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WO2009150090A2 - Préparations cosmétiques pour éviter les odeurs corporelles - Google Patents

Préparations cosmétiques pour éviter les odeurs corporelles Download PDF

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Publication number
WO2009150090A2
WO2009150090A2 PCT/EP2009/056856 EP2009056856W WO2009150090A2 WO 2009150090 A2 WO2009150090 A2 WO 2009150090A2 EP 2009056856 W EP2009056856 W EP 2009056856W WO 2009150090 A2 WO2009150090 A2 WO 2009150090A2
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Prior art keywords
polymer
primary
secondary amino
polymers
use according
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German (de)
English (en)
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WO2009150090A3 (fr
Inventor
Nicole Hildebrandt
Volker Wendel
Bernd Bruchmann
Daniel SCHÖNFELDER
Guido Vandermeulen
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BASF SE
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BASF SE
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • A61K8/88—Polyamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/87—Application Devices; Containers; Packaging
    • A61K2800/874—Roll-on

Definitions

  • the present invention relates to the use of at least one polythyleneimine different, primary and / or secondary amino-containing polymer in cosmetic preparations for reducing the formation of saturated and unsaturated C6-Ci2-aldehydes from the unsaturated fatty acids of the skin and / or the scalp caused body odor.
  • Apocrine sweat is a complex mixture that contains sebum and other fats, steroids, cholesterol and about 10% protein.
  • Axillary body odor is essentially due to volatile short- and medium-chain fatty acids formed from branched long-chain fatty acids released by cleavage of skin lipids. From the long-chain branched fatty acids, the hydrolytic enzymes of Corynebacterium A form both short-chain C2-C5 fatty acids and medium-chain C6-Ci2 fatty acids, which are mainly responsible for the axillary body odor.
  • Another class of compounds that also results from the bacterial decomposition of the sweat components and contributes to body odor are saturated and unsaturated aldehydes, especially those with a chain length of C6-C12, in particular hexanal, heptanal, octenal and nonenal. These are formed by ⁇ -cleavage from the hydroperoxides, which are formed under the action of 5-lipoxygenase on unsaturated fatty acids.
  • Haze et al. (The Journal of Investigative Dermatology 2001, 16, 4, 520-524) describe as a possible cause of unpleasant body odor from people over the age of about 40 years compared to younger people increased concentration of 2-nonenal of the skin.
  • the increased concentration of 2-nonenal is due to an increased concentration of omega-7 and omega-10 unsaturated fatty acids, which are oxidatively degraded by atmospheric oxygen via hydroperoxides to unsaturated aldehydes.
  • EP 983727, EP1 129693 and EP1588627 describe the use of saccharides such as ⁇ , ⁇ -trehalose or malitol for inhibiting the formation of volatile aldehydes or the degradation of fatty acids.
  • Me-.beta.-cyclodextrins are capable of adsorbing offensive odorous volatile compounds.
  • JP 2001095908 describes the use of ethanolamine in filters for the adsorption of unsaturated aldehydes. Although ethanolamine binds aldehydes, it is not uncontroversial in terms of its cosmetic use.
  • EP 955035 describes the prevention of body odor by using anti-oxidants (culen), lipoxygenase inhibitors (tranexamic acid) or bacteriocides (dihydrofarnesol) in cosmetic preparations.
  • JP2007044422 describes the use of hydroxyalkylamines in deodorants to reduce the odor caused by aldehydes. Although hydroxyalkylamines bind aldehydes, they are harmful to health and irritating.
  • DE 10237458 describes carnosine-containing cosmetic formulations for the reduction of 2-nonenal-induced body odor of the elderly.
  • DE 3047774 describes the use of polyethyleneimine for the absorption of odor-active substances which are produced by fatty acids, aldehydes, ketones, amines and sulfides. Described are uses in cosmetics, room deodorants, air filters and for the impregnation of shoe soles.
  • polyethyleneimine is cosmetically unsuitable because of its toxicity and the residual monomers and the resulting low molecular weight by-products, such as aziridine.
  • Nippon Keshohin Gijutsusha Kaishi (2000), 34 (4), 379-386 describes the use of thiotaurine to inhibit the formation of 2-nonenal.
  • EP 1275404 describes the use of oxidized cyclodextrins for the complexation of odor-causing compounds.
  • the binding of the odor-causing compounds by means of cyclodextrins is based on the formation of complexes, is reversible and the odor-causing compounds can be released again.
  • preparations should be made available which, with the lowest possible amount of active substance, reduce the unpleasant and disturbing effects of 2-nonenal and similar compounds and thus create advantageous products, especially for the elderly.
  • the polymers to be used according to the invention contain primary and / or secondary amino groups. In a further preferred embodiment of the invention, the polymers to be used according to the invention contain primary amino groups. In a further preferred embodiment of the invention, the polymers to be used according to the invention contain primary and secondary amino groups.
  • the use according to the invention is characterized in that the polymer containing primary and / or secondary amino groups is selected from the group consisting of polyamides, polyurethanes, polyureas, polymers with covalently bonded amino acids, oligo- and polysaccharides containing amino groups, polymers with covalently bound hydrazine, Vinylamine polymers, allylamine polymers, peptides, polyisobutenes, polyallylamines and mixtures thereof.
  • the polymer containing primary and / or secondary amino groups is selected from the group consisting of hyperbranched polyamides containing primary and / or secondary amino groups, primary and / or secondary amino-containing hyperbranched polyurethanes, primary and / or secondary amino groups containing hyperbranched polyester amides and hyperbranched polyureas containing primary and / or secondary amino groups.
  • DB degree of branching
  • DB [%] 100 * (T + Z) / (T + Z + L) where T is the average number of terminal monomer units, Z is the average number of branched monomer units, and L is the average number of linear monomer units
  • Hyperbranched polyamides are described in particular in WO 2006018125,
  • Hyperbranched polyurethanes and polyurethane ureas are described in particular in WO2004101624, WO199702304 and DE19904444. These references are hereby incorporated by reference in their entirety.
  • Hyperbranched polyureas are described in particular in WO2003066702, WO2005044897 and WO2005075541. These references are hereby incorporated by reference in their entirety.
  • Hyperbranched polyesteramides are described in particular in WO2006018126. This reference is hereby incorporated by reference in its entirety.
  • the polymer containing primary and / or secondary amino groups is selected from oligo- and polysaccharides containing primary and / or secondary amino groups.
  • oligosaccharides and polysaccharides are described in Shigehiro Hirano et al, Carbohydrate Research 144 (1985) 338-341, which is hereby incorporated by reference.
  • the polymer containing primary and / or secondary amino groups is selected from vinylamine polymers.
  • Vinylamine containing polymers are known, cf. US-A-4,421,602, US-A-5,334,287, EP-A-0 216 387, US-A-5,981,689, WO-A-00/63295 and
  • R 5 to R 9 independently of one another are hydrogen, C 1 -C 20 -alkyl, -aryl or -alkylaryl.
  • the N-vinylcarboxamide polymers are e.g. obtainable by polymerizing N-vinylformamide, N-vinyl-N-methylformamide, N-vinylacetamide, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide and N-vinylpropionamide.
  • the stated monomers can either be polymerized alone or copolymerized with other monomers.
  • Such suitable monomers are, for example, selected from the group consisting of acrylic acid, methacrylic acid, ethacrylic acid, alpha-chloroacrylic acid, crotonic acid, maleic acid, maleic anhydride, itaconic acid, citraconic acid, mesaconic acid, glutaconic acid, aconitic acid and fumaric acid.
  • the salts of the abovementioned acids in particular the sodium, potassium and ammonium salts.
  • the monomers can be used as such or as mixtures with one another.
  • suitable monomers are the vinyl esters of saturated carboxylic acids of 1 to 6 carbon atoms such as vinyl formate, vinyl acetate, vinyl propionate and vinyl butyrate and vinyl ethers such as C 1 to C 6 alkyl vinyl ethers, for example methyl or ethyl vinyl ether.
  • suitable comonomers are esters, amides and nitriles of ethylenically unsaturated C 3 -C 6 -carboxylic acids, for example methyl acrylate, methyl methacrylate, ethyl acrylate and ethyl methacrylate, acrylamide and methacrylamide and also acrylonitrile and methacrylonitrile.
  • suitable monomers are carboxylic acid esters which are derived from glycols or polyalkylene glycols, in each case only one OH group being esterified, for example hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, hydroxypropyl methacrylate, hydroxybutyl methacrylate and acrylic acid monoesters of polyalkylene glycols a further molar mass of from 500 to 10,000.
  • esters of ethylenically unsaturated carboxylic acids with aminoalcohols for example dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, diethylaminoethyl acrylate, diethylaminoethyl methacrylate, dimethylaminopropyl acrylate, dimethylaminopropyl methacrylate, diethylaminopropyl acrylate, dimethylaminobutyl acrylate, diethylaminobutyl acrylate or N-tert. methacrylate.
  • aminoalcohols for example dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, diethylaminoethyl acrylate, diethylaminoethyl methacrylate, dimethylaminopropyl acrylate, dimethylaminopropyl methacrylate, diethylaminopropyl
  • the basic acrylates can be used in the form of the free bases, the salts with mineral acids such as hydrochloric acid, sulfuric acid or nitric acid, the salts with organic acids such as formic acid, acetic acid, propionic acid or sulfonic acids or in quaternized form.
  • Suitable quaternizing agents are, for example, dimethyl sulfate, diethyl sulfate, methyl chloride, ethyl chloride or benzyl chloride.
  • Suitable comonomers are amides of ethylenically unsaturated carboxylic acids such as acrylamide, methacrylamide and N-alkyl mono- and diamides of monoethylenically unsaturated carboxylic acids having alkyl radicals of 1 to 6 carbon atoms, e.g. N-methylacrylamide, N, N-dimethylacrylamide, N-methylmethacrylamide, N-ethylacrylamide, N-propylacrylamide and tert-butylacrylamide and basic (meth) acrylamides, such as e.g.
  • N-vinylpyrrolidone N-vinylcaprolactam
  • acrylonitrile methacrylonitrile
  • N-vinylimidazole substituted N-vinylimidazoles, such as e.g. N-vinyl-2-methylimidazole, N-vinyl-4-methylimidazole, N-vinyl-5-methylimidazole, N-vinyl-2-ethylimidazole and N-vinylimidazolines
  • N-vinylimidazoline N-vinyl-2-methylimidazo-Nn and N-vinyl-2-ethylimidazoline.
  • N-vinylimidazoles and N-vinylimidazolines are also used, except in the form of the free bases, in neutralized or quaternized form with mineral acids or organic acids, the quaternization preferably being carried out with dimethyl sulfate, diethyl sulfate, methyl chloride or benzyl chloride. Also suitable are diallyldialkylammonium halides, e.g. Diallyldimethylammonium chloride.
  • Suitable comonomers also suitable (Lubrizol AMPS ®, Fa.) Sulfonic acid or phosphonic acid group-containing monoethylenically unsaturated monomers such as 2-acrylamido-2-methylpropane-sulfonic acid, vinyl sulfonic acid or vinyl are nylphosphonklare.
  • Preferred polymers are the at least partially hydrolyzed homopolymers of aforementioned N-vinylcarboxamide monomers.
  • Suitable precursors for the suitable polymers are, for example, copolymers which
  • the monomers preferably contain no acid groups.
  • N-vinylformamide with - vinyl formate, vinyl acetate, vinyl propionate, acrylonitrile, N-vinylcaprolactam, N-vinylurea, N-vinylpyrrolidone or C 1 to C 6 alkyl vinyl ethers are available.
  • the polymers containing N-vinylamine units are obtainable.
  • the hydrolysis of the above-described polymers is carried out by known methods by the action of acids, bases, metallic catalysts or enzymes.
  • acids are used as hydrolysis agents
  • the vinylamine units of the polymers are present as the ammonium salt
  • bases eg with metal hydroxides, in particular with alkali metal hydroxides and alkaline earth metal hydroxides
  • the hydrolysis can also be carried out with the aid of ammonia or amines.
  • acids are used as hydrolysis agents, these are preferably mineral acids, such as hydrogen halides, which can be used in gaseous form or as an aqueous solution.
  • acids are concentrated hydrochloric acid, sulfuric acid, nitric acid or phosphoric acid and organic acids, such as C1- to C5-carboxylic acids, and aliphatic or aromatic sulfonic acids.
  • organic acids such as C1- to C5-carboxylic acids, and aliphatic or aromatic sulfonic acids.
  • molar equivalents of an acid are required per formyl group equivalent in the polymers containing N-vinylformamide units.
  • the hydrolysis of the polymers containing N-vinylformamide units proceeds significantly faster than the polymers containing N-vinylacetamide units.
  • the comonomer units present in the copolymer can also be chemically modified. For example, from vinyl acetate units, vinyl alcohol units, from methyl acrylate, are produced. ter units acrylic acid units and of acrylonitrile units acrylamide or acrylic acid units.
  • the homo- and copolymers containing vinylamine units may furthermore contain amidine units which are formed by reaction of formic acid with two adjacent amino groups or by intramolecular reaction of amino groups with adjacent amide groups.
  • the polymers containing vinylamine units can be used in salt-containing and salt-free form.
  • desalination ultrafiltration is suitable.
  • the polymers containing vinylamine units also include at least partially hydrolyzed graft polymers of, for example, N-vinylformamide on polyalkylene glycols, polyvinyl acetate, polyvinyl alcohol, polyvinylformamides, polysaccharides such as starch, oligosaccharides or monosaccharides.
  • the graft polymers are obtainable by free-radically polymerizing, for example, N-vinylformamide in aqueous medium in the presence of at least one of the stated grafting bases together with further copolymerizable monomers and then hydrolyzing the grafted vinylformamide units at least partially in the manner described above to give vinylamine units.
  • the polymers containing vinylamine units may optionally also be crosslinked.
  • Crosslinked polymers can be obtained by two different methods. For example, it is possible to carry out the polymerization of N-vinylcarboxylic amides in the presence of a crosslinking agent.
  • Suitable crosslinkers are monomers which contain at least two ethylenically unsaturated double bonds, for example butanediol diacrylate, butanediol dimethacrylate, N, N'-methylenebisacrylamide, divinylurea, divinyldioxane, diacrylates or dimethacrylates of polyethylene glycols having a molecular weight of, for example, 100 to 10,000, preferably 200 to 500, Pentaerythritol triallyl ether, trimethylolpropane triacrylate and triacrylates or trimethacrylates of alkoxylated trimethylolpropane alkoxylated with from 3 to 90, preferably from 6 to 60, moles of ethylene oxide and / or propylene oxide.
  • polymers containing vinylamine units can also be crosslinked by reacting them with at least bifunctional compounds such as diepoxides, epihalohydrins, dihaloalkanes and / or dicarboxylic acids.
  • crosslinkers are bischlorohydrin ethers or bisepoxides of polyethylene glycols having molecular weights of from 100 to 500, glutaric dialdehyde, succinic acid or 1,2-dichloroethane.
  • the polymers suitable for the use according to the invention are preferably at least partially hydrolyzed homopolymers and copolymers of N-vinylcarboxamide monomers, such as homo- and copolymers of N-vinylformamide, N-vinylacetamide or N-methyl-N-vinylacetamide, in particular Homopolymers of N-vinylformamide and / or copolymers of N-vinylformamide with a monomer selected from the group consisting of acrylic acid, vinyl acetate, vinyl alcohol, vinylpyrrolidone, acrylamide and mixtures thereof.
  • N-vinylcarboxamide monomers such as homo- and copolymers of N-vinylformamide, N-vinylacetamide or N-methyl-N-vinylacetamide, in particular Homopolymers of N-vinylformamide and / or copolymers of N-vinylformamide with a monomer selected from the group consisting of acrylic acid, vinyl acetate, vinyl alcohol
  • the total amount of N-vinylcarboxamide units, in particular the N-vinylformamide and / or N-vinylacetamide units of the polymers is from 1 to 100, preferably at least 50, more preferably at least 70, most preferably at least 80 and especially hydrolyzed to at least 90%.
  • Brand Lupamin ® or Luresin ® are for example those (BASF) for use in the invention suitable polyvinylamines.
  • the polymer containing primary and / or secondary amino groups is selected from the group consisting of allylamine polymers.
  • allylamine polymers Such polymers and their preparation are in
  • the polymer containing primary and / or secondary amino groups is selected from the group consisting of polyisobutenes containing primary and / or secondary amino groups.
  • polyisobutenes and processes for their preparation are described, for example, in EP 244616 A1, which is hereby incorporated by reference in its entirety.
  • the polymer containing primary and / or secondary amino groups is selected from polymers containing primary and / or secondary amino groups, including covalently bonded amino acids.
  • the use according to the invention is characterized in that the polymer containing primary and / or secondary amino groups is a cocondensate of lysine with amines.
  • the polymer containing primary and / or secondary amino groups is a cocondensate of lysine with amines.
  • the use according to the invention is characterized in that the polymers containing primary and / or secondary amino groups are cocondensates of lysine with carboxylic acids, lactams or Aminocarboxylic acids are.
  • Such polymers and their preparation are described in US 6034204, which is hereby incorporated by reference.
  • the use according to the invention is characterized in that the polymers containing primary and / or secondary amino groups are crosslinked polylysine derivatives.
  • Such polymers and their preparation are described in WO 00/71600, which is hereby incorporated by reference.
  • the use according to the invention is characterized in that the polymers containing primary and / or secondary amino groups are alkoxylated polylysine derivatives.
  • the polymers and their preparation are described in WO 00/71601, which is hereby incorporated by reference.
  • the use according to the invention is characterized in that the polymers are selected from polypeptides (peptides of at least 10 amino acids), polyamino acids or such polymers which contain copolymerized monomers which have a covalent bond to an amino acid.
  • the use according to the invention is characterized in that the polymer containing primary and / or secondary amino groups is a polyamino acid.
  • the polyamino acid may in particular be a homo- or hetero-polyamino acid, a homo-polyamino acid being particularly preferred.
  • the polyamino acid may consist of naturally occurring and / or synthetic amino acids, with naturally occurring amino acids, in particular ⁇ -aminocarboxylic acids, in particular ⁇ -aminocarboxylic acids having an L configuration, being preferred.
  • the amino acids are at least trifunctional amino acids.
  • a trifunctional amino acid is understood to mean an amino acid which, in addition to the carboxyl and ⁇ -amino group, is another organic functional group, in particular a further hydroxyl, thiol, guanine or amino group, preferably a further amino group , having.
  • the polyamino acid particularly preferably contains at least one amino acid from the group comprising cysteine, methionine, tryptophan, histidine, arginine, lysine, ornithine, aspartic acid, glutamic acid and derivatives thereof, particularly preferably lysine.
  • a preferred polyamino acid is ⁇ -polylysine, as produced, for example, by Chisso (Japan) (described in T. Yoshida, T. Nagasawa, Appl. Microbiol., Biotechnol., 2003, 62, 2, JP 2002330797 and JP 2004123630 , to which reference is hereby made in its entirety).
  • the polyamino acid has a linear structure.
  • the polyamino acid has a branched, preferably hyperbranched, structure.
  • the polymer containing primary and / or secondary amino groups is selected from polymers obtainable by condensation of a) lysine, arginine, ornithine, tryptophan or mixtures thereof with b) at least one co-condensable compound selected from the group consisting of: Group consisting of optionally substituted or functionalized amines, optionally substituted or functionalized nonproteinogenic carboxylic acids, optionally substituted alcohols, and urea, guanidine and melamine.
  • the use according to the invention is characterized in that the polymer containing primary and / or secondary amino groups contains incorporated monomers which have a covalent bond to an amino acid, preferably lysine.
  • Suitable monomers are those which form an ester or an amide bond with an amino acid.
  • Suitable monomers are, for example, esters or amides of (meth) acrylic acid and amino acids.
  • a preferred polymer of this type contains (meth) acrylic acid-amino acid amide copolymerized.
  • R 1 is hydrogen or methyl, preferably methyl.
  • R 1 is hydrogen or methyl, preferably methyl.
  • Particularly preferred is a use which is characterized in that the polymer containing primary and / or secondary amino groups polylysine, more preferably poly- ⁇ -lysine (poly-alpha-lysine) and / or poly- ⁇ -lysine (poly-epsilo-lysine). Lysine), with poly- ⁇ -lysine being particularly preferred.
  • the molecular weight M w of the polyamino acids suitable for the use according to the invention is preferably in the range of 500 and 200,000 g / mol, more preferably in the range of 1,000 to 50,000 g / mol, more preferably in the range of 1,500 to 40,000 g / mol preferably in the range from 2000 to 30,000 g / mol, more preferably in the range from 3,000 to 20,000 g / mol, more preferably in the range from 2,500 to 15,000, in particular in the range from 5,000 g / mol to 15,000 g / mol.
  • the polymer containing primary and / or secondary amino groups is selected from hyperbranched polypeptides.
  • Hyperbranched polypeptides in the context of this invention are understood as meaning uncrosslinked macromolecules composed of amino acids which are structurally as well as molecularly nonuniform. They can be constructed on the one hand, starting from a central molecule analogous to dendrimers, but with uneven chain length of the branches. On the other hand, they can also be linear, with functional side groups, or, as a combination of the two extremes, linear and branched parts of the molecule.
  • hyperbranched polypeptides are hyperbranched polylysines, for the synthesis of which, in principle, three processes are known: Process 1 is based on the ring-opening polymerization of ⁇ -protected L-lysine-N-carboxyanhydrides (NCAs) with a nucleophilic starter;
  • NCAs ⁇ -protected L-lysine-N-carboxyanhydrides
  • Method 2 uses derivatives of L-lysine * 2 HCl activated at the carboxyl group
  • method 3 involves the direct thermal polymerization of L-lysines.
  • Hyperbranched poly (L-lysines) prepared by this method have been described by Klok et al. (WO 2003/1064452 and Macromolecules 2002, 35, 8718-8723). Furthermore, such prepared hyperbranched poly (L-lysines) of Rodriguez-Hernandez et al. (Biomacromolecules 2003, 4, 249-258). Structurally similar hyperbranched block copolymers have also been described by Birchall et al. (Chem. Commun. 1998, 1335-1 336).
  • WO 2007/0601 19 describes a process for the preparation of uncrosslinked hyperbranched polylysines in which
  • uncrosslinked hyperbranched polylysines having a weight-average molecular weight Mw of up to 750,000 Da, preferably up to 700,000 Da, particularly preferably up to 650,000 Da, very particularly preferably up to 600,000 Da and in particular up to 550,000 Da.
  • uncrosslinked hyperbranched polylysines having a weight-average molecular weight M w of more than 5,000 Da, preferably more than 7,500 Da, more preferably more than 10,000 Da, very preferably more than 12,000 Da, in particular more than 15,000 Da, specifically to produce more than 20,000 Da and even more than 25,000 Da.
  • Cosmetic preparations preferred according to the invention are deodorants, antiperspirants, washing, shower and bath preparations and body lotions.
  • Preferred cosmetic preparations are, for example, washing, showering and bathing preparations.
  • washing, showering and bathing preparations are liquors of liquid to gelatinous consistency, such as transparent soaps, luxury soaps, deodorants, cream soaps, baby soaps, skin protection soaps, abrasive soaps and syndets, pasty soaps, greases and washing pastes, liquid washing -, shower and bath preparations, such as washing lotions, shower baths and gels, bubble baths, oil baths and scrub preparations, shaving foams, lotions and creams understood.
  • the cosmetic deodorant or antiperspirant preparations containing at least one polymer containing primary and / or secondary amino groups can be used as powder, in stick form, as aerosol spray, pump spray, liquid and gel roll on application, cream, gel and as impregnated flexible substrate present.
  • Deodorant or antiperspirant sticks may be in gelled, anhydrous wax base and based on W / O emulsions and O / W emulsions. Gel sticks can be prepared on the basis of fatty acid soaps, dibenzylidenesorbitol, N-acylamino acid amides, 12-hydroxystearic acid and other gelling agents.
  • Aerosol sprays, pump sprays, roll on applications and creams can be used as water-in-oil emulsion, oil-in-water emulsion, silicone oil-in-water emulsion, water-in-oil microemulsion, oil-in-water emulsion.
  • Microemulsion, anhydrous suspension, alcoholic and hydroalcoholic solution, aqueous gel and as an oil All mentioned preparations can be thickened, for example on the basis of fatty acid soaps, dibenzylidene sorbitol, N-acyl amino acid amides, 12-hydroxystearic acid, polyacrylates from Carbopol ® type, polyacrylamides and polysaccharides, which may be chemically and / or physically modified.
  • the emulsions and microemulsions may be transparent, translucent or opaque.
  • the cosmetic preparation in the sense of the present invention is a solution or emulsion or dispersion, it is possible to use as solvent:
  • Oils such as, for example, triglycerides of capric or caprylic acid or the oils mentioned below under "Oils, fats and / or waxes", - Fats, waxes and other natural and synthetic fatty substances, preferably esters of fatty acids with alcohols of low C number with, for example, isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids;
  • Alcohols, diols or polyols and their ethers preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products.
  • ethanol isopropanol
  • propylene glycol glycerol
  • ethylene glycol ethylene glycol monoethyl or monobutyl ether
  • propylene glycol monomethyl monoethyl or monobutyl ether
  • diethylene glycol monomethyl or monoethyl ether diethylene glycol monomethyl or monoethyl ether and analogous products.
  • mixtures of the abovementioned solvents are used.
  • water can be another ingredient.
  • the cosmetic preparations in addition to the primary and / or secondary amino-containing polymer further contain at least one oil and / or fat phase.
  • the cosmetic preparation based on the total weight of the preparation, in the range of 0.01 to 10 wt .-%, preferably from 0.1 to 5 wt .-%, particularly preferably from 0.2 to 2 wt .-% the primary and / or secondary amino group-containing polymers.
  • the cosmetic preparations preferably contain oils, fats and / or waxes. These include fatty acids, fatty alcohols, natural and synthetic cosmetic oil components as well as natural and synthetic waxes, which can be in solid or liquid aqueous or oily dispersion.
  • the ingredients used for the cosmetic preparations are those oils, fats and / or waxes which are listed on page 28, line 39 to page 34, line 22 of WO 2006/106140 and in paragraphs [0029] to [0039] of DE 10257738 A1 are described. The content of this text is hereby incorporated by reference.
  • the content of oils, fats and waxes is preferably at most 50, more preferably at most 30, more preferably at most 20% by weight, based on the total weight of the cosmetic preparations.
  • the cosmetic preparations may further comprise at least one water-soluble
  • Water solubility is understood according to the invention that at least 5 wt .-% of the alcohol at 20 0 C in water clearly dissolve or - in the case of long-chain or polymeric alcohols - by heating the water-alcohol mixture to 50 0 C to 60 0 C. can be brought into solution.
  • Alcohols to be used advantageously in the cosmetic preparations are described in paragraphs [0040] and [0041] of DE 10257738 A1. The content of this text is hereby incorporated by reference.
  • Cosmetic preparations which are a skin cleansing or shampooing agent preferably contain at least one anionic, nonionic or amphoteric surfactant, or else mixtures of such substances, the active ingredient used in the aqueous medium according to the invention and adjuvants, as they are usually used for this purpose.
  • the surfactant or mixtures of these substances may be present in a concentration between 1% and 50% by weight in the shampoo.
  • Cosmetic preparations for the treatment and care of the hair containing the active ingredient used according to the invention may be in the form of emulsions which are of the non-ionic or anionic type.
  • Nonionic emulsions contain, in addition to water, oils or fatty alcohols which may, for example, also be polyethoxylated or polypropoxylated, or else mixtures of the two organic components. These emulsions optionally contain cationic surfactants.
  • cosmetic preparations for the treatment and care of the hair may be in the form of gels which, in addition to an effective content of the active ingredient according to the invention and solvents customarily used therefor, preferably water, are also organic thickeners, for example gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably Methylcelluloses, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose or inorganic thickening agents, for example aluminum silicates, for example bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
  • the thickener is contained in the gel, for example, in an amount between 0.1 and 30 wt .-%, preferably between 0.5 and 15 wt .-%.
  • Aqueous cosmetic cleansing compositions according to the invention or low-water or anhydrous cleaning agent concentrates intended for aqueous cleansing may comprise anionic, cationic, nonionic and / or amphoteric surfactants.
  • the cosmetic preparations further contain at least one surfactant in addition to the primary and / or secondary amino group-containing polymer.
  • surfactants anionic, cationic, nonionic and / or amphoteric surfactants can be used.
  • Surfactants are amphiphilic substances that can dissolve organic, nonpolar substances in water.
  • Sarcosinates for example myristoyl sarcosine, TEA-lauroyl sarcosinate, sodium lauroyl sarcosinate and sodium cocoyl sarcosinate, sulfonic acids and their salts, such as
  • Acyl isethionates for example sodium or ammonium cocoyl isethionate Sulfosuccinates, for example dioctyl sodium sulphosuccinate, disodium laureth sulphosuccinate, disodium lauryl sulphosuccinate and disodium undecylenamido MEA sulphosuccinate, disodium PEG-5 lauryl citrate sulphosuccinate and derivatives,
  • Alkyl ether sulfates for example sodium, ammonium, magnesium, MIPA, TIPA laureth sulfate, sodium myreth sulfate and sodium C12-13 pareth sulfate,
  • Alkyl sulfates for example sodium, ammonium and TEA lauryl sulfate. Further advantageous anionic surfactants are
  • Taurates for example sodium lauroyl taurate and sodium methyl cocoyl taurate
  • Ether carboxylic acids for example sodium laureth-13 carboxylate and sodium PEG-6 cocamide carboxylate, sodium PEG-7 olive oil carboxylate
  • Phosphoric acid esters and salts such as, for example, DEA-oleth-10-phosphate and dilaureth-4-phosphate,
  • Alkyl sulfonates for example sodium coconut monoglyceride sulfate, sodium C 12-14 olefin sulfonate, sodium lauryl sulfoacetate and magnesium PEG-3 cocamide sulfate, acylglutamates such as di-TEA-palmitoyl aspartate and sodium caprylic / capric glutamate,
  • Acyl peptides for example palmitoyl hydrolyzed milk protein, sodium cocoyl-hydrolysed soy protein and sodium / potassium cocoyl-hydrolyzed collagen, and carboxylic acids and derivatives such as lauric acid, aluminum stearate, magnesium alkoxide and zinc undecylenate, ester carboxylic acids, for example calcium stearyl lactate, laureth-6 citrate and sodium PEG-4 Lauramidcarboxylate
  • Advantageous washing-active cationic surfactants for the purposes of the present invention are quaternary surfactants.
  • Quaternary surfactants contain at least one N atom covalently linked to 4 alkyl or aryl groups.
  • alkylbetaine, alkylamidopropylbetaine and alkylamidopropylhydroxysultaine are advantageous.
  • Further advantageous cationic surfactants are further provided.
  • Advantageous washing-active amphoteric surfactants are acyl / dialkylethylenediamines, for example sodium acylamphoacetate, disodium acylamphodipropionate, disodium alkylamphodiacetate, sodium acylamphohydroxypropylsulfonate, disodium acylamphodiacate, sodium acylamphopropionate, and N-coconut fatty acid amidoethyl-N-hydroxyethylglycinate sodium salts.
  • acyl / dialkylethylenediamines for example sodium acylamphoacetate, disodium acylamphodipropionate, disodium alkylamphodiacetate, sodium acylamphohydroxypropylsulfonate, disodium acylamphodiacate, sodium acylamphopropionate, and N-coconut fatty acid amidoethyl-N-hydroxyethylglycinate sodium salts.
  • amphoteric surfactants are N-alkylamino acids, for example aminopropylalkylglutamide, alkylaminopropionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate.
  • Advantageous washing-active nonionic surfactants are N-alkylamino acids, for example aminopropylalkylglutamide, alkylaminopropionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate.
  • Alkanolamides such as cocamide MEA / DEA / MIPA, Esters formed by esterification of carboxylic acids with ethylene oxide, glycerol, sorbitan or other alcohols,
  • Ethers for example ethoxylated alcohols, ethoxylated lanolin, ethoxylated polysiloxanes, propoxylated POE ethers, alkylpolyglycosides such as lauryl glucoside, decyl glycoside and cocoglycoside, glycosides having an HLB value of at least 20 (for example BeififG 128V (Wacker)).
  • nonionic surfactants are alcohols and amine oxides, such as cocoamidopropylamine oxide.
  • Preferred anionic, amphoteric and nonionic shampoo surfactants are mentioned, for example, in "Cosmetics and Hygiene from Head to Toe", ed. W. Limbach, 3rd edition, Wiley-VCH, 2004, pp.131-134, which is mentioned at this point in Among the alkyl ether sulfates, particular preference is given to sodium alkyl ether sulfates based on di- or tri-ethoxylated lauryl and myristyl alcohol.
  • Arnidopropylbetaine are virtually insignificant as sole washing raw materials, since their foaming behavior and their thickening are only moderately pronounced. In contrast, these surfactants have an excellent skin and eye mucosa compatibility. In combination with anionic surfactants, their mildness can be synergistically improved. Preferred is the use of cocamidopropyl betaine.
  • Arnphotoacetates / Arnphodiacetates as amphoteric surfactants, have a very good skin and mucous membrane compatibility and can have a hair conditioning effect or increase the care effect of additives. They are similar to the betaines used to optimize alkyl ether sulfate formulations. Most preferred are sodium cocoamphoacetate and disodium cocoamphodiacetate.
  • Alkyl polyglycosides are nonionic washing raw materials. They are mild, have good universal properties, but lather weakly. For this reason, they are preferably used in combination with anionic surfactants. Sorbitan esters also belong to the nonionic washing raw materials. Because of their excellent mildness they are preferred for use in baby shampoos. As weak foaming agents, they are preferably used in combination with anionic surfactants.
  • Cosmetic preparations which are cosmetic cleansing preparations for the skin may be in liquid or solid form.
  • they preferably comprise at least one anionic, nonionic or amphoteric surface-active substance or mixtures thereof and auxiliaries as are customarily used therefor.
  • the surface-active substance can be present in a concentration of between 1 and 94% by weight in the cleaning preparations, based on the total weight of the preparations.
  • Cosmetic preparations which are a shampooing agent contain, in addition to an effective content of primary and / or secondary amino groups, preferably at least one anionic, nonionic or more amphorous surface-active substance or mixtures thereof, and auxiliaries, as are usually used for this purpose.
  • the surfactant may be present in a concentration between 1% and 94% by weight in the shampoo.
  • the cosmetic preparations in addition to the primary and / or secondary amino-containing polymer further contain at least one oil and / or fat phase and at least one surfactant.
  • advantageous polysorbates are, for example
  • the polysorbates are used advantageously in a concentration of 0.1 to 5 and in particular in a concentration of 1, 5 to 2.5 wt .-%, based on the total weight of the preparation individually or as a mixture of polysorbates several.
  • the cosmetic preparations contain in a preferred embodiment at least one antiperspirant active ingredient.
  • Antiperspirant active substances which are advantageously to be used are described in paragraph [0046] of DE 10257738 A1, to which reference is hereby made in full.
  • the conditioning agents used for the cosmetic preparations are preferably those conditioning agents which are described on page 34, line 24 to page 37, line 10 of WO 2006/106140. The content of said text is hereby incorporated by reference.
  • Liquid and gel forms may contain thickeners.
  • suitable thickeners are in "cosmetics and hygiene from head to toe", ed. W. Limbach, 3rd edition, Wiley-VCH, 2004, p.235-236 called , to which reference is made in full at this point.
  • Suitable thickeners for the cosmetic preparations are described, for example, on page 37, line 12 to page 38, line 8 of WO 2006/106140. The content of said text is hereby incorporated by reference.
  • the cosmetic preparations may also contain preservatives. Preparations with high water contents must be reliably protected against contamination. Suitable preservatives for the cosmetic preparations are described, for example, on page 38, line 10 to page 39, line 18 of WO 2006/106140. The content of said text is hereby incorporated by reference.
  • complexing agents such as salts of ethylenediaminetetraacetic acid, nitrilotriacetic acid, iminodisuccinic acid or phosphates are added.
  • UV light protection filter In order to stabilize the ingredients contained in the cosmetic preparations, such as dyes and perfume oils against changes by UV light, UV light protection filters, such as. As benzophenone derivatives are incorporated. Suitable UV protection filters for the cosmetic preparations are, for example, on page 39, line 20 to page 41, line 10 of WO
  • the cosmetic preparations preferably also contain antioxidants. According to the invention, all antioxidants suitable or used for cosmetic applications can be used as antioxidants. Suitable antioxidants for the cosmetic preparations are, for example, on page 41, line 12 to page 42 line 33 of WO 2006/106140 described. The content of said text is hereby incorporated by reference.
  • Buffers ensure the pH stability of the cosmetic preparations. Predominantly used are citrate, lactate and phosphate buffers.
  • Solubilizers They are used to clearly dissolve nourishing oils or perfume oils and to keep them clear even in the cold.
  • the most common solubilizers are ethoxylated nonionic surfactants, eg. B. hydrogenated and ethoxylated castor oils.
  • Germ-inhibiting agents can also be used. These generally include all suitable preservatives having specific activity against Gram-positive bacteria, e.g. Triclosan (2,4,4'-trichloro-2'-hydroxydiphenyl ether), chlorhexidine (1,1'-hexamethylenebis [5- (4-chlorophenyl) biguanide), and TTC (3,4,4'-trichlorocarbanilide). Quaternary ammonium compounds are also suitable in principle and are preferably used for disinfecting soaps and washing lotions. Also numerous fragrances have antimicrobial properties. Also, a large number of essential oils or their characteristic ingredients such. Clove oil (eugenol), mint oil (menthol) or thyme oil (thymol), show a pronounced antimicrobial activity.
  • Triclosan 2,4,4'-trichloro-2'-hydroxydiphenyl ether
  • chlorhexidine (1,1'-hexamethylenebis [5- (4-chlorophenyl) bigu
  • the antibacterial substances are usually used in concentrations of about 0.1 to 0.3 wt .-%.
  • Dispersant When in the cosmetic preparations insoluble drugs, e.g. Antidandruff active ingredients or silicone oils, dispersed and kept in suspension in the long term, must dispersants and thickeners such. For example, magnesium aluminum silicates, bentonites, fatty acyl derivatives, polyvinylpyrrolidone or hydrocolloid, z. As xanthan gum or carbomers are used. According to the invention, preservatives are present in a total concentration of at most 2, preferably at most 1, 5 and particularly preferably at most 1% by weight, based on the total weight of the cosmetic preparations.
  • insoluble drugs e.g. Antidandruff active ingredients or silicone oils
  • thickeners such as magnesium aluminum silicates, bentonites, fatty acyl derivatives, polyvinylpyrrolidone or hydrocolloid, z.
  • xanthan gum or carbomers are used.
  • preservatives are present in a total concentration of at most 2, preferably at most 1, 5 and particularly preferably
  • Suitable propellants for sprayable from aerosol containers cosmetic preparations in the context of the present invention are the usual known volatile, liquefied propellants, such as hydrocarbons (propane, butane, isobutane), dimethyl ether and mixtures of hydrocarbons and dimethyl ether suitable, which can be used alone or in mixture , Also, compressed air is advantageous to use.
  • hydrocarbons propane, butane, isobutane
  • dimethyl ether dimethyl ether
  • mixtures of hydrocarbons and dimethyl ether suitable
  • compressed air is advantageous to use.
  • the person skilled in the art knows that there are per se nontoxic propellants which would in principle be suitable for the realization of the present invention in the form of aerosol preparations, but which should nevertheless be dispensed with because of a harmful effect on the environment or other concomitant circumstances, in particular fluorocarbons and chlorofluorocarbons (CFCs).
  • CFCs chlorofluorocarbons
  • Cosmetic preparations for the purposes of the present invention may also be present as gels which, in addition to an effective content of polymer containing primary and / or secondary amino groups and solvents conventionally used for it, preferably water, or organic thickeners, for example gum arabic, xanthan gum, sodium alginate, cellulose Derivatives, preferably methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose or inorganic thickening agents, e.g. For example, aluminum silicates such as bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
  • polymer containing primary and / or secondary amino groups and solvents conventionally used for it preferably water, or organic thickeners, for example gum arabic, xanthan gum, sodium alginate, cellulose Derivatives, preferably methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose
  • the thickener is in the gel, based on the gel, for example in an amount between 0.1 and 30 wt .-%, preferably between 0.5 and 15 wt .-%, included.
  • Gels used according to the invention usually contain alcohols of low C number, for example ethanol, isopropanol, 1,2-propanediol, glycerol and water or an abovementioned oil in the presence of a thickener, which in the case of oily-alcoholic gels is preferably silica or an aluminum silicate, in aqueous-alcoholic or alcoholic gels, preferably a polyacrylate.
  • Emulsions according to the invention for the purposes of the present invention are advantageous and contain e.g. Fats, oils, waxes and / or other fatty substances, as well as water and one or more emulsifiers, as they are commonly used for such a type of formulation.
  • the lipid phase of the cosmetic emulsions according to the invention can advantageously be selected from: mineral oils, mineral waxes
  • Oils such as triglycerides of capric or caprylic acid, also natural oils such. Castor oil or the oils mentioned above under "Oils, fats and / or waxes"
  • Fats, waxes and other natural and synthetic fats preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol,
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • a further subject matter of the invention is a process for reducing the body odor caused by the formation of saturated and unsaturated C 6 -C 12 aldehydes from the unsaturated fatty acids of the skin and / or the scalp, characterized in that a cosmetic preparation containing at least one, of polyethyleneimine, primary and / or secondary amino group-containing polymer is brought into contact with the skin and / or the scalp.
  • the inner wall of a 50 ml vial was coated with a polymer film.
  • 600 ml of a 50 wt .-% aqueous solution of polymer were filled into the ampoule and the water was removed with constant rotation of the ampoule by heating.
  • 0.1 wt .-% 2-nonenal was added to the vial, this incubated for 1 hour at 40 0 C and then analyzed a sample of the gas phase by means of head-space GC.
  • Table 1 The results are summarized in the following Table 1.
  • the high-viscosity polymer was discharged hot, poured onto a cooling plate and then finely ground in a mortar.
  • the product was dissolved in water to give a 50% by weight solution.
  • the aqueous solution was filtered and measured by GPC.
  • the GPC analysis was carried out by column combination of OHpak SB-803 HQ and SB-804 HQ (Shodex) in aqueous solution with the addition of 0.1 mol / L sodium bicarbonate at 30 0 C at a flow rate of 0.5 mL / min and polyethylene oxide as standard.
  • a UV detector was used, which worked at a wavelength of 230 nm.
  • the stirrer was turned on. After reaching the maximum internal temperature (about 160 0 C) was condensed under autogenous pressure for 4 hours. Thereafter, the kettle was on the cooler in the distillate vessel in about 45 min. relaxed (distilled). The kettle was closed and the reaction mixture was condensed at maximum self-adjusting internal temperature for another 2 hours under autogenous pressure. Thereafter, the kettle was again on the cooler in the distillate vessel in about 30 min. relaxed (distilled). Thereafter, the kettle was slowly evacuated and the reaction mixture was condensed at full vacuum for a further 5 hours. Thereafter, the vacuum was removed, the boiler vented with nitrogen and the outside temperature lowered to 90 0 C. When reaching an internal temperature of about 120 0 C, water was added for 15 minutes.
  • phase A and B were heated independently to about 80 0 C. Thereafter, phase B was stirred into phase A and the mixture was homogenized. It was then allowed to cool to about 40 0 C and added phase C with stirring. Thereafter, with further stirring and homogenization, the mixture was allowed to cool to room temperature.
  • Phases A and B were heated independently to about 80 ° C. Thereafter, phase B was stirred into phase A and the mixture was homogenized. It was then allowed to cool to about 40 0 C and added phase C with stirring. Thereafter, with further stirring and homogenization, the mixture was allowed to cool to room temperature.
  • Example 5
  • phase A and B were heated independently to about 80 0 C. Thereafter, phase B was stirred into phase A and the mixture was homogenized. It was then allowed to cool to about 40 0 C and added phase C with stirring. Thereafter, with further stirring and homogenization, the mixture was allowed to cool to room temperature.
  • various preparations such as e.g. dispersion; pH adjustment; Swelling or a special method of preparation may be necessary.
  • the polymers may be in suitable encapsulated form.
  • the polymers can be incorporated in the aqueous phase.
  • the polymers can be used in the oil phase.
  • the polymers can be used both in the aqueous and in the oil phase.
  • the polymers can be incorporated with the perfume at about 40 0 C.
  • the polymers can be subsequently incorporated into the emulsion.
  • Another cream gel is prepared in which instead of the polymer of Example 1, the polymer of Example 2 is used.
  • Ceteareth-6 Stearyl Alcohol 1, 5 2.0 1, 5
  • Another antiperspirant stick is prepared by using the polymer of Example 2 instead of the polymer of Example 1.
  • a further antiperspirant roll-on is produced in which the polymer from example 2 is used instead of the polymer from example 1.
  • Another deodorant spray is prepared in which instead of the polymer of Example 1, the polymer of Example 2 is used.
  • Another liquid soap is prepared by using the polymer of Example 2 instead of the polymer of Example 1.

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Abstract

L'invention concerne l'utilisation d'au moins un polymère contenant des aminogroupes primaires et/ou secondaires, différents du polyéthylénium, servant à réduire les odeurs corporelles par formation de 5 aldéhydes saturés ou des aldéhydes C 6-C 12 non saturés à partir des acides gras non saturés produits par la peau et/ou le cuir chevelu
PCT/EP2009/056856 2008-06-12 2009-06-04 Préparations cosmétiques pour éviter les odeurs corporelles Ceased WO2009150090A2 (fr)

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WO2011141266A1 (fr) 2010-04-15 2011-11-17 Basf Se Procédé de fabrication de mousses de polyuréthane ignifugées
DE102011077075A1 (de) * 2011-06-07 2012-12-13 Beiersdorf Ag Wirkstoffkombinationen aus Epsilon-Polylysin und einem oder mehreren Alkylglucosiden
DE102011077071A1 (de) * 2011-06-07 2012-12-13 Beiersdorf Ag Wirkstoffkombinationen aus Epsilon-Polylysin und Climbazol
DE102011077040A1 (de) * 2011-06-07 2012-12-13 Beiersdorf Ag Wirkstoffkombinationen aus å-Polylysin (Epsilon-Polylysin) und einem oder mehrerenethoxylierten und/oder propoxylierten Alkanolen
WO2012168049A3 (fr) * 2011-06-07 2013-09-12 Beiersdorf Ag Utilisation de ε-polylysine (epsilon-polylysine) pour améliorer l'hydrorésistance de formulations cosmétiques ou dermatologiques
WO2013010708A3 (fr) * 2011-07-21 2013-09-26 Henkel Ag & Co. Kgaa Agent de traitement capillaire tensioactif contenant de la poly-l-lysine ii
WO2013010710A3 (fr) * 2011-07-21 2013-10-03 Henkel Ag & Co. Kgaa Agent de traitement capillaire tensioactif contenant de la poly-l-lysine i
WO2012168360A3 (fr) * 2011-06-07 2013-10-03 Beiersdorf Ag Associations de principes actifs à base de ε-polylysine (epsilon-polylysine) et de piroctone olamine et/ou de climbazole
US20150196477A1 (en) * 2014-01-15 2015-07-16 The Procter & Gamble Company Methods of reducing malodor and bacteria
WO2016030188A1 (fr) * 2014-08-26 2016-03-03 Henkel Ag & Co. Kgaa Produits cosmétiques anti-transpirants contenant des protéines de synthèse, exempts d'halogénures et/ou d'hydroxyhalogénures d'aluminium et/ou de zirconium
WO2019175041A1 (fr) * 2018-03-15 2019-09-19 Basf Se Composition appropriée pour des soins capillaires
WO2021004845A1 (fr) * 2019-07-08 2021-01-14 Basf Se Copolymère à ramification lysine
WO2022122574A1 (fr) * 2020-12-07 2022-06-16 Unilever Ip Holdings B.V. Compositions antitranspirantes

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WO2011141266A1 (fr) 2010-04-15 2011-11-17 Basf Se Procédé de fabrication de mousses de polyuréthane ignifugées
WO2012168360A3 (fr) * 2011-06-07 2013-10-03 Beiersdorf Ag Associations de principes actifs à base de ε-polylysine (epsilon-polylysine) et de piroctone olamine et/ou de climbazole
DE102011077075A1 (de) * 2011-06-07 2012-12-13 Beiersdorf Ag Wirkstoffkombinationen aus Epsilon-Polylysin und einem oder mehreren Alkylglucosiden
DE102011077040A1 (de) * 2011-06-07 2012-12-13 Beiersdorf Ag Wirkstoffkombinationen aus å-Polylysin (Epsilon-Polylysin) und einem oder mehrerenethoxylierten und/oder propoxylierten Alkanolen
EP2535040A3 (fr) * 2011-06-07 2013-09-04 Beiersdorf AG Combinaisons de substances actives à base dýepsilon-polylysine et d'un ou plusieurs alkanols éthoxylés et/ou propoxylés
WO2012168049A3 (fr) * 2011-06-07 2013-09-12 Beiersdorf Ag Utilisation de ε-polylysine (epsilon-polylysine) pour améliorer l'hydrorésistance de formulations cosmétiques ou dermatologiques
DE102011077071A1 (de) * 2011-06-07 2012-12-13 Beiersdorf Ag Wirkstoffkombinationen aus Epsilon-Polylysin und Climbazol
WO2013010708A3 (fr) * 2011-07-21 2013-09-26 Henkel Ag & Co. Kgaa Agent de traitement capillaire tensioactif contenant de la poly-l-lysine ii
WO2013010710A3 (fr) * 2011-07-21 2013-10-03 Henkel Ag & Co. Kgaa Agent de traitement capillaire tensioactif contenant de la poly-l-lysine i
WO2015108809A1 (fr) * 2014-01-15 2015-07-23 The Procter & Gamble Company Méthodes de réduction de mauvaises odeurs et de bactéries
US20150196477A1 (en) * 2014-01-15 2015-07-16 The Procter & Gamble Company Methods of reducing malodor and bacteria
WO2016030188A1 (fr) * 2014-08-26 2016-03-03 Henkel Ag & Co. Kgaa Produits cosmétiques anti-transpirants contenant des protéines de synthèse, exempts d'halogénures et/ou d'hydroxyhalogénures d'aluminium et/ou de zirconium
WO2019175041A1 (fr) * 2018-03-15 2019-09-19 Basf Se Composition appropriée pour des soins capillaires
JP2021518341A (ja) * 2018-03-15 2021-08-02 ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ ヘアケアに適した組成物
WO2021004845A1 (fr) * 2019-07-08 2021-01-14 Basf Se Copolymère à ramification lysine
WO2022122574A1 (fr) * 2020-12-07 2022-06-16 Unilever Ip Holdings B.V. Compositions antitranspirantes
US20240000690A1 (en) * 2020-12-07 2024-01-04 Conopco, Inc., D/B/A Unilever Antiperspirant compositions

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