WO2014158381A1 - Cross-linked ethylsulfonated dihydroxypropyl cellulose - Google Patents
Cross-linked ethylsulfonated dihydroxypropyl cellulose Download PDFInfo
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- WO2014158381A1 WO2014158381A1 PCT/US2014/015538 US2014015538W WO2014158381A1 WO 2014158381 A1 WO2014158381 A1 WO 2014158381A1 US 2014015538 W US2014015538 W US 2014015538W WO 2014158381 A1 WO2014158381 A1 WO 2014158381A1
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F7/00—Compounds of aluminium
- C01F7/02—Aluminium oxide; Aluminium hydroxide; Aluminates
- C01F7/04—Preparation of alkali metal aluminates; Aluminium oxide or hydroxide therefrom
- C01F7/06—Preparation of alkali metal aluminates; Aluminium oxide or hydroxide therefrom by treating aluminous minerals or waste-like raw materials with alkali hydroxide, e.g. leaching of bauxite according to the Bayer process
- C01F7/062—Digestion
- C01F7/0633—Digestion characterised by the use of additives
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F7/00—Compounds of aluminium
- C01F7/02—Aluminium oxide; Aluminium hydroxide; Aluminates
- C01F7/04—Preparation of alkali metal aluminates; Aluminium oxide or hydroxide therefrom
- C01F7/06—Preparation of alkali metal aluminates; Aluminium oxide or hydroxide therefrom by treating aluminous minerals or waste-like raw materials with alkali hydroxide, e.g. leaching of bauxite according to the Bayer process
- C01F7/0646—Separation of the insoluble residue, e.g. of red mud
- C01F7/0653—Separation of the insoluble residue, e.g. of red mud characterised by the flocculant added to the slurry
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F7/00—Compounds of aluminium
- C01F7/02—Aluminium oxide; Aluminium hydroxide; Aluminates
- C01F7/04—Preparation of alkali metal aluminates; Aluminium oxide or hydroxide therefrom
- C01F7/14—Aluminium oxide or hydroxide from alkali metal aluminates
- C01F7/144—Aluminium oxide or hydroxide from alkali metal aluminates from aqueous aluminate solutions by precipitation due to cooling, e.g. as part of the Bayer process
- C01F7/145—Aluminium oxide or hydroxide from alkali metal aluminates from aqueous aluminate solutions by precipitation due to cooling, e.g. as part of the Bayer process characterised by the use of a crystal growth modifying agent other than aluminium hydroxide seed
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/005—Crosslinking of cellulose derivatives
-
- 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
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0021—Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B5/00—Preparation of cellulose esters of inorganic acids, e.g. phosphates
- C08B5/14—Cellulose sulfate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/16—Esters of inorganic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/02—Dextran; Derivatives thereof
Definitions
- bauxite ore is pulverized, slurried with caustic solution, and then digested at elevated temperatures and pressures.
- the caustic solution dissolves oxides of aluminum, forming an aqueous sodium aluminate solution.
- the caustic-insoluble constituents of bauxite ore are then separated from the aqueous phase containing the dissolved sodium aluminate. Solid alumina trihydrate product is precipitated out of the solution and collected as product.
- the pulverized bauxite ore may be fed to a slurry mixer where an aqueous slurry is prepared.
- the slurry makeup solution is typically spent liquor (described below) and added caustic solution.
- This bauxite ore slurry is then passed through a digester or a series of digesters where the available alumina is released from the ore as caustic-soluble sodium aluminate.
- the digested slurry is then cooled, for instance to about 220 degrees F, employing a series of flash tanks wherein heat and condensate are recovered.
- the aluminate liquor leaving the flashing operation contains insoluble solids, which solids consist of the insoluble residue that remains after, or are precipitated during, digestion.
- the coarser solid particles may be removed from the aluminate liquor with a "sand trap", cyclone or other means.
- the finer solid particles may be separated from the liquor first by settling and then by filtration, if necessary.
- the clarified sodium aluminate liquor is then further cooled and seeded with alumina trihydrate crystals to induce precipitation of alumina in the form of alumina trihydrate, Al(OH) 3 .
- the alumina trihydrate particles or crystals are then classified into various size fractions and separated from the caustic liquor.
- the remaining liquid phase, the spent liquor is returned to the initial digestion step and employed as a digestant after reconstitution with caustic.
- one of the key steps is that of precipitation of the alumina trihydrate from the clarified sodium aluminate liquor.
- the clarified sodium aluminate liquor also referred to as "green liquor”
- the precipitation tank(s) it is cooled under agitation to induce the precipitation of alumina from solution as alumina trihydrate.
- the fine particle alumina trihydrate acts as seed crystals which provide nucleation sites and agglomerate together and grow as part of this precipitation process.
- Alumina trihydrate crystal formation (the nucleation, agglomeration and growth of alumina trihydrate crystals), and the precipitation and collection thereof, are critical steps in the economic recovery of aluminum values by the Bayer process.
- Bayer process operators strive to optimize their crystal formation and precipitation methods so as to produce the greatest possible product yield from the Bayer process while producing crystals of a given particle size distribution.
- a relatively large particle size is beneficial to subsequent processing steps required to recover aluminum metal.
- Undersized alumina trihydrate crystals, or fines, generally are not used in the production of aluminum metal, but instead are recycled for use as fine particle alumina trihydrate crystal seed.
- the particle size of the precipitated trihydrate crystals determines whether the material is to be ultimately utilized as product (larger crystals) of as seed (smaller crystals).
- the classification and capture of the different sized trihydrate particles is therefore an important step in the Bayer process.
- This separation or recovery of alumina trihydrate crystals as product in the Bayer process, or for use as precipitation seed, is generally achieved by settling, cyclones, filtration and/or a combination of these techniques. Coarse particles settle easily, but fine particles settle slowly. Typically, plants will use two or three steps of settling in order to classify the trihydrate particles into different size distributions corresponding to product and seed. In particular, in the final step of classification a settling vessel is often used to capture and settle the fine seed particles. Within the settling steps of the classification system, flocculants can be used to enhance particle capture and settling rate.
- the overflow of the last classification stage is returned to the process as spent liquor.
- This spent liquor will go through heat exchangers and evaporation and eventually be used back in digestion.
- any trihydrate particles reporting to the overflow in this final settling stage will not be utilized within the process for either seed or product.
- Effectively such material is recirculated within the process, creating inefficiencies. Therefore, it is important to achieve the lowest possible concentration of solids in the overflow of the last stage of classification to maximize the efficiency of the process. As described for example in U.S. Pat. No.
- the invention relates to a method for improving the Bayer process for the production of alumina from bauxite ore.
- the invention concerns the use of cross-linked polysaccharides, specifically cross-linked dextran or cross-linked dihydroxypropyl cellulose to improve the performance of unit operations within the Bayer process, in particular to enhance the settling of fine alumina trihydrate crystals.
- the cross linked cellulose comprises covalently cross-linked mixed cellulose ether containing predominantly 2,3-dihydroxypropyl ethers. It may also comprise ethylsulfonate ethers.
- cross-linked cellulose ether Key characteristic of such cross-linked cellulose ether are the presence of 2,3-dihydroxylpropyl groups and the covalent cross-linking achieved under homogenous reaction conditions resulting in significant viscosity increases of the in water dissolved polymer.
- a surprisingly unique characteristic of the so prepared dihydroxypropyl ethers is their capability to enhance the flocculation of aluminum trihydrate solids from a highly alkaline, pregnant process liquors in the Bayer process.
- Consisting Essentially of means that the methods and compositions may include additional steps, components, ingredients or the like, but only if the additional steps, components and/or ingredients do not materially alter the basic and novel characteristics of the claimed methods and compositions.
- “Dextran” is a polysaccharide characterized as being an a-D-1,6 glucose-linked glucan with side chains 1-3 linked to the backbone units of the polysaccharide.
- "Dihydroxypropyl cellulose” means a cellulose derivative with the addition of 1,2-dihydroxypropyl ether group to the cellulose backbone.
- “Hydrocy clone” means a device to classify, separate or sort particles in a liquid suspension based on the ratio of their centripetal force to fluid resitance, in particular for dense and coarse particles, and low for light and fine particles, they often have a cylindrical section at the top where liquid is being fed tangentially and a conical base, and they often have two exits on the axis: the smaller on the bottom (for underflow) and a larger one at the top (for overflow), generally the underflow is the denser or coarser fraction, while the overflow is the lighter or finer fraction.
- Liquor or “Bayer liquor” means a caustic, liquid medium that has run through a Bayer process in an industrial facility.
- Polysaccharide means a polymeric carbohydrate having a plurality of repeating units comprised of simple sugars, the C-O-C linkage formed between two such joined simple sugar units in a polysaccharide chain is called a glycosidic linkage, and continued condensation of monosaccharide units will result in polysaccharides, common polysaccharides are amylose and cellulose, both made up of glucose monomers, polysaccharides can have a straight chain or branched polymer backbone including one or more sugar monomers, common sugar monomers in polysaccharides include glucose, galactose, arabinose, mannose, fructose, rahmnose, and xylose.
- Slurry means a mixture comprising a liquid medium within which fines (which can be liquid and/or finely divided solids) are dispersed or suspended, when slurry is sparged, the tailings remain in the slurry and at least some of the concentrate adheres to the sparge bubbles and rises up out of the slurry into a froth layer above the slurry, the liquid medium may be entirely water, partially water, or may not contain any water at all.
- surfactant is a broad term which includes anionic, nonionic, cationic, and zwitterionic surfactants. Enabling descriptions of surfactants are stated in Kirk-Othmer, Encyclopedia of Chemical Technology, Third Edition, volume 8, pages 900-912, and in McCutcheon's Emulsifiers and Detergents, both of which are incorporated herein by reference.
- Thickener or “Settler” means a vessel used to effect a solid-liquid separation of a slurry, often with the addition of flocculants, the vessel constructed and arranged to receive a slurry, retain the slurry for a period of time sufficient to allow solid portions of the slurry to settle downward (underflow) away from a more liquid portion of the slurry (overflow), decant the overflow, and remove the underflow.
- Thickener underflow and thickener overflow are often passed on to filters to further separate solids from liquids.
- the preferred flocculant of the trihydrate solids in the process is a crosslinked polysaccharide.
- Preferred polysaccharides include dextran and dihydroxypropyl cellulose.
- the flocculant is added in the range of 0.1 to 100 ppm. The most preferred dose range for the flocculant is 0.3 to 20 ppm.
- the cross linked cellulose can comprise covalently cross-linked mixed cellulose ether containing 2,3-dihydroxypropyl ethers.
- cross linked cellulose is predominantly 2,3- dihydroxypropyl ethers. In at least one embodiment the cross linked cellulose is predominantly 2,3- dihydroxypropyl ethers. In at least one embodiment the cross linked cellulose is predominantly 2,3- dihydroxypropyl ethers. In at least one embodiment the cross linked
- polysaccharide/cellulose also comprises ethylsulfonate ethers.
- Key characteristic of such cross-linked cellulose ether are the presence of 2,3-dihydroxylpropyl groups.
- the reagent used to convert cellulose to dihydroxypropyl cellulose is glycidol.
- Another suitable reagents is 3-chloro-l,2- propanediol.
- the dihydroxypropyl cellulose is further modified to contain additional anionic charge. This may be accomplished by reacting the dihydroxypropyl cellulose with sodium vinylsulfonate and/or sodium chloroacetate.
- the cross-linkages in the ethylsulfonated dihydroxypropyl cellulose are formed at least in part by reaction with a reagent such as epichlorohydrin, divinylsulfone, glycerol diglycidyl ether, polyethyleneglycol diglycidyl ether, neopentylglycol diglycidyl ether, resorcinol diglycidyl ether, 1,2- dichloroethane, N.N-methylene bisacrylamide, and 1,4-benzoquinone, and any combination thereof.
- a reagent such as epichlorohydrin, divinylsulfone, glycerol diglycidyl ether, polyethyleneglycol diglycidyl ether, neopentylglycol diglycidyl ether, resorcinol diglycidyl ether, 1,2- dichloroethane, N.N-methylene bisacrylamide, and 1,4-benzo
- the cross-linking agents produce bonds between the individual polymer chains of ethylsulfonated dihydroxypropyl cellulose that are stable in aqueous alkaline media.
- Ether linkages as produced by epichlorohydrin or diglyccidyl ethers belong to these group of bonds.
- the cross-linked polysaccharide is dextran.
- the cross-linked dihydroxypropyl cellulose is produced by addition of dextran or dihydroxypropyl cellulose to an alkaline solution containing sodium hydroxide, potassium hydroxide, or other alkali metals or water soluble alkaline earth metal hydroxide, to provide a causticized polymer solution having a pH in the range of 11 to 14.
- the causticized polysaccharide is then reacted with an appropriate bifunctional cross -linking agent. As described at least in U.S. Pat. Nos.
- polysaccharides can be achieved. Surprisingly the maximum performance of cross-linked dextran is superior to the maximum performance using conventional dextran at any dose. Additionally, for cross-linked polysaccharides, the dose at which continued addition results in no further performance benefits is increased.
- composition comprising 5% cross-linked dextran will perform at least as well as a 10% composition of dextran, and in some cases better.
- reagent/polysaccharide can be varied between, but is not limited to, about 0 to 0.2.
- the ratio can be varied between, but is not limited to, 0 to 0.1, most preferably 0.005 to 0.08.
- Appropriate cross-linking is achieved as measured by an increase in the solution viscosity of at least 10% above the original solution viscosity.
- the composition is added to liquor in a trihydrate classification circuit of said alumina trihydrate production process.
- the composition can be added to said liquor at one or more locations in a Bayer process where solid- liquid separation occurs.
- the composition can be added to said liquor at one or more locations in a Bayer process where it inhibits the rate of nucleation of one or more alumina hydrate crystals in said process.
- the composition can be added to said liquor at one or more locations in a Bayer process where it reduces the rate of scale formation in said process. In at least one embodiment the composition can be added to said liquor at one or more locations in a Bayer process where it facilitates red mud clarification in the process.
- composition can be added in combination with or according to any of the compositions and methods disclosed US Patent 8,252,266.
- cellulose dissolving wood pulp, bahia pulp, Solucell 350, disintegrated on a Retsch mill with a 1 mm screen
- 50 gram of cellulose was charged to a 1500 ml cylindrical reaction flask equipped with an overhead stirrer in the form of a double helix.
- the cellulose was suspended in 800 gram of 2-methyl-2-butanol and the reaction flask was closed.
- the suspension was kept at ambient temperature and deoxygenated with a bottom nitrogen purge while the stirrer rotated at 250 rpm.
- the bottom nitrogen purge was kept for 30 minutes. At this point the bottom nitrogen purge was changed to top nitrogen blanket and 69.1 gram of a 25% sodium hydroxide solution was added to the suspended cellulose fiber slurry.
- the cellulose slurry was continuously stirred and the temperature was gradually increased from ambient to 80°C over a period of 60 minutes.
- 69 g of glycidol (Aldrich) was added at a feed rate of 1 ml/minute to the stirred alkalized cellulose slurry.
- the temperature of the slurry was kept at 80°C and controlled by heating or cooling.
- the mixture was kept at temperature for another 20 minutes.
- 14 gram of a solution of sodium vinylsulfonate (Aldrich) was added to the warm (80°C) and stirred mixture at a feed rate of 1 ml/minute. After completed addition the mixture was stirred at 80°C for another 60 minutes.
- a product sample taken at this point was completely water-soluble.
- the slurried mixture of the alkalized cellulose ether was neutralized with acetic acid (approximately 29.5 g) against phenolphthalein (pink to clear).
- acetic acid approximately 29.5 g
- phenolphthalein pink to clear
- the crude 2,3-dihydroxypropyl-ethylsulfonated cellulose was isolated as a moist filter cake from the reaction slurry via filtration.
- the filter cake was dried in a tow step process. Most of the organic volatiles were removed in a once through air, drying oven at 60°C over a period of 60 minutes.
- the reaming water in the crude cellulose ether was evaporated at 0.01 mmHg and a temperature not exceeding 25°C over a period of 46 hours.
- the cellulose slurry was continuously stirred and the temperature was gradually increased from ambient to 80°C over a period of 60 minutes. 59 g of glycidol (Aldrich) was added at a feed rate of 1 ml/minute to the stirred alkalized cellulose slurry. After completed addition the mixture was stirred at 80°C for another 60 minutes. A product sample taken at this point was virtually free of suspended solids.
- the slurried mixture of the alkalized cellulose ether was neutralized with acetic acid (approximately 22.6 g) against phenolphthalein (pink to clear). The crude 2,3-dihydroxypropyl cellulose was isolated as a moist filter cake from the reaction slurry via filtration.
- the filter cake was dried in a tow step process. Most of the organic volatiles were removed in a once through air, drying oven at 60°C over a period of 60 minutes.
- the reaming water in the crude cellulose ether was evaporated at 0.01 mmHg and a temperature not exceeding 25°C over a period of 16 hours. 117.3 grams of a crude dry product were isolated containing 26% sodium acetate and 74% 2,3-dihydroxypropyl cellulose.
- a 2% solution of the crude, dry cellulose ether had a viscosity of 36 cps (30 rpm, 22°C, spindle LS62).
- AGU anhydrous glucose monomer unit of 2,3-dihydroxypropyl- ethylsulfonated cellulose
- the dihydroxypropyl cellulose ether has as DS (degree of substitution, number of dihydroxypropyl groups per monomeric glucose unit in the cellulose chain) in the range of 0.5 to 3.0.
- the preferred DS of the dihydroxypropyl cellulose ether is in the range of 1.5 to 2.5.
- the dihydroxypropyl cellulose ether can have in addition to the DS in the range of 1.5 to 2.5 a MS (multiple degree of substitution, average number of dihydroxypropyl groups per single hydroxide appendage on the monomeric glucose unit in the cellulose chain) of greater or equal to 1.
- the dihydroxypropyl cellulose ether has anionic substituents.
- the dihydroxypropyl cellulose ether has anionic substituents were the DS of the anionic component is greater then 0 and less then 0.5.
- the preferred anionic substituent on the dihydroxypropyl cellulose ether is a ethylsulfonate group.
- the dihydroxypropyl ethylsulfonated cellulose has been cross-linked under homogeneous or heterogeneous conditions.
- ethylsulfonated cellulose ether is of covalent nature.
- the cross-linking of the dihydroxypropyl ethylsulfonated cellulose ether had the effect of increasing its molecular weight and its solution viscosity.
- the dihydroxypropyl ethylsulfonated cellulose had before cross-linking a Brookfield viscosity in the range of 10 to 100 cps at 30 rpm, 20°C, and 2% actives content and after cross-linking a Brookfield viscosity in the range of 200 to 3000 cps at 30 rpm, 20°C, and 2%.
- the cross-linked dihydroxypropyl ethylsulfonated cellulose is capable of enhancing the flocculation of aluminum trihydrate solids from pregnant process liquors in the Bayer process.
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Biochemistry (AREA)
- Geology (AREA)
- Materials Engineering (AREA)
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- General Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Molecular Biology (AREA)
- Nutrition Science (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
Abstract
Description
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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AU2014242325A AU2014242325B2 (en) | 2013-03-13 | 2014-02-10 | Cross-linked ethylsulfonated dihydroxypropyl cellulose |
CA2904522A CA2904522C (en) | 2013-03-13 | 2014-02-10 | Cross-linked ethylsulfonated dihydroxypropyl cellulose |
CN201480013653.1A CN105073642B (en) | 2013-03-13 | 2014-02-10 | The ethyl sulfonation dihydroxypropyl cellulose of crosslinking |
BR112015022243-9A BR112015022243B1 (en) | 2013-03-13 | 2014-02-10 | METHOD TO PRODUCE ALUMINA USING A BAYER PROCESS |
JP2016500226A JP2016517385A (en) | 2013-03-13 | 2014-02-10 | Cross-linked ethyl sulfonated dihydroxypropyl cellulose |
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US13/798,761 | 2013-03-13 | ||
US13/798,761 US9102995B2 (en) | 2010-08-09 | 2013-03-13 | Cross-linked ethylsulfonated dihydroxypropyl cellulose |
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PCT/US2014/015538 WO2014158381A1 (en) | 2013-03-13 | 2014-02-10 | Cross-linked ethylsulfonated dihydroxypropyl cellulose |
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CN (1) | CN105073642B (en) |
AU (1) | AU2014242325B2 (en) |
BR (1) | BR112015022243B1 (en) |
CA (1) | CA2904522C (en) |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2018148308A1 (en) * | 2017-02-07 | 2018-08-16 | Kemira Oyj | Selective polysaccharide flocculants for bauxite ore beneficiation |
US10427950B2 (en) | 2015-12-04 | 2019-10-01 | Ecolab Usa Inc. | Recovery of mining processing product using boronic acid-containing polymers |
US20220396639A1 (en) * | 2021-06-15 | 2022-12-15 | Hyundai Motor Company | Method for preparing nanocellulose using nonionic surfactants |
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CN106279453B (en) * | 2015-05-28 | 2019-12-10 | 易媛 | Cross-linked high molecular compound, preparation method thereof, hydrogel, water-based fracturing fluid and application |
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2014
- 2014-02-10 JP JP2016500226A patent/JP2016517385A/en active Pending
- 2014-02-10 WO PCT/US2014/015538 patent/WO2014158381A1/en active Application Filing
- 2014-02-10 AU AU2014242325A patent/AU2014242325B2/en active Active
- 2014-02-10 CN CN201480013653.1A patent/CN105073642B/en active Active
- 2014-02-10 BR BR112015022243-9A patent/BR112015022243B1/en active IP Right Grant
- 2014-02-10 CA CA2904522A patent/CA2904522C/en active Active
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Also Published As
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BR112015022243A2 (en) | 2017-07-18 |
CA2904522C (en) | 2020-06-30 |
AU2014242325A1 (en) | 2015-11-05 |
AU2014242325B2 (en) | 2016-12-15 |
JP2016517385A (en) | 2016-06-16 |
BR112015022243B1 (en) | 2022-02-15 |
CN105073642A (en) | 2015-11-18 |
CN105073642B (en) | 2017-06-20 |
CA2904522A1 (en) | 2014-10-02 |
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