WO2022112132A1 - Verfahren zur sterilisierung und konservierung von getränken - Google Patents

Verfahren zur sterilisierung und konservierung von getränken Download PDF

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Publication number
WO2022112132A1
WO2022112132A1 PCT/EP2021/082336 EP2021082336W WO2022112132A1 WO 2022112132 A1 WO2022112132 A1 WO 2022112132A1 EP 2021082336 W EP2021082336 W EP 2021082336W WO 2022112132 A1 WO2022112132 A1 WO 2022112132A1
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WO
WIPO (PCT)
Prior art keywords
formula
compounds
alkyl
beverage
compound
Prior art date
Application number
PCT/EP2021/082336
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German (de)
English (en)
French (fr)
Inventor
Jens Bitzer
Thomas Henkel
Marcus Taupp
Original Assignee
Lanxess Deutschland Gmbh
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 Lanxess Deutschland Gmbh filed Critical Lanxess Deutschland Gmbh
Priority to EP21806774.2A priority Critical patent/EP4250953A1/de
Priority to CN202180079832.5A priority patent/CN116507218A/zh
Publication of WO2022112132A1 publication Critical patent/WO2022112132A1/de

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Classifications

    • 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
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/42—Preservation of non-alcoholic beverages
    • A23L2/44—Preservation of non-alcoholic beverages by adding preservatives
    • 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

Definitions

  • the invention relates to a method for sterilizing and preserving beverages using specific glycolipids and dialkyl dicarbonates in specific weight ratios, the preserved beverages produced and the use of specific glycolipids for sterilizing and preserving beverages.
  • Food preservatives such as salt, sugar, and vinegar have been used for generations, and while they are relatively safe to use, their preservative effects are limited in both how long they last and the types of foods and beverages they can be used on.
  • preservatives, such as salt and vinegar in higher concentrations can affect the taste and health effects of the product.
  • Antimicrobial agents such as quaternary ammonium compounds, alcohols, chlorinated phenols, parabens and paraben salts, imidazolidinyl urea, phenoxyethanol, p-hydroxybenzoate, and small carboxylic acids such as benzoic acid, sorbic acid, salicylic acid, and lactic acid are among the commonly used preservatives with antimicrobial activity for body care and sometimes also in food , formic acid, propionic acid or corresponding salts. Formaldehyde releasers and isothiazolinones can also be used.
  • sausages, meat and meat preserves, stabilizers are often added that reduce water activity, such as potassium and/or sodium nitrites and -nitrates.
  • Smoke is also commonly used to preserve meat products, with the undesirable side effect of forming polycyclic aromatic hydrocarbons, which have carcinogenic properties.
  • Glycolipids are known from WO-A 2012/167920, which can be used as preservatives in beverages, cosmetics, foods, pharmaceuticals, medical devices or packaging materials.
  • dialkyl dicarbonates in particular of dimethyl dicarbonate (Velcorin®) for preserving beverages, is known, for example from EP-A 2161999.
  • glycolipids of this application in combination with at least one dialkyl dicarbonate, have a particularly high preservative effect in beverages and have a synergistic effect.
  • the carbohydrate residue R is preferably a trisaccharide. This trisaccharide particularly preferably contains at least one xylopyranose unit and/or at least one glucopyranose unit.
  • the carbohydrate radical R is preferably a radical of the formula (II). wherein rings A, B and C are independently monosaccharide residues containing at least one hydroxyl group which may optionally be acylated. Preferably rings A and B are xylopyranose residues and ring C is a glucopyranose residue.
  • esters can also be present intramolecularly, in the form of a lactone.
  • an ester bond is formed between the carboxyl function of the linear fatty acid residue and a terminal hydroxyl group of the carbohydrate residue R.
  • each of the hydroxyl groups of the carbohydrate residue R and/or the linear fatty acid residue can be esterified by a carboxylic acid. It is preferably an aliphatic, branched, straight-chain or cyclic carboxylic acid with a Ci-Ci2-alkyl radical. It is particularly preferably an aliphatic carboxylic acid with a Ci-C 6 -alkyl radical.
  • the carboxylic acids by which the hydroxyl groups of the carbohydrate residue R and/or of the linear fatty acid residue are esterified are very particularly preferably acetic acid and isovaleric acid.
  • 1, 2 or 3 hydroxyl groups of the carbohydrate residue R of the formula (I) and/or of the linear fatty acid residue are esterified by a carboxylic acid. It is preferably an aliphatic, branched, straight-chain or cyclic carboxylic acid with a Ci-Ci2-alkyl radical. It is particularly preferably an aliphatic, straight-chain carboxylic acid with a Ci-C 6 -alkyl radical. Even more preferably, one or two hydroxyl groups of the carbohydrate residue R of formula (I) are esterified by acetic acid and/or one hydroxyl group by isovaleric acid. The aliphatic, straight-chain carboxylic acid is very particularly preferably isovaleric acid.
  • At least one of the hydroxyl groups of the carbohydrate residue R of the formula (I) is esterified with a carboxylic acid having at least three carbon atoms. At least one of the hydroxyl groups of the carbohydrate residue R of the formula (I) is preferably esterified with an isovaleryl group.
  • the carbohydrate radical R is particularly preferably a compound of the formula (III) Bonding to an oxygen atom of the lipid group of the formula (I) (
  • R 2 is -H, alkali metal or an equivalent of an alkaline earth metal cation, or -Ci-C 6 -alkyl; preferably -H or alkali metal or an equivalent of an alkaline earth metal cation; and
  • R 2 , R 6 and R 7 H.
  • the compound of the formula (I) is at least one compound of the formulas (VA) to (VD) or mixtures of these compounds
  • salts within the meaning of the invention are alkali metal and/or alkaline earth metal salts, particularly preferably alkali metal salts.
  • the compounds of formula (V) are specific glycolipids.
  • the compounds of the formulas (I) to (V) are obtained from fungi by fermentation.
  • the preparation of these compounds is known, for example, from WO-A 2012/167920.
  • the compounds of the formula (I) are preferably obtained from the fungi as mixtures in the form of an extract. These can then be further purified, for example by column chromatography, such as in particular by high-pressure column chromatography, or by filtration and precipitation. The purification processes are known to those skilled in the art, for example from WO-A 2012/167920.
  • the fungus Dacryopinax sphatularia of the strain MUCL 53181 is used to prepare the compounds of the formulas (I) to (V).
  • the compounds of the formula (I) are used as mixtures.
  • mixtures of the compounds of the formula (V-A), formula (V-B), formula (V-C) and the compounds of the formula (V-D) are used. Preference is given to mixtures of the compounds of the formula (V-A) and compounds of the formula (V-B) and compounds of the formula (V-C) and compounds of the formula (V-D) in an amount of 30% by weight to 96% by weight, based on the total dry mass of the compounds used Compounds of formula (I) used.
  • Dialkyl dicarbonates are preferably compounds of the formula (VI) wherein
  • R 9 and R 10 independently represent straight-chain or branched C 1 -C 5 alkyl, cycloalkyl, C 2 -C 5 alkenyl or C 2 -C 5 alkynyl, each of which is optionally substituted one or more times, identically or differently, by halogen; nitro; cyano; Ci-C 6 alkoxy; dialkylamino; or phenyl which is optionally substituted one or more times, identically or differently, by halogen; nitro; cyano; alkyl; haloalkyl; alkoxy; haloalkoxy; acyl; acyloxy; alkoxycarbonyl; carboxyl, preferred
  • R 9 and R 10 independently represent straight-chain or branched Ci-Cs-alkyl or C2-Cs-alkenyl, particularly preferred
  • R 9 and R 10 are, independently of one another, straight-chain or branched Ci-C 5 -alkyl or C3-alkenyl, and are very particularly preferred
  • R 9 and R 10 are independently methyl, ethyl, isopropyl, tert-butyl, tert-amyl, allyl or benzyl.
  • Dialkyl dicarbonate is particularly preferably diethyl dicarbonate or dimethyl dicarbonate, in particular dimethyl dicarbonate.
  • Dimethyl dicarbonate is preferably used in a mixture with 100 ppm to 500 ppm phosphates.
  • the preparation of this mixture and the possibility for Stabilization of dimethyl dicarbonate with phosphorus compounds is known, for example, from US Pat. No. 8,207,368.
  • the compounds of the formula (I) are used in the beverages preferably in a concentration of 1 to 30 ppm, particularly preferably of 1 to 20 ppm and even more preferably in a concentration of 1 to 15 ppm.
  • Dialkyl dicarbonates are preferably used in the beverages in a concentration of 20 ppm to 150 ppm, particularly preferably 30 to 100 ppm.
  • the weight ratio of the compounds of formula (I) and the dialkyl dicarbonates is preferably from 1:30 to 1:60.
  • the weight ratio of the compounds of formula (I) and the dialkyl dicarbonates is 1:30 to 1:60 and the concentration of the dialkyl dicarbonates is 10 to 300 ppm in the beverages.
  • 1 ppm to 30 ppm of the compounds of the formula (I) and 50 to 300 ppm of dialkyl dicarbonates, in particular dimethyl dicarbonate, are used in a weight ratio of 1:10 to 1:70, the amount of the compounds of the formula ( I) must be chosen so that the amount of dialkyl dicarbonates in the beverage is less than or equal to 300 ppm.
  • Beverages within the meaning of the invention are aqueous products for drinking, typically including water, consumed for thirst quenching, nourishment, savoring or enjoyment and/or for other functional purposes, for example for the delivery of drugs or other functional materials be able.
  • beverages are preferably aqueous products for drinking which contain at least 60% by weight of water.
  • these products may also contain flavorings, sugars, emulsifiers, artificial and natural flavor enhancers, buffering agents, acids or other consumable beverage additives.
  • Beverages particularly preferably contain 80 to 90% by weight water, 2 to 8% by weight artificial and/or natural flavorings, 4 to 8% by weight sucrose and 4 to 14% by weight acidulants, such as preferably citric acid and sugar other than sucrose.
  • beverages contain 80 to 90% by weight water, 0.1 to 10% by weight artificial and/or natural flavorings, 4 to 8% by weight sucrose and 0.1 to 4% by weight acidifiers, such as preferably citric acid and Sugar unlike sucrose.
  • Other beverage additives can preferably be included.
  • the sum of water, artificial and/or natural flavorings, sucrose, acidifier and sugar other than sucrose in the beverages is > 90% by weight.
  • further compounds such as, for example and preferably, emulsifiers, artificial and natural flavor enhancers and buffer substances can be included.
  • Beverages are preferably water, flavored water, fortified water, flavored beverages, carbonated water, flavored seltzer or soda water, juices, cola, lemon-lime, ginger beer, and root beer beverages that are carbonated in the manner of soft drinks, and beverages that are Health or wellness benefits may be provided by the presence of metabolically active substances such as vitamins, amino acids, proteins, carbohydrates, lipids or polymers thereof, such products may also be formulated to contain milk, coffee or tea (e.g. green tea) or other vegetable solids , syrup, diet drinks, carbonated soft drinks, fruit juices e.g. B.
  • B. impart one of the aforementioned fruit juices and contain more than 0% fruit juice but less than 100% fruit juice, fruit-flavored beverages, vegetable juices, preferably tomato juice, beet juice, carrot juice, celery juice, vegetable-containing beverages that impart the flavor of one of the aforementioned vegetable juices and containing more than 0% vegetable juice but less than 100% vegetable juice, isotonic beverages, non-isotonic beverages, soft drinks containing a fruit juice, coffee, tea, tea beverages made from tea concentrate. Extracts or powders, drinkable milk products, eg drinkable yoghurts (drinking yoghurt), kefir or buttermilk, hot chocolate, chocolate powder/mixtures, drinkable soy products, non-diet milk, preferably.
  • drinkable milk products eg drinkable yoghurts (drinking yoghurt), kefir or buttermilk, hot chocolate, chocolate powder/mixtures, drinkable soy products, non-diet milk, preferably.
  • coconut milk alcoholic beverages, preferably malt beverages, wine, beer, distilled liqueurs, spirits, sparkling wine, champagne or liqueurs, fruit smoothies, horchata (vegetable and/or rice components that go into a drink processed), sports drinks, energy drinks, health drinks, shakes, protein drinks (e.g. milk, soy, rice or other), drinkable soy yoghurts, low-acid drinks as defined in US 21 CFR Part 113. Acidified drinks as defined in US 21 CFR Part 114, nectars, tonics, frozen carbonated beverages, frozen non-carbonated beverages, liquid meal substitutes, infant formulas, and combinations or blends thereof.
  • a "juice” is the aqueous liquid expressed or extracted from one or more fruits or vegetables, purees of the edible parts of one or more fruits or vegetables, or concentrates of that liquid or puree.
  • Carbonated drinks are also referred to as carbonated drinks within the scope of the patent application.
  • Beverages to which no carbon dioxide is added are also referred to as non-carbonated beverages within the scope of the patent application.
  • At least one compound of the formula (I) is first added to the beverage in step a.) and then at least one dialkyl dicarbonate is added to the beverage in step b.).
  • the addition can take place at any temperatures and pressures.
  • the compounds of the formula (I) and the dialkyl dicarbonates are preferably added at from 15 to 30.degree.
  • the compounds of the formula (I) are added either as a solid, preferably in powder form, or as a stock solution in water, which is preferably introduced with stirring.
  • the addition to the drink or the corresponding aqueous precursors, which are preferably placed in a tank, can be done at any time manually or mechanically via a corresponding dosing device.
  • the compounds of the formula (I) and the dialkyl dicarbonates can also be initially taken and the beverages or the precursors of the beverages can be added thereto.
  • a point in time before the finished beverage is filled is preferably selected.
  • the dosing into the beverage preferably takes place at least 2 hours before the beverage is filled.
  • a stock solution is preferably used, preferably in a concentration of 0.1 to 10% by weight, particularly preferably in a concentration of 1-5% by weight.
  • the compounds of the formula (I) are preferably dissolved in water (for example 10 g in one liter of water) at room temperature while stirring for 2-3 minutes using a hand mixer (eg KitchenAid 5KHB1231).
  • the dialkyl dicarbonates can be added as a liquid manually or mechanically via a metering device. The addition preferably takes place with the aid of a dosing pump, preferably before the finished beverage is filled.
  • the amount of the compounds of formula (I) and/or the dialkyl dicarbonates in the beverages after addition is preferably not measured but calculated.
  • the compounds of the formula (I) used and the dialkyl dicarbonates act against infestation and/or decomposition by microorganisms, such as, for example and preferably, bacteria, fungi or yeasts.
  • the compounds of the formula (I) used and the dialkyl dicarbonates have a controlling effect on a number of microorganisms such as fermentative yeasts, molds or fermentative bacteria.
  • the mixtures of compounds of the formula (I) and the dialkyl dicarbonates preferably act against Aspergillus brasiliensis, Aspergillus niger Byssochlamys fulva, Dekkera bruxellensis, Saccharomyces cerevisiae, Mycoderma, Brettanomyces spp, Lactobacillus brevis, Lactobacillus buchneri, Lactobacillus plantarum, Zygosaccharomyces bailii and Candida intermedia.
  • the mixtures of compounds of the formula (I) and the dialkyl dicarbonates act particularly preferably against Saccharomyces cerevisiae, Zygosaccharomyces bailii and Candida intermedia.
  • the beverages produced according to the method according to the invention are also encompassed by the invention.
  • the compounds of the formula (I) used in the beverages and the dialkyl dicarbonates surprisingly have a synergistic effect in the range according to the invention and are highly effective against microorganisms. Outside the scope of the invention, their effect is rather poor or even antagonistic.
  • the total amount of the compounds of the formula (I) used was 95% by weight, based on the dry matter.
  • DMDC dimethyl dicarbonate
  • the non-carbonated apple juice from Rewe “Beste Wahl Apfelsaft” from PET bottles was used as the test matrix, diluted 1:1 with sterilized tap water with a pH of 3.56.
  • the specification in mg/l represents a concentration specification. 1 mg/l is 1 ppm.
  • glycolipids The compounds of the formula (I) are referred to below as glycolipids. Table 2
  • the beverage samples for determining the minimum inhibitory concentration (MIC) were created by directly pipetting DMDC or a 5% stock solution of the natural glycolipids into the test matrix and then shaking for an adequate distribution.
  • the MIC was determined by using only the glycolipids or DMDC in the test matrix in accordance with DIN 58940-8.
  • the initial test solution was serially diluted with the test matrix so that each subsequent solution contained 50% of the previous drug concentration, while maintaining the nutrient concentration (test matrix).
  • the MIC is defined as the minimum concentration of drug that inhibits cell growth, determined by counting viable cells after 72 hours of incubation on agar plates.
  • Example 2 (according to the invention)
  • the MIC was determined according to DIN 58940-8 using combinations of glycolipids and DMDC in the test matrix.
  • the initial test solution was serially diluted with the test matrix as described in Example 1.
  • FIC Index is calculated according to the formula:
  • FICI FIC (Component 1) + FIC (Component 2),
  • the FICI is calculated as ⁇ 1, the two components 1 and 2 behave synergistically; the lower the FICI ( ⁇ 1), the stronger the synergistic effect of the two components together. If the FICI is ⁇ 0.5 then the synergy is considered very strong.
  • test matrix (apple juice with water, 1:1) was contaminated with 100 cfu/ml of a mixture of three yeasts (Candida intermedia, Saccharomyces cerevisiae, Zygosaccharomyces bailii; all independently isolated from beverage samples and stored in our own strain collection). As described in Example 1, the MIC values were determined after incubation at 28° C. for two weeks for the individual components and for combinations of both components.
  • An apple juice drink was prepared using the example recipe as in described in Table 9:
  • the amount of compounds of formula (I) in the beverages is 5 ppm.
  • Carbonated Beverage The ingredients were combined in a tank at 25°C in the order named in the table and mixed into a syrup. In this step, 10.34% of the above amount of water was used. After each addition, the ingredients were homogenized using a centrifugal pump via a tank-in-tank mixing system. The aqueous glycolipid stock solution was then added with gentle stirring. The syrup was then mixed with carbonated water in proportion to volume using an Ortmann + Herbst intermix (consisting of vacuum degassing, carbonation and buffer tank). The product was transferred from the buffer tank to the Kosme filling machine using a frequency-controlled centrifugal pump. The VDT dosing pump was integrated in the product line Touch (Serial No.
  • Non-carbonated drink
  • the ingredients were added at 25°C in a tank in the order named in the table. After each addition, the ingredients were homogenized using a centrifugal pump via a tank-in-tank mixing system. The aqueous glycolipid stock solution was then added with gentle stirring. The finished product was then transferred directly from the batch tank to the Kosme filling machine using a frequency-controlled centrifugal pump. 90mg/l of dimethyl dicarbonate were injected into the product line using a VDT Touch dosing pump (serial no. 90332615). The apple juice drink was then filled into 0.5L PET bottles.
  • a total of 404 bottles were filled. These were stored at room temperature for 35 days. The filled product was then inspected for visual changes caused by microbiological factors. For this purpose, each bottle was individually positioned in front of a light source and checked for sediment formation, turbidity, flocculation, mycelium formation or similar deviations. After the end of the incubation period, none of the bottles showed any changes that indicated microbiological contamination.
  • 5 samples from the beginning, middle and end of production were each plated in duplicate on MRS (De Man, Rogosa and Sharpe) and OSA (Orange Serum Agar) and aerobically at 30°C for 3 days (MRS) and 5 days ( OSA) incubated. The germ count displayed was ⁇ 1 CFU/ml.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Microbiology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Non-Alcoholic Beverages (AREA)
PCT/EP2021/082336 2020-11-27 2021-11-19 Verfahren zur sterilisierung und konservierung von getränken WO2022112132A1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP21806774.2A EP4250953A1 (de) 2020-11-27 2021-11-19 Verfahren zur sterilisierung und konservierung von getränken
CN202180079832.5A CN116507218A (zh) 2020-11-27 2021-11-19 用于对饮料进行灭菌和防腐的方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20210418.8 2020-11-27
EP20210418 2020-11-27

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WO2022112132A1 true WO2022112132A1 (de) 2022-06-02

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EP (1) EP4250953A1 (zh)
CN (1) CN116507218A (zh)
AR (1) AR124124A1 (zh)
CO (1) CO2021015657A1 (zh)
WO (1) WO2022112132A1 (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4292441A1 (de) * 2022-06-13 2023-12-20 LANXESS Deutschland GmbH Vorrichtung und verfahren zum konservieren von getränken
WO2024046710A1 (de) * 2022-08-31 2024-03-07 Lanxess Deutschland Gmbh Vorrichtung und verfahren zum konservieren von getränken

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7074447B2 (en) 2001-04-28 2006-07-11 Laboratories Miret, S.A. Antimicrobial composition comprising potassium sorbate and LAE
WO2008014889A2 (de) * 2006-07-29 2008-02-07 Lanxess Deutschland Gmbh Konservierungsmittel auf basis von carbonsäureanhydriden
EP2161999A1 (de) 2007-06-23 2010-03-17 Lanxess Deutschland GmbH VERFAHREN ZUR MIKROBIELLEN STABILISIERUNG VON GETRÄNKEN MIT EINEM PH VON GRÖßER ALS 4,2 MIT DIALKYLDICARBONATEN
DE102008048714A1 (de) * 2008-09-24 2010-03-25 Lanxess Deutschland Gmbh Verfahren zur Konservierung von Getränken
US8207368B2 (en) 2006-04-22 2012-06-26 Lanxess Deutschland Gmbh Stabilization of diesters of dicarbonic acid
WO2012167920A1 (en) 2011-06-10 2012-12-13 Intermed Discovery Gmbh Long chain glycolipids useful to avoid perishing or microbial contamination of materials
WO2017178497A1 (en) * 2016-04-13 2017-10-19 Imd Natural Solutions Gmbh Formulation systems for antimicrobial glycolipids

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7074447B2 (en) 2001-04-28 2006-07-11 Laboratories Miret, S.A. Antimicrobial composition comprising potassium sorbate and LAE
US8207368B2 (en) 2006-04-22 2012-06-26 Lanxess Deutschland Gmbh Stabilization of diesters of dicarbonic acid
WO2008014889A2 (de) * 2006-07-29 2008-02-07 Lanxess Deutschland Gmbh Konservierungsmittel auf basis von carbonsäureanhydriden
EP2161999A1 (de) 2007-06-23 2010-03-17 Lanxess Deutschland GmbH VERFAHREN ZUR MIKROBIELLEN STABILISIERUNG VON GETRÄNKEN MIT EINEM PH VON GRÖßER ALS 4,2 MIT DIALKYLDICARBONATEN
DE102008048714A1 (de) * 2008-09-24 2010-03-25 Lanxess Deutschland Gmbh Verfahren zur Konservierung von Getränken
WO2012167920A1 (en) 2011-06-10 2012-12-13 Intermed Discovery Gmbh Long chain glycolipids useful to avoid perishing or microbial contamination of materials
WO2017178497A1 (en) * 2016-04-13 2017-10-19 Imd Natural Solutions Gmbh Formulation systems for antimicrobial glycolipids

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4292441A1 (de) * 2022-06-13 2023-12-20 LANXESS Deutschland GmbH Vorrichtung und verfahren zum konservieren von getränken
WO2024046710A1 (de) * 2022-08-31 2024-03-07 Lanxess Deutschland Gmbh Vorrichtung und verfahren zum konservieren von getränken

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CO2021015657A1 (es) 2023-05-29
CN116507218A (zh) 2023-07-28
AR124124A1 (es) 2023-02-15
EP4250953A1 (de) 2023-10-04

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