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WO2007063043A1 - Composition antimicrobienne améliorée - Google Patents

Composition antimicrobienne améliorée Download PDF

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Publication number
WO2007063043A1
WO2007063043A1 PCT/EP2006/068932 EP2006068932W WO2007063043A1 WO 2007063043 A1 WO2007063043 A1 WO 2007063043A1 EP 2006068932 W EP2006068932 W EP 2006068932W WO 2007063043 A1 WO2007063043 A1 WO 2007063043A1
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WO
WIPO (PCT)
Prior art keywords
product
composition
ppm
natamycin
lysine
Prior art date
Application number
PCT/EP2006/068932
Other languages
English (en)
Inventor
Jacobus Stark
Nicole Liliane Dutreux
Original Assignee
Dsm Ip Assets B.V.
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 Dsm Ip Assets B.V. filed Critical Dsm Ip Assets B.V.
Publication of WO2007063043A1 publication Critical patent/WO2007063043A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/195—Antibiotics
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729—Organic compounds; Microorganisms; Enzymes
    • A23B2/742—Organic compounds containing oxygen
    • A23B2/754—Organic compounds containing oxygen containing carboxyl groups
    • A23B2/758—Carboxylic acid esters
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729—Organic compounds; Microorganisms; Enzymes
    • A23B2/762—Organic compounds containing nitrogen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/105—Aliphatic or alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/111—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/142—Amino acids; Derivatives thereof
    • A23K20/147—Polymeric derivatives, e.g. peptides or proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/195—Proteins from microorganisms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin

Definitions

  • the present invention discloses anti-microbial compositions to prevent microbial spoilage in foodstuffs, agricultural products, pharmaceutical products, adhesives, paints, inks and cosmetics.
  • Examples of fresh food products particularly sensitive to bacterial spoilage are dairy products (e.g. cheese, cottage cheese, ricotta, cream cheese, sour cream and yogurt), meat or fish products (e.g. hamburgers, sausages and pate), (processed) eggs, (processed) fruits, (processed) vegetables or grains such as boiled or steamed rice, spaghetti and cooked vegetables.
  • dairy products e.g. cheese, cottage cheese, ricotta, cream cheese, sour cream and yogurt
  • meat or fish products e.g. hamburgers, sausages and pate
  • processed eggs e.g. hamburgers, sausages and pate
  • processed eggs e.g. hamburgers, sausages and pate
  • processed eggs e.g. hamburgers, sausages and pate
  • processed eggs e.g. hamburgers, sausages and pate
  • processed processed foods are not eaten directly after processing thereby permitting bacteria, which survived the production process (e.g. spore formers) or bacteria introduced by post-contamination to grow
  • the invention provides novel natural improved anti-microbial compositions and methods for preserving foodstuffs, agricultural products, adhesives, paints, inks, cosmetics and pharmaceutical products by applying the composition of the invention. Unexpectedly, we have found that the composition of the invention is stable, and effective against a broad- spectrum of microbe.
  • the invention provides a composition comprising an epsilon-poly- L-lysine and an anti-fungal agent, wherein the anti-fungal agent is selected from the group consisting of natamycin, sorbic acid, propionic acid, benzoic acid, and salts of these compounds.
  • the combination of the components together works synergistically and is more effective against microbial growth than each agent taken separately.
  • composition of the invention may contain a further anti-fungal agent, wherein the further anti-fungal agent is selected from the group consisting of: 1. a weak acid preservative such as sorbic acid, propionic acid, benzoic acid, a p- hydroxybenzoic acid, lactic acid, citric acid, acetic acid or an alkali metal or alkali earth metal salt thereof or a polyphosphate;
  • a weak acid preservative such as sorbic acid, propionic acid, benzoic acid, a p- hydroxybenzoic acid, lactic acid, citric acid, acetic acid or an alkali metal or alkali earth metal salt thereof or a polyphosphate
  • a polyene anti-microbial compound preferably natamycin
  • dimethyl dicarbonate 7. a biphenyl-, a diphenyl-, an orthophenylphenol- or a thiabendazole- ;
  • an inorganic acid such as hydrochloric acid
  • imidazole such as imazalil
  • an anti-microbial compound known in the art for use as a preservative for food products, crop protection or after-harvest treatment of fruits, vegetables or cereals, pharmaceutical or cosmetic products.
  • the combination of these components together works synergistically such that the combination is more effective against microbial growth than each agent taken separately.
  • the composition of the invention consists of a ⁇ -Poly-L- lysine and an anti-fungal agent, wherein the anti-fungal agent is selected from the group consisting of natamycin, sorbic acid, propionic acid, benzoic acid, and salts of these compounds.
  • epsilon-poly-L-lysine is equivalent to ⁇ -Poly-L-lysine.
  • ⁇ - Poly-L-lysine is a homo-poly amino acid in which the carboxyl group is linked to the ⁇ - amino group of L-lysine, which is an essential amino acid.
  • Epsilon-poly-L-lysine contains in general from 25 to 35 L-lysine residues.
  • an epsilon poly-L-lysine means at least one epsilon poly-L-lysine having from 25 to 35 L-lysine residues.
  • Epsilon-Poly-L-lysine is a stable natural fermentation compound.
  • This compound is produced during aerobic fermentation of Streptomyces albulus. It is on the market under the brand name Save-Ory® (Chisso, Japan).
  • the anti-bacterial activity of ⁇ -Poly-L-lysine is based on the electrostatic absorption of ⁇ -Poly-L-lysine to the cell surface on the basis of its poly-cationic properties.
  • Epsilon-Poly-L-lysine is particularly effective against Gram-positive bacteria, especially of the genus Bacillus. But, in practice it is not efficient enough to prevent the growth of Gram-negative bacteria in foods. Only at very high concentrations some inhibition is observed.
  • natamycin refers to the anti-fungal agent also known as pimaricin. Natamycin has been used for more than 30 years to prevent outgrowth of fungi on cheeses and sausages. Natamycin is on the market under the brand name of Delvocid® or Natamax®, a powder composition containing 50% (w/w) of natamycin and 50% (w/w) of lactose. Natamycin has a MIC (Minimal Inhibition Concentration) of less than 10 ppm for most food born fungi while its solubility in water is from 30 to 50 ppm. Natamycin can easily be applied to prevent spoilage by fungi in food products. However, the low solubility of natamycin has limited its use to the surface treatment of cheese and fluids e.g. juices, lemonades, wine and yoghurt.
  • Salts of benzoic acid, propionic acid and ascorbic acid are well-known in the art, especially their methyl, calcium, sodium and potassium salts.
  • potassium sorbate is used.
  • the composition of the invention comprises: ⁇ -Poly-L-lysine preferably in an amount of 20 to 1 000 000 ppm, more preferably 100 to 300 000 ppm and natamycin preferably in an amount of 5 to 50 000 ppm, more preferably in an amount of 10 to 20 000 ppm, or potassium sorbate, preferably in an amount of 1000-500 000 ppm, more preferably in an amount of 5000 to100 000 ppm.
  • composition of the invention comprises: ⁇ -Poly-L-lysine preferably in an amount of 20 to 1 000 000 ppm, more preferably
  • 100 to 300 000 ppm and acetic acid, sodium acetate preferably in an amount of 0.001 to 3% (w/w) each, more preferably in an amount of 0.05 to 0.3% (w/w) and/or sodium chloride preferably in an amount of 1 to 99% (w/w) and/or natamycin preferably in an amount of 5 to 50 000 ppm, more preferably in an amount of 10 to 20 000 ppm, or potassium sorbate, preferably in an amount of 1000-500 000 ppm, more preferably in an amount of 5000 to 100 000 ppm.
  • the composition of the invention can be used for any type of applications in food products, agricultural products, adhesives, paints, inks, cosmetic products or pharmaceutical products.
  • the composition may be a liquid composition, a coating emulsion, a dry formulation such as a powder, a granulate or a tablet.
  • Each constituent of the composition of the invention may be applied separately to the product to be treated.
  • the composition of the invention is first prepared, subsequently added to the product to be treated.
  • the skilled person would know how to choose the best suited concentration for each constituent of the composition.
  • a liquid composition is used in an immersion treatment or a spraying treatment.
  • the immersion liquid may be of any kind.
  • a surfactant may be of advantage, in particular for treating objects with a hydrophobic surface.
  • the composition of the invention is a composition suitable for treating agricultural products such as fruits, vegetable, flower bulbs and seed.
  • Preferred fruits are citrus fruit, bananas, pine apple, apple, peer, strawberry and the like.
  • a preferred citrus fruit is orange.
  • the composition of the invention is a pharmaceutical preparation suitable for topical application.
  • suitable pharmaceutical preparations are lotions, creams and ointments.
  • the composition of the invention is a glue, preferably a water-based or water-thinned glue, including glues based on starch or modified starch and casein.
  • the composition of the invention is an ink or paint, preferably a water-based or water-thinned ink or paint.
  • the composition may be used to protect the ink or paint itself, but can also be used to protect the surface to which the ink or paint is applied.
  • the composition of the invention is used in a coating.
  • the coating may for example be applied to domestic appliances, work surfaces for domestic and industrial use, architectural and other engineering products, garden furniture and marine vessels.
  • the composition of the invention may further comprise water and/or salt and/or any component selected from the group consisting of a solvent, a surfactant, a carrier, a thickener.
  • a preferred carrier is fumed silica.
  • Preferred solvents are an alcoholic solvent comprising one or more lower alcohols (C1-C4), an aqueous acid, an aqueous alkali, glacial acetic acid or mixtures of an alcoholic solvent comprising one or more lower alcohol with either an aqueous acid, an aqueous alkali or glacial acetic acid.
  • Preferred surfactants are sodium lauryl sulphate, dioctyl sulphosuccinate, calcium chloride, or surfactants of the non-ionic types, for example those, which are known under the brand names TweenTM, SpanTM, BrijTM, and MyrjTM.
  • a thickener may be any thickener known in the art for use in food products.
  • Preferred thickeners are hydroxypropylmethylcellulose (HPMC), and/or gums, and/or carrageenan and/or methylcellulose.
  • Preferred gums are xanthan gum and/or gellan gum and/or arabic gum.
  • the invention provides a method for treating a product with the composition of the invention.
  • the composition can be added to the product to be treated at any moment or step of processing of the product.
  • the composition can be added to the end product before packaging, during processing or to any ingredients used to prepare the products.
  • Each constituent of the composition of the invention can be added separately to the product to be treated.
  • the composition is first prepared and subsequently added to the product to be treated.
  • the advantage of the present invention is that it allows the production of microbiologically stable and safe products with low concentration of anti-microbials.
  • the innovative composition can be used to preserve microbiological safety and/or stability in all kind of products.
  • the product is a food product such as a dairy product, e.g.
  • ice cream mixes yoghurt, any type of cheese, e.g. cottage cheese, ricotta, cream cheese, sour cream.
  • Other preferred food products are hot-baked flour products, spreads, margarines, sauce, dressings, any rice-containing product or any other foodstuffs distributed at ambient or chilled temperatures.
  • Other preferred food products are beverages like fruit juice, wine.
  • the addition of the composition of the invention to food products is furthermore expected to reduce or completely eliminate moulds, yeasts and bacterial outgrowth on the food products in the time frame comprised between the end of the processing of the product, size reduction included, and commercial sale. This time frame varies with the type of food, the distribution and sale conditions.
  • the product to be treated is such that its surface will be in contact with oxygen at the end of its processing and/or later on if a reduction of size occurs.
  • a product which has been treated with a composition of the invention.
  • the product is a water-containing product for example a food product, which comprises the composition of the invention.
  • the product treated with the composition of the invention comprises: - ⁇ -Poly-L-lysine preferably in an amount of 2 to 2 000 ppm, more preferably 10 to
  • 300 ppm and natamycin preferably in an amount of 0.5 to 50 ppm, more preferably in an amount of 1 to 20 ppm, or potassium sorbate, preferably in an amount of 100-3000 ppm, more preferably in an amount of 400 to 2500 ppm.
  • the product treated with the composition of the invention comprises: ⁇ -Poly-L-lysine preferably in an amount of 2 to 2 000 ppm, more preferably 10 to 300 ppm and acetic acid, sodium acetate, preferably in an amount of 0.001 to 3% (w/w) each, more preferably in an amount of 0.05 to 0.3% (w/w) and/or sodium chloride preferably in an amount of 1 to 99% (w/w) and/or natamycin preferably in an amount of 0.5 to 50 ppm, more preferably in an amount of 1 and 20 ppm, or potassium sorbate, preferably in an amount of 100 to 3000 ppm, more preferably in an amount of 400 to 2500 ppm.
  • composition of the invention to obtain a product, for example a food product, comprising the composition of the invention.
  • a method for treating a product for example a food product, with the composition of the invention.
  • the invention relates to a method for protecting a product against microbial spoilage by applying the composition of the invention.
  • the product may be a food product, an agricultural product, a cosmetic product, a water- based paint, a water-based ink, or a water-based glue.
  • the composition may be applied by any suitable means, be it by mixing with, incorporation in or surface application onto the earlier mentioned products. Before, during or after the addition of the composition to the product, other ingredients such as colorants, texturals etc. may be added as well to the product.
  • Example 1 Inhibition of Aspergillus niger by natamycin, ⁇ -Poly-L-lysine and a combination thereof
  • DSM strain 402 The behaviour of the mould Aspergillus niger (DSM strain 402) was studied in the presence of natamycin and ⁇ -Poly-L-lysine.
  • Two commercially available products were used as sources of the products tested: Delvocid (DSM; 50% natamycin) and Save-Ory PL-50TM (Chisso; 50% polylysin).
  • Delvocid DSM
  • Save-Ory PL-50TM Choso; 50% polylysin
  • Table 1 Behaviour of A. niger in the presence of natamycin and/or ⁇ -Poly-L-lysine
  • natamycin and polylysin + Concentration of active components: natamycin and polylysin +: Growth observed -: No growth observed
  • Example 2 Inhibition of Kluyveromyces marxianus by natamycin, ⁇ -Poly-L- lysine and a combination thereof
  • the behaviour of the yeast Kluyveromyces marxianus was studied in the presence of natamycin and ⁇ -Poly-L-lysine.
  • Two commercially available products were used as sources of the products tested: Delvocid (DSM; 50% natamycin) and Save-Ory GA-30TM (Chisso; 1.75% polylysin).
  • Delvocid DSM
  • Save-Ory GA-30TM Choso; 1.75% polylysin.
  • the effect of these products on the growth of K. marxianus was tested in Potato Dextrose Broth (Difco, pH 5 [PDB]).
  • PDB PDB was supplemented with various levels of the products mentioned. Subsequently, the broths were inoculated with yeast cells, which had been cultured overnight in PDB at 25°C, prior to use (final level 8x10 2 cells/ml). During storage in multiwell plates at 25°C, the behaviour of K. marxianus was studied using OD measurements (turbidity indicating growth).
  • Example 3 Inhibition of Aspergillus niger by K-sorbate, ⁇ -Poly-L-lysine and a combination thereof
  • Example 4 Inhibition of Kluyveromyces marxianus by K-sorbate, ⁇ -Poly-L- lysine and a combination thereof
  • K-sorbate Aldrich, 99% K- sorbate
  • Save-Ory PL-50TM Choisso; 50% polylysin
  • Save-Ory GA-30TM Choisso; 1.75% polylysin
  • PDB PDB was supplemented with various levels of the products mentioned. Subsequently, the broths were inoculated with yeast cells, which had been cultured overnight in PDB at 25°C, prior to use (final level 8x10 2 cells/ml). During storage in multiwell plates at 25°C, the behaviour of K. marxianus was studied using OD measurements (turbidity indicating growth). The results, presented in table 4, indicate that combinations of low levels of K- sorbate and polylysin, individually not sufficient to inhibit growth of K. marxianus, are able to inhibit growth of the yeast.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Wood Science & Technology (AREA)
  • Microbiology (AREA)
  • Molecular Biology (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)

Abstract

La présente invention concerne une composition comprenant de la epsilon-poly-L-lysine et un agent antifongique. La composition a une meilleure activité antimicrobienne. L'invention concerne également des procédés servant à conserver des aliments, des produits agricoles, des adhésifs, des peintures, des encres, des produits cosmétiques et des produits pharmaceutiques en appliquant la composition de l'invention. La composition de l'invention est stable et efficace contre un large spectre de microbes.
PCT/EP2006/068932 2005-11-29 2006-11-27 Composition antimicrobienne améliorée WO2007063043A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP05111429 2005-11-29
EP05111430.4 2005-11-29
EP05111430 2005-11-29
EP05111429.6 2005-11-29

Publications (1)

Publication Number Publication Date
WO2007063043A1 true WO2007063043A1 (fr) 2007-06-07

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011077071A1 (de) * 2011-06-07 2012-12-13 Beiersdorf Ag Wirkstoffkombinationen aus Epsilon-Polylysin und Climbazol
CN113215856A (zh) * 2021-06-08 2021-08-06 辽宁大学 接触型纸质文物综合保护剂及其制备方法和应用

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0254419A2 (fr) * 1986-06-24 1988-01-27 Chisso Corporation Agent pour prévenir les maladies à virus des plantes
JPH0453475A (ja) * 1990-06-22 1992-02-21 Chisso Corp 食品保存用酢酸製剤
EP0501373A2 (fr) * 1991-02-28 1992-09-02 Chisso Corporation Gel de protéine de petit-lait et procédé pour sa production
JPH0541969A (ja) * 1990-12-13 1993-02-23 Okuno Seiyaku Kogyo Kk 食品用保存剤
EP0599652A2 (fr) * 1992-11-25 1994-06-01 Chisso Corporation Stabilisateurs de réaction enzymatique et préservatifs enzymatiques
JPH0716087A (ja) * 1993-06-30 1995-01-20 Taishiyoo Technos:Kk 食品の保存方法
JPH11123070A (ja) * 1997-10-23 1999-05-11 Chisso Corp 食品保存剤
EP1062880A1 (fr) * 1998-02-16 2000-12-27 Yoshinori Hisamori Ltd. Naito Aliments congeles et procede de production correspond

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0254419A2 (fr) * 1986-06-24 1988-01-27 Chisso Corporation Agent pour prévenir les maladies à virus des plantes
JPH0453475A (ja) * 1990-06-22 1992-02-21 Chisso Corp 食品保存用酢酸製剤
JPH0541969A (ja) * 1990-12-13 1993-02-23 Okuno Seiyaku Kogyo Kk 食品用保存剤
EP0501373A2 (fr) * 1991-02-28 1992-09-02 Chisso Corporation Gel de protéine de petit-lait et procédé pour sa production
EP0599652A2 (fr) * 1992-11-25 1994-06-01 Chisso Corporation Stabilisateurs de réaction enzymatique et préservatifs enzymatiques
JPH0716087A (ja) * 1993-06-30 1995-01-20 Taishiyoo Technos:Kk 食品の保存方法
JPH11123070A (ja) * 1997-10-23 1999-05-11 Chisso Corp 食品保存剤
EP1062880A1 (fr) * 1998-02-16 2000-12-27 Yoshinori Hisamori Ltd. Naito Aliments congeles et procede de production correspond

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Composition of antibacterial agent for food and kitchenware", DERWENT, 9 January 2002 (2002-01-09), XP002366882 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011077071A1 (de) * 2011-06-07 2012-12-13 Beiersdorf Ag Wirkstoffkombinationen aus Epsilon-Polylysin und Climbazol
CN113215856A (zh) * 2021-06-08 2021-08-06 辽宁大学 接触型纸质文物综合保护剂及其制备方法和应用

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