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WO1999000400A1 - Ether de silicium d'oligoglycoside d'alkyle et/ou d'alcenyle - Google Patents

Ether de silicium d'oligoglycoside d'alkyle et/ou d'alcenyle Download PDF

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Publication number
WO1999000400A1
WO1999000400A1 PCT/EP1998/003622 EP9803622W WO9900400A1 WO 1999000400 A1 WO1999000400 A1 WO 1999000400A1 EP 9803622 W EP9803622 W EP 9803622W WO 9900400 A1 WO9900400 A1 WO 9900400A1
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WIPO (PCT)
Prior art keywords
alkyl
carbon atoms
alkenyl
ethers
silicone
Prior art date
Application number
PCT/EP1998/003622
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German (de)
English (en)
Inventor
Oliver Rhode
Original Assignee
Cognis Deutschland Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis Deutschland Gmbh filed Critical Cognis Deutschland Gmbh
Priority to AU82157/98A priority Critical patent/AU8215798A/en
Publication of WO1999000400A1 publication Critical patent/WO1999000400A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Definitions

  • the invention relates to alkyl and / or alkenyl oligoglycoside ethers which are obtained by ring opening of epoxy silicone ethers with glycosides, a process for their preparation and their use for the preparation of surface-active agents.
  • Alkyl oligoglucosides are nonionic surfactants with excellent foaming properties.
  • the emulsifying power of these surfactants leaves something to be desired, which is why many attempts have been made in the past to change the hydrophilicity or lipophilicity of this class of compounds by derivatization, i.e. adapt to the desired requirements.
  • condensation products of alkyl oligoglucosides with ethylene oxide or oligoglycerols are known.
  • European patent EP-B1 0612759 also relates to a process for the preparation of special alkyl glucoside silicone ethers, in which mono- or oligosaccharides are first reacted with unsaturated alcohols and the resulting alkenyl glycosides are then condensed with an Si-bonded hydrogen-containing organosilicon compound.
  • These surfactant silicone compounds show a significantly improved emulsifying capacity, but are not entirely satisfactory in terms of stabilizing emulsions at higher temperatures.
  • Another disadvantage is their complex production, since allyl glucosides have to be used for their production and there are high occupational safety requirements for the acetalization of glucose with allyl alcohol.
  • the object of the present invention was therefore to provide new glycosidic silicone compounds which have improved application properties and in particular are easier to produce.
  • the invention relates to alkyl and / or alkenyl oligoglycoside silicone ethers which are obtained by using alkyl and / or alkenyl oliglycosides of the formula (I),
  • R 1 represents an alkyl and / or alkenyl radical with 4 to 22 carbon atoms
  • G for a sugar radical with 5 or 6 carbon atoms and p for numbers from 1 to 10
  • basic catalysts with epoxysilicone ethers of the formula (II) in which R 1 represents an alkyl and / or alkenyl radical with 4 to 22 carbon atoms, G for a sugar radical with 5 or 6 carbon atoms and p for numbers from 1 to 10, in the presence of basic catalysts with epoxysilicone ethers of the formula (II) ,
  • R 2 stands for alkyl radicals with 1 to 4 carbon atoms, q for 0 or 1 and n and m independently of one another for numbers from 1 to 5.
  • the new glycosidic silicone compounds not only have excellent emulsifying properties, but also reliably stabilize emulsions even after prolonged storage at elevated temperatures. They also have lipophilic properties, which is why they are also suitable as polar oil bodies, especially as substitutes for conventional silicone oils of the polysiloxane type. Another advantage is their extremely simple manufacture.
  • the invention further relates to a process for the preparation of alkyl and / or alkenyl oligogiycosidesiiiconether, in which alkyl and / or alkenyl oliglycosides of the formula (I),
  • R 1 represents an alkyl and / or alkenyl radical with 4 to 22 carbon atoms
  • G for a sugar radical with 5 or 6 carbon atoms and p for numbers from 1 to 10
  • basic catalysts with epoxysilicone ethers of the formula (II) in which R 1 represents an alkyl and / or alkenyl radical with 4 to 22 carbon atoms, G for a sugar radical with 5 or 6 carbon atoms and p for numbers from 1 to 10, in the presence of basic catalysts with epoxysilicone ethers of the formula (II) ,
  • R 2 stands for alkyl radicals with 1 to 4 carbon atoms, q for 0 or 1 and n and m independently of one another for numbers from 1 to 5.
  • Alkyl and alkenyl oligoglycosides are known nonionic surfactants which follow the formula (I)
  • R 1 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms
  • p is a number from 1 to 10.
  • the alkyl and / 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 (I) indicates 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.
  • 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, preference is given to those alkyl and / or alkenyl oligoglycosides 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.
  • 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, palm oleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and the technical mixtures described above, which can be obtained as well as their technical mixtures.
  • Alkyl oligoglucosides based on hydrogenated Ci2 / i4 coconut alcohol with a DP of 1 to 3 are preferred.
  • Epoxysilicon ethers of the type mentioned are known substances which can be prepared by the customary methods of preparative chemistry. They are available, for example, under the brand name Silan-Z-6040 from Dow Corning. Epoxysilicon ethers of the formula (II) are preferably used in which R 2 is methyl, p is 1 and n and m is 1 or 3. The glycosides and the silicone ethers are usually used in a molar ratio of 1: 0.95 to 1: 1, 2, preferably 1: 1 to 1.1.
  • the selection of the basic catalyst is not critical per se. Basically, alkali and / or alkaline earth metal hydroxides, oxides, carbonates, bicarbonates, C 1 -C 4 -alcoholates and ammonia, alkylamines and / or alkanolamines can be used. Typical examples are sodium hydroxide, potassium hydroxide, magnesium oxide, sodium carbonate, sodium hydrogen carbonate, sodium methylate, methylamine, ethanolamine and the like.
  • the catalysts are usually used in amounts of 0.1 to 10, preferably 1 to 5,% by weight, based on the glycosides.
  • the opening of the epoxy ring of the silicone ether through the primary hydroxyl group of the glycoside can be carried out in a manner known per se.
  • the ring opening of epoxides with glucosides is described in principle in DE-A1 4223581 (Henkel).
  • the reaction is preferably carried out at temperatures in the range from 60 to 100.degree. In principle, lower temperatures are possible if the glucoside is liquid under these conditions and a lower reaction speed is acceptable. Temperatures above 100 ° C can lead to decomposition of the sugar body and are therefore less advantageous.
  • the new glycosidic silicone ethers reduce the interfacial tension and promote the emulsification of otherwise immiscible phases. They are also suitable as substitutes for polysiloxane oils, i.e. as a polar oil body.
  • Another object of the invention therefore relates to their use as surfactants for the production of surface-active agents and as emulsifiers or oil bodies for the production of cosmetic and / or pharmaceutical preparations in which they are used in amounts of 1 to 90, preferably 5 to 75 and in particular 10 to 25 % By weight, based on the composition, may be present.
  • the new glycosidic silicones are used together with alkyl oligoglucosides and optionally pearlescent waxes to produce foam-strong, storage-stable silicone shampoos with excellent conditioning and conditioning properties as well as brilliant pearlescence.
  • the new glycosidic silicone ethers can be used together with further anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants.
  • anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxymixed ether etherates, sulfate (sulfate) amate sulfate ethersulfate, mono - sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotrigly
  • anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of non-ionic 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 or glucoronic acid amide (in particular, glucoronic acid amide) vegetable oils, glucoronic acid amide, glucoronic acid amide, and / or glucoronic acid amide (glucoronic acid amide), in particular, glucoronic acid amide, glucoronic acid amide, (V), glucoronic acid amide, (v) Products on wheat basis), polyol fatty acid esters, sugar est
  • 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.
  • Preparations which are produced using the new glycosidic silicone ethers can furthermore contain, as further auxiliaries and additives, oil bodies, emulsifiers, superfatting agents, pearlescent waxes, stabilizers, consistency agents, thickeners, cation polymers, Contain silicone compounds, biogenic agents, anti-dandruff agents, film formers, preservatives, hydrotropes, solubilizers, UV light protection filters, insect repellents, self-tanners, perfume oils, dyes and the like.
  • 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 alkylphenols with 8 to 15 C atoms in the Alkyl group;
  • alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs
  • polystyrene resin e.g. Polyglycerol polyricinoleate or polyglycerol poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable;
  • 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 - glucoside) and polyglucosides (eg cellulose);
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters and sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are mixtures of homologs, 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 known from DE-PS 20 24 051 as refatting agents for cosmetic preparations.
  • C ⁇ / 18-alkyl mono- and oligoglycosides their preparation and their use as surface-active substances are known from the literature. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • glycoside residue both monoglycosides in which a cyclic sugar residue is giycosidically bound to the fatty alcohol is, as well as oligomeric glycosides with a degree of oligomerization up to preferably 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 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.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C ⁇ / i ⁇ -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.
  • 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.
  • quaternary emulsifiers are also suitable, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • 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 are: alkylene glycol esters, especially ethylene glycol distearate; Fatty acid alkanolamides, especially coconut fatty acid diethanolamide; Partial glycerides, 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
  • Suitable thickeners are, for example, 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 di-esters of fatty acids, polyacrylates, (for example 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 sodium chloride and ammonium chloride.
  • polysaccharides in particular xanthan gum, guar guar, agar a
  • 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® 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.
  • 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.
  • dihaloalkylene such as e.g. Dibromobutane
  • 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
  • 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, candelilla wax, montan wax, paraffin wax or microwaxes, if appropriate in combination with hydrophilic waxes, for example cetylstearyl alcohol or partial glycerides.
  • Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used as stabilizers.
  • biogenic active ingredients are tocopherol, tocopherol acetate and tocopherol.
  • Climbazole, octopirox and zinc pyrethione can be used as antidandruff agents.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinyl-pyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Montmohlonite, clay minerals, pemulene and alkyl-modified carbopol types can serve as swelling agents for aqueous phases.
  • UV light protection filters are organic substances that 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.
  • 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.
  • 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
  • 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;
  • 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,
  • 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 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.
  • 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.
  • DP 1.6

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Abstract

Ces nouveaux éthers de silicium d'oligoglycoside d'alkyle et/ou d'alcényle sont obtenus en faisant réagir des oligoglycosides d'alkyle et/ou d'alcényle de formule (I): R1O-[G]p, dans laquelle R1 désigne un radical alkyle et/ou alcényle de 4 à 22 atomes de carbone, G un radical glucidique de 5 à 6 atomes de carbone et p vaut 1 à 10, avec des éthers de silicium époxyde de formule (II), dans laquelle R2 désigne des radicaux alkyle de 1 à 4 atomes de carbone, q vaut 0 ou 1 et n et m valent indépendamment l'un de l'autre 1 à 5, en présence de catalyseurs basiques. Ces substances sont utiles comme agents tensioactifs, en particulier comme émulsifiants, mais aussi comme corps gras et comme substituts de polysiloxane pour préparer des produits tensioactifs, notamment des compositions cosmétiques.
PCT/EP1998/003622 1997-06-25 1998-06-16 Ether de silicium d'oligoglycoside d'alkyle et/ou d'alcenyle WO1999000400A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU82157/98A AU8215798A (en) 1997-06-25 1998-06-16 Alkyl and/or alkenyl oligoglycoside silicon ethers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1997127030 DE19727030A1 (de) 1997-06-25 1997-06-25 Alkyl- und/oder Alkenyloligoglykosidsiliconether
DE19727030.1 1997-06-25

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WO1999000400A1 true WO1999000400A1 (fr) 1999-01-07

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7001591B1 (en) * 1999-04-10 2006-02-21 Cognis Deutschland Gmbh & Co. Kg Cosmetic preparations containing silicone compounds and esters of hydroxycarboxylic acids and alk(en)yl oligoglycosides
US7166276B2 (en) 2001-10-26 2007-01-23 The Procter & Gamble Company Silicone elastomer emulsion cosmetic composition comprising colorant inclusive internal phase
US7404966B2 (en) 2000-07-10 2008-07-29 The Procter & Gamble Company Transfer-resistant makeup removing compositions
US7772214B2 (en) 2000-07-10 2010-08-10 The Procter & Gamble Company Emulsion cosmetic compositions comprising an emulsifying crosslinked siloxane elastomer

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DE19936324A1 (de) 1999-08-02 2001-02-22 Geodur Cis Ag Zug Gemisch zur Behandlung von Abfallmaterial
DE10233963A1 (de) * 2002-07-25 2004-02-12 Itn-Nanovation Gmbh Verwendung von Silanen in kosmetischen Mitteln und Verfahren zur Haarbehandlung

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WO1994029324A1 (fr) * 1993-06-04 1994-12-22 Bayer Aktiengesellschaft Hydrocarbures polyhydroxyles modifies au siloxanyl
US5428142A (en) * 1993-10-20 1995-06-27 Siltech Inc. Silicone based glycosides
US5498703A (en) * 1993-10-20 1996-03-12 Siltech Inc. Silanol based glycosides

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US7404966B2 (en) 2000-07-10 2008-07-29 The Procter & Gamble Company Transfer-resistant makeup removing compositions
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AU8215798A (en) 1999-01-19

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