WO1998049998A2 - Use of glycosidic silicon compounds for producing cosmetic and/or pharmaceutical preparations - Google Patents

Abstract

The invention relates to the use of glycosidic silicon compounds for producing cosmetic and/or pharmaceutical preparations, said compounds being of formula (I) R2xR13-xSiO-[(SiR1R2O)m-(SiR12O)n]y-SiR13-xR2x, wherein R1 represents hydrogen or an optionally substituted alkyl and/or alkenyl radical with 1 to 18 carbon atoms, R2 represents a radical of formula (II) R3(R4O)c[G]p wherein R3 represents alkylene radicals with 1 to 18 carbon atoms, R4 represents alkylene radicals with 2 to 4 carbon atoms, G represents glycoside radicals with 5 to 12 carbon atoms, p represents numbers from 1 to 10 and c represents 0 or numbers from 1 to 20, m represents 0 or numbers from 1 to 200, n represents 0 or numbers from 1 to 1000, x represents 0 or 1 and y represents 0 or numbers from 1 to 1200, on the condition that (I) contains at least one radical R2.

Description

Use of glycosidic silicone compounds for the production of cosmetic and / or pharmaceutical preparations

Field of the Invention

The application relates to the use of glycosidic silicone compounds as emulsifiers for the production of cosmetic or pharmaceutical preparations and preparations which contain these substances together with selected surfactants.

State of the art

Silicones are used in skin and hair cosmetics as additives to influence grip and shine. An overview of the use of conventional silicones in cosmetics can be found, for example, by K. Schnurrbusch in Seifen-Fette-Öle-Wwachs 100, 173, 1974). The combination of alkyl glucosides with silicones in the cosmetics is known from the publications EP-A2 0398177 (Kao) and DE-A1 4231659.

In the documents JP-A1 Hei 07/041414, JP-A1 Hei 07/041415, JP-A1 Hei 07/041416, and JP-A1 Hei 07/041417 (Shiseido) and the patent US 5,550,219 (Siltech), sugar-modified silicones and described their use in cosmetics. Anionic, cationic and nonionic alkyl glucoside silicone ethers are known from the publications WO 94/29322, WO 94/29323 and WO 94/29324 (Bayer). Glycosidically substituted silicone compounds, a process for their preparation and the use of the substances as surfactants are known from European Patent EP-B1 0612759 (Wacker); however, these substances have not yet been proposed for use in cosmetics.

The so-called "build-up" effect can be disadvantageous when using conventional silicone polymers, such as of the dimethylpolysiloxane type. This is to be understood to mean that a layer of polymers builds up on the skin or hair when repeated use of silicone-containing products which is difficult to remove by simple washing, especially with hair this can lead to stress and possible impairment of further treatments such as waves or dyeing. There is therefore a desire for silicone compounds with sufficient water solubility that are removed again when cleaning the skin and hair. At the same time, these substances should have at least equally good, preferably better, finishing properties than conventional silicone oils and, for example, give skin and hair a pleasant sensory feeling. Another problem is that silicones do not have sufficient biodegradability for a number of applications, so that there is also a particular interest in the market for silicone compounds which are more easily accessible to degradation by microorganisms. Another market need is for silicones with emulsifying properties which give emulsions sufficient phase stability even after prolonged storage at elevated temperature and do not cause changes in viscosity.

Accordingly, the object of the present invention was to provide emulsifiers for use in cosmetics and pharmacy which fulfill the complex task described above.

Description of the invention

The invention relates to the use of glycosidic silicone compounds of the formula (I),

R2 _x Ri ₃ .χSiO - [(SiRiR20) _m - (SiRi2θ) n] ySiRi ₃ .χR2 _x (I)

in which R ^{1 is} hydrogen or an optionally substituted alkyl and / or alkenyl radical having 1 to 18 carbon atoms, R ^{2 is} a radical of the formula (II),

R ³ for alkylene radicals with 1 to 18 carbon atoms, R ⁴ for alkylene radicals with 2 to 4 carbon atoms, G for glycoside radicals with 5 to 12 carbon atoms, p for numbers from 1 to 10, c for 0 or numbers in the range from 1 to 20, m stands for 0 or numbers in the range from 1 to 200, n for 0 or numbers in the range from 1 to 1000, x for 0 or 1 and y for 0 or numbers in the range from 1 to 1200, with the proviso that (I) at least contains a radical R ² for the production of cosmetic and / or pharmaceutical preparations.

Surprisingly, it has been found that glycosidic silicone compounds have surface tension-reducing effects and are particularly suitable as emulsifiers for the production of cosmetic or pharmaceutical preparations, especially emulsions. A special The advantage of using the emulsifiers is that the resulting emulsions neither separate nor change the viscosity even when stored at elevated temperature. In contrast to conventional silicone compounds, the glycosidic species prove to be satisfactorily biodegradable. Because of their surfactant properties, they can also be easily removed from the skin and hair, which counteracts the otherwise undesirable "build-up" effect, ie permanent accumulation of the substances is reliably avoided. At the same time, the giycosidic silicone compounds show an improved hair finish compared to conventional products and a more brilliant shine.

Glycosidic silicone compounds

The giycosidic silicone compounds to be used according to the invention are known substances which can be obtained by the relevant methods of preparative organic chemistry. The substances are usually produced by reacting mono- or oligosaccharides with unsaturated alcohols and then condensing the resulting alkenyl glycoside, then with an organosilicon compound containing Si-bonded hydrogen. A detailed description of the process can be found in EP-B1 0612759, already cited at the outset. The general formula also encompasses those glycosidic silicone compounds which are obtained by mixing the organosilicon compounds with a mixture of alkenylglycosides and α-olefins with 4 to 10 Reacts carbon atoms. The resulting products have a comb-like structure with excellent adhesion properties and can, for example, be substituted with a glycoside at every second to tenth position.

Examples of suitable saccharides that can be used as starting materials for the glycosidic silicone compounds are ribose, xylose, arabinose, glucose, mannose, galactose, fructose, sorbose, fucose, rhamnose, sucrose, lactose, maltose and their hydrates. Glucose or glucose monohydrate are preferably used. The radical R ³ in formula (II) is preferably derived from an unsaturated alcohol having 3 to 10 carbon atoms, the double bond of which is in the 1,2 position. Vinyl alcohol, allyl alcohol, 3-butenyl alcohol and 3-methyl-3-butenyl alcohol are particularly suitable for this. These alcohols can also be adducts of 1 to 10, preferably 2 to 8, moles of ethylene, propylene and / or butylene oxide. The silicone component of the glycosidic silicone compounds to be used according to the invention can be derived from α-hydrogenorganopolysiloxanes and / or α, ω-dihydrogenorganopolysiloxanes, as are mentioned below by way of example:

(1) H-Si (CH ₃ ) ₂ -0-Si (CH ₃ ) ₃ ,

(2) H-Si (CH ₃ ) ₂ -0-Si (CH ₃ ) 2H, (3) H- [Si (CH ₃ ) 2-0] ₄ -Si (CH ₃ ) ₂ -H,

(4) H- [Si (CH ₃ ) ₂ -0] ₉ -Si (CH ₃ ) 2-H,

(5) H-Si (CH ₃ ) 2-0- [Si (CH ₃ ) 2-0] ι ₅ -Si (CH3) 2-H,

(6) H-Si (CH3) 2-0- [Si (CH ₃ ) 2-0] i8-Si (CH ₃ ) 2-H and

(7) H-Si (CH3) 2-0- [Si (C2H ₅ ) 2-0] ιo-Si (CH3) 2-H

Also suitable as silicone components are organopolysiloxanes containing α, ω-triorganylsiioxy groups and Si-bonded hydrogen, for example:

(8) (CH ₃ ) 3SiO-SiHCH3θ-Si (CH ₃ ) 3,

(9) (CH ₃ ) 3SiO [SiHCH ₃ 0] 2Si (CH3) 3,

(10) (CH ₃ ) 3SiO [SiHCH ₃ 0] 3Si (CH3) 3,

(11) (CH3) 3SiO [SiHCH ₃ 0] ₄ Si (CH ₃ ) 3 and

(12) (CH3) ₃ SiO [Si (CH3) 2θ] 5o [SiHCH ₃ 0] ₅ Si (CH3) 3,

structures (1) and (8) are particularly preferred as starting materials. The proportion of the glycosidic silicone compounds in the preparations can be 0.01 to 10 and preferably 0.5 to 5% by weight.

Oil body

For the purposes of the present invention, the glycosidic silicone compounds can be used together with oil bodies. 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 C6-C22 fatty alcohols, esters of branched C6-Ci3-carboxylic acids with linear Cβ-C∑ come, for example, as oil bodies ∑-fatty alcohols, esters of linear C6-C22 fatty acids with branched alcohols, especially 2-ethylhexanol, esters of linear and / or branched fatty acids with polyhydric alcohols (such as propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, triglyce de based Cβ-Cio fatty acids, liquid mono- / di- / triglyceride mixtures based on Cβ-Ciβ fatty acids, esters of C6-C22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, especially benzoic acid, vegetable oils, branched primary alcohols, substituted cyclohexanes , linear C6-C22 fatty alcohol carbonates, Guerbet carbonates, esters of benzoic acid with linear and / or branched Cβ-C22 alcohols (eg Finso lv® TN), ring-opening products of epoxidized fatty acid esters with polyols such as glycerol, trimethylolpropane or pentaerythritol, dialkyl ethers (eg Sovermol®), silicone oils and / or aliphatic or naphthenic hydrocarbons. The proportion of the oil particles in the preparations can be 5 to 95, preferably 10 to 70 and in particular 15 to 50% by weight. Co-emulsifiers

Furthermore, the glycosidic silicone compounds can also be used together with other emulsifiers. Examples of suitable co-emulsifiers are nonionic surfactants from at least one of the following groups:

(b1) 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 carbon atoms, on fatty acids with 12 to 22 carbon atoms and on alkylphenols with 8 to 15 carbon atoms in the alkyl group; (b2) Ci2 / i8 fatty acid monoesters and diesters of adducts of 1 to 30 moles of ethylene oxide

Glycerin; (b3) Glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated

Fatty acids with 6 to 22 carbon atoms and their ethylene oxide addition products; (b4) alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs; (b5) adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hardened castor oil; (b6) polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricinoleate or polyglycerol poly-12-ydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable; (b7) adducts of 2 to 15 moles of ethylene oxide with castor oil and / or hardened castor oil; (b8) partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids,

Ricinoleic acid and 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 (e.g. cellulose); (b9) trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates; (b10) wool wax alcohols;

(b11) polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives; (b12) mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE-PS 1165574 and / or mixed esters of fatty acids with 6 to 22 carbon atoms, methyl glucose and

Polyols, preferably glycerin and (b13) polyalkylene glycols.

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 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are out DE-PS 20 24 051 known as a refatting agent for cosmetic preparations.

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 coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxyl -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 Cocamidopropyl Betaine is particularly preferred. Suitable emulsifiers are ampholytic surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a Cβ-alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2 / i8-acylsarcosine. In addition to the ampholytic emulsifiers, quaternary emulsifiers are also suitable, those of the esterquat type, preferably methyl-quaternized difatty acid ethanolamine ester salts, being particularly preferred. The proportion of the co-emulsifiers can be from 1 to 50, preferably from 10 to 25,% by weight, based on the glycosidic silicone compounds.

Surfactants

In addition to the glycosidic silicone compounds, the preparations may also contain anionic, nonionic, cationic, amphoteric and / or zwitterionic surfactants. Typical examples of anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, alkylether sulfonates, glycerol ether sulfonates, α-methyl ester sulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxymixed ether sulfates (fatty acid) sulfate acids, monoglysulfate ethersulfate (fatty ether sulfate), monoglysulfate (mono) sulfate, monoglysulfate Mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N-acyl amino acids such as, for example, acyl lactate fatty acids, alkyl acyl glycate fatty acids, acyl glucosate fatty acids, acyl glucosate fatty acid, acyl glucosate fatty acid, acyl glucosate fatty acid, acyl glucosate fatty acids, acyl glucosate fatty acids, acyl glucosate fatty acid, acyl glucate fats, acyl glucosate fatty acid, acyl glucosate fats, acyl glucosate fats, acyl glucosate fats and acyl glucosate fats and alkyl (ether) phosphates. If the anionic surfactants polyglycol ether chains contain, they can have a conventional, but preferably a narrow homolog distribution. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers or mixed formals, optionally partially oxidized alk (en) yl oligoglycosides, alkyl glucoramide acid derivatives (glucoramide amide derivatives), especially vegetable products based on wheat), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution. Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts. Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, reference is made to relevant reviews, for example J.Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp. 54-124 or J.Falbe (ed.), "Catalysts, Surfactants and mineral oil additives ", Thieme Verlag, Stuttgart, 1978, pp. 123-217.

Other auxiliaries and additives

For the purposes of the invention, the glycosidic silicone compounds can be used together with other auxiliaries and additives, such as, for example, superfatting agents, stabilizers, waxes, consistency enhancers, thickeners, cation polymers, silicone compounds, biogenic agents, anti-dandruff agents, film formers, preservatives, hydrotropes, solubilizers, UV light protection filters , Insect repellents, self-tanners, perfume oils and dyes. Typical products in which the substances can be used are, for example, hair shampoos, conditioners, hair treatments, shower baths, foam baths, shaving agents, hand creams, skin lotions, sunscreens, self-tanning agents, skin care creams, ointments and the like.

Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, soyasterins, ethoxylated soyasterines, acylated soyasterines, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers. Mainly fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycerides come into consideration as consistency agents. A combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxy stearates is preferred. Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, furthermore higher molecular weight polyethylene glycol mono- and di-esters of fatty acids, polyacrylates (eg Carbopole® from Goodrich or Synthalene® from Sigma), polyacrylamides, polyvinyl alcohol and polyvinylpyrrolidone, 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 oligoglucosides as well as electrolytes such as table salt and ammonium chloride.

Suitable cationic polymers are, for example, cationic cellulose derivatives, e.g. a quaternized hydroxyethyl cellulose available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers such as e.g. Luviquat® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as e.g. Amidomethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyaminopolyamides such as e.g. described in FR-A 2252840 and its crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, condensation products of dihaloalkylene such as e.g. Dibromobutane with bisdialkylamines such as Bis-dimethylamino-1, 3-propane, cationic guar gum such as e.g. 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 of Miranol.

Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine- and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature. Typical examples of fats are glycerides, beeswax, camamauba wax, candelilia wax, montan wax, paraffin wax or microwaxes, if appropriate in combination with hydrophilic waxes, for example cetylstearyl alcohol or partial glycerides. Pearlescent waxes which can be used are, in particular, mono- and difatty acid esters of polyalkylene glycols, partial glycerides or esters of fatty alcohols with polybasic carboxylic acids or hydroxycarboxylic acids. Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used as stabilizers. Biogenic active substances are to be understood, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes. Climbazole, octopirox and zinc pyrethione can be used as antidandruff agents. Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymers, polymers 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.

UV light protection filters are organic substances which are able to absorb ultraviolet rays and the absorbed energy in the form of longer-wave radiation, e.g. To give off heat again. Typical examples are 4-aminobenzoic acid and its esters and derivatives (e.g. 2-ethylhexyl p-dimethylaminobenzoate or p-dimethylaminobenzoic acid octyl ester), methoxy cinnamic acid and its derivatives (e.g. 4-methoxy cinnamic acid 2-ethylhexyl ester), benzophenones (e.g. oxybenzone, 2-hydroxy-4-methoxybenzophenone), dibenzoylmethane, salicylate ester, 2-phenylbenzimidazole-5-sulfonic acid, 1- (4-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione, 3- (4'-methyl) benzylideboron-nan-2-one, methylbenzylidene camphor and the like. Finely dispersed metal oxides or salts are also suitable for this purpose, such as, for example, titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc) and barium sulfate. 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. 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 are superoxide dismutase, tocopherols (vitamin E) and ascorbic acid (vitamin C).

Hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior. Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. 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;

Methylol 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.

Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid. N, N-diethyl-m-touluamide, 1, 2-pentanediol or Insect repellent 3535 are suitable as insect repellents, and dihydroxyacetone is suitable as a self-tanner.

Perfume oils include extracts from flowers (lavender, roses, jasmine, neroli), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway seeds, juniper), fruit peels (bergamot, lemon, oranges), roots (Macis, Angelica, Celery, Cardamom, Costus, Iris, Calmus), woods (sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemon grass, sage, thyme), needles and branches (spruce , Fir, pine, mountain pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials such as musk, civet and castoreum are also suitable. Ambroxan, eugenol, isoeugenol, citronellal, hydroxycitronellal, geraniol, citronellol, geranyl acetate, citral, ionone and methylionone are suitable as synthetic or semi-synthetic perfume oils.

The dyes which can be used are those which are suitable and approved for cosmetic purposes, as described, for example, in the publication "Cosmetic Dyes" by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, p.81-

106 are compiled. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.

The total proportion of auxiliaries and additives can be 1 to 60, preferably 5 to 40,% by weight, based on the preparations. The agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used.

Industrial applicability

In a particularly preferred embodiment of the invention, the glycosidic silicone compounds with further surfactants are used as emulsifier compounds. In this regard, blends with sugar surfactants of the alkyl and / or alkenyl oligoglycoside type have given excellent results. Accordingly, a further subject of the invention relates to cosmetic and / or pharmaceutical preparations containing

(a) glycosidic silicone compounds of formula (I) and

(b) alkyl and / or alkenyl oligoglycosides, the weight ratio here being in the range from 1:99 to 99: 1, preferably 10:90 to 90:10 and in particular 30:70 to 70:30.

Alkyl and / or alkenyl olefin glycosides

Alkyl and alkenyl oligoglycosides are known nonionic surfactants which follow the formula (III)

R ⁵ 0- [G *] _p (III)

in which R ^{5 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. They can be obtained according to the relevant procedures in preparative organic chemistry. As representative of the extensive literature, reference is made here to the documents EP-A1 0301298 and WO 90/03977.

The alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose. The preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides. The index number p in the general formula (III) gives the degree of oligomerization (DP), i.e. H. the distribution of mono- and oligoglycosides is on and stands for a number between 1 and 10. While p must always be an integer in a given compound and here can take on the values p = 1 to 6, the value p is for a certain alkyl oligo - glycoside is an analytically calculated value that usually represents a fractional number. Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, those alkyl and / or alkenyl oligoglycosides are preferred whose degree of oligomerization is less than 2.0 and in particular between 1.2 and 1.6.

The alkyl or alkenyl radical R ⁵ 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. Alkyl oligoglucosides of chain length Cβ-C10 (DP = 1 to 3) are preferred which are obtained as a preliminary step in the separation of technical Cβ-Ciβ-coconut fatty alcohol by distillation and are contaminated with a proportion of less than 6% by weight of Ci2-alcohol can as well as alkyl oligoglucosides based on technical C _θ / n-oxo alcohols (DP = 1 to 3). The alkyl or alkenyl radical R ⁵ 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, palm

n oleyl 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 described above. Alkyl oligoglucosides based on hydrogenated Ci2 / i4 coconut alcohol with a DP of 1 to 3 are preferred.

Examples

Various hair shampoos with giycosidic silicone compounds (recipes 1 to 7) or conventional silicones (comparison recipe V1) were tested by a panel of 20 subjects in the well-known half-side test regarding grip and gloss on a scale from 1 (= pleasant soft feel, brilliant gloss) to 5 (= hard, blunt). For the qualitative determination of the accumulation of oil on the hair, strands of hair were treated 10 times alternately with the test formulations and dried and then ashed. A strong accumulation of oil bodies was marked in the table with (+), if only little or no portions of oil bodies were detectable, this is marked with (-). The results are averages.

Table 1

Hair shampoos: grip and shine (quantities as% by weight)

*) Commercial products from Wacker-Chemie GmbH, Munich (DE)

The hair after-treatment agents 8 to 14 and the comparative product V2 were tested in the same way. The results are summarized in Table 2. Table 2

Hair aftertreatment: handle and shine (quantities as% by weight)

The panel tests show that the use of the glycosidic silicone compounds gives preparations which, when applied to the hair, are judged better than the comparison formulations with conventional silicones and at the same time have the advantage that there is no "build-up effect".

Claims

claims 1. Use of glycosidic silicone compounds of the formula (I), R2 _x Ri3.χSiO - [(SiRiR20) _m - (SiRi2θ) n] ySiRi ₃ .χR ² χ (I) in which R ^{1 is} hydrogen or an optionally substituted alkyl and / or alkenyl radical having 1 to 18 carbon atoms, R ^{2 is} a radical of the formula (II),

R ³ for alkylene residues with 1 to 18 carbon atoms, R ⁴ for alkylene residues with 2 to 4 carbon atoms, G for glycoside residues with 5 to 12 carbon atoms, p for numbers from 1 to 10, c for 0 or numbers in the range from 1 to 20, m stands for 0 or numbers in the range from 1 to 200, n for 0 or numbers in the range from 1 to 1000, x for 0 or 1 and y for 0 or numbers in the range from 1 to 1200, with the proviso that (I) contains at least one radical R ² for the production of cosmetic and / or pharmaceutical preparations. 2. Use according to claim 1, characterized in that the giykosidische silicone compounds in amounts of 0.01 to 10 wt .-% - based on the preparations - used. 3. Use according to claims 1 and 2, characterized in that the giycosidic silicone compounds are used together with oil bodies. 4. Use of claims 1 to 3, characterized in that the giycosidic silicone compounds are used together with co-emulsifiers. 5. Cosmetic and / or pharmaceutical preparations containing (a) glycosidic silicone compounds of formula (I) and (b) alkyl and / or alkenyl oligoglycosides. 6. Preparations according to claim 5, characterized in that they contain glycosides of the formula (III),

in which R ^{5 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.