WO2015091048A1 - Agents de conditionnement pour fibres kératiniques comprenant un dérivé d'acide pyroglutamique - Google Patents

Agents de conditionnement pour fibres kératiniques comprenant un dérivé d'acide pyroglutamique Download PDF

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Publication number
WO2015091048A1
WO2015091048A1 PCT/EP2014/076858 EP2014076858W WO2015091048A1 WO 2015091048 A1 WO2015091048 A1 WO 2015091048A1 EP 2014076858 W EP2014076858 W EP 2014076858W WO 2015091048 A1 WO2015091048 A1 WO 2015091048A1
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acid
group
hair
weight
unsaturated
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PCT/EP2014/076858
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German (de)
English (en)
Inventor
Edith Von Aspern
Thomas Hippe
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Henkel Ag & Co. Kgaa
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    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/002—Preparations for repairing the hair, e.g. hair cure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/004—Preparations used to protect coloured hair

Definitions

  • compositions for the treatment of keratinic fibers, in particular human hair which significantly improve the conditioning properties and the gloss and feel of keratinic fibers, especially human hair, over prior art compositions.
  • the compositions according to the invention contain as essential ingredients at least one selected cationic surfactant and at least one selected derivative of pyrrolidonecarboxylic acid (PCA).
  • keratinous fibers especially human hair
  • human hair is today treated in a variety of ways with hair cosmetic preparations.
  • compositions for use on keratinic fibers, in particular human hair not only have to have good cleansing and conditioning and care properties, but should continue to be well tolerated and even with frequent use do not lead to excessive defatting or dryness and split ends.
  • the feeling of the keratin fibers after cosmetic treatments is an essential criterion, whether the corresponding composition is perceived by the consumer as pleasant.
  • the sensor technology and in particular the feel of a composition are thus essential effects that the consumer can experience.
  • compositions which not only care for the keratinic fibers, in particular human hair, but moreover perceptibly and tangibly change their sensory and in particular haptic properties of the surface of keratinic fibers, in particular human hair.
  • the compositions should regenerate and balance the structure, in particular inside the keratinic fibers, in particular the human hair.
  • the compositions should be easy and inexpensive to produce.
  • Silicones are known for their excellent hair conditioning properties. However, silicones have the disadvantage that they have to be synthesized with high energy expenditure and in some cases are very persistent in the environment. There is therefore a desire in certain consumer groups for silicone-free cosmetic products. The present application was therefore based on the further object of providing a good hair conditioning agent which offers excellent conditioning properties without the use of silicones.
  • a cosmetic composition comprising, in a cosmetic carrier, at least one selected cationic surfactant and at least one selected derivative of the pyrrolidonecarboxylic acid, fulfills the stated objectives in an ideal manner.
  • the use of this combination of active ingredients leads to surprisingly good properties of the treated hair, in particular to improved combing, to improved gloss and to improved elasticity as well as to a markedly increased wash resistance of the color dyed hair, as well as to a longer shelf life with a simultaneous better forming performance Welling procedures, such as water wave and perm, or with smoothing agents for frizzy hair.
  • the subject of the present application is therefore a cosmetic composition for the conditioning of keratinic fibers, contained in a cosmetic carrier
  • R1, R2 and R3 each independently of one another mean:
  • branched or linear alkyl radical having 1 to 4 carbon atoms, which may contain at least one hydroxyl group, or
  • n 1 to 200, preferably 1 to 100, particularly preferably 1 to 50, and particularly preferably 1 to 20 with R 5 in the meaning of hydrogen, methyl or ethyl,
  • hydroxyalkylene group having one to four, preferably two to three, carbon atoms which may be branched or linear and which contains one to three hydroxy groups, preferably a group selected from> CHOH, -CH 2 CHOH-, -CHOHCHOH-, -CH 2 CHOHCH 2 - ,> C (CH 2 OH) 2 ,> C (CH 2 OH) 2 , -CH 2 CHOHCHOH-, -CH 2 CH (CH 2 OH) - and hydroxybutyl radicals,
  • R6 represents a saturated or unsaturated, branched or linear or a cyclic saturated or unsaturated alkyl radical having 6 to 30, preferably 1 1 to 21, particularly preferably 15 to 17, carbon atoms containing at least one hydroxy group and optionally can furthermore be alkoxylated with 1 to 100 ethylene oxide units and / or 1 to 100 propylene oxide units, or
  • R7 is a saturated or unsaturated, branched or linear or a cyclic saturated or unsaturated alkyl radical having 6 to 30 carbon atoms, which may contain at least one hydroxy group, and which optionally further with 1 to 100 ethylene oxide units and / or 1 can be alkoxylated to 100 propylene oxide units, or
  • R 8 -NH- in which R 8 represents a linear or branched acyl or alkyl radical having in each case 6 to 30 C atoms, which may be saturated or unsaturated and / or substituted by at least one OH group, and
  • Q is a physiologically acceptable organic or inorganic anion, if none of the radicals R 1, R 2, R 3 is a free electron pair,
  • Hair treatment compositions in the context of the present invention are, for example, hair shampoos, hair conditioners, conditioning shampoos, hair conditioners, hair treatments, hair packs, hair tonics, hair dye shampoos or combinations thereof.
  • the hair conditioning compositions such as hair conditioners, hair treatments, hair wraps, hair oils and lotions both as leave-on, so as on the hair until the next hair wash remaining products, as well as rinse-off, so few seconds to a few hours after the Application again rinsed products, understood by the hair treatment compositions according to the invention.
  • combability is meant according to the invention both the combability of the wet fiber and the combability of the dry fiber.
  • the grip defines the tactility of a fiber collective, whereby the person skilled in the art senses and evaluates the parameters "fullness” and "suppleness” of the fiber collective.
  • Shaping is understood to mean the ability to give a shape change to a group of previously treated keratin-containing fibers, in particular human hair. Hair cosmetics also speak of hair styling. Restructuring in the context of the invention is to be understood as a reduction of the damage of keratinic fibers which has arisen due to a great variety of influences. Here, for example, the restoration of natural strength plays an essential role. Restructured fibers are characterized by improved gloss, improved grip and ease of combing. In addition, they have improved strength and elasticity. Furthermore, a successful restructuring can be physically detected as a melting point increase compared to the damaged fiber. The higher the melting point of the hair, the firmer the structure of the fiber.
  • wash fastness is to be understood as meaning the preservation of the original color with regard to nuance and / or intensity when the keratinic fiber is exposed to the repeated influence of aqueous agents, in particular surfactant-containing agents such as shampoos.
  • compositions according to the invention comprising the combination of active substances according to the invention are distinguished by a markedly improved state of the keratinic fibers with respect to the moisture balance of the keratinic fibers.
  • the combination of active substances according to the invention leads to a clear protection of the keratinic fibers from the effects of heat, for example during blow-drying of keratinic fibers.
  • compositions according to the invention lead to a significantly delayed re-soiling of the keratinic fibers.
  • the cosmetic carrier according to the invention is preferably an aqueous cosmetic carrier which contains at least 30% by weight of water, based on the weight of the composition according to the invention.
  • aqueous-alcoholic cosmetic carriers are aqueous solutions containing from 3 to 50% by weight, based on the weight of the composition according to the invention, of at least one C 2 -C 6 -alcohol, in particular ethanol or propanol, isopropanol, 1, 2-propylene glycol, butanol, isobutanol, tert-butanol, n-pentanol, iso-pentanols, especially 3-methyl-1-butanol, n-hexanol, iso-hexanols, ethylene glycol, glycerol, 1, 2-pentane diol, 1, 5-pentanediol, 2-methyl-2,4-pentanediol, 1, 2-hexanediol or 1, 6-hexanediol to understand.
  • the compositions of the invention may additionally contain other organic solvents, such as methoxybutanol, benzyl alcohol or
  • Cationic surfactants of the formula (Tkat 1-3) are the first group of compulsory ingredients of the compositions according to the invention.
  • Q is a physiologically acceptable anion, for example, halides such as chloride or
  • Preferred physiologically acceptable anion Q are halide ions, sulfate ions, phosphate ions, methosulfate ions, ethosulfate ions and organic ions such as lactate, citrate, tartrate and acetate ions. Preference is given to methosulfates, ethosulfates and halide ions, in particular chloride.
  • the at least one cationic surfactant of the formula (Tkat 1-3) is preferably present in the compositions according to the invention in a total amount of from 0.2 to 10.0% by weight, particularly preferably from 1.0 to 5.0% by weight, most preferably from 1.5 to 4.0% by weight, based in each case on the weight of the composition.
  • a first preferred embodiment of the invention is characterized in that the at least one cationic surfactant is selected from compounds of the formula (Tkat1 -3), wherein R1 and R2 and R3 are methyl and
  • A represents a linear hydroxyalkylene group having three carbon atoms containing a hydroxy group, preferably the group -CH 2 CHOHCH 2 -, and
  • R4 stands for R6-COO-
  • R 6 is a saturated linear alkyl radical having 1 1 to 21 carbon atoms and
  • Q stands for methosulfates, ethosulfates or chloride.
  • a particularly preferred cationic surfactant of this type is selected from 3-behenoyloxy-2-hydroxypropyltrimethylammonium chloride.
  • Cationic surfactants of this type are preferably in the compositions according to the invention in a total amount of 0.2 to 5.0 wt .-%, particularly preferably from 0.5 to 3.0 Wt .-%, most preferably from 1, 0 to 2.0 wt .-%, each based on the weight of the composition.
  • a further preferred embodiment of the invention is characterized in that the at least one cationic surfactant is selected from compounds of the formula (Tkat1-3), wherein R 1 is methyl and
  • R 2 and R 3 form a heterocyclic unsaturated alkylene group substituted with a saturated or unsaturated linear alkyl group of 6 to 20 carbon atoms,
  • A stands for the group -CH2-CH2-
  • R4 is R8-NH-
  • R8 is a linear acyl radical having 6 to 30 C atoms, preferably 10 to 20 C atoms, which is saturated or unsaturated, and
  • Q stands for methosulfates, ethosulfates or chloride.
  • a particularly preferred cationic surfactant of this type is selected from Quaternium-87.
  • Another, also particularly preferred, cationic surfactant of this type is selected from quaternium-27.
  • Cationic surfactants of this type are in the compositions according to the invention preferably in a total amount of 0.2 to 5.0 wt .-%, particularly preferably from 0.5 to 3.0 wt .-%, most preferably from 1, 0 to 2.0 wt. %, in each case based on the weight of the composition.
  • compositions preferred according to the invention comprise a mixture of the cationic surfactant types as characterized respectively in the subclaims 2 and 3 or 4 and 5.
  • Particularly preferred compositions according to the invention contain one of the following surfactant combinations:
  • the second essential ingredient according to the invention is glyceryl monopyroglutamate monooleate according to Formal (PCA-I),
  • compositions according to the invention comprise the glyceryl monopyroglutamate monooleate in a total amount of from 0.1 to 5% by weight, preferably from 0.2 to 1% by weight, based on the weight of the composition.
  • compositions according to the invention for further enhancing the hair conditioning effect of the combination of cationic surfactant according to formula (Tkat 1-3) and the glyceryl monopyroglutamate monooleate contain at least one cationic polymer in a total amount of 0.01 to 5.0 wt .-%, based on the Weight of the composition.
  • Preferred cationic polymers are selected from the following cationic polymers:
  • Suitable cationic polymers derived from natural polymers are cationic derivatives of polysaccharides, for example, cationic derivatives of cellulose, starch or guar.
  • Cationic polysaccharides have the general formula G-O-B-N + R a RbRc A ⁇
  • G is an anhydroglucose residue, for example starch or cellulose anhydroglucose
  • B is a divalent linking group, for example, alkylene, oxyalkylene, polyoxyalkylene or hydroxyalkylene;
  • R a , Rb and R c are independently alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl or alkoxyaryl each having up to 18 carbon atoms, wherein the total number of carbon atoms in R a , Rb and R c is preferably not more than 20;
  • a " is a common counteranion and is preferably chloride.
  • the cationic celluloses are preferred.
  • Cationic celluloses are available in the market with varying degrees of substitution, cationic charge density, nitrogen content and molecular weights.
  • the following cationic celluloses are highly preferred according to the invention.
  • Polyquaternium-67 (Amerchol) is available commercially for example under the names Polymer ® SL or polymer ® SK. Under the trade designation Mirustyle CP ® of the company. Croda another most preferred cellulose is available. This is a trimonium and cocodonium hydroxyethyl cellulose as derivatized cellulose with the INCI name Polyquaternium-72. Polyquaternium-72 can be used pre-dissolved both in solid form and already in aqueous solution.
  • Suitable cationic polymers derived from synthetic polymers are, for example, copolymers
  • A1 from 0.1 to 50%, preferably from 10 to 50% (based on the total number of monomers in the copolymer) of monomers of the formula (Ia)
  • X is chloride, sulphate, methosulphate,
  • the monomer A2 represents 50 to 99.9%, preferably 50 to 90% (based on the total number of monomers in the copolymer) of the copolymer;
  • hair treatment compositions according to the invention which are characterized in that the ratio of (Y: z) 4: 1 to 1: 2, preferably 4: 1 to 1: 1 amounts to.
  • hair treatment compositions according to the invention are preferred in which the copolymer A has a molecular weight of 10,000 to 20 million gmol -1 , preferably 100,000 to 10 million gmol -1 , more preferably 500,000 to 5 Million gmo and more particularly from 1, 1 million to 2.2 million gmol -1 .
  • a most preferred polymer constructed as previously shown is commercially available under the name Polyquaternium-74.
  • Another highly preferred cationic synthetic polymer is an optionally crosslinked homopolymer, poly (methacryloyloxyethyltrimethylammonium chloride) having the INCI name Polyquaternium-37.
  • poly (methacryloyloxyethyltrimethylammonium chloride) having the INCI name Polyquaternium-37.
  • Rheocare ® CTH Cosmetic Rheologies
  • Synthalen® ® CR (3V Sigma) in trade.
  • the homopolymer is preferably used in the form of a non-aqueous polymer dispersion.
  • Such polymer dispersions are available under the names Salcare ® SC 95 and Salcare ® SC 96 in the trade.
  • Hair treatment agents according to the invention contain Polyquaternium-37 by weight in amounts of 0.001 to 5 wt.%, Preferably 0.0025 to 2.5 wt.%, Particularly preferably 0.005 to 1 wt.%, More preferably 0, 0075 to 0.75 wt .-% and in particular 0.01 to 0.5 wt .-%.
  • compositions of the invention may further contain at least one sugar surfactant.
  • nonionic surfactants are those based on sugar. On the one hand, this is preferably an alkyl or alkenyl oligoglycoside.
  • These nonionic emulsifiers are known nonionic surfactants according to formula (I), R 1 0- [G] P (I)
  • R is an alkyl or alkenyl radical having 4 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms
  • p is a number from 1 to 10.
  • the alkyl and alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • the index number p in the general formula (I) indicates the degree of oligomerization (DP), ie the distribution of monoglycerides and oligoglycosides, and stands for a number between 1 and 10.
  • the value p for a given alkyloligoglycoside is an analytically determined arithmetic variable, which usually represents a fractional number. Preference is given to using alkyl and / or alkenyl oligoglycosides having an average degree of oligomerization p of from 1.1 to 3.0. Preferred are those alkyl and / or Alkenyloligoglykoside whose degree of oligomerization is less than 1, 7 and in particular between 1, 2 and 1, 4.
  • the alkyl or alkenyl radical R can be derived from primary alcohols having 4 to 22, preferably 8 to 22 carbon atoms.
  • Typical examples are butanol, caproic alcohol, caprylic alcohol, capric alcohol, undecyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, iso-stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol, natural fatty alcohols such as coconut alcohol and technical mixtures , .
  • Oramix® examples are - grades from Seppic, for example Oramix® NS 10 Plantacare® ® - types, such as Plantacare® ® 2000UP, Plantacare® ® 1200UP, Plantacare® ® 810UP, Plantacare® ® 818UP.
  • sugar-based emulsifier may be a fatty acid N-alkylpolyhydroxyalkylamide of formula (II),
  • R 3 is hydrogen, an alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms and [Z] is a linear or branched polyhydroxyalkyl radical having 3 to 12 carbon atoms and 3 to 10 hydroxyl groups stands.
  • the fatty acid N-alkylpolyhydroxyalkylamides are derived from reducing sugars with 5 or 6 carbon atoms, in particular from the glucose.
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (III):
  • the fatty acid N-alkylpolyhydroxyalkylamides used are preferably glucamides of the formula (III) in which R 3 is hydrogen or an alkyl group and R 2 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitic acid, stearic acid, Isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachidic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • the nonionic sugar-based surfactant is preferably contained in the compositions of the invention in amounts of 0.001-3.0% by weight, based on the total agent. Amounts of 0.01-2.0% by weight are particularly preferred.
  • compositions according to the invention may optionally contain further conventional ingredients. These are especially added to give the compositions other desired properties, such as an anti-dandruff or increasing volume etc. These ingredients will now be described.
  • fatty alcohols As fatty alcohols (fatal) it is possible to use saturated, mono- or polyunsaturated, branched or linear fatty alcohols. Saturated and linear fatty alcohols are preferably used with a C chain length of C6-Cis, preferably Cs-Cis and most preferably C10-Ci6. Mono- or polyunsaturated fatty alcohols and also branched and unsaturated or branched and saturated fatty alcohols are preferably used with a C chain length of C6-C30, preferably C10 to C22 and very particularly preferably of C12-C22.
  • the fatty alcohols are preferably contained in a total amount of 0.1-10% by weight, more preferably 2-5% by weight, based in each case on the total composition.
  • fatty acids can be used linear and / or branched, saturated and / or unsaturated fatty acids having 6 to 30 carbon atoms. Preference is given to fatty acids having 10 to 22 carbon atoms. Among these could be mentioned, for example, isostearic as the commercial products Emersol ® 871 and Emersol ® 875, and isopalmitic acids such as the commercial product Edenor ® IP 95, and all other products sold under the trade names Edenor ® (BASF) fatty acids.
  • fatty acids are caproic acid, caprylic acid, 2- Ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid, and technical mixtures thereof.
  • Particularly preferred are usually the fatty acid cuttings obtainable from coconut oil or palm oil; In particular, the use of stearic acid is usually preferred.
  • the amount used is 0, 1 to 3 wt.%, Based on the total mean.
  • the amount is preferably 0.5-2% by weight, with amounts of 0.8-1% by weight being particularly advantageous.
  • cosmetic oils may additionally be included.
  • 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.
  • Suitable cosmetic oils include:
  • ester oils are understood as meaning the esters of - or polybasic C 6 - C 30 fatty acids with monohydric or polyhydric C 2 -C 30 fatty alcohols. Preference is given to the monoesters of fatty acids with monohydric alcohols having 2 to 24 carbon atoms.
  • fatty acid components used in the esters are caproic acid, caprylic acid, 2-ethylhexanoic acid, isononanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, Gadoleic acid, behenic acid and erucic acid and their technical mixtures.
  • fatty alcohol components in the ester oils are isopropyl alcohol, glycerol, caproic alcohol, capryl alcohol, 2-ethylhexyl alcohol, nonyl alcohol, isononyl 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, erucyl alcohol and brassidyl alcohol, and technical mixtures thereof.
  • ester oils may also be alkoxylated with ethylene oxide, propylene oxide or mixtures of ethylene oxide and propylene oxide.
  • the alkoxylation can be found both on the fatty alcohol part and on the fatty acid part and on both parts of the ester oils.
  • R 1 in this case represents a saturated or unsaturated, branched or linear, cyclic saturated cyclic unsaturated acyl radical having 6 to 30 carbon atoms,
  • AO is ethylene oxide, propylene oxide or butylene oxide
  • X is a number between 1 and 200, preferably 1 and 100, more preferably between 1 and 50, most preferably between 1 and 20, most preferably between 1 and 10 and most preferably between 1 and 5,
  • R 2 represents a saturated or unsaturated, branched or linear, cyclic saturated cyclic unsaturated alkyl, alkenyl, alkynyl, phenyl or benzyl radical having from 6 to 30 carbon atoms.
  • fatty acid moieties used as radical R1 in the esters are caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid , Arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures.
  • ester oils examples include benzyl alcohol, isopropyl alcohol, caproic alcohol, capryl alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, Li - nolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and their technical mixtures.
  • a particularly preferred ester oil according to the invention is obtainable, for example, under the INCI name PPG-3 benzyl ether myristate.
  • ester oils are to be understood as meaning:
  • Dicarboxylic acid esters such as di-n-butyl adipate, di- (2-ethylhexyl) adipate, di (2-ethylhexyl) succinate and diisotridecyl acelate and diol esters such as ethylene glycol dioleate, ethylene glycol diisotridecanoate, propylene glycol di (2-ethylhexanoate) , Propylene glycol di-isostearate, propylene glycol di-pelargonate, butanediol di-isostearate, neopentyl glycol dicaprylate, as well as
  • Fatty acid partial glycerides ie monoglycerides, diglycerides and their technical mixtures.
  • Typical examples are mono- and / or diglycerides based on caproic, caprylic, 2-ethylhexanoic, capric, lauric, isotridecanoic, myristic, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petro-, linoleic Arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures. Preference is given to using oleic acid monoglycerides.
  • oils natural oils.
  • oils are amaranth seed oil, apricot kernel oil, argan oil, avocado oil, babassu oil, cottonseed oil, borage seed oil, camelina oil, thistle oil, peanut oil, grapefruit seed oil, grapefruit seed oil, hemp oil, hazelnut oil, elderflower seed oil, currant oil.
  • triglyceride oils such as the liquid portions of beef tallow as well as synthetic triglyceride oils.
  • ester oils are isopropyl myristate, glycerin carbonate, dicaprylyl carbonate, isopropyl palmitate, PPG-3 benzyl ether myristates, cetyl oleate and oleyl erucate and mixtures of at least two of these ester oils. Most preferred are mixtures of ester oils when one of the ester oils is dicaprylyl carbonate or isopropyl myristate. Most preferred are mixtures of and with these two ester oils.
  • ester oils with the latter two oils are in a ratio of 10: 1 to 1: 1, preferably 5: 1 to 1: 1, more preferably 5 : 1 to 3: 1 with respect to the respective amounts of the ester oils.
  • the at least one ester oil is present in the compositions according to the invention in a total amount of from 0.01 to 7.5% by weight, preferably from 0.01 to 5.0% by weight, particularly preferably from 0.05 to 5.0% by weight, most preferably from 0.2 to 5.0% by weight, based on the weight of the composition of the invention.
  • the compounds are available as commercial products 1, 3-di- (2-ethyl-hexyl) -cyclohexane (Cetiol ® S), and di-n-octyl ether (Cetiol ® OE) may be preferred.
  • the total amount is 0.1-10% by weight, preferably 0.1-1.5% by weight and more preferably
  • Emulsifiers which can be used according to the invention are, for example
  • Sterols both from animal tissue (zoosterols, cholesterol, lanosterol) and from plant fats (phytosterols, ergosterol, stigmasterol, sitosterol) or from fungi and yeasts (mycosterols),
  • Phospholipids lecithins, phopshatidylcholines
  • Fatty acid esters of sugars and sugar alcohols such as sorbitol
  • Polyglycerols and polyglycerol derivatives such as polyglycerol poly-12-hydroxystearate
  • emulsifiers for the compositions according to the invention may be phospholipids.
  • phospholipid both natural and synthetic phospholipids are useful. Preferred are phospholipids on a natural basis.
  • phospholipids in particular compounds of the formula (phosphol-I) can be used.
  • y is an integer of 0 to 2
  • x is an integer of 1 to 3, provided that the sum of x and y is 3.
  • M is hydrogen, one equivalent of an alkali or alkaline earth metal cation, an ammonium cation or an alkyl radical having 1 to 4 carbon atoms which is optionally substituted by one or more hydroxy groups.
  • M is a sodium cation.
  • B in the formula (Phosphol-I) of the phospholipids to be used according to the invention is one equivalent of a physiologically tolerated anion.
  • anion e.g. Chloride, bromide, iodide, sulfate, perchlorate, tetrafluoroborate, tetraphenylborate and tetrachlorozincate.
  • the chloride ion e.g. Chloride, bromide, iodide, sulfate, perchlorate, tetrafluoroborate, tetraphenylborate and tetrachlorozincate.
  • the chloride ion e.g. Chloride, bromide, iodide, sulfate, perchlorate, tetrafluoroborate, tetraphenylborate and tetrachlorozincate.
  • the chloride ion e.g. Chloride, bromid
  • R in the formula (phosphol-1) is a radical of the formula (II) in which z is an integer from 1 to 4, in particular 3, and R and R 2 independently of one another are a C 1 - to C 4 -alkyl radical which is optionally substituted by one or more hydroxy group (s) or an acyl group.
  • A represents, according to the invention, one of the moieties -O-CH 2 -CH 2 -CH 2 -, -O-CH 2 -CH 2 - or -O-CH 2 -CHOH-CH 2 -, the moiety -O-CH 2 -CHOH-CH 2 - being particularly preferred ,
  • Particularly preferred saturated radicals R 3 are the radical of stearic acid and also the radicals of the mixture of the fatty acids which are obtained from coconut oil.
  • a particularly preferred unsaturated radical R 3 is the radical of linoleic acid.
  • Examples of the ci to C4-alkyl groups mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl groups are preferred alkyl groups. Very particular preference is given to methyl groups.
  • Very particularly preferred phospholipids of the formula (phosphol-1) are the substances known under the INCI names linoleneamidopropyl PG-dimonium chlorides phosphates, cocamidopropyl PG-dimonium chlorides phosphates and stearamidopropyl PG-dimonium chlorides phosphates. These are sold, for example, by the company Mona under the trade names Phospholipid EFA® , Phospholipid PTC® and Phospholipid SV® .
  • glycerol phospholipids which are obtained, for example, as lecithins or phosphatidylcholines, for example from egg yolk or plant seeds, in particular soybeans, are used as phospholipids according to the invention.
  • Phospholipids are in particular phosphoglycerides.
  • Glycero-phospholipids which are particularly suitable according to the invention are obtained from soybeans.
  • the phosphatidylcholines, phosphatidylethanolamines, phosphatidylserines and phosphatidylinositols and mixtures of these substances are particularly preferred.
  • the particularly preferred phosphatidylcholines have the formula (phosphol-II),
  • the radicals R and R 2 each independently of one another are an acyl group of fatty acids having a carbon number of 8 to 30 C atoms, preferably 10 to 24 and particularly preferably 12 to 22 C atoms.
  • the Fettchu rereste can be both saturated and mono- or polyunsaturated.
  • the saturated acyl radicals of C 12 -C 22 -fatty acids are preferred.
  • phosphatidylethanolamines which are preferred according to the invention are those of the formula (phospholyl) or (phosphol-11b),
  • radicals R and R 2 have the same meaning as shown for formula (phosphol-III). Particular preference is given to phosphatidylethanolamines in which R and R 2 independently of one another represent saturated acyl radicals of fatty acids having 16 or 18 carbon atoms, in particular a palmitoyl or stearoyl radical.
  • phosphatidylserines preferred according to the invention are those of the structural formula (IIIa) or (IIIb)
  • R and R 2 have the same meaning as shown for formula (phosphol-II).
  • Particularly preferred are phosphatidylserines in which R and R 2 independently represent saturated acyl radicals of fatty acids having 16 or 18 carbon atoms, in particular a palmitoyl or stearoyl radical.
  • the phosphatidylinositols preferred according to the invention have the structural formula (IVa) or (IVb)
  • R and R 2 have the same meaning as set forth for formula (phosphol-II).
  • R are acyl radicals of palmitic acid, stearic acid and arachidic acid preferred; particularly preferred is a stearic acid acyl radical.
  • R 2 is particularly preferably a linear saturated C 2- fatty acid acyl radical (arachoyl radical).
  • the glycerophospholipids used according to the invention have an iodine value of not more than 10, preferably of not more than 5.
  • a preferred phospholipid according to the invention is commercially available under the name Emulmetik® 100 (BASF).
  • the phospholipids according to the invention are present in the compositions in concentrations of 0.1% by weight to 7.5% by weight, preferably from 0.1% by weight to 5% by weight, very particularly preferably in amounts of 0.1% by weight .% Up to 3 wt.% And most preferably in amounts of 0, 1 to 1, 5 wt.% Contained.
  • 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.
  • the cationic polymers may be homopolymers or copolymers wherein the quaternary nitrogen groups are contained either in the polymer chain or preferably as a substituent on one or more of the monomers.
  • the ammonium group-containing monomers may be copolymerized with non-cationic monomers.
  • Suitable cationic monomers are unsaturated, free-radically polymerizable compounds which carry at least one cationic group, in particular ammonium-substituted vinyl monomers such as, for example, trialkylmethacryloxyalkylammonium, trialkylacryloxyalkylammonium, dialkyldiallylammonium and quaternary vinylammonium monomers having cyclic, cationic nitrogen-containing groups such as pyridinium, imidazolium or quaternary Pyrrolidones, eg Alkylvinylimidazolium, alkylvinylpyridinium, or alkylvinylpyrrolidone salts.
  • the alkyl groups of these monomers are preferably lower alkyl groups such as C1 to C7 alkyl groups, more preferably C1 to C3 alkyl groups.
  • the ammonium group-containing monomers may be copolymerized with non-cationic monomers.
  • Suitable comonomers are, for example, acrylamide, methacrylamide; Alkyl and dialkylacrylamide, alkyl and dialkylmethacrylamide, alkylacrylate, alkylmethacrylate, vinylcaprolactone, vinylcaprolactam, vinylpyrrolidone, vinylester, e.g. Vinyl acetate, vinyl alcohol, propylene glycol or ethylene glycol, wherein the alkyl groups of these monomers are preferably C 1 - to C 7 -alkyl groups, particularly preferably C 1 - to C 3 -alkyl groups.
  • Suitable polymers having quaternary amine groups are the polymers described in the CTFA Cosmetic Ingredient Dictionary under the names Polyquaternium, such as methylvinylimidazolium chloride / vinylpyrrolidone copolymer (Polyquaternium-16) or quaternized vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer (Polyquaternium-11).
  • cationic polymers for example vinylpyrrolidone / dimethylaminoethyl copolymer available under the trade names Gafquat ® 755 N and Gafquat ® 734, United States is marketed by Gaf Co. and of which the Gafquat ® 734 is particularly preferred suitable.
  • cationic polymers are, for example, those from BASF, Germany under the trade name Luviquat.RTM ® HM 550 displaced copolymer of polyvinylpyrrolidone and imidazoliminemethochloride that ® by Calgon / USA under the trade name Merquat Plus 3300 sold ter- polymer of dimethyldiallylammonium chloride, sodium acrylate and acrylamide and sold by the company ISP under the trade name Gafquat ® HS 100 vinylpyrrolidone / Methacrylamidopropyltrimethylammonium chloride copolymer.
  • R -H or -CH 3 , R 2 , R 3 and R 4 are independently selected from C 1-4-
  • Alkyl, alkenyl or hydroxyalkyl groups, m 1, 2, 3 or 4, n is a natural number and
  • Polymers are those inventively preferred for which at least one of the following
  • R is a methyl group
  • R 2 , R 3 and R 4 are methyl groups
  • m is 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.
  • Suitable cationic guar derivatives are marketed under the trade name Jaguar ® and have the INCI name guar hydroxypropyltrimonium chloride. Further particularly suitable cationic guar derivatives are also used by the company. Hercules under the name N-Hance ® commercially. Other cationic guar derivatives are marketed by the company. BASF under the name Cosmedia® ®. A preferred cationic guar derivative is the commercial product AquaCat® ® from. Hercules.
  • a suitable chitosan is sold, for example, by Kyowa Oil & Fat, Japan under the trade name Flonac ®.
  • a preferred chitosan is carboxylate Chitosoniumpyrrolidon- that is, for example, sold under the name Kytamer ® PC by Amerchol, USA.
  • Further chitosan derivatives are Hydagen® ® CMF, Hydagen® ® HCMF and Chitolam ® NB / 101 freely available under the trade names in the trade.
  • honey for example the commercial product Honeyquat ® 50,
  • polymeric dimethyldiallylammonium salts and their copolymers with esters and amides of acrylic acid and methacrylic acid Under the names Merquat ® 100 (poly (dimethyl diallyl ammonium chloride)) and Merquat ® 550 (dimethyldiallylammonium chloride-acrylamide copolymer), commercially available products are examples of such cationic polymers, vinyl pyrrolidone-vinyl imidazolium methochloride copolymers, as are sold under the names Luviquat ® FC 370, FC 550, FC 905 and HM 552 are offered,
  • Vinylpyrrolidone-vinylcaprolactam-acrylate terpolymers such as those offered with acrylic acid esters and acrylamides as the third monomer building commercially, for example, under the name Aquaflex ® SF 40.
  • 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.
  • cationized protein hydrolysates are to be counted among the cationic polymers, wherein the underlying protein hydrolyzate from the animal, for example from collagen, milk or keratin, from the plant, for example from wheat, corn, rice, potatoes, soy or almonds, marine life forms, for example from fish collagen or algae, or biotechnologically derived protein hydrolysates.
  • the cationic protein hydrolysates and derivatives according to the invention those mentioned under the INCI names in the "International Cosmetic Ingredient Dictionary and Handbook", (seventh edition 1997, The Cosmetic, Toiletry and Fragrance Association 1 101 17 th Street, NW, Suite 300, Washington, DC 20036-4702) and commercially available products.
  • the additional cationic polymers are preferably contained in the compositions according to the invention in amounts of from 0.01 to 10% by weight, based on the total agent. Levels of 0.05 to 5 wt .-% are particularly preferred.
  • amphoteric polymers can be used as polymers.
  • the term "amphoteric polymers” encompasses both those polymers which contain in the molecule both free amino groups and free -COOH or SCbH groups and are capable of forming internal salts, as well as zwitterionic polymers which contain quaternary ammonium groups and -COO or SCb ' groups, and those polymers comprising -COOH or SOsH groups and quaternary ammonium groups.
  • Amphoteric and / or cationic polymers preferred according to the invention are those polymers in which a cationic group is derived from at least one of the following monomers: (i) monomers having quaternary ammonium groups of the general formula (monol),
  • R and R 2 independently of one another represent hydrogen or a methyl group and R 3 , R 4 and R 5 independently of one another represent alkyl groups having 1 to 4 carbon atoms, Z denotes an NH group or an oxygen atom, n denotes an integer of 2 to 5 and A () is the anion of an organic or inorganic acid,
  • R 6 and R 7 independently of one another represent a (C 1 to C 4) -alkyl group, in particular for a methyl group and
  • R 8 -CH CR 9 -COOH (mono 3)
  • R 8 and R 9 are independently hydrogen or methyl groups.
  • acrylic acid is preferably used as the monomer (ii) for the polymers mentioned.
  • amphoteric polymers are copolymers of at least one monomer (monol) or (mono 2) with the monomer (mono 3), in particular copolymers of the monomers (mono 2) and (mono 3).
  • amphoteric polymers are copolymers of diallyl dimethyl ammonium chloride and acrylic acid. These copolymers are sold under the INCI name Polyquaternium-22, among others, with the trade name Merquat ® 280 (Nalco).
  • amphoteric polymers according to the invention may additionally contain one monomer (mono 4).
  • R 0 and R independently of one another are hydrogen or methyl groups and R 2 is a hydrogen atom or a (C 1 to C 8) -alkyl group.
  • Amphoteric polymers based on a comonomer (Mono4) which are very particularly preferably used according to the invention are terpolymers of diallyldimethylammonium chloride, acrylamide and acrylic acid. These copolymers are marketed ® under the INCI name Polyquaternium-39, among others, with the trade name Merquat Plus 3330 (Nalco).
  • amphoteric polymers can generally 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.
  • amphoteric polymers are contained in the agents according to the invention preferably in amounts of 0.01 to 10 wt .-%, based on the total agent. Amounts of 0.01 to 5 wt .-% are particularly preferred.
  • the anionic polymers 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 can be completely or partly example, be 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 the sulfonic acid group to be wholly or partly present as sodium, potassium, ammonium, mono- or triethanolammonium salt ,
  • the homopolymer of 2-acrylamido-2-methylpropansulfon 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. Such a polymer is contained in the commercial product Sepigel ® 305 from SEPPIC.
  • Simulgel ® 600 as a compound with isohexadecane and polysorbate-80 Natriumacryloyldimethyltaurat copolymers have proved to be particularly effective according to the invention.
  • anionic homopolymers are uncrosslinked and crosslinked polyacrylic acids. Allyl ethers of pentaerythritol, of sucrose and of 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 polymers are preferably contained in the agents according to the invention in amounts of from 0.05 to 10% by weight, based on the total agent. Amounts of 0.1 to 5 wt .-% are particularly preferred.
  • the agents according to the invention may 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 Vinylpyrro- lidon / vinyl acetate copolymers, are also preferred nonionic polymers.
  • Cellulose ethers such as hydroxypropyl cellulose, hydroxyethyl cellulose and hydroxypropylcellulose Methylhy- as for example under the trademark Culminal® ® and Benecel ® (Aqualon) and Natrosol ® grades (Hercules) are sold.
  • Starch and its derivatives in particular starch, such as Structure XL ® (National Starch), a multifunctional, salt-tolerant starch;
  • the nonionic polymers are preferably contained in the compositions according to the invention in amounts of from 0.05 to 10% by weight, based on the total agent. Amounts of 0, 1 to 5 wt .-% are particularly preferred.
  • the preparations used contain a plurality, in particular two, different polymers of the same charge and / or in each case an ionic and a amphoteric and / or nonionic polymer.
  • the polymers (P) are preferably present in the compositions used according to the invention in amounts of from 0.01 to 30% by weight, based on the total composition. Amounts of from 0.01 to 25, in particular from 0.01 to 15 wt .-%, are particularly preferred.
  • the agents according to the invention preferably contain at least one silicone polymer selected from the group of dimethiconols and / or the group of amino-functional silicones and / or the group of dimethicones and / or the group of cyclomethicones. These ingredients are described below.
  • the dimethicones according to the invention can be both linear and branched as well as cyclic or cyclic and branched.
  • Linear dimethicones can be represented by the following structural formula (Sil):
  • Branched dimethicones can be represented by the structural formula (Sil 1):
  • the radicals R and R 2 are each independently hydrogen, a methyl radical, a C 2 to C 30 linear, saturated or unsaturated hydrocarbon radical, a phenyl radical and / or an aryl radical.
  • the numbers x, y and z are integers and each run independently from 0 to 50,000.
  • the molecular weights of the dimethicones are between 1000 D and 10,000,000 D.
  • the viscosities are between 100 and 10,000,000 cPs measured at 25 ° C. with the aid of a glass capillary viscometer according to the Dow Corning Corporate Test Method CTM 0004 of 20 July 1970.
  • Preferred viscosities are between 1,000 and 5,000,000 CPs, very special preferred viscosities are between 10,000 and 3,000,000 cPs.
  • the most preferred range is between 50,000 and 2,000,000 cps. Most preferred are viscosities around the range of about 60,000 cps.
  • Particularly preferred cosmetic or dermatological preparations according to the invention are characterized in that they contain at least one silicone of the formula (Sil .2)
  • 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.
  • the dimethicones (Sil) are present in the compositions according to the invention in amounts of from 0.01 to 10% by weight, preferably from 0.01 to 8% by weight, particularly preferably from 0.1 to 7.5% by weight and in particular from 0.1 to 5 wt.% Based on the total composition.
  • Particularly preferred agents according to the invention contain one or more amino-functional silicones.
  • Such silicones may e.g. by the formula (Si-2)
  • R is a hydrocarbon or a hydrocarbon radical having from 1 to about 6
  • Q is a polar radical of the general formula -R HZ
  • R is a divalent linking group bonded to hydrogen and the radical Z composed of carbon and hydrogen atoms, carbon, hydrogen and oxygen atoms or carbon, hydrogen and nitrogen atoms, and
  • Z is an organic, amino-functional group containing at least one amino-functional group
  • b takes values in the range of about 1 to about 3,
  • a + b is less than or equal to 3
  • c is a number in the range of about 1 to about 3, 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 in the range of from about 20 to about 10,000, preferably from about 125 to about
  • M is a suitable silicone end group as known in the art
  • Z is according to formula (Si-2) an organic, amino-functional radical containing at least one functional amino group.
  • a possible formula for said Z is NH (CH 2) z NH 2, where z is an integer greater than or equal to 1.
  • Another possible formula for said Z is -NH (CH 2) z (CH 2) zzNH, wherein both z and zz independently of one another are an integer greater than or equal to 1, this structure comprising diamino ring structures, such as piperazinyl.
  • Said Z is most preferably a -NHCH 2 CH 2 NH 2 radical.
  • Z is -N (CH 2) z (CH 2) zzNX 2 or -NX 2, wherein each X of X 2 is independently selected from the group consisting of hydrogen and alkyl groups of 1 to 12 carbon atoms, and zz is 0.
  • Q according to formula (Si-2) is most preferably a polar amino-functional radical of formula - CH 2 CH 2 CH 2 NHCH 2 CH 2 NH 2.
  • ⁇ assumes values in the range of 0 to 2
  • b takes values in the range of 2 to 3
  • a + b is less than or equal to 3
  • c is a number in the range of 1 to 3.
  • cationic silicone oils such as, for example, the commercially available products Dow Corning (DC) 929 Emulsion, DC 2-2078, DC 5-71 13, SM-2059 (General Electric) and SLM-55067 (Wacker).
  • Particularly preferred agents according to the invention are characterized in that they contain at least one amino-functional silicone of the formula (Si 3-a)
  • n and n are numbers whose sum (m + n) is between 1 and 2000, preferably between 50 and 150, where n preferably values of 0 to 1999 and in particular of 49 to 149 and m preferably values of 1 to 2000 , in particular from 1 to 10 assumes.
  • silicones are referred to as trimethylsilylamodimethicones according to the INCI declaration and are available, for example, under the name Q2-7224 (manufacturer: Dow Corning, a stabilized trimethylsilylamodimethicone).
  • compositions according to the invention which contain at least one amino-functional silicone of the formula (Si-3b)
  • R is -OH, (optionally ethoxylated and / or propoxylated) (C1 to C20) -
  • R ' represents -OH, a (C1 to C2o) alkoxy group or a -CH3 group and
  • n1 and n2 are numbers whose sum (m + n1 + n2) is between 1 and 2000, preferably between 50 and 150, the sum (n1 + n2) preferably having values from 0 to 1999 and in particular from 49 to 149 and m preferably values of
  • silicones are according to the INCI declaration as Amodimethicone, or as a functionalized Amodimethicone, such as bis (C13-15 alkoxy) PG Amodimethicone (for example, as a commercial product: DC 8500 Dow Corning available), Trideceth-9 PG-Amodimethicone (For example, available as a commercial product Silcare Silicone SEA Clariant).
  • Suitable diquaternary silicones are selected from compounds of the general formula (Si3c) [RR 2 R 3 N + - A - SiR 7 R 8 - (O-SiR 9 R 0) n - O - SiR R 12 - A - N + R 4 R 5 R 6 ] 2X " (Si 3c)
  • R 1 to R 6 independently of one another are C 1 to C 22 -alkyl radicals which may contain hydroxyl groups and where preferably at least one of the radicals has at least 8 C atoms and the remaining radicals have 1 to 4 C atoms,
  • radicals R 7 to R 12 independently of one another, are identical or different and are C 1 - to C 10 -alkyl or phenyl,
  • A is a divalent organic compound group
  • n is a number from 0 to 200, preferably from 10 to 120, more preferably from 10 to 40, and X "is an anion.
  • the divalent linking group is preferably a C1 to C12 alkylene or alkoxyalkylene group which may be substituted with one or more hydroxyl groups. Particularly preferred is the group - (CH 2 ) 3-0-CH 2 -CH (OH) -CH 2 -.
  • the anion X " may be a halide ion, an acetate, an organic carboxylate or a compound of the general formula RSO3 " , wherein R has the meaning of C1 to C4 alkyl radicals.
  • a preferred diquaternary silicone has the general formula (Si3d)
  • A is the group - (CH 2 ) 3 - O - CH 2 - CH (OH) - CH 2 -,
  • R is an alkyl radical having at least 8 C atoms and n is a number from 10 to 120.
  • Suitable silicone polymers having two terminal quaternary ammonium groups are among
  • Cosmetic or dermatological preparations preferred according to the invention are characterized in that, based on their weight, they contain 0.01 to 10% by weight, preferably 0.01 to 8
  • Wt.% Particularly preferably 0, 1 to 7.5 wt.% And in particular 0.2 to 5 wt.% Amino-functional (s) silicone (s) and / or diquaternary silicone.
  • the compositions according to the invention may comprise at least one polyammonium-polysiloxane compound.
  • the polyammonium-polysiloxane compounds can be obtained, for example, under the trade name Baysilone® from GE Bayer Silicones.
  • Baysilone TP 391 1, SME 253 and SFE 839 are preferred.
  • Very particular preference is given to the use of Baysilone TP 391 1 as the active component of the compositions according to the invention.
  • the polyammonium-polysiloxane compounds are present in a total amount of from 0.01 to 10% by weight, preferably from 0.01 to 7.5, particularly preferably from 0.01 to 5.0% by weight, very particularly preferably from 0 , 05 to 2.5 wt .-%, each with respect to the total composition included.
  • EP 1887024 A1 describes novel cationic amino-functional silicones which in particular enhance the gloss in agents for the care of surfaces, for example human Hair, improve.
  • These cationic silicone polymers are characterized in that they have a silicone backbone and at least one polyether part and furthermore at least one part with an ammonium structure.
  • Examples of the preferred cationic silicone polymers for the purposes of the present invention are, in addition to the compounds of the aforementioned EP 1887024 A1, in particular the compounds with the INCI designations: Silicone Quaternium-1, Silicone Quaternium-2, Silicone Quaternium-3, Silicone Quaternium-4 Silicone Quaternium-5, Silicone Quaternium-6, Silicone Quaternium-7, Silicone Quaternium-8, Silicone Quaternium-9, Silicone Quaternium-10, Silicone Quaternium-1 1, Silicone Quaternium-12, Silicone Quaternium-15, Silicone Quaternium 16, Silicone Quaternium-17, Silicone Quaternium-18, Silicone Quaternium-20, Silicone Quaternium-21, Silicone Quaternium-22 as well as Silicone Quaternium-2 Panthenol Succinate and Silicone Quaternium-16 / Glycidyl Dimethicone Crosspolymer. Most preferred is Silicone Quaternium-22. This raw material is sold
  • the abovementioned cationic amino-functional silicone polymers are present in the compositions according to the invention in amounts of from 0.01 to 20% by weight, preferably in amounts of from 0.05 to 10% by weight and very particularly preferably in amounts of from 0.1 to 7.5% by weight .% contain.
  • the very best results are obtained with amounts of 0, 1 to 5 wt.%, In each case based on the total composition of the respective agent.
  • the cyclic dimethicones designated as cyclomethicones according to INCI are also preferably used according to the invention.
  • cosmetic or dermatological preparations according to the invention are preferred which contain at least one silicone of the formula (Si-4)
  • x is a number from 3 to 200, preferably from 3 to 10, more preferably from 3 to 7 and in particular 3, 4, 5 or 6 stands.
  • Agents which are likewise preferred according to the invention are characterized in that they contain at least one silicone of the formula (Si-5)
  • R is identical or different radicals from the group -H, -phenyl, -benzyl, -CH 2 -CH (CH 3 ) Ph, the Ci-20-alkyl radicals, preferably -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CH (CH 3 ) 2 , -CH 2 CH 2 CH 2 H 3, -CH 2 CH (CH 3 ) 2, -CH (CH 3 ) CH 2 CH 3 , -C (CH 3 ) 3 , x and y represent a number from 0 to 200, preferably from 0 to 10, more preferably from 0 to 7 and especially 0, 1, 2, 3, 4, 5 or 6, and n is a number from 0 to 10, preferably from 1 to 8 and especially for 2, 3, 4, 5, 6 stands.
  • silicones in addition to the dimethicones, dimethiconols, amodimethicones and / or cyclo- Methiconen water-soluble silicones may be included in the compositions of the invention.
  • Corresponding hydrophilic silicones are selected, for example, from the compounds of the formulas (Si-6) and / or (Si-7).
  • Particularly preferred water-soluble silicone-based surfactants are selected from the group of dimethicone copolyols which are preferably alkoxylated, in particular polyethoxylated or polypropoxylated.
  • Dimethicone copolyols are understood according to the invention as meaning preferably polyoxyalkylene-modified dimethylpolysiloxanes of the general formulas (Si-6) or (Si-7):
  • radical R represents a hydrogen atom, an alkyl group having 1 to 12 C atoms, an alkoxy group having 1 to 12 C atoms or a hydroxyl group
  • radicals R 'and R denote alkyl groups having 1 to 12 C atoms
  • x is an integer from 1 to 100, preferably from 20 to 30
  • y is an integer from 1 to 20, preferably from 2 to 10
  • a and b are integers from 0 to 50, preferably from 10 to 30 ,
  • dimethicone copolyols according to the invention are, for example, the products sold commercially under the trade names SILWET (Union Carbide Corporation) and DOW CORNING.
  • Particularly preferred dimethicone copolyols according to the invention are Dow Corning 190 and Dow Corning 193.
  • the dimethicone copolyols are present in the compositions according to the invention in amounts of from 0.01 to 10% by weight, preferably from 0.01 to 8% by weight, particularly preferably from 0.1 to 7.5% by weight and in particular from 0.1 to 5% by weight. % of dimethicone copolyol based on the composition.
  • the dimethiconols preferred according to the invention can be both linear and branched as well as cyclic or cyclic and branched.
  • Linear dimethiconols can be represented by the following structural formula (Si8-I):
  • Branched dimethiconols can be represented by the structural formula (Si8 - II):
  • the radicals R and R 2 are each independently hydrogen, a methyl radical, a C 2 to C 30 linear, saturated or unsaturated hydrocarbon radical, a phenyl radical and / or an aryl radical.
  • the numbers x, y and z are integers and each run independently from 0 to 50,000.
  • the molecular weights of the dimethiconols are between 1000 D and 10,000,000 D.
  • the viscosities are between 100 and 10,000,000 cPs measured at 25 ° C. with the aid of a glass capillary viscometer according to the Dow Corning Corporate Test Method CTM 0004 of 20 July 1970.
  • Preferred viscosities are between 1,000 and 5,000,000 cPs, most preferred viscosities are between 10,000 and 3,000,000 cps. The most preferred range is between 50,000 and 2,000,000 cps.
  • Examples of such products include the following commercial products: Dow Corning 1 -1254 Fluid, Dow Coming 2-9023 Fluid, Dow Corning 2-9026 Fluid, Abil OSW 5 (Degussa Care Specialties), Dow Corning 1401 Fluid, Dow Corning 1403 Fluid Dow Corning 1501 Fluid, Dow Corning 1784 HVF Emulsion, Dow Corning 9546 Silicone Elastomer Blend, SM555, SM2725, SM2765, SM2785 (all four aforementioned GE Silicones), Wacker-Belsil CM 1000, Wacker-Belsil CM 3092, Wacker-Belsil CM 5040, Wacker-Belsil DM 3096, Wacker-Belsil DM 31 12 VP, Wacker-Belsil DM 8005 VP, Wacker-Belsil DM 60081 VP (all Wacker-Chemie GmbH mentioned above).
  • the dimethiconols (Si8) are present in the compositions according to the invention in amounts of from 0.01 to 10% by weight, preferably from 0.01 to 8% by weight, particularly preferably from 0.1 to 7.5% by weight and in particular from 0.1 to 5% by weight of dimethiconol based on the composition.
  • compositions according to the invention with the combination of active substances according to the invention are protein hydrolysates and / or their derivatives (P).
  • protein hydrolysates of both vegetable and animal or marine or synthetic origin can be used.
  • Animal protein hydrolysates are, for example, elastin, collagen, keratin, silk and milk protein hydrolysates, which may also be present in the form of salts.
  • Further preferred vegetable protein hydrolysates according to the invention are, for example, soybean, almond, pea, moringa, potato and wheat protein hydrolysates. Such products are, for example, under the trademarks Gluadin ® (BASF), diamine ® (Diamalt) ® (Inolex), Hydrosoy ® (Croda), hydro Lupine ® (Croda), hydro Sesame ® (Croda), Hydro tritium ® (Croda), Crotein ® (Croda) and Puricare ® LS 9658 from Laboratoires Serobi unanimouss.
  • Further preferred protein hydrolysates according to the invention are of maritime origin. These include, for example, collagen hydrolyzates of fish or algae as well as protein hydrolysates of mussels or pearl hydrolyzates. Examples of pearl extracts according to the invention are the commercial products Pearl Protein Extract BG ® or Crodarom ® Pearl.
  • the protein hydrolysates (P) are present in the compositions in concentrations of 0.001% by weight to 20% by weight, preferably from 0.05% by weight to 15% by weight and most preferably in amounts of 0.05% by weight. up to 5% by weight.
  • compositions of the invention can be further increased by a 2-pyrrolidi- ⁇ -5-carboxylic acid and its derivatives (J).
  • the sodium salt is most preferred.
  • the amounts used in the inventive compositions are 0.05 to 10 wt.%, Based on the total agent, particularly preferably 0, 1 to 5, and in particular 0.1 to 3 wt.%.
  • compositions according to the invention with the active ingredient combination according to the invention are vitamins, provitamins or vitamin precursors.
  • Vitamins, pro-vitamins and vitamin precursors are particularly preferred, which are assigned to the groups A, B, C, E, F and H.
  • vitamin A includes retinol (vitamin Ai) and 3,4-didehydroretinol (vitamin A2).
  • the ß-carotene is the provitamin of retinol.
  • vitamin A component according to the invention for example, vitamin A acid and its esters, vitamin A aldehyde and vitamin A alcohol and its esters such as the palmitate and the acetate into consideration.
  • the agents according to the invention preferably contain the vitamin A component in amounts of 0.05-1% by weight, based on the total preparation.
  • the vitamin B group or the vitamin B complex include u. a .:
  • Vitamin B1 (thiamine)
  • Vitamin B2 (riboflavin)
  • Vitamin B3 the compounds nicotinic acid and nicotinamide (niacinamide) are often performed.
  • Preferred according to the invention is the nicotinic acid amide which is contained in the agents used according to the invention preferably in amounts of from 0.05 to 1% by weight, based on the total agent.
  • Vitamin Bs pantothenic acid, panthenol and pantolactone.
  • Panthenol and / or pantolactone are preferably used in the context of this group.
  • Derivatives of panthenol which can be used according to the invention are, in particular, the esters and ethers of panthenol and also cationically derivatized panthenols.
  • Individual representatives are, for example, panthenol triacetate, panthenol monoethyl ether and its monoacetate, and cationic panthenol derivatives.
  • Pantothenic acid is preferably used as a derivative in the form of the more stable calcium salts and sodium salts (Ca-pantothenate, Na-pantothenate) in the present invention.
  • Vitamin ⁇ (pyridoxine and pyridoxamine and pyridoxal).
  • the stated compounds of the vitamin B type, in particular vitamin B3, Bs and ⁇ , are preferably present in the agents according to the invention in amounts of 0.05-10% by weight, based on the total agent. Amounts of 0, 1-5 wt .-% are particularly preferred.
  • Vitamin C (ascorbic acid). Vitamin C is used in the inventive compositions preferably in amounts of 0, 1 to 3 wt .-%, based on the total agent. Use in the form of palmitic acid ester, glucosides or phosphates may be preferred. The use in combination with tocopherols may also be preferred.
  • Vitamin E tocopherols, especially ⁇ -tocopherol.
  • Tocopherol and its derivatives which include in particular the esters such as the acetate, the nicotinate, the phosphate and the succinate, are preferably present in the agents according to the invention in amounts of 0.05-1% by weight, based on the total agent.
  • Vitamin F is usually understood as meaning essential fatty acids, in particular linoleic acid, linolenic acid and arachidonic acid.
  • Vitamin H is the compound (3aS, 4S, 6aR) -2-oxohexahydrothienol [3,4-d] -imidazole-4-valeric acid, for which, however, the trivial name biotin has meanwhile prevailed.
  • Biotin is preferably present in the compositions according to the invention in amounts of from 0.0001 to 1.0% by weight, in particular in amounts of from 0.001 to 0.01% by weight.
  • compositions according to the invention preferably contain vitamins, provitamins and vitamin precursors from groups A, B, E and H. Panthenol, pantolactone, pyridoxine and its derivatives as well as nicotinic acid amide and biotin are particularly preferred.
  • a particularly preferred group of ingredients in the cosmetic compositions according to the invention are the betaines mentioned below: carnitine, carnitine tartrate, carnitine magnesium citrate, acetyl carnitine, betalaines, 1,1-dimethyl-proline, choline, choline chloride, choline bi- tartrate, choline dihydrogen citrate and those described in US Pat Literature referred to as betaine compound ⁇ , ⁇ , ⁇ trimethylglycine.
  • Carnitine, histidine, choline and betaine are preferably used.
  • the active ingredient used is L-carnitine tartrate.
  • taurine is exclusively 2-aminoethanesulfonic acid and a derivative is understood to mean the explicitly mentioned derivatives of taurine.
  • Derivatives of taurine include N-monomethyltaurine, ⁇ , ⁇ -dimethyltaurine, tauryllysylate, taurine tartrate, taurine ornithithate, lysyl taurine and ornithyl taurine.
  • Further taurine derivatives for the purposes of the present invention are taurocholic acid and hypotaurine.
  • agents according to the invention which - based on their weight - 0.0001 to 10.0 wt .-%, preferably 0.0005 to 5.0 wt .-%, particularly preferably 0.001 to 2.0 wt .-% and In particular, 0.001 to 1, 0 wt .-% taurine and / or a derivative of taurine included.
  • the compositions according to the invention contain biochinones.
  • suitable biochinones are understood as meaning one or more ubiquinone (s) and / or plastoquinone (s).
  • the inventions Ubiquinones which are preferred according to the invention have the following formula:
  • Coenzyme Q-10 is most preferred.
  • compositions of the invention contain purine and / or purine derivatives in narrower ranges.
  • preferred cosmetic compositions according to the invention are characterized in that they contain, based on their weight, from 0.001 to 2.5% by weight, preferably from 0.0025 to 1% by weight, particularly preferably from 0.005 to 0.5% by weight and in particular from 0.01 to 0.1% by weight of purine (s) and / or purine derivative (s).
  • Cosmetic agents preferred according to the invention are characterized in that they contain purine, adenine, guanine, uric acid, hypoxanthine, 6-purinethiol, 6-thioguanine, xanthine, caffeine, theobromine or theophylline. In hair cosmetic preparations, caffeine is most preferred.
  • the cosmetic agent contains ectoine ((S) -2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid.
  • agents which, based on their weight, are from 0.00001 to 10.0% by weight, preferably from 0.0001 to 5.0% by weight and in particular from 0.001 to 3% by weight, of the active compounds from A group formed by carnitine, taurine, coenzyme Q-10, ectoine, a B-series vitamin, a purine and its derivatives or physiologically acceptable salts.
  • the agents according to the invention should additionally contain at least one UV light protection filter.
  • UVB filters can be oil-soluble or water-soluble.
  • oil-soluble substances are e.g. to call:
  • 4-aminobenzoic acid derivatives preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and 4- (dimethylamino) benzoic acid amyl ester;
  • Esters of cinnamic acid preferably 4-methoxycinnamic acid 2-ethylhexyl ester, 4-methoxycinnamic acid propyl ester, 4-methoxycinnamic acid isoamyl ester, 2-cyano-3-phenylcinnamic acid 2-ethylhexyl ester (octocrylene);
  • Esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate, homomenthyl salicylate;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • Esters of benzalmalonic acid preferably di-2-ethylhexyl 4-methoxybenzmalonate
  • Triazine derivatives e.g. 2,4,6-Trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1, 3,5-triazine and
  • Suitable water-soluble substances are:
  • Sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts;
  • Sulfonic acid derivatives of the 3-benzylidene camphor e.g. 4- (2-oxo-3-bomylidenemethyl) benzene sulfonic acid and 2-methyl-5- (2-oxo-3-bomylidene) sulfonic acid and salts thereof.
  • UV-A filter in particular derivatives of benzoylmethane come into question, such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione or 1-phenyl-3 (4'-isopropylphenyl) -propane-1,3-dione.
  • the UV-A and UV-B filters can also be used in mixtures.
  • insoluble pigments in particular finely dispersed metal oxides or salts, such as titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates, in particular talc, furthermore barium sulfate and zinc stearate, are suitable for this purpose.
  • the particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They may have a spherical shape, but it is also possible to use those particles which have an ellipsoidal or otherwise deviating shape from the spherical shape.
  • plant extracts (L) in the compositions according to the invention gives rise to further advantages.
  • the plant extracts can be used according to the invention both in pure and in diluted form. If they are used in diluted form, they usually contain about 2 to 80 wt .-% of active substance and as a solvent used in their extraction agent or extractant mixture.
  • the cosmetic agents may contain further active ingredients, auxiliaries and additives, such as, for example, acidulants such as citric acid and lactic acid, dimethylisosorbide and cyclodextrins, dyes for staining the agent, anti-dandruff agents such as Piroctone Olamine, zinc Omadine and climbazole, complexing agents such as EDTA, NTA, ⁇ -alaninediacetic acid and phosphonic acids, opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers, pearlescing agents such as ethylene glycol mono- and distearate and PEG-3-distearate, pigments, stabilizers for hydrogen peroxide and other oxidants, blowing agents such as Propane-butane mixtures, N2O, dimethyl ether, CO2 and air, antioxidants, perfume oils, fragrances and fragrances.
  • auxiliaries and additives such as, for example, acidulants such as cit
  • compositions according to the invention are of particular importance.
  • a further subject of the invention is the use of a composition according to the invention or preferred according to the invention for improving the resistance of the surface of keratinic fibers to physical damage.
  • Physical damage is understood according to the invention to be the action of UV light, the action of heat during blow-drying, mechanical effects during combing and brushing of the hair.
  • Another object of the present invention is the use of a composition according to the invention or preferred according to the invention for improving the washout stability of the color of dyed keratinic fibers.
  • Another subject of the invention is a hair treatment process in which a cosmetic composition according to claim 1 is applied to the hair and is rinsed by the hair after a contact time.
  • the exposure time is preferably 5 seconds to 100 minutes, more preferably 1 to 45 minutes, and most preferably 2 to 30 minutes.
  • a cosmetic composition according to claim 1 is applied to the hair and remains there.
  • “remaining on the hair” means that the agent is not rinsed out of the hair immediately after it has been used, but in this case the agent remains on the hair for more than 100 minutes until the next hair wash.
  • hair conditioner formulation according to the invention was provided using known preparation methods:
  • the following two hair conditioner formulations (according to the invention, comparative formulation) were applied to 5 persons in the half-side test and assessed their application properties by 2 trained hairdressers.
  • the hair of the test persons was first washed with a shampoo. Subsequently, the main hair was parted: on one half of the head, the hair was treated with the conditioner according to the invention, on the other half of the head, the hair was treated with the non-inventive conditioner.
  • hair conditioner according to the invention
  • the trained hairdressers came to the following reviews:
  • the assessment values are from a scale of zero to 1. Values below 0.25 represent statistically insignificant differences. Values of 0.25 to 0.5 represent a small improvement over the comparison recipe. Values above 0.5 represent a statistically significant improvement over the comparison formula.
  • the formulation according to the invention helped the treated hair to significantly better wet combability.
  • Cetearyl alcohol (31, 5% by weight)

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Abstract

La présente invention concerne des compositions permettant de traiter des fibres kératiniques, notamment des cheveux humains, qui améliorent nettement les caractéristiques de conditionnement, ainsi que la brillance et la douceur au toucher de fibres kératiniques, notamment de cheveux humains, par rapport aux compositions connues de l'état de la technique. Les compositions selon l'invention contiennent comme composants principaux au moins un tensioactif cationique sélectionné et au moins un dérivé d'acide pyroglutamique sélectionné.
PCT/EP2014/076858 2013-12-20 2014-12-08 Agents de conditionnement pour fibres kératiniques comprenant un dérivé d'acide pyroglutamique WO2015091048A1 (fr)

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DE102013226946.3A DE102013226946A1 (de) 2013-12-20 2013-12-20 Konditioniermittel für keratinische Fasern mit PCA-Derivat
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CN109431910A (zh) * 2018-12-27 2019-03-08 湖南御家化妆品制造有限公司 皮肤屏障修复组合物及其应用
CN109431910B (zh) * 2018-12-27 2021-08-31 湖南御家化妆品制造有限公司 皮肤屏障修复组合物及其应用

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