CA2232334A1 - Flavour extract - Google Patents

Flavour extract

Info

Publication number
CA2232334A1
CA2232334A1 CA002232334A CA2232334A CA2232334A1 CA 2232334 A1 CA2232334 A1 CA 2232334A1 CA 002232334 A CA002232334 A CA 002232334A CA 2232334 A CA2232334 A CA 2232334A CA 2232334 A1 CA2232334 A1 CA 2232334A1
Authority
CA
Canada
Prior art keywords
mixture
co2
extraction
flavour
flavours
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.)
Abandoned
Application number
CA002232334A
Other languages
French (fr)
Inventor
Sven Heyland
Christoph Cerny
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.)
Societe des Produits Nestle SA
Original Assignee
Societe des Produits Nestle SA
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
Priority to EP97201469.0 priority Critical
Priority to EP97201469A priority patent/EP0878135B1/en
Application filed by Societe des Produits Nestle SA filed Critical Societe des Produits Nestle SA
Publication of CA2232334A1 publication Critical patent/CA2232334A1/en
Application status is Abandoned legal-status Critical

Links

Classifications

    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/21Synthetic spices, flavouring agents or condiments containing amino acids
    • A23L27/215Synthetic spices, flavouring agents or condiments containing amino acids heated in the presence of reducing sugars, e.g. Maillard's non-enzymatic browning
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10Natural spices, flavouring agents or condiments; Extracts thereof
    • A23L27/11Natural spices, flavouring agents or condiments; Extracts thereof obtained by solvent extraction
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/201Compounds of unspecified constitution characterised by the chemical reaction for their preparation

Abstract

Process for the extraction of flavours in which a mixture is prepared containing, at least, a source of sulphur, a reducing sugar, a phosphate compound and water, this mixture is heated, this mixture is subjected to a CO2 counter-current liquid extraction and a separation is then performed on the CO2 loaded with flavours, so as to obtain a liquid flavour extract.

Description

Flavour extract The present invention relates to a process for the extraction of flavours, and to the use of these flavours for making food compositions.

The extraction of flavours in the presence of polar solvents is known.

The extraction of meat or fish flavours using water as a polar solvent is particularly known. The flavour extract isolated by means of this type of extraction contains flavours but also non-volatile compounds which are important to the taste.
Thus, US 3957745 describes a process for the preparation of a mixture of flavours in which a source of sulphur, i.e.
inorganic sulphur and/or an amino acid, reacts with an alpha-hydroxycarbonyl, a beta-epoxycarbonyl or an alpha-epoxycarbonyl in the presence of at least one polarsolvent, at a temperature of 65-200~C and a pressure of 1 to 100 atm, so as to produce flavours and the flavours are then separated from the residue, particularly by filtration. These flavours are particularly used to modify the flavour note or the taste of a food product.

It is further known to use CO2 to extract spices and herbs or to isolate flavours of oil, fats, fruits or coffee, for example.
Thus, US 3477856 describes a process for the isolation of volatile flavours from fruit juices or essences in which a liquid CO2 extraction is performed on a fruit juice or essence, the phase containing the flavours is separated from the residual fruit juice or essence phase and the CO2 contained in this phase is then evaporated so as to isolate a liquid extract containing volatile fruit flavours.

Further, US 4328255 describes a process for the extraction of a coffee oil containing flavours in a stable form, in which a supercritical CO2 extraction is performed on roasted coffee at no less than 80 atm and at a temperature greater than 31.3~C.

The object of the present invention is to propose a simple and rapid process enabling volatile flavours to be extracted. In addition, the process according to the present invention has the advantage of enabling very concentrated flavours to be obtained.

To this end, in the process for the extraction of flavours according to the present invention, a mixture is prepared containing, at least, a source of sulphur, a reducing sugar, a phosphate compound and water, this mixture is heated at 50-180~C for 30 min to 5 h, this mixture is subjected to a CO2 counter-current liquid extraction at 70-350 bar and a separation is then performed on the CO2 loaded with flavours, so as to obtain a liquid flavour extract.

Hereafter in the description, the expression "phosphate compound" will be used to refer to phosphate, biphosphate or a polyphosphate.

In addition, hereafter in the description, the expression "extraction yield" will be used to refer to the ratio of the quantity of flavour extract obtained according to the present invention to the quantity of starting mixture.

Surprisingly, it has been found that the process according to the present invention allows volatile flavours to be extracted simply and rapidly.

For this purpose, then, a mixture is prepared containing, at least, a source of sulphur, a reducing sugar, a phosphate compound and water. A mixture may be prepared containing, at least, 1-30~ of a source of sulphur, 1-30%
of a reducing sugar, 1-15% of a phosphate compound and 25-55% of water, for example.

A mixture may be prepared containing glutathione, cysteine, thiamine and/or inorganic sulphur, for example, as the source of sulphur.

A mixture may be prepared containing glucose and/or xylose, for example, as the reducing sugar.

A mixture may be prepared containing a phosphate compound, particularly in such a way as to maintain the pH of the mixture at a value of between 4.5-7.5 inclusive. Phosphate, biphosphate or a polyphosphate is therefore used as the phosphate compound. An ammonium phosphate is preferably used.

This mixture is thus heated at 50-180~C for 30 min to 5 h so as to carry out a Maillard reaction, i.e. so as to make the reducing function of the sugar react with the amine function of the source of sulphur or of another compound contained in the mixture. If the source of sulphur does not have an amine function, ammonium phosphate may be used as the phosphate compound, for example, so as to carry out the Maillard reaction. The phosphate compound contained in the mixture acts as a catalyst during this reaction, in addition to its buffer capacity. In this way the flavours of the mixture are developed. This step may be performed with agitation, particularly in a double casing reactor such as that marketed by Schmizo A.G., Luzerner Strasse 27, CH-4665 Zofingen, so as to obtain a homogeneous reaction, for example.

A CO2 counter-current liquid extraction is then performed on this mixture at 70-350 bar. This counter-current extraction may be performed in an extractor, particularly in a column extractor in which the mixture is fed in through the top of the column and the CO2 is fed in through the bottom of the column, for example.

The flavour note of the flavour extract may particularly be varied according to the temperature at which the CO2 counter-current liquid extraction at 70-350 bar is performed on the mixture.

Thus, in a first preferred embodiment of the present process, the CO2 counter-current liquid extraction may be performed on the mixture at 20-31~C so as to reinforce the sulphurous flavour note of the flavour extract, for example. The counter-current liquid extraction is thus carried out in the presence of liquid CO2.

In a second preferred embodiment of the process, the CO2 counter-current liquid extraction may be performed on the mixture at a temperature greater than 31~C and less than 100~C, for example. The counter-current liquid extraction is thus carried out in the presence of super-critical CO2.
5-20 kg of CO2/kg of mixture may be used to perform the counter-current liquid extraction, for example. The extraction yield may be increased by increasing the quantity of CO2/kg of mixture, for example.
An extraction residue on the one hand and, on the other hand, the CO2 loaded with flavours, which leaves at the top of the extractor column and which is then passed into the separator, are then recovered.

A separation is then performed on the CO2 loaded with flavours so as to obtain a liquid flavour extract. This separation may be performed in a separator in which the temperature of the medium is lowered to ambient temperature and the pressure of the medium is lowered to a value of less than 40 bar so as to reduce the solubility of the flavours in the CO2 and to enable a liquid flavour extract to be isolated, for example.

The liquid flavour extract thus obtained may be dried on a support, such as maltodextrin or a starch, so as to obtain the flavour extract in the form of a powder, for example.

The SFF 5860 extraction unit, marketed by Separex Chimie Fine, 5, rue Jean Monod-BP 9, F-54520 Champigneulles, may particularly be used for the extraction step and the separation step.

The CO2 may be recompressed and reintroduced into the extractor for another extraction, for example.

In addition, the extraction residue, which still contains about 20~ original flavours, as well as reaction products such as the phosphate compound and the colouring compounds which are not volatile, may be recovered, for example. This extraction residue may particularly be mixed with salt, soy sauce and/or yeast extract. This mixture may then be dried with a drying support, such as maltodextrin, so as to obtain a flavouring powder, for example.
The present invention also provides the flavour extract obtained according to the process and its use for the preparation of a food composition. Indeed, the flavour extract made in this way, in liquid or dried form, may advantageously be used for the preparation of a food composition, for example. It may particularly be used for the preparation of cooked dishes, sauces or stocks so as to modify their flavour note, for example.

The process for the extraction of flavours and the flavour extracts according to the present invention are described in more detail by means of the analytical tests below. The percentages are given by weight, unless otherwise specified.

Test 1: Extraction yield as a function of the quantity of CO2, the temperature and the pressure during the counter-current liquid extraction step 5 samples of flavour extract are prepared, obtained by implementing the process according to the present invention. The conditions of the counter-current liquid extraction step are varied (the quantity of CO2, the temperature and the pressure) for the preparation of these 5 samples, and their extraction yield is then compared.
For this purpose, a mixture is prepared containing 8.37 cysteine, 8.37~ thiamine, 1.90~ xylose, 20.29~ glucose, 10.38~ diammonium phosphate, 2.15~ onion extract, 1.32 sodium hydroxide and 47.36~ water.
This mixture is heated at 100~C for 4 h so as to carry out the Maillard reaction between the reducing function of the xylose and the glucose and the amine function of the thiamine, the cysteine and the diammonium phosphate and thus to develop the flavours of the mixture.

A CO2 counter-current liquid extraction is then performed in a column extractor in which the mixture is fed in through the top of the column and the CO2 is fed in through the bottom of the column.
For the different tests performed, the temperature and pressure conditions and the quantity of CO2 used during CA 02232334 l998-04-23 this CO2 counter-current liquid extraction are indicated in Table I below.

The CO2 loaded with flavours, which leaves at the top of the extraction column, is then recovered and subjected to a separation in a separator so as to remove the CO2 and to isolate the liquid flavour extract. For this purpose, the solubility of the flavours in the CO2 is reduced by lowering the temperature in the extractor to a temperature less than or equal to 20~C and lowering the pressure to a pressure of less than 40 bar.

The removed CO2 is recompressed and reintroduced into the extractor for another extraction.

The flavour extract is dried using maltodextrin as the drying support.

For each test performed, the extraction yield is calculated by calculating the ~6 of flavour extract isolated in relation to the quantity of starting mixture used.

The results of the different tests performed are shown in Table I below.

Table I

extraction yield (~) tests pressure (bar) temperature (~C) a b c 1 100 75 2.75 4.907.25 2 70 20 1.15 2.052.70 3 140 40 1.90 3.905.40 4 280 77 5.15 8.6511.90 280 20 1.55 2.653.75 key: (a) 5 kg CO2/kg of mixture (b) 10 kg CO2/kg of mixture (c) 15 kg CO2/kg of mixture The results of these tests highlight the fact that the extraction yield of the flavours is better when a greater quantity of CO2 is used. Indeed, for the 5 tests carried out, an increase in the extraction yield is observed depending on whether 5, 10 or 15 kg CO2/kg of mixture was used during the counter-current liquid extraction on the mixture.
In addition, the results of these tests highlight the fact that the extraction yield of the flavours is also better when the counter-current liquid extraction is performed on the mixture at elevated temperature. Indeed, tests 1, 3 and 4 give better yield results. For these tests, a counter-current liquid extraction was performed on the mixture with super-critical CO2.
The results of these tests also show that the flavour extraction yield is better when a CO2 counter-current liquid extraction is performed on the mixture under high pressure.
Finally, the fact that the density of the CO2 has no influence on the extraction yield of the flavours is highlighted.

Thus the extraction yield of the flavours is better when the CO2 counter-current liquid extraction is performed on the mixture at elevated temperature, under high pressure and in the presence of a significant quantity of CO2.

Test 2: Sensory evaluation of the flavour extract A sensory evaluation is carried out on samples containing a flavour extract obtained by implementing the process according to the present invention.

~or this purpose, 5 flavour extracts are prepared in accordance with the process of the present invention.
During the preparation of these 5 extracts, a counter-current liquid extraction is performed on the mixture, as described in test 1, in the presence of 15 kg of C02 and under different temperature and pressure conditions. The temperature and pressure conditions for the preparation of these 5 extracts are shown in Table II below.

5 samples are then made by mixing 0.2 g/l of each extract made in this way per litre of hot water, also containing 2 g/l salt and 1 g/l MSG.

At the same time, a reference sample is made by adding 4 g/l of the mixture, as described in test 1, per litre of hot water, also containing 2 g/l salt and 1 g/l monosodium glutamate.

These 5 samples, together with the reference sample, are then tasted by 5 taste testers so as to describe and compare their flavour note.

The sensory evaluation of these 5 samples and that of the reference sample are shown in Table II below.

Table II

sample extraction conditions flavour note pressure (bar) temperature (~C) reference meat, bitter, sulphur taste 1 100 75 meat 2 70 20 meat, sulphur taste 3 140 40 meat 4 280 77 meat 280 20 meat, sulphur taste The sensory evaluation enables the fact that the 5 samples made in this way have a good meat flavour to be highlighted.
In addition, this evaluation highlights the fact that, when the counter-current liquid extraction is carried out at low temperature, i.e. with the aid of liquid CO2, a flavour extract having a sulphurous flavour note is isolated.

Test 3: Evaluation of the extraction yield with the aid of flavour indicators A sample of flavour extract, obtained by implementing the process according to the present invention, is prepared. To make this sample, a CO2 counter-current liquid extraction is performed on the starting mixture at a pressure of 280 bar, a temperature of 77~C and in the presence of 15 kg of The extraction yield is evaluated with the aid of flavour indicators. For this purpose, the concentration of 3 flavour indicators is measured in the starting mixture and in the flavour extract: 2,5-dimethyl-4-hydroxy-3(2H)-furanone, acetic acid and sulphurol, having similar chemical properties and a similar polarity to those of the other relevant flavour compounds contained in the flavour extract.

The concentration of acetic acid is determined enzymatically using the 148261 enzymatic kit marketed by Boehringer Mannheim, CP 6343, Industrie Strasse 7, CH-Rotkreuz.

The concentration of sulphurol, which is a degradation product of thiamine, is determined by gas phase chromatography.

Finally the concentration of 2,5-dimethyl-4-hydroxy-3(2H)-furanone is determined by marking with an isotope, ~131 by the method described by Sen et al. (Sen et al., Lebensm Wiss Technol 24: 364-369, 1991).

The concentration values of the 3 flavour indicators in the starting mixture and in the flavour extract, as well as the extraction yields of these 3 flavour indicators, are shown in Table III below.

Table III

flavour concentration in concentration in extraction indicator starting mixture flavour extract yield (%) (mg/kg) (mg/kg) a 76 308 48 b 470 2800 71 c 12400 7300 70 key: (a) 2,5-dimethyl-4-hydroxy-3(2H)-furanone (b) acetic acid (c) sulphurol The results shown in Table III highlight the fact that the flavour indicators were, in fact, extracted when the extraction process according to the present invention was implemented. In addition, the fact is highlighted that even the highly polar flavours, which are very difficult to extract by distillation, are extracted during the extraction according to the present invention. Indeed, 2,5-dimethyl-4-hydroxy-3(2H)-furanone, which is a highly polar flavour, has also been extracted. An extraction yield value of 48~ is obtained for this flavour indicator. It is therfore assumed that this flavour was probably partially decomposed during the extraction process according to the present invention.

The following examples are given as an illustration of an industrial use, in the foodstuffs sector, of the flavour extracts according to the present invention. In the examples below, the percentages are given by weight unless otherwise indicated.
Example 1 A beef stock is prepared using a flavour extract obtained by implementing the process according to the present invention.

For this purpose, a mixture is prepared containing 8.37 cysteine, 8.37~ thiamine, 1.90% xylose, 20.29~ glucose, 10.38~ diammonium phosphate, 2.15~ onion extract, 1.32 sodium hydroxide and 47.36~ water.

This mixture is heated to 100~C for 4h so as to carry out the Maillard reaction between the reducing function of the xylose and the glucose, and the amine function of the thiamine, the cysteine and the diammonium phosphate and to develop the flavours of the mixture in this way.

A CO2 counter-current liquid extraction is then performed in an extractor, in which the mixture is fed in through the top of the extraction column and the CO2 is fed in through the bottom of the extraction column. This extraction is performed in the presence of 15 kg of CO2 at a temperature of 77~C and a pressure of 280 bar.

The CO2 loaded with flavours, which leaves at the top of the extraction column, is then recovered and subjected to separation in a separator so as to remove the CO2 and isolate the liquid flavour extract. For this purpose the solubility of the flavours in the CO2 is reduced by lowering the temperature to a temperature less than or equal to 20~C and the pressure to a pressure of less than 40 bar in the extractor.

The extraction and the separation are performed in an SFF
5860 extraction unit, marketed by Separex Chimie Fine, F-54250 Champigneulles.
The CO2 which has been removed is recompressed and reintroduced into the extractor for another extraction.

The flavour extract is dried, using maltodextrin as the drying support.

At the same time a composition is prepared containing 373 g maltodextrin, 190 g salt, 100 g yeast extract, 90 g dextrose, 80 g starch, 65 g beef fat, 36 g sugar, 5 g caramel colour, 2.5 g onions, 2 g citric acid, 1 g pepper, 0.5 g garlic, 0.5 g thyme and 0.5 g marjoram.

0.8 g of the flavour extract, 1.2 g salt and 19 g of this composition are then added to 1 l of hot water.

CA 02232334 l998-04-23 A reference is also made by mixing 19 g of the composition and 1.2 g salt into 1 l of hot water.

The flavour note of the beef stock prepared with the flavour extract obtained by implementing the process according to the present invention is then compared with that of the reference stock.

The stock made with the flavour extract has a very pronounced beef flavour whereas the reference stock has a very weak meat flavour.

Example 2 A chicken stock is prepared using a flavour extract obtained by implementing the process according to the present invention.

For this purpose, a flavour extract is prepared as described in Example 1.

At the same time, a composition is prepared containing 378 g maltodextrin, 190 g salt, 100 g yeast extract, 91 g dextrose, 80 g starch, 65 g chicken fat, 36 g sugar, 0.5 g caramel colour, 2.5 g turmeric, 2 g citric acid, 1 g pepper, 0.5 g garlic, 0.5 g rosemary and 0.5 g ginger.

0.8 g of the flavour extract, 19 g of this composition and 1.2 g salt are then added to 1 l of hot water.
A reference stock is also prepared from 1 l of hot water into which 19 g of the composition and 1.2 g salt are mlxed .

The flavour note of the chicken stock prepared with the flavour extract obtained by implementing the process CA 02232334 l998-04-23 according to the present invention is then compared with that of the reference stock.

The stock made with the flavour extract has a very pronounced chicken flavour whereas the reference stock has a flavour bearing little resemblance to that of chicken.

Claims (9)

1. Process for the extraction of flavours in which:
- a mixture is prepared containing, at least, a source of sulphur, a reducing sugar, a phosphate compound and water, - this mixture is heated at 50-180°C for 30 min to 5 h, - this mixture is subjected to a CO2 counter-current liquid extraction at 70-350 bar, - a separation is then performed on the CO2 loaded with flavours, so as to obtain a liquid flavour extract.
2. Process according to claim 1, in which a mixture is prepared containing, at least, 1-30% of a source of sulphur, 1-30% of a reducing sugar, 1-15% of a phosphate compound and 25-55% water.
3. Process according to claim 1, in which the mixture contains glutathione, cysteine, thiamine and/or an inorganic sulphur as the source of sulphur.
4. Process according to claim 1, in which 5-20 kg of CO2/kg of mixture are used to perform the counter-current extraction.
5. Process according to claim 1, in which the CO2 counter-current liquid extraction is performed on the mixture at 20-31°C.
6. Process according to claim 1, in which a CO2 counter-current liquid extraction is performed on the mixture at a temperature greater than 31°C and less than 100°C.
7. Process according to claim 1, in which the liquid flavour extract is dried so as to obtain a powdered flavour extract.
8. Flavour extract obtained by implementing the process according to one of claims 1 to 7.
9. Use of a flavour extract according to claim 8 for the preparation of a food composition.
CA002232334A 1997-05-15 1998-04-23 Flavour extract Abandoned CA2232334A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP97201469.0 1997-05-15
EP97201469A EP0878135B1 (en) 1997-05-15 1997-05-15 Process for preparing and extracting aromas

Publications (1)

Publication Number Publication Date
CA2232334A1 true CA2232334A1 (en) 1998-11-15

Family

ID=8228322

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002232334A Abandoned CA2232334A1 (en) 1997-05-15 1998-04-23 Flavour extract

Country Status (10)

Country Link
EP (1) EP0878135B1 (en)
JP (1) JPH10324891A (en)
AT (1) AT214237T (en)
AU (1) AU729695B2 (en)
BR (1) BR9801636A (en)
CA (1) CA2232334A1 (en)
DE (2) DE69711025D1 (en)
DK (1) DK0878135T3 (en)
ES (1) ES2171826T3 (en)
SG (1) SG770080A1 (en)

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US9309436B2 (en) 2007-04-13 2016-04-12 Knauf Insulation, Inc. Composite maillard-resole binders
US9416248B2 (en) 2009-08-07 2016-08-16 Knauf Insulation, Inc. Molasses binder
US9434854B2 (en) 2005-07-26 2016-09-06 Knauf Insulation, Inc. Binders and materials made therewith
US9447281B2 (en) 2007-01-25 2016-09-20 Knauf Insulation Sprl Composite wood board
US9469747B2 (en) 2007-08-03 2016-10-18 Knauf Insulation Sprl Mineral wool insulation
US9492943B2 (en) 2012-08-17 2016-11-15 Knauf Insulation Sprl Wood board and process for its production
US9493603B2 (en) 2010-05-07 2016-11-15 Knauf Insulation Sprl Carbohydrate binders and materials made therewith
US9505883B2 (en) 2010-05-07 2016-11-29 Knauf Insulation Sprl Carbohydrate polyamine binders and materials made therewith
US9828287B2 (en) 2007-01-25 2017-11-28 Knauf Insulation, Inc. Binders and materials made therewith

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TW200744473A (en) * 2006-04-19 2007-12-16 Specialites Pet Food Use of inorganic phosphate compounds as palatability enhancers of flavours generated by thermal reactions in wet pet foodstuffs
US20170112167A1 (en) * 2014-05-15 2017-04-27 Specialites Pet Food Palatability enhancers comprising amino reactants and carbonyl compounds for use in cat food
CN104293487B (en) * 2014-10-17 2016-08-17 湖北中烟工业有限责任公司 The method of fermentation of grape extracts produced by reacting a Maillard flavor cigarette

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US9926464B2 (en) 2005-07-26 2018-03-27 Knauf Insulation, Inc. Binders and materials made therewith
US9434854B2 (en) 2005-07-26 2016-09-06 Knauf Insulation, Inc. Binders and materials made therewith
US9745489B2 (en) 2005-07-26 2017-08-29 Knauf Insulation, Inc. Binders and materials made therewith
US9464207B2 (en) 2005-07-26 2016-10-11 Knauf Insulation, Inc. Binders and materials made therewith
US10000639B2 (en) 2007-01-25 2018-06-19 Knauf Insulation Sprl Composite wood board
US9447281B2 (en) 2007-01-25 2016-09-20 Knauf Insulation Sprl Composite wood board
US9828287B2 (en) 2007-01-25 2017-11-28 Knauf Insulation, Inc. Binders and materials made therewith
US9309436B2 (en) 2007-04-13 2016-04-12 Knauf Insulation, Inc. Composite maillard-resole binders
US9469747B2 (en) 2007-08-03 2016-10-18 Knauf Insulation Sprl Mineral wool insulation
US10053558B2 (en) 2009-08-07 2018-08-21 Knauf Insulation, Inc. Molasses binder
US9416248B2 (en) 2009-08-07 2016-08-16 Knauf Insulation, Inc. Molasses binder
US9493603B2 (en) 2010-05-07 2016-11-15 Knauf Insulation Sprl Carbohydrate binders and materials made therewith
US9505883B2 (en) 2010-05-07 2016-11-29 Knauf Insulation Sprl Carbohydrate polyamine binders and materials made therewith
US9492943B2 (en) 2012-08-17 2016-11-15 Knauf Insulation Sprl Wood board and process for its production
US10183416B2 (en) 2012-08-17 2019-01-22 Knauf Insulation, Inc. Wood board and process for its production

Also Published As

Publication number Publication date
BR9801636A (en) 1999-05-04
AT214237T (en) 2002-03-15
EP0878135B1 (en) 2002-03-13
EP0878135A1 (en) 1998-11-18
DK0878135T3 (en) 2002-06-17
ES2171826T3 (en) 2002-09-16
AU729695B2 (en) 2001-02-08
SG770080A1 (en) 2000-01-25
DE69711025T2 (en) 2002-08-22
AU6593698A (en) 1998-11-19
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