(12) Patent Application Publication (10) Pub. No.: US 2015/0118173 A1 Farwick Et Al

Home , Aluminium diacetate, Sodium alum

US 2015O1 18173A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0118173 A1 Farwick et al. (43) Pub. Date: Apr. 30, 2015

(54) FORMULATION COMPRISING CAPRYLIC (30) Foreign Application Priority Data ACD ETHANOLAMIDE AND/OR CAPRIC ACD ETHANOLAMIDE IN COMBINATION Apr. 27, 2012 (DE) ...... 102O122069992 WITH AN ALUMNIUM SALT AND ITS USE Publication Classification (71) Applicant: EVONIK INDUSTRIES AG, Essen (DE) (51) Int. Cl. A61O 1700 (2006.01) (72) Inventors: Mike Farwick, Essen (DE); Oliver A61O5/00 (2006.01) Springer, Wesel (DE); Matthias A61O 15/00 (2006.01) Mentel, Dortmund (DE); Stefan A61O 19/00 (2006.01) Bergfried, Essen (DE) A618/26 (2006.01) A618/42 (2006.01) (73) Assignee: EVONIK INDUSTRIES AG, Essen (52) U.S. Cl. (DE) CPC ...... A61O 17/005 (2013.01); A61K 8/26 (2013.01); A61K 8/42 (2013.01); A61O 15/00 (21) Appl. No.: 14/397,379 (2013.01); A61O 19/00 (2013.01); A61O5/006 (2013.01); A61 K 2800/5922 (2013.01) (22) PCT Filed: Mar. 28, 2013 (57) ABSTRACT (86) PCT NO.: PCT/EP2013/056670 The invention relates to a formulation comprising caprylic S371 (c)(1), acid ethanolamide and/or capric acid ethanolamide in com (2) Date: Oct. 27, 2014 bination with an aluminium salt and to its use. Patent Application Publication Apr. 30, 2015 Sheet 1 of 3 US 201S/O118173 A1

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XYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYY MEA 2% is ACH 2% & MEA 2+ACH 2% Figure 1 Patent Application Publication Apr. 30, 2015 Sheet 2 of 3 US 201S/O118173 A1

Patent Application Publication Apr. 30, 2015 Sheet 3 of 3 US 201S/O118173 A1

Figure 3 US 2015/01 18173 A1 Apr. 30, 2015

FORMULATION COMPRISING CAPRYLC regards its antimicrobial effect, in particular on the skin of ACD ETHANOLAMIDE AND/OR CAPRIC living beings and thus in particular for use in cosmetic appli ACIDETHANOLAMIDE IN COMBINATION cations. WITH AN ALUMNIUM SALT AND ITS USE DESCRIPTION OF THE INVENTION FIELD OF THE INVENTION 0010 Surprisingly, it has been found that the combination 0001. The invention relates to a formulation comprising described below of caprylic acid ethanolamide and/or capric caprylic acid ethanolamide and/or capric acid ethanolamide acid ethanolamide (C8- or 10-MEA) with ACH has a syner in combination with an aluminium salt and to its use. gistic effect in deodorant applications. 0011. The present invention therefore provides formula PRIOR ART tions comprising at least one compound of the general for 0002 Antimicrobial active ingredients are used widely in mula (I) cosmetic deodorants or antiperspirants, antidandruff and antiacne formulations, footcare and intimate hygiene compo sitions and also oral hygiene and dental care products. formula (I) 0003 Body odour is formed primarily when the initially odourless perspiration is decomposed by microorganisms on --~-l. the skin. Only the microbial degradation products cause the H unpleasant Sweat odour. This arises in particular wherever there is a high density of Sweat glands and also a high density of odour-producing microbes, such as for example in the where armpits, in intimate areas or on the feet. The microbes respon sible for this, however, often do not belong exclusively to the R'—C, His or—CoHo genus Corynebacterium. 0012 and an aluminium salt. 0004 Our natural skin flora includes many different bac 0013 The invention further provides the use of the formu teria, including staphylococci, certain streptococci, occasion lation according to the invention for reducing the growth of ally enterococci, corynebacteria and propionibacteria. They microorganisms, in particular on a Surface, and also for reduc live on the skin, sometimes in the pores, in Sweat glands and ing human body odour. Sweatducts, and also in the oral cavity. A variety of fungi also 0014. It is an advantage of the present invention that the occur on the skin. formulations are stable in nonpolar and polar (in particular 0005 Certain skin disorders are also connected with alcoholic or aqueous) systems since no hydrolysis or alco excessive growth of undesired microorganisms on the skin. holysis take place under the required conditions. Thus, acne interalia is caused by uncontrolled multiplication 0015. It is also an advantage that the effectiveness is of the anaerobic skin bacterium Propionibacterium acnes. largely constant over the entire pH range of the possible Candida albicans is responsible for the formation of thrush, cosmetic formulations. dandruff is associated interalia with the fungus Pilz. Malasse 0016. It is a further advantage that the formulations have Zia furfur: good skin compatibility. 0006. In the area of oral hygiene, microorganisms play an 0017. It is another advantage that they contribute to reduc essential role e.g. in the formation of caries and plaque. The ing the ACH content in antiperspirants. most important cause of dental caries is for example Strepto 0018. The use according to the invention, in cases where it COCC tiS initita F2S. is a use on a living species, is exclusively a cosmetic and a 0007. The most important strategies for controlling body non-therapeutic use. odour are odour masking (by means of fragrances), odour 0019. Unless stated otherwise, all of the stated percent absorption, control of the microorganisms involved in odour ages (%) are percentages by mass. In connection with the formation by means of antimicrobial Substances, and the present invention, the term “aluminium chlorohydrate' is influencing of the sebaceous gland activity by means of anti understood as meaning the salts of the general empirical perspirants. Of particular importance here are antiperspirants formula AlCl(OH), in particular AlCl(OH)s. containing aluminium chlorohydrate (ACH), although these 0020 Preference is given in particular to formulations have the disadvantage that they leave behind traces of use on according to the invention which are characterized in that the clothing. aluminium salt is selected from the group comprising, pref 0008 WO2011032924 describes the use of certain amides erably consisting of including caproic acid isopropanolamide, caprylic acid iso aluminium acetate, aluminium behenate, aluminium ben propanolamide, capric acid isopropanolamide, lauric acid Zoate, aluminium bromohydrate, aluminium butoxide, alu isopropanolamide, caprylic acid monoethanolamide, minium calcium Sodium silicate, aluminium caprylate, alu caprylic acid diethanolamide and caprylic acid N-methyl minium capryloyl hydrolyzed collagen, aluminium chloride, ethanolamide for reducing the growth of microorganisms and aluminium chlorohydrate, aluminium chlorohydrex, alu as a constituent of cosmetic formulations and proposes, minium chlorohydrex PEG, aluminium chlorohydrex PG, among many other compounds which can additionally be aluminium citrate, aluminium diacetate, aluminium diben co-used, also aluminium salts such as aluminium chlorohy Zoate/stearate hydroxide, aluminium dicetyl phosphate, alu drate, aluminium zirconium tetrachlorohydrex GLY, alu minium dichlorohydrate, aluminium dichlorohydrex PEG, minium Zirconium pentachlorohydrate and alum. aluminium dichlorohydrex PG, aluminium dilinoleate, alu 0009. It was an object of the invention to provide an active minium dimyristate, aluminium distearate, aluminium glyci ingredient combination which has excellent properties as nate, aluminium hydrogenated tallow glutamate, aluminium US 2015/01 18173 A1 Apr. 30, 2015 hydroxy bis-methylene bis-di-t-butylphenyl phosphate, alu self-tanning compositions, foot lotion, foot spray, body minium iron calcium magnesium germanium silicates, alu lotion, body gel, body spray, body milk, body Scrub, body oil, minium iron calcium magnesium Zirconium silicates, alu body butter. minium iron silicates, aluminium isopropoxide, aluminium 0023 Examples of lipcare products are lip balm, lip isostearate, aluminium isoStearates/laurates/palmitates, alu cream, lipcare stick. minium isostearates/laurates/stearates, aluminium isostear 0024. The cosmetic or pharmaceutical formulations ates/myristates, aluminium isostearates/palmitates, alu according to the invention can contain e.g. at least one addi minium isoStearates/stearates, aluminium isostearyl glyceryl tional component, selected from the group of phosphate, aluminium laccate, aluminium lactate, aluminium emollients, lanolate, aluminium/magnesium hydroxide Stearate, alu emulsifiers, minium magnesium oxide, aluminium methionate, alu thickenerS/viscosity regulators/stabilizers, minium myristate, aluminium myristates/palmitates, alu UV light protection filters, minium PCA, aluminium phenolsulphonate, aluminium antioxidants, sesquichlorohydrate, aluminium sesquichlorohydrex PEG, hydrotropes (or polyols), aluminium sesquichlorohydrex PG, aluminium starch octe solids and fillers, nylsuccinate, aluminium Stearate, aluminium Stearates, alu film formers, minium Stearoyl glutamate, aluminium Sucrose octasulphate, pearlescent additives, aluminium Sulphate, aluminium triformate, aluminium triph deodorant and antiperspirant active ingredients, osphate, aluminium tristearate, aluminium undecylenoyl col insect repellents, lagen amino acids, aluminium Zinc oxide, aluminium Zirco Self-tanning agents, nium trichlorohydrate, aluminium Zirconium trichlorohydrex preservatives, GLY, aluminium Zirconium tetrachlorohydrate, aluminium conditioners, zirconium tetrachlorohydrex GLY, aluminium zirconium tet perfumes, rachlorohydrex PEG, aluminium zirconium tetrachlorohy dyes, drex PG, aluminium Zirconium pentachlorohydrate, alu minium Zirconium pentachlorohydrex GLY, aluminium odour absorbers, Zirconium octachlorohydrate, aluminium Zirconium cosmetic active ingredients, octachlorohydrex GLY ammonium alum, ammonium silver care additives, Zinc aluminium silicate, calcium aluminium borosilicate, Superfatting agents, cobalt aluminium oxide, magnesium/aluminium/hydroxide/ Solvents. carbonate, magnesium aluminium silicate, magnesium/alu 0025. Substances which can be used as exemplary repre minium/zincfhydroxide/carbonate, potassium alum, potas sentatives of the individual groups are known to the person sium aluminium polyacrylate, silver magnesium aluminium skilled in the art and can be found for example in the German phosphate, sodium alum, Sodium aluminate, sodium alu application DE 102008.001788.4. This patent application is minium chlorohydroxy lactate, Sodium/aluminium hydrox hereby incorporated by reference and thus forms part of the ide/oxalate? Sulphate, Sodium/aluminium/iron hydroxide/ox disclosure. alate? sulphate, Sodium/aluminium/iron/sulphate/citrate/ 0026. For cases of using the formulation according to the hydroxide, Sodium/aluminium/iron/Sulphate/oxalate/ invention on inanimate surfaces, said formulations are in hydroxide, Sodium/aluminium/iron/sulphate?tartarate/ particular cleaning and care compositions for domestic, hydroxide, sodium aluminium lactate, sodium phosphorus/ industrial and institutional applications such as, for example, Zinc? calcium/silicon/aluminium/silver oxides, sodium disinfectants, disinfectant cleaners, foam cleaners, floor potassium aluminium silicate, sodium silicoaluminate, cleaners, carpet cleaners, upholstery cleaners, floor care Sodium silver aluminium silicate, tromethamine magnesium products, marble cleaners, parquet cleaners, stone and aluminium silicate and alum, in particular aluminium chlo ceramic floor cleaners, wipe-care products, stainless steel rohydrate. cleaners, glass cleaners, dishwashing detergents, plastic cleaners, sanitary cleaners, wood cleaners, leather cleaners, 0021 Preference is given to formulations according to the laundry detergents, laundry care compositions, disinfectant invention which are cosmetic or pharmaceutical formula detergents, heavy-duty detergents, gentle detergents, wool tions. detergents, fabric conditioners, impregnation compositions. 0022 Cosmetic or pharmaceutical formulations accord 0027. It is obvious that mixtures of compounds of the ing to the invention can be used as skincare, face care, head general formula (I) can be present in formulations according care, bodycare, intimate care, footcare, haircare, nailcare, to the invention. It is advantageous if such a formulation is dental care, lip care or oral care product or antiperspirant/ characterized in that mixtures of compounds are present in deodorant product. Examples of haircare products are hair which the weight ratio of compounds of the general formula washing compositions, hair treatments, hair conditioners, (I) with an R= -CHs to compounds of the general formula hair fluid, hair gel, hair tonic, hair wax, hair lacquer, hair (I) with an R= -CH is in a range from 5:95 to 95.5, spray, hair cream, hairmousse, hair balm, antidandruff sham particularly preferably from 35:65 to 65:35. poo. Examples of bodycare products are shower bath, cream 0028. However, it has been found that the presence of a bath, cream gel, shower oil, shower gel, washing gel, washing high fraction of compounds similar to the compounds of the scrub, cleansing lotion, face mask, facial toner, facial Scrub, general formula (I), characterized by an R with a chain other eye cream, night cream, cleansing mask, lotion pads, cleans than —CHs or —CH has a negative influence. ing wipes, cleansing lotion, cleansing milk, cleansing gel. 0029 Consequently, preferred formulations according to aftershave gel, aftershave balm, Sun milk, afterSun products, the invention are characterized in that, in the formulation, less US 2015/01 18173 A1 Apr. 30, 2015

than 80% by weight, preferably less than 40% by weight, in 0036. The formulations according to the invention can particular less than 20% by weight, of compounds of the also be used in the sector of oral hygiene products, in which general formula (II) case use in mouthwash solutions or toothpastes is recom mended in particular. 0037. They can also be used in combination with other formula (II) O active ingredients which have effectiveness gaps in areas in which the formulations according to the invention are effec OH tive for said purpose. Thus, the use of preservatives can be --~H s reduced or in some cases it is even possible to completely dispense with classical preservatives. where 0038. The invention further provides the use of at least one R’-organic radical with a chain length of less than 7 or of the formulations according to the invention for reducing greater than 9, based on the total weight of the compounds of the growth of microorganisms. the general formula (I) and (II) are present. 0039. As a result of the use according to the invention of 0030. In this connection, RandR of the general formula the formulations according to the invention, it is possible for (I) and (II) are independent of one another, R and R2 in the example to reduce the number of microorganisms in the for general formula (I) and (II) preferably being identical. mulation itself. This corresponds to the basic concept of a 0031 Preferably formulations according to the invention preservative. are in particular characterized in that they comprise 0.001% 0040. However, the use according to the invention is pref by weight to 20% by weight, preferably 0.01% by weight to erably carried out on a surface. Preferably, the surface in the 10% by weight, particularly preferably 0.1% by weight to 5% use according to the invention is the Surface of a human or by weight, of at least one compound of the general formula animal body part, in particular the skin, the hair or the teeth, (I), based on the total formulation. with use on the skin being particularly preferred. 0032 Formulations according to the invention are in par ticular characterized in that they comprise 0.01 to 50% by 0041. These surfaces generally have undesired microor weight, preferably 0.1% by weight to 35% by weight, par ganisms such as, for example, bacteria, specifically Coryne ticularly preferably 1.0% by weight to 20% by weight, of at bacterium xerosis, Corynebacterium jeikeium, Corynebacte least one aluminium salt, based on the total formulation. rium minutissinum, Propionibacterium aCneS, 0033. The formulations according to the invention can be Staphylococcus aureus, Staphylococcus epidermidis, Strep used as a multitude of formulations for applications in the tococcus sobrinus and Streptococcus mutans. Fungi (includ home, industry, pharmacy and cosmetics. They are particu ing yeasts) likewise also occur here, thus for example repre larly suitable as effective components in deodorants, which sentatives of the genera Microsporum, Epidermiphyton, may be present in the form of aerosol sprays, pump sprays, Trichphyton, and also Candida albicans or Malassezia firfir: roll-on formulations, deodorant sticks, W/O or O/W emul 0042 Consequently, a use characterized in that the micro sions (e.g. creams or lotions) or wipes. The active ingredients/ organisms are Gram-positive, in particular coryneform, bac active ingredient combinations known from the prior art can teria, and in particular likewise the aforementioned species. be co-used in these formulations, such as e.g. triclosan, eth ylhexylglycerol, farnesol, polyglycerol caprate or caprylate, 0043. In a further preferred embodiment of the use accord triethyl citrate, penta(carboxymethyl)diethylenetriamine ing to the invention, the Surface on which the use takes place (pentetic acid), pentylene glycol, propylene glycol, ethanol, is the Surface of an inanimate object. Examples of Such Sur Zinc ricinoleate, cyclodextrins, silver and its salts or Zinc faces are surfaces of tiles, wood, glass, ceramic, linoleum, oxide. plastic, painted surfaces, leather, materials, fibres. Preferably, 0034. However, application is not limited to use in deodor Such objects come into daily contact several times directly or ants, but may be advantageous wherever it is desirable to indirectly through people or animals. Preferably, the surface control microorganisms or their growth, Such as e.g. in inti of Such objects experiences Soiling as a result of the afore mate hygiene articles, antiacne or antidandruff products, mentioned contact. Examples of Such objects are which can be present in the form of customary leave-on or window panes and windowsills, shower partitions, rinse-off formulations, such as e.g. creams, lotions, sham floorings Such as carpets, tiles, laminates, parquet, cork floor poos, washing solutions, hair conditioners, wipes and similar formulations. Use of the formulations according to the inven ings, marble, Stone and fine Stoneware floors tion in footcare compositions is also advantageous; footcare household ceramics Such as toilets, wash basins, bidets, compositions are understood as meaning not only composi showertrays, bathtubs, door handles, fittings, tions that are to be applied directly to the skin, but the term domestic appliances such as washing machines, dryers, dish likewise encompasses for example deodorizing shoe insoles. washers, sinks made of ceramic or stainless steel, furniture 0035. For antiacne products, the formulations according Such as tables, chairs, benches, work Surfaces, to the invention can optionally also comprise known antiacne active ingredients, such as e.g. dibenzoyl peroxide, salicylic windows, pots and pans, crockery and cutlery, acid, phytosphingosine, tretinoin, isotretinoin or plant laundry, in particular laundry worn close to the body (“under extracts. Similarly, in the case of antidandruff products, com wear binations with known antidandruffactive ingredients, such as e.g. climbazole, Zinc pyrethione, selenium compounds (for watercraft, vehicles and aircraft, such as cars, buses, motor example selenium Sulphide), piroctone olamine (octopiroX) boats and sail boats or plant extracts, can be used. tools such as Surgical instruments, vacuum cleaners. US 2015/01 18173 A1 Apr. 30, 2015

0044 Engines, pipelines, tanks and devices for transpor 0053 FIG. 3: parameter L* in the CIELAB colour space. tation, processing and storage in food processing. On the left deodorant stick test formulation A, on the right 0045 Consequently, in this connection, it is the use of the deodorant stick test formulation B. compounds of the general formula (I) in cleaning and care compositions for domestic, industrial and institutional trade. EXAMPLE 1. 0046. The invention also further provides the use of at least Effectiveness Testing of the Sweat-Odour-Inhibiting one formulation according to the invention for reducing Effect human body odour. 0054 The study was carried out in the “Incomplete Block 0047. The invention also further provides the use of at least design, randomized and double-blind. Two products were one formulation according to the invention for reducing the applied for each subject (half-side test) under the armpits in whitening effect. As a comparison formulation to which the the form of a pump spray. Three professional Sniffers carried reduced whitening effect refers, a formulation based only on out the evaluations. The group of subjects comprised 50 the aluminium salt is used in particular which, in quantitative healthy volunteers, 33 female and 17 male aged from 20 to 65 terms, has the same Sweat-odour-inhibiting effect as the whit years with a detectable body odour under the armpits. The ening-effect-reduced formulation. Subjects were committed to only wearing clothing made of 0.048 Among the uses according to the invention, in each pure cotton. The clothing, which was worn throughout the case preference is given to using those formulations which are study, was not allowed to have been treated with perfumed specified above as preferred formulations. detergents or fabric softeners. The study took place in the 0049. The invention further provides a method for reduc month of August. ing the growth of microorganisms, involving the steps 0055. During a preconditioning phase of ten days, the a) provision of a formulation according to the invention, in Subjects were committed to using only a nonperfumed Soap particular of a cosmetic or pharmaceutical formulation, without antibacterial ingredients for cleaning their armpits. The cleaning of the armpits was carried out in accordance b) application of the formulation to the surface to be treated, with a stipulated procedure for a period of 30 seconds. in particular skin, hair or teeth, in an effective amount, 0056. During the main phase, the application of the test c) leaving the formulation on the surface to be treated for a products was carried out after drying the armpits in a stan time which suffices to ensure the reduction in the growth of dardized form and with a defined amount of 5 pump strokes the microorganisms and (ca. 0.7–0.8 g). Each subject applied two test products, one d) optionally washing out or rinsing off the formulation. under the right armpit and one under the left armpit. 0050. The examples given below describe the present 0057 The evaluation was carried out during the main invention by way of example without intending to limit the phase by three trained testers in each case six hours after the invention, the scope of application of which arises from the last washing operation (starting value) and six hours after a entire description and the claims, to the embodiments speci single application of the test products. TABLE 1. Clear deodorant pump spray test formulations. Data in mass percent. To produce the formulations, customary formulation processes known to the person skilled in the art were used. MEA 2% -- Raw material Vehicle MEA 2% ACH2% ACH2% A TEGO (R) Alkanol L 23 P (Laureth-23) 2.0% 2.0% 2.0% 2.0% TAGAT (R) CH40 (PEG-40 2.0% 2.0% 2.0% 2.0% Hydrogenated Castor Oil) Water 94% 92% 90% 88% Propylene Glycol 2.0% 2.0% 2.0% 2.0% B Caprylicicapric acid ethanolamide 2.0% 2.0% (50% in Propylene Glycol) Aluminium Chlorohydrate (50% in 2.0% 2.0% Water) C Citric Acid (10% in Water) pH 4.5 pH 4.5 pH 4.5 pH 4.5 fied in the examples. The following figures form part of the 0.058 The degree of Sweat odour was evaluated using a examples. scale from Zero to five (0=not perceptible, 1 =very slight, 0051 FIG. 1: effect on odour after six hours of the formu 2=slight, 3-distinct, 4-strong, 5–very strong). Perceptible lation according to the invention compared to individual com differences by comparison between the right and the left ponents. In each case, the change relative to vehicle formu lation is shown. The results for all test products were armpits were assessed with a difference of at least one value normalized beforehandby deducting the starting value (Sweat on the evaluation scale. odour without treatment). 0059. The olfactory assessment takes place six hours after 0052 FIG. 2: photographic documentation of the whiten a single product application. All evaluations were carried out ing effect after converting the RGB colour image into a binary in a specially climatized room, as a result of which a constant (black-white) image. Left: formulation A, right: formulation atmosphere with a room temperature of 22+1° C. and relative B. atmospheric humidity of 50+5% was ensured. US 2015/01 18173 A1 Apr. 30, 2015

0060. As the study showed, a reduction in the Sweat odour Multi Probe Adapter System MPA (Courage+Khazaka Elec compared with the vehicle formulation could be achieved tronic GmbH) were used to determine the parameter L* in the after a single application of the test products. The decrease in CIELAB colour space. The parameter L* indicates the light sweat odour is lowest (-0.11) in the group which applied ness and has the end points black (L=0) and white (L=100). “ACH 2%', whereas the decrease in Sweat odour was more The parameter L* was determined in each case by ten-fold marked (-0.22) in the “MEA 2% group. By combining measurement at various points of the deodorant Stick test identical concentrations of the two active ingredients, a formulation applied to the foam rubber. The average values of reduction in Sweat odour was observed in the "MEA these ten measurements are given in each case. 2%+ACH 2% group which was more marked (-0.41) than one would have expected from the sum of the individual 0065. As the photographic documentation (FIG. 2) shows, effects (-0.22+-0.11=-0.33). Consequently, by combining the whitening effect after a two-fold spreading of the deodor the two active ingredients “MEA 2% and “ACH 2%, an ant sticks was reduced if some of the aluminium salt in the unforeseeable and Surprising synergy effect was found. deodorant stick test formulation is replaced with caprylic/ capric acid ethanolamide. EXAMPLE 2 0066. Likewise, by measuring the lightness (L*) of the deodorant stick test formulations applied to the foam rubber, Reduction in the Whitening of Aluminium it could be shown that the formation of white deodorant traces Salt-Containing Deodorant Care Products is reduced (FIG. 3). 0061. After applying deodorant care products, in particu 0067 Consequently, a reduced whitening effect was lar aluminium salt-containing deodorant care products, very achieved by replacing some of the aluminium salt with often white traces on skin and clothing are detected by the caprylic/capric acid ethanolamide. consumer. These white traces are mostly perceived as annoy ing and there are therefore efforts to reduce the whitening effect after applying deodorant care products. One approach Example Formulations here is the reduction of aluminium salt-containing compo nents in the deodorant care formulation with a constant or 0068 Example Formulation PEG-Free Deodorant Roll even improved effectiveness of the product. O 0062. The aim was therefore to investigate whether by Swapping aluminium salts with caprylic/capric acid ethano lamide in a deodorant Stick formulation it is possible to reduce Raw material Percent by mass TEGO (R) Care PS (Methyl Glucose 1.75 the formation of white traces after applying the deodorant Sesquistearate) Stick, in particular on dark clothing. TEGO (R) Care PL 4 (Polyglyceryl-4 Laurate) O.25 0063 For this purpose, two deodorant stick formulations TEGOSOFT (R) XC (Phenoxyethyl Caprylate) 4.OO were produced, the first containing 10% aluminium Zirco TEGOSOFT (RE (PPG-15 Stearyl Ether) 3.00 nium tetrachlorohydrex GLY, whereas in the second this Caprylicicapric acid ethanolamide 2.00 TEGODEO (RPY 88 (Zinc Ricinoleate) 1.00 amount was reduced to 5% and topped up with 5% caprylic/ Propylene Glycol 2.00 capric acid ethanolamide (Table 2). Water ad 100 Aluminium Chlorohydrate (50% in Water) 1S.OO TABLE 2 NATROSOL (R) 25OHHR (Hydroxyethylcellulose) 0.75 Microcare (R) MEM (Dipropylene Glycol; Deodorant stick test formulations. Data in mass percent. To produce Methylparaben; Ethylparaben; Aqua: O.80 the formulations, customary formulation processes known to the Methylisothiazolinone, Thor GmbH) person skilled in the art were used. Perfume C.S. Raw material A. B A. TEGO (R) Alkanol 1618 (Cetearyl Alcohol) 18.0 18.0 0069. Example Formulation Antimicrobial Body Lotion Hydrogenated Castor Oil 2.5 2.5 TEGO (R) Care 165 (Glyceryl Stearate; PEG-100 1.O 1.O Stearate) Raw material Percent by mass Cyclomethicone 51.5 51.5 TEGOSOFT (R) MM (Myristyl Myristate) 1.O 1.O TEGO (R) Care PSC 3 (Polyglyceryl-3 2.50 TEGOSOFT (R) CR (Cetyl Ricinoleate) 1.O 1.O Dicitrate/Stearate) B TEGOSOFT (R) PBE (PPG-14. Butyl Ether) 1O.O 1O.O TEGO (R) Alkanol 18 (Stearyl Alcohol) 1.OO C Talc 3.0 3.0 TEGIN (R) M Pellets (Glyceryl Stearate) 1...SO Aerosil R972 (Silica Dimethyl Sillylate) 1.O 1.O TEGOSOFT (RAC (Isoamyl Cocoate) S.OO D Aluminium Zirconium Tetrachlorohydrex GLY 1O.O S.O TEGOSOFT (R) CT (Caprylic/Capric Triglyceride) S.OO E Caprylicicapric acid ethanolamide S.O Caprylicicapric acid ethanolamide 1.OO F Perfume 1.O 1.O Water ad 100 Glycerin 3.00 TEGO (R) Carbomer 134 O.2O TEGOSOFT (R) XC (Phenoxyethyl Caprylate) 2.OO 0064. In each case 0.2 g of the deodorant stick test formu LACTIL (R) (Sodium Lactate; Sodium PCA: Glycine; 2.0 lations (Table 1) were applied alongside one another by two Fructose; Urea; Niacinamide: Inositol: Sodium fold spreading (back and forth) of the respective deodorant Benzoate; Lactic Acid) stick on a stretch of ca. 10 cm on black foam rubber. The Preservative C.S. photographic documentation of the whitening effect was car Perfume C.S. ried out about six hours after application. Additionally, Skin Colorimeter(R) CL 400 colour measurement probe and C+K US 2015/01 18173 A1 Apr. 30, 2015 6

0070. Example Formulation Antiperspirant/Deodorant -continued Stick Raw material Percent by mass

Raw material Percent by mass Perfume C.S. Aluminium Chlorohydrate (Reach 501 Solution, 3O.OO TEGOSOFT (RAPS (PPG-11 Stearyl Ether) S.OO Reheis) TEGOSOFT (RAPM (PPG-3 Myristyl Ether) S.OO TEGO (R) Alkanol 18 (Stearyl Alcohol) 16.25 Preservative C.S. Hydrogenated Castor Oil 1.75 Cyclopentasiloxane (and) Cyclohexasiloxane 42.00 AEROSIL R972 V (Silica Dimethylsilylate) 3.00 (0074 Example Formulation Deodorizing Wet Wipe Solu MICRO DRY ULTRAFINE (Aluminium 2O.OO tion Chlorohydrate, Reheis) TEGO (R) Cosmo P813 (Polyglyceryl-3 Caprylate) OSO TEGODEO (R) LYS (Zinc Ricinoleate; Lysine: 4.OO Propylene Glycol) Raw material Percent by mass Caprylicicapric acid ethanolamide 2.50 TEGO (R) Betain F (Cocamidopropyl Betaine) 2.00 TEGO (R) Betain 810 (Capryl/Capramidopropyl 1...SO Betaine) Propylene Glycol 0.75 0071 Example Formulation W/O Antiperspirant Aerosol REWODERM (R) LI 63 (PEG-30 Glyceryl Cocoate) OSO Spray Citric Acid Monohydrate OSO TEGODEO (R) HY77 (Zinc Ricinoleate: 1.00 Triethanolamine; Dipropylene Glycol; Lactic Acid) Raw material Percent by mass Sprlie capric acid ethanolamide 9. ABIL (R) EM 90 (Cetyl PEG/PPG-10/1 Dimethicone) 2.OO Tetrasodium EDTA O.10 ISOLAN (R) GPS (Polyglyceryl-4 Diisostearate/ 2.OO Citric Acid Monohydrate pH 5.5 Polyhydroxystearate/Sebacate) Preservative C.S. TEGOSOFT (RTN (C12-15 Alkyl Benzoate) 8.OO Perfume C.S. Cyclopentasiloxane 2S.OO Caprylicicapric acid ethanolamide 2.OO Perfume 1.OO (0075. Example Formulation Deodorant Wipes Solution Water 34.20 Aluminium Chlorohydrate (Reach 501, Reheis) 2O.OO Propylene Glycol S.OO Euxyl (R) PE 9010 (Phenoxyethanol, O.80 Raw material Percent by mass Ethylhexylglycerin; Schilke & Mayr GmbH) TAGAT (R) CH40 (PEG-40 Hydrogenated Castor Oil) 3.0 TEGO (R) Alkanol L 23 P (Laureth-23) 3.0 TEGODEO (R) LYS (Zinc Ricinoleate; Lysine: 3.0 0072 Example Formulation Antiperspirant/Deodorant Propylene Glycol) Aerosol Spray (Water-Free) Caprylicicapric acid ethanolamide 1.5 Farnesol O.2 Perfume O.S Water 84.8 Raw material Percent by mass Dipropylene Glycol 4.0 Citric Acid (50% in water) C.S. Cyclopentasiloxane SO.OO Preservative C.S. Disteardimonium Hectorite 3.00 Perfume S.OO Aerosil R972 (Silica Dimethyl Sillylate) 2.00 Aluminium Chlorohydrate 2S.OO (0076 Example Formulation Deodorant Foot Gel with TEGOSOFTR TN (C12-15 Alkyl Benzoate) 8.00 Alcohol Caprylicicapric acid ethanolamide 2.00 Ethanol S.OO Raw material Percent by mass 0073. Example Formulation O/W Antiperspirant/Deodor- TEGODEO (R) CW 90 (Zinc Ricinoleate: 2.20 ant Roll-on Tetrahydroxypropyl Ethylenediamine; Laureth-3: Propylene Glycol) TEGO (R) Alkanol L4 (Laureth-4) 4.40 Alcohol 32.35 Raw material Percent by mass Neutrol TE (Tetrahydroxypropyl Ethylenediamine, 3.75 BASFSE) TEGO (R) Alkanol S 20 P (Steareth-20) 1.00 Lactic Acid (90%) O.20 TEGO (R) Alkanol S 2 Pellets (Steareth-2) 2.20 Menthol OSO TEGOSOFT (R) liquid (Cetearyl Ethylhexanoate) 2.00 Caprylicicapric acid ethanolamide 2.00 TEGOSOFT (RAPS (PPG-11 Stearyl Ether) 2.00 TEGO (R) Carbomer 140 (Carbomer) 1...SO ABIL (R) 350 (Dimethicone) OSO Water 48.86 Caprylicicapric acid ethanolamide 3.00 Panthenol O.20 Glycerin 3.00 Propylene Glycol 2.00 Water 52.30 Colour 2.04 TEGODEO (R) LYS (Zinc Ricinoleate; Lysine: 4.OO Propylene Glycol) US 2015/01 18173 A1 Apr. 30, 2015

0077. Example Formulation Clear Hand Conditioning Gel aluminium Zinc oxide, aluminium Zirconium trichlorohy drate, aluminium zirconium trichlorohydrex GLY, aluminium Zirconium tetrachlorohydrate, aluminium Zirconium tetra Raw material Percent by mass chlorohydrex GLY, aluminium zirconium tetrachlorohydrex ABIL (R) EM 90 (Cetyl PEG/PPG-10/1 Dimethicone) 2.OO PEG, aluminium zirconium tetrachlorohydrex PG, alu ABIL(R) OSW 5 (Cyclopentasiloxane: 2.OO minium Zirconium pentachlorohydrate, aluminium Zirco Dimethiconol) nium pentachlorohydrex GLY, aluminium Zirconium TEGOSOFT (R) OP (Ethylhexyl Palmitate) 4.OO octachlorohydrate, aluminium Zirconium octachlorohydrex TEGOSOFT (R) OS (Ethylhexyl Stearate) 4.OO Cyclopentasiloxane (and) Cyclohexasiloxane 7.OO GLY ammonium alum, ammonium silver Zinc aluminium TEGOSOFT (R) CO (Cetyl Ethylhexanoate) 2.OO silicate, calcium aluminium borosilicate, cobalt aluminium Perfume C.S. oxide, magnesium/aluminium/hydroxide/carbonate, magne Caprylicicapric acid ethanolamide 1...SO sium aluminium silicate, magnesium/aluminium/Zinc?hy Water 14.40 Magnesium Sulphate Heptahydrate O.80 droxide/carbonate, potassium alum, potassium aluminium Propylene Glycol 45.OO polyacrylate, silver magnesium aluminium phosphate, Glycerin 18.00 Sodium alum, Sodium aluminate, sodium aluminium chloro Triclosan O.30 hydroxy lactate, Sodium/aluminium hydroxide/oxalate/sul Preservative C.S. phate, sodium/aluminium/iron hydroxide/oxalate/sulphate, Sodium/aluminium/iron/Sulphate/citrate/hydroxide, Sodium/ 1. A formulation comprising: aluminium/iron/sulphate/oxalate/hydroxide, sodium/alu at least one compound of formula (I) minium/iron/sulphate?tartarate/hydroxide, sodium alu minium lactate, sodium phosphorus/Zinc? calcium/silicon/ aluminium/silver oxides, sodium potassium aluminium formula (I) silicate, sodium silicoaluminate, sodium silver aluminium O silicate, tromethamine magnesium aluminium silicate and alum. ---- OH s 3. The formulation according to claim 1, wherein the alu H minium salt is aluminium chlorohydrate. 4. The formulation according to claim 1, further compris where ing less than 80% by weight of compounds of formula (II) R'= C, His or -CoHo, and an aluminium salt. formula (II) 2. The formulation according to claim 1, wherein the alu O minium salt is selected from aluminium acetate, aluminium behenate, aluminium benzoate, aluminium bromohydrate, R !---- aluminium butoxide, aluminium calcium Sodium silicate, H aluminium caprylate, aluminium capryloyl hydrolyzed col lagen, aluminium chloride, aluminium chlorohydrate, alu minium chlorohydrex, aluminium chlorohydrex PEG, alu where minium chlorohydrex PG, aluminium citrate, aluminium R’—an organic radical with a chain length of less than 7 or diacetate, aluminium dibenzoate/stearate hydroxide, alu greater than 9. minium dicetyl phosphate, aluminium dichlorohydrate, alu based on the total amount of the compounds of the formula minium dichlorohydrex PEG, aluminium dichlorohydrex (I) and (II). PG, aluminium dilinoleate, aluminium dimyristate, alu 5. The formulation according to claim 1, wherein the at minium distearate, aluminium glycinate, aluminium hydro least one compound of formula (I) is present in an amount genated tallow glutamate, aluminium hydroxy bis-methylene from 0.001 to 20% by weight, based on the total formulation. bis-di-t-butylphenyl phosphate, aluminium iron calcium 6. The formulation according to claim 1, wherein the alu magnesium germanium silicates, aluminium iron calcium minium salt is present in amount from 0.01 to 50% by weight, magnesium Zirconium silicates, aluminium iron silicates, based on the total formulation. aluminium isopropoxide, aluminium isostearate, aluminium isostearates/laurates/palmitates, aluminium isostearates/lau 7. The formulation according claim 1, wherein the at least rates/stearates, aluminium isostearates/myristates, alu one compound of formula (I) includes a mixture of com minium isostearates/palmitates, aluminium isostearates/ pounds of formula (I) wherein some of the compounds of Stearates, aluminium isostearyl glyceryl phosphate, formula (I) of the mixture have R = CHs and other of the aluminium laccate, aluminium lactate, aluminium lanolate, compounds of formula (I) of the mixture have R= -CH aluminium/magnesium hydroxide Stearate, aluminium mag and wherein a weight ratio of the compounds of formula (I) nesium oxide, aluminium methionate, aluminium myristate, with R= -CHs to compounds of formula (I) with R= - aluminium myristates/palmitates, aluminium PCA, alu CH is in a range from 5:95 to 95:5. minium phenolsulphonate, aluminium sesquichlorohydrate, 8. The formulation according to claim 1, further compris aluminium sesquichlorohydrex PEG, aluminium sesquichlo ing a deodorant active ingredient or an antiperspirant active rohydrex PG, aluminium starch octenylsuccinate, aluminium ingredient. Stearate, aluminium Stearates, aluminium Stearoylglutamate, 9. The formulation accordingly to claim 1, further com aluminium Sucrose octasulphate, aluminium Sulphate, alu prising at least one antimicrobial active ingredient. minium triformate, aluminium triphosphate, aluminium 10. The formulation according to claim 1, further compris tristearate, aluminium undecylenoyl collagen amino acids, ing at least one foot care additive. US 2015/01 18173 A1 Apr. 30, 2015

11. The formulation according to claim 1, further compris 15. The method according to claim 14, wherein the micro ing at least one antiacne active ingredient. organism is of the genera Microsporum, Epidermiphyton, 12. The formulation according to claim 1, further compris Trichphyton or Gram-positive bacteria. ing at least one antidandruff ingredient. 16. A method for reducing human body odor, said method 13. (canceled) comprising: 14. A method for reducing the growth of microorganisms, applying a formulation comprising at least one compound said method comprising: of formula (I) applying a formulation comprising at least one compound of formula (I) formula (I)

formula (I) O --~ OH s H where R'= C, His or -CoHo, and where an aluminium salt to human skin or to an article of manu R"—C7Hisl or -CH; and facture. an aluminium salt to an area in which a microorganism 17. (canceled) grOWS.