FI72530B - Fluorerat katjonbytarmembran och laminat samt foerfarande foer dess framstaellning. - Google Patents

Fluorerat katjonbytarmembran och laminat samt foerfarande foer dess framstaellning. Download PDF

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Publication number
FI72530B
FI72530B FI801733A FI801733A FI72530B FI 72530 B FI72530 B FI 72530B FI 801733 A FI801733 A FI 801733A FI 801733 A FI801733 A FI 801733A FI 72530 B FI72530 B FI 72530B
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FI
Finland
Prior art keywords
membrane
cation exchange
carboxylic acid
fluorinated
exchange membrane
Prior art date
Application number
FI801733A
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English (en)
Finnish (fi)
Other versions
FI801733A (fi
FI72530C (sv
Inventor
Kyoji Kimoto
Hirotsugu Miyauchi
Jukichi Ohmura
Mikio Ebisawa
Toshioki Hane
Original Assignee
Asahi Chemical Ind
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP6788979A external-priority patent/JPS55160007A/ja
Priority claimed from JP54067888A external-priority patent/JPS6045653B2/ja
Priority claimed from JP54085852A external-priority patent/JPS5910658B2/ja
Priority claimed from JP9030279A external-priority patent/JPS5616460A/ja
Priority claimed from JP9030179A external-priority patent/JPS5912116B2/ja
Application filed by Asahi Chemical Ind filed Critical Asahi Chemical Ind
Publication of FI801733A publication Critical patent/FI801733A/fi
Publication of FI72530B publication Critical patent/FI72530B/fi
Application granted granted Critical
Publication of FI72530C publication Critical patent/FI72530C/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/78—Halides of sulfonic acids
    • C07C309/79—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms
    • C07C309/82—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms of a carbon skeleton substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/78—Halides of sulfonic acids
    • C07C309/79—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms
    • C07C309/84—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms of a carbon skeleton substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • C08F214/00—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 halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/184—Monomers containing fluorine with fluorinated vinyl ethers
    • 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
    • C08F214/00—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 halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/26—Tetrafluoroethene
    • C08F214/262—Tetrafluoroethene with fluorinated vinyl ethers
    • 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
    • C08F216/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F216/12—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
    • C08F216/14—Monomers containing only one unsaturated aliphatic radical
    • C08F216/1466—Monomers containing sulfur
    • C08F216/1475—Monomers containing sulfur and oxygen
    • 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
    • C08F8/04—Reduction, e.g. hydrogenation
    • 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
    • C08F8/12—Hydrolysis
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/20—Manufacture of shaped structures of ion-exchange resins
    • C08J5/22—Films, membranes or diaphragms
    • C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
    • C08J5/2218—Synthetic macromolecular compounds
    • C08J5/2231—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds
    • C08J5/2237—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2327/00—Characterised by the use of homopolymers or 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 halogen; Derivatives of such polymers
    • C08J2327/02—Characterised by the use of homopolymers or 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 halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/12—Characterised by the use of homopolymers or 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 halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (20)

1. Fluorerat katjonbytarmembran innehällande huvudsakligen följande aterkommande enheter (C), (D) och (E): (C) -tCF2-CF2-> (D) tCF2-CF* X (E) tCF2-CF* Y kännetecknat därav, att CF3 X är -0- ( CF2CF0)k~ (CF2 ) £-S03M och CF3 Y är -0-(CF2CF0)k(CF2)m-C02M i vilka formler k är 0 eller 1, £ är ett heltal 3-5, M är H, en metall- eller ammoniumjon och m är lika med (?.-l) och att det upp-visas en densitet av karboxylsyragrupp av atminstone 20 % pa mem-branets ena yta, varvid karboxylsyragruppens densitet gradvis mins-kar fran nämnda ena yta av membranet mot membranets inre.
2. Fluorerat katjonbytarmembran enligt patentkravet 1, k ä n-netecknat därav, att förhallandet mellan antalet aterkommande enheter (C)/[(D) + [E)] är inom intervallet 1,5-14.
3. Fluorerat katjonbytarmembran enligt patentkravet 2, k ä n-netecknat därav, att nämnda förhallande är inom interval- 72530 69 let 3-11.
4. Fluorerat katjonbytarmembran enligt nagot av patentkraven 1-3, kännetecknat därav, att karboxylsyragruppens den-si tet pä membranets ena yta är 40 % eller högre.
5. Fluorerat katjonbytarmembran enligt patentkravet 4, k ä n-netecknat därav, att karboxylsyragruppens densitet pa membranets ena yta är 60 % eller högre.
6. Fluorerat katjonbytarmembran enligt nagot av patentkraven 1-5, kännetecknat därav, att karboxylsyragruppens densitet minskar mot membranets inre med en gradient av högst 20 %/μιη.
7. Fluorerat katjonbytarmembran enligt patentkravet 6, k ä n-netecknat därav, att karboxylsyragruppens densitet upp-nar i huvudsak värdet noli % vid ett djup av högst i av membranets totala tjocklek fran ytan.
8. Fluorerat katjonbytarmembran enligt nagot av patentkraven 1-7, kännetecknat därav, att k är 0.
9. Fluorerat katjonbytarmembran enligt nagot av patentkraven 1-8, kännetecknat därav, att l är 3.
10. Fluorerat katjonbytarmembran enligt patentkravet l,k ä n-netecknat därav, att det är förstärkt med ett förstärk-ningsmaterial.
11. Fluorerat katjonbytarmembran innehallande ett membran enligt patentkravet 1, kännetecknat därav, att pa membranets ena yta vilken uppvisar en lägre densitet av karboxyl-syragrupp laminerats ett fluorerat katjonbytarmembran innehallande sulfonsyragrupper.
12. Fluorerat katjonbytarmembran enligt patentkravet 11, kännetecknat därav, att det fluorerade katjonbytar-membranet som innehaller sulfonsyragrupper bestär i huvudsak av enheterna (C): (C) tCF2-CF2)- och följande aterkommande enhet (F): (F) tCF2-CF* CF3 O-(CF2CFO)p"-(CH2)q-S03M i vilken p" är 0 eller 1, q är ett heltal 3-5 och M betecknar det- 70 72 5 30 samma som i patentkravet 1, varvid förhallandet mellan antalet aterkommande enheter (C)/(F) är (C)/(F) < (C)/[(D) + (E)]
13. Fluorerat katjonbytarmembran enligt patentkravet 11 eller 12, känneteckna t därav, att tjockleken av det katjonbytarmembran som innehaller en sulfonsyragrupp Mr i eller högre av det laminerade membranets totala tjocklek.
14. Fluorerat katjonbytarmembran enligt patentkravet 11 eller 12, kännetecknat därav, att membranet förstärkts med ett förstärkningsmaterial.
15. Fluorerat katjonbytarmembran enligt patentkravet 14, kännetecknat därav, att förstärkningsmaterialet är inbäddat i membranet med sulfonsyragrupper.
16. Förfarande för att framställa ett fluorerat katjonbytarmembran enligt patentkravet 1, kännetecknat därav, att ett ytlager av ett membran av en fluorerad kopolymer innehal-lande i huvudsak följande aterkommande enheter (C) och (H): (C) tCF2-CF2* (H) fCF2-CF* CF3 O- ( CF2CFO) j^- ( cf2 ) £-S02X" i vilken k är noll eller 1, l är ett heltal 3-5 och X" är Cl eller Br, med en vattenlösning av atminstone ett reduktionsmedel som är en reduktionsduglig oorganisk syra, dess sait eller hydrazin, i närvaro av atminstone en organisk förening med 1-12 kolatomer, som är en karboxylsyra eller en sulfonsyra.
17. Förfarande enligt patentkravet 16, kännetecknat därav, att man använder en blandlösning innehallande den organiska föreningen upplöst i den vattenhaltiga lösningen av re-duktionsmedlet.
18. Förfarande enligt patentkravet 16, kännetecknat därav, att reduktionsmedlet är en reduktionsduglig oorganisk syra.
19. Förfarande enligt patentkravet 16, kännetecknat därav, att den organiska föreningen är en C]_-Ci2-karboxyl-syra.
20. Förfarande för framställning av ett fluorerat katjonby-
FI801733A 1979-05-31 1980-05-28 Fluorerat katjonbytarmembran och laminat samt förfarande för dess fram ställning. FI72530C (sv)

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
JP6788979A JPS55160007A (en) 1979-05-31 1979-05-31 Novel fluorinated copolymer and production thereof
JP6788879 1979-05-31
JP6788979 1979-05-31
JP54067888A JPS6045653B2 (ja) 1979-05-31 1979-05-31 新規なフツ素化陽イオン交換膜及びその製造方法
JP54085852A JPS5910658B2 (ja) 1979-07-09 1979-07-09 新規なフツ素化ビニルエ−テル化合物及びその製法
JP8585279 1979-07-09
JP9030279A JPS5616460A (en) 1979-07-18 1979-07-18 Novel fluorinated carboxylic acid derivative and its preparation
JP9030279 1979-07-18
JP9030179 1979-07-18
JP9030179A JPS5912116B2 (ja) 1979-07-18 1979-07-18 新規なフッ素化酸フッ化物及びその製造方法

Publications (3)

Publication Number Publication Date
FI801733A FI801733A (fi) 1980-12-01
FI72530B true FI72530B (fi) 1987-02-27
FI72530C FI72530C (sv) 1987-06-08

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Application Number Title Priority Date Filing Date
FI801733A FI72530C (sv) 1979-05-31 1980-05-28 Fluorerat katjonbytarmembran och laminat samt förfarande för dess fram ställning.

Country Status (12)

Country Link
US (4) US4329434A (sv)
BR (1) BR8003432A (sv)
CA (2) CA1185398A (sv)
DE (4) DE3050439C2 (sv)
FI (1) FI72530C (sv)
FR (4) FR2457880B1 (sv)
IN (1) IN154418B (sv)
IT (1) IT1193942B (sv)
NL (1) NL184740C (sv)
NO (1) NO153398C (sv)
PT (1) PT72131B (sv)
SE (1) SE449999B (sv)

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GB1518387A (en) * 1975-08-29 1978-07-19 Asahi Glass Co Ltd Fluorinated cation exchange membrane and use thereof in electrolysis of an alkali metal halide
JPS5833249B2 (ja) 1975-09-19 1983-07-19 旭硝子株式会社 含フツ素陽イオン交換樹脂膜
BG23472A1 (sv) 1975-12-05 1977-09-15
JPS5284191A (en) * 1975-12-30 1977-07-13 Asahi Glass Co Ltd Improved f-contg. cation exchange resin membrane
NO145235C (no) * 1976-08-06 1982-02-10 Montedison Spa Oxafluoralkansyrer eller sulfonsyrederivater for anvendelse som reaktanter ved dannelse av ionebytterharpikser
JPS5349090A (en) * 1976-10-15 1978-05-04 Asahi Glass Co Ltd Preparation of fluorinated plymer containing ion exchange group
JPS5359842U (sv) * 1976-10-25 1978-05-22
FR2388013B1 (fr) * 1977-04-20 1985-08-02 Du Pont Polymeres fluores echangeurs d'ions contenant des groupes carboxyliques, leur preparation et leur utilisation dans des cellules d'electrolyse chlore-alcali
FR2388012A1 (fr) * 1977-04-20 1978-11-17 Du Pont Polymere fluore echangeur d'ions contenant des groupes carboxyliques et pellicules et membranes constituees de ce polymere
US4176215A (en) * 1978-03-13 1979-11-27 E. I. Du Pont De Nemours And Company Ion-exchange structures of copolymer blends useful in electrolytic cells

Also Published As

Publication number Publication date
SE8003901L (sv) 1980-12-01
DE3046501C2 (de) 1987-04-23
FR2508039B1 (sv) 1985-02-15
FR2457880B1 (sv) 1986-07-04
FR2473533A1 (fr) 1981-07-17
DE3050782C2 (sv) 1988-05-26
IN154418B (sv) 1984-10-27
DE3020057A1 (de) 1981-05-27
FR2473533B1 (fr) 1986-02-28
CA1185398A (en) 1985-04-09
NL184740C (nl) 1989-10-16
DE3050439A1 (sv) 1982-07-22
IT1193942B (it) 1988-08-31
BR8003432A (pt) 1981-01-05
SE449999B (sv) 1987-06-01
FR2483431B1 (fr) 1986-03-21
NO153398B (no) 1985-12-02
US4555369A (en) 1985-11-26
NO153398C (no) 1986-03-12
FR2457880A1 (sv) 1980-12-26
DE3050439C2 (sv) 1989-11-09
US4597913A (en) 1986-07-01
NL8003174A (nl) 1980-12-02
IT8022468A0 (it) 1980-05-30
FR2508039A1 (sv) 1982-12-24
FI801733A (fi) 1980-12-01
FR2483431A1 (fr) 1981-12-04
PT72131B (en) 1981-09-24
NO801637L (no) 1980-12-01
US4329434A (en) 1982-05-11
US4510328A (en) 1985-04-09
PT72131A (en) 1980-12-01
DE3020057C2 (sv) 1987-06-25
CA1168263A (en) 1984-05-29
FI72530C (sv) 1987-06-08
DE3046501A1 (de) 1983-02-17

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