WO2020118371A1 - Résine pour le dessalement et processus de régénération - Google Patents

Résine pour le dessalement et processus de régénération Download PDF

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Publication number
WO2020118371A1
WO2020118371A1 PCT/AU2019/051367 AU2019051367W WO2020118371A1 WO 2020118371 A1 WO2020118371 A1 WO 2020118371A1 AU 2019051367 W AU2019051367 W AU 2019051367W WO 2020118371 A1 WO2020118371 A1 WO 2020118371A1
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WO
WIPO (PCT)
Prior art keywords
resin
ion exchange
polymer
exchange resin
regeneration
Prior art date
Application number
PCT/AU2019/051367
Other languages
English (en)
Inventor
Richard Mark Pashley
Mojtaba Taseidifar
Tanita Gettongsong
Original Assignee
Newsouth Innovations Pty Limited
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 claimed from AU2018904715A external-priority patent/AU2018904715A0/en
Application filed by Newsouth Innovations Pty Limited filed Critical Newsouth Innovations Pty Limited
Priority to US17/312,221 priority Critical patent/US20220025091A1/en
Priority to AU2019399663A priority patent/AU2019399663A1/en
Publication of WO2020118371A1 publication Critical patent/WO2020118371A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J49/00—Regeneration or reactivation of ion-exchangers; Apparatus therefor
    • B01J49/50—Regeneration or reactivation of ion-exchangers; Apparatus therefor characterised by the regeneration reagents
    • B01J49/53—Regeneration or reactivation of ion-exchangers; Apparatus therefor characterised by the regeneration reagents for cationic exchangers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J43/00—Amphoteric ion-exchange, i.e. using ion-exchangers having cationic and anionic groups; Use of material as amphoteric ion-exchangers; Treatment of material for improving their amphoteric ion-exchange properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J49/00—Regeneration or reactivation of ion-exchangers; Apparatus therefor
    • B01J49/50—Regeneration or reactivation of ion-exchangers; Apparatus therefor characterised by the regeneration reagents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J49/00—Regeneration or reactivation of ion-exchangers; Apparatus therefor
    • B01J49/50—Regeneration or reactivation of ion-exchangers; Apparatus therefor characterised by the regeneration reagents
    • B01J49/57—Regeneration or reactivation of ion-exchangers; Apparatus therefor characterised by the regeneration reagents for anionic exchangers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
    • C08F220/585—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/06—Amines
    • C08G12/08—Amines aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/40—Chemically modified polycondensates

Definitions

  • This disclosure relates, in general, to a resin for providing improved desalination efficiency and to a process of regeneration of the resin.
  • anion exchange and cation exchange resin beads are mixed together to produce a combined ion exchange effect. Because the anion exchange resin beads and cation exchange resin beads are regenerated separately via acid and base washing, the mixed beads must be able to be separated. The densities of the beads are commonly different, to facilitate simple separation of the resin beads.
  • Ion exchange (I EX) resins have been used for many years in various water treatment related practices. For example, mixed-bed ion exchange resins have been used to remove scale forming ions, such as Ca2+ and Mg2+, from feedwater and to produce high quality water (i.e. comparable to distilled water) from tap water. Such resins could also be used, potentially, for the desalination of fairly concentrated brackish water and even seawater, without the need for high pumping pressures, extensive pre-treatment or high thermal energy input.
  • scale ions such as Ca2+ and Mg2+
  • An ion-exchange resin may be referred to as“spent” when the majority of the mobile counter-ions associated with the charged functional groups in the resin have been replaced with the other ions of similar charge.
  • a desalination process to remove NaCI from water the water passes through (i.e. elutes through) both a cation-exchange resin, in which the mobile counter-ion is exchanged with the cation (e.g. Na+) in the water, and an anion-exchange resin, in which the mobile counter-ion is exchanged with the anion (e.g. CI-) in the water.
  • the mobile counter-ion of the cation-exchange resin is typically H+ and the mobile counter-ion of the anion-exchange resin is typically OH-.
  • the cation-exchange resin and the anion-exchange resin are in the form of beads housed in an ion-exchange column.
  • the resin beads are firstly separated into the beads of the cation-exchange resin and the beads of the anion-exchange resin, and each component is then washed separately with a regenerating solution.
  • a regenerating acid solution is used to wash and thereby remove the exchanged cation on the cation-exchange resin.
  • regenerating basic solution is used to wash and thereby remove the exchanged anion on the anion-exchange resin. Further washing steps (usually using the product water) are then subsequently used to rinse the regenerating solution away from the resin.
  • an ion exchange resin comprising a polymer having strong acid and strong base groups on the same polymer.
  • the resin comprises a high density of polymers having strong acid and strong base groups on the same polymer.
  • the strong acid and strong base groups are in close proximity to one another on the polymer.
  • the disclosure further relates to a mixed bead resin for high salt level desalination.
  • the disclosed ion exchange resin may have the benefit of providing for efficient ion exchange or desalination and may also have the benefit of efficient regeneration.
  • the broad concept of a resin comprising strong acid and strong base groups on a single polymer within the resin creates this efficiency of ion exchange due to the closeness of the groups (within nanometres rather than millimetres of one another).
  • the efficiency of ion exchange or desalination may be improved because the location of the exchanging ions is relatively close.
  • the regeneration of this resin requires a new method which is also disclosed herein.
  • the resin material may allow for the simultaneous exchange of anions and cations, within the same molecular group, which may improve the efficiency of desalination, especially at the higher concentrations approaching seawater levels.
  • Sustainable and low energy desalination for brackish water offers a viable alternative to reverse osmosis in many areas which can be used in combination with a novel membrane process for the closed-cycle regeneration of the resin.
  • an ion exchange resin comprising strong acid and strong base groups on the same polymer chain.
  • a chemically cross-linked ampholytic polymer resin or a cross-linked zwitterionic polymer resin are located on the same polymer chain, wherein the ampholytic polymer resin and the zwitterionic polymer resin each contain strong acid and base groups on the same polymer chain.
  • the ion exchange resin is provided for high salt level water desalination.
  • Also disclosed is a process of regeneration of an ion-exchange resin the process comprising washing the resin with concentrated ammonium bicarbonate solution.
  • recovery is performed with hollow fibre membranes and used in closed cycle resin regeneration.
  • This method of regeneration could also be applied to spent inorganic ion exchange materials, such as zeolites.
  • Fig. 1 shows a schematic diagram of the difference between separate bead ion exchange and ion exchange on the same polymer.
  • Fig. 2 shows a schematic diagram of ion exchange regeneration using ammonium bicarbonate solutions.
  • Fig. 3 shows swelling of a gel resin of one embodiment of the disclosure in salt solutions having a range of concentrations.
  • Fig. 4 shows a schematic diagram of the membrane process used for the thermal decomposition of ammonium bicarbonate solutions.
  • Fig. 5 shows a graphical representation of the typical adsorption results for crosslink hydrogel for MgSCU and NaCI at different concentrations.
  • Fig.6 shows typical adsorption equilibria for hydrogel and zwitterionic gels in a series of NaCI solutions.
  • Fig. 7 shows the product of the polyampholytic resin synthesis.
  • Fig. 8 shows the product of powdered zwitterionic ion exchange resin.
  • an ion exchange resin for high salt level water desalination comprising strong acid and strong base groups on the same polymer chain.
  • the resin has a high concentration of strong acid and strong base groups on single polymer chains within the resin.
  • the resin comprises either a chemically cross-linked ampholytic polymer resin or a cross-linked zwitterionic polymer resin on the same polymer chain, wherein the ampholytic polymer resin and the zwitterionic polymer resin each contain strong acid and base groups on the same polymer chain.
  • ampholytic polymer resin was prepared by one-step co-polymerisation of an anionic monomer, a cationic monomer and a cross-linking agent using an initiator.
  • the anionic monomer comprises 2-acrylamido-2-methylpropanesulphonic acid sodium salt solution.
  • the cationic monomer comprises 3-(methacryloylamino) propyl- trimethylammonium chloride solution.
  • the crosslinking agent comprises ethylene glycol di methacrylate.
  • crosslinking agent and initiator comprises glutaraldehyde and alpha- ketoglutaric acid.
  • the ratio of anionic monomercationic monomer: cross linking agent is 1 :1 :2; with a lower level of a suitable radical initiator.
  • the strong acid and strong base groups are less than 10000 nm apart. In some forms the distance between the strong acid and base group is less than 20000 nm. In some forms the distance between the strong acid and base group on a single polymer is less than 5000 nm. In some forms the distance between the strong acid and the strong base group on a single polymer is in the nm range rather than the mm range.
  • the process is performed in situ.
  • the resin is synthesised by synthesis of two different strong acid/strong base resins.
  • the resins comprise a chemical cross-linked polyampholytic resin and a crosslinked zwitterionic polymer, both resins containing strong acid and base groups on the same polymer. These resins are provided in a mixed bead resin for desalination of water.
  • zwitterionic polymer are used independently.
  • the resin could be replaced by an inorganic ion exchange material, such as a suitable ion absorbing, powdered zeolite.
  • Disclosed also is a method of treating water using a resin having a high density of strong acid and strong base groups located on single polymers within the resin. Further disclosed is a method of regenerating the resin by washing in ammonium bicarbonate solution.
  • the common ion exchange process using mixtures of anion exchanging or cation exchanging beads, may behave very differently to ion exchange of both anions and cations on the same polymer.
  • the exchanging groups may be only nms apart. This may allow for simultaneous or otherwise more efficient ion exchange. This is distinct from ion exchange where the exchanging groups are on separate polymers and may be mms apart.
  • a method of regeneration which may be achieved in situ without separation of the mixed resin beads.
  • the method comprises using concentrated ammonium bicarbonate solutions to displace the resin adsorbed Na + and Cl ions with NH4 + and HCO 3 ions.
  • ammonium bicarbonate offers an alternative method because it is a thermolytic salt, which is capable of decomposing in aqueous solution at low temperatures. The complete decomposition of AB into its individual constituents may be observed above 60 °C, which is described by the reaction:
  • a bubble column evaporator (BCE) process could facilitate the thermal decomposition of AB solutions (both dilute and concentrated) at lower solution temperatures (of around 45°C) and at a faster rate.
  • AB solutions have a wide variety of industrial applications. For instance, AB solution is used as a draw solution in desalination. Therefore, simultaneous separation of NH 3 and CO 2 gases from an aqueous NH 4 HCO 3 solution with low energy consumption is a key issue for the commercialisation of FO desalination. Also, it has been recently demonstrated that AB solutions can be used in the regeneration step for ion exchange resins and this step is one of the biggest drawbacks with the use of ion exchange resins because it requires a large volume of acid and base. Hence, using an AB solution as regenerant can resolve this issue and finally, the decomposition of AB solution can provide drinking water for human consumption.
  • Recycling of the AB solutions may in some forms also be effectively carried out using membrane transport systems with hollow fibre membranes which may be used as an alternative for solution separation because it has many potential advantages, such as low operating pressure, temperature, ease of process scale-up, fast mass-transfer and durability of the membrane, over traditional evaporation or RO technology.
  • Hollow fiber membranes also targeted for industrial applications (as opposed to medical ones, e.g., blood
  • membrane distillation may be performed using commercial microporous hydrophobic hollow fibre polypropylene (PP) membranes to study the effects of various operating conditions including feed solution temperature, mass flow rate and concentration on gas removal and water recovery efficiencies
  • PP hollow fibre polypropylene
  • membrane transport was used via a silicone based hollow fibre diffusion membrane and a PTFE hydrophobic pore membrane, for the controlled thermal
  • Example 1 Chemically x-linked hydrogel: 2-acrylamido-2-methylpropanesulphonic acid sodium salt solution (AMPS) (anionic monomer), 3-(methacryloylamino) propyl- trimethylammonium chloride solution (MPTC) (cationic monomer), ethylene glycol di methacrylate (EGDMA) (crosslinking agent), 25 % Glutaraldehyde (GA) and alpha- ketoglutaric acid (initiator) were used for synthesis.
  • AMPS 2-acrylamido-2-methylpropanesulphonic acid sodium salt solution
  • MPTC 3-(methacryloylamino) propyl- trimethylammonium chloride solution
  • EGDMA ethylene glycol di methacrylate
  • GGDMA crosslinking agent
  • GGDMA Glutaraldehyde
  • G alpha- ketoglutaric acid
  • glutaraldehyde and dimethyl formamide (DMF) and 1 ,3-propane sultone were used as reactants for synthesis of the zwitterionic compounds.
  • Several salts 98 % sodium chloride, 99 % sodium sulphate, magnesium chloride (AR grade) and magnesium sulphate (AR grade); were used to study swelling and electrical conductivity properties. All chemicals were purchased from Sigma-Aldrich, Australia as a reagent grade. 365 nm, 230 Volts, 8 Watts UV-lamp and 365 nm Ultraviolet Crosslinker replacement tubes were purchased from John Morris Scientific Pty Ltd.
  • Example 2 zwitterionic polymer resin: 1 ,3- propane sultone, p-phenylene diamine, glutaraldehyde and dimethyl formamide were purchased from Sigma-Aldrich, Australia, each as reagent grade.
  • An alternative possible resin was selected from a range of zwitterionic polymers. The one selected is shown below.
  • This resin was prepared using 5 mmol of p-phenylene diamine in 20 ml_ of DMF and 5 mmol of glutaraldehyde in 20 ml_ of DMF were prepared separately in a different beaker. The solution was mixed and refluxed at 80°C for 1 hr. Then, 15 mmol of 1 ,3-propane sultone in 10 ml_ of DMF was added in the reaction and refluxed at 70°C for 3 hr. The final product was washed several times with hot water to remove residual unreacted chemicals.
  • the structure of the resin is given below:
  • UV polymerisation method for production of the crosslinked ampholytic gel.
  • the UV reactions used 8 Watts at 250 volts, with a 365 nm ultraviolet lamp, for 15 hours. After reaction, the product was immersed in water for 1 week to allow the product to equilibrate and to wash out the residue unreacted chemicals.
  • the polymeric products showed a large absorption of water (i.e. swelling).
  • swelling in water and a range of 0.2M salts over several days is shown in Figure 3 for the 1 : 1 : 1 :2 resin sample.
  • the equilibrium swelling in salts corresponded to about 90% water in the clear gel.
  • Table 1 Shows the ratio of monomers, initiator and crosslink agent used in various synthesis reactions. In this table the initiator concentrations 1- 4 refer to the ratio of monomers and 0.25% mole of initiator (i.e. for , with‘4’ corresponding to 1%).
  • Ammonium bicarbonate solutions were prepared at a concentration of 0.03 M. Electrical conductivity values of all the solutions were measured using a EUTECH CON 700
  • NH4HCO3 solutions were heated up to 80°C to decompose the solution to ammonium (NH3) and carbon dioxide gases (CO2) just prior to entry into a membrane separator unit using an electrical gas heater (stainless steel tube wrapped with an electrical tape, Duo- Tape Cat. No. is AWH-051-020, HTS/Amptek Company, Stafford, Texas, USA).
  • the temperature of the inlet solution was continuously controlled and monitored using an AC Variac electrical supply and thermocouple.
  • the room temperature air intake flowrate was fixed at 25 l.min-1.
  • the gas phase counter-flow collected ammonia (NH3) and carbon dioxide gases (CO2), which were continuously separated through the membrane contactors by a diffusion process.
  • the final solution was collected and cooled down to room temperature before measuring electrical conductivities using a EUTECH CON 700 Conductivity Bench.
  • the recovery system is shown schematically in Figure 4.
  • NH 4 HCO 3 solution 60 is delivered to a heater column 61 which is measured by a
  • thermometer 62 and controlled by a Variac AC 64.
  • the solution is heated to 80 °C and delivered to membrane contactors 65 to separate it into ammonia and carbon dioxide 66 and residual water 67.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Water Treatment By Electricity Or Magnetism (AREA)

Abstract

L'invention concerne une résine échangeuse d'ions comprenant un polymère ayant un acide fort et des groupes de bases forts sur le même polymère. Dans certains modes de réalisation, la résine comprend une haute densité de polymères ayant un acide fort et des groupes de bases forts sur le même polymère. Dans certains modes de réalisation, l'acide fort et les groupes de bases forts sont proches l'un de l'autre sur le polymère. L'invention concerne en outre une résine à billes mélangées pour le dessalement à haut niveau de sel.
PCT/AU2019/051367 2018-12-12 2019-12-12 Résine pour le dessalement et processus de régénération WO2020118371A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US17/312,221 US20220025091A1 (en) 2018-12-12 2019-12-12 Resin for desalination and process of regeneration
AU2019399663A AU2019399663A1 (en) 2018-12-12 2019-12-12 Resin for desalination and process of regeneration

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2018904715 2018-12-12
AU2018904715A AU2018904715A0 (en) 2018-12-12 Resin material and regeneration method for desalination

Publications (1)

Publication Number Publication Date
WO2020118371A1 true WO2020118371A1 (fr) 2020-06-18

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011127364A2 (fr) * 2010-04-09 2011-10-13 Lubrizol Advanced Materials, Inc. Combinaison de polymères cationiques et ampholytiques réticulés pour des applications aux soins personnels et de ménage
US20130233093A1 (en) * 2012-03-08 2013-09-12 Christopher A. Pohl Sorption of water from a sample using a polymeric drying agent
WO2014067605A1 (fr) * 2012-11-01 2014-05-08 Merck Patent Gmbh Modification superficielle de supports de base poreux
WO2018035573A1 (fr) * 2016-08-26 2018-03-01 Newsouth Innovations Pty Limited Procédé de dessalement

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011127364A2 (fr) * 2010-04-09 2011-10-13 Lubrizol Advanced Materials, Inc. Combinaison de polymères cationiques et ampholytiques réticulés pour des applications aux soins personnels et de ménage
US20130233093A1 (en) * 2012-03-08 2013-09-12 Christopher A. Pohl Sorption of water from a sample using a polymeric drying agent
WO2014067605A1 (fr) * 2012-11-01 2014-05-08 Merck Patent Gmbh Modification superficielle de supports de base poreux
WO2018035573A1 (fr) * 2016-08-26 2018-03-01 Newsouth Innovations Pty Limited Procédé de dessalement

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHANDRASEKARA, N.P. ET AL.: "Study of a New Process for the Efficient Regeneration of Ion-Exchange Resins", DOCTORAL THESIS, August 2016 (2016-08-01), XP055719075 *
TARANNUM, NAZIA ET AL.: "Synthesis and Characterization of Zwitterionic Organogels Based on Schiff Base Chemistry", JOURNAL OF APPLIED POLYMER SCIENCE, vol. 118, no. 5, 30 June 2010 (2010-06-30), pages 2821 - 2832, XP055719074 *

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