Classifications

• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
  • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
  • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
  • A23L3/3463—Organic compounds; Microorganisms; Enzymes
  • A23L3/3481—Organic compounds containing oxygen
  • A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
  • A23L3/3517—Carboxylic acid esters
• • 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
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
• • 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
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
  • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
  • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23K—FODDER
  • A23K30/00—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23K—FODDER
  • A23K30/00—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs
  • A23K30/10—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs of green fodder
  • A23K30/15—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs of green fodder using chemicals or microorganisms for ensilaging

Definitions

• the invention is related to an antimicrobic composition and its use as a substance inhibiting the growth of detrimental microbes.
• mixtures of organic acids particularly propionic acid and formic acid, or mixtures of organic acids and their ammonium salts, or salts of organic acids are used to prevent Salmonella in poultry forage.
• the products are either solutions or solids.
• the publication WO 92/21239 discloses an antimicrobic composition against, e.g., Salmonella, containing a polyunsaturated C 5 -C ⁇ 4 monocarboxylic acid, such as sorbic acid or its derivative, together with a substituted or an unsubstituted aromatic carboxylic acid, such as benzoic acid or its salt or ester.
• the compositions may also contain organic or inorganic acids. Formic acid is not presented among the numerous acids listed in the publication.
• Esters of parahydroxylbenzoic acid such as propylparaben, possibly together with butylated hydroxyanisole, are known to have an inhibiting effect on the growth of Salmonella (Proc. Int. Symp. Food Microbiol., 1 1th Meeting 1980, 377-84 (1981); J. Food Prot. (1980), 43(3), 191-4).
• compositions containing C C 4 monocarboxylic acid and esters of unsubstituted or substituted benzoic acid are effective in preventing Salmonella and other detrimental microbes and inhibiting the growth thereof.
• the antimicrobic composition according to the invention comprises a first antimicrobic component consisting of a first subcomponent a) which is an unsubstituted or substituted C]-C monocarboxylic acid.
• the preferred amount is about 60-98 weight-% of the weight of the anitimicrobial component.
• the unsubstituted or substituted C C 4 monocarboxylic acid is an acid selected from: formic acid, acetic acid, propionic acid, n-butyric acid, isobutyric acid, glycolic acid, lactic acid, hydroxybutyric acid, pyruvic acid, acetacetic acid, and a mixture thereof, preferably formic acid, acetic acid, propionic acid, lactic acid or a mixture thereof, most preferably formic acid or a mixture of formic acid and propionic acid.
• the antimicrobic composition according to the invention comprises an antimicrobic component consisting of a second component which is an ester of an unsubstituted or substituted benzoic acid.
• the antimicrobic component preferably contains about 1-20 weight-%, and preferably about 2-10 weight-% of an ester of unsubstituted or substituted benzoic acid.
• the ester of the unsubstituted or the substituted benzoic acid is selected from esters of an unsubstituted benzoic acid and from those of a benzoic acid substituted with one or more alkyls, halogens, nitros, hydroxies, and/or aminos.
• Especially preferred esters comprise esters of benzoic acid or those of p-hydroxybenzoic acid.
• the ester of the unsubstituted or the substituted benzoic acid is the ester of the unsubstituted or substituted benzoic acid and an alcohol which is selected from: benzoic alcohol, methanol, ethanol, n-propanol, isopropanol, n-butyl alcohol, and isobutyl alcohol.
• Especially preferred ester- forming alcohols include methanol, ethanol, n-propanol, and isopropanol.
• Alcohols containing several hydroxyl groups that are viable for the ester of benzoic acid of the invention include, e.g., glycols, such as 1,2-propanediol, and triols, such as glycerol.
• esters include methyl benzoate, ethyl benzoate, n-propyl benzoate. isopropyl benzoate, methyl-p-hydroxylic benzoate, ethyl-p-hydroxylic benzoate, n-propyl-p-hydroxylic benzoate, isopropyl-p-hydroxylic benzoate, and butyl-p-hydroxylic benzoate.
• the advantageous embodiments of the invention thus contain activators that accelerate the decomposition of the ester. Tests have also indicated that compositions that catalyze the decomposition of esters, can also decompose carboxylic acid, formic acid in particular.
• Typical activators include mineral acids, such as sulphuric acid, hydrochloric acid, nitric acid, and phosphoric acid or a mixture thereof. Regarding mineral acids, hydrochloric acid is a stronger catalyser than nitric acid.
• the antimicrobic component of the composition according to the invention also comprises about 0.02-20 weight-%, preferably about 0.5-10 weight-% of the ester of C]-C 4 monocarboxylic acid that acts synergistically with the ester of the unsubstituted or the substituted benzoic acid, with C r C 4 alcohol.
• Typical such esters include methylester, ethylester or propylester of formic acid, acetic acid or propionic acid. These substances are preferably obtained when C C-, alcohol, preferably propanol, is added to the composition in situ.
• the antimicrobic component may contain other compositions that improve the preservation power, such as C 4 -C carboxylic acids, such as free benzoic acid, isobutyric acid or octanic acid, or corresponding alcohols; monoglycerides of C 8 -C 16 carboxylic acids or other bactericidal or bacteriostatic surface-active compositions, dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, adipic acid, pimelic acid, suberic acid.
• C 4 -C carboxylic acids such as free benzoic acid, isobutyric acid or octanic acid, or corresponding alcohols
• monoglycerides of C 8 -C 16 carboxylic acids or other bactericidal or bacteriostatic surface-active compositions dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, adipic acid, pimelic acid, suberic acid.
• polykarboxylic acids such as polyacrylic acid, or copolymeric acids formed between unsaturated compounds that are polymerised with acrylic acid and polyacrylic acid
• hydroxycarboxylic acids, dicarboxylic acids or polycarboxylic acids such as sorbic acid, ascorbic acid, cinnamic acid, salicylic acid, tartaric acid or maleic acid
• complexing agents such as EDTA, DTPA; or derivatives, such as salts or esters, of all the above-mentioned acids.
• the mixture may, depending on the application of use, further contain salts affecting as preservatives, including salts of magnesium, zink and copper, compositions that adjust animal nutrients or the salt content of the mixture or that buffer its pH, including ammonium phosphate or potassium sulphate; imidiatzolindylurea, phenolic compositions and sulphonic acids, such as lignosulphonates, or aldehydes, such as formadehyde.
• components acting as antioxidants such as butylated hydroxyanisole or hydroxytoluene, or esters of gallic acid can be added to the mixture.
• compositions according to the invention can also contain other compounds that react with water in an acidly manner, such as organic or inorcanig acids or polyacids, or compounds that form acids in a solution.
• the acids may also be in a partly neutralised form, such as ammonium salts, for instance.
• the compositions that form acids include inorganic or organic salts or acid anhydrides that react in an acidly manner.
• the freezing point of the antimicrobic liquid component of the composition according to the invention is a few degrees above freezing point if its CpC, acid content is high and the water content very low at the same time. By increasing the water content, the melting point can be lowered considerably when desired.
• a preferred water content is about 1-30 weight-% and preferably about 5-20 weight-%.
• the preservatives according to the invention are either in the form of a solution or in a solid form.
• the advantages of the solid state include better security during transport, a slight smell, and an easy dispensing.
• the composition comprises, in addition to the antimicrobic component, also a solid corpuscular carrier.
• the weight ratio between the antimicrobic component and the corpuscular carrier is in the range of 1 : 10 - 10: 1, preferably in the range of 3:7 - 7:3.
• the specific surface of the corpuscular carrier has to be large enough, preferably at least about 10, and more preferably at least about 100 m 2 /g.
• the approximate particle size of the corpuscular carrier is preferably 0.01-20 mm. most preferably about 0.1-2 mm.
• the corpuscular substance mentioned above is preferably selected from the following: inorganic corpuscular substances based on silicium dioxide and/or alumina, such as siliceous earth, moler earth, silicic acid, silica, alumina, bentonite, montmorrillonite, perlite, steatite, chlorite, expanded vermiculite, calcium silicate, sodium aluminium silicate, and zeolites, inorganic salts that dissolve sparingly in water and organic acids, and organic substances such as synthetic polymers, cellulose, cellulose derivatives, lignin and lignin derivatives.
• inorganic corpuscular substances based on silicium dioxide and/or alumina such as siliceous earth, moler earth, silicic acid, silica, alumina, bentonite, montmorrillonite, perlite, steatite, chlorite, expanded vermiculite, calcium silicate, sodium aluminium silicate, and zeolites, inorganic salts
• the solid composition according to the invention ranges from fairly dry to fairly moist.
• the former is easy to dispense also in lower temperatures, the latter may cake together in temperatures lower than the melting point of the liquid phase but when the temperature is increased, it is again easy to process.
• the processibility can be even improved by powdering with a fine solidifying agent or other powder.
• the composition according to the invention comprises an antimicrobic substance that is preferably absorbed in the corpuscular substance.
• Particularly good preservative fluids include those that are easy to handle by dispensing devices, such as granular mineral absorbents, including moler earth, and lumpy celluloses.
• Solic compositions are thus prepared by absorbing a composition in liquid form as such in a large-area inorganic or organic absorbent, such as silica, clay mineral, or cellulose or mixtures thereof.
• Solid compositions may also be prepared so that its liquid ingredients or liquid compositions of the ingredients are separately absorbed in similar or different absorbents, which are finally mixed together. At the same time, other possible solid ingredients may be added.
• the composition according to a particularly preferred embodiment of the invention is in a solid particle-like form so that the mineral acids and other possible compositions that unstabilize formic acid or the ester of the unsubstituted or substituted benzoic acid are situated in different particles than the formic acid and the said benzoic acid esters.
• the antimicrobic substance is absorbed in the first part of the corpuscular substance, and the substance that accelerates the hydrolysis of the ester of the unsubstituted or the substituted benzoic acid is absorbed in the second part of the corpuscular substance.
• a particularly preferred embodiment of the antimicrobic composition according to the invention is obtained with a composition comprising: 1) an antimicrobic component comprising: a) about 50-99.8 weight-% of unsubstituted or substituted C C 4 monocarboxylic acid, b) about 0.2-30 weight-% of the unsubstituted or the substituted ester of benzoic acid, c) about 0-20 weight-% of a substance that causes a hydrolysis of the ester of the unsubstituted or the substituted benzoic acid, d) about 0-20 weight-% of the ester of C r C monocarboxylic acid with alcohol that acts synergistically with the ester of the unsubstituted or the substituted benzoic acid,
• This preferred embodiment also comprises the advantageous components and parametric relations which are presented above separately.
• the invention is related to the use of any of the compositions described above as a substance inhibiting the growth of hazardous microbes, such as .Salmonella, in forage material and forage products and the like.
• the composition may also be used to preserve green forage or grain, to improve the hygiene of cattle sheds and the like, or to disinfect devices, equipment, and packages.
• Example 2 A test was conducted as in the previous example but using another forage sample. The following results were obtained:
• Example 3 SALMONELLA
• the Salmonella infantis used in the test had originally been isolated from a chicken and cultivated in buffered peptone water.
• sets of dilution were made in peptone water by using different amounts of preservatives.
• the growth of bacteria was observed by a Bioscreen device (Labsystems, Finland). The device automatically measures, from the set of samples, the cloudiness that depicts bacterial growth as a function of time.
• Figs. 1 acetic acid
• 2 acetic acid with 2.5 weight-% of EB and 2.5 weight-% of propyl formate
• composition weight fractions
• both acids activate the decomposition of both the ester and the formic acid.
• hydrochloric acid was used, a considerable amount of carbon monoxide gas had formed already during one week in an incubator, and the amount of benzoic acid was so large that some of it had crystallized.
• This composition that is rich in hydrochloric acid is thus suitable to be used only when no preservation time is required of the product.
• Example 4A The test of Example 4A was repeated so that propyl benzoate was used instead of ethyl benzoate.
• the amount of propyl benzoate in the sample containing sulphuric acid was 1.68 weight fractions, and 0.14 weight fractions in the sample containing hydrochloric acid. Both solutions remained clear.
• Liquid mixtures were absorbed in a solid absorbent according to the next table.
• the obtained products were packed in impermeable bottles which were kept in increased temperatures.
• the amount of carbon monoxide generated as a breakdown product of the formic acid was analyzed from the gas phase of the bottles by using gas chromatograph. The following results were obtained:
• Damolin was the same as the one used in the previous example.
• Zeothix 265 is a precipitated silicic acid (Huber Corporation).
• the cellulose was commercial sheet cellulose which was used to make pieces of about 1mm x 1mm by shredding it first with a shredder to form strips, which were then fed in transversally and, finally, oversized pieces were screened out.
• Mixture 7/1 was granular and easy to process.
• Mixture 7/2 felt dry but did not flow as easily as the former mixture.
• Mixture 7/3 was fine and dry, but vault-fo ⁇ ning, and thus more difficult to dispense.
• Mixture 7/4 maintained its block-like form and remained relatively easy to process, even though it felt damp.
• the hardness of its pieces could be further improved by powdering the mixture with small amounts of a salt-like substance which form a slightly soluble formiate such as calcium or magnesium formiates.
• a salt-like substance which form a slightly soluble formiate
• Such substances include, e.g., finely powdered calcium chloride, calcium carbonate, dolomite, and calcium sulphate.
• 60 parts by weight of a granular absorbent was mixed with 40 parts by weight of a mixture of strong formic acid, sulphuric acid, and ethyl benzoate in a ratio of 85: 10:5.
• Another mixture was made with a similar approximate composition by mixing together a) 90 parts by weight of a mixture containing 60 weight-% of the absorbent and 40 weight-% of a mixture of formic acid and ethyl benzoate in a ratio of 94.4:5.6. and b) 10 parts by weight of a mixture containing 40 weight-% of sulphuric acid and 60 weight-% of the absorbent.
• compositions according to the following table were prepared:
• FA(EB) a mixture with 93.9 parts by weight of formic acid and 4.1 parts by weight of ethyl benzoate, and 0.03 parts by weight of benzoic acid.

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• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Polymers & Plastics (AREA)
• Engineering & Computer Science (AREA)
• Zoology (AREA)
• Food Science & Technology (AREA)
• Health & Medical Sciences (AREA)
• Environmental Sciences (AREA)
• Wood Science & Technology (AREA)
• General Health & Medical Sciences (AREA)
• Dentistry (AREA)
• Microbiology (AREA)
• Plant Pathology (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Animal Husbandry (AREA)
• Nutrition Science (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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• 1995
  • 1995-02-06 FI FI950512A patent/FI100376B/fi not_active IP Right Cessation
• 1996
  • 1996-02-05 EP EP96901371A patent/EP0808101A1/en not_active Withdrawn
  • 1996-02-05 WO PCT/FI1996/000065 patent/WO1996024247A1/en not_active Application Discontinuation
  • 1996-02-05 AU AU45422/96A patent/AU4542296A/en not_active Abandoned
  • 1996-02-05 EE EE9700169A patent/EE9700169A/et unknown
  • 1996-02-05 AU AU45421/96A patent/AU4542196A/en not_active Abandoned
  • 1996-02-05 EP EP96901370A patent/EP0808100A1/en not_active Withdrawn
  • 1996-02-05 WO PCT/FI1996/000066 patent/WO1996024248A1/en not_active Application Discontinuation
• 1997
  • 1997-08-04 NO NO972097A patent/NO304671B1/no unknown

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