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WO2001037790A1 - Utilisation d'esters d'acide gras d'alkyle et/ou d'alcenyloligoglucoside, afin d'ameliorer l'evaluation sensorielle d'emulsions - Google Patents

Utilisation d'esters d'acide gras d'alkyle et/ou d'alcenyloligoglucoside, afin d'ameliorer l'evaluation sensorielle d'emulsions Download PDF

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Publication number
WO2001037790A1
WO2001037790A1 PCT/EP2000/011854 EP0011854W WO0137790A1 WO 2001037790 A1 WO2001037790 A1 WO 2001037790A1 EP 0011854 W EP0011854 W EP 0011854W WO 0137790 A1 WO0137790 A1 WO 0137790A1
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Prior art keywords
acid
alkyl
esters
fatty
carbon atoms
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PCT/EP2000/011854
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German (de)
English (en)
Inventor
Achim Ansmannn
Rolf Kawa
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Cognis Deutschland Gmbh & Co. Kg
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Application filed by Cognis Deutschland Gmbh & Co. Kg filed Critical Cognis Deutschland Gmbh & Co. Kg
Priority to EP00989901A priority Critical patent/EP1244417A1/fr
Priority to JP2001539407A priority patent/JP2003514836A/ja
Publication of WO2001037790A1 publication Critical patent/WO2001037790A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids

Definitions

  • the invention relates to the use of alkyl and / or alkenyl oligoglycoside fatty acid esters to improve the sensory assessment of emulsions.
  • oil-soluble bases are required, the task of which is to transport polar ingredients, such as active ingredients or moisture, through the lipid barrier of the skin.
  • polar ingredients such as active ingredients or moisture
  • a large number of natural and synthetic oils are suitable for this purpose, for example almond or avocado oil or ester oils based on short-chain triglycerides.
  • the oil components in the above-mentioned agents also have a nourishing effect, which is directly related to skin oiling.
  • the consumer desires products that impart a non-sticky, quickly occurring and long-lasting feeling of smoothness and suppleness to the skin and that are also rich.
  • the subjective sensation on the skin can be correlated and objectified with the physicochemical parameter of the oil body spreading on the skin, as described by U. Zeidler in fats, soaps, paints. 87, 403 (1985). Accordingly, cosmetic oil bodies can be divided into low-spreading (below 300 mm 2 / 10min), medium-spreading (approx. 300 to 1000 mm 2 / 10min) and high-spreading oils (above 1000 mm 2 / 10min). If a high-spreading oil is used in a given formulation as an oil body, the desired feeling of skin smoothing is achieved very quickly, but the experience does not last long.
  • the object of the present invention was to provide new agents which impart a non-sticky, rapidly occurring and long-lasting feeling of smoothness and suppleness to the skin and which are also rich.
  • the invention relates to the use of alkyl and / or alkenyl oligoglycoside fatty acid esters to improve the sensory assessment of emulsions.
  • alkyl and / or alkenyl oligoglycoside fatty acid esters are able to improve the sensory assessment of emulsions and thus impart a rapidly occurring and long-lasting feeling of smoothness and suppleness to the skin. In addition, they have a rich consistency.
  • esters of alkyl and / or alkenyl oligoglycosides and fatty acids which are hereinafter referred to briefly as “glycoside esters”, are known from the prior art. Although they are usually methylglucoside esters, they are also the preparation of the esters with higher fatty acids is carried out in a manner known per se, ie by alkaline-catalyzed esterification of the starting materials, which are explained in more detail below. Usually, technical mixtures of products with different degrees of substitution are obtained during the esterification. However, mono- and especially diesters or their technical mixtures are preferred as Dispersants in amounts of 5 to 30, preferably 10 to 20 wt .-% - based on the final concentration - used. Alkyl and / or alkenyl oligoglycosides
  • Alkyl and / or alkenyl oligoglycosides are known nonionic surfactants which follow the formula (I)
  • R 1 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms
  • p is a number from 1 to 10.
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • the index number p in the general formula (I) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
  • Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, preference is given to those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
  • the alkyl or alkenyl radical PO 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, 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 18, carbon atoms.
  • Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and their technical mixtures, which can be obtained as described above.
  • Alkyl oligoglucosides based on hydrogenated Ci2 / i4 coconut alcohol with a DP of 1 to 3 are preferred.
  • Fatty acids are understood to mean aliphatic or aromatic, mono- or polyvalent, optionally hydroxy-functionalized fatty acids of the formula (II)
  • R 2 CO represents a linear or branched acyl radical having 6 to 22 carbon atoms.
  • Fatty acids of the formula (II) are preferably used, in which R 2 CO represents a linear acyl radical having 16 to 18 carbon atoms.
  • Typical examples are monofatty acids such as caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, aradoleic acid, araoleic acid, elaoleic acid stearic acid as well as their technical mixtures.
  • Palmitic acid and stearic acid, isostearic acid and / or oleic acid are particularly preferred.
  • corresponding C6 -C 2 -difatty acids can also be used, so that adipic acid and dodecanedioic acid are also suitable.
  • hydroxy-functionalized polyvalent fatty acids can also be used, such as, for example, hydroxystearic acid.
  • Cosmetic and / or pharmaceutical preparations which contain the glycoside esters according to the invention in the emulsions can furthermore contain, as further auxiliaries and additives, mild surfactants, emulsifiers, oil bodies, superfatting agents, pearlescent waxes, consistency agents, thickeners, polymers, silicone compounds, fats, waxes, stabilizers , biogenic agents, deodorants, antidandruff agents, film formers, swelling agents, UV light protection factors, antioxidants, hydrotropes, preservatives, insect repellents, self-tanners, solubilizers, perfume oils, dyes, germ-inhibiting agents and the like.
  • mild surfactants emulsifiers
  • emulsifiers oil bodies, superfatting agents, pearlescent waxes, consistency agents, thickeners, polymers, silicone compounds, fats, waxes, stabilizers , biogenic agents, deodorants, antidandruff agents, film formers, swelling agents, UV light protection factors, antioxidants,
  • Suitable mild, i.e. surfactants that are particularly compatible with the skin are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ether carboxylic acids, alkyl oligoglucosides, fatty acid glucamides or alkyl amide fatty acid proteins, and alkyl amide fatty acid proteins, preferably protein amide fatty acid proteins, or alkyl amide fatty acid proteins, or alkyl amide fatty acid proteins, or alkyl amido fatty acid proteins, preferably protein-based fatty acid proteins or alkyl amide fatty acid proteins, alkyl amide fatty acid proteins, and alkyl amido fatty acid proteins.
  • Suitable emulsifiers are nonionic surfactants from at least one of the following groups: (1) Adducts of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 C atoms, with fatty acids with 12 to 22 C atoms and with alkylphenols with 8 to 15 C atoms in the alkyl group;
  • alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs
  • 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 as well as 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (eg sorbitol), alkyl glucosides (eg methyl glucoside, butyl glucoside, butyl glucoside, - coside) and polyglucosides (eg cellulose);
  • 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 mixtures of homologs, the medium of which Degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • Ci2 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE 2024051 PS as refatting agents for cosmetic preparations.
  • C8 / ⁇ -alkyl mono- and oligoglycosides their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosac charidene 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 oligomeric glycosides with a degree of oligomerization of up to about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxylm -hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a C ⁇ -alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -S0 3 H 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, cocoacylaminoethylamino propionate and Ci2 / i8-acylsarcosine.
  • quaternary emulsifiers are also suitable, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • Guerbet alcohols are formed as oil bodies on the basis of fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C6-C22 fatty acids with linear C6-C22 fatty alcohols, esters of branched C6-C 3 carboxylic acids with linear C6- C22 fatty alcohols, esters of linear C ⁇ -C ⁇ fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of hydroxycarboxylic acids with linear or branched C6-C 2 fatty alcohols, especially dioctyl malates, esters of linear and / or branched fatty acids with polyhydric alcohols (such as propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, triglycerides based on C ⁇ -Cio fatty acids, liquid mono- / di- / triglyceride mixtures based on C ⁇ -Cis fatty acids,
  • Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid realanolamides 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, 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
  • 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, 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 trimethylolpropane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides as well as electrolytes such as sodium chloride and ammonium chloride.
  • polysaccharides in particular xanthan gum, guar guar, agar
  • 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 polyglycols and amines, quaternized collagen polypeptides, such as, for example, lauryldimonium hydroxy propyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as amidomethicones, copolymers of adipic acid and dimethylaaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers
  • Suitable anionic, zwitterionic, amphoteric and nonionic polymers are, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and esters thereof, uncrosslinked and polyol-crosslinked polyacrylic acids, acrylamidopropyl trimethylammonium chloride / acrylate Copolymers, octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxyproyl methacrylate copolymers, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymers, vinyl pyrrolidone / dimethylaminoethyl methacrylate / vinyl caprolact
  • 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, carnauba wax, candelilla wax, montan wax, paraffin wax, hydrogenated castor oils, fatty acid esters solid at room temperature or micro waxes, optionally in combination with hydrophilic waxes, e.g. Cetyl stearyl alcohol or partial glycerides in question.
  • Metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate are used.
  • Biogenic active substances are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes.
  • Antiperspirants such as aluminum chlorohydates are suitable as deodorant active ingredients. These are colorless, hygroscopic crystals that easily dissolve in the air and arise when aqueous aluminum chloride solutions are evaporated.
  • Aluminum chlorohydrate is used 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)].
  • aluminum hydroxylactates and acidic aluminum / zirconium salts can also be used.
  • Esterase inhibitors can be added as further deodorant active ingredients. These are preferably trialkyl citrates such as 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 include sterolsulfates or phosphates, such as, for example, lanosterol, cholesterol, campesterin, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and their esters, such as, for example, glutaric acid, glutaric acid monoethyl esters, glutaric acid diethyl esters, adipic acid monoesters, adipic acid monoesters, adipic acid monoesters and adipic acid monoesters , Diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and their esters such as citric acid, malic acid, tartaric acid or tartaric acid diethyl esters.
  • sterolsulfates or phosphates such as, for example, lanosterol, cholesterol, campesterin, stigmasterol and sitosterol sulfate or phosphate
  • 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, pemules 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, for example 3- (4-methylbenzylidene) camphor as described in EP 0693471 B1;
  • 4-aminobenzoic acid derivatives preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate esters of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate, 4-methoxycinnamate propyl esters, 4-methoxycinnamic acid isoamyl ester 2-cyano-3,3-phenylcinnamic acid 2-ethylhexyl esters (octocrylene);
  • esters of salicylic acid preferably salicylic acid 2-ethylhexyl ester, salicylic acid 4-isopropylbenzyl ester, salicylic acid homomenthyl esters;
  • 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;
  • Propane-1,3-dione e.g. 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1,3-dione; Ketotricyclo (5.2.1.0) decane derivatives, as described in EP 0694521 B1.
  • Possible water-soluble substances are:
  • Sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts;
  • Sulfonic acid derivatives of 3-benzylidene camphor e.g. 4- (2-oxo-3-bomylidenemethyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bornylidene) sulfonic acid and their salts.
  • benzoylmethane such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione, 4-tert-butyl
  • benzoylmethane such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione, 4-tert-butyl
  • typical 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 are ellipsoidal or which differ in some other way from the spherical shape To have shape. So-called micro- or nanopigments 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 DL-carnosine, D-camosine, L-camosine 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. dihydroliponic 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 thiopropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (eg buthioninsulfoximines, homocysteine sulfoximine, butioninsulfones, penta-, hexa-, heptathioninsulfoximine) in very small amounts compatible dosages (e.g.
  • ⁇ -hydroxy fatty acids e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g.
  • 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 3535 insect repellants are suitable as insect repellents, and dihydroxyacetone is suitable as a self-tanning agent.
  • Perfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peels (bergamot, lemon, oranges), roots (mace, angeiica, 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 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 methylphenyl glycinate, allyl cyclohexyl propylate pylate propylate propionate.
  • 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, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal
  • the ketones include, for example, the jonones, oc-isomethylionone 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 of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, for example sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • bergamot oil dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, ⁇ -hexylcinnamaldehyde, geraniol, benzyl acetone, cyclamen aldehyde, linalool, Boisambrene Forte, 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 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.
  • germ-inhibiting agents are preservatives with a specific action against gram-positive bacteria, such as, for example, 2,4,4'-trichloro-2'-hydroxydiphenyl ether, chlorhexidine (1,6-di- (4-chlorophenyl-biguanido) -hexane) or TCC (3,4,4'-trichlorocarbanilide).
  • gram-positive bacteria such as, for example, 2,4,4'-trichloro-2'-hydroxydiphenyl ether, chlorhexidine (1,6-di- (4-chlorophenyl-biguanido) -hexane) or TCC (3,4,4'-trichlorocarbanilide).
  • Numerous fragrances and essential oils also have antimicrobial properties.
  • Typical examples are the active ingredients eugenol, menthol and thymol in clove, mint and thyme oil.
  • terpene alcohol famesol (3,7, 11-trimethyl yl-2,6, 10-dodecatrien-1-ol), which is present in linden flower oil and has a lily of the valley smell.
  • Glycerol monolaurate has also proven itself as a bacteriostatic.
  • the proportion of the additional germ-inhibiting agents is usually about 0.1 to 2% by weight, based on the solids content of the preparations.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.
  • the agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used.
  • Examples 1 to 3 comparative examples V1 to V6.
  • a panel consisting of 5 experienced people tested formulations based on a standard skin cream for their subjective feeling of smoothness. On the basis of this, a scale between 1 (hardly any smoothing or rapid decrease in the feeling of smoothness) and 6 (quick, even feeling of smoothness) and the richness of the formulation were assessed on a scale of 1 to 6.
  • the information in Table 1 represents mean values. Examples 1 to 3 are according to the invention, and Examples V1 and V2 are used for comparison.

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Abstract

La présente invention concerne l'utilisation d'esters d'acide gras d'alkyle et/ou d'alcényloligoglucoside, afin d'améliorer l'évaluation sensorielle d'émulsions.
PCT/EP2000/011854 1999-11-25 2000-11-27 Utilisation d'esters d'acide gras d'alkyle et/ou d'alcenyloligoglucoside, afin d'ameliorer l'evaluation sensorielle d'emulsions WO2001037790A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP00989901A EP1244417A1 (fr) 1999-11-25 2000-11-27 Utilisation d'esters d'acide gras d'alkyle et/ou d'alcenyloligoglucoside, afin d'ameliorer l'evaluation sensorielle d'emulsions
JP2001539407A JP2003514836A (ja) 1999-11-25 2000-11-27 エマルジョンの感覚的評価を改善するためのアルキルおよび／またはアルケニルオリゴグリコシド脂肪酸エステルの使用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19956606.2 1999-11-25
DE1999156606 DE19956606A1 (de) 1999-11-25 1999-11-25 Verwendung von Alkyl- und/oder Alkenyloligoglykosid-Fettsäureestern zur Verbesserung der sensorischen Beurteilung von Emulsionen

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WO2001037790A1 true WO2001037790A1 (fr) 2001-05-31

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PCT/EP2000/011854 WO2001037790A1 (fr) 1999-11-25 2000-11-27 Utilisation d'esters d'acide gras d'alkyle et/ou d'alcenyloligoglucoside, afin d'ameliorer l'evaluation sensorielle d'emulsions

Country Status (4)

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EP (1) EP1244417A1 (fr)
JP (1) JP2003514836A (fr)
DE (1) DE19956606A1 (fr)
WO (1) WO2001037790A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0427210A2 (fr) * 1989-11-06 1991-05-15 Lion Corporation Agent tensioactif non ionique
US5603940A (en) * 1993-10-08 1997-02-18 L'oreal Oil-in-water emulsion which may be used for obtaining a cream
FR2748937A1 (fr) * 1996-05-24 1997-11-28 Ulice Sa Utilisation d'alpha-alklyglucosides et d'esters d'alpha-alkylglucosides en tant qu'agents emulsionnants anti-microbiens
EP0987011A1 (fr) * 1998-08-17 2000-03-22 L'oreal Composition cosmétique et/ou dermatologique contenant de l'acide salicylique ou un dérivé d'acide salicylique et son utilisation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0427210A2 (fr) * 1989-11-06 1991-05-15 Lion Corporation Agent tensioactif non ionique
US5603940A (en) * 1993-10-08 1997-02-18 L'oreal Oil-in-water emulsion which may be used for obtaining a cream
FR2748937A1 (fr) * 1996-05-24 1997-11-28 Ulice Sa Utilisation d'alpha-alklyglucosides et d'esters d'alpha-alkylglucosides en tant qu'agents emulsionnants anti-microbiens
EP0987011A1 (fr) * 1998-08-17 2000-03-22 L'oreal Composition cosmétique et/ou dermatologique contenant de l'acide salicylique ou un dérivé d'acide salicylique et son utilisation

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DE19956606A1 (de) 2001-05-31
EP1244417A1 (fr) 2002-10-02
JP2003514836A (ja) 2003-04-22

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