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 relates to compositions suitable for preserving green forage, fresh cuttings, grain or other organic material, and for controlling hazardous micro ⁇ organisms, containing an ester of unsubstituted or substituted benzoic acid.
• the AIV process when preserving green forage, the AIV process is used so that the pH of the forage mass to be preserved is lowered to about 4 or less by adding acidic com- pounds and by means of the lactic acid fermentation occurring in it.
• mineral acids, organic acids, specifically formic acid, acetic acid, and propionic acid, as well as acidic salts are used.
• Patent publication FI63328 to Lampila discloses the use of benzoic acid as an addi- tive in acidic preservatives for preserving green forage and the like, decreasing ad ⁇ verse fermentation and increasing the sugar content.
• the preservatives according to the publication contain 2 %-60 % of benzoic acid or a derivative, considered as benzoic acid.
• Patent publication PCT/FI93/00068 discloses stabile compositions containing 5-25 wt-% of benzoic acid or p-hydroxybenzoic acid or the salt or ester thereof which, in addition to other possible components, contain formic acid, acetic acid, and/or propionic acid or their esters.
• Patent application FI920886 discloses preservatives that contain benzoic acid or its salts and ethyl formate and, possibly, C ⁇ - C carboxylic acids.
• Patent publication GB 2 193 078 presents compositions for preserving moist hay, comprising acetic acid, propionic acid, or preferably sorbic acid which contains magnesium oxide, zinc oxide, and soluble Cu(II), preferably at a ratio of 100: 10 - 20: 1.
• Patent publication DE 3 540 771 discloses a provision of formic acid esters of 1,2- propanediol in preserving animal forage and treating drinking water.
• the esters act on coliform bacteria in particular.
• Patent publication JP 57 018 601 discloses the use of carboxyl acids and their de ⁇ rivatives (such as chlorides, esters, anhydrides, amides, and nitriles) and salts in solutions of 10 "3 - 10 "1 M as pesticides against different plant diseases.
• Patent publication US 3 745 027 discloses the preserving of foodstuffs, such as meat, fruits, and vegetables against moulding and bacterial germs, by cooking them in a solution containing 25-90 wt-% of polyalcohols and 0.5-1 wt-% of fungicide.
• the fungicides include sorbic acid, propionic acid, and benzoic acid, and their salts and esters.
• patent publication US 3 404 987 discloses the use of propionic acid, sorbic acid, benzoic acid, essence niobe, ethyl benzoate, and the edible alkali salts and alkaline earth salts of the said acids to protect foodstuffs against micro-orga- nisms.
• 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 Salmo ⁇ nella in poultry forage.
• the products are either solutions or solids.
• solid forage for hens, cows, pigs, etc. containing 20 wt-% of moisture, at the most, can be preserved without drying by using a preservative that contains sorbic acid or sorbates together with a physiologi ⁇ cally-harmless organic or inorganic acid or its salt.
• the carcasses of dead animals are disinfected by treating them with solutions containing, in addition to acetic acid, propionic acid, citric acid, and hydrochloric acid, also medium-chain fatty acids, such as Cio fatty acids.
• the mixture is reported to have an effect on, e.g., Salmo ⁇ nella typhirium and Escherichia coli.
• lauryl monoglyceride i.e. monolaurine
• lauryl monoglyceride i.e. monolaurine
• Methylparaben, Propylparaben, and EDTA is well-known in preserving cosmetic protein-bearing emulsions.
• Preservative of green forage absorbed in natural zeolite or synthetic zeolite is known from patent SU 1 461 398. It contains 10-50 wt-% of organic acids, such as formic acid, acetic acid, and propionic acid, and 10-60 wt-% of zeolite while the rest com ⁇ prise salts of inorganic acids or salts of water-soluble organic acids, such as Na- benzoate, Na-salicylate, or Na-acetyl salicylate.
• PCT publication 91/11192 discloses a solid product containing acid and intended for the preservation of green forage or for an additive of animal forage, in which the acid is absorbed in siliceous earth, preferably in granular clay-bearing siliceous earth, 'moler earth'.
• the above forage preservatives leave a lot to be desired, particularly when preserv ⁇ ing predried green forage, whereby the grass is cut and left lying on the surface of the ground to be predried before embaling or siloing. During this stage, mould, bacteria, yeast and their germs may go into the forage from the ground so that the lot is easily spoiled.
• compositions containing about 5-25 wt-% of benzoic acid compo ⁇ nent, disclosed in FI 920887 and PCT/FI93/00068 generally yield good results in preserving predried green forage, they still have defects. If sufficient amounts of expensive stabilising agents are not used, slight crystallisation may occur in the pre ⁇ servative during long-term cold-storage. It would also be advisable to decrease the amount of benzoic acid component, partly because of the expensive price; partly because it stains machines in such concentrations and forms a light-coloured, ben- zoic acid-bearing layer of dirt on the machine when drying, which is difficult to re ⁇ move.
• Another defect of present preservatives is frequently that, after the bale or the silo of forage has been opened, the forage that so far had been well-preserved, may deterio- rate fast when its sugars start to ferment. It would be advisable to preserve the for ⁇ age so that some sugars remain but, nevertheless, postfermentation is as minor as possible.
• the crop When not dried, the crop is preserved either as coarsely powdered or as whole wheat.
• the moisture of the grain is about 30-35 % and the pres ⁇ ervation is generally effected by using the same preservatives according to the AIV process as in the preservation of green forage.
• the con ⁇ ventional preservatives for green forage are not effective enough but propionic acid, for example, is used, which is expensive. Therefore, it would be advisable to find more cost-effective preservative compositions also for grain preservation.
• a preservative composition containing esters of unsub ⁇ stituted or substituted benzoic acid comprising an ester component 1) which is the ester of an unsubstituted or substituted benzoic acid with C] - C 9 alcohol or a mixture of such esters, and an ester component 2) that acts syn ⁇ ergistically with said ester component 1) and is the ester of unaromatic - C 20 car- boxylic acid with C ⁇ - C 9 alcohol.
• the acid of the ester component 1) is an unsubstituted or substituted benzoic acid.
• Ci - C 9 alco ⁇ hols of ester component 1) or 2) include primary and secondary saturated or unsaru- rated alcohols which possibly contain more than one hydroxyl group and whose chain is either straight or branched.
• Saturated alcohols include, e.g., methanol, etha ⁇ nol, n-propanol, isopropanol, butanols, particularly n-butanol and isobutanol, penta- nols, hexanols, heptanols, octanols, particularly n-octanol and 2-ethylhexanol, and nonanols.
• Alcohols containing several hydroxyl groups include glycols, such as 1,2- propanediol, and triols. such as glycerol.
• Preferred alcohols comprise Ci - C 4 alco- hols, such as ethanol, propanol, and butanol.
• a viable aromatic alcohol is, e.g., ben ⁇ zoic alcohol.
• the preferred esters of ester component 1) include methyl esters, ethyl esters, n- propyl esters, isopropyl esters, n-butyl esters, isobutyl esters, n-amyl esters, isoamyl esters, n-octyl esters, or 2-ethylcapryl esters of benzoic acid or p-hydroxybenzoic acid. Even more preferred are methyl benzoates, ethyl benzoates, propyl benzoates, isopropyl benzoates, butyl benzoates, and isobutyl benzoates; particularly preferred are ethyl benzoate, propyl benzoate, and isopropyl benzoate.
• the unaromatic - C 20 carboxyl acids of ester component 2) include saturated or unsaturated mono-, di-, or tricarboxylic acids which may contain hydroxyl groups.
• saturated monocarboxylic acids include formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, capronic acid, ca- prylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, and myristinic acid.
• Di- carboxylic acids include oxalic acid, malonic acid, succinic acid, glutaric acid, adipinic acid, pimelic acid, and suberic acid with their alkyl and hydroxy deriva ⁇ tives.
• Hydroxycarboxylic acids include glycolic and lactic acids, saccharic acids, tartaric acid, maleic acid, and citric acid. Unsaturated acids include fumaric acid, maleic acid, sorbic acid, oleinic acid, linolic acid, linolenic acid, and ricinic acid.
• esters of ester component 2 comprise esters which, when hydrolysing in their object of use, at the same time form acids which function as preservatives, the acids including formic acid, acetic acid, propi- onic acid, lactic acid, octanoic acid, 2-ethylhexylic acid, or sorbic acid; or alcohols such as octyl alcohol, acting as a preservative.
• esters of ester component 2) include propyl, isopropyl, butyl, and isobutyl esters of formic acid, propionic acid, and lactic acid; the most preferred is propyl propionate.
• the preservation power of ester component 2) alone may be unsatisfactory. There ⁇ fore, it is assumed that the synergy is based on the fact that this ester, independent of the application, improves the adhesion, the migration, and the absorption of ester component 1) on the surfaces of the material to be preserved and on those of the bacterium, yeast, or the like to be controlled. Such synergy had not been detected earlier.
• the synergy of the preservative according to the invention is always materialised when there are present both the ester component 1), i.e., the ester of an unsubsti ⁇ tuted or substituted benzoic acid with C ⁇ - C 9 alcohols, and ester component 2), i.e., the ester of unaromatic - C 2 o carboxylic acid with - C alcohol.
• ester component 1 the ester component 1
• ester component 2 i.e., the ester of unaromatic - C 2 o carboxylic acid with - C alcohol.
• the relative weight moieties of ester component 1 ) and ester com ⁇ ponent 2) in the composition range between about 10: 1 - 1:5, preferably between about 4: 1 - 1 :2, most preferably between about 2: 1 - 1 : 1.5.
• preservative composition according to the invention may also contain other preservative components. These include the preservatives listed in the preceding survey of the literary, therefore, the publications and their English equivalents mentioned in the survey are incorporated here by reference.
• the application of the preservative composition of the invention in ⁇ tended particularly for the preservation according to the AIV process contains acid component 3). Its purpose is to lower the pH of the treated object to 4 or less. Re- garding the invention, the quality of the acid is not critical.
• the acid component may be an organic or inorganic acid or a polyacid, or a composition that forms acid in a solution.
• the acid component contains organic Ci - C 20 acid, and preferably Ci - C 4 acid.
• Viable organic acids include particularly formic acid, acetic acid, propionic acid, and lactic acid, preferably formic acid, but other carboxylic acids or polycarboxylic acids, such as citric acid, can also be used.
• Inorganic acids include hydrochloric acid, sulphuric acid, or phosphoric acid, pref ⁇ erably phosphoric acid. They may be partly neutralised.
• Compositions that form acids include inorganic or organic salts or acid anhydrides that react in an acid man ⁇ ner.
• the acid components can also be produced chemically in the course of the preservation according to the invention; for example, by using lactic acid fermenta ⁇ tion controlled by enzymes and or bacterium inoculation.
• the acid component is a formic acid, acetic acid, lactic acid and/or propionic acid, possibly neutralised, pref ⁇ erably formic acid, of about 10-100, preferably about 30-100, and more preferably 60-100 wt-%.
• the preservative composition of the invention contains about 70-90 wt-% of formic acid, about 0-10 wt-% of or- thophosphoric acid, and about 1.5-3 wt-% of the ester composition according to the invention, and water.
• the preservative composition according to the invention may contain various total quantities of said ester components 1) and 2).
• the minimum content of ester component 1) in the preservative composition is about 0.25 wt-%, preferably about 0.5 wt-%, and most preferably about 1 wt-%.
• the maximum content of ester component 1) is about 10 wt-%, prefera ⁇ bly about 5 wt-%, and most preferably about 2.5 wt-%.
• the wt-% is given as ben- zoic acid and the moieties are advantageous when acid component 3) is also present.
• the mixture can contain other com ⁇ positions that improve the preservation power, including C 4 - C M carboxylic acids, such as free benzoic acid, isobutyric acid, or octanoic acid, or corresponding alco- hols; monoglycerides of C 8 - C ⁇ 6 carboxylic acids, or other bactericidal or bacte- riostatic surface-active compositions; dicarboxylic acids, such as oxalic acid, malo- nic acid, succinic acid, adipinic acid, pimelic acid, suberic acid, fumaric acid, or maleic acid; polycarboxylic acids, such as polyacrylic acid, or copolymer acids formed between unsaturated compositions that are polymerised with polyacrylic acid and acrylic acid: hydroxy carboxylic acids, hydroxy dicarboxylic acids, or hy- droxypolycarboxylic acids, such as sorbic acid, ascorbic acid, cin
• the mixture may contain metallic salts affecting as preservatives, including salts of magnesium, zinc, and copper, compositions that adjust animal nutrients or the salt content of the mixture or that buffer its pH, in ⁇ cluding ammonium phosphate or lemery salt; imidiatzolindylurea, phenolic com ⁇ positions and sulphonic acids, such as lignosulphonates, or aldehydes, such as for ⁇ maldehyde.
• components acting as antioxidants such as butylated hy- droxyanisole or hydroxytoluene, or esters of gallic acid can be added to the mixture.
• the preservative compositions according to the invention are manufactured by sim ⁇ ply mixing ester components 1) and 2) and possible other components, such as an acid component with each other.
• the preservative mixture is in soluble form at conventional temperatures. It can also be brought into solid form by absorbing it into large-area clay mineral, silica, or other absorption body.
• the composition ac ⁇ cording to the invention can also be used to treat or preserve other organic materials.
• organic materials include cuttings of beet produced as a by-product of sugar manufacturing, liquor forage, mash, distiller's grain, by-products used as forage for food industry, forage, or forage additives, as well as organic products intended for human nutri- tion.
• it can be used to improve the hygiene of cattle sheds and other con ⁇ structions, of plants and devices, whereby it is used to control hazardous micro ⁇ organisms.
• Organic material preserved by using the composition according to the invention can be used, not only for nutrition, but also for raw material in industrial processes. For instance, grain preserved by the composition according to the inven- tion gives increased sugar content, so that its use as raw material in alcohol manu- facture implies increased alcohol yield. At the same time, the drying of grain is avoided, which is an energy-consuming process.
• compositions When compositions are used in products intended for human or animal nutrition, their components must be chosen from compositions acceptable for additives of for ⁇ age or food.
• ester mixtures of the invention are not corrosive and they do not have pungent odours.
• the acid solutions containing them are better in these proportions than those without them.
• the invention is also related to a method for preserving green forage, fresh cuttings, grain, or the like.
• ester component 1) which is the ester of unsubsti ⁇ tuted or substituted benzoic acid with C t - C alcohol, or a mixture of such esters
• another ester component 2) that acts synergistically with said ester component 1) and is the ester of unaromatic Ci - C 20 carboxylic acid with Ci - C 9 alcohol, is added to a preservative containing an acid component 3) at the farm or some other place shortly before use or in connection with the use, so that a composition of the above-mentioned type that acts synergistically is produced as the effective mixture.
• Fig. 1 presents the amounts of acetic acid and lactic acid in forage when the pre- servative contains different amounts of ethyl benzoate, propyl formate, or the mix ⁇ ture thereof (Example 5),
• Fig. 2 presents the postfermentation of forage samples removed from storage, as indicated by maturity (Example 6), Fig. 3 shows how the efficacy of acetic acid is improved in prevention of salmonella when the combination of ethyl benzoate and propyl formate is used.
• Example 1 growing in solution/yeast
• Preservative amount 0 % 0.1 % 0.5 % 1.0 %
• the ethyl esters and propyl esters of the benzoic acid worked best of the individual preserva ⁇ Ves tested, being clearly efficacious at a dose of 0.1 %.
• the combination of the two did not increase the efficacy.
• the ethyl esters and propyl esters of the formic acid and the propionic acid alone did not yield sufficient inhibition of yeast even at a dose of 1.0 % in the test conditions.
• Surprising synergy was indicated when mixing an ester, which alone was not very efficacious, with benzoates, the composition obtained worked even better than the benzoate alone, even though the content of benzoate in these combinations was only half as large.
• Preservative amount 0 % 0.1 % 0.5 % 1.0 %
• Ethyl benzoate was the most efficacious of the individual preservatives. When es ⁇ ters of formic acid and propionic acid, which were inefficious or low-efficacious per se, were mixed with it, the result was improved as compared with ethyl benzoate alone. The best result was obtained by the mixture of ethyl benzoate and propyl formate.
• Example 3 growing in solution/propionic acid and lactic acid/yeast
• Tests according to Example 1 were conducted by using, as preservatives, 80 wt-% of propionic acid or 80 wt-% of lactic acid which contained the total of 5 wt-% of ethyl benzoate (EB) and/or propyl formate (PF).
• the dose of the preservative in the solution was 0.5 wt-%. The following results were obtained:
• Sample 3F containing ethyl benzoate yielded a reasonable result at a dose of 0.5 wt- %, even though the growth had been clearly started on the second day.
• sample 3G according to the invention containing lactic acid and synergistic ester composi ⁇ tion, in which the amount of ethyl benzoate is only half of that in Sample 3F, yeast has not grown during 3 days enough to change the turbulence reading of the initial state.
• the growth in Sample 3E with no esters and in Sample 3H containing propyl formate is very remarkable.
• Example 2 A test according to Example 2 was conducted by using acetic acid of 80 wt-% as the preservative solution, containing esters ethyl benzoate (EB) and/or propyl formate (PF). With doses of preservative of 0.5 and 0.2 wt-%, no growth could be perceived in any of the samples. With a dose of OJ wt-%, the following results were obtained, indicating that the growth of E. Coli was the slowest to start in solution 4C contain ⁇ ing the synergistic ester composition:
• timothy grass and meadow fescue was cut and measured into batches of 1 kg each and treated with different preservatives based on formic acid. The samples were enclosed into air-impermeable plastic bags. 5 parallel bag tests were conducted on each preservative. The doses of preservatives comprised 5 litres / a ton of forage.
• Barley seeds were preserved by means of different preservative solutions containing acid.
• the moisture level of barley was 43 wt-%.
• the preservative was measured by spraying on an Archimedean conveyor. Two grades of dose were used, 1.8 1 and 1.44 1 per hundred kilos of seeds.
• the former corresponds to the recommended dose of propionic acid for seeds with such moisture content, the latter is 20 % less.
• the seeds were stored in barrels.
• the Salmonella infantis that was 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 for the test by using different amounts of preservatives. The growth of bacteria was observed by a Bioscreen device (Labsystems, Finland). The device measures automatically the cloudiness that implies the growth of bacteria from the set of samples as a function of time. The results are shown in Figs. 3 A (acetic acid) and 3B (acetic acid containing 2.5 wt-% of EB and 2.5 wt-% of PF).
• Inhibition of growth of Salmonella can be perceived in the acetic acid concentration of 0.5 wt-% but when 5 wt-% of the ester composition of the invention was mixed with the ace ⁇ tic acid, in a ratio of 1 : 1 of ethyl benzoate + propyl formate, the growth could be inhibited even by an amount of 0.3 wt-% of preservative.
• a solution was made, containing 78 wt-% of formic acid, 2 wt-% of phosphoric acid, 1.25 wt-% of ethyl benzoate, 1.25 wt-% of propyl formate, and 17.5 wt-% of water. 55 weight fractions of moler earth (Damolin K 0.5-1 mm) was saturated with 45 weight fractions of the solution. A solid preservative was obtained which was easy to measure.

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• 1995
  • 1995-02-06 FI FI950512A patent/FI100376B/fi not_active IP Right Cessation
• 1996
  • 1996-02-05 EP EP96901370A patent/EP0808100A1/en not_active Withdrawn
  • 1996-02-05 EE EE9700169A patent/EE9700169A/et unknown
  • 1996-02-05 EP EP96901371A patent/EP0808101A1/en not_active Withdrawn
  • 1996-02-05 AU AU45421/96A patent/AU4542196A/en not_active Abandoned
  • 1996-02-05 AU AU45422/96A patent/AU4542296A/en not_active Abandoned
  • 1996-02-05 WO PCT/FI1996/000065 patent/WO1996024247A1/en not_active Application Discontinuation
  • 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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