WO2000018779A1 - Melanges de produits tensio-actifs - Google Patents

Melanges de produits tensio-actifs Download PDF

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Publication number
WO2000018779A1
WO2000018779A1 PCT/EP1999/006864 EP9906864W WO0018779A1 WO 2000018779 A1 WO2000018779 A1 WO 2000018779A1 EP 9906864 W EP9906864 W EP 9906864W WO 0018779 A1 WO0018779 A1 WO 0018779A1
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Prior art keywords
acid
mixtures
fatty
alcohol
carbon atoms
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PCT/EP1999/006864
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German (de)
English (en)
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Oliver Rhode
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Cognis Deutschland Gmbh
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Publication of WO2000018779A1 publication Critical patent/WO2000018779A1/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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives

Definitions

  • the invention relates to surfactant mixtures which are obtained by acetalization of glycoses with fatty alcohols and subsequent ethoxylation of the resulting mixtures.
  • Surfactant mixtures of alkyl oligoglycosides and ionic and nonionic surfactants, such as, for example, fatty alcohol ethoxylates, can be used in formulations for washing-up detergents and cleaning agents and are notable for special cleaning properties.
  • ionic and nonionic surfactants such as, for example, fatty alcohol ethoxylates
  • the documents EP-B1 0075996 (Procter & Gamble) and DE-A1 4039223 (Hüls) describe the combination of alkyl oligoglucosides with fatty alcohol ethoxylates in aqueous cleaning agents.
  • the preparation of these surfactant mixtures is very time-consuming and also cost-intensive, since the compounds are produced separately from one another and only then are the individual components mixed.
  • the object of the invention was therefore to provide mixtures of alkyl oligoglycosides and fatty alcohol ethoxylates in the simplest possible way, which have special surface-active properties.
  • the invention relates to surfactant mixtures which are obtained by
  • mixtures of alkyl oligoglycosides and fatty alcohols can be selectively converted to alkyl oligoglycoside / fatty alcohol ethoxylates.
  • the closes Invention discovered that the ethylene oxide reacts practically exclusively with the primary hydroxyl group of the alcohol, while addition products of ethylene oxide onto the alkyl oligoglycosides, which are suspected of not being sufficiently biodegradable, are formed only in very small amounts. In this way, mixtures of alkyl oligoglycosides and fatty alcohol ethoxylates are formed in a simple manner, which not only have excellent surface-active properties, but are also very readily biodegradable.
  • Another object of the invention relates to a method for producing surfactant mixtures, in which
  • the glycoses that can be used as starting materials can be aldoses or ketoses with 5 or 6 carbon atoms, e.g. the monosaccarides act glucose, fructose and mannose. However, glucose is preferably used. Disaccarides such as maltose, lactose and saccarose can also be used.
  • the alkyl and / or alkenyl oligoglycosides which are preferably formed in the acetalization are thus alkyl and / or alkenyl oligoglucosides.
  • Fatty alcohols which serve as a further feed component, are to be understood as primary aliphatic alcohols of the formula (I)
  • R 1 represents an aliphatic, linear or branched hydrocarbon radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds.
  • Typical examples are capronic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolenyl alcohol, linolenyl alcohol Arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and their technical mixtures, which are obtained, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxo synthesis and as a monomer fraction in the dimerization of unsatur
  • the acetalization can be carried out in a manner known per se, for example by introducing the glycose, optionally dehydrating, adding the calculated excess of fatty alcohol, heating to about 70 to 80 ° C. and 1 to 5% by weight of the acidic catalyst, such as, for example Sulfuric acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, sulfosuccinic acid, preferably dissolved in a further portion of fatty alcohol, metered in continuously.
  • the acetalization is usually carried out at temperatures in the range from 100 to 112 ° C. and under reduced pressure (typically 20 mbar).
  • the end point of the reaction ie the desired conversion, can be calculated from the ratio of the amount of condensation water separated off to the theoretically possible amount.
  • a degree of implementation in the range of 60 to 90% of theory is sought; a range from 70 to 80, preferably around 75% of theory has proven to be optimal.
  • a content of alkyl and / or alkenyl oligoglycoside specified for the surfactant compound can be controlled both via the excess of fatty alcohol and via the conversion: if the excess of fatty alcohol is large, a defined content of acetalization product in the compound is obtained with a comparatively higher conversion achieved than vice versa.
  • glycosides and fatty alcohols are reacted in a molar ratio of 1: 2 to 1:10, preferably 1: 4 to 1: 8.
  • a base for example sodium hydroxide and / or magnesium oxide
  • the unconverted glycoside is then filtered off at temperatures in the range from 70 to 95, preferably 80 to 90 ° C., it usually being possible to use a conventional type pressure filter.
  • the filtrate can also be between different Filter units are circulated.
  • Depth filters from Seitz are suitable as filter types, the pore size being in a range from 10 to 1000 ⁇ m.
  • the end point of the filtration cycle is reached when the filtrate appears clear (“blank”) and a further improvement in the color quality can no longer be observed.
  • alkyl and alkenyl oligoglycosides formed in the acetalization are known nonionic surfactants which follow the formula (II)
  • R 2 represents an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
  • G represents a glycoside radical having 5 or 6 carbon atoms
  • p represents numbers from 1 to 10.
  • Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably produced. 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 1.5.
  • the reaction mixture of alkyl oligoglycoside and fatty alcohol obtained from the acetalization which depending on the use ratio and degree of conversion in a weight ratio in the range from 1: 2 to 1:10 and preferably 1: 4 to 1: 8, is usually 0.1 to 5, preferably 0.5 to 3 and in particular 1 to 2% by weight of a basic catalyst, preferably calcined or hydrophobized hydrocalcite, are added and transferred to an autoclave. Before carrying out the reaction, it is recommended to evacuate the autoclave at least 3 times and to vent it with nitrogen.
  • the ethoxylation is usually carried out at temperatures from 100 to 180, preferably at 120 to 170 and in particular at 140 to 160 ° C.
  • ethylene oxide is added in portions, a molar ratio of alkyl oligoglycoside / fatty alcohol: ethylene oxide of 1: 1 to 1:50, preferably 1: 5 to 1:30 and in particular 1:10 to 1:20 being aimed for.
  • the ethoxylation is usually carried out in a pressure range from 1 to 50, preferably 1 to 30, bar and a reaction time of 2 to 12, preferably 4 to 8 hours.
  • the mixture is stirred for about 30 to 60 min, the autoclave is cooled, the pressure is released and the catalyst is separated off, if necessary, using a filter funnel.
  • the surface-active agents can be detergents, dishwashers, cleaning agents, fabric softeners, cosmetic preparations for the care and cleaning of skin, hair, and oral and dental care products.
  • the surfactant mixtures according to the invention can be used to produce cosmetic preparations, such as, for example, hair shampoos, hair lotions, bubble baths, creams, gels, lotions or ointments.
  • These agents can also be used as further auxiliaries and additives, mild surfactants, oil bodies, emulsifiers, superfatting agents, pearlescent waxes, stabilizers, consistency agents, thickeners, polymers, silicone compounds, biogenic agents, deodorants, antidandruff agents, film formers, preservatives, hydrotropes, solubiizers, UV light protection factors, Contain antioxidants, insect repellents, self-tanners, perfume oils, dyes and the like.
  • Suitable mild, i.e. particularly skin-compatible surfactants are fatty alcohol polyglycol-giycolethersulfate, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid taurides, fatty acid glutamates, ether carboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkylamidobetaines and / or protein fatty acid condensates, the latter preferably based on wheat proteins.
  • Finsolv® TN linear or branched, symmetrical or asymmetrical dialkyl ethers with 6 to 22 carbon atoms per alkyl group, ring opening products of epoxidized fatty acid esters with polyols, silicone oils and / or aliphatic or naphthenic hydrocarbons.
  • Suitable emulsifiers are nonionic surfactants from at least one of the following groups:
  • alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs
  • polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricin oleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimerostearate. 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 glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (eg sorbitol), alkyl glucosides (eg methyl glucoside, butyl glucoside -glucoside) and polyglucosides (eg cellulose);
  • 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.
  • C ⁇ _ / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 2024051 as refatting agents for cosmetic preparations.
  • Cs / i ⁇ 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.
  • glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oiigomeric 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 cocoalkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl -3-carboxylmethyl-3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethyl carboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate,
  • 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 -SOßH group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid, each with about 8 to 18 C. Atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2 / ⁇ -acylsarcosine.
  • ampholytic Quaternary emulsifiers are also suitable, those of the esterquat type, preferably methylquaternized 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 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-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred.
  • 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 diesters of fatty acids, polyacrylates (for example 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 trimethyloipropane, 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 agar
  • 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, for example, Luviquat® (BASF) , Condensation products of polygylenes and amines, quaternized collagen polypeptides, such as lauryldimonium hydroxypropyl hydroicyzed collagen (Lamequat®L Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, such as amidomethicones, copolymers of adipic acid and dimethyl-aminohydroxynol / sand-aminohydroxy-mole (aminohydroxynol) / s
  • Anionic, zwitterionic, amphoteric and nonionic polymers include, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobomylacrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and polyesters and their esters, unmembranes - thylammonium chloride / acrylate copolymers, octylacrylamide / methyl methacrylate / tert.
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds which can be both liquid and resinous at room temperature.
  • suitable volatile silicones can also be found by Todd et al. in Cosm.Toil. 91, 27 (1976).
  • Typical examples of fats are glycerides, waxes include Beeswax, camauba wax, candelilla wax, montan wax, paraffin wax, hydrogenated castor oils, fatty acid esters or micro waxes solid at room temperature, optionally in combination with hydrophilic waxes, e.g. Cetylstearyl alcohol or partial glycerides in question.
  • Metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate can be used.
  • biogenic active substances examples include tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, To understand phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes.
  • Deodorants come e.g. Antiperspirants such as aluminum chlorohydates are possible. These are colorless, hygroscopic crystals that easily melt in the air and are produced when aqueous aluminum chloride solutions are evaporated. Aluminum chlorohydrate is used to manufacture 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)].
  • an aluminum chlorohydrate that corresponds to the formula [Al2 (OH) sCI] * 2.5 H2O and whose use is particularly preferred is commercially available under the trademark Locron® from Hoechst AG, Frankfurt / FRG [cf. J.Pharm.Pharmacol. 26, 531 (1975)].
  • Locron® from Hoechst AG, Frankfurt / FRG [cf. J.Pharm.Pharmacol. 26, 531 (1975)].
  • aluminum hydroxyl actates and acidic aluminum / zirconium salts can also be used. Esterase inhibitors can be added as further deodorant active ingredients.
  • trialkyl citrates such as trimethyl 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.
  • esterase inhibitors are dicarboxylic acids and esters thereof such as glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, adipic acid ester, malonic acid and Malonklathyiester, acids Hydroxycarbnon- and esters thereof 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 include 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 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.
  • 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 release the absorbed energy in the form of longer-wave radiation, for example heat.
  • UVB filters can be oil-soluble or water-soluble. Examples of oil-soluble substances are:
  • 3-benzylidene camphor or 3-benzylidene norcampher and its derivatives e.g. 3- (4-methylbenzylidene) camphor as described in EP-B1 0693471;
  • 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, isoamyl 4-methoxycinnamate, 2-cyano-3,3-henylcinnamate, 2-ethylhexyl ester (oc-tocrylene);
  • esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylic acid, homomenthyl salicylic acid;
  • 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 triazone, as described in EP-A1 0818450;
  • Propane-1,3-dione e.g. 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1,3-dione;
  • Sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid and their salts;
  • Sulfonic acid derivatives of 3-benzylidene camphor e.g. 4- (2-oxo-3-bornylidene-methyl) benzenesulphonic acid and 2-methyl-5- (2-oxo-3-bomylidene) sulfonic acid and their salts.
  • UV-A filters -4'- methoxydibenzoyl-methane (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.
  • insoluble light protection pigments namely finely dispersed metal oxides or salts, are also suitable for this purpose.
  • 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. So-called micro or nano pigments are preferably used in sunscreens. Micronized zinc oxide is preferably used.
  • UV light protection filters can be found in the overview by P.Finkel in S ⁇ FW-Journal 122, 543 (1996).
  • 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 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-carnosine and their derivatives (e.g. anserine) , Carotenoids, carotenes (e.g.
  • ⁇ -carotene, ⁇ -carotene, lycopene and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (e.g. dihydroiiponic acid), aurothioglucose, propylthiouracil and other thiols (e.g.
  • thioredoxin glutathione, cysteine, Cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters) and their salts , Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g.
  • buthioninsulfoximines homocysteine sulfoximine, butioninsulfones, penta-, hexa-, himinath.
  • n very low tolerable doses e.g. pmol to ⁇ mol / kg
  • metal chelators e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin
  • ⁇ -hydroxy acids e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. humic acid
  • vitamin E acetate
  • vitamin A and derivatives vitamin A palmitate
  • coniferyl benzoate of the benzoin resin Rutinic acid and its derivatives, -Glycosylrutin, Ferulaklare, Furfurylidenglucitol, Camosin, Butylhydroxytoluol, Butylhydroxy-anisole, Nordihydroguajakharzäure, Nordihydroguajaretklare, Trihydroxybutyrophenon, uric acid and their derivatives, Mannose and its derivatives, Zinc, Zinc, superoxide, Z-Oxygen, Z-Oxide, their derivatives, Zinc oxide, Z-Oxygen, Z-Oxygen-Z, for example, Zinc and its derivatives, Zinc oxide, Z-Oxide, Z-Oxygen, Z-Oxygen, Z-Oxygen, Z-Oxygen, Z-Oxygen, Z-Oxygen, Z-Oxygen, Z-
  • 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;
  • 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,
  • Aminosugars such as glucamine.
  • 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-touluamide, 1, 2-pentanediol or Insect repellent 3535 are suitable as insect repellents, and dihydroxyacetone is suitable as a self-tanner.
  • 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, cumin, juniper), fruit peel (bergamot, lemon, Oranges), roots (Macis, Angelica, Celery, cardamom, costus, iris, calmus), woods (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), needles and twigs (spruce, fir, pine) , Mountain pines), resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • 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, dimethylbenzylcarbinylacetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl methyl phenyl glycinate, allyl cyclohexyl undylpropyl propylate-stylpropionate, stylionyl pentate.
  • the ethers include, for example, benzyl ethyl ether
  • the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellalal, lilial and bourgeonal
  • the ketones include, for example, the jonones, oc-iso-methionone and methyl cedryl ketone , the alcohols anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol
  • the hydrocarbons mainly include the terpenes and balsams.
  • fragrance oils 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.
  • 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.
  • the surfactant mixtures can also be used for the production of detergents, preferably liquid detergents, which have a nonaqueous fraction in the range from 5 to 50 and preferably 15 to 35% by weight. In the simplest case, these are aqueous solutions of the surfactant mixtures mentioned.
  • the liquid detergents can, however, also be essentially water-free detergents. In the context of this invention, "essentially anhydrous" means that the agent preferably contains no free water which is not bound as water of crystallization or in a comparable form. In some cases, small amounts of free water are tolerable, especially in amounts up to 5% by weight.
  • liquid detergents may also have other typical ingredients, such as, for example, solvents, hydrotropes, bleaches, builders, viscosity regulators, enzymes, enzyme stabilizers, optical brighteners, soil repellants, foam inhibitors, inorganic salts and fragrances and colorants, provided that these are sufficiently stable in an aqueous environment.
  • solvents such as, for example, solvents, hydrotropes, bleaches, builders, viscosity regulators, enzymes, enzyme stabilizers, optical brighteners, soil repellants, foam inhibitors, inorganic salts and fragrances and colorants, provided that these are sufficiently stable in an aqueous environment.
  • suitable organic solvents are monofunctional and / or polyfunctional alcohols having 1 to 6 carbon atoms, preferably having 1 to 4 carbon atoms.
  • Preferred alcohols are ethanol, 1, 2-propanediol, glycerol and mixtures thereof.
  • the compositions preferably contain 2 to 20% by weight and in particular 5 to 15% by weight of ethanol or any mixture of ethanol and 1, 2-propanediol or in particular of ethanol and glycerol. It is also possible that the preparations either contain, in addition to the mono- and / or polyfunctional alcohols having 1 to 6 carbon atoms or solely polyethylene glycol with a relative molecular weight between 200 and 2000, preferably up to 600, in amounts of 2 to 17% by weight .
  • toluenesulfonate, xylenesulfonate, cumene sulfonate or mixtures thereof can be used as hydrotropes.
  • bleaching agents are, for example, peroxy carbonate, citrate perhydrates and salts of peracids, such as perbenzoates, peroxyphthalates or diperoxydodecanedioic acid. They are usually used in amounts of 8 to 25% by weight.
  • the use of sodium perborate monohydrate in amounts of 10 to 20% by weight and in particular 10 to 15% by weight is preferred. Due to its ability to bind free water with the formation of tetrahydrate contributes to increasing the stability of the agent. Preferably, however, the preparations are free from such bleaching agents
  • Suitable builders are ethylenediaminetetraacetic acid, nit ⁇ lot ⁇ essigsaure, citric acid and inorganic phosphonic acids, such as the neutral sodium salts of 1-hydroxyethane-1, 1, -d ⁇ phosphonate, which are present in amounts of 0.5 to 5, preferably 1 to 2% by weight can
  • Viscosity regulators which can be used are, for example, hardened castor oil, salts of long-chain fatty acids, which are preferably present in amounts of 0 to 5% by weight and in particular in amounts of 0.5 to 2% by weight, for example sodium, potassium, aluminum, magnesium and Titanium stearates or the sodium and / or potassium salts of behenic acid, and further polymeric compounds are used.
  • the latter preferably include polyvinylpyrrolidone, urethanes and the salts of polymeric polycarboxylates, for example homopolymeric or copolymeric polyacrylates, polymethacrylates and in particular copolymers of acrylic acid with maleic acid, preferably such from 50% to 10% maleic acid
  • the relative molecular weight of the homopolymers is generally between 1000 and 100000, that of the copolymers between 2000 and 200000, preferably between 50,000 and 120,000, based on the free acid.
  • Water-soluble polyacrylates are also particularly suitable, for example with about 1% of a polyallyleth
  • the sucrose is cross-linked and the molecular weight is above one million.
  • the cross-linked polyacrylates are preferably used in amounts not exceeding 1% by weight, preferably in amounts of 0 , 2 to 0.7% by weight.
  • the agents can additionally contain about 5 to 20% by weight of a partially esterified copolyme ⁇ sate, as described in European patent application EP-A 0367049.
  • These partially esterified polymers are obtained by copolyme ⁇ sation of (a) at least one C -C28 olefins or mixtures of at least one C -C28 olefins with up to 20 mol% of C 2 -C 6 -alkyl vinyl ethers and (b) ethylenically unsaturated dicarboxylic acid anhydrides with 4 to 8 carbon atoms in a molar ratio of 1 1 to copolymers with K -Values from 6 to 100 and subsequent partial esterification of the copolymensates with reaction products such as -CC 3 -alcohol len, Cs-C22 fatty acids, -C-Ci2-alkylphenols, secondary C2-C 3 o-amines or their mixtures with at least one C ⁇ -Ct alkylene oxide or tetrahydrofuran and hydrolysis of the anhydride groups of the copolymers to carboxyl groups, the partial esterification of the copoly
  • Preferred copolymers contain as ethylenically unsaturated dicarboxylic anhydride maleic anhydride.
  • the partially esterified copolymers can be present either in the form of the free acid or, preferably, in partially or completely neutralized form the Copolymensate in the form of an aqueous solution, in particular in the form of a 40 to 50 wt .-% solution used.
  • the copolymers not only contribute to the primary and secondary washing performance of the liquid washing and cleaning agent, but also bring about a desired reduction in the viscosity of the concentrated liquid washing agent.
  • the use of these partially esterified copolymers gives concentrated aqueous liquid detergents which are flowable under the sole influence of gravity and without the action of other shear forces.
  • the concentrated aqueous liquid detergents preferably contain partially esterified copolymers in amounts of 5 to 15% by weight and in particular in amounts of 8 to 12% by weight.
  • Suitable enzymes are those from the class of proteases, lipases, amylases, cellulases or mixtures thereof. Enzymes obtained from bacterial strains or fungi such as Bacillus subtilis, Bacillus licheniformis and Streptomyces griseus are particularly suitable. Proteases of the subtilisin type and in particular proteases which are obtained from Bacillus lentus are preferably used. Their proportion can be about 0.2 to about 2% by weight. The enzymes can be adsorbed on carriers and / or embedded in coating substances in order to protect them against premature decomposition. In addition to the mono- and polyfunctional alcohols and the phosphonates, the agents can contain further enzyme stabilizers.
  • sodium formate 0.5 to 1% by weight sodium formate can be used. It is also possible to use proteases which are stabilized with soluble calcium salts and a calcium content of preferably about 1.2% by weight, based on the enzyme.
  • proteases which are stabilized with soluble calcium salts and a calcium content of preferably about 1.2% by weight, based on the enzyme.
  • boron compounds for example boric acid, boron oxide, borax and other alkali metal borates such as the salts of orthoboric acid (H3BO3), metaboric acid (HBO2) and pyrobic acid (tetraboric acid H2B4O7), is particularly advantageous.
  • Suitable soil repellants are substances which preferably contain ethylene terephthalate and / or polyethylene glycol terephthalate groups, the molar ratio of ethylene terephthalate to polyethylene glycol terephthalate being in the range from 50:50 to 90:10.
  • the molecular weight of the linking compounds Polyethylene glycol units is in particular in the range from 750 to 5000, ie the degree of ethoxylation of the polymers containing polyethylene glycol groups can be approximately 15 to 100.
  • the polymers are characterized by an average molecular weight of approximately 5000 to 200,000 and can have a block, but preferably one Preferred polymers are those with molar ratios of ethylene terephthalate / polyethylene glycol terephthalate of from about 65:35 to about 90:10, preferably from about 70:30 to 80:20. Also preferred are those polymers which have linking polyethylene glycol units with a molecular weight from 750 to 5000, preferably from 1000 to about 3000 and a molecular weight of the polymers of about 10,000 to about 50,000. Examples of commercially available polymers are the products Milease® T (ICI) or Repelotex® SRP 3 (Rhône-Poulenc).
  • foam inhibitors When used in machine washing processes, it can be advantageous to add conventional foam inhibitors to the agents.
  • Soaps of natural or synthetic origin with a high content of Ci8-C24 fatty acids are suitable.
  • Suitable non-surfactant-like foam inhibitors are, for example, organopolysiloxanes and their mixtures with microfine, optionally silanized silica, and paraffins, waxes, microcrystalline waxes and their mixtures with silanized silica or bistearylethylenediamide.
  • Mixtures of different foam inhibitors are also used with advantages, e.g. those made of silicone, paraffins or waxes.
  • the foam inhibitors, in particular silicone- or paraffin-containing foam inhibitors are preferably bound to a granular, water-soluble or dispersible carrier substance. Mixtures of paraffins and bistearylethylenediamides are particularly preferred.
  • the pH of the concentrated agents according to the invention and in particular of the preferred concentrated agents is generally 7 to 10.5, preferably 7 to 9.5 and in particular 7 to 8.5. Higher pH values, for example above 9, can be set by using small amounts of sodium hydroxide solution or alkaline salts such as sodium carbonate or sodium silicate.
  • the liquid detergents according to the invention generally have viscosities between 150 and 10,000 mPas (Brookfield viscometer, spindle 1, 20 revolutions per minute, 20 ° C.). Viscosities between 150 and 5000 mPas are preferred for the essentially water-free agents.
  • the viscosity of the aqueous compositions is preferably below 2000 mPas and in particular between 150 and 1000 mPas.
  • the resulting mixture contained the alkyl oligoglycoside, with a DP of 1.45, and dodecanol in a weight ratio of 1: 3.8. 648 g of the glycoside / fatty alcohol mixture were transferred to a 2 l stirred autoclave and 6.5 g (corresponding to 1% by weight) of hydrophobicized hydrocalcite were added.
  • the autoclave was closed and alternately evacuated three times and flushed with nitrogen.
  • the pressure reactor was then heated to 150 ° C. and 1209 g (27.5 mol) of ethylene oxide were added in portions, the pressure rising to 5 bar.
  • the autoclave was cooled, the pressure was released and the catalyst was separated off using a suction filter.
  • the mixture contained practically exclusively ethoxylated lauryl alcohol with an average degree of ethoxylation of 6; the proportion of ethoxylated glucoside was less than 1% by weight.
  • the resulting mixture contained the alkyl oligoglycosides (DP of 1.45) and the fatty alcohols in a weight ratio of 1: 3.9.
  • 662 g of the glycoside fatty alcohol mixture were transferred to a 2 l stirred autoclave and 6.6 g (corresponding to 1% by weight) of hydrophobicized hydrocalcite were added.
  • the autoclave was closed and alternately evacuated three times and flushed with nitrogen.
  • the pressure reactor was then heated to 150 ° C. and 1735 g (39.5 mol) of ethylene oxide were added in portions, the pressure rising to 7 bar. After a reaction time of 9 h and one After stirring for 30 min, the autoclave was cooled, the pressure was released and the catalyst was separated off using a suction filter.
  • the mixture contained practically exclusively ethoxylated lauryl alcohol with an average degree of ethoxylation of 7; the proportion of ethoxylated glucoside was less than 1.5% by weight.
  • the resulting mixture contained the alkyl oligoglycoside, with a DP of 1.45, and dodecanol in a weight ratio of 1: 3.8. 648 g of the glycoside / fatty alcohol mixture was transferred to a 2 l stirred autoclave and 6.5 g (corresponding to 1% by weight) of calcined hydrocalcite were added.
  • the autoclave was closed and alternately evacuated three times and flushed with nitrogen.
  • the pressure reactor was then heated to 160 ° C. and portions of 1813 g (41.25 mol) of ethylene oxide were added, the pressure rising to 10 bar.
  • the autoclave was cooled, the pressure was released and the catalyst was separated off using a suction filter.
  • the mixture contained practically exclusively ethoxylated lauryl alcohol with an average degree of ethoxylation of 4.5; the proportion of ethoxylated glucoside was less than 1% by weight.
  • the resulting mixture contained the alkyl oligoglycoside, with a DP of 1.47, and dodecanol in a weight ratio of 1: 3.75.
  • 641 g of the glycoside / fatty alcohol mixture were transferred to a 2 l stirred autoclave and 6.4 g (corresponding to 1% by weight) of hydrophobicized hydrocalcite were added.
  • the autoclave was closed and alternately evacuated three times and flushed with nitrogen.
  • the pressure reactor was then heated to 155 ° C. and 2387 g (54.3 mol) of ethylene oxide were added in portions, the pressure rising to 8 bar.
  • the autoclave was cooled, the pressure was released and the catalyst was separated off using a suction filter.
  • the mixture contained practically exclusively ethoxylated lauryl alcohol with an average degree of ethoxylation of 8; the proportion of ethoxylated glucoside was less than 2% by weight.
  • the resulting mixture contained cetylstearylglycoside and cetylstearyl alcohol in a weight ratio of 1: 5. 810 g of the glucoside.
  • the fatty alcohol mixture was transferred to a 2 liter stirred autoclave and 8.1 g (corresponding to 1% by weight) of calcined hydrocalcite were added.
  • the autoclave was closed and alternately evacuated three times and flushed with nitrogen.
  • the pressure reactor was then heated to 160 ° C. and 1737 g (39.5 mol) of ethylene oxide were added in portions, the pressure rising to 5 bar. After a reaction time of 4 h and a subsequent stirring time of 30 min, the autoclave was cooled, the pressure was released and the catalyst was separated off using a suction filter.
  • the mixture contained practically exclusively ethoxylated lauryl alcohol with an average degree of ethoxylation of 6; the proportion of ethoxylated glucoside was less than 1% by weight

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Abstract

L'invention concerne l'utilisation de mélanges de produits tensio-actifs et un procédé de fabrication de ces mélanges caractérisé en ce que (a) des glucoses sont acétalisés, de façon connue en soi, avec des alcools gras, et (b) les mélanges résultants sont ensuite éthoxylés. Ces mélanges d'alkyloligo-glucoside-éthoxylate d'alcools gras peuvent être utilisés dans des agents tensio-actifs, de préférence, dans des agents détergents pour lavage manuel de la vaisselle.
PCT/EP1999/006864 1998-09-25 1999-09-16 Melanges de produits tensio-actifs WO2000018779A1 (fr)

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DE10021310A1 (de) * 2000-05-02 2001-11-15 Friedrich Schardt Haarwasser
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CN102786556B (zh) * 2011-05-19 2014-12-10 扬州晨化新材料股份有限公司 制备十八烷基葡萄糖苷的方法

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Publication number Priority date Publication date Assignee Title
DE4115149A1 (de) * 1991-05-08 1992-11-12 Henkel Kgaa Verfahren zur herstellung von fettalkoholpolyalkylenglycolethern
EP0699206A1 (fr) * 1993-05-21 1996-03-06 Henkel Kgaa Emulsifiants non ioniques
WO1997020018A1 (fr) * 1995-11-25 1997-06-05 Henkel Kommanditgesellschaft Auf Aktien Produits de depart liquides pour agents de lavage, de rinçage et de nettoyage

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GR76287B (fr) * 1981-09-28 1984-08-04 Procter & Gamble
DE4039223A1 (de) * 1990-12-08 1992-06-11 Huels Chemische Werke Ag Fluessige waschmittel

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4115149A1 (de) * 1991-05-08 1992-11-12 Henkel Kgaa Verfahren zur herstellung von fettalkoholpolyalkylenglycolethern
EP0699206A1 (fr) * 1993-05-21 1996-03-06 Henkel Kgaa Emulsifiants non ioniques
WO1997020018A1 (fr) * 1995-11-25 1997-06-05 Henkel Kommanditgesellschaft Auf Aktien Produits de depart liquides pour agents de lavage, de rinçage et de nettoyage

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