EP2276456A1 - Antimicrobial cosmetic preparations - Google Patents

Antimicrobial cosmetic preparations

Info

Publication number
EP2276456A1
EP2276456A1 EP09745484A EP09745484A EP2276456A1 EP 2276456 A1 EP2276456 A1 EP 2276456A1 EP 09745484 A EP09745484 A EP 09745484A EP 09745484 A EP09745484 A EP 09745484A EP 2276456 A1 EP2276456 A1 EP 2276456A1
Authority
EP
European Patent Office
Prior art keywords
cationic
styrene
sodium
active substances
surfactants
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP09745484A
Other languages
German (de)
French (fr)
Inventor
Horst Argembeaux
Katrin Counradi
Heike FÖLSTER
Maren Meyer
Michael WÖHRMANN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beiersdorf AG
Original Assignee
Beiersdorf AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP2276456A1 publication Critical patent/EP2276456A1/en
Ceased legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00Anti-perspirants or body deodorants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005Antimicrobial preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations

Definitions

  • the human body is overgrown with microorganisms throughout the skin. These live, as it were, in a symbiosis with humans, their perfect, permanent removal would lead to pathological changes. This symbiosis works only if the concentration of microorganisms and their biodiversity are in an optimal balance. If this balance is disturbed, it can lead to unpleasant to pathological changes in the skin or unpleasant perceptions from subsequent processes.
  • germicidal agents In cosmetics and medicine, active substances are known which have an antimicrobial effect and can thus influence the balance of the skin flora. By skillfully selecting and concentrating such active ingredients in suitable matrix formulations, it is possible for a person skilled in the art to develop products which specifically combat microorganism-induced cosmetic or pathological secondary problems. A distinction is made between such agents that kill specific or all germs and those that remove germs from surfaces and bind to themselves. Germicidal agents carry the risk of intolerance reactions, as they can not destroy the cells of the microorganisms as cell toxins, in addition, can form resistances that can adversely affect the balance of the skin flora. Another negative aspect of germicidal agents is their effectiveness kinetics, the use for short-term treatments such. As a cleaning process followed by rinsing, impossible.
  • Anti-microbial agents are commonly referred to as antiadhesives and show no such negative effects. They bind germs without killing them and thus inactivate their action on the skin. The formation of resistance is excluded in consequence. They also have no cell-destroying effect, which eliminates the risk of such induced intolerance reactions and they act immediately.
  • Surfactants are amphiphilic substances that can dissolve organic, nonpolar substances in water. Due to their specific molecular structure with at least one hydrophilic and one hydrophobic part of the molecule, they provide for a lowering of the surface tension of the water, the wetting of the skin, the facilitation of dirt removal and dissolution, a gentle rinsing and - as desired - for foam regulation.
  • hydrophilic portions of a surfactant molecule are usually polar functional groups, for example -COO " , -OSO 3 2" , -SO 3 " , while the hydrophobic portions are generally non-polar hydrocarbon residues of the hydrophilic part of the molecule, whereby four groups can be distinguished:
  • Anionic surfactants generally have carboxylate, sulfate or sulfonate groups as functional groups. In aqueous solution, they form negatively charged organic ions in an acidic or neutral medium. Cationic surfactants are almost exclusively characterized by the presence of a quaternary ammonium group. In aqueous solution they form positively charged organic ions in an acidic or neutral environment. Amphoteric surfactants contain both anionic and cationic groups and behave accordingly in aqueous solution depending on the pH as anionic or cationic surfactants. They have a positive charge in a strongly acidic environment and a negative charge in an alkaline environment. In the neutral pH range, however, they are zwitterionic, as the following example is intended to illustrate:
  • Non-ionic surfactants are polyether chains. Nonionic surfactants do not form ions in an aqueous medium.
  • acylglutamates for example sodium acylglutamate, di-TEA-palmitoylaspartate and sodium caprylic / capric glutamate,
  • acyl peptides for example palmitoyl-hydrolyzed milk protein, sodium cocoyl-hydrolysed soy protein and sodium / potassium cocoyl-hydrolyzed collagen,
  • sarcosinates for example myristoyl sarcosine, TEA-lauroyl sarcosinate, sodium lauroyl sarcosinate and sodium cocoyl sarcosinate,
  • taurates for example sodium lauroyl taurate and sodium methyl cocoyl taurate
  • Carboxylic acids and derivatives such as
  • carboxylic acids for example lauric acid, aluminum stearate, magnesium alkoxide and zinc undecylenate,
  • Ester carboxylic acids for example calcium stearoyl lactylate, laureth-6-citrate and sodium PEG-4-lauramide carboxylate,
  • Ether carboxylic acids for example sodium laureth-13-carboxylate and sodium PEG-6-cocamide carboxylate,
  • Phosphoric acid esters and salts such as DEA-oleth-10-phosphate and dilaureth-4-phosphate,
  • Sulfonic acids and salts such as
  • alkylsulfonates for example sodium, sodium C 12 -14 olefinsulfonates fin-sulfonate, sodium lauryl sulfoacetate and magnesium PEG-3 cocamide sulfate,
  • Sulfosuccinates for example dioctyl sodium sulphosuccinate, disodium laureth sulphosuccinate, disodium lauryl sulphosuccinate, disodium undecylenamido MEA sulphosuccinate and PEG-5 lauryl citrate sulphosuccinate. and sulfuric acid esters, such as
  • alkyl ether sulfate for example sodium, ammonium, magnesium, MIPA, TIPA laureth sulfate, sodium myreth sulfate and sodium C 12-13 pareth sulfate,
  • Alkyl sulfates for example sodium, ammonium and TEA lauryl sulfate.
  • Quaternary surfactants contain at least one N atom covalently bonded to 4 alkyl and / or aryl groups. This results in a positive charge regardless of the pH.
  • Advantageous quaternary surfactants are alkyl betaine, alkyl amidopropyl betaine and alkyl amidopropyl hydroxysulfain.
  • Cationic surfactants can furthermore preferably be selected from the group of quaternary ammonium compounds, in particular benzyltrialkylammonium chlorides or bromides, such as, for example, benzyldimethylstearylammonium chloride, alkyltrialkylammonium salts, for example cetyltrimethylammonium chloride or bromide, alkyldimethylhydroxyethylammonium chlorides or bromides, Dialkyldimethylammonium chlorides or bromides, alkylamidethyltrimethylammonium ether sulfates, alkylpyridinium salts, for example lauryl or cetylpyrimidinium chloride, imidazoline derivatives and compounds having a cationic character such as amine oxides, for example alkyldimethylamine oxides or alkylaminoethyldimethylamine oxides. Cetyltrimethylammonium salts are particularly advantageous to use.
  • acyl / dialkylethylenediamine for example sodium acylamphoacetate, disodium acyl amphodipropionate, disodium alkyl amphodiacetate, sodium acylamphohydroxypropyl sulfonate, disodium acyl amphodiacetate and sodium acyl amphopropionate,
  • N-alkylamino acids for example aminopropylalkylglutamide, alkylaminopropionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate.
  • D. Nonionic surfactants for example aminopropylalkylglutamide, alkylaminopropionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate.
  • alkanolamides such as cocamide MEA / DEA / MIPA
  • amine oxides such as cocoamidopropylamine oxide
  • Ethers for example ethoxylated / propoxylated alcohols, ethoxylated / propoxylated esters, ethoxylated / propoxylated glycerol esters, ethoxylated / propoxylated triglyceride esters, ethoxylated propoxylated lanolin, ethoxylated / propoxylated polysiloxanes, propoxylated POE ethers and alkyl polyglycosides such as lauryl glucoside, Decyl glycoside and cocoglycoside.
  • antimicrobial cosmetic preparations containing a cationic styrene / acrylate copolymer obtainable by copolymerization of butyl acrylate, ethyltrimonium chloride methacrylate and styrene and at most 20 wt .-% surfactants to overcome the disadvantages of the prior art.
  • Such cationic styrene / acrylate copolymers in combination with surface-active substances such.
  • emulsifiers or surfactants enhance the anti-adhesive effect or at least not reduce it.
  • Formulations with higher levels of surfactants show similar effects when the proportion of anionic surfactants is very low.
  • such formulations do not show any increased surfactant adsorption on the skin and are thus excellently compatible.
  • the surface-active substances are selected from the group of anionic, cationic, amphoteric or nonionic surfactants or mixtures thereof. It is preferred if the content of anionic surface-active substances is at most 5% by weight, preferably at most 3% by weight, particularly preferably at most 2.5% by weight. It is preferred if the cationic styrene / acrylate copolymer is a polymer with the INCI name "butyl acrylate / ethyltrimonium chloride methacrylates / styrene copolymer.” Polymers whose cationic charges are free from degradation or Activation protected and so are still effective even after a long time. Such protection can be provided, for example, by the cationic group of adjacent nonionic side chains. Such polymers are for. As described in US 20050003163.
  • a particularly advantageous deodorant effect is a butyl acrylate / ethyltrimonium chloride methacrylate / styrene copolymer, which is sold by Dow Reichhold Specialty Latex under the trade name PolySaf TM 5600.
  • PolySaf 5600 is offered as a - 40% aqueous suspension and can be easily incorporated into a wide variety of cosmetic formulations.
  • the invention also includes the use of preparations according to any one of the preceding claims as deodorants, deodorizing products, personal care, shower or anti-acne products.
  • the reference substances used were the raw materials TEXAPON N 70 (LES Cognis), active content 70% and REWOTERIC AM C (CAA Evonik Goldschmidt), active content 32.5%. The contents given refer to the reference substances used; To calculate the absolute surfactant contents, the results given must be corrected by the activity content deviating from 100%.
  • Cocoamphoacetate (30) shower formulation with chitosan containing 2.1% LES, 7.2% sodium
  • Cocoamphoacetate 2.9% Cocamidopropyl Betaine (20) shower formulation without new cat. Polymer with 2.1% LES, 10.1%
  • Sodium cocoamphoacetate 0.00 corresponds to ⁇ determination limit (0.15 ⁇ g / mL)
  • Betaine 0.00 corresponds to ⁇ determination limit (0.1 ⁇ g / mL)
  • Bacteria of a LINK (overnight culture) are centrifuged off, washed with buffer, fixed in 70% EtOH for 30 min and stained with propidium iodide. The excess dye is removed by washing several times. The bacteria are incubated for 1 h with the raw materials (anti-adhesives). Subsequently, the bacterial suspensions are incubated with human corneocytes, which are obtained from the forearm of a subject, for 1 h at RT (room temperature). After this adhesion period, the bacteria-corneocyte complexes are obtained by separation of the non-adherent bacteria and the adhesion rate is determined by flow cytometry and controlled microscopically.
  • the rate of adhesion of the control batch, in which bacteria (not pretreated) and Comeozyten are incubated, is defined as 100% relative Adphosungsrate. All other approaches are calculated in relation to it. Values ⁇ 100% indicate an inhibition of bacterial adhesion, values> 100% an increased bacterial adhesion.
  • the graph below shows the relative rates of adhesion after incubation with a cationic example polymer (PolySaf 5600, 40% aqueous dispersion) and surfactant mixtures with and without cationic polymer.
  • the example polymer shows a very good reduction in bacterial adhesion to 19% relative adhesion rate. Both surfactant formulations show a slight influence on the adhesion (85% and 95%, respectively). Surfactant formulation 1 with a higher content of anionic surfactants shows a strong influence on the effectiveness of the cationic polymer. In contrast, surfactant formulation 2, with a significantly lower content of anionic surfactants, can even increase the effectiveness of the example polymer (to 14% relative adhesion rate).
  • Fig. Anti-adhesive effectiveness of surfactant formulations.
  • the following graph shows the influence of the cationic polymer PolySaf 5600 (as a 40% aqueous dispersion) on the relative adhesion rate.
  • the polymer alone reduces the relative adhesion rate to a value of 19%.
  • the effectiveness of the PolySaf 5600 polymer is at a similar level (relative adhesion rate of 22%) while the formulation itself has no effect. See Figure 4
  • formulations based on such combinations may contain other components, e.g. Preservatives, stabilizers, buffering agents, thickeners, perfumes, pearlescing agents, opacifiers, complexing agents, humectants, solvents, dyes, oils, extracts, vitamins, antioxidants, UV filters.
  • Preservatives e.g. Preservatives, stabilizers, buffering agents, thickeners, perfumes, pearlescing agents, opacifiers, complexing agents, humectants, solvents, dyes, oils, extracts, vitamins, antioxidants, UV filters.
  • the combination with other Deowirkstoffen such as triclosan, chlorhexidine or the naturally occurring compounds such as Famesol, 2-butyl octanoic acid and phenoxyethanol.
  • the combination with aluminum salts such as aluminum hydroxychloride (aluminum chlorohydrate) or aluminum / zirconium salts may be preferred.
  • Example formulations for a variety of applications are deodorant applications, deodorant showers, personal care products, anti-dandruff shampoo, foot bath, skin care, facial cleansing or anti-acne products.
  • the liquid phase obtained by mixing together the respective components is filled with a propane-butane mixture (2.7) in a ratio of 39:61 in aerosol containers.
  • the liquid phase obtained by mixing the respective components together with a propane-butane mixture (2.7) in the ratio 17:83 filled in aerosol container.
  • the liquid phase obtained by mixing together the respective components is filled with a propane-butane mixture (2.7) in the ratio 19:81 in aerosol containers.
  • the pH of the shower gels is 4.8 - 5.3:
  • the viscosity is between 2000 and 5000 mPa.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

Disclosed are antimicrobial cosmetic preparations containing a cationic styrene/acrylate copolymer obtained by copolymerizing butyl acrylate, ethyltrimonium chloride methacrylate, and styrene, and a maximum of 20 percent by weight of surfactants.

Description

Beiersdorf AG Beiersdorf AG
HamburgHamburg
Antimikrobielle kosmetische ZubereitungenAntimicrobial cosmetic preparations
Der Körper des Menschen ist auf der gesamten Haut von Mikroorganismen bewachsen. Diese leben quasi in einer Symbiose mit dem Menschen, ihre vollkommene, dauerhafte Beseitigung würde zu krankhaften Veränderungen führen. Diese Symbiose funktioniert aber nur wenn die Konzentration der Mikroorganismen und deren Artenvielfalt sich in einem optimalen Gleichgewicht befinden. Wird dieses Gleichgewicht gestört, kann es zu unangenehmen bis krankhaften Veränderungen der Haut bzw. unangenehmen Wahrnehmungen aus Folgeprozessen kommen.The human body is overgrown with microorganisms throughout the skin. These live, as it were, in a symbiosis with humans, their perfect, permanent removal would lead to pathological changes. This symbiosis works only if the concentration of microorganisms and their biodiversity are in an optimal balance. If this balance is disturbed, it can lead to unpleasant to pathological changes in the skin or unpleasant perceptions from subsequent processes.
Beispiele solcher Folgeerscheinungen sind z. B. üble Gerüche, Schuppen, Akne.Examples of such consequences are z. As bad smells, dandruff, acne.
In der Kosmetik und der Medizin sind Wirkstoffe bekannt, die antimikrobiell wirken und somit das Gleichgewicht der Hautflora beeinflussen können. Durch geschickte Auswahl und Konzentration solcher Wirkstoffe in geeigneten Matrixformulierungen gelingt es dem Fachmann Produkte zu entwickeln, die durch Mikroorganismen hervorgerufenen kosmetische oder pathologische Folgeprobleme gezielt bekämpfen. Man unterscheidet dabei solche Wirkstoffe, die spezifische oder alle Keime töten und solche, die Keime von Oberflächen entfernen und an sich binden. Keimtötende Wirkstoffe bergen das Risiko von Unverträglichkeitsreaktionen, da sie als Zellgifte nicht ausschließlich die Zellen der Mikroorganismen zerstören können, zudem können sich Resistenzen bilden, die das Gleichgewicht der Hautflora negativ beeinflussen können. Ein weiterer negativer Aspekt keimtötender Wirkstoffe ist deren Wirksamkeitskinetik, die den Einsatz für Kurzzeitbehandlungen, wie z. B. einem Reinigungsprozess mit anschließendem Abspülen, unmöglich macht.In cosmetics and medicine, active substances are known which have an antimicrobial effect and can thus influence the balance of the skin flora. By skillfully selecting and concentrating such active ingredients in suitable matrix formulations, it is possible for a person skilled in the art to develop products which specifically combat microorganism-induced cosmetic or pathological secondary problems. A distinction is made between such agents that kill specific or all germs and those that remove germs from surfaces and bind to themselves. Germicidal agents carry the risk of intolerance reactions, as they can not destroy the cells of the microorganisms as cell toxins, in addition, can form resistances that can adversely affect the balance of the skin flora. Another negative aspect of germicidal agents is their effectiveness kinetics, the use for short-term treatments such. As a cleaning process followed by rinsing, impossible.
Keimentfernende Wirkstoffe werden allgemein als Antiadhäsiva bezeichnet und zeigen keine derart negativen Effekte. Sie binden Keime ohne sie zu töten und inaktivieren somit deren Wirkung auf der Haut. Die Bildung von Resistenzen ist in Folge dessen ausgeschlossen. Sie haben auch keine zellzerstörende Wirkung, was das Risiko von derart hervorgerufenen Unverträglichkeitsreaktionen ausschließt und sie wirken sofort.Anti-microbial agents are commonly referred to as antiadhesives and show no such negative effects. They bind germs without killing them and thus inactivate their action on the skin. The formation of resistance is excluded in consequence. They also have no cell-destroying effect, which eliminates the risk of such induced intolerance reactions and they act immediately.
DE 19503423 beschreibt Kohlehydrate, die eine derart antiadhäsive Wirkung haben, darüberhi- naus zeigen Chitinderivate, z. B. Chitosan wie in DE 102005048776 beschrieben, und viele ka- tionische Polymere gleichfalls eine derart antiadhäsive Wirkung. Dennoch hat sich der Einsatz solcher Wirkstoffe nicht durchgesetzt. Als Grund dafür ist eine nur unzureichende antiadhäsiver Wirkung vieler dieser Wirkstoffe und eine häufig auftretende Inaktivierung durch den Einfluss der Matrixformulierung anzusehen. Manche, wie z. B. Chitosan wirken darüberhinaus als Deposition Aids, was zu einer Anreicherung reizender Noxen wie z. B. Tenside auf der Haut und somit zu einer potenziellen Reizquelle führt.DE 19503423 describes carbohydrates which have such an antiadhesive effect; moreover, chitin derivatives, eg. Chitosan as described in DE 102005048776, and many tionische polymers also such an anti-adhesive effect. Nevertheless, the use of such agents has not prevailed. The reason for this is considered to be an insufficient antiadhesive effect of many of these active ingredients and a frequent inactivation due to the influence of the matrix formulation. Some, such as B. Chitosan also act as deposition Aids, resulting in an accumulation of irritating Noxen such. B. surfactants on the skin and thus leads to a potential source of irritation.
Tenside sind amphiphile Stoffe, die organische, unpolare Substanzen in Wasser lösen können. Sie sorgen, bedingt durch ihren spezifischen Molekülaufbau mit mindestens einem hydrophilen und einem hydrophoben Molekülteil, für eine Herabsetzung der Oberflächenspannung des Wassers, die Benetzung der Haut, die Erleichterung der Schmutzentfernung und -lösung, ein leichtes Abspülen und - je nach Wunsch - für Schaumregulierung.Surfactants are amphiphilic substances that can dissolve organic, nonpolar substances in water. Due to their specific molecular structure with at least one hydrophilic and one hydrophobic part of the molecule, they provide for a lowering of the surface tension of the water, the wetting of the skin, the facilitation of dirt removal and dissolution, a gentle rinsing and - as desired - for foam regulation.
Bei den hydrophilen Anteilen eines Tensidmoleküls handelt es sich meist um polare funktionelle Gruppen, beispielweise -COO", -OSO3 2", -SO3 ", während die hydrophoben Teile in der Regel unpolare Kohlenwasserstoffreste darstellen. Tenside werden im allgemeinen nach Art und Ladung des hydrophilen Molekülteils klassifiziert. Hierbei können vier Gruppen unterschieden werden:The hydrophilic portions of a surfactant molecule are usually polar functional groups, for example -COO " , -OSO 3 2" , -SO 3 " , while the hydrophobic portions are generally non-polar hydrocarbon residues of the hydrophilic part of the molecule, whereby four groups can be distinguished:
• anionische Tenside,Anionic surfactants,
• kationische Tenside,Cationic surfactants,
• amphotere Tenside und• amphoteric surfactants and
• nichtionische Tenside.• nonionic surfactants.
Anionische Tenside weisen als funktionelle Gruppen in der Regel Carboxylat-, Sulfat- oder SuI- fonatgruppen auf. In wässriger Lösung bilden sie im sauren oder neutralen Milieu negativ geladene organische Ionen. Kationische Tenside sind beinahe ausschließlich durch das Vorhandensein einer quarternären Ammoniumgruppe gekennzeichnet. In wässriger Lösung bilden sie im sauren oder neutralen Milieu positiv geladene organische Ionen. Amphotere Tenside enthalten sowohl anionische als auch kationische Gruppen und verhalten sich demnach in wässriger Lösung je nach pH-Wert wie anionische oder kationische Tenside. Im stark sauren Milieu besitzen sie eine positive und im alkalischen Milieu eine negative Ladung. Im neutralen pH-Bereich hingegen sind sie zwitterionisch, wie das folgende Beispiel verdeutlichen soll:Anionic surfactants generally have carboxylate, sulfate or sulfonate groups as functional groups. In aqueous solution, they form negatively charged organic ions in an acidic or neutral medium. Cationic surfactants are almost exclusively characterized by the presence of a quaternary ammonium group. In aqueous solution they form positively charged organic ions in an acidic or neutral environment. Amphoteric surfactants contain both anionic and cationic groups and behave accordingly in aqueous solution depending on the pH as anionic or cationic surfactants. They have a positive charge in a strongly acidic environment and a negative charge in an alkaline environment. In the neutral pH range, however, they are zwitterionic, as the following example is intended to illustrate:
RNH2 +CH2CH2COOH X" (bei pH=2) X" = beliebiges Anion, z.B. Cl" RNH 2 + CH 2 CH 2 COOH X " (at pH = 2) X " = any anion, eg Cl "
RNH2 +CH2CH2COO" (bei pH=7)RNH 2 + CH 2 CH 2 COO " (at pH = 7)
RNHCH2CH2COO- B+ (bei pH=12) B+ = beliebiges Kation, z.B. Na+ Typisch für nicht-ionische Tenside sind Polyether-Ketten. Nicht-ionische Tenside bilden in wässrigem Medium keine Ionen.RNHCH 2 CH 2 COO-B + (at pH = 12) B + = any cation, eg Na + Typical of non-ionic surfactants are polyether chains. Nonionic surfactants do not form ions in an aqueous medium.
A. Anionische TensideA. Anionic surfactants
Vorteilhaft zu verwendende anionische Tenside sindAdvantageously used anionic surfactants are
Acylaminosäuren (und deren Salze), wieAcylamino acids (and their salts), such as
1. Acylglutamate, beispielsweise Natriumacylglutamat, Di-TEA-palmitoylaspartat und Natrium Caprylic/ Capric Glutamat,1. acylglutamates, for example sodium acylglutamate, di-TEA-palmitoylaspartate and sodium caprylic / capric glutamate,
2. Acylpeptide, beispielsweise Palmitoyl-hydrolysiertes Milchprotein, Natrium Cocoyl- hydrolysiertes Soja Protein und Natrium-/ Kalium-Cocoyl-hydrolysiertes Kollagen,2. acyl peptides, for example palmitoyl-hydrolyzed milk protein, sodium cocoyl-hydrolysed soy protein and sodium / potassium cocoyl-hydrolyzed collagen,
3. Sarcosinate, beispielsweise Myristoyl Sarcosin, TEA-Iauroyl Sarcosinat, Natrium- lauroylsarcosinat und Natriumcocoylsarkosinat,3. sarcosinates, for example myristoyl sarcosine, TEA-lauroyl sarcosinate, sodium lauroyl sarcosinate and sodium cocoyl sarcosinate,
4. Taurate, beispielsweise Natriumlauroyltaurat und Natriummethylcocoyltaurat,4. taurates, for example sodium lauroyl taurate and sodium methyl cocoyl taurate,
5. Acyllactylate, Lauroyllactylat, Caproyllactylat5. Acyl lactylates, lauroyl lactylate, caproyl lactylate
6. Alaninate6. Alaninates
Carbonsäuren und Derivate, wieCarboxylic acids and derivatives, such as
1. Carbonsäuren, beispielsweise Laurinsäure, Aluminiumstearat, Magnesiumalkanolat und Zinkundecylenat,1. carboxylic acids, for example lauric acid, aluminum stearate, magnesium alkoxide and zinc undecylenate,
2. Ester-Carbonsäuren, beispielsweise Calciumstearoyllactylat, Laureth-6-Citrat und Natrium PEG-4-Lauramidcarboxylat,2. Ester carboxylic acids, for example calcium stearoyl lactylate, laureth-6-citrate and sodium PEG-4-lauramide carboxylate,
3. Ether-Carbonsäuren, beispielsweise Natriumlaureth-13-Carboxylat und Natrium PEG-6-Cocamide Carboxylat,3. Ether carboxylic acids, for example sodium laureth-13-carboxylate and sodium PEG-6-cocamide carboxylate,
Phosphorsäureester und Salze, wie beispielsweise DEA-Oleth-10-Phosphat und Dilaureth-4 Phosphat,Phosphoric acid esters and salts such as DEA-oleth-10-phosphate and dilaureth-4-phosphate,
Sulfonsäuren und Salze, wieSulfonic acids and salts, such as
1. Acyl-isethionate, z. B. Natrium-/ Ammoniumcocoyl-isethionat,1. Acyl-isethionates, z. B. sodium / ammonium cocoyl isethionate,
2. Alkylarylsulfonate,2. alkylaryl sulphonates,
3. Alkylsulfonate, beispielsweise Natriumcocosmonoglyceridsulfat, Natrium C12-14 Ole- fin-sulfonat, Natriumlaurylsulfoacetat und Magnesium PEG-3 Cocamidsulfat,3. alkylsulfonates, for example sodium, sodium C 12 -14 olefinsulfonates fin-sulfonate, sodium lauryl sulfoacetate and magnesium PEG-3 cocamide sulfate,
4. 4. Sulfosuccinate, beispielsweise Dioctylnatriumsulfosuccinat, Dinatriumlaurethsul- fosuccinat, Dinatriumlaurylsulfosuccinat, Dinatriumundecylenamido-MEA-Sul- fosuccinat und PEG-5 Laurylcitrat Sulfosuccinat. sowie Schwefelsäureester, wie4. 4. Sulfosuccinates, for example dioctyl sodium sulphosuccinate, disodium laureth sulphosuccinate, disodium lauryl sulphosuccinate, disodium undecylenamido MEA sulphosuccinate and PEG-5 lauryl citrate sulphosuccinate. and sulfuric acid esters, such as
1. Alkylethersulfat, beispielsweise Natrium-, Ammonium-, Magnesium-, MIPA-, TIPA- Laurethsulfat, Natriummyrethsulfat und Natrium C12-13-Parethsulfat,1. alkyl ether sulfate, for example sodium, ammonium, magnesium, MIPA, TIPA laureth sulfate, sodium myreth sulfate and sodium C 12-13 pareth sulfate,
2. Alkylsulfate, beispielsweise Natrium-, Ammonium- und TEA-Laurylsulfat.2. Alkyl sulfates, for example sodium, ammonium and TEA lauryl sulfate.
B. Kationische TensideB. Cationic surfactants
Vorteilhaft zu verwendende kationische Tenside sindAdvantageously to use cationic surfactants
1. Alkylamine,1. alkylamines,
2. Alkylimidazole,2. alkylimidazoles,
3. Ethoxylierte Amine und3. Ethoxylated amines and
4. Quaternäre Tenside.4. Quaternary surfactants.
5. Esterquats5. Esterquats
Quaternäre Tenside enthalten mindestens ein N-Atom, das mit 4 Alkyl- und/oder Arylgruppen kovalent verbunden ist. Dies führt, unabhängig vom pH Wert, zu einer positiven Ladung. Vorteilhafte quaternäre Tenside sind Alkylbetain, Alkylamidopropylbetain und Alkyl-amidopropylhy- droxysulfain. Kationische Tenside können ferner bevorzugt im Sinne der vorliegenden Erfindung gewählt werden aus der Gruppe der quatemären Ammoniumverbindungen, insbesondere Ben- zyltrialkylammoniumchloride oder -bromide, wie beispielsweise Benzyldimethylstea- rylammoπiumchlorid, ferner Alkyltrialkylammoniumsalze, beispielsweise beispielsweise Cetyltri- methylammoniumchlorid oder -bromid, Alkyldimethylhydroxyethylammoniumchloride oder - bromide, Dialkyldimethylammoniumchloride oder -bromide, Alkylamidethyltrimethylammonium- ethersulfate, Alkylpyridiniumsalze, beispielsweise Lauryl- oder Cetylpyrimidiniumchlorid, Imida- zolinderivate und Verbindungen mit kationischem Charakter wie Aminoxide, beispielsweise Al- kyldimethylaminoxide oder Alkylaminoethyldimethylaminoxide. Vorteilhaft sind insbesondere Cetyltrimethylammoniumsalze zu verwenden.Quaternary surfactants contain at least one N atom covalently bonded to 4 alkyl and / or aryl groups. This results in a positive charge regardless of the pH. Advantageous quaternary surfactants are alkyl betaine, alkyl amidopropyl betaine and alkyl amidopropyl hydroxysulfain. Cationic surfactants can furthermore preferably be selected from the group of quaternary ammonium compounds, in particular benzyltrialkylammonium chlorides or bromides, such as, for example, benzyldimethylstearylammonium chloride, alkyltrialkylammonium salts, for example cetyltrimethylammonium chloride or bromide, alkyldimethylhydroxyethylammonium chlorides or bromides, Dialkyldimethylammonium chlorides or bromides, alkylamidethyltrimethylammonium ether sulfates, alkylpyridinium salts, for example lauryl or cetylpyrimidinium chloride, imidazoline derivatives and compounds having a cationic character such as amine oxides, for example alkyldimethylamine oxides or alkylaminoethyldimethylamine oxides. Cetyltrimethylammonium salts are particularly advantageous to use.
C. Amphotere TensideC. Amphoteric surfactants
Vorteilhaft zu verwendende amphotere Tenside sindAdvantageously used amphoteric surfactants
1. Acyl-/dialkylethylendiamin, beispielsweise Natriumacylamphoacetat, Dinatriumacyl- amphodipropionat, Dinatriumalkylamphodiacetat, Natriumacylamphohydroxy- propylsulfonat, Dinatriumacylamphodiacetat und Natriumacylamphopropionat,1. acyl / dialkylethylenediamine, for example sodium acylamphoacetate, disodium acyl amphodipropionate, disodium alkyl amphodiacetate, sodium acylamphohydroxypropyl sulfonate, disodium acyl amphodiacetate and sodium acyl amphopropionate,
2. N-Alkylaminosäuren, beispielsweise Aminopropylalkylglutamid, Alkylaminopropion- säure, Natriumalkylimidodipropionat und Lauroamphocarboxyglycinat. D. Nicht-ionische Tenside2. N-alkylamino acids, for example aminopropylalkylglutamide, alkylaminopropionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate. D. Nonionic surfactants
Vorteilhaft zu verwendende nicht-ionische Tenside sindAdvantageously used nonionic surfactants are
1. Alkohole1. Alcohols
2. Alkanolamide, wie Cocamide MEA/ DEA/ MIPA,2. alkanolamides, such as cocamide MEA / DEA / MIPA,
3. Aminoxide, wie Cocoamidopropylaminoxid,3. amine oxides, such as cocoamidopropylamine oxide,
4. Ester, die durch Veresterung von Carbonsäuren mit Ethylenoxid, Glycerin, Sorbitan oder anderen Alkoholen entstehen,4. Esters formed by esterification of carboxylic acids with ethylene oxide, glycerol, sorbitan or other alcohols,
5. Ether, beispielsweise ethoxylierte/propoxylierte Alkohole, ethoxylierte/ propoxylierte Ester, ethoxylierte/ propoxylierte Glycerinester, ethoxylierte/ propoxylierte Cholesterine, ethoxylierte/ propoxylierte Triglyceridester, ethoxyliertes propoxyliertes Lanolin, ethoxylierte/ propoxylierte Polysiloxane, propoxylierte POE-Ether und Alkyl- polyglycoside wie Laurylglucosid, Decylglycosid und Cocoglycosid.5. Ethers, for example ethoxylated / propoxylated alcohols, ethoxylated / propoxylated esters, ethoxylated / propoxylated glycerol esters, ethoxylated / propoxylated triglyceride esters, ethoxylated propoxylated lanolin, ethoxylated / propoxylated polysiloxanes, propoxylated POE ethers and alkyl polyglycosides such as lauryl glucoside, Decyl glycoside and cocoglycoside.
6. Sucroseester, -Ether6. sucrose ester, ether
7. Polyglycehnester, Diglycerinester, Monoglycerinester7. Polyglycehnester, Diglycerolester, Monoglycerinester
8. Methylglucosester, Ester von Hydroxysäuren8. Methyl glucose esters, esters of hydroxy acids
Vorteilhaft ist ferner die Verwendung einer Kombination von anionischen und/oder amphoteren Tensiden mit einem oder mehreren nicht-ionischen Tensiden.It is also advantageous to use a combination of anionic and / or amphoteric surfactants with one or more nonionic surfactants.
Erfindung:Invention:
Es wurde überraschend festgestellt, dass antimikrobielle kosmetische Zubereitungen enthaltend ein kationisches Styrol / Acrylat Copolymer erhältlich durch Copolymerisation aus Butylacrylat, Ethyltrimoniumchlorid-methacrylat und Styrol und höchstens 20 Gew.-% oberflächenaktive Substanzen den Nachteilen des Standes der Technik abhelfen. Solche kationischen Styrol / Acrylat Copolymere in Kombination mit oberflächenaktiver Substanzen wie z. B. Emulgatoren oder Tensiden verstärken die antiadhäsive Wirkung oder reduzieren sie zumindestens nicht. Formulierungen mit höheren Gehalten an Tensiden zeigen analoge Effekte, wenn der Anteil anionischer Tenside sehr gering ist. Darüber hinaus zeigen derartige Formulierungen keinerlei verstärkte Tensidadsorbtion auf der Haut und sind somit ausgezeichnet verträglich.It has surprisingly been found that antimicrobial cosmetic preparations containing a cationic styrene / acrylate copolymer obtainable by copolymerization of butyl acrylate, ethyltrimonium chloride methacrylate and styrene and at most 20 wt .-% surfactants to overcome the disadvantages of the prior art. Such cationic styrene / acrylate copolymers in combination with surface-active substances such. As emulsifiers or surfactants enhance the anti-adhesive effect or at least not reduce it. Formulations with higher levels of surfactants show similar effects when the proportion of anionic surfactants is very low. Moreover, such formulations do not show any increased surfactant adsorption on the skin and are thus excellently compatible.
Dabei ist es von Vorteil, wenn die oberflächenaktiven Substanzen aus der Gruppe der anionischen, kationischen, amphoteren oder nichtionischen Tenside bzw. deren Gemischen gewählt werden. Bevorzugt ist es, wenn der der Gehalt anionischer oberflächenaktiver Substanzen höchstens 5 Gew.-%, bevorzugt höchstens 3 Gew.-%, besonders bevorzugt höchstens 2,5 Gew.-% ist. Bevorzugt ist es, wenn das kationische Styrol / Acrylat Copolymer ein Polymer mit der INCI-Bezeichnung „Butyl Acrylate/Ethyltrimonium Chloride Methacrylate/Styrene Copolymer" ist. Besonders vorteilhaft sind Polymere, deren kationische Ladungen vor Abbau bzw. In- aktivierung geschützt und so auch nach längerer Dauer noch wirksam sind. Ein derartiger Schutz kann beispielsweise durch der kationischen Gruppe benachbarte nichtionische Seitenketten erfolgen. Solche Polymere sind z. B. in US 20050003163 beschrieben.It is advantageous if the surface-active substances are selected from the group of anionic, cationic, amphoteric or nonionic surfactants or mixtures thereof. It is preferred if the content of anionic surface-active substances is at most 5% by weight, preferably at most 3% by weight, particularly preferably at most 2.5% by weight. It is preferred if the cationic styrene / acrylate copolymer is a polymer with the INCI name "butyl acrylate / ethyltrimonium chloride methacrylates / styrene copolymer." Polymers whose cationic charges are free from degradation or Activation protected and so are still effective even after a long time. Such protection can be provided, for example, by the cationic group of adjacent nonionic side chains. Such polymers are for. As described in US 20050003163.
Besonders vorteilhaft bezüglich der deodorierenden Wirkung ist dabei ein Butyl Acryla- te/Ethyltrimonium Chloride Methacrylate/Styrene Copolymer, was von der Firma Dow Reichhold Specialty Latex unter dem Handelsnamen PolySaf™5600 vertrieben wird. PolySaf 5600 wird als - 40%ige wässrige Suspension angeboten und lässt sich gut in verschiedenste kosmetische Rezepturen einarbeiten.A particularly advantageous deodorant effect is a butyl acrylate / ethyltrimonium chloride methacrylate / styrene copolymer, which is sold by Dow Reichhold Specialty Latex under the trade name PolySaf ™ 5600. PolySaf 5600 is offered as a - 40% aqueous suspension and can be easily incorporated into a wide variety of cosmetic formulations.
Besonders von Vorteil ist es, wenn das kationische Styrol / Acrylat Copolymer in Aktivgehalten von 0,01 bis 4 Gew.-%, bevorzugt von 0,1 bis 3 Gew.-%, besonders bevorzugt von 0,5 bis 2 Gew.-% vorliegt. Die Erfindung umfasst auch die Verwendung von Zubereitungen nach einem der vorangehenden Patentansprüche als Deodorantien, deodorierende Produkte, Intimpflegemittel, Dusch- oder, Anti- Akne-Produkte.It is particularly advantageous if the cationic styrene / acrylate copolymer in active contents of 0.01 to 4 wt .-%, preferably from 0.1 to 3 wt .-%, particularly preferably from 0.5 to 2 wt .-% is present. The invention also includes the use of preparations according to any one of the preceding claims as deodorants, deodorizing products, personal care, shower or anti-acne products.
Versuche zur Untersuchung der Tensidadsorbtion zeigen, dass es zu keiner verstärkten Tensi- dadsorption kommt. Im folgenden werden die Methode und Ergebnisse der durchgeführten Tensidadsorptionstests beschrieben:Attempts to investigate the Tensidadsorbtion show that there is no increased Tensidadsadsorption. The following describes the method and results of the surfactant adsorption tests carried out:
Ziel:Aim:
Quantitative Bestimmung der Substantiv aufgezogenen Menge von Sodium Laureth Sulfate,Quantitative determination of the noun-fed amount of sodium laureth sulfate,
Cocamidopropyl Betaine und Sodium Cocoamphoacetate aus Duschformulierungen auf derCocamidopropyl betaines and sodium cocoamphoacetate from shower formulations on the
Haut (Duschformulierungen mit bzw. ohne beschriebenes kationisches Polymer ((PolySaf 5600;Skin (shower formulations with or without described cationic polymer ((PolySaf 5600;
40% wässrige Dispersion) bzw. mit Chitosan). Die Probenentnahme erfolgte nach einmaliger40% aqueous dispersion) or with chitosan). The sample was taken after one-time
Anwendung. Application.
Durchführung: Probandenzahl: 20Execution: Number of test persons: 20
Anwendung:Application:
Die Unterarm-Areale (Fläche = 4,91 cm2) wurden mit 500 μl_ Produkt 30s eingeschäumt, anschließend mit 1 L Wasser abgespült und mit Zellstoff trockengetupft. Die Extraktion der Areale wurde mit 1 ml_ 1 %iger Triton X-100 Lösung durchgeführt. Die Extrakte wurden 1 :10 mit Wasser verdünnt, filtriert und anschließend direkt vermessen. Die quantitative Bestimmung von So- dium Laureth Sulfate (LES), Cocamidopropyl Betaine (CAPB) und Sodium Cocoamphoacetate (CAA) erfolgte mittels LC-MS (externe Standardkalibrierung). Als Referenzsubstanzen wurden die Rohstoffe TEXAPON N 70 (LES Cognis), Aktivgehalt 70% und REWOTERIC AM C (CAA Evonik Goldschmidt), Aktivgehalt 32,5%, verwendet. Die angegebenen Gehalte beziehen sich auf die verwendenten Referenzsubstanzen; zur Berechnung der absoluten Tensidgehalte müssen die angegebenen Ergebnisse um den von 100% abweichenden Aktivgehalt korrigiert werden.The forearm areas (area = 4.91 cm 2 ) were foamed with 500 ul_ product 30s, then rinsed with 1 L of water and blotted dry with pulp. Extraction of the areas was performed with 1 ml of 1% Triton X-100 solution. The extracts were diluted 1:10 with water, filtered and then measured directly. Quantitative determination of sodium laureth sulfate (LES), cocamidopropyl betaine (CAPB) and sodium cocoamphoacetate (CAA) was performed by LC-MS (external standard calibration). The reference substances used were the raw materials TEXAPON N 70 (LES Cognis), active content 70% and REWOTERIC AM C (CAA Evonik Goldschmidt), active content 32.5%. The contents given refer to the reference substances used; To calculate the absolute surfactant contents, the results given must be corrected by the activity content deviating from 100%.
Ergebnisse:Results:
Test iTest i
Probencodierungsample coding
(01 ) Unbehandelt(01) Untreated
(10) Standarddusche mit 6,5% Sodium Laureth Sulfate (ohne Chitosan)(10) Standard shower with 6.5% sodium laureth sulfate (without chitosan)
(20) Duschformulierung ohne Chitosan mit 2,1% LES, 7,2% Sodium(20) Shower formulation without chitosan with 2.1% LES, 7.2% sodium
Cocoamphoacetate (30) Duschformulierung mit Chitosan mit 2,1 % LES, 7,2% SodiumCocoamphoacetate (30) Shower formulation with chitosan containing 2.1% LES, 7.2% sodium
Cocoamphoacetatecocoamphoacetates
Ergebnis:Result:
Deutlich erhöhte Adsorption von Sodium Laureth Sulfate und Sodium Cocoamphoacetate aus der Duschformulierung mit Chitosan (30) 01 10 20 30Significantly Increased Adsorption of Sodium Laureth Sulfate and Sodium Cocoamphoacetate from the Shower Formulation with Chitosan (30) 01 10 20 30
Cocoamphoace- Cocoamphoace- Cocoamphoace- Cocoamphoace-Cocoamphoace Cocoamphoace Cocoamphoace Cocoamphoace
Proband LES (μg/Areal) tat (μg/Areal) LES (μg/Areal) tat (μg/Areal) LES (μg/Areal) tat (μg/Areal) LES (μg/Areal) tat (μg/Areal)Test person LES (μg / areal) tat (μg / areal) LES (μg / areal) tat (μg / areal) LES (μg / areal) tat (μg / areal) LES (μg / areal) tat (μg / areal)
1-1 0,08 0,38 11 ,84 0,41 7,47 42,57 29,23 121,451-1 0.08 0.38 11, 84 0.41 7.47 42.57 29.23 121.45
1-2 0,05 0,30 13,22 0,45 5,87 35,41 34,68 156,191-2 0.05 0.30 13.22 0.45 5.87 35.41 34.68 156.19
2-1 0,06 0,00 10,20 0,29 5,26 27,82 17,91 74,652-1 0.06 0.00 10.20 0.29 5.26 27.82 17.91 74.65
2-2 0,07 0,00 11,39 0,35 5,82 30,81 20,53 76,652-2 0.07 0.00 11.39 0.35 5.82 30.81 20.53 76.65
3-1 0,04 0,00 6,12 0,22 3,66 20,69 39,84 129,733-1 0,04 0,00 6,12 0,22 3,66 20,69 39,84 129,73
3-2 0,02 0,00 7,49 0,29 2,41 13,54 30,96 104,363-2 0.02 0.00 7.49 0.29 2.41 13.54 30.96 104.36
4-1 0,03 0,00 8,13 0,26 4,30 21,50 15,34 77,814-1 0.03 0.00 8.13 0.26 4.30 21.50 15.34 77.81
4-2 0,02 0,00 8,40 0,27 4,77 29,45 16,90 70,004-2 0.02 0.00 8.40 0.27 4.77 29.45 16.90 70.00
5-1 0,06 0,32 13,46 0,77 5,53 36,13 15,85 96,835-1 0.06 0.32 13.46 0.77 5.53 36.13 15.85 96.83
5-2 0,04 0,32 1 1,85 0,35 4,93 31,62 28,16 134,785-2 0.04 0.32 1 1.85 0.35 4.93 31.62 28.16 134.78
6-1 0,05 0,00 1 1,98 0,46 5,00 34,39 24,52 107,596-1 0.05 0.00 1 1.98 0.46 5.00 34.39 24.52 107.59
6-2 0,04 0,00 9,98 0,34 5,25 31,60 18,54 74,376-2 0.04 0.00 9.98 0.34 5.25 31.60 18.54 74.37
7-1 0,00 0,00 14,47 0,63 5,96 37,41 34,1 1 134,707-1 0.00 0.00 14.47 0.63 5.96 37.41 34.1 1 134.70
7-2 0,00 0,00 13,37 0,52 7,00 37,53 51,68 226,507-2 0.00 0.00 13.37 0.52 7.00 37.53 51.68 226.50
8-1 0,14 0,00 25,01 0,93 10,07 73,65 49,27 200,598-1 0.14 0.00 25.01 0.93 10.07 73.65 49.27 200.59
8-2 0,09 0,00 19,82 0,70 7,23 51,95 45,14 201,918-2 0.09 0.00 19.82 0.70 7.23 51.95 45.14 201.91
9-1 0,25 0,36 12,24 0,45 7,09 36,35 24,30 81,459-1 0.25 0.36 12.24 0.45 7.09 36.35 24.30 81.45
9-2 0,20 0,50 11,02 0,49 6,64 31,06 19,92 64,979-2 0,20 0,50 11,02 0,49 6,64 31,06 19,92 64,97
10-1 0,06 0,00 10,03 0,30 4,47 23,31 23,01 113,5710-1 0.06 0.00 10.03 0.30 4.47 23.31 23.01 113.57
10-2 0,06 0,00 12,79 0,47 5,22 28,54 30,77 141,3410-2 0.06 0.00 12.79 0.47 5.22 28.54 30.77 141.34
1 1-1 0,05 0,00 1 1,09 0,35 3,21 19,89 14,64 45,291 1-1 0.05 0.00 1 1.09 0.35 3.21 19.89 14.64 45.29
11-2 0,04 0,00 13,46 0,40 3,85 18,61 14,75 52,1511-2 0.04 0.00 13.46 0.40 3.85 18.61 14.75 52.15
12-1 0,08 0,58 19,98 0,70 11,30 59,93 26,97 1 11,2412-1 0.08 0.58 19.98 0.70 11.30 59.93 26.97 1 11.24
12-2 0,08 0,77 14,9» 0,52 9,40 55,78 30,61 141,8312-2 0.08 0.77 14.9 »0.52 9.40 55.78 30.61 141.83
13-1 0,05 0,19 14,16 0,49 3,87 25,26 1 1,76 41,4313-1 0.05 0.19 14.16 0.49 3.87 25.26 1 1.76 41.43
13-2 0,08 0,22 13,36 0,44 4,82 26,61 14,25 65,4413-2 0.08 0.22 13.36 0.44 4.82 26.61 14.25 65.44
14-1 0,03 0,00 5,68 0,00 2,37 11,88 8,77 32,4314-1 0.03 0.00 5.68 0.00 2.37 11.88 8.77 32.43
14-2 0,03 0,25 . _ 2,93 16,58 10,67 40,0914-2 0.03 0.25. _ 2,93 16,58 10,67 40,09
15-1 0,02 0,00 4,86 0,00 2,76 14,99 7,69 24,7015-1 0.02 0.00 4.86 0.00 2.76 14.99 7.69 24.70
15-2 0,02 0,00 5,78 0,22 3,49 21,36 1 1,09 39,6015-2 0.02 0.00 5.78 0.22 3.49 21.36 1 1.09 39.60
16-1 0,39 0,00 14,04 0,39 7,43 48,40 14,52 73,4316-1 0.39 0.00 14.04 0.39 7.43 48.40 14.52 73.43
16-2 0,49 0,00 9,43 0,32 7,98 50,97 20,28 110,6716-2 0.49 0.00 9.43 0.32 7.98 50.97 20.28 110.67
17-1 0,02 0,32 3,86 0,00 2,11 9,76 8,07 22,1817-1 0.02 0.32 3.86 0.00 2.11 9.76 8.07 22.18
17-2 0,02 0,00 4,72 0,00 1,93 10,45 14,32 45,8417-2 0.02 0.00 4.72 0.00 1.93 10.45 14.32 45.84
18-1 0,10 0,00 5,62 0,23 2,70 15,03 13,23 52,4218-1 0.10 0.00 5.62 0.23 2.70 15.03 13.23 52.42
18-2 0,09 0,00 7,69 0,22 2,23 13,69 14,31 57,7418-2 0.09 0.00 7.69 0.22 2.23 13.69 14.31 57.74
19-1 0,15 0,00 16,06 0,44 2,45 8,90 6,34 14,0119-1 0.15 0.00 16.06 0.44 2.45 8.90 6.34 14.01
19-2 0,15 0,00 12,89 0,30 3,03 9,86 5,21 14,4119-2 0.15 0.00 12.89 0.30 3.03 9.86 5.21 14.41
20-1 0,07 0,00 14,48 0,36 5,40 34,86 1 1,06 46,5320-1 0.07 0.00 14.48 0.36 5.40 34.86 1 1.06 46.53
20-2 0,08 0,00 14,91 0,36 3,09 18,02 12,28 52,6220-2 0.08 0.00 14.91 0.36 3.09 18.02 12.28 52.62
Mittelwert 0,08 0,11 1 1,53 0,38 5,01 29,15 21,04 86,84Mean 0.08 0.11 1 1.53 0.38 5.01 29.15 21.04 86.84
Stabw 0,10 0,19 4,48 0,20 2,28 15,15 11,70 52,19Stabw 0,10 0,19 4,48 0,20 2,28 15,15 11,70 52,19
Var % 115,8% 173,4% 38,8% 53,8% 45,6% 52,0% 55,6% 60,1%Var% 115.8% 173.4% 38.8% 53.8% 45.6% 52.0% 55.6% 60.1%
Sodiumcocoamphoacetat: 0,00 entspricht < Bestimmungsgrenze (0,15 μg/Areal)Sodium cocoamphoacetate: 0.00 corresponds to <determination limit (0.15 μg / areal)
Siehe Abbildung 1See Figure 1
Test 2Test 2
Probencodierungsample coding
(01 ) unbehandelt(01) untreated
(10) Duschformulierung mit Chitosan mit 2,1% LES, 7,2% Sodium(10) Shower formulation with chitosan with 2.1% LES, 7.2% sodium
Cocoamphoacetate, 2,9% Cocamidopropyl Betaine (20) Duschformulierung ohne neues kat. Polymer mit 2,1% LES, 10,1%Cocoamphoacetate, 2.9% Cocamidopropyl Betaine (20) Shower formulation without new cat. Polymer with 2.1% LES, 10.1%
Cocamidopropyl Betaine (30) Duschformulierung mit neuem kat. Polymer (PolySaf 5600 (40% wässrigeCocamidopropyl Betaine (30) Shower formulation with new cat. Polymer (PolySaf 5600 (40% aqueous
Dispersion)) mit 2,1% LES, 10,1% Cocamidopropyl Betaine Ergebnis:Dispersion)) with 2.1% LES, 10.1% cocamidopropyl betaines Result:
Deutlich erhöhte Adsorption von Sodium Laureth Sulfate aus der Formulierung mit Chitosan (10) im Vergleich zu den Duschformulierungen mit neuem kat. Polymer (30) bzw. Placebo (20). Auch Betain wird im Verhältnis zur eingesetzten Menge stärker adsorbiert sowie zusätzlich Sodium Cocoamphoacetate (nicht im Diagramm aufgeführt), so dass die gesamte Tensidmenge, die aus der Formulierung (10) mit Chitosan auf der Haut adsorbiert wird, um ein Vielfaches höher ist als aus der Formulierung mit dem neuem kat. Polymer.Significantly increased adsorption of sodium laureth sulfate from the formulation with chitosan (10) compared to the shower formulations with new cat. Polymer (30) or placebo (20). Also, betaine is more strongly adsorbed in relation to the amount used and in addition sodium cocoamphoacetate (not shown in the diagram), so that the total amount of surfactant adsorbed on the skin from the formulation (10) with chitosan is many times higher than that Wording with the new kat. Polymer.
01 10 20 3001 10 20 30
Cocoampho Cocoampho;Cocoampho Cocoampho;
LES Betain cetat LES Betain cetat LES Betain LES BetainLES Betain cetat LES Betain cetat LES Betain LES betaine
Proband (μg/Areal) (μg/Areal) (μg/Areal) (μg/Areal) (μg/Areal) (μg/Areal) (μg/Areal) (μg/Areal) (μg/Areal) (μg/Areal)Subject (μg / Areal) (μg / Areal) (μg / Areal) (μg / Areal) (μg / Areal) (μg / Areal) (μg / Areal) (μg / Areal) (μg / Areal) (μg / Areal) )
1 1,59 0,84 0,00 40,00 59,35 159,33 12,13 57,51 4,67 26,481 1.59 0.84 0.00 40.00 59.35 159.33 12.13 57.51 4.67 26.48
2 3,16 0,54 0,00 28,35 21,93 68,23 15,21 31,20 7,09 25,962 3.16 0.54 0.00 28.35 21.93 68.23 15.21 31.20 7.09 25.96
3 2,18 0,58 0,00 31,42 28,67 90,67 17,64 46,69 8,16 38,073 2.18 0.58 0.00 31.42 28.67 90.67 17.64 46.69 8.16 38.07
4 1,O5 0,00 0,00 42,95 66,17 211,84 14,27 69,75 12,08 85,794 1, O 5 0.00 0.00 42.95 66.17 211.84 14.27 69.75 12.08 85.79
5 0,83 0,00 0,00 36,19 58,87 167,87 7,24 29,13 2,47 13,715 0.83 0.00 0.00 36.19 58.87 167.87 7.24 29.13 2.47 13.71
6 1,40 0,66 0,00 27,01 40,47 120,81 4,50 31,35 13,57 68,126 1.40 0.66 0.00 27.01 40.47 120.81 4.50 31.35 13.57 68.12
7 0,49 0,00 0,00 16,54 19,09 64,07 5,06 15,86 2,23 10,987 0.49 0.00 0.00 16.54 19.09 64.07 5.06 15.86 2.23 10.98
8 0,34 0,00 0,00 32,49 43,24 127,62 10,52 45,30 5,47 30,008 0.34 0.00 0.00 32.49 43.24 127.62 10.52 45.30 5.47 30.00
9 1,52 0,61 0,00 54,91 72,99 209,49 18,03 94,15 10,81 80,409 1.52 0.61 0.00 54.91 72.99 209.49 18.03 94.15 10.81 80.40
10 0,15 0,00 0,00 31,19 34,24 105,99 7,28 21,68 3,86 24,9710 0.15 0.00 0.00 31.19 34.24 105.99 7.28 21.68 3.86 24.97
11 1,67 0,00 0,00 47,91 62,66 156,55 6,70 26,53 51,70 69,3611 1.67 0.00 0.00 47.91 62.66 156.55 6.70 26.53 51.70 69.36
I2 2,31 0,49 0,00 33,87 49,26 125,16 8,84 38,07 3,70 21,88I 2 2.31 0.49 0.00 33.87 49.26 125.16 8.84 38.07 3.70 21.88
13 0,42 0,00 0,00 28,26 42,99 108,87 7,65 47,76 2,49 19,7713 0.42 0.00 0.00 28.26 42.99 108.87 7.65 47.76 2.49 19.77
14 2,18 0,66 0,00 37,72 60,23 155,66 14,17 91,34 6,07 49,3714 2.18 0.66 0.00 37.72 60.23 155.66 14.17 91.34 6.07 49.37
I5 1,49 0,48 0,14 28,50 49,46 131,69 8,89 49,08 5,68 50,30I 5 1.49 0.48 0.14 28.50 49.46 131.69 8.89 49.08 5.68 50.30
16 1,67 0,46 0,00 18,49 23,40 65,64 7,74 32,48 3,55 20,1916 1.67 0.46 0.00 18.49 23.40 65.64 7.74 32.48 3.55 20.19
17 2,62 0,00 0,00 21,06 23,05 70,76 8,40 37,87 4,46 21,5717 2.62 0.00 0.00 21.06 23.05 70.76 8.40 37.87 4.46 21.57
18 1,1 1 0,79 0,00 32,24 42,72 1 19,12 12,18 60,33 4,15 31,1418 1.1 1 0.79 0.00 32.24 42.72 1 19.12 12.18 60.33 4.15 31.14
19 0,64 0,00 0,00 26,50 28,66 84,59 5,74 16,74 2,76 17,7619 0.64 0.00 0.00 26.50 28.66 84.59 5.74 16.74 2.76 17.76
20 3,53 2,37 0,00 39,23 58,91 168,83 9,23 43,03 5,10 24,3020 3.53 2.37 0.00 39.23 58.91 168.83 9.23 43.03 5.10 24.30
Mittelwert 1,52 0,42 0,01 32,74 44,32 125,64 10,07 44,29 8,00 36,51Mean 1.52 0.42 0.01 32.74 44.32 125.64 10.07 44.29 8.00 36.51
Stabw 0,94 0,56 0,03 9,44 16,59 45,01 4,04 21,77 10,78 22,78Stabw 0.94 0.56 0.03 9.44 16.59 45.01 4.04 21.77 10.78 22.78
Var % 61,7% 131,5% 447,2% 28,8% 37,4% 35,8% 40,1% 49,2% 134,6% 62,4%Var% 61.7% 131.5% 447.2% 28.8% 37.4% 35.8% 40.1% 49.2% 134.6% 62.4%
Sodium Cocoamphoacetat: 0,00 entspricht < Bestimmungsgrenze (0,15 μg/mL) Betain: 0,00 entspricht < Bestimmungsgrenze (0,1 μg/mL)Sodium cocoamphoacetate: 0.00 corresponds to <determination limit (0.15 μg / mL) Betaine: 0.00 corresponds to <determination limit (0.1 μg / mL)
Siehe Abbildung 2See Figure 2
Versuche zur Untersuchung der antiadhäsiven Wirkung zeigen eine sehr gute Reduktion der bakteriellen Adhäsion durch erfindungsgemäfSe Zubereitungen. Durchführung:Attempts to investigate the antiadhesive effect show a very good reduction of bacterial adhesion by preparations according to the invention. Execution:
Bakterien einer LINK (Übernacht-Kultur) werden abzentrifugiert, mit Puffer gewaschen, 30 min in 70% EtOH fixiert und mit Propidiumiodid gefärbt. Der überschüssige Farbstoff wird durch mehrmaliges Waschen entfernt. Die Bakterien werden für 1 Std. mit den Rohstoffen (Anti- Adhäsiva) inkubiert. Anschließend werden die Bakteriensuspensionen mit humanen Corneocy- ten, die vom Unterarm eines Probanden gewonnen werden, 1 Std. bei RT (Raumtemperatur) inkubiert. Nach dieser Adhäsionsperiode werden die Bakterien-Corneocyten-Komplexe durch Abtrennung der nicht-adhärenten Bakterien gewonnen und die Adhäsionsrate durchflusszyto- metrisch bestimmt und mikroskopisch kontrolliert. Die Adhäsionsrate des Kontrollansatzes, in dem Bakterien (nicht vorbehandelt) und Comeozyten inkubiert werden, wird als 100 % relative Adhäsionsrate definiert. Alle anderen Ansätze werden in Relation dazu berechnet. Werte < 100% zeigen eine Inhibition der bakteriellen Adhäsion an, Werte > 100 % eine verstärkte bakterielle Adhäsion an.Bacteria of a LINK (overnight culture) are centrifuged off, washed with buffer, fixed in 70% EtOH for 30 min and stained with propidium iodide. The excess dye is removed by washing several times. The bacteria are incubated for 1 h with the raw materials (anti-adhesives). Subsequently, the bacterial suspensions are incubated with human corneocytes, which are obtained from the forearm of a subject, for 1 h at RT (room temperature). After this adhesion period, the bacteria-corneocyte complexes are obtained by separation of the non-adherent bacteria and the adhesion rate is determined by flow cytometry and controlled microscopically. The rate of adhesion of the control batch, in which bacteria (not pretreated) and Comeozyten are incubated, is defined as 100% relative Adhäsungsrate. All other approaches are calculated in relation to it. Values <100% indicate an inhibition of bacterial adhesion, values> 100% an increased bacterial adhesion.
In folgender Grafik sind die relativen Adhäsionsraten nach Inkubation mit einem kationischen Beispielpolymer (PolySaf 5600; 40%ige wässrige Dispersion) und Tensidmischungen mit und ohne kationisches Polymer dargestellt.The graph below shows the relative rates of adhesion after incubation with a cationic example polymer (PolySaf 5600, 40% aqueous dispersion) and surfactant mixtures with and without cationic polymer.
Das Beispielpolymer zeigt eine sehr gute Reduktion der bakteriellen Adhäsion auf 19% relative Adhäsionsrate. Beide Tensidformulierungen zeigen einen leichten Einfluss auf die Adhäsion (auf 85, bzw. 95%). Tensidformulierung 1 mit einem höheren Gehalt an anionischen Tensiden zeigt eine starke Beeinflussung der Wirksamkeit des kationischen Polymers. Tensidformulierung 2 hingegen, mit einem deutlich geringeren Gehalt an anionischen Tensiden, kann die Wirksamkeit des Beispielpolymers sogar noch steigern (auf 14% relative Adhäsionsrate).The example polymer shows a very good reduction in bacterial adhesion to 19% relative adhesion rate. Both surfactant formulations show a slight influence on the adhesion (85% and 95%, respectively). Surfactant formulation 1 with a higher content of anionic surfactants shows a strong influence on the effectiveness of the cationic polymer. In contrast, surfactant formulation 2, with a significantly lower content of anionic surfactants, can even increase the effectiveness of the example polymer (to 14% relative adhesion rate).
Siehe Abbildung 3See Figure 3
Abb. : Anti-adhäsive Wirksamkeit von Tensidformulierungen.Fig.: Anti-adhesive effectiveness of surfactant formulations.
Folgende Grafik zeigt den Einfluss des kationischen Polymers PolySaf 5600 (als 40% wässrige Dispersion) auf die relative Adhäsionsrate. Das Polymer alleine reduziert die relative Adhäsionsrate auf einen Wert von 19%. In eine Deoformulierung eingearbeitet liegt die Wirksamkeit des Polymers PolySaf 5600 auf einem ähnlichen Niveau (relative Adhäsionsrate von 22%), während die Formulierung selbst keinerlei Einfluss aufweist. Siehe Abbildung 4The following graph shows the influence of the cationic polymer PolySaf 5600 (as a 40% aqueous dispersion) on the relative adhesion rate. The polymer alone reduces the relative adhesion rate to a value of 19%. When incorporated into a de-formulation, the effectiveness of the PolySaf 5600 polymer is at a similar level (relative adhesion rate of 22%) while the formulation itself has no effect. See Figure 4
Abb. : Anti-adhäsive Wirksamkeit kationischer Polymere in DeoformulierungenFig.: Anti-adhesive effectiveness of cationic polymers in deodorizing
Darüber hinaus können Formulierungen auf Basis solcher Kombinationen weitere Komponenten enthalten wie z.B. Konservierungsmittel, Stabilisatoren, Puffersubstanzen, Verdickungsmittel, Parfüms, Perlglanzmittel, Trübungsmittel, Komplexierungsmittel, Feuchthaltemittel, Lösemittel, Farbstoffe, Öle, Extrakte, Vitamine, Antioxidantien, UV-Filter.In addition, formulations based on such combinations may contain other components, e.g. Preservatives, stabilizers, buffering agents, thickeners, perfumes, pearlescing agents, opacifiers, complexing agents, humectants, solvents, dyes, oils, extracts, vitamins, antioxidants, UV filters.
Ebenfalls bevorzugt kann die Kombination mit weiteren Deowirkstoffen wie beispielsweise Tric- losan, Chlorhexidin oder die natürlich vorkommenden Verbindungen wie Famesol, 2-butyl- octansäure und Phenoxyethanol sein. Auch die Kombination mit Aluminiumsalzen wie Aluminiumhydroxychlorid (Aluminiumchlorohydrat) oder Aluminium/Zirkoniumsalze kann bevorzugt sein.Also preferred may be the combination with other Deowirkstoffen such as triclosan, chlorhexidine or the naturally occurring compounds such as Famesol, 2-butyl octanoic acid and phenoxyethanol. Also, the combination with aluminum salts such as aluminum hydroxychloride (aluminum chlorohydrate) or aluminum / zirconium salts may be preferred.
Beispielformulierungen für unterschiedliche Anwendungsbereiche sind Deo-Applikationen, Deo- Duschen, Intimpflegemittel, Antischuppenshampoo, Fußbad, -pflege, Gesichtsreinigung oder Anti Akne Produkte. Example formulations for a variety of applications are deodorant applications, deodorant showers, personal care products, anti-dandruff shampoo, foot bath, skin care, facial cleansing or anti-acne products.
Beispielrezepturen:Example recipes:
Beispiel 15 Example 15
Beispiel 17 Example 17
Die durch Zusammenmischung der jeweiligen Bestandteile erhaltene flüssige Phase wird mit einem Propan-Butan-Gemisch (2.7) im Verhältnis 39:61 in Aerosolbehälter abgefüllt.The liquid phase obtained by mixing together the respective components is filled with a propane-butane mixture (2.7) in a ratio of 39:61 in aerosol containers.
Beispiel 18Example 18
Die durch Zusammenmischung der jeweiligen Bestandteile erhaltene flüssige Phase wird mit einem Propan-Butan-Gemisch (2.7) im Verhältnis 17:83 in Aerosolbehälter abgefüllt. The liquid phase obtained by mixing the respective components together with a propane-butane mixture (2.7) in the ratio 17:83 filled in aerosol container.
Beispiel 19Example 19
Beispiel 21 -23 Example 21 -23
Beispiel 24 Beispiel 25Example 24 Example 25
Beispiel 26Example 26
Die durch Zusammenmischung der jeweiligen Bestandteile erhaltene flüssige Phase wird mit einem Propan-Butan-Gemisch (2.7) im Verhältnis 19:81 in Aerosolbehälter abgefüllt. The liquid phase obtained by mixing together the respective components is filled with a propane-butane mixture (2.7) in the ratio 19:81 in aerosol containers.
Beispiel 27:Example 27:
Beispiel 28:Example 28:
Beispiel 29 - RezepturenExample 29 - Recipes
Der pH-Wert der Duschgele beträgt 4,8 - 5,3: Die Viskosität liegt zwischen 2000 und 5000 mPa. The pH of the shower gels is 4.8 - 5.3: The viscosity is between 2000 and 5000 mPa.

Claims

Patentansprüche claims
1. Antimikrobielle kosmetische Zubereitungen enthaltend ein kationisches Styrol / Acrylat Copolymer erhältlich durch Copolymerisation aus Butylacrylat, Ethyltrimoniumchlorid- methacrylat und Styrol und höchstens 20 Gew.-% oberflächenaktive Substanzen.1. Antimicrobial cosmetic preparations containing a cationic styrene / acrylate copolymer obtainable by copolymerization of butyl acrylate, Ethyltrimoniumchlorid- methacrylate and styrene and at most 20 wt .-% of surface-active substances.
2. Zubereitung nach Patentanspruch 1 dadurch gekennzeichnet, dass die oberflächenaktiven Substanzen aus der Gruppe der anionischen, kationischen, amphoteren oder nichtionischen Tenside bzw. deren Gemischen gewählt werden.2. Preparation according to claim 1, characterized in that the surface-active substances from the group of anionic, cationic, amphoteric or nonionic surfactants or mixtures thereof are selected.
3. Zubereitungen nach einem der vorangehenden Patentansprüche dadurch gekennzeichnet, dass der Gehalt an oberflächenaktiven Substanzen höchstens 15 Gew.-% ist.3. Preparations according to one of the preceding claims, characterized in that the content of surface-active substances is at most 15 wt .-%.
4. Zubereitungen nach einem der vorangehenden Patentansprüche 1 oder 2 dadurch gekennzeichnet, dass der Gehalt anionischer oberflächenaktiver Substanzen höchstens 5 Gew.-% ist.4. Preparations according to one of the preceding claims 1 or 2, characterized in that the content of anionic surface-active substances is at most 5 wt .-%.
5. Zubereitungen nach Anspruch 1 , 2 oder 3 dadurch gekennzeichnet, dass der Gehalt an anionischen oberflächenaktiven Substanzen höchstens 4 Gew.-% ist.5. Preparations according to claim 1, 2 or 3, characterized in that the content of anionic surface-active substances is at most 4 wt .-%.
6. Zubereitungen nach Anspruch 1 , 2, 3 oder 4 dadurch gekennzeichnet, dass der Gehalt an anionischen oberflächenaktiven Substanzen höchstens 2,5 Gew.-% ist.6. Preparations according to claim 1, 2, 3 or 4, characterized in that the content of anionic surface-active substances is at most 2.5 wt .-%.
7. Zubereitung nach einem der vorangehenden Patentansprüchen, dadurch gekennzeichnet, dass die kationischen Ladungen des kationischen Styrol / Acrylat Copolymers durch benachbarte nichtionische Seitenketten vor Abbau bzw. Inaktivierung geschützt sind.7. Preparation according to one of the preceding claims, characterized in that the cationic charges of the cationic styrene / acrylate copolymer are protected by adjacent nonionic side chains from degradation or inactivation.
8. Zubereitung nach einem der vorangehenden Patentansprüchen, dadurch gekennzeichnet, dass das kationisches Styrol / Acrylat Copolymer ein Polymer mit der INCI-Bezeichnung „Butyl Acrylate/Ethylthmonium Chloride Methacrylate/Styrene Copolymer" ist.8. Preparation according to one of the preceding claims, characterized in that the cationic styrene / acrylate copolymer is a polymer with the INCI name "butyl acrylates / Ethylthmonium Chloride Methacrylates / Styrene Copolymer".
9. Zubereitungen nach einem der vorangehenden Patentansprüche dadurch gekennzeichnet, dass das kationische Styrol / Acrylat Copolymer in Aktivgehalten von 0,01 bis9. Preparations according to one of the preceding claims, characterized in that the cationic styrene / acrylate copolymer in active contents of 0.01 to
4 Gew.-%, bevorzugt von 0,1 bis 3 Gew.-%, besonders bevorzugt von 0,5 bis 2,0 Gew.-% vorliegt. 4 wt .-%, preferably from 0.1 to 3 wt .-%, particularly preferably from 0.5 to 2.0 wt .-% is present.
0. Verwendung von Zubereitungen nach einem der vorangehenden Patentansprüche als Deodorantien, deodorierende Produkte, Intimpflegemittel, Dusch- oder Anti-Akne- Produkte. 0. Use of preparations according to one of the preceding claims as deodorants, deodorants, personal hygiene products, shower or anti-acne products.
EP09745484A 2008-05-13 2009-03-18 Antimicrobial cosmetic preparations Ceased EP2276456A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008001726A DE102008001726A1 (en) 2008-05-13 2008-05-13 ANTIMICROBIAL COSMETIC PREPARATION
PCT/EP2009/001993 WO2009138150A1 (en) 2008-05-13 2009-03-18 Antimicrobial cosmetic preparations

Publications (1)

Publication Number Publication Date
EP2276456A1 true EP2276456A1 (en) 2011-01-26

Family

ID=40749280

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09745484A Ceased EP2276456A1 (en) 2008-05-13 2009-03-18 Antimicrobial cosmetic preparations

Country Status (3)

Country Link
EP (1) EP2276456A1 (en)
DE (1) DE102008001726A1 (en)
WO (1) WO2009138150A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9717930B2 (en) 2013-03-12 2017-08-01 The Procter & Gamble Company Antiperspirant compositions
MX359860B (en) 2013-03-12 2018-10-11 Procter & Gamble Solid stick antiperspirant compositions.
MX367383B (en) 2014-06-30 2019-08-19 Procter & Gamble Method of manufacturing stick comprising antiperspirant.
WO2016003948A1 (en) 2014-06-30 2016-01-07 The Procter & Gamble Company Personal care compositions and methods

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009137016A2 (en) * 2008-05-06 2009-11-12 Mallard Creek Polymers, Inc. Antimicrobial and antistatic polymers and methods of using such polymers on various substrates

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19503423A1 (en) 1995-02-03 1996-08-08 Beiersdorf Ag Antiadhesive agents
US7491753B2 (en) 2003-07-03 2009-02-17 Mallard Creek Polymers, Inc. Antimicrobial and antistatic polymers and methods of using such polymers on various substrates
DE102005048776A1 (en) 2005-10-07 2007-04-12 Beiersdorf Ag Deodorizing cleaning preparation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009137016A2 (en) * 2008-05-06 2009-11-12 Mallard Creek Polymers, Inc. Antimicrobial and antistatic polymers and methods of using such polymers on various substrates

Also Published As

Publication number Publication date
DE102008001726A1 (en) 2009-11-19
WO2009138150A1 (en) 2009-11-19

Similar Documents

Publication Publication Date Title
EP2881381B1 (en) Polyglycerine partial esters, their preparation and use
KR101090045B1 (en) Concentrated ingredient for treating and/or modifying surfaces and the use thereof in cosmetic compositions
WO2009138194A1 (en) Cosmetic preparations against dandruff
EP3122316B1 (en) Oil-in-water emulsions containing 4-hydroxyacetophenone and anionic emulsifiers
EP2931378B1 (en) Cosmetic preparations with a flow point
WO2009135683A1 (en) Haircare formulations with cationically amphoteric polymers
EP1366742B1 (en) Mild hair conditioning shampoo comprising quaternised guar and cellulose derivatives
EP2276456A1 (en) Antimicrobial cosmetic preparations
DE10355716A1 (en) Cosmetic preparations containing creatine and / or creatine derivatives and / or creatinine and / or creatinine derivatives and organic thickeners
EP1384467B1 (en) Shampoo for fine and greasy hair
WO2003007908A2 (en) Cosmetic or dermatological preparations having a long-term cooling action
WO2018172332A1 (en) Foaming cleaning preparation containing polyquaternium-16 polymers
EP1872771A2 (en) Hair care cleaning preparation with special dry hair sensor technology
EP1880712A2 (en) Hair cleaning compounds with special sensor capability
EP1366738A1 (en) Conditioning shampoo
DE10123989A1 (en) Use of salts(s) of trivalent or tetravalent metal ion with oligo- or polysaccharide(s) in composition for reducing production of and/or for removing sebum
DE10050155A1 (en) Stabilization of cosmetic or dermatological emulsions, hydrogels or oleogels useful eg as skin-care or make-up compositions is by addition of desferrioxamine
DE19643586A1 (en) Topical sterol formulation for use as deodorant
DE102004027329A1 (en) Cosmetic preparation, useful as cosmetic cleaning preparation, shower gel, shampoo and/or face cleaner, comprises alkylethercarboxylate, ethoxylated glycerin, ethoxylated glycerin fatty acid ester and water
DE10111048A1 (en) Alpha-lipoic acid is used in cosmetics or dermatological compositions as an agent to regenerate stressed (especially aged) skin
WO2019149425A1 (en) Cleaning preparation containing polyquaternium-6 polymers
EP1366739A1 (en) Conditioning shampoo
DE102004027325A1 (en) Cosmetic preparation, useful e.g. as cosmetic cleaning preparation, shampoo and face cleaner, comprises alkyl ether carboxylate, ethoxylated glycerin, N-acylamino acid and water
DE10240029A1 (en) Synergistic antimycotic combinations of climbazole, piroctone olamine and undecyleneamidopropyl betaine, useful for combating seborrheic disorders, especially dandruff
DE10034137A1 (en) Active ingredient combinations of 3-iodo-2-propynyl butyl carbamate and one or more 4-hydroxybenzoic acid esters and preparations containing such active ingredient combinations

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20101213

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA RS

RIN1 Information on inventor provided before grant (corrected)

Inventor name: WOEHRMANN, MICHAEL

Inventor name: MEYER, MAREN

Inventor name: FOELSTER, HEIKE

Inventor name: COUNRADI, KATRIN

Inventor name: ARGEMBEAUX, HORST

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20131115

REG Reference to a national code

Ref country code: DE

Ref legal event code: R003

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED

18R Application refused

Effective date: 20151128