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EP3236917A1 - Utilisation d'octénidine comme principe actif déodorant - Google Patents

Utilisation d'octénidine comme principe actif déodorant

Info

Publication number
EP3236917A1
EP3236917A1 EP15800779.9A EP15800779A EP3236917A1 EP 3236917 A1 EP3236917 A1 EP 3236917A1 EP 15800779 A EP15800779 A EP 15800779A EP 3236917 A1 EP3236917 A1 EP 3236917A1
Authority
EP
European Patent Office
Prior art keywords
octenidine
weight
preparation
ethylhexylglycerol
mixture
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
EP15800779.9A
Other languages
German (de)
English (en)
Inventor
Bernd Traupe
Laura PRIEBE
Inken GROTH
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 EP3236917A1 publication Critical patent/EP3236917A1/fr
Ceased legal-status Critical Current

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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions

Definitions

  • the invention is the use of octenidine as a deodorant active ingredient in cosmetic or dermatological preparations.
  • the invention moreover relates to the use of a mixture of octenidine and ethylhexylgylcerol in specific weight ratios to one another and a certain proportion by weight of the mixture in a cosmetic or dermatological preparation.
  • the mixture can be used as a deodorizing agent.
  • Octenidine dihydrochloride or shortened octenidine (A / octyl-1- [10- (4-octyliminopyridin-1-yl) decyl] pyridin-4-imine, A /, / ⁇ '- (decane-1, 10-diyldi- 1 (4 - /) - pyridyl-4-ylidene) bis (octylammonium) dichloride))
  • a /, / ⁇ '- (decane-1, 10-diyldi- 1 (4 - /) - pyridyl-4-ylidene) bis (octylammonium) dichloride) is known as a broad-spectrum antiseptic for the disinfection of skin and mucous membranes as well as for wound disinfection.
  • Octenidine acts bactericidal against both gram-positive and -negative bacteria, virucidal against lipophilic viruses such as the herpes simplex virus and the hepatitis B virus. It also acts fungicidal, but not against spores.
  • Octenidine is used in combination with phenoxyethanol, 1-propanol or 2-propanol as disinfectants, mouthwashes or wound gels.
  • Ethylhexyglycerol is a known cosmetic ingredient.
  • Sensidin® DO from Schuelke & Mayr is known, comprising ethylhexylglycerol and octenidine HCl, as also described by way of example in DE 10028638 A1 and DE 601 29 705 T2.
  • a combination of active substances comprising at least 1, 0 wt .-% 1- or 2- (C1 to C24 alkyl) glycerol ether (Glycerinmonoalkylether), at least 0.2 wt .-% Bispyridiniumalkan, at least 1, 5 wt .-% polyol and at least 0.0005 wt .-% antioxidants disclosed.
  • DE 4240674 C2 describes the combination of ethylhexylglycerol and other deowir core.
  • the ratio of glycerol monoalkyl ether to the other deodorant composition constituents is in the range from 50: 1 to 1:50, preferably 10: 1 to 1:10 and particularly preferably in the range from 5: 1 to 1: 1.
  • WO 2009106467 A2 discloses compositions comprising octenidine and stabilizers, e.g. Antioxidants, EDTA or UV filters, and adjuvants, e.g. Emulators, described in aqueous preparation.
  • stabilizers e.g. Antioxidants, EDTA or UV filters
  • adjuvants e.g. Emulators
  • WO 9820095 A2 describes combinations of octenidine with alcohols and hydroxycarboxylic acids.
  • EP 1982696 A1 discloses antiseptic gels based on poloxamers comprising octenidine and / or polihexamide as active ingredients.
  • one or more polyols and / or one or more surfactants selected from the group c1) comprises nonionic surfactant and c2) quaternary ammonium compound.
  • DE 102010044787 A1 discloses macroemulsions with octenidine.
  • the macroemulsion has as a particularly advantageous feature a liquid-crystalline system whose liquid crystals, also called mesophases, possess properties of liquid and solid states.
  • the emulsion forms a liquid-crystalline system even without octenidine. This system is not destroyed by the addition of octenidine, so that is obtained by incorporation of octenidine in a macroemulsion such a liquid-crystalline system or generated.
  • Antiperspirants (AT) or deodorants (deodorants) are used to eliminate or prevent body odor that results when the odorless fresh sweat is decomposed by microorganisms.
  • the usual cosmetic deodorants are based on different active principles.
  • deodorant In common usage there is not always a clear distinction between the terms “deodorant” and “antiperspirant”. Rather, especially in German-speaking countries, products for use in the armpit area are referred to as deodorants or “deodorants”, irrespective of the question of whether an antiperspirant effect is also present.
  • Antiperspirants are antiperspirants that, in contrast to the deodorants which generally prevent microbial decomposition of already formed perspiration, are said to prevent the secretion of sweat at all.
  • Sweat odor consists to a large extent of branched-chain fatty acids, which are released by bacterial enzymes from odorless sweat.
  • Classic deodorizing agents counteract this by reducing the growth of bacteria.
  • antimicrobial agents do not per se also deodorant.
  • a deodorizing effect is only present when the active ingredient, after application to the skin, leads to a reduction in the substances responsible for the malodor, such as bacteria, in particular Corynebacterium jeikeium (C. jeikeium).
  • C. jeikeium Corynebacterium jeikeium
  • One challenge therefore is to identify active ingredients that, in addition to being skin friendly, are deodorising and can be used as a deodorizer. Applicable means that a skin irritation or other impairments are avoided.
  • Another challenge is to provide a non-perfumed base recipe for deodorizing cosmetics that have deodorant activity. That It is desirable to provide cosmetic deodorizing preparations which do not require perfume ingredients.
  • perfume ingredients if possible in small quantities and especially flexible, i. various perfumes, to be able to work. This has not succeeded with the previously known blends of known active ingredients.
  • octenidine as a deodorant active in cosmetic or dermatological preparations, wherein the proportion of octenidine in the range of
  • 0, 1 wt.% Up to 0.5 wt.%, In particular in the range of 0, 15 wt.% To 0.25 wt.%, Preferably in the range to 0.2 wt.%, Based on the total mass of the preparation , is elected.
  • octenidine is preferably used in combination with ethylhexylglycerol in a weight ratio of octenidine to ethylhexylglycerol of 0.35 to 1 to 10 to 1, in particular in the range of 0.7 to 1 to 3 to 1, preferably in the range of 1.7 to 1 to 2.5 to 1 selected.
  • the combination of octenidine and ethylhexylglycerol is preferably provided in the following blends or combinations.
  • the use of the combination of octenidine and ethylhexylglycerol in the claimed ratio and proportions by weight in cosmetic or dermatological preparations is preferred
  • the proportions by weight of these blends are in the range of 9 to
  • Propylene glycol has no effect on the deodorant activity of octenidine and does not show itself any desodoriende effect, as is clear for example from the studies of Figures 2 and 4.
  • ethylhexylglycerol surprisingly exhibits an effect on the deodorizing activity of octenidine.
  • cosmetic preparations for example as deodorants or antiperspirants, which comprise octenidine and / or ethylhexylglycerol.
  • deodorants or antiperspirants which comprise octenidine and / or ethylhexylglycerol.
  • octenidine is present in the proportions according to the invention and in particular in the claimed weight ratios to ethylhexylglycerol.
  • octenidine per se acts as a deodorant active in these ratios and proportions.
  • the invention is therefore also the use of octenidine to a certain weight proportion and preferably in combination with Ethylhexylglycerin in a certain weight ratio as a deodorant active ingredient.
  • Octenidine is preferably used as a deodorant active ingredient in cosmetic or dermatological preparations.
  • the preparations may comprise one or more further deodorant and / or anti-perspirant substances. However, it is preferred that the preparations used according to the invention comprise no further antiperspirant substances, in particular no aluminum salts.
  • preparations of the invention are free of additional Deowirkern, especially free of perfume ingredients.
  • Free from means that the proportion of these substances is below 0.01% by weight, based on the total mass of the preparation, as a result of which accidentally introduced impurities of possibly deodorizing or antiperspirant substances are included, which, however, due to their low content, do not contain any Have effects.
  • octenidine has deodorizing properties and that this surprisingly depends advantageously on the ratio to ethylhexylglycerol as well as on the total amount used.
  • a mixture of octenidine hydrochloride and ethylhexylglycerol in a weight ratio of 0.1 to 1 showed inadequate activity, so that this mixture can not be used in this concentration in order to achieve in particular a 48h deodorant activity from unscented aerosol spray formulations.
  • the bacterium C. jeikeium (DSM 7171) is spread from a cryotube according to EN 12353 on a corresponding agar plate (C + T agar) and incubated at 30 ° C for 48 hours. From the grown bacteria, a second passage as liquid culture (AC medium), which was incubated for 8 h at 30 ° C, applied.
  • the liquid culture is adjusted to 0.1 after an OD determination and diluted 1: 8 with thickened medium (AC medium + 0.2% agar). This bacterial suspension was then used for the test.
  • 25 ⁇ bacteria are applied to the skin (bacterial count of 1 * 10 5 / cm 2 ) and evenly distributed with a spatula.
  • 10 mg of the active substance mixtures (A) are likewise pipetted onto the skin and distributed.
  • 2 punches are mixed with 500 ⁇ Ab Springfieldpuffer and with the spatula for 30 sec. rinsed.
  • the bacteria are plated by means of a spiral plater.
  • the plate with the pig skin is for 20 min. incubated at 30 ° C and a humidity of about 90%.
  • all skin punches are covered with 500 ⁇ Ab Hughespuffer and for 1 min. sonicated in an ultrasonic bath.
  • 200 ⁇ of the rinsed solutions are pipetted to 800 ⁇ disinhibition medium.
  • the investigations demonstrate a potency of octenidine to a weight fraction of 0.1 to 0.2 wt.%, Based on the total mass of the preparation, which consists only of octenidine, ethylhexylglycerol, propylene glycol and water.
  • mixtures B comprising 19.8% octenidine, 19.8% ethylhexyl glycerol, the remainder propylene glycol, based on the total mass of mixture B, were tested against control K + (water) by means of a pig skin assay (FIG. 1).
  • 1% of mixture B comprises thus 0.198% by weight of octenidine, 0.198% by weight of ethylhexylglycerol and 0.604% by weight of propylene glycol, based on the total mass of the tested preparation comprising mixture B and solvent water (then to 99% by weight).
  • 0.75% blend B comprises 0.1485 weight% octenidine
  • 0.5% blend B contains 0.099% octenidine
  • 0.25% blend B comprises 0.0495% octenidine.
  • the weight ratio of octenidine to ethylhexylglycerol in Blend B is 0.198% by weight to 0.198% by weight, i. 1 to 1.
  • Mixtures C comprise 20% octenidine, 10% ethylhexyl glycerol, balance propylene glycol, based on the total mass of the mixture C.
  • Figure 3 shows the results of the pigskin assay of mixtures C versus control K + (water).
  • 1% of mixture C comprises thus 0.2% by weight of octenidine, 0.1% by weight of ethylhexylglycerol and 0.7% by weight of propylene glycol, based on the total mass of the tested preparation comprising mixture A and solvent water (then to 99% by weight) ).
  • 0.75% mixture C comprises 0.15% by weight octenidine, 0.5% mixture C 0.1% octenidine and 0.25% mixture C comprises 0.05% octenidine.
  • the weight ratio of octenidine to ethylhexylglycerol in the mixture C is 0.2 to 0.1, i. 2 to 1.
  • the investigations show that a bacterial reduction on the skin after 20 minutes at a value of 1000 CFU / ml shows an effective deodorizing effect.
  • the sniff test (SNK) is used to determine an i.d.R. 48-hour deodorant efficacy of cosmetic formulations after single use.
  • the application of the test product and the measurement of the effectiveness take place in the user-relevant area, the armpit.
  • the target is the odor intensity of the armpit sweat.
  • the measurement is performed as described below.
  • the determination of the deodorizing activity is realized by the use of valid and accepted measurement methods and evaluation methods.
  • the study design is designed so that deodorizing activities can be demonstrated as follows:
  • the measurement is made by a subjective, olfactory assessment of the intensity of armpit sweat through a sniffer panel.
  • the odor intensity of the armpit sweat is evaluated for a comparative assessment of the odor samples according to the absolute scale values from 0 (no sweat odor) to 5 (very strong sweat odor).
  • the score "X" for foreign smells eg cigarette smoke, perfume, etc.
  • the score "X" for foreign smells is assigned in pairs for each L (left) and R (right) pairs of glasses R and L of a test person are opened one after the other and then only then is an assessment given for each sample.
  • a coded test sample (coding according to Wl 7 MAT 100) in a contralateral comparison against the untreated control is tested.
  • the cosmetic or dermatological preparations according to the invention may further contain cosmetic adjuvants and active ingredients such as are commonly used in such preparations, for.
  • cosmetic adjuvants and active ingredients such as are commonly used in such preparations, for.
  • agents, preservatives, preservatives, bactericides, lipids, substances for preventing foaming, dyes and color pigments, thickeners, moisturizing and / or moisturizing substances or other conventional ingredients of a cosmetic or dermatological formulation such as polyols, polymers, foam stabilizers, organic solvents or silicone derivatives if the additive does not impair or preclude the required properties with regard to their effectiveness.
  • Preferred preparations comprising the combination of octenidine and ethylhexylglycerol are to be selected from:
  • alcoholic solutions preferably ethanol
  • Emulsions preferably water in oil
  • propellant-containing preparations in particular W / O aerosols, or oil-containing aerosols
  • the preparations according to the invention are preferably provided as atomizer formulations with an alcohol content, preferably ethanol, between 30 and 99% by weight, based on the total mass of the preparation without propellant gases.
  • this formulation provides as a body spray, allows a pleasing and pleasing application, avoiding the influence of additional formulation ingredients.
  • the mixing ratio of the alcoholic solution or W / O emulsion summarized as preparation (2.), with propellant preferably in the range of 20 to 40 wt.%, In particular 30 wt.%, Active substance solution to 60 to 80 wt. %, in particular 70 wt.%, propellant to choose.
  • these propellant-containing preparations (3.) furthermore contain octenidine in the range from 0.1% by weight up to 0.5% by weight, based on the total mass of the preparation without propellant gas.
  • the weight ratio of the octenidine-containing preparations (2) to propellant gas is preferably selected in the range from 10% by weight to 90% by weight to 70% by weight to 30% by weight, based now on the total mass of the propellant-containing preparation (3. ).
  • the ratio is in the range of 15% preparation to 85% propellant, or 30% to 70% and in particular 60% preparation to 40% propellant gas.
  • the proportion of perfume or perfume ingredients is therefore preferably selected in the range of less than 0.5 wt.%, In particular less than 0.2 wt.%, Advantageously less than
  • Aerosol spray alcoholic
  • the liquid phase (2.) obtained by mixing together the respective constituents is filled with a propane-butane mixture (2: 7) in a ratio of 39:61 into aerosol containers.
  • Aerosol spray suspension :
  • the liquid phase obtained by mixing together the respective components is filled with a propane-butane mixture (2: 7) in the ratio 39:61 in aerosol containers.

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)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'octénidine dans une proportion comprise entre 0,1 et 0,5 % en poids présente une action déodorante et peut être employée comme principe actif déodorant dans des préparations cosmétiques. L'association d'octénidine et d'éthylhexylglycérine dans un rapport pondéral octénidine/éthylhexylglycérine compris entre 0,4/1 et 10/1 présente en outre une très bonne efficacité déodorante.
EP15800779.9A 2014-12-22 2015-11-24 Utilisation d'octénidine comme principe actif déodorant Ceased EP3236917A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102014226763 2014-12-22
PCT/EP2015/077451 WO2016102132A1 (fr) 2014-12-22 2015-11-24 Utilisation d'octénidine comme principe actif déodorant

Publications (1)

Publication Number Publication Date
EP3236917A1 true EP3236917A1 (fr) 2017-11-01

Family

ID=54703962

Family Applications (1)

Application Number Title Priority Date Filing Date
EP15800779.9A Ceased EP3236917A1 (fr) 2014-12-22 2015-11-24 Utilisation d'octénidine comme principe actif déodorant

Country Status (3)

Country Link
EP (1) EP3236917A1 (fr)
BR (1) BR112017013208B1 (fr)
WO (1) WO2016102132A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2022527332A (ja) * 2019-04-01 2022-06-01 スリーエム イノベイティブ プロパティズ カンパニー 抗菌組成物
DE102020214352A1 (de) 2020-11-16 2022-05-19 Beiersdorf Aktiengesellschaft Pumpspray mit Deowirkern

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4240674C2 (de) * 1992-11-26 1999-06-24 Schuelke & Mayr Gmbh Desodorierende Wirkstoffe
DE10028638A1 (de) * 2000-06-09 2001-12-20 Schuelke & Mayr Gmbh Lagerstabile Zusammensetzungen von Glycerinmonoalkylethern
DE102005002643B4 (de) * 2005-01-19 2007-11-22 Schülke & Mayr GmbH Zusammensetzungen für die hygienische Händedesinfektion und die desinfizierende Händewaschung
DE102008011692A1 (de) * 2008-02-28 2009-09-10 Schülke & Mayr GmbH Wirkstoffkombination und deren Verwendung
DE102010044787A1 (de) * 2010-09-09 2012-03-15 Beiersdorf Ag Makroemulsionen mit verbesserter Deodorantwirksamkeit
DE102010044785A1 (de) * 2010-09-09 2012-03-15 Beiersdorf Ag Octenidindihydrochlorid als Co-Emulgator in Mikroemulsionen
RU2014149076A (ru) * 2012-05-08 2016-06-27 Мерк Патент Гмбх Применение простых эфиров циклогексанола, обладающих антимикробными свойствами

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
None *
See also references of WO2016102132A1 *

Also Published As

Publication number Publication date
BR112017013208A2 (pt) 2018-02-06
BR112017013208B1 (pt) 2021-06-08
WO2016102132A1 (fr) 2016-06-30

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