EP2276456A1 - Antimicrobial cosmetic preparations - Google Patents
Antimicrobial cosmetic preparationsInfo
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions 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
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier 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
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing 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
Description
Claims
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)
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)
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)
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 |
-
2008
- 2008-05-13 DE DE102008001726A patent/DE102008001726A1/en not_active Ceased
-
2009
- 2009-03-18 EP EP09745484A patent/EP2276456A1/en not_active Ceased
- 2009-03-18 WO PCT/EP2009/001993 patent/WO2009138150A1/en active Application Filing
Patent Citations (1)
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 |
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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 |
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