WO2000044340A1 - Cosmetic and/or pharmaceutical preparations - Google Patents

Cosmetic and/or pharmaceutical preparations

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Publication number
WO2000044340A1
WO2000044340A1 PCT/EP2000/000382 EP0000382W WO0044340A1 WO 2000044340 A1 WO2000044340 A1 WO 2000044340A1 EP 0000382 W EP0000382 W EP 0000382W WO 0044340 A1 WO0044340 A1 WO 0044340A1
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WO
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Patent type
Prior art keywords
acid
example
fatty
atoms
carbon
Prior art date
Application number
PCT/EP2000/000382
Other languages
German (de)
French (fr)
Inventor
Rolf Kawa
Bernd Fabry
Original Assignee
Cognis Deutschland Gmbh
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/411Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52Stabilizers

Abstract

The invention relates to cosmetic and/or pharmaceutical preparations containing (a) UV-A filters having an enamine structure, and (b) oil components and/or emulsifiers with a polarity of between 1.0 and 4.0 Debye. The above compositions are characterized in that they are especially photostable.

Description

Cosmetic and / or pharmaceutical preparations

Field of the Invention

The invention is in the field of sun protection agents and relates to new preparations which UV-A filter enamine together with oil components and / or emulsifiers of a defined polarity included.

State of the art

The cosmetic sunscreen products protect the human skin not only from the direct effects of UV-A and UV-B radiation, thus against sunburn, but also against the indirect consequences in the form of skin aging and skin cancer. Therefore, usually organic filter substances are used, which are due to their chemical structure, are capable of absorbing ultraviolet light. The inclusion of the UV radiation, electrons are added to an excited state in the filter molecule. The energy stored is then released again in the form of heat radiation, said photostable molecules in their ground state energy return while entering a chemical change in photo unstable filters, such as isomerization or a radical degradation.

In particular, the protection against UV-A radiation is becoming increasingly important, as this form of radiation into the deeper layers of the skin while penetrating cell-damaging phototoxic and photo may cause allergic reactions. Latest studies show for example that irreversible photodamage in the form of Bindegewebsdegeneration, Hautcarcino- men and Spinalomen are possible. A particularly effective UV-A-filter the market is the Butyl Methoxydibenzoylmethane, but which has a low photostability. 12 degradation products are known so far for this molecule, which previously existed on the phototoxic potential of these substances is no reliable evidence. the existence of a certain sensitization potential, therefore, can not be excluded for the user of sunscreen.

An interesting alternative to butyl methoxydibenzoylmethane represent enamine derivatives, such as those described in German patent application DE 19712033 A1 (BASF) are described. Although these materials have a high photostability, but less than that required by the cosmetics industry 100 -% - mark. Accordingly, the object of the present inventions has dung were to provide new formulations based on said filter available that a greater photostability comprise 98%.

Description of the Invention

The invention relates to cosmetic and / or pharmaceutical preparations containing

(A) UV-A filter enamine and

(B) oil components and / or emulsifiers of a polarity in the range of 1 to 4, preferably 1, 5 to 3.5 Debye.

It has surprisingly been found that the combination of the specific UV-A filter with cosmetic ingredients a defined polarity inhibits photodegradation, while in admixture with materials such as a lower polarity photostability is further reduced.

UV-A filter

In the component (a) to be used UV-A filters with enamine is known substances which are described for example in the already mentioned German patent application DE 19712033 A1. Preferably, the filter follow the formula (I),

(I)

in which the double bond in the E or Z configuration is present and R 1 is COOR 5, COR 5, CONR5R6, CN, 0 = S (-R 5) = 0, 0 = S (-OR 5) = 0, R 2 is COOR 6, COR 6, CONR 5 R 6, CN, 0 = S (-R 6) = 0, 0 = S (-OR 6) = 0 R 8 0-P (-OR 7) = 0 , R 3 is hydrogen, an optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical having in each case up to 18 carbon atoms, R 4 represents an optionally substituted aromatic or heteroaromatic radical having 5 to 12 ring atoms, and R 5 to R 8 are independently hydrogen, an open-chain or branched aliphatic, araliphatic, cycloaliphatic or optionally substituted aromatic radical having up to 18 carbon atoms, where the radicals R 3 to R 8 each other, each atoms together with the carbon to which they are overall tied together a 5 - or 6-membered ring may form, which may be further fused to optionally.

In a preferred embodiment of the invention, UV-A filters of formula (I) contained in the in the media, R 3 represents hydrogen, R 1 CN, COOR 5 and COR 5, and R 2 is CN, COOR 6 and COR 6 , where R 5 and R 6 independently of one another open-chain or branched aliphatic or optionally substituted aromatic radicals having up to 8 carbon atoms. Particularly preferred are compounds of formula (I) in which R 3 is hydrogen,, R 1 CN, COOR 5 and COR 5, and R 2 is CN, COOR 6 and COR 6 wherein R 5 and R 6 independently of one another open-chain or mean branched aliphatic or optionally substituted aromatic radicals having up to 8 carbon atoms and R 4 represents an optionally substituted aromatic or heteroaromatic group with up to 10 carbon atoms in the ring, especially a substituted phenyl, thienyl, furyl, pyridyl, indolyl or naphthylene and particularly preferably represents an optionally substituted phenyl or thienyl. As substituents both lipophilic and hydrophilic substituents with, for example up to 20 carbon atoms. Lipophilic, that is oil solubility of the compounds of formula (I) reinforcing radicals are aliphatic or cycloaliphatic radicals nocarbonyl- in particular alkyl radicals having 1 bis 18 carbon atoms, alkoxy, mono and dialkylamino, alkoxycarbonyl, mono- and dialkylamino, mono - and Dialkylaminosulfonylreste, further cyano, nitro, bromo, chloro, iodo or fluoro substituents. Hydrophilic, that is, the water solubility of the compounds of formula (I) enabling radicals are carboxy and sulfoxy and in particular their salts with any physiologically acceptable cations such as alkali metal salts or as the trialkylammonium salts, such as tri (hydroxyalkyl) ammonium salts or the 2-methyl propane -1-ol-2-ammonium salts. Furthermore alkylammonium come up with any physiologically tolerated anions into consideration. Suitable alkoxy radicals are those having 1 to 12 carbon atoms, preferably having 1 to 8 carbon atoms. For example, the following radicals are:

• methoxy isopropoxy

• n-propoxy 1-methylpropoxy-

• n-butoxy n-pentoxy

• 2-methylpropoxy- 3-methylbutoxy

• 1.1-dimethylpropoxy 2.2-dimethylpropoxy

• hexoxy 1 -methyJ-1 -ethylpropoxy-

• heptoxy octyloxy

• 2-ethylhexoxy-

The mono- or dialkylamino groups include for example those into consideration, the alkyl radicals contain 1 to 8 carbon atoms, such as methyl, n-propyl, n-butyl, 2-methylpropyl, 1, 1-dimethylpropyl, hexyl, heptyl -, 2-ethylhexyl, isopropyl, 1-methylpropyl, n-pentyl, 3-methylbutyl, 2,2-di- methylpropyl, 1-methyl-1 -ethylpropyl- and octyl. These residues are equally included in the mono- and Dialkylaminocarbonyi- and sulfonyl. Alkoxycarbonyl radicals are, for example, esters containing the above-mentioned alkoxy radicals or radicals of higher alcohols, for example with up to 20 carbon atoms, such as iso-Ci5 alcohol.

Oil components and emulsifiers

Regarding the selection of oil components and emulsifiers provides its polarity is the decisive criterion. The dipole moment of the substances in question, for example, according to the formula of Onsager [see. Soap oils-fats waxes, 115, 459-61 (1989)] are calculated.

As oil components of the required polarity particular Guerbet alcohols based on fatty alcohols having 6 to 18, preferably atoms 8 to 10 carbon, esters of branched C6-Ci3-carboxylic acids with linear C6-C22-fatty alcohols, esters of branched of linear C6-C22-fatty acids with alcohols, especially 2-ethylhexanol, esters of hydroxycarboxylic acids with linear or branched C6-C22-fatty alcohols, in particular dioctyl Malate, esters of linear and / or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer diol or tri mertriol) and / or Guerbet liquid mono- / di- / triglyceride mixtures based on Cε- Ciβ-fatty acids, esters of C6-C22-fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of CΣ-CiΣ dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon atoms or polyols having 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C22 fatty alcohol carbonates, Guerbet carbonates, esters of benzoic acid with linear and / or branched C6-C22-alcohols (for example, Finsolv® TN), linear or branched, symmetrical or asymmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, ring opening products of epoxidized fatty acid esters with polyols contemplated.

As suitable emulsifiers for example, nonionic surfactants from at least one of the following groups:

(1) Addition products of 2 to 30 mol ethylene oxide and / or 0 to 5 mol propylene oxide onto linear fatty alcohols having 8 to 22 carbon atoms, onto fatty acids having 12 to 22 carbon atoms and with alkylphenols having 8 to 15 carbon atoms in the alkyl group;

(2) Ci2.i8 acid monoesters and diesters of Aniagerungsprodukten of 1 to 30 mol ethylene oxide onto glycerol; (3) sorbitan mono- and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and their Ethylenoxidaniagerungsprodukte;

(4) alkyl mono- and oligoglycosides having 8 to 22 carbon atoms in the alkyl group and ethosulfate xylierte analogues;

(5) polyglycerol esters, such as Polyglycerinpoiyricinoleat, polyglycerol poly-12-hydroxystearate or polyglycerol dimerate isostearate. Also suitable are mixtures of compounds from several of these classes;

(6) partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, sugar alcohols (for example sorbitol), alkyl glucosides (for example methyl glucoside, butyl glucoside, lauryl glucoside) and Polygluco- side ( for example cellulose);

(7) mono-, di- and trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates and salts thereof;

(8) wool wax alcohols;

(9) as well as polyalkylene glycols

(10) glycerol carbonate.

The addition products of ethylene oxide and / or propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters and sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. They are homolog mixtures whose average alkoxylation corresponds to the ratio between the quantities of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out, corresponds. Ci2 / i8-fatty acid mono- and diesters of addition products of ethylene oxide onto glycerol are known from DE 2024051 as refatting agents for cosmetic preparations.

Cβ / 18 alkyl mono- and oligoglycosides, their preparation and their use are known from the prior art. They are prepared, in particular, by reacting glucose or oligosaccharides with primary alcohols having 8 to 18 carbon atoms. With regard to the glycoside radical, both monoglycosides, in which a cyclic sugar radical is glycosidically bonded to the fatty alcohol, and also oligomeric glycosides with a degree of oligomerization are suitable preferably up to about. 8 The degree of oligomerization here is a statistical average value which is typical of such technical products homolog distribution.

Furthermore, zwitterionic surfactants can be used as emulsifiers. Zwitterionic surfactants are surface-active compounds which carry at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule. Particularly suitable zwitterionic surfactants are the betaines such as N-alkyl-N, N- dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinates, for example pyldimethylammoniumglycinat the Kokosacyiaminopro-, and 2-alkyl-3-carboxylmethyl -3-hydroxyethylimidazoline carboxymethylglycinat each having 8 to 18 carbon atoms in the alkyl or acyl group as well as the Kokosacylaminoethylhydroxyethyl-. Particular preference is known by the CTFA name Cocamidopropyl Betaine fatty acid amide derivative. Likewise suitable emulsifiers are ampholytic surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a C / .β-alkyl or -acyl group in the molecule nogruppe at least one free amino and contain at least one -COOH or -Sθ3H group and are capable of forming inner salts. Examples of suitable ampholytic surfactants are N-alkyl glycines, N-Al kylpropionsäuren, N-alkyl aminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylamine having in each case about minoessigsäuren 8 to 18 C atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethyl aminopropionate and CiΣ / iβ sarcosine. Besides ampholytic emulsifiers, quaternary emulsifiers are contemplated, those of the esterquat type, preferably methyl-di- fatty acid triethanolamine esters salts, being particularly preferred.

commercial Applications

In a preferred embodiment of the invention, the cosmetic and / or pharmaceutical preparations containing

(A) from 0.1 to 5, preferably 1 to 3 wt .-% UV-A filter enamine and

(B) from 0.5 to 50, preferably 5 to 25 wt .-% oil components and / or emulsifiers having a polarity in the range from 1, 0 to 4.0, preferably 1, 5 to 3.5 Debye,

with the proviso that the quantities with water and optionally further auxiliaries and additives add up to 100 wt .-%.

Cosmetic and / or pharmaceutical preparations

The agents, such as creams, gels, lotions, alcoholic and aqueous / alcoholic solutions, emulsions, wax / fat compounds, stick preparations, powders or ointments, may also grow as further auxiliaries and additives mild surfactants, superfatting agents, pearlescent, consistency factors, thickeners, polymers, silicone compounds, fats, waxes, stabilizers, biogenic agents, deodorants, antidandruff agents, film formers, swelling agents, further UV light protection factors, antioxidants, hydrotropes, preservatives, insect-pellentien, self-tanning agents, solubilizers, perfume oils, dyes, germ inhibitors and the like.

Typical examples of suitable mild, ie particularly skin-compatible surfactants are fatty alcohol polyglycolethersuifate, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, carboxylic acids, fatty acid taurides, fatty acid glutamates, α-olefin sulfonates, ether, alkyl oligoglucosides, fatty acid glucamides, alkylamidobetaines and / or protein fatty acid condensates, preferably based on wheat proteins.

Superfatting agents may be used such as for example, lanolin and lecithin and polyether thoxylierte or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the latter also serving as foam stabilizers.

Pearlescent waxes are, for example, alkylene glycol esters, especially ethylene glycol distearate; Fatty acid, especially Kokosfettsäurediethanoiamid; Partial glycerides, especially stearic acid monoglyceride; Esters of polybasic, optionally hydroxysubstituted 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 at least 24 carbon atoms in total, especially laurone and distearyl ether; Fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring opening products of olefin epoxides having 12 to 22 carbon atoms with fatty alcohols having 12 to 22 carbon atoms and / or polyols having 2 to 15 carbon atoms and 2 to 10 hydroxyl groups and mixtures thereof.

The consistency factors mainly used are fatty alcohols or hydroxyfatty alcohols containing 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 to and / or fatty acid N-methylglucamides of identical chain length and / or polyglycerol poly-12- hydroxystearates is. Suitable thickeners are, for example, Aerosil types (hydrophilic silicas), polysaccharides, more especially xanthan gum, guar-guar, agar-agar, alginates and tyloses, carboxymethyl cellulose and Hyd roxyethylcel I ulose, further lenglycolmono- high molecular weight polyethylene and diesters of fatty acids, polyacrylates (eg Carbopols® from Goodrich or Synthalene® from Sigma), poly-acrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols for example pentaerythritol or trimethylolpropane, fatty alcohol koholethoxyl ate having a narrowed homolog distribution or alkyl oligoglucosides, and electrolytes such as sodium chloride and ammonium chloride.

Suitable cationic polymers are for example cationic cellulose derivatives, for example, a quaternized hydroxyethylcellulose obtainable under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallyl ammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers, for example Luviquat (BASF) , condensation products of polyglycols and amines, quaternized collagen polypeptides such as, for example, lauryl ryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grunau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, for example, amodimethicone, copolymers of adipic acid and dimethylaminohydroxypropyl (Cartaretine® / Sandoz ), copolymers of acrylic acid (dimethyldiallylammonium chloride with Merquat® 550 / Chemviron), polyaminopolyamides nopolyamide, such as described in FR 2252840 A, and crosslinked water-soluble polymers thereof, cationic chitin derivatives such as quaternized Chito san, optionally in microcrystalline distribution, condensation products of dihaloalkyls, for example dibromobutane, with bis-dialkylamines, for example bis-dimethylamino-1,3-propane, cationic guar gum, such as Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers such as, for example, Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol.

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.Butylaminoethylmethacrylat / 2 Hydroxyproyl methacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, vinylpyrrolidone / dimethylaminoethyl methacrylate-vinylcaprolactam terpolymers, and optionally derivatized cellulose ethers and silicones.

Suitable silicone compounds are, for example, dimethyl polysiloxanes, Methylphenylpolysilo- Xane, cyclic silicones and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glycoside- and / or alkyl-modified silicone compounds which may be both liquid and resin-like at room temperature. Also suitable are simethicones, which are mixtures of dimethicones with an average chain length of 200 to 300 Dimethylsi- Loxan units and hydrogenated silicates. A detailed review of suitable volatile silicones is found in Todd et al. in Cosm. 91, 27 (1976). Typical examples of fats are glycerides while suitable waxes are inter alia beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax, hydrogenated castor oils, solid at room temperature fatty acid ester or microcrystalline waxes, optionally in combination with hydrophilic waxes, for example cetyl stearyl alcohol or partial glycerides. Metal salts of fatty acids, such as magnesium, aluminum and / or zinc stearate or ricinoleate may be used.

Biogenic agents are, for example, tocopherol, tocopherol acetate, Tocopherolpal- palmitate, palmitate, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides to understand essential oils, plant extracts and vitamin complexes.

Suitable deodorizers eg antiperspirants such as aluminum chlorohydrates eligible. These are colorless, hygroscopic crystals which readily deliquesce in air and which accumulate when aqueous aluminum chloride solutions evaporation. Aluminum chlorohydrate is used for the preparation of antiperspirant and deodorant preparations and probably acts by partially blocking the sweat glands by protein and / or polysaccharides ridfällung [cp. J.Soc. Cosm.Chem. 24, 281 (1973)]. Under the brand Locron® Hoechst AG, Frankfurt / FRG, for example, is, an aluminum trade to the formula [Al 2 (OH) 5 Cl] * corresponds to 2.5 H2O and its use is particularly preferred [see. J.Pharm.Pharmacol. 26, 531 (1975)]. Besides the chlorhydrates Aluminiumhydro- can xylactate and acidic aluminum / zirconium salts are used. As another deodorizers are esterase inhibitors. These are preferably trialkyl citrate such as trimethyl citrate, tripropyl, triisopropyl, tributyl citrate and especially triethyl citrate (Hydagen® CAT, Henkel KGaA, Dusseldorf / FRG). The substances inhibit enzyme activity and thus reduce odor formation. Probably The free acid liberated by the cleavage of the citric acid ester, reducing the pH value on the skin, characterized in that the enzymes are inhibited. Further substances that come into consideration as esterase inhibitors are sterol sulfates or phosphates, for example lanosterol, cholesterol, bovine Campeste-, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof such as glutaric acid, monoethyl glutarate, diethyl glutarate, carbnonsäuren adipic acid, adipic säuremonoethylester, malonic acid and diethyl malonate, hydroxy and esters thereof such as citric acid, malic acid, tartaric acid or tartaric acid diethyl ester. Antibacterial active ingredients that influence the germ flora and kill perspiration-decomposing bacteria or inhibit their growth, can also be included in the pin preparations. Examples include chitosan, phenoxyethanol and Chlorhexidingluco- nat. Particularly effective are also 5-chloro-2- (2,4-dichlorophenoxy) phenol has proven that is sold under the trademark Irgasan® from Ciba-Geigy, Basle / CH.

As anti-dandruff agents Climbazol, Octopirox® and zinc pyrithione. Customary film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyviny Ipyrrolidon, vinylpyrrolidone-vinyl acetate copolymers, polymers of Acrylsäu- rereihe, quaternary cellulose derivatives, collagen, hyaluronic acid and salts thereof and similar compounds. Suitable swelling agents for aqueous phases are montmorillonites, clay mineral substances serve, Pemulen and alkyl-modified Carbopol types (Goodrich). Other suitable polymers and swelling agents can Lochhead's review in Cosm. 108, 95 (1993) are taken.

Under UV light protection factors are, for example liquid at room temperature or crystalline present, organic substances (light protection filters) to be understood, that are able to absorb ultraviolet rays and give off the absorbed energy again in the form of longer-wave radiation, for example heat. UVB filters can be oil-soluble or water soluble. Oil-soluble substances are to be mentioned:

• 3-benzylidene camphor or 3-benzylidene norcamphor and derivatives thereof, for example 3- (4-methyl benzylidene) camphor as described in EP 0693471 B1;

• 4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) benzoic acid 2-ethylhexyl ester, 4- (dimethylamino) benzoic acid 2-octyl ester and 4- (dimethylamino) benzoesäureamylester;

• esters of cinnamic acid, preferably 4-methoxycinnamic acid 2-ethylhexyl ester, 4-Methoxyzimt-acid-repropylester, 4-methoxycinnamic acid isoamyl ester 2-cyano-3,3-phenylcinnamate, 2-ethylhexyl (Octocrylene);

• esters of salicylic acid, preferably 2-ethylhexyl salicylate, 4-isopropyl benzyl salicylate;

• derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;

• esters of benzalmalonic acid, preferably 4-methoxy-2-ethylhexyl ester;

• 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;

• propane-1, 3-diones, for example 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1, 3-dione;

• ketotricyclo (5.2.1.0) decane derivatives as described in EP 0694521 B1.

Water-soluble substances are: • 2-phenylbenzimidazole-5-sulfonic acid and alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and glucammonium;

• sulphonic acid derivatives of benzophenones, preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts;

• sulphonic acid derivatives of 3-benzylidenecamphor, eg 4- (2-oxo-3-bomylidenme- thyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bornylidene) sulfonic acid and salts thereof.

Typical UV-A filters are, in particular, derivatives of benzoylmethane, for example 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione, 4-tert-butyl -4'-methoxy-dibenzoylmethane (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. Besides the soluble substances mentioned, insoluble light-blocking pigments, ie finely dispersed metal oxides or salts used for this purpose in question. Examples of suitable metal oxides are in particular zinc oxide and titanium dioxide and also oxides of iron, zirconium, silicon, manganese, aluminum and cerium and mixtures thereof. As salts of silicates can be used (talc), barium sulfate or zinc stearate. The oxides and salts are used in the form of the pigments for skincare and skin-protective emulsions and decorative cosmetics. The particles should have a mean diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. You can have a spherical shape, but it is also such particles are used which have an ellipsoidal or otherwise deviates from the spherical shape. The pigments can also be surface treated, ie be hydrophilicized or hydrophobicized. Typical examples are coated titanium dioxides, for example Titandioxid T 805 (Degussa) or Eusolex® T2000 (Merck). Suitable hydrophobic coating materials are, above all, silicones and particularly Trialkoxyoctyl- silanes or simethicone. In sunscreens, so-called micro or nano pigments are preferably used. Preferably micronized zinc oxide is used. Further suitable UV light protection filters in the review by P. Finkel in SFW-Journal 122, 543 (1996).

Besides the two aforementioned groups of primary sun protection factors, secondary sun protection agents can be used of the antioxidant type which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates into the skin. Typical examples thereof are amino acids (for example glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (for example urocanic acid) and derivatives thereof, peptides, such as DL-carnosine, D-carnosine, L-carnosine and derivatives thereof (for example anserine) , carotenoids, carotenes (for example α-carotene, beta-carotene, lycopene) and derivatives thereof, chlorogenic acid and derivatives thereof, lipoic acid and derivatives thereof (for example dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (for example thioredoxin, Glu tathion, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, cholesteryl and glyceryl esters) and their salts , dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (for example Buthioninsulfoximine, homocysteine ​​sulfoximine, Butioninsulfone, penta-, hexa-, Heptathionin- sulfoximine) in very low tolerated doses (for example pmol to .mu.mol / kg), further (metal) - chelators (for example α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (for example citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof, unsaturated fatty acids and their derivatives (eg γ- linolenic acid, linoleic acid, oleic acid), folic acid and derivatives thereof, ubiquinone and ubiquinol and derivatives thereof, vitamin C and derivatives (for example ascorbyl palmitate, Mg ascorbyl phosphate, Ascorbyla - acetate), tocopherols and derivatives (for example vitamin e acetate), vitamin A and derivatives (vitamin-A-palmitate PAL) and coniferyl benzoate of benzoin, rutinic acid and derivatives thereof, α-glycosyl rutin,

Ferulic acid, Furfurylidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole, Nordihydrogu- ajakharzsäure, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof, superoxide dismutase, zinc and derivatives thereof (for example ZnO, ZnS0) selenium and derivatives thereof (for example selenium this said active ingredients methionine), stilbenes and derivatives thereof (for example stilbene oxide, trans-stilbene oxide) and the derivatives suitable according to the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids).

To improve the flow behavior, hydrotropes, polyols such as ethanol, isopropyl alcohol, or the like. Polyols which are suitable here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. The polyols can also contain further functional groups, especially amino groups, or be modified with nitrogen. Typical examples are

• glycerol;

• 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;

• technical oligoglycerol mixtures with a self condensation degree of 1, 5 to 10, for example technical diglycerol mixtures with a diglycerol content of 40 to 50 wt .-%;

• Methyolverbindungen, such as in particular trimethylolethane, trimethylolpropane, trimethyl-olbu- tan, pentaerythritol and dipentaerythritol;

• Niedrigalkylglucoside, in particular those having 1 to 8 carbon atoms in the alkyl radical, for example methyl and butyl glucoside;

• atoms, sugar alcohols having 5 to 12 carbon atoms, such as sorbitol or mannitol, • Sugar having 5 to 12 carbon, for example glucose or sucrose;

• amino sugars, for example glucamine;

• dialcohol, 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 compounds listed in B Annex 6, Part A and the cosmetics regulations are suitable. Suitable insect repellents are N, N-diethyl-m-toluamide, 1, 2-pentanediol or insect repellent 3535, as self dihydroxyacetone ceton suitable.

As perfume oils are mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flowers (lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peels (bergamot, lemon, orange), roots (mace, angelica, celery, cardamom, costus, iris, Calmus), woods (pinewood, sandalwood, guaiac wood, cedarwood, rosewood), herbs and grasses (tarragon, lemon grass, sage, thyme) needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials in question, for example civet and beaver. 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, acetate Benzyla-, zylcarbinylacetat phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, Dimethylben-, phenylethyl acetate, Linalyl benzoate, benzyl formate, ethyl methyl phenylglycinate, Allylcyclohexylpropionat, Styrallylpropionat 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, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxy citronellal, lilial and bourgeonal, the ketones include the ionones, oc-isomethylionone and methyl alcohols are anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenyl ethyl alcohol and terpineol and the hydrocarbons include mainly the terpenes and balsams. Preferably, however, mixtures of different odorants, which together produce a pleasing fragrance note. Essential oils of lower volatility, which are mostly used as aroma components, are also suitable as perfume oils, eg sage oil, chamomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, lime blossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum, labolanum and lavender oil. Preferably, bergamot oil, dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, α-hexylcinnamaldehyde, geraniol, benzyl acetone, cyclamen aldehyde, linalool, Boisambrene Forte, Ambroxan, indole, hedione, Sandelice, lemon oil, Man- be darinenöl, orange oil, allyl amyl glycolate, Cyclovertal, lavandin , muscatel sage oil, ß-DA mascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-e-Super, Fixolide NP, Evernyl, Iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romillat, irotyl and floramat alone or in mixtures, used.

The dyes suitable for cosmetic purposes, and authorized substances may be used, such as those described in the publication "Cosmetic Colourants" Commission of the Deutsche Forschungsgemeinschaft, Verlag Chemie, Weinheim, 1984, S.81-106 are summarized. These dyes are normally used in concentrations of 0.001 to 0.1 wt .-%, based on the total mixture.

Typical examples of germ inhibitors are preservatives which act specifically against gram-positive bacteria such as 2,4,4'-trichloro-2'-hydroxydiphenyl ether, chlorhexidine (1, 6- di (4-chlorophenyl-biguanido) hexane) or TCC (3,4,4-trichloro). Numerous perfumes and essential oils also have antimicrobial properties. Typical examples are the active ingredients eugenol, menthol and thymol in clove, mint and thyme oil. An interesting natural deodorant is terpene alcohol farnesol the (3,7, 11-trimethyl-2,6,10-dodecatrien-1-ol), which is present in lime blossom oil and has a lily of the valley odor. Glycerol monolaurate has also proved to be a bacteriostatic agent. The percentage content of the additional germ-inhibiting agents is normally about 0.1 to 2 wt .-% - in relation to the on the solids content of the preparations.

The total percentage content of auxiliaries and additives can be 1 to 50, preferably 5 to 40 wt .-% - based on the preparation - be. The formulations may be produced by standard hot - made or hot processes; are preferably produced by the phase inversion temperature method.

Examples

The photostability of different UV-A filter optionally mixed with different oil components and emulsifiers was determined according to the published by Merck occasion of the APV seminar semi- nar of 17-18.09.1997 in Fulda method. The results are summarized in Table 1 below. Examples 1 to 6 are according to the invention, Examples C1 and C2 are intended for comparison.

Table 1 photostability

In Table 2 below, a number of formulation examples found. The compositions 1, 3, 5, 9 to 11, 13, 16, and 21 to 22 represent creams, all other lotions.

table 2

Formulation Examples (cont.) - quantities in wt .-%

Claims

claims
1. Cosmetic and / or pharmaceutical preparations containing
(A) UV-A filter enamine and
(B) oil components and / or emulsifiers having a polarity in the range from 1, 0 to 4.0 Debye.
2. Preparations according to claim 1, characterized in that they contain UV-A filters of formula (I),
IIR 1 -C = C-NH-R *
(I)
in the double bond is in the E or Z configuration and R 1 is COOR 5, COR 5, CONRSR6, CN, 0 = S (-R 5) = 0, 0 = S (-OR 5) = 0, R 8 0 -P (-OR 7) = 0, R 2 is COOR 6, COR 6, CONR 5 R 6, CN, 0 = S (-R 6) = 0 0, = S (-OR 6) = 0, R 8 0- P (-OR 7) = 0, R 3 is hydrogen, an optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical having in each case up to 18 carbon atoms, R 4 represents an optionally substituted aromatic or heteroaromatic radical having 5 to 12 ring atoms, and R are 5 to R 8 are independently hydrogen, an open-chain or branched aliphatic, araliphatic, cycloaliphatic or optionally substituted aromatic radical having up to 18 carbon atoms, where the radicals R 3 to R 8 each other, in each case together with the carbon atoms to which they are attached are, may form a 5- or 6-membered ring, which may optionally be fused on.
3. Preparations according to Claims 1 and / or 2, characterized in that they contain UV-A filters of formula (I) in which R 3 is hydrogen, R 1 CN, COOR 5 and COR 5, and R 2 is CN, COOR 6 and COR 6, where R 5 and R 6 independently of one another open-chain or branched aliphatic or optionally substituted aromatic radicals having up to 8 carbon atoms.
4. Preparations according to at least one of claims 1 to 3, characterized in that they contain UV-A filters of formula (I), in which R 4 represents optionally substituted by hydrophilic o- the lipophilic substituent is phenyl.
5. Preparations according to claim 4, characterized in that R 4 stands for an alkoxyphenyl or Alkoxycarbonylphenylrest.
6. Preparations according to claim 4, characterized in that R 4 stands for a phenyl radical which water-solubilizing substituents, selected from the group consisting of carboxylate, sulfonate or ammonium residues.
7. Preparations according to at least one of claims 1 to 6, characterized in that they contain oil components selected from the group consisting of Guerbet alcohols based on fatty alcohols having 6 to 18 carbon atoms, esters of branched C6-Ci3-carboxylic acids liquid with linear C6-C22-fatty alcohols, esters of linear Cδ- C22-fatty acids with branched alcohols, esters of hydroxycarboxylic acids with linear or branched C6-C22-fatty alcohols, esters of linear and / or branched fatty acids with polyhydric alcohols and / or Guerbet alcohols, mono- / di- / triglyceride mixtures based on C6-CI8 fatty acids, esters of C6-C22-fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, esters of C2-Ci2-dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon atoms or polyols having 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, branched primary alcohols, substituted cyclohex anes, linear and branched C6-C22-Fettalkoholcarbonaten, Guerbet betcarbonaten, esters of benzoic acid with linear and / or branched C6-C22-alcohols, linear or branched, symmetrical or unsymmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, and ring-opening products of epoxidized Fettsäureestern with polyols.
8. Preparations according to at least one of claims 1 to 7, characterized in that they contain nonionic emulsifiers selected from the group formed by addition products of from 2 to 30 mol ethylene oxide and / or 0 to 5 mol propylene oxide onto linear fatty alcohols having 8 to 22 carbon atoms, onto fatty acids having 12 to 22 carbon atoms and onto alkylphenols having 8 to 15 carbon atoms in the alkyl group; Ci2 i8-fatty acid mono- and diesters of addition products of 1 to 30 mol ethylene oxide onto glycerol; Sorbitan mono- and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and ethylene oxide adducts thereof; Alkyl mono- and oligoglycosides containing 8 to 22 carbon atoms in the alkyl radical and ethoxylated analogs thereof; Polyglycerines- tern, partial esters based on linear, branched, unsaturated or saturated Ce / 22-fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, sugar alcohols, alkyl glucosides and polyglucosides; Mono-, di- and trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates and salts thereof; Wool wax alcohols; Polyalkylene lenglycolen and glycerol.
9. Preparations according to at least one of claims 1 to 8, characterized in that they contain anionic, cationic and / or zwitterionic emulsifiers.
at least one of claims 1 to 9, characterized in 10. preparations that they
(A) 0.1 to 5 wt .-% UV-A filter enamine and
(B) 0.5 to 50 wt .-% oil components and / or emulsifiers having a polarity in the range from 1, 0 to 4.0 Debye
included, with the proviso that the quantitative data with water and optionally other auxiliaries and additives to make 100 wt .-% complementary.
PCT/EP2000/000382 1999-01-28 2000-01-19 Cosmetic and/or pharmaceutical preparations WO2000044340A1 (en)

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US6485713B1 (en) 2002-03-05 2002-11-26 The C. P. Hall Company Sunscreen compositions and methods and materials for producing the same
US6537529B1 (en) 2002-03-05 2003-03-25 The C.P. Hall Company Sunscreen compositions and methods and materials for producing the same
WO2003075877A2 (en) * 2002-03-05 2003-09-18 The C.P. Hall Company Sunscreen compositions as well as methods and materials for producing the same, wherein the photodecay rate of the filter system is reduced by controlling the polarity of the solvent system
US6800274B2 (en) 2002-09-17 2004-10-05 The C.P. Hall Company Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition
US6890521B2 (en) 2002-09-06 2005-05-10 The C.P. Hall Company Photostabilization of a sunscreen composition with low levels of an α-cyano-β, β-diphenylacrylate
US6899866B2 (en) 2002-09-06 2005-05-31 Cph Innovations Corporation Photostabilization of a sunscreen composition with a combination of an α-cyano-β, β-diphenylacrylate compound and a dialkyl naphithalate
US6919473B2 (en) 2002-09-17 2005-07-19 Cph Innovations Corporation Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition
US6926887B2 (en) 2002-09-17 2005-08-09 The C.P. Hall Company Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition
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WO2003075877A3 (en) * 2002-03-05 2003-12-18 Cp Hall Co Sunscreen compositions as well as methods and materials for producing the same, wherein the photodecay rate of the filter system is reduced by controlling the polarity of the solvent system
US6770270B2 (en) 2002-03-05 2004-08-03 The C.P. Hall Company Methods of making and selling a sunscreen composition
US6485713B1 (en) 2002-03-05 2002-11-26 The C. P. Hall Company Sunscreen compositions and methods and materials for producing the same
US6890521B2 (en) 2002-09-06 2005-05-10 The C.P. Hall Company Photostabilization of a sunscreen composition with low levels of an α-cyano-β, β-diphenylacrylate
US6899866B2 (en) 2002-09-06 2005-05-31 Cph Innovations Corporation Photostabilization of a sunscreen composition with a combination of an α-cyano-β, β-diphenylacrylate compound and a dialkyl naphithalate
US6800274B2 (en) 2002-09-17 2004-10-05 The C.P. Hall Company Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition
US6962692B2 (en) 2002-09-17 2005-11-08 Cph Innovations Corp. Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition
US6926887B2 (en) 2002-09-17 2005-08-09 The C.P. Hall Company Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition
US6919473B2 (en) 2002-09-17 2005-07-19 Cph Innovations Corporation Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition
US7534420B2 (en) 2004-02-25 2009-05-19 Hallstar Innovations Corp. Compounds derived from polyanhydride resins with film-forming, UV-absorbing, and photostablizing properties, compositions containing same, and methods of using the same
US7550134B2 (en) 2004-02-25 2009-06-23 Hallstar Innovations Corp. Compounds derived from polyanhydride resins with film-forming, UV-absorbing, and photostabilizing properties, compositions containing same, and methods of using the same
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US7648697B2 (en) 2004-02-25 2010-01-19 Hallstar Innovations Corp. Compounds derived from polyanhydride resins with film-forming, UV-absorbing, and photostabilizing properties, compositions containing same, and methods of using the same
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