EP2928604A1 - Ionenaustauschharz mit chelatbildenden eigenschaften, verfahren zur herstellung davon und verwendungen davon - Google Patents

Ionenaustauschharz mit chelatbildenden eigenschaften, verfahren zur herstellung davon und verwendungen davon

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Publication number
EP2928604A1
EP2928604A1 EP13801541.7A EP13801541A EP2928604A1 EP 2928604 A1 EP2928604 A1 EP 2928604A1 EP 13801541 A EP13801541 A EP 13801541A EP 2928604 A1 EP2928604 A1 EP 2928604A1
Authority
EP
European Patent Office
Prior art keywords
resin
phenolic
group
formaldehyde
hydrogen atom
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Withdrawn
Application number
EP13801541.7A
Other languages
English (en)
French (fr)
Inventor
Stéphane PELLET-ROSTAING
Guilhem ARRACHART
Ahmad KENAAN
Stéphanie GRACIA
Raphaël TURGIS
Véronique Dubois
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.)
Centre National de la Recherche Scientifique CNRS
Universite Montpellier 2 Sciences et Techniques
Commissariat a lEnergie Atomique et aux Energies Alternatives CEA
Original Assignee
Centre National de la Recherche Scientifique CNRS
Universite Montpellier 2 Sciences et Techniques
Commissariat a lEnergie Atomique et aux Energies Alternatives CEA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Centre National de la Recherche Scientifique CNRS, Universite Montpellier 2 Sciences et Techniques, Commissariat a lEnergie Atomique et aux Energies Alternatives CEA filed Critical Centre National de la Recherche Scientifique CNRS
Publication of EP2928604A1 publication Critical patent/EP2928604A1/de
Withdrawn legal-status Critical Current

Links

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
    • B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming 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
    • B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/16—Organic material
    • B01J39/18—Macromolecular compounds
    • B01J39/19—Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/68—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water
    • C02F1/683—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water by addition of complex-forming compounds
    • 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
    • C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
    • C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
    • C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
    • C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
    • G—PHYSICS
    • G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
    • G21F—PROTECTION AGAINST X-RADIATION, GAMMA RADIATION, CORPUSCULAR RADIATION OR PARTICLE BOMBARDMENT; TREATING RADIOACTIVELY CONTAMINATED MATERIAL; DECONTAMINATION ARRANGEMENTS THEREFOR
    • G21F9/00—Treating radioactively contaminated material; Decontamination arrangements therefor
    • G21F9/04—Treating liquids
    • G21F9/06—Processing
    • G21F9/12—Processing by absorption; by adsorption; by ion-exchange
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
    • C02F2001/425—Treatment of water, waste water, or sewage by ion-exchange using cation exchangers
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/006—Radioactive compounds

Definitions

  • the invention relates to the field of radionuclide decontamination of aqueous media in which these radionuclides are present in small amounts.
  • the invention relates to an ion exchange resin, of the formo-phenolic type, which has chelating properties, which has a selectivity to both cesium and strontium and which is therefore as such, particularly adapted to coextract (that is to say, extract in a grouped manner) these two elements of an aqueous medium in which they are located, this aqueous medium can be a freshwater medium or a seawater environment.
  • the invention also relates to a process for preparing this resin as well as to uses of said resin.
  • the invention is likely to find applications in all situations where it may be desirable to decontaminate an aqueous medium of cesium and / or strontium and, in particular, in the nuclear industry to treat aqueous liquid effluents which affect the environment.
  • one and / or the other of these two elements which are likely to be produced by nuclear facilities, either as part of their normal operation (for example, in the context of an activity of reprocessing spent nuclear fuel) either accidentally.
  • Irradiated nuclear fuel reprocessing plants produce so-called low and intermediate-level aqueous liquid effluents (FA-MA), which contain a number of radionuclides resulting from nuclear fission and corrosion of fuel cladding. , and therefore need to be treated for extract these radionuclides.
  • FA-MA low and intermediate-level aqueous liquid effluents
  • To the effluents resulting from the reprocessing of the irradiated nuclear fuels are added the effluents of washing of the contaminated equipment as well as the effluents related to possible nuclear incidents.
  • Cesium 137 and strontium 90 are among the radionuclides whose extraction is more specifically targeted because they are abundant in irradiated nuclear fuels (and of which in the aqueous liquid effluents resulting from the reprocessing of these fuels) and their period of approximately 30 years makes them particularly radiotoxic. Moreover, this period is too long for the decay to take place within a reasonable time interval.
  • the decontamination of aqueous effluents FA-MA is generally carried out by means of purification systems based on the use of ion exchange resins (sulfonic, carboxylic, formo-phenolic, ...) or by processes of coprecipitation.
  • ion exchange resins sulfonic, carboxylic, formo-phenolic, ...)
  • processes of coprecipitation have limitations, namely that co-precipitation generates large volumes of waste in the form of sludge and thus leads to large volumes of storage, while the ion exchange resins currently used have a low ability to extract metal ions in a grouped manner.
  • the possibility of extracting radionuclides in a grouped manner from aqueous liquid effluents is a key point for treating these effluents while producing a minimum of waste.
  • formo-phenolic polymer resins which are also known as phenol-formaldehyde resins and which are obtained by the polycondensation of phenolic compounds and formaldehyde, typically in a basic medium, can be used to extract cesium and strontium from an aqueous saline medium.
  • K.A. K. Ebraheem et al. (Sep. Sci.Technol., 35 (13), 2115-2125 (2000), reference [4]) incorporated 8-hydroxyquinoline in bisphenol A and formaldehyde resins, and studied the behavior of resins thus obtained with respect to lanthanum, cerium, neodymium, samarium and gadolinium;
  • the DTPA is present in the polymer matrix forming the resin without being immobilized on this matrix, which, taking into account the solubility of this compound in the aqueous phase, may lead to its release by the resin during the use of the latter in an aqueous medium and, therefore, to an alteration, even a loss, of its chelating properties.
  • the purpose of the inventors is to provide new ion exchange resins with chelating properties that are selective both for cesium and strontium and In this way, these two elements of an aqueous medium can be grouped together and their chelating properties are not likely to be altered during use.
  • the goal of the inventors is also that the synthesis of these resins is simple to implement and can be achieved at costs compatible with their use on an industrial scale.
  • At least one first phenolic monomer, chelating which corresponds to the following general formula (I):
  • n 0, 1 or 2
  • R2, R3, R 4, R 5 represent independently each other a hydrogen atom, -OH, an alkyl group in Ci to Ci 0, alkoxy, Ci to Ci 0 aryl, an aryloxy group, a -SO 3 H group, a -COOR group in which R represents a hydrogen atom or a C 1 -C 10 alkyl group, a -P (O) (OR) (OR ') group or a -C (O) NRR 'group in which R and R' are, independently of each other, a hydrogen atom or a C 1 -C 10 alkyl group; with the proviso that at least one of R 1 to R 5 is -OH and at least two of R 1 to R 5 are hydrogen;
  • the resin according to the invention is a formophenolic type resin which is functionalized with chelating groups derived from ethylene diamine tetraacetic acid (EDTA), diethylene triamine pentaacetic acid (DTPA) or acid. triethylene tetramine hexaacetic acid (HTTA) but in which the chelating groups are an integral part of the polymer matrix of the resin since the latter is obtained by condensation of a first phenolic monomer carrying these chelating groups, a second phenolic monomer and formaldehyde .
  • EDTA ethylene diamine tetraacetic acid
  • DTPA diethylene triamine pentaacetic acid
  • HTTA triethylene tetramine hexaacetic acid
  • this resin has been shown to have a selectivity, not only towards cesium but also towards strontium, as will be demonstrated in Example 3 below.
  • C 1 -C 10 alkyl group means any alkyl group, linear or branched, which is formed by at least one carbon atom and at most ten carbon atoms such as a methyl, ethyl or propyl group such as ⁇ -propyl or isopropyl, butyl such as ⁇ -butyl, sec-butyl, isobutyl or ieri-butyl, pentyl as ⁇ -pentyl, sec-pentyl or isopentyl, hexyl as ⁇ -hexyl or isohexyl, heptyl as ⁇ -heptyl or isoheptyl, octyl as ⁇ -octyl or isooctyl, nonyl as n-nonyl or isononyl, decyl as ⁇ -decyl or isodecyl, etc. ;
  • C 1 -C 10 alkoxy group means any linear or branched O-alkyl group which is formed by at least one carbon atom and at most ten carbon atoms such as a methoxy, ethoxy or propoxy group; , isopropoxy, butoxy such as ⁇ -butoxy, sec-butoxy or isobutoxy, pentoxy as ⁇ -pentoxy, sec-pentoxy or iso-pentoxy, hexoxy as ⁇ -hexoxy or isohexoxy, heptoxy as ⁇ -heptoxy or isoheptoxy, octoxy as ⁇ -octoxy or isooctoxy, nonoxy such as ⁇ -nonoxy or isononoxy, decoxy as ⁇ -decoxy or isodecoxy, etc .;
  • Aryl group means any group derived from an arene, that is to say from a hydrocarbon whose formula is derived from benzene, such as a phenyl, benzyl, naphthyl, o-tolyl or m-tolyl group; p-tolyl, o-xylyl, m-xylyl, p-xylyl, phenethyl, etc .; and by
  • Aryloxy group means any O-aryl group in which the aryl group is as defined above such as, for example, phenoxy, benzyloxy, naphthyloxy, o-tolyloxy, m-tolyloxy, p-tolyloxy, o- xylyloxy, m-xylyloxy, p-xylyloxy, phenethyloxy, etc.
  • alkyl and alkoxy groups which comprise from 1 to 6 carbon atoms, aryl groups which are chosen from phenyl, benzyl and phenethyl groups, the phenyl group being especially preferred - and aryloxy groups which are selected from phenoxy, benzyloxy and phenethyloxy, phenyloxy being most preferred.
  • the first phenolic monomer preferably corresponds to the general formula (I) above in which R 3 represents a -OH group, Ri and R 5 both represent a hydrogen atom, while m, n, R 2 and R 4 have the same meaning as above.
  • the first phenolic monomer corresponds to the general formula (I) above wherein m is 2, R 3 is -OH, R 1, R 2 and R 5 all represent a hydrogen atom, R 4 represents a hydrogen atom or a -OH group, while n has the same meaning as above.
  • Phenolic monomers which correspond to the above general formula (I) in which m is 2, R 3 represents a group -OH, R 1, R 2 , R 4 and R 5 all represent a hydrogen atom, while n is 0 or 1, are most preferred.
  • the second phenolic monomer can be any phenolic compound which is capable of conducting, by condensation with formaldehyde, a formophenolic resin provided that this compound does not meet the general formula (I) below. before.
  • it can be any compound which comprises at least one benzene ring at least one carbon atom of which bears an -OH group and at least two carbon atoms of which carry a hydrogen atom but which do not meets the general formula (I) above.
  • the second phenolic monomer preferably comprises 1 to 4 benzene rings, which can either be connected two by two through a vertex or via an atom, for example oxygen, or a group, by -CH 2 - or -C (CH 3 ) 2 -, forming a bridge, or be contiguous to each other, each of these benzene rings having at least one carbon atom carrying a -OH group and at least two carbon atoms carrying a hydrogen atom.
  • the second phenolic monomer can be chosen from phenol, catechol (or 1,2-dihydroxybenzene), resorcinol (or 1,3-dihydroxybenzene), hydroquinone (or 1,4-dihydroxybenzene), hydroxyquinol (or 1,2,4-trihydroxybenzene), phloroglucinol (or 1,3,5-trihydroxybenzene), pyrogallol (or 1,2,3-trihydroxybenzene), benzenetetrol (or 1,2,3,5-tetrahydroxybenzene), cresols (m-, o- and p-cresol), xylenols (2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2 , 6-xylenol, 3,4-xylenol and 3,5-xylenol), hydroxybenzoic acids (2-hydroxybenzoic acid, 3-hydroxybenzoic acid and 4-hydroxy
  • the second phenolic monomer is preferably chosen from dihydroxybenzenes (cathecol, resorcinol and hydroquinone) and calix [4] resorcinarene, resorcinol being very particularly preferred.
  • the resin according to the invention may in particular be obtained by a process which comprises:
  • reaction medium comprising the first and second phenolic monomers, formaldehyde and a strong base
  • step a) the application of a heat treatment to the reaction medium thus prepared to obtain the formation of the resin by polycondensation of the first and second phenol monomers and formaldehyde.
  • step a) may in particular be carried out by:
  • step a) use is preferably made of:
  • a molar ratio between the first phenolic monomer and the second phenolic monomer which is between 0.1 and 5 and, more preferably, between 0.5 and 2;
  • a molar ratio between formaldehyde and the first and second phenolic monomers which is between 2 and 10 and, more preferably, between 2 and 4;
  • a molar ratio between the strong base and the first and second phenolic monomers which is between 0.5 and 2.5 and more preferably between 1 and 2;
  • a molar ratio between the water (which is present in the aqueous solution of strong base) and the first and second phenolic monomers which is between 25 and 500 and, more preferably, between 50 and 150.
  • the strong base is preferably a metal hydroxide such as an alkali metal hydroxide of the lithium hydroxide type, sodium hydroxide, potassium hydroxide or cesium hydroxide, or an alkaline earth metal hydroxide of calcium hydroxide type, strontium hydroxide or barium hydroxide.
  • a metal hydroxide such as an alkali metal hydroxide of the lithium hydroxide type, sodium hydroxide, potassium hydroxide or cesium hydroxide, or an alkaline earth metal hydroxide of calcium hydroxide type, strontium hydroxide or barium hydroxide.
  • Sodium hydroxide is most preferred.
  • the heat treatment preferably consists in heating the reaction medium to a temperature of between 95 ° C. and 130 ° C. and, more preferably, between 95 ° C. and 110 ° C., for 16 hours at 96 hours and, better still, 48 to 96 hours.
  • the process may advantageously furthermore comprise the reduction of the resin obtained in stage b) in the form of particles, for example by grinding, these particles preferably measuring from 0.05 to 1 mm, the washing the particles thus obtained with aqueous solutions, for example alternately acidic and basic, and drying the particles thus washed, for example in an oven.
  • aqueous solutions for example alternately acidic and basic
  • An ion exchange resin is thus obtained, which has chelating properties and is ready to be used for extracting cesium or strontium from an aqueous medium containing one of these elements, or even more to extract these two elements grouped together if they are both present in the same aqueous medium.
  • the subject of the invention is also the use of an ion exchange resin with chelating properties, as defined above, for extracting cesium and / or strontium from an aqueous medium in which one and / or the other of these elements are present.
  • the resin is used to co-extract cesium and strontium from an aqueous medium in which these two elements are present.
  • the aqueous medium is preferably an industrial aqueous liquid effluent and, in particular, an aqueous liquid effluent from the nuclear industry such as, for example, a low and medium activity effluent resulting from the reprocessing of irradiated nuclear fuel, or any other aqueous liquid effluent containing radio-contaminants.
  • the extraction of cesium and / or strontium from an aqueous medium, whether it be a freshwater or seawater medium, using a resin according to the invention is extremely simple to implement since it is sufficient to put this resin in contact with the aqueous medium, for example in a stirred reactor or in a column, for a time sufficient to allow cesium and / or strontium to be complexed by the resin, and then separate the resin from the aqueous medium.
  • the first phenolic monomer of general formula (I) can be obtained by reaction of a compound of general formula (II) below: in which n is 0, 1 or 2, with a compound of general formula (III) below:
  • R lr R 2, R 3, R 4, R 5 represent independently each other a hydrogen atom, -OH, an alkyl group in Ci to Ci 0, a alkoxy Ci-Ci 0, an aryl group, an aryloxy group, an -S0 3 H group, a -COOR group wherein R represents a hydrogen atom or an alkyl group C1 to 0, a group -P (O) (OR) (OR ') or a group -C (O) NRR' in which R and R 'independently of one another represent a hydrogen atom or a C 1 -C 10 alkyl group ; with the proviso that at least one of R 1 to R 5 is -OH and at least two of R 1 to R 5 are hydrogen; using procedures adapted from those described in the literature (Lauren et al., Eur J.
  • FIG. 1 represents, in graphic form, the values of the distribution coefficient (K D in ml / g) and of the extraction percentage (E) obtained for strontium during tests consisting in extracting cesium and strontium from a aqueous solution simulating a seawater diluted to 200 ppm sodium and doped with cesium and strontium, at a concentration of 10 -4 M, with two resins according to the invention (ETRF-Na and DTRF-Na) and by varying the amount of resin used from 0.5 g to 25 g / l of aqueous solution.
  • K D in ml / g the distribution coefficient
  • E extraction percentage
  • FIG. 2 represents, in graphical form, the values of the distribution coefficient (K D in ml / g) and of the extraction percentage (E) obtained for cesium in tests consisting in extracting cesium and strontium from a aqueous solution simulating a seawater diluted to 200 ppm sodium and doped with cesium and strontium, at a concentration of 10 -4 M, with two resins according to the invention (ETRF-Na and DTRF-Na) and by varying the quantity of resin used from 0.5 g to 25 g / l of aqueous solution DETAILED DESCRIPTION OF PARTICULAR EMBODIMENTS
  • n 1 for DTPA-bis-dopamide.
  • R 4 represents a hydrogen atom or an -OH group, while n is 0 or ln is 0 or 1
  • the products are dissolved in ethanol (32 ml for the two products resulting from the condensation with dopamine and 65 ml for the two products resulting from the condensation with tyramine), then precipitated in diethyl ether (150 mL). The precipitates are filtered and then washed with diethyl ether before drying in vacuo.
  • the returns are in all cases of the order of 80%.
  • Resins according to the invention are synthesized using:
  • NaOH sodium hydroxide
  • CsOH cesium hydroxide
  • a chelating monomer / phenol monomer / formaldehyde / strong base / H 2 0 molar ratio of 0.5 / 0.5 / 2.5 / 1.5 / 100.
  • the chelating monomer (0.5 mmol) and the phenolic monomer (0.5 mmol) are first solubilized in a solution of NaOH or CsOH (1.5 mmol in 100 mmol H 2 0). The resulting solution is stirred at room temperature or at 0 ° C and formaldehyde (2.5 mmol) is added to this solution. The reaction mixture is stirred for 24 hours after which it is heated in an oven under air at 100 ° C for 96 hours.
  • solution 1 ultrapure water (milli-Q TM water) doped with cesium and strontium (in the form of CsCl and SrCl 2 chlorides) at a concentration of 10 -4 M;
  • solution 2 a solution simulating a seawater diluted at 200 ppm (parts per million) of sodium and doped with cesium and strontium (in the form of CsCl and SrCl 2 chlorides) at a concentration of 10 -4 M;
  • solution 3 a solution simulating a seawater diluted with 200 ppm of sodium and 25 ppm of calcium, doped with cesium and strontium (in the form of chlorides CsCl and SrCl 2 ) at a concentration of 10 -4 M.
  • K D the coefficient of distribution
  • ml / g the coefficient of distribution
  • Ci initial concentration of the cation in solution (in mg / L);
  • V volume of solution (in mL);
  • Ci initial concentration of the cation in solution (in mg / L);
  • Tables II and III below show the K D , E and FD values obtained for cesium and strontium respectively, with the twenty-two resins synthesized in Example 2 and solutions 1 and 2, and using 1 g of resin per L of solution.
  • Table IV shows the K D and E values obtained for strontium, with the ETRF-Na and DTRF-Na resins synthesized in Example 2 above and solutions 2 and 3, by varying the amount of resin used per L solution of 0.5 g to 25 g. Table IV
  • FIG. 1 represents, in graphic form, the results presented in Table IV above for solution 2, while FIG. 2 represents, also in graphical form, the K D and E values obtained for cesium, with the ETRF-Na and DTRF-Na resins synthesized in Example 2 above and the solution 2, made it vary the amount of resin used per L of solution (from 0.5 g to 25 g)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Polymers & Plastics (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Physics & Mathematics (AREA)
  • General Engineering & Computer Science (AREA)
  • High Energy & Nuclear Physics (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
EP13801541.7A 2012-12-04 2013-12-03 Ionenaustauschharz mit chelatbildenden eigenschaften, verfahren zur herstellung davon und verwendungen davon Withdrawn EP2928604A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1261620A FR2998816B1 (fr) 2012-12-04 2012-12-04 Resine echangeuse d'ions a proprietes chelatantes, son procede de preparation et ses utilisations
PCT/EP2013/075406 WO2014086788A1 (fr) 2012-12-04 2013-12-03 Résine échangeuse d'ions à propriétés chélatantes, son procédé de préparation et ses utilisations

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EP2928604A1 true EP2928604A1 (de) 2015-10-14

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EP13801541.7A Withdrawn EP2928604A1 (de) 2012-12-04 2013-12-03 Ionenaustauschharz mit chelatbildenden eigenschaften, verfahren zur herstellung davon und verwendungen davon

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EP (1) EP2928604A1 (de)
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Publication number Priority date Publication date Assignee Title
JPS6051491B2 (ja) * 1980-03-22 1985-11-14 ユニチカ株式会社 フェノ−ル・アルデヒド系・キレ−ト樹脂の製造法及び吸着処理法
WO2009150983A1 (ja) * 2008-06-12 2009-12-17 日立化成工業株式会社 フェノール類ノボラック樹脂の製造方法及びフェノール類ノボラック樹脂を用いたレジンコーテットサンド

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FR2998816A1 (fr) 2014-06-06
WO2014086788A1 (fr) 2014-06-12

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