WO2000061103A1

WO2000061103A1 - Cosmetic preparations

Info

Publication number: WO2000061103A1
Application number: PCT/EP2000/003014
Authority: WO
Inventors: Karl Heinz Schmid; Bernd Fabry; Hermann Hensen; Josef Koester
Original assignee: Cognis Deutschland Gmbh
Priority date: 1999-04-10
Filing date: 2000-04-05
Publication date: 2000-10-19
Also published as: DE19916209A1; EP1169018A1; DE19916209C2; AU4746300A; JP2002541179A

Abstract

The invention relates to cosmetic preparations containing (a) hydroxycarboxylic acid alkyl- and/or -alkenyloligoglycoside esters and (b) cationic compounds.

Description

Cosmetic preparations

Field of the Invention

The invention is in the field of cosmetics and relates to preparations which contain special esters of hydroxycarboxylic acids together with cationic compounds, and to the use of the mixtures for the production of cosmetic preparations.

State of the art

The consumer makes a wide variety of demands on cosmetic preparations. For example, if it is a shampoo or shower gel, the cleaning effect is paramount, while creams and lotions are dominated by the nourishing aspects. Irrespective of this, all of these products should have the highest skin and mucous membrane compatibility and at the same time be as environmentally compatible as possible. In the selection of the raw materials for such products, special importance is attached to those which not only consistently meet the requirements mentioned, but which, owing to their diverse properties, can be used in very different preparations, for example both in hair products and in skin care products. An example of such a group of substances is represented by cationic compounds, the substantive properties of which can be used both in hair treatment for conditioning, antistatic treatment and a reduction in combing work, and to improve the sensory properties, in particular the soft feel of the skin. Both monomeric compounds, which are typical cationic surfactants, and polymers are suitable for this purpose. There is a sustained desire to improve the substantive properties of these substances or to achieve the same effects with a reduced amount used.

The object of the invention was therefore to use cationic compounds to provide new cosmetic preparations which are distinguished from the prior art in particular by improved skin and hair softening and reduced combing work. Description of the invention

The invention relates to cosmetic preparations containing

(a) Hydroxycarboxylic acid alkyl and / or alkenyl oligoglycoside esters and

(b) cationic compounds.

Surprisingly, it was found that the addition of the special hydroxycarboxylic acid esters to the cationic compounds, which are preferably (b1) monomeric cationic surfactants and in particular esterquats, and / or (b2) cationic polymers, leads to improved substantivity, which is particularly true results in reduced combing work and improved antistatic equipment. At the same time, skin and hair are given an improved soft feel.

Hydroxycarboxylic acid alkyl and / or alkenyl oligonucleotides

Esters of hydroxycarboxylic acids and alkyl and alkenyl oligoglycosides which form component (a) are known nonionic surfactants which follow the formula (I),

OH

I RiOOC-C-CH-COOR *

(I)

I I

X Y

in which X represents hydrogen or a CH2COOR ³ group, Y represents hydrogen or a hydroxyl group, R ¹ , R ² and R ³ independently of one another represent hydrogen, an alkali or alkaline earth metal, ammonium, alkylammonium, hydroxyalkylammonium, glucammonium or the rest an alkyl and / or alkenyl oligoglycoside of the formula (II),

R ⁴ 0- [G] _P (II)

in which R ^{4 is} an alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p is a number from 1 to 10, with the provisos that in the event that X is a CH2COOR ³ group, Y is hydrogen and at least one of the radicals R ¹ , R ² and R ^{3 represents} a glycoside radical. The production and use of these substances as high-foaming surfactants in cosmetic preparations is known from European patent EP 0258814 B1 (Auschem), to which reference should be made in full here.

The acid component of the nonionic surfactants can be derived from malic acid, tartaric acid or citric acid and their mixtures. Depending on the number of hydroxyl groups present in the acid component, mono-, di- or triesters and their technical mixtures can be present. However, preference is given to using monoesters or mixtures with a high monoester content, which can be obtained by a person skilled in the art in accordance with the teaching of EP 0258814 B1 already mentioned.

The alkyl and / or alkenyl oligogiycoside component can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose. The preferred nonionic surfactants are thus esters of alkyl and / or alkenyl oligoglucosides. The index number p in the general formula (II) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10. While p in a given compound must always be an integer and here can assume the values p = 1 to 6 in particular, the value p for a certain alkyl oligoglycoside is an analytically determined arithmetic parameter, which usually represents a fractional number. Esters are preferably used whose alkyl and / or alkenyl oligogiycoside component has an average degree of oligomerization p of 1.1 to 3.0. From an application point of view, preference is given to those alkyl and / or alkenyl oligoglycoside esters whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4. The alkyl or alkenyl radical R ¹ can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capro alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis. Preference is given to Cg-Cn- or Cβ-C-io-alkyl oligoglucoside esters with a DP = 1 to 3, the alkyl radical of which is derived from corresponding oxo alcohols or alcohols, which is used as a preliminary step in the separation of technical C ₈ -C ₈ -8 coconut oil alcohol by distillation accumulate and can be contaminated with a proportion of less than 6 wt .-% Cι ₂ alcohol. The alkyl or alkenyl radical R ¹ can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and their technical mixtures, which can be obtained as well as their technical mixtures. Alkyl oligoglucoside esters based on hardened C-i2 / ι ₄ coconut are preferred. alcohol with a DP of 1 to 3. Such products are commercially available under the Eucarol® brand.

The invention includes the knowledge that mixtures of hydroxycarboxylic acid alkyl and / or alkenyl glycoside esters and alkyl and / or alkenyl oligoglycosides together with cationic compounds show particularly good performance properties. In the simplest case, such further preparations can be prepared by mixing the three components. In a particular embodiment of the invention, however, cationic compounds are used together with hydroxycarboxylic acid glycoside esters which still contain 1 to 50, preferably 5 to 25 and in particular 10 to 15% by weight of unesterified glycosides.

Esterquats

In a first preferred embodiment of the invention, the cationic compounds which form component (b) are monomeric cationic surfactants, preferably those which are commercially available under the name esterquats. This generally means quaternized fatty acid triethanolamine ester salts. These are known substances that can be obtained using the relevant methods of preparative organic chemistry. In this connection, reference is made to international patent application WO 91/01295 (Henkel), according to which triethanolamine is partially esterified with fatty acids in the presence of hypophosphorous acid, air is passed through and then quaternized with dimethyl sulfate or ethylene oxide. German patent DE 4308794 C1 (Henkel) also discloses a process for the preparation of solid ester quats, in which the quaternization of triethanolamine esters is carried out in the presence of suitable dispersants, preferably fatty alcohols. Overviews on this topic have been published, for example, by R.Puchta et al. in Tens.Surf.Det., 30, 186 (1993), M.Brock in Tens.Surf.Det. 30: 394 (1993) R. Lagerman et al. in J.Am.Oil.Chem.Soc, 71, 97 (1994) and I.Shapiro in Cosm.Toil. 109, 77 (1994) appeared. The quaternized fatty acid triethanolamine ester salts follow the formula (III)

R ⁸

I [R5CO- (OCH2CH ₂ ) mOCH2CH2-N ⁺ -CH2CH2θ- (CH ₂ CH2θ) nR ⁶ ] X "

(III)

in the R ⁵ CO for an acyl radical having 6 to 22 carbon atoms, R ⁶ and R ⁷ independently of one another for hydrogen or R ⁵ CO, R ⁸ for an alkyl radical with 1 to 4 carbon atoms or one (CH2CH2θ) _q H group, m, n and p in total for 0 or numbers from 1 to 12, q for numbers from 1 to 12 and X for halide, alkyl sulfate or alkyl phosphate. Typical examples of ester quats which can be used in the context of the invention are products based on caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachic acid, behenic acid and erucic acid and their technical mixtures , as they occur, for example, in the pressure splitting of natural fats and oils. Technical Ci2 / i8 coconut fatty acids and in particular partially hardened C16 / 18 tallow or palm fatty acids as well as high elaidic acid Ci6 / 18 fatty acid cuts are preferably used. The fatty acids and the triethanolamine can be used in a molar ratio of 1.1: 1 to 3: 1 to produce the quaternized esters. With regard to the application properties of the ester quats, an application ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous. The preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical Cie / iβ-tallow or palm fatty acid (iodine number 0 to 40). From an application point of view, quaternized fatty acid triethanolamine ester salts of the formula (III) have proven to be particularly advantageous in which R ⁵ CO for an acyl radical having 16 to 18 carbon atoms, R ⁶ for R CO, R ⁷ for hydrogen, R ⁸ for a methyl group, m, n and p is 0 and X is methyl sulfate. In addition to the quaternized fatty acid triethanolamine ester salts, quaternized ester salts of fatty acids with diethanolalkylamines of the formula (IV) are also suitable as esterquats.

R «

I [R5CO- (OCH2CH2) mOCH2CH ₂ -N ⁺ -CH2CH2θ- (CH ₂ CH2θ) nR ⁶ ] X-

(IV)

I.

R ⁹

in which R ⁵ CO represents an acyl radical having 6 to 22 carbon atoms, R ^{6 represents} hydrogen or R ⁵ CO, R ⁸ and R ⁹ independently of one another for alkyl radicals having 1 to 4 carbon atoms, m and n in total for 0 or numbers of 1 to 12 and X represents halide, alkyl sulfate or alkyl phosphate. Finally, a further group of suitable ester quats are the quaternized ester salts of fatty acids with 1,2-dihydroxy-propyldialkylamines of the formula (V)

[R8.N ⁺ -CH ₂ CHCH2θ- (CH2CH2θ) nR ⁶ ] X-

(V) I in which R ⁵ CO for an acyl radical with 6 to 22 carbon atoms, R ⁶ for hydrogen or R ⁵ CO, R ⁸ , R ¹⁰ and R ¹¹ independently of one another for alkyl radicals with 1 to 4 carbon atoms, m and n in total for 0 or numbers from 1 to 12 and X represents halide, alkyl sulfate or alkyl phosphate. With regard to the selection of the preferred fatty acids and the optimal degree of esterification, the examples given for (III) also apply to the esterquats of the formulas (IV) and (V).

Tetraalkylammonium compounds

Instead of the ester quats it is also possible to use tetraalkylammonium compounds, which are usually referred to as quaternary ammonium compounds (QAV) and preferably follow the formula (VI)

R14

in which R ^{14 represents} a linear or branched, saturated or unsaturated hydrocarbon radical with 12 to 22 carbon atoms or a benzyl radical, R ¹⁴ and R ¹⁵ independently of one another for R ¹² or an optionally hydroxy-substituted alkyl radical with 1 to 10 carbon atoms, R ¹⁵ for an optionally hydroxy-substituted one Alkyl radical with 1 to 4 carbon atoms and X represents halide, alkyl sulfate or alkyl phosphate. Typical examples are dimethyldistearylammonium chloride, cetyltrimethylammonium chloride or benzyltrimethylammonium chloride.

Cationic polymers

In a further embodiment of the invention, the cationic compounds which form component (b) can be polymers. Suitable cationic polymers are, for example, cationic cellulose derivatives, such as, for example, a quaternized hydroxyethyl cellulose, which is available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole Polymers such as Luviquat® (BASF), condensation products of polyglycols and nurses, quaternized collagen polypeptides such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grunau), quaternized wheat polypeptides polyethyleneimine, cationic

Silicone polymers, such as amidomethicones, copolymers of adipic acid and dimethylamino-hydroxypropyldiethylenetπamm (Cartaretιne® / Sandoz), copolymers of acrylic acid with dimethyl-diallylammonium chloride (Merquat® 550 / Chemvιron), polyaminopolyamides, as described in FR.225, as described in FR Polymers, cationic chitin derivatives such as, for example, quaternized chitosan, optionally microcrystalline, condensation products of dihaloalkylene, such as, for example, dibromobutane with bisdialkylamines, such as, for example, bis-dimethylamino-1,3-propane, cationic guar gum, such as, for example, Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers such as Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol

Typically, the preparations can contain components (a) and (b) in a weight ratio of 11 to 10 1. If the cationic compounds are monomeric cationic surfactants, the use ratio is preferably 1 1 to 5 1, while in the case of cation polymers rather higher operating ratios, such as 5 1 to 10 1, are used. In total, the mixtures of components (a) and (b) are usually present in the preparations in amounts of 0.5 to 20, preferably 1 to 15 and in particular 2 to 10 Wt .-% - based on the means - included

Industrial applicability

The preparations according to the invention, which contain the special hydroxycarboxylic acid esters together with the cationic compounds, especially the monomeric cationic surfactants and / or the cationic polymers, lead to a lasting improvement in the wet and dry combability, the antistatic finish and the sensory assessment of skin and Another object of the invention therefore relates to the use of the mixtures for the production of cosmetic preparations in which they are present in amounts of 0.5 to 20, preferably 1 to 15 and in particular 5 to 10% by weight, based on the composition can

Cosmetic and / or pharmaceutical preparations

The mixtures according to the invention can be used for the production of cosmetic preparations, such as, for example, hair shampoos, hair lotions, bubble baths shower baths, creams, gels, lotions, alcoholic and water / alcoholic solutions, emulsions, wax / fat compositions, stick Serve preparations powders or ointments These agents can also be used as further auxiliaries and additives, mild surfactants, oil emulsifiers, superfatting agents, pearlescent waxes, consistency agents, thickeners, polymers, silicone compounds, fats, waxes, stabilizers, biogenic agents, deodorants, antidandruff agents, film formers, swelling agents, UV light protection factors, Contain antioxidants, hydrotropes, preservatives, insect repellents, self-brown solubilizers, perfumes, dyes, germ-inhibiting agents and the like

Typical examples of suitable mild, ie particularly skin-compatible, surfactants are fatty alcohol polyglycol ether sulfates, monoglycene sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid esters, fatty acid glutamates, α-olefin sulfonucs, alkyl amide, fatty amides, fatty amides, carboxamides or protein fatty acid condensates, the latter preferably based on wheat proteins

Guerbet alcohols based on fatty alcohols with 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C6-C22 fatty acids with linear C&C22 fatty alcohols, esters of branched C6-C ₃ carboxylic acids with linear Cε-C are examples of oil bodies ΣΣ fatty alcohols, such as Myπstylmyristat, Myπstylpalmitat, Myπstylstearat, Myπstylisostearat, myristyl, Myπstyl- behenate, Myπstylerucat, Cetylmynstat, cetyl palmitate, cetyl stearate, Cetylisostearat, cetyl oleate, Ce tylbehenat, Cetylerucat, Stearylmyristat, Stearyipalmitat, stearyl stearate, Stearylisostearat, Steary - loleat, sostearylisostearat stearyl, Stearylerucat, Isostearylmyπstat, isostearyl, Isostearylstearat, I, Isostearyloieat, isostearyl behenate, Isostearyloleat, oleyl, oleyl palmitate, oleyl stearate, oleyl isostearate, oleate, Oleylbehenat, oleyl, Behenylmynstat, behenyl palmitate, behenyl, Behenylisostearat, behenyl oleate, behenyl , Behenylerucate, erucyl - myristat, erucyl palmitate, erucyl stearate, erucyi isostearate, erucyl oleate, erucyl behenate and erucylerucat. In addition, esters of linear Cε-C∑∑ fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of hydroxycarboxylic acids with linear or branched C6-C22 fatty alcohols, in particular dioctyl malates, esters of linear and / or branched fatty acids with polyhydric alcohols (such as propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, Tπglycende based on Cδ-Cio fatty acids, liquid mono- / di- / Tπglyceπdmιschungen based on Cβ-Ciβ-fatty acids, esters of C6-C ₂ 2 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C∑-Ci∑-dicarboxylic acids with linear or branched alcohols with 1 to 22 carbon atoms or polyols with 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, Substituted cyclohexanes, linear and branched Ce-C∑∑ fatty alcohol carbonates, Guerbet carbonates, esters of benzoic acid with linear and / or ve branched C6-C22 alcohols (eg Finsolv® TN), linear or branched, symmetrical or unsymmetrical dialkyl ethers with 6 to 22 carbon atoms per alkyl group ring opening products of epoxidized fatty acid esters with polyols, lyols, silicone oils and / or aliphatic or naphthenic hydrocarbons, such as, for example, squalane, squalene or dialkylcyclohexanes.

Examples of suitable emulsifiers are nonionic surfactants from at least one of the following groups:

(1) Adducts of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 C atoms, with fatty acids with 12 to 22 C atoms and with alkylphenoies with 8 to 15 C atoms in the Alkyl group;

(2) Ci2 / i8 fatty acid monoesters and diesters of adducts of 1 to 30 moles of ethylene oxide with glycerol;

(3) glycerol monoesters and diesters and sorbitan monoesters and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and their ethylene oxide addition products;

(4) alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs;

(5) adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hardened castor oil;

(6) polyol and especially polyglycerol esters, e.g. Polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimer isostearate. Mixtures of compounds from several of these classes of substances are also suitable;

(7) adducts of 2 to 15 moles of ethylene oxide with castor oil and / or hardened castor oil;

(8) partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid as well as 12-hydroxystearic acid and glycerin, polyglycerin, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside , Lauryl glucoside) and polyglucosides (eg cellulose);

(9) mono-, di- and trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates and their salts;

(10) wool wax alcohols;

(11) polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives;

(12) mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE 1165574 PS and / or mixed esters of fatty acids with 6 to 22 carbon atoms, methyl glucose and polyols, preferably glycerol or polyglycerol,

(13) polyalkylene glycols and

(14) Glycerol carbonate. The adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are homolog mixtures, the middle of which Degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out. Ci2 / ιs fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE 2024051 PS as refatting agents for cosmetic preparations.

Cδ / is alkyl mono- and oligoglycosides, their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms. Regarding the glycoside residue, both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to about 8 are suitable. The degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.

Zwitterionic surfactants can also be used as emulsifiers. Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the coconut acylaminopropyldimethylammonium glycinate, and 2-alkylmethyl-carboxylate -3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate. The fatty acid amide derivative known under the CTFA name of Cocamidopropyl Betaine is particularly preferred. Suitable emulsifiers are ampholytic surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a Cβ / iβ-alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SOßH group in the molecule and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-aikylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylamino acetic acid each with 8 to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylamino propionate and Ci2 / i8-acylsarcosine. Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.

Pearlescent waxes, for example, are: alkylene glycol esters, especially ethylene glycol distearate; Fatty acid alkanolamides, especially coconut fatty acid diethanolamide; Partialglyceπde, especially stearic acid monoglyceride; Esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; Fatty substances, such as, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which have a total of at least 24 carbon atoms, especially lauron and distearyl ether; Fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring opening products of olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms and / or polyols with 2 to 15 carbon atoms and 2 to 10 hydroxyl groups and mixtures thereof.

Suitable consistency agents are primarily fatty alcohols or hydroxy fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and, in addition, partial glycerides, fatty acids or hydroxy fatty acids. A combination of these substances with alkyl oligoglucosides and / or fatty acid N-methyl glucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred. Suitable thickeners are, for example, Aerosil types (hydrophilic silicas), polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, ( e.g. Carbopole® from Goodrich or Synthalene® from Sigma), polyacrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosulfide and electrolytes such as ammonium chloride and ammonium chloride.

Suitable anionic, zwitterionic, amphoteric and nonionic polymers are, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / Vinylacryiat copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and esters thereof, uninjured and polyol-crosslinked polyacrylic acids, acrylamidopropyl - Trimethyiammonium chloride / acrylate copolymers, octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxyproyl methacrylate copolymers, polyvinylpyrrolidone, vinyl pyrrolidone / vinyl acetate copolymers, vinyl pyrrolidone / dimethylaminoethyl methacrylate and acrylate, if appropriate, and vinylamino / vinyl methacrylate / acrylate / methacrylate / acrylate / vinyl amide methacrylate / methacrylate / methacrylate / methacrylate / acrylate / methacrylate / acrylate / methacrylate / methacrylate / methacrylate / methacrylate / acrylate / methacrylate / acrylate / methacrylate / methacrylate / methacrylate / acrylate / methacrylate / acrylate / vinylamine acrylate / methacrylate and optionally / vinylamino / methacrylate / acrylate / methacrylate / acrylate / methacrylate / methacrylate / methacrylate / methacrylate / methacrylate / methacrylate in / in) and / or vinyl pyrrolidone / dimethylaminoethyl methacrylate as in the case of . Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenyipolysiloxanes, cyclic silicones and ammo-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glycoside- and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature. Simethicones, which are mixtures of dimethicones with an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicates, are also suitable. A detailed overview of suitable volatile silicones can also be found by Todd et al. in Cosm.Toil. 91, 27 (1976).

Typical examples of fats are glycides, waxes include natural waxes, such as Candelilla wax, carnauba wax, japan wax, esparto grass wax, cork wax, guaruma wax, rice-germ oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, walnut, lanolin (wool wax), pretzel fat, ceresin, ozokerite (earth wax), petrolatum, paraffin waxes chemically modified waxes (hard waxes), e.g. Montanester waxes, Sasol waxes, hydrogenated jojoba waxes and synthetic waxes, such as Polyalkylene waxes and polyethylene glycol waxes in question.

Metal salts of fatty acids, such as e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate are used.

Biogenic active substances are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamine complexes.

Antiperspirants such as aluminum chlorohydates are suitable as deodorant active ingredients. These are colorless, hygroscopic crystals that easily dissolve in the air and arise when aqueous aluminum chloride solutions are evaporated. Aluminum chlorohydrate is used in the manufacture of antiperspirant and deodorant preparations and is likely to act by partially occluding the sweat glands through protein and / or polysaccharide precipitation [cf. J. Soc. Cosm.Chem. 24, 281 (1973)]. For example, an aluminum chlorohydrate that corresponds to the formula [Al2 (OH) 5CI] * 2.5 H2O and whose use is particularly preferred is commercially available under the brand Locron® from Hoechst AG, Frankfurt / FRG [cf. J.Pharm.Pharmacol. 26, 531 (1975)]. In addition to the chlorohydrates, aluminum hydroxylactates and acidic aluminum / zirconium salts can also be used. Esterase inhibitors can be added as further deodorant active ingredients. These are preferably trialkyl citrates such as methyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and in particular triethyl citrate (Hydagen® CAT, Henkel KGaA, Düsseldorf / FRG). The substances inhibit enzyme activity and thereby reduce odor. The cleavage of the citric acid ester probably releases the free acid, which lowers the pH value on the skin to such an extent that the enzymes are inhibited. Further substances which can be considered as esterase inhibitors are sterol sulfates or phosphates, such as, for example, lanosterol, cholesterol, campesterin, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and their esters, such as, for example, glutaric acid, glutaric acid monoethyl ester, and glutaric acid diethyl ester , Adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester, hydroxycarboxylic acids and their esters such as citric acid, malic acid, tartaric acid or tartaric acid diethyl ester. Antibacterial agents that influence the bacterial flora and kill sweat-killing bacteria or inhibit their growth can also be contained in the stick preparations. Examples of these are chitosan, phenoxyethanol and chlorhexidine gluconate. 5-Chloro-2- (2,4-dichlorophen-oxy) phenol, which is sold under the Irgasan® brand by Ciba-Geigy, Basel / CH, has also proven to be particularly effective.

Climbazole, octopirox and zinc pyrethione can be used as antidandruff agents. Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds. Montmorillonites, clay minerals, pemulene and alkyl-modified carbopol types (Goodrich) can serve as swelling agents for aqueous phases. Further suitable polymers or swelling agents can be found in the overview by R. Lochhead in Cosm.Toil. 108, 95 (1993).

UV light protection factors are understood to mean, for example, organic substances (light protection filters) which are liquid or crystalline at room temperature and which are able to absorb ultraviolet rays and absorb the energy absorbed in the form of longer-wave radiation, e.g. To give off heat again. UVB filters can be oil-soluble or water-soluble. As oil-soluble substances e.g. to call:

3-benzylidene camphor or 3-benzylidene norcampher and its derivatives, e.g. 3- (4-methylbenzylidene) camphor as described in EP 0693471 B1;

4-aminobenzoic acid derivatives, preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate;

• Esters of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate, propyl 4-methoxycinnamate, 2-cyano-3,3-phenylcinnamate-2-ethylhexyl ester (octocrylene) 4-methoxycinnamate; Esters of salicylic acid, preferably salicylic acid 2-ethylhexyl ester, salicylic acid 4-isopropyl benzyl ester, salicylic acid homomethyl ester;

Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2J'-dihydroxy-4-methoxybenzophehone;

Esters of benzalmalonic acid, preferably di-2-ethylhexyl 4-methoxybenzmalonate;

Triazine derivatives, e.g. 2,4,6-trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1, 3,5-triazine and octyl

Triazon, as described in EP 0818450 A1;

Propane-1,3-dione, e.g. 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1,3-dione;

Ketotricyclo (5.2.1.0) decane derivatives, as described in EP 0694521 B1.

Possible water-soluble substances are:

• 2-phenylbenzimidazole-5-sulfonic acid and its alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and glucammonium salts;

• sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts;

Sulfonic acid derivatives of 3-benzylidene camphor, e.g. 4- (2-oxo-3-bomylidenemethyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bornylidene) sulfonic acid and their salts.

Derivatives of benzoylmethane, such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione, 4-tert-butyl, are particularly suitable as typical UV-A filters -4'-methoxy-dibenzoylmethane (Parsol 1789), or 1-phenyl-3- (4'-isopropylphenyl) propane-1,3-dione. The UV-A and UV-B filters can of course also be used in mixtures. In addition to the soluble substances mentioned, insoluble light protection pigments, namely finely dispersed metal oxides or salts, are also suitable for this purpose. Examples of suitable metal oxides are, in particular, zinc oxide and titanium dioxide and, in addition, oxides of iron, zirconium, silicon, manganese, aluminum and cerium and mixtures thereof. Silicates (talc), barium sulfate or zinc stearate can be used as salts. The oxides and salts are used in the form of the pigments for skin-care and skin-protecting emulsions and decorative cosmetics. The particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They can have a spherical shape, but it is also possible to use particles which have an ellipsoidal shape or shape which differs from the spherical shape in some other way. The pigments can also be surface-treated, ie hydrophilized or hydrophobicized. Typical examples are coated titanium dioxides such as titanium dioxide T 805 (Degussa) or Eusolex® T2000 (Merck). Silicones, and in particular trialkoxyoctylsilanes or simethicones, are particularly suitable as hydrophobic coating agents. So-called micro- or nanopigments used. Micronized zinc oxide is preferably used. Further suitable UV light protection filters can be found in the overview by P.Finkel in SÖFW-Journal 122, 543 (1996).

In addition to the two aforementioned groups of primary light stabilizers, secondary light stabilizers of the antioxidant type can also be used, which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin. Typical examples include amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carosin and their derivatives (e.g. Anserine), carotenoids, carotenes (e.g. α-carotene, ß-carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (e.g. dihydroliponic acid), aurothioglucose, propylthiouracii and other thiols (e.g. thioredoxin, glyutathione, Cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g. buthioninsulfoximines, homocysteine sulfoximine, butioninsulfones, penta-, hexa-, himinathionine sulfoxin) n very low tolerable doses (e.g. pmol to μmol / kg), also (metal) chelators (e.g. α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids

(e.g. citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g. γ-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (for example ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopheroia and derivatives (for example vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl benzoate of the benzoin, rutinic acid and their derivatives, α-glycosyl rutin, ferulic acid, furfurylidene glucitol, carnosine, butylated hydroxytoluene, butylated hydroxyanisole, nordic hydroguajak resin acid, nordihydroguajaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and their derivatives, eg zinc oxide dismutase (zinc oxide dismutase) ZnS0 ₄ ) selenium and its derivatives (eg selenium methionine), stilbenes and their derivatives (eg stilbene oxide, trans-stilbene oxide) and the inventive Suitable derivatives (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active substances.

Hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior. Poiyols which come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. The polyols can also contain further functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are • glycerin;

Alkylene glycols, such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;

Technical oligoglycerol mixtures with a degree of self-condensation of 1.5 to 10, such as technical diglycerol mixtures with a diglycerol content of 40 to 50% by weight;

• Methyl compounds, such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;

• Lower alkyl glucosides, in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;

Sugar alcohols with 5 to 12 carbon atoms, such as sorbitol or mannitol,

• Sugar with 5 to 12 carbon atoms, such as glucose or sucrose;

Aminosugars, such as glucamine;

• Dialcohol amines, such as diethanolamine or 2-amino-1, 3-propanediol.

Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the other classes of substances listed in Appendix 6, Parts A and B of the Cosmetics Ordinance. N, N-diethyl-m-toluamide, 1, 2-pentanediol or 3535 insect repellants are suitable as insect repellants, and dihydroxyacetone is suitable as a self-tanning agent.

Perfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), Needles and twigs (spruce, fir, pine, mountain pine), resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials, such as civet and castoreum, are also suitable. Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl methylphenyl glycinate, allyl cyclohexyl benzylatepylpionate, allyl cyclohexyl propyl pionate. The ethers include, for example, benzyl ethyl ether, the aldehydes, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and Bourgeonal, to the ketones eg the Jonone, oc-isomethytionone and methylcedryl ketone, to the alcohols anethole, citronellol, eugenol. Isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, the hydrocarbons mainly include the terpenes and balms. However, preference is given to using mixtures of different fragrances which together produce an appealing fragrance. Essential oils of low volatility, which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil. Bergamot oil, dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, α-hexylcinnamaldehyde, geraniol, benzylacetone, cyclamaldehyde, linalool, boisambrene forte, ambroxan, indole, hedione, sandelice, lemon oil, manalatyl allyl oil, oramino allyl oil, orlamine oil, orolamine oil, orolamine oil, orolamine oil, orolamine oil, orangolin oil, orolamine oil, orolamine oil, oraline oil, oraline oil, orolamine oil, oraline oil, oraline oil , Lavandin oil, muscatel sage oil, ß-da- mascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-E-Super, Fixolide NP, Evernyi, Iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romilllate, irotyl and floramate alone Mixtures used.

The dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes" by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.

Typical examples of germ-inhibiting agents are preservatives with a specific action against gram-positive bacteria, such as, for example, 2,4,4'-trichloro-2'-hydroxydiphenyl ether, chlorhexidine (1,6-di- (4-chlorophenyl-biguanido) hexane) or TCC (3,4,4'-trichlorocarbanilide). Numerous fragrances and essential oils also have antimicrobial properties. Typical examples are the active ingredients eugenol, menthol and thymol in clove, mint and thyme oil. An interesting natural deodorant is the terpene alcohol farnesol (3,7, 11-trimethyl yl-2,6, 10-dodecatrien-1-ol), which is present in the linden blossom oil and has a lily of the valley smell. Glycerol monolaurate has also proven itself as a bacteriostatic. The proportion of the additional germ-inhibiting agents is usually about 0.1 to 2% by weight, based on the solids content of the preparations.

The total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition. The agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used. Examples

Dry combability was examined with the approval of electrostatic charging. A relative humidity of 20% was set. The conditioning time was 12 h at 30 ° C. The measurement was carried out using the charge tapping on a double Faraday cage after 10 combs. The error in the measurements was 2.5% on average, the statistical certainty was at least 99.9%.

Wet combability was investigated on brown hair (Alkinco # 6634, strand length 12 cm, strand mass 1 g). After the zero measurement, the strands were soaked with 100 ml of the test formulations. After a contact time of 5 minutes, the strands were rinsed out under running water (1 l / min, 38 ° C.) for 1 minute. The strands were measured again and compared with the zero measurement. The error in the measurements was 2% on average, the statistical certainty was at least 99%. A detailed description of the measurement methods can be found in J.Soc.Cosm.Chem., 24, 782 (1973).

The results are summarized in Table 1. Examples 1 to 8 are according to the invention, examples V1 to V8 are used for comparison. All quantities are understood as% by weight.

Table 1 Improvement of combability

Table 1

Combability Improvement - Continued

Claims

claims

1. Cosmetic and / or pharmaceutical preparations containing

(a) Hydroxycarboxylic acid alkyl and / or alkenyl oligoglycoside esters and

(b) cationic compounds.

2. Preparations according to claim 1, characterized in that they contain as component (a) hydroxy-carboxylic acid alkyl and / or alkenyl oligoglycoside esters of the formula (I),

OH

(I)

I I X Y

in which X represents hydrogen or a CH2COOR ³ group, Y represents hydrogen or a hydroxyl group, R ¹ , R ² and R ³ independently of one another represent hydrogen, an alkali or alkaline earth metal, ammonium, alkylammonium, hydroxyalkylammonium, glucammonium or the rest of an alkyl - and / or alkenyl oligoglycoside of the formula (II),

R ⁴ 0- [G] _p dl)

in which R ^{4 is} an alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p is a number from 1 to 10, with the provisos that in the event that X represents a CH2COOR ³ group, Y represents hydrogen and at least one of the radicals R ¹ , R ² and R ^{3 represents} a glycoside radical.

3. Preparations according to claims 1 and / or 2, characterized in that they contain esters of malic acid, tartaric acid and / or citric acid with alkyl and / or alkenyl oligoglycosides.

4. Preparations according to at least one of claims 1 to 3, characterized in that they contain esters which still contain 1 to 50 wt .-% unesterified glycosides.

5. Preparations according to at least one of claims 1 to 4, characterized. that they contain monomeric cationic surfactants and / or cationic polymers as component (b).

6. Preparations according to at least one of claims 1 to 5, characterized in that they contain as component (b1) monomeric cationic surfactants of the esterquat and / or tetraalkylammonium salt type.

7. Preparations according to at least one of claims 1 to 6, characterized in that they contain, as component (b2), cationic polymers which are selected from the group formed by cationic cellulose derivatives, cationic starches, copolymers of diallylammonium salts and acrylamides , quaternized Vinyipyrroli- don / Vinyiimidazol polymers., condensation products of polyglycols and amines, quaternized collagen polypeptides, quaternized Weizenpolypeptiden, polyethyleneimines, cationic Siliconpoiymeren, copolymers of adipic acid and Dimethylaminohydroxypropyl- diethylenetriamine, copolymers of acrylic acid with dimethyldiallylammonium chloride, nopolyamiden polyamides, cationic chitin derivatives, condensation products from dihaloalkylene, cationic guar gums and / or quaternized ammonium salt polymers.

8. Preparations according to at least one of claims 1 to 7, characterized in that they contain components (a) and (b) in a weight ratio of 1: 1 to 10: 1.

9. Preparations according to at least one of claims 1 to 8, characterized in that they contain the mixtures of components (a) and (b) in total in amounts of 0.5 to 20 wt .-% - based on the composition.

10. Use of mixtures containing

(a) Hydroxycarboxylic acid alkyl and / or alkenyl oligoglycoside esters and

(b) cationic compounds

for the manufacture of cosmetic preparations.