METHOD FOR PRODUCING FLUORINE-CONTAINING COMPOUND HAVING IODINE ATOM CONTENT REDUCED

Abstract

The purpose of the present invention is to obtain a fluorine-containing compound which is easily stabilized without irradiation of ultraviolet light, by efficiently converting a CI bond in an iodine-containing compound having a group represented by CFRfI (wherein Rf is a fluorine atom or a perfluoroalkyl group) to a CH bond. A method for producing a fluorine-containing compound having an iodine atom content reduced than the following iodine-containing compound, which comprises subjecting an iodine-containing compound having a group represented by CFRfI (wherein Rf is a fluorine atom or a perfluoroalkyl group) to deiodinating treatment in the presence of an organic peroxide and a hydrogen-containing compound having a group represented by CHR.sup.1CHR.sup.2CHR.sup.3 (wherein R.sup.1, R.sup.2 and R.sup.3 are each independently a hydrogen atom or an alkyl group).

Claims

1. A method for producing a fluorine-containing compound having an iodine atom content reduced than the following iodine-containing compound, which comprises subjecting an iodine-containing compound having a group represented by the following formula (1i) or a group represented by the following formula (2i), to deiodinating treatment in the presence of an organic peroxide and a hydrogen-containing compound having a group represented by the following formula (3): ##STR00012## in the formula (1i), Rf is a fluorine atom or a perfluoroalkyl group; in the formula (2i), the ring containing Rf is a 5- or 6-membered ring, Rf is a perfluoroalkylene group having a linear or branched structure, which may have an etheric oxygen atom, and R.sup.a and R.sup.b are each independently a fluorine atom, a C.sub.1-5 perfluoroalkyl group or a C.sub.1-5 perfluoroalkoxy group, and in the formula (3), R.sup.1, R.sup.2 and R.sup.3 are each independently a hydrogen atom or an alkyl group.

2. The method according to claim 1, wherein the fluorine-containing compound has a group represented by the following formula (1h) or a group represented by the following formula (2h): ##STR00013## Rf in the formula (1 h) and Rf, R.sup.a and R.sup.b in the formula (2h) are as defined above.

3. The method according to claim 1, wherein the iodine-containing compound is a compound represented by the following formula (4), or a compound represented by the following formula (5):
Q.sup.1-CFRfIFormula (4)
Q.sup.2-(CFRfI).sub.2Formula (5) in the formula (4), Rf is a fluorine atom or a perfluoroalkyl group, and Q.sup.1 is a fluorine atom or a polyfluoroalkyl group which may have an etheric oxygen atom, and in the formula (5), Rf are each independently a fluorine atom or a perfluoroalkyl group, and Q.sup.2 is a polyfluoroalkylene group which may have an etheric oxygen atom.

4. The method according to claim 1, wherein the iodine-containing compound is a polymer compound which has at least one CI bond, wherein all of hydrogen atoms bonded to carbon atoms are substituted by fluorine atoms.

5. The method according to claim 1, wherein the organic peroxide has a 10 hour half-life temperature of from 10 C. to 150 C.

6. The method according to claim 5, wherein the hydrogen-containing compound is an alkane.

7. The method according to claim 1, wherein the total number of moles of the organic peroxide is from 0.0005 to 5 times to the total number of moles of iodine atoms in the iodine-containing compound.

8. The method according to claim 1, wherein the total number of moles of the hydrogen-containing compound is from 5 to 500 times to the total number of moles of iodine atoms in the iodine-containing compound.

9. The method according to claim 1, wherein the iodine-containing compound is treated in a fluorine-containing solvent.

10. The method according to claim 1, wherein the concentration of the iodine-containing compound is from 0.1 to 50 mass % to the reaction liquid in the solution of the fluorine-containing solvent.

11. The method according to claim 1, wherein the concentration of the hydrogen-containing compound is from 0.1 to 30 mass % to the reaction liquid in the solution of the fluorine-containing solvent.

12. The method according to claim 1, wherein the heating temperature in the deiodinating treatment of the iodine-containing compound is between T C. and T+80 C., where T C. is the 10-hour half-life temperature of the organic peroxide.

13. The method according to claim 1, wherein the iodine atom content in the fluorine-containing compound is at most 10% of the iodine atom content in the iodine-containing compound.

Description

EXAMPLES

[0148] In the following Examples, Ex. 1 to 8, 10, 12 to 15, 21 to 26 and 30 are Examples of the present invention, and Ex. 9, 11 and 27 to 29 are Comparative Examples.

[0149] (Iodine-Containing Compounds)

PHVE-I: CF.sub.3CF.sub.2CF.sub.2OCF(CF.sub.3)CF.sub.2OCF.sub.2CF.sub.2I

[0150] (Monomer (m1))

8IVE: CF.sub.2CFOCF.sub.2 CF(CF.sub.3)OCF.sub.2 CF.sub.2I(m1-1)

[0151] (Monomer (m2))

[0152] PDD:

##STR00009##

[0153] (Monomer (m2))

BVE: CF.sub.2CFOCF.sub.2CF.sub.2CFCF.sub.2(m24-1)

[0154] (Monomer (m3))

[0155] PSVE:

CF.sub.2CFOCF.sub.2CF(CF.sub.3)OCF.sub.2CF.sub.2SO.sub.2F(m31-1)

[0156] BSVE-2E:

##STR00010##

[0157] (Monomer (m4))

TFE: CF.sub.2CF.sub.2(m4-1)

[0158] (Organic Peroxides)

[0159] IPP: diisopropyl peroxydicarbonate

[0160] PBPV: t-butyl peroxypivalate

[0161] (Solvents)

[0162] HFC-52-13p: CF.sub.3(CF.sub.2).sub.5H,

[0163] HCFC-141b: CH.sub.3CCl.sub.2F,

[0164] HCFC-225cb: CClF.sub.2CF.sub.2CHClF,

[0165] HCFC-225: mixture of CClF.sub.2 CF.sub.2CHClF and CF.sub.3CF.sub.2CHCl.sub.2.

[0166] [Synthesis of 8IVE (m1-1)]

[0167] 8IVE (m1-1) was synthesized in the same manner as the method described in Huaxue Xuebao, Vol. 47, No. 7, 1989, pp. 720-723.

[0168] [Synthesis Example for Branched Polymer (1)]

[0169] A branched polymer (1) having units based on 8IVE (m1-1) and units based on BVE (m24-1) was synthesized as follows.

[0170] Into a Hastelloy autoclave having an internal capacity of 120 mL, 3.67 g (7.5 mmol) of 8IVE was charged. A liquid having 1.546 g (7.5 mmol) of IPP dissolved in about 15 g of HFC-52-13p and 18.77 g (67.5 mmol) of BVE were added, and finally HFC-52-13p was added. The total amount of HFC-52-13p added, was 44.01 g. Using liquid nitrogen, freeze/degassing was repeated twice to return the temperature to approximately 0 C., and then, nitrogen gas was introduced until 0.3 MPaG. The autoclave was set in a water bath, followed by stirring for 4 hours while maintaining the internal temperature at 45 C. Then, the temperature was raised to 55 C. over a period of 10 minutes, followed by stirring for 1 hour. Further, the temperature was raised to 65 C. over 10 minutes, followed by stirring for 1 hour, whereupon the temperature was raised to 70 C. over a period of 5 minutes, followed by stirring for one hour. Then, the autoclave was immersed in ice water and cooled to at most 20 C., to terminate the reaction.

[0171] The reaction liquid was transferred to a beaker from the autoclave, and about 110 g of HFC-52-13p was added. About 110 g of n-hexane was added, followed by stirring and being left overnight. The content of the beaker was transferred to an eggplant flask, and the solvent was distilled off by an evaporator, followed by vacuum drying at 60 C. for about 200 hours, to obtain 20.65 g of a solid (a branched polymer (1)). The mass average molecular weight calculated as polymethyl methacrylate measured by GPC was 8,700.

[0172] The branched polymer (1) was dissolved in perfluorobenzene, and .sup.19F-NMR (the chemical shift of perfluorobenzene was set to be 162.7 ppm, the same applies hereinafter) was measured, whereby the ratio of the number of terminals of BVE units bonded to iodine atoms, to the number of OCF.sub.2CF.sub.2I groups based on 8IVE units with iodine atoms undissociated, was found to be 29:71 from the ratio of the peaks at from 44 to 54 ppm to the peak in the vicinity of 62 ppm, and thus, it was confirmed that this polymer contained branched molecular chains. The iodine atom content obtained by the elemental analysis was 3.4 mass %, and from this value, the molar ratio (8IVE/BVE) of units derived from 8IVE (m1-1) to units derived from BVE (m24-1) was calculated to be 1/12.

[0173] [Synthesis Example for Branched Multi-Segmented Copolymer (2)]

[0174] A branched multi-segmented copolymer (2) comprising a segment having units based on 8IVE (m1-1) and units based on PDD (m21-1), and a segment having units based on TFE (m4-1) and units based on BSVE-2E (m32-1), was synthesized as follows.

[0175] In a Hastelloy autoclave having an internal capacity of 230 mL, 5.72 g (11.7 mmol) of 8IVE was charged. A liquid having 0.241 g (1.17 mmol) of IPP dissolved in 5 g of HCFC-225cb and 25.63 g (105.0 mmol) of PDD were added, and finally HCFC-225cb was added. The total amount of HCFC-225cb added, was 118.42 g. Using liquid nitrogen, freeze/degassing was repeated twice, to return the temperature to about 0 C., and then, nitrogen gas was introduced until 0.3 MPaG (G denotes gauge pressure, the same applies hereinafter). The autoclave was set in a water bath, followed by stirring for 8 hours while maintaining the internal temperature at 45 C. After the stirring, the autoclave was immersed in ice water and cooled to at most 20 C. to terminate the reaction.

[0176] The jelly-like product was transferred to a beaker from the autoclave, and HCFC-225cb was added. The total amount was 214 g. After stirring for 5 minutes by a magnetic stirrer, 261 g of n-hexane was added to coagulate the polymer, followed by stirring continuously for 30 minutes. Vacuum filtration was conducted, and the obtained polymer was washed with n-hexane. The polymer was returned to the beaker, and HCFC-225cb was added to bring the total amount to be 214 g, followed by stirring for 5 minutes. 261 g of n-hexane was added to coagulate the polymer, followed by stirring for 30 minutes. Vacuum filtration was conducted, followed by washing with n-hexane, and then, again HCFC-225cb was added and stirred in the same manner, followed by agglomeration with n-hexane, filtration and washing with n-hexane. Then, drying was conducted in a vacuum oven at 60 C. to a constant weight, to obtain 23.75 g of a white powdery polymer (2).

[0177] With respect to the polymer (2), the content of iodine atoms was examined by the elemental analysis and found to be 2.8 mass %. From this value, the molar ratio (8IVE/PDD) of units derived from 8IVE (m1-1) to units derived from PDD (m21-1) in the polymer (2) was calculated to be 1/17 (5.6/94.4). The mass average molecular weight of the polymer (2) calculated as polymethyl methacrylate obtained by GPC was 18,700. The polymer (2) was dissolved in perfluorobenzene, and .sup.19F-NMR was measured, whereby it was found that units derived from PDD bonded to iodine atoms were present and the polymer (2) was confirmed to have branched structures. The ratio of units derived from PDD to which iodine atoms were bonded, to units derived from 8IVE where iodine atoms were not dissociated, was found to be 46:54 from the ratio of the peaks at from 42 to 47 ppm to the peak in the vicinity of 62 ppm in .sup.19F-NMR (solvent: perfluorobenzene).

[0178] Into a Hastelloy autoclave having an internal capacity of 230 mL, 6.99 g of the polymer (2) and 260.32 g of BSVE-2E, were charged, and the autoclave was closed, whereupon the gas phase was replaced with nitrogen. The temperature was raised to 40 C., followed by stirring for 12 hours to dissolve the polymer (2). After cooling to room temperature, 18.3 mg of IPP dissolved in 1.73 g of HFC-52-13p was added, and by using liquid nitrogen, freeze/degassing was repeated twice. While raising the temperature, TFE was introduced continuously, and the temperature and pressure were held constant at a temperature 40 C. under a pressure of 0.50 MPaG. Upon expiration of 10 minutes after the temperature became constant at 40 C., consumption of TFE began. Upon expiration of 4.3 hours after the TFE feed amount reached 2.37 g under the constant pressure, the autoclave was cooled to 10 C. TFE in the autoclave was purged to terminate the reaction.

[0179] After the product was diluted with 15 g of HCFC-225, 200 g of HCFC-141b was added, to precipitate the polymer, followed by filtration. The polymer was dissolved again in 150 g of HCFC-225 and precipitated by addition of 50 g of n-hexane and 140 g of HCFC-141 b, followed by filtration. The operation of dissolution and precipitation was carried out again by using the same amount of the solvent. Then, the polymer was dried at 80 C. under reduced pressure overnight, to obtain 13.3 g of a copolymer (2) being a branched multi-segmented copolymer comprising a precursor of a segment (B) consisting of units derived from TFE (m4-1) and units derived from BSVE-2E (m32-1), and a segment (A) consisting of units derived from PDD (m21-1) and units derived from 8IVE (m1-1).

[0180] The molar ratio of the units in the segment (B) obtained from .sup.19F-NMR (solvent: perfluorobenzene) of the copolymer (2), was TFE/BSVE-2E=78.9/21.1, and the ion exchange capacity of the segment was calculated to be 2.00 meq/g dry resin. The ion exchange capacity of the copolymer (2) obtained by a titration method was 1.22 meq/g dry resin.

[0181] The peak of the measured GPC chart was one, and the mass average molecular weight of the copolymer (2) calculated as polymethyl methacrylate was 101,000.

[0182] [Synthesis Example for Branched Polymer (3)]

[0183] Copolymerization of 8IVE and PDD was carried out in the same manner as the above synthesis of the polymer (2), to obtain a polymer (3) having an iodine content of 2.2 mass % and containing a branched molecular chain wherein the molar ratio of 8IVE to PDD was 1:22. The mass average molecular weight of the polymer (3) calculated as polymethyl methacrylate obtained by GPC was 18,900.

[0184] [Synthesis Example for Branched Multi-Segmented Copolymer (4)]

[0185] By the same operation as the synthesis for the branched multi-segmented copolymer (2), a branched polymer was synthesized which had a segment made of a copolymer of 8IVE and PDD (the molar ratio of the units was 8IVE/PDD=5.0/95.0) and a segment made of a copolymer of TFE and BSVE-2E (the molar ratio of the units was TFE/BSVE-2E=79.1/20.9). The ion exchange capacity was 1.42 meq/g dry resin.

Ex. 1

[0186] Into a Hastelloy autoclave having an internal capacity of 34 mL, PHVE-I, IPP (diisopropyl peroxydicarbonate) being an organic peroxide as the radical generating source, n-hexane as the hydrogen-containing compound, HCFC-225cb (1,3-dichloro-1,1,2,2,3-pentafluoropropane) as a solvent, were added. Using liquid nitrogen, freeze/degassing was repeated twice to return the temperature to about 0 C., and then nitrogen gas was introduced until 0.3 MPaG, followed by heat treatment at 70 C. for 7 hours.

[0187] In the above charging, the total amount of the charged liquid was 18 g, and the concentration of PHVE-I was made to be 5 mass %. The ratio of the total number of moles of the organic peroxide (IPP) to the total number of moles of iodine atoms in PHVE-I was made to be 2. The concentration of the hydrogen-containing compound (hexane) was made to be 10 mass %. At that time, the ratio of the total number of moles of the hydrogen-containing compound (hexane) to the total number of moles of iodine atoms in PHVE-I was 13.4.

[0188] The yield of CF.sub.3CF.sub.2CF.sub.2OCF(CF.sub.3)CF.sub.2OCF.sub.2CF.sub.2H (hereinafter referred to as PHVE-H) obtained, was 96.8%.

Ex. 2 to 11

[0189] Heat treatment was conducted in the same manner as in Ex. 1 except that the following conditions were changed as shown in Table 1. The yield of the obtained PHVE-H is shown in Table 1. [0190] The concentration of PHVE-I in the HCFC-225cb solution. [0191] The type of the radical-generating source (organic peroxide), and the ratio of the total number of moles of the radical generating source to the total number of moles of iodine atoms in PHVE-I. [0192] The type of the chain transfer agent, the total number of moles of the chain transfer agent to the total number of moles of iodine atoms in PHVE-I, and the concentration of the chain transfer agent in the HCFC-225cb solution.

[0193] Further, In Ex. 8, the reaction temperature was made to be 60 C., and in Ex. 11, the reaction temperature was made to be 75 C.

TABLE-US-00001 TABLE 1 PHVE-I Radical Chain transfer agent Concen- generating Concen- tration source tration Yield Ex. (mass %) Type Ratio Type Ratio (mass %) (%) 1 5 IPP 2 n-hexane 13.4 10 96.8 2 5 IPP 0.5 n-hexane 13.4 10 96.9 3 5 IPP 0.1 n-hexane 13.4 10 96.6 4 5 IPP 0.1 n-hexane 1.0 0.74 28.5 5 5 IPP 0.01 n-hexane 13.4 10 74.7 6 5 IPP 0.002 n-hexane 13.4 10 29.8 7 0.5 IPP 0.1 n-hexane 13.4 1 97.2 8 5 IPP 0.1 n-hexane 13.4 10 96.7 9 5 IPP 0.1 Toluene 12.6 10 Not reacted 10 5 PBPV 0.5 n-hexane 13.4 10 94.3 11 5 AIBN 0.1 n-hexane 13.4 10 Not reacted

Ex. 12

[0194] The reaction was conducted under the same conditions as in Ex. 3, except that instead of PHVE-I, CF.sub.3CF.sub.2CF.sub.2OCF(CF.sub.3)CF.sub.2OCF(CF.sub.3)I was used. The obtained product was CF.sub.3CF.sub.2CF.sub.2OCF(CF.sub.3)CF.sub.2OCF(CF.sub.3)H, and the yield was 98.1%.

Ex. 13

[0195] In a stainless steel autoclave having an internal capacity of 110 mL, IPP as the organic peroxide and n-hexane as the hydrogen-containing compound were added to a solution having 1.35 g of the branched polymer (1) dissolved in HCFC-225cb. Using liquid nitrogen, freeze/degassing was repeated twice, to return the temperature to about 0 C., and then nitrogen gas was introduced until 0.3 MPaG, followed by stirring at 70 C. for 7 hours.

[0196] In the above reaction, the concentration of the branched polymer (1) to HCFC-225cb was made to be 2 mass %. The ratio of the total number of moles of the organic peroxide (IPP) to the total number of moles of iodine atoms in the branched polymer (1) was made to be 2. The concentration of the hydrogen-containing compound (n-hexane) to the total charged weight was made to be 1 mass %. At that time, the ratio of the total number of moles of the hydrogen-containing compound to the total number of moles of iodine atoms in the branched polymer (1) was 22.

[0197] With respect to the reaction product, using a perfluorobenzene solvent, .sup.19F-NMR measurement was conducted, whereby it was found that the peaks due to CF.sub.2I bonds had disappeared, and .sup.1H-NMR measurement was conducted whereby a peak (triplet) due to a H atom in CF.sub.2H was observed at 6.0 ppm.

Ex. 14

[0198] The treatment of the branched polymer (1) was carried out in the same manner as in Ex. 13, except that the ratio of the total number of moles of the organic peroxide (IPP) to the total number of moles of iodine atoms in the branched polymer (1) was made to be 0.5.

[0199] With respect to the reaction product, using a perfluorobenzene solvent, .sup.19F-NMR measurement was conducted, whereby it was found that the peaks due to CF.sub.2I bonds had disappeared, and .sup.1H-NMR measurement was conducted whereby a peak (triplet) due to a H atom in CF.sub.2H was observed at 6.0 ppm.

Ex. 15

[0200] In Ex. 13, the object to be treated was changed from the branched polymer (1) to the branched polymer (3). Further, the concentration of the branched polymer (3) to HCFC-225cb was changed to be 1.5 mass %. The ratio of the total number of moles of the organic peroxide (IPP) to the total number of moles of iodine atoms in the branched polymer (3) was made to be 0.5. The concentration of the hydrogen-containing compound (n-hexane) to the total charged weight was made to be 1 mass %. At that time, the total number of moles of the hydrogen containing compound to the total number of moles of iodine atoms in the branched polymer (1) was 45. The treatment was carried out by setting other conditions in the same manner as in Ex. 13.

[0201] With respect to the reaction product, using a perfluorobenzene solvent, .sup.19F-NMR measurement was conducted, whereby it was found that the peaks at from 42 to 47 ppm and the peak in the vicinity of 62 ppm due to fluorine atoms bonded to the same carbon atom as the iodine atom had disappeared. .sup.1H-NMR was measured whereby a triplet due to a H atom in CF.sub.2H was observed at 6.0 ppm, and a doublet due to a H atom based on the following structure was observed at 6.6 ppm.

##STR00011##

Ex. 21

[0202] With respect to the branched multi-segmented copolymer (2), the iodine atom content was measured by the elemental analysis and found to be 0.9 mass %.

[0203] In a Hastelloy autoclave having an internal capacity of 34 mL, IPP as the organic peroxide, n-hexane as the hydrogen-containing compound and additional HCFC-225cb were added to a solution having 0.45 g of the copolymer (2) dissolved in HCFC-225cb at a concentration of 3 mass %. Using liquid nitrogen, freeze/degassing was repeated twice to return the temperature to about 0 C., and then, nitrogen gas was introduced until 0.3 MPaG, followed by heat treatment at 70 C. for 7 hours.

[0204] In the above reaction, the concentration of the copolymer (2) to the total charged amount was made to be 2 mass %. The ratio of the total number of moles of the organic peroxide to the total number of moles of iodine atoms in the copolymer (2) was made to be 16.4. The concentration of the hydrogen-containing compound (n-hexane) to the total charged amount was made to be 1 mass %. The ratio of the total number of moles of the hydrogen-containing compound to the total number of moles of iodine atoms in the copolymer (2) was 82.

[0205] The residual iodine content in the polymer after the heat treatment was measured by the elemental analysis and found to be 0.02%.

Ex. 22 to 29

[0206] Heat treatment was carried out in the same manner as in Ex. 21, except that the following conditions were changed as shown in Table 2. The yield of the polymer after the heat treatment is shown in Table 2. [0207] The concentration of the copolymer (2) in the total charged liquid. [0208] The ratio of the total number of moles of the organic peroxide to the total number of moles of iodine atoms in the copolymer (2). [0209] The type of the chain transfer agent, and the ratio of the total number of moles of the chain transfer agent to the total numbers of moles of iodine atoms in the copolymer (2).

[0210] Further, In Ex. 28, the reaction conditions were set to be such that heating at 60 C. for 5 hours, was followed by heating at 70 C. for 3 hours.

TABLE-US-00002 TABLE 2 Co- Iodine polymer atom (2) content Concen- Organic Chain transfer agent Concen- tration peroxide Concen- tration Ex. (mass %) Type Ratio Type Ratio tration (mass %) 21 2 IPP 16.4 n-hexane 82 1 0.02 22 2 IPP 8.2 n-hexane 82 1 0.02 23 2 IPP 4.1 n-hexane 82 1 0.03 24 2 IPP 1.6 n-hexane 82 1 0.04 25 4 IPP 4.1 n-hexane 41 1 0.04 26 2 IPP 16.4 Isohexane 82 1 0.02 27 2 IPP 16.4 Nil 0.2 28 2 IPP 16.4 Nil 0.07 29 2 IPP 16.4 Methanol 220 1 0.41

Ex. 30

[0211] With respect to the branched multi-segmented copolymer (4), the iodine atom content was measured by the elemental analysis and found to be 0.49 mass %.

[0212] This polymer was dissolved in a HCFC-225cb solvent, and the reaction was conducted at 70 C. for 7 hours in the same manner as in Ex. 21. However, in the above reaction, the concentration of the copolymer (4) to the total charged amount was made to be 2 mass %. The ratio of the total number of moles of the organic peroxide (IPP) to the total number of moles of iodine atoms in the copolymer (4) was made to be 5.4. The concentration of the hydrogen-containing compound (n-hexane) in the total charged amount was made to be 1 mass %. The ratio of the total number of moles of the hydrogen-containing compound to the total number of moles of iodine atoms in the copolymer (4) was 150.

[0213] After the reaction, the temperature was returned to room temperature, and then, a HCFC-225cb solution of IPP (concentration 3 mass %) was added. The ratio of the total number of moles of IPP to the total number of moles of iodine atoms in the copolymer (4) originally charged, was 5.5. The same operation was again carried out to conduct the reaction at 70 C. for 7 hours. With respect to the obtained polymer, the elemental analysis was carried out, whereby iodine atoms were not detected (less than 0.01 mass %).

INDUSTRIAL APPLICABILITY

[0214] The fluorine-containing polymer compound containing fluorosulfonyl groups obtainable by the present invention is useful as an intermediate for an electrolyte material for polymer electrolyte fuel cells. Further, it may be used as an intermediate for other applications (water electrolysis, hydrogen peroxide production, ozone production, proton permselective membrane to be used for spent acid recovery, etc.; sodium chloride electrolysis, diaphragm for redox flow battery, cation exchange membrane for electrodialysis to be used for desalting or salt production, moisture-removing membrane, humidifying membrane, acid catalyst for chemical reactions, a sensor, gas separation membrane, etc.). The fluorine-containing polymer compound containing no ionic groups obtainable by the process of the present invention, is useful as insulating film for a semiconductor device or electronic circuit board, optical waveguide material, antireflection material, sealing material, water repellent, oil repellent, etc.

[0215] This application is a continuation of PCT Application No. PCT/JP2016/084325, filed on Nov. 18, 2016, which is based upon and claims the benefit of priority from Japanese Patent Application No. 2015-227178 filed on Nov. 20, 2015. The contents of those applications are incorporated herein by reference in their entireties.