CA1094731A - Chelate exchange resins from aminopyridines - Google Patents
Chelate exchange resins from aminopyridinesInfo
- Publication number
- CA1094731A CA1094731A CA254,883A CA254883A CA1094731A CA 1094731 A CA1094731 A CA 1094731A CA 254883 A CA254883 A CA 254883A CA 1094731 A CA1094731 A CA 1094731A
- Authority
- CA
- Canada
- Prior art keywords
- resin
- picolylamine
- carbon atoms
- group
- alkyl
- 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
- 239000011347 resin Substances 0.000 title claims abstract description 172
- 229920005989 resin Polymers 0.000 title claims abstract description 172
- 239000013522 chelant Substances 0.000 title claims abstract description 47
- 150000003927 aminopyridines Chemical class 0.000 title 1
- 239000010949 copper Substances 0.000 claims abstract description 80
- 229910052802 copper Inorganic materials 0.000 claims abstract description 50
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 49
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000011159 matrix material Substances 0.000 claims abstract description 36
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229920000642 polymer Polymers 0.000 claims abstract description 17
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 16
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229920001577 copolymer Polymers 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 239000011324 bead Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 238000011084 recovery Methods 0.000 claims description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 8
- 239000000908 ammonium hydroxide Substances 0.000 claims description 8
- 229920006037 cross link polymer Polymers 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- -1 hydroxycarbonyl)alkyl group Chemical group 0.000 claims description 5
- VLMNYMSCQPXJDR-UHFFFAOYSA-N 2-(pyridin-2-ylmethylamino)ethanol Chemical group OCCNCC1=CC=CC=N1 VLMNYMSCQPXJDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000006294 amino alkylene group Chemical group 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- OOTKJPZEEVPWCR-UHFFFAOYSA-N n-methyl-1-pyridin-2-ylmethanamine Chemical group CNCC1=CC=CC=N1 OOTKJPZEEVPWCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 229910001431 copper ion Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- KXZQYLBVMZGIKC-UHFFFAOYSA-N 1-pyridin-2-yl-n-(pyridin-2-ylmethyl)methanamine Chemical group C=1C=CC=NC=1CNCC1=CC=CC=N1 KXZQYLBVMZGIKC-UHFFFAOYSA-N 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 25
- 229910052742 iron Inorganic materials 0.000 abstract description 8
- 230000002378 acidificating effect Effects 0.000 abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 3
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract description 2
- 229920001568 phenolic resin Polymers 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 239000012458 free base Substances 0.000 description 13
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 11
- 239000002002 slurry Substances 0.000 description 10
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 238000011068 loading method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 235000013350 formula milk Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000012508 resin bead Substances 0.000 description 5
- 235000011149 sulphuric acid Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910000365 copper sulfate Inorganic materials 0.000 description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 229940116441 divinylbenzene Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical group OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical class Cl* 0.000 description 2
- 238000007265 chloromethylation reaction Methods 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 235000016768 molybdenum Nutrition 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- WOZCYBXTBXAJSA-UHFFFAOYSA-N 2-(chloromethyl)buta-1,3-diene Chemical compound ClCC(=C)C=C WOZCYBXTBXAJSA-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical group NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- HABAXTXIECRCKH-UHFFFAOYSA-N bis(prop-2-enyl) butanedioate Chemical compound C=CCOC(=O)CCC(=O)OCC=C HABAXTXIECRCKH-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000003841 chloride salts Chemical group 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005363 electrowinning Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000009854 hydrometallurgy Methods 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- ZGELEKWHABCERO-UHFFFAOYSA-N n-methyl-n'-(pyridin-2-ylmethyl)ethane-1,2-diamine Chemical compound CNCCNCC1=CC=CC=N1 ZGELEKWHABCERO-UHFFFAOYSA-N 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 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
- 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
-
- 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
- C08F8/44—Preparation of metal salts or ammonium salts
-
- 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
- C08G8/28—Chemically modified polycondensates
-
- 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
- C08G85/00—General processes for preparing compounds provided for in this subclass
- C08G85/004—Modification of polymers by chemical after-treatment
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US587,185 | 1975-06-16 | ||
| US05/587,185 US4031038A (en) | 1975-06-16 | 1975-06-16 | Water insoluble chelate exchange resins having a crosslinked polymer matrix and pendant thereto a plurality of methyleneaminopyridine groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1094731A true CA1094731A (en) | 1981-01-27 |
Family
ID=24348737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,883A Expired CA1094731A (en) | 1975-06-16 | 1976-06-15 | Chelate exchange resins from aminopyridines |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US4031038A (enExample) |
| JP (1) | JPS5850138B2 (enExample) |
| AU (1) | AU508278B2 (enExample) |
| CA (1) | CA1094731A (enExample) |
| DE (1) | DE2626623C2 (enExample) |
| FR (1) | FR2314927A1 (enExample) |
| GB (1) | GB1546839A (enExample) |
| IT (1) | IT1061690B (enExample) |
| ZA (1) | ZA763517B (enExample) |
| ZM (1) | ZM7576A1 (enExample) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL117268B1 (en) * | 1978-07-26 | 1981-07-31 | Politechnika Gdanska | Method of recovery of copper and accompanying metals from sulphide ores,post-flotation deposits and waste products in metallurgical processing of copper oresiz sernistykh rud,flotacionnykh osadkov i iz proizvodstvennykh otchodov metallurgicheskojj pererabotki mednykh rud |
| US4246350A (en) * | 1979-03-01 | 1981-01-20 | The Dow Chemical Company | Protein immobilization on chelating resins |
| CA1119416A (en) * | 1979-08-14 | 1982-03-09 | Juraj Babjak | Process for nickel removal from concentrated aqueous cobaltous sulfate solutions |
| US4298380A (en) * | 1980-02-14 | 1981-11-03 | Bochkarev Ellin P | Process for purifying low-melting metals from impurities |
| DE3011393A1 (de) * | 1980-03-25 | 1981-10-01 | Riedel-De Haen Ag, 3016 Seelze | Chelatbildender ionenaustauscher auf basis eines organischen polymers und verfahren zu seiner herstellung |
| US4320099A (en) * | 1980-07-28 | 1982-03-16 | Inco Limited | Process for nickel removal from concentrated aqueous cobaltous sulfate solutions |
| US4371506A (en) * | 1981-06-18 | 1983-02-01 | Himsley Engineering Limited | Ammoniacal elution of copper from ion exchange resins |
| US4451375A (en) * | 1983-08-25 | 1984-05-29 | The Dow Chemical Company | Iodine adsorption via picolylamine ion exchange resins |
| US4978724A (en) * | 1983-11-23 | 1990-12-18 | Applied Immunesciences, Inc. | Method of preparing derivatized polystyrene for spectroscopic studies |
| GB2166140B (en) * | 1984-10-27 | 1989-06-07 | Ion Exchange | Novel adsorbents for use in the purification of water and other chemicals and a process for preparing same |
| FR2578447B1 (fr) * | 1985-03-08 | 1987-05-15 | Inst Francais Du Petrole | Procede de regeneration d'un catalyseur usage par une solution aqueuse de peroxyde d'hydrogene stabilisee par un compose organique |
| US4670180A (en) * | 1985-04-26 | 1987-06-02 | Miyoshi Yushi Kabushiki Kaisha | Metal scavenger and metal scavenging process |
| US4680357A (en) * | 1985-05-28 | 1987-07-14 | The Dow Chemical Company | Interpolymers of ethylene and alkenyl pyridines and preparation thereof |
| GB8525648D0 (en) * | 1985-10-17 | 1985-11-20 | British Petroleum Co Plc | Separation process |
| US4619744A (en) * | 1985-10-28 | 1986-10-28 | Phillips Petroleum Company | Recovery of heavy metals from aqueous solutions |
| US4666683A (en) * | 1985-11-21 | 1987-05-19 | Eco-Tec Limited | Process for removal of copper from solutions of chelating agent and copper |
| US4871779A (en) * | 1985-12-23 | 1989-10-03 | The Dow Chemical Company | Ion exchange/chelation resins containing dense star polymers having ion exchange or chelate capabilities |
| US4755298A (en) * | 1986-12-04 | 1988-07-05 | The Dow Chemical Company | Process for removing boron ions from aqueous solutions |
| US4741831A (en) * | 1986-12-04 | 1988-05-03 | The Dow Chemical Company | Process and composition for removal of metal ions from aqueous solutions |
| US5068419A (en) * | 1986-12-18 | 1991-11-26 | Uop | Separation of an organic acid from a fermentation broth with an anionic polymeric adsorbent |
| US4924027A (en) * | 1986-12-18 | 1990-05-08 | Uop | Separation of salts of citric acid from fermentation broth with a weakly basic anionic exchange resin adsorbent |
| US6528292B1 (en) | 1987-05-29 | 2003-03-04 | Aventis Pharmaceuticals Holdings Inc. | Derivatized polystyrene and other polymer supports for spectroscopic studies |
| US4883608A (en) * | 1987-11-18 | 1989-11-28 | Southwest Research Institute | Polymeric decontamination composition |
| US5180822A (en) * | 1988-09-21 | 1993-01-19 | Reilly Industries, Inc. | Highly selective chelating resins and monomers for their preparation |
| US5269905A (en) * | 1990-04-30 | 1993-12-14 | Elf Atochem North America, Inc. | Apparatus and process to regenerate a trivalent chromium bath |
| US5178746A (en) * | 1990-11-05 | 1993-01-12 | Bio-Recovery Systems, Inc. | Method for purification of trivalent chromium electroplating baths |
| DE4038192A1 (de) * | 1990-11-30 | 1992-06-04 | Degussa | Verfahren zur herstellung von 1,3-propandiol |
| US5141965A (en) * | 1991-03-28 | 1992-08-25 | The Dow Chemical Company | Resins having improved exchange kinetics |
| US5182026A (en) * | 1991-03-28 | 1993-01-26 | The Dow Chemical Company | Resins having improved exchange kinetics |
| US5112873A (en) * | 1991-03-28 | 1992-05-12 | The Dow Chemical Company | Resins having improved exchange kinetics |
| CN1043013C (zh) * | 1993-06-24 | 1999-04-21 | 黑龙江省科学院石油化学研究所 | 醋酸溶液中钴锰离子的离子交换回收方法 |
| US5641887A (en) * | 1994-04-01 | 1997-06-24 | University Of Pittsburgh | Extraction of metals in carbon dioxide and chelating agents therefor |
| US5872257A (en) * | 1994-04-01 | 1999-02-16 | University Of Pittsburgh | Further extractions of metals in carbon dioxide and chelating agents therefor |
| US6183815B1 (en) | 1994-04-01 | 2001-02-06 | University Of Pittsburgh | Method and composition for surface treatment of metals |
| CA2147307A1 (en) * | 1994-04-20 | 1995-10-21 | Dean Butler | Noble metal recovery |
| US5759716A (en) | 1996-04-08 | 1998-06-02 | Ensci Inc | Battery element containing metal inhibiting additives |
| US6268081B1 (en) | 1996-07-02 | 2001-07-31 | Ensci Inc | Battery element containing efficiency improving additives |
| US6350541B1 (en) | 1996-07-02 | 2002-02-26 | Ensci Inc. | Battery element containing efficiency improving additives |
| US6514639B2 (en) | 1998-03-20 | 2003-02-04 | Ensci Inc | Negative plate element for a lead acid battery containing efficiency improving additives |
| US6284930B1 (en) * | 1999-07-30 | 2001-09-04 | E.I. Du Pont De Nemours And Company | Process for the preparation of 3-hydroxypropanal |
| US6350420B1 (en) * | 1999-10-15 | 2002-02-26 | Bhp Minerals International, Inc. | Resin-in-pulp method for recovery of nickel and cobalt |
| US6638143B2 (en) * | 1999-12-22 | 2003-10-28 | Applied Materials, Inc. | Ion exchange materials for chemical mechanical polishing |
| US6395061B1 (en) | 2000-03-07 | 2002-05-28 | Bhp Minerals International Inc. | Process for organic acid bioleaching of ore |
| EP1394196A1 (en) * | 2002-08-16 | 2004-03-03 | Rohm And Haas Company | Resin for solid phase synthesis |
| US8126950B2 (en) * | 2003-09-29 | 2012-02-28 | Agency For Science, Technology And Research | Method for performing a domain transformation of a digital signal from the time domain into the frequency domain and vice versa |
| US20050252547A1 (en) * | 2004-05-11 | 2005-11-17 | Applied Materials, Inc. | Methods and apparatus for liquid chemical delivery |
| DE102006004953A1 (de) * | 2006-02-01 | 2007-08-02 | Lanxess Deutschland Gmbh | Chelatharze in der Metallgewinnung |
| EP1964811B1 (en) * | 2007-02-28 | 2016-11-30 | China Petrochemical Development Corporation | Method for preparing hydroxylammonium phosphate |
| US20090022638A1 (en) * | 2007-07-19 | 2009-01-22 | Duilio Rossoni | Ion exchanger for winning metals of value |
| DE102007034732A1 (de) | 2007-07-23 | 2009-01-29 | Lanxess Deutschland Gmbh | Verfahren zur Herstellung von Chelatharzen |
| DE102007034733A1 (de) * | 2007-07-23 | 2009-01-29 | Lanxess Deutschland Gmbh | Verfahren zur Herstellung monodisperser Chelatharze |
| DE102007034731A1 (de) | 2007-07-23 | 2009-01-29 | Lanxess Deutschland Gmbh | Chelatharze |
| DE102008012223A1 (de) * | 2008-03-03 | 2009-09-10 | Lanxess Deutschland Gmbh | Picolylaminharze |
| DE102008012224A1 (de) * | 2008-03-03 | 2009-09-10 | Lanxess Deutschland Gmbh | Picolylaminharze |
| EP2330137B1 (de) | 2009-12-04 | 2013-06-26 | LANXESS Deutschland GmbH | Methylenaminoethylsulfonsäure-Chelatharze |
| WO2011109151A1 (en) * | 2010-03-03 | 2011-09-09 | 3M Innovative Properties Company | Ligand guanidinyl functionalized polymers |
| CN102085490A (zh) * | 2010-12-27 | 2011-06-08 | 天津博纳艾杰尔科技有限公司 | 一种固相萃取混合填料及固相萃取柱 |
| EP2664016A1 (en) | 2011-01-11 | 2013-11-20 | ETV Energy Ltd. | Membranes suitable for use as separators and electrochemical cells including such separators |
| BR112013019627A2 (pt) * | 2011-02-01 | 2019-09-24 | Vale Sa | purificação direta de efluente de lixiviação de níquel laterítico |
| CN102172516B (zh) * | 2011-03-28 | 2013-05-15 | 天津博纳艾杰尔科技有限公司 | 一种树脂包覆硅胶吸附材料 |
| WO2014031382A1 (en) | 2012-08-21 | 2014-02-27 | Dow Global Technologies Llc | Elution of metal ions from chelating resin using amino acid eluant |
| WO2014040138A1 (en) * | 2012-09-14 | 2014-03-20 | The University Of Queensland | Resin scavenging of nickel and cobalt |
| CN104704008B (zh) | 2012-10-10 | 2016-10-26 | 罗门哈斯公司 | 包括侧位芳基环氧基团的水不溶性共聚物 |
| JP5850966B2 (ja) * | 2014-03-07 | 2016-02-03 | 株式会社アライドマテリアル | コバルト抽出用溶液、コバルト溶液、およびコバルト回収方法 |
| US11306007B2 (en) | 2016-09-20 | 2022-04-19 | National Research Council Of Canada | Ferro-cavitation processes for target metal separation |
| CN108976325B (zh) * | 2018-08-06 | 2020-07-31 | 海南师范大学 | 一种偕胺肟基吡啶螯合树脂及其制备方法 |
| CN110453070A (zh) * | 2019-03-11 | 2019-11-15 | 西安蓝晓科技新材料股份有限公司 | 一种直接从红土镍矿浸提液中提取回收镍的方法 |
| CN111118895B (zh) * | 2019-12-16 | 2022-06-10 | 浙江工商大学 | 聚丙烯腈基-5-氨基-2-甲氧基吡啶螯合纤维及其合成方法和应用 |
| GB2607883A (en) * | 2021-06-11 | 2022-12-21 | Johnson Matthey Hydrogen Technologies Ltd | Electrocatalyst ink |
| CN119219821A (zh) * | 2024-12-03 | 2024-12-31 | 江苏金杉新材料有限公司 | 用于湿法冶金的苯乙烯系阴离子树脂及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2875162A (en) * | 1956-10-12 | 1959-02-24 | Dow Chemical Co | Vinylphenyl aliphatic aminocarboxylic acid polymers |
| US2980607A (en) * | 1957-05-10 | 1961-04-18 | Dow Chemical Co | Treatment of aqueous liquid solutions of chelate-forming metal ions with chelate exchange resins |
| US3337480A (en) * | 1966-05-31 | 1967-08-22 | Dow Chemical Co | Preparation of chelate cationexchange resins |
| US3473921A (en) * | 1969-01-06 | 1969-10-21 | Technion Res & Dev Foundation | Method for recovery of noble metals |
| US3873668A (en) * | 1973-03-27 | 1975-03-25 | Du Pont | Cupric, nickelous and argentous ion-selective chelating resins |
| US3998924A (en) * | 1975-08-04 | 1976-12-21 | The Dow Chemical Company | Recovery of non-ferrous metals from acidic liquors with a chelate exchange resin in presence of iron(III) |
-
1975
- 1975-06-16 US US05/587,185 patent/US4031038A/en not_active Expired - Lifetime
-
1976
- 1976-06-14 ZA ZA763517A patent/ZA763517B/xx unknown
- 1976-06-14 DE DE2626623A patent/DE2626623C2/de not_active Expired
- 1976-06-15 AU AU14894/76A patent/AU508278B2/en not_active Expired
- 1976-06-15 GB GB24768/76A patent/GB1546839A/en not_active Expired
- 1976-06-15 CA CA254,883A patent/CA1094731A/en not_active Expired
- 1976-06-15 FR FR7618140A patent/FR2314927A1/fr active Granted
- 1976-06-16 ZM ZM75/76A patent/ZM7576A1/xx unknown
- 1976-06-16 JP JP51070936A patent/JPS5850138B2/ja not_active Expired
- 1976-06-16 IT IT49967/76A patent/IT1061690B/it active
-
1977
- 1977-03-25 US US05/781,100 patent/US4098867A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51151688A (en) | 1976-12-27 |
| ZM7576A1 (en) | 1977-05-23 |
| AU508278B2 (en) | 1980-03-13 |
| AU1489476A (en) | 1977-12-22 |
| FR2314927B1 (enExample) | 1979-08-17 |
| DE2626623A1 (de) | 1977-01-20 |
| IT1061690B (it) | 1983-04-30 |
| GB1546839A (en) | 1979-05-31 |
| DE2626623C2 (de) | 1986-09-11 |
| ZA763517B (en) | 1977-07-27 |
| US4031038A (en) | 1977-06-21 |
| JPS5850138B2 (ja) | 1983-11-09 |
| FR2314927A1 (fr) | 1977-01-14 |
| US4098867A (en) | 1978-07-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |