WO2018106109A1 - Composition de traitement de viande et son utilisation - Google Patents

Composition de traitement de viande et son utilisation Download PDF

Info

Publication number
WO2018106109A1
WO2018106109A1 PCT/NL2017/050816 NL2017050816W WO2018106109A1 WO 2018106109 A1 WO2018106109 A1 WO 2018106109A1 NL 2017050816 W NL2017050816 W NL 2017050816W WO 2018106109 A1 WO2018106109 A1 WO 2018106109A1
Authority
WO
WIPO (PCT)
Prior art keywords
meat
nitrite
treatment composition
vegetable extract
composition
Prior art date
Application number
PCT/NL2017/050816
Other languages
English (en)
Inventor
Gerrit Anthon Rene HILHORST
Jacobus Johannes Adriana Maria Verheezen
Prita PRITAWARDANI
Saurabh Kumar
Original Assignee
Purac Biochem 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 Purac Biochem B.V. filed Critical Purac Biochem B.V.
Priority to AU2017371469A priority Critical patent/AU2017371469B2/en
Priority to EP17817928.9A priority patent/EP3550990A1/fr
Priority to CA3046317A priority patent/CA3046317A1/fr
Priority to BR112019011563-3A priority patent/BR112019011563B1/pt
Publication of WO2018106109A1 publication Critical patent/WO2018106109A1/fr
Priority to US16/432,774 priority patent/US20190297906A1/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L3/00Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454Preservation 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
    • A23L3/358Inorganic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B4/00General methods for preserving meat, sausages, fish or fish products
    • A23B4/14Preserving with chemicals not covered by groups A23B4/02 or A23B4/12
    • A23B4/18Preserving with chemicals not covered by groups A23B4/02 or A23B4/12 in the form of liquids or solids
    • A23B4/24Inorganic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L13/00Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/40Meat products; Meat meal; Preparation or treatment thereof containing additives
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L13/00Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/40Meat products; Meat meal; Preparation or treatment thereof containing additives
    • A23L13/42Additives other than enzymes or microorganisms in meat products or meat meals
    • A23L13/428Addition of flavours, spices, colours, amino acids or their salts, peptides, vitamins, yeast extract or autolysate, nucleic acid or derivatives, organic acidifying agents or their salts or acidogens, sweeteners, e.g. sugars or sugar alcohols; Addition of alcohol-containing products
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L13/00Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/40Meat products; Meat meal; Preparation or treatment thereof containing additives
    • A23L13/42Additives other than enzymes or microorganisms in meat products or meat meals
    • A23L13/432Addition of inorganic compounds, e.g. minerals; oligo-elements
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L13/00Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/40Meat products; Meat meal; Preparation or treatment thereof containing additives
    • A23L13/45Addition of, or treatment with, microorganisms

Definitions

  • This invention relates to a meat treatment composition for increasing the resistance of meat to microbial spoilage and/or for enhancing reddening of meat and/or for reducing moisture loss incurred during cooking, refrigerating, freezing, thawing and/or storage of meat.
  • Industrial processing of meat for human consumption usually aims to provide (processed) meat products that combine an appealing appearance and flavor with microbial safety and prolonged shelf-life. Consumers evaluate meat products on the basis of a number of sensory attributes. Color, juiciness, flavor, and tenderness are believed to represent the most relevant sensory attributes of processed meat products.
  • the characteristic cured color can be derived from the concentration of heme pigments (myoglobin, hemoglobin), their chemical states and additives such as nitrogen oxides and reducing agents.
  • heme pigments myoglobin, hemoglobin
  • the characteristic cured color is a result of the chemical reaction between compounds derived from added nitrite/nitrate and the naturally occurring red myoglobin leading to the simultaneous formation of the bright red nitrosylmyoglobin, in which an axial ligand nitric oxide (NO) is coordinated to the central Fe 2+ in heme.
  • NO axial ligand nitric oxide
  • Nitrate generally supplied by sodium nitrate or potassium nitrate, is used as a source for nitrite (N0 2 " ).
  • Meat spoilage and rancidity affects not only appearance and/or sensory attributes, but also safety. Unwanted growth of certain aerobic and anaerobic bacteria that contaminate the meat during processing are the main cause.
  • measures to preserve meat by elimination of bacteria or at least reducing outgrowth thereof have been known (and practiced) for ages.
  • Early preservation techniques of meat mainly involved drying, storing in salt (pickling), smoking, fermenting and/or (pre-) cooking. These processing methods, while effective for preserving the meat and preventing it from becoming spoiled or rancid, drastically change the overall visual and sensorial characteristics of the meat products. In more modern times, freezing has become a common and effective way to retard the growth of bacteria that may be present on the surface of meat.
  • Nitrite can cause the formation of unwanted compounds in cured meat, like N-nitrosamines which are questionable in regard to health. These compounds can be formed in principle due to the reaction of nitrite with secondary amines and amino acids in muscle proteins as well as in the gastrointestinal tract. Consumers are becoming increasingly aware of these safety issues. Consequently, food manufacturers are looking to replace part or all of the nitrite with other, more natural-like, food ingredients. Accordingly, a need exists for improved products for increasing the resistance of meat to microbial spoilage and/or for enhancing reddening of meat, while at the same time supporting a more "clean and consumer friendly" label statement.
  • US 2011/0300591 describes a method for converting nitrates to nitrites, wherein nitrates are converted to nitrites by bacteria belonging to the Staphylococcus vitulinus specie having nitrate reductase activity (NRA) , in the presence of lactic acid bacteria, at a pH comprised between 5.2 and 9.
  • the nitrates may be contained in a liquid buffer preparation, i.e. a neutral medium containing nitrates which have been recovered after extraction from a natural source of nitrates, such as, a leek or spinach leaf, a fragment of celery, of onion or of cabbage, etc.
  • US 2012/027896 describes a method of treating a fresh meat product, comprising:
  • the source of the sodium nitrite or sodium nitrate is preferably a natural source such as vegetable powders.
  • An example of a natural source of sodium nitrite or sodium nitrate that could be used is VEG STABLETM 504, manufactured by Florida Food Products, Inc. of Eustis, Florida, or other vegetable based ingredients containing nitrites or fermented nitrates.
  • WO 2016/100299 describes a process for treating an animal muscle portion to form an enhanced muscle portion comprising:
  • providing a comminuted meat emulsion having a pH of from about 6.5 to about 9.5, the comminuted meat emulsion being prepared from a first animal muscle tissue;
  • compositions which can be used in meat treatment in order to achieve one or more of the aforementioned objectives, which compositions have been formulated as a concentrated liquid and show good stability during storage.
  • the present inventors surprisingly found that this can be accomplished with concentrated liquid meat treatment compositions comprising a combination of a buffered food acid component in the form of partially or completely neutralized acetic acid; and a nitrite source in the form of a cultured vegetable extract.
  • the meat treatment compositions of the present invention exhibit excellent shelf stability in that nitrite content of the composition remains constant for a prolonged period of time.
  • the present compositions are based on ingredients that, depending on the forms in which they are provided, can be labeled as 'natural ingredients' .
  • the meat treatment composition of the present invention not only can be applied to increase the resistance of meat to microbial spoilage and/or to enhance the reddening of meat and/or to decrease moisture loss incurred during cooking, refrigerating, freezing thawing and/or storage of meat, but is also highly advantageous in view of food regulations and labeling requirements.
  • a particularly beneficial finding underlying the present invention is that the combination of the partially/completely neutralized acetic acid with the cultured vegetable extract as a single concentrated liquid product enhances the (chemical) stability of the preservative composition, notably of the nitrite per se.
  • the nitrite content in the concentrated compositions of the invention is more stable, under various storage conditions, than that of nitrite containing curing agents not comprising the neutralized acetic acid.
  • meat processors it is an additional advantage for meat processors to be able to store sizable amounts of a curing agent without concerns as to the level of activity at the time of use.
  • the invention provides concentrated liquid meat treatment compositions comprising such combinations of neutralized acetic acid and cultured vegetable extract; methods and uses involving the treatment of meat with said compositions; as well as the meat products that are accordingly obtained.
  • a meat treatment composition comprising:
  • a buffered food acid component comprising a total amount of partially or completely neutralized acetic acid of at least 5 wt.%, based on the total weight of the composition
  • a nitrite source in the form of a cultured vegetable extract wherein said meat treatment composition is a liquid having a pH value of 6.0 or higher; wherein the meat treatment composition contains at least 0.1 wt.% nitrite, based on the total weight of the composition.
  • the compositions of the present invention are particularly suited for use as a food additive, more in particular for use in meat treatment.
  • the meat treatment composition as well as the components used to produce them are typically 'food grade', meaning that they are acceptable for use in foods and, more in particular, that they would be considered not to be harmful or toxic to a mammal upon consumption of the food products containing them, i.e. when applied at the levels taught herein.
  • the term 'buffered food acid component' is used to refer to a partially or completely neutralized food-grade organic acid.
  • the buffered food acid component typically comprises salts of the respective food-grade organic acid(s), including acetic acid, optionally in combination with the corresponding food-grade organic acid(s) in free acid form. Since, in accordance with the present invention, the buffered food-grade acid exists as a solution, the buffered food acid component may also be viewed as a combination of acid anions and a stoichiometric amount of metal cations or a sub-stoichiometric amount of metal cations in combination with a corresponding amount of hydrogen ions. Whenever quantities of the buffered food acid component are given herein, the total quantity of free acid(s) and corresponding salts is referred to, unless specifically indicated otherwise.
  • the buffered food acid component may (optionally) comprise food-grade organic acids selected from the group consisting of lactic acid, citric acid, propionic acid, malic acid, cinnamic acid and mixtures thereof.
  • a meat treatment composition as defined herein wherein the buffered food acid component comprises buffered vinegar.
  • vinegar is used to denote the liquid obtained by the acetous fermentation of an alcoholic liquid, containing at least 4 grams of acetic acid per 100 ml, in particular a vinegar that can be declared 'natural', e.g. in terms of the FDA guidelines. According to said guidelines "natural” means minimally processed and containing no synthetic ingredients or processing aids (cf. Food Labeling: Nutrient Content Claims General Principles, Petitions, Definitions of Terms, 56 Fed. Reg. at 60,466).
  • the preservative system comprises a non-neutralized, partly neutralized or completely neutralized vinegar selected from the group consisting of white vinegar, brandy vinegar, alcoholic vinegar, balsamic vinegar, wine vinegar, malt vinegar, beer vinegar, potato vinegar, rice vinegar, apple vinegar, cherry vinegar, and cane vinegar.
  • the vinegar is cane vinegar.
  • the acetic acid content of the vinegar is at least 5 % (w/w), more preferably at least 7.5 % (w/w), even more preferably at least 10 % (w/w). It is also possible to make use of vinegar that has been pre-concentrated to a certain extent.
  • Such products are commercially available and typically have an acetic acid content between 20 and 30 % (w/w).
  • the acetic acid content of the vinegar is at least 20 % (w/w), more preferably at least 25 % (w/w), e.g. about 29 or 30 % (w/w).
  • a common measure for indicating the acetic acid content of vinegar is the grain strength.
  • the grain strength is the acetic acid content expressed in g/1, so 50 grain vinegar is about 5% (w/w) acetic acid.
  • the vinegar is at least 200 grain, more preferably at least 250 grain.
  • commercial food-grade vinegars are offered at 200 grain and 300 grain. In one preferred embodiment of the invention, a 300 grain vinegar is used.
  • the food-grade organic acid is combined with a (food-grade) alkalizing agent.
  • Preferred alkalizing agents comprise metal hydroxides or metal salts or combinations thereof.
  • metal hydroxides comprise sodium hydroxide, potassium hydroxide, calcium hydroxide or combinations thereof.
  • An example of a metal salt comprises metal carbonate.
  • Such compositions will comprise a mixture of free organic acid and one or more acid salts or such compositions will comprise one or more acid salts without free organic acid, depending on the relative amounts of the food-grade organic acid and the alkalizing agent, as will be understood by those skilled in the art.
  • the meat treatment composition comprises a buffered vinegar, which typically is obtainable by combining a natural vinegar with an alkalizing agent, preferably a metal hydroxide as for example potassium hydroxide or calcium hydroxide or a metal salt, such as a metal carbonate.
  • a buffered vinegar is obtainable by combining a natural vinegar with sodium hydroxide, potassium hydroxide, calcium hydroxide or a combination thereof.
  • the meat treatment compositions according to the present invention preferably have a total content of partially or completely neutralized food-grade organic acid of not more than 99.9 wt.%, based on the total dry solids weight of the composition, more preferably of not more than 99.5 wt.%, even more preferably within the range of 10-99 wt.%, still more preferably 15-98 wt.%, still more preferably 20-95 wt.%.
  • the meat treatment compositions according to the present invention preferably have a total content of a food grade acid selected from acetic acid, lactic acid, propionic acid, and mixtures thereof, in partially or completely neutralized form, of not more than 99.9 wt.%, based on the total dry solids weight of the composition, more preferably of not more than 99.5 wt.%, more preferably within the range of 10-99 wt.%, still more preferably 15-98 wt.%, still more preferably 20-95 wt.%
  • the meat treatment compositions according to the present invention preferably have a total content of acetic acid in partially or completely neutralized form, of not more than 99.9 wt.%, based on the total dry solids weight of the composition, more preferably of not more than 99.5 wt.%, more preferably within the range of 10-99 wt.%, still more preferably 15-98 wt.%, still more preferably 20-95 wt.%.
  • the meat treatment composition according to the present invention comprises the food-grade acid anions and metal cations in a molar ratio of at least 1 :0.2, preferably at least 1 :0.5, more preferably at least 1 :0.75.
  • the meat treatment composition of the present invention further comprises a nitrite source in the form of a cultured vegetable extract.
  • the nitrite source is a vegetable extract containing significant amounts of nitrate, which has been contacted and incubated with viable micro-organisms under conditions suitable for said micro-organisms to convert nitrate into nitrite by their inherent metabolism.
  • the term "vegetable extract” is used to refer to a composition of matter derived from food-grade plant materials, typically by mainly physical treatment of plant material, such as by cutting, macerating, pressing, soli-liquid extractions, concentrating, drying, etc.
  • the vegetable extract is a liquid fraction derived from food-grade plant materials, which may also be referred to as a vegetable juice.
  • Embodiments are also envisaged wherein vegetable juice solids are provided in concentrated or in partially or completely dried form. The use of vegetable juice and/or vegetable (juice) concentrate is particularly preferred, in accordance with the invention.
  • the food-grade plant material may be any nitrate-containing plant containing a significant amount of nitrate.
  • the plant material comprises fresh plant parts, such as, in particular, leafs, flowers, stems and/or roots.
  • the nitrate concentration of the plant material is at least about 100 ppm, e.g. at least about 200 ppm, at least about 300 ppm, at least about 400 ppm, at least about 500 ppm, at least about 600 ppm, or at least about 700 ppm.
  • the nitrate concentration of the plant material is preferably 24,000 ppm or less, e.g., about 20,000 ppm or less, about 15,000 ppm or less, about 10,000 ppm or less, about 8000 ppm or less, about 5000 ppm or less, about 3000 ppm or less, about 2500 ppm or less, or about 2000 ppm or less.
  • Suitable plant materials include, but are not limited to, celery, beet, spinach, lettuce, cabbage, cucumber, eggplant, mushroom, green pepper, butternut squash, zucchini, mixed salad greens, carrot, artichoke, green bean, lima bean, broccoli, cauliflower, collard green, com, mustard, okra, onion, Chinese pea pod, black eyed pea, green pea, potato, turnip, sauerkraut, radish and the like.
  • Other edible plant material containing significant amounts of nitrate also can be used. Any mixture or combination of plant materials can be used in accordance with the invention.
  • the nitrite source is derived from celery juice or extract.
  • the vegetable extract has a nitrate concentration of at least about 100 ppm, e.g., at least about 200 ppm, at least about 300 ppm, at least about 400 ppm, at least about 500 ppm, at least about 600 ppm, or at least about 700 ppm.
  • the nitrate concentration of vegetable extract is preferably 24,000 ppm or less, e.g. about 20,000 ppm or less, about 15,000 ppm or less, about 10,000 ppm or less, about 8000 ppm or less, about 5000 ppm or less, about 3000 ppm or less, about 2500 ppm or less, or about 2000 ppm or less.
  • the vegetable extract, juice or concentrate comprises celery extract, celery juice or celery concentrate.
  • Suitable commercial products are available from commercial suppliers such as from Florida Food Products Inc., under the product names 'Veg Stable '5 ' 50 and 'Veg Stable* 502'; from Diana Naturals, under the product name 'Celery juice concentrate', and from Vegetable Juices, Inc.
  • Any organism capable of converting nitrate to nitrite can be used in the process of the present invention.
  • Suitable organisms include but are not limited to yeast, fungi, and bacteria.
  • the organism can be, for example, E. coli, Rhodobacter sphaeroides, Paracoccus pantotrophus, Wautersia eutropha, Bradyrhizobium japonicum, any Pseudomonas species, Campylobacter jejunii, Wollinella succinogenes, Haemophylus influenzae, Shewanella oneidensis, Desulfitobacterium hafniense, Rhodobacter capsulatus, Klebsiella pneumoniae, Bacillus subtilis, the genus Cyanobacteria, any Synechococcus species, the genus Haloferax, the genus Haloarcula, and Thermus thermophilus.
  • the organism is a single strain or combination of bacterial strains within the Micrococcaceae family, including Micrococcus and Staphylococcus, Gram-positive cocci, including Enterococcus, Lactococcus, Leuconostoc, Pediococcus, Streptococcus, and Staphylococcus, and all lactic acid bacteria.
  • the organism or organisms useful in the context of the invention include M. varians, S. carnosus, S. vitulinus, S. xylosus or a combination thereof.
  • Embodiments of the invention are also envisaged, wherein the conversion of nitrate into nitrite is accomplished using a suitable enzyme preparation, typically a preparation comprising nitrate reductase.
  • the nitrite source of the meat treatment composition according to the present invention is a composition obtainable by a process comprising the steps of:
  • a liquid vegetable extract preferably a vegetable juice or vegetable (juice) concentrate
  • the incubating step is optionally followed by one or more purification steps.
  • the one or more purification steps of the cultured vegetable extract comprise centrifugation and/or filtration of the cultured vegetable extract, with the proviso that the purification does not result in a nitrite level, on dry solids weight basis, of above 90 %, above 80 %, above 70 % or above 60 %.
  • the process does not involve any processing aimed at purification or isolation of the nitrite, other than solid- liquid separation and/or concentration.
  • the cultured vegetable extract as obtained in step iii) is used directly as the nitrite source in the present meat treatment compositions.
  • Cultured vegetable extracts in accordance with the invention may typically contain, besides nitrite, sugars, fiber, protein, vitamins and calcium.
  • the nitrite source comprises at least 5 wt.%, based on the total dry solids weight of the composition, preferably at least 7.5 wt.%, more preferably at least 10 wt.% of one or more components selected from the group consisting of sugars, protein, fiber, vitamins and calcium.
  • the meat treatment composition comprises at least 0.5 wt.%, based on the total dry solids weight of the composition, preferably at least 1 wt.%, more preferably at least 2 wt.% of one or more components selected from the group consisting of sugars, protein, fiber, vitamins and calcium.
  • the vegetable extract comprises cultured celery extract, such as e.g. the products 'Veg Stable" 5 504', 'Veg Stable* 506' or ' Veg Stable*' 528', available Florida Food Products, Inc. and the products Accel 2000H and Accel XP, available from Kerry Inc.
  • cultured celery extract such as e.g. the products 'Veg Stable" 5 504', 'Veg Stable* 506' or ' Veg Stable*' 528', available Florida Food Products, Inc. and the products Accel 2000H and Accel XP, available from Kerry Inc.
  • the meat treatment composition of the present invention in one embodiment, comprises nitrite in an amount of between 0.05 and 5 wt.%, based on the total dry solids weight of the composition, more preferably between 0.1 and 4 wt.%, most preferably 0.2 wt.% or 3 wt.%).
  • the molar ratio of the (partially or completely neutralized) food-grade acid(s) to nitrite is at least 3/1, preferably it is within the range of 5/1 -100./1, most preferably within the range of 20./ 1- 40./1.
  • the meat treatment composition of the present invention in another embodiment, comprises nitrite, nitrate or a mixture thereof in a combined amount of between 0.05 and 5 wt.%, based on the total dry solids weight of the composition, more preferably between 0.1 and 4 wt.%, most preferably 0.2 wt.% or 3 wt.%; in combination with viable nitrate converting micro-organisms, preferably a micro-organism as defined herein before, in an amount of at least 1000 cfu/kg of dry solids.
  • the molar ratio of the (partially or completely neutralized) food-grade acid(s) to the total amount of nitrite and nitrate is at least 3/1, preferably it is within the range of 5/1 - 100. /I , most preferably within the range of 20./ 1 -40./ 1.
  • a buffered food acid component and/or a nitrite sources obtained by fermentation may comprise detectable amounts of other dispersed or dissolved solids besides the acid component and/or the nitrite.
  • Typical examples of such other dispersed or dissolved solids include sugars, such as glucose, fructose and sucrose; organic acids and/or salts thereof, such as lactic acid, citric acid, pyruvic acid, malic acid, succinic acid, formic acid and acetic acid; nitrogen containing substances, such as amino acids, peptides and proteins; nucleic acid components such as DNA and RNA fragments, nucleotides and nucleosides; cell membrane phospholipids; vitamins; trace elements; and pigments.
  • the meat treatment composition of the invention will comprise one or more components produced using fermentative process, which components are typically used in non- or only partially purified form
  • the liquid meat treatment composition will typically comprise at least one, at least two, at least three, at least four or at least five components selected from the group consisting of fructose, glucose, sucrose, lactic acid and salts thereof, citric acid and salts thereof, pyaivic acid and salts thereof, malic acid and salts thereof, succinic acid and salts thereof, formic acid and salts thereof, acetic acid and salts thereof, propionic acids and salts thereof, amino acids, peptides and proteins.
  • the liquid meat treatment composition comprises at least 0.5 wt.%, based on the total dry solids weight of the composition, preferably at least 1 wt.%, more preferably at least 2 wt.% of one or more components selected from the group consisting of fructose, glucose, sucrose, citric acid and salts thereof, pyruvic acid and salts thereof, malic acid and salts thereof, succinic acid and salts thereof, formic acid and salts thereof, acetic acid and salts thereof, propionic acids and salts thereof, amino acids, peptides and proteins.
  • the meat treatment composition as defined herein does not contain substantial amounts of phosphate. More preferably, the meat treatment composition of the invention, comprises less than 5 wt.%, based on the total dry solids weight of the composition, of phosphate, preferably less than 1 wt.%, more preferably less than 0.5 wt.%.
  • salt may be added to the meat treatment composition as an additional curing agent.
  • meat treatment compositions are provided comprising more than 0.1 wt.%, more than 0.5 wt.%, more than 1.0 wt.%, more than 2.5 wt. % or more than 5 wt.% of salt, based on the total dry solids weight of the composition
  • the concentrated liquid meat treatment composition of the present invention can be produced intended for dilution with water prior to use. This is particularly convenient when the meat treatment is not performed at the site where the meat treatment composition is produced, so as to reduce the volume of water in the product to be stored and transported, which has obvious advantages.
  • the meat treatment composition that is formulated as a concentrated liquid is referred to as a 'concentrate' .
  • the concentrate typically comprises a buffered food acid component and a nitrite source in combination with water. Such concentrates are typically intended for dilution with water before use. Such concentrates preferably have a total dry solids content within the range of 7-100 wt.%, most preferably within the range of 10-45 wt.%. Such concentrates will typically comprise a total amount of partially or completely neutralized food-grade organic acid, based on the total weight of the composition, within the range of 7-80 wt.%, most preferably within the range of 10-50 wt.%.
  • Such concentrates will typically comprise nitrite, based on the total weight of the concentrate, in an amount within the range of 0. 15-1.5 wt.%, most preferably within the range of 0.2- 0.75 wt.%.
  • such concentrates will comprise nitrite and nitrate in a combined amount of at least 0.1 wt.%, based on the total weight of the concentrate, more preferably in an amount within the range of 0.15-1.5 wt.%, most preferably within the range of 0.2-0.75 wt.%.
  • a ready-to-use liquid comprising the meat treatment composition as defined herein.
  • ready-to-use liquids are also referred to herein as 'brine'.
  • the brine will typically have a total dry solids content of at least 3 wt.%, more preferably within the range of 5.-100 wt.%, most preferably within the range of 20-40 wt.%.
  • the ready-to-use liquid has a pH of 6.0 or higher .
  • Such brines will typically comprise a total amount of partially or completely neutralized food- grade organic acid, of at least 1 wt.%, based on the total weight of the composition, more preferably within the range of 1.5- 10 wt.%, most preferably within the range of 2-5 wt.%.
  • Such brines will typically comprise nitrite in an amount of at least 0.01 wt.%, based on the total weight of the brine, more preferably in an amount within the range of 0.025-0. 1 wt.%, most preferably within the range of 0.04-0.07 wt.%.
  • such brines will comprise nitrite and nitrate in a combined amount of at least 0.01 wt.%, based on the total weight of the brine, more preferably in an amount within the range of 0.025-0.1 wt.%, most preferably within the range of 0.04-0.07 wt.%.
  • the meat treatment compositions according to the present invention preferably have a pH of 6.0 or higher. More preferably, the meat treatment compositions according to the present invention have a pH within the range of 6.5-1 1, more preferably a pH within the range of 7-10.
  • the meat treatment compositions of the invention are typically produced by combining the buffered food acid component with the nitrite source.
  • Compositions that can suitably be used as the buffered food acid component and the nitrite source in accordance with the invention are commercially available.
  • the buffered food acid component as well as the nitrite source can be used in liquid as well as in solid form.
  • a method of producing a meat treatment composition as described herein before comprises the steps of combining:
  • a buffered food acid component comprising partially or completely neutralized food-grade acetic acid
  • the pH of the composition is adjusted to obtain a value within the ranges described herein before. If the pH needs to be increased this is preferably done by adding an appropriate amount of an alkali metal hydroxide. If it is desired to lower the pH of the meat treatment composition after combining the buffered food acid component and the nitrite source, this may suitably be done using an appropriate amount of the food acid, i.e. in free acid form, even though the use of mineral acids for this purpose is not excluded.
  • both the buffered food acid component and the nitrite source may be used in liquid or dry powder form. If one or both of the components are used in dry powder form, it is envisaged that the method comprises reconstitution of the respective components in a suitable quantity of water, e.g. in tap water, before combining it with the other component. Embodiments are also envisaged wherein both components are in dry powder form and are blended and subsequently reconstituted in water. In the method of the invention, the ingredients are typically agitated for a period of time sufficient to form a homogeneous liquid, which may be a dispersion or solution.
  • a third aspect of the invention concerns a method of treating meat to increase the resistance of microbial spoilage and/or to enhance reddening of meat and/or to reduce and/or compensate for moisture loss during cooking and/or during other kinds of processing, such as cooking, refrigerating, cooling, freezing, thawing and/or storage of meat.
  • a method as defined herein wherein the meat is treated with a meat treatment composition of the invention, typically in the form of a liquid referred to here above as the 'ready-to-use liquid' or 'brine'.
  • the method of the invention typically comprises the steps of:
  • the method according to the present invention is suitable and beneficial for the treatment of most conventional meat products typically offered for human consumption, regardless of the source and/or form in which it is offered.
  • the meat is selected from the group consisting of whole muscle meat, cuts or slices of whole muscle meat, ground or comminuted muscle meat and emulsified meat.
  • the meat is fresh meat, which may be in the form of whole muscle meat, cuts or slices of whole muscle meat or ground or comminuted muscle meat.
  • the term 'fresh' means that the meat has not been treated by cooking in between removal from the animal carcass and the treatment according to the invention.
  • the meat is uncooked meat.
  • the meat has been stored, typically under refrigeration for some time in between removal from the animal carcass and the treatment according to the invention.
  • the meat is obtained from beef cattle, pork, lamb, poultry, and game, most preferably from pork, chicken and turkey.
  • the actual amount of brine used for treating meat and/or the weight gain of the meat will vary depending on the method of treating the meat, the type of meat, and the particular meat treatment composition used.
  • the meat is treated with a sufficient amount of the brine and in a manner sufficient to cause a weight increase in the range of 2-20%, more preferably in the range of 5-15%.
  • the meat is treated with a composition in the form of a liquid brine as defined herein before, in quantities providing a weight ratio of brine to meat within the range of 1/10-1/2, preferably within the range of 1/8-1/3, more preferably within the range of 1/7-1/4.
  • the meat is treated with a brine as defined herein before, in quantities providing a level of nitrite of between 2 mg per kg of meat and 800 mg per kg of meat, preferably a level of nitrite between 4 mg per kg of meat and 600 mg per kg of meat, more preferably a level of nitrite between 5 mg per kg of meat and 500 mg per kg of meat.
  • the meat is treated with a brine as defined herein before, in quantities providing a level of the food-grade buffered acid of between 1000 mg per kg of meat and 10000 mg per kg of meat, preferably a level of nitrite between 2000 mg per kg of meat and 9000 mg per kg of meat, more preferably a level of nitrite between 3000 mg per kg of meat and 8000 mg per kg of meat as for example a level of nitrite of 6000 mg per kg meat (6000 ppm).
  • the methods for treating the meat may utilize any method that is known and/or conventionally used for combining fresh meat and a brine product.
  • meat may be treated with the composition of the invention by dispersing it throughout the fresh meat. Suitable methods include injecting, pumping, spraying, soaking, dipping or otherwise dispersing the composition into or onto the meat.
  • the method may comprise tumbling, kneading, massaging or otherwise manipulate the meat to further disperse the composition throughout the meat.
  • the composition is injected under pressure into the meat as part of an automated commercial meat production step. Suitable injectors may be set to pump a particular volume of the composition into each piece of meat.
  • the brine may simply be added to the meat followed by tumbling, kneading or massaging of the meat so as to cause the brine to be evenly distributed throughout the meat.
  • the treated meat may then be molded or otherwise shaped to form any number of food products including patties, sausages, wieners and luncheon meats.
  • the meat may subsequently be cooked until the desired internal temperature is reached, packaged and refrigerated or frozen.
  • the meat may be packaged, cooked then refrigerated or frozen.
  • a further aspect of the invention concerns a meat product obtainable by the method as defined herein.
  • Such treated meat may have an increased resistance to microbial spoilage.
  • the nitrite content of the treated meat has an increased stability.
  • the treated meat possesses a higher total water content when cooking commences, which may result in a higher water content remaining after cooking meat even if normal water loss occurs during cooking. Instead or in addition, the treated meat may have a reduced tendency to lose water during cooking.
  • the coloration of treated meat may also be retained for a longer period of time, such that the meat has a more desirable appearance for a longer time.
  • a further aspect of the invention concerns the use of a meat treatment composition as defined herein before, for increasing the resistance of meat to microbial spoilage and/or for enhancing reddening of meat and/or for reducing moisture loss incurred during cooking, and/or storage of meat.
  • the invention has been described by reference to certain embodiments discussed above. It will be recognized that these embodiments are susceptible to various modifications and alternative forms well known to those of skill in the art.
  • Example 1 Preparation of a liquid meat treatment composition
  • Verdad® N5 or Verdad® N16 As food acid components vinegar sold under the name Verdad® N5 or Verdad® N16, manufactured by Corbion, is used. A buffered food acid is obtainable by neutralizing Verdad® N5 or Verdad® N16 with a 50 % KOH or 50 % NaOH solution to a pH of 5.7 and 7.8 respectively.
  • a suitable cultured celery extract is commercially available under the tradename Veg Stable Veg Stable® 528, manufactured by Florida Food Products Inc.
  • the meat treatment composition is obtainable by combining vinegar neutralized with KOH or NaOH followed by a blending with Veg Stable® 528.
  • Example 2 Enhanced stability of nitrite in the meat treatment composition
  • composition A to F The performance of six different meat treatment compositions (composition A to F) is evaluated :
  • Composition A comprises 2000 g celery ferment (Veg Stable ® 528);
  • Composition B comprises 1466 g vinegar (Verdad* N5) and 533.35 g celery ferment (Veg Stable ® 528);
  • Composition C comprises 1526.7 g of buffered vinegar to a pH of 7 (Verdad* N5 neutralized with 50 % KOH to a pH of 7) and 473.47 g celery ferment (Veg Stable ® 528);
  • Composition D comprises 1542,8 g of buffered vinegar to a pH of 8 (Verdad * N5 neutralized with 50 % KOH to a pH of 8) and 458.26 g celery ferment (Veg Stable ® 528);
  • Composition E comprises 720.8 g of a buffered vinegar as in composition D, which was concentrated to a dry matter content of 63% and 479.96 g celery ferment (Veg Stable* 528); and
  • Composition F comprises 1636.35 g Verdad* N 16 and 363.68 g celery ferment (Veg Stable ® 528).
  • the content of nitrite is for example measured with a high performance liquid chromatography (HPLC) anion method.
  • the stability of the nitrite in function of the time is determined of the compositions A to F by measuring the nitrite content after 1 week, 2 weeks, 4 weeks, 6 weeks, 8 weeks and 13 weeks.
  • composition IX E and F show a good stability of nitrite even after 6, 8 or 13 weeks.
  • compositions D and E show a better stability of nitrite at a temperature of 40 °C.
  • Brines were prepared on the basis of the recipes shown in in Table 3, using composition B and composition D of Example 2. C omposition B and D were applied at equal dosage levels of celery ferment and acetate/acetic acid.
  • Brine 1 had a pH of 5.2.
  • Brine 2 had a pH of 7.9
  • composition 2 The cooking yield was found to be higher for the composition according to the invention than for the reference composition, namely 99.4% (composition 2) against 97.2% (composition 1).
  • the measured Lab color values confirmed what was clearly visible to the naked eye, i.e. the ham pieces treated with brine 2 had retained most of the original reddish color, whereas the ham pieces treated with brine 1 had become much more pale during storage.
  • Example 4 Application of meat treatment compositions in pork ham
  • Pieces of pork ham were prepared in the same way as in Example 3.
  • the ham yield after cooking was found to be 96.5% for the reference composition 1 and 98.1% for composition 2 (composition according to the invention).
  • the color of the treated ham pieces was monitored under the same conditions as in Example 3.
  • the Lab color values of the ham pieces were measured directly after brine treatment and after 7 days of storage

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Mycology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Meat, Egg Or Seafood Products (AREA)

Abstract

L'invention concerne une composition liquide et concentrée de traitement de viande qui comporte une combinaison d'un composant acide alimentaire, tamponné sous la forme d'acide acétique partiellement ou totalement neutralisé, et d'une source de nitrite sous la forme d'un extrait végétal cultivé. La composition de traitement de viande présente une excellente stabilité de conservation en ce que la teneur en nitrite de la composition reste constante pendant une longue période.
PCT/NL2017/050816 2016-12-06 2017-12-06 Composition de traitement de viande et son utilisation WO2018106109A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU2017371469A AU2017371469B2 (en) 2016-12-06 2017-12-06 Meat treatment composition and use thereof
EP17817928.9A EP3550990A1 (fr) 2016-12-06 2017-12-06 Composition de traitement de viande et son utilisation
CA3046317A CA3046317A1 (fr) 2016-12-06 2017-12-06 Composition de traitement de viande et son utilisation
BR112019011563-3A BR112019011563B1 (pt) 2016-12-06 2017-12-06 Composição líquida concentrada para tratamento de carne, método de produção de uma composição líquida concentrada para tratamento de carne e método para tratar carne
US16/432,774 US20190297906A1 (en) 2016-12-06 2019-06-05 Meat treatment composition and use thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201662430729P 2016-12-06 2016-12-06
US62/430,729 2016-12-06
EP16202436.8 2016-12-06
EP16202436 2016-12-06

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US16/432,774 Continuation US20190297906A1 (en) 2016-12-06 2019-06-05 Meat treatment composition and use thereof

Publications (1)

Publication Number Publication Date
WO2018106109A1 true WO2018106109A1 (fr) 2018-06-14

Family

ID=57539039

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL2017/050816 WO2018106109A1 (fr) 2016-12-06 2017-12-06 Composition de traitement de viande et son utilisation

Country Status (1)

Country Link
WO (1) WO2018106109A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020181016A1 (fr) * 2019-03-04 2020-09-10 Broussard Robert R Produits alimentaires favorisant la santé et leur procédé de conception et de fabrication
WO2020245407A1 (fr) 2019-06-05 2020-12-10 Purac Biochem B.V. Composition pour conserver ou améliorer la qualité de la viande transformée
WO2020245405A1 (fr) 2019-06-05 2020-12-10 Purac Biochem B.V. Composition pour conserver ou améliorer la qualité de viande transformée
WO2021206724A1 (fr) 2020-04-10 2021-10-14 Purac Biochem B.V. Composition d'oignons fermentés
WO2021260033A1 (fr) 2020-06-23 2021-12-30 Purac Biochem B.V. Composition permettant de conserver et/ou d'améliorer la qualité de produits à base de viande
WO2021262144A1 (fr) 2020-06-23 2021-12-30 Purac Biochem B.V. Composition pour conserver ou améliorer la qualité de produits carnés
US20220386635A1 (en) * 2021-04-18 2022-12-08 Kemin Industries, Inc. Nitrite replacement (curing aids) containing natural ingredients
WO2023062216A1 (fr) 2021-10-14 2023-04-20 Purac Biochem B.V. Composition d'oignons fermentés

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080305213A1 (en) * 2007-06-11 2008-12-11 Kerry Group Services International, Ltd. Method and composition for preparing cured meat products
US20100310738A1 (en) * 2009-06-04 2010-12-09 Wti, Inc. Method of processing meat
US20110300591A1 (en) 2008-12-11 2011-12-08 Danisco A/S Bacterial Compositions of Staphylococcus Vitulinus Having Nitrate Reductase Activity and of Lactic Acid Bacteria and Methods Using These Compositions
US20120027896A1 (en) 2010-07-30 2012-02-02 Hormel Foods Corporation Fresh Meat Color in Vacuum Packaged or Modified Atmosphere Packaged Fresh Meat Products
WO2016100299A1 (fr) 2014-12-15 2016-06-23 Cargill, Incorporated Procédé d'amélioration des parties de muscle et produits

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080305213A1 (en) * 2007-06-11 2008-12-11 Kerry Group Services International, Ltd. Method and composition for preparing cured meat products
US20110300591A1 (en) 2008-12-11 2011-12-08 Danisco A/S Bacterial Compositions of Staphylococcus Vitulinus Having Nitrate Reductase Activity and of Lactic Acid Bacteria and Methods Using These Compositions
US20100310738A1 (en) * 2009-06-04 2010-12-09 Wti, Inc. Method of processing meat
US20120027896A1 (en) 2010-07-30 2012-02-02 Hormel Foods Corporation Fresh Meat Color in Vacuum Packaged or Modified Atmosphere Packaged Fresh Meat Products
WO2016100299A1 (fr) 2014-12-15 2016-06-23 Cargill, Incorporated Procédé d'amélioration des parties de muscle et produits

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SEBRANEK ET AL: "Cured meat products without direct addition of nitrate or nitrite: what are the issues?", MEAT SCIENCE, ELSEVIER SCIENCE, GB, vol. 77, no. 1, 23 June 2007 (2007-06-23), pages 136 - 147, XP022126947, ISSN: 0309-1740, DOI: 10.1016/J.MEATSCI.2007.03.025 *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020181016A1 (fr) * 2019-03-04 2020-09-10 Broussard Robert R Produits alimentaires favorisant la santé et leur procédé de conception et de fabrication
WO2020245407A1 (fr) 2019-06-05 2020-12-10 Purac Biochem B.V. Composition pour conserver ou améliorer la qualité de la viande transformée
WO2020245405A1 (fr) 2019-06-05 2020-12-10 Purac Biochem B.V. Composition pour conserver ou améliorer la qualité de viande transformée
EP4183263A1 (fr) 2019-06-05 2023-05-24 Purac Biochem B.V. Composition pour maintenir ou améliorer la qualité de viande transformée
EP4205557A1 (fr) 2019-06-05 2023-07-05 Purac Biochem B.V. Composition pour maintenir ou améliorer la qualité de viande transformée
WO2021206724A1 (fr) 2020-04-10 2021-10-14 Purac Biochem B.V. Composition d'oignons fermentés
WO2021204995A1 (fr) 2020-04-10 2021-10-14 Purac Biochem B.V. Composition d'oignon fermenté
WO2021260033A1 (fr) 2020-06-23 2021-12-30 Purac Biochem B.V. Composition permettant de conserver et/ou d'améliorer la qualité de produits à base de viande
WO2021262144A1 (fr) 2020-06-23 2021-12-30 Purac Biochem B.V. Composition pour conserver ou améliorer la qualité de produits carnés
WO2021260030A1 (fr) 2020-06-23 2021-12-30 Purac Biochem B.V. Composition pour conserver ou améliorer la qualité de produits carnés
US20220386635A1 (en) * 2021-04-18 2022-12-08 Kemin Industries, Inc. Nitrite replacement (curing aids) containing natural ingredients
WO2023062216A1 (fr) 2021-10-14 2023-04-20 Purac Biochem B.V. Composition d'oignons fermentés

Similar Documents

Publication Publication Date Title
WO2018106109A1 (fr) Composition de traitement de viande et son utilisation
US11071304B2 (en) Method and composition for preparing cured meat products
US20230404090A1 (en) Method of producing a vinegar-derived food additive
Choi et al. Evaluation of sodium lactate as a replacement for conventional chemical preservatives in comminuted sausages inoculated with Listeria monocytogenes
Montiel et al. Effect of high pressure treatments on smoked cod quality during refrigerated storage
AU2017371469B2 (en) Meat treatment composition and use thereof
Mahmoudzadeh et al. Quality assessment of fish burgers from deep flounder (Pseudorhombus elevatus) and brushtooth lizardfish (Saurida undosquamis) during storage at-18ºC
US11576407B2 (en) Preservation of meat products
Cho et al. Survival of Escherichia coli O157: H7 and Listeria monocytogenes during kimchi fermentation supplemented with raw pork meat
CN101026961A (zh) 用于保存鲜肉的抗菌剂
Aksu et al. Effect of modified atmosphere packaging, storage period, and storage temperature on the residual nitrate of sliced-pastırma, dry meat product, produced from fresh meat and frozen/thawed meat
Gul et al. Safety of meat and poultry
US20170273323A1 (en) Preservation of meat products
JPH04349846A (ja) 食肉の保存法と保存用組成物
Sadeghi-Mehr et al. Sensory, physicochemical and microbiological properties of dry-cured formed ham: comparison of four different binding systems
WO2016060562A1 (fr) Conservation de produits carnés
Ezeama et al. The influence of fermentation and salting on the bacterial, chemical and sensory characteristics of catfish (Clarias buthupogon) based marinate in Nigeria
KR20240063922A (ko) 완충 유기산의 기능을 향상시키기 위한 천연 향료 및 천연 훈연 향료의 용도 및 이의 생성 방법
KR100387434B1 (ko) 김치발효공정을 이용한 유산균 식이섬유함유 발효육의제조방법
CN111543600A (zh) 一种改善香肠色泽、降低亚硝胺和生物胺的制备方法
Günşen et al. The effect of modified atmosphere packaging on extending shelf-lifes of cold storaged marinated seafood salad
Shahin Production of Ready to Eat Sausage by New Method
LU503488B1 (en) Preparation method for improving color of sausage and reducing contents of nitrosamines and biogenic amines
Bozkurt et al. Sucuk: Turkish Dry-Fermented Sausage
BR112019011563B1 (pt) Composição líquida concentrada para tratamento de carne, método de produção de uma composição líquida concentrada para tratamento de carne e método para tratar carne

Legal Events

Date Code Title Description
DPE1 Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17817928

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 3046317

Country of ref document: CA

NENP Non-entry into the national phase

Ref country code: DE

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112019011563

Country of ref document: BR

ENP Entry into the national phase

Ref document number: 2017371469

Country of ref document: AU

Date of ref document: 20171206

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 2017817928

Country of ref document: EP

Effective date: 20190708

ENP Entry into the national phase

Ref document number: 112019011563

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20190604