CA1331252C - Fluoroelastomer compositions containing a tetraalkylammonium halide and vulcanization accelerator - Google Patents
Fluoroelastomer compositions containing a tetraalkylammonium halide and vulcanization acceleratorInfo
- Publication number
- CA1331252C CA1331252C CA000574493A CA574493A CA1331252C CA 1331252 C CA1331252 C CA 1331252C CA 000574493 A CA000574493 A CA 000574493A CA 574493 A CA574493 A CA 574493A CA 1331252 C CA1331252 C CA 1331252C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- chloride
- vulcanization accelerator
- metal
- quaternary phosphonium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 229920001973 fluoroelastomer Polymers 0.000 title claims abstract description 43
- -1 tetraalkylammonium halide Chemical class 0.000 title claims abstract description 26
- 238000004073 vulcanization Methods 0.000 title claims abstract description 21
- 229910052751 metal Inorganic materials 0.000 claims abstract description 41
- 239000002184 metal Substances 0.000 claims abstract description 41
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 229930185605 Bisphenol Natural products 0.000 claims abstract description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 13
- 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 claims abstract description 10
- 229920001198 elastomeric copolymer Polymers 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000002318 adhesion promoter Substances 0.000 claims abstract description 8
- 150000008442 polyphenolic compounds Polymers 0.000 claims abstract description 8
- 150000004023 quaternary phosphonium compounds Chemical group 0.000 claims abstract description 8
- 150000004820 halides Chemical class 0.000 claims abstract description 7
- 239000000178 monomer Substances 0.000 claims abstract description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 5
- HMQONDPNQIFUQR-UHFFFAOYSA-N 4-[2-(2,3-difluoro-4-hydroxyphenyl)propan-2-yl]-2,3,5,6-tetrafluorophenol Chemical group FC=1C(=C(C=CC1C(C)(C)C1=C(C(=C(C(=C1F)F)O)F)F)O)F HMQONDPNQIFUQR-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical group [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 11
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 11
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical group [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 claims description 8
- 125000005496 phosphonium group Chemical group 0.000 claims description 8
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229920001897 terpolymer Polymers 0.000 claims description 5
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 5
- 150000004714 phosphonium salts Chemical class 0.000 claims description 3
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical group [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 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 6
- 239000004615 ingredient Substances 0.000 description 5
- 239000000395 magnesium oxide Substances 0.000 description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 5
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 5
- 150000002736 metal compounds Chemical class 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 4
- 239000000920 calcium hydroxide Substances 0.000 description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 229910000975 Carbon steel Inorganic materials 0.000 description 2
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- PVXOJLLWTFSXQR-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;phenoxide Chemical compound [O-]C1=CC=CC=C1.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 PVXOJLLWTFSXQR-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 239000004203 carnauba wax Substances 0.000 description 2
- 235000013869 carnauba wax Nutrition 0.000 description 2
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 2
- LISODHVYQSLGJD-UHFFFAOYSA-M (1-ethoxy-1-oxopropan-2-yl)-triphenylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C(=O)OCC)C1=CC=CC=C1 LISODHVYQSLGJD-UHFFFAOYSA-M 0.000 description 1
- FWBSWSPGFNAXPP-UHFFFAOYSA-M (2,4-dichlorophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].ClC1=CC(Cl)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FWBSWSPGFNAXPP-UHFFFAOYSA-M 0.000 description 1
- SXBZWSKQLDBYIL-UHFFFAOYSA-M (2-cyanophenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].N#CC1=CC=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 SXBZWSKQLDBYIL-UHFFFAOYSA-M 0.000 description 1
- AVCQGKKIISOHIY-UHFFFAOYSA-N (2-ethoxy-2-oxo-1-phenylethyl)-triphenylphosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C(C(=O)OCC)C1=CC=CC=C1 AVCQGKKIISOHIY-UHFFFAOYSA-N 0.000 description 1
- VJVZPTPOYCJFNI-UHFFFAOYSA-M (2-ethoxy-2-oxoethyl)-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)OCC)C1=CC=CC=C1 VJVZPTPOYCJFNI-UHFFFAOYSA-M 0.000 description 1
- HUYKZYIAFUBPAQ-UHFFFAOYSA-N (2-hydroxyphenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1O HUYKZYIAFUBPAQ-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
- AZHSDLYDKBEFLL-UHFFFAOYSA-M (4-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=CC(C)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AZHSDLYDKBEFLL-UHFFFAOYSA-M 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical group FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DMUPYMORYHFFCT-UHFFFAOYSA-N 1,2,3,3,3-pentafluoroprop-1-ene Chemical group FC=C(F)C(F)(F)F DMUPYMORYHFFCT-UHFFFAOYSA-N 0.000 description 1
- LSRJROPWJQJYFT-UHFFFAOYSA-M 2,2,3,3,4,4,5,5-octafluoropentyl(trioctyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CC(F)(F)C(F)(F)C(F)(F)C(F)F LSRJROPWJQJYFT-UHFFFAOYSA-M 0.000 description 1
- LLMLGZUZTFMXSA-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzenethiol Chemical compound SC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LLMLGZUZTFMXSA-UHFFFAOYSA-N 0.000 description 1
- YDTQPVLNTJMRQW-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl-trioctylphosphanium Chemical compound CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCOCCOC YDTQPVLNTJMRQW-UHFFFAOYSA-N 0.000 description 1
- VIKPDPHNYHUZQW-UHFFFAOYSA-M 2-methylpropyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(C)C)C1=CC=CC=C1 VIKPDPHNYHUZQW-UHFFFAOYSA-M 0.000 description 1
- WBLRBQCSSBJIPF-UHFFFAOYSA-N 3-bromo-1,1,2,3-tetrafluorobut-1-ene Chemical compound CC(F)(Br)C(F)=C(F)F WBLRBQCSSBJIPF-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- NIIFINHILCUHNF-UHFFFAOYSA-M 4-cyanobutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC#N)C1=CC=CC=C1 NIIFINHILCUHNF-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004614 Process Aid Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 102100035115 Testin Human genes 0.000 description 1
- 101710070533 Testin Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- XNLRQNJMFXPKOX-UHFFFAOYSA-M butyl(trioctyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CCCC)(CCCCCCCC)CCCCCCCC XNLRQNJMFXPKOX-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 150000004761 hexafluorosilicates Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
- AHCKRTXGDNIJSK-UHFFFAOYSA-N methyl(trioctyl)phosphanium Chemical compound CCCCCCCC[P+](C)(CCCCCCCC)CCCCCCCC AHCKRTXGDNIJSK-UHFFFAOYSA-N 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
- HMWWZNGANFYVPX-UHFFFAOYSA-M methyl(trioctyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCC[P+](C)(CCCCCCCC)CCCCCCCC HMWWZNGANFYVPX-UHFFFAOYSA-M 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- LVLZXBIWQHFREA-UHFFFAOYSA-N phenol;phosphane Chemical compound [PH4+].[O-]C1=CC=CC=C1 LVLZXBIWQHFREA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- QVBRLOSUBRKEJW-UHFFFAOYSA-M tetraoctylphosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QVBRLOSUBRKEJW-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- OXFPPKPXLQFGDS-UHFFFAOYSA-M triphenyl-[[3-(trifluoromethyl)phenyl]methyl]phosphanium;chloride Chemical compound [Cl-].FC(F)(F)C1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 OXFPPKPXLQFGDS-UHFFFAOYSA-M 0.000 description 1
- AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 1
- 229920005609 vinylidenefluoride/hexafluoropropylene copolymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011787 zinc oxide 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/132—Phenols containing keto groups, e.g. benzophenones
-
- 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)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/197,506 US4868234A (en) | 1987-04-28 | 1988-04-27 | Fluoroelastomer compositions containing a tetraalkylammonium halide and vulcanization accelerator |
| US197,506 | 1988-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1331252C true CA1331252C (en) | 1994-08-02 |
Family
ID=22729692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000574493A Expired - Fee Related CA1331252C (en) | 1988-04-27 | 1988-08-11 | Fluoroelastomer compositions containing a tetraalkylammonium halide and vulcanization accelerator |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4868234A (enExample) |
| EP (1) | EP0339126B1 (enExample) |
| JP (1) | JPH01292055A (enExample) |
| BR (1) | BR8804125A (enExample) |
| CA (1) | CA1331252C (enExample) |
| DE (1) | DE3885887T2 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4868234A (en) * | 1987-04-28 | 1989-09-19 | E. I. Du Pont De Nemours And Company | Fluoroelastomer compositions containing a tetraalkylammonium halide and vulcanization accelerator |
| DE4109951C2 (de) * | 1991-03-26 | 1993-12-23 | Reinz Dichtungs Gmbh | Blech-Elastomer-Flachdichtung |
| US5262490A (en) * | 1992-08-24 | 1993-11-16 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium compounds |
| IT1269845B (it) * | 1994-05-27 | 1997-04-15 | Ausimont Spa | Composizioni fluoroelastomeriche vulcanizzabili |
| IT1269846B (it) * | 1994-05-27 | 1997-04-15 | Ausimont Spa | Composizioni fluoroelastomeriche vulcanizzabili |
| JP3890630B2 (ja) * | 1996-07-31 | 2007-03-07 | ユニマテック株式会社 | 含フッ素エラストマー組成物 |
| US6077624A (en) * | 1997-08-14 | 2000-06-20 | Valence Technology, Inc. | Lithium ion cells with improved thermal stability |
| US6239223B1 (en) | 1997-09-05 | 2001-05-29 | Chemfab Corporation | Fluoropolymeric composition |
| JP3924877B2 (ja) * | 1997-11-14 | 2007-06-06 | ユニマテック株式会社 | 含フッ素エラストマー用加硫促進剤の製造法 |
| US6746794B2 (en) | 2001-06-12 | 2004-06-08 | Tech Drive, Inc | Thermal runaway inhibitors |
| US6887927B2 (en) * | 2002-08-27 | 2005-05-03 | 3M Innovative Properties Company | Fluoropolymer compositions containing a nitrogen cure site monomer and a sulfone or sulfoxide compound |
| US6911512B2 (en) * | 2003-10-10 | 2005-06-28 | 3M Innovative Properties Company | Powder coating fluoropolymer compositions with aromatic materials |
| CN1989202B (zh) * | 2004-07-28 | 2010-10-06 | 大金工业株式会社 | 可过氧化物硫化的含氟弹性体组合物 |
| JP5179502B2 (ja) | 2006-10-13 | 2013-04-10 | スリーエム イノベイティブ プロパティズ カンパニー | モノヒドロキシ芳香族材料を含有する粉末コーティングフルオロポリマー組成物 |
| JP5394106B2 (ja) * | 2009-03-26 | 2014-01-22 | パナソニック株式会社 | 面状発光素子に対する給電方法 |
| FR2985215B1 (fr) | 2011-12-28 | 2014-09-19 | Saint Gobain Performance Plast | Revetements polymeres deposes sur des substrats par des techniques de projection thermique |
| CN103182808A (zh) | 2011-12-28 | 2013-07-03 | 圣戈班高功能塑料集团 | 一种包括含氟聚合物表面层以及非氟聚合物过渡层的多层复合物 |
| EP2867019B1 (en) | 2012-06-29 | 2023-01-18 | Saint-Gobain Performance Plastics Pampus GmbH | Slide bearing comprising a primer system as adhesion promoter |
| KR101663975B1 (ko) | 2012-09-28 | 2016-10-12 | 생―고뱅 퍼포먼스 플라스틱스 팜푸스 게엠베하 | 조합성 접착 슬라이드 층을 가지는 무-보수 슬라이드 베어링 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933732A (en) * | 1972-09-28 | 1976-01-20 | E. I. Du Pont De Nemours And Company | Fluoroelastomer composition and curing process |
| US3997705A (en) * | 1974-07-11 | 1976-12-14 | Dynamit Nobel Aktiengesellschaft | Method of coagulating a fluoro-elastomer from an aqueous dispersion thereof |
| JPS5111138A (en) * | 1974-07-16 | 1976-01-29 | Esb Inc | Denchibariaa oyobi denchi narabini sonoseizohoho |
| US4111111B1 (en) * | 1975-08-04 | 1995-03-14 | Charles H Willsey | Seperating mechanism for egg breaking machine |
| JPS5240655A (en) * | 1975-09-25 | 1977-03-29 | Tatsumi Seiki Co Ltd | Device for selecting needle in knitting machine |
| US4115481A (en) * | 1977-09-16 | 1978-09-19 | E. I. Du Pont De Nemours And Company | Fluoroelastomer blend composition |
| 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 |
| US4496682A (en) * | 1983-06-01 | 1985-01-29 | E. I. Du Pont De Nemours And Company | Curable fluoropolymer containing aromatic amine |
| DK310484A (da) * | 1983-06-30 | 1984-12-31 | Montedison Spa | Elastomerpraeparat baseret paa vinylidenfluorid |
| IT1190369B (it) * | 1985-06-19 | 1988-02-16 | Montefluos Spa | Composizioni covulcanizzabili di fluoroelastomeri a migliorata stabilita' chimica |
| JPS6286044A (ja) * | 1985-10-11 | 1987-04-20 | Asahi Glass Co Ltd | 加硫可能な組成物 |
| US4868234A (en) * | 1987-04-28 | 1989-09-19 | E. I. Du Pont De Nemours And Company | Fluoroelastomer compositions containing a tetraalkylammonium halide and vulcanization accelerator |
-
1988
- 1988-04-27 US US07/197,506 patent/US4868234A/en not_active Expired - Lifetime
- 1988-08-11 CA CA000574493A patent/CA1331252C/en not_active Expired - Fee Related
- 1988-08-13 EP EP88113193A patent/EP0339126B1/en not_active Expired - Lifetime
- 1988-08-13 DE DE3885887T patent/DE3885887T2/de not_active Expired - Lifetime
- 1988-08-16 JP JP63202802A patent/JPH01292055A/ja active Granted
- 1988-08-16 BR BR8804125A patent/BR8804125A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3885887T2 (de) | 1994-05-19 |
| BR8804125A (pt) | 1990-03-27 |
| EP0339126B1 (en) | 1993-11-24 |
| JPH0518357B2 (enExample) | 1993-03-11 |
| US4868234A (en) | 1989-09-19 |
| DE3885887D1 (de) | 1994-01-05 |
| EP0339126A1 (en) | 1989-11-02 |
| JPH01292055A (ja) | 1989-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |