EP1301543A1 - Procede de preparation d'oligomeres de galactomannanes - Google Patents
Procede de preparation d'oligomeres de galactomannanesInfo
- Publication number
- EP1301543A1 EP1301543A1 EP01954095A EP01954095A EP1301543A1 EP 1301543 A1 EP1301543 A1 EP 1301543A1 EP 01954095 A EP01954095 A EP 01954095A EP 01954095 A EP01954095 A EP 01954095A EP 1301543 A1 EP1301543 A1 EP 1301543A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- galactomannan
- oligomers
- water
- mixture
- extruder
- 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- Withdrawn
Links
- 229920000926 Galactomannan Polymers 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 42
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 title claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000001125 extrusion Methods 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 8
- 239000007800 oxidant agent Substances 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 5
- 239000000843 powder Substances 0.000 claims description 9
- 235000013305 food Nutrition 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000003905 agrochemical Substances 0.000 claims description 5
- 239000004566 building material Substances 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 5
- 238000005553 drilling Methods 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 238000004043 dyeing Methods 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- -1 pharmaceutical Substances 0.000 claims description 3
- 244000007835 Cyamopsis tetragonoloba Species 0.000 claims 1
- 238000010411 cooking Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 12
- 239000002245 particle Substances 0.000 description 10
- 244000303965 Cyamopsis psoralioides Species 0.000 description 5
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- 229930182830 galactose Natural products 0.000 description 3
- 229960003082 galactose Drugs 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000011295 pitch Substances 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
- 235000017399 Caesalpinia tinctoria Nutrition 0.000 description 2
- 240000008886 Ceratonia siliqua Species 0.000 description 2
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 2
- 229920002907 Guar gum Polymers 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229920000161 Locust bean gum Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000388430 Tara Species 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000593 degrading effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001033 granulometry Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000000665 guar gum Substances 0.000 description 2
- 235000010417 guar gum Nutrition 0.000 description 2
- 229960002154 guar gum Drugs 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000711 locust bean gum Substances 0.000 description 2
- 235000010420 locust bean gum Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 108010011619 6-Phytase Proteins 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 244000037364 Cinnamomum aromaticum Species 0.000 description 1
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 1
- 125000003436 D-mannopyranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000035092 Neutral proteases Human genes 0.000 description 1
- 108091005507 Neutral proteases Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 229940025131 amylases Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 235000010491 tara gum Nutrition 0.000 description 1
- 239000000213 tara gum Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 235000001019 trigonella foenum-graecum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0087—Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof
Definitions
- the present invention relates to a process for the preparation of oligomers of at least one galactomannan by treating it by cooking-extrusion. It also relates to the oligomers obtained or capable of being obtained by this process, as well as their uses.
- the invention further relates to the compositions based on the above oligomers.
- Galactomannans are nonionic polysaccharides extracted from the albumen of legume seeds of which they constitute the reserve carbohydrate. They are especially known and used as a texture agent and in particular for their viscosifying, thickening, stabilizing, water-retaining, and film-forming properties. Among the most widely used are guar gum, locust bean gum, and tara gum.
- the different galactomannans are distinguished by the proportion of D-mannopyranose and D-galactopyranose units which are represented by their mannose / galactose ratio (hereinafter M / G). Although variable from one species to another, the mannose / galactose ratio is about 1 for fenugreek, 2 for guar, 3 for tara, and 4 for locust bean.
- polysaccharides are all the more advantageous because, by their nature, they are compatible with other compounds and therefore can be used in combination with these to produce synergistic effects, inter alia, in terms of texture.
- locust bean gum in combination with xanthan gum can lead to gels of different strengths and more or less elastic consistencies.
- Native galactomannans are highly hydrophilic polymers which, at low concentrations, lead to very viscous solutions. Depending on the intended application, this aspect may limit their use.
- the properties of galactomannans can be linked to their molecular mass.
- galactomannans whose texturing properties and in particular the thickening or viscosifying property can be adjusted.
- the classic routes of access to galactomannans of different molecular weights are:
- EP 0130946 for the oxidative depolymerization process in the presence of alkali, and for the basic route in the presence of oxygen,
- the enzymatic depolymerization which has the advantage of allowing a selective cleavage of the galactomannan (compared to the chemical process) is a process which is not economically advantageous. In addition, in some cases, it is difficult to deactivate the enzyme at the end of the reaction without degrading the depolymerized product.
- the present invention aims to overcome the drawbacks mentioned above by proposing a process which is simple and economical to implement and in which the resulting oligomers are free of secondary products.
- Another object of the present invention is to provide a process for the preparation of galactomannan oligomers continuously.
- the present invention which relates to a process for the preparation of oligomers of at least one galactomannan, characterized in that a mixture comprising at least one galactomannan in solid form and of water, but devoid of oxidizing agent and acid, to a cooking-extrusion treatment, the specific mechanical energy of which is between 140 and 200 Wh / kg and the temperature at the top of the product is between 80 and 180 ° C.
- the specific mechanical energy is between 150 and 200 Wh / kg.
- a subject of the invention is also the galactomannan oligomers obtained or capable of being obtained by the above-mentioned process.
- oligomer of galactomannans means galactomannans whose viscosity is lower than that of the galactomannans introduced into the cooker-extruder.
- the viscosity of the product thus extruded can be measured by various methods, in particular by a Brookfield RVT 500 device (20 rpm) at 25 ° C. in a solution at 0.5% by weight of distilled water. More particularly, the ratio of the viscosities of the oligomers obtained on the starting galactomannans is less than or equal to 4/5, advantageously less than or equal to 3/5.
- the galactomannans can be used alone or as a mixture.
- the galactomannans non-limiting mention may be made of galactomannans having a mannose / galactose ratio (M / G) of at most 5, and more particularly guar, carob, cassia and tara.
- the galactomannan is guar.
- the galactomannan is advantageously in the form of a powder.
- the powder can be obtained by conventional grinding means such as grinding in mills of the type: - cylinder mills for powder of average particle size 100 mesh, that is to say a flour having at most 1% by mass of particles greater than 80 mesh and at most 10% by mass of particles less than 200 mesh;
- type mesh 200 that is to say a powder having no particles greater than 80 mesh and having at most 60% by mass of smaller particles at 200 mesh, and
- ° mesh type 175 that is to say a powder having at most 1% by mass of particles greater than 80 mesh and at most 75% by mass of particles less than 200 mesh.
- the powder can be used as it is or after treatment with suitable enzymes such as, for example, alkaline, acidic and / or neutral proteases; of the
- Iipases phytases; alkaline, acidic and / or neutral phosphatases; amylases.
- the treatment with enzymes is carried out by conventional and known methods.
- the particle size of said powder can fluctuate between 10 and 150 microns. In the case of treated powders, this particle size is more particularly from 20 to 60 microns, preferably from 30 to 50 microns.
- Granulometry measurements can be carried out by the laser granulometry technique, using a MALVERN granulometer, sold by the company Malvern Instruments S.A.
- the mixture comprises water.
- the amount of water introduced into the extruder is generally such that the amount of water represents in the mixture at least 50%, preferably at least 53%, by weight relative to the total weight of the mixture.
- Such a proportion of water makes it possible in particular to reduce the variations in pressures which can, when these variations are too great, make the implementation of this process difficult, if not impossible.
- this amount of water is less than or equal to 65%, preferably 62%, by weight relative to the total weight of the mixture.
- the mixture comprising at least one galactomannan in solid form and water, is generally produced in the cooking-extrusion processing machine (introduction in parallel).
- water is preferably mixed with the galactomannan before introduction into the machine (preconditioning).
- the preconditioning water is advantageously introduced at a temperature of the order of 90 ° C or in the form of vapor.
- the water which is introduced in parallel into the extruder is preferably introduced into a module having a temperature between 50 and 70 ° C.
- the depolymerization of galactomannans into galactomannan oligomers according to this process does not require the presence of at least one oxidizing or acidic agent.
- oxidizing agents such as in particular hydrogen peroxide, nitric acid, and their mixtures, are not introduced. It is the same for acids, such as in particular lactic acid, tartaric acid, citric acid, phosphoric acid, sulfuric acid and their mixtures.
- the above mixture is then subjected to controlled conditions of temperature and pressure so that the galactomannan undergoes no degradation and only depolymerization.
- the temperature at the top of the product in the cooker-extruder is advantageously between 80 ° C and 180 ° C, preferably between 100 ° C and 150 ° C.
- the screw speeds preferentially vary between 110 and 300 rpm and advantageously between 110 and 150 rpm.
- the flow rate of pulverulent material is preferably between 18 and 30 kg / h ("wet" material, the dry material representing 90-92% by weight of the wet material), advantageously between 20 and 25 kg / h.
- the residence time is variable and will of course depend on the desired viscosity and the operating conditions, in particular the cooking-extrusion apparatus used, the screw speed and the feed rate. In general, it is less than 1 minute.
- the product thus extruded can undergo another or possibly several other passages in the cooker-extruder.
- the extruded oligomers obtained according to the process of the present invention are recovered and advantageously undergo a drying step.
- This drying step is advantageously carried out so as to obtain a moisture content of between 8 and 12% by weight relative to the total weight of the product obtained (oligomers + water), while preventing the oligomers from degrading.
- this step is advantageously carried out by heating to a temperature between 30 and 60 ° C, preferably between 35 and 45 ° C.
- the process of the invention is advantageously carried out continuously.
- the process of the invention can be carried out in any type of cooker-extruder.
- a twin-screw extruder is used.
- the following devices can in particular be cited: the twin-screw models BC21, BC 45, BC72, BC82 from the company Clextral, the twin screw extruder ZSK 40 from the company Werner & Pfleiderer Gmbh, the models
- the twin screw extruder with co-rotating and co-penetrating screws
- Clextral BC 45 of 66kW.
- the screws can comprise sections with positive action of different pitches, sections with negative pitches (counter-threads) or sections made up of mixing discs. Generally, the screws are made up of a succession of these different types of sections.
- the extruder is equipped with one or more modules, therefore of variable length
- each module has a length of 200mm in the case of the Clextral BC 45
- the machine has a length of sheath which can vary from 600 to 1400 mm (i.e. in the case of the Clextral BC 45 the sheath consists of 3 to 7 modules).
- These modules are either sealed or pierced with one or more orifices (allowing in particular the introduction of materials into the extruder or degassing).
- the temperature of the sheath can be regulated in particular by a heat-transfer fluid, by heating collars or induction coils or by a combined system, in particular by heating by a thermal induction system and by cooling by circulation of cold water.
- the first part of this sheath that is to say the part for supplying reagents, often materialized by the (or both) first module (s) pierced with orifices, is at a temperature between 15 and 50 ° C and the rest of the sleeves is regulated at a temperature advantageously between 50 ° C and 180 ° C, preferably between 60 ° C and 150 ° C.
- the temperature can vary from one module to another.
- a die assembly At the end of the terminal sheath is assembled a die assembly: a front plate and a generally cylindrical die.
- a knife is placed on the external face of the die which makes it possible to cut the extruded product into sections of defined length.
- the temperature at the top of the product is called the temperature at the end of the machine, generally at the level of the front plate, just before the die and the product outlet.
- the present invention also relates to the galactomannan oligomers obtained or capable of being obtained by the process according to the invention.
- the invention also relates to the uses of the galactomannan oligomers obtained or capable of being obtained by the process of the invention, in the cosmetic, dyeing, food, detergency, agrochemical, industrial formulations, pharmaceuticals, building materials industries. , drilling fluids.
- the invention finally relates to the compositions based on galactomannan oligomers obtained or capable of being obtained by the process of the invention, in the cosmetic, dyeing, food, detergency, agrochemical fields, those of industrial, pharmaceutical formulations , building materials, drilling fluids. Concrete but nonlimiting examples of the invention will now be presented.
- the cooker-extruder used is the BC 45 from Clextral co-rotating twin-screw model of 66kW with a sheath length of 1000mm (5 modules) with a negative pitch zone and 3 heating zones.
- the starting galactomannan is guar gum (MEYPRO® - GUAR CSA 200/50 from the company MEYHALL).
- the products obtained after extrusion are dried in an oven at 40 ° C. in order to stabilize them at a humidity of between 8 and 12% by weight.
- Samples 1, 2 and 3 are ground and only the fraction less than 100 ⁇ m is used by reference to the particle size of the control sample. Viscosity is measured at using a Brookfield model 500 RVT device under the following conditions: 0.5% solution in distilled water, dispersion with ultraturax for 20 seconds at 9500 rpm, the viscosity being measured at 20 rpm at 25 ° C after 24 hours.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0009333 | 2000-07-17 | ||
FR0009333A FR2811667B1 (fr) | 2000-07-17 | 2000-07-17 | Procede de preparation d'oligomeres de galactomanannes |
PCT/FR2001/002288 WO2002006352A1 (fr) | 2000-07-17 | 2001-07-13 | Procede de preparation d'oligomeres de galactomannanes |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1301543A1 true EP1301543A1 (fr) | 2003-04-16 |
Family
ID=8852576
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01954095A Withdrawn EP1301543A1 (fr) | 2000-07-17 | 2001-07-13 | Procede de preparation d'oligomeres de galactomannanes |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1301543A1 (fr) |
AU (1) | AU2001276446A1 (fr) |
FR (1) | FR2811667B1 (fr) |
MA (1) | MA25828A1 (fr) |
WO (1) | WO2002006352A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2787219C1 (ru) * | 2022-04-27 | 2022-12-30 | Федеральное государственное бюджетное научное учреждение "Федеральный исследовательский центр "Красноярский научный центр Сибирского отделения Российской академии наук" (ФИЦ КНЦ СО РАН, КНЦ СО РАН) | Способ сульфатирования галактоглюкоманнана древесины сосны сульфаминовой кислотой |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6884884B2 (en) | 2001-06-11 | 2005-04-26 | Rhodia, Inc. | Galactomannan compositions and methods for making and using same |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2042559A1 (fr) * | 1990-08-10 | 1992-02-11 | Chokyun Rha | Derives de polysaccharide a faible poids moleculaire utilises dans les aliments |
EP0613907A3 (fr) * | 1993-03-04 | 1995-05-24 | Genzyme Ltd | Réduction contrÔlée du poids moléculaire de polymères. |
FR2802932A1 (fr) * | 1999-12-27 | 2001-06-29 | Rhodia Food S A S | Procede de preparation d'oligomeres de galactomannanes |
-
2000
- 2000-07-17 FR FR0009333A patent/FR2811667B1/fr not_active Expired - Fee Related
-
2001
- 2001-07-13 AU AU2001276446A patent/AU2001276446A1/en not_active Abandoned
- 2001-07-13 WO PCT/FR2001/002288 patent/WO2002006352A1/fr not_active Application Discontinuation
- 2001-07-13 EP EP01954095A patent/EP1301543A1/fr not_active Withdrawn
-
2003
- 2003-01-17 MA MA27002A patent/MA25828A1/fr unknown
Non-Patent Citations (1)
Title |
---|
See references of WO0206352A1 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2787219C1 (ru) * | 2022-04-27 | 2022-12-30 | Федеральное государственное бюджетное научное учреждение "Федеральный исследовательский центр "Красноярский научный центр Сибирского отделения Российской академии наук" (ФИЦ КНЦ СО РАН, КНЦ СО РАН) | Способ сульфатирования галактоглюкоманнана древесины сосны сульфаминовой кислотой |
Also Published As
Publication number | Publication date |
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MA25828A1 (fr) | 2003-07-01 |
AU2001276446A1 (en) | 2002-01-30 |
FR2811667A1 (fr) | 2002-01-18 |
FR2811667B1 (fr) | 2003-02-21 |
WO2002006352A1 (fr) | 2002-01-24 |
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