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WO2008035101A2 - Compositions desinfectantes - Google Patents

Compositions desinfectantes Download PDF

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Publication number
WO2008035101A2
WO2008035101A2 PCT/GB2007/003606 GB2007003606W WO2008035101A2 WO 2008035101 A2 WO2008035101 A2 WO 2008035101A2 GB 2007003606 W GB2007003606 W GB 2007003606W WO 2008035101 A2 WO2008035101 A2 WO 2008035101A2
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WO
WIPO (PCT)
Prior art keywords
emulsion
composition
oil
disinfectant
phase
Prior art date
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Ceased
Application number
PCT/GB2007/003606
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English (en)
Other versions
WO2008035101A3 (fr
Inventor
Lars Kilaas
Inga Aasen
Anne Dyrli
Heidi Johnsen
Jo Klaveness
Petter Mehren
Julian Cockbain
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MAINSANI AS
Original Assignee
MAINSANI AS
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Filing date
Publication date
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Publication of WO2008035101A2 publication Critical patent/WO2008035101A2/fr
Publication of WO2008035101A3 publication Critical patent/WO2008035101A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08Oxygen or sulfur directly attached to an aromatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N33/00Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02Amines; Quaternary ammonium compounds
    • A01N33/12Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N49/00Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof

Definitions

  • This invention relates to disinfectant emulsion compositions, in particular to compositions for use in hand disinfection by medical personnel (e.g. physicians, surgeons, nurses) and by food production workers and by others where hand disinfection is needed or wanted.
  • medical personnel e.g. physicians, surgeons, nurses
  • the invention provides a disinfectant emulsion composition, in particular a composition for disinfecting human or animal external body surfaces and especially hands, having a continuous phase having dissolved therein a first antimicrobial agent and a discontinuous phase having dissolved therein a second antimicrobial agent.
  • the disinfectant emulsion compositions of the invention may be water-in-oil or oil-in-water emulsions or indeed may use two immiscible solvents neither of which is aqueous. Nonetheless the use of oil-in-water emulsions is preferred.
  • the first and second antimicrobial agents are preferably immiscible with the solvent bases for the phase in which they are not dissolved.
  • the composition comprise a cationic surfactant and that the oil phase contains an oil-soluble, water-immiscible antimicrobial agent and the aqueous phase comprises a disinfectant polymeric polycationic species, and optionally an alcohol.
  • the aqueous phase however may be substantially alcohol-free, e.g. with an alcohol content of less than 5% wt., especially less than 1% wt.
  • the emulsion compositions of the invention will typically be supplied in stable form packaged in cartridges for insertion into dispensers, eg wall mounted dispensers. In view of this, it is especially desirable that they remain in emulsion form from packaging to dispensing rather than being provided in a non-emulsion form for conversion into an emulsion, eg by shaking, immediately before administration.
  • the emulsion should be stable to the extent that it is not broken on standing for a period of less than 1 day, especially less than 10 days.
  • compositions of the invention are preferably packaged in sealed cartridges which may be attached to a disinfectant dispenser, preferably an automated dispenser having a pump for disinfectant dosing, e.g. onto the hands of the user.
  • a disinfectant dispenser preferably an automated dispenser having a pump for disinfectant dosing, e.g. onto the hands of the user.
  • Such cartridges form a further aspect of the invention.
  • the invention provides a sealed cartridge having a fluid reservoir with an outlet port adapted to engage with a disinfectant dispenser, said reservoir containing a disinfectant composition, preferably an emulsion and especially preferably a composition according to the invention.
  • the cartridge volume i.e. the maximum liquid content, preferably lies in the range of 10 ml to 10 litre, more preferably 50 ml to 5 litres, especially preferred from 100 ml to 4 litres.
  • the invention provides a method of disinfecting the hands of a human subject, e.g. a health care worker, food producer or other user, which method comprises spraying an emulsion according to the invention over the hands of said subject, rubbing said emulsion onto said hands, optionally rinsing said emulsion from said hands, and optionally drying said hands.
  • the quantity of emulsion applied will generally be in the range 0.1 to 10 mL, especially 0.2 to 5 mL.
  • the emulsion is preferably maintained on the hands for at least 30 seconds, more preferably at least 1 minute.
  • the disinfectant might be washed off but is preferably not washed off so as to obtain a long term disinfectant effect.
  • the oil phase preferably makes up no more than 50% of the volume, more preferably no more than 30%, especially no more than 25%.
  • the oil phase preferably makes up at least 2% of the volume, more preferably at least 5%, especially at least 10%.
  • the balance of the volume is the aqueous phase and any solid phase. If a solid phase is present it preferably makes up no more than 5% of the volume, especially no more than 2%.
  • the oil phase preferably is in microdroplet , nanodroplet or nanoparticulate form, e.g. having a mode particle diameter of 10 run to lO ⁇ m, especially 20 run to 2 ⁇ m, particularly 20 to 500 ran, especially 50 to 200 ran.
  • Mode particle diameter may readily be determined using a particle size analyser, e.g. a Coulter LS-230 apparatus.
  • the emulsions of the invention will typically be prepared by emulsification of an aqueous component and an oil component, e.g. using standard emulsification techniques and apparatus. Preparation of oil-in-water emulsions in which the oil droplets are nanoparticulate is described for example in WO 2005/02782 and WO 96/23409.
  • the aqueous and oil components preferably contain the ingredients of each phase of the emulsion in solution form before emulsification takes place.
  • the aqueous component for the preparation of the emulsion may comprise as a base an alcohol :water mixture in a volume ratio of 10:90 to 90:10, preferably 20:80 to 80:20, particularly 30:70 to 70:30, especially 35:65 to 50:50, eg 38:62 to 48:52.
  • the alcohol used is preferably a Ci_ 6 alkanol, e.g. methanol, ethanol, n-propanol, iso-propanol, n-butanol, etc.
  • the oil component for the preparation of the emulsion preferably comprises as a base a mono, di or triglyceride, particularly preferably of marine (e.g. fish oil) or plant origin, especially a plant oil, or a mixture of two or more such materials .
  • Particularly preferred plant oils include soybean oil, sunflower oil, safflower oil, rapeseed oil, olive oil, corn oil, peanut oil and almond oil, especially peanut oil and almond oil.
  • oil base e.g. mineral oils.
  • aliphatic hydrocarbons as the oil base, or as the majority of the oil base, is generally not preferred.
  • the aqueous phase in the emulsions of the invention preferably contains a dissolved polycationic species, i.e. a compound having a plurality of cationic groups, particularly one having a minimum of 10 cationic groups.
  • the polycationic species may contain the cationic groups as part of the polymer backbone; alternatively they may be pendant from the polymer backbone.
  • Suitable polycations include oligo- and polypeptides having pendant amino functions as well as other synthetic polyamines.
  • the polycation comprises a carbon backbone with fused thereto nitrogen- containing heteroatomic rings, e.g. azacyclopentane or azacyclohexane rings.
  • the polycation comprises quaternary ammonium cationic groups .
  • One category of such polycations includes polymers or copolymers of diallyldialkyl ammonium compounds, e.g. polydiallyldimethyl ammonium chloride (poly-DADMAC) .
  • PoIy-DADMACs are available commercially from Sigma-Aldrich.
  • the molecular weight of such polycations will be in the range 1000-2000000 Da, especially 50 to 1000 kDa.
  • the polycation will preferably be used at a concentration of 0.0001 to 5 wt% relative to the weight of the basic aqueous component (i.e. relative to the total weight of water and alcohol), more preferably 0.001 to 2.0 wt%, especially 0.01 to 0.8 wt%.
  • the oil-soluble water-immiscible antimicrobial reagent used in the emulsions of the invention may be any physiologically tolerable material having these properties .
  • it is a phenolic compound, especially preferably a phenolic found in plants.
  • examples of such compounds include thymol, eugenol, and carvacrol. Thymol is especially preferred.
  • Antimicrobial alcohols such as linalool may desirably be used.
  • the use of chlorhexidine and hexachlorophene is also preferred.
  • the oil-soluble antimicrobial is preferably used at a concentration of up to 40 wt% relative to the total weight of the oil phase, especially 1 to 25 wt%, particularly 2 to 20 wt% .
  • antimicrobials are both water and organic solvent/oil soluble and can be introduced into either or both of the oil and aqueous components from which the emulsion is prepared, e.g. chlorhexidine .
  • the emulsion also preferably contains a cationic surfactant which serves, i.a., to facilitate emulsification and to stabilise the resulting emulsion.
  • a cationic surfactant which serves, i.a., to facilitate emulsification and to stabilise the resulting emulsion.
  • Particularly preferably at least one such surfactant is dissolved in the aqueous component and at least one such surfactant is dissolved in the oil component before emulsification.
  • Such surfactants may be the same, but preferably are different.
  • at least one such surfactant is a quaternary ammonium compound, and it is particularly preferred that the oil and aqueous components each contain a different quaternary ammonium cationic surfactant.
  • a phospholipid or a phospholipid derivatized to enhance surfactant or emulsifier properties, is used.
  • Such phospholipids may typically be of plant, marine or animal origin. Where a derivatized phospholipid is used, it will generally be desirable also to introduce a further water-soluble compound, eg a quaternary ammonium salt.
  • At least one of the cationic surfactants is a quaternary fatty amine alcoholate, e.g. an ethoxylate.
  • a quaternary fatty amine alcoholate e.g. an ethoxylate.
  • examples of such compounds include Stepantex VK90 from Stepan Ltd and Silsense Q-Plus from Noveon Inc, Cleveland, Ohio, US.
  • At least one of the cationic surfactants is a fatty quaternary amine, e.g. a fatty trimethyl ammonium compound or a fatty pyridinium compound, for example cetyl trimethyl ammonium chloride (CTAC) or cetyl pyridinium chloride (CPC), especially CTAC.
  • CTAC cetyl trimethyl ammonium chloride
  • CPC cetyl pyridinium chloride
  • CTAC cetyl trimethyl ammonium chloride
  • CTAB cetyl trimethylammonium bromide
  • Lanquat BC50 dialkyldimethylammonium carbonates • and behentrimonium chloride.
  • Benzalkonium chloride a mixture of benzyl dimethyl alkyl ammonium salts, is especially preferred.
  • the cationic surfactants are preferably used at a concentration in the aqueous component of 0.01 to 20%wt, especially at least 0.05%wt, preferably at least 0.1%wt and preferably no more than 15%wt, especially no more than 10%wt (eg 0.5 to 20 %wt., especially 2 to 15 %wt., particularly 5 to 10 %wt.), and 0.01 to 30 %wt. in the oil component, especially up to 20%wt, eg 1 to 20 %wt., particularly 5 to 15 %wt .
  • the resulting emulsion will to a significant extend distribute at the oil- water phase boundary and their total concentration in the overall emulsion is preferably 0.005 to 2 %wt., particularly 0.2 to 1.5 %wt . , especially 0.5 to 1 %wt .
  • such surfactants of course distribute heavily at the oil/water interface and the can be added to one or both of the oil and water components from which the emulsion is prepared.
  • the preferred contents may be derived from the values specified in the previous paragraph and the selected weight ratio of the oil and water phases .
  • Most of the surfactants are soluble in water and some are soluble in organic solvents (eg benzene, ether, chloroform, etc) and so can be introduced into the oil component in dissolved form.
  • organic solvents eg benzene, ether, chloroform, etc
  • benzalkonium chloride and cetyl pyridinium chloride are typical candidates for introduction into either or both of the oil and aqueous components from which the emulsions are then prepared.
  • the emulsion compositions of the invention may contain further ingredients.
  • further ingredients include, in particular, further antimicrobial agents, skin softening agents, abrasives, colorants, odors, pH modifiers, viscosity modifiers, emulsion stabilizers, antimicrobial potency enhancers, etc.
  • the emulsion compositions include a skin softener, e.g. a polyol or polyether, for example glycol, propylene glycol or polyethylene glycol. Typically this may be included at concentrations of 0.01 to 10 %wt. relative to the total composition weight, especially 0.1 to 5 %wt., particularly 0.3 to 3 %wt .
  • a skin softener e.g. a polyol or polyether, for example glycol, propylene glycol or polyethylene glycol.
  • this may be included at concentrations of 0.01 to 10 %wt. relative to the total composition weight, especially 0.1 to 5 %wt., particularly 0.3 to 3 %wt .
  • abrasive e.g. silica
  • the particle size for the abrasive will typically be 50 to 500 ⁇ m.
  • the abrasive will conveniently be present as less than 5% vol of the total emulsion volume, especially less than 2% vol.
  • a cellulose ether e.g. hydroxypropylmethylcellulose, for example at a concentration of 0.1 to 10% wt. relative to the weight of the aqueous base, particularly 0.2 to 5% wt.
  • a phospholipid, or phospholipid derivative, emulsion stabiliser is used, eg at a concentration of up to 20%wt, preferably 1 to 15%wt, particularly 3 to 10%wt, relative to the total weight of the (rest of) the oil component.
  • antimicrobial potency enhancers for use in the emulsions of the invention, mention may be made of chelating agents such as EDTA and DTPA and salts thereof.
  • antimicrobial agents examples include: hexachlorophene benzalkonium chloride, cetyl pyridinium chloride, didecyldimethylammonium chloride, dibromopropamidine and chlorhexidine. Typically these will be present at 0.01 to 5 %wt., especially 0.05 to 4% wt .
  • the pH modifiers where used, will preferably serve to bring the pH of the aqueous phase to 5 to 7.5, especially 5.5 to 6.5. pH modifiers conventionally used in topical pharmaceutical, cosmetic and disinfectant products may be used.
  • the cartridge containing the compositions of the invention will typically have a liquid content (i.e. an emulsion content) of 10 to 10000 mL, especially 100 to 4000 mL.
  • the cartridges may be of glass, metal, plastic or less preferably plastic or foil lined paper and may be rigid or, more preferably, flexible. Besides having an outlet port through which the emulsion may be expelled, they may also be provided with an inlet port for gas or air to replace expelled emulsion or to expel the emulsion.
  • Numerous liquid dispenser cartridges are known from the prior art and cartridge design need not be explained in detail herein.
  • Figure 1 is a schematic cross-sectional drawing of one embodiment of a cartridge according to the invention.
  • a cartridge 1 comprising a reservoir 2 containing a emulsion disinfectant composition 3.
  • the cartridge has a neck 4 adapted for snap fitting into a dispenser (not shown) and providing an outlet port 5 sealed by membrane 6.
  • a mixture of Amygdalae Oleum (10 g) and hexadecane (0,1 g) was emulsified in distilled water (10 g) containing cetyl pyridinium chloride (CPC) (0,03g) using an ultrasonic device, LabSonic 2000 (head diameter 2 cm) at 200W for 2 min.
  • the mean emulsion droplet size (by number) was 0.263 ⁇ m (CV: 63%) measured in a' COULTER LS 230.
  • Thymol (0,2g) and Stepantex VK90 (0.2g) were mixed in Aracidis Oleum (1.6Og).
  • the resulting solution was emulsified in distilled water (17.8Ig) containing CTAC (O.l ⁇ g) and PEDAC (P-141) (0.009g) .
  • the emulsification was performed using an ultrasonic device, LabSonic 2000 (head diameter 2 cm) at 200W for 2 min.
  • the mean emulsion droplet size (by number) was 78 nm (CV: 58%) measured in a COULTER LS 230.
  • the emulsion was added to a suspension of bacteria in water. After the test time, a sample was removed and diluted with a neutralizing reagent. The solution and a control was put in stripes on agar plates at a series of log • dilutions and after incubation for a couple of days the number of bacterial colonies was counted.
  • Emulsion comprising ethanol, benzalkonium chloride and thymol
  • Benzalkonium chloride 50 mg
  • Thymol 50 mg
  • the mixture was stirred for 5 minutes using an IKA Ultra Turrax at 24 000 rpm.
  • the product obtained was a white emulsion.
  • the product was stable on standing at room temperature for days.
  • the emulsion was also stable during centrifugation using an Eppendorf MiniSpin Plus centrifuge (1 minute, 2000 rpm) .
  • ClinOleic® is a commercial product from Baxter for parenteral administration. 1000 ml ClinOleic® contains: purified olive oil and purified soya bean oil (4:1) 200 grams; phospholipids from egg 12 grams; glycerol 22.5 grams; sodium hydroxide q.s. ad pH 6-8; and water to 1000 ml.
  • Emulsions comprising benzalkonium chloride and various phenols based on soya bean oil/olive oil/phospholipids
  • Benzalkonium chloride and various phenols were added to ClinOleic® emulsion and mixed for 5 minutes using IKA Ultra Turrax at 24 000 rpm.
  • the amounts of components in the emulsions are shown in Table 2 below.
  • Emulsion ClinOleic® Benzalkonium T L E C
  • Example 5 All emulsions prepared in Example 5 were stable on standing at room temperature for days. For extended evaluation of stability, the emulsions were centrifugated using an Eppendorf MiniSpin Plus centrifuge (3 minutes, 4000 rpm) . All emulsions were stable. More extensive centrifugation (3 minutes, 8000 rpm) destroyed all emulsions including pure ClinOleic®.
  • Emulsions comprising cetylpyridinium chloride and various phenols based on soya bean oil/olive oil/phospholipids
  • Cetylpyridinium chloride and various phenols or alcohols were added to ClinOleic® emulsion and mixed for 5 minutes using IKA. Ultra Turrax at 24 000 rpm. The amounts of the components in each of the emulsions are shown in Table 3 below.
  • Example 7 All emulsions prepared in Example 7 were stable on standing at room temperature for days. Centrifugation studies, as described in Example 6, showed that all emulsions were stable.
  • Emulsions comprising thymol and cetylpyridinium chloride based on peanut oil
  • Cetylpyridinium chloride and thymol were added to a mixture of peanut oil and water. The amount of components in each mixture are shown in Table 4 below. The mixtures were shaken for 1 minute using a SM ESPE CapMix shaker. The emulsions were stable at room temperature for days .
  • Emulsion no. Peanut oil Water Thymol Cetylpyridinium chloride mg mg mg mg
  • Emulsions comprising thymol and 1, 2-dipalmitoyl-sn- glycero-3-phosphomethanol based on peanut oil
  • Thymol and the sodium salt of 1, 2-dipalmitoyl-s ⁇ - glycero-3-phosphomethanol were added to a mixture of peanut oil and water.
  • the amounts of the components in each emulsion are shown in Table 5 below.
  • the mixtures were shaken using a SM ESPE CapMix shaker for 1 minute.
  • the mixtures were stable at room temperature for days .
  • Emulsions comprising thymol and benzalkonium chloride based on peanut oil/phosphomethanol derivative
  • Benzalkonium chloride (5 mg) was added to the emulsions of Intermediate 1, and the mixtures were shaken for 1 minute using 3M ESPE CapMix shaker.
  • Emulsions comprising thymol and 1, 2-distearoyl-sn- glycero-3-phosphate based on peanut oil
  • Emulsions comprising thymol and cetylpyridinium chloride based on peanut oil/ phospholipids
  • Cetyl pyridinium chloride (5 mg) was added to the emulsions of Intermediate 2, and the mixtures were shaken for 1 minute using a 3M ESPE CapMix shaker.
  • Emulsions comprising cetylpyridinium chloride/benzalkonium chloride and hexachlorophene/chlorhexidine based on soya bean oil/olive oil/phospholipids
  • Emulsions comprising two antimicrobial agents were prepared by shaking a mixture of the agents with CinOleic® for 1 minute using a 3M ESPE CapMix shaker.
  • the compositions of the various emulsions are shown in Table 6 below.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Insects & Arthropods (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne une composition d'émulsion désinfectante contenant une phase continue dans laquelle est dissous un premier agent antimicrobien et une phase discontinue dans laquelle est dissous un deuxième agent antimicrobien.
PCT/GB2007/003606 2006-09-21 2007-09-21 Compositions desinfectantes Ceased WO2008035101A2 (fr)

Applications Claiming Priority (2)

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GB0618657A GB0618657D0 (en) 2006-09-21 2006-09-21 Compositions
GB0618657.1 2006-09-21

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WO2008035101A2 true WO2008035101A2 (fr) 2008-03-27
WO2008035101A3 WO2008035101A3 (fr) 2008-12-18

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DE102010013081A1 (de) * 2010-03-26 2011-09-29 B. Braun Melsungen Ag Antimikrobielle Öl in Wasser Emulsion
WO2013083588A1 (fr) * 2011-12-06 2013-06-13 Unilever N.V. Composition microbicide
WO2013083580A1 (fr) * 2011-12-06 2013-06-13 Unilever N.V. Composition microbicide
WO2013083590A1 (fr) 2011-12-06 2013-06-13 Unilever N.V. Procédé de désinfection d'une surface
US20130336899A1 (en) * 2010-10-11 2013-12-19 Purdue Research Foundation Antimicrobial formulations that aid in wound healing
US8945596B2 (en) 2008-10-20 2015-02-03 Conopco, Inc. Antimicrobial composition
ITBO20130530A1 (it) * 2013-09-26 2015-03-27 Chemia S P A Pesticida a base di estratti naturali
US8992901B2 (en) 2010-05-31 2015-03-31 Conopco, Inc. Skin treatment composition
EP2787821B1 (fr) 2011-12-06 2016-08-17 Unilever N.V. Composition antimicrobienne
US9693941B2 (en) 2011-11-03 2017-07-04 Conopco, Inc. Liquid personal wash composition

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CA2801143C (fr) 2009-09-24 2017-09-26 Unilever Plc Agent desinfectant comprenant de l'eugenol, du terpineol et du thymol
MX2013006435A (es) 2010-12-07 2013-07-03 Unilever Nv Composicion para cuidado oral.

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8945596B2 (en) 2008-10-20 2015-02-03 Conopco, Inc. Antimicrobial composition
DE102010013081A1 (de) * 2010-03-26 2011-09-29 B. Braun Melsungen Ag Antimikrobielle Öl in Wasser Emulsion
US8992901B2 (en) 2010-05-31 2015-03-31 Conopco, Inc. Skin treatment composition
US20130336899A1 (en) * 2010-10-11 2013-12-19 Purdue Research Foundation Antimicrobial formulations that aid in wound healing
US9693941B2 (en) 2011-11-03 2017-07-04 Conopco, Inc. Liquid personal wash composition
US20150051297A1 (en) * 2011-12-06 2015-02-19 Rohm And Haas Company Method for disinfecting a surface
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EP2787821B1 (fr) 2011-12-06 2016-08-17 Unilever N.V. Composition antimicrobienne
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ITBO20130530A1 (it) * 2013-09-26 2015-03-27 Chemia S P A Pesticida a base di estratti naturali

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