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WO2000069410A1 - Preparations cosmetiques et/ou pharmaceutiques - Google Patents

Preparations cosmetiques et/ou pharmaceutiques Download PDF

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Publication number
WO2000069410A1
WO2000069410A1 PCT/EP2000/004025 EP0004025W WO0069410A1 WO 2000069410 A1 WO2000069410 A1 WO 2000069410A1 EP 0004025 W EP0004025 W EP 0004025W WO 0069410 A1 WO0069410 A1 WO 0069410A1
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WO
WIPO (PCT)
Prior art keywords
acid
alkyl
oil
fatty
carbon atoms
Prior art date
Application number
PCT/EP2000/004025
Other languages
German (de)
English (en)
Inventor
Markus Sumser
Werner Seipel
Hermann Hensen
Holger Tesmann
Original Assignee
Cognis Deutschland Gmbh
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Filing date
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Publication of WO2000069410A1 publication Critical patent/WO2000069410A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • 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
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/70—Biological properties of the composition as a whole

Definitions

  • the invention relates to preparations containing alkyl and / or alkenyl oligoglycosides, fatty acid partial glycerides and fungicides and the use thereof for the production of cosmetic and / or pharmaceutical preparations.
  • Cosmetic preparations for cleaning and maintaining human skin and hair can contain fungicides in addition to surface-active substances, such as anionic or amphoteric surfactants. At the present time, these active ingredients are introduced into cosmetic preparations by a hot process, which is therefore associated with high costs. In addition, the agents available on the market have an insufficient dermatological tolerance and often lead to drying out of the skin and hair.
  • the object of the invention was therefore to provide means which enable cold processing of fungicides, such as climbazole. Furthermore, these mixtures should counteract drying of the skin and hair when used. In addition, it should be ensured that these agents are also stable over a longer storage period and have a particularly good dermatological tolerance.
  • the invention relates to cosmetic and / or pharmaceutical preparations containing
  • fungicides such as climbazole
  • fungicides can be processed cold in cosmetic preparations if they have been mixed with alkyl and / or alkenyl oligoglycosides and partial glycerides.
  • these mixtures show good moisturizing properties and thus counteract drying out.
  • the improved dermatological compatibility of these agents and the increased storage stability are also advantageous.
  • Alkyl and alkenyl oligoglycosides which form component (a) 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
  • x 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 alkyl or alkenyl radical R 1 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capro alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14 carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, 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.
  • Preferred are alkyl oligoglucosides based on hydrogenated C12 / coconut alcohol with a DP of 1 to 3.
  • the preparations according to the invention can contain the alkyl and alkenyl oligoglycosides in amounts of 0 , 5 to 50, preferably 1 to 30 and in particular 5 to 20% by weight, based on the preparation and calculated as a solid
  • the selected fatty acid partial glycendes which form component (b), are known substances which can be prepared by the relevant methods of preparative organic chemistry.
  • Fatty acid partial glycendes ie usually technical mixtures of mono- and diglycene, are usually obtained by transesterification the corresponding T ⁇ glyce ⁇ de with Glyce- ⁇ n or obtained by targeted esterification of fatty acids
  • the separation of unreacted starting materials and the enrichment of monoglycides in the mixtures is usually carried out by molecular distillation.
  • the partial glycides of the present invention are preferably by esterification of Glycenn with oleic acid, isostearic acid, Prepared behenic acid or isobehenic acid
  • the isobehenic acid is the hardened monomer fraction which arises in the dimensioning of erucic acid.
  • the invention includes the finding that technical mono- / diglycend mixtures in d he application shows an even better dermatological compatibility than the pure monoglycides. Accordingly, those technical fatty acid mono- / di-glyceride are preferred which have a molar ratio of mono- to diester in the range from 10 90 to 90 10 and in particular 80 20 to 50 50
  • the preparations according to the invention can contain the partial glycene in amounts of 0.5 to 30, preferably 1 to 10 and in particular 2 to 5% by weight, based on the preparation and calculated as a solid Fungicides
  • the fungicides which are suitable as component (c) are preferably oil-soluble substances.
  • suitable fungicides are azoxystrobin, benalaxyl, carben- dazim, chlorothalonil, cupfer, cymoxanil, cyproconazole, diphenoconazole, dinocap, epoxiconazole, fluazinam, flusilazole, flutriafol, Folpel, fosetyl-aluminum, hexaconoxyl-methyl, cresaconazol-mole, kresaconazol-mole Metconazole, Myclobutanil, Ofurace, Phentinhydroxid, Prochloraz, Pyremethanil, Soufre, Tebucanazol, and Tetraconazole and their mixtures.
  • Climbazol (Baypival®, Bayer) is preferably used.
  • the preparations according to the invention can contain the fungicides in amounts of 0.01 to 10, preferably 0.1 to 5 and in particular 1 to 2% by weight, based on the preparation and calculated as a solid.
  • esters which may be present as optional component (d), is generally understood to mean quaternized fatty acid triethanolamine ester salts. These are known substances that can be obtained using the relevant methods of preparative organic chemistry. In this connection, reference is made to international patent application WO 91/01295 (Henkel), according to which triethanolamine is partially esterified with fatty acids in the presence of hypophosphorous acid, air is passed through and then quaternized with dimethyl sulfate or ethylene oxide. German patent DE 4308794 C1 (Henkel) also discloses a process for the production of solid ester quats, in which the quaternization of triethanolamine esters is carried out in the presence of suitable dispersants, preferably fatty alcohols.
  • suitable dispersants preferably fatty alcohols.
  • R 2 CO for an acyl radical with 6 to 22 carbon atoms
  • R 3 and R 4 independently of one another for hydrogen or R 2 CO
  • R 5 for an alkyl radical with 1 to 4 carbon atoms or a (CH ⁇ CH ⁇ OJqH group, m , n and p in total stand for 0 or numbers from 1 to 12, q stands for numbers from 1 to 12 and
  • X stands for halide, alkyl sulfate or alkyl phosphate .
  • ester quats which in the sense of the invention can be used are products based on caproic acid, caprylic acid, capinic acid, lau ⁇ nsaure, my ⁇ stinsaure, palmitic acid, isosteanic acid, stearic acid, oleic acid, elaidic acid, arachinic acid, behenic acid and erucic acid, as well as their technical blends and their splitting, such as natural fetting, such as in natural fats Oils accumulate Technical Ci2 / i8 coconut fatty acids and in particular partially hardened Ci6 / ⁇ s tallow or palm fatty acids and high-elaidic acid-rich Ci6 / ⁇ s fatty acid cut are preferably used.
  • the fatty acids and the triethanolamine in a molar ratio of 1.1 can be used to prepare the quaternized esters up to 3 1 are used
  • an output ratio of 1.2 1 to 2.2 1, preferably 15 1 to 1.9 1 has proven to be particularly advantageous.
  • the preferred ester quats are technical mixtures of mono- , Di- and T ⁇ esters with an average degree of esterification from 1, 5 to 1 9 and are derived from technical C.6 / .8 tallow or palm fatty acid (iodine number 0 to 40).
  • quaternized fatty acid methyl ester salts of the formula (II) have been found to be particularly advantageous proven in which R 2 CO stands for an acyl radical with 16 to 18 carbon atoms, R 3 for R 2 CO, R 4 for hydrogen, R 5 for a methyl group, m, n and p for 0 and X for methyl sulfate
  • quaternized ester salts of fatty acids with diethanolalkylamines of the formula (III) are also suitable as ester quats.
  • R 2 CO stands for an acyl radical with 6 to 22 carbon atoms
  • R 3 for hydrogen or R 2 CO
  • R 5 and R 6 independently of one another for alkyl radicals with 1 to 4 carbon atoms
  • m and n in total for 0 or numbers of 1 to 12
  • X represents halide, alkyl sulfate or alkyl phosphate
  • suitable ester quats are substances in which the ester bond is replaced by an amide bond and which preferably follow the formula (V) based on diethylenetriamine,
  • R 2 CO is an acyl radical having 6 to 22 carbon atoms
  • R 3 is hydrogen or R 2 CO
  • R 7 and R 8 are independently alkyl radicals having 1 to 4 carbon atoms
  • X is halide, alkyl sulfate or alkyl phosphate.
  • amide ester quats are available on the market, for example, under the name Incroquat (Croda).
  • esterquats of the formulas (III) to (V).
  • the esterquats usually come on the market in the form of 50 to 90% strength by weight alcoholic solutions, which can be diluted with water if required.
  • the preparations according to the invention can contain the esterquats in amounts of 0 to 20, preferably
  • Chitosans which can be included as optional component (s), are biopolymers and are included in the group of hydrocolloids. From a chemical point of view, these are partially deacetylated chitins of different molecular weights that contain the following - idealized - monomer unit:
  • chitosans are cationic biopolymers under these conditions.
  • the positively charged chitosans can and will interact with oppositely charged surfaces therefore used in cosmetic hair and body care products and pharmaceutical preparations (cf. Ullmann 's Encyclopedia of Industrial Chemistry, 5th Ed., Vol. A6, Weinheim, Verlag Chemie, 1986, pp. 231-232).
  • Overviews on this topic are also available, for example, from B. Gesslein et al. in HAPPI 27, 57 (1990), 0. Skaugrud in Drug Cosm. Ind. 148: 24 (1991) and E. Onsoyen et al.
  • chitosans is based on chitin, preferably the shell remains of crustaceans, which are available in large quantities as cheap raw materials.
  • the chitin is used in a process that was first developed by Hackmann et al. has been described, usually first deproteinized by adding bases, demineralized by adding mineral acids and finally deacety- lated by adding strong bases, it being possible for the molecular weights to be distributed over a broad spectrum.
  • Appropriate methods are, for example, made from Makromol. Chem. 177, 3589 (1976) or French patent application FR 2701266 A.
  • Preferred types are those as disclosed in German patent applications DE 4442987 A1 and DE 19537001 A1 (Henkel) and which have an average molecular weight of 800,000 to 1,200,000 Daltons, a Brookfield viscosity (1% by weight in glycolic acid ) below 5000 mPas, a degree of deacetylation in the range from 80 to 88% and an ash content of less than 0.3% by weight.
  • chitansans as typical cationic biopolymers, anionically or nonionically derivatized chitosans, such as carboxylation, succinylation or alkoxylation products, as described, for example, in German patent DE 3713099 C2 (L'Oreal ) and the German patent application DE 19604180 A1 (Henkel).
  • the preparations according to the invention can contain chitosans in amounts of 0.1 to 10, preferably 0.5 to 5 and in particular 1 to 3% by weight, based on the preparation and calculated as a solid.
  • the preparations according to the invention can contain 0.1 to 20 and preferably 0.5 to 10 and in particular 1 to 5% by weight of anionic and / or amphoteric or zwitterionic surfactants.
  • anionic surfactants are alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxymixer ether sulfates, amine sulfate acid, (monoglycerate) fatty (ether) sulfate (monoglyidate) sulfate - And dialkyl sulfosuccinates, mono- and dialkyl sulfo
  • anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of Amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • the surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, reference is made to relevant reviews, for example, J. Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp. 54-124 or J. Falbe (ed.), "Catalysts, Tenside und Mineralöladditive ", Thieme Verlag, Stuttgart, 1978, pp. 123-217.
  • Another object of the invention relates to the use of the preparations according to the invention for the production of cosmetic and / or pharmaceutical preparations, for example hair and body care products, preferably hair care products.
  • a typical cosmetic and / or pharmaceutical preparation is composed as follows:
  • the preparations according to the invention can also be used as further auxiliaries and Additives oil bodies, emulsifiers, superfatting agents, pearlescent waxes, consistency enhancers, polymers, silicone compounds, fats, waxes, stabilizers, biogenic agents, deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, UV light protection factors, antioxidants, hydrotropes, preservatives, self-insulin repellants, insect repellants, insect repellants, Perfume oils, dyes and the like included.
  • esters of linear C ⁇ -C ⁇ fatty acids with branched alcohols in particular 2-ethylhexanol
  • esters of hydroxycarboxylic acids with linear or branched C6-C22 fatty alcohols in particular dioctyl malates
  • esters of linear and / or branched fatty acids with polyhydric alcohols such as propylene glycol, dimer diol or trimer triol
  • polyhydric alcohols such as propylene glycol, dimer diol or trimer triol
  • Guerbet alcohols triglycerides based on C ⁇ -Cio fatty acids
  • liquid mono- / di- / triglyceride mixtures based on C6-C ⁇ fatty acids
  • esters of C6-C22- Fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids especially benzoic acid, esters of C ⁇ -Ci ⁇ dicarboxylic acids with linear or branched alcohols with 1
  • 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
  • adducts of 2 to 15 moles of ethylene oxide with castor oil and / or hardened castor oil (8) partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid as well as 12-hydroxystearic acid and glycerin, polyglycerin, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside, butyl glucoside, - coside) and polyglucosides (eg cellulose);
  • partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid as well as 12-hydroxystearic acid and glycerin, polyglycerin, pentaerythritol, dipentaerythritol, sugar alcohols (e
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters, and sorbitan mono- and diesters with fatty acids or with castor oil are known, commercially available products. whose average 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.
  • C12 / 18 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE 2024051 PS as refatting agents for cosmetic preparations.
  • C ⁇ / is 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.
  • the 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.
  • polyglycerol esters are polyglyceryl-2 dipolyhydroxystearate (Dehymuls® PGPH), polyglycerol-3-diisostearate (Lameform® TGI), polyglyceryl-4 isostearate (Isolan® Gl 34), polyglyceryl-3 oleates, diisostearoyl polyglyearylate-3 (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 Isost
  • 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-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2 / i8-acylsarcosine.
  • quaternary emulsifiers can also be used.
  • Substances such as, for example, lanolin and lecithin, and also 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 polyglycine poly-12-hydroxystearates is preferred.
  • 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.
  • Luviquat® such as Luviquat® (BASF), 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, such as, for example, amidomethicones, copolymers of adipose and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyaminopolyamides, as described for example in FR 2252840 A, and their crosslinked water-soluble polymers, cationic chitin derivatives such as, for example, quaternized chitosan microcrystalline distribution, condensation products from dihaloalkylene, such as dibro
  • 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 / Acrylate copolymers, octylacrylamide / methyl methacrylate / tert.butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymers, vinyl pyrrolidone / dimethylaminoethyl methacrylate / vinyl caprolactam terpolymers and
  • 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.
  • Simethicones which are mixtures of dimethicones with an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicates, are also suitable.
  • a detailed overview of 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 natural waxes such as candelilla wax, camauba wax, Japanese 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), Bürzelfett, Ceresin, Ozokerit (Erdwachs), Petrolatum, paraffin waxes.
  • natural waxes such as candelilla wax, camauba wax, Japanese 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), Bürzelfett, Ceresin, Ozokerit (Erdwachs), Petrolatum, paraffin waxes.
  • Micro waxes such as montan ester waxes, Sasol waxes, Hydrogenated jojoba waxes and synthetic waxes, such as, for example, polyalkylene waxes and polyethylene glycol waxes, are possible.
  • hard waxes such as montan ester waxes, Sasol waxes, Hydrogenated jojoba waxes and synthetic waxes, such as, for example, polyalkylene waxes and polyethylene glycol waxes, are possible.
  • Metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate or hydroxyalkylated forms of guar (manufactured by Rhodia), such as hydroxypropyl guar (Jaguar® HP-105), are used.
  • the preparations according to the invention can contain hydroxyalkylated guar in amounts of 0.01 to 20, preferably 0.1 to 5 and in particular 0.5 to 2% by weight, based on the preparation and calculated as a solid.
  • Biogenic active ingredients are, for example, tocopherol, tocopheroiacetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes.
  • Cosmetic deodorants counteract, mask 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 which act as germ-inhibiting agents, enzyme inhibitors, odor absorbers or odor maskers.
  • germ-inhibiting agents such as.
  • 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, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, Monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarb- non-acids and their esters such as citric acid, malic acid, tartaric acid or tartaric acid diethyl ester, as well as 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
  • Suitable odor absorbers are substances that 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 must remain unaffected. Odor absorbers are not effective against bacteria. They contain, for example, a complex zinc salt of ricinoleic acid or special, largely odorless fragrances, which are known to the person skilled in the art as "fixators", such as, for example, the main component. 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 of flowers, stems and leaves, fruits, fruit peels, roots, woods, herbs and grasses, needles and branches as well as resins and balms. Animal raw materials, such as civet and castoreum, are also suitable. 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, benzyl ethyl ether, the aldehydes e.g.
  • the linear alkanals with 8 to 18 carbon atoms citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal, to the ketones e.g. Jonones and methylcedryl ketone, the alcohols anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, the hydrocarbons mainly include the terpenes and balsams. However, preference is given to using mixtures of different fragrances which together produce an appealing fragrance.
  • Essential 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.
  • 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:
  • auxiliaries such. B. thickeners or complexing agents and / or
  • non-aqueous solvents such as e.g. 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 e.g. Aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate and their 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, for. B. with amino acids such as glycine.
  • conventional oil-soluble and water-soluble auxiliaries can be present in smaller amounts in antiperspirants.
  • Such oil soluble aids can e.g. his:
  • water-soluble additives are e.g. Preservatives, water-soluble fragrances, pH adjusters, e.g. Buffer mixtures, water soluble thickeners, e.g. water-soluble natural or synthetic polymers such as e.g. 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- dichlo ⁇ henyl) r-2- (1 H -imidazol-1-ylmethyl) -1, 3-dioxylan-c-4-ylmethoxyphenyl ⁇ piperazine, selenium disulfide, sulfur colloidal, sulfur polyethyleneglycolsorbitan monooleate , Sulfuric ricinole polyhexylate, sulfuric tar distillates, salicylic acid (or in combination with hexachlorophene), undexylenic acid monoethanolamide sulfosuccinate sodium salt, Lamepon® UD (protein undecylenic acid condensate, zinc pyre
  • Common film formers are, for example, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic 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. 108, 95 (1993).
  • 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 absorb the energy absorbed in the form of longer-wave radiation, e.g. To give off heat again.
  • UVB filters can be oil-soluble or water-soluble. As oil-soluble substances e.g. to call:
  • 3-benzylidene camphor or 3-benzylidene norcampher and its derivatives e.g. 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, propyl 4-methoxycinnamate, 2-cyano-3,3-phenylcinnamate 2-ethylhexyl 4-methoxycinnamate (octo-crylene);
  • esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate, homomethyl salicylic acid;
  • 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 such as 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);
  • 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-sulfonic acid and its salts
  • Sulfonic acid derivatives of 3-benzylidene camphor such as 4- (2-oxo-3-bomylidenemethyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bornyiidene) sulfonic acid and their salts.
  • UV-A filters -4'-methoxydibenzoyl-methane (Parsol 1789), 1-phenyl-3- (4'-isopropylphenyl) propane-1,3-dione and enamine compounds, as described in DE 19712033 A1 (BASF).
  • 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.
  • the pigments can also be surface treated, i.e. are hydrophilized or hydrophobized.
  • Typical examples are coated titanium dioxides, e.g. Titanium dioxide T 805 (Degussa) or Eusolex® T2000 (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. 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, ß-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 thio propionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g.
  • buthioninsulfoximines homocysteine sulfoximine, butioninsulfones, penta-, hexa-, himinathion
  • very ge wrestle 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 its derivatives, unsaturated fatty acids and their derivatives (e.g.
  • 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, 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
  • 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 Ordinance.
  • insect repellents N, N-diethyl-m-toluamide, 1, 2- Pentanediol or ethyl butylacetylaminopropionate in question; 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, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (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 e.g.
  • the ethers include, for example, benzyl ethyl ether, the aldehydes e.g.
  • the linear alkanals with 8 to 18 carbon atoms citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal, to the ketones e.g. the jonones, cc-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, 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 and in particular 10 to 20% 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.
  • Hair shampoo formulations amounts in% by weight
  • the shamo formulations according to the invention could be produced in a cold process by adding the further components (cf. Table 2).
  • the further components cf. Table 2.
  • climbazole it was only possible to incorporate climbazole by heating the mixtures.
  • these mixtures produced in a cold process also show good dermatological compatibility.
  • they are characterized by stable viscosities and high storage stability (++).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne de nouvelles préparations cosmétiques et/ou pharmaceutiques contenant (a) des oligoglucosides d'alkyle et/ou d'alcène, (b) des glycérides partiels d'acide gras et (c) des fungicides.
PCT/EP2000/004025 1999-05-14 2000-05-05 Preparations cosmetiques et/ou pharmaceutiques WO2000069410A1 (fr)

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DE1999122230 DE19922230A1 (de) 1999-05-14 1999-05-14 Kosmetische und/oder pharmazeutische Zubereitungen
DE19922230.4 1999-05-14

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11433070B2 (en) 2019-06-28 2022-09-06 The Procter & Gamble Company Synergistic anti-inflammatory compositions
US11701316B2 (en) 2020-12-18 2023-07-18 The Procter & Gamble Company Synergistic anti-inflammatory compositions
US11980612B2 (en) 2020-06-26 2024-05-14 The Procter & Gamble Company Synergistic anti-inflammatory compositions
US12226505B2 (en) 2018-10-25 2025-02-18 The Procter & Gamble Company Compositions having enhanced deposition of surfactant-soluble anti-dandruff agents

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10035991A1 (de) 2000-07-24 2002-02-14 Polichem Sa Nagellackzusammensetzung
DE102012220148A1 (de) 2012-11-06 2014-05-08 Beiersdorf Ag Verfahren zur Herstellung von Climbazol-haltigen kosmetischen Formulierungen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993022912A1 (fr) * 1992-05-12 1993-11-25 Church & Dwight Company Compositions fongicides
US5525263A (en) * 1993-01-26 1996-06-11 Wella Aktiengesellschaft Hair and body cleaning composition
DE19619645A1 (de) * 1996-05-15 1997-11-20 Henkel Kgaa Haarbehandlungsmittel

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Publication number Priority date Publication date Assignee Title
DE4033928A1 (de) * 1990-10-25 1992-04-30 Henkel Kgaa Oel-in-wasser-emulsionen
DE4308794C1 (de) * 1993-03-18 1994-04-21 Henkel Kgaa Verfahren zur Herstellung von festen Esterquats mit verbesserter Wasserdispergierbarkeit
DE19540853A1 (de) * 1995-11-03 1997-05-07 Henkel Kgaa Haarbehandlungsmittel
DE19738641C1 (de) * 1997-09-04 1999-07-01 Henkel Kgaa Esterquats auf Zimtsäurebasis

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993022912A1 (fr) * 1992-05-12 1993-11-25 Church & Dwight Company Compositions fongicides
US5525263A (en) * 1993-01-26 1996-06-11 Wella Aktiengesellschaft Hair and body cleaning composition
DE19619645A1 (de) * 1996-05-15 1997-11-20 Henkel Kgaa Haarbehandlungsmittel

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12226505B2 (en) 2018-10-25 2025-02-18 The Procter & Gamble Company Compositions having enhanced deposition of surfactant-soluble anti-dandruff agents
US11433070B2 (en) 2019-06-28 2022-09-06 The Procter & Gamble Company Synergistic anti-inflammatory compositions
US11980612B2 (en) 2020-06-26 2024-05-14 The Procter & Gamble Company Synergistic anti-inflammatory compositions
US11701316B2 (en) 2020-12-18 2023-07-18 The Procter & Gamble Company Synergistic anti-inflammatory compositions

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