WO2011095372A1 - Composition de conservateur - Google Patents

Composition de conservateur Download PDF

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Publication number
WO2011095372A1
WO2011095372A1 PCT/EP2011/050220 EP2011050220W WO2011095372A1 WO 2011095372 A1 WO2011095372 A1 WO 2011095372A1 EP 2011050220 W EP2011050220 W EP 2011050220W WO 2011095372 A1 WO2011095372 A1 WO 2011095372A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
preservative
preservative composition
diacetyl
weight
Prior art date
Application number
PCT/EP2011/050220
Other languages
English (en)
Inventor
Ronnie Nirmala
Nimish Harshadrai Shah
Original Assignee
Unilever Nv
Unilever Plc
Hindustan Unilever 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 Nv, Unilever Plc, Hindustan Unilever Limited filed Critical Unilever Nv
Publication of WO2011095372A1 publication Critical patent/WO2011095372A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0056—Spread 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/06—Preservation of finished products
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/06—Preservation of finished products
    • 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
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives

Definitions

  • This invention relates to a preservative composition. It particularly relates to the preservative food compositions and preservative cosmetic compositions.
  • Multiple-use products such as spreads, margarine etc are typically consumed over several days. Such products, particularly during prolonged use over several days, are likely to be contaminated by contact with hands of the user or contacts with other food materials, or objects such as spoon or knife or due to ariborned contamination during use.
  • One of the problems of multiple-use products is to ensure microbial safety of foods during use, particularly during prolonged use over several days.
  • the problem of preservation during prolonged use for multiple-use products is also a common problem in the area of cosmetic compositions such as shampoos, creams and lotions, and cleaning compositions such as body wash, hand wash and shower gel compositions.
  • Potassium sorbate is typically used in spreads as preservative.
  • Commonly used food preservatives such as potassium sorbate, although efficacious against yeast and mould, are relatively ineffective against bacterial pathogens belonging to Enterobacteriaceae,
  • sorbates and benzoates are relatively less efficacious when the spreads have relatively higher pH.
  • preservatives like potassium sorbate act as a fungistatic agent, but have relartively low fungicidal activity.
  • compositions have relatively high antimicrobial efficacy to the preservative compositions.
  • such compositions have relatively high antibacterial efficacy against both gram positive and gram negative bacteria over prolonged use over several weeks, and also have efficacy against spoilage agents such as yeast and mould.
  • a preservative composition comprising 0.01 to 2% by weight diacetyl and 0.01 to 1 % by weight cinnamic aldehyde.
  • diacetyl as used herein means 2,3-butanedione.
  • the preservative composition comprises 0.01 to 2% by weight, preferably 0.02 to 1 % by weight, more preferably 0.02 to 0.5%, and most preferably from 0.03 to 0.1 % by weight diacetyl.
  • the preservative composition comprises 0.01 to 1 % by weight, preferably 0.01 to 0.5% by weight, more preferably 0.02 to 0.1 %, and most preferably from 0.02 to 0.08 % by weight cinaamic aldehyde.
  • the preservative composition may be a food composition, a cosmetic composition or a cleaning composition.
  • composition means an edible composition.
  • composition means any composition used for topical application.
  • cleaning composition means any composition used for cleaning a substrate.
  • the substrate may be skin, fabric or hard surface such as metal or plastic.
  • the preservative composition is a cosmetic or a cleaning composition, more preferably a cosmetic composition.
  • the preservative composition is a food composition.
  • the preservative composition is a food composition
  • the preservative composition is in form of an emulsion.
  • the emulsion may be water in oil emulsion or oil in water emulsion.
  • Preferred preservative food compositions include spreads, and the spreads preferably include margarine, mayonnaise and butter.
  • the preservative composition comprises preferably greater than 5%, more preferably greater than 15%, and most preferably greater than 30% by weight water. It is particularly preferred that the preservative composition comprises greater than 40% water.
  • the preservative composition may comprise preferably less than 99% by weight, more preferably less than 90% by weight, most preferably less than 80% by weight water.
  • the preservative composition comprising preferred amounts of water are particularly prone to spoilage due to yeast/mould and to the contamination by pathogenic gram negative and/or gram positive bacteria.
  • the preservative composition comprises at least 5% by weight fat. It is particularly preferred that the preservative food compositions comprise fat.
  • the preservative composition may comprise up to 90% by weight fat.
  • the preservative composition comprises preferably from 10 to 70 wt% more preferably from 20 to 60 wt%, most preferably from 30 to 40 wt% fat.
  • the fat consists predominantly of triglycerides.
  • the fat can be a single fat or a combination of fats.
  • the fat or fat blend may comprise vegetable or animal fats which may be hydrogenated, interesterified or fractionated and combinations thereof.
  • Suitable animal fats may consist of butterfat or tallow.
  • Suitable vegetable fats can for example be selected from the group comprising bean oil, sunflower oil, palm kernel oil, coconut oil, palm oil, rapeseed oil, cotton seed oil, maize oil, or their fractions, or a combination thereof.
  • Interesterified fat blends of these fats or optionally with other fats are also encompassed in the invention. It is preferred that the fat comprises poly unsaturated fatty acids (PUFA).
  • PUFA poly unsaturated fatty acids
  • Preferred PUFA may be selected from the group comprising linoleic acid, linolenic acid, alpha linolenic acid (ALA) docosahexaenoic acid (DHA), docosapentaenoic acid (DPA), eicosapentaenoic acid (EPA), eicosatetraenoic acid, and stearidonic acid.
  • Preferred PUFA are omega-6 or omega-3 fatty acids.
  • Other preferred PUFA are long-chain PUFA (LC-PUFA).
  • Most preferred PUFA are ALA, DHA and EPA.
  • at least 20 wt% of the fat are PUFA, more preferred at least 30 wt% and even more preferred more than 40 wt% and most preferred more than 50 wt% of the fat is polyunsaturated.
  • At least 2 wt% of the fat are omega-3 fatty acids, more preferably at least 5 wt%, most preferably at least 10 wt%.
  • the composition comprises 2-40 wt%, even more preferred 5-30 wt%, and most preferred 7-20 wt% omega-3 fatty acids on fat.
  • preservative composition comprise fat when the preservative composition is a food composition. pH of the composition
  • the preservative composition is preferably characterized in that pH of the preservative composition is greater than 3.
  • the pH of the preservative composition is preferably greater than 4, more preferably greater than 4.2, and most preferably greater than 4.8.
  • the conventional preservative agents such as potassium sorbate or sodium benzoate which are acid salts provide antimicrobial activity only in dissociated acid form, i.e. at a pH lower than pKa of the corresponding acid.
  • benzoates are not likely to be effective antimicrobial agents when the preservative
  • composition has pH greater than 4.2 (corresponding to pKa of the benzoic acid).
  • sorbates are not likely to be effective antimicrobial agents when the preservative composition has pH greater than 4.8 (corresponding to pKa of the sorbic acid).
  • the pH of the preservative composition is preferably less than 9, more preferably less than 8, most preferably less than 7.5. It is particularly preferred that pH of the preservative composition is less than or equal to 7.0.
  • MIC minimum inhibitory concentration
  • microorganisms- Yeast and Mould were treated with a cocktail of individual cultures as tabulated below.
  • Mould inoculum was prepared by growing mould cultures on Potato Dextrose Agar (PDA) plates at 25 deg C for 5-7 days till good sporulation was achieved. The spores were harvested using 0.1 % Tween 20. The harvested spore suspension was counted using a haemocytometer and inoculum adjusted to give a spore count of -7 log-io units. An equal amount of individual culture suspensions were pooled together to get the cocktail inoculum. Assay mediae Tryptic Soya Agar (TSA) was used for bacterial cocktails and Potato Dextrose Agar (PDA) for Yeast and Mould cocktails. These were commercial media sourced from Difco.
  • TSA Tryptic Soya Agar
  • PDA Potato Dextrose Agar
  • test antimicrobial was added to achieve the required concentration. The contents were mixed in a vortex and poured into the plate.
  • the plates were marked into required no. of zones (e.g. TSA plates were divided into five zones for the four bacterial cocktails and bacillus spores) and inoculate the agar plate by spot inoculation with 10 ⁇ of ⁇ 10 6 cfu/ml of bacterial and bacillus spore cocktails and ⁇ 10 5 cfu/ml yeast or mould cocktail.
  • compositions comprising diacetyl and cinnamic aldehyde at selective levels provide surprising benefit in inhibiting growth of bacteria, yeast and mould.
  • compositions show efficacy against a broad spectrum of pathogens including gram positive (L, S, and B) as well as gram negative (E) bacteria.
  • compositions comprising 0.05% by weight diacetyl and 0.025% by weight an essential oil. The results are tabulated below. The result for composition comprising 0.05% by weight diacetyl and 0.025% by weight cinnamic aldehyde are reproduced for convenience. Table 3: Comparison of antimicrobial efficacy of essential oils
  • the kill curves are constructed by plotting the cfu/ml surviving at each time point in the presence and absence of the antimicrobial agent. When used to determine the additive or synergistic effect between two (or more) antimicrobial agents, kill curves are constructed for a fixed concentration of each antimicrobial agent alone and in combination and are compared to that of the control (no active) at each time point.
  • Organisms Used The cocktails used were same as those used for the MIC assay, except that for moulds, only spores were used. All strains used were food product isolates from contaminated dressings and spread products.
  • Media used Commercial media, sourced from Difco were used in the experimentation. The media composition is given in Annex 3.
  • TSA Tryptic Soya Agar
  • the flasks which were found to be heavily turbid on visual observation were sampled for counts and subsequently discarded.
  • the non-turbid flasks were followed in time till 28 days. Similar procedure was followed for yeast and mould cocktails also, except that the media used was Yeast peptone Broth and the samples were plated on Potato Dextrose Agar.
  • the final yeast and mould concentration in the flasks was 1 -5 * 10 ⁇ 5 cfu/ml.
  • Results The counts obtained for each test sample were plotted against respective time points to obtain a measure of the kill kinetics.
  • composition (%) Day 0 Day 1 Day 2 Day 7
  • composition (%) Day 0 Day 1 Day 2 Day 7
  • composition comprising diacetyl and cinnamic aldehyde efficaciously reduces the concentration of microorganisms over time.
  • composition according to the present invention is highly efficacious across a range of pH of the compositions.
  • KISSAN® Real Vegetarian Mayonnaise (Hindustan Unilever Limited, India) was used in the experiments. Mayonnaise was incorporated with five different levels of Diacetyl and Cinnamic aldehyde combinations. These were coded and presented to a panel of seven panellists. The test samples were compared with the control product which was the normal formulation without test additives and panellist were asked to score the test samples as acceptable or unacceptable with respect to the control in terms of odour, taste and mouthfeel (Acceptable: at par with the control, Unacceptable: Strange sensorial as compared to the control).
  • the acceptability score was expressed as a ratio of number of panellists that find the product to be acceptable to the total number of panellists. Thus the higher ratio indicates better acceptability
  • Table 5 Sensory evaluation of mayonnaise
  • MIC assay described earlier was used to evaluate efficacy against various microorganisms that can potentially cause skin and/or respiratory infections. All the tests were at pH of 7.
  • compositions according to the present invention are efficacious in inhibiting growth of microorganisms that can potentially cause skin and/or respiratory infections
  • Diacetyl (0.05%) and cinnamic aldehyde (0.025%) were added to commercially available cosmetic compositions, and these compositions were evaluated by a group comprising 5 panellists for sensory perception, in particular for smell and tactile feel. The results are tabulated below Table 7: Sensory Evaluation of cosmetic compositions comprising Diacetyl and Cinnamic aldehyde
  • compositions according the present invention provide antimicrobial efficacy without compromising sensory and tactile properties

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Biochemistry (AREA)
  • Plant Pathology (AREA)
  • Emergency Medicine (AREA)
  • Agronomy & Crop Science (AREA)
  • Birds (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention porte sur une composition de conservateur comprenant 0,01 à 2 % en poids de diacétyle et 0,01 à 1 % en poids d'aldéhyde cinnamique.
PCT/EP2011/050220 2010-02-03 2011-01-10 Composition de conservateur WO2011095372A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN0280/MUM/2010 2010-02-03
IN280MU2010 2010-02-03
EP10161429 2010-04-29
EP10161429.5 2010-04-29

Publications (1)

Publication Number Publication Date
WO2011095372A1 true WO2011095372A1 (fr) 2011-08-11

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ID=43821748

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/050220 WO2011095372A1 (fr) 2010-02-03 2011-01-10 Composition de conservateur

Country Status (1)

Country Link
WO (1) WO2011095372A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014165969A1 (fr) * 2013-04-12 2014-10-16 Perry Lidster Mélanges antimicrobiens d'une substance bactéricide dérivée d'huile essentielle et d'un fongicide dérive d'huile essentielle rallongeant la durée de conservation des denrées agricoles périssables.
WO2014169003A3 (fr) * 2013-04-09 2014-12-18 Arch Chemicals, Inc. Composition multifonctionnelle pour des formulations cosmétiques

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0576780A2 (fr) * 1992-06-10 1994-01-05 Valio Oy Une souche de microorganisme, une préparation bactérienne comprenant cette souche, emploi de cette souche et de cette préparation pour le contrôle de lepores et de moisissures

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0576780A2 (fr) * 1992-06-10 1994-01-05 Valio Oy Une souche de microorganisme, une préparation bactérienne comprenant cette souche, emploi de cette souche et de cette préparation pour le contrôle de lepores et de moisissures

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BATTISTUZZI GIANFRANCO ET AL: "An efficient palladium-catalyzed synthesis of cinnamaldehydes from acrolein diethyl acetal and aryl iodides and bromides.", ORGANIC LETTERS, vol. 5, no. 5, 6 March 2003 (2003-03-06), pages 777 - 780, XP002587633, ISSN: 1523-7060 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014169003A3 (fr) * 2013-04-09 2014-12-18 Arch Chemicals, Inc. Composition multifonctionnelle pour des formulations cosmétiques
US9987209B2 (en) 2013-04-09 2018-06-05 Arch Chemicals, Inc. Multi-functional composition for cosmetic formulations
WO2014165969A1 (fr) * 2013-04-12 2014-10-16 Perry Lidster Mélanges antimicrobiens d'une substance bactéricide dérivée d'huile essentielle et d'un fongicide dérive d'huile essentielle rallongeant la durée de conservation des denrées agricoles périssables.
US11576377B2 (en) 2013-04-12 2023-02-14 Verséa Holdings Inc. Antimicrobial mixtures of an essential oil derived bactericide and an essential oil derived fungicide which extend the shelf-life of perishable agricultural commodities

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