WO2005004601A1

WO2005004601A1 - Secondary alcohols used as antimicrobial agents

Info

Publication number: WO2005004601A1
Application number: PCT/EP2004/051078
Authority: WO
Inventors: Aurelia Reckziegel; Horst Surburg; Florian Wolf; Jürgen Rabenhorst
Original assignee: Symrise Gmbh & Co. Kg
Priority date: 2003-07-08
Filing date: 2004-06-09
Publication date: 2005-01-20
Also published as: EP1651037A1; DE10330697A1

Abstract

Disclosed is the use of a compound of formula (I) as an agent against gram-positive bacteria, wherein m and n independently represent 0 and 1, R1 to R6 independently represent hydrogen or methyl, and A represents a phenyl group that is optionally substituted with additional C1 to C5 alkyl substituents, a norborane-2-yl group, or a pinane-3-yl group.

Description

Secondary alcohols as antimicrobial agents

The present invention relates to the use of certain secondary alcohols as active ingredients against Gram-positive bacteria, as are particularly responsible for (a) body odor, (b) impure skin and / or acne, and (c) bad breath and / or bad breath. Some of the compounds that can be used according to the invention are new, as are the preparations in which they are used.

The healthy warm-blooded organism, especially the healthy human skin and mucous membrane, is populated with a large number of non-pathogenic microorganisms. This so-called microflora of the skin or mucous membrane is not only harmless, it represents an important protection for the defense against opportunistic or pathogenic germs. In contrast, other microorganisms can improve the condition of the healthy ones

Skin and mucous membrane, e.g. also significantly influence their smell.

There is a constant need for substances and agents with antimicrobial properties. In particular, antimicrobial agents are sought, the antibacterial spectrum (antibiogram) of which includes Gram-positive bacteria. It is already known that certain alcohols have an antimicrobial effect. In practice, primary alcohols such as. B. Famesol, a primary sesquiterpene alcohol. However, farnesol and other primary alcohols with antimicrobial properties have a sensitizing and allergenic potential, so that their use is increasingly no longer tolerated.

It was therefore the primary object of the present invention to provide compounds which are active against Gram-positive bacteria. In addition, the compounds to be specified should have a possibly slight intrinsic odor, be easy to incorporate into antibacterial preparations, be stable in the usual cosmetic formulations and also under the required application conditions, and be readily accessible, ie. H. be producible by simple chemical reactions and be well tolerated, d. H. do not cause unacceptable health effects when used-

The aforementioned object is achieved by using a compound of the formula I.

as an active ingredient against Gram-positive bacteria in which m and n are independently 0 and 1,

R ¹ to R ^{6 are} independently hydrogen or methyl and

A is a phenyl group optionally substituted with a further C, - to C ₅ - substituted alkyl substituents, a norbornane-2-yl or a Pinaπ- 3-yl-Grυppe.

Preferably at least one group R ¹ to R ⁶ present in the compound of formula I to be used according to the invention is methyl (ie if m = n = 0 one of the substituents R ¹ or R ² ; if m = 0 and n = 1 one of the substituents R ¹ , R ² , R ³ and R ⁴ ; if m = 1 and n = 0 one of the substituents R ¹ , R ² , R ⁵ and R ⁶ ), if A is a phenyl group or a monoalkyl-substituted phenyl group.

The alcohols to be used according to the invention are secondary alcohols which comprise an aryl radical (group A). The use of the compounds of the formula I for combating gram-positive bacteria did not result from the prior art.

J. Agric-Food Chem-1993 (41), 2447-2450 (Kubo et al.) Discloses that certain secondary alcohols such as 2-undecanol and geranylacetol are effective against Streptococcus mutans (a gram-positive bacterium), and in one recent publication in Bioorg. Med. Chem. 1995 (3), 873-880 (Kubo et al.) Supplementary information on the antimicrobial activity of secondary alcohols against a number of Gram-positive bacteria is disclosed, but there is no indication of the applicability of secondary alcohols which are listed under the formula I fall.

Although WO 01/85120 A1 relates to the use of the secondary alcohol 6,10-dimethyI-5,9-undecadien-2-ol as an antimicrobial active ingredient, it also gives no indication of the usability of secondary alcohols which come under the formula I.

DE 100 25 124 A1 describes combinations of active ingredients which comprise a glycerol monoalkyl ether and an aryl-substituted alcohol. It is not excluded that the glycerol monoalkyl ether is combined with a secondary aryl-substituted alcohol, but the primary alcohols phenoxyethanoi, anise alcohol and 2-methyl-5-phenyl-pentan-1-ol and the tertiary alcohol phenyl-dimethylethylcarbonol are particularly preferred , It is not disclosed that aryl-substituted alcohols alone can have an effect against Gram-positive bacteria, and this applies in particular to aryl-substituted secondary alcohols.

US 4,006,218 (Sipos) discloses the use of certain phenylalkanols, including secondary alcohols, as enhancers (potentiators) of the antimicrobial activity of an antimicrobial agent. There is no indication of the antimicrobial activity of the phenylalkanols used for the purpose of reinforcement.

EP 0 919 607 A2 discloses additives for the physical and / or microbiological stabilization of the liquid or viscous composition of a lubricant, the additive being an aromatic alcohol, which can also be secondary. However, it is not disclosed which germs the additive should be effective against; however, it is generally stated that

Cooling lubricant compositions are microbiologically stabilized. However, since cooling lubricants are usually only colonized by bacteria that are Gram-negative, EP 0 919 607 A2 at least gives no indication that they are used as an additive

Stabilization of aromatic lubricants usable in cooling lubricants have an antibacterial effect against Gram-positive bacteria

Finally, reference is made to DE 4 447 361 A1, which discloses the use of primary arylalkyl alcohols as antimicrobial active ingredients

As can already be seen from the above assessment of various publications, numerous studies on the antimicrobial activity of alcohols have been carried out in the past decades. It is therefore extremely surprising that it has not hitherto been recognized that the compounds of the formula I to be used according to the invention have a very excellent activity against Having Gram-positive bacteria For use in practice, the compounds of the formula I are particularly suitable because they have at most a low intrinsic odor and can be prepared by simple chemical reactions. The secondary alcohols of the formula I are active substances against Gram-positive bacteria in particular can be used in cosmetic, oral hygiene and / or dermatological preparations

Although the present invention generally uses a compound of formula I

with the meanings of the substituents mentioned as

Active ingredient against Gram-positive bacteria, it is particularly preferred, the compound of formula I against Gram-positive bacteria

to be used, which are selected from the group consisting of (a) body odor, (b) impure skin and / or acne and (c) bad breath and / or bad breath causing bacteria. Gram-positive bacteria are known to the person skilled in the art, which are responsible for the unpleasant body conditions according to (a) - (c).

Gram-positive bacteria that cause body odor are bacteria e.g. B. from the genera Corynebacterium, Staphyiococcus, Micrococcus and Brevibacterium, in particular Corynebacterium xerosis, Staphyiococcus epidermidis and Staphyiococcus hominis, Micrococcus luteus and / or Micrococcus sedentarius and Brevibacterium epidermidis.

Gram-positive bacteria that verusacheπ impure skin and / or acne are, for example, bacteria of the genus Propionibacterium, in particular Propionibacterium acnes.

Gram-positive bacteria that cause bad breath and / or bad breath are, for example, bacteria of the genera Actinomyces, Eubacterium, Rothia and Stomatococcus, in particular Actinomyces viscosus, Eubacterium brachy, Eubacterium nodatum, Eubacterium saburreum, Eubacterium timidum and Eubacterium denticus and Roth Stomatococcus mucilaginosus.

The secondary alcohols of formula (!) Harmonize with a variety of common cosmetic auxiliaries and additives. The compounds of formula I can therefore be incorporated into a wide variety of dosage forms and preparations. Preparations to be applied to the skin which contain compounds of the formula I are able to determine the number of Gram-positive bacteria responsible for the respective phenomenon or the particular impairment according to the above

Enumeration (a) to (c) are responsible for reducing, while the microflora of the contacted skin is protected. Preparations which contain the compounds of the formula I are regularly distinguished by good skin tolerance, provided that none of the other constituents contained in the preparation cause an intolerance.

The above remarks apply in particular to deodorants, especially those against body odor and bad breath, which contain the secondary alcohols of the formula I. Such deodorants have good skin tolerance (including

Tolerance to the mucous membrane) and - provided a sufficient dosage of the compound of the formula I to be used according to the invention - have an activity over a longer period of time, of the order of magnitude of at least half a day, without their action noticeably diminishing.

Preferred among the compounds of the formula I are those for which: m + n = 0 or 2. These compounds have a particularly high activity against Gram-positive bacteria.

Compounds of the formula I which have at least three, preferably at least four, CH ₃ groups are further preferred, since these too are regularly particularly active against Gram-positive bacteria.

In the compounds of formula I to be used according to the invention, group A is preferably phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 4-isobutylphenyl, 2,4-dimethylphenyl, 3,4 -Dimethyiphenyl, 2,5-dimethylphenyl, 2,4,5-trimethylphenyl, 2,4,6-trimethylphenyl,

Norbornan-2-yI or Pinan-3-yl, again preferably

at least one of the groups R ¹ to R ^{β is} methyl if A is phenyl or a monoalkyl-substituted phenyl. The following compounds of the formula I are particularly preferred as active substances against Gram-positive bacteria:

Among these particularly preferred compounds are 4- (2,4,5-trimethylphenyl) -2-butanol (compound 14), 3-methyl-4- (2,4,5-trimethylphenyl) -2-butanol (compound 4), 4- (4-isopropylphenyl) -3-methyl-2-butanol (Compound 11), 4- (4-isobutylphenyl) -3-methyl-2-butanol (Compound 6), 3-methyl-4- (2,4 , 6-trimethyIphenyl) -2-butanol

(Compound 8), 4- (3,4-dimethylphenyl) -3-methyl-2-butanol (Compound 17), 4- (3,4-dimethylphenyl) -2-butanol (Compound 18), 4- (2, 4- dimethylphenyl) -3-methyl-2-butanol (compound 12), 4- (2,4-dimethylphenyl) -2-butanol (compound 13), new. The mentioned antimicrobial properties of the secondary alcohols of the formula (I) to be used according to the invention relate to all diastereomeric and, if applicable, enantiomeric forms and any mixtures thereof.

The invention also relates to methods for controlling Gram-positive bacteria, the bacteria being contacted with an antimicrobially effective amount of a compound of the formula I or a mixture of at least two different compounds of the formula I. The compounds of the formula I mentioned above apply here Meanings of the substituents, the information relating to the particularly preferred compounds of the formula I of course also continuing to apply.

According to a related aspect, the invention also relates to a method for controlling (a) body odor caused by Gram-positive bacteria (b) impure skin and / or acne caused by Gram-positive bacteria and / or (c) bad breath caused by Gram-positive bacteria and / or bad breath, the Gram-positive bacteria being contacted with an antimicrobially effective amount of a compound of the formula I or a mixture of at least two different compounds of the formula I. The meanings of the substituents already mentioned at the outset and the explanations for those also apply preferred compounds of formula I.

For the purpose of contacting, the compound of the formula I is usually applied flat to the area of the skin (including the mucous membrane)

of the human and animal body, which is affected by the Gram-positive bacteria to be controlled. The form of application depends crucially on the dosage form of the compound of formula I to be used (see below). Although the method according to the invention will generally serve cosmetic purposes, there is also a therapeutic purpose in some cases. The term “control” encompasses both the treatment of existing impairments (in particular by undesirable, bacterially caused odors) and the corresponding prophylaxis.

The preparation of the secondary alcohols of the formula I to be used according to the invention in which R ¹ = H and m, n = 0 succeeds according to scheme 1.

Scheme 1

The preparation of the secondary alcohols of the formula (I) to be used according to the invention in which R ¹ = H; R ³ = H and m = 0.1, succeed according to scheme 2

Scheme 2

Hydrogenation / reduction

The preparation of the secondary alcohols of the formula (I) in which R ¹ = H; R ³ = H; R ⁵ = H, succeeds according to scheme 3

Scheme 3

An α, β-unsaturated ketone is first prepared by an aldol reaction of a suitable aldehyde with a methyl ketone (J. March, Advanced Organic Chemistry, 4 ed., J. Wiley, New York, 1992, pp. 937-944). In a subsequent step, the double bond and the keto group are hydrogenated. If necessary, only the double bond can be hydrogenated first and then the keto group can be reduced (J. March, Advanced Organic Chemistry, 4 * ¹ ed., J. Wiley, New York, 1992, pp. 771-783; 910-920). A suitable aldehyde is reacted in a Grignard reaction with a methyl magnesium halide (J. March, Advanced Organic Chemistry, 4 ^lh ed., J. Wiley, New York, 1992, pp. 920-931). If double bonds are present, the corresponding saturated compounds can be obtained by catalytic hydrogenation (Scheme 4).

Scheme 4

Preparations according to the invention, in particular cosmetic, oral hygiene and dermatological preparations, comprise an antibacterially effective amount of a compound of the formula I (the information above regarding the substituents and the preferred compounds correspondingly apply), and at least one further ingredient which is suitable for a z. B. cosmetic, oral hygiene or dermatological preparation is typical. In this context, with reference to EP 0919607 A2 already discussed, it should be pointed out that

that the preparations according to the invention cannot usually be used as a lubricant for the mechanical processing or processing of materials. In particular, the preparations according to the invention generally do not contain any corrosion inhibitor (organic boron compounds), no EP active ingredient (sulfur and phosphorus additives), no defoamer, no formaldehyde releaser and no boric acid

The compounds of formula I to be used according to the invention can also be used to prevent the spoilage of organic substances and preparations, in particular the spoilage of cosmetic, dermatological and oral hygiene preparations, by infestation with gram-positive bacteria. In a corresponding method according to the invention for preventing the If a cosmetic and therapeutic formulation is infected with gram-positive bacteria, the formulation is mixed with an antibacterially effective amount of one or more compounds of the formula I, the statements made above regarding the substituents and the compounds of the formula I to be used with preference apply accordingly. The compounds of the formula I are preferably used in a concentration of 0.05-10% by weight, based on the total mass of the substance or formulation.

As mentioned, the secondary alcohols of the formula (I) harmonize with a large number of customary cosmetic auxiliaries and additives, above all because the compounds of the formula (I) have no or only a very slight odor. This applies in particular to the formulations which are customary in deodorant or antiperspirant formulations

Perfume ingredients - The combination of astringents, predominantly aluminum salts such as aluminum hydroxychloride, with the antimicrobial substances according to the invention of the formula (I) in one and the same composition is also advantageous.

One or more antimicrobial compounds of the formula (I) can be used in preparations. The total content of secondary alcohols according to the invention is usually in the range from 0.005 to 50% by weight, preferably in the range from 0.01 to 20% by weight. , particularly preferably 0.1 to 5% by weight of the compounds according to the invention, and very particularly preferably 0.5 to 3% by weight, based on the total weight of the preparation.

The compounds of formula (I) are preferably used in cosmetic, oral hygiene or dermatological preparations. The compounds according to the invention can be incorporated without difficulty into common cosmetic, oral hygiene or dermatological preparations, advantageously in pump sprays, aerosol sprays, creams, ointments, tinctures, lotions, toothpastes, mouthwashes, tooth gels, nail care products (e.g. nail polishes, nail polish removers, nail balms) and the like -

The compounds according to the invention can also be microencapsulated, spray-dried, present as inclusion complexes or as extrusion products and used in this form and incorporated, for example, in formulations. If appropriate, the properties of the active compounds modified in this way can be modified by so-called "coating" with suitable materials a more targeted release can be further optimized, for which purpose wax-like plastics such as, for example, polyvinyl alcohol are preferably used. The microencapsulation of the active compounds can be carried out, for example, by the so-called coacervation process with the aid of capsule materials, for example made of polyurethane-like substances or soft gelatin

Spray drying of an emulsion or dispersion containing the active ingredient can be produced, whereby modified starches, proteins, dextrin and vegetable gums can be used as carriers. Inclusion complexes can e.g. by adding dispersions of the active ingredient and cyclodextrins or urea derivatives in a suitable solvent, e.g. Water. Extrusion products can be obtained by fusing the active ingredients with a suitable waxy substance and by extrusion with subsequent solidification, if appropriate in a suitable solvent, e.g. Isopropanol,

It is also possible and possibly advantageous to combine the compounds of the formula (I) to be used according to the invention with other cosmetic, oral hygiene and / or dermatological active substances, for example with other antimicrobial, antimycotic or antiviral substances.

Preparations according to the invention can contain auxiliaries of the kind normally used in cosmetic or therapeutic preparations, for example preservatives, abrasives, antibacterial agents, anti-inflammatory agents, anti-irritants, anti-irritants, antimicrobials, antioxidants, astringents, antiseptics, antistatic agents, binders, buffers, buffers, buffers, buffers. Carrier materials, chelating agents, cell stimulants, cleaning agents, caring agents, surface-active substances, deodorising agents, plasticizers, bactericides, emulsifiers, enzymes, essential oils, film formers, fixatives, foaming agents, foam stabilizers, substances for preventing foaming, foam boosters, gelling agents , moisturizing agents, moisturizing substances, moisturizing substances, bleaching agents, optically brightening agents, dirt-repellent agents, friction-reducing agents, lubricants, opacifiers, opaque agents, brighteners, polymers, powders, proteins, abrasives,

Silicones, skin soothing agents, skin cleansing agents, skin care agents, skin healing agents, cooling agents, skin cooling agents, warming agents, skin warming agents, stabilizers, UV absorbing agents, UV filters, suspending agents, thickening agents, vitamins, oils, waxes, fats, Phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, α-hydroxy acids, polyhydroxy fatty acids, plasticizers, dyes, color-protecting agents, pigments, flavors, flavorings, perfumes, fragrances or other common components of such preparations such as alcohols, polyols, electrolytes, organic solvents or Silikonderivate-

Fragrances and flavors that can be combined with the secondary alcohols of the formula (I) in cosmetic, oral hygiene or dermatological preparations can be found, for example, in Bauer, Garbe, Surburg, Common Fragrance and Flavor Materials, Wiley-VCH, 4th ed. , 2001 or in S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969, self-published.

Moreover, the preparations according to the invention can also UV absorbers (UV filters) such as Neo Heiiopane ^® contain such protection from sunlight. Suitable light stabilizers are, for example, organic UV absorbers from the class of 4-aminobenzoic acid and derivatives, salicylic acid derivatives, benzophenone derivatives,

Dibenzoylmethane derivatives, diphenylacrylates, 3-imidazol-4-yl-acrylic acid and their esters, benzofuran derivatives, benzylidene malonate derivatives, polymeric UV absorbers, containing one or more organosilicon residues, cinnamic acid derivatives, camphor derivatives, trianilino -s- triazine derivatives, 2-hydroxyphenylbenzotriazole derivatives, 2-

Phenylbenzimidazole-5-sulfonic acid and its salts, anthranilic acid menthyl ester, benzotriazole derivatives.

The list of UV absorbers mentioned below, which can advantageously be used in preparations according to the invention, is of course not intended to be limiting: 4-aminobenzoic acid, 4-aminobenzoic acid ethyl ester, 4-dimethylaminobenzoic acid 2-ethylhexyl ester, 4-aminobenzoic acid glycerol ester, salicylic acid homo- menthyl esters (homosalates), salicylic acid 2-ethylhexyl ester,

Triethanolamine salicylate, 4-isopropylbenzyl salicylate,

Anthranilsäurementhylester, ethyl diisopropyl cinnamate, 2-ethylhexyl p-methoxy cinnamate, methyl diisopropyl cinnamate, isoamyl p-methoxy cinnamate, di-ethanol amine p-methoxy cinnamate, 3,3-isano-ethyl-p-methoxy cinnamate, 2-isano-ethyl p-methoxy cinnamate Ethyl-2-cyano-3,3'-diphenyl acrylate, 2-phenylbenzimidazole-5-sulphonic acid and its salts, 3- (4'-trimethylammonium) -benzzylidenebornan-2-one-methylsulfate, terephthalylidene-dibornanesulfonic acid and salts , 4-t-butyl-4'-methoxy-dibenzoylmethane, ß-imidazole-4 (5) -acrylic acid (urocanic acid), 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, Di-hydroxy-4-methoxybenzophenone, 2,4-

Dihydroxybenzophenone, tetrahydroxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4-n-octoxy-benzophenone, 2-hydroxy-4-melhoxy-4'-methylbenzophenone, '37 (4 ' -Sulfo) benzyI-iden- bornan-2-one and its salts, 3- (4'-methylbenzylidene) camphor, 3-benzyl-idencampher, 3,3 '- (1,4-phenylenedimethine) -bis- (7, 7-dimethyl-2-oxo-bicyclo- [2.2.1] heptane-1-methanesulfonic acid and its salts, 4-isopropyldibenzoyl-methane, 2,4,6-trianilino- (p-carbo-2'-ethylhexyl-1 ' - oxy) -1, 3,5-triazine, phenylene-1, 4-bis- (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and its salts, especially the corresponding sodium, potassium or tri-ethanolamine Salts, in particular the disodium salt, 2,2 '- (1,4-phenylene) -bis- (1 H -benzimidazole-4,6-disulfonic acid), monosodium salt, N - [(2 and 4) - [2- ( oxobom-3-ylidene) methyl] benzyl] acrylamide polymer, phenol, 2- (2H-benzotriazol-2-yl) -4-methyl-6- (2-methyl-3 (1,3,3, 3-tetramethyl-1- (trimethylsilyl) oxy) disiloxyanyl) propyl), 4,4 '- [(6- [4- (1,1, dimethyl) aminocarbonyl) -

phenylamino] -1,3,5-triazine-2,4-diyl) diimino] bis (2-ethylhexyl benzoate), 2,2'-methylene-bis- (6- (2H-benzotriazol-2-yl ) -4-1, 1, 3,3-tetramethylbutyl) phenol), 2,4-bis- [4- (2-ethylhexyloxy) -2-hydroxyphenyl] - 1,3,5-triazine, benzylidene malonate polysiloxane, Glyceryl ethyl hexao-dimethoxy cinnamate, disodium 2,2'-dihydroxy-4,4'-dimethoxy-5,5'-disulfo-benzophenone, dipropylene glycol salicylate, sodium hydroxymethoxybenzophenone suifonate, 4,4 ', 4- (1 , 3,5-triazine-2,4,6-triyltriimino) tris-benzoic acid tris (2-ethylhexyl ester), 2,4-bis - [{(4- (2-ethylhexyloxy) -2-hydroxy} -phenyl] -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis - [{(4- (3-sulfonato) -2-hydroxypropyloxy) -2-hydroxy} phenyl ] -6- (4-methoxyphenyl) -1,3,5-triazine sodium salt, 2,4-bis - [{(3- (2-propyloxy) -2-hydroxy-propyloxy) -2-hydroxy} -phenyl] -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis - [{4- (2-ethylhexyioxy) -2-hydroxy} phenyl] -6- [4- (2-methoxyethylcarbonyl) phenyl amino] -1,3,5-triazine, 2,4-bis - [{4- (3- (2-propyloxy) -2-hydroxypropylox y) -2-hydro-xy} phenyl] -6- [4- (2-ethylcarboxyl) phenylamino] -1,3,5-triazine, 2,4-bis - [{4- (2-ethyl- hexyloxy) - 2-hydroxy} -phenyI] -6- (1-methyl-pyrrol-2-yl -) - 1, 3,5-triazine, 2,4-bis - [{4-tris (trimethylsiloxysilylpropylθ3ty ) -2-hydroxy} phenyl] -6- (4-methoxyphenyl) -1, 3,5-triazine, 2,4-bis - [{4- (2 "-methylpropenylθ55y) -2-hydroxy} phenyl] -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis - [{4-

(1 ', 1', 1 ', 3'5', 5 ', 5'-heptamethylsiloxy-2 "-methyl-propyloxy) -2-hydroxy} phenyl] -6- (4-methoxyphenyl) -1,3 , 5-triazine.

The amount of non-particulate UV absorber (one or more compounds) in preparations according to the invention is preferably 0.001 to 30% by weight. The total amount of filter substances is preferably 0.1 to 30% by weight, particularly preferably 0.2 to 10 % By weight, in particular 0.5 to 8% by weight, based on the total weight of the preparation.

In addition, particulate UV filters or inorganic pigments can be used, which can optionally be hydrophobized, such as the oxides of titanium (TiO ₂ ), zinc (ZnO), iron (Fe ₂ O ₃ ), zirconium (ZrO ₂ ), silicon (SiO ₂ ), manganese (for example MnO), aluminum (Al ₂ O ₃ ), cerium (for example Ce ₂ O ₃ ) and / or mixtures thereof.

Antioxidants suitable and / or customary for cosmetic and / or dermatological applications can be used in the preparations according to the invention.

The antioxidants are advantageously selected from the group consisting of amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-camosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. α-carotene, ß-carotene, lycopene) and their derivatives, lipoic acid and their derivatives (e.g. dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystine , Cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-lininoyl, choleεteryl and glyceryl esters) and their salts, Diiauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g. buthioninsulfoximines, homocysteine sulfoximines, buthioninsulfones, penta-, hexa-, heptoximinin), very achieve tolerable dosages (e.g. pmol to μmol / kg), also (metal) chelators (e.g. α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts , Bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g. γ-linolenic acid, linoleic acid, oleic acid), folic acid and their derivatives, ubiquinone and ubiquiole and their derivatives, vitamin C and derivatives (e.g.

Ascorbyl palmitate, Mg-Ascor byl phosphate, ascorbyl acetate), tocopherols and derivatives (e.g. vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) as well as konyferyl benzoate of benzoin, rutinic acid and its derivatives, ferulic acid and its derivatives, butylated hydroxytoluene, Bu- tylhydroxyanisole, nordihydroguajakh resinic acid, nordihydroguajaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (e.g. ZnO, ZnS0 ₄ ) selenium and its derivatives (e.g. selenomethionine), stilbenes and their derivatives (e.g. stilbene oxide), transbenzene and the derivatives suitable according to the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active substances mentioned. The above list is not limiting.

The amount of the antioxidants (one or more compounds) in preparations according to the invention is preferably 0.001 to 30% by weight, particularly preferably 0.05 to 20% by weight, in particular 1 to 10% by weight, based on the total weight of the preparation ,

If vitamin E and / or its derivatives represent the antioxidant (s), it is advantageous to choose their respective concentration from the range from 0.001 to 10% by weight, based on the total weight of the preparation.

If vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant or antioxidants, it is advantageous for their respective concentration to be in the range from 0.001 to 10% by weight, based on the total weight of the preparation , to choose. Examples of surface-active substances which can advantageously be used in preparations according to the invention are conventional soaps, for example fatty acid salts of sodium, alkyl sulfates, alkyl ether sulfates, alkane and alkylbenzenesulfonates, sulfoacetates, sulfobetaines, sarcosinates, amidosulfobetaines, sulfosuccinates, sulfosuccinic acid

haibester, alkyl ether carboxylates, protein-fatty acid condensates, alkyl betaines and amidobetaines, fatty acid alkanolamides, polyglycol ether derivatives.

The surface-active substance can be present in a concentration between 1% by weight and 50% by weight in the shampooing agent, or in the washing, showering or bathing preparation.

Cosmetic and dermatological preparations according to the invention can be in various forms, such as those e.g. are usually used for this type of preparation. So you can e.g. a solution, an emulsion of the type water-in-oil (W / O) or of the type oil-in-water (O / W), or a multiple emulsion, for example of the type water-in-oil-in-water (W / O / W), a gel, a hydro-dispersion, a solid stick or an aerosol

If the cosmetic or dermatological preparation according to the invention is a solution or lotion, the following can be used as solvents: water or aqueous solutions; Oils, such as triglycerides of capric or caprylic acid, but preferably castor oil; - Fats, waxes and other natural and synthetic fat bodies, preferably esters of fatty acids with alcohols with a low C number, for example with isoprapanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids with a low C number or with fatty acids; Alcohols, diols or polyols of low C number, and their ethers, preferably ethanol, isoprapanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether,

Propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and similar products.

Mixtures of the abovementioned solvents are used in particular. Water can also be a component of alcoholic solvents.

Preparations according to the invention are often preferably emulsions and contain e.g. the fats, oils, waxes and other fat bodies mentioned, and also water and an emulsifier, as is usually used for such a type of formulation.

Preparations according to the invention can be present as gels and then usually contain alcohols of low C number, e.g. Ethanol, isoprapanol, 1,2-propanediol, glycerol and water or an oil mentioned above in the presence of a thickener which is preferably silicon dioxide or an aluminum silicate in the case of oily-alcoholic gels, and is preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.

Cosmetic and dermatological preparations according to the invention can be present as gels which, in addition to at least one compound according to the invention and solvents usually used therefor, also include organic thickening agents, for example gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose or inorganic Thickeners, for example aluminum silicates such as bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate, are contained. The thickener is in the gel, for example, in an amount between 0.1 and 30% by weight, preferably between 0.5 and 15 % By weight.

Preparations according to the invention may be in the form of solid sticks and then contain e.g. natural or synthetic waxes, fatty alcohols or fatty acid esters. Lip care sticks and deodorant sticks ("deodorant sticks") are preferred.

Suitable blowing agents for cosmetic or dermatological preparations according to the invention which can be sprayed from aerosol containers are the customary known volatile, liquefied blowing agents, e.g. Hydrocarbons (propane, butane, isobutane) are suitable, which can be used alone or in a mixture with one another. Compressed air can also be used advantageously.

It is often advantageous to buffer preparations according to the invention. A pH range of 3.5 - 7.5 is advantageous. It is particularly favorable to choose the pH in a range from 4.0 to 6.5.

The cosmetic, oral hygiene and / or dermatological preparations according to the invention can be used to treat the skin, hair, teeth and oral mucosa in the sense of dermatological treatment or treatment in the sense of nourishing cosmetics. But they can also be used in make-up products in decorative cosmetics or in oral hygiene.

For use, the cosmetic, oral hygiene and / or dermatological formulations according to the invention are applied in a sufficient amount to the skin, teeth, gums and oral mucosa and tongue and / or hair in the manner customary for cosmetics and dermatics.

Oral hygiene products (oral hygiene preparations) in the present invention include the formulations familiar to the person skilled in the art for cleaning and maintaining the oral cavity and the

Throat cavity and breath freshening understood - Known and common oral hygiene formulations are creams, gels, pastes, foams, emulsions, suspensions, areosols, sprays as well as capsules, granules, lozenges, tablets, candies or chewing gums, without this list Dosage forms are limiting with regard to the possible uses. Such formulations serve to clean and care for tooth substance and oral cavity and to refresh the breath. If the secondary alcohols 10 of the formula (I) to be used according to the invention are incorporated into deodorants, these deodorants can be, for example, liquid as an aerosol spray, pump spray, gel, roll-on and the like or as a solid preparation, for example as a stick or powder available. Cosmetic and / or dermal tological preparations which are in the form of a sunscreen are also advantageous. These advantageously additionally contain at least one UVA filter and / or at least one UVB filter and / or at least one inorganic pigment. Preparations according to the invention for treating the hair are, for example, shampooing agents, preparations which are used when the hair is rinsed or after the shampooing, before or after the permanent wave treatment, before or after the coloring or decolorization of the hair, for preparations for blow-drying or inlaying the hair, preparations for coloring or decoloring, for a hairdressing and treatment lotion, a hair lacquer or around permanent wave products. In a preferred embodiment, the preparations are anti-dandruff agents, such as anti-dandruff shampoos.

Cosmetic preparations according to the invention which are a shampooing agent or a washing, showering or bathing preparation preferably contain at least one anionic, nonionic or amphoteric surface-active substance or mixtures thereof.

Is there a cosmetic or dermatological preparation according to the invention in the form of a lotion which is rinsed out and e.g. before or after decolorization, before or after shampooing, between two shampooing steps, before or after permanent wave treatment, these are e.g. aqueous or aqueous-alcoholic solutions, which may contain surface-active substances, preferably non-ionic or cationic surface-active substances, the concentration of which is between 0.1 and 10% by weight, preferably between 0.2 and 5% by weight, can lie. This cosmetic or dermatological preparation can also be an aerosol with the auxiliaries usually used for it.

A cosmetic preparation according to the invention in the form of a lotion that is not rinsed out, in particular a lotion for inlaying the hair, a lotion that is used for blow-drying the hair, a styling and treatment lotion, is generally an aqueous, alcoholic or aqueous-alcoholic Solution and contains at least one cationic, anionic, non-ionic or amphoteric polymer or mixtures thereof. Cosmetic and dermatological preparations according to the invention for the treatment and care of the hair can be present as emulsions which are of the non-ionic or anionic type. In addition to water, non-ionic emulsions contain oils or fatty alcohols, which can be polyethoxylated or polypropoxylated, for example, or also mixtures of the two organic components. This emul

Sions may contain cationic surface-active substances. Anionic emulsions are preferably of the soap type and contain at least one ethoxylated or propoxylated organic compound according to the invention with an anionic or non-ionic character.

The following examples are intended to illustrate the embodiments of the present invention. Percentages always refer to percentages by weight, unless other information is given. , Preparation of secondary alcohols of the formula I: 1.1 - (alkylphenyl) butan-2-o! E:

General rule:

290.4 g (5 mol) of acetone, 330 g of water and 13.3 g (0.33 mol) of sodium hydroxide are placed in a 2 l stirred flask. The aromatic aldehyde (2.5 mol) is dissolved in 100 g of acetone and metered in in 1 hour. After stirring for a further 90 minutes at 25 ° C., glacial acetic acid is neutralized and the excess acetone is distilled off at normal pressure. The residue is extracted twice with 200 ml of toluene. The organic phase is separated off and washed with water. The residue remaining after distilling off the toluene is distilled to isolate the 4- (alkylphenyl) -3-buten-2-one. 1 mol of the 4- (alkylphenyl) -3-buten-2-one obtained is in 300 ml of ethanol in the presence of 3% by weight of Raney nickel hydrogenated at a temperature of 20-40 ° C. and a hydrogen pressure of 10 to 20 bar. After the theoretically calculated amount of hydrogen has been taken up, the hydrogenation is terminated, the catalyst is filtered off and the batch is freed from the solvent. The 4 ~ (alkylphenyl) butan-2-ol obtained as a residue is purified by distillation.

1.2. 4- (alkylphenyl) -3-methyl-butan-2-o e!

General instructions: 433 g (6 mol) of methyl ethyl ketone and 1.5 mol of the aromatic aldehyde are placed in a 2-1 stirred flask and heated to 60.degree. 100 g of 50% strength sulfuric acid are metered in over a period of 1.5 hours. After stirring for 4-6 hours at 60-65 ° C., the mixture is cooled, neutralized with sodium bicarbonate solution and the excess methyl ethyl ketone is distilled off under normal pressure. The residue is extracted twice with 200 ml of toluene. The organic phase is separated off and washed with water. The residue which remains after the toluene has been distilled off is distilled to isolate the 4- (alkylphenyl) -3-methyl-buten-2-one - 1 mol of the 4- (alkylphenyl) -3- obtained. buten-2-one is hydrogenated in 300 ml of ethanol in the presence of 3% by weight of Raney nickel at a temperature of 180 ° C. and a hydrogen pressure of 10 to 20 bar. After the theoretically calculated amount of hydrogen has been taken up, the hydrogenation is terminated, the catalyst is filtered off and the batch is freed from the solvent. The 4- (alkylphenyl) butan-2-ol obtained as a residue is purified by distillation. In this way, for example, the following were obtained: a) 4- (2,4,5-trimethylphenyl) -2-butanol from 2,4,5-trimethylbenzaldehyde:

¹ H NMR (200 MHz; CDCI ₃ , δ ppm): 1.24 (d, J = 6.2 Hz, 3H), 1.62-1.75 (m, 2H), 2.19 (s, 6H), 2.25 (s, 3H), 2.50-2.76 (m, 2H), 3.77 (sext-, J = 6.2 Hz, 1H), 6.91 (s, 2H). ¹³ C NMR (200 MHz; CDCI ₃ , δ ppm): 18-6, 19.10, 19-18, 23-56, 29.03, 39.90, 67-83, 130-11, 131.51, 132.85, 133.74, 25 133.79, 137.33 , Odor: very low intensity; slightly reseda-like after styrolyl alcohol b) 3-methyl-4- (2-methylphenyl) -2-butanol from 2-methylbenzaldehyde:

¹ H NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.4: 1): 0.88 (d, J = 6.77 Hz, 3H), 1.21 (d, J = 6.38 Hz, 3H), 1.34 (d, J = 5.27 Hz, 1H), 1.70-1.88 (m, 1H), 2.29 (dd, J = 13.5 Hz, J = 9.74 Hz, 1H), 2.32 (s, 3H), 2.83 (dd, J = 13.5 Hz, J = 5.7 Hz, 1H), 3.71-3.85 (m, 1H), 7.10-7.14 (m, 4H). ³ C NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.4: 1): 13.59, 19.47, 19.56, 36.30, 40.27, 70.41, 125.77, 129.94, 130.12 (2C), 136.14, 139.16.

Smell: Almost odorless, slightly citrusy

c) 4- (4-isopropylphenyl) -3-methyl-2-butanol from 4-isoprapylbenzaldehyde:

¹ H NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.3: 1): 0.86 (d, J = 6.84 Hz, 3H), 1.21 (d, J = 6.39 Hz, 3H), 1.24 (d, J = 6.92 Hz, 6H), 1.70-1.88 (m, 1 H), 2.32 (dd, J = 13.4 Hz, J = 9.3 Hz, 1 H), 2.77 (hept., J = 6.98 Hz, 1H), 2.82 (dd, J = 13.4 Hz, J = 5.92 Hz, 1H), 3.62-3.92 (m, 1H), 7.0-7.20 (m, 4H). ¹³ C NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.3: 1): 13.62, 20.39, 24.04 (2C), 33.61, 38.79, 41.68, 70.21, 126.11, 126.13, 128.90 (2C), 138.27, 146.06 ,

Odor: Almost odorless, slightly watery-citric

d) 4- (4-isobutylphenyl) -3-methyl-2-butanol from 4-isobutylbenzaldehyde:

¹ H NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.07: 1): 0.86 (d, J

= 6.81 Hz, 3H), 0.89 (d, J = 6.6 Hz, 6H), 1.21 (d, J = 6.31 Hz, 3H), 1.70-1.88 (m, 1H), 1.70-1.95 (m, 1H), 2.32 (dd, J = 13.4 Hz, J = 9.3 Hz, 1H),

2.44 (d, J = 7.13 Hz, 2H), 2.78 (dd, J = 13.4 Hz, J = 9.4 Hz, 1H), 3.62-

3.92 (.1H), 7.0-7.20 (.4H). ¹³ C NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.07: 1): 13.56, 20.46, 22.36 (2C), 30.21, 38.88, 41.71, 44.99, 70.28, 128.70, 128.85, 128.86 (2C), 138.10 , 138.95. Odor: slightly rosy, citric e) 3-methyl-4- (2,4,5-trimethylphenyl) -2-butanoI from 2,4,5-trimethylbenzaldehyde:

Η NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.1: 1): 0.87 (d, J = 10 6.8 Hz, 3H), 1.22 (d, J = 6.3 Hz, 3H), 1.66 -1.88 (m, 1H), 2.20 (s, 9H), 2.2-2.3 (m, 1H), 2.6-2.8 (m, 1H), 3.70-3.82 (m, 1H), 6.8 (s, 1H), 6.9 (s, 1H). ¹³ C NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.1: 1): 14.64, 18.91, 19.19 (2C), 19.64, 35.84, 41.16, 71.77, 131.22, 131.52, 133.29, 133.38, 133.72, 136.37.

15 Odor: almost odorless, slightly flowery, cinnamon-like f) 3-methyl-4- (2,4,6-trimethylphenyl) -2-butanol from 2,4,6-trimethylbenzaldehyde:

20 H NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.1: 1): 0.86 (d, J = 6.9 Hz, 3H), 1.25 (d, J = 6.3 Hz, 3H), 1.70 -1.90 (m, 1H), 2.24 (s, 3H), 2.29 (s, 6H), 2.42 (dd, J = 13.6 Hz, J = 9.7 Hz, 1H), 2.8 (dd, J = 13 , 6 Hz, J = 9.7 Hz, 1H), 3.70-3.82 (m, 1H), 6.8 (s, 2H). ¹³ C NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.1: 1): 14.60, 20.34, 20.41 (2C), 20.75,

25 31.57, 40.81, 72.33, 128.85, 128.94, 134.78, 134.84, 136.47, 136.59.

Odor: slightly weakly fresh, celery 4- (3,4-dimethylphenyl) -3-methyl-2-butanol from 3,4-dimethylbenzaldehyde

¹ H NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.1: 1): 0.86 (d, J = 6.8 Hz, 3H), 1.19 (d, J = 6.41 Hz, 3H), 1.70 -1.86 (m, 1H), 2.23 (s, 6H), 2.33 (dd, J = 13.3 Hz, J = 8.8 Hz, 1H), 2.72-2.80 (m, 1H), 3.66-3.76 (m, 1H), 6.7-7.1 (m, 3H). ¹³ C NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.1: 1): 14.56, 19.27, 19.73, 20.36, 38.73, 41.73, 70.25, 126.38, 129.35, 130.34, 133.66, 136.13, 138.26.

Odor: Slightly rosy, somewhat lactonic h) 4- (3,4-dimethylphenyl) -2-butanol from 3,4-dimethylbenzaldehyde

¹ H NMR (200 MHz; CDCI ₃ , δ ppm): 1.22 (d, J = 6.1 Hz, 3H), 1.68-1.80 (, 2H), 2.22 (s, 3H), 2.23 (s, 3H), 2.45-2.80 (m, 2H), 3.82 (sext. J = 6.1 Hz, 1H), 6.90-7.10 (m, 3H). ³ C NMR (200 MHz; CDCI ₃ , δ ppm): 19.26, 19.72, 23.48, 31.61, 40.95, 67.43, 125.58, 129.50, 129.62, 133.72, 136.31, 139.33

Odor: Odorless i) 4- (2,4-Dimethylphenyi) -3-methyl-2-butanol from 2,4-

dimethylbenzaldehyde

¹ H NMR (200 MHz; CDCI ₃ , δ ppm, mixture of isomers 1.1: 1): 0.87 (d, J =

6.5 Hz, 3H), 1.22 (d, J = 6.3 Hz, 3H), 1.70-1.86 (m, 1H), 2.28 (s, 6H),

2.36 (dd, J = 13.4 Hz, J = 8.9 Hz, 1H), 2.86 (dd, J = 13.5 Hz, J = 8.9 Hz, 1H), 3.66-3.82 (m, 1H), 6.7-7.06 (m, 3H). ¹³ C NMR (200 MHz; CDCI3, δ

ppm, mixture of isomers 1.1: 1): 14.57, 19.44, 19.64, 20.86, 35.87, 40.97, 71.74, 126.19, 129.81, 130.95, 135.18, 136.00, 138.02.

Odor: almost odorless, uncharacteristic j) 4- (2,4-dimethylphenyl) -2-butanol from 2,4-dimethylbenzaldehyde

¹ H NMR (200 MHz; CDCI ₃ , δ ppm): 1.24 (d, J = 6.2 Hz, 3H), 1.65-1.75 (m, 2H), 2.28 (s, 6H), 2.45-2.80 (m, 2H), 3.86 (sext. J = 6.1 Hz), 6.90-7.10 (, 3H). ¹³ C NMR (200 MHz; CDCl ₃ , δ ppm): 19.16, 20.85, 23.53, 29.03, 39.69, 67.68, 126.48, 128.58, 130.89, 135.19, 135.54, 137.02. Smell: Almost odorless, uncharacteristic

2. WIHK values

2.1 Determination of the minimum inhibitory concentration

The minimum inhibitory concentration (MIC) of the claimed substances was determined in the serial dilution test (H. Brandis, G. Pulverer: Textbook of Medical Microbiology. 6th revised edition, Gustav Fischer Verlag Stuttgart, 1988; page 200ff.) Against various cosmetically relevant germs. The test was transferred to the microtiter plate format and the MIC value was used to determine the concentration at which no significant increase in turbidity compared to the controls was observed after 16 hours of incubation at the wavelength of 620 nm.

The results are shown in Table 2.

Table 2:

2.2 In-vitro test for bad breath reduction

The test is based on the work of Goldberg and Rosenberg (Production of Oral Malodor in an in vitro System, S. Goldberg and. Rosenberg, pp.143 - 150, in: Bad Breath- A multidisciplinary Approach, Eds: D. van Steenberghe, M. Rosenberg, Leuven University Press, 1996) and was adapted for better reproducibility.

A sterile liquid medium, which is inoculated with fresh morning saliva, is incubated for a few days in a Coy box at 37 "C and then smelled by an inspector panel.

An intense, typical bad breath has developed. Controls that have not been vaccinated have only a weak smell of media. As a control for the tests, Triclosan ^{® was added} in a concentration of 0.05%. The inoculated tubes had the same smell after incubation as the non-inoculated tubes.

The use of typical aroma substances for oral care applications, when using 0.1% concentrations in the test, usually showed a very unpleasant mixed smell, which came from the mixture

of the bad breath with the aroma substance - partly the aroma substance was no longer perceptible, since it was apparently broken down by the microorganisms of the saliva.

When using the substances described in Table 2, no odor similar to triclosan could be determined up to the specified minimum active concentrations.

Other flavorings known to be antimicrobial, such as eugenol and thymol, also suppressed bad breath formation at 0.1% use concentration, but had the disadvantage of the very distinct intrinsic odor.

Analogous to the MIC, the minimum active concentration (MWK) will silt up in the present case, at which the formation of bad breath is inhibited.

Table 3:

3. Formulation examples

Example 3.1 W / O cream

Paraffin oil 10.00 10.00 10.00

Ozokerite 4.00 4.00 4.00

Vaseline 4.00 4.00 4.00 vegetable oil 10.00 10.00 10.00

Wool wax alcohol 2.00 2.00 2.00

Aluminum stearate 0.40 0.40 0.40

4- (4-isopropylphenyl) -3-methyl-2- 1.00 - - butanol

4- (2,4,5-Trimethylphβnyl) -2-butanol 1.00

3-methyl-4- (2,4,6-trimethylphenyl) -2-1.00 butanol

Perfume, preservatives q.s. q.s. q.s.

Water, VES ad 100.00 ad 100.00 ad 100.00

Example 3-2 O W Lotion

Paraffin oil 5.00 5.00 5.00

Isopropyl palmitate 5.00 5.00 5.00

Cetyl alcohol 2.00 2.00 2.00

Beeswax 2.00 2.00 2.00

Ceteareth-20 2.00 2.00 2.00

PEG-20 glyceryl stearate 1.50 1.50 1.50

Glycerin 3.00 3.00 3.00

4- (4-isobutylphenyl) -3-methyl-2-butanol 1, 00

4- (4-tert-butylphenyl) -3-methyl-2- 1.00 butanol

3,3-dimethyl-4 (2,4,6-trimethylphenyl) -2- - 1.00 butanol

Perfume, preservatives qsqsqs water, VES ad 100.00 ad 100.00 ad 100.00

Example 3-3 O W Cream

Vegetable oil 10.00 10.00 10.00

Cetyl alcohol 2.00 2.00 2.00

Glycerol monostearate 1.50 1.50 1.50

PEG-30 glyceryl stearate 2.00 2.00 2.00

Glycerin 3.00 3.00 3.00

Isopropyl Palm Cat 5.00 5.00 5.00

Carbopol 980 (neutralized) 0.30 0.30 0.30

4- (4-isobutylphenyl) -3-methyl-2-butanol 1.00 - -

4-Bicyc! O [2.2.1] hept-2-yi-3-methyl-2- - 1.00 - butanol

4- (3,4-dimethylphenyl) -2-butanol 1.00 perfume, preservatives qsqsqs water, VES ad 100.00 ad 100.00 ad 100.00

Example 3-4 ointment

Vaseline 36.00 36.00 36.00

Ceresin 10.00 10.00 10.00

Zinc oxide 4.00 4.00 4.00

Vegetable oil 20.00 20.00 20.00

4- (2,4,5-trimethylphenyl) -2-butanol 0.02 - -

3-methyl- (2-methylphenyl) -2-butanol - 0.02 -

4- (4-tert-butylphenyl) -3-methyl-2-butanol - - 0.02

Perfume, preservatives q.s. q.s. q.s.

Paraffin oil ad 100.00 ad 100.00 ad 100.00

Example 3.5 Skin Oil

Cetyl palmitate 3.00 3.00 C12-15 alkyl benzoate 2.00 2.00 2.00 polyisobutene 10.00 10.00 10.00

Squalane 2.00 2.00 2.00

4- (2,4,5-trimethylphenyl) -3-methyl-2-0.50 butanol

4- (4-isobutylphenyl) -3-methyl-2-butanoi 0.50

3,3-dimethy-4-phenyl-2-butanol 0.50

Perfume, preservatives q.s. q.s. q.s.

Paraffin oil ad 100.00 ad 100.00 ad 100.00

Example 3.6 Lipstick

Ceresin 8.00 8.00 8.00

Beeswax 4.00 4.00 4.00

Carnauba wax 2.00 2.00 2.00

Vaseline 40.00 40.00 40.00

Hydrogenated castor oil 4.00 4.00 4.00

Caprylic / Capric Triglyceride 6.00 6.00 6.00

3-methyl-4- (2,4,5-trimethyl) -2-butanol 0.02

5,5-Dimethyi-6- (3-methylphenyl) -2-0.02 butanol

4- (4-isobutylphenyl) -3-methyl-2-butanol - - 0.02

Perfume, preservatives q.s. q.s. q.s.

Paraffin oil ad 100.00 ad 100.00 ad 100.00

Example 3-7 Care Mask

PEG-50 lanolin 0.50 0.50 0.50

Glyceryl stearate 2.00 2.00 2.00

Sunflower seed oil 3.00 3.00 3.00

Bentonite 8.00 8.00 8.00

Kaolin 35.00 35.00 35.00

Zinc oxide 5.00 5.00 5.00

3,3-dimethyl-4-phenyl-2-butaπol 1.00 - -

5,5-dimethyl-6- (3-methylphenyl) -2-hexanol - 1.00 -

3-methyl 4- (2,4-dimethylphenyl) -2-butanol - - 1.00

Perfume, preservatives q.s. q.s. q.s.

Water ad 100.00 ad 100.00 ad 100.00

Example 3-8

Shower preparation with moisturizer

Cocoamidodiacetate 10.00 10.00 10.00

Sodium lauryl sulfate 25.00 25.00 25.00

Potassium Cocyl Hydrolyzed Collagen 5.00 5.00 5.00

Macadamia nut oil 5.00 5.00 5.00

Sodium chloride 0.60 0.60 0.60

3-methyl-4- (2,4,6-trimethylphenyl) -2-butanol 0.30

4- (2,5-dimethylphenyl) -3,3-dimethyl-2--0.30 butanol

3-methyl 4- (3,4-dimethylphenyl) -2-butanol 0.30

Perfume, preservatives q.s. q.s. q.s.

Water ad 100.00 ad 100.00 ad 100.00

Example 3.9 Soap bar

Na salt from taig fatty acids 60.00 60.00 60.00 Na salt from coconut oil 28.00 28.00 28.00

Sodium chloride 0.50 0.50 0.50

4- (2,4,5-trimethylphenyl) -3-methyl-2- 1.00 butanol

4- (2,4,6-trimethylphenyl) -2-butanol - 1.00

3,3-dimethyl-4- (2,4,6-trimethylphenyl) -2- - - 1.00 butanol

Perfume, preservatives q.s. q.s. q.s.

Water ad 100.00 ad 100.00 ad 100.00

Example 3.10 Syndet soap

Sodium lauric isulfate 30.00 30.00 30.00

Sodium sulfosuccinate 10.00 10.00 10.00

Potassium cocoyl hydrolyzed collagen 2.00 2.00 2.00

Dimethicone Copolyol 2.00 2.00 2.00

Paraffin 2.00 2.00 2.00

Corn starch 10.00 10.00 10.00

Talcum 10.00 10.00 10.00

Glycerin 3.00 3.00 3.00

3-methyl- - (2,4,6-trimethylphenyl) -2-butanol 1, 00

4- (2,5-dimethylphenyl) -3,3-dimethyl-2- 1.00 butanol

3-methyl 4- (3,4-dimethylphenyl) -2-butanol - - 1.00

Perfume, preservatives q.s. q.s. q.s.

Water ad 100.00 ad 100.00 ad 100.00

Example 3.11

Hair care products I II III

TEA cocoyl hydrolyzed collagen 30.00 30.00 30.00

Monoethanolamine lauryl sulfate 25.00 25.00 25.00

Almond oil 2.00 2.00 2.00

Sodium chloride 1.00 1.00 1.00

4- (3,4-dimethylphenyl) -2-butanol 1.00 - -

4- (4-t-butylphenyl) -3-methyl-2-butanol - 1.00 -

4- (4-isobutylphenyl) -3-methyl-2-butanol - - 1.00

Perfume, preservatives q.s. q.s. q.s.

Water ad 100.00 ad 100.00 ad 101

Example 3.12

Care shampoo I II III

Sodium lauryl sulfate 34.00 34.00 34.00

Disodium lauryl sulfosuccinate 6.00 6.00 6.00

Cocoamidopropyl betaine 10.00 10.00 10.00

Glycol distearate 5.00 5.00 5.00

3-methyl- (4-methylphenyl) -2-butanol 0.02 - -

3-methyl- (2-methylphenyl) -2-butanol - 1.00 -

4-Bicydo [2.2.1] hept-2-yl-3-methyl-2- 1.00 butanol

Perfume, preservatives q.s. q.s. q.s.

Water ad 100.00 ad 100.00 ad 100.00

Example 3.13

Hair conditioner I II III

Cocoamidopropyl betaine 5.00 5.00 5.00

Cetyl alcohol 2.00 2.00 2.00

Propylene glycol 2.00 2.00 2.00

Citric acid 0.30 0.30 0.30

4-Bicyclo [2.2.1] hept-2-yl-2-butanol 1.00

4- (2,6,6-trimethylbicyclo [3.1.1] hept-3-yl) - 1.00 2-butanol

3-methyl-6-phenyl-2-hexanol 1.00

Perfume, preservatives q.s. q.s. q.s.

Water ad 100.00 ad 100.00 ad 100.00

Example 3.14 Hair Fixer

Polyvinylpyrrolidone / vinyl acetate / 5.00 5.00 5.00

Vinyl propionate copolymer

Ethanol 45.00 45.00 45.00

6- (4-isopropylphenyl) -3-methyl-2-hexanol 1.00

3,3-dimethyl-4-phenyl-2-butanol - 1.00

5,5-dimethyl-6- (3-methylphenyl) -2- - - 1.00 hexanol

Perfume, preservatives qsqsqs water ad 100.00 ad 100.00 ad 100.00

Example 3-15 Foot Cream

Soluan 5 2.00 2.00 2.00

Methyl salicylate 5.00 5.00 5.00

Caprylic / Capric Triglyceride 10.00 10.00 10.00

Stearic acid 5.00 5.00 5.00

Cetyl alcohol 1.00 1.00 1.00

Glycerin 2.00 2.00 2.00

Dimethicon 1.00 1.00 1.00

Carbopol 984 0.50 0.50 0.50

Triethanolamine 1.50 1.50 1.50

3-methyl-4- (2,4-dimethylphenyI) -2-butanol 1.00 - -

4- (2,4-dimethylphenyl) -2-butanol - 1.00 -

4- (2,4,5-trimethylphenyl) -2-butanol - - 1.00

Perfume, preservatives q.s. q.s. q.s.

Water ad 100.00 ad 100.00 ad 100.00

Example 3.16

Aerosol spray I II III

Octyldodecanol 0.50 0.50 0.50

3-methyl-4- (2,4,6-trimethylphenyl) -2-0.20 butanol

3-methyl-4- (3,4-dimethylphenyl) -2-butanol - 0.20

4- (2,5-dimethylphenyl) -3,3-dimethyl-2- - - 0.20 butanol

Perfume, preservatives q.s. q.s. q.s.

Ethanol ad 100.00 ad 100.00 ad 100.00

The liquid phase obtained by mixing the respective components together is filled into an aerosol container together with a propane-butane mixture (2: 7) in a ratio of 39:61.

Example 3-17

Pump spray I II III

PEG-40 hydrogenated castor oil 2.00 2.00 2.00

Glycerin 1.00 1.00 1.00

4- (3,4-dimethylphenyl) -2-butanol 0.20 4- (4-t-butylphenyl) -3-methyl-2-butanol 0.20 4- (4-isobutylphenyl) -3-methyl-2- butanol 0.20 perfume, preservatives qs q.s. q.s. Water ad 100.00 ad 100.00 ad 100.00

Example 3.18 Roll-on-Gel

1,3-butylene glycol 2.00 2.00 2.00

PEG-40 hydrogenated castor oil 2.00 2.00 2.00

Hydroxyethyl cellulose 0.50 0.50 0.50

4- (2,6,6-trimethylbicyclo [3.1.1] hept-3-yl) -2-0.30 butanol

4- (2,4,6-trimethylphenyl) -2-butanol - 0.30

4- (2,4,5-trimethylphenyl) -3-methyl-2-butaπol - 0.30

Perfume, preservatives q.s. q.s. q.s.

Water ad 100.00 ad 100.00 ad 100.00

Example 3.19

Gel toothpaste with effectiveness against bad breath I (%) II (%) IM (%)

Na carboxymethyl cellulose 0.40 0.40 0.40

Sorbitol, 70% 72.00 72.00 72.00

PEG 1500 3.00 3.00 3.00

Na saccharinate 0.07 0.07 0.07

Na fluoride 0.24 0.24 0.24

PHB ethyl ester 0.15 0.15 0.15

Aroma 1.0 1.00 1.00

3-methyl-6-phenyl-2-hexanol 0.50 1.50 3.00

Abrasive silica 11.00 11.00 11.00

Thickening silica 6.00 6.00 6.00

SDS 1.40 1.40 1.40

Distilled water Ad 100.00 Ad 100.00 Ad 10 (

Example 3.20

Toothpaste against PIaque with effectiveness against bad breath I (%) II (%) III (%)

Na carboxymethyl cellulose 1.00 1.00 1.00

Glycerin 86% 12.50 12.50 12.50

Sorbitol 70% 29.00 29.00 29.00

Na saccharinate 0.20 0.20 0.20

Na fluoride 0.22 0.22 0.22

AzacycIoheptan-2,2-diphosphonic acid, 1.00 1.00 1.00

Disodium salt (AHP)

Bromochlorophene 0.10 0.10 0.10

Aroma 1.10 1.10 1.10

3,3-Dimethy! -4-phenyl-2-butanol 0.50 1.50 3.00

Abrasive silica 15.00 15.00 15.00

Thickening silica 5.00 5.00 5.00

SDS 1.50 1.50 1.50

Distilled water Ad 100.00 Ad 100.00 Ad 101

Example 3.21

Carragenan 0.90 0.90 0.90

Glycerin 86% 15.00 15.00 15.00

Sorbitol 70% 25.00 25.00 25.00

I (%) II (%) III (%)

PEG 1000 3.00 3.00 3.00

Na fluoride 0.24 0.24 0.24

Tetra potassium diphosphate 4.50 4.50 4.50

Tefranosodium diphosphate 1.50 1.50 1.50

Na saccharinate 0.40 0.40 0.40

Precipitated silica 20.00 20.00 20.00

Titanium dioxide 1.00 1.00 1.00

PHB methyl ester 0.10 0.10 0.10

Aroma 1.10 1.10 1.10

3,3-dimethyl-4-phenyl-2- 0.50 1.50 3.00 butanol

SDS 1.30 1.30 1.30

Distilled water Ad 100.00 Ad 100.00 Ad 100.00

Example 3.22

Toothpaste for sensitive teeth with effectiveness against bad breath I (%) II (%) III (%)

Na carboxymethyl cellulose 0.70 0.70 0.70

Xanthan Gu 0.50 0.50 0.50

I (%) II (%) III (%)

Glycerin 86% 15.00 15.00 15.00

Sorbitol 70% 12.00 12.00 12.00

K-nitrate 5.00 5.00 5.00

Na monofluorophosphate 0.80 0.80 0.80

PHB methyl ester 0.15 0.15 0.15

PHB propyl ester 0.05 0.05 0.05

Na saccharinate 0.20 0.20 0.20

Aroma 1.00 1.00 1.00

4-bicyclo [2-2-1] hept-2-yl-2- 0.50 1.50 3.00 butanol

Ca carbonate 35.00 35.00 35.00

Silicon 1.00 1.00 1.00

SDS 1.50 1.50 1.50

Distilled water Ad 100.00 Ad 100.00 Ad 100.00

Example 3.23

Mouthwash with fluoride and effectiveness against bad breath I (%) II (%) III (%)

EthanoI 94.7% 7.00 7.00 7.00

Glycerin 86% 12.00 12.00 12.00

Na fluoride 0.05 0.05 0.05

Pluronic F-127 1, 40 1.40 1.40

Na phosphate buffer pH 7.0 1.10 1.10 1.10

Sorbic acid 0.20 0.20 0.20

Na saccharinate 0.10 0.10 0.10

Aroma 0.15 0.15 0.15

4- (2,4,5-trimethylphenyl) - 0.10 0.20 0.40

2-butanol

Dye 0.01 0.01 0.01

Distilled water Ad 100.00 Ad 100.00 Ad 100.00

Example 3.24

Bad breath chewing gum I (%) II (%) III (%)

Chewing gum base 21.00 21.00 21.00

Glucose syrup 16.50 16.50 16.50

Glycerin 0.50 0.50 0.50

Icing sugar 60.00 59.00 57.50

Aroma 1.50 1.50 1.50

3-methyl- (2- 0.50 1.50 3.00 methylphenyl) -2-butanol

Example 3-25

Sugar-free chewing gum for bad breath l (%) II (%) III (%)

Chewing gum base 30.00 30.00 30.00

Sorbitol powder. 38.00 37.00 35.50

Palatinite 9.50 9.50 9.50

Xyiite 2.00 2.00 2.00

Mannitol 3.00 3.00 3.00

Aspartame 0.10 0.10 0.10

Acesulfame K 0.10 0.10 0.10

Emulsifier / emulsifier 0.30 0.30 0.30

Sorbitol 70% 14.00 14.00 14.00

Glycerin 1.00 1.00 1.00

Aroma 1.50 1.50 1.50

6- (4-isopropylphenyl) -3- 0.50 1.50 3.00 methyl-2-hexanol

Example 3-36 "Water in Oil" Emulsion with UVA / B Broadband Protection

For part A, all substances except the zinc oxide were heated to 85 ° C. and the zinc oxide was carefully dispersed in the mixture. The components of Part B were mixed, heated to 85 ° C and added to Part A with stirring. Part C was added to the mixture of parts A and B and the mixture was then homogenized using a dispersing tool.

Claims

Expectations

1. Use of a compound of formula I.

as an active ingredient against Gram-positive bacteria, where m and n are independently 0 and 1,

R ¹ to R ^{6 are} independently hydrogen or methyl and

A is a phenyl group which is optionally substituted by further C to C ₅ alkyl substituents, a norboran-2-yI or a pinan-3-yl group.

2. Use according to claim 1, wherein at least one group R ¹ to R ⁶ present in the compound is methyl if A is a phenyl group or a monoalkyl-substituted phenyl group.

3. Use according to one of the preceding claims, wherein the gram-positive bacteria are selected from the group consisting of: (a) body odor causing, (b) impure skin and / or acne causing, (c) bad breath and / or bad Respiratory bacteria.

4. Use according to one of the preceding claims, wherein the Gram-positive bacteria are selected from the group of

Bacteria causing body odor, which consists of bacteria of the genera Corynebacterium, Staphyiococcus, Micrococcus and Brevibacterium, in particular Corynebacterium xerosis,

Staphylococcus epidermidis, Staphyiococcus hominis, Micrococcus luteus, Micrococcus sedentarius and Brevibacterium epidermidis.

5. Use according to one of claims 1-3, wherein the gram-positive bacteria are selected from the group of impure skin and / or acne-causing bacteria of the genus Propionibacterium, in particular Propionibacterium acnes.

6. Use according to any one of claims 1-3, wherein the gram-positive bacteria are selected from the group of bad breath and / or bad breath-causing bacteria of the genera Actinomyces, Eubacterium, Rothia and Stomatococcus, in particular Actinomyces viscosus, Eubacterium brachy, Eubacterium nodatum, Eubacterium saburreum, Eubacterium timidum Eubacterium yurrii, Rothia denticariosus and Stomatococcus mucilaginosus.

7. Use according to one of the preceding claims, wherein the following also applies to the compound of the formula I: m + n - = 0 or 2.

8. Use according to one of the preceding claims, wherein the compound of formula I has at least three CH ₃ groups.

9. A method for controlling Gram-positive bacteria, the bacteria being contacted with an antimicrobially effective amount of a compound of the formula I according to claim 1 or a mixture of at least two different compounds of the formula I according to claim 1.

10. A method for controlling (a) body odor caused by Gram-positive bacteria (b) impure skin and / or acne caused by Gram-positive bacteria and / or (c) bad breath and / or bad breath caused by Gram-positive bacteria, taking the gram-positive bacteria with an antimicrobial

effective amount of a compound of formula I according to claim 1 or a mixture of at least two different compounds of formula I according to claim 1 can be contacted.

11. 4- (2,4,5-Trimethylphenyl) -2-butanol (Compound 14), 3-methyl-4- (2,4,5-trimethylphenyl) -2-butanol (Compound 4), 4- (4 -Isopropylphenyl) - 3-methyl-2-butanol (compound 11), 4- (4-isobutylphenyl) -3-methyl-2-butanol (compound 6), 3-methyl-4- (2,4,6-trimethylphenyi ) -2-butanol (compound 8), 4- (3,4-dimethylphenyl) -3-methyl-2-butanol (compound 17), 4- (3,4-dimethylphenyl) -2-butanol (compound 18), 4- (2,4-dimethylphenyl) -3-methyl-2-butanol (compound 12), 4- (2,4-dimethylphenyl) -2-butanoI (compound 13).

12. A preparation comprising an antibacterially effective amount of a compound according to claim 11, and at least one further component.

13. A method for preventing the infestation of a cosmetic substance or formulation with gram-positive bacteria, the substance or formulation being mixed with an antibacterially effective amount of one or more compounds of the formula I according to claim 1.