JP2000510501A - フルオロエラストマ組成物 - Google Patents
フルオロエラストマ組成物Info
- Publication number
- JP2000510501A JP2000510501A JP09525506A JP52550697A JP2000510501A JP 2000510501 A JP2000510501 A JP 2000510501A JP 09525506 A JP09525506 A JP 09525506A JP 52550697 A JP52550697 A JP 52550697A JP 2000510501 A JP2000510501 A JP 2000510501A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- group
- ether
- salt
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 136
- 229920001973 fluoroelastomer Polymers 0.000 title description 33
- 229920001971 elastomer Polymers 0.000 claims abstract description 106
- 239000005060 rubber Substances 0.000 claims abstract description 60
- 150000002170 ethers Chemical class 0.000 claims abstract description 51
- 239000000806 elastomer Substances 0.000 claims abstract description 46
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims description 40
- -1 aliphatic ether salt Chemical class 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 8
- 239000011737 fluorine Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 125000001033 ether group Chemical group 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Chemical group 0.000 claims description 6
- 150000004703 alkoxides Chemical class 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 238000000465 moulding Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical group FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910052787 antimony Chemical group 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052785 arsenic Inorganic materials 0.000 claims description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
- 230000001588 bifunctional effect Effects 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000006551 perfluoro alkylene group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001449 anionic compounds Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229910001412 inorganic anion Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 150000002891 organic anions Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000000446 fuel Substances 0.000 abstract description 6
- 239000000463 material Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- 150000002009 diols Chemical class 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000000518 rheometry Methods 0.000 description 9
- 239000002253 acid Chemical group 0.000 description 8
- 150000004010 onium ions Chemical class 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 239000004971 Cross linker Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 6
- 239000010702 perfluoropolyether Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 238000002386 leaching Methods 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 4
- 238000003801 milling Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- MGZDDCVCLLEWOR-UHFFFAOYSA-N acetic acid;tributylphosphane Chemical compound CC(O)=O.CCCCP(CCCC)CCCC MGZDDCVCLLEWOR-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 229920002449 FKM Polymers 0.000 description 2
- 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 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-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
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 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
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical compound [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- HISNRBVYBOVKMB-UHFFFAOYSA-N stibonium Chemical compound [SbH4+] HISNRBVYBOVKMB-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 229920003249 vinylidene fluoride hexafluoropropylene elastomer Polymers 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- UTCOUOISVRSLSH-UHFFFAOYSA-N 1,2-Anthracenediol Chemical compound C1=CC=CC2=CC3=C(O)C(O)=CC=C3C=C21 UTCOUOISVRSLSH-UHFFFAOYSA-N 0.000 description 1
- SXWIAEOZZQADEY-UHFFFAOYSA-N 1,3,5-triphenylbenzene Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1 SXWIAEOZZQADEY-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical class CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- YTCHAEAIYHLXBK-UHFFFAOYSA-N 2-chloro-1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=C(Cl)C(F)(F)F YTCHAEAIYHLXBK-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CHDJKORCDHLKSR-UHFFFAOYSA-N C=1C=C(O)C=CC=1C(C)(C=CCC)C1=CC=C(O)C=C1 Chemical compound C=1C=C(O)C=CC=1C(C)(C=CCC)C1=CC=C(O)C=C1 CHDJKORCDHLKSR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 229920006172 Tetrafluoroethylene propylene Polymers 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000007513 acids Chemical group 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- XQJHRCVXRAJIDY-UHFFFAOYSA-N aminophosphine Chemical compound PN XQJHRCVXRAJIDY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 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
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 229920001198 elastomeric copolymer Polymers 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 125000005348 fluorocycloalkyl group Chemical group 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000013022 formulation composition Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 238000007734 materials engineering Methods 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical class COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000010074 rubber mixing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 150000003497 tellurium Chemical class 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/653,526 | 1996-05-24 | ||
| US08/653,526 US5681881A (en) | 1996-05-24 | 1996-05-24 | Fluoroelastomer compositions |
| PCT/US1996/015272 WO1997045480A1 (en) | 1996-05-24 | 1996-09-24 | Fluoroelastomer compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000510501A true JP2000510501A (ja) | 2000-08-15 |
| JP2000510501A5 JP2000510501A5 (enExample) | 2004-10-07 |
Family
ID=24621238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP09525506A Pending JP2000510501A (ja) | 1996-05-24 | 1996-09-24 | フルオロエラストマ組成物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5681881A (enExample) |
| EP (1) | EP0902806B1 (enExample) |
| JP (1) | JP2000510501A (enExample) |
| KR (1) | KR20000015908A (enExample) |
| CN (1) | CN1090647C (enExample) |
| AU (1) | AU7244396A (enExample) |
| CA (1) | CA2253619A1 (enExample) |
| DE (1) | DE69632922T2 (enExample) |
| WO (1) | WO1997045480A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008524375A (ja) * | 2004-12-16 | 2008-07-10 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロポリマーの硬化組成物 |
| JP2012531493A (ja) * | 2009-06-25 | 2012-12-10 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロポリマー用の硬化組成物 |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6096428A (en) * | 1998-04-09 | 2000-08-01 | 3M Innovative Properties Company | Multi-layer compositions comprising a fluoropolymer |
| IT1306200B1 (it) * | 1999-01-14 | 2001-05-30 | Ausimont Spa | Composizioni vulcanizzabili di fluoroelastomeri. |
| US6452038B1 (en) | 2000-06-28 | 2002-09-17 | 3M Innovative Properties Company | Fluoroalkyloxy dispersant |
| US6372838B1 (en) * | 2000-06-28 | 2002-04-16 | 3M Innovative Properties Company | Fine latex and seed method of making |
| US6384124B1 (en) * | 2000-06-28 | 2002-05-07 | 3M Innovative Properties Company | Non-film-forming electrophoretic latexes in fluorocarbon solvents |
| US6890995B2 (en) * | 2001-01-31 | 2005-05-10 | 3M Innovative Properties Company | Fluoropolymer compositions |
| US6844388B2 (en) | 2001-04-12 | 2005-01-18 | 3M Innovative Properties Company | Fluoropolymer compositions containing a nitrogen cure site monomer |
| US6803425B2 (en) | 2001-04-12 | 2004-10-12 | 3M Innovative Properties Company | Fluoropolymers having pendant imidate structures |
| US6562889B2 (en) | 2001-04-18 | 2003-05-13 | 3M Innovative Properties Company | Dispersant in non-polar solvent |
| US6794457B2 (en) | 2001-04-30 | 2004-09-21 | 3M Innovative Properties Company | Fluoropolymer curing system containing a nitrogen cure site monomer |
| US6956085B2 (en) * | 2003-02-14 | 2005-10-18 | 3M Innovative Properties Company | Fluoroelastomer compositions |
| US20040236028A1 (en) * | 2003-05-21 | 2004-11-25 | Ming-Hong Hung | Fluoroelastomer composition having excellent low temperature properties |
| EP1699829A1 (en) * | 2003-12-30 | 2006-09-13 | 3M Innovative Properties Company | Fluoropolymer coagulation method and composition |
| US7079304B2 (en) * | 2004-01-23 | 2006-07-18 | The Lubrizol Corporation | Structured fluid compositions for electrophoretically frustrated total internal reflection displays |
| US7294677B2 (en) * | 2005-08-25 | 2007-11-13 | 3M Innovative Properties Company | Catalyst for making fluoroelastomer compositions and methods of using the same |
| US20090042166A1 (en) * | 2005-12-29 | 2009-02-12 | Craig Bradley D | Abrasive tool including agglomerate particles and an elastomer, and related methods |
| WO2010080309A2 (en) * | 2008-12-19 | 2010-07-15 | 3M Innovative Properties Company | Cure system for fluoroelastomer gum |
| US8105430B2 (en) * | 2009-06-30 | 2012-01-31 | Alberta Research Council Inc. | Aircraft anti-icing fluids formulated with nanocrystalline cellulose |
| GB201108963D0 (en) * | 2011-05-27 | 2011-07-13 | 3M Innovative Properties Co | Composite materials comprising polyamides and fluoroelastomers |
| CN111742004B (zh) | 2018-02-19 | 2022-07-19 | 3M创新有限公司 | 可固化组合物 |
| EP3755739A1 (en) | 2018-02-19 | 2020-12-30 | 3M Innovative Properties Company | Curable fluoroelastomer composition |
| US11859074B2 (en) | 2018-06-13 | 2024-01-02 | 3M Innovative Properties Company | Curable fluoroelastomer composition |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3318854A (en) * | 1953-04-03 | 1967-05-09 | Minnesota Mining & Mfg | Fluorinated elastomeric copolymers |
| DE1078329B (de) * | 1955-04-27 | 1960-03-24 | Du Pont | Verfahren zur Herstellung eines elastischen Mischpolymerisats aus Vinylidenfluorid und einem anderen Fluorolefin |
| US3159609A (en) * | 1956-10-26 | 1964-12-01 | Du Pont | Copolymers of perfluorovinyl ethers |
| US2968649A (en) * | 1958-12-04 | 1961-01-17 | Du Pont | Elastomeric terpolymers |
| US3125599A (en) * | 1961-06-15 | 1964-03-17 | Xoxcf | |
| US3250807A (en) * | 1963-08-23 | 1966-05-10 | Du Pont | Dicarboxylic acids of fluorocarbon ethers and fluorides, esters, amides and salts thereof |
| NL148300B (nl) * | 1964-01-02 | 1976-01-15 | Edison Soc | Werkwijze ter bereiding van polyoxyperfluormethylenen. |
| NL6709067A (enExample) * | 1964-04-09 | 1968-01-08 | ||
| US3442942A (en) * | 1964-04-09 | 1969-05-06 | Montedison Spa | Fluorinated oxygen containing acyl fluorides |
| US3467635A (en) * | 1964-10-30 | 1969-09-16 | Du Pont | Copolymers of tetrafluoroethylene and olefins curable to elastomers |
| US3505411A (en) * | 1966-10-11 | 1970-04-07 | Minnesota Mining & Mfg | Perfluoroalkylene oxide polymers |
| DE1745169B2 (de) * | 1967-02-09 | 1977-04-21 | Montecatini Edison S.P.A., Mailand (Italien) | Fluorierte lineare polyaether und verfahren zu ihrer herstellung |
| US3849504A (en) * | 1967-03-10 | 1974-11-19 | Minnesota Mining & Mfg | Perfluoropolyethers and process for making |
| US4094911A (en) * | 1969-03-10 | 1978-06-13 | Minnesota Mining And Manufacturing Company | Poly(perfluoroalkylene oxide) derivatives |
| US3810874A (en) * | 1969-03-10 | 1974-05-14 | Minnesota Mining & Mfg | Polymers prepared from poly(perfluoro-alkylene oxide) compounds |
| US3810875A (en) * | 1970-09-08 | 1974-05-14 | D Rice | Fluorine-containing block copolymers |
| US3876654A (en) * | 1970-12-23 | 1975-04-08 | Du Pont | Fluoroelastomer composition |
| US3752787A (en) * | 1972-01-28 | 1973-08-14 | Du Pont | Fluoroelastomer composition containing a triarylphosphorane vulcanization accelerator |
| US4287320A (en) * | 1974-08-01 | 1981-09-01 | Minnesota Mining And Manufacturing Company | Composition of fluoroelastomer and diorganosulfuroxide |
| 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 |
| DK553478A (da) * | 1977-12-14 | 1979-06-15 | Montedison Spa | Vulkaniserbare blandinger paa basis af vinylidenfluoridelastomere samt fremgangsmaade til vulkanisering af saadanne blandinger |
| US4233421A (en) * | 1979-02-26 | 1980-11-11 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition containing sulfonium curing agents |
| US4450263A (en) * | 1979-08-30 | 1984-05-22 | Minnesota Mining And Manufacturing Company | Fluoropolymer gum of vinylidene fluoride, hexafluoropropene, and bromodifluoroethylene |
| US4263414A (en) * | 1979-08-30 | 1981-04-21 | Minnesota Mining And Manufacturing Company | Vulcanizable blend of bromine-containing fluoropolymer and fluorosilicone gums |
| US4358559A (en) * | 1981-11-19 | 1982-11-09 | Minnesota Mining And Manufacturing Company | Tacky fluoroelastomer compositions |
| US4446270A (en) * | 1982-11-22 | 1984-05-01 | Minnesota Mining And Manufacturing Company | Vulcanizing fluorocarbon elastomers with one or a mixture of aromatic compounds having hydroxyl and oxyallyl groups |
| US5086123A (en) * | 1984-02-27 | 1992-02-04 | Minnesota Mining And Manufacturing Company | Fluoroelastomer compositions containing fluoroaliphatic sulfonamides as curing agents |
| CA1266750A (en) * | 1985-02-26 | 1990-03-13 | Giuseppe Marchionni | Bifunctional and monofunctional perfluoropolyethers having brominated end groups and a controlled molecular weight |
| IT1200801B (it) * | 1985-10-17 | 1989-01-27 | Ausimont Spa | Addittivi coadiuvanti di lavorazione per gomme vulcannizzabilli mediante perossidi |
| IT1188202B (it) * | 1985-11-15 | 1988-01-07 | Ausimont Spa | Composizioni elastomeriche vulcanizzabili di fluoroelastomeri |
| IT1209669B (it) * | 1985-11-15 | 1989-08-30 | Ausimont Spa | Composizioni vulcanizzabili fluoroelastomeri aventi migliorate caratteristiche di processabilita'e di stabilita' chimica. |
| IT1222804B (it) * | 1987-10-02 | 1990-09-12 | Ausimont Spa | Additivi coadiuvanti al distacco degli stampi di gomme vulcanizzabili mediante perossidi |
| US4882390A (en) * | 1988-04-01 | 1989-11-21 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium compounds |
| US5266650A (en) * | 1990-10-11 | 1993-11-30 | Minnesota Mining And Manufacturing Company | Curing fluorocarbon elastomers |
| US5384374A (en) * | 1991-01-11 | 1995-01-24 | Minnesota Mining And Manufacturing Company | Curing fluorocarbon elastomers |
| DE69233097T2 (de) * | 1991-01-11 | 2004-05-06 | Dyneon Llc, Oakdale | Fluorelastomerzusammensetzung |
| JP3277571B2 (ja) * | 1992-10-02 | 2002-04-22 | 日本メクトロン株式会社 | 低硬度フッ素ゴム組成物 |
| IT1271422B (it) * | 1993-10-15 | 1997-05-28 | Ausimont Spa | Procedimento per la preparazione di copolimeri del tetrafluoroetilene con altri monomeri perfluorurati |
-
1996
- 1996-05-24 US US08/653,526 patent/US5681881A/en not_active Expired - Lifetime
- 1996-09-24 CN CN96180304A patent/CN1090647C/zh not_active Expired - Fee Related
- 1996-09-24 KR KR1019980709460A patent/KR20000015908A/ko not_active Withdrawn
- 1996-09-24 JP JP09525506A patent/JP2000510501A/ja active Pending
- 1996-09-24 EP EP96933875A patent/EP0902806B1/en not_active Expired - Lifetime
- 1996-09-24 DE DE69632922T patent/DE69632922T2/de not_active Expired - Lifetime
- 1996-09-24 WO PCT/US1996/015272 patent/WO1997045480A1/en not_active Ceased
- 1996-09-24 CA CA002253619A patent/CA2253619A1/en not_active Abandoned
- 1996-09-24 AU AU72443/96A patent/AU7244396A/en not_active Abandoned
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008524375A (ja) * | 2004-12-16 | 2008-07-10 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロポリマーの硬化組成物 |
| KR101218467B1 (ko) * | 2004-12-16 | 2013-01-04 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 불소중합체용 경화 조성물 |
| TWI391432B (zh) * | 2004-12-16 | 2013-04-01 | 3M Innovative Properties Co | 用於氟聚合物之硬化組合物 |
| JP2012531493A (ja) * | 2009-06-25 | 2012-12-10 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロポリマー用の硬化組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0902806B1 (en) | 2004-07-14 |
| WO1997045480A1 (en) | 1997-12-04 |
| KR20000015908A (ko) | 2000-03-15 |
| DE69632922D1 (de) | 2004-08-19 |
| EP0902806A1 (en) | 1999-03-24 |
| CN1090647C (zh) | 2002-09-11 |
| CN1219183A (zh) | 1999-06-09 |
| CA2253619A1 (en) | 1997-12-04 |
| DE69632922T2 (de) | 2005-08-25 |
| AU7244396A (en) | 1998-01-05 |
| US5681881A (en) | 1997-10-28 |
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