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WO2013092277A1 - Procédé antimicrobien et composition - Google Patents

Procédé antimicrobien et composition Download PDF

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Publication number
WO2013092277A1
WO2013092277A1 PCT/EP2012/074964 EP2012074964W WO2013092277A1 WO 2013092277 A1 WO2013092277 A1 WO 2013092277A1 EP 2012074964 W EP2012074964 W EP 2012074964W WO 2013092277 A1 WO2013092277 A1 WO 2013092277A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
antimicrobial
antimicrobial composition
substituted
branched
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
PCT/EP2012/074964
Other languages
English (en)
Inventor
Robert Joseph CORNMELL
Stephen Golding
Ian Peter STOTT
Katherine Mary Thompson
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.)
Hindustan Unilever Ltd
Unilever NV
Conopco Inc
Original Assignee
Hindustan Unilever Ltd
Unilever NV
Conopco Inc
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 Hindustan Unilever Ltd, Unilever NV, Conopco Inc filed Critical Hindustan Unilever Ltd
Publication of WO2013092277A1 publication Critical patent/WO2013092277A1/fr
Anticipated expiration legal-status Critical
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
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • C11D3/2051—Dihydric alcohols cyclic; polycyclic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

Definitions

  • Sanitising and disinfecting soap or cleaning compositions are of great benefit to individuals, since proper use generally may reduce the number of germs and pathogens the individual is exposed to. Thus, such compositions may for instance play an important role in reducing the occurrence and spread of infectious diseases.
  • Sanitising and disinfecting soap compositions comprising chlorine-based antimicrobial agent such as triclosan are also known.
  • Such compositions require a rather long contact time to provide efficacious antimicrobial action.
  • users, in particular children do not spend a long time on cleansing and as a result cleaning with such compositions does not provide adequate prevention from surface or topical infection or adequate protection against diseases.
  • the user, in spite of cleaning his hands, is generally likely to end up with relatively inadequate bacterial removal from his skin. Therefore, he may cause contamination of further animate and/or inanimate surfaces and contribute to the spreading of pathogens and consequent diseases.
  • Users in general and children in particular who wash contaminated hands before meals with slow-acting antimicrobial compositions for a relatively short time are at risk of contracting diseases.
  • the antimicrobial in the compositions are in contact with the substrate for less than a few minutes after which the surface is either wiped off or rinsed with water. These short time scales of cleaning action are ineffective in providing the desired benefit since most known antimicrobials commonly used in such products take several hours to provide the desired kill of microbes.
  • a particular problem of typical terpinoid and phenolic antimicrobial agents is that they are generally well-perceptible due to their olfactory properties. Although the latter may - at least for some species - be appreciated in certain fragrance compositions, they are considered too intense by some users when they are applied at concentrations efficacious in rapid disinfection. Additionally, a lower concentration of odoriferous compounds or the availability of antimicrobial compounds that are less or not odoriferous allows greater flexibility to the manufacturer in providing alternative scents to his composition at lower doses. Hence there is a need to provide alternative antimicrobial compositions and methods that preferably require lower concentrations and/or have a more acceptable sensory profile.
  • JP 2009215261 A, and EP 1816180 A1 disclose the use of 2-(4-alkyl-cyclohex-1 -yl)- propane-1 ,2-diols as synthetic intermediates in the synthesis of other LCD-relevant materials.
  • compositions that contribute to reducing the required contact time in a method for disinfection of a surface.
  • an antimicrobial composition comprising:
  • the carrier is selected from the group consisting of water, ethanol, isopropanol, and mixtures thereof if the composition is free from surfactant; and wherein the one or more substituted cyclohexyl-propanediols have the following structure
  • R-i is selected from
  • the invention provides use of one or more substituted cyclohexyl- propanediols for improved hygiene, wherein the wherein the substituted cyclohexyl- propanediols have the following structure
  • the surface is skin.
  • a surface like the hands, face, body, or the oral cavity is contacted with the composition of the invention.
  • composition may be applied to the surface by any suitable means known to the skilled person.
  • a suitable means may be pouring, dropping, spraying or wiping in case of liquid compositions.
  • the carrier or the dissolution medium during later application is water-based, it may be advantageous if the one or more substituted cyclohexylpropanediols are sufficiently water-soluble.
  • the one or more substituted cyclohexylpropanediols are sufficiently water-soluble if they are soluble to at least the minimum concentration required in the antimicrobial composition according to the invention. Therefore, even more preferably, Ri is ethyl or propyl.
  • the one or more substituted cyclohexyl-propanediols are selected from the group consisting of
  • the one or more substituted cyclohexyl-propanediols are selected from the group consisting of
  • the invention preferably relates to a method, wherein the disinfection time T of said method is less than 300 seconds, preferably less than 60 seconds, and more preferably less than 15 seconds; wherein T is defined as the time that elapses from the moment of adding the composition to a microbial culture until the number of microbes per unit volume of the culture is reduced by a factor of 100 000; and wherein the initial number of microbes preferably exceeds about 100 000 000 microbes per millilitre and wherein the composition is preferably a liquid composition.
  • the disinfecting action (as may be expressed in terms of the disinfection time T) of the method is preferably determined according to the protocol of Example 1 as described hereinafter.
  • This test relates to a standardised test environment in which the microbial culture is kept in suspension.
  • a similarly suitable test is the standard suspension method described in European Standard EN 1276, with the proviso that the disinfection time is adapted to suit the above criteria as will be clear to a person skilled in the art.
  • one of the test methods as described in WO 2010/046238 may for instance be applied to establish the disinfecting action.
  • test methods may preferably also be used by the skilled person to determine the optimal concentrations of the one or more substituted cyclohexylpropanediols in an antimicrobial composition according to the present invention.
  • the invention preferably relates to a method according to the present invention, wherein the surface disinfection time T2 of said method is less than 60 seconds, preferably less than 15 seconds, wherein T2 is defined as the time starting from the moment of applying the composition to the surface to be disinfected after which the number of microbes per unit area is reduced by a factor of 10000 (i.e. a 4 log reduction), wherein the initial number of microbes preferably exceeds 10 3 , more preferably 10 5 , and even more preferably 10 7 microbes per square centimeter.
  • Such tests may for instance be performed as described in WO 2010/046238, or as described in European Standards EN 13697:2001 and EN 1500:1997.
  • compositions according to the second aspect of the invention are compositions according to the second aspect of the invention.
  • an antimicrobial composition comprising:
  • R-i is selected from linear or branched Ci to C 1 0 alkyl, and linear or branched C 2 to Cio alkenyl.
  • the antimicrobial composition according to the second aspect of the invention preferably is suitable for use in the method according to the first aspect of the invention.
  • the antimicrobial composition according to the second aspect of the invention comprises 0.001 to 5% by weight of the one or more substituted cyclohexylpropanediols.
  • the composition comprises preferably 0.005 to 4.5 wt-%, more preferably 0.01 to 4 wt-%, even more preferably 0.02 to 3 wt-%, yet more preferably 0.03 to 2 wt-%, still more preferably 0.04 to 1 wt-%, even more preferably 0.05 to 0.75 wt-% and still more preferably 0.1 to 0.5 wt-% of the
  • Ri is selected from linear or branched Ci to C1 0 alkyl, and linear or branched C 2 to C1 0 alkenyl.
  • Ri may for instance be a methyl, ethyl, propyl, isopropyl, ie f-butyl, allyl, (pent-3-en-2-yl) or n-decyl group.
  • the different isomers resulting from cis-trans isomerism across the 1 ,4-disubstituted cyclohexyl ring are contemplated. However, compounds comprising a trans- ⁇ ,4)-substituted cyclohexyl moiety are preferred.
  • Ri is selected from linear or branched Ci to C 6 alkyl and linear or branched C 2 to C 6 alkenyl. More preferably, Ri is selected from linear or branched C 2 to C 5 alkyl and linear or branched C 2 to C 5 alkenyl. R-i preferably is an alkyl group.
  • the carrier or the dissolution medium during later application is water-based, it may be advantageous if the one or more substituted cyclohexylpropanediols are sufficiently water-soluble.
  • the one or more substituted cyclohexylpropanediols are sufficiently water-soluble if they are soluble to at least the minimum concentration required in the antimicrobial composition according to the invention. Therefore, even more preferably, Ri is ethyl or propyl.
  • the one or more substituted cyclohexyl-propanediols are selected from the group consisting of
  • the one or more substituted cyclohexyl-propanediols are selected from the group consisting of
  • the carrier in the composition according to the second aspect of the invention can be any carrier as described below.
  • the carrier is selected from the group consisting of water, ethanol, isopropanol, and mixtures thereof and more preferably from ethanol, isopropanol and mixtures thereof. Therefore, if the antimicrobial composition is free from surfactant, it preferably comprises from 1 to 99% by weight of the carrier, wherein said carrier is selected from the group consisting of water, ethanol and isopropanol and mixtures thereof and wherein said carrier is preferably selected from ethanol, isopropanol and mixtures thereof.
  • the antimicrobial compositions according to step (i) of the first aspect of the invention and according to the second aspect of the invention comprise a carrier.
  • the carrier is preferably selected from the group consisting of water, oil, solvent, inorganic particulate material, starch and mixtures thereof.
  • the carrier is preferably from 0.1 to 99% by weight of the composition.
  • the antimicrobial composition may be in form of a solid, liquid, gel, paste or soft solid and the carrier may be selected by a person skilled in the art depending on the format of the antimicrobial composition.
  • the antimicrobial composition may for instance, preferably be an antimicrobial anhydrous stick personal care composition on a purely oil/solvent base wherein the composition has a water content of less than 0.01 % by weight, and wherein the composition preferably is free of water.
  • the antimicrobial composition may for instance, preferably be an antimicrobial propellant-drivable personal care composition, also comprising a propellant.
  • the most preferred product format has an emulsion base (water and oil being the carrier), e.g. soap products in liquid, solid, lotion or semisolid form for hand wash, face wash, body wash, or shaving applications; toothpaste/ dentifrices for oral care applications or products for hard surface cleaning in bars or liquids form.
  • emulsion base water and oil being the carrier
  • soap products in liquid, solid, lotion or semisolid form for hand wash, face wash, body wash, or shaving applications
  • toothpaste/ dentifrices for oral care applications or products for hard surface cleaning in bars or liquids form.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Public Health (AREA)
  • Emergency Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Detergent Compositions (AREA)

Abstract

La présente invention concerne un procédé pour la désinfection impliquant une composition antimicrobienne, une composition antimicrobienne appropriée pour l'utilisation dans un tel procédé et des composés antimicrobiens. Elle concerne en particulier une composition antimicrobienne pour des applications de soins personnels, de soins bucco-dentaires ou de nettoyage de surface dure. On a trouvé que les compositions comprenant des cyclohexylpropanediols substitués sélectionnés et un support fournissent une action antimicrobienne. Dans un aspect préféré, les compositions de l'invention comprennent aussi 1 à 80% en poids de tensioactif.
PCT/EP2012/074964 2011-12-22 2012-12-10 Procédé antimicrobien et composition Ceased WO2013092277A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP11195251.1 2011-12-22
EP11195251 2011-12-22

Publications (1)

Publication Number Publication Date
WO2013092277A1 true WO2013092277A1 (fr) 2013-06-27

Family

ID=47324165

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/074964 Ceased WO2013092277A1 (fr) 2011-12-22 2012-12-10 Procédé antimicrobien et composition

Country Status (1)

Country Link
WO (1) WO2013092277A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5322638A (en) * 1989-12-19 1994-06-21 Hoffmann-La Roche Inc. Halophenyl substituted dioxanes
DE19811456A1 (de) 1998-03-17 1999-09-23 Merck Patent Gmbh Flüssigkristallines Medium
EP1816180A1 (fr) 2006-02-07 2007-08-08 Merck Patent GmbH Composés mésogènes, milieu liquide cristallin, et affichage à cristaux liquides
JP2009215261A (ja) 2008-03-12 2009-09-24 Fujifilm Corp ２−シクロヘキシル−１，３−ジオキサン化合物
WO2010046238A1 (fr) 2008-10-20 2010-04-29 Unilever Nv Composition antimicrobienne
WO2011023582A2 (fr) * 2009-08-26 2011-03-03 Basf Se Utilisation de 1,3-diols comme biocides

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5322638A (en) * 1989-12-19 1994-06-21 Hoffmann-La Roche Inc. Halophenyl substituted dioxanes
DE19811456A1 (de) 1998-03-17 1999-09-23 Merck Patent Gmbh Flüssigkristallines Medium
EP1816180A1 (fr) 2006-02-07 2007-08-08 Merck Patent GmbH Composés mésogènes, milieu liquide cristallin, et affichage à cristaux liquides
JP2009215261A (ja) 2008-03-12 2009-09-24 Fujifilm Corp ２−シクロヘキシル−１，３−ジオキサン化合物
WO2010046238A1 (fr) 2008-10-20 2010-04-29 Unilever Nv Composition antimicrobienne
WO2011023582A2 (fr) * 2009-08-26 2011-03-03 Basf Se Utilisation de 1,3-diols comme biocides

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
"EN 13697 Quantitative Surface Test of Bactericidal Activity", ATS LABS, 2001
"McCutcheon's Emulsifiers and Detergents", MANUFACTURING CONFECTIONERS COMPANY
BREZESINSKI, G.; KUSCHEL, F., MOLECULAR CRYSTALS AND LIQUID CRYSTALS, vol. 191, 1990, pages 295 - 300
F GIESSELMANN; R GERMER; A SAIPA, J. CHEM. PHYS., vol. 123, no. 3, 2005, pages 034906,1 - 034906,6
H. STACHE: "Tenside-Taschenbuch, 2nd Edn.", 1981, CARL HAUSER VERLAG
S DIELE; E GEISSLER; H M VORBRODT; H ZASCHKE, MOLECULAR CRYSTALS AND LIQUID CRYSTALS, vol. 102, no. 6-7, 1984, pages 181 - 6
S S BLOCK: "Disinfection, Sterilisation and Preservation, 5th edition,", 2001, LIPPINCOTT, WILLIAMS AND WILKINS
SCHWARTZ; PERRY: "Surface Active Agents", vol. 1, 1949, INTERSCIENCE
SCHWARTZ; PERRY; BERCH: "SURFACE ACTIVE AGENTS", vol. 2, 1958, INTERSCIENCE
UNKNOWN: "EN 1276 Quantitative Suspension for Bactericidal Activity", ATS LABS
UNKNOWN: "EN 1500: 1997. Chemical disinfectants and antiseptics-Hygienic handrub-Test method and requirements (phase 2/step2).", ALCOHOL ARTICLE SUMMARIES

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