EP2473164A2 - Étherguanidines antimicrobiennes - Google Patents

Étherguanidines antimicrobiennes

Info

Publication number
EP2473164A2
EP2473164A2 EP10736660A EP10736660A EP2473164A2 EP 2473164 A2 EP2473164 A2 EP 2473164A2 EP 10736660 A EP10736660 A EP 10736660A EP 10736660 A EP10736660 A EP 10736660A EP 2473164 A2 EP2473164 A2 EP 2473164A2
Authority
EP
European Patent Office
Prior art keywords
acid
general formula
phase
ether
formulation
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.)
Withdrawn
Application number
EP10736660A
Other languages
German (de)
English (en)
Inventor
Oliver Springer
Peter Muss
Peter Lersch
Ursula Maczkiewitz
Mike Farwick
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.)
Evonik Operations GmbH
Original Assignee
Evonik Goldschmidt GmbH
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 Evonik Goldschmidt GmbH filed Critical Evonik Goldschmidt GmbH
Publication of EP2473164A2 publication Critical patent/EP2473164A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/43—Guanidines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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

Definitions

  • the invention relates to the use of ether guanidines as antimicrobial active ingredient in particular cosmetic and / or pharmaceutical preparations.
  • Antimicrobial agents are widely used in cosmetic deodorants, anti-dandruff and anti-acne formulations, foot care and intimate hygiene products, oral hygiene and dental care products, and disinfectants.
  • Body odor arises especially when the initially odorless sweat is decomposed by microorganisms on the skin. Only the microbial decomposition products cause the unpleasant smell of sweat. This arises especially where there is a high density of sweat glands and also a high density of odoriferous germs such as Corynebacterium xerosis is present, such. B. under the armpits.
  • Certain skin diseases are also associated with excessive growth of unwanted microorganisms on the skin.
  • acne is caused by uncontrolled proliferation of the anaerobic skin bacterium Propionibacterium acnes. Thrush or candidosis is triggered by Candida albicans. Dandruff is brought, inter alia, in connection with the fungus Malassezia Furfur.
  • microorganisms play an important role, for example in the development of caries and dental plaque.
  • Streptococcus mutans is responsible for the formation of caries.
  • antimicrobial agents in cosmetic formulations, especially in cosmetic deodorants, anti-dandruff shampoos and anti-acne creams, is well known in the art.
  • deodorant preparations ranges from solid formulations via liquid or creamy O / W or W / O emulsions to aqueous, alcoholic or oil-containing liquid systems.
  • formulations cover a wide pH range, which can range from about 2 to about 12.
  • Triclosan (5-chloro-2- (2,4-dichlorophenoxy) phenol) shows the antimicrobial activity against a broad spectrum of microorganisms. Due to the
  • guanidine derivatives are described as constituents of skin cosmetics. However, there is no indication of antimicrobial activity of the guanidine derivatives.
  • biocidal guanidine compounds are described, which should be characterized by a large range of action and good bactericidal activity. It is further described that the agents can be used alone, in solution as well as in ointment bases and creams.
  • the object of the invention was to provide active substances which have anti-microbial properties and are suitable for incorporation into cosmetic and pharmaceutical formulations.
  • the etherguanidines described below also have very good antimicrobial properties and can be very easily used in cosmetic and / or pharmaceutical preparations. Furthermore, the compounds are characterized by a selective control of unwanted microorganisms, especially those that are located on the skin.
  • the present invention therefore relates to
  • ether guanidines have both a good stability and a good formability. They also cause a clear effect even at low concentrations, are non-toxic, are very well tolerated by the skin and hair, have a high compatibility with other ingredients and can be formulated without problems.
  • An advantage of the present invention is that the compounds are stable in non-polar and polar (especially alcoholic or aqueous) systems, since no hydrolysis or alcoholysis takes place under the required conditions.
  • Another advantage is that the effectiveness in the entire pH range of the possible cosmetic formulations is largely constant.
  • Another advantage is that the compounds have good skin tolerance.
  • ether guanidines used below, it should be understood not only the ether guanidines themselves but also their salts or hydrates.
  • formulations includes so-called “leave-on” products such as creams, lotions, pump or aerosol sprays,
  • Wipes, deodorant and roll-on formulations such as shower gels, liquid soaps,
  • Oral hygiene products such as mouthwashes or toothpastes
  • Cleaning products such as detergents, household cleaners (floor, kitchen, bathroom cleaners), but without being limited to these.
  • the present invention thus relates to the use of at least one ether guanidine of the general formula (I)
  • R 1 -CH 2 -CH 2 -CH 2 -OR 3 with R 3 linear or branched hydrocarbon radical having 6 to 22 carbon atoms, and
  • R 2 H or an optionally branched, optionally double bond-containing hydrocarbon radical having 1 to 22 C atoms, is, to reduce the growth of microorganisms, especially on a surface.
  • the reduction of the growth of microorganisms can be carried out either by merely inhibiting the growth and associated normal demise of the microorganisms or by killing the organisms by the compound of general formula (I), wherein an active killing of the microorganisms is preferred.
  • (I) is preferably used in a dosage form as a cosmetic and pharmaceutical formulation, preferably antidandruff agents are excluded.
  • a preferred embodiment is the use according to the invention of the at least one ether guanidine of the general formula (I) in deodorant formulations.
  • a further, preferred embodiment represents the use according to the invention of the at least one ether guanidine of the general formula (I) in oral hygiene formulations, such as, for example, toothpaste and mouthwash.
  • a further, preferred embodiment represents the use according to the invention of the at least one ether guanidine of the general formula (I) in intimate hygiene formulations.
  • a further, preferred embodiment represents the use according to the invention of the at least one ether guanidine of the general formula (I) in anti-acne formulations.
  • a further, preferred embodiment represents the use according to the invention of the at least one ether guanidine of the general formula (I) in cleaning products.
  • Etherguanidines of the general formula (I) which are preferably used according to the invention are those in which the radicals R 2 are exclusively hydrogen atoms.
  • the ether guanidines of the general formula (I) are those in which the hydrocarbon radical R has 12 to 18 carbons, and in particular in which the hydrocarbon radical R has 12 to 15 carbon atoms. It is apparent that mixtures of two or more compounds of the general formula (I ) can be used according to the invention.
  • mixtures of a plurality of ether guanidines of the general formula (I) are used, in particular mixtures of those mentioned above as being preferred.
  • mixtures are used in which both hydrocarbon radicals R 3 with 12 and with 13, 14 and 15
  • Carbon atoms are present and each in one
  • the ether guanidines can according to the invention as a salt z. B. used as the salt of an organic or inorganic acid become.
  • the Etherguanidine z. B. according to the invention as the salt of at least one of the acids selected from the group of substituted or unsubstituted, preferably unsubstituted carboxylic acids (mono-, di- and polycarboxylic acids), such as.
  • Benzoic acid o- / m- / p-toluic acid, o- / m- / p-hydroxybenzoic acid, salicylic acid, 3- / 4-hydroxybenzoic acid, phthalic acid, terephthalic acid, or their fully or partially hydrogenated derivatives such as hexahydro- or tetrahydrophthalic acid; Amino acids, such as.
  • Glycine alanine, beta-alanine, valine, leucine, phenylalanine, tyrosine, serine, threonine, methionine, cysteine, cystine, proline, hydroxyproline, pipecolic acid, tryptophan, aspartic acid, asparagine, glutamic acid, glutamine, lysine, histidine, ornithine, Arginine, or aminobenzoic acid; Alkylsulfonic acids, such as. For example, methanesulfonic acid or
  • Arylsulfonklaren such.
  • the preparation of the Etherguanidine can be done in a conventional manner.
  • the preparation of the ether guanidines based on the preparation of alkylguanidines can be carried out by guanidylation of the corresponding amines.
  • the production of alkylguanidines is e.g. in DE-C-506 282.
  • alkylamines are guanidylated in an alcoholic solution with cyanamide in the presence of a protonic acid.
  • the products are obtained as crystalline salts.
  • the preparation of the etherguanidines used according to the invention can be carried out in an analogous manner by reacting etheramines in an alcoholic solution with cyanamide in the presence of a protonic acid.
  • the preparation of the etherguanidines used according to the invention can also be carried out by reacting the etheramines with guanidylating agents other than cyanamide.
  • guanidylating agents other than cyanamide.
  • a list of other guanidylating agents and methods can be found i.a. in EP 1 462 463, Ullmann's Encyclopedia of Industrial Chemistry "Guanidines and Derivatives" chapter 2.4 or Houben-Weyl, E 4, 608-624.
  • the etheramines to be used can be obtained in a simple manner by reacting corresponding alcohols R -OH, where R has the abovementioned meaning, with acrylonitrile according to the following reaction scheme: R-OH + -N * RO * ⁇ NH 2
  • Etheramine A detailed description of the preparation of such etheramines can be found e.g. For example, be taken from EP 1 219 597.
  • Etheramines are commercially available products and are used i.a. offered by the company Tomah Products (USA) under the trade name Tomamine® and the company Evonik Degussa GmbH under the trade name Adogen®.
  • the use according to the invention of the ether guanidines for example, the number of microorganisms in a solution, in particular in a cosmetic or pharmaceutical formulation, can be reduced. This corresponds to the basic idea of a preservative. Preferably, however, the use according to the invention is carried out on a surface.
  • the surface in the use according to the invention is preferably the surface of a human or animal body part, in particular the skin, the hair or the teeth.
  • microorganisms such as bacteria and fungi (including yeasts), especially Corynebacterium xerosis, Propionibacterium acnes, Staphylococcus epidermidis, Candida albicans, Streptococcus mutans, Malassezia furfur.
  • a use characterized in that the microorganisms are gram-positive, in particular coryneform bacteria is preferred.
  • the compounds of the general formula (I) are used according to the invention in the case that the surface is that of a living species, preferably in the form of a formulation. Further preferred uses are, in particular, those uses which serve in the form of the formulations described below, in particular in the form of the preferred formulations described below.
  • the invention further provides a formulation, in particular a cosmetic or pharmaceutical formulation, comprising at least one ether guanidine of the general formula (I)
  • formulations according to the invention contain etherguanidines of the general formula (I) or preferred mixtures thereof mentioned above as being preferably used.
  • Formulations according to the invention preferably comprise from 0.1 to 15% by weight of at least one compound of the general formula (I), based on the total formulation.
  • creams, lotions, solutions, waters, emulsions such as W / O, O / W, PIT emulsions (known as phase inversion emulsions, PIT), microemulsions and multiple emulsions are used to prepare the cosmetic and / or pharmaceutical preparations , Gels, sprays, aerosols and foam aerosols.
  • the cosmetic or pharmaceutical formulations according to the invention may e.g. contain at least one additional component selected from the group of
  • UV light protection filters
  • Hydrotropes (or polyols),
  • etherguanidines of general formula (I) can be used in a variety of formulations for household, industrial, pharmaceutical and cosmetic applications. They are particularly suitable as effective Components in deodorants which may be in the form of aerosol sprays, pump sprays, RoIl-on formulations, deodorant sticks, W / O or O / W emulsions (eg creams or lotions) or wipes.
  • the active compounds / active substance combinations known from the prior art can be used in these formulations, for example triclosan, ethylhexylglycerol, aluminum chlorohydrate, aluminum zirconium tetrachlorohydrex GLY, aluminum zirconium pentachlorohydrate, farnesol, polyglycerol caprylate or caprylate, triethyl citrate, penta (carboxymethyl) diethylenetriamine (pentetic acid), pentylene glycol, propylene glycol, ethanol, zinc ricinoleate, cyclodextrins or zinc oxide.
  • triclosan ethylhexylglycerol
  • aluminum chlorohydrate aluminum zirconium tetrachlorohydrex GLY
  • aluminum zirconium pentachlorohydrate farnesol
  • polyglycerol caprylate or caprylate triethyl citrate
  • the application is not limited to the use in deodorants, but may be advantageous wherever a control of microorganisms or their growth is desired, such as in intimate hygiene products, anti-acne products, in the form of the usual leave-on or rinse-off Formulations may be present, such as creams, lotions, washing solutions, wipes and similar formulations.
  • the substances according to the invention can optionally also be used in combination with known anti-acne active substances, such as, for example, dibenzoyl peroxide, salicylic acid, phytopsingingin, tretinoin, isotretinoin or plant extracts.
  • known anti-acne active substances such as, for example, dibenzoyl peroxide, salicylic acid, phytopsingingin, tretinoin, isotretinoin or plant extracts.
  • anti-dandruff active substances such as climbazole, zinc pyrethione, selenium compounds (for example selenium sulfide), piroctone olamine (octopirox) or plant extracts.
  • the substances according to the invention can also be used in the field of oral hygiene products, whereby the use in mouthwash solutions or toothpastes in particular is recommended here.
  • preservatives can be reduced or possibly even completely dispensed with classical preservatives.
  • (I) can also contain from 0 to 10 wt .-%, preferably from 0.1 to 7.5 wt .-% of one or more
  • Emulsifiers from 0 to 10% by weight, preferably from 0.1 to 7.5
  • % By weight of one or more consistency factors, from 0 to 10% by weight, preferably from 0.1 to 7.5% by weight, of one or more, preferably cationic, surfactants and / or polymers having one or more quaternary ammonium groups and / or from 0 to 20
  • Wt .-% preferably from 0.1 to 17.5 wt .-% of one or more cosmetic oils or emollients and optionally conventional excipients and additives in conventional concentrations.
  • the rest can z. B. water (ad 100 wt .-% water).
  • Another object of the invention is a method for reducing the growth of microorganisms, comprising the steps
  • test germs were inoculated from a stock culture on an agar-containing Caso medium (Merck, Darmstadt, Germany) and incubated at 25 to 37 ° C for 24 hours to 48 hours, depending on the germ. From this preculture a Casoschrägagarrschreibchen was inoculated and again incubated under the same conditions.
  • the products to be tested were prepared as stock solution containing 10 g of ethanol, 0.68 g of macrogolglycerol hydroxystearate 40 (Cremophor® RH40, Omikron, Neckarwestheim, Germany), 1 g of the active substance to be tested and 38.32 g of bidistilled water. This solution was mixed 1: 1 with the seed suspension in the test and gave a drug concentration in the test of 1%. If a drug concentration lower than 1% is tested, the Wirkstoffstammlöung was set correspondingly less concentrated. The ether guanidine was tested from Example 1, and bidistilled water as a negative control.
  • Preservative qs Preparation: Water and glycerin were mixed. Then the carbomer was added slowly with vigorous stirring and continued stirring until completely swollen. Subsequently, the remaining ingredients of the recipe were added step by step.
  • Phase A and B were heated separately to 80 0 C. Subsequently, phase B was added to A and homogenized. Then the emulsion was cooled with stirring to about 30 0 C. The perfume was added during the cooling process below 40 ° C.
  • Example 6 Anti-Acne Facial Lotion
  • Phase A and B were heated separately to 80 0 C. Subsequently, phase B was added to A and homogenized. Then the emulsion was cooled with stirring to 60 0 C and phase C was added. It was briefly homogenized again. The emulsion was further cooled with stirring to about 30 0 C. Phase D and then phase Z were added during the cooling process below 40 0 C.
  • Example 7 Anti-dandruff shampoo
  • Phase A was heated to about 65 ° C until the glycol distearate was melted and then cooled to 45 ° C. Then, the ingredients of Phase B were added to Phase A, step by step, in the order given.
  • Phase C the carbomer was dispersed in water and stirred until completely swollen. Subsequently, Polyquaternium-10 was added and stirred until it was also complete had swollen. Then neutralization with NaOH. Subsequently, Phase C was added to the remainder of the formulation. Lastly, the ingredients of Phase D and Phase Z were added sequentially.
  • Palmitamidopropyltrimonium Chloride 1.5%
  • Phase A The ingredients of Phase A were mixed step by step.
  • Phase B was prepared by dissolving the ether guanidine in water. Subsequently, the polyquaternium-10 was added and the solution was stirred until completely swollen. Subsequently, Phase B was added to Phase A. Finally, phases C and Z were added sequentially.
  • Example 11 Clear hair tonic with anti-dandruff action
  • Example 12 Deodorant spray with propane / butane
  • Phase A was heated to 50 ° C. Subsequently, phase B was added without heating.
  • Phase A and B were heated to 80 0 C. Then Phase B was added to A and homogenized. The mixture was then cooled to 30 ° C. with stirring and phase Z was added.
  • Preservative qs Preparation The ingredients were mixed step by step at 80 ° C. in the order given. This was cooled with stirring to 75 0 C and the product is packaged in the drive sleeves.
  • Phase A and B were heated to 70-75 0 C. Then Phase B was added to A and homogenized. With stirring, it was then cooled to 30 0 C. During the cooling process, phase C was added below 40 ° C.
  • Example 17 O / W lotion for Wipes (suitable for acne skin)
  • Glyceryl stearates Ceteth-20 3.0%
  • Phase A and B were heated to 80 0 C. Then Phase B was added to A and homogenized. With stirring, the emulsion was then cooled to 30 0 C.
  • Citric acid 10% q.s.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Birds (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne l'utilisation d'au moins une étherguanidine représentée par les formules générales (I) et/ou de son sel ou hydrate, dans laquelle R1 = -CH2-CH2-CH2-O-R3,R3 étant un reste hydrocarbure linéaire ou ramifié portant 6 à 22 atomes de carbone et R2 étant H ou un reste hydrocarbure éventuellement ramifié, contenant éventuellement des liaisons doubles, portant 6 à 22 atomes de carbone, pour la réduction de la croissance de micro-organismes. L'invention concerne également des formulations cosmétiques et pharmaceutiques contenant au moins une étherguanidine représentée par les formules générales (I).
EP10736660A 2009-08-31 2010-07-19 Étherguanidines antimicrobiennes Withdrawn EP2473164A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009029010A DE102009029010A1 (de) 2009-08-31 2009-08-31 Antimikrobielle Etherguanidine
PCT/EP2010/060404 WO2011023465A2 (fr) 2009-08-31 2010-07-19 Étherguanidines antimicrobiennes

Publications (1)

Publication Number Publication Date
EP2473164A2 true EP2473164A2 (fr) 2012-07-11

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ID=43524805

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10736660A Withdrawn EP2473164A2 (fr) 2009-08-31 2010-07-19 Étherguanidines antimicrobiennes

Country Status (5)

Country Link
US (1) US20120134948A1 (fr)
EP (1) EP2473164A2 (fr)
BR (1) BR112012004380A2 (fr)
DE (1) DE102009029010A1 (fr)
WO (1) WO2011023465A2 (fr)

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US9456969B2 (en) 2013-09-05 2016-10-04 The Procter & Gamble Company Scalp care composition
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JP7103944B2 (ja) * 2016-02-16 2022-07-20 ローディア オペレーションズ パーソナルケア組成物及び該組成物の使用方法
MX2019000424A (es) 2016-07-19 2019-03-28 Evonik Degussa Gmbh Uso de poliolesteres para la produccion de revestimientos plasticos porosos.
US10463596B1 (en) 2018-06-28 2019-11-05 The Procter And Gamble Company Scalp care composition with well dispersed particulate scalp benefit agents
EP3816247B1 (fr) 2019-10-28 2022-12-07 Evonik Operations GmbH Mélange de durcisseur
CN119912926B (zh) * 2025-04-01 2026-02-27 新疆科力新技术发展股份有限公司 水基环空保护液及其制备方法

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DE102009029010A1 (de) 2011-03-03
WO2011023465A3 (fr) 2012-02-16
WO2011023465A2 (fr) 2011-03-03
US20120134948A1 (en) 2012-05-31

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