JP5485491B2 - 電子部品製造に用いるのに適する超クリーンフルオロエラストマー - Google Patents
電子部品製造に用いるのに適する超クリーンフルオロエラストマー Download PDFInfo
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- JP5485491B2 JP5485491B2 JP2004524943A JP2004524943A JP5485491B2 JP 5485491 B2 JP5485491 B2 JP 5485491B2 JP 2004524943 A JP2004524943 A JP 2004524943A JP 2004524943 A JP2004524943 A JP 2004524943A JP 5485491 B2 JP5485491 B2 JP 5485491B2
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- JP
- Japan
- Prior art keywords
- perfluoropolymer
- fluoropolymer
- perfluorinated
- curing
- fluorinated
- 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.)
- Expired - Lifetime
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- 229920001973 fluoroelastomer Polymers 0.000 title claims description 48
- 238000004519 manufacturing process Methods 0.000 title description 14
- 239000000203 mixture Substances 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 42
- -1 sulfonyl radical Chemical class 0.000 claims description 34
- 229920005548 perfluoropolymer Polymers 0.000 claims description 33
- 239000000178 monomer Substances 0.000 claims description 31
- 238000001723 curing Methods 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 29
- 150000001768 cations Chemical class 0.000 claims description 25
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- 150000002978 peroxides Chemical class 0.000 claims description 19
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 239000006185 dispersion Substances 0.000 claims description 15
- 239000003999 initiator Substances 0.000 claims description 14
- 125000002560 nitrile group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 150000003841 chloride salts Chemical class 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 238000004132 cross linking Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 5
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 5
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims description 5
- 150000001451 organic peroxides Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 4
- 238000010556 emulsion polymerization method Methods 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims 1
- 229920002313 fluoropolymer Polymers 0.000 description 57
- 239000004811 fluoropolymer Substances 0.000 description 57
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- 150000003839 salts Chemical class 0.000 description 23
- 239000000460 chlorine Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 15
- 238000007720 emulsion polymerization reaction Methods 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 11
- 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 10
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 150000002825 nitriles Chemical class 0.000 description 10
- 229920006169 Perfluoroelastomer Polymers 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 239000004816 latex Substances 0.000 description 9
- 229920000126 latex Polymers 0.000 description 9
- 239000004530 micro-emulsion Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000002835 absorbance Methods 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 230000015271 coagulation Effects 0.000 description 7
- 238000005345 coagulation Methods 0.000 description 7
- 229920001971 elastomer Polymers 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910021645 metal ion Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 238000010257 thawing Methods 0.000 description 5
- AYCANDRGVPTASA-UHFFFAOYSA-N 1-bromo-1,2,2-trifluoroethene Chemical group FC(F)=C(F)Br AYCANDRGVPTASA-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- TXEIIPDJKFWEEC-UHFFFAOYSA-N tafamidis Chemical compound O1C2=CC(C(=O)O)=CC=C2N=C1C1=CC(Cl)=CC(Cl)=C1 TXEIIPDJKFWEEC-UHFFFAOYSA-N 0.000 description 4
- 235000012431 wafers Nutrition 0.000 description 4
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 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 3
- 239000002879 Lewis base Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- YOALFLHFSFEMLP-UHFFFAOYSA-N azane;2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoic acid Chemical compound [NH4+].[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YOALFLHFSFEMLP-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 3
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 150000004010 onium ions Chemical class 0.000 description 3
- FYJQJMIEZVMYSD-UHFFFAOYSA-N perfluoro-2-butyltetrahydrofuran Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F FYJQJMIEZVMYSD-UHFFFAOYSA-N 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 3
- 125000005270 trialkylamine group Chemical group 0.000 description 3
- TWIYDBQRYCWOAU-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfinic acid Chemical compound OS(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F TWIYDBQRYCWOAU-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229920001774 Perfluoroether Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- XQJHRCVXRAJIDY-UHFFFAOYSA-N aminophosphine Chemical compound PN XQJHRCVXRAJIDY-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000001112 coagulating effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 150000002463 imidates Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- AQZYBQIAUSKCCS-UHFFFAOYSA-N perfluorotripentylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AQZYBQIAUSKCCS-UHFFFAOYSA-N 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- CZMILNXHOAKSBR-UHFFFAOYSA-N tetraphenylazanium Chemical compound C1=CC=CC=C1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CZMILNXHOAKSBR-UHFFFAOYSA-N 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- AXFFGMPNSZVEDX-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19,20,20,21,21,22,22,23,23,24,24,24-pentacontafluorotetracosane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AXFFGMPNSZVEDX-UHFFFAOYSA-N 0.000 description 1
- LWRNQOBXRHWPGE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8a-heptadecafluoro-8-(trifluoromethyl)naphthalene Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(C(F)(F)F)(F)C(F)(F)C(F)(F)C(F)(F)C21F LWRNQOBXRHWPGE-UHFFFAOYSA-N 0.000 description 1
- QIROQPWSJUXOJC-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(trifluoromethyl)cyclohexane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F QIROQPWSJUXOJC-UHFFFAOYSA-N 0.000 description 1
- YSGKVOMJRCQYMT-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]-2-(trifluoromethoxy)ethane Chemical compound FC(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)(F)OC(F)(F)F YSGKVOMJRCQYMT-UHFFFAOYSA-N 0.000 description 1
- YCMPCPHVHGPYHB-UHFFFAOYSA-N 1,1-diethyl-2,2-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N(CC)CC)C1=CC=CC=C1 YCMPCPHVHGPYHB-UHFFFAOYSA-N 0.000 description 1
- IEKMPJDJWCSGKX-UHFFFAOYSA-N 1,2,3,4,5,6,7,8,9,9-decafluorofluorene Chemical compound FC1(F)C2=C(F)C(F)=C(F)C(F)=C2C2=C1C(F)=C(F)C(F)=C2F IEKMPJDJWCSGKX-UHFFFAOYSA-N 0.000 description 1
- JDCMOHAFGDQQJX-UHFFFAOYSA-N 1,2,3,4,5,6,7,8-octafluoronaphthalene Chemical compound FC1=C(F)C(F)=C(F)C2=C(F)C(F)=C(F)C(F)=C21 JDCMOHAFGDQQJX-UHFFFAOYSA-N 0.000 description 1
- USPWUOFNOTUBAD-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F USPWUOFNOTUBAD-UHFFFAOYSA-N 0.000 description 1
- HFWOSHMLDRSIDN-UHFFFAOYSA-N 1,3,5-trinitroso-1,3,5-triazinane Chemical compound O=NN1CN(N=O)CN(N=O)C1 HFWOSHMLDRSIDN-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 1
- DAVCAHWKKDIRLY-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)OC=C DAVCAHWKKDIRLY-UHFFFAOYSA-N 0.000 description 1
- WFJINAXLTGKWLB-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2,3,3-hexafluoro-3-(trifluoromethoxy)propane Chemical compound FC(F)(F)OC(F)(F)C(F)(F)C(F)(F)OC=C WFJINAXLTGKWLB-UHFFFAOYSA-N 0.000 description 1
- YKWORVRLPTZONH-UHFFFAOYSA-N 1-ethenoxy-1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propane Chemical compound FC(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC=C YKWORVRLPTZONH-UHFFFAOYSA-N 0.000 description 1
- FCHGUOSEXNGSMK-UHFFFAOYSA-N 1-tert-butylperoxy-2,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(OOC(C)(C)C)=C1C(C)C FCHGUOSEXNGSMK-UHFFFAOYSA-N 0.000 description 1
- LYIPDZSLYLDLCU-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-3-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoroethenoxy)propan-2-yl]oxypropanenitrile Chemical compound FC(F)=C(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C#N LYIPDZSLYLDLCU-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- ODBCKCWTWALFKM-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-yne Chemical compound CC(C)(C)OOC(C)(C)C#CC(C)(C)OOC(C)(C)C ODBCKCWTWALFKM-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
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- CBNXGQUIJRGZRX-UHFFFAOYSA-N 5-[4-fluoro-3-(trifluoromethyl)phenyl]furan-2-carbaldehyde Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C1=CC=C(C=O)O1 CBNXGQUIJRGZRX-UHFFFAOYSA-N 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 241001441571 Hiodontidae Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
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- 125000000129 anionic group Chemical group 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
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- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- UZCPNEBHTFYJNY-UHFFFAOYSA-N benzyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 UZCPNEBHTFYJNY-UHFFFAOYSA-N 0.000 description 1
- QSRFYFHZPSGRQX-UHFFFAOYSA-N benzyl(tributyl)azanium Chemical compound CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 QSRFYFHZPSGRQX-UHFFFAOYSA-N 0.000 description 1
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- BNQRPLGZFADFGA-UHFFFAOYSA-N benzyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 BNQRPLGZFADFGA-UHFFFAOYSA-N 0.000 description 1
- JGTUMZJDTJDJJR-UHFFFAOYSA-N benzyl-tris(dimethylamino)phosphanium Chemical compound CN(C)[P+](N(C)C)(N(C)C)CC1=CC=CC=C1 JGTUMZJDTJDJJR-UHFFFAOYSA-N 0.000 description 1
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
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- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 1
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- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- BLYOHBPLFYXHQA-UHFFFAOYSA-N n,n-bis(prop-2-enyl)prop-2-enamide Chemical compound C=CCN(CC=C)C(=O)C=C BLYOHBPLFYXHQA-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical group FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 229950011087 perflunafene Drugs 0.000 description 1
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 1
- LOQGSOTUHASIHI-UHFFFAOYSA-N perfluoro-1,3-dimethylcyclohexane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)C1(F)F LOQGSOTUHASIHI-UHFFFAOYSA-N 0.000 description 1
- 125000005460 perfluorocycloalkyl group Chemical group 0.000 description 1
- UWEYRJFJVCLAGH-IJWZVTFUSA-N perfluorodecalin Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)[C@@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@@]21F UWEYRJFJVCLAGH-IJWZVTFUSA-N 0.000 description 1
- 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 1
- QKENRHXGDUPTEM-UHFFFAOYSA-N perfluorophenanthrene Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C3(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C3(F)C(F)(F)C(F)(F)C21F QKENRHXGDUPTEM-UHFFFAOYSA-N 0.000 description 1
- 239000010702 perfluoropolyether Chemical group 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical compound C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OSWMMVUHYHQYCV-UHFFFAOYSA-N tetrabenzylazanium Chemical compound C=1C=CC=CC=1C[N+](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 OSWMMVUHYHQYCV-UHFFFAOYSA-N 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- YFZDLRVCXDBOPH-UHFFFAOYSA-N tetraheptylazanium Chemical compound CCCCCCC[N+](CCCCCCC)(CCCCCCC)CCCCCCC YFZDLRVCXDBOPH-UHFFFAOYSA-N 0.000 description 1
- DTIFFPXSSXFQCJ-UHFFFAOYSA-N tetrahexylazanium Chemical compound CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC DTIFFPXSSXFQCJ-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-UHFFFAOYSA-N 0.000 description 1
- IUVXCVGGLRYGFE-UHFFFAOYSA-N tetraphenyl-lambda5-arsane hydrochloride Chemical compound C1=CC=C(C=C1)[AsH](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.Cl IUVXCVGGLRYGFE-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- BTMIENSZKMNLRR-UHFFFAOYSA-N tributyl(2-methoxypropyl)phosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CC(C)OC BTMIENSZKMNLRR-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39922902P | 2002-07-29 | 2002-07-29 | |
| US60/399,229 | 2002-07-29 | ||
| PCT/US2003/023530 WO2004011510A1 (en) | 2002-07-29 | 2003-07-25 | Ultraclean fluoroelastomer suitable for use in the manufacturing of electronic components |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012009419A Division JP5778589B2 (ja) | 2002-07-29 | 2012-01-19 | 電子部品製造に用いるのに適する超クリーンフルオロエラストマー |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005534751A JP2005534751A (ja) | 2005-11-17 |
| JP2005534751A5 JP2005534751A5 (enExample) | 2009-01-08 |
| JP5485491B2 true JP5485491B2 (ja) | 2014-05-07 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004524943A Expired - Lifetime JP5485491B2 (ja) | 2002-07-29 | 2003-07-25 | 電子部品製造に用いるのに適する超クリーンフルオロエラストマー |
| JP2012009419A Expired - Fee Related JP5778589B2 (ja) | 2002-07-29 | 2012-01-19 | 電子部品製造に用いるのに適する超クリーンフルオロエラストマー |
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| Application Number | Title | Priority Date | Filing Date |
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| EP (1) | EP1525237B2 (enExample) |
| JP (2) | JP5485491B2 (enExample) |
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| CN (2) | CN101974188B (enExample) |
| AU (1) | AU2003256929A1 (enExample) |
| RU (1) | RU2005101205A (enExample) |
| WO (1) | WO2004011510A1 (enExample) |
| ZA (1) | ZA200501644B (enExample) |
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| KR101143208B1 (ko) * | 2002-07-29 | 2012-05-18 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 전자 부품의 제조에 사용하기에 적합한 초청정플루오로엘라스토머 |
| EP1576020B1 (en) * | 2002-12-23 | 2011-01-26 | 3M Innovative Properties Company | Fluoroplastic polymers having nitrogen-containing cure sites |
| WO2005000917A1 (en) * | 2003-01-29 | 2005-01-06 | Greene, Tweed Of Delaware, Inc. | Bisaminopehnyl-based curatives curatives and amidine-based curatives and cure accelerators for perfluoroelastomeric compositions. |
| US20040214956A1 (en) | 2003-01-29 | 2004-10-28 | Greene, Tweed Of Delaware, Inc. | Bisaminophenyl-based curatives and amidine-based curatives and cure accelerators for perfluoroelastomeric compositions |
| US7514506B2 (en) | 2004-03-31 | 2009-04-07 | Greene, Tweed Of Delaware, Inc. | Fast curing fluoroelastomeric compositions, adhesive fluoroelastomeric compositions and methods for bonding fluoroelastomeric compositions |
| US20060024370A1 (en) * | 2004-07-29 | 2006-02-02 | Cephalon France | Modafinil oral lyophilizate |
| DE602006013623D1 (de) * | 2005-05-02 | 2010-05-27 | Daikin Ind Ltd | Verfahren zur herstellung von fluorhaltigem polymer |
| US7488781B2 (en) | 2005-05-25 | 2009-02-10 | Gore Enterprise Holdings, Inc. | High purity transparent perfluoroelastomer parts and a process to produce the same |
| US20060270780A1 (en) * | 2005-05-25 | 2006-11-30 | Ping Xu | High purity perfluoroelastomer composites and a processes to produce the same |
| CN101821301B (zh) * | 2007-10-12 | 2012-06-27 | 3M创新有限公司 | 制备纯净含氟聚合物的方法 |
| JP5452508B2 (ja) * | 2008-02-29 | 2014-03-26 | スリーエム イノベイティブ プロパティズ カンパニー | 低カルボニル末端基率を有するペルフルオロエラストマー |
| JP2011529977A (ja) | 2008-07-31 | 2011-12-15 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロポリマー組成物並びにその製造及び使用方法 |
| GB0814955D0 (en) | 2008-08-18 | 2008-09-24 | 3M Innovative Properties Co | Azide-containing fluoropolymers and their preparation |
| EP2445939B1 (en) * | 2009-06-25 | 2020-09-23 | 3M Innovative Properties Company | Curing compositions for fluoropolymers |
| GB201012944D0 (en) * | 2010-08-02 | 2010-09-15 | 3M Innovative Properties Co | Peroxide curable fluoroelastomers containing modifiers and iodine or bromine endgroups |
| JP5986102B2 (ja) * | 2010-12-17 | 2016-09-06 | スリーエム イノベイティブ プロパティズ カンパニー | マイクロエマルジョン及びマイクロエマルジョンを用いて作製されたフルオロポリマー |
| US20130053519A1 (en) * | 2011-08-31 | 2013-02-28 | E. I. Du Pont De Nemours And Company | Acid resistant fluoroelastomer compositions |
| JP6143798B2 (ja) | 2012-02-10 | 2017-06-07 | スリーエム イノベイティブ プロパティズ カンパニー | 耐食コーティング |
| US9976045B2 (en) | 2013-11-07 | 2018-05-22 | 3M Innovative Properties Company | Fluoropolymer coatings comprising aziridine compounds |
| EP3066169A1 (en) | 2013-11-07 | 2016-09-14 | 3M Innovative Properties Company | Fluoropolymer coatings comprising aziridine compounds and non-fluorinated polymer |
| JP6608587B2 (ja) * | 2014-10-17 | 2019-11-20 | 三菱ケミカル株式会社 | 半導体リソグラフィー用材料の製造方法および製造装置 |
| CN107690452B (zh) * | 2015-05-29 | 2020-12-04 | 3M创新有限公司 | 包含*唑的全氟弹性体组合物 |
| JP2019510856A (ja) * | 2016-03-24 | 2019-04-18 | ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． | フルオロエラストマー組成物 |
| WO2018078015A1 (en) * | 2016-10-27 | 2018-05-03 | Solvay Specialty Polymers Italy S.P.A. | Fluoroelastomer composition |
| EP3632939B1 (en) * | 2017-06-02 | 2023-07-26 | AGC Inc. | Modified polytetrafluoroethylene and method for producing same |
| GB201807544D0 (en) * | 2018-05-09 | 2018-06-20 | 3M Innovative Properties Co | Fluoropolymers with very low amounts of a fluorinated alkanoic acid or its salts |
| EP3807344B1 (en) | 2018-06-12 | 2023-12-27 | 3M Innovative Properties Company | Fluoropolymer coating compositions comprising aminosilane curing agents, coated substrates and related methods |
| US11866602B2 (en) | 2018-06-12 | 2024-01-09 | 3M Innovative Properties Company | Fluoropolymer compositions comprising fluorinated additives, coated substrates and methods |
| CN114630874B (zh) | 2019-11-04 | 2023-12-05 | 3M创新有限公司 | 包含具有烯键式不饱和基团和电子供体基团的固化剂的含氟聚合物组合物及用其涂覆的基底 |
| WO2021088198A1 (en) * | 2019-11-04 | 2021-05-14 | 3M Innovative Properties Company | Electronic telecommunications articles comprising crosslinked fluoropolymers and methods |
| TW202244165A (zh) * | 2021-02-17 | 2022-11-16 | 美商3M新設資產公司 | 抗黏全氟彈性體物品及製造方法 |
| US20240381528A1 (en) * | 2021-07-30 | 2024-11-14 | The Chemours Company Fc, Llc | Flexible laminate material |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4035565A (en) * | 1975-03-27 | 1977-07-12 | E. I. Du Pont De Nemours And Company | Fluoropolymer containing a small amount of bromine-containing olefin units |
| NL189567C (nl) * | 1977-12-14 | 1993-05-17 | Montedison Spa | Vulcaniseerbare mengsels op basis van elastomere copolymeren van vinylideenfluoride, werkwijze om deze te vulcaniseren en voorwerpen geheel of gedeeltelijk bestaande uit de zo verkregen gevulcaniseerde mengsels. |
| US4281092A (en) * | 1978-11-30 | 1981-07-28 | E. I. Du Pont De Nemours And Company | Vulcanizable fluorinated copolymers |
| IT1187684B (it) * | 1985-07-08 | 1987-12-23 | Montefluos Spa | Procedimento per la preparazione di fluoroelastomeri vulcanizzabili e prodotti cosi' ottenuti |
| JPS62260807A (ja) * | 1986-05-07 | 1987-11-13 | Nippon Mektron Ltd | 含フッ素重合体の製造方法 |
| US5266650A (en) * | 1990-10-11 | 1993-11-30 | Minnesota Mining And Manufacturing Company | Curing fluorocarbon elastomers |
| DE4233824A1 (de) * | 1992-10-08 | 1994-04-14 | Hoechst Ag | Verfahren zur Aufarbeitung wäßriger Dispersionen von Fluorthermoplasten |
| US5285002A (en) * | 1993-03-23 | 1994-02-08 | Minnesota Mining And Manufacturing Company | Fluorine-containing polymers and preparation and use thereof |
| DE69408460T2 (de) * | 1993-07-16 | 1998-05-20 | Du Pont | Hochreine fluorelastomerzusammensetzungen |
| IT1265461B1 (it) | 1993-12-29 | 1996-11-22 | Ausimont Spa | Fluoroelastomeri comprendenti unita' monomeriche derivanti da una bis-olefina |
| CN1117775C (zh) | 1995-02-06 | 2003-08-13 | 纳幕尔杜邦公司 | 四氟乙烯和六氟丙烯的非弹性的无定形共聚物及其涂层制品 |
| JP3223776B2 (ja) * | 1995-03-31 | 2001-10-29 | 日本メクトロン株式会社 | 含フッ素エラストマー組成物 |
| IT1273608B (it) * | 1995-04-28 | 1997-07-08 | Ausimont Spa | Fluoroelastomeri sostanzialmente privi di terminali polari e relativo processo di preparazione |
| DE69610099T2 (de) * | 1995-06-30 | 2001-05-10 | E.I. Du Pont De Nemours And Co., Wilmington | Verfahren zur herstellung von fluor-enthaltenden polymeren |
| JP3082626B2 (ja) * | 1995-07-19 | 2000-08-28 | 日本メクトロン株式会社 | 含フッ素エラストマー組成物 |
| IT1276980B1 (it) * | 1995-10-20 | 1997-11-03 | Ausimont Spa | Composizioni fluoroelastomeriche |
| IT1276979B1 (it) | 1995-10-20 | 1997-11-03 | Ausimont Spa | Composizioni fluoroelastomeriche |
| WO1998023655A1 (en) * | 1996-11-25 | 1998-06-04 | E.I. Du Pont De Nemours And Company | Perfluoroelastomer composition having improved processability |
| US5936060A (en) * | 1996-11-25 | 1999-08-10 | E. I. Du Pont De Nemours And Company | Perfluoroelastomer composition having improved processability |
| US6114452A (en) * | 1996-11-25 | 2000-09-05 | E. I. Du Pont De Nemours And Company | Perfluoroelastomer composition having excellent heat stability |
| US5677389A (en) * | 1996-11-25 | 1997-10-14 | E. I. Du Pont De Nemours | Perfluoroelastomer composition having enhanced curing performance |
| JP4110736B2 (ja) * | 1998-03-25 | 2008-07-02 | ダイキン工業株式会社 | 含フッ素エラストマーの金属含有量低減化方法 |
| US6281296B1 (en) | 1998-08-10 | 2001-08-28 | Dupont Dow Elastomers L.L.C. | Curable perfluoroelastomer composition |
| WO2000042100A1 (en) * | 1999-01-12 | 2000-07-20 | Daikin Industries, Ltd. | Crosslinkable elastomer composition and formed article prepared from said composition |
| US6593416B2 (en) * | 2000-02-01 | 2003-07-15 | 3M Innovative Properties Company | Fluoropolymers |
| US6720360B1 (en) * | 2000-02-01 | 2004-04-13 | 3M Innovative Properties Company | Ultra-clean fluoropolymers |
| WO2001092351A2 (en) * | 2000-06-01 | 2001-12-06 | 3M Innovative Properties Company | High purity fluoropolymers |
| KR101143208B1 (ko) * | 2002-07-29 | 2012-05-18 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 전자 부품의 제조에 사용하기에 적합한 초청정플루오로엘라스토머 |
-
2003
- 2003-07-25 KR KR1020057001550A patent/KR101143208B1/ko not_active Expired - Fee Related
- 2003-07-25 EP EP03771966.3A patent/EP1525237B2/en not_active Expired - Lifetime
- 2003-07-25 AU AU2003256929A patent/AU2003256929A1/en not_active Abandoned
- 2003-07-25 US US10/627,461 patent/US6943228B2/en not_active Expired - Lifetime
- 2003-07-25 CN CN2010102967849A patent/CN101974188B/zh not_active Expired - Lifetime
- 2003-07-25 CN CNA038175207A patent/CN1671757A/zh active Pending
- 2003-07-25 JP JP2004524943A patent/JP5485491B2/ja not_active Expired - Lifetime
- 2003-07-25 KR KR1020117004987A patent/KR101143122B1/ko not_active Expired - Fee Related
- 2003-07-25 WO PCT/US2003/023530 patent/WO2004011510A1/en not_active Ceased
- 2003-07-25 RU RU2005101205/04A patent/RU2005101205A/ru not_active Application Discontinuation
-
2005
- 2005-02-24 ZA ZA200501644A patent/ZA200501644B/xx unknown
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- 2012-01-19 JP JP2012009419A patent/JP5778589B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005534751A (ja) | 2005-11-17 |
| WO2004011510A1 (en) | 2004-02-05 |
| KR101143208B1 (ko) | 2012-05-18 |
| CN101974188B (zh) | 2012-05-30 |
| JP5778589B2 (ja) | 2015-09-16 |
| AU2003256929A1 (en) | 2004-02-16 |
| JP2012072417A (ja) | 2012-04-12 |
| KR20050033623A (ko) | 2005-04-12 |
| CN101974188A (zh) | 2011-02-16 |
| US6943228B2 (en) | 2005-09-13 |
| US20040024134A1 (en) | 2004-02-05 |
| KR20110040964A (ko) | 2011-04-20 |
| RU2005101205A (ru) | 2005-08-10 |
| ZA200501644B (en) | 2005-09-06 |
| KR101143122B1 (ko) | 2012-05-08 |
| EP1525237B1 (en) | 2015-01-21 |
| CN1671757A (zh) | 2005-09-21 |
| EP1525237A1 (en) | 2005-04-27 |
| EP1525237B2 (en) | 2021-01-27 |
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