JP2004524425A - フルオロポリマー組成物 - Google Patents
フルオロポリマー組成物 Download PDFInfo
- Publication number
- JP2004524425A JP2004524425A JP2002582105A JP2002582105A JP2004524425A JP 2004524425 A JP2004524425 A JP 2004524425A JP 2002582105 A JP2002582105 A JP 2002582105A JP 2002582105 A JP2002582105 A JP 2002582105A JP 2004524425 A JP2004524425 A JP 2004524425A
- Authority
- JP
- Japan
- Prior art keywords
- fluoropolymer
- composition
- composition according
- alkyl
- nitrogen
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 143
- 229920002313 fluoropolymer Polymers 0.000 title claims abstract description 121
- 239000004811 fluoropolymer Substances 0.000 title claims abstract description 119
- 239000000178 monomer Substances 0.000 claims abstract description 53
- 239000003054 catalyst Substances 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000001450 anions Chemical class 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 10
- 239000002243 precursor Substances 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000006698 induction Effects 0.000 claims abstract description 7
- 229910052787 antimony Chemical group 0.000 claims abstract description 6
- 229910052785 arsenic Inorganic materials 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 5
- 239000011574 phosphorus Substances 0.000 claims abstract description 5
- 239000011593 sulfur Chemical group 0.000 claims abstract description 5
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 4
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000001965 increasing effect Effects 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract 6
- -1 oxy, carbonyl Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000002978 peroxides Chemical class 0.000 claims description 16
- 229920001973 fluoroelastomer Polymers 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 14
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 13
- 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 claims description 12
- 239000000945 filler Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002560 nitrile group Chemical group 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 239000006229 carbon black Substances 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 239000004848 polyfunctional curative Substances 0.000 claims description 7
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical class FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 229920001897 terpolymer Polymers 0.000 claims description 5
- 230000032683 aging Effects 0.000 claims description 4
- 229910052783 alkali metal Chemical group 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 229910052784 alkaline earth metal Chemical group 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003918 triazines Chemical class 0.000 claims description 4
- 238000004073 vulcanization Methods 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 230000000052 comparative effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000011417 postcuring Methods 0.000 claims description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- BTMIENSZKMNLRR-UHFFFAOYSA-N tributyl(2-methoxypropyl)phosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CC(C)OC BTMIENSZKMNLRR-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 2
- PCAXITAPTVOLGL-UHFFFAOYSA-N 2,3-diaminophenol Chemical compound NC1=CC=CC(O)=C1N PCAXITAPTVOLGL-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 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 claims description 2
- QSRFYFHZPSGRQX-UHFFFAOYSA-N benzyl(tributyl)azanium Chemical compound CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 QSRFYFHZPSGRQX-UHFFFAOYSA-N 0.000 claims description 2
- QUCVNPJIPOQRLJ-UHFFFAOYSA-N benzyl(triphenyl)azanium Chemical compound C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 QUCVNPJIPOQRLJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 238000007493 shaping process Methods 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 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 claims description 2
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 claims description 2
- YFZDLRVCXDBOPH-UHFFFAOYSA-N tetraheptylazanium Chemical compound CCCCCCC[N+](CCCCCCC)(CCCCCCC)CCCCCCC YFZDLRVCXDBOPH-UHFFFAOYSA-N 0.000 claims description 2
- DTIFFPXSSXFQCJ-UHFFFAOYSA-N tetrahexylazanium Chemical compound CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC DTIFFPXSSXFQCJ-UHFFFAOYSA-N 0.000 claims description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 2
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical group C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 claims description 2
- GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 claims description 2
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000006737 (C6-C20) arylalkyl group Chemical group 0.000 claims 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims 1
- 239000012018 catalyst precursor Substances 0.000 claims 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims 1
- 125000006551 perfluoro alkylene group Chemical group 0.000 claims 1
- 238000001723 curing Methods 0.000 description 56
- 239000003795 chemical substances by application Substances 0.000 description 31
- 229920001971 elastomer Polymers 0.000 description 17
- 239000005060 rubber Substances 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 238000012545 processing Methods 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- 150000002825 nitriles Chemical class 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 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 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000000518 rheometry Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 229920001774 Perfluoroether Polymers 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 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 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 239000012632 extractable Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 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
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- XQJHRCVXRAJIDY-UHFFFAOYSA-N aminophosphine Chemical compound PN XQJHRCVXRAJIDY-UHFFFAOYSA-N 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
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 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 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010438 heat treatment Methods 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
- 238000010348 incorporation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 241000894007 species Species 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- FQQANIIWRNLXFA-UHFFFAOYSA-L tetrabutylphosphanium;carbonate Chemical compound [O-]C([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC.CCCC[P+](CCCC)(CCCC)CCCC FQQANIIWRNLXFA-UHFFFAOYSA-L 0.000 description 2
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 2
- WUMVZXWBOFOYAW-UHFFFAOYSA-N 1,2,3,3,4,4,4-heptafluoro-1-(1,2,3,3,4,4,4-heptafluorobut-1-enoxy)but-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)F WUMVZXWBOFOYAW-UHFFFAOYSA-N 0.000 description 1
- BZPCMSSQHRAJCC-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,5-nonafluoro-1-(1,2,3,3,4,4,5,5,5-nonafluoropent-1-enoxy)pent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F BZPCMSSQHRAJCC-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
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- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
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- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 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
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- CHPGDDYKLVMZGY-UHFFFAOYSA-M tetraphenylstibanium;chloride Chemical compound C=1C=CC=CC=1[Sb](C=1C=CC=CC=1)(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 CHPGDDYKLVMZGY-UHFFFAOYSA-M 0.000 description 1
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- RJQOTGXQEMQSQF-UHFFFAOYSA-M tributyl(2-methoxypropyl)phosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CC(C)OC RJQOTGXQEMQSQF-UHFFFAOYSA-M 0.000 description 1
- UDRBACREFJVZDG-UHFFFAOYSA-M tributyl(2-methoxypropyl)phosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC(C)OC UDRBACREFJVZDG-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/50—Phosphorus bound to carbon only
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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| US28353501P | 2001-04-12 | 2001-04-12 | |
| US10/122,489 US6844388B2 (en) | 2001-04-12 | 2002-04-11 | Fluoropolymer compositions containing a nitrogen cure site monomer |
| PCT/US2002/011601 WO2002083756A1 (en) | 2001-04-12 | 2002-04-12 | Fluoropolymer compositions |
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| JP2009058256A Division JP5197445B2 (ja) | 2001-04-12 | 2009-03-11 | フルオロポリマー組成物 |
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| JP2004524425A true JP2004524425A (ja) | 2004-08-12 |
| JP2004524425A5 JP2004524425A5 (enExample) | 2005-12-22 |
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| JP2009058256A Expired - Fee Related JP5197445B2 (ja) | 2001-04-12 | 2009-03-11 | フルオロポリマー組成物 |
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| JP2009058256A Expired - Fee Related JP5197445B2 (ja) | 2001-04-12 | 2009-03-11 | フルオロポリマー組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6844388B2 (enExample) |
| EP (1) | EP1379565B1 (enExample) |
| JP (2) | JP2004524425A (enExample) |
| CN (1) | CN1294165C (enExample) |
| AT (1) | ATE504626T1 (enExample) |
| DE (1) | DE60239672D1 (enExample) |
| WO (1) | WO2002083756A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009161767A (ja) * | 2001-04-12 | 2009-07-23 | Three M Innovative Properties Co | フルオロポリマー組成物 |
| JP2010514913A (ja) * | 2007-01-03 | 2010-05-06 | ソルヴェイ・ソレクシス・インコーポレーテッド | フルオロエラストマー組成物 |
| KR20120054586A (ko) * | 2009-06-25 | 2012-05-30 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 플루오로중합체를 위한 경화 조성물 |
| JP2022514843A (ja) * | 2018-12-20 | 2022-02-16 | スリーエム イノベイティブ プロパティズ カンパニー | 非晶質全フッ素化ポリマーの乾燥粉末ブレンド、その製造方法、及び乾燥粉末ブレンドから誘導される物品 |
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|---|---|---|---|---|
| US6890995B2 (en) * | 2001-01-31 | 2005-05-10 | 3M Innovative Properties Company | Fluoropolymer compositions |
| US6803425B2 (en) * | 2001-04-12 | 2004-10-12 | 3M Innovative Properties Company | Fluoropolymers having pendant imidate structures |
| US6794457B2 (en) * | 2001-04-30 | 2004-09-21 | 3M Innovative Properties Company | Fluoropolymer curing system containing a nitrogen cure site monomer |
| US6828914B2 (en) * | 2001-08-16 | 2004-12-07 | Battery Alert Ltd. | In-use unambiguously determining the near-end-of-life state of a combustion engine battery |
| JP2006506513A (ja) * | 2002-11-20 | 2006-02-23 | スリーエム イノベイティブ プロパティズ カンパニー | ニトリル末端基を有するフルオロポリマーを製造する方法 |
| US6956085B2 (en) * | 2003-02-14 | 2005-10-18 | 3M Innovative Properties Company | Fluoroelastomer compositions |
| EP1699829A1 (en) * | 2003-12-30 | 2006-09-13 | 3M Innovative Properties Company | Fluoropolymer coagulation method and composition |
| DE602005003074T2 (de) | 2004-08-25 | 2008-08-14 | Asahi Glass Co., Ltd. | Fluorocopolymer |
| US7402630B2 (en) * | 2004-12-16 | 2008-07-22 | 3M Innovative Properties Company | Curing compositions for fluoropolymers |
| US7300985B2 (en) * | 2004-12-21 | 2007-11-27 | 3M Innovative Properties Company | Fluoropolymers having pendant amidoxime or amidrazone structures |
| US20060270780A1 (en) * | 2005-05-25 | 2006-11-30 | Ping Xu | High purity perfluoroelastomer composites and a processes to produce the same |
| US7488781B2 (en) * | 2005-05-25 | 2009-02-10 | Gore Enterprise Holdings, Inc. | High purity transparent perfluoroelastomer parts and a process to produce the same |
| US7294677B2 (en) * | 2005-08-25 | 2007-11-13 | 3M Innovative Properties Company | Catalyst for making fluoroelastomer compositions and methods of using the same |
| 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 |
| WO2010147815A2 (en) * | 2009-06-19 | 2010-12-23 | 3M Innovative Properties Company | Low temperature curable amorphous fluoropolymers |
| US20110143138A1 (en) * | 2009-12-10 | 2011-06-16 | 3M Properties Company | Perfluoroelastomer bonding |
| US20110152487A1 (en) * | 2009-12-17 | 2011-06-23 | 3M Innovative Properties Company | Peroxide cured partially fluorinated elastomers |
| JP7645800B2 (ja) | 2018-12-20 | 2025-03-14 | スリーエム イノベイティブ プロパティズ カンパニー | 非晶質全フッ素化ポリマーのラテックスブレンド及びそれから誘導される物品 |
| WO2021079849A1 (ja) * | 2019-10-23 | 2021-04-29 | Ａｇｃ株式会社 | 含フッ素共重合体組成物および架橋ゴム物品 |
| WO2022229752A1 (en) * | 2021-04-30 | 2022-11-03 | 3M Innovative Properties Company | Curable fluoroelastomer compositions containing quaternary phosphonium hydroxybenzoate catalysts |
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-
2002
- 2002-04-11 US US10/122,489 patent/US6844388B2/en not_active Expired - Lifetime
- 2002-04-12 DE DE60239672T patent/DE60239672D1/de not_active Expired - Lifetime
- 2002-04-12 JP JP2002582105A patent/JP2004524425A/ja not_active Withdrawn
- 2002-04-12 EP EP02725650A patent/EP1379565B1/en not_active Expired - Lifetime
- 2002-04-12 WO PCT/US2002/011601 patent/WO2002083756A1/en not_active Ceased
- 2002-04-12 CN CNB028081226A patent/CN1294165C/zh not_active Expired - Fee Related
- 2002-04-12 AT AT02725650T patent/ATE504626T1/de not_active IP Right Cessation
-
2009
- 2009-03-11 JP JP2009058256A patent/JP5197445B2/ja not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009161767A (ja) * | 2001-04-12 | 2009-07-23 | Three M Innovative Properties Co | フルオロポリマー組成物 |
| JP2010514913A (ja) * | 2007-01-03 | 2010-05-06 | ソルヴェイ・ソレクシス・インコーポレーテッド | フルオロエラストマー組成物 |
| KR20120054586A (ko) * | 2009-06-25 | 2012-05-30 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 플루오로중합체를 위한 경화 조성물 |
| KR101684719B1 (ko) | 2009-06-25 | 2016-12-08 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 플루오로중합체를 위한 경화 조성물 |
| JP2022514843A (ja) * | 2018-12-20 | 2022-02-16 | スリーエム イノベイティブ プロパティズ カンパニー | 非晶質全フッ素化ポリマーの乾燥粉末ブレンド、その製造方法、及び乾燥粉末ブレンドから誘導される物品 |
| JP7706367B2 (ja) | 2018-12-20 | 2025-07-11 | スリーエム イノベイティブ プロパティズ カンパニー | 非晶質全フッ素化ポリマーの乾燥粉末ブレンド、その製造方法、及び乾燥粉末ブレンドから誘導される物品 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1379565B1 (en) | 2011-04-06 |
| EP1379565A1 (en) | 2004-01-14 |
| JP5197445B2 (ja) | 2013-05-15 |
| US20020177666A1 (en) | 2002-11-28 |
| CN1501947A (zh) | 2004-06-02 |
| ATE504626T1 (de) | 2011-04-15 |
| DE60239672D1 (de) | 2011-05-19 |
| JP2009161767A (ja) | 2009-07-23 |
| US6844388B2 (en) | 2005-01-18 |
| CN1294165C (zh) | 2007-01-10 |
| WO2002083756A1 (en) | 2002-10-24 |
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