CA1162565A - Polymere fluore echangeur d'ions, a teneur de carboxyles, et methode de preparation connexe - Google Patents

Polymere fluore echangeur d'ions, a teneur de carboxyles, et methode de preparation connexe

Info

Publication number: CA1162565A
Authority: CA; Canada
Prior art keywords: groups; side chains; sulfonyl; pendant side; film
Prior art date: 1977-04-20
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

Application number

CA000394991A

Other languages

English (en)

Inventor

Walther G. Grot

Charles J. Molnar

Paul R. Resnick

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

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.)

1977-04-20

Filing date

1982-01-26

Publication date

1984-02-21

1978-04-18 Priority claimed from CA301,530A external-priority patent/CA1126443A/fr

1982-01-26 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1982-01-26 Priority to CA000394991A priority Critical patent/CA1162565A/fr

1984-02-21 Application granted granted Critical

1984-02-21 Publication of CA1162565A publication Critical patent/CA1162565A/fr

Status Expired legal-status Critical Current

Links

229920003303 ion-exchange polymer Polymers 0.000 title abstract description 10
238000000034 method Methods 0.000 title description 16
230000008569 process Effects 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 18
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 14
229910052783 alkali metal Inorganic materials 0.000 claims description 10
150000001340 alkali metals Chemical class 0.000 claims description 9
150000001342 alkaline earth metals Chemical class 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 5
229920000642 polymer Polymers 0.000 abstract description 59
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract description 38
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 38
239000012528 membrane Substances 0.000 abstract description 36
229910052731 fluorine Inorganic materials 0.000 abstract description 25
150000003839 salts Chemical class 0.000 abstract description 25
239000000203 mixture Substances 0.000 abstract description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 21
229910052760 oxygen Inorganic materials 0.000 abstract description 21
239000001301 oxygen Substances 0.000 abstract description 21
239000000178 monomer Substances 0.000 abstract description 20
238000007254 oxidation reaction Methods 0.000 abstract description 16
230000003647 oxidation Effects 0.000 abstract description 15
230000009467 reduction Effects 0.000 abstract description 15
239000011737 fluorine Substances 0.000 abstract description 14
229920002313 fluoropolymer Polymers 0.000 abstract description 13
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 11
125000002128 sulfonyl halide group Chemical group 0.000 abstract description 6
229920002554 vinyl polymer Polymers 0.000 abstract description 5
238000005868 electrolysis reaction Methods 0.000 abstract description 4
238000007334 copolymerization reaction Methods 0.000 abstract description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
239000000460 chlorine Substances 0.000 description 35
210000004379 membrane Anatomy 0.000 description 35
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 31
239000000243 solution Substances 0.000 description 28
-1 perfluoroalkyl radical Chemical class 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
229910052801 chlorine Inorganic materials 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 22
229920001577 copolymer Polymers 0.000 description 21
239000010410 layer Substances 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
235000019000 fluorine Nutrition 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
239000002243 precursor Substances 0.000 description 15
238000006722 reduction reaction Methods 0.000 description 15
239000007800 oxidant agent Substances 0.000 description 14
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 13
229940099408 Oxidizing agent Drugs 0.000 description 13
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 13
239000003513 alkali Substances 0.000 description 12
238000005342 ion exchange Methods 0.000 description 12
239000002253 acid Substances 0.000 description 11
OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical class [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 description 11
229960001760 dimethyl sulfoxide Drugs 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 8
TUFKHKZLBZWCAW-UHFFFAOYSA-N 2-(1-ethenoxypropan-2-yloxy)ethanesulfonyl fluoride Chemical compound C=COCC(C)OCCS(F)(=O)=O TUFKHKZLBZWCAW-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 7
125000001153 fluoro group Chemical group F* 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
239000007789 gas Substances 0.000 description 7
230000007062 hydrolysis Effects 0.000 description 7
238000006460 hydrolysis reaction Methods 0.000 description 7
239000002609 medium Substances 0.000 description 7
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 6
239000007788 liquid Substances 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical group FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
150000003863 ammonium salts Chemical class 0.000 description 5
150000001735 carboxylic acids Chemical class 0.000 description 5
239000003518 caustics Substances 0.000 description 5
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 5
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000000463 material Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
239000002344 surface layer Substances 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
230000000875 corresponding effect Effects 0.000 description 4
239000004744 fabric Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
239000003014 ion exchange membrane Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
125000001453 quaternary ammonium group Chemical group 0.000 description 4
239000002904 solvent Substances 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical class [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000002585 base Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000012267 brine Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
230000001143 conditioned effect Effects 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
230000006872 improvement Effects 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000010186 staining Methods 0.000 description 3
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
238000012360 testing method Methods 0.000 description 3
NJIRSTSECXKPCO-UHFFFAOYSA-M 3-[n-methyl-4-[2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]anilino]propanenitrile;chloride Chemical compound [Cl-].C1=CC(N(CCC#N)C)=CC=C1\C=C\C1=[N+](C)C2=CC=CC=C2C1(C)C NJIRSTSECXKPCO-UHFFFAOYSA-M 0.000 description 2
MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229910006095 SO2F Inorganic materials 0.000 description 2
239000004809 Teflon Substances 0.000 description 2
229920006362 Teflon® Polymers 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
238000005349 anion exchange Methods 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
229940117975 chromium trioxide Drugs 0.000 description 2
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
239000003999 initiator Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000002245 particle Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical group [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
229910000343 potassium bisulfate Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000001603 reducing effect Effects 0.000 description 2
230000003014 reinforcing effect Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000000126 substance Substances 0.000 description 2
229940124530 sulfonamide Drugs 0.000 description 2
150000003456 sulfonamides Chemical class 0.000 description 2
125000000542 sulfonic acid group Chemical group 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
UUUGYDOQQLOJQA-UHFFFAOYSA-L vanadyl sulfate Chemical compound [V+2]=O.[O-]S([O-])(=O)=O UUUGYDOQQLOJQA-UHFFFAOYSA-L 0.000 description 2
229910000352 vanadyl sulfate Inorganic materials 0.000 description 2
238000005406 washing Methods 0.000 description 2
229940124024 weight reducing agent Drugs 0.000 description 2
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
TXGPGHBYAPBDAG-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-4,4-bis(trifluoromethyl)cyclobutane Chemical compound FC(F)(F)C1(C(F)(F)F)C(F)(F)C(F)(F)C1(F)F TXGPGHBYAPBDAG-UHFFFAOYSA-N 0.000 description 1
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical class [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
229910003206 NH4VO3 Inorganic materials 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
241000206607 Porphyra umbilicalis Species 0.000 description 1
229910006080 SO2X Inorganic materials 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000007942 carboxylates Chemical group 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
VYZAMTAEIAYCRO-YPZZEJLDSA-N chromium-50 Chemical compound [50Cr] VYZAMTAEIAYCRO-YPZZEJLDSA-N 0.000 description 1
230000001112 coagulating effect Effects 0.000 description 1
239000010941 cobalt Chemical class 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical class [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000001246 colloidal dispersion Methods 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Chemical class 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
XGFJCRNRWOXGQM-UHFFFAOYSA-N hot-2 Chemical compound CCSC1=CC(OC)=C(CCNO)C=C1OC XGFJCRNRWOXGQM-UHFFFAOYSA-N 0.000 description 1
229960000443 hydrochloric acid Drugs 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000007654 immersion Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000003475 lamination Methods 0.000 description 1
230000007774 longterm Effects 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
229910052748 manganese Chemical class 0.000 description 1
239000011572 manganese Chemical class 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
DLHYHXMSPLUHRA-UHFFFAOYSA-N perfluoromethylcyclohexane Chemical compound FC1C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)C(F)(F)F DLHYHXMSPLUHRA-UHFFFAOYSA-N 0.000 description 1
YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012783 reinforcing fiber Substances 0.000 description 1
238000009738 saturating Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000626 sulfinic acid group Chemical group 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
150000008054 sulfonate salts Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical class [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical class [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
229940041260 vanadyl sulfate Drugs 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
238000004876 x-ray fluorescence Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Manufacture Of Macromolecular Shaped Articles (AREA)

CA000394991A 1977-04-20 1982-01-26 Polymere fluore echangeur d'ions, a teneur de carboxyles, et methode de preparation connexe Expired CA1162565A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000394991A CA1162565A (fr)	1977-04-20	1982-01-26	Polymere fluore echangeur d'ions, a teneur de carboxyles, et methode de preparation connexe

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US78972677A	1977-04-20	1977-04-20
US789,726		1977-04-20
CA301,530A CA1126443A (fr)	1977-04-20	1978-04-18	Procede d'obtention d'un polymere fluore echangeur d'ions, et contenant des groupements carboxyliques
CA000394991A CA1162565A (fr)	1977-04-20	1982-01-26	Polymere fluore echangeur d'ions, a teneur de carboxyles, et methode de preparation connexe

Publications (1)

Publication Number	Publication Date
CA1162565A true CA1162565A (fr)	1984-02-21

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CA000394991A Expired CA1162565A (fr)	1977-04-20	1982-01-26	Polymere fluore echangeur d'ions, a teneur de carboxyles, et methode de preparation connexe

Country Status (1)

Country	Link
CA (1)	CA1162565A (fr)

1982
- 1982-01-26 CA CA000394991A patent/CA1162565A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-02-21	MKEX	Expiry

Publication	Publication Date	Title
US4267364A (en)	1981-05-12	Fluorinated ion exchange polymer containing carboxylic groups, process for making same, and film and membrane thereof
US4544458A (en)	1985-10-01	Fluorinated ion exchange polymer containing carboxylic groups, process for making same, and film and membrane thereof
CA1185398A (fr)	1985-04-09	Membrane fluoree echangeuse de cations, et sa fabrication
US4085071A (en)	1978-04-18	Ion exchange polymer film, consisting of fluorinated polymer with N-monosubstituted sulfonamido groups method and apparatus for electrolysis of alkali or alkaline earth metal halide
CA1148566A (fr)	1983-06-21	Copolymere fluore et preparation
US3969285A (en)	1976-07-13	Heat-treated fluorocarbon sulfonylamine cation permselectivity
CA1119350A (fr)	1982-03-02	Membranes d'echange d'ions faites de copolymeres en melange
US6670424B1 (en)	2003-12-30	Ross-linked sulphonated polymers and their preparation process
EP0025644B1 (fr)	1983-12-28	Membrane échangeuse de cations en polymère fluoré pour l'électrolyse, procédé pour sa préparation et procédé pour l'électrolyse d'une solution acqueuse d'un halogénure de métal alcalin
CA1126443A (fr)	1982-06-22	Procede d'obtention d'un polymere fluore echangeur d'ions, et contenant des groupements carboxyliques
AU613202B2 (en)	1991-07-25	Organic polymeric material and ion-exchange membrane produced therefrom
CA1079914A (fr)	1980-06-24	Methode de preparation d'une membrane d'echange de cations
EP0053455B1 (fr)	1985-07-24	Fabrication d'une membrane échangeuse de cations en polymère fluoré et procédé d'électrolyse utilisant cette membrane
DE2558393A1 (de)	1976-06-24	Membrane fuer elektrochemische zellen und verfahren zu ihrer herstellung
CA1133425A (fr)	1982-10-12	Polymere fluore echangeur d'ions, contenant des groupements carboxyles; pellicule et membrane qui en sont tirees
CA1209527A (fr)	1986-08-12	Pile electrolytique a face lisse de diaphragme du cote cathode
EP0079157B1 (fr)	1986-06-04	Procédé d'estérification de polymères fluorés d'acides carboxyliques
US4030988A (en)	1977-06-21	Process for producing halogen and metal hydroxides with cation exchange membranes of improved permselectivity
US4026783A (en)	1977-05-31	Electrolysis cell using cation exchange membranes of improved permselectivity
US4487668A (en)	1984-12-11	Fluorinated ion exchange polymer containing carboxylic groups, and film and membrane thereof
CA1139780A (fr)	1983-01-18	Procede d'obtention d'un polymere echangeur d'ions qui soit fluore et contienne des groupements carboxyliques
US4113585A (en)	1978-09-12	Method and apparatus for electrolysis of alkali or alkaline earth metal halide
CA1142693A (fr)	1983-03-08	Polymere fluore, echangeur d'ions, contenant des groupes carboxyliques, et methode pour les preparer
US4414338A (en)	1983-11-08	Cation exchange membrane
TW202346456A (zh)	2023-12-01	製備官能化聚合物之方法