atoms in the alkyl group and up to 12 glycol ether groups in the molecule, sulfosuccinic acid mono- and dialkyl esters having 8 to 18 C atoms in the alkyl group and sulfosuccinic acid monoalkylpolyoxyethylester with 8 to 18 C atoms in the alkyl group and 1 to 6 oxyethyl groups, Monoglycerdisulfate, alkyl and Alkenyletherphosphate and Eiweissfettkladensate.
  • cationic surfactants of the quaternary ammonium compound type 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.
  • Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one -COO () or -SO 3 ' " ' group in the molecule
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as N-alkyl-N , N-dimethylammonium glycinates, for example cocoalkyldimethylammoniumglycinate, N-acylaminopropyl-N, N-dimethylammoniumglycinates, for example cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines having A preferred zwitterionic surfactant is the fatty acid amide derivative known by the INCI name cocamidopropyl betaine.
  • Ampholytes are understood as meaning those surface-active compounds which, apart from a C 8 -C 24 -alkyl or -acyl group in the molecule, contain at least one free amino group and at least one -COOH or -SO 3 H group and are capable of forming internal salts.
  • ampholytes are N-alkylglycines, N-alkylpropionic 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 ampholytes are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 -C 18 acylsarcosine.
  • compositions according to the invention contain the ingredients or active substances in a cosmetically acceptable carrier.
  • Preferred cosmetically acceptable carriers are aqueous, alcoholic or aqueous-alcoholic media with preferably at least 10% by weight of water, based on the total agent.
  • alcohols it is possible in particular to include the lower alcohols having 1 to 4 carbon atoms usually used for cosmetic purposes, such as, for example, ethanol and isopropanol.
  • at least one (C 1 to C 4 ) monoalkyl alcohol in the inventive compositions in particular in an amount of 1 to 50 wt .-% in particular of Use 5 to 30 wt .-%. This is in turn preferred in particular for the packaging as pump foam or aerosol foam.
  • Particularly suitable as additional co-solvents are unbranched or branched hydrocarbons such as pentane, hexane, isopentane and cyclic hydrocarbons such as cyclopentane and cyclohexane.
  • particularly preferred water-soluble solvents are glycerol, ethylene glycol and propylene glycol in an amount of up to 30% by weight, based on the total agent.
  • compositions according to the invention preferably contain from 0.01 to 30% by weight of glycerol and / or propylene glycol and / or polyethylene glycol and / or polypropylene glycol, based on the total agent.
  • the agents preferably have a pH of 2 to 11.
  • the pH range between 2 and 8 is particularly preferred.
  • the pH value in the context of this document refers to the pH at 25 ° C., unless stated otherwise.
  • compositions of the invention may further contain the auxiliaries and additives which are usually added to conventional styling.
  • auxiliaries and additives in particular additional care substances are mentioned.
  • a silicone oil and / or a silicone gum can be used as a care material.
  • Silicone oils or silicone gums which are suitable according to the invention are in particular dialkyl and alkylaryl siloxanes, for example dimethylpolysiloxane and methylphenylpolysiloxane, and also their alkoxylated, quaternized or else anionic derivatives. Preference is given to cyclic and linear polydialkylsiloxanes, their alkoxylated and / or aminated derivatives, dihydroxypoly-dimethylsiloxanes and polyphenylalkylsiloxanes.
  • Silicone oils cause a wide variety of effects. For example, at the same time they influence the dry and wet combability, the grip of dry and wet hair and the shine.
  • silicone oils is understood by the person skilled in the art as meaning several structures of silicon-organic compounds. Initially, this is understood to mean the dimethiconols.
  • Examples of such products include the following commercial products: Botanisil NU-150M (Botanigenics), Dow Coming 1-1254 Fluid, Dow Corning 2-9023 Fluid, Dow Corning 2-9026 Fluid, Ultrapure Dimethiconol (Ultra Chemical), Unisil SF- R (Universal Preserve), X-21-5619 (Shin-Etsu Chemical Co.), Abil OSW 5 (Degussa Care Specialties), ACC DL-9430 Emulsion (Taylor Chemical Company), AEC Dimethiconol & Sodium Dodecylbenzenesulfonate (A & E Connock (Perfumery & Cosmetics) Ltd.), BC Dimethiconol Emulsion 95 (Basildon Chemical Company, Ltd.), Cosmetic Fluid 1401, Cosmetic Fluid 1403, Cosmetic Fluid 1501, Cosmetic Fluid 1401 DC (all aforementioned Chemsil Silicones, Inc.), Dow Corning 1401 Fluid, Dow Corning 1403 Fluid, Dow Corning 1501 Fluid, Dow Corning 1784 HVF
  • Dimethicones form the second group of silicones which may be present according to the invention. These may be both linear and branched as well as cyclic or cyclic and branched.
  • Dimethicone copolyols form another group of silicones that are suitable.
  • Corresponding dimethicone copolyols are commercially available and are sold, for example, by Dow Corning under the name Dow Corning® 5330 Fluid.
  • the teaching according to the invention also encompasses the fact that the dimethiconols, dimethicones and / or dimethicone copolymers can already be present as an emulsion.
  • the corresponding emulsion of dimethiconols, dimethicones and / or dimethicone copolyols can be prepared both after the preparation of the corresponding dimethiconols, dimethicones and / or dimethicone copolyols from these and the conventional methods of emulsification known to the person skilled in the art.
  • both cationic, anionic, nonionic or zwitterionic surfactants and emulsifiers can be used as auxiliaries for the preparation of the corresponding emulsions.
  • the emulsions of dimethiconols, dimethicones and / or dimethicone copolyols can also be prepared directly by an emulsion polymerization process. Such methods are also well known to the person skilled in the art.
  • the droplet size of the emulsified particles is according to the invention 0.01 to 10000 microns, preferably 0.01 to 100 .mu.m, more preferably 0.01 to 20 microns and most preferably 0 , 01 to 10 ⁇ m.
  • the particle size is determined by the method of light scattering. If branched dimethiconols, dimethicones and / or dimethicone copolyols are used, it is to be understood that the branching is greater than a random branching, which occurs randomly due to impurities of the respective monomers.
  • branched dimethiconols, dimethicones and / or dimethicone copolyols are therefore to be understood as meaning that the degree of branching is greater than 0.01%.
  • a degree of branching is greater than 0.1%, and most preferably greater than 0.5%.
  • the degree of branching is determined from the ratio of the unbranched monomers to the branching monomers, that is, the amount of tri- and tetrafunctional siloxanes.
  • both low-branched and highly branched dimethiconols, dimethicones and / or dimethicone copolyols can be very particularly preferred.
  • Particularly suitable silicones are amino-functional silicones, in particular the silicones, which are summarized under the INCI name Amodimethicone. It is therefore preferred according to the invention if the agents according to the invention additionally contain at least one amino-functional silicone. These are silicones which have at least one, optionally substituted, amino group. These silicones are referred to as amodimethicone according to the INCI nomenclature and are available for example in the form of an emulsion as a commercial product Dow Corning ® 939 or as a commercial product Dow Corning ® 949 in a mixture with a cationic and a nonionic surfactant.
  • those amino-functional silicones are used which have an amine number above 0.25 meq / g, preferably above 0.3 meq / g and especially preferably above 0.4 meq / g.
  • 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.
  • the agents contain the silicones preferably in amounts of from 0.01% by weight to 15% by weight, particularly preferably from 0.05 to 2% by weight, based on the total agent.
  • the agent may contain, for example, at least one protein hydrolyzate and / or one of its derivatives.
  • Protein hydrolysates are product mixtures obtained by acid, alkaline or enzymatically catalyzed degradation of proteins (proteins). According to the invention, the term protein hydrolyzates also means total hydrolyzates as well as individual amino acids and their derivatives as well as mixtures of different amino acids.
  • the molecular weight of the protein hydrolysates which can be used according to the invention is between 75, the molecular weight for glycine, and 200,000, preferably the molecular weight is 75 to 50,000 and very particularly preferably 75 to 20,000 daltons.
  • protein hydrolysates of both vegetable and animal or marine or synthetic origin can be used.
  • Animal protein hydrolysates are, for example, elastin, collagen, keratin, silk and milk protein 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 and Co), Lexein ® (Inolex) sericin (Pentapharm) and kerasol tm ® (Croda) sold.
  • the protein hydrolysates are present in the agents according to the invention, for example, in concentrations of from 0.01% by weight to 20% by weight, preferably from 0.05% by weight to 15% by weight and very particularly preferably in amounts of 0 , 05 wt .-% up to 5 wt .-%, each based on the total application preparation included.
  • the agent according to the invention may further comprise at least one vitamin, a provitamin, a vitamin precursor and / or one of their derivatives.
  • vitamins, provitamins and vitamin precursors are preferred, which are usually assigned to groups A, B, C, E, F and H.
  • vitamin A includes retinol (vitamin A 1 ) and 3,4-didehydroretinol (vitamin A 2 ).
  • the ß-carotene is the provitamin of retinol.
  • vitamin A component for example, vitamin A acid and its esters, vitamin A aldehyde and vitamin A alcohol and its esters such as the palmitate and the acetate into consideration.
  • the agents contain the vitamin A component preferably in amounts of 0.05-1% by weight, based on the total application preparation.
  • Vitamin B 1 thiamin
  • vitamin B 2 riboflavin
  • vitamin B 3 nicotinic acid and / or nicotinamide (niacinamide)
  • vitamin B 5 pantothenic acid, panthenol and Pantolactone
  • vitamin B 6 pyridoxine and pyridoxamine and pyridoxal
  • vitamin C ascorbic acid
  • vitamin E tocopherols, in particular ⁇ -tocopherol
  • vitamin F lactinoleic acid and / or linolenic acid
  • vitamin H vitamin H.
  • the agents according to the invention preferably contain vitamins, provitamins and vitamin precursors from groups A, B, C, E and H. Panthenol, pantolactone, pyridoxine and its derivatives as well as nicotinamide and biotin are particularly preferred.
  • the addition of panthenol increases the flexibility of the polymer film formed using the composition of the present invention.
  • the compositions according to the invention may contain panthenol instead of or in addition to glycerol and / or propylene glycol.
  • the agents according to the invention contain panthenol, preferably in one Amount of 0.05 to 10 wt .-%, particularly preferably 0.1 to 5 wt .-%, each based on the total agent.
  • compositions according to the invention may further contain at least one plant extract.
  • these extracts are produced by extraction of the whole plant. However, it may also be preferred in individual cases, the extracts exclusively from flowers and / or
  • compositions according to the invention mixtures of several, especially two, different plant extracts.
  • Mono- or oligosaccharides can also be used as a care substance in the compositions according to the invention.
  • Both monosaccharides and oligosaccharides, such as cane sugar, can be used.
  • Lactose and raffinose The use of monosaccharides is preferred according to the invention. Among the monosaccharides, in turn, those compounds which contain 5 or 6 carbon atoms are preferred.
  • Suitable pentoses and hexoses are, for example, ribose, arabinose, xylose, lyxose,
  • Arabinose, glucose, galactose and fructose are preferably used carbohydrates; Very particular preference is given to using glucose which is suitable both in the D - (+) or L - (-) configuration or as a racemate.
  • Uronic acids sucgar acids
  • sugar alcohols sugar alcohols
  • glycosides are used according to the invention.
  • Preferred sugars are gluconic acid, glucuronic acid, sugar acid, mannose acid and mucic acid.
  • Preferred sugar alcohols are sorbitol, mannitol and dulcitol.
  • Preferred glycosides are the methylglucosides.
  • the monosaccharides or oligosaccharides used are usually made from natural raw materials such as
  • Configurations e.g., D-glucose, D-fructose and D-galactose.
  • the mono- or oligosaccharides are preferred in the agents according to the invention in one
  • the agent may further contain at least one lipid as a care substance.
  • Lipids suitable according to the invention are phospholipids, for example soya lecithin, egg lecithin and cephalins, and also the substances known under the INCI names linoleic amidopropyl PG-dimonium chlorides phosphates, cocamidopropyl PG-dimonium chlorides phosphates and stearamidopropyl PG-dimonium chlorides phosphates. These are sold, for example, by the company Mona under the trade names Phospholipid EFA® , Phospholipid PTC® and Phospholipid SV® .
  • the agents according to the invention preferably contain the lipids in amounts of from 0.01 to 10% by weight, in particular from 0.1 to 5% by weight, based on the total application preparation.
  • oil bodies are suitable as a care substance.
  • the natural and synthetic cosmetic oil bodies include, for example: vegetable oils.
  • vegetable oils examples include sunflower oil, olive oil, soybean oil, rapeseed oil, almond oil, jojoba oil, orange oil, wheat germ oil, peach kernel oil and the liquid portions of coconut oil.
  • triglyceride oils such as the liquid portions of beef tallow as well as synthetic triglyceride oils.
  • Ester oils are to be understood as meaning the esters of C 6 - C 30 fatty acids with C 2 - C 30 fatty alcohols. The monoesters of the fatty acids with alcohols having 2 to 24 carbon atoms are preferred.
  • isopropyl myristate IPM Rilanit ®
  • isononanoic acid C16-18 alkyl ester Cetiol ® SN
  • 2-ethylhexyl palmitate Cegesoft ® 24
  • stearic acid-2-ethylhexyl ester Cetiol ® 868
  • cetyl oleate glycerol tricaprylate, Kokosfettalkohol- caprate / caprylate (Cetiol ® LC)
  • n-butyl stearate oleyl erucate
  • isopropyl palmitate IPP Rilanit ®
  • oleyl Oleate Cetiol ®
  • hexyl laurate Cetiol ® A
  • di-n-butyl adipate Cetiol ® B
  • myrist IPM Rilanit ®
  • Dicarboxylic acid esters such as di-n-butyl adipate, di- (2-ethylhexyl) adipate, di- (2-ethylhexyl) succinate and di-isotridecyl acelate
  • diol esters such as ethylene glycol dioleate, ethylene glycol diisotridecanoate, propylene glycol di (2- ethylhexanoate), propylene glycol diisostearate, propylene glycol di-pelargonate, butanediol diisostearate, neopentyl glycol dicaprylate, symmetrical, asymmetrical or cyclic esters of carbonic acid with fatty alcohols, for example described in DE-OS 197 56 454, glycerol carbonate or dicaprylyl carbonate (Cetiol ® CC),
  • Fatty acid partial glycerides which are understood to mean monoglycerides, diglycerides and their technical mixtures. With the use of technical products production reasons may still contain small amounts of triglycerides.
  • the partial glycerides preferably follow the formula (D4-I), CH 2 O (CH 2 CH 2 O) m R 1
  • R 3 in the R 1 , R 2 and R 3 is independently of one another hydrogen or a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22, preferably 12 to 18, Carbon atoms are provided with the proviso that at least one of these groups is an acyl radical and at least one of these groups is hydrogen.
  • the sum (m + n + q) is 0 or numbers from 1 to 100, preferably 0 or 5 to 25.
  • R 1 is an acyl radical and R 2 and R 3 are hydrogen and the sum (m + n + q) is 0.
  • Typical examples are mono- and / or diglycerides based on caproic, caprylic, 2-ethylhexanoic, capric, lauric, isotridecanoic, myristic, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic , Elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures.
  • oleic acid monoglycerides are used.
  • the amount used of the natural and synthetic cosmetic oil bodies in the compositions according to the invention is usually from 0.1 to 30% by weight, based on the total application preparation, preferably from 0.1 to 20% by weight, and in particular from 0.1 to 15% by weight. %.
  • UV filter By adding a UV filter, both the agents themselves and the treated fibers can be protected from the harmful effects of UV radiation.
  • at least one UV filter is added to the agent.
  • the suitable UV filters are not subject to any general restrictions with regard to their structure and their physical properties. On the contrary, all UV filters which can be used in the cosmetics sector and whose absorption maximum lies in the UVA (315-400 nm), in the UVB (280-315 nm) or in the UVC ( ⁇ 280 nm) range are suitable. UV filter with an absorption maximum in the UVB range, in particular in the range from about 280 to about 300 nm, are particularly preferred.
  • the UV filters preferred according to the invention can be selected, for example, from substituted benzophenones, p-aminobenzoic acid esters, diphenylacrylic acid esters, cinnamic acid esters, salicylic acid esters, benzimidazoles and o-aminobenzoic acid esters.
  • UV filters which can be used according to the invention are 4-aminobenzoic acid, N, N, N-trimethyl-4- (2-oxoborn-3-ylidenemethyl) aniline methylsulfate, 3,3,5-trimethylcyclohexyl salicylate (homosalates), 2-hydroxy-4-methoxy-benzophenone (benzophenone-3; Uvinul ® M 40, Uvasorb MET ®, ® Neo Heliopan BB, Eusolex ® 4360), 2-phenylbenzimidazole-5-sulfonic acid and potassium, sodium and triethanolamine salts ( Phenylbenzimidazole Sulfonic Acid; Parsol ® HS; Neo Heliopan Hydro ®), 3,3 '- (1, 4-phenylenedimethylene) bis (7,7-dimethyl-2-oxo-bicyclo [2.2.1] hept-1- yl-methane sulfonic acid) and salts thereof, 1- (4-tert-butyl
  • the UV filters are usually contained in amounts of 0.01-5 wt .-%, based on the total application preparation. Amounts of 0.1-2.5 wt .-% are preferred.
  • the composition according to the invention also contains one or more substantive dyes. This allows the treated keratin fiber not only to be temporarily patterned when the agent is applied, but also dyed at the same time. This may be particularly desirable if only a temporary dyeing is desired, for example, with eye-catching fashion colors, which can be removed again by simple washing from the keratinic fiber.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred substantive dyes are those having the international designations or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange 1, HC Red 1, HC Red 1, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 11, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 known compounds and 1, 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1, 4-bis (ß-hydroxyethyl) - amino-2-nitrobenzene, 3-nitro-4- (ß-hydroxyethyl ) -aminophenol, 2- (2'
  • the dyes which are also known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51 are very particularly preferred cationic substantive dyes of group (c).
  • the cationic direct dyes, which are sold under the trademark Arianor ®, according to the invention are also very particularly preferred cationic direct dyes.
  • the agents according to the invention according to this embodiment preferably contain the substantive dyes in an amount of 0.001 to 20 wt .-%, based on the total agent.
  • the agents according to the invention are free of oxidation dye precursors.
  • Oxidation dye precursors are classified into so-called developer components and coupler components.
  • the developer components form the actual dyes under the influence of oxidizing agents or of atmospheric oxygen with one another or with coupling with one or more coupler components.
  • compositions according to the invention can be carried out in all forms customary for styling agents, for example in the form of solutions which can be applied to the hair as hair lotions or pump or aerosol spray, in the form of creams, emulsions, waxes, gels or surfactant-containing foaming solutions or other preparations suitable for use on the hair.
  • Hair creams and gels generally contain structurants and / or thickening polymers which serve to give the products the desired consistency.
  • Structurants and / or thickening polymers are typically used in an amount of from 0.1 to 10% by weight, based on the total product. Amounts of 0.5 to 5 wt .-%, in particular 0.5 to 3 wt .-% are preferred.
  • the agents according to the invention are preferably used as pump spray, aerosol spray, pump foam or aerosol foam.
  • the agents according to the invention are packaged in a dispensing device, which is either an additionally filled with a propellant compressed gas container ("aerosol container”) or a non-aerosol container.
  • a dispensing device which is either an additionally filled with a propellant compressed gas container ("aerosol container”) or a non-aerosol container.
  • the pressurized gas containers are defined as “aerosol containers”.
  • aerosol container a container under normal pressure is defined in reverse to the aerosol definition, with the aid of which a product is distributed by means of mechanical action by a pumping system.
  • the agents according to the invention are packaged as aerosol hair foam or aerosol hair spray.
  • the agent according to the invention therefore preferably additionally contains at least one propellant.
  • Propellants suitable according to the invention are selected, for example, from N 2 O, dimethyl ether, CO 2 , air, alkanes having 3 to 5 carbon atoms, such as propane, n-butane, isobutane, n-pentane and isopentane, and mixtures thereof. Preference is given to dimethyl ether, propane, n-butane, isobutane and mixtures thereof.
  • said alkanes, mixtures of said alkanes or mixtures of said alkanes with dimethyl ether are used as sole blowing agent.
  • the invention expressly also includes the concomitant use of propellants of the type of chlorofluorocarbons, but in particular of fluorocarbons.
  • the sizes of the aerosol droplets or of the foam bubbles and the respective size distribution can be set for a given spraying device.
  • blowing agent used varies depending on the specific composition of the composition, the packaging used and the desired product type, such as hair spray or hair foam.
  • aerosol foam products contain the propellant preferably in amounts of 1 to 35 wt .-%, based on the total product. Amounts of 2 to 30 wt .-%, in particular from 3 to 15 wt .-% are particularly preferred. Aerosol sprays generally contain larger amounts of propellant.
  • the blowing agent is used in this case in an amount of 30 to 98 wt .-%, based on the total product. Amounts of 40 to 95 wt .-%, in particular from 50 to 95 wt .-% are particularly preferred.
  • the aerosol products can be prepared in the usual way.
  • all constituents of the respective agent with the exception of the propellant, are introduced into a suitable pressure-resistant container. This is then closed with a valve.
  • the desired amount of blowing agent is introduced.
  • isopentane is preferably suitable as a propellant, which is incorporated into the compositions according to the invention and is packaged in the first chamber of the two-chamber aerosol container.
  • at least one further propellant other than isopentane is made up, which builds up a higher pressure in the two-chamber aerosol container than the isopentane.
  • the blowing agents of the second chamber are preferably selected from N 2 O, dimethyl ether, CO 2 , air, alkanes having 3 or 4 carbon atoms (such as propane, n-butane, isobutane) and mixtures thereof.
  • alkanes having 3 or 4 carbon atoms such as propane, n-butane, isobutane
  • a preferred embodiment of the agents according to the invention are aerosol hair foams or
  • Aerosol hair sprays containing the previously described inventive agent and at least one propellant.
  • Preferred agents and propellants of the invention aerosol hair show ms or
  • Aerosol hair sprays as well as the respective amounts of blowing agent correspond to the above
  • a second object of the invention is the use of the compositions according to the invention for the temporary deformation of hair and / or hair care.
  • compositions according to the invention and products which contain these agents are distinguished in particular by the fact that they give treated hair a very strong, lasting hairstyle hold, although the hair remains flexible. If the product is formulated as a hair foam, a stable, fine-pored and creamy foam forms, which can be distributed evenly and without dripping on the hair.
  • a third object of the invention is a method for treating keratin-containing fibers, in particular human hair, wherein a means according to the first subject of the invention is foamed to a foam using a dispenser and the resulting foam is applied to the keratin-containing fibers.
  • the keratin-containing fibers are brought into shape and this form is fixed by the means of the first subject of the invention.
  • Preferred according to the invention are the abovementioned dispensers (vide supra).
  • a fourth subject of the invention is a method for treating keratin-containing fibers, in particular human hair, wherein an agent according to the first subject of the invention is applied as a spray to the keratin-containing fibers using a dispensing device. It is inventively preferred that the keratin-containing fibers are brought into shape and this form is fixed by the means of the first subject of the invention.
  • Preferred according to the invention are the abovementioned dispensers (vide supra).
  • the formulations A to E were each filled into an aerosol container, which fulfills the following technical parameters: Aluminum storage container with valve Product 522983 PV10697 from Pecision (Deutsche refzisions-Ventil GmbH).
  • the aerosol container was filled with a propellant gas mixture of propane / butane (47% by weight of propane, 50% by weight of butane, 3% by weight of isobutane), resulting in a weight ratio of formulation to propellant gas of 92 to 8.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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Abstract

L'invention concerne une préparation pour le traitement de fibres kératiniques, en particulier de cheveux humains, qui contient, dans un véhicule cosmétiquement acceptable (a) au moins un polymère cationique amphiphile comprenant au moins un motif structural de formule (I), au moins un motif structural de formule (II), au moins un motif structural de formule (III), et au moins un motif structural de formule (IV), dans lesquelles R1 et R4 représentent indépendamment l'un de l'autre un atome d'hydrogène ou un groupe méthyle, X1 et X2 représentent indépendamment l'un de l'autre un atome d'oxygène ou un groupe NH, A1 et A2 représentent indépendamment l'un de l'autre un groupe éthane-1,2-diyle, propane-1,3-diyle ou butane-1,4-diyle, R2, R3, R5 et R6 représentent indépendamment les uns des autres un groupe alkyle C1 à C4, R7 représente un groupe alykle C8 à C30, et (b) au moins un polymère filmogène et/ou fixant choisi parmi le chitosane et ses dérivés. L'invention concerne en outre l'utilisation desdites préparations pour la mise en forme temporaire des cheveux et pour les soins capillaires, en particulier sous forme de spray capillaire aérosol ou de mousse capillaire aérosol.
EP09780872A 2008-08-18 2009-07-21 Préparation pour fibres kératiniques, contenant au moins un polymère cationique amphiphile spécial et au moins un polymère additionnel filmogène et/ou fixant choisi parmi le chitosane et ses dérivés Withdrawn EP2323618A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008038107A DE102008038107A1 (de) 2008-08-18 2008-08-18 Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer und mindestens ein zusätzliches filmbildendes und/oder festigendes Polymer ausgewählt aus Chitosan und dessen Derivaten
PCT/EP2009/059351 WO2010020501A2 (fr) 2008-08-18 2009-07-21 Préparation pour fibres kératiniques, contenant au moins un polymère cationique amphiphile spécial et au moins un polymère additionnel filmogène et/ou fixant choisi parmi le chitosane et ses dérivés

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EP2323618A2 true EP2323618A2 (fr) 2011-05-25

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US (1) US20110165109A1 (fr)
EP (1) EP2323618A2 (fr)
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WO2012075274A1 (fr) 2010-12-01 2012-06-07 Isp Investments Inc. Compositions de coiffage durables et leurs utilisations
DE102010055814A1 (de) * 2010-12-23 2012-06-28 Henkel Ag & Co. Kgaa Zusammensetzungen zur Formgebung keratinischer Fasern
US20170360679A1 (en) * 2016-06-21 2017-12-21 Zotos International, Inc. Chitosan: Aldehyde Film-Coated Fibers or Hairs, Related Methods and Compositions
DE102016219838A1 (de) * 2016-10-12 2018-04-12 Henkel Ag & Co. Kgaa Wirkstoffmischungen für Stylingmittel

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US3753968A (en) 1971-07-01 1973-08-21 Westvaco Corp Selective reaction of fatty acids and their separation
DE3139438A1 (de) 1981-10-03 1983-04-21 Henkel KGaA, 4000 Düsseldorf Verwendung kolloidaler loesungen von seidenfibroin in haarkosmetischen mitteln und haarshampoo
DE19736906A1 (de) * 1997-08-25 1999-03-04 Henkel Kgaa Verfahren zur Herstellung von sulfatierten Fettsäurealkylenglykolestern
DE19738866A1 (de) 1997-09-05 1999-03-11 Henkel Kgaa Schaumarme Tensidmischungen mit Hydroxymischethern
DE19756454C1 (de) 1997-12-18 1999-06-17 Henkel Kgaa Verwendung von Glycerincarbonat
US6149898A (en) * 1998-06-22 2000-11-21 The Procter & Gamble Company Hair styling compositions containing silicone microemulsions and cationic non-polymeric liquids
FR2785183B1 (fr) 1998-11-04 2002-04-05 Oreal COMPOSITION TINCTORIALE CONTENANT UN COLORANT DIRECT CATIONIQUE ET UNE PYRAZOLO-[1,5-a]- PYRIMIDINE A TITRE DE BASE D'OXYDATION, ET PROCEDES DE TEINTURE
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GB9925056D0 (en) * 1999-10-23 1999-12-22 Univ Cranfield Preparation of biologically-active molecules by template polymerization
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DE102008038107A1 (de) 2010-02-25
US20110165109A1 (en) 2011-07-07
WO2010020501A3 (fr) 2010-04-15

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