EP1202640A1 - Hops acid antibacterial compositions - Google Patents

Hops acid antibacterial compositions

Info

Publication number
EP1202640A1
EP1202640A1 EP00950791A EP00950791A EP1202640A1 EP 1202640 A1 EP1202640 A1 EP 1202640A1 EP 00950791 A EP00950791 A EP 00950791A EP 00950791 A EP00950791 A EP 00950791A EP 1202640 A1 EP1202640 A1 EP 1202640A1
Authority
EP
European Patent Office
Prior art keywords
composition according
hops
composition
acid
group
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP00950791A
Other languages
German (de)
English (en)
French (fr)
Inventor
William King
Xintian Ming
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Solvay USA Inc
Original Assignee
Rhodia Inc
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 Rhodia Inc filed Critical Rhodia Inc
Priority claimed from US09/626,851 external-priority patent/US6475537B1/en
Publication of EP1202640A1 publication Critical patent/EP1202640A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • 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
    • A23B2/733—Compounds of undetermined constitution obtained from animals or plants
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9794—Liliopsida [monocotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/382—Vegetable products, e.g. soya meal, wood flour, sawdust
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/51—Chelating agents

Definitions

  • the present invention relates to a process for reducing the level or retarding the outgrowth of bacteria on food and nonfood products by treatment with a composition which includes one or more safe and suitable hops acids or hops acid derivatives or hops resins or hops resin derivatives and one or more surfactants, surface active agents, chelators, antioxidants and/or organic acids. More specifically, the process comprises using as an ingredient or applying to a food surface or a nonfood product a composition comprising beta hops acids and one or more nonionic surfactants, chelators, antioxidants and/or organic acids in order to reduce or eliminate gram positive spoilage or pathogenic bacteria, and especially strains of the harmful pathogen Listeha monocytogenes.
  • gram positive bacteria such as Listeria monocytogenes, Staphlococcus aureus, Bacillus cereus, Clostridium botulinum and the like
  • miscellaneous gram positive spoilage bacteria such as lactobacilli, bacilli, streptomyces, and micrococci species may cause reduction in the shelf life and appeal of processed foods and high moisture consumer care products. Both pathogenic and spoilage bacteria occur most commonly at the surfaces of foods or consumer care ingredients, which come into contact with undesirable bacteria by contamination from environmental sources.
  • hops beta acids in fatty acid containing foods has prevented them from being used commercially as natural anti-microbial agents for control of listeria or other gram positive pathogens. Further, it is unlikely that hops acid activity would prove effective in the water in oil emulsions common among most consumer care products.
  • the ability to tag the hops acids in the aqueous phase of such systems is a property that would dramatically increase their value as anti-microbials in either food or consumer care products containing high oil or fatty acid levels.
  • composition which has as a first component, at least one compound selected from the group consisting of hops acids, hops acid derivatives, hops resins, and hops resin derivatives; and as a second component, at least one compound selected from the group consisting of food grade surfactants, surface active agents, chelators, antioxidants, and organic acids provides excellent antibacterial properties, especially against potentially harmful gram positive bacteria of the Listeria genus and can easily be applied to the foods or consumer products based on oil in water emulsions.
  • One embodiment of the present invention comprises an antibacterial composition
  • an antibacterial composition comprising: (a) a first component having at least one compound selected from the group consisting of hops acids, hops acid derivatives, hops resins, and hops resin derivatives; and (b) a second component having at least one compound selected from the group consisting of food grade surfactants and surface active agents.
  • a composition containing beta hops acids and a food grade surfactant or surface agent which is either a nonionic surfactant, a propylene glycol, or a mixture thereof.
  • the present invention provides a method for reducing, retarding, or even eliminating gram positive bacteria, and especially the Listeria monocytogenes, in food products comprising the step of treating the surfaces of said food product with a bacteristatically or bactericidally effective amount of a composition comprising: (a) a first component having at least one compound selected from the group consisting of hops acids, hops acid derivatives, hops resins, and hops resin derivatives; and (b) one or more food grade surfactants and/or surface active agents.
  • An additional object of the present invention is to provide a novel composition having substantially greater antibacterial properties than previously observed for the individual components of the composition.
  • An additional object of the present invention is to provide a product which is easily applied to all surfaces of a food product which is potentially susceptible to bacterial degradation.
  • a final object of the present invention is to provide a product which can work well under the partitioning conditions of a fat or oil in water emulsion.
  • the present invention provides a novel antibacterial composition and its use in a process for reducing, retarding, or totally eliminating harmful bacteria, preferably from food surfaces.
  • the novel antibacterial composition comprises: (a) one or more hops acids or hops acid derivatives or hops resins or hops resin derivatives or mixtures thereof; and (b) one or more food grade surfactants or surface active agents or chelators, or antioxidants, or organic acids, or mixtures thereof, preferably food grade surfactants or surface active agents or mixtures thereof.
  • the first component of the novel composition is one or more hops acids, or hops acid derivatives, or hops resins, or hops resin derivatives, or mixtures thereof.
  • the bitter acids component of the hops used in beer making and particularly the beta-acids have now been found to be useful as bactericides in food products.
  • the most prevalent groups of bitter acids found as components of hops are the alpha-acids and the beta-acids, also referred to as humulones and lupulones, respectively. Both contribute bitterness to beer, but the alpha-acids are much more intense in this regard than the beta-acids.
  • a by-product of the operation is a product which contains approximately 61 weight percent beta-acids, the remainder consisting essentially of hops resins. This by-product can be standardized with malto-dextrin or other food grade carrier, spray-dried, and used as an antibacterial food ingredient.
  • a preferred beta hops acids component is commercially available as a natural flavor extract containing 1 weight percent beta hops acids.
  • the alpha-acids contained in hops are commonly known as humulone, cohumulone and adhumulone, while the beta-acids contained in hops are commonly known as lupulone, colupulone and adlupulone.
  • Derivatives of the hops acids or hops resins which have demonstrated antibacterial properties such as hexahydrocolupulone and tetrahydroisohumulone, as disclosed in U.S. Patent No. 5,455,038, are specifically contemplated for use in association with the present invention.
  • Also considered as specifically contemplated for use in association with the present invention is the use of the acid salt forms of the hops acids or hops resins.
  • the hop acid or resin or derivative thereof is added to the food product in amounts between about 0.1 to about 50 ppm (by weight of solution used for treatment), more preferably between about 0.40 to about 20 ppm.
  • the preferred second component of the novel composition comprises one or more food grade surfactants or surface active agents.
  • surface active agent is intended to also include what is commonly known as a protective colloid.
  • the surfactant employed preferably is a food grade emulsifier with a high hydrophilic lipophilic balance (HLB) value. Such values should range from about 10 to about 16. Suitable emulsifiers preferably have also been approved for use in foods since many of the applications for the present invention reside in the food and drug industries.
  • the emulsifier is selected from the group consisting of polyoxyethylene sorbitan esters, sorbitan esters, monoglycerides, diglycerides, lecithin, polyglycerols, sodium stearoyl-2-lactylate, stearyl-2-lactylic acid, polyoxystearates, acetylated monoglycerides and mixtures thereof.
  • sorbitan esters and polyoxyethylene sorbitan esters are the emulsifiers of choice. The above list is considered only a representative listing as the present invention contemplates the use of any food grade surfactant .
  • Particularly preferred commercially available surfactants include: Tween- 80, a trademark of ICI Americas Inc. for polyoxyethylene sorbitol ester; Tween- 80, a trademark of ICI Americas Inc. for polyoxyethylene sorbitol ester; Tween- 80, a trademark of ICI Americas Inc. for polyoxyethylene sorbitol ester; Tween- 80, a trademark of ICI Americas Inc. for polyoxyethylene sorbitol ester; Tween- 80, a trademark of ICI Americas Inc. for polyoxyethylene sorbitol ester; Tween- 80, a trademark of ICI Americas Inc. for polyoxyethylene sorbitol ester; Tween- 80, a trademark of ICI Americas Inc. for polyoxyethylene sorbitol ester; Tween- 80, a trademark of ICI Americas Inc. for polyoxyethylene sorbitol ester; Tween- 80, a trademark of ICI Americas Inc. for polyoxy
  • a surfactant When a surfactant is used in combination with the hops acids or resins or hops acid or resin derivatives, it is added in an amount ranging from about 0.1 to 10%, more preferably between 0.5 to 5% of the treatment composition.
  • a food grade surface active agent other than a surfactant can be selected.
  • Protective colloids such as polyvinyl alcohol are also specifically considered for use in accordance herewith.
  • a surface active agent other than a surfactant is used in combination with the hops acids or hops acid derivatives, it is added in an amount ranging from about 0.1 to 20%, more preferably between 0.5 to 10% of the treatment composition.
  • hops acids or hops acid derivatives with both a surfactant and a surface active agent other than a surfactant is also specifically contemplated as falling within the scope of the present invention.
  • the second component of the compositions of this invention can comprise a chelating agent; preferably one selected from the group consisting of citrates, disodium ethylenediaminetetraacetate (Na 2 EDTA), dicalcium ethylenediaminetetraacetate (CaEDTA), ethylene glycol-bis(beta-aminoethyl ether)-tetraacetic acid (EGTA), and mixtures thereof.
  • a chelating agent comprises sodium citrate.
  • the second component of the compositions of this invention can comprise an antioxidant; preferably one selected from the group consisting of butylated hydroxyanisole, butylated hydroxytoluene, mono- tertbutylhydroquinone (TBHQ), propylgallate ascorbic acid, tocopherols, and mixtures thereof.
  • the antioxidant comprises butylated hydroxyanisole.
  • the second component of the compositions of this invention can comprise an organic acid; preferably one selected from the group consisting of acetic acid, lactic acid, propionic acid, benzoic acid, sorbic acid, and their salts.
  • additives which can be present in the inventive composition include, but are not limited to the following materials: other antibacterial agents, natural or synthetic seasonings, oils, and/or flavors, dyes and/or colorants, vitamins, minerals, nutrients, enzymes, binding agents such as guar gum and xanthan gum and the like.
  • other antibacterial agents such as natural or synthetic seasonings, oils, and/or flavors, dyes and/or colorants, vitamins, minerals, nutrients, enzymes, binding agents such as guar gum and xanthan gum and the like.
  • the addition of these materials is not considered critical to the success of the present invention and this addition would be considered to be within the skill of the artisan.
  • the antimicrobial composition of the present invention may be used in connection with any food or high moisture consumer care product that is susceptible to bacterial growth or degradation.
  • Typical food products include, but are not limited to fruits and vegetables including derived products, grain and grain derived products, dairy foods, cooked meats, poultry, and seafood.
  • the composition is used in connection with meat, poultry and/or seafood, home meal replacements, soups, deli salads, processed cheese, tofu, beverages, or other ready to eat food products.
  • Typical consumer care applications include, but are not limited to moisture containing cosmetics, oral care products, skin care products, hair care products, eye care products, feminine hygiene products, liquid soaps, shampoos, and detergents.
  • the novel composition may be applied to the food surface.
  • application of the composition of matter to the food surface may either be a direct application or an indirect application such as by first coating a packaging material or casing and subsequently bringing the packaging material or casing into intimate contact with the food surface.
  • the use of the term "food surface” is defined to include any and all internal or external surfaces of the food product being treated.
  • composition according to the present invention is most readily used by mixing along with the other ingredients in a blended food or consumer care product, but should also be effective to treat the surface of solid food products by a rinse, spray, packaging material, or by application to the interior of such products, e.g., by injection.
  • the composition may be applied as a marinate, breading, seasoning rub, glaze, colorant mixture, and the like, the key criteria being that the antimicrobial composition be available to the surface subject to bacterial degradation.
  • the composition may be indirectly placed into contact with the food surface by applying the composition to food packaging and thereafter applying the packaging to the food surface. The optimum amount to be used will depend on the composition of the particular food product to be treated and the method used for applying the composition to the food surface, but can be determined by simple experimentation.
  • compositions of this invention are effective against gram positive bacteria including, but not limited to the following bacteria: Listeria bacteria such as Listeria monocytogenes, Staphylococcus bacteria such as Staphylococcus aureus, Clostridia bacteria, Bacillus bacteria, micrococci, streptococci, or other lactic acid bacteria. Under certain conditions, use of the inventive composition reduces bacterial levels to levels undetectable by standard enrichment techniques.
  • Beta Hop Acid BHA
  • Table 1 shows that at a concentration of 0.125 ppm BHA and 2% Tween-80, the bactericidal system has a 3 log reduction of the target bacteria, while less then 1 log deduction is observed at the same concentration of BHA without Tween-80. At higher concentrations of BHA, the BHA and Tween-80 combination virtually eliminates the bacteria levels to less than 10/ml. Thus, the composition of BHA and Tween-80 demonstrate a synergistic activity of greater then 20 times that of BHA alone. Table 1
  • BHA used is a raw extract preparation that contains about 5000 ppm pure beta hop acids.
  • the BHA and propylene glycol combination virtually eliminate the bacteria, i.e., the combination reduces the levels to less than 10/ml.
  • the composition of BHA and propylene glycol demonstrates a synergistic activity enhancement of greater then 20 times that of BHA alone.
  • BHA used is a raw extract preparation that contains about 5000 ppm pure beta hop acids.
  • Beta Hop Acid BHA
  • beta hop acid preparation contains about 0.97% pure beta hop acids.
  • Beta Hop Acid BHA
  • Table 2 shows that at a concentration of 50 ppm BHA preparation and 100 ppm butylated hydroxyanisole, the bactericidal composition causes a 6 log reduction in the target bacteria, while less then 4 log reduction is observed at the same concentration of BHA preparation without butylated hydroxyanisole.
  • the composition of BHA preparation and an antioxidant demonstrates a synergistic effect against L. monocytogenes.
  • beta hop acid preparation contains about 0.97% pure beta hop acids.
  • Beta Hop Acid BHA
  • organic acids against Listeria monocytogenes BHA
  • beta hop acid preparation contains about 0.97% pure beta hop acids.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Zoology (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
EP00950791A 1999-07-27 2000-07-27 Hops acid antibacterial compositions Withdrawn EP1202640A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US14575399P 1999-07-27 1999-07-27
US145753P 1999-07-27
US09/626,851 US6475537B1 (en) 2000-07-27 2000-07-27 Hops acid antibacterial compositions
PCT/US2000/020484 WO2001006877A1 (en) 1999-07-27 2000-07-27 Hops acid antibacterial compositions
US626851 2000-07-27

Publications (1)

Publication Number Publication Date
EP1202640A1 true EP1202640A1 (en) 2002-05-08

Family

ID=26843263

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00950791A Withdrawn EP1202640A1 (en) 1999-07-27 2000-07-27 Hops acid antibacterial compositions

Country Status (6)

Country Link
EP (1) EP1202640A1 (enExample)
JP (1) JP2003528807A (enExample)
AU (1) AU6384100A (enExample)
CA (1) CA2377192A1 (enExample)
MX (1) MXPA02000878A (enExample)
WO (1) WO2001006877A1 (enExample)

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AU2003270103B2 (en) * 2002-05-17 2007-01-25 S.S. Steiner, Inc. Improved application for hop acids as anti-microbial agents
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EP1539255A1 (en) * 2002-09-19 2005-06-15 John I. Haas, Inc. The use of hop acids as an antimicrobial agent to sanitise food processing facilities
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WO2006040189A1 (en) * 2004-10-15 2006-04-20 Rhodia Chimie Composition comprising a hop extract benefit agent
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EP2082739A1 (en) * 2008-01-25 2009-07-29 PURAC Biochem BV Lactylates for the prevention and treatment of infections caused by gram-positive bacteria in animals
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JP2013233093A (ja) * 2012-05-07 2013-11-21 Panex:Kk パテ含有食品の製造方法
CA2897371C (en) 2013-01-07 2022-08-30 John I. Haas, Inc. Compositions and methods for controlling a honey bee parasitic mite infestation
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CN103444788A (zh) * 2013-09-10 2013-12-18 苏州莲花岛生态农业专业合作社 一种啤酒花植物源纳米缓释油悬浮剂及其制备方法
CN103478170A (zh) * 2013-09-18 2014-01-01 中国海洋石油总公司 一种适用于高氨氮高cod水质的溴类杀生剂的制法
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Also Published As

Publication number Publication date
CA2377192A1 (en) 2001-02-01
JP2003528807A (ja) 2003-09-30
MXPA02000878A (es) 2002-10-23
AU6384100A (en) 2001-02-13
WO2001006877A1 (en) 2001-02-01

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