WO2009150090A2 - Cosmetic preparations for reducing skin odor - Google Patents

Abstract

The invention relates to the use of at least one polymer which is different from polyethylene imine and which contains primary and/or secondary amino groups in cosmetic preparations for reducing the body odor caused by the formation of saturated and unsaturated C₆-C₁₂ aldehydes from the unsaturated fatty acids of the skin and/or the scalp.

Description

 Cosmetic preparations for reducing skin odor

description

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 β-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 α, α-trehalose or malitol for inhibiting the formation of volatile aldehydes or the degradation of fatty acids.

Journal of Inclusion Phenomena and Macrocyclic Chemistry (2003), 44 (1-4), 241-245, discloses that Me-.beta.-cyclodextrins are capable of adsorbing offensive odorous volatile compounds.

US 2003224077 describes that fatty acid oxidation is reduced by promoting the production of endogenous superoxide dismutase. Use in cosmetic

0 Fig. / Seq Applications find extracts of filamentous, non-photosynthetic bacteria.

DE 10257738 describes the use of N-alkylamino acid salts as inhibitors of 5-lipoxygenase, which reduces the formation of unsaturated aldehydes on the skin.

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. However, 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.

From a cosmetic preparation for the reduction of unwanted skin odors one expects the natural biology of the skin, fragrance neutrality, efficacy with respect to deodorization, ie avoidance and / or elimination of body odor, avoidance of the formation of resistant strains of bacteria, avoidance of accumulation lation of the active ingredients on the skin, harmlessness in the event of overdosage or other improper use, good cosmetic application, easy handling (eg as a liquid) and universal usability in a wide variety of cosmetic and external preparations, excellent skin and mucous membrane compatibility and use of environmentally friendly substances.

It was therefore an object of the present invention to develop cosmetically and dermatologically acceptable ingredients which are suitable as a basis for cosmetic preparations for the reduction of undesired odors of the skin, and which do not have the disadvantages of the prior art. A further object of the invention was to provide cosmetic bases for deodorising cosmetic preparations which are distinguished by good skin tolerance.

In particular, 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.

These objects have been achieved by the use of at least one polymer other than polyethyleneimine containing primary and / or secondary amino groups in cosmetic preparations for reducing the unsaturated fatty acids formed by the formation of saturated and unsaturated C 6 -C 12 aldehydes

Skin and / or the scalp caused body odor.

With the use of these cosmetic preparations there is a reduction of body odor, which is predominantly, but not exclusively, caused by 2-nonenal. This is especially true for the reduction of body odor in people older than about 40 years.

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.

Preferably, 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. In a preferred embodiment of the invention, 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.

For the definition of dendrimeric and hyperbranched polymers see also PJ. Francisco, J. Am. Chem. Soc. 1952, 74, 2718 and H. Frey et al., Chemistry - A European

Journal, 2000, 6, no. 14, 2499. In the context of the present invention, "hyperbranched" means that the degree of branching (DB) is 10 to 99.9%, preferably 20 to 99%, particularly preferably 20 to 95% DB is defined as 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 For the definition of the degree of branching see also H. Frey et al., Acta Polym. 1997, 48, 30.

Hyperbranched polyamides are described in particular in WO 2006018125,

US Pat. No. 4,407,666, US Pat. No. 6,543,600, US Pat. No. 2,230,555,909, US Pat. No. 6,300,424, US Pat. No. 5,514,764, WO 9208749, and unpublished German patent application DE 102004039101.7. These references are hereby incorporated by reference in their entirety.

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.

In a further preferred embodiment of the invention, the polymer containing primary and / or secondary amino groups is selected from oligo- and polysaccharides containing primary and / or secondary amino groups. Such oligosaccharides and polysaccharides are described in Shigehiro Hirano et al, Carbohydrate Research 144 (1985) 338-341, which is hereby incorporated by reference. In a further preferred embodiment of the invention, 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

US-A-6,121,409. They are prepared by at least partial hydrolysis of open-chain N-vinylcarboxamide units containing polymers. N-Vinylcarbonsäureamid monomers have a structure according to the general formula: CR ⁵ R ⁶ = CR ⁷ NR ⁸ C (O) R ⁹

where 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.

As monoethylenically unsaturated monomers which are copolymerized with the N-vinylcarboxamides, in principle all compounds copolymerizable therewith are suitable.

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. Also suitable are the half-esters of monoethylenically unsaturated dicarboxylic acids having 4 to 10, preferably 4 to 6, carbon atoms, eg. B. of maleic acid such as monomethyl maleate. Also suitable are 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.

Further examples of 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. Further 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. Further examples of 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. Further suitable comonomers are 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. 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.

Further 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. Dimethylaminoethylacrylamide, dimethylaminoethylmethacrylamide, diethylaminoethylacrylamide, diethylaminoethylmethacrylamide, dimethylaminopropylacrylamide, diethylaminopropylacrylamide, dimethylaminopropylmethacrylamide and diethylaminopropylmethacrylamide.

Further suitable comonomers are N-vinylpyrrolidone, N-vinylcaprolactam, acrylonitrile, methacrylonitrile, N-vinylimidazole and 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 such as 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 nylphosphonsäure.

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

95 to 5 mol%, preferably 90 to 10 mol% of at least one N-vinylcarboxylic acid amide and

5 to 95 mol%, preferably 10 to 90 mol% of other copolymerizable monoethylenically unsaturated monomers in copolymerized form. The monomers preferably contain no acid groups.

In order to prepare polymers containing N-vinylamine units, preference is given to homopolymers of N-vinylformamide or of copolymers obtained by copolymerizing

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. By a subsequent, at least partial hydrolysis of the homopolymers or the copolymers to form vinylamine units from the copolymerized N-vinylformamide units, 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. When acids are used as hydrolysis agents, the vinylamine units of the polymers are present as the ammonium salt, while the hydrolysis with bases (eg with metal hydroxides, in particular with alkali metal hydroxides and alkaline earth metal hydroxides) gives rise to the free amino groups. In special cases, the hydrolysis can also be carried out with the aid of ammonia or amines. If 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. Preferably used 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. For example, from 0.05 to 2, in particular from 1 to 1.5, 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. If copolymers of the suitable N-vinylcarboxamides with other comonomers undergo hydrolysis, 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.

On an industrial scale, it is advantageous to neutralize polymers prepared by solution polymerization with sodium hydroxide solution and polymers prepared by water-in-water emulsion polymerization by means of acid, in particular sulfuric acid. The degree of hydrolysis of the homopolymers determines the content of polymers of vinylamine units.

It is known that 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. For 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. However, 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. Examples of such 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.

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.

In a further preferred embodiment of the invention, the polymer containing primary and / or secondary amino groups is selected from the group consisting of allylamine polymers. Such polymers and their preparation are in

US 4,749,759 and US 4,812,540, to which reference is hereby made.

In a preferred embodiment of the invention, the polymer containing primary and / or secondary amino groups is selected from the group consisting of polyisobutenes containing primary and / or secondary amino groups. Such polyisobutenes and processes for their preparation are described, for example, in EP 244616 A1, which is hereby incorporated by reference in its entirety.

In a further preferred embodiment of the invention, 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.

In one embodiment of the invention, 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. Such polymers and their preparation are described in US 61 11057, to which reference is hereby made.

In a further embodiment of the invention, 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.

Such uncrosslinked or crosslinked cocondensates are also described in DE-A 19940955 and DE-A 10041559, to which reference is hereby made.

In a further embodiment of the invention, 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.

In a further embodiment of the invention, the use according to the invention is characterized in that the polymers containing primary and / or secondary amino groups are alkoxylated polylysine derivatives. Such polymers and their preparation are described in WO 00/71601, which is hereby incorporated by reference. Preferably, 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.

In a particularly preferred embodiment of the invention, 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 α-aminocarboxylic acids, in particular α-aminocarboxylic acids having an L configuration, being preferred. Preferably, the amino acids are at least trifunctional amino acids. In the context of the present invention, a trifunctional amino acid is understood to mean an amino acid which, in addition to the carboxyl and α-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 ε-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). Advantageously, the polyamino acid has a linear structure. In a particularly preferred embodiment of the invention, the polyamino acid has a branched, preferably hyperbranched, structure.

In a further preferred embodiment of the invention, 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.

Such polymers are described in DE 100 41 559 A1, to which reference is hereby made in its entirety.

In a further preferred embodiment of the invention, 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.

The preparation of the corresponding monomers is described, for example, in EP 1156031 A1 and in the documents of the associated International Search Report, to which reference is hereby made in its entirety. Preference is given to a polymer which contains (meth) acrylic acid lysine amides of the general formulas I and / or II in copolymerized form.

wobei R¹ Wasserstoff oder Methyl, bevorzugt Methyl ist. Besonders bevorzugt ist eine Verwendung, die dadurch gekennzeichnet ist, dass das primäre und/oder sekundäre Aminogruppen enthaltende Polymer Polylysin, weiter bevorzugt Poly-α-Lysin (Poly-alpha-Lysin) und/oder Poly-ε-Lysin (Poly-epsilon-Lysin) ist, wobei Poly-ε-Lysin besonders bevorzugt ist.

wherein 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-α-lysine (poly-alpha-lysine) and / or poly-ε-lysine (poly-epsilo-lysine). Lysine), with poly-ε-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.

In a very particularly preferred embodiment of the invention, 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.

Particularly preferred 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 ε-protected L-lysine-N-carboxyanhydrides (NCAs) with a nucleophilic starter;

Method 2 uses derivatives of L-lysine ^* 2 HCl activated at the carboxyl group, method 3 involves the direct thermal polymerization of L-lysines.

Method 1:

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).

Method 2:

Further hyperbranched polylysines were prepared in a one-pot synthesis with activation of the carboxyl group by N-hydroxysuccinimide (NHS) (TL Menz and T. Chapman, Polym. Prep. 2003, 44 (2), 842-743). Method 3:

The thermal polymerization of free lysine is known and was carried out under different reaction conditions:

- Plaquet and co-workers (Biochimie 1975, 57 1395-1396) - Harada (Bull. Chem. Soc., Japan 1959, 32, 1007-1008)

- Rohlfing et al. (Archives of Biochemistry and Biophysics 1969, 130, 441-448) - WO 00/171600

- Fox et al. (BioSystems 1976, 8, 40-44)

Furthermore, WO 2007/0601 19 describes a process for the preparation of uncrosslinked hyperbranched polylysines in which

- (A) a salt of lysine with at least one acid,

(B) optionally at least one amino acid other than lysine,

- (C) optionally at least one di- or polycarboxylic acid or its copolyme-risersfähige derivatives and

(D) if appropriate, at least one diamine or polyamine or their copolymerizable derivatives,

- (E) optionally in at least one solvent at a temperature of 120 to 200 ⁰ C - in the presence of at least one catalyst (F) selected from the group consisting of

- (F1) tertiary amines and amidines,

- (F2) basic alkali metal, alkaline earth metal or quaternary ammonium salts and

- (F3) alkanolates, alkanoates, chelates or organometallic compounds of the metals of groups INA to VIIIA or IB to VB in the Periodic Table of the Elements.

With this process, it is possible to produce 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.

With this process, it is furthermore possible to use 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.

Reference is made to the above references in its entirety.

Cosmetic preparations

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.

For the purposes of the present invention, 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. Water microemulsion, silicone oil in water

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.

If the cosmetic preparation in the sense of the present invention is a solution or emulsion or dispersion, it is possible to use as solvent:

- water or aqueous solutions

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. In particular, mixtures of the abovementioned solvents are used. For alcoholic solvents, water can be another ingredient.

In a preferred embodiment of the invention, the cosmetic preparations in addition to the primary and / or secondary amino-containing polymer further contain at least one oil and / or fat phase.

According to the invention, 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.

Oils, fats and / or waxes

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. Advantageously, 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.

alcohols

The cosmetic preparations may further comprise at least one water-soluble

Contain alcohol. 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.

surfactants

It is advantageous to use primary and / or secondary amino-containing polymers in cleansing products for the skin and hair. 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. According to the invention, 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. In a preferred embodiment of the invention, the cosmetic preparations further contain at least one surfactant in addition to the primary and / or secondary amino group-containing polymer. As surfactants anionic, cationic, nonionic and / or amphoteric surfactants can be used. Surfactants are amphiphilic substances that can dissolve organic, nonpolar substances in water. Due to their specific molecular structure with at least one hydrophilic and one hydrophobic part of the molecule, they ensure a reduction in the surface tension of the water, the wetting of the skin, the facilitation of dirt removal and dissolution, easy rinsing and, as desired, for foam control. Advantageous washing-active anionic surfactants in the context of the present invention are

- Acylamino acids and their salts, such as acylglutamates, in particular sodium acylglutamate

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

- Alkylarylsulfonates.

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. For example, alkylbetaine, alkylamidopropylbetaine and alkylamidopropylhydroxysultaine are advantageous. Further advantageous cationic surfactants are further

- alkylamines,

- Alkylimidazole and - ethoxylated amines and in particular their salts.

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.

Further advantageous amphoteric surfactants are N-alkylamino acids, for example aminopropylalkylglutamide, alkylaminopropionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate. Advantageous washing-active nonionic surfactants are

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)).

Further advantageous 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. In addition to the polymer containing primary and / or secondary amino groups, 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.

It is inventively advantageous if one or more surface-active substances in a concentration of 1 to 30% by weight, preferably in a concentration 5 from 25 to% by weight and very particularly preferably in a concentration of 10 to 20% by weight, respectively be used based on the total weight of the preparation.

In a preferred embodiment of the invention, 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.

Polysorbate

As washing-active agents also Polysorbate can be beneficial in the cosmetic

Preparations are incorporated.

For the purposes of the invention, advantageous polysorbates are, for example

- polyoxyethylene (20) sorbitan monolaurate (Tween ^® 20, CAS No. 9005-64-5-).

- polyoxyethylene (4) sorbitan monolaurate (Tween ^® 21, CAS No. 9005-64-5).

- polyoxyethylene (4) sorbitan monostearate (Tween ^® 61, CAS No. 9005-67-8).

- polyoxyethylene (20) sorbitan tristearate (Tween ^® 65, CAS No. 9005-71 -4.) - polyoxyethylene (20) sorbitan monooleate (Tween ^® 80, CAS No. 9005-65-6-).

- polyoxyethylene (5) sorbitan monooleate (Tween ^® 81, CAS No. 9005-65-5).

- polyoxyethylene (20) sorbitan trioleate (Tween ^® 85, CAS 9005-70-3 number.). Particularly advantageous

- polyoxyethylene (20) sorbitan monopalmitate (Tween ^® 40, CAS 9005-66-7 number.), And - polyoxyethylene (20) sorbitan monostearate (. Tween ^® 60, CAS No. 9005-67-8-).

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.

Antiperspirant components

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.

conditioners If desired, 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.

rheology modifiers

Liquid and gel forms may contain thickeners. For washing, showering and bathing preparations, especially for shampoos and hair care products 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.

preservative

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: Since the raw materials and even the cosmetic preparations themselves are sometimes made in steel equipment, the end products can be iron in

Contain trace amounts. In order to prevent these impurities from adversely affecting the product quality via reactions with dyes and perfume oil components, 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

2006/106140 described. The content of said text is hereby incorporated by reference.

Antioxidants: 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: 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: Furthermore, 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.

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.

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. Of course, 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). 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. 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, e.g. in the form of a cream, a lotion, a cosmetic milk 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,

Propylene glycol or glycerin, or esters of fatty alcohols with low C-alkanoic acids or with fatty acids;

- alkyl benzoates;

- 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. Examples

Nonenal absorption by polymers per se

The inner wall of a 50 ml vial was coated with a polymer film. For this purpose, 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. Then, 0.1 wt .-% 2-nonenal (based on polymer) 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. The results are summarized in the following Table 1.

Table 1: Headspace GC results

Value residual Nonenal rest Nonenal

(ppm) (%)

2-nonenal (reference) 854 100 ε-polylysine (K value = 19.8) ^* (Example 2) 10 17 2 ε-polylysine (K value = 19.8) ^* (Example 2) 6.7 23 2 , 7 hyperbranched polylysine (Example 1) 6.6 5 0.6 ^* The K value was measured from a 1 wt .-% aqueous solution at 25 ° C;

As a reference value, a blank measurement with 2-Nonenal in an empty vial was performed. The results show that all investigated polymers reduce the concentration in the gas space. The pH of the film-forming polymer solution does not matter.

Nonenal absorption by cosmetic emulsions

Approximately 300 mg of each sample was placed on a gauze bandage and weighed into a 20 ml ampoule. The vial was then purged with argon and sealed. Thereafter, 1-10 μl of a solution of 2-nonenal in 1,4-dioxane were added. The ampoule was heated at 40 ^° C. for 1 hour. The subsequent analysis was performed with SPME (Solid Phase Micro Extraction). SPME enables the concentration of volatile and nonvolatile compounds from aqueous and gaseous matrices for GC, GC / MS and HPLC analysis and is known to the person skilled in the art.

synthesis Examples

Example 1 Synthesis of a hyperbranched polyamide from lysine, monohydrochloride (hyperbranched polylysine):

In a 4L four-necked flask equipped with stirrer, internal thermometer, gas inlet tube and descending condenser with vacuum connection and collecting vessel, 1000 g of L-lysine monohydrochloride, 219.1 g of sodium hydroxide, 150.0 g of water and 0.1 g of dibutyltin dilaurate were added and the mixture is heated with stirring to an internal temperature of 150 ⁰ C. After 5 hours of reaction time, water was distilled off under reduced pressure (200 mbar), after passing the largest amount of water, the temperature slowly increased to 180 ⁰ C and the pressure was reduced to 10 mbar. After 8 hours, 380 g of water were collected as distillate. The high-viscosity polymer was discharged hot, poured onto a cooling plate and then finely ground in a mortar. For further processing, the product was dissolved in water to give a 50% by weight solution. To determine the molecular weight distribution, 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. For detection, a UV detector was used, which worked at a wavelength of 230 nm.

Example 1 Reactant Water [wt M n [g mol- ¹ ] Mw [g moi- ¹ ]

L-lysine, mono- 50 4. 800 1 1. 500 hydrochloride

Example 2: Synthesis of ε-polylysine by polycondensation of L-lysine

Template: 15 kg L-lysine monohydrate 1, 5 g sodium hypophosphite

Feed: 12 kg of deionized water

After melting the template (at about 155 ° C) under a nitrogen atmosphere, 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.

Example 3:

O / W base emulsion with 1% by weight polyvinylamine K value 89.9

production:

The phases 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.

Example 4:

O / W base emulsion with 1% by weight polyvinylamine K value 49.5

production:

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:

O / W base emulsion as reference

production:

The phases 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.

Further examples of cosmetic preparations

General instructions for handling the polymers

1. For the polymers, various preparations such as e.g. dispersion; pH adjustment; Swelling or a special method of preparation may be necessary.

2. The polymers may be in suitable encapsulated form.

3. The polymers can be incorporated in the aqueous phase.

4. The polymers can be used in the oil phase.

5. The polymers can be used both in the aqueous and in the oil phase.

6. The polymers can be incorporated with the perfume at about 40 ⁰ C.

7. The polymers can be subsequently incorporated into the emulsion.

8. The preparation of the polymers, the incorporation of the components and the polymers in the corresponding phases and the preparation of the formulations is known in the art and thus not described for the individual formulations.

The following recipe examples are intended to illustrate the use according to the invention without, however, restricting the invention to them.

Example formulations for body lotions

O / W emulsion base

INCI% by weight% by weight% by weight

Ceteareth-25 1, 5 2.0 2.5

Ceteareth-6, Stearyl Alcohol 2.5 2.0 1, 5

Cetyl Alcohol 2.0 2.5 3.0

Cetearyl ethylhexanoate 4.0 5.0 7.0

Hydrogenated polyisobutenes 5.0 2.5 1, 5

Polymer from Example 1 0.2-2.0 0.2-2.0 0.2-2.0

Propylene Glycol 3.0 4.0 5.0

Preservative q.s q.s. q.s.

Aqua ad 100 ad 100 ad 100

Another O / W base emulsion is prepared by using the polymer of Example 2 instead of the polymer of Example 1.

Care Lotion (Type W / O) INCI% by weight% by weight% by weight

PEG-7 Hydrogenated Castor OiI 6.0 5.0 4.5 Mineral OiI, Lanolin Alcohol 2.5 3.0 4.0 PEG-45 / Dodecyl Glycol Copolymer 2.0 2.5 3.0 Isopropyl myristate 6.0 5.0 4.0 Caprylic / Capric Triglycerides 5.0 6.0 7.0 Cyclopentasiloxanes, Cyclohexasiloxanes 5.0 2.0 3.0 Propylene Glycol 3.0 4.0 5.0 Magnesium Stearate 0.75 0.5 0.6 Magnesium Sulfate 0.45 0.5 0.6 Disodium EDTA 0.15 0.1 0.05 Polymer from Example 1 0.2-2.0 0.2-2.0 0.2-2.0 Tocopheryl Acetate 2.0 3.0 1, 0 Tocopherol 0.2 0.1 0.5 Preservative qs qs q.s. Aqua ad 100 ad 100 ad 100

Another care lotion is prepared in which instead of the polymer of Example 1, the polymer of Example 2 is used. Cremegel

INCI% by weight% by weight% by weight

Acrylates / C 10-30 alkyl acrylates 0.5 0.2 0.1

Crosspolymer

Caprylic / Capric triglycerides, 1, 5 0.9 2.0

Sodium acrylate copolymer

Ceteareth-25 2.5 2.0 1, 5

Hydrogenated polyisobutenes 10.0 20.0 15.0

Polymer from Example 1 0.2-2.0 0.2-2.0 0.2-2.0

Propylene Glycol 3.0 5.0 4.0

Sodium hydroxides 0.15 0.05 0.025

Preservative q.s q.s. q.s.

Aqua ad 100 ad 100 ad 100

Another cream gel is prepared in which instead of the polymer of Example 1, the polymer of Example 2 is used.

Example formulations for deodorants / antiperspirants

Deolotion

INCI% by weight% by weight% by weight

Ceteareth-25 1, 5 2.0 1, 0

Ceteareth-6, Stearyl Alcohol 1, 5 2.0 1, 5

PEG-40 Hydrogenated Castor OiI 2.0 1, 0 2.5

Glyceryl Stearate 2.0 1, 5 2.5

Cetyl Alcohol 2.0 3.0 2.5

Hydrogenated Coco-Glycerides 2.0 1, 5 0.5

Decyl Oleate 8.0 10.0 15.0

Polymer from Example 1 0.2-2.0 0.2-2.0 0.2-2.0

Famesol 0.3 1, 0 0.5

Preservative q.s q.s. q.s.

Fragrance q.s q.s. q.s.

Aqua ad 100 ad 100 ad 100

Another deolotion is prepared in which instead of the polymer of Example 1, the polymer of Example 2 is used. antiperspirant

INCI% by weight% by weight% by weight

PEG-40 Hydrogenated Castor OiI 5.0 6.0 3.5

Stearyl Alcohol 26.0 30.0 22.0

Isopropyl palmitate 2.5 10.0 1, 5

Cyclopentasiloxanes, cyclohexasiloxanes 55.0 45.0 50.0

Bisabolol 0.2 0.1 0.5

Polymer from Example 1 0.2-2.0 0.2-2.0 0.2-2.0

Aluminum Chlorohydrate 10.0 5.0 20.0

Alcohol - 3,5 1, 5

Preservative q.s q.s. q.s.

Fragrance q.s q.s. q.s.

Another antiperspirant stick is prepared by using the polymer of Example 2 instead of the polymer of Example 1.

Antiperspirant roll-on

INCI% by weight% by weight% by weight

PEG-40 Hydrogenated Castor OiI 4.0 3.0 2.0

Aluminum zirconium pentachlorohydrate 15.0 5.0 10.0

Famesol 0.1 0.3 0.15

Bisabolol 0.2 0.5 0.1

Polyquaternium-16 1, 5 2.0 3.0

Polymer from Example 1 0.2-2.0 0.2-2.0 0.2-2.0

Hydroxyethyl cellulose 0.5 0.3 0.4

Propylene Glycol 5.0 3.5 3.0

Alcohol 20.0 15.0 25.0

Aqua ad 100 ad 100 ad 100

Preservative q.s q.s. q.s.

Fragrance q.s q.s. q.s.

A further antiperspirant roll-on is produced in which the polymer from example 2 is used instead of the polymer from example 1.

Deodorant spray

INCI% by weight% by weight% by weight

PEG-40 Hydrogenated Castor OiI 1, 0 1, 0 0.5

Polymer from Example 1 0.2-2.0 0.2-2.0 0.2-2.0

Triclosan 0.5 0.3 0.1

Triethyl citrate 2.5 2.0 -

Alcohol 45.0 60.0 40.0

Propylene Glycol 1, 5 2.0 2.5

Aqua ad 100 ad 100 ad 100

Fragrance q.s q.s. q.s.

Bottling: 40% active ingredient solution + 60% butane

Another deodorant spray is prepared in which instead of the polymer of Example 1, the polymer of Example 2 is used.

Example formulations for bath preparations

oil bath

INCI% by weight% by weight

PEG-40 Hydrogenated Castor OiI 24.0 10.0

PEG-7 Glyceryl Cocoate 37.0 ad 100

MIPA-Laureth Sulfate, Laureth-4, Cocamide DEA - 30.0

Cetearyl Ethylhexanoate 15.0 20.0

Caprylic / Capric Triglycerides 14.0 -

Avocado (Persea Gratissima) OiI - 20,0

Panthenol, Propylene Glycol 1, 0 -

Bisabolol 0.1 0.2

Tocopheryl Acetates - 1, 0

Tocopherol - 0.2

Polymer from Example 1 0.2-2.0 0.2-2.0

Preservative q.s q.s.

Fragrance q.s q.s.

Aqua ad 100 -

Another oil bath is prepared by using the polymer of Example 2 instead of the polymer of Example 1. Example formulations for washing preparations

liquid soap

INCI% by weight

Sodium cocoyl isethionate 3.0

Cocamide DEA 2.0

Sodium Laureth Sulfate 13.0

Cocamidopropyl Betaine 6.0

Disodium EDTA 0.1

Polymer from Example 1 0.2-2.0

Sodium Chloride q.s.

Citric Add q.s.

Preservative q.s

Fragrance q.s

Color additive q.s.

Aqua ad 100

Another liquid soap is prepared by using the polymer of Example 2 instead of the polymer of Example 1.

Washing pump foam

INCI% by weight

Poloxamer 188 5.0

Polyquaternium-44 3.8

Cocamidopropyl betaine 15.0

Glycerol 1, 0

Polymer from Example 1 0.2-2.0

Preservative q.s

Fragrance q.s

Aqua ad 100

Another wash pump foam is prepared in which instead of the polymer of Example 1, the polymer of Example 2 is used.

Example formulations for shower preparations

shower gel

INCI% by weight% by weight

PEG-7 Glyceryl Cocoate 2.0 5.0

MIPA-Laureth Sulfate, Laureth-4, Cocamide DEA 2.0 5.0

Cocamide DEA 5,0 -

Propylene Glycol, PEG-55 Propylene Glycol Oleate 3.0 5.0

Sodium Laureth Sulfate 20.0 15.0

Cocamidopropyl Betaine 5.0 10.0

Sodium Laureth Sulfate, Glycol Distearate, Cocamide 5.0 -

MEA, Laureth-10

Polyquaternium 44 2.0 3.0

Hydrogenated polyisobutenes 5.0 2.5

Polymer from Example 1 0.2-2.0 0.2-2.0

Preservative q.s. q.s.

Fragrance q.s. q.s.

Aqua ad 100 ad 100

Another shower gel is prepared in which instead of the polymer of Example 1, the polymer of Example 2 is used.

Claims

claims 1. Use of at least one polymer other than polyethyleneimine, containing primary and / or secondary amino groups in cosmetic preparations for reducing the formation of saturated and unsaturated C6-C22 aldehydes from the unsaturated fatty acids of the skin and / or the scalp caused body odor. 2. Use according to claim 1, characterized in that the primary and / or secondary amino-containing polymer is selected from the A group consisting of polyamides, polyurethanes, polyureas, polymers containing covalently bonded amino acids, oligo- and polysaccharides containing amino groups, vinylamine polymers, allylamine polymers, polypeptides, polyisobutenes containing amino groups and mixtures thereof. 3. Use according to one of claims 1 or 2, characterized in that the primary and / or secondary amino-containing polymer contains covalently bound lysine. 4. Use according to one of claims 1 to 3, characterized in that the primary and / or secondary amino-containing polymer is polylysine. 5. Use according to one of claims 1 to 4, characterized in that the primary and / or secondary amino-containing polymer is α- and / or ε-polylysine. 6. Use according to any one of claims 3 to 5, characterized in that the primary and / or secondary amino-containing polymer is hyperbranched polylysine. 7. Use according to one of claims 1 to 3, characterized in that the polymer containing primary and / or secondary amino groups contains (meth) acrylic acid lysine amide in copolymerized form. 8. Use according to one of claims 1 or 2, characterized in that the primary and / or secondary amino group-containing polymer is a vinylamine polymer. 9. Use according to one of claims 1 to 8, characterized in that the cosmetic preparation, based on the total weight of the preparation tion, in the range of 0.01 to 5 wt .-% of the primary and / or secondary amino-containing polymer. 10. Use according to one of claims 1 to 9, characterized in that the cosmetic preparation is selected from deodorants, antiperspirants, washing, showering and bathing preparations and body lotions. 1 1. A method for reducing the body odor caused by the formation of saturated and unsaturated C6-Ci2-aldehydes from the unsaturated fatty acids of the skin and / or the scalp, characterized in that a cosmetic preparation containing at least one as in one of claims 1 to 10 defined, primary and / or secondary amino-containing polymer is brought into contact with the skin and / or the scalp.