CN105175589A - 在含氟聚合物树脂的制备中所利用的氟醚羧酸或盐的去除 - Google Patents
在含氟聚合物树脂的制备中所利用的氟醚羧酸或盐的去除 Download PDFInfo
- Publication number
- CN105175589A CN105175589A CN201510673885.6A CN201510673885A CN105175589A CN 105175589 A CN105175589 A CN 105175589A CN 201510673885 A CN201510673885 A CN 201510673885A CN 105175589 A CN105175589 A CN 105175589A
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- CN
- China
- Prior art keywords
- salt
- carboxylic acid
- fluorine ether
- product
- ether carboxylic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000003839 salts Chemical class 0.000 title claims abstract description 131
- 229920002313 fluoropolymer Polymers 0.000 title claims abstract description 66
- 239000004811 fluoropolymer Substances 0.000 title claims abstract description 64
- 239000011347 resin Substances 0.000 title claims abstract description 45
- 229920005989 resin Polymers 0.000 title claims abstract description 45
- 229920001774 Perfluoroether Polymers 0.000 title abstract 6
- 150000001735 carboxylic acids Chemical class 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 224
- -1 alkali metal cation Chemical class 0.000 claims abstract description 124
- 238000000034 method Methods 0.000 claims abstract description 64
- 239000006227 byproduct Substances 0.000 claims abstract description 49
- 239000000178 monomer Substances 0.000 claims abstract description 36
- 239000006185 dispersion Substances 0.000 claims abstract description 32
- 239000003999 initiator Substances 0.000 claims abstract description 27
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000002245 particle Substances 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 165
- 239000011737 fluorine Substances 0.000 claims description 162
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 49
- 238000006114 decarboxylation reaction Methods 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000002250 absorbent Substances 0.000 claims description 14
- 230000002745 absorbent Effects 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 230000009466 transformation Effects 0.000 claims description 9
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 238000003795 desorption Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 38
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
- 239000012736 aqueous medium Substances 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000012985 polymerization agent Substances 0.000 abstract 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 46
- 239000004721 Polyphenylene oxide Substances 0.000 description 41
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 41
- 229920000570 polyether Polymers 0.000 description 41
- 239000004094 surface-active agent Substances 0.000 description 38
- 239000002253 acid Substances 0.000 description 23
- 238000006116 polymerization reaction Methods 0.000 description 19
- 239000011833 salt mixture Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 11
- 239000012986 chain transfer agent Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 229920001971 elastomer Polymers 0.000 description 10
- 239000000806 elastomer Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 9
- 229920001519 homopolymer Polymers 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000012674 dispersion polymerization Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- GVEUEBXMTMZVSD-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohex-1-ene Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C GVEUEBXMTMZVSD-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000005352 clarification Methods 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- YSYRISKCBOPJRG-UHFFFAOYSA-N 4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(F)OC(C(F)(F)F)(C(F)(F)F)O1 YSYRISKCBOPJRG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000002242 deionisation method Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 3
- 238000005304 joining Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 239000002594 sorbent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000002912 waste gas Substances 0.000 description 3
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 description 2
- JMGNVALALWCTLC-UHFFFAOYSA-N 1-fluoro-2-(2-fluoroethenoxy)ethene Chemical compound FC=COC=CF JMGNVALALWCTLC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004160 Ammonium persulphate Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 239000004812 Fluorinated ethylene propylene Substances 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000004159 Potassium persulphate Substances 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000019395 ammonium persulphate Nutrition 0.000 description 2
- 230000003698 anagen phase Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 150000005826 halohydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000006911 nucleation Effects 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229920009441 perflouroethylene propylene Polymers 0.000 description 2
- 238000005502 peroxidation Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 235000019394 potassium persulphate Nutrition 0.000 description 2
- 238000003822 preparative gas chromatography Methods 0.000 description 2
- 238000011112 process operation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 238000002098 selective ion monitoring Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 description 1
- MLRCQIICAYVJHD-UHFFFAOYSA-N 1-but-1-enoxybut-1-ene Chemical compound CCC=COC=CCC MLRCQIICAYVJHD-UHFFFAOYSA-N 0.000 description 1
- PEEJGKOZOSHKNF-UHFFFAOYSA-N 1-ethenoxy-2-ethoxypropane;sulfuryl difluoride Chemical compound FS(F)(=O)=O.CCOC(C)COC=C PEEJGKOZOSHKNF-UHFFFAOYSA-N 0.000 description 1
- XTXQXZPIBVPGMZ-UHFFFAOYSA-N 1-ethenoxypropan-2-yloxybenzene Chemical compound C=COCC(C)OC1=CC=CC=C1 XTXQXZPIBVPGMZ-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- QMIWYOZFFSLIAK-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene Chemical compound FC(F)(F)C(=C)C(F)(F)F QMIWYOZFFSLIAK-UHFFFAOYSA-N 0.000 description 1
- ZXABMDQSAABDMG-UHFFFAOYSA-N 3-ethenoxyprop-1-ene Chemical compound C=CCOC=C ZXABMDQSAABDMG-UHFFFAOYSA-N 0.000 description 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- HYWVMDJRPASBJK-UHFFFAOYSA-N COC(CCOC(COC=C)C)=O Chemical class COC(CCOC(COC=C)C)=O HYWVMDJRPASBJK-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229920001780 ECTFE Polymers 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229920004463 Voltalef® Polymers 0.000 description 1
- 150000001265 acyl fluorides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
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- 238000006555 catalytic reaction Methods 0.000 description 1
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- 238000000576 coating method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
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- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 239000008232 de-aerated water Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
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- 239000004446 fluoropolymer coating Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000003988 headspace gas chromatography Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000004966 inorganic peroxy acids Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
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- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
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- 229910021645 metal ion Inorganic materials 0.000 description 1
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- 238000012544 monitoring process Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical group OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
-
- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/14—Treatment of polymer emulsions
- C08F6/16—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/36—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- 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
- C08F114/00—Homopolymers 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
- C08F114/18—Monomers containing fluorine
- C08F114/26—Tetrafluoroethene
-
- 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
- C08F14/00—Homopolymers and 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
- C08F14/18—Monomers containing fluorine
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
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| US5189808P | 2008-05-09 | 2008-05-09 | |
| US61/051898 | 2008-05-09 | ||
| CN2009801167502A CN102015779A (zh) | 2008-05-09 | 2009-05-08 | 在含氟聚合物树脂的制备中所利用的氟醚羧酸或盐的去除 |
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| CN2009801167502A Division CN102015779A (zh) | 2008-05-09 | 2009-05-08 | 在含氟聚合物树脂的制备中所利用的氟醚羧酸或盐的去除 |
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| CN105175589A true CN105175589A (zh) | 2015-12-23 |
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| CN2009801167502A Pending CN102015779A (zh) | 2008-05-09 | 2009-05-08 | 在含氟聚合物树脂的制备中所利用的氟醚羧酸或盐的去除 |
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| EP (1) | EP2285841B1 (enExample) |
| JP (1) | JP5778028B2 (enExample) |
| CN (2) | CN105175589A (enExample) |
| WO (1) | WO2009137734A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113156033A (zh) * | 2020-12-11 | 2021-07-23 | 广州广电计量检测股份有限公司 | 一种空气中氢氟醚溶剂的热解析-气相色谱-质谱检测方法 |
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| WO2009014167A1 (ja) * | 2007-07-24 | 2009-01-29 | Daikin Industries, Ltd. | 新規化合物、その製造方法及びフルオロポリマーの製造方法 |
| US8329813B2 (en) * | 2009-05-08 | 2012-12-11 | E I Du Pont De Nemours And Company | Thermal reduction of fluoroether carboxylic acids or salts from fluoropolymer dispersions |
| EP2927246B1 (en) | 2013-01-23 | 2017-10-25 | Daikin Industries, Ltd. | Method for recovering fluorine-containing ether |
| US9574027B2 (en) * | 2013-03-11 | 2017-02-21 | The Chemours Company Fc, Llc | Fluoropolymer resin treatment employing sorbent to reduce fluoropolymer resin discoloration |
| US9694333B2 (en) | 2014-04-18 | 2017-07-04 | 3M Innovative Properties Company | Recovery of branched fluorinated emulsifiers |
| CN105418908B (zh) * | 2015-12-31 | 2019-03-29 | 天津市长芦化工新材料有限公司 | 一种全氟聚醚酰氟水解过程乳化现象解决方法 |
| WO2018181904A1 (ja) | 2017-03-31 | 2018-10-04 | ダイキン工業株式会社 | フルオロポリマーの製造方法、重合用界面活性剤及び界面活性剤の使用 |
| EP3858871A1 (en) | 2017-03-31 | 2021-08-04 | Daikin Industries, Ltd. | Composition comprising a fluoropolymer |
| JP6939916B2 (ja) | 2018-02-08 | 2021-09-22 | ダイキン工業株式会社 | フルオロポリマーの製造方法、重合用界面活性剤、界面活性剤の使用及び組成物 |
| US11767379B2 (en) | 2018-03-01 | 2023-09-26 | Daikin Industries, Ltd. | Method for manufacturing fluoropolymer |
| WO2019172382A1 (ja) | 2018-03-07 | 2019-09-12 | ダイキン工業株式会社 | フルオロポリマーの製造方法 |
| JP6959600B2 (ja) * | 2019-03-05 | 2021-11-02 | 三井・ケマーズ フロロプロダクツ株式会社 | ガスクロマトグラフィー質量分析用溶媒 |
| US12503560B2 (en) | 2019-04-16 | 2025-12-23 | Daikin Industries, Ltd. | Method for producing fluoropolymer powder |
| US20220251251A1 (en) | 2019-04-26 | 2022-08-11 | Daikin Industries, Ltd. | Fluoropolymer aqueous dispersion production method and fluoropolymer aqueous dispersion |
| JP7564452B2 (ja) | 2019-04-26 | 2024-10-09 | ダイキン工業株式会社 | フルオロポリマー水性分散液の製造方法 |
| CN118146427A (zh) | 2019-07-23 | 2024-06-07 | 大金工业株式会社 | 含氟聚合物的制造方法、聚四氟乙烯组合物和聚四氟乙烯粉末 |
| JP7741413B2 (ja) | 2021-06-11 | 2025-09-18 | ダイキン工業株式会社 | 含フッ素エラストマー水性分散液の製造方法、組成物および水性分散液 |
| CN114015033B (zh) * | 2021-09-30 | 2024-06-18 | 四川弘氟新材料有限公司 | 一种含氟聚醚羧酸型表面活性剂及其制备方法 |
| WO2025024411A1 (en) * | 2023-07-24 | 2025-01-30 | The Chemours Company Fc, Llc | Processes of fluorinated residual reduction in fluoropolymers |
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| CN1505645A (zh) * | 2001-05-02 | 2004-06-16 | 3M | 制备氟聚合物的无乳化剂水乳液聚合方法 |
| US20070015864A1 (en) * | 2005-07-15 | 2007-01-18 | 3M Innovative Properties Company | Method of making fluoropolymer dispersion |
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| US3271341A (en) * | 1961-08-07 | 1966-09-06 | Du Pont | Aqueous colloidal dispersions of polymer |
| US3291843A (en) * | 1963-10-08 | 1966-12-13 | Du Pont | Fluorinated vinyl ethers and their preparation |
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| FR2286153A1 (fr) * | 1974-09-24 | 1976-04-23 | Ugine Kuhlmann | Procede de polymerisation ou de copolymerisation en emulsion du fluorure de vinylidene |
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| US4552631A (en) * | 1983-03-10 | 1985-11-12 | E. I. Du Pont De Nemours And Company | Reinforced membrane, electrochemical cell and electrolysis process |
| US4569978A (en) * | 1984-07-25 | 1986-02-11 | Pennwalt Corporation | Emulsion polymerization of vinylidene fluoride polymers in the presence of trichlorofluoromethane as chain transfer agent |
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| IT1274591B (it) * | 1994-08-05 | 1997-07-18 | Ausimont Spa | Processo per la preparazione di poliossiperfluoroalcani idrogeno terminati |
| US5637748A (en) * | 1995-03-01 | 1997-06-10 | E. I. Du Pont De Nemours And Company | Process for synthesizing fluorinated nitrile compounds |
| US5763552A (en) * | 1996-07-26 | 1998-06-09 | E. I. Du Pont De Nemours And Company | Hydrogen-containing flourosurfacant and its use in polymerization |
| US5969067A (en) * | 1996-09-13 | 1999-10-19 | E.I. Dupont De Nemours And Company | Phosphorus-containing fluoromonomers and polymers thereof |
| US5866711A (en) * | 1996-09-13 | 1999-02-02 | E. I. Du Pont De Nemours And Company | Fluorocyanate and fluorocarbamate monomers and polymers thereof |
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| WO2009001894A1 (ja) * | 2007-06-28 | 2008-12-31 | Daikin Industries, Ltd. | ポリテトラフルオロエチレン水性分散液及びその製造方法 |
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2009
- 2009-05-06 US US12/436,273 patent/US20090281261A1/en not_active Abandoned
- 2009-05-08 WO PCT/US2009/043222 patent/WO2009137734A1/en not_active Ceased
- 2009-05-08 JP JP2011508693A patent/JP5778028B2/ja not_active Expired - Fee Related
- 2009-05-08 CN CN201510673885.6A patent/CN105175589A/zh active Pending
- 2009-05-08 EP EP09743720A patent/EP2285841B1/en not_active Not-in-force
- 2009-05-08 CN CN2009801167502A patent/CN102015779A/zh active Pending
-
2015
- 2015-04-02 US US14/676,865 patent/US20150203427A1/en not_active Abandoned
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1172122A (zh) * | 1996-07-01 | 1998-02-04 | 奥西蒙特公司 | Vdf聚合方法 |
| CN1505645A (zh) * | 2001-05-02 | 2004-06-16 | 3M | 制备氟聚合物的无乳化剂水乳液聚合方法 |
| US20070015864A1 (en) * | 2005-07-15 | 2007-01-18 | 3M Innovative Properties Company | Method of making fluoropolymer dispersion |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113156033A (zh) * | 2020-12-11 | 2021-07-23 | 广州广电计量检测股份有限公司 | 一种空气中氢氟醚溶剂的热解析-气相色谱-质谱检测方法 |
| CN113156033B (zh) * | 2020-12-11 | 2023-11-24 | 广电计量检测集团股份有限公司 | 一种空气中氢氟醚溶剂的热解析-气相色谱-质谱检测方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2285841A1 (en) | 2011-02-23 |
| WO2009137734A1 (en) | 2009-11-12 |
| JP2011520020A (ja) | 2011-07-14 |
| US20090281261A1 (en) | 2009-11-12 |
| JP5778028B2 (ja) | 2015-09-16 |
| CN102015779A (zh) | 2011-04-13 |
| EP2285841B1 (en) | 2012-11-14 |
| US20150203427A1 (en) | 2015-07-23 |
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