CA1158397A - Selective ion exchange resins - Google Patents
Selective ion exchange resinsInfo
- Publication number
- CA1158397A CA1158397A CA000372848A CA372848A CA1158397A CA 1158397 A CA1158397 A CA 1158397A CA 000372848 A CA000372848 A CA 000372848A CA 372848 A CA372848 A CA 372848A CA 1158397 A CA1158397 A CA 1158397A
- Authority
- CA
- Canada
- Prior art keywords
- ion exchange
- resin
- exchange resin
- polymeric ion
- imidazole
- 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.)
- Expired
Links
- 239000003456 ion exchange resin Substances 0.000 title claims abstract description 17
- 229920003303 ion-exchange polymer Polymers 0.000 title claims abstract description 17
- 239000011347 resin Substances 0.000 claims abstract description 46
- 229920005989 resin Polymers 0.000 claims abstract description 46
- -1 imidazoyl Chemical group 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 12
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 7
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 6
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 5
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 125000003277 amino group Chemical group 0.000 claims abstract 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000005342 ion exchange Methods 0.000 claims description 3
- 230000002411 adverse Effects 0.000 claims description 2
- 125000006384 methylpyridyl group Chemical group 0.000 claims description 2
- 239000000178 monomer Substances 0.000 abstract description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 17
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 13
- 239000010949 copper Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910017052 cobalt Inorganic materials 0.000 description 8
- 239000010941 cobalt Substances 0.000 description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- 229940116441 divinylbenzene Drugs 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- MOUNHKKCIGVIDI-UHFFFAOYSA-L disodium;4-hydroxy-7-[(5-hydroxy-7-sulfonatonaphthalen-2-yl)carbamoylamino]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].OC1=CC(S([O-])(=O)=O)=CC2=CC(NC(=O)NC=3C=C4C=C(C=C(C4=CC=3)O)S([O-])(=O)=O)=CC=C21 MOUNHKKCIGVIDI-UHFFFAOYSA-L 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- KXZQYLBVMZGIKC-UHFFFAOYSA-N 1-pyridin-2-yl-n-(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CNCC1=CC=CC=N1 KXZQYLBVMZGIKC-UHFFFAOYSA-N 0.000 description 1
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical compound C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-UHFFFAOYSA-N 0.000 description 1
- VLMNYMSCQPXJDR-UHFFFAOYSA-N 2-(pyridin-2-ylmethylamino)ethanol Chemical compound OCCNCC1=CC=CC=N1 VLMNYMSCQPXJDR-UHFFFAOYSA-N 0.000 description 1
- DDHFQLXEZRPRKC-UHFFFAOYSA-N 2-ethyl-1h-imidazol-5-amine Chemical compound CCC1=NC(N)=CN1 DDHFQLXEZRPRKC-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- JPJMLQRVGZBWPD-UHFFFAOYSA-N 2-methyl-1h-imidazol-5-amine Chemical compound CC1=NC=C(N)N1 JPJMLQRVGZBWPD-UHFFFAOYSA-N 0.000 description 1
- YINAQTWWZMXVOK-UHFFFAOYSA-N 3-ethenylpyridine-2-carbaldehyde;1h-imidazole Chemical compound C1=CNC=N1.C=CC1=CC=CN=C1C=O YINAQTWWZMXVOK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 101100270435 Mus musculus Arhgef12 gene Proteins 0.000 description 1
- 101100326677 Onchocerca volvulus crt-1 gene Proteins 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- GZETWZZNDACBTQ-UHFFFAOYSA-N [Cl].C=C Chemical group [Cl].C=C GZETWZZNDACBTQ-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910001429 cobalt ion Inorganic materials 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910001453 nickel ion Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- 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
- B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C08F26/00—Homopolymers and 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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/06—Homopolymers and 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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/28—Condensation with aldehydes or ketones
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
Landscapes
- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ZA80/1458 | 1980-03-12 | ||
| ZA801458 | 1980-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1158397A true CA1158397A (en) | 1983-12-06 |
Family
ID=25574602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000372848A Expired CA1158397A (en) | 1980-03-12 | 1981-03-12 | Selective ion exchange resins |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4401629A (OSRAM) |
| AU (1) | AU535322B2 (OSRAM) |
| BE (1) | BE887872A (OSRAM) |
| CA (1) | CA1158397A (OSRAM) |
| DE (1) | DE3108943A1 (OSRAM) |
| FR (1) | FR2477904A1 (OSRAM) |
| GB (1) | GB2071120B (OSRAM) |
| NL (1) | NL8101170A (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2071120B (en) | 1980-03-12 | 1984-07-11 | Nat Inst Metallurg | Polymeric ion exchange resins |
| US4533621A (en) * | 1983-07-19 | 1985-08-06 | Konishiroku Photo Industry Co., Ltd. | Photographic element with imadazole dye mordant |
| GB8431305D0 (en) * | 1984-12-12 | 1985-01-23 | Ici Plc | Extraction of metals |
| US4619744A (en) * | 1985-10-28 | 1986-10-28 | Phillips Petroleum Company | Recovery of heavy metals from aqueous solutions |
| DE4128837C2 (de) * | 1991-08-30 | 2001-02-22 | Iab Ionenaustauscher Gmbh | Verfahren zur Entfernung von Kupfer und/oder Nickel aus wäßrigen Medien |
| US5455359B1 (en) * | 1993-10-01 | 1998-05-05 | Res Corp Technologies Inc | Metal ion binding monomer and polymer |
| US5626648A (en) * | 1995-07-17 | 1997-05-06 | Bhp Minerals International Inc. | Recovery of nickel from bioleach solution |
| EP1964811B1 (en) * | 2007-02-28 | 2016-11-30 | China Petrochemical Development Corporation | Method for preparing hydroxylammonium phosphate |
| CN115124655B (zh) * | 2022-06-27 | 2023-05-05 | 福州大学 | 一种含咪唑基有机聚合物材料的制备及应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE971934C (de) * | 1952-07-17 | 1959-04-16 | Bayer Ag | Verfahren zur Herstellung von Polymerisaten |
| FR1345250A (fr) * | 1961-11-29 | 1963-12-06 | Basf Ag | Polymères cationiques |
| US3473901A (en) * | 1963-02-08 | 1969-10-21 | Rohm & Haas | Fuel compositions |
| US3772259A (en) * | 1965-07-12 | 1973-11-13 | American Cyanamid Co | 2-vinyl-1-cycloamidinepropionamide polymers |
| US3488294A (en) * | 1966-01-17 | 1970-01-06 | Petrolite Corp | Process of inhibiting corrosion of ferrous metals and alloys employing a polyvinyl heterocyclic polymer |
| US3826787A (en) * | 1973-09-21 | 1974-07-30 | American Cyanamid Co | Regular alternating copolymers of styrene and imidazolines and their derivatives |
| US4006247A (en) * | 1974-05-06 | 1977-02-01 | American Cyanamid Company | Unsaturated imidazolines |
| DE2547970C2 (de) * | 1975-10-27 | 1982-02-04 | Röhm GmbH, 6100 Darmstadt | Filmbildende wäßrige Kunststoffdispersionen und ihre Verwendung als Bindemittel für wäßrige Anstrichfarben |
| ZA775398B (en) * | 1977-09-07 | 1979-04-25 | Nat Inst Metallurg | Selective ion exchange media |
| US4254087A (en) * | 1979-07-25 | 1981-03-03 | The Dow Chemical Company | Extraction of copper, nickel and cobalt using alkylaromatic sulfonic acids and chelating amines |
| GB2071120B (en) | 1980-03-12 | 1984-07-11 | Nat Inst Metallurg | Polymeric ion exchange resins |
-
1981
- 1981-03-06 GB GB8107113A patent/GB2071120B/en not_active Expired
- 1981-03-10 FR FR8104726A patent/FR2477904A1/fr active Granted
- 1981-03-10 DE DE19813108943 patent/DE3108943A1/de not_active Ceased
- 1981-03-10 BE BE0/204067A patent/BE887872A/fr not_active IP Right Cessation
- 1981-03-10 US US06/242,410 patent/US4401629A/en not_active Expired - Fee Related
- 1981-03-11 NL NL8101170A patent/NL8101170A/nl not_active Application Discontinuation
- 1981-03-11 AU AU68246/81A patent/AU535322B2/en not_active Ceased
- 1981-03-12 CA CA000372848A patent/CA1158397A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE887872A (fr) | 1981-07-01 |
| US4401629A (en) | 1983-08-30 |
| GB2071120B (en) | 1984-07-11 |
| AU535322B2 (en) | 1984-03-15 |
| NL8101170A (nl) | 1981-10-01 |
| DE3108943A1 (de) | 1982-01-14 |
| GB2071120A (en) | 1981-09-16 |
| AU6824681A (en) | 1981-09-17 |
| FR2477904B1 (OSRAM) | 1985-04-19 |
| FR2477904A1 (fr) | 1981-09-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |