JP2015505894A - ポリヒドロキシ硬化性フルオロエラストマー組成物 - Google Patents
ポリヒドロキシ硬化性フルオロエラストマー組成物 Download PDFInfo
- Publication number
- JP2015505894A JP2015505894A JP2014547450A JP2014547450A JP2015505894A JP 2015505894 A JP2015505894 A JP 2015505894A JP 2014547450 A JP2014547450 A JP 2014547450A JP 2014547450 A JP2014547450 A JP 2014547450A JP 2015505894 A JP2015505894 A JP 2015505894A
- Authority
- JP
- Japan
- Prior art keywords
- processing aid
- metal compound
- curable composition
- compound processing
- unsaturated metal
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 229920001973 fluoroelastomer Polymers 0.000 title claims abstract description 35
- 239000006057 Non-nutritive feed additive Substances 0.000 claims abstract description 23
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 18
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 16
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 15
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 5
- -1 polydimethylsiloxane Polymers 0.000 claims description 43
- 229920001577 copolymer Polymers 0.000 claims description 8
- MFWYAJVOUCTAQI-UHFFFAOYSA-N bis[[ethenyl(dimethyl)silyl]oxy]-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C=C MFWYAJVOUCTAQI-UHFFFAOYSA-N 0.000 claims description 3
- OOGRAMOPTBMVKO-UHFFFAOYSA-N bis[[ethenyl(dimethyl)silyl]oxy]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](O[Si](C)(C)C=C)(O[Si](C)(C)C=C)C1=CC=CC=C1 OOGRAMOPTBMVKO-UHFFFAOYSA-N 0.000 claims description 3
- FEHYCIQPPPQNMI-UHFFFAOYSA-N ethenyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C=C)OC1=CC=CC=C1 FEHYCIQPPPQNMI-UHFFFAOYSA-N 0.000 claims description 3
- HOMYFVKFSFMSFF-UHFFFAOYSA-N ethenyl-[ethenyl(diphenyl)silyl]oxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=C)O[Si](C=C)(C=1C=CC=CC=1)C1=CC=CC=C1 HOMYFVKFSFMSFF-UHFFFAOYSA-N 0.000 claims description 3
- GGJQEMXRDJPGAH-UHFFFAOYSA-N ethenyl-ethoxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=C)(OCC)C1=CC=CC=C1 GGJQEMXRDJPGAH-UHFFFAOYSA-N 0.000 claims description 3
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 claims description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 2
- KPWVUBSQUODFPP-UHFFFAOYSA-N ethenyl-(ethenyl-methyl-phenylsilyl)oxy-methyl-phenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(C=C)O[Si](C)(C=C)C1=CC=CC=C1 KPWVUBSQUODFPP-UHFFFAOYSA-N 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 12
- 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 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 9
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 229930185605 Bisphenol Natural products 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- 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 6
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 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 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 150000004820 halides Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- QAERDLQYXMEHEB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoroprop-1-ene Chemical group FC(F)=CC(F)(F)F QAERDLQYXMEHEB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-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
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 150000004714 phosphonium salts Chemical group 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- AKOGNYJNGMLDOA-UHFFFAOYSA-N (4-acetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=C(OC(C)=O)C=C1 AKOGNYJNGMLDOA-UHFFFAOYSA-N 0.000 description 1
- RAHOAHBOOHXRDY-UHFFFAOYSA-M (4-chlorophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=CC(Cl)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RAHOAHBOOHXRDY-UHFFFAOYSA-M 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- QYMQYPBAGDZNMY-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoroethenoxy)propan-2-yl]oxybenzene Chemical compound FC(F)=C(F)OC(F)(F)C(F)(C(F)(F)F)OC1=C(F)C(F)=C(F)C(F)=C1F QYMQYPBAGDZNMY-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 1
- LLMLGZUZTFMXSA-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzenethiol Chemical group SC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LLMLGZUZTFMXSA-UHFFFAOYSA-N 0.000 description 1
- GPASWZHHWPVSRG-UHFFFAOYSA-N 2,5-dimethylbenzene-1,4-diol Chemical compound CC1=CC(O)=C(C)C=C1O GPASWZHHWPVSRG-UHFFFAOYSA-N 0.000 description 1
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 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
- 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 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 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
- 239000000370 acceptor Substances 0.000 description 1
- QZEDYSGIQVMNJU-UHFFFAOYSA-N acetic acid 2-(2-hydroxyphenyl)sulfonylphenol Chemical compound S(=O)(=O)(C1=C(C=CC=C1)O)C1=C(C=CC=C1)O.C(C)(=O)O.C(C)(=O)O QZEDYSGIQVMNJU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical compound [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- VERMEZLHWFHDLK-UHFFFAOYSA-N benzene-1,2,3,4-tetrol Chemical class OC1=CC=C(O)C(O)=C1O VERMEZLHWFHDLK-UHFFFAOYSA-N 0.000 description 1
- PKMDZVYQEANDCP-UHFFFAOYSA-M benzhydryl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C1=CC=CC=C1C([P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 PKMDZVYQEANDCP-UHFFFAOYSA-M 0.000 description 1
- NHOGNKSDKIMSIY-UHFFFAOYSA-M benzyl(trioctyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CC1=CC=CC=C1 NHOGNKSDKIMSIY-UHFFFAOYSA-M 0.000 description 1
- VUUQSOCJUCSVBN-UHFFFAOYSA-M benzyl(trioctyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CC1=CC=CC=C1 VUUQSOCJUCSVBN-UHFFFAOYSA-M 0.000 description 1
- BNQRPLGZFADFGA-UHFFFAOYSA-N benzyl(triphenyl)phosphanium Chemical class 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
- WTEPWWCRWNCUNA-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 WTEPWWCRWNCUNA-UHFFFAOYSA-M 0.000 description 1
- 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 1
- QJASHBOLMJLVCN-UHFFFAOYSA-M benzyl-(dimethylamino)-diphenylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(N(C)C)CC1=CC=CC=C1 QJASHBOLMJLVCN-UHFFFAOYSA-M 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000005323 carbonate salts Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical group 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004761 hexafluorosilicates Chemical group 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical class C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- KAPIAHDQNOMXFU-UHFFFAOYSA-M methyl(trioctyl)phosphanium;acetate Chemical compound CC([O-])=O.CCCCCCCC[P+](C)(CCCCCCCC)CCCCCCCC KAPIAHDQNOMXFU-UHFFFAOYSA-M 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- AUMCHVFPISJOMZ-UHFFFAOYSA-N phenol tetrabutylazanium tributyl(methyl)azanium Chemical compound C1(=CC=CC=C1)O.C1(=CC=CC=C1)O.C(CCC)[N+](CCCC)(CCCC)CCCC.C[N+](CCCC)(CCCC)CCCC AUMCHVFPISJOMZ-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- GDESWOTWNNGOMW-UHFFFAOYSA-N resorcinol monobenzoate Chemical compound OC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 GDESWOTWNNGOMW-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HISNRBVYBOVKMB-UHFFFAOYSA-N stibonium Chemical class [SbH4+] HISNRBVYBOVKMB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 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
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- QVBRLOSUBRKEJW-UHFFFAOYSA-M tetraoctylphosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QVBRLOSUBRKEJW-UHFFFAOYSA-M 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- FBEVECUEMUUFKM-UHFFFAOYSA-M tetrapropylazanium;chloride Chemical compound [Cl-].CCC[N+](CCC)(CCC)CCC FBEVECUEMUUFKM-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-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
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
- KSMYREBPTSSZDR-UHFFFAOYSA-M tributyl(prop-2-enyl)phosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC=C KSMYREBPTSSZDR-UHFFFAOYSA-M 0.000 description 1
- WMEXYKGUFOEYRE-UHFFFAOYSA-M trioctyl-[[3-(trifluoromethyl)phenyl]methyl]phosphanium;chloride Chemical compound [Cl-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CC1=CC=CC(C(F)(F)F)=C1 WMEXYKGUFOEYRE-UHFFFAOYSA-M 0.000 description 1
- FKMJROWWQOJRJX-UHFFFAOYSA-M triphenyl(prop-2-enyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC=C)C1=CC=CC=C1 FKMJROWWQOJRJX-UHFFFAOYSA-M 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5425—Silicon-containing compounds containing oxygen containing at least one C=C bond
-
- 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
- C08K5/13—Phenols; Phenolates
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/5403—Silicon-containing compounds containing no other elements than carbon or hydrogen
-
- 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
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
-
- 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
- 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
- C08L27/16—Homopolymers or copolymers or vinylidene fluoride
-
- 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
- C08L27/22—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 modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
- C08L43/04—Homopolymers or copolymers of monomers containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
- C08L2312/08—Crosslinking by silane
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Sealing Material Composition (AREA)
Abstract
Description
A)ポリヒドロキシ硬化性フルオロエラストマー;
B)ポリヒドロキシ硬化剤;
C)硬化促進剤;および
D)ケイ素元素に結合した少なくとも1個のビニルまたはアリル基を有するシロキサンを含む不飽和金属化合物加工助剤
を含む、硬化性フルオロエラストマー組成物を提供する。
のビスフェノール類が含まれる。好ましいポリヒドロキシ化合物には、ヘキサフルオロイソプロピリデン−ビス(4−ヒドロキシ−ベンゼン)(すなわち、ビスフェノールAFまたはBPAF);4,4’−イソプロピリデンジフェノール(すなわち、ビスフェノールA);4,4’−ジヒドロキシジフェニルスルホン;およびジアミノビスフェノールAFが含まれる。上に示されたビスフェノールの式を参照すると、Aがアルキレンである場合、それは、例えば、メチレン、エチレン、クロロエチレン、フルオロエチレン、ジフルオロエチレン、プロピリデン、イソプロピリデン、トリブチリデン、ヘプタクロロブチリデン、ヘプタフルオロブチリデン、ペンチリデン、ヘキシリデン、および1,1−シクロヘキシリデンであり得る。Aがシクロアルキレン基である場合、それは、例えば、1,4−シクロヘキシレン、2−クロロ−1,4−シクロヘキシレン、シクロペンチレン、または2−フルオロ−1,4−シクロヘキシレンであり得る。さらに、Aは、m−フェニレン、p−フェニレン、o−フェニレン、メチルフェニレン、ジメチルフェニレン、1,4−ネフチレン、3−フルオロ−1,4−ナフチレン、および2,6−ナフチレンなどのアリーレン基であり得る。式
ムーニー粘度は、ASTM D−1646(大形ロータ、条件ML 1+10分、121℃で測定)に従って決定した。
硬化特性は、以下の条件下でMonsanto Moving Die Rheometer(MDR2000)装置を用いて測定した。
移動ダイ周波数:1.66Hz
振動振幅:0.5
温度:177℃(特に断りのない限り)
試験継続時間:24分
MH:最大トルクレベル(dN・m単位)
ML:最低トルクレベル(dN・m単位)
ts2:MLを超えて2単位上昇までの分
t50:最大トルクの50%までの分
t90:最大トルクの90%までの分
実施例1および比較例Aの硬化性組成物は、2ロールミルで成分を配合することによって作製した。配合は、表Iに示す。組成物のムーニー粘度も、表Iに示す。ムーニー粘度は、本発明のシロキサンによって9.9%減少した。
Claims (11)
- A)ポリヒドロキシ硬化性フルオロエラストマー;
B)ポリヒドロキシ硬化剤;
C)硬化促進剤;および
D)ケイ素元素に結合した少なくとも1個のビニルまたはアリル基を有するシロキサンを含む不飽和金属化合物加工助剤
を含む、硬化性フルオロエラストマー組成物。 - 前記不飽和金属化合物加工助剤が、1,5−ジビニル−3,3−ジフェニル−1,1,5,5−テトラメチルトリシロキサンである、請求項1に記載の硬化性組成物。
- 前記不飽和金属化合物加工助剤が、1,3−ジビニル−1,3−ジフェニル−1,3−ジメチルジシロキサンである、請求項1に記載の硬化性組成物。
- 前記不飽和金属化合物加工助剤が、1,5−ジビニルヘキサメチルトリシロキサンである、請求項1に記載の硬化性組成物。
- 前記不飽和金属化合物加工助剤が、1,3−ジビニルテトラフェニルジシロキサンである、請求項1に記載の硬化性組成物。
- 前記不飽和金属化合物加工助剤が、ビニル末端ポリジメチルシロキサンである、請求項1に記載の硬化性組成物。
- 前記不飽和金属化合物加工助剤が、ビニル末端ジフェニルシロキサン−ジメチルシロキサンコポリマーである、請求項1に記載の硬化性組成物。
- 前記不飽和金属化合物加工助剤が、ビニルメチルシロキサンホモポリマーである、請求項1に記載の硬化性組成物。
- 前記不飽和金属化合物加工助剤が、ビニルジフェニルエトキシシランである、請求項1に記載の硬化性組成物。
- 前記不飽和金属化合物加工助剤が、アリルトリメトキシシランである、請求項1に記載の硬化性組成物。
- 前記不飽和金属化合物加工助剤が、ビニルトリフェノキシシランである、請求項1に記載の硬化性組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161570873P | 2011-12-15 | 2011-12-15 | |
US61/570,873 | 2011-12-15 | ||
PCT/US2012/069597 WO2013090642A1 (en) | 2011-12-15 | 2012-12-13 | Polyhydroxy curable fluoroelastomer compositions |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015505894A true JP2015505894A (ja) | 2015-02-26 |
JP6084233B2 JP6084233B2 (ja) | 2017-02-22 |
Family
ID=47501474
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014547450A Active JP6084233B2 (ja) | 2011-12-15 | 2012-12-13 | ポリヒドロキシ硬化性フルオロエラストマー組成物 |
Country Status (5)
Country | Link |
---|---|
US (2) | US9102814B2 (ja) |
EP (1) | EP2791241B1 (ja) |
JP (1) | JP6084233B2 (ja) |
CN (1) | CN104136528B (ja) |
WO (2) | WO2013090582A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023195469A1 (ja) * | 2022-04-05 | 2023-10-12 | ダイキン工業株式会社 | フッ素ゴム架橋用組成物および成形品 |
WO2023195471A1 (ja) * | 2022-04-05 | 2023-10-12 | ダイキン工業株式会社 | フッ素ゴム架橋用組成物および成形品 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3521339B1 (en) * | 2016-12-09 | 2024-02-07 | Daikin Industries, Ltd. | Polymer, composition, and molded article |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01198646A (ja) * | 1987-10-30 | 1989-08-10 | Japan Synthetic Rubber Co Ltd | 架橋可能なゴム組成物および架橋ゴム製品 |
JPH09268245A (ja) * | 1996-03-29 | 1997-10-14 | Nichias Corp | フッ素系樹脂組成物、その製造法および成形品 |
JPH10101879A (ja) * | 1996-09-26 | 1998-04-21 | Japan Synthetic Rubber Co Ltd | フッ素ゴム組成物 |
WO2002044263A1 (en) * | 2000-12-01 | 2002-06-06 | Dupont Dow Elastomers L.L.C. | Fluoroelastomer composition having excellent processability and low temperature properties |
JP2005528516A (ja) * | 2002-06-06 | 2005-09-22 | ダウ・コーニング・コーポレイション | フルオロカーボンエラストマーシリコーン硬化物 |
US20070013101A1 (en) * | 2002-06-06 | 2007-01-18 | Dow Corning Corporation | Fluorocarbon elastomer silicone vulcanizates |
US20070197726A1 (en) * | 2004-06-30 | 2007-08-23 | Igor Chorvath | Fluoroplastics Containing Fluorocarbon-Silicone Elastomers |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3876654A (en) | 1970-12-23 | 1975-04-08 | Du Pont | Fluoroelastomer composition |
DK553478A (da) | 1977-12-14 | 1979-06-15 | Montedison Spa | Vulkaniserbare blandinger paa basis af vinylidenfluoridelastomere samt fremgangsmaade til vulkanisering af saadanne blandinger |
JPS5923578B2 (ja) | 1978-05-01 | 1984-06-02 | ダイキン工業株式会社 | フツ素ゴム組成物 |
US4394489A (en) * | 1982-02-25 | 1983-07-19 | E. I. Du Pont De Nemours & Co. | Fluoroelastomer curatives |
CA1265288A (en) * | 1984-11-22 | 1990-01-30 | E. I. Du Pont De Nemours And Company | Curable fluoroelastomer composition |
US4957975A (en) | 1988-03-14 | 1990-09-18 | E. I. Du Pont De Nemours And Company | Fluoroelastomer composition with low tendency to foul molds |
US4882390A (en) | 1988-04-01 | 1989-11-21 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium compounds |
US4912171A (en) | 1988-04-01 | 1990-03-27 | Minnesota Mining And Manufacturing Company | Fluoroelastomer curing process with phosphonium compound |
US5554680A (en) | 1994-02-16 | 1996-09-10 | E. I. Du Pont De Nemours And Company | Heat-resistant perfluoroelastomer composition |
IT1269846B (it) | 1994-05-27 | 1997-04-15 | Ausimont Spa | Composizioni fluoroelastomeriche vulcanizzabili |
US5591804A (en) | 1995-12-21 | 1997-01-07 | Minnesota Mining And Manufacturing Company | Fluorinated onium salts, curable compositions containing same, and method of curing using same |
US6329469B1 (en) | 1998-08-21 | 2001-12-11 | Dupont Dow Elastomers, L.L.C. | Fluoroelastomer composition having excellent processability and low temperature properties |
US6652641B2 (en) * | 1998-11-30 | 2003-11-25 | The Yokohama Rubber Co., Ltd. | Process for production of modified carbon black for rubber reinforcement and rubber composition containing modified carbon black |
US6512035B1 (en) * | 2000-05-15 | 2003-01-28 | Bridgestone Corporation | Processability of silica-reinforced rubber containing a monofunctional alkyl tin compound |
ATE304577T1 (de) | 2000-12-01 | 2005-09-15 | 3M Innovative Properties Co | Härtbare fluorelastomer-zusammensetzungen enthaltend hydrosiloxane oder hydrosilazane |
US6916871B2 (en) | 2001-10-31 | 2005-07-12 | 3M Innovative Properties Company | Composition and method for making a fluoroelastomer |
EP1454740B1 (en) * | 2003-03-04 | 2006-02-08 | 3M Innovative Properties Company | Method of bonding a fluoroelastomer layer to a silicone rubber layer, laminate for use in said method and article produced therewith |
CN102516690A (zh) * | 2011-10-27 | 2012-06-27 | 青岛开世密封工业有限公司 | 胶板用氟橡胶配方 |
-
2012
- 2012-11-14 US US13/676,586 patent/US9102814B2/en active Active
- 2012-11-14 US US13/676,399 patent/US9074074B2/en active Active
- 2012-12-13 EP EP12812454.2A patent/EP2791241B1/en active Active
- 2012-12-13 WO PCT/US2012/069519 patent/WO2013090582A1/en active Application Filing
- 2012-12-13 WO PCT/US2012/069597 patent/WO2013090642A1/en unknown
- 2012-12-13 JP JP2014547450A patent/JP6084233B2/ja active Active
- 2012-12-13 CN CN201280061775.9A patent/CN104136528B/zh active Active
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01198646A (ja) * | 1987-10-30 | 1989-08-10 | Japan Synthetic Rubber Co Ltd | 架橋可能なゴム組成物および架橋ゴム製品 |
US4942202A (en) * | 1987-10-30 | 1990-07-17 | Japan Synthetic Rubber Co., Ltd. | Rubber composition and vulcanized rubber product |
JPH09268245A (ja) * | 1996-03-29 | 1997-10-14 | Nichias Corp | フッ素系樹脂組成物、その製造法および成形品 |
JPH10101879A (ja) * | 1996-09-26 | 1998-04-21 | Japan Synthetic Rubber Co Ltd | フッ素ゴム組成物 |
WO2002044263A1 (en) * | 2000-12-01 | 2002-06-06 | Dupont Dow Elastomers L.L.C. | Fluoroelastomer composition having excellent processability and low temperature properties |
JP2004514776A (ja) * | 2000-12-01 | 2004-05-20 | デュポン ダウ エラストマーズ エルエルシー | 優れた加工性および低温特性を有するフルオロエラストマー組成物 |
JP2005528516A (ja) * | 2002-06-06 | 2005-09-22 | ダウ・コーニング・コーポレイション | フルオロカーボンエラストマーシリコーン硬化物 |
JP2005528515A (ja) * | 2002-06-06 | 2005-09-22 | ダウ・コーニング・コーポレイション | フルオロカーボンエラストマーシリコーン硬化物 |
US20060041064A1 (en) * | 2002-06-06 | 2006-02-23 | Gerald Gornowicz | Fluorocarbon elastomer silicone vulcanizates |
US20070013101A1 (en) * | 2002-06-06 | 2007-01-18 | Dow Corning Corporation | Fluorocarbon elastomer silicone vulcanizates |
US20070197726A1 (en) * | 2004-06-30 | 2007-08-23 | Igor Chorvath | Fluoroplastics Containing Fluorocarbon-Silicone Elastomers |
JP2008505205A (ja) * | 2004-06-30 | 2008-02-21 | ダウ・コーニング・コーポレイション | フッ化炭素シリコーンエラストマー含有フッ化プラスチック |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023195469A1 (ja) * | 2022-04-05 | 2023-10-12 | ダイキン工業株式会社 | フッ素ゴム架橋用組成物および成形品 |
WO2023195471A1 (ja) * | 2022-04-05 | 2023-10-12 | ダイキン工業株式会社 | フッ素ゴム架橋用組成物および成形品 |
JP7492172B2 (ja) | 2022-04-05 | 2024-05-29 | ダイキン工業株式会社 | フッ素ゴム架橋用組成物および成形品 |
JP7492173B2 (ja) | 2022-04-05 | 2024-05-29 | ダイキン工業株式会社 | フッ素ゴム架橋用組成物および成形品 |
Also Published As
Publication number | Publication date |
---|---|
US9102814B2 (en) | 2015-08-11 |
CN104136528A (zh) | 2014-11-05 |
US20130158197A1 (en) | 2013-06-20 |
CN104136528B (zh) | 2016-08-24 |
EP2791241B1 (en) | 2018-11-28 |
WO2013090642A1 (en) | 2013-06-20 |
US9074074B2 (en) | 2015-07-07 |
EP2791241A1 (en) | 2014-10-22 |
WO2013090582A1 (en) | 2013-06-20 |
JP6084233B2 (ja) | 2017-02-22 |
US20130158200A1 (en) | 2013-06-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6020440A (en) | Process for curing elastomeric vinylidene fluoride copolymers | |
JP2007031702A (ja) | フルオロエラストマー組成物、それらの調製、及びそれらの使用 | |
JP6084233B2 (ja) | ポリヒドロキシ硬化性フルオロエラストマー組成物 | |
JP6221085B2 (ja) | ポリヒドロキシ硬化性フルオロエラストマー組成物 | |
JPH09118797A (ja) | 臭素含有フルオロエラストマーを含む硬化性組成物 | |
EP1349892B1 (en) | Composition for making a fluoroelastomer | |
JP4437954B2 (ja) | 硬化性耐塩基性フルオロエラストマー | |
US6916871B2 (en) | Composition and method for making a fluoroelastomer | |
JP5319771B2 (ja) | 処理助剤を含有するフルオロエラストマー組成物 | |
US8227535B2 (en) | Polyhydroxy curable fluoroelastomer compositions | |
JPH0479376B2 (ja) | ||
US20090306303A1 (en) | Curable base-resistant fluoroelastomers | |
US6916887B2 (en) | Curable base-resistant fluoroelastomers |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20151214 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20151215 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20160909 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160913 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20161202 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20161227 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170124 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6084233 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |