EP2844350A2 - Produit de traitement capillaire contenant un (des) organopolysiloxane(s) à terminaison hydroxy et un (des) agent(s) de conditionnement - Google Patents

Produit de traitement capillaire contenant un (des) organopolysiloxane(s) à terminaison hydroxy et un (des) agent(s) de conditionnement

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Publication number
EP2844350A2
EP2844350A2 EP13705824.4A EP13705824A EP2844350A2 EP 2844350 A2 EP2844350 A2 EP 2844350A2 EP 13705824 A EP13705824 A EP 13705824A EP 2844350 A2 EP2844350 A2 EP 2844350A2
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
acid
oil
polymers
oils
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP13705824.4A
Other languages
German (de)
English (en)
Inventor
Erik Schulze Zur Wiesche
Markus Semrau
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 EP2844350A2 publication Critical patent/EP2844350A2/fr
Ceased 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
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/892—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a hydroxy group, e.g. dimethiconol
    • 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
    • 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
    • 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

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.
  • combination preparations have been developed to reduce the burden of the usual multi-stage process, especially in direct application by consumers.
  • These preparations contain, in addition to the usual components, for example for the cleaning of the hair, in addition to active ingredients which were formerly reserved for the hair aftertreatment agents.
  • the consumer thus saves an application step; At the same time, packaging costs are reduced because one product is less needed.
  • the known active ingredients can not cover all needs sufficiently. There is therefore still a need for active ingredients or combinations of active substances for cosmetic products with good care properties and good biodegradability. Especially in surfactant- and / or electrolyte-containing formulations, there is a need for additional skin care ingredients that can be easily incorporated into known formulations and are not weakened in their action due to incompatibilities with other ingredients.
  • Silicones and among them, amino-functional silicones are known as conditioners in hair-treatment agents, and such products are widely used in the market.
  • conditioners amino-functional silicones
  • such products are widely used in the market.
  • equally good or better effects should be achieved even with significantly reduced quantities.
  • the products should improve the grip, combability, softness and volume of the hair or hairstyle and significantly minimize the contact angle of water droplets on the treated hair, which is a measure of product performance.
  • a first object of the present invention is a cosmetic composition containing in a cosmetically acceptable medium
  • At least one conditioning agent selected from synthetic oils, mineral oils, vegetable oils, fluorinated or perfluorinated oils, natural or synthetic waxes, ceramide-type compounds, carboxylic acid esters, silicones other than the silicones of formulas (I), anionic polymers, nonionic polymers, cationic polymers, amphoteric polymers, cationic proteins, cationic protein hydrolyzates, cationic surfactants, and the mixtures of these various compounds, and
  • R is a monovalent unsubstituted or halogen-substituted hydrocarbon radical having 1 to 20 carbon atoms
  • R is a monovalent unsubstituted or halogen-substituted hydrocarbon radical having 1 to 20 carbon atoms, -OR 4 or -OH, R 4 is an alkyl radical having 1 to 6 carbon atoms,
  • G is a group of general formula (II)
  • R 5 is an alkyl radical having 1 to 20 carbon atoms
  • the agent according to the invention is a cosmetic agent. While there used to be a distinction between “body care” and “decorative cosmetics” in the care of the human body and in the beautification of its appearance, these products are today collectively defined as the "cosmetic center”.
  • '(1) cosmetic products within the meaning of this Act are substances or preparations of substances intended to be used externally on the human or in the oral cavity for the purpose of cleansing, care or to influence the appearance or odor of the body or to convey olfactory impressions; unless they are predominantly intended to alleviate or eliminate disease, suffering, bodily injury or pathological condition.
  • ⁇ 4 LMBG is not yet adapted to the EU Cosmetics Directive, the cosmetics six functions (cleanse, perfume, change appearance, affect body odor, protect and keep in good condition) zuwel.
  • the cosmetic products are substances or preparations made of substances for the cleaning or care of dentures same.
  • cosmetic products for example for skin care (bath preparations, skin washing and cleaning agents, skin care products, ocular cosmetics, lip care products, nail care products, personal hygiene products, foot care products), those having a specific action (sunscreens, skin tanning agents, depigmenting agents, deodorants , Antihidrotika, depilatories, shaving, fragrance), such as dental &. Oral care (dentifrice and oral hygiene products, dentifrices, denture adhesives) and those for hair care (shampoos, hair care products, hair hardening agents, hair shaping agents, color change agents).
  • skin care bath preparations, skin washing and cleaning agents, skin care products, ocular cosmetics, lip care products, nail care products, personal hygiene products, foot care products
  • those having a specific action unsunscreens, skin tanning agents, depigmenting agents, deodorants , Antihidrotika, depilatories, shaving, fragrance
  • Oral care dentifrices, denture adhesives
  • hair care
  • Cosmetic compositions preferred according to the invention are selected from the group of shower gels, shower baths, dentifrices, mouthwashes, hair shampoos, hair conditioners, conditioning shampoos, hair sprays, hair rinses, hair treatments, hair wraps, hair tonics, perming solutions, hair dye shampoos, hair dyes, hair fixatives, hair dressings, hair styling Preparations, Fönwell lotions, mousses, hair gels, hair waxes or combinations thereof.
  • Hair care agents in the context of the present invention are, for example, hair shampoos, hair conditioners, conditioning shampoos, hair sprays, hair rinses, hair treatments, hair wraps, hair tonics, perming solutions, hair dye shampoos, hair dyes , Hair setting, hair products, hair styling Preparations, Fönwell lotions, mousses, hair gels, hair waxes or combinations thereof.
  • 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 have improved cosmetic properties (in hair, for example, 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 when applied to the skin (for example, by a foam bath or shower gel), result in improved suppleness of the skin.
  • the agents according to the invention contain as the first essential ingredient at least one hydroxy-terminated organopolysiloxane of the general formula (I)
  • R is a monovalent unsubstituted or halogen-substituted
  • Hydrocarbon radical having 1 to 20 carbon atoms
  • R is a radical R, -OR 4 or -OH
  • R 4 is an alkyl radical having 1 to 6 carbon atoms
  • G is a group of general formula (II)
  • R 5 is an alkyl radical having 1 to 20 carbon atoms
  • b mean integer values of at least 1.
  • compositions according to the invention contain at least one hydroxy-terminated organopolysiloxane of the general formula (Ia):
  • R, R, R 2 , R 3 , R 5 , a and b are as defined above.
  • the radical R can be a monovalent unsubstituted or halogen-substituted hydrocarbon radical having 1 to 20 carbon atoms, an OH group or a radical OR 4 , where R 4 in turn represents an alkyl radical having 1 to 6 carbon atoms.
  • Preferred radicals R are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, hydroxy, methoxy, ethoxy , n-propoxy and iso-propoxy radicals.
  • Particularly preferred agents according to the invention comprise at least one hydroxy-terminated organopolysiloxane of the general formula (Ia-1) and / or (Ia-2) and / or (Ia-3) and / or (Ia-4) and / or (Ia-5 ) and / or (la-6) and / or (la-7) and / or (la-8) and / or (la-9) as disclosed in the priority document on pages 6 and 7.
  • R is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, phenyl Radicals, wherein R is most preferably methyl, ethyl or phenyl.
  • Preferred cosmetic compositions according to the invention contain at least one hydroxy-terminated organopolysiloxane of the general formula (I) in which the radicals R 2 , R 3 are independently selected from ethylene, n-propylene, isobutylene or n-butylene radicals.
  • R 2 is an n-propylene radical and R 3 is simultaneously an ethylene radical, so that the moiety G is preferably a group
  • Very particularly preferred agents according to the invention accordingly comprise at least one hydroxy-terminated organopolysiloxane of the general formula (I-1) and / or (I-2) and / or (I-3) and / or (I-4) and / or (Ie -5) and / or (le-6) and / or (le-7) and / or (le-8) and / or (le-9) with the definitions for R as given in formula (I) and as in Priority document on pages 14 and 15 disclosed, with particularly preferred R are methyl, ethyl or phenyl radicals.
  • Very particularly preferred cosmetic compositions according to the invention are characterized in that they contain at least one hydroxy-terminated organopolysiloxane of the general formula (I) in which R 5 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl Isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl radicals, wherein R 5 is most preferably methyl, ethyl, n-propyl or isopropyl.
  • R 5 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl Isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl radicals, wherein R 5 is most preferably methyl, ethyl, n-propyl or isopropyl.
  • R 5 methyl
  • the subscript a stands for integer values of 100 to 1500.
  • a denotes integer values of at least 200, in particular at least 500 and at most 1300, particularly preferably at most 1100 and in particular at most 900.
  • Compositions according to the invention in which a has values of 220 to 910 are particularly preferred.
  • the index b stands for integer values of at least 1.
  • b preferably denotes integer values of at most 100, in particular at most 50, preferably at most 10 and in particular at most 5.
  • Compositions according to the invention in which b has the values 1, 2, 3, 4 or 5 are particularly preferred.
  • a and b are chosen so that the organopolysiloxane of the formula (I) under normal conditions (20 ° C, 1013.25 mbar) has a viscosity (Brookfield RTV, spindle 4, 20 rev / min) of at least 100 mPas, preferably at least 1000 mPas, more preferably at least 5000 mPas and in particular at least 15,000 mPas.
  • the Viscosity not more than 500,000 mPas, preferably not more than 200,000 mPas, more preferably not more than 100,000 mPas and in particular not more than 60,000 mPas.
  • Compositions according to the invention in which the organopolysiloxane of the formula (I) has viscosities of from 17,000 to 55,000 mPas are particularly preferred.
  • the amine number of the organopolysiloxane of the formula (I) is preferably at least 0.001 mmol / g, more preferably at least 0.01 mmol / g. More preferably, the amine number is at most 5 mmol / g, more preferably at most 1 mmol / g, even more preferably at most 0.1 mmol / g, and most preferably at most 0.05 mmol / g.
  • Compositions according to the invention in which the organopolysiloxane of the formula (I) has amine numbers of from 0.015 to 0.045 mmol / g are particularly preferred.
  • organopolysiloxane (s) of the formula (I) can be used in varying amounts, depending on the intended use of the agents according to the invention.
  • Preferred cosmetic agents according to the invention are characterized in that they contain 0.00001 to 10% by weight, preferably 0.0001 to 7.5% by weight, particularly preferably 0.001 to 5% by weight, based on their weight preferably 0.01 to 3 wt .-% and in particular 0, 1 to 1 wt .-% organopolysiloxane (s) of the formula (I).
  • Nonionic components which are particularly suitable here are ethoxylates of decanol, undecanol, dodecanol, tridecanol, etc. Ethoxylated tridecanols have proven to be particularly suitable, which are incorporated with particular preference into the compositions according to the invention.
  • particularly preferred cosmetic compositions contain - based on their weight - 0.00001 to 5 wt .-%, preferably 0.0001 to 3.5 wt .-%, particularly preferably 0.001 to 2 wt .-%, more preferably 0.01 up to 1% by weight and in particular from 0.1 to 0.5% by weight branched, ethoxylated tridecanol (INCI name: trideceth-5) or ⁇ -isotridecyl-hydroxypolyglycol ether (INCI name: Trideceth-10) or mixtures thereof.
  • organopolysiloxane (s) of the formula (I) have both hydroxy and alkoxy groups.
  • Cosmetic compositions which are particularly preferred according to the invention comprise organopolysiloxane (e) of the formula (I) in which the molar ratio hydroxy / alkoxy is in the range from 0.2: 1 to 0.4: 1, preferably in the range from 1: 0.8 to 1: 1, 1 lies.
  • the average molecular weight of the organopolysiloxane (e) of the formula (I) is preferably from 2,000 to 200,000, and more preferably from 5,000 to 100,000, especially from 10,000 to 50,000 daltons.
  • compositions in which the weight-average molecular weight of the organopolysiloxane (s) of the formula (I) contained in them is in the range from 2,000 to 1,000,000 gmol 1 , preferably in the range from 5,000 to 200,000 gmol -1 , are preferred.
  • 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 can be chosen Styragel columns ⁇ , as eluent THF and flow rate 1 ml / min.
  • the detection preferably takes place by means of refractometry and UV meter.
  • the use of the organopolysiloxane (s) of the formula (I) is preferably carried out as an oil-in-water emulsion.
  • the oil-in-water emulsion may contain one or more surfactants.
  • the surfactants may be of any type, preferably cationic and / or nonionic.
  • the number-average average size of the silicone droplets in the emulsion is preferably between 3 nm and 500 nm, particularly preferably between 5 nm and 60 nm (inclusive) and in particular between 10 nm and 50 nm (inclusive).
  • compositions according to the invention in which the organopolysiloxane (s) of the formula (I) are present in the form of an oil-in-water emulsion in which the number-average size of the silicone particles in the emulsion is in the range from 3 to 500 nm, preferably Range of 5 to 60 nm, are preferred according to the invention.
  • compositions of the invention is a conditioning agent selected from synthetic oils, mineral oils, vegetable oils, fluorinated or perfluorinated oils, natural or synthetic waxes, ceramide-type compounds, carboxylic acid esters, silicones other than the silicones of formulas (I), anionic polymers , nonionic polymers, cationic polymers, amphoteric polymers, cationic proteins, cationic protein hydrolyzates, cationic surfactants and the mixtures of these various compounds.
  • a conditioning agent selected from synthetic oils, mineral oils, vegetable oils, fluorinated or perfluorinated oils, natural or synthetic waxes, ceramide-type compounds, carboxylic acid esters, silicones other than the silicones of formulas (I), anionic polymers , nonionic polymers, cationic polymers, amphoteric polymers, cationic proteins, cationic protein hydrolyzates, cationic surfactants and the mixtures of these various compounds.
  • conditioning agent means any compound capable of improving at least one cosmetic property of keratinous material, such as hair, for example softness, suppleness, feel, entanglement or static chargeability.
  • the at least one conditioning agent can be water-soluble or water-insoluble.
  • Water-insoluble conditioning agents may be solid, liquid or pasty at 25 ° C and 1013 mbar and may be in the form of oils, waxes, resins or gums.
  • Water-insoluble conditioning agents can also be present in disperse form, which preferably have number-average particle or droplet sizes of 2 nm to 100 ⁇ m, preferably of 30 nm to 20 ⁇ m. The number average particle size is determined by means of a granulometer. Water-insoluble conditioning agents dissolve in water at 25 ° C to less than 0.1% by weight, i. they do not form macroscopically isotropic, transparent solutions under these conditions.
  • Synthetic oils for example polyolefins, in particular poly-alpha-olefins, can be selected from: polyolefins of the hydrogenated or non-hydrogenated polybutene type or of the hydrogenated or nonhydrogenated polyisobutene type.
  • Isobutylene oligomers having molar masses of less than 1000 and mixtures thereof with polyisobutylenes having molar masses greater than 1000, for example from 1000 to 15000, can preferably be used.
  • Cosmetic compositions preferred according to the invention are characterized in that the synthetic oil (s) are polyolefins of the hydrogenated or unhydrogenated polybutene type or of the hydrogenated or nonhydrogenated polydecine type.
  • these oil bodies have a melting point less than 50 ° C, more preferably less than 45 ° C, most preferably less than 40 ° C, most preferably less than 35 ° C and most preferably the cosmetic oils at a temperature less than 30 ° C flowable.
  • these oils are defined and described in more detail.
  • the natural and synthetic cosmetic oils include, for example:
  • 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. Also suitable, however, are other triglyceride oils such as the liquid portions of beef tallow as well as synthetic triglyceride oils.
  • the compounds are available as commercial products 1, 3-di- (2-ethyl-hexyl) - cyclohexane (Cetiol ® S), and di-n-octyl ether (Cetiol ® OE) may be preferred.
  • 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.
  • Examples of fatty acid components used in the esters are caproic, caprylic, 2-ethylhexanoic, capric, lauric, isotridecanoic, myristic, palmitic, palmitoleic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic Behenic acid and erucic acid and their technical mixtures which are obtained, for example, in the pressure splitting of natural fats and oils, in the oxidation of aldehydes from Roelen's oxo synthesis or the dimerization of unsaturated fatty acids.
  • fatty alcohol components in the ester oils are isopropyl alcohol, caproic alcohol, capryl alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, Elaidyl alcohol, Petroselinylalkohol, Linolylalkohol, Linolenylalkohol, Elaeostearylalkohol, Arachylalkohol, Gadoleylalkohol, Behenylalkohol, Erucylalkohol and Brassidylalkohol as well as their technical mixtures, which eg in the high-pressure hydrogenation of technical methyl esters on basis of fats and oils or aldehydes from the Roelen oxo synthesis as well as Monomerfrtress with the dimerization of uns
  • 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- caprinatV caprylate (Cetiol ® LC)
  • n-butyl stearate oleyl erucate
  • isopropyl palmitate Rosanit ® IPP
  • oleyl Oleate Cetiol ®
  • hexyl laurate Cetiol ® A
  • di-n-butyl adipate Cetiol ® B
  • 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,
  • Fatty acid partial glycerides ie 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),
  • R 3 in the R, R 2 and R 3 are 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 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 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 acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid. acid, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic, elaeostearic, arachidic, gadoleic, behenic and erucic acid, and technical mixtures thereof.
  • oleic acid monoglycerides are used.
  • Natural oils include, for example, amaranthsamenol, apricot kernel oil, argan oil, avocado oil, babassu oil, cottonseed oil, borage seed oil, camelinaol, thistle oil, peanut oil, pomegranate seed oil, grapefruit seed oil, hemp oil, hazelnut oil, elderflower seed oil, currant seed oil, jojoba oil, cocoa butter, linseed oil, macadamia nutol, corn oil, almond oil, marula oil , Evening primrose oil, olive oil, palm oil, rapeseed oil, rice oil, sea buckthorn fruit oil, sea buckthorn seed oil, sesame oil, shea butter, soybean oil, sunflower oil, grapeseed oil, walnut oil or wild rose oil.
  • the teaching of the invention also includes that at least two of the natural oils listed in the above table can be mixed together.
  • the natural oils must be selected so that the sum of the fatty acids palmitic acid, stearic acid and linoleic acid gives at least 50% by weight of the sum of the total fatty acids.
  • Preferred mixtures of the natural oils are amaranthsamenol with at least one sea buckthorn oil, amaranthsamenol with shea butter, amaranthsamenol with camelinaol, amaranthsamenol with olive oil, amaranthsamenol with macadamianussol, olive oil with at least one seabuckthorn oil, olive oil with camelinaol, olive oil with shea butter, macadamianussol and at least one seabuckthorn oil, macadamianussol with shea butter.
  • more than three of the natural oils should not be mixed together.
  • Argan oil is one of the most preferred natural oils.
  • Preferred cosmetic compositions according to the invention are characterized in that the vegetable oil (s) under sunflower oil, corn oil, soybean oil, avocado oil, jojoba oil, pumpkin seed oil, grapeseed oil, sesame oil, hazelnut oil, fish oils, glycerol tricaprocaprylate or vegetable or animal oils of the formula R 9 COOR 10 , wherein R 9 is the radical of a higher fatty acid of 7 to 29 carbon atoms and R 0 is a linear or branched hydrocarbon chain of 3 to 30 carbon atoms, natural or synthetic essential oils.
  • waxes As natural or synthetic waxes (Fatwax), solid paraffins or isoparaffins, carnauba waxes, beeswaxes, candelilla waxes, ozokerites, ceresin, spermaceti, sunflower wax, fruit waxes such as apple wax or citrus wax, microwaxes of PE or PP can be used according to the invention.
  • Preferred cosmetic compositions according to the invention are characterized in that the wax or waxes are selected from carnauba wax, candelilla wax, alfawax, paraffin wax, ozokerite, vegetable waxes, animal washing, polyethylene waxes or polyolefin waxes.
  • ceramide type compounds can be selected from natural and synthetic ceramides, glycoceramides, pseudoceramides, and neoceramides.
  • Preferred representatives of these groups are 2-N-linoleoylaminooctadecane-1,3-diol, 2-N-oleoylaminooctadecane-1,3-diol, 2-N-palmitoylaminooctadecane-1,3-diol, 2-N-stearoylaminooctadecane-1, 3-diol, 2-N-behenoylaminooctadecane-1,3-diol, 2-N- [2-hydroxypalmitoyl] aminooctadecane-1, 3-diol, 2-N-stearoylaminooctadecane-1, 3,4-triol and such as N stearoyl phytosphingosine, 2-N-palmitoylaminohexadecane-1,3-diol, bis (N-hydroxyethyl-N-cetyl) malonamide, N- (2-hydroxy
  • Preferred cosmetic compositions according to the invention are characterized in that the ceramide-type compounds are selected from 2-N-linoleoylamino-octadecane-1,3-diol, 2-N-oleoylamino-octadecane-1,3-diol, 2-N-palmitoylamino octadecane-1,3-diol, 2-N-stearoylamino-octadecane-1,3-diol, 2-N-behenoylamino-octadecane-1,3-diol, 2-N- [2-
  • Fatty alcohols are to be understood as meaning primary aliphatic alcohols of the formula R 1 OH in which R is an aliphatic, linear or branched hydrocarbon radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds.
  • Typical examples are caprylic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol , Erucylalkohol and brassidyl alcohol and their technical mixtures, for example, in the high pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from the Roelen oxo synthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols incurred.
  • Alkoxylated fatty alcohols with 1 to 15 moles of alkylene oxide can also be used as conditioning agents, or polyglycerylated compounds with 1 to 6 moles of glycerol.
  • Monocarboxylic acid can be used with particular preference as a conditioner. These are selected, for example, from linear or branched, saturated or unsaturated aliphatic C 1 -C 2 -6 monoesters of linear or branched, saturated or unsaturated aliphatic C 1 -C -acyl alcohols, the total carbon atom number in the esters being 10 or more.
  • conditioning agents are dihydroabietyl behenate; Octyldodecylbehenat; Isocetylbehenat; cetyl lactate; C 12 -C 15 alkyl lactate; isostearyl lactate; lauryl; Linoleyllactat; Oleyllactat; (Iso) stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; oleate; Isocetyl isostearate, isocetyl laurate, isocetyl stearate, isodecyl octanoate, isodecyl oleate, isononyl isononanoate, isostearyl palmitate, methyl acetylricinoleate, myristyl stearate, octyl isononanoate, 2-
  • C4-C22 D1- or Tricarbpnklar of C1-C22 alcohols and mono-, di- or tricarboxylic acid esters of C 2 -C 2 6 di-, tri-, tetra- or pentahydroxy alcohols can also be used.
  • compositions according to the invention wherein the carboxylic acid esters are ethyl palmitate and isopropyl palmitate, 2-ethylhexyl palmitate, 2-octyl decyl palmitate, alkyl myristates, hexyl stearate, butyl stearate, isobutyl stearate; Dioctylmalat, hexyl laurate, 2-hexyldecyl laurate, isononyl isononanoate and cetyloctanoate are selected according to the invention are preferred.
  • Silicones which differ from the silicones of the formula (I) used according to the invention can also be used as conditioning agents.
  • Preferred agents according to the invention are characterized in that they comprise at least one further silicone, preferably a silicone, which is selected from:
  • polyalkyl siloxanes polyaryl siloxanes, polyalkylaryl siloxanes which are volatile or nonvolatile, straight chain, branched or cyclic, crosslinked or uncrosslinked;
  • grafted silicone polymers having a non-silicone organic backbone consisting of an organic backbone formed from organic monomers containing no silicone grafted with at least one polysiloxane macromer in the chain and optionally at least one chain end;
  • silicones other than the silicones of the formula (I) are non-volatile polyorganosiloxanes selected from polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, silicone gums, silicone resins, organofunctional group-modified polyorganosiloxanes and mixtures thereof.
  • polyalkylsiloxanes are selected from:
  • polyaryl siloxanes are selected from:
  • said silicone gums are selected from polydiorganosiloxanes having number average molecular weights in the range 200,000 to 1,000,000 and used as such or in admixture with a solvent;
  • the resins are selected from resins composed of R 3 SiOi / 2 , R 2 S 1 O 2/2, RS 1 O 3/2, and S 1/24 / 2 units, wherein the group R is a hydrocarbon group having 1 to 16 carbon atoms or a phenyl group;
  • the organomodified silicones are selected from silicones structurally bearing one or more organofunctional groups bonded through a hydrocarbon group.
  • compositions according to the invention contain the further silicone (s) preferably in amounts of from 0.1 to 10% by weight, preferably from 0.25 to 7% by weight and in particular from 0.5 to 5% by weight. %, in each case based on the total mean. Preferred silicones are described below.
  • x is a number from 0 to 100, preferably from 0 to 50, more preferably from 0 to 20 and in particular 0 to 10.
  • silicones are called DIMETHICONE according to the INCI nomenclature.
  • the following compounds are preferably those compounds of the formula Si-I: (CH 3 ) 3 Si-O-Si (CH 3 ) 3, (CH 3 ) 3 Si-O- (CH 3 ) 2 Si 0-Si (CH 3 ) 3 , (CH 3 ) 3 Si - [0- (CH 3 ) 2 Si] 2 -O-Si (CH 3 ) 3 , (CH 3 ) 3 Si - [0- (CH 3 ) 2 Si] 3 -0-Si (CH 3 ) 3 , (CH 3 ) 3 Si - [0- (CH 3 ) 2 Si] 4 -O-Si (CH 3 ) 3 , (CH 3 ) 3 Si [0- (CH 3 ) 2 Si] 5 -O-Si (CH 3 ) 3 , (CH 3 ) 3 Si [0- (CH 3 ) 2 Si] 6 -O-Si (CH 3 ) 3 ,
  • Preferred silicones which can be used according to the invention have viscosities of 0.2 to 2 mm 2 s -1 at 20 ° C., silicones having viscosities of 0.5 to 1 mm 2 s -1 being particularly preferred.
  • Particularly preferred agents according to the invention contain one or more organomodified silicones, since the performance properties of the silicones can be adapted even more in detail to the intended use by the modification.
  • Cosmetic compositions preferred according to the invention are characterized in that the organomodified silicones are chosen from polyorganosiloxanes which contain a) polyethyleneoxy and / or polypropyleneoxy groups, b) substituted or unsubstituted aminated groups, c) thiol groups, d) alkoxylated groups, e) hydroxyalkyl groups, f) acyloxyalkyl groups, g) carboxyalkyl groups, h) 2-hydroxyalkylsulfonate groups, i) 2-hydroxyalkylthiosulfonate groups, j) hydroxyacylamino groups.
  • Particularly preferred agents according to the invention contain one or more amino-functional silicones. Such silicones may, for example, be represented by the formula
  • R in the above formula is a hydrocarbon or a hydrocarbon radical having 1 to about 6 carbon atoms
  • Q is a polar radical of the general formula -R HZ, wherein R is a divalent linking group attached to hydrogen and the radical Z.
  • Z is an organic, amino-functional radical containing at least one amino-functional group; "a” assumes values in the range of about 0 to about 2, “b” assumes values in the range of about 1 to about 3, “a” + “b” is less than or equal to 3, and “c” is a number in the range from about 1 to about 3, and x is a number ranging from 1 to about 2,000, preferably from about 3 to about 50, and most preferably from about 3 to about 25, and y is a number ranging from about 20 to about 10,000 , preferably from about 125 to about 10,000, and most preferably from about 150 to about 1,000, and M is a suitable silicone end group as known in the art, preferably trimethylsiloxy.
  • Non-limiting examples of the groups represented by R include alkyl groups such as methyl, ethyl, propyl, isopropyl, isopropyl, butyl, isobutyl, amyl, isoamyl, hexyl, isohexyl and the like; Alkenyl radicals such as vinyl, halovinyl, alkylvinyl, allyl, haloallyl, alkylallyl; Cycloalkyl radicals such as cyclobutyl, cyclopentyl, cyclohexyl and the like; Phenyl radicals, benzyl radicals, halohydrocarbon radicals such as 3-chloropropyl, 4-bromobutyl, 3,3,3-trifluoropropyl, chlorocyclohexyl, bromophenyl, chlorophenyl and the like, and sulfur containing radicals such as mercaptoethyl, mercaptopropyl,
  • R examples include methylene, ethylene, propylene, hexamethylene, decamethylene, - CH 2 CH (CH 3 ) CH 2 -, phenylene, naphthylene, -CH 2 CH 2 SCH 2 CH 2 -, -CH 2 CH 2 OCH 2 -, -OCH 2 CH 2 -, -OCH 2 CH 2 CH 2 -, -CH 2 CH (CH 3 ) C (O) 2 -, - (CH 2 ) 3 CC (O) 2 CH 2 -, -C 6 H 4 C 6 H 4 -, -C 6 H 4 CH 2 C 6 H 4 -; and - (CH 2 ) 3 C (O) SCH 2 CH 2 -.
  • Z is an organic, amino-functional radical containing at least one functional amino group.
  • a possible formula for Z is NH (CH 2 ) Z NH 2 , wherein z is 1 or more.
  • Another possible formula for Z is -NH (CH 2 ) Z (CH 2 ) ZZ NH, wherein both z and zz are independently 1 or more, which structure includes diamino ring structures, such as piperazinyl.
  • Z is most preferably a -NHCH 2 CH 2 NH 2 radical.
  • Z is - N (CH 2 ) Z (CH 2 ) ZZ NX 2 or -NX 2 , wherein each X of X 2 is independently selected from the group consisting of hydrogen and alkyl groups of 1 to 12 carbon atoms, and zz is 0.
  • Q is most preferably a polar, amine functional group of the formula -CH 2 CH 2 CH 2 NHCH 2 CH 2 NH 2 .
  • "a” assumes values in the range of about 0 to about 2
  • "b” takes values in Range from about 2 to about 3
  • "a” + “b” is less than or equal to 3
  • "c” is a number ranging from about 1 to about 3.
  • the molar ratio of R a Qb SiO ( 4 . a -b) / 2 units to the R c SiO (4 c) / 2 units ranges from about 1: 2 to 1:65, preferably from about 1: 5 to about 1:65, and most preferably about 1:15 to about 1:20.
  • the various variable substituents in the above formula may be different for the various silicone components present in the silicone blend.
  • Preferred agents according to the invention are characterized in that they contain an amino-functional silicone of the formula (Si-II)
  • G is -H, a phenyl group, -OH, -O-CH 3 , -CH 3 , -O-CH 2 CH 3 , -CH 2 CH 3 , -O-
  • a is a number between 0 and 3, in particular 0;
  • b is a number between 0 and 1, in particular 1,
  • n and n are numbers whose sum (m + n) is between 1 and 2000, preferably between 50 and 150, where n is preferably values from 0 to 1999 and in particular from 49 to 149 and m preferably values from 1 to 2000, in particular from 1 to 10,
  • R - R ' is a monovalent radical selected from
  • each Q is a chemical bond, -CH 2 -, -CH 2 -CH 2 -, -CH 2 CH 2 CH 2 -, -C (CH 3 ) 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 C (CH 3 ) 2 -, -CH (CH 3 ) CH 2 CH 2 -,
  • R " is identical or different radicals from the group -H, -phenyl, -benzyl, -CH 2 - CH (CH 3 ) Ph, the Ci_ 20 -alkyl radicals, preferably -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , - CH (CH 3 ) 2 , -CH 2 CH 2 CH 2 H 3 , -CH 2 CH (CH 3 ) 2 , -CH (CH 3 ) CH 2 CH 3 , -C (CH 3 ) 3 , and A represents an anion, which is preferably selected from chloride, bromide, iodide or methosulfate.
  • Particularly preferred agents according to the invention are characterized in that they contain at least one amino-functional silicone of the formula (Si-IIa) (CH 3 ) 3 Si - [O-Si (CH 3 ) 2 ] n [OSi (CH 3)] m - OSi (CH 3 ) 3 (Si-Ila),
  • n and n are numbers whose sum (m + n) is between 1 and 2000, preferably between 50 and 150, where n preferably values of 0 to 1999 and in particular of 49 to 149 and m preferably values of 1 to 2000 , in particular from 1 to 10 assumes.
  • compositions according to the invention which are an amino-functional silicone of the formula (Si-IIb)
  • n1 and n2 are numbers whose sum (m + n1 + n2) is between 1 and 2,000, preferably between 50 and 150 , where 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, particularly preferably 0.25 to 7.5% by weight and in particular 0, 5 to 5 wt.% Amino-functional silicone (s) included.
  • agents according to the invention which contain at least one silicone of the formula Si-III
  • rO-SifCH rO-SifCH,, L- (Si-III) in which x is a number from 3 to 200, preferably from 3 to 10, more preferably from 30 to 7 and especially 3, 4, 5 or 6.
  • Cyclic silicones of 3 to 7, preferably 4 to 5, Si atoms are, for example, octamethylcyclotetrasiloxane, available as "Volatile Silicone 7207" (Union Carbide) or "Silbione 70045 V 2" (Rhodia Chemie), decamethylcyclopentasiloxane, available as "Volatile Silicone 7158". (Union Carbide) and "Silbione 70045 V 5" (Rhodia Chimie) and mixtures thereof.
  • Cyclocopolymers of the dimethylsiloxane / methylalkylsiloxane type are, for example, "Volatile Silicone FZ 3109" (Union Carbide), having the structure:
  • mixtures of cyclic silicones with organosilicone compounds such as the mixture of octamethylcyclotetrasiloxane and tetratrimethylsilyl pentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and oxy-1,1'-bis (2,2,2 ', 2', 3,3 '-hexatrimethylsilyloxy) neopentane.
  • 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 or y is a number from 0 to 200, preferably from 0 to 10, more preferably from 0 to 7 and in particular 0, 1, 2, 3, 4, 5 or 6, and n is a number from 0 to 10, preferably from 1 to 8 and especially for 2, 3, 4, 5, 6 stands.
  • the silicones are preferably water-soluble. Agents preferred according to the invention are characterized in that they contain at least one water-soluble silicone.
  • Most particularly preferred cosmetic compositions are characterized in that the silicones among the trimethylsilyl-terminated polyalkylsiloxanes, dimethylsilanol-terminated polyalkylsiloxanes, polyalkylarylsiloxanes, mixtures of two PDMSs formed from a gum and an oil of different viscosities, mixtures of organosiloxanes and cyclic silicones, Organopolysiloxane resins are selected.
  • conditioning agents used silicones are, for example
  • Mirasil® oils (Rhodia Chimie) like 70 047 V 500 000 200 series oils (Dow Corning), such as DC200 with a viscosity of 60,000 cSt (mm 2 / s) Viscasil® oils (General Electric)
  • Dimethiconols such as oils of the 48 series (Rhodia Chimie)
  • Silicone Copolymer F-755 SWS Silicones
  • Abil Wax 2428, 2434 and 2440 Goldschmidt
  • conditioning agents it is also possible to use water-soluble conditioning agents, preferably from the groups of the anionic polymers, the nonionic polymers, the cationic polymers, the amphoteric polymers, the cationic proteins and protein hydrolysates, the cationic surfactants and mixtures of these substances.
  • anionic polymers which can support the action of the active ingredient according to the invention are anionic polymers which have carboxylate and / or sulfonate groups.
  • anionic monomers from which such polymers may consist are acrylic acid, methacrylic acid, crotonic acid, maleic anhydride and 2-acrylamido-2-methylpropanesulfonic acid.
  • the acidic groups may be wholly or partly present as sodium, potassium, ammonium, mono- or triethanolammonium salt.
  • Preferred monomers are 2-acrylamido-2-methylpropanesulfonic acid and acrylic acid.
  • Anionic polymers which contain 2-acrylamido-2-methylpropanesulfonic acid as the sole or co-monomer can be found to be particularly effective, it being possible for all or some of the sulfonic acid group to be present as sodium, potassium, ammonium, mono- or triethanolammonium salt , More preferably, the homopolymer of 2-acrylamido-2-methyl propane sulfonic acid, which is commercially available, for example under the name Rheothik ® 1 1-80 is.
  • copolymers of at least one anionic monomer and at least one nonionic monomer are preferable to use copolymers of at least one anionic monomer and at least one nonionic monomer.
  • anionic monomers reference is made to the substances listed above.
  • Preferred nonionic monomers are acrylamide, methacrylamide, acrylic esters, methacrylic esters, vinylpyrrolidone, vinyl ethers and vinyl esters.
  • Preferred anionic copolymers are acrylic acid-acrylamide copolymers and in particular polyacrylamide copolymers with sulfonic acid-containing monomers.
  • a particularly preferred anionic copolymer consists of 70 to 55 mol% of acrylamide and 30 to 45 mol% of 2-acrylamido-2-methylpropanesulfonic acid, wherein the sulfonic acid group is wholly or partly in the form of sodium, potassium, ammonium, mono- or triethanolammonium Salt is present.
  • This copolymer may also be crosslinked, with crosslinking agents preferably polyolefinically unsaturated compounds such as tetraallyloxyethane, allylsucrose, allylpentaerythritol and methylene-bisacrylamide are used.
  • crosslinking agents preferably polyolefinically unsaturated compounds such as tetraallyloxyethane, allylsucrose, allylpentaerythritol and methylene-bisacrylamide are used.
  • crosslinking agents preferably polyolefinically unsaturated compounds such as tetraallyloxyethane, allylsucrose, allylpentaerythritol and methylene-bisacrylamide are used.
  • Such a polymer is contained in the commercial product Sepigel ® 305 from SEPPIC.
  • This compound which in addition to the polymer component contains a hydrocarbon mixture (Ci 3 -Ci 4 -lsopar
  • anionic homopolymers are uncrosslinked and crosslinked polyacrylic acids. Allyl ethers of pentaerythritol, sucrose and propylene may be preferred crosslinking agents. Such compounds are for example available under the trademark Carbopol ® commercially.
  • Copolymers of maleic anhydride and methyl vinyl ether, especially those with crosslinks, are also color-retaining polymers.
  • a 1, 9-decadiene crosslinked maleic acid methyl vinyl ether copolymer is available under the name ® Stabileze QM.
  • the anionic polymer is selected from:
  • A- ⁇ is a methylene group, optionally via a heteroatom, such as oxygen or sulfur, to the carbon atom of the unsaturated group or, when n is greater than 1, to the adjacent methylene group is bonded
  • R-1 is a hydrogen atom, phenyl or benzyl
  • R 2 is a hydrogen atom, a lower alkyl group or carboxy
  • R 3 is a hydrogen atom, a lower alkyl group, the group -CH 2 COOH, phenyl or benzyl;
  • Polymers having units derived from a sulfonic acid such as
  • Vinylsulfonic acid, styrenesulfonic acid, acrylamidoalkylsulfonic acid are vinylsulfonic acid, styrenesulfonic acid, acrylamidoalkylsulfonic acid.
  • the anionic polymer is selected from:
  • amphoteric polymers can be used as constituents as polymers for increasing the action of the active ingredient according to the invention.
  • amphoteric polymers includes both those polymers which contain in the molecule both free amino groups and free -COOH or S0 3 H groups and which are capable of forming internal salts, as well as zwitterionic polymers which in the molecule have quaternary ammonium groups and -COO ' or -S0 3 ' groups, and those polymers comprising -COOH or S0 3 H groups and quaternary ammonium groups.
  • amphopolymer suitable is the acrylic resin commercially available as Amphomer ®, which is a copolymer of tert-butylaminoethyl methacrylate, N- (1, 1, 3,3-tetramethylbutyl) -acrylamide and two or more monomers from the group of acrylic acid, Represents methacrylic acid and its simple esters.
  • Amphomer ® is a copolymer of tert-butylaminoethyl methacrylate, N- (1, 1, 3,3-tetramethylbutyl) -acrylamide and two or more monomers from the group of acrylic acid, Represents methacrylic acid and its simple esters.
  • amphoteric polymers are those polymers which are composed essentially
  • R 22 -CH CR 23 -CO-Z- (C n H 2n ) -N (+) R 24 R 25 R 26 A (_) (IV)
  • R 22 and R 23 independently of one another represent hydrogen or a methyl group and R 24 , R 25 and R 26 independently of one another represent alkyl groups having 1 to 4 carbon atoms.
  • Atoms, Z is an NH group or an oxygen atom, n is an integer from 2 to 5 and A ⁇ 'is the anion of an organic or inorganic acid
  • R 27 and R 28 are independently hydrogen or methyl groups.
  • These compounds can be used both directly and in salt form, which is obtained by neutralization of the polymers, for example with an alkali metal hydroxide, according to the invention.
  • Very particular preference is given to those polymers in which monomers of the type (a) are used in which R 24 , R 25 and R 26 are methyl groups, Z is an NH group and A ⁇ _) is a halide, methoxysulfate or ethoxy sulfate Ion is; Acrylamidopropyl trimethyl ammonium chloride is a particularly preferred monomer (a).
  • Acrylic acid is preferably used as monomer (b) for the stated polymers.
  • the amphoteric polymer is selected from polymers having units derived from: a) at least one monomer selected from acrylamides or methacrylamides substituted on the nitrogen with an alkyl group;
  • At least one basic comonomer such as esters of acrylic acid and methacrylic acid with primary, secondary, tertiary and quaternary amino substituents, and the quaternization product of dimethylaminoethyl methacrylate with dimethyl sulfate or diethyl sulfate.
  • the agents according to the invention may furthermore contain nonionogenic polymers.
  • Suitable nonionic polymers are, for example:
  • Vinylpyrrolidone / vinyl ester copolymers as sold, for example, under the trademark Luviskol ® (BASF).
  • Luviskol ® VA 64 and Luviskol ® VA 73, each vinylpyrrolidone / vinyl acetate copolymers are also preferred nonionic polymers.
  • Cellulose ethers such as hydroxypropylcellulose, hydroxyethylcellulose and methylhydroxypropylcellulose, as sold, for example, under the trademarks Culminal ® and Benecel ® (AQUALON).
  • Siloxanes These siloxanes can be both water-soluble and water-insoluble. Both volatile and nonvolatile siloxanes are suitable, nonvolatile siloxanes being understood as meaning those compounds whose boiling point is above 200 ° C. under normal pressure.
  • Preferred siloxanes are polydialkylsiloxanes, such as Polydimethylsiloxane, Polyalkylarylsiloxane, such as polyphenylmethylsiloxane, ethoxylated polydialkylsiloxanes and polydialkylsiloxanes containing amine and / or hydroxyl groups.
  • the nonionic polymer is selected from:
  • Cationic polymers are polymers which have groups in the main and / or side chain which may be “temporary” or “permanent” cationic.
  • “permanently cationic” refers to those polymers which have a cationic group independently of the pH of the agent These are generally polymers which contain a quaternary nitrogen atom, for example in the form of an ammonium group
  • Preferred cationic groups are quaternary ammonium groups in particular, those polymers in which the quaternary ammonium group are bonded via a CI_ 4 hydrocarbon group to a synthesized from acrylic acid, methacrylic acid or derivatives thereof, polymer backbone, have proved to be particularly suitable.
  • R 8 -H or -CH 3
  • R 9 , R 20 and R 2 are independently selected from C-
  • 4 alkyl, alkenyl or hydroxyalkyl groups, m 1, 2, 3 or 4, n is a natural number and X "is a physiologically acceptable organic or inorganic anion, and copolymers consisting essentially of the in formula (III In the context of these polymers, preference is given to those according to the invention for which at least one of the following conditions applies:
  • R 8 is a methyl group - R 9 , R 20 and R 2 are methyl groups
  • m has the value 2.
  • Suitable physiologically tolerated counterions X " are, for example, halide ions, sulfate ions, phosphate ions, methosulfate ions and organic ions such as lactate, citrate, tartrate and acetate ions, preference being given to halide ions, in particular chloride.
  • a particularly suitable homopolymer is, if desired, crosslinked, poly (methacryloyloxyethyltrimethylammonium chloride) with the INCI name Polyquaternium-37.
  • the crosslinking can be carried out with the aid of poly olefinically unsaturated compounds, for example divinylbenzene, tetraallyloxyethane, methylenebisacrylamide, diallyl ether, polyallylpolyglyceryl ethers, or allyl ethers of sugars or sugar derivatives such as erythritol, pentaerythritol, arabitol, mannitol, sorbitol, sucrose or glucose.
  • Methylenebisacrylamide is a preferred crosslinking agent.
  • the homopolymer is preferably used in the form of a nonaqueous polymer dispersion which should not have a polymer content of less than 30% by weight.
  • 50% polymer content other components: mineral oil (INCI name: mineral oil) and tridecyl-polyoxypropylene-polyoxyethylene ether (INCI name: PPG-1 -Trideceth-6) under the names Salcare ® SC 95 ) and Salcare ® SC 96 (about 50% polymer content, additional components: mixture of diesters of propylene glycol with a mixture of caprylic and capric acid (INCI name: propylene glycol Dicaprylate / Dicaprate) and tridecyl polyoxypropylene-polyoxyethylene-ether (INCI Designation: PPG-1 trideceth-6)) are commercially available.
  • Copolymers with monomer units of the formula contain (II I) as non-ionic monomer, preferably acrylamide, methacrylamide, acrylic acid and methacrylic acid alkyl esters CI_ 4 d-4-alkyl ester.
  • nonionic monomers preferably acrylamide, methacrylamide, acrylic acid and methacrylic acid alkyl esters CI_ 4 d-4-alkyl ester.
  • the acrylamide is particularly preferred.
  • These copolymers can also be crosslinked, as described above in the case of the homopolymers.
  • a copolymer preferred according to the invention is the crosslinked acrylamide-methacryloyloxyethyltrimethylammonium chloride copolymer.
  • Such copolymers in which the monomers are present in a weight ratio of about 20:80, are commercially available as approximately 50% non-aqueous polymer dispersion 92 under the name Salcare ® SC.
  • quaternized cellulose derivatives such as under the trade names Celquat ® and polymer
  • JR® 400 are preferred quaternized cellulose derivatives
  • cationized honey for example the commercial product Honeyquat® 50,
  • cationic guar derivatives in particular those sold under the trade names Cosmedia®Guar and Jaguar®,
  • Quaternary group polysiloxanes such as the commercially available products Q2-7224 (manufactured by Dow Corning, a stabilized trimethylsilylamodimethicone), Dow Corning ® 929 Emulsion (containing a hydroxylamino-modified silicone which is also known as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer : Th. Goldschmidt; diquaternary polydimethylsiloxanes, quaternium-80),
  • Such compounds are sold under the names Gafquat ® 734 and Gafquat ® 755 commercially,
  • Vinylpyrrolidone vinylimidazoliummethochloride copolymers such as those offered under the names Luviquat.RTM ® FC 370, FC 550, FC 905 and HM 552,
  • Polyquaternium 27 known polymers with quaternary nitrogen atoms in the polymer main chain.
  • Can be used as cationic polymers are sold under the names Polyquaternium-24 (commercial product z. B. Quatrisoft ® LM 200), known polymers.
  • copolymers of vinylpyrrolidone such as the commercial products Copolymer 845 (manufactured by ISP), Gaffix ® VC 713 (manufactured by ISP), Gafquat ® ASCP 101 1, Gafquat ® HS 1 10, Luviquat ® 8155 and Luviquat ® MS 370 are available.
  • cationic polymers of the present invention are usually contain an amino group present at certain pH values as a quaternary ammonium group and hence cationic.
  • chitosan and its derivatives are preferred, such as for example, under the trade designations Hydagen ® CMF, Hydagen® ® HCMF, Kytamer ® PC and Chitolam ® NB / 101 are freely available commercially.
  • chitosans are deacetylated, in different degrees of deacetylation and varying degrees of degradation (molecular weights) are commercially available. Their preparation is, for example, in DE 44 40 625 A1 and in DE 1 95 03 465 A1,.
  • particularly useful chitosans have a degree of deacetylation of at least 80% and a molecular weight of 5 '10 5 to 5' 10 6 (g / mol).
  • the chitosan must be converted into the salt form. This can be done by dissolving in dilute aqueous acids. Suitable acids are both mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid and organic acids, for example low molecular weight carboxylic acids, polycarboxylic acids and hydroxycarboxylic acids. Furthermore, higher molecular weight alkyl sulfonic acids or alkyl sulfuric acids or organophosphoric acids can be used, provided that they have the required physiological compatibility.
  • Suitable acids for converting the chitosan into the salt form are, for example, acetic acid, glycolic acid, tartaric acid, malic acid, citric acid, lactic acid, 2-pyrrolidinone-5-carboxylic acid, benzoic acid or salicylic acid. Preference is given to using low molecular weight hydroxycarboxylic acids, for example glycolic acid or lactic acid.
  • preferred cosmetic compositions according to the invention are characterized in that the cationic amphiphilic polymers are chosen from quaternized cellulose derivatives and polyacrylates having aminated side chains.
  • compositions are characterized in that the cationic polymers are selected from polymers having units with primary, secondary, tertiary and / or quaternary amino groups either as part of the polymer backbone or on a side substituent directly attached thereto.
  • cationic polymer is selected from cationic cyclopolymers, cationic polysaccharides, quaternary polymers of vinylpyrrolidone and vinylimidazole, and mixtures thereof.
  • cyclopolymer is selected from the homopolymers of diallyldimethylammonium chloride and the copolymers of diallyldimethylammonium chloride and acrylamide.
  • compositions are characterized in that the cationic polysaccharides are selected from hydroxyethyl celluloses which have reacted with an epoxide substituted with a trimethylammonium group.
  • compositions are characterized in that the cationic polysaccharides are selected from guar gums modified with a 2,3-epoxypropyltrimethylammonium salt.
  • the preparations used contain a plurality of, in particular two different polymers of the same charge and / or in each case an ionic and an amphoteric and / or nonionic polymer.
  • the term polymer also means special preparations of polymers, such as spherical polymer powders.
  • Various methods are known for producing such microspheres from different monomers, for example by special polymerization processes or by dissolving the polymer in a solvent and spraying it into a medium in which the solvent can evaporate or diffuse out of the particles.
  • Suitable polymers are, for example, polycarbonates, polyurethanes, polyacrylates, polyolefins, polyesters or Polyamides. Particularly suitable are those spherical polymer powders whose primary particle diameter is less than 1 ⁇ m.
  • Such products based on a polymethacrylate copolymer are, for example, under the trademark Polytrap ® Q5-6603 (Dow Corning) in the trade.
  • Other polymer powders for example based on polyamides (nylon 6, nylon 12) having a particle size of 2 - (10 ⁇ (90%) and a specific surface area of about 10 m 2 / g under the trade name Orgasol ® 2002 DU Nat Cos Atochem SA, Paris).
  • spherical polymer powders which are suitable for the purpose according to the invention are, for example, the polymethacrylates (Micropearl M) from SEPPIC or (Plastic Powder A) from NIKKOL, the styrene-divinylbenzene copolymers (Plastic Powder FP) from NIKKOL, the polyethylene and polypropylene AKZO powder (ACCUREL EP 400) or silicone polymers (Silicone Powder X2-1605) from Dow Corning or spherical cellulose powders.
  • the polymethacrylates (Micropearl M) from SEPPIC or (Plastic Powder A) from NIKKOL
  • Plastic Powder FP styrene-divinylbenzene copolymers
  • ACCUREL EP 400 polyethylene and polypropylene AKZO powder
  • silicone polymers Silicone Powder X2-1605
  • the polymers are contained in the agents according to the invention preferably in amounts of from 0.01 to 10% by weight, based on the total agent. Amounts of 0.1 to 5, especially from 0, 1 to 3 wt .-%, are particularly preferred.
  • conditioning agents used silicones are, for example
  • Luviset CA 66 (BASF)
  • Rhodopas AD 310 Rhodia Chimie
  • Micropearl RQ 750 (Matsumoto) and Luhydran A 848 S (BASF)
  • Uraflex XP 401 UZ and Uraflex XP 402 UZ (DSM Resins)
  • Vidogum GH 175 (Unipectin)
  • Gafquat® (ISP), e.g., "Gafquat® 734" or "Gafquat® 755"
  • Mirapol® A 15, Mirapol® AD1, Mirapol® AZ1 and Mirapol® 175 (Miranol)
  • Salcare® SC 95 and Salcare® SC 96 (Ciba)
  • Crotein® BTA Croquat® L, Croquat® M, Croquat® S, Crotein® Q (Croda) Lexein® QX 3000 (Inolex)
  • Hydrotriticum WQ or QM Hydrotriticum QL, Hydrotriticum QS.
  • cosmetic compositions of the present invention which further preferably contain the conditioning agent (s) in a total amount of from 0.001 to 20% by weight, preferably from 0.01 to 15% by weight from 0.1 to 10 wt .-% and in particular from 025 to 5 wt .-%, based on the total weight of the composition.
  • 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 use being referred to as surfactants or as emulsifiers and being selected from anionic, cationic, zwitterionic, ampholytic and nonionic surfactants and emulsifiers.
  • Cosmetic agents 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 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.
  • anionic surfactants and emulsifiers 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,
  • Alpha-sulfofatty acid methyl esters of fatty acids having 8 to 30 carbon atoms are alpha-sulfofatty acids having 8 to 30 carbon atoms.
  • R CO is a linear or branched acyl radical having 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds and X is hydrogen, an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium, for example acylglutamates, which derived from fatty acids having 6 to 22, preferably 12 to 18 carbon atoms, such as, for example, C 12/14 or C 12/18 coconut fatty acid, lauric acid, myristic acid, palmitic acid and / or stearic acid, in particular sodium N-cocoyl and sodium N-stearoyl-L-glutamate,
  • esters of a hydroxy-substituted di- or tricarboxylic acid of the general formula (II)
  • X H or a -CH 2 COOR group
  • esters of sulfosuccinic acid or sulfosuccinates of general formula (III) are examples of esters of sulfosuccinic acid or sulfosuccinates of general formula (III),
  • Esters of tartaric acid and citric acid with alcohols which are addition products of approximately 2-15 molecules of ethylene oxide and / or propylene oxide with C 8 -22 fatty alcohols represent
  • Monoglyceride sulfates and monoglyceride ether sulfates Monoglyceride sulfates and monoglyceride ether sulfates.
  • Preferred anionic surfactants and emulsifiers are acylglutamates, acyl isethionates, acyl sarcosinates and acyl taurates, each with a linear or branched acyl radical having 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds, which in particularly preferred embodiments of an octanoyl, decanoyl, lauroyl , Myristoyl, palmitoyl and stearoyl radical, esters of tartaric acid, citric acid or succinic acid or the salts of these acids with alkylated glucose, in particular the products with the INCI name Disodium Coco-Glucoside Citrate, Sodium Coco-Glucoside Tartrate and Disodium Coco-glucosides sulfosuccinates, alkyl polyglycol ether sulfates and ether carboxylic acids having 8 to 18 carbon atoms in the alkyl group and up to 12 ethoxy groups in the
  • Zwitterionic surfactants and emulsifiers are surface-active compounds which contain at least one quaternary ammonium group and at least one in the molecule - carry or -S0 3 ⁇ _) group - COO ⁇ _).
  • 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.
  • alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acid salts having 10 to 18 C atoms in the alkyl group and up to 12 glycol ether groups in the molecule and sulfosuccinic acid mono- and dialkyl esters having 8 to 18 C atoms in the alkyl group and sulfosuccinic monoalkylpolyoxyethylester with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups.
  • Particularly preferred anionic surfactants are the alkali metal or ammonium salts of lauryl ether sulfate having a degree of ethoxylation of 2 to 4 EO.
  • Particularly preferred cosmetic agents according to the invention are characterized in that they contain, based on their weight, from 0.1 to 20% by weight, preferably from 0.25 to 17.5% by weight and in particular from 5 to 15% by weight of anionic ( s) surfactant (s), more preferred Fatty alcohol ether sulfates of the formula
  • n represents values of from 5 to 21, preferably from 7 to 19, particularly preferably from 9 to 17 and in particular from 1 to 13 and k for values of 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, preferably 1, 2 or 3 and especially 2
  • M is a cation from the group Na + , K + NH 4 + , Mg 2+ , Zn 2+ , preferably Na + ,
  • Zwitterionic surfactants and emulsifiers are surface-active compounds which contain at least one quaternary ammonium group and at least one in the molecule - carry or -S0 3 ⁇ _) group - COO ⁇ _).
  • 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 surface-active compounds which, apart from a C 8 - contain at least one free amino group and at least one -COOH or -S0 3 H group and alkyl or acyl group capable of forming inner salts - C 2 4 are.
  • 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 the d 2 -C 8 -acylsarcosine.
  • Particularly preferred cosmetic agents according to the invention are characterized in that they contain amphoteric surfactant (s) from the groups of N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines , N-alkyl sarcosines, 2-alkylaminopropionic acids each having about 8 to 24 carbon atoms in the alkyl group, alkylaminoacetic acids each having about 8 to 24 carbon atoms in the alkyl group, N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate C12 - Ci 8 - acylsarcosine, N-alkyl - ⁇ , ⁇ -dimethylammonium glycinates, for example, cocoalkyl dimethylammoni
  • -Atomen in the alkyl or acyl group Kokosacylaminoethylhydroxyethylcarboxymethyl- glycinate, which is known under the INCI name cocamidopropyl betaine compounds which contain compounds known by the INCI name Disodium Cocoamphodiacetate, preferred agents comprising the amphoteric surfactant (s) in amounts of from 0.5 to 9% by weight, preferably from 0.75 to 8 wt .-% and in particular from 1 to 7.5 wt .-%, each based on the total agent.
  • amphoteric surfactant (s) in amounts of from 0.5 to 9% by weight, preferably from 0.75 to 8 wt .-% and in particular from 1 to 7.5 wt .-%, each based on the total agent.
  • Particularly preferred cosmetic agents contain as amphoteric surfactants betaines of the formula (Bet-I)
  • R is a straight-chain or branched, saturated or mono- or polyunsaturated alkyl or alkenyl radical having 8 to 24 carbon atoms.
  • surfactants are referred to the INCI nomenclature as Amidopropylbetaine, wherein the representatives derived from coconut fatty acids are preferred and are referred to as Cocoamidopropylbetaine.
  • surfactants of the formula (Bet-I) which are a mixture of the following representatives: H 3 C- (CH 2 ) 7-C (O) -NH- (CH 2 ) 3 N + (CH 3 ) 2 CH 2 COO ⁇ , H 3 C- (CH 2) 9 -C (0) -NH- (CH 2) 3 N + (CH 3) 2 CH 2 COO "H 3 C- (CH 2) 11 -C ( 0) -NH- (CH 2) 3 N + (CH 3) 2 CH 2 COO ⁇ , H 3 C- (CH 2) 13 -C (0) -NH- (CH 2) 3 N + (CH 3) 2 CH 2 COO "H 3 C- (CH 2) 15 -C (0) -NH- (CH 2) 3 N + (CH
  • agents according to the invention are preferred which, based on their weight, are from 0.25 to 8% by weight, more preferably from 0.5 to 7% by weight, more preferably from 0.75 to 6.5% by weight and in particular 1 to 5.5 wt .-% of surfactant (s) of the formula (Bet-I) included.
  • the cosmetic agents according to the invention may be used with particular preference as amphoteric surfactants betaines of the formula (Bet-II)
  • R is a straight-chain or branched, saturated or mono- or polyunsaturated alkyl or alkenyl radical having 8 to 24 carbon atoms.
  • surfactants are referred to according to the INCI nomenclature as amphoacetates, wherein the representatives derived from coconut fatty acids are preferred and are referred to as cocoamphoactetates.
  • surfactants of this type also always contain betaines of the formula (Bet-I 1a)
  • R is a straight-chain or branched, saturated or mono- or polyunsaturated alkyl or alkenyl radical having 8 to 24 carbon atoms and M is a cation.
  • surfactants are referred to according to the INCI nomenclature as Amphodiacetate, wherein the representatives derived from coconut fatty acids are preferred and are referred to as Cocoamphodiactetate.
  • agents according to the invention are preferred which, based on their weight, are from 0.25 to 8% by weight, more preferably from 0.5 to 7% by weight, more preferably from 0.75 to 6.5% by weight and in particular 1 to 5.5 wt .-% of surfactant (s) of the formula (Bet-II) included.
  • nonionic surfactants are alkyl polyglycosides. Accordingly, cosmetic agents according to the invention are preferred which contain as nonionic surfactants-based on their weight-0, 1 to 20 wt .-% alkylpolyglycosides of the general formula RO- (Z) x , wherein R is alkyl, Z for sugar and x for the Number of sugar units is.
  • Alkylpolyglycosides are nonionic surfactants made entirely from renewable resources (sugar building blocks, predominantly glucose, for example from corn starch and fatty alcohol, for example from coconut oil). Alkyl polyglycosides are accessible by acid-catalyzed reaction (Fischer reaction) of sugars, especially glucose (or starch) or butyl glycosides with fatty alcohols.
  • alkyl monoglucoside alkyl aD and - ⁇ -D-glucopyranoside and small amounts -glucofuranoside
  • alkyldiglucosides -isomaltoside, maltosides, etc.
  • Alkyl oligoglucosides maltotriosides, tetraosides etc.
  • the average degree of polymerization of commercial products whose alkyl radicals are in the range C8-C16 is 1, 2-1, 5.
  • alkylpolyglycosides corresponding to the general formula RO - (Z) x , where R is alkyl, Z is sugar and x is the number of sugar units.
  • R is alkyl
  • Z is sugar
  • x is the number of sugar units.
  • sugar building block Z it is possible to use any desired mono- or oligosaccharides.
  • sugars with 5 or 6 carbon atoms and the corresponding oligosaccharides are used.
  • Such sugars are, for example, glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, altrose, mannose, gulose, idose, talose and sucrose.
  • Preferred sugar building blocks are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkylpolyglycosides which can be used according to the invention contain on average 1, 1 to 5 sugar units. Alkyl polyglycosides having x values of 1.1 to 2.0 are preferred. Very particular preference is given to alkyl glycosides in which x is 1: 1 to 1, 8.
  • surfactants which can be used particularly advantageously in the compositions according to the invention, especially in admixture with alkylpolyglycosides, are glutamates, asparaginates and sulfoacetates.
  • cosmetic agents according to the invention are preferred which contain, based on their weight, 0.1 to 20% by weight of fatty acid glutamates (acylglutamates) and / or fatty acid asparaginates (acylasparaginates) and / or alkylsulfoacetates (sulfoacetic acid alkyl esters).
  • acylglutamates are anionic surfactants derived from fatty acids having 6 to 22, preferably 12 to 18 carbon atoms, such as C12 / 14 or C12 / 18 coconut fatty acid, lauric acid, myristic acid, palmitic acid and / or stearic acid. Particularly preferred are sodium N-cocoyl and sodium N-stearoyl-L-glutamate
  • compositions according to the invention may contain the alkyl and / or alkenyl oligoglucosides and the acyl glutamates in a weight ratio of 1:99 to 99: 1, preferably 10:90 to 90:10 and in particular 80:20 to 50:50.
  • acylasparaginates are anionic surfactants derived from fatty acids having 6 to 22, preferably 12 to 18, carbon atoms, such as, for example, C12 / 14 or C12 / 18 coconut fatty acid, lauric acid, myristic acid, palmitic acid and / or stearic acid. Particularly preferred are sodium N-cocoyl and sodium N-stearoyl-L-aspartate
  • the agents according to the invention may also contain the alkyl and / or alkenyl oligoglucosides and the acylasparaginates in a weight ratio of 1:99 to 99: 1, preferably 10:90 to 90:10 and in particular 80:20 to 50:50.
  • the use of the sodium salt of sulfoacetic acid with the INCI is particularly preferred.
  • Sodium lauryl sulphoacetate is a white, free-flowing powder which reacts neutrally, with good foaming power, wetting power and dispersibility.
  • 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.
  • Particularly preferred hair cleansing and conditioning agents according to the invention are characterized in that they contain as cationic care substance - based on their weight - 0.05 to 7.5 wt .-%, preferably 0, 1 to 5 wt .-%, particularly preferably 0, From 2 to 3.5% by weight and in particular from 0.25 to 2.5% by weight of cationic surfactant (s) from the group of quaternary ammonium compounds and / or esterquats and / or amidoamines, with preferred cationic surfactant (s) is / are selected from alkyltrimethylammonium chlorides having preferably 10 to 18 carbon atoms in the alkyl radical and / or dialkyldimethylammonium chlorides having preferably 10 to 18 carbon atoms in the alkyl radical and / or trialkylmethylammonium chlorides having preferably 10 to 18 carbon atoms in the alkyl radical and / or cetyltrimethylammonium chloride and / or stearyltrimethylammonium chlor
  • compositions according to the invention can be further enhanced by using certain care substances.
  • care substances are preferably selected from certain groups of known care substances, since these care substances perfectly harmonize with the silicones used according to the invention in terms of formulation and the care effect.
  • Cosmetic agents preferred according to the invention are characterized in that they additionally contain care substance (s) in amounts of from 0.001 to 10% by weight, preferably from 0.005 to 7.5% by weight, particularly preferably from 0.01 to 5% by weight Wt .-% and in particular 0.05 to 2.5 wt .-%, with preferred care substance (s) are selected from the group L-carnitine and / or its salts; Panthenol and / or panthothenic acid; the 2-furanones and / or their Derivatives, in particular pantolactone; Taurine and / or its salts; niacinamide; ubiquinone; Ectoin; Allantoin.
  • care substance (s) are selected from the group L-carnitine and / or its salts; Panthenol and / or panthothenic acid; the 2-furanones and / or their Derivatives, in particular pantolactone; Taurine and / or its salts; niacinamide; ubiquino
  • the silicones are combined with at least one care substance which is selected from L-carnitine and / or its salts, panthenol and / or pantothenic acid, 2-furanones and / or their derivatives, in particular pantolactone, taurine and / or its Salts, niacinamide, ubiquinones, ectoine, allantoin.
  • care substance which is selected from L-carnitine and / or its salts, panthenol and / or pantothenic acid, 2-furanones and / or their derivatives, in particular pantolactone, taurine and / or its Salts, niacinamide, ubiquinones, ectoine, allantoin.
  • the inventive combination of organopolysiloxane and conditioning agent (s) can be further increased in their care properties, if certain proteolipids are incorporated in the inventive compositions.
  • 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) 0- or -N + (R '" 2 ) R iv - or -N (R'") R iv - or -C (O) -N (R V ) R VI - .
  • 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, wherein the amino group may be free or protonated and the carboxy groups may be free or deprotonated.
  • 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.
  • 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 free or protonated and the carboxy groups may be free or deprotonated.
  • Further preferred oligopeptides additionally contain arginine, which is preferably bound to isoleucine.
  • Cosmetic agents 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-Ile-Arg, where the amino groups are 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.
  • Cosmetic agents which are further 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-Ile-Arg-Val, the amino groups being 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 which contain at least one proteolipd of the formula (I) in which R "has at least one amino acid sequence Leu-Tyr-Glu-Glu-Glu-Ile-Arg-Val-Leu, where the amino groups free or protonated and the carboxy groups may be free or 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 are, for example, under the trademarks Gluadin ® (Cognis), diamine ® (Diamalt) ® (Inolex) and Crotein ® (Croda) available.
  • the residue 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 " is 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 ) 17 -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 ) 17 -CH 3 .
  • protein hydrolysates in addition to the proteolipids. These enhance the effect of the proteolipids and are in turn 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) included.
  • cosmetic agents which are preferred according to the invention are therefore characterized by being transparent or translucent.
  • NTU Nephelometrie Turbidity Unit
  • an agent according to the invention may also contain UV filters (I).
  • the UV filters to be used according to the invention 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 filters 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 are usually present in the compositions according to the invention in amounts of 0.1 to 5% by weight, based on the total composition. Levels of 0.4-2.5 wt .-% are preferred.
  • the agents according to the invention may contain emulsifiers (F).
  • Emulsifiers effect at the phase interface the formation of water- or oil-stable adsorption layers, which protect the dispersed droplets against coalescence and thus stabilize the emulsion.
  • Emulsifiers are therefore constructed like surfactants from a hydrophobic and a hydrophilic part of the molecule. Hydrophilic emulsifiers preferably form O / W emulsions and hydrophobic emulsifiers preferably form W / O emulsions.
  • An emulsion is to be understood as meaning a droplet-like distribution (dispersion) of a liquid in another liquid under the expense of energy in order to create stabilizing phase interfaces by means of surfactants.
  • the selection of these emulsifying surfactants or emulsifiers depends on the substances to be dispersed and the respective outer phase and the fineness of the emulsion.
  • Emulsifiers which can be used according to the invention are, for example
  • Glucosides mixtures of alkyl (oligo) and fatty alcohols for example, the commercially available product ® Montanov 68,
  • Sterols are understood to mean a group of steroids which carry a hydroxyl group on C-atom 3 of the steroid skeleton and are isolated both from animal tissue (zoosterines) and from vegetable fats (phytosterols). Examples of zoosterols are cholesterol and lanosterol. Examples of suitable phytosterols are ergosterol, stigmasterol and sitosterol. Mushrooms and yeasts are also used to isolate sterols, the so-called mycosterols.
  • Phospholipids include, in particular, the glucose phospholipids which are obtained, for example, as lecithins or phosphatidylcholines from, for example, egg yolks or plant seeds (for example soybeans).
  • Polyglycerols and polyglycerol derivatives such as polyglycerol poly-12-hydroxystearate (commercial product Dehymuls ® PGPH),
  • Linear and branched fatty acids with 8 to 30 C atoms and their Na, K, ammonium, Ca, Mg and Zn salts.
  • the agents according to the invention preferably contain the emulsifiers in amounts of 0.1 to 25% by weight, in particular 0.5 to 15% by weight, based on the total agent.
  • compositions according to the invention may preferably contain at least one nonionic emulsifier having an HLB value of 8 to 18.
  • Nonionic emulsifiers with an HLB value of 10 to 15 may be particularly preferred according to the invention.
  • the anionic polymers (G2) are anionic polymers which have carboxylate and / or sulfonate groups.
  • anionic monomers from which such polymers may consist are acrylic acid, methacrylic acid, crotonic acid, maleic anhydride and 2-acrylamido-2-methylpropanesulfonic acid.
  • the acidic groups may be wholly or partly present as sodium, potassium, ammonium, mono- or triethanolammonium salt.
  • Preferred monomers are 2-acrylamido-2-methylpropanesulfonic acid and acrylic acid.
  • Anionic polymers which contain 2-acrylamido-2-methylpropanesulfonic acid as the sole or co-monomer can be found to be particularly effective, it being possible for all or some of the sulfonic acid group to be present as sodium, potassium, ammonium, mono- or triethanolammonium salt ,
  • the homopolymer of 2-acrylamido-2-methyl propane sulfonic acid which is commercially available, for example under the name Rheothik ® 1 1-80 is.
  • copolymers of at least one anionic monomer and at least one nonionic monomer are preferable to use copolymers of at least one anionic monomer and at least one nonionic monomer.
  • anionic monomers reference is made to the substances listed above.
  • Preferred nonionic monomers are acrylamide, methacrylamide, acrylic esters, methacrylic esters, vinylpyrrolidone, vinyl ethers and vinyl esters.
  • Preferred anionic copolymers are acrylic acid-acrylamide copolymers and in particular polyacrylamide copolymers with sulfonic acid-containing monomers.
  • a particularly preferred anionic copolymer consists of 70 to 55 mol% of acrylamide and 30 to 45 mol% of 2-acrylamido-2-methylpropanesulfonic acid, wherein the sulfonic acid group is wholly or partly in the form of sodium, potassium, ammonium, mono- or triethanolammonium Salt is present.
  • This copolymer can also be crosslinked, with crosslinking agents preferably polyolefinically unsaturated Compounds such as tetraallyloxyethane, allylsucrose, allylpentaerythritol and methylene-bisacrylamide are used.
  • crosslinking agents preferably polyolefinically unsaturated Compounds such as tetraallyloxyethane, allylsucrose, allylpentaerythritol and methylene-bisacrylamide are used.
  • Such a polymer is contained in the commercial product Sepigel ® 305 from SEPPIC.
  • the use of this compound, which in addition to the polymer component contains a hydrocarbon mixture (Ci 3 -Ci 4 -lsoparaffin) and a nonionic emulsifier (laureth-7), has proved to be particularly advantageous in the context of the teaching of the invention.
  • Simulgel ® 600 as a compound with isohexade
  • anionic homopolymers are uncrosslinked and crosslinked polyacrylic acids. Allyl ethers of pentaerythritol, sucrose and propylene may be preferred crosslinking agents. Such compounds are for example available under the trademark Carbopol ® commercially.
  • Copolymers of maleic anhydride and methyl vinyl ether, especially those with crosslinks, are also color-retaining polymers.
  • a 1, 9-decadiene crosslinked maleic acid methyl vinyl ether copolymer is available under the name ® Stabileze QM.
  • the agents according to the invention may contain nonionic polymers (G4).
  • Suitable nonionic polymers are, for example:
  • Vinylpyrrolidone / vinyl ester copolymers as sold, for example, under the trademark Luviskol ® (BASF).
  • Luviskol ® VA 64 and Luviskol ® VA 73, each vinylpyrrolidone / vinyl acetate copolymers are also preferred nonionic polymers.
  • Cellulose ethers such as hydroxypropyl cellulose, hydroxyethyl cellulose and hydroxypropylcellulose Methylhy-, as sold for example under the trademark Culminal® ® and Benecel ® (AQUALON) and Natrosol ® grades (Hercules).
  • Starch and its derivatives in particular starch, such as Structure XL ® (National Starch), a multifunctional, salt-tolerant starch;
  • Siloxanes These siloxanes can be both water-soluble and water-insoluble. Both volatile and nonvolatile siloxanes are suitable, nonvolatile siloxanes being understood as meaning those compounds whose boiling point is above 200 ° C. under normal pressure.
  • Preferred siloxanes are polydialkylsiloxanes, such as, for example, polydimethylsiloxane, polyalkylarylsiloxanes, such as, for example, polyphenylmethylsiloxane, ethoxylated polydialkylsiloxanes and polydialkylsiloxanes which contain amine and / or hydroxyl groups.
  • the preparations comprise a plurality of, in particular two, different polymers of the same charge and / or in each case an ionic and an amphoteric and / or nonionic polymer.
  • the other polymers (G) are contained in the agents according to the invention preferably in amounts of 0.05 to 10 wt .-%, based on the total agent. Amounts of 0.1 to 5, in particular from 0.1 to 3 wt .-%, are particularly preferred.
  • Another object of the present invention is a method for the treatment of keratinous fibers, in which a hair treatment agent according to the invention is applied to the keratinic fibers and rinsed again after a contact time of a few seconds to 45 minutes.
  • Another object of the present invention is the use of hair treatment compositions according to the invention.

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Abstract

L'invention concerne des compositions cosmétiques comprenant, dans un milieu cosmétiquement acceptable, au moins un agent de conditionnement choisi parmi les huiles synthétiques, les huiles minérales, les huiles végétales, les huiles fluorées ou perfluorées, les cires naturelles ou synthétiques, les composés de type céramide, les esters d'acide carboxylique, les silicones différents des silicones de formule (I), les polymères anioniques, les polymères non ioniques, les polymères cationiques, les polymères amphotères, les protéines cationiques, les hydrolysats de protéines cationiques, les tensioactifs cationiques ainsi que les mélanges de ces différents composés et au moins un organopolysiloxane à terminaison hydroxy de formule générale (I), dans laquelle R représente un radical hydrocarbure monovalent, non substitué ou substitué par halogène, ayant 1 à 20 atomes de carbone, R1 représente un radical hydrocarbure monovalent, non substitué ou substitué par halogène, ayant 1 à 20 atomes de carbone, -OR4 ou -OH, R4 représente un radical alkyle possédant 1 à 6 atomes de carbone, G désigne un groupe de formule générale (II), dans laquelle R2, R3 représentent indépendamment l'un de l'autre un radical hydrocarbure bivalent possédant 1 à 6 atomes de carbone, des motifs CH2 non voisins pouvant être remplacés par des motifs choisis parmi -C(=0)-, -O-, et -S-, - A R5-C(=0)-, R5 représente un radical alkyle ayant 1 à 20 atomes de carbone, a peut prendre les valeurs entières de 100 à 1 500 et b peut prendre les valeurs entières supérieures ou égales à 1. Ces compositions cosmétiques améliorent de nombreuses propriétés des surfaces corporelles, en particulier des cheveux, traitées avec ces compositions et permettent en particulier d'obtenir une réduction des angles de contact des cheveux, outre une peignabilité et un toucher améliorés.
EP13705824.4A 2012-04-26 2013-02-26 Produit de traitement capillaire contenant un (des) organopolysiloxane(s) à terminaison hydroxy et un (des) agent(s) de conditionnement Ceased EP2844350A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102012206949A DE102012206949A1 (de) 2012-04-26 2012-04-26 Haarbehandlungsmittel mit hydroxy-terminierten Organopolysiloxan(en) und Konditioniermittel(n)
PCT/EP2013/053822 WO2013159955A2 (fr) 2012-04-26 2013-02-26 Produit de traitement capillaire contenant un (des) organopolysiloxane(s) à terminaison hydroxy et un (des) agent(s) de conditionnement

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EP2844350A2 true EP2844350A2 (fr) 2015-03-11

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US (1) US20150044155A1 (fr)
EP (1) EP2844350A2 (fr)
JP (1) JP2015514787A (fr)
DE (1) DE102012206949A1 (fr)
WO (1) WO2013159955A2 (fr)

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DE102013225844A1 (de) * 2013-12-13 2015-06-18 Henkel Ag & Co. Kgaa Kosmetische Zusammensetzung enthaltend eine Kombination aus Oligopeptiden und Ceramiden
CA3189438A1 (fr) 2020-07-21 2022-01-27 Chembeau LLC Formulations cosmetiques a base de diester et leurs utilisations

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JPS5813700A (ja) 1981-07-17 1983-01-26 花王株式会社 食器用洗浄剤組成物
EP0217274A3 (fr) 1985-09-30 1988-06-29 Kao Corporation Composition cosmétique pour les cheveux
DE3708451A1 (de) 1987-03-16 1988-10-06 Henkel Kgaa Zwitterionische polymere und deren verwendung in haarbehandlungsmitteln
DE3725030A1 (de) 1987-07-29 1989-02-09 Henkel Kgaa Oberflaechenaktive hydroxysulfonate
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DE4413686C2 (de) 1994-04-20 1996-10-24 Henkel Kgaa Kationische Zuckertenside, Verfahren zu ihrer Herstellung und deren Verwendung
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US20150044155A1 (en) 2015-02-12
JP2015514787A (ja) 2015-05-21
WO2013159955A3 (fr) 2014-11-13
WO2013159955A2 (fr) 2013-10-31
DE102012206949A1 (de) 2013-10-31

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