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EP1620067A1 - Preparations cosmetiques et/ou pharmaceutiques - Google Patents

Preparations cosmetiques et/ou pharmaceutiques

Info

Publication number
EP1620067A1
EP1620067A1 EP04728534A EP04728534A EP1620067A1 EP 1620067 A1 EP1620067 A1 EP 1620067A1 EP 04728534 A EP04728534 A EP 04728534A EP 04728534 A EP04728534 A EP 04728534A EP 1620067 A1 EP1620067 A1 EP 1620067A1
Authority
EP
European Patent Office
Prior art keywords
acid
alkyl
contain
partial esters
alcohols
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP04728534A
Other languages
German (de)
English (en)
Inventor
Ansgar Behler
Almud Folge
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cognis IP Management GmbH
Original Assignee
Cognis IP Management 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 IP Management GmbH filed Critical Cognis IP Management GmbH
Publication of EP1620067A1 publication Critical patent/EP1620067A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • 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
    • 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
    • A61Q5/006—Antidandruff preparations
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/08—Polycarboxylic acids containing no nitrogen or sulfur
    • 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 is in the field of cosmetics and relates to preparations which contain certain sugar surfactants in combination with hydroxycarboxylic acid partial esters of alkoxylated alcohols, the use of the mixtures for the production of cosmetic and / or pharmaceutical preparations and the use of such mixtures in detergents and cleaning agents.
  • Alkyl oligoglycosides are surface-active substances which, put simply, combine the foam strength of anionic surfactants with the dermatological compatibility of nonionic surfactants. Because of these two properties and the compatibility with practically all other cosmetic ingredients, the glycosides have now secured a firm place in the field of hand dishwashing detergents and especially cosmetics. Nevertheless, alkyl oligoglucosides still have shortcomings. The base foam is sufficient, but the foam stability is significantly lower than that of alkyl ether sulfates. Furthermore, a further improvement of the eye mucosa would be advantageous.
  • German Offenlegungsschrift DE-A-199 455 78 discloses cosmetic preparations which contain alk (en) yl oligoglycosides and also hydroxycarboxylic acid partial esters of alcohols having 10 to 18 carbon atoms. Cosmetic preparations of this type are notable for good dermatological compatibility, in particular special eye mucous membrane compatibility with good foaming kinetics. However, such surfactant mixtures as an aqueous formulation do not have the desired long-lasting clear appearance.
  • the object of the present invention was to provide new preparations based on alk (en) yl oligoglycosides, which are characterized in that, in addition to improved dermatological compatibility, in particular compatibility with the eye mucous membrane, and at the same time advantageous foaming kinetics, improved foam stability and clear Have appearance as an aqueous formulation.
  • the invention relates to cosmetic and / or pharmaceutical preparations containing
  • the preparations according to the invention are notable for excellent skin and eye mucous membrane compatibility and also have strong foaming behavior and high foam stability even in hard water, even when exposed to high levels of fat. It has also been found that the mixtures in water give long-lasting clear formulations.
  • 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. They can be obtained according to the relevant procedures in preparative organic chemistry.
  • 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 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, capronic 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, palmoleyl 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.
  • Alkyl oligoglucosides based on hardened Ci 2 / are preferred. 4 coconut alcohol with a DP of 1 to 3.
  • Hydroxycarboxylic acid partial esters of alkoxylated alcohols are known compounds.
  • the substances which form component (b) are preferably esters of alkoxylated alcohols with hydroxycarboxylic acids having 1 to 6 Carbon atoms, especially esters of hydroxycarboxylic acids, which are selected from the group formed by lactic acid, tartaric acid, malic acid and citric acid and their self-condensation products.
  • the corresponding esters of citric acid are particularly suitable.
  • Citric acid partial esters which are also referred to as alkyl ether citrates, have been known compounds for a long time and have also found their way into cosmetic products.
  • EP 282 289 A1 cosmetic compositions which contain monoalkylcitronic acid salts of alcohols having 1 to 7 moles of ethoxylated alcohols having 10 to 18 carbon atoms.
  • citric acid esters of alcohols with 1 to 20 moles of ethoxylated alcohols with 8 to 20 carbon atoms are known, which can be mono-, di- or triesters. According to this document, citric acid esters produced from 1 mol of citric acid and 2 mol with a 7 mol ethoxylated alcohol mixture of C11, C12 and C13 alcohols show low irritation potential and acceptable foaming power.
  • citric acid esters to improve the washability of oil-containing cosmetic compositions.
  • the citric acid esters are esters of alcohols having 5 to 30 mol of ethoxylated alcohols having 12 to 18 carbon atoms. These can be mono-, di- and / or triesters. According to the examples, in particular the mono- or diesters of ethoxylated with 7 or 9 moles.
  • coconut alcohol which always also contains unsaturated alcohols, is suitable.
  • the esters for example, have a moderate foam behave, where the monoesters of lauryl alcohol ethoxylated with 3 and 6 moles of ethylene oxide show better foaming behavior than the diesters, while the esters with 9 moles of ethylene oxide as diesters are better than the monoesters.
  • the partial esters (component b) contained according to the invention are anionic surfactants, i.e. mainly compounds that still contain at least one free carboxyl group. Accordingly, it can be acidic esters or their neutralization products.
  • the partial esters are preferably in the form of the alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and / or glucammonium salts.
  • the partial esters are preferably mixtures which contain more than 55% by weight, in particular more than 65% by weight, based on the mixture, of compounds with at least one free carboxyl group.
  • the citric acid partial esters are very particularly preferably mixtures with about 25 to 60% by weight monoesters, 10 to 40% by weight diesters and 5 to 15% by weight triester. Up to 10% by weight can be present as free hydroxycarboxylic acid.
  • Very particularly suitable mixtures of the citric acid partial esters have a weight ratio of monoester to diester in the range from 3: 1 to 10: 1, in particular from 5: 1 to 8: 1.
  • the hydroxycarboxylic acid partial esters are derived from alkoxylated alcohols, preferably from alkoxylated aliphatic fatty alcohols having 6 to 22 carbon atoms. They are preferably derived from ethoxylated alcohols having 6 to 22 carbon atoms and in particular from those of the general formula (II)
  • R 2 is a linear or branched alkyl and / or alkenyl radical having 6 to 22 carbon atoms and n is a number from 1 to 50.
  • Compounds of formula (II) with a degree of ethoxylation n of 1 to 20 are preferred.
  • Typical examples are the adducts of on average 1 to 20, preferably 1 to 10 and in particular 1 to 8 moles of ethylene oxide with capron 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, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and their technical mixtures, which are used, for example, in high-pressure hydrogenation technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols.
  • Adducts of 1 to 10 moles of ethylene oxide with technical fatty alcohols with 12 to 18 carbon atoms, such as, for example, coconut, palm, palm kernel or tallow fatty alcohol, are preferred.
  • a particularly suitable fatty alcohol mixture contains 65-75% by weight of C12, 20 to 30% by weight of C14, 0-5% by weight of C16 and 0 to 5% by weight of C18 alcohols.
  • This alcohol mixture is commercially available, for example as Dehydol LS TM, a commercial product from Cognis Germany GmbH &. Co. KG.
  • Another particularly suitable fatty alcohol mixture contains 45-60% by weight of C12, 15 to 30% by weight of C14, 5-15% by weight of C16 and 8 to 20% by weight of C18 alcohol.
  • This alcohol mixture is also commercially available, for example as Dehydol LT TM, a commercial product from Cognis Deutschland GmbH & Co. KG.
  • the cosmetic preparations according to the invention can contain the alkyl and / or alkenyl oligoglycosides (component a) and hydroxycarboxylic acid partial esters of alkoxylated alcohols (component b) in a weight ratio of 1:99 to 99: 1, preferably 5:95 to 95: 5, preferably 10:90 to 90:10, particularly preferably 25:75 to 75:25 and in particular 40:60 to 60:40.
  • the preparations are generally in the form of aqueous solutions or pastes which have a solids content (corresponding to the active substance content or the non-aqueous content) of 5 to 50, preferably 10 to 35 and in particular 15 to 25% by weight.
  • the mixtures according to the invention of (a) alkyl and / or alkenyl oligoglycosides and (b) hydroxycarboxylic acid partial esters of ethoxylated alcohols are notable for being particularly compatible with the skin and eye mucous membranes and can also be formulated clearly in hard water without causing any signs of separation.
  • Another object of the present invention therefore relates to their use for the production of cosmetic and / or pharmaceutical preparations in which they can be present in amounts of 0.1 to 50, preferably 1 to 30 and in particular 2 to 15% by weight.
  • the preparations according to the invention can furthermore be used in washing and cleaning preparations in which they can be present in amounts of 0.1 to 50, preferably 1 to 30 and in particular 2 to 15% by weight.
  • the mixtures according to the invention can be used to produce cosmetic and / or pharmaceutical preparations, such as hair shampoos, hair lotions, foam baths, shower baths, creams, gels, lotions, alcoholic and aqueous / alcoholic solutions, emulsions, wax / fat masses, stick preparations, powders or ointments , or for the production of washing and cleaning preparations.
  • cosmetic and / or pharmaceutical preparations such as hair shampoos, hair lotions, foam baths, shower baths, creams, gels, lotions, alcoholic and aqueous / alcoholic solutions, emulsions, wax / fat masses, stick preparations, powders or ointments , or for the production of washing and cleaning preparations.
  • agents can also be used as further auxiliaries and additives, mild surfactants, oil bodies, emulsifiers, superfatting agents, pearlescent waxes, consistency agents, thickening agents, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, stabilizers, biogenic active ingredients, deodorants, antiperspirants, Contain anti-dandruff agents, film formers, swelling agents, UV light protection factors, antioxidants, hydrotropes, preservatives, insect repellents, self-tanners, tyrosine inhibitors (depigmentation agents), solubilizers, perfume oils, dyes and the like.
  • mild surfactants oil bodies, emulsifiers, superfatting agents, pearlescent waxes, consistency agents, thickening agents, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, stabilizers, biogenic active ingredients, deodorants, antiperspirants, Contain anti-dandruff agents
  • Suitable mild, i.e. particularly skin-compatible surfactants are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or Dialkylsulfo- succinate, glutamate fatty acid taurides, fatty acid, betaine ⁇ -olefinsulfonates, ether carboxylic acids, fatty acid glucamides, alkylamido and / or protein fatty acid condensates, the latter preferably based on wheat proteins.
  • Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C 6 -C 22 fatty acids with linear C 6 -C 22 fatty alcohols, esters of branched C 6 -C 3 carboxylic acids are examples of oil bodies with linear C 6 -C 22 fatty alcohols, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl rucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl isostearate, cetyl isostearate, cetyl isostearate, Stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl eru
  • esters of linear G 6 -C 22 fatty acids with branched alcohols in particular 2-ethylhexanol
  • esters of linear and / or branched fatty acids are also suitable polyhydric alcohols (such as propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, triglycerides based on C ⁇ -Cio fatty acids, liquid mono- / di- / triglyceride mixtures based on G ⁇ -C-i ⁇ fatty acids, esters of and / or Guerbet alcohols with aromatic carboxylic acids, especially benzoic acid, esters of C2-Ci 2 -dicarboxylic acids with linear or branched alcohols with 1 to 22 carbon atoms or polyols with 2 to 10 carbon atoms and 2 to 6
  • 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, such as, for example, squalane, squalene or dialkylcyclohexanes.
  • Suitable emulsifiers are, for example, nonionic surfactants from at least one of the following groups:
  • Partial esters of polyglycerol (average degree of self-condensation 2 to 8), polyethylene glycol (molecular weight 400 to 5000), trimethylolpropane, pentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, Bu- tylglucoside, laurylglucoside) and polyglucosides (eg cellulose) with saturated and / or unsaturated, linear or branched fatty acids with 12 to 22 carbon atoms and / or hydroxycarboxylic acids with 3 to 18 carbon atoms and their adducts with 1 to 30 moles of ethylene oxide;
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols or with castor oil are known, commercially available products. These are mixtures of homologs, the average degree of alkoxylation of which is the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate, with which the addition reaction is carried out.
  • Ci 2 / i 8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE 2024051 as refatting agents for cosmetic preparations.
  • Suitable partial glycerides are Hydroxystearinklamo- noglycerid, hydroxystearic acid diglyceride, isostearic acid, isostearic klarediglycerid, rid oleic acid monoglyceride, oleic acid diglyceride, Ricinolklaremoglycerid, Ricinolklarediglycerid, Linolklaremonoglycerid, Linolklarediglycerid, linolenic acid monoglyceride, Linolenchurediglycerid, Erucaklaremonoglycerid, Erucaklarediglyce-, Weinklaremonoglycerid, Weinklarediglycerid, Citronenklamonoglycerid, Citronendiglycerid, Malic acid monoglyceride, malic acid diglyceride and their technical mixtures, which may still contain minor amounts of triglyceride from the manufacturing process. Addition products of 1 to 30, preferably 5
  • polyglycerol esters are polyglyceryl-2 dipolyhydroxystearate (Dehymuls® PGPH), polyglycerol-3-diisostearate (Lameform® TGI), polyglyceryl-4 isostearate (Isolan® Gl 34), polyglyceryl-3 oleates, diisostearoyl polygly- ceryl-3 diisostearate (Isolan® PDI), polyglyceryl-3 methylglucose distearate (Tego Care® 450), polyglyceryl-3 beeswax (Cera Bellina®), polyglyceryl-4 caprate (polyglycerol caprate T2010 / 90), polyglyceryl-3 cetyl Ether (Chimexane® NL), Polyglyceryl-3 Distearate (Cremophor® GS 32) and Polyglyceryl Polyricinoleate (Admul® WOL 1403) Polyglyceryl Dimerate I
  • polystyrene resin examples include the mono-, di- and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like which are optionally reacted with 1 to 30 mol of ethylene oxide.
  • 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-NN-dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the cocosacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxylate - Hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-NN-dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example 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 G ⁇ -alkyl or -acyl group, contain at least one free amino group and at least one - COOH or -SO 3 H group in the molecule and are capable of forming internal salts.
  • Particularly preferred ampholytic surfactants are N-coconut alkyl aminopropionate, coconut acyl amino amino propionate and Ci 2 / i 8 acyl sarcosine.
  • cation surfactants are also suitable as emulsifiers, those of the ester quat 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 that can be used are, for example: 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 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 hydroxyfatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycerides, fatty acids or hydroxyfatty 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, Aerosil types (hydrophilic silicas), polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, ( eg
  • surfactants such as, for example, ethoxylated fatty acid glycerides, _ester- of fatty acids_with - polyols.-such as - for example - pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides, and electro
  • 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, for example, lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, e.g. Amodimethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyaminopolyamides, 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-D nethylamino-1, 3-propane, cationic guar gum, such as e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers, e.g. Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol.
  • dihaloalkylene such as e.g. Dibromobutane with bisdialkylamines, such as ⁇ bis-D nethylamino-1, 3-propane
  • cationic guar gum such as e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese
  • quaternized ammonium salt polymers e.g. Mir
  • 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 their esters, non-crosslinked acrylamide and polyamides of acrylamide and polyamides with non-crosslinked acrylamide and polyamides, non-crosslinked acrylamide and polyamides, with non-crosslinked polyacrylamide and with polyesters, non-crosslinked acrylamide and polyammonyl acrylate - loride / 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 are both liquid and resinous at room temperature can.
  • Farther Suitable are simethicones, which are mixtures of dimethicones with an average _Ke-tten ⁇ äDge - von_20-0 bjs_ 30QJ3imethylsiloxane units and hydrogenated silicates.
  • suitable volatile silicones can also be found by Todd et al. in Cosm.Toil. 91_ s 29 (1976).
  • fats are glycerides
  • waxes include natural waxes such as Candelilla wax, camauba wax, japan wax, esparto grass wax, cork wax, guaruma wax, rice germ oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, walnut, lanolin (wool wax), pretzel fat, ceresin, ozokerite (earth wax), petrolatum, paraffin wax; chemically modified waxes (hard waxes), e.g. Montan ester waxes, Sasol waxes, hydrogenated jojoba waxes and synthetic waxes, such as Polyalkylene waxes and polyethylene glycol waxes in question.
  • natural waxes such as Candelilla wax, camauba wax, japan wax, esparto grass wax, cork wax, guaruma wax, rice germ oil wax, sugar cane wax, ouricury wax, montan wax, beeswa
  • lecithins In addition to fats, fat-like substances such as lecithins and phospholipids can also be used as additives.
  • lecithins to mean those glycerophospholipids which are formed from fatty acids, glycerol, phosphoric acid and choline by esterification. Lecithins are therefore often referred to in the professional world as phosphatidylcholines (PC).
  • PC phosphatidylcholines
  • Examples of natural lecithins are the cephalins, which are also referred to as phosphatidic acids and are derivatives of 1,2-diacyl-sn-glycerol-3-phosphoric acids.
  • phospholipids are usually understood to be mono- and preferably diesters of phosphoric acid with glycerol (glycerol phosphates), which are generally classed as fats.
  • glycerol phosphates glycerol phosphates
  • sphingosines or sphingolipids are also suitable.
  • Metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate can be used.
  • Biogenic active substances are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamins.
  • deodorants counteract, hide or eliminate body odors. Body odors arise from the action of skin bacteria on apocrine sweat, whereby unpleasant smelling breakdown products are formed. Accordingly, deodorants contain active ingredients that act as germ inhibitors, enzyme inhibitors, odor absorbers or odor maskers. As a germ-inhibiting agent, all substances that are effective against gram-positive bacteria are basically suitable, such as.
  • B._4-Hydroxybenzoic acid and its salts and esters N- (4-chlorophenyl) -N ' - (3,4-dichlorophenyl) urea, 2,4,4 ' -trichloro-2'-hydroxy-diphenyl ether (triclosan ), 4-chloro-3,5-dimethylphenol, 2,2 ' -methylene-bis (6-bromo-4-chlorophenol), 3-methyl-4- (1-methylethyl) phenol, 2-benzyl-4-chlorophenol , 3- (4- Chlo ⁇ henoxy) -1, 2-propanedioI, 3-iodo-2-propynyl butyl carbamate, chlorhexidine, 3,4,4 ' - trichlorocarbanilide (TTC), antibacterial fragrances, thymol, thyme oil, eugenol, clove oil, menthol, Mint oil, farnesol, phenoxyethanol
  • Esterase inhibitors are suitable as enzyme inhibitors. These are preferably 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.
  • 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.
  • esterase inhibitors include sterol sulfates or phosphates, such as, for example, lanosterol, cholesterol, campesteric, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and their esters, such as, for example, glutaric acid, mono-glutarate, Diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and their esters such as citric acid, malic acid, tartaric acid or tartaric acid diethyl ester and zinc glycinate.
  • sterol sulfates or phosphates such as, for example, lanosterol, cholesterol, campesteric, stigmasterol and sitosterol sulfate or phosphate
  • dicarboxylic acids and their esters such as, for example, glutaric acid, mono-glutarate, Diethy
  • Suitable as odor absorbers are substances which absorb odor-forming compounds and can retain them to a large extent. They lower the partial pressure of the individual components and thus also reduce their speed of propagation. It is important that perfumes have to remain unaffected. Odor absorbers are not effective against bacteria. They contain, for example, the main component of a complex zinc salt of ricinoleic acid or special, largely odorless fragrances that are known to the person skilled in the art as "fixators", such as, for example, B. extracts of Labdanum or Styrax or certain abietic acid derivatives. Fragrance agents or perfume oils act as odor maskers and, in addition to their function as odor maskers, give the deodorants their respective fragrance.
  • Perfume oils are, for example, mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flowers, stems and leaves, fruits, fruit peels, roots, woods, herbs and grasses, needles and twigs as well as resins and balms. Animal raw materials, such as civet and castoreum, are also suitable. Typical synthetic fragrance compounds Bonds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type.
  • Fragrance compounds of the ester type are, for example, benzyl acetate, p-tert-butylcyclohexyl acetate, linalyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, allyl cyclohexyl propionate, styrallyl propionate and benzyl salicylate.
  • the ethers include, for example, benzyl ethyl ether
  • the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetal dehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal
  • the ketones include, for example, the jonones and methylcedryl ketone
  • the alcohols are anethole
  • Citronellol Citronellol
  • eugenol isoeugenol
  • geraniol linalool
  • the hydrocarbons mainly include the terpenes and balsams.
  • fragrance oils of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labdanum oil and lavandin oil.
  • Antiperspirants reduce sweat formation by influencing the activity of the eccrine sweat glands and thus counteract armpit wetness and body odor.
  • Aqueous or anhydrous formulations of antiperspirants typically contain the following ingredients:
  • non-aqueous solvents such as As ethanol, propylene glycol and / or glycerin.
  • Salts of aluminum, zirconium or zinc are particularly suitable as astringent antiperspirant active ingredients.
  • suitable antiperspirant Active ingredients are, for example, aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, __ aluminum sesquichlorohydrate and. whose_ complex compounds e.g. B. with propylene glycol-1, 2nd Aluminum hydroxyallantoinate, aluminum chloride tartrate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate and their complex compounds z. B. with amino acids such as glycine.
  • oil-soluble and water-soluble auxiliaries can be present in smaller amounts in antiperspirants.
  • oil soluble aids can e.g. his:
  • water-soluble additives are e.g. Preservatives, water-soluble fragrances, pH adjusting agents, e.g. Buffer mixtures, water soluble thickeners, e.g. water-soluble natural or synthetic polymers such as Xanthan gum, hydroxyethyl cellulose, polyvinyl pyrrolidone or high molecular weight polyethylene oxides.
  • Octopirox® (1-hydroxy-4-methyl-6- (2,4,4-trimythylpentyl) -2- (1 H) -pyridone monoethanolamine salt
  • Baypival Pirocton Olamin
  • Ketoconazol® (4-acetyl -1 - ⁇ - 4- [2- (2.4-dichlorophenyl) r-2- (1 H -imidazol-1-ylmethyl) -1, 3-dioxylan-c-4-ylmethoxyphenyl ⁇ piperazine, selenium disulfide, sulfur colloidal, sulfur polyethyleneglycolsorbitan monooleate , Sulfuric ricinole polyhexylate,
  • Sulfur tar distillates Sulfur tar distillates, salicylic acid (or in combination with hexachlorophene), undexylene acid monoethanolamide sulfosuccinate sodium salt, Lamepon® UD (protein undecylenic acid condensate, zinc pyrethione, aluminum pyrition and magnesium pyrithione / dipyrithione magnesium sulfate) can be used.
  • 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.
  • UV light protection factors are, for example, liquid at room temperature or JiDsiaIIJD_v r-üegende.orgarjis_cl ⁇ e Su ⁇ . (Light protection filter), 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:
  • 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-ethylhexyl 2-cyano-3,3-phenylcinnamate (octocrylene);
  • esters of salicylic acid preferably salicylic acid 2-ethylhexyl ester, salicylic acid 4-isopropylbenzyl ester, salicylic acid homomethyl ester;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone
  • 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 0818450 A1 or dioctyl butamido triazone (Uvasorb ® HEB);
  • 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 a shape which differs in some other way from the spherical shape.
  • the pigments can also be surface-treated, ie hydrophilized or hydrophobicized.
  • Typical examples are coated titanium dioxide, such as titanium dioxide T 805 (Degussa) or Eusolex® T20 ⁇ 0 (Merck). Silicones, and in particular trialkoxyoctylsilanes or simethicones, are particularly suitable as hydrophobic coating agents. So-called micro- or nanopigments are preferably used in sunscreens. Micronized zinc oxide is preferably used. Further suitable 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. urocanin
  • I acid and their derivatives
  • peptides such as D, L-camosine, D-carnosine, L-camosine and their derivatives (eg anserine), carotenoids, carotenes (eg ⁇ -carotene, ⁇ -carotene, lycopin) and their derivatives
  • Chlorogenic acid and its derivatives e.g. dihydroliponic acid
  • aurothioglucose 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 their derivatives (esters, ethers, pepti- de, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g.
  • buthioninsulfoximines homocysteine sulfoximine, butioninsulfones, penta-, hexa-, heptathioninsulfoximine
  • very low tolerable dosages 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 bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g.
  • ⁇ -linolenic acid linoleic acid, oleic acid
  • folic acid and its derivatives ubiquinone and ubiquinol and their derivatives
  • vitamin C and derivatives e.g. ascorbyl palmitate, Mg ascorbyl phosphate, ascorbylacetate
  • tocopherols and derivatives e.g.
  • vitamin E- acetate vitamin E and derivatives (vitamin A palmitate) and coniferyl benzoate of benzoin, rutinic acid and its derivatives, ⁇ -glycosyl rutin, ferulic acid, furfurylidene glucitol, carnosine, butyl - hydroxytoluene, butylated hydroxyanisole, nordihydroguajakh resin acid, nordihydroguajaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, superoxide dismutase, zinc and its derivatives (eg ZnO, ZnSO 4 ) selenium and its derivatives (eg selenium methionine) and their derivatives (for example stilbene oxide, trans-stilbene oxide) and the derivatives (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active substances which are suitable according to the invention
  • 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.
  • the polyols can also contain further functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are
  • Alkylene glycols such as 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, trimethylthylbutane, 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,
  • Dialcohol amines such as diethanolamine or 2-amino-1, 3-propanediol.
  • Suitable preservatives are, for example - phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the other classes of substances listed in Appendix 6, Parts A and B of the Cosmetics Regulation.
  • N, N-diethyl-m-toluamide, 1, 2-pentanediol or ethyl butylacetylaminopropionate are suitable as insect repellents, and dihydroxyacetone is suitable as a self-tanning agent.
  • Arbutin, kojic acid, coumaric acid and ascorbic acid (vitamin C) can be used as tyrosine inhibitors, which prevent the formation of melanin and are used in depigmenting agents.
  • Perfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot te, 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 pine), resins and balsams (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 e.g.
  • Ethers include, for example, benzylethyl ether, the aldehydes, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetalde- hyd, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal, the ketones, for example the jonones, ⁇ -isomethylionone and methylcedryl ketone, the alcohols Anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpinol, the hydrocarbons mainly include terpenes and balms.
  • fragrance oils which are mostly used as aroma components
  • perfume oils are suitable as perfume oils.
  • perfume oils eg. Sage oil.
  • bergamot oil dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, ⁇ -hexylcinnamaldehyde, geraniol, benzyl acetone, cyclamen aldehyde, linalool, Boisambrene Porte, Ambroxan, indole, hedione, Sandelice, lemon oil, mandarin oil, orange oil, allyl amyl glycolate, Cyclovertal, lavandin oil, muscatel Sage oil, ß-damascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-E-Super, Fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romilllate, irot
  • the dyes which can be used are the 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.
  • Ci 2 / i 4 coconut alkyl oliogoglucoside available as Plantacare 1200UP TM from Cognis Deutschland GmbH & Co. KG
  • the preparation was carried out analogously to c) from citric acid and dehydol LS.
  • a light yellow, cloudy, separating liquid was obtained with the following characteristics: saponification number: 385, acid number: 234, free citric acid: 3.4% by weight,
  • the saponification number (VZ) was determined in accordance with DGF CV 3.
  • the acid number (SZ) was determined in accordance with DIN 53402 example 1
  • Example 2 Analogously to Example 1, 10 g of the citric acid ester prepared according to b) and 20 g of Plantacare 1200 UP TM were dissolved in 170 g of distilled water (active substance content 20% by weight). The pH was adjusted to 6.4 with citric acid. A clear, bare liquid was obtained.

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Abstract

L'invention concerne des préparations cosmétiques et/ou pharmaceutiques à fort pouvoir moussant, qui contiennent : (a) des alkyloligoglycosides et/ou des alkényloligoglycosides et (b) des esters partiels d'acide hydroxycarboxylique d'alcools alcoxylés.
EP04728534A 2003-04-30 2004-04-21 Preparations cosmetiques et/ou pharmaceutiques Withdrawn EP1620067A1 (fr)

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DE10319399A DE10319399A1 (de) 2003-04-30 2003-04-30 Kosmetische und/oder pharmazeutische Zubereitungen
PCT/EP2004/004207 WO2004096963A1 (fr) 2003-04-30 2004-04-21 Preparations cosmetiques et/ou pharmaceutiques

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DE102007018983A1 (de) * 2007-04-21 2008-10-23 Cognis Ip Management Gmbh Agrochemische Zubereitungen
JP2009209121A (ja) * 2008-03-06 2009-09-17 Kose Corp メラノソーム輸送阻害剤、及び皮膚外用剤
FR2942974B1 (fr) * 2009-03-11 2011-03-18 Agro Ind Rech S Et Dev Ard Compositions emulsionnantes a base de polyglycosides d'alkyle et d'esters
EP2336290A1 (fr) * 2009-12-15 2011-06-22 Cognis IP Management GmbH Préparations en forme de gel
US10253236B2 (en) * 2013-10-31 2019-04-09 Amril Ag Environmental friendly well treatment fluids comprising an ester

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US4172887A (en) * 1973-11-30 1979-10-30 L'oreal Hair conditioning compositions containing crosslinked polyaminopolyamides
IT1201411B (it) * 1985-03-26 1989-02-02 Rol Raffineria Olii Lubrifican Tesnioattivi derivati dall'acido citrico
DE3723826A1 (de) * 1987-07-18 1989-01-26 Henkel Kgaa Verfahren zur herstellung von alkylglykosiden
US5576425A (en) * 1988-10-05 1996-11-19 Henkel Kommanditgesellschaft Auf Aktien Process for the direct production of alkyl glycosides
DE4302315A1 (de) * 1993-01-28 1994-08-04 Henkel Kgaa Oberflächenaktive Mischungen
IL108500A (en) * 1994-01-31 1998-06-15 Zohar Detergent Factory Fatty alcohol sulphates in granular form and process for their preparation
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