WO2002008372A1 - Compositions antimicrobiennes - Google Patents

Compositions antimicrobiennes Download PDF

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Publication number
WO2002008372A1
WO2002008372A1 PCT/EP2001/007889 EP0107889W WO0208372A1 WO 2002008372 A1 WO2002008372 A1 WO 2002008372A1 EP 0107889 W EP0107889 W EP 0107889W WO 0208372 A1 WO0208372 A1 WO 0208372A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
terpene
nonionic
cationic
component
Prior art date
Application number
PCT/EP2001/007889
Other languages
English (en)
Inventor
Martin Vincent Jones
Kenneth Leslie Rabone
Original Assignee
Unilever Plc
Unilever Nv
Hindustan Lever Limited
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 Unilever Plc, Unilever Nv, Hindustan Lever Limited filed Critical Unilever Plc
Priority to AU2001287591A priority Critical patent/AU2001287591A1/en
Publication of WO2002008372A1 publication Critical patent/WO2002008372A1/fr

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Classifications

    • 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
    • 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
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • 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
    • C11D3/18—Hydrocarbons
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/50—Derivatives of urea, thiourea, cyanamide, guanidine or urethanes
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • the invention relates to an antimicrobial composition and in particular to a specific combination of components which provide a synergistic anti-microbial action.
  • Hard-surface cleaning compositions generally comprise one or more surfactants, and, optionally, one or more hygiene agents.
  • the surfactants used in such cleaning compositions are selected from anionic, nonionic, amphoteric and cationic surfactants.
  • Nonionics are very commonly used due to their effectiveness on fatty soils and the ease with which their foaming can be controlled. Of these surfactants, nonionics are reported as showing low biocidal activity, whereas certain anionic, cationic and amphoteric surfactants show biocidal activity under specific conditions of, for example, pH and concentration.
  • the biocidal activity of surfactants is, with a few notable exceptions, low and it is commonplace to add a separate hygiene agent to compositions.
  • Typical hygiene agents include strong acids, alkalis, phenolics and oxidants such as peracids and hypohalites. These, of which a typical example is hypochlorite, are generally highly reactive species which exhibit this reactivity in terms of one or more of, short shelf life, toxic, corrosive and irritant properties. In general, these reactive components are required at relatively high levels in formulations.
  • Other less chemically reactive hygiene agents such as 2 , 4, 4 ' -trichloro-2 ' -hydroxy diphenyl ether (available in the marketplace as IRGASA DP300 [RTM] ) , are effective at relatively low concentrations but are more expensive than simpler species and may be specific as regards their spectrum of activity.
  • EP 0126545 discloses abrasive, hard-surface cleaning compositions comprising terpenes or benzyl alcohol and nonionic surfactants to provide for cleaning of greasy and particulate soils.
  • the compositions disclosed are preferably of pH 8-11.
  • WO 89/12673 discloses acaricidal compositions which comprise benzyl alcohol (as an acaricide) and nonionic surfactants.
  • the pH of the formulation is preferably 7.5-12.5 neat and 3.0-10.0 on dilution.
  • the surfactants used are specialised and mixed to give extremely low interfacial tension and comprise either a phenol ethoxylate or an amphoteric surfactant .
  • Cationic surfactants are included in the exemplary formulations to con er antimicrobial properties .
  • WO 93/11211 discloses the use of low levels of phenol derivatives and oxyethylated aliphatic alcohol derivatives in alkaline hard surface cleaning compositions .
  • the maximum level of phenol derivative is 0.03%wt.
  • WO 94/14942 discloses neutral cleaning compositions which contain a combination of alcohols including benzyl alcohol together with ethoxylated nonionic surfactants .
  • the pH range specified for these compositions is 9-5.
  • US 4311618 discloses cleaning formulations which can contain a broad range of nonionic surfactants of H B ranging from 5- 20 and optionally substituted aromatic alcohols and/or phenols as hygiene agents.
  • Natural phenolics are known to include a number of biocidal compounds including Thymol and Carvacrol (Daouk et al . J. Food Prot (1995) 58 (10) 1147-9) which have been shown to be effective against moulds, yeasts and bacteria (J Essent. Oil. Res. (1995) 7 (3) 299-303).
  • a 'disinfectant' can be understood to be a hygiene agent that shows a 100,000 fold or better reduction in the number of viable micro-organisms in a specified culture when used at a level of around 0.5 wt% . This is generally known as a ' 5 log kill' .
  • alkyl polyglycoside (APG) surfactants show a synergy with relatively low molecular weight alcohols and organic acids as regards hygiene and discloses compositions which comprise APG and organic acids. These compositions are used at strongly acidic pH, generally below pH 3.
  • WO 98/01524 discloses a marked synergy as regards antimicrobial effectiveness between aromatic alcohols or phenols, other than phenol itself and ethoxylated alkanol nonionic surfactants, outside of the physiological pH range,
  • a composition comprising a nonionic surfactant, a compatible cationic biocide, a terpene-like component and a source of alkalinity which ensures a pH of at least 8.5 in the composition, wherein the combination of at least two of the nonionic, cationic and terpene-like components provides a synergistic antimicrobial action which is greater than the additive anti-microbial action of the at least two individual components .
  • compatible cationic biocide refers to a cationic biocide that, by virtue of its structure (for example, a cationic polymer) is not deactivated by nonionic surfactant (for example, by micellisation) .
  • terpene-like component refers to one or more compounds related to the monoterpenes and monoterpenoids .
  • CIO compounds based on two isoprene units that is:
  • the compounds may be acyclic, (as Citral, Citronellal, Citronellol and Geraniol) or alicyclic (as Terpineol, Limonene and Menthol) bridged alicyclic (as Pinene or
  • the terpene-like component is present in the composition in an amount of at least 0.1% by weight, suitably between 0.1 and 2% by weight.
  • the terpene-like component consists of Citral, Thymol or a combination of Citral and Thymol .
  • the combination of terpene-like component and nonionic surfactant is especially effective against Gram-negative microbes .
  • the cationic biocide should be effective against Gram positive microorganisms.
  • the cationic biocide is a biguanide, typically polyhexamethylenebiguanide (PHMB) , and ideally PHMB known sold under the trade name VANTOCIL IB.
  • PHMB polyhexamethylenebiguanide
  • VANTOCIL IB PHMB known sold under the trade name VANTOCIL IB.
  • the cationic should be present in an amount of at least 0.1% by weight and preferably not more than 2% by weight.
  • the cationic is present at between 0.1 and 1% by weight .
  • Suitable nonionic surfactants include alkoxylated alcohols, preferably ethoxylated alcohols.
  • Suitable nonionic detergent active compounds can be broadly described as compounds produced by the condensation of alkylene oxide groups, which are hydrophilic in nature, with an organic hydrophobic compound which may be aliphatic or alkyl aromatic in nature.
  • the length of the hydrophilic or polyoxyalkylene radical which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
  • the preferred alkoxylated alcohols are selected from the group comprising ethoxylated alcohols of the general formula :
  • R 1 is straight or branched, C 8 to C 18 alkyl or hydroxyalkyl and m is, on average, 1-14.
  • Ethoxylated alcohols suitable for use in the present invention include NEODOL 91-8 available in the marketplace from Shell.
  • the nonionic is present in an amount of at least 1% by weight, suitably between 5 and 10% by weight.
  • the composition includes an iodophore, typically iodine.
  • a preferred composition according to the invention comprises:
  • such a composition comprises:
  • composition will have a pH of less than or equal to 12, preferably between 9 and 11.
  • the composition may include a builder that is effective at maintaining the biocidal action of the cationic biocide in the presence of hardness ions.
  • the builder will comprises an alkaline metal carbonate as a precipitant builder.
  • Other builders are well known from laundry formulations, for example, sodium tripolyphosphate . complexing agents such as ethylene diamine tetra-acetic acid, sodium salt may also be used. Mixtures of sodium carbonate and sodium bicarbonate are also useful.
  • Such carbonate builder systems have been found to provide a high reserve alkalinity that is useful for instances where the composition is diluted. By reserve alkalinity is meant the ability of a formulation to maintain a high pH on dilution.
  • compositions according to the invention are suitable for use neat or in dilution.
  • the composition may be diluted in a solvent, typically water, at amounts up to 50, preferably 100, more preferably 600 times their weight. It has been found that such diluted compositions not only provide an effective antimicrobial effect but also provide disinfectancy .
  • ⁇ disinfectant or " disinfectancy” should be taken as meaning the ability to reduce microbial numbers by five orders of magnitude from an initial inoculum N 0 of about 10 s microbes per millilitre, that is a 5 log reduction (that is, log 10 (N 0 /N) • 5, where N is the residual number of microbes) .
  • the invention also relates to a use of a composition according to the invention to disinfect a surface, and to the use, in a process for the preparation of a disinfecting composition for the treatment of a surface, which composition has a pH of at least 8.5, of a nonionic, typically ethoxylated, detergent, a cationic surfactant and a terpene-like component.
  • the invention also relates to a disinfectant composition
  • a disinfectant composition comprising a nonionic surfactant and a cationic biocide which is compatible with the nonionic, wherein the combination of the nonionic and cationic components provides a synergistic antimicrobial action which is greater than the additive anti-microbial action of the two individual components.
  • the cationic biocide is a biguanide, especially PHMB.
  • the composition further comprises a source of alkalinity which ensures a pH of at least 8.5 in the composition.
  • the invention also relates to the use of a composition according to the invention as an antibacterial, especially disinfecting, agent and the use, in a process for the preparation of a disinfecting composition for the treatment of non-living surfaces, of said composition.
  • Micro-organisms were taken from slopes and cultured at 37 degrees C (bacteria) or 28 degrees C (yeast) with constant agitation for 24 hours in nutrient broth (bacteria) or Sabouraud-dextrose liquid (yeast) . Cells were recovered by centrifugation (10 min, 4100 rpm and resuspended in A strength Ringer's buffer to give a suspension of 10 9 - 10 10 cfus/ml. Test solutions were prepared according to the examples laid out below in sterile distilled water. Sufficient bacterial suspension was added to each test solution to give a final concentration of 10 8 bacteria/ml.
  • test solution was added aseptically to 9ml of inactivation liquid (3% (w/v) Tween 80 TM, 0.3% (w/v) lecithin, 0.1% (w/v) Bacteriological peptone made up in pH7.2 phosphate buffer and then serially diluted into X A strength Ringer's buffer.
  • inactivation liquid 3% (w/v) Tween 80 TM, 0.3% (w/v) lecithin, 0.1% (w/v) Bacteriological peptone made up in pH7.2 phosphate buffer and then serially diluted into X A strength Ringer's buffer.
  • Viable organisms were determined by culturing on nutrient or Tryptone-soya peptone agar (bacteria) and Malt Extract agar for 48 hours at 37 degrees C (bacteria) or 28 degrees C (yeast) .
  • the minimum concentration of each test formulation required to achieve disinfectancy was determined from the extent by which the formulation could be diluted and still disinfect, wherein disinfectancy is achieved if there is a 10 5 reduction in viable organisms by the diluted formulation.
  • the data of Table 2 illustrates the change in the microbicidal susceptibility with water hardness particularly of Ps . aeruginosa as reflected by the increase in the minimum disinfection concentration.
  • the data of Table 3 illustrates the change in the minimum disinfection concentration for Ps . aeruginosa as a function of formulation composition.
  • Table 4 The data of Table 4 is shown as a 2-dimentional representation of a 3-dimentional response surface in Figure 2 clearly showing the combination of Neodol 91-8 and Vantocil IB required to obtain the maximum dilutability as exemplified by the smallest value for the minimum disinfection concentration (MDC) .

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

Abstract

L'invention concerne une composition antimicrobienne comprenant un tensio-actif non ionique, éventuellement un composant de type terpène, un biocide cationique compatible avec le tensio-actif non ionique et le composant de type terpène, et une source d'alcalinité permettant d'assurer un pH d'au moins 8,5 dans la composition. La combinaison d'au moins deux des éléments du groupe comprenant les composants non ionique, cationique et de type terpène, permet d'obtenir une action antimicrobienne synergique supérieure à l'action antimicrobienne additive d'au moins deux composants individuels.
PCT/EP2001/007889 2000-07-21 2001-07-09 Compositions antimicrobiennes WO2002008372A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001287591A AU2001287591A1 (en) 2000-07-21 2001-07-09 Antimicrobial compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP00306225.4 2000-07-21
EP00306225 2000-07-21

Publications (1)

Publication Number Publication Date
WO2002008372A1 true WO2002008372A1 (fr) 2002-01-31

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Family Applications (1)

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PCT/EP2001/007889 WO2002008372A1 (fr) 2000-07-21 2001-07-09 Compositions antimicrobiennes

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AU (1) AU2001287591A1 (fr)
WO (1) WO2002008372A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013504553A (ja) * 2009-09-10 2013-02-07 ユニバーシティ オブ サリー 抗菌性組成物
US10201160B2 (en) 2014-05-21 2019-02-12 Boss Holdings Inc. Antimicrobial composition for protecting wood
US10433545B2 (en) * 2016-07-11 2019-10-08 Ecolab Usa Inc. Non-streaking durable composition for cleaning and disinfecting hard surfaces
US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2049149A1 (fr) * 1969-06-03 1971-03-26 Goldschmidt Ag Th Melange biocide synergique
US3787566A (en) * 1969-07-29 1974-01-22 Holliston Labor Inc Disinfecting aerosol compositions
JPS579717A (en) * 1980-06-20 1982-01-19 Nippon Shinyaku Co Ltd Germicidal composition
US4455250A (en) * 1981-01-12 1984-06-19 American Cyanamid Company Stable liquid hard surface cleanser composition containing DGH and a quaternary germicide
JPH04173900A (ja) * 1990-11-05 1992-06-22 Raku:Kk 洗浄剤組成物
US5308610A (en) * 1993-02-08 1994-05-03 Bowman Ronald W Odor control composition and method of using same
EP0848907A1 (fr) * 1996-12-21 1998-06-24 B. Braun Medical AG Préparation désinfectante pulvérisable

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2049149A1 (fr) * 1969-06-03 1971-03-26 Goldschmidt Ag Th Melange biocide synergique
US3787566A (en) * 1969-07-29 1974-01-22 Holliston Labor Inc Disinfecting aerosol compositions
JPS579717A (en) * 1980-06-20 1982-01-19 Nippon Shinyaku Co Ltd Germicidal composition
US4455250A (en) * 1981-01-12 1984-06-19 American Cyanamid Company Stable liquid hard surface cleanser composition containing DGH and a quaternary germicide
JPH04173900A (ja) * 1990-11-05 1992-06-22 Raku:Kk 洗浄剤組成物
US5308610A (en) * 1993-02-08 1994-05-03 Bowman Ronald W Odor control composition and method of using same
EP0848907A1 (fr) * 1996-12-21 1998-06-24 B. Braun Medical AG Préparation désinfectante pulvérisable

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 199231, Derwent World Patents Index; Class A97, AN 1992-255795, XP002154436 *
PATENT ABSTRACTS OF JAPAN vol. 006, no. 073 (C - 101) 8 May 1982 (1982-05-08) *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013504553A (ja) * 2009-09-10 2013-02-07 ユニバーシティ オブ サリー 抗菌性組成物
US10201160B2 (en) 2014-05-21 2019-02-12 Boss Holdings Inc. Antimicrobial composition for protecting wood
US10433545B2 (en) * 2016-07-11 2019-10-08 Ecolab Usa Inc. Non-streaking durable composition for cleaning and disinfecting hard surfaces
US10945431B2 (en) 2016-07-11 2021-03-16 Ecolab Usa Inc. Non-streaking durable composition for cleaning and disinfecting hard surfaces
US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests

Also Published As

Publication number Publication date
AU2001287591A1 (en) 2002-02-05

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