CA1186277A - Membranes fluoropolymeriques obtenues par rayonnement et traitement a l'acide carboxylique fluore - Google Patents

Membranes fluoropolymeriques obtenues par rayonnement et traitement a l'acide carboxylique fluore

Info

Publication number: CA1186277A
Authority: CA; Canada
Prior art keywords: membrane; process according; fluoropolymeric; carboxylic acid; monomer
Prior art date: 1981-12-03
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

CA000391440A

Other languages

English (en)

Inventor

Michael V. Markus

George H. Barnett

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.)

Orica Ltd

Original Assignee

ICI Australia Ltd

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.)

1981-12-03

Filing date

1981-12-03

Publication date

1985-04-30

1981-12-03 Application filed by ICI Australia Ltd filed Critical ICI Australia Ltd

1981-12-03 Priority to CA000391440A priority Critical patent/CA1186277A/fr

1985-04-30 Application granted granted Critical

1985-04-30 Publication of CA1186277A publication Critical patent/CA1186277A/fr

Status Expired legal-status Critical Current

Links

239000012528 membrane Substances 0.000 title claims abstract description 74
229920002313 fluoropolymer Polymers 0.000 title claims description 5
239000004811 fluoropolymer Substances 0.000 title claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 title abstract description 5
238000000034 method Methods 0.000 claims abstract description 44
230000008569 process Effects 0.000 claims abstract description 37
239000000178 monomer Substances 0.000 claims abstract description 19
230000005855 radiation Effects 0.000 claims abstract description 14
238000005868 electrolysis reaction Methods 0.000 claims abstract description 7
229920001577 copolymer Polymers 0.000 claims abstract description 6
150000003254 radicals Chemical class 0.000 claims abstract 2
239000000463 material Substances 0.000 claims description 12
-1 hydroxyl ions Chemical class 0.000 claims description 11
238000013508 migration Methods 0.000 claims description 6
JULFZFLHGXXVRA-UHFFFAOYSA-N 2,2,3,4,4-pentafluorobut-3-enoic acid Chemical compound OC(=O)C(F)(F)C(F)=C(F)F JULFZFLHGXXVRA-UHFFFAOYSA-N 0.000 claims description 5
238000007334 copolymerization reaction Methods 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
150000007942 carboxylates Chemical group 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
238000005341 cation exchange Methods 0.000 claims description 2
238000010894 electron beam technology Methods 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
QARLOMBMXGVKNV-UHFFFAOYSA-N 1,2,2-trifluoroethenesulfonyl fluoride Chemical compound FC(F)=C(F)S(F)(=O)=O QARLOMBMXGVKNV-UHFFFAOYSA-N 0.000 claims 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
230000001678 irradiating effect Effects 0.000 claims 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
230000000379 polymerizing effect Effects 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
239000003513 alkali Substances 0.000 description 12
229920000557 Nafion® Polymers 0.000 description 11
239000000243 solution Substances 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 6
229910001514 alkali metal chloride Inorganic materials 0.000 description 5
239000000126 substance Substances 0.000 description 5
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
239000007788 liquid Substances 0.000 description 4
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
229910052753 mercury Inorganic materials 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
230000006872 improvement Effects 0.000 description 3
239000010410 layer Substances 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
239000000758 substrate Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
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
231100000987 absorbed dose Toxicity 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000008901 benefit Effects 0.000 description 2
125000002843 carboxylic acid group Chemical group 0.000 description 2
238000007385 chemical modification Methods 0.000 description 2
239000003792 electrolyte Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
238000002386 leaching Methods 0.000 description 2
QMCHYTVPUAJEMM-UHFFFAOYSA-N n-[2-(4-benzhydrylpiperazin-1-yl)ethyl]-2,6-dimethyl-3-nitropyridin-4-amine Chemical compound CC1=NC(C)=CC(NCCN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1[N+]([O-])=O QMCHYTVPUAJEMM-UHFFFAOYSA-N 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000002344 surface layer Substances 0.000 description 2
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical class FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
229920003935 Flemion® Polymers 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229940023913 cation exchange resins Drugs 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
230000032798 delamination Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
RLPLVYSUMVIZCJ-UHFFFAOYSA-N ethyl 2,2,3,4,4-pentafluorobut-3-enoate Chemical compound CCOC(=O)C(F)(F)C(F)=C(F)F RLPLVYSUMVIZCJ-UHFFFAOYSA-N 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010559 graft polymerization reaction Methods 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000003475 lamination Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
230000003405 preventing effect Effects 0.000 description 1
238000007789 sealing Methods 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007784 solid electrolyte Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
230000008961 swelling Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000004804 winding Methods 0.000 description 1

Landscapes

Manufacture Of Macromolecular Shaped Articles (AREA)

CA000391440A 1981-12-03 1981-12-03 Membranes fluoropolymeriques obtenues par rayonnement et traitement a l'acide carboxylique fluore Expired CA1186277A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000391440A CA1186277A (fr)	1981-12-03	1981-12-03	Membranes fluoropolymeriques obtenues par rayonnement et traitement a l'acide carboxylique fluore

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000391440A CA1186277A (fr)	1981-12-03	1981-12-03	Membranes fluoropolymeriques obtenues par rayonnement et traitement a l'acide carboxylique fluore

Publications (1)

Publication Number	Publication Date
CA1186277A true CA1186277A (fr)	1985-04-30

Family

ID=4121552

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000391440A Expired CA1186277A (fr)	1981-12-03	1981-12-03	Membranes fluoropolymeriques obtenues par rayonnement et traitement a l'acide carboxylique fluore

Country Status (1)

Country	Link
CA (1)	CA1186277A (fr)

1981
- 1981-12-03 CA CA000391440A patent/CA1186277A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-04-30	MKEX	Expiry

Publication	Publication Date	Title
US4602045A (en)	1986-07-22	Cation-exchange resins and use as membranes in electrolytic cells
EP0032021B1 (fr)	1985-03-27	Résine échangeuse de cations et sa production, membrane permsélective à base de celle-ci, et procédé de production d'une membrane
US4169023A (en)	1979-09-25	Electrolytic diaphragms, and method of electrolysis using the same
US4090931A (en)	1978-05-23	Anode-structure for electrolysis
US4605685A (en)	1986-08-12	Method for preparation of graft polymeric membranes
US4012303A (en)	1977-03-15	Trifluorostyrene sulfonic acid membranes
US4101395A (en)	1978-07-18	Cathode-structure for electrolysis
US4339473A (en)	1982-07-13	Gamma radiation grafting process for preparing separator membranes for electrochemical cells
CA1185558A (fr)	1985-04-16	Methode d'electrolyse de l'eau
CA1046457A (fr)	1979-01-16	Diaphragmes electrolytiques et mode d'electrolyse
US4113922A (en)	1978-09-12	Trifluorostyrene sulfonic acid membranes
US4396727A (en)	1983-08-02	Cation exchange membrane and process for producing the same
US4166014A (en)	1979-08-28	Electrolytic diaphragms, and method of electrolysis using the same
EP0056896B2 (fr)	1989-11-23	Procédé d'extraction de polymères fluorés
US4923611A (en)	1990-05-08	Novel anion-exchange membrane
EP0057065B1 (fr)	1984-05-16	Fabrication d'une membrane échangeuse de cations et cellule d'électrolyse contenant cette membrane
US4154909A (en)	1979-05-15	Process for producing cation exchange membrane by treatment of fluorinated polymer containing sulfonyl halide groups with amine and vinyl monomer
CA1186277A (fr)	1985-04-30	Membranes fluoropolymeriques obtenues par rayonnement et traitement a l'acide carboxylique fluore
US4481306A (en)	1984-11-06	Polymerization process
CA1059062A (fr)	1979-07-24	Procede d'electrolyse par membrane d'halogenures alcalino-metalliques
JPS6055033A (ja)	1985-03-29	陽イオン交換膜の製造方法
FI73703C (fi)	1987-11-09	Foerfarande foer behandling av ett selektivt genomslaeppligt fluorpolymermembran.
CA1082133A (fr)	1980-07-22	Cathode d'electrolyse
JPS5939453B2 (ja)	1984-09-22	陽イオン交換体の製造方法
CA1052858A (fr)	1979-04-17	Membranes d'acide trifluostyrene sulfonique