DE3018132A1 - Anti-acne and deodorant skin-care preparations - contg. amino:methylene-malonic acid derivs. which inhibit esterase and lipase enzymes secretions from skin bacteria - Google Patents
Anti-acne and deodorant skin-care preparations - contg. amino:methylene-malonic acid derivs. which inhibit esterase and lipase enzymes secretions from skin bacteriaInfo
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- DE3018132A1 DE3018132A1 DE19803018132 DE3018132A DE3018132A1 DE 3018132 A1 DE3018132 A1 DE 3018132A1 DE 19803018132 DE19803018132 DE 19803018132 DE 3018132 A DE3018132 A DE 3018132A DE 3018132 A1 DE3018132 A1 DE 3018132A1
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- malonic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
Description
"Hautpflegemittel" "Skin care products"
Gegenstand der Erfindung sind Hautpflegemittel mit einem Gehalt an N-substituierten Aminomethylenmalonsäurederivaten.The invention relates to skin care products with a content of N-substituted aminomethylene malonic acid derivatives.
Es ist allgemein bekannt, daß unter den auf der Hautoberfläche vorhandenen Bakterien einige, wie zum Beispiel insbesondere Corynabacterium Acnes, Lipasen und Esterasenausscheiden, die auf den Hauttalg und andere auf der Haut vorhandene Triglyceride einwirken und daraus Fettsäuren freisetzen. Diese, durch enzymatische Spaltungsreaktionen erhaltenen Fettsäuren, sind neben anderen Faktoren die Ursache für unangenehme und unästhetische Hautausschläge, die vor allem im Gesicht und auf dem oberen Teil des Thorax und Rückens auftreten. Auf Grund dieser Erkenntnisse sind bereits enzyminhibierende Substanzen in kosmetischen Zusammensetzungen zur Vermeidung dieser nachteiligen Erscheinungen und zur Erhaltung-der Hautgesundheit eingesetzt worden, ohne daß bisher allgmeine durchgreifende Erfolge erzielt werden konnten. Es hat daher12 nicht an Versuchen gefehlt weitere Substanzen aufzufinden, die sich zur Bekämpfung dieser Hautveränderungen in kosmetischen Zusammensetzungen einsetzen lassen.It is well known that among those present on the surface of the skin Some bacteria, such as in particular Corynabacterium acnes, lipases and Secretion of esterases, which are found on sebum and other triglycerides present on the skin act and release fatty acids from it. This, through enzymatic cleavage reactions obtained fatty acids, among other factors, are the cause of unpleasant and unsightly rashes, especially on the face and on the upper part of the Thorax and back occur. On the basis of this knowledge there are already enzyme-inhibiting Substances in cosmetic compositions to avoid these disadvantageous Appearances and for the maintenance of the skin health have been used without that so far general sweeping successes could be achieved. It therefore has 12 not There is a lack of attempts to find further substances that can be used to combat this Allow skin changes to be used in cosmetic compositions.
Es wurde nun gefunden, daß Hautpflegemittel mit einem Gehalt an N-substituierten Aminomethylenmalonsäurederivaten der allgemeinen Formel in der R1 und R2 unabhängig voneinander für Wasserstoff, ein Alkylgruppe mit 1 bis 14 Kohlenstoffatomen eine Aryl-oder eine Aralkylgruppe, sowie beide gemeinsam mit dem Stickstoffatom für einen Heterocyclus, X und Y unabhängig voneinander für eine Alkoxycarbonylgruppe mit 1 - 4 Kohlenstoffatomen, eine gegebenenfalls substituierte Carbamoyl- oder Cyangruppe stehen, sich auf Grund von deren enzyminhibierenden Wirkungen gut zur Bekämpfung derartiger Hautveränderungen und zur Erhaltung der Hautgesundheit eignen.It has now been found that skin care products containing N-substituted aminomethylene malonic acid derivatives of the general formula in which R1 and R2 independently represent hydrogen, an alkyl group with 1 to 14 carbon atoms, an aryl or an aralkyl group, and both together with the nitrogen atom for a heterocycle, X and Y independently of one another for an alkoxycarbonyl group with 1-4 carbon atoms, one optionally Substituted carbamoyl or cyano groups are, due to their enzyme-inhibiting effects, are well suited for combating such skin changes and for maintaining skin health.
Die oben definierten N-substituierten Aminomethylenmalonsäurederivate können auch als Wirkstoffe in Deodorantien verwendet werden.The N-substituted aminomethylene malonic acid derivatives defined above can also be used as active ingredients in deodorants.
Die Herstellung der in den erfindungsgemäßen Hautpilegemitteln einzusetzenden N-substiuierten Aminomethylenmalonsäurederivate kann nach allgemein bekannten Verfahren der organischen Synthese erfolgen. Ein vorteilhaftes Herstellungsverfahren besteht in der Reaktion eines entsprechenden Alkoxymethylenmalonsäurederivats mit einem primären, sekundären Amin oder Ammoniak. Als für die Umsetzung geeignete Alkoxymethylenmalonsäure-Derivate kommen zum Beispiel Methoxymethylen-, Ethoxymethylen-, Butoxymethylen-malonsäuredimethylester, -malonsSurediethylester, -malonsäuredipropylester-, -malonsäuredibutylester, Ethoxymethylenmalonsäure-monoethylester-amid,-N,N-diethylamid, 3-Ethoxy-2-cyanacrylsäureethylester und Ethoxymethylenmalonsäuredinitril in Frage.The production of those to be used in the skin care agents according to the invention N-substituted aminomethylene malonic acid derivatives can be prepared by generally known processes organic synthesis. An advantageous one production method consists in the reaction of a corresponding alkoxymethylene malonic acid derivative with a primary, secondary amine or ammonia. As alkoxymethylene malonic acid derivatives suitable for the reaction for example methoxymethylene, ethoxymethylene, butoxymethylene malonic acid dimethyl ester, -malonic acid diethyl ester, -malonic acid dipropyl ester, -malonic acid dibutyl ester, ethoxymethylene malonic acid monoethyl ester amide, -N, N-diethylamide, 3-ethoxy-2-cyanoacrylic acid ethyl ester and ethoxymethylene malonic acid dinitrile in question.
Als für die Herstellung der erfindungsgemäß einzusetzenden N-substituierten Aminomethylenmalonsäurederivate aus den entsprechenden Alkoxymethylenderivaten geeignete Amine sind zum Beispiel Methyl-, Dimethyl-, Ethyl-, Diethyl-, Propyl-, Dipropyl-, Methylpropyl-, 2-Propyl-, Di-2-propyl-, Butyl-, Dibutyl-, 2-Butyl-, sek. Butyl-, tert. Butyl-, Hexyl-, Dihexyl-, 2-Ethylhexyl-, Octyl-, Ethyloctyl-, Decyl-, Dodecyl-, Ethanol-, Diisopropanol-, 3-Methoxypropyl-, 3- (2-Ethylhexoxy ) -propyl-, Benzylamin, Anilin, N-Methyl-, N-Ethyl-, N-Propyl-, N-Butylanilin, Piperidin, 2-Methyl-, 3-Methyl-, 4-Methylpiperidin, 2,6-Dimethyl-, 3,5-Dimethylpiperidin, Morpholin, 2,6-Dimethylmorpholin und Indolenin zu nennen.As for the preparation of the N-substituted to be used according to the invention Aminomethylene malonic acid derivatives from the corresponding alkoxymethylene derivatives are suitable Amines are, for example, methyl, dimethyl, ethyl, diethyl, propyl, dipropyl, Methylpropyl, 2-propyl, di-2-propyl, butyl, dibutyl, 2-butyl, sec. Butyl, tert. Butyl, hexyl, dihexyl, 2-ethylhexyl, octyl, ethyl octyl, decyl, dodecyl, Ethanol, diisopropanol, 3-methoxypropyl, 3- (2-ethylhexoxy) propyl, benzylamine, Aniline, N-methyl-, N-ethyl-, N-propyl-, N-butylaniline, piperidine, 2-methyl-, 3-methyl-, 4-methylpiperidine, 2,6-dimethyl-, 3,5-dimethylpiperidine, morpholine, 2,6-dimethylmorpholine and indolenine.
Als in den erfindungsgemäßen Hautpflegemitteln einzusetzende N-substituierte Aminomethylenmalonsäurederivate sind danach zum Beispiel N-Methylanilino-, 3,5-Dimethylpiperidino-, N-Methyl-p-anisidino-, N-Ethylanilino-, N-Propylanilino-, 3-Methoxyanilino-, N-Isobutylanilino-, Dimethylamino-, Diethylamino-, Butylamino-, Hexylamino-, Dibutylamino-, Octylamino-, Dodecylamino-, Benzylamino-, 2,5-Dimethoxyanilino-, 3, 4-Dimethoxyanilino-, Indoleninomethylenmalonsäurediethylester anzuführen.As N-substituted ones to be used in the skin care products according to the invention Aminomethylene malonic acid derivatives are then, for example, N-methylanilino, 3,5-dimethylpiperidino, N-methyl-p-anisidino-, N-ethylanilino-, N-propylanilino-, 3-methoxyanilino-, N-isobutylanilino-, Dimethylamino, diethylamino, butylamino, hexylamino, dibutylamino, octylamino, Dodecylamino, benzylamino, 2,5-dimethoxyanilino, 3, 4-dimethoxyanilino, indoleninomethylene malonic acid diethyl ester to cite.
Die erfindungsgemäßen Hautpflegemittel enthalten die als Wirkstoffe zur Erhaltung der Hautgesundheit und Bekämpfung genannter Hautveränderungen wie z. B. Akne oder Seborrhoea oleosa dienenden N-substituierten Aminomethylenmalonsäurederivate in einer Menge von o,5 bis 30 Gewichtsprozent, vorzugsweise 3 bis 15 Gewichtsprozent, bezogen auf die gesamte Präparation.The skin care products according to the invention contain them as active ingredients to maintain skin health and combat skin changes mentioned such as z. B. acne or seborrhoea oleosa serving N-substituted aminomethylene malonic acid derivatives in an amount of 0.5 to 30 percent by weight, preferably 3 to 15 percent by weight, based on the entire preparation.
Die erfindungsgemäßen Hautpflegemittel werden in Gestalt der für diese Zwecke üblichen Präparationen vorliegen, also Cremes, Gele, Lotionen, Hautmilch, Badeöle, Salben, Pomaden, Masken, Seifen und Aerosole. Ihre Herstellung erfolgt nach den für derartige Präparat ionen üblichen Verfahren. Dabei werden die als Wirkstoff dienenden N-substituierten Aminomethylenmalonsäurederivate mit den für die Hautpflegemittel als Basismaterial dienenden organischen Substanzen wie Wachsen, Fetten, ölen, Alkoholen, Mineralölen vermischt und danach mit den weiteren Bestandteilen der Hautpflegemittel wie Netzmitteln, Emulgatoren, Verdickungsmitteln, Konservierungsmitteln, Parfüms, Wasser, Lösungsmitteln, Treibgasen zum fertigen Endprodukt konfektioniert. Die Mengen der in den erffindungsgemäßen Hautpflegemitteln außer den N-substituierten Aminomethylenmalonsäurederivaten vorhandenen Rezepturbestandteile bewegen sich in den für vergleichsweise Produkte üblichen Größenordnungen.The skin care products according to the invention are in the form of those for this For the purpose of common preparations, i.e. creams, gels, lotions, skin milk, Bath oils, ointments, pomades, masks, soaps and aerosols. Your production takes place according to the usual procedures for such preparations. They are used as an active ingredient Serving N-substituted aminomethylene malonic acid derivatives with those for skin care products organic substances such as waxes, fats, oils, alcohols, Mineral oils mixed and then with the other ingredients of the skin care products such as wetting agents, emulsifiers, thickeners, preservatives, perfumes, Water, solvents, propellants made up into the finished end product. The quantities those in the skin care products according to the invention apart from the N-substituted aminomethylene malonic acid derivatives existing recipe components move in those for comparatively products usual orders of magnitude.
Die nachfolgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn jedoch hierauf zu beschränken.The following examples are intended to illustrate the subject matter of the invention in greater detail explain without, however, restricting it to this.
Beispiele Zunächst wird die Herstellung der in den erfindungsgemäßen Hautpfle gemitteln eingesetzten N-sub s-t ituerten Aminomethylenmalons äurederivat e beschrieben. Examples First, the production of the in the invention N-substituted aminomethylene malonic acid derivative used in skin care agents e described.
A) N-Methylanilinomethylenmalonsäure-diethylester Zu einer Lösung von 30 g (139 mMol) Ethoxymethylenmalonsäurediethylester in 100 ml Ethanol wurden unter Rühren 179 g (167 mMol) N-Methylanilin getropft.A) N-methylanilinomethylene malonic acid diethyl ester To a solution of 30 g (139 mmol) of diethyl ethoxymethylene malonate in 100 ml of ethanol were 179 g (167 mmol) of N-methylaniline were added dropwise with stirring.
Nach 1,5-stUndigem Rühren wurde noch 1,5 Stunden zum Sieden erhitzt, Ethanol abdestilliert, in Ether aufgenommen, die erhaltene Lösung zuerst mit stark verdünnter Salzsäure und danach mit Wasser gewaschen, mit Natriumsulfat getrocknet und das Reaktionsprodukt nach Entfernen des Ethers unter vermindertem Druck destilliert. Es wurden 26 g N-ethylanilinomethylenmalonsäurediethylester vom Kp. 1550 C bei o-,o8 mbar 20 und einem Brechungsindex nD : 1,5660 erhalten. After stirring for 1.5 hours, the mixture was heated to boiling for a further 1.5 hours, Distilled off ethanol, taken up in ether, the resulting solution first with strong dilute hydrochloric acid and then washed with water, dried with sodium sulfate and after removing the ether, the reaction product is distilled under reduced pressure. There were 26 g of N-ethylanilinomethylene malonic acid diethyl ester of boiling point 1550 C at o-, o8 mbar 20 and a refractive index nD: 1.5660.
Nach dem Umkristallisieren schmilzt die Substanz bei 53 bis 550 C. After recrystallization, the substance melts at 53 to 550 C.
In analoger Weise wurden die nachstehend aufgeführten Substanzen aus den entsprechenden Ausgangsmaterialien erhalten. The substances listed below were produced in an analogous manner obtained from the appropriate starting materials.
B) 3,5-Dimethylpiperidinomethylenmalonsäure-diethylester Kp. 139° C/0,08 mbar nD20 1,5120 C) N-Methyl-p-anisidinomethylenmalonsäure-diethylester Schmp. 84 bis 860 C D) N-Ethylanilinomethylenmalonsäure-diethylester 20 Kp. 153° C/1 mbar nD 1,5540 E) N-Propylanilinomethylenmalonsäure-diethylester 20 Kp. 160° C/0,13 mbar nD20 1,5490 F) N-Isobutylanilinomethylenmalonsäure-diethylester 20 Kp. 154° C/0,13 mbar nD 1,5427 G) 3-Methoxyanilinomethylenmalonsäure diethylester nD20 1,5846 H) Dimethylaminomethylenmalonsäure-diethylester 20 Kp. 1320 0/0,66 mbar nD 1,5081 I) Diethylaminomethylenmalonsäure-diethylester 20 Kp. 1210 C/0,13 mbar nD 1,4997 K) Butylaminomethylenmalonsäure-diethylester 20 Kp. 149° C/0,92 mbar nD 1,4991 L) Hexylaminomethylenmalonsäure-diethylester 20 Kp. 139° C/0,16 mbar nD 1,4940 M) Dibutylaminomethylenmalonsäure-diethylester 20 Kp. 131° C/0,11 mbar nD 1,4900 N) Octylaminomethylenmalonsäure-diethylester 20 Kp.158° C/0,16 mbar nD 1,4903 O) Dodecylaminomethylenmalonsäure-diethylester 20 nD 1,4863 P) Benzylaminomethylenmalonsäure-diethylester Schmp. 68 bis 700 C Q) 2,5-Dimethoxyanilinomethylenmalonsäure-diethylester Schmp. 76 bis 780 C R) 3,4-Dimethoxyanllinomethylenmalonsäure-diethylester Schmp. 54 bis 550 C S ) Indolinomethylenmalonsäure-diethylester 20 Kp. 176/0,13 mbar nD 1,6028 Zur Feststellung der enzyminhibierenden Wirksanikeit wurde folgende Testmethodik verwendet. Es wurden Jeweils 0,2 Mol in 10 bis 20 ml physiologischer Natriumchlorid-Lösung Substrat eingesetzt. Als Testenzyme dienten: Esterase aus Schweine leber (Carboxylic-esterhydrolase EC 3.1.1.1) Spezifische Aktivität: circa 100 U/mg, Einsatzkonzentration: 1 mg in 16 ml Lösung.B) Diethyl 3,5-dimethylpiperidinomethylene malonate, boiling point 139 ° C / 0.08 mbar nD20 1.5120 C) N-methyl-p-anisidinomethylene malonic acid diethyl ester, mp. 84 to 860 C D) N-Ethylanilinomethylene malonic acid diethyl ester 20 kp. 153 ° C / 1 mbar nD 1.5540 E) N-propylanilinomethylene malonic acid diethyl ester 20 kp. 160 ° C / 0.13 mbar nD20 1.5490 F) Diethyl N-isobutylanilinomethylene malonic acid 20 bp. 154 ° C / 0.13 mbar nD 1.5427 G) 3-methoxyanilinomethylene malonic acid diethyl ester nD20 1.5846 H) Dimethylaminomethylene malonic acid diethyl ester 20 Kp. 1320 0 / 0.66 mbar nD 1.5081 I) Diethylaminomethylene malonic acid diethyl ester 20 bp. 1210 C / 0.13 mbar nD 1.4997 K) Butylaminomethylene malonic acid diethyl ester 20 bp. 149 ° C / 0.92 mbar nD 1.4991 L) diethyl hexylaminomethylene malonate 20 bp. 139 ° C / 0.16 mbar nD 1.4940 M) Dibutylaminomethylene malonic acid diethyl ester 20 Kp. 131 ° C / 0.11 mbar nD 1.4900 N) Octylaminomethylene malonic acid diethyl ester 20 bp 158 ° C / 0.16 mbar nD 1.4903 O) Dodecylaminomethylene malonic acid diethyl ester 20 nD 1.4863 P) Benzylaminomethylene malonic acid diethyl ester Mp. 68 to 700 C Q) 2,5-dimethoxyanilinomethylene malonic acid diethyl ester, mp. 76 to 780 C R) 3,4-dimethoxyanllinomethylene malonic acid diethyl ester, melting point 54 to 550 C S) Indolinomethylene malonic acid diethyl ester 20 Kp. 176 / 0.13 mbar nD 1.6028 The following was used to determine the enzyme-inhibiting efficacy Test methodology used. Each 0.2 mole in 10 to 20 ml became more physiological Sodium chloride solution substrate used. The following were used as test enzymes: Esterase from Pig liver (carboxylic ester hydrolase EC 3.1.1.1) Specific activity: approx 100 U / mg, use concentration: 1 mg in 16 ml solution.
Als Substrat diente Citronensäuretriethylester.Citric acid triethyl ester served as the substrate.
Lipase aus Rhizopus arrhizus (Triacylglycerolacylhydrolase EC 3.1.1.3) Spezifische Aktivität: circa i 200 U/mg, Einsatzkonzentration: 0,25 mg in 20 ml Lösung Als Substrat diente Olivenöl. Zur Stabilisierung der Emulsion wurde Natriumdesoxycholat und Gummi arabicum verwendet. Die Hemmwerte wurden bestimmt durch azidimetrischen Vergleich der Kontrolle mit der durch die Prüfsubstanz gehemmten Reaktion und in % ausgedrückt.Lipase from Rhizopus arrhizus (Triacylglycerol acylhydrolase EC 3.1.1.3) Specific activity: approx. 200 U / mg, use concentration: 0.25 mg in 20 ml Solution Olive oil served as the substrate. Sodium deoxycholate was used to stabilize the emulsion and gum arabic are used. The inhibition values were determined by acidimetric Comparison of the control with the reaction inhibited by the test substance and in % expressed.
Als Konzentration für die Hemmsubstanzen wurden 2 500 ppm gewählt.The concentration chosen for the inhibiting substances was 2,500 ppm.
Die bei den Testen festgestellten Hemmwerte sind nachstehender Tabelle
1 zu entnehmen:
Tabelle 1
Hautpflegesalbe gegen Akne Gemisch aus höhermolekularem Fettalkohol 30,0 Gewichtsteile Wachsestern u. mineral. Fetten (Amphocerin K(R)) ölsäuredecylester 10,0 Gewichtsteile Produkt A 10,0 Gewichtsteile Wasser 50,0 Gewichtsteile Hautpflegrecreme in Gelform gegen Akne Cetylstearylalkohl mit circa 30 Mol Ethylenoxid 14,0 Gewichtsteile Polyol Fettsäure-Ester (Cetiol HE (R)) 20,0 Gewichtsteile 2-Octyldodecanol 5>0 Gewichtsteile Produkt M 3,0 Gewichtsteile Wasser 58,0 Gewichtsteile Hautpflegecreme gegen Akne Kolloiddisperses Gemisch aus 90 Teilen Cetylstearylalkohol und 10 Teilen Natrium-Cetylstearylsulfat 15,0 Gewichtsteile Reisstärke 5,0 Gewichtsteile Puderfarbe 1,0 Gewichtsteile Titandioxid 2,0 Gewichtsteile Produkt N 5,0 Gewichtsteile Wasser 72,0 Gewichtsteile Hautpflegestift gegen Akne Cetylalkohol 5,0 Gewlchtsteile Bienenwachs weiß 30,0 Gewichtsteile Walrat 20,0 Gewichtsteile 2-Octyldodecanol 25,0 Gewichtsteile Paraffinöl 8,0 Gewichtsteile Zinkoxid 5,0 Gewichtsteile Puderfarbe braun 3,0 Gewichtsteile Produkt 0 4,0 Gewichtsteile Hautpflegelotion gegen Akne Kolloiddisperses Gemisch aus 90 Teilen Cetylstearylalkohol und 10 Teilen Natrium-Cetylstearylsulfat 3,0 Gewichtsteile ölsäuredecylester 5,0 Gewichtsteile Produkt I 5,0 Gewichtsteile Wasser 87, 0 Gewichtsteile Hautpflegeöl genen Akne Ölsäuredecylester 15,0 Gewichtsteile 2-Octyldodecanol 10,0 Gewichtsteile Capryl/Caprinsäuretriglycerid 30,0 Gewichtsteile Paraffinöl 35,0 Gewichtsteile Produkt H 10,0 GewichtsteileSkin care ointment against acne Mixture of high molecular weight fatty alcohol 30.0 parts by weight wax esters and minerals. Fetten (Amphocerin K (R)) oleic acid decyl ester 10.0 parts by weight of product A 10.0 parts by weight of water 50.0 parts by weight Skin care cream in gel form against acne cetostearyl alcohol with about 30 moles of ethylene oxide 14.0 parts by weight Polyol fatty acid ester (Cetiol HE (R)) 20.0 parts by weight 2-octyldodecanol 5> 0 Parts by weight of product M 3.0 parts by weight of water 58.0 parts by weight of skin care cream Against acne colloidal mixture of 90 parts of cetostearyl alcohol and 10 parts Sodium cetyl stearyl sulfate 15.0 parts by weight rice starch 5.0 parts by weight powder color 1.0 parts by weight of titanium dioxide 2.0 parts by weight of product N 5.0 parts by weight of water 72.0 parts by weight skin care stick against acne cetyl alcohol 5.0 parts by weight beeswax white 30.0 parts by weight whale rat 20.0 parts by weight 2-octyldodecanol 25.0 parts by weight Paraffin oil 8.0 parts by weight zinc oxide 5.0 parts by weight powder paint brown 3.0 parts by weight Product 0 4.0 parts by weight Skin care lotion against acne colloidal disperses Mixture of 90 parts of cetyl stearyl alcohol and 10 parts of sodium cetyl stearyl sulfate 3.0 parts by weight of oleic acid decyl ester 5.0 parts by weight of product I 5.0 parts by weight Water 87.0 parts by weight skin care oil genes acne oleic acid decyl ester 15.0 parts by weight 2-octyldodecanol 10.0 parts by weight caprylic / capric acid triglyceride 30.0 parts by weight Paraffin oil 35.0 parts by weight of product H 10.0 parts by weight
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803018132 DE3018132A1 (en) | 1980-05-12 | 1980-05-12 | Anti-acne and deodorant skin-care preparations - contg. amino:methylene-malonic acid derivs. which inhibit esterase and lipase enzymes secretions from skin bacteria |
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| DE19803018132 DE3018132A1 (en) | 1980-05-12 | 1980-05-12 | Anti-acne and deodorant skin-care preparations - contg. amino:methylene-malonic acid derivs. which inhibit esterase and lipase enzymes secretions from skin bacteria |
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| DE3018132A1 true DE3018132A1 (en) | 1981-11-19 |
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Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0207287A2 (en) * | 1985-06-04 | 1987-01-07 | Bayer Ag | Indole derivatives, process for their preparation and cosmetic preparation containing them |
| WO1999048471A1 (en) * | 1998-03-24 | 1999-09-30 | The Procter & Gamble Company | Polyalkoxy copolymers as lipase inhibitors and their compositions |
| DE10063867A1 (en) * | 2000-12-21 | 2002-07-11 | Haarmann & Reimer Gmbh | Compositions for protecting human skin and hair against the damaging effects of ultraviolet radiation, comprise new or known N-substituted anilinomethylene malonic acid derivatives |
| DE102011086019A1 (en) | 2011-11-09 | 2012-08-02 | Henkel Ag & Co. Kgaa | Cosmetic product useful for preventing body odor, comprises composition comprising antiperspirant or deodorant active substance, water, and agent for dissolving or suspending active substance, propellant, and aerosol dispensing device |
| DE102011089430A1 (en) | 2011-12-21 | 2012-08-23 | Henkel Ag & Co. Kgaa | Use of a specified hydrocarbon, obtained from non-fossil biomass, as a blowing agent for spray products, preferably a cosmetic product, pharmaceutical product, air care product, home care product or a product for the car or paint care |
| DE102011087980A1 (en) | 2011-12-08 | 2012-09-06 | Henkel Kgaa | Cosmetic and non-therapeutic use of platycodin e.g. for influencing natural pigmentation process of hair and its follicles in armpit region, for reducing shaving or epilation frequency, and as active substance in topically applied agents |
| WO2013079349A1 (en) | 2011-12-02 | 2013-06-06 | Henkel Ag & Co. Kgaa | Cosmetic aerosol spray with lasting freshness effect |
| DE102011088967A1 (en) | 2011-12-19 | 2013-06-20 | Henkel Ag & Co. Kgaa | Deodorants and antiperspirants with stabilized antioxidant |
| DE102011089012A1 (en) | 2011-12-19 | 2013-06-20 | Henkel Ag & Co. Kgaa | Textile-friendly antiperspirants |
| WO2013092208A2 (en) | 2011-12-22 | 2013-06-27 | Henkel Ag & Co. Kgaa | Antiperspirant suspension spray with improved active ingredient release and reduced soiling of textiles |
| DE102011089340A1 (en) | 2011-12-21 | 2013-06-27 | Henkel Ag & Co. Kgaa | PEG-free antiperspirant oil-in-water emulsions with improved feel |
| DE102012222692A1 (en) | 2012-12-11 | 2013-09-05 | Henkel Ag & Co. Kgaa | Cosmetic composition useful as antiperspirant and deodorant, comprises 2-benzylheptan-1-ol, and rosemary extract |
| DE102012224156A1 (en) | 2012-12-21 | 2014-06-26 | Henkel Ag & Co. Kgaa | Textile-friendly nonaerosol antiperspirants with hydroxycarboxylic acids |
| WO2014095688A2 (en) | 2012-12-21 | 2014-06-26 | Henkel Ag & Co. Kgaa | Textile-sparing, non-aerosol antiperspirants with methanesulphonic acid |
| DE102012224157A1 (en) | 2012-12-21 | 2014-06-26 | Henkel Ag & Co. Kgaa | Textile-friendly antiperspirant sprays with hydroxycarboxylic acids |
| DE102012224142A1 (en) | 2012-12-21 | 2014-06-26 | Henkel Ag & Co. Kgaa | Textile-friendly antiperspirant sprays with methanesulfonic acid |
| DE102014217316A1 (en) | 2014-08-29 | 2016-03-03 | Henkel Ag & Co. Kgaa | Low-electrolyte preparations against body odor |
-
1980
- 1980-05-12 DE DE19803018132 patent/DE3018132A1/en not_active Withdrawn
Cited By (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0207287A2 (en) * | 1985-06-04 | 1987-01-07 | Bayer Ag | Indole derivatives, process for their preparation and cosmetic preparation containing them |
| EP0207287A3 (en) * | 1985-06-04 | 1988-05-11 | Bayer Ag | Indole derivatives, process for their preparation and cosmetic preparation containing them |
| US4792609A (en) * | 1985-06-04 | 1988-12-20 | Bayer Aktiengesellschaft | Indoline and 1,2,3,4-tetrahydroquinoline N(dicarboalkoxyvinyl) substituted derivatives |
| WO1999048471A1 (en) * | 1998-03-24 | 1999-09-30 | The Procter & Gamble Company | Polyalkoxy copolymers as lipase inhibitors and their compositions |
| US6461601B1 (en) | 1998-03-24 | 2002-10-08 | The Proctor & Gamble Company | Polyalkoxy copolymers as lipase inhibitors and their compositions |
| DE10063867A1 (en) * | 2000-12-21 | 2002-07-11 | Haarmann & Reimer Gmbh | Compositions for protecting human skin and hair against the damaging effects of ultraviolet radiation, comprise new or known N-substituted anilinomethylene malonic acid derivatives |
| DE102011086019A1 (en) | 2011-11-09 | 2012-08-02 | Henkel Ag & Co. Kgaa | Cosmetic product useful for preventing body odor, comprises composition comprising antiperspirant or deodorant active substance, water, and agent for dissolving or suspending active substance, propellant, and aerosol dispensing device |
| WO2013079349A1 (en) | 2011-12-02 | 2013-06-06 | Henkel Ag & Co. Kgaa | Cosmetic aerosol spray with lasting freshness effect |
| DE102011087662A1 (en) | 2011-12-02 | 2013-06-06 | Henkel Ag & Co. Kgaa | Cosmetic aerosol spray with lasting freshness effect |
| DE102011087980A1 (en) | 2011-12-08 | 2012-09-06 | Henkel Kgaa | Cosmetic and non-therapeutic use of platycodin e.g. for influencing natural pigmentation process of hair and its follicles in armpit region, for reducing shaving or epilation frequency, and as active substance in topically applied agents |
| WO2013092185A2 (en) | 2011-12-19 | 2013-06-27 | Henkel Ag & Co. Kgaa | Textile-sparing antiperspirants |
| DE102011088967A1 (en) | 2011-12-19 | 2013-06-20 | Henkel Ag & Co. Kgaa | Deodorants and antiperspirants with stabilized antioxidant |
| DE102011089012A1 (en) | 2011-12-19 | 2013-06-20 | Henkel Ag & Co. Kgaa | Textile-friendly antiperspirants |
| WO2013092114A2 (en) | 2011-12-19 | 2013-06-27 | Henkel Ag & Co. Kgaa | Deodorants and antiperspirants having stabilized antioxidant |
| DE102011089340A1 (en) | 2011-12-21 | 2013-06-27 | Henkel Ag & Co. Kgaa | PEG-free antiperspirant oil-in-water emulsions with improved feel |
| WO2013092186A2 (en) | 2011-12-21 | 2013-06-27 | Henkel Ag & Co. Kgaa | Peg-free antiperspirant oil-in-water emulsions having improved feel |
| DE102011089430A1 (en) | 2011-12-21 | 2012-08-23 | Henkel Ag & Co. Kgaa | Use of a specified hydrocarbon, obtained from non-fossil biomass, as a blowing agent for spray products, preferably a cosmetic product, pharmaceutical product, air care product, home care product or a product for the car or paint care |
| US9186304B2 (en) | 2011-12-21 | 2015-11-17 | Henkel Ag & Co. Kgaa | Peg-free antiperspirant oil-in-water emulsions having improved feel |
| DE102011089560A1 (en) | 2011-12-22 | 2013-06-27 | Henkel Ag & Co. Kgaa | Antiperspirant suspension spray with improved drug release and reduced textile soiling |
| WO2013092208A2 (en) | 2011-12-22 | 2013-06-27 | Henkel Ag & Co. Kgaa | Antiperspirant suspension spray with improved active ingredient release and reduced soiling of textiles |
| DE102012222692A1 (en) | 2012-12-11 | 2013-09-05 | Henkel Ag & Co. Kgaa | Cosmetic composition useful as antiperspirant and deodorant, comprises 2-benzylheptan-1-ol, and rosemary extract |
| WO2014095688A2 (en) | 2012-12-21 | 2014-06-26 | Henkel Ag & Co. Kgaa | Textile-sparing, non-aerosol antiperspirants with methanesulphonic acid |
| DE102012224157A1 (en) | 2012-12-21 | 2014-06-26 | Henkel Ag & Co. Kgaa | Textile-friendly antiperspirant sprays with hydroxycarboxylic acids |
| DE102012224142A1 (en) | 2012-12-21 | 2014-06-26 | Henkel Ag & Co. Kgaa | Textile-friendly antiperspirant sprays with methanesulfonic acid |
| DE102012224133A1 (en) | 2012-12-21 | 2014-06-26 | Henkel Ag & Co. Kgaa | Textile-friendly nonaerosol antiperspirants with methanesulfonic acid |
| US9095520B2 (en) | 2012-12-21 | 2015-08-04 | Henkel Ag & Co. Kgaa | Textile friendly non-aerosol antiperspirants with a hydroxy acid |
| DE102012224156A1 (en) | 2012-12-21 | 2014-06-26 | Henkel Ag & Co. Kgaa | Textile-friendly nonaerosol antiperspirants with hydroxycarboxylic acids |
| US9549883B2 (en) | 2012-12-21 | 2017-01-24 | Henkel Ag & Co. Kgaa | Textile friendly nonaerosol-antiperspirants with methansulfonic |
| DE102014217316A1 (en) | 2014-08-29 | 2016-03-03 | Henkel Ag & Co. Kgaa | Low-electrolyte preparations against body odor |
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