DE2351927A1 - Deodorising cosmetic compsns. - contg. lichen acid derivs, have enhanced antimicrobial activity - Google Patents

Abstract

The cosmetic contains a mono-/di- ester/either of usnic acid, evernic acid, psoromic acid and/or vulpinic acid. These lichen derivs., esp that of usnic acid (1, 3-dihydroxy -7, 9-dioxo-4,8-diacetyl-2, 9a-dimethyl-7, 8, 9, 9a-tetrahydro-dibenzofuran), exhibit increased solubility in the organic solvents, fats etc. commonly used in cosmetic formulations and their anti-microbial activity thereby enhanced even at rel. low concns. The cosmetic pref. contains the mono-/di- ethyl/ispropyl either or the mono-/di-lactate/acetate of usnic acid in amts. of 0.01-5.0, esp. 0.01-0.5, wt. %. Up to 0.1 wt. % (based on formulation) of other, known, deodorants/antimicrobials may be used in the cosmetic (e.g. 2,2'-dihydroxy-3, 3', 5, 5', 6, 6'-hexachloro-diphenylmethane, 2, 4, 4'-trichloro-2'-hydroxy-phenyl either, 3, 5, 4'-tribromo-salicylanilide or 3, 4, 4'-trichloro-carbanilide). The cosmetic, which is active against gram-positive skin germs, may be used in any conventional form, e.g. lotion, cream, stick and, esp. in power sprays or in alcohol-contg. aerosol formulations.

Description

PATEN ΓΑ NW BJ.TE
DR. W. KINZEBACH - DIPL.-ING. O. HELLEBRAND 2351927

8 Munich 80 October 16, 1973 ■ Walpurgisstrasse 6 Telephone: 0811/470 50 34 Telegrams: Hekipat (Munich)

ORISSA DREBIKG GMBH

2 Hamburg 26
Borstelmannsweg 169-171

-ee- middle-, KE.

f 1

The invention relates to a deodorant cosmetic agent with germ-inhibiting properties.

It is "known to have antimicrobial substances in deodorants to use. These substances have the task of the bacterial decomposition of sweat and thus the To prevent the occurrence of unpleasant smelling decomposition products. There are numerous antimicrobial agents Substances, but only relatively few, meet the special requirements of a cosmetic in practice.

The object of the present invention is to create a deodorant cosmetic agent that is good on the skin and Compatible with the mucous membrane, practically non-toxic and very good even at low concentrations of antimicrobial active ingredient has a good deodorizing effect and, moreover, can be used in all preparation forms customary in cosmetics.

retroactively
changed

509817/1134

It has now been found that "certain derivatives of lichen acids, in particular the esters and ethers of usnic acid, evernic acid, psoromic acid and vulpinic acid for the production of surprisingly effective and well-tolerated deodorants can be used.

Surprisingly, the antimicrobial effectiveness of the abovementioned lichen acids is determined by their conversion Esters or ethers are not impaired, but at the same time the solubility in organic solvents, fats, fat-like solvents Substances and other auxiliaries for cosmetic preparations significantly improved.

Usnic acid (1,3-dihydroxy-7,9-dioxo-4,8-diacetyl-2,9a-dimethyl-7,8,9,9a-tetrahydro-dibenzofuran) can be isolated from the lichen Usnea barbata but also from other lichens. she is a narrow-spectrum antibiotic that is particularly effective against gram-positive pathogens, Neisseria and mycobacteria (cf. H. Ippen, "Index Pharmacorum", Georg Thieme Verlag, Stuttgart, 1968, page 401) and is in many auxiliary materials, such as fats and fat-like substances necessary for the manufacture Pharmaceutical preparations used are either insoluble or only slightly soluble. They also had orientation Experiments have shown that when usnic acid and the other lichen acids are used in conventional preparations, these Acids had to be used in inappropriately high concentrations. By the esterification or etherification according to the invention of the abovementioned lichen acids, in particular usnic acid, is - as already mentioned above - the solubility in organic Solvents, fats, fat-like substances and other auxiliaries for cosmetic preparation forms have been significantly improved and, surprisingly, the antimicrobial effectiveness improved and expanded, so that these lichen acid derivatives in relatively low concentrations used in cosmetic products can be.

- 2 509817/1134

The production of the esters or ethers of the uznic acid and the other lichen acids mentioned above takes place in per se known Way. The esterification can, for example, be carried out in the presence of acidic catalysts and water-binding agents are, by reaction with ketenes or carboxylic anhydrides or by reaction with acid chlorides in the presence of a Base. The esterification methods known for the esterification of phenols are preferably used.

The mono- and diesters of organic mono- and dicarboxylic acids are advantageous. The mono-diesters of the Üsnic acid are particularly advantageous of lactic acid, acetic acid, propionic acid, butyric acid, malonic acid, fumaric acid, maleic acid, succinic acid, Glutaric acid, malic acid, tartaric acid and the like and the like Esters of the other lichen acids mentioned above.

The etherification of lichen acids also takes place in a manner known per se Way, for example by treatment with haloalkyl in the presence of alkalis, by treatment with mono- or dialkyl sulfate in alkaline solution, by treatment with a diazoalkane etc .. The mono- and di-methyl-, ethyl, isopropyl, propyl, glyceryl, sorbitol and polyglycol ethers of the Üsnic acid and the other above-mentioned lichen acids, including the ethers, which are formed by attachment of ethylene oxide arise.

! The agent according to the invention thus contains an organic mono- or

Diester or ether of a lichen acid, especially the Usnin

j acid, evernic acid, psoromic acid or vulpic acid or a

mixture of these lichen acid derivatives and an organic solvent

! agents as well as the usual basic substances of cosmetic preparation

j shape.

The agent according to the invention preferably contains an usnic acid monoester or diester of acetic acid, lactic acid, propionic acid

- 3 5098 17/1 1.34

acid, butyric acid, malonic acid, maleic acid, fumaric acid, succinic acid, Malic acid, tartaric acid, glutaric acid or a corresponding mono- or diester of any of the others mentioned above Lichen acids or a usnic acid mono- or dimethyl, ethyl, isopropyl, propyl, glyceryl, sorbitol or polyglycol ether or one created by the addition of ethyl dioxide Usnic acid mono- or diether or a corresponding ether of one of the other named lichen acids or a mixture this ether and / or ester.

Usnic acid mono- and diethyl ethers are particularly advantageous, the usnic acid mono- and diisopropyl ethers and the usnic acid mono- and diesters of lactic acid and acetic acid.

The deodorant properties of the agent according to the invention can be further increased by adding relatively small amounts of other antimicrobially active substances which are particularly suitable and used for the production of deodorants, for example by adding 2,2'-dihydroxy-3,3 ', 5 , 5 ', 6,6'-hexachlorodiphenylmethane;2,4,4'-trichloro-2'-hydroxyphenylether;3,5,4'-tribromosalicylanilide;3,4,4'-trichlorocarbanilide or by adding mixtures of these substances, which often have a synergistic effect. To achieve an optimal effect, an addition of 0.1% by weight, based on the total product, is completely sufficient. Commercial products of known bacteriostatics and disinfectants that can be used in the agents according to the invention are, for example, bromochlorophene (2,2'-dihydroxy-3,3'-dibromo-5,5'-dichlorodiphenylmethane), Irgasan CF 3, Bronopol,; Dioxin, Germall, p-hydroxybenzoic acid esters, quaternary ammonium compounds, substituted and unsubstituted phenols and aldehydes, such as formaldehyde, acetaldehyde, glyoxal, glyoxylic acid ^: and glutaraldehyde. -;

The agent according to the invention is used in amounts of 0.01-5.0, preferably 0.01-2.0% by weight, in particular 0.01-0.5 used in cosmetic preparations.

509817/1134

The agent according to the invention, in particular the usnic acid ester and -ether-containing agents, has the surprising advantage that Even in low concentrations, it has a remarkably favorable antimicrobial effect compared to skin-specific gram-positive ones Has germs and is very suitable for the production of deodorants in all preparation forms, such as lotions, Creams, stick-shaped preparations, powders and sprays are suitable.

The agent according to the invention is particularly suitable for the preparation of sprays, both as so-called powder sprays as well as ordinary aerosol sprays. The compositions according to the invention are particularly advantageous in alcohol-containing compositions Aerosol preparations.

The following examples serve to further illustrate agents according to the invention;

1) Deodorant stick: Weight% Components 3.0 C ethyl stearyl alcohol 27.0 2-octyldodecanol 3.0 Coconut fatty acid monoethanolamide 8.0 Stearic acid 0.1 Usnic acid isopropyl ether 51.9 Ethanol 96% 2.0 1,2 propylene glycol 3.0 38 $ aqueous solution of sodium hydroxide 2.0 Perfume

100.0

- 5 0 9 817/1134

2) Deodorant spray: Components

2-octyldodecanol 5.00

Ethanol 96% 43.95

Usnic acid ethyl ether 0.05

Perfume 1.00

technical mixture of difluorodichloromethane and

Tetrafluorodichloroethane in a ratio of 40:60 '50 .00

100.00

50981.7 / 1 134

Claims (6)

PATEHIA N PROVERBS Deodorant cosmetic agent containing an organic mono- or di-ester or ether of usnic acid, Evernic acid, psoromic acid or vulpinic acid or a mixture of these compounds and an organic solvent, as well as customary ones Basic substances for cosmetic preparation forms. 2. Means according to claim 1, containing a usnic acid mono- or diesters of acetic acid, lactic acid, propionic acid, butyric acid, malonic acid, maleic acid, fumaric acid, succinic acid, Malic acid, tartaric acid, glutaric acid or a corresponding mono- or diester of evernic acid, psoromic acid or vulpinic acid and / or a usninsäureraono- or -di-methyl-, -ethyl-, -isopropyl-, -propyl-, -glyceryl-, -sorhit- or -polyglycolether or a usnic acid mono- or diether formed by the addition of ethylene oxide or a corresponding ether Evernic acid, psoromic acid or vulpinic acid or a mixture of these ethers and / or esters. 3. Composition according to claim 1 or 2, containing an usnic acid ester or ether according to claim 2 or a mixture of these Ether and / or ester. 4-. Agent according to one of Claims 1 "to 3, containing Usnic acid mono- or diethyl ether, usnic acid mono- or diiso-; propyl ether or a usnic acid mono- or diester of milk: '. - 7 5098 17/1134 : acid or acetic acid or a corresponding ether or ester of evernic acid, psoromic acid or volipic acid or a Mixture of these ethers and / or esters. ' 5. Means according to claim 4, containing usnic acid mono- ! or diethyl ether, usnic acid mono- or diisopropyl ether I or a usnic acid mono- or diester of lactic acid or ; Acetic acid or a mixture of these ethers and / or esters. I. 6. Agent according to one of claims 1 Ms 5, containing ; also 2,2'-dihydroxy-3, 3 ', 5,5', o ^ -hexachlorodiphenylmethane, j 2,4,4'-trichloro-2'-hydroxyphenyl ether, 3,5,4'-trit> romsalicyl- I anilide or 3,4,4'-trichlorocarbanilide or mixtures of these 'Substances. - 8 509817/1 134