Compositions for controlling microorganisms, comprising an effective content of enzymatically prepared esters of polyglycerol

Abstract

The invention relates to compositions for controlling microorganisms, with an effective content of enzymatically prepared mixtures of fatty acid monoesters and fatty acid diesters of polyglycerol.

Description

RELATED APPLICATIONS

[0001] This application claims priority to German application 101 19 694.6, first Apr. 20, 2001, herein incorporated by reference.

BACKGROUND OF THE INVENTION

[0002] 1. Field of the Invention

[0003] The invention relates to compositions for controlling microorganisms, comprising an effective content of enzymatically prepared esters of polyglycerol.

[0004] 2. Description of the Related Art

[0005] A large number of antimicrobial chemical substances and mixtures of these substances are known for controlling microorganisms (Gram-positive bacteria, Gram-negative bacteria, mycobacteria, dermatophytes, yeasts, fungi and hyphal fungi, viruses and spores) which are present on the surface of skin and hair, clothing, devices for body cleansing and bodycare such as, for example, in the dental sector, medical instruments, but also rooms and fitments; said substances and mixtures are divided according to their intended use into disinfectants, preservatives, antiseptics and cosmetic active ingredients, to name but a few.

[0006] The main representatives of these groups are: aldehydes, such as formaldehyde, glyoxal or glutaraldehyde; phenol derivatives, such as 2,2′-dihydroxybiphenyl and 4-chloro-3-methylphenol; quaternary ammonium compounds, cationic surfactants, such as benzalkonium chloride, cetrimonium bromide, cetylpyridinium chloride; amphoteric surfactants, and also compounds which release active oxygen, such as, for example, hydrogen peroxide, organic peracids, alkyl peroxides or alkyl hydroperoxides.

[0007] However, these compounds have a number of disadvantages since they do not meet, or only meet inadequately, the diverse requirements which are placed on them in practice, such as, for example broad activity spectrum, short contact times at low temperatures, good skin compatibility, low toxicity, material compatibility.

[0008] Aldehyde- or phenol-based disinfectants are regarded as being toxicologically and ecologically unacceptable, often lead to sensitizations, in particular of the skin and respiratory organs, and moreover have a characteristic, pungent and unpleasant odor. Some are also potential carcinogens.

[0009] Quaternary ammonium compounds (quats) are for the most part toxicologically acceptable, have no or only very low skin- sensitization and are virtually odorless. However, they have a considerable skin-irritative effect. As in the case of the use of aldehydes, the use of quats may lead to undesired deposits and films on the surfaces treated; these are optically disadvantageous and can only be removed again by customary cleansing processes with difficulty or not at all.

[0010] DE-A-42 37 081 discloses cosmetic deodorants which comprise, as active ingredients, fatty acid esters of di- and triglycerol prepared by chemical means. According to the teaching therein, only the monoesters are effective for controlling Gram-positive bacteria.

[0011] These monoesters can be prepared according to known chemical processes of the prior art (DE-A-38 18 293) by alkaline-catalyzed reaction of a 1.5 to 2.5-fold molar excess of fatty acids or fatty acid derivatives with isopropylidene derivatives of di- and triglycerol, subsequent purification of the reaction product and subsequent acidic hydrolysis or alcoholysis of the isopropylidene groups. When the reaction is complete, the solution has to be neutralized and the monoesters have to be isolated and purified. As well as the multistage nature of the synthesis, in the case of diglycerol derivatives, the use of equimolar amounts of epichlorohydrin is additionally to be regarded as a disadvantage of this route.

[0012] In addition, enzymatically catalyzed processes for the preparation of polyglycerol fatty acid esters are also known. In this connection, D. Charlemagne and M. D. Legoy (JAOCS 1995, Vol. 72, no. 1, 61-65) adsorb firstly the polyglycerol to the same amount of silica gel before allowing it to react in suspension with fatty acid methyl esters with lipase catalysis. The main disadvantage here is the loss of the expensive enzyme which is separated off together with the silica gel by filtration when the reaction is complete. S. Matsumura, M. Maki, K. Toshima and K. Kawada (J. Jpn. Oil Chem. Soc. 1999, Vol. 48, No. 7, 681-692) utilize a modification of this process in order to synthesize polyglycerol esters using 20% by weight of enzyme. According to the teaching given in DE-A-42 37 081, they carry out further purification at high expenditure by means of column chromatography in order to obtain pure monoesters with the known antimicrobial activities.

OBJECTS OF THE INVENTION

[0013] It was therefore an object of the invention to find compositions for controlling microorganisms which largely remedy the described disadvantages of the compositions of the prior art, display high antimicrobial action and can be prepared in an uncomplicated manner from readily accessible raw materials by an economically feasible and ecologically acceptable process.

[0014] It was surprising and could not have been foreseen by the person skilled in the art on the basis of the teachings of the prior art that mixtures of fatty acid mono-, di- and -triesters of polyglycerol which have been prepared by enzymatically catalyzed reaction have comparable and sometimes even significantly better activities in the control of microorganisms than the monoesters prepared by chemical synthesis or enzymatic preparation and purification.

BRIEF DESCRIPTION OF THE DRAWINGS

[0015] FIG. 1 is a graph depicting the effectiveness of diglycerol monocaprate not according to the invention against Corynebacterium xerosis, Staphylococcus epidermidis, and Candida albicans.

[0016] FIG. 2 is a graph depicting the effectiveness of diglycerol caprate from Example 1 not according to the invention against Corynebacterium xerosis, Staphylococcus epidermidis, and Candida albicans.

[0017] FIG. 3 is a graph depicting the effectiveness of polyglycerol 3-caprate from Example 2 not according to the invention against Corynebacterium xerosis, Staphylococcus epidermidis, and Candida albicans.

[0018] FIG. 4 is a graph depicting the effectiveness of diglycerol caprylate from Example 3 not according to the invention against Corynebacterium xerosis, Staphylococcus epidermidis, and Candida albicans.

[0019] FIG. 5 is a graph depicting the effectiveness of polyglycerol-3-caprylate not according to the invention against Corynebacterium xerosis, Staphylococcus epidermidis, and Candida albicans.

SUMMARY OF THE INVENTION

[0020] The invention therefore provides antimicrobial compositions for controlling microorganisms which have an effective content of mixes of fatty acid mono- and diesters of polyglycerol, in particular of di- and/or triglycerol, prepared by lipase or esterase catalysis.

[0021] The invention further provides for the use of antimicrobial mixtures of fatty acid monoesters and fatty acid diesters of polyglycerol, in particular of di- and/or triglycerol, prepared by enzymatically catalyzed (trans)esterification for the preparation of disinfectants, sterilizing compositions, antiseptics, preservatives, which are suitable for the sterilization and disinfection of surfaces and surgical instruments, and preservation, in particular for preservation of cosmetic or dermatological compositions such a composition for body cleansing, bodycare,blemished skin or acne. Moreover, the compositions are also suitable for the preservation of foods and can also be used for the antimicrobial finishing of food packagings. The antimicrobial compositions according to the invention are particularly suitable, due to their mildness, for the preparation of cosmetic preparations for controlling body odor, for controlling dandruff and for controlling blemished skin. Suitable microbes controlled ny the inventive antimicrobial mixture include, Gram-positive bacteria, Gram-negative bacteria, mycobacteria, dermatophytes, yeasts, fungi and hyphal fungi, viruses or spores.

[0022] This invention further provide for a process for preparing the invention composition which comprises reacting at least one fatty acid or fatty acid ester and at least one polyglycerol in the presence of enzymatic catalysts such as a lipase or an esterase.

DETAILED DESCRIPTION

[0023] The polyglycerols used according to the invention are, firstly, linear compounds of the general formula

HO—CH2—CH(OH)—CH2—O—[CH2—CH(OH)—CH2—O]n—H

[0024] in which n=1-9, preferably 1-6, in particular 1-3, specifically 1 and 2. Moreover, the polyglycerols used can also be branched and contain cyclic proportions.

[0025] They are liquids which are highly viscous at room temperature and which, in addition to diglycerol, primarily comprise the more highly condensed oligomers of glycerol. For the purposes of the present invention, particular preference is given to using technical-grade mixtures of polyglycerols which usually comprise diglycerol, triglycerol, tetraglycerol and pentaglycerol.

[0026] They can, for example, be prepared industrially by base-catalytic condensation of glycerol or else by hydrolysis and condensation of epichlorohydrin. Moreover, polyglycerols are also accessible by polymerization of glycidol. Separation and isolation of the individual polyglycerols is possible by treatment with the various means known in the prior art. An overview by G. Jakobson of the various synthetic routes can be found in “Fette Seifen Anstrichmittel”, 1986, volume 88, No. 3, 101-106. The various structural possibilities for polyglycerol can be checked in H. Dolhaine, W. Preuβ and K. Wollmann (Fette Seifen Anstrichmittel 1984, volume 86, No. 9, 339-343).

[0027] Commercially available products are generally mixtures of polyglycerols with varying degrees of condensation; their maximum degree of condensation can usually be up to 10 and in exceptional cases may be even greater. They comprise about 0 to 5% by weight of glycerol, 15 to 40% by weight of diglycerol, 30 to 55% by weight of triglycerol, 10 to 25% by weight of tetraglycerol, 0 to 10% by weight of higher oligomers.

[0028] The polyglycerols preferably used according to the invention comprise about 15 to about 35% by weight of diglycerol, about 38 to about 52% by weight of triglycerol, about 15 to about 25% by weight of tetraglycerol, <about 10% by weight of higher oligomers and <about 2% by weight of cyclic compounds. Particular preference is given to using polyglycerols which comprise only or predominantly diglycerol.

[0029] The fatty acids and fatty acid derivatives, and mixtures thereof, to be used in preference for the purposes of the present invention are derived from straight-chain or branched, saturated, mono- or polyunsaturated carboxylic acid and fatty acid radicals having preferably 6 to 14 carbon atoms, more preferably 8 to 12, in particular 8 to 10, carbon atoms in the main chain. These derivatives optionally contain double bonds and/or hydroxyl groups.

[0030] The fatty acid derivatives which may be used are all customary derivatives which take part in (trans)esterification reactions. According to the invention, the fatty acid derivatives are particularly preferably chosen from fatty acid alkyl esters having 1 to 4 carbon atoms in the alcohol radical.

[0031] The fatty acids or esters thereof used are, individually or in mixtures, fatty acids, such as caproic acid, caprylic acid, capric acid, 2-ethylhexanoic acid, undecylenic acid, lauric acid and myristic acid. In principle, all fatty acids with a similar chain distribution are suitable.

[0032] Preference is given to using caprylic acid and capric acid.

[0033] The quantitative ratio of fatty acid or fatty acid derivatives to polyglycerol is set so that there is an excess of hydroxyl groups compared with fatty acid radicals in the reaction mixture. For the purposes of the present invention, preference is given to setting the quantitative ratio of moles of fatty acid derivatives to moles of polyglycerol to a ratio from about 0.25:1 to about 4:1, in particular about 0.5:1 to about 2:1.

[0034] The enzymatic (trans)esterification by means of enzymes, in particular immobilized enzymes, is preferably carried out with those enzymes chosen from the group of lipases, esterases or proteases, in particular lipases. They have enzyme catalysis activity for ester bonds, in particular for hydrolysis, esterification and transesterification. Such lipases are described in WO 90/09451. Moreover, the product Novozym® 435 from Novozymes as an immobilized lipase system is known and commercially available. This enzyme is particularly preferably used for the purposes of the present invention.

[0035] The polyglycerol fatty acid esters according to the invention consist, in summary, of a mixture of compounds of varying degree of esterification which can comprise considerable proportions of nonesterified polyglycerol. The polyglycerol used as a basis can here be uniform or, for its part, again be a mixture of products of varying degree of condensation.

[0036] Moreover, the compositions according to the invention for controlling microorganisms can, depending on the intended use, also comprise anionic, nonionic, cationic and/or amphoteric surfactants customary in this field.

[0037] Typical examples of such surfactants are:

[0038] 1. Nonionic surfactants based on alkylene oxides, such as ethoxylates of long-chain branched alcohols, ethoxylates of sorbitan esters, propylene oxide-ethylene oxide copolymers, hydroxyalkyl fatty acid amides, polydimethylsiloxane-polyalkylene oxide copolymers, sugar-based surfactants, such as alkyl polyglycosides, alkyl glycoside esters, N-acylglucamides and polyglycerol esters,

[0039] 2. anionic surfactants, such as alkyl sulfates and alkyl ether sulfates, α-olefinsulfonates, fatty acid ester sulfonates, alkylarylsulfonates, sulfosuccinates, alkyl or alkoxyalkyl phosphates, taurates, N-acylamino acid derivatives, sarcosinates, isethionates and soaps,

[0040] 3. cationic surfactants, such as alkyltrimethylammonium salts, fatty acid esters of di- or triethanolammonium salts, alkylimidazolinium salts, acylamidopropyldimethylammonium salts, cationically derivatized polydimethylsiloxanes,

[0041] 4. zwitterionic and amphoteric surfactants, such as betaines, sulfobetaines, amine oxides and amphoacetates.

[0042] The compositions according to the invention for controlling microorganisms are, for example, sterilizing compositions, disinfectants, disinfectant cleaning compositions, all-purpose cleaners, sanitary cleaners, bath cleaners, machine dishwashing detergents, laundry detergents, cosmetic cleansers and care compositions. Cosmetic compositions based on the described enzymatically prepared polyglycerol fatty acid esters are used, in particular, for controlling body odor, dandruff or for controlling skin blemishes. They can be formulated as such in the form of homogeneous liquids, as gels, as ointments, as wax-like or emulsion-like preparations Particularly in the emulsion form, they comprise oils, such as ester oils, volatile or low-volatile silicone derivatives, such as decamethylcyclopentasiloxane, paraffin oils and the like.

[0043] It may be advantageous to co-use other antimicrobial substances in the compositions according to the invention for controlling microorganisms. As such, mention may be made of triclosan, famesol, glycerol monolaurate or 2-ethylhexyloxyglycerol. Depending on the intended use, as well as said surfactants, they may also comprise the auxiliaries and additives specific in each case, for example solvents, builders, foam inhibitors, salts, bleaches, bleach activators, optical brighteners, graying inhibitors, solubilizers, thickeners, fragrances and dyes, emulsifiers, biogenic active ingredients, such as plant extracts and vitamin complexes. Suitable solvents are, in particular, water or alcohols, such as, for example, ethanol, propanol, isopropanol, 2-methyl-2-propanol, propylene glycol, dipropylene glycol or glycerol.

[0044] The amounts of such additives to be used in each case are, depending on the nature of the respective product, known to the person skilled in the art or, where necessary, can be readily determined by simple experimentation.

[0045] Other possible uses for the compositions according to the invention is their use as preservatives in foods and in food packagings, where they are usually used in concentrations of from about 0.01 to about 5% by weight, preferably about 0.1 to about 1% by weight The esters according to the invention can simply be added to foods in the corresponding amount. The polyglycerol esters are used in packaging by, for example, impregnating papers with a solution or emulsion of the esters, or by spraying films with corresponding preparations of the esters. The esters can also be added before or during the shaping process of the packagings, such as extrusion.

EXAMPLES

[0046] The working examples below represent preferred reactions of the present invention, but are not suitable for limiting the invention thereto

Example 1

Diglycerol Caprate

[0047] 415 g of diglycerol and 431 g of capric acid were weighed into a three-necked flask fitted with precision glass stirrer and attached distillation bridge, and 16.9 g of Novozym® 435 were added at 60° C. The water of reaction which formed was removed in a water-jet vacuum until the acid number of the reaction mixture has dropped to a value below 2. To separate off the enzyme, the product was finally filtered

Example 2

Polyglycerol-3 Caprate

[0048] 460 g of a polyglycerol characterized by the following distribution (% by weight): 0.2 of glycerol, 32.6 of diglycerol, 41.2 of triglycerol, 14.8 of tetraglycerol, 3.9 of pentaglycerol, 1.9 of hexaglycerol, 5.4 of higher polyglycerols and 345 g of capric acid were weighed into a three-necked flask fitted with precision glass stirrer and attached distillation bridge, and 16.1 g of Novozym® 435 were added at 60° C. The water of reaction which formed was removed in a water-jet vacuum until the acid number of the reaction mixture dropped to a value below 2. To separate off the enzyme, the product was finally filtered.

Example 3

Diglycerol Caprylate

[0049] 415 g of diglycerol and 361 g of caprylic acid were weighed into a three-necked flask fitted with precision glass stirrer and attached distillation bridge, and 15.5 g of Novozym® 435 were added at 60° C. The water of reaction which formed was removed in a water-jet vacuum until the acid number of the reaction mixture dropped to a value below 2. To separate off the enzyme, the product was finally filtered.

Example 4

Polyglycerol-3 Caprylate

[0050] 579 g of a polyglycerol characterized by the following distribution (% by weight): 0.2 of glycerol, 32.6 of diglycerol, 41.2 of triglycerol, 14.8 of tetraglycerol, 3.9 of pentaglycerol, 1.9 of hexaglycerol, 5.4 of higher polyglycerols and 363 g of caprylic acid were weighed into a three-necked flask fitted with precision glass stirrer and attached distillation bridge, and 18.8 g of Novozym® 435 were added at 60° C. The water of reaction which formed was removed in a water-jet vacuum until the acid number of the reaction mixture dropped to a value below 2. To separate off the enzyme, the product was finally filtered.

Example 5

Microbiological Tests

[0051] The effectiveness of the products according to the invention was established using the challenge test (in accordance with the European Pharmaceuticals Directive). It was found that the products according to the invention are far superior compared with the prior art.

[0052] Carrying out the Microbiological Tests:

[0053] A) Against Corynebacterium xerosis, Staphylococcus epidermidis and Candida albicans

[0054] 1 Samples and Material

[0055] 11.1. Samples

[0056] a. Diglycerol monocaprate (D-caprate A, Solvay Alkali GmbH; comparison substance according to the prior art)

[0057] b. Diglycerol caprate (working example 1)

[0058] c. Polyglycerol-3 caprate (working example 2)

[0059] d. Diglycerol caprylate (working example 3)

[0060] e. Polyglycerol-3 caprylate (working example 4)

[0061] 1.2. Test Microbes

[0062] Corynebacterium xerosis DSM 20743

[0063] Staphylococcus epidermidis DSM 3269

[0064] Candida albicans ATCC 10231

[0065] 1.3. Media Used

[0066] Nutrient media:

[0067] CSL: Casein peptone-soybean meal peptone solution

[0068] CSA: Casein peptone-soybean meal peptone agar

[0069] Sabouraud-glucose broth/agar

[0070] Dilution liquid with inactivation additives

[0071] NaCl-peptone buffer solution with inactivator (3% of Tween® 80, 0.3% of lecithin, 0.1% of histidine, 0.5% of Na thiosulfate)

[0072] 2. Method

[0073] 2.1. Preparation of the Test Solutions

[0074] On the day before the investigation, test solutions of 0.1% (w/v) in CSL were prepared from each sample. For this, 100 ml of CSL were heated to 60° C. in each case in a water bath. From each sample, 0.1 g was weighed into 100 ml of CSL in each case at 60° C. The preparations were shaken vigorously by hand and left overnight at 30° C. in an incubator.

[0075] 2.2. Preparation of the Test Microbe Suspensions

[0076] Cultivate Corynebacterium xerosis over 3 to 4 days. Isolate other microbes in broth or by elutriation.

[0077] 2.3. Contamination of the Samples and Determination of the Reduction in Number of Microbes

[0078] For each test microbe, 20 ml of each test solution were introduced into sterile 50 ml brown glass bottles with glass beads and contaminated with 0.2 ml of microbe suspension. As controls, 20 ml of CSL were carried over per test microbe without sample. The contaminated samples were shaken for 3 mm on a shaking machine and kept in an incubator at 30° C. until removed.

[0079] At the removal points (1, 2, 3, 24 and 48 hours), 1 ml was taken from each preparation and transferred to in each case 9 ml of NaCl-peptone buffer solution with inactivator and the colony number was determined.

[0080] The 0 hours values given were the colony numbers of the test microbe suspension used taking into consideration the 10-2 dilution upon sample contamination.

[0081] 3. Results

[0082] The individual results of the samples are shown in FIGS. 1 to 5. Also shown on each diagram are the microbe populations of an active-ingredient-free blind sample as control value after incubation for 24 hours.

[0083] B) Against Malassezia furfur

[0084] In the same procedure as described under A, the effectiveness of di glycerol caprylate, as prepared in working example 3, was tested against M. furfur. M. furfur is causally related to the formation of dandruff.

[0085] Diglycerol caprylate was dissolved in water to give a solution containing 3.0% by weight. This solution is treated with microbial suspension, homogenized by shaking and incubated at 30° C. A second solution without the addition of diglycerol caprylate is also prepared as control.

[0086] The following results were obtained

Sampling, time (h)	0	1	2	4	24
Control, no. of microbes/ml	1 × 105	n.d.	nd.	n.d.	1 × 104
0.3% Diglycerol caprylate,	1 × 105	<10	<10	<10	<10
no. of germs/ml
n.d. = not determined

Example 6

Cosmetic Formulations

[0087] Examples of formulations in which the products according to the invention can be used are given below

Formulation 1: Clear Deodorant Pumpspray
Phase A:
Product from example 4           0.30%
Trideceth-12                     2.00%
Dipropylene glycol               4.00%
Perfume                          0.90%
Phase B:
Water                            ad 100.00
Preservative                     q.s.
Citric acid (50% strength)       q.s.
The constituents given under phase A were combined with
stirring in the order given and then slowly topped up with
water (phase B). The pH is adjusted to 5.5 with citric acid.
Formulation 2: O/W emulsion (sprayable)
Phase A:
Glycerol stearate (and) Ceteth-20 3.00%
(e.g. TEGINACID ® H, Degussa)
Stearyl alcohol                  1.00%
Product from example 4           0.30%
Dimethicones                     0.50%
Cetearylethyl hexanoate          4.00%
Caprylic/capric triglyceride     4.00%
Phase B:
Glycerol                         3.00%
Water                            ad 100.00%
Citric acid (50% strength)       pH = 6 − 7
Preservative                     q.s.
Perfume                          q.s.
Phases A and B are heated to 70 to 75° C. Phase A was added
with stirring to phase B and then homogenized. The mixture was
cooled with stirring to 30° C.
Important: If phase A is to be introduced initially, phase B must be
added without stirring.
Formulation 3: Clear Deodorant Roll On
Phase A:
Product from example 4           0.30%
Trideceth-12                     2.00%
Dipropylene glycol               2.00%
Perfume                          0.50%
PEG-14 dimethicones              1.00%
Water                            ad 65.00%
Phase B:
Hydroxyethylcellulose (2% in water) 35.00%
Preservative                     q.s.
Citric acid (50% strength)       q.s.
The constituents given under phase A were combined with
stirring in the order given. Phase A is added with stirring to
phase B. The pH is adjusted to 5.5 with citric acid.
Formulation 4: Anionic household cleaner (concentrate)
Phase A:
Product according to the invention 4.00%
Ethanol                          10.00%
Trideceth-12                     5.00%
Cocamidopropylbetaine (˜38%      13.20%
active ingredient content)
Sodium lauryl ether sulfate      35.80%
Phase B:
Water                            ad 100.00%
The constituents given under phase A are combined with
stirring in the order given and then slowly topped up
with water (phase B).

Example 7

Cosmetic Application Test

[0088] Two formulations were used. These are formulation 2 from example 6 and, as placebo, the same formulation in which the product according to the invention (from example 4) has been replaced by nonesterified polyglycerol with the same composition. The armpit odor of 20 subjects is tested before and after application of formulation 2 or the placebo formulation by three experts. In detail, the test involves the following steps:

[0089] 1. The armpit was washed with soap, the odor is evaluated by experts.

[0090] 2. The product was applied once in one armpit. After 6 and 24 h, the odor is tested and the difference is evaluated.

[0091] The result of this investigation was that, both after 6 and also after 24 hours' use, a significant improvement in the odor of the armpit treated according to the invention compared with the placebo-treated armpit is established.

Example 8

Preserving a Food

[0092] Potato salad consisting of 750 g of cooked and finely chopped potatoes, 25 g of finely chopped onions, 1.2 g of cooking salt, 10 ml of vinegar (comprising 6% acetic acid) and 200 g of mayonnaise is treated with 0.5% of the polyglycerol ester from example 4.

[0093] To check on bacteria and yeasts the potato salad was stored for 72 hours at 30° C. Afterwards the following numbers of germs were determined.

[0094] Potato salad without polyglycerol ester: 1.2·106 number of germs/ml

[0095] Potato salad with polyglycerol ester: 1.3·103 number of germs/ml

[0096] To check on yeasts and fungi the potato salad was stored for 72 hours at 25° C. Afterwards the following numbers of germs were determined:

[0097] Potato salad without polglycerol ester: 6.7·104 number of germs/ml

[0098] Potato salad with polyglycerol ester: 2.5·101 number of germs/ml

[0099] The potato salad without polyglycerol ester showed after 96 hours storage clearly visible blueish mould, whereas the potato salad with polyglycerol ester was visually unchanged.

[0100] The above description of the invention is intended to be illustrative and not limiting. Various changes or modifications in the embodiments described herein may occur to those skilled in the art. These changes can be made without departing from the scope or specification of the invention.

Claims

1. A composition for controlling microorganisms, which comprises an effective amount of enzymatically prepared mixture of fatty acid esters of polyglycerol.

2. The composition as claimed in claim 1, wherein the fatty acid esters are mono- and diesters of di- and/or triglycerol.

3. The composition as claimed in claim 1, wherein fatty acid esters of polyglycerol are mono- and diesters and the ratio of mono- to diesters is in the range from about 20:80 to about 80:20.

4. The composition as claimed in claim 1, wherein the polyglycerol is of the formula

5. The composition according to claim 1, wherein the fatty acid ester has at least six carbon atoms and is straight chained or branched, optionally containing hydroxyl groups and/or double bonds.

6. The composition according to claim 1, wherein the polyglycerol is obtained by the condensation of glycerol, by the hydrolysis and condensation of epichlorohydrin; or by the polymerization of glycidol.

7. A composition for controlling microorganisms which comprises an effective amount of enzymatically-prepared mixtures of fatty acid esters of polyglycerols wherein said fatty acid mixtures of polyglycerols are obtained by esterifying polyglycerols with fatty acids or fatty acid esters in the presence of an enzymatic catalyst.

8. The composition according to claim 7, wherein the fatty acids or esters thereof are caproic acid, caprylic acid, capric acid, 2-ethylhexanoic acid, undecylenic acid, lauric acid, myristic acid or mixture of any of the foregoing.

9. The composition according to claim 7, wherein the ratio of the moles fatty acids or fatty acid esters to polyglycerols is from about 0.25:1 to about 4:1.

10. The composition according to claim 7, wherein the enzymatic catalyst is a lipase or an esterase.

11. A method for controlling the growth Gram-positive bacteria, Gram-negative bacteria, mycobacteria, dermatophytes, yeasts, fungi and hyphal fungi, viruses or spores in an area or disinfecting an area where said Gram-positive bacteria, Gram-negative bacteria, mycobacteria, dermatophytes, yeasts, fungi and hyphal fungi, viruses or spores reside which comprises applying or adding to said area a composition according to claim 1.

12. A disinfectant, disinfectant cleaner, sterilizing composition, antiseptic or preservative which comprises a composition according to claim 1.

13. A method of preserving food which comprises adding a composition according to claim 1 to said food.

14. A food packaging material which comprises a composition according to claim 1.

15. A cosmetic formulation which comprises composition according to claim 1.

16. The cosmetic formulation according to claim 15, wherein said formulation is for body cleansing or body care.

17. The cosmetic formulation according to claim 15, wherein is for treating acne or blemished skin.

18. A method for treating acne or blemished skin in a subject in need thereof which comprises applying to the skin of said subject a formulation according to claim 17.

19. A deodorant which comprises a composition according to claim 1.

20. A hair care product which comprises a composition according to claim 1.

21. A method for reducing body odor in a subject which comprises applying a deodorant according to claim 19 to said subject.

22. A method for reducing the formation of dandruff in a subject which comprises applying a hair care product according to claim 20 to said subject.

23. A process for preparing a composition according to claim 1, which comprises reacting at least one fatty acid or a fatty acid ester and at least one polyglycerol in the presence of an enzymatic catalyst wherein said enzymatic catalyst is a lipase or an esterase.