CN1215117C - 具有良好低温特性的氟碳弹性组合物 - Google Patents
具有良好低温特性的氟碳弹性组合物 Download PDFInfo
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- CN1215117C CN1215117C CNB031594441A CN03159444A CN1215117C CN 1215117 C CN1215117 C CN 1215117C CN B031594441 A CNB031594441 A CN B031594441A CN 03159444 A CN03159444 A CN 03159444A CN 1215117 C CN1215117 C CN 1215117C
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- composition
- perfluorinated
- formula
- compound
- polyol
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- 239000000203 mixture Substances 0.000 title claims abstract description 63
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 title claims abstract description 11
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 17
- 150000002170 ethers Chemical class 0.000 claims abstract description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 8
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 239000003431 cross linking reagent Substances 0.000 claims abstract 4
- -1 aromatic polyol Chemical class 0.000 claims description 34
- 229920005862 polyol Polymers 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000003077 polyols Chemical group 0.000 claims 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 claims description 11
- 239000000178 monomer Substances 0.000 claims description 9
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 4
- 229920000768 polyamine Chemical class 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims 1
- 150000004010 onium ions Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 14
- MHNPWFZIRJMRKC-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical compound F[C]=C(F)F MHNPWFZIRJMRKC-UHFFFAOYSA-N 0.000 abstract 1
- 238000007493 shaping process Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000004513 sizing Methods 0.000 description 36
- 239000003795 chemical substances by application Substances 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 20
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229920001971 elastomer Polymers 0.000 description 18
- 239000003292 glue Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 150000002894 organic compounds Chemical class 0.000 description 12
- LREAZWJEBORMTB-UHFFFAOYSA-N bis(2-methylpropyl)phosphane Chemical compound CC(C)CPCC(C)C LREAZWJEBORMTB-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000806 elastomer Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 241001441571 Hiodontidae Species 0.000 description 5
- PRPAGESBURMWTI-UHFFFAOYSA-N [C].[F] Chemical compound [C].[F] PRPAGESBURMWTI-UHFFFAOYSA-N 0.000 description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 5
- 239000000920 calcium hydroxide Substances 0.000 description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 5
- 235000011116 calcium hydroxide Nutrition 0.000 description 5
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000395 magnesium oxide Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 229920001973 fluoroelastomer Polymers 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XSQHUYDRSDBCHN-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C)(C#N)C(C)C XSQHUYDRSDBCHN-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 3
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IXIMRXNEIJHZCJ-UHFFFAOYSA-N 4-propoxy-1-(4-propoxybut-1-enoxy)but-1-ene Chemical compound C(CC)OCCC=COC=CCCOCCC IXIMRXNEIJHZCJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 239000004160 Ammonium persulphate Substances 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 235000019395 ammonium persulphate Nutrition 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
- 125000003118 aryl group Chemical group 0.000 description 2
- OWKYBAIIYSYUJL-UHFFFAOYSA-N benzyl-bis(2-methylpropyl)phosphanium chloride Chemical compound [Cl-].CC(C)C[PH+](CC(C)C)CC1=CC=CC=C1 OWKYBAIIYSYUJL-UHFFFAOYSA-N 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- GYQSSCGWAJWHCK-UHFFFAOYSA-N dimethylaminophosphanium;chloride Chemical compound [Cl-].CN(C)[PH3+] GYQSSCGWAJWHCK-UHFFFAOYSA-N 0.000 description 2
- 239000003344 environmental pollutant Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000000643 oven drying Methods 0.000 description 2
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 231100000719 pollutant Toxicity 0.000 description 2
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- MJRPMUINYAOXRW-UHFFFAOYSA-N tributylphosphane;hydrochloride Chemical compound [Cl-].CCCC[PH+](CCCC)CCCC MJRPMUINYAOXRW-UHFFFAOYSA-N 0.000 description 2
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 1
- XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 description 1
- VMDHJUFWJBPLEE-UHFFFAOYSA-N 1-ethoxy-1-methoxybutan-1-ol Chemical class CCCC(O)(OC)OCC VMDHJUFWJBPLEE-UHFFFAOYSA-N 0.000 description 1
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 1
- YYVRSUMXFIIYRW-UHFFFAOYSA-N 1-propoxybutan-1-ol Chemical class CCCOC(O)CCC YYVRSUMXFIIYRW-UHFFFAOYSA-N 0.000 description 1
- WUIDISBMRXFHGJ-UHFFFAOYSA-N 1-propoxypentan-1-ol Chemical compound CCCCC(O)OCCC WUIDISBMRXFHGJ-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KGDXUHLUKKWAJP-UHFFFAOYSA-N 2-propoxypentanoic acid Chemical compound CCCOC(C(O)=O)CCC KGDXUHLUKKWAJP-UHFFFAOYSA-N 0.000 description 1
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-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
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 101100030424 Bombyx mori PPAE gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 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
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical compound [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000013475 authorization 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
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- UZCPNEBHTFYJNY-UHFFFAOYSA-N benzyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 UZCPNEBHTFYJNY-UHFFFAOYSA-N 0.000 description 1
- WCHPXAFAEZGCMB-UHFFFAOYSA-M benzyl(tributyl)phosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC1=CC=CC=C1 WCHPXAFAEZGCMB-UHFFFAOYSA-M 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- CXUFAAUKTHVLAL-UHFFFAOYSA-N butylphosphanium;chloride Chemical compound [Cl-].CCCC[PH3+] CXUFAAUKTHVLAL-UHFFFAOYSA-N 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 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
- 230000004927 fusion Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical group 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- UHNWOJJPXCYKCG-UHFFFAOYSA-L magnesium oxalate Chemical compound [Mg+2].[O-]C(=O)C([O-])=O UHNWOJJPXCYKCG-UHFFFAOYSA-L 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FZFZFCIODKYFEV-UHFFFAOYSA-N pentan-1-amine;hydrochloride Chemical compound Cl.CCCCCN FZFZFCIODKYFEV-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NRZGVGVFPHPXEO-UHFFFAOYSA-M tetraphenylarsanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NRZGVGVFPHPXEO-UHFFFAOYSA-M 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- QRCJOCOSPZMDJY-UHFFFAOYSA-N valnoctamide Chemical compound CCC(C)C(CC)C(N)=O QRCJOCOSPZMDJY-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/779297 | 1997-01-06 | ||
| US08/779,297 US5891965A (en) | 1997-01-06 | 1997-01-06 | Low temperature perfluoroether-containing fluoroelastomers |
| PCT/US1998/000098 WO1998030631A1 (en) | 1997-01-06 | 1998-01-06 | Perfluoroether-containing fluoroelastomers with good low temperature characteristics |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB988016680A Division CN100371383C (zh) | 1997-01-06 | 1998-01-06 | 氟碳弹性组合物的固化方法和固化的含氟弹性体及其制品 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1495228A CN1495228A (zh) | 2004-05-12 |
| CN1215117C true CN1215117C (zh) | 2005-08-17 |
Family
ID=25115949
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB031594441A Expired - Fee Related CN1215117C (zh) | 1997-01-06 | 1998-01-06 | 具有良好低温特性的氟碳弹性组合物 |
| CNB988016680A Expired - Fee Related CN100371383C (zh) | 1997-01-06 | 1998-01-06 | 氟碳弹性组合物的固化方法和固化的含氟弹性体及其制品 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB988016680A Expired - Fee Related CN100371383C (zh) | 1997-01-06 | 1998-01-06 | 氟碳弹性组合物的固化方法和固化的含氟弹性体及其制品 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5891965A (https=) |
| EP (1) | EP0950078B1 (https=) |
| JP (1) | JP4134283B2 (https=) |
| KR (1) | KR100516575B1 (https=) |
| CN (2) | CN1215117C (https=) |
| AU (1) | AU6016298A (https=) |
| CA (1) | CA2274775C (https=) |
| DE (1) | DE69801981T2 (https=) |
| WO (1) | WO1998030631A1 (https=) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69914923T2 (de) * | 1998-08-21 | 2004-12-09 | Dupont Dow Elastomers L.L.C., Wilmington | Fluoroelastomerzusammensetzung mit exzellenter verarbeitbarkeit und gute eigenschaften bei niedrigen temperaturen |
| US6294627B1 (en) * | 1998-08-31 | 2001-09-25 | Dyneon Llc | Low temperature fluorocarbon elastomers |
| US6255535B1 (en) * | 1999-12-22 | 2001-07-03 | Dyneon Llc | Fluorine containing allylethers and higher homologs |
| US6482979B1 (en) | 1999-12-22 | 2002-11-19 | Dyneon Llc | Perfluorinated acid fluorides and preparation thereof |
| US6890995B2 (en) * | 2001-01-31 | 2005-05-10 | 3M Innovative Properties Company | Fluoropolymer compositions |
| US6794457B2 (en) * | 2001-04-30 | 2004-09-21 | 3M Innovative Properties Company | Fluoropolymer curing system containing a nitrogen cure site monomer |
| US7304115B2 (en) * | 2003-12-30 | 2007-12-04 | 3M Innovative Properties Company | Fluoropolymer coagulation method and composition |
| ITMI20041571A1 (it) * | 2004-07-30 | 2004-10-30 | Solvay Solexis Spa | Perfluoroelastomeri |
| US7402630B2 (en) * | 2004-12-16 | 2008-07-22 | 3M Innovative Properties Company | Curing compositions for fluoropolymers |
| GB0427913D0 (en) * | 2004-12-21 | 2005-01-19 | 3M Innovative Properties Co | Fluoropolymer for making a fluoroelastomer |
| US7294677B2 (en) * | 2005-08-25 | 2007-11-13 | 3M Innovative Properties Company | Catalyst for making fluoroelastomer compositions and methods of using the same |
| US20070135577A1 (en) * | 2005-12-09 | 2007-06-14 | Shefelbine Terri A | Intermediate elastomer compositions |
| US8217126B2 (en) * | 2007-11-09 | 2012-07-10 | E I Du Pont De Nemours And Company | Fluoroolefin monomers and copolymers thereof |
| GB2459672A (en) * | 2008-04-30 | 2009-11-04 | 3M Innovative Properties Co | Linear short-chained perfluorinated alkoxy allyl ethers and their preparation |
| US20090306303A1 (en) * | 2008-06-09 | 2009-12-10 | Dupont Peformance Elastomers L.L.C. | Curable base-resistant fluoroelastomers |
| JP5547807B2 (ja) | 2009-06-25 | 2014-07-16 | 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 |
| US9540461B2 (en) | 2011-06-27 | 2017-01-10 | Solvay Specialty Polymers Italy S.P.A. | Fluorinated unsaturated compound and polymers obtainable therefrom |
| CN104093780B (zh) | 2011-11-09 | 2016-09-14 | 3M创新有限公司 | 用于含氟聚合物的固化组合物 |
| WO2017083688A1 (en) | 2015-11-13 | 2017-05-18 | 3M Innovative Properties Company | Compositions including a bimodal blend of amorphous fluoropolymers and their uses |
| KR20180104305A (ko) | 2016-01-21 | 2018-09-20 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 플루오로중합체의 적층 가공 |
| TW201815845A (zh) | 2016-05-17 | 2018-05-01 | ３Ｍ新設資產公司 | 包括二氟亞乙烯與四氟乙烯的共聚物之組成物及其使用方法 |
| US20190344496A1 (en) | 2016-12-20 | 2019-11-14 | 3M Innovative Properties Company | Composition including fluoropolymer and inorganic filler and method of making a three-dimensional article |
| EP3625201B1 (en) | 2017-05-19 | 2021-09-29 | 3M Innovative Properties Company | Methods of making a polyfluorinated allyl ether and compounds relating to the methods |
| CN111511711A (zh) | 2017-12-21 | 2020-08-07 | 3M创新有限公司 | 制备多官能多氟化合物的方法 |
| WO2020016718A1 (en) * | 2018-07-20 | 2020-01-23 | 3M Innovative Properties Company | Vinylidene fluoride fluoropolymers containing perfluorinated allyl ethers |
| US20210292533A1 (en) * | 2018-08-13 | 2021-09-23 | 3M Innovative Properties Company | Curable fluoroelastomer composition |
| RU2018141773A (ru) | 2018-11-27 | 2020-05-27 | 3М Инновейтив Пропертиз Компани | Композиции полимерных процессинговых добавок и изделия, полученные с использованием указанных композиций |
| CN113195613A (zh) | 2018-12-17 | 2021-07-30 | 3M创新有限公司 | 包含可固化含氟聚合物和固化剂的组合物及其制备和使用方法 |
| JP2022535815A (ja) | 2019-06-04 | 2022-08-10 | スリーエム イノベイティブ プロパティズ カンパニー | 多官能性フッ素化化合物、その化合物から製造されるフッ素化ポリマー、及び関連方法 |
| CN113950505B (zh) | 2019-06-28 | 2023-05-30 | 3M创新有限公司 | 羟基官能化三嗪化合物、包含此类化合物的可固化含氟聚合物组合物以及由其制得的固化制品 |
| WO2021046266A1 (en) | 2019-09-05 | 2021-03-11 | 3M Innovative Properties Company | Composition and article including fluoropolymer and branched silsesquioxane polymer |
| WO2021137084A1 (en) | 2019-12-30 | 2021-07-08 | 3M Innovative Properties Company | Composition including fluoropolymer, benzoyl peroxide, and crosslinker and related articles and methods |
| WO2021214664A1 (en) | 2020-04-21 | 2021-10-28 | 3M Innovative Properties Company | Particles including polytetrafluoroethylene and process for making a three-dimensional article |
| WO2022114109A1 (ja) * | 2020-11-30 | 2022-06-02 | セントラル硝子株式会社 | フルオロエラストマー組成物、フッ素ゴム成形体、フッ素ゴム成形体製造用架橋剤、フッ素ゴム成形体製造用架橋促進剤、混合塩およびオニウム塩 |
| US20240132643A1 (en) | 2021-02-26 | 2024-04-25 | 3M Innovative Properties Company | Process for Making a Fluoropolymer and Fluoropolymer Made Therefrom |
| WO2022189938A1 (en) | 2021-03-10 | 2022-09-15 | 3M Innovative Properties Company | Branched silsesquioxane polymer and compositions and articles including the same |
| WO2023224824A1 (en) | 2022-05-17 | 2023-11-23 | Dupont Specialty Products Usa, Llc | Method of making halo (alkyl vinyl) ether monomers and fluorinated polymers made with the halo (alkyl vinyl) ether monomer |
| CN120584153A (zh) | 2023-01-27 | 2025-09-02 | 杜邦特种产品美国有限责任公司 | 氟聚合物组合物以及由其制成的制品 |
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| US3029227A (en) * | 1956-08-20 | 1962-04-10 | Minnesota Mining & Mfg | Cross-linking and cross-linking agents |
| US2975163A (en) * | 1956-10-29 | 1961-03-14 | Minnesota Mining & Mfg | Fluorine containing organic compounds and preparation thereof |
| 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 (https=) * | 1964-04-09 | 1968-01-08 | ||
| US3442942A (en) * | 1964-04-09 | 1969-05-06 | Montedison Spa | Fluorinated oxygen containing acyl fluorides |
| GB1193122A (en) * | 1966-03-24 | 1970-05-28 | Allied Chem | Novel Fluoroperhaloisopropyl Methyl Ethers |
| US3715378A (en) * | 1967-02-09 | 1973-02-06 | Montedison Spa | Fluorinated peroxy polyether copolymers and method for preparing them from tetrafluoroethylene |
| US3504411A (en) * | 1967-10-11 | 1970-04-07 | Westinghouse Electric Corp | Process for producing an electrode tip |
| US3876654A (en) * | 1970-12-23 | 1975-04-08 | Du Pont | Fluoroelastomer composition |
| US3849594A (en) * | 1973-05-25 | 1974-11-19 | Westinghouse Electric Corp | Multi-picture tv system with audio and doding channels |
| US4287320A (en) * | 1974-08-01 | 1981-09-01 | Minnesota Mining And Manufacturing Company | Composition of fluoroelastomer and diorganosulfuroxide |
| DK553478A (da) * | 1977-12-14 | 1979-06-15 | Montedison Spa | Vulkaniserbare blandinger paa basis af vinylidenfluoridelastomere samt fremgangsmaade til vulkanisering af saadanne blandinger |
| US4206138A (en) * | 1978-08-08 | 1980-06-03 | E. I. Du Pont De Nemours And Company | Perfluoroallyl fluorosulfate and its sultone and polymers |
| US4233421A (en) * | 1979-02-26 | 1980-11-11 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition containing sulfonium curing agents |
| US4275225A (en) * | 1979-03-14 | 1981-06-23 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
| US4273729A (en) * | 1979-03-14 | 1981-06-16 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
| US4273728A (en) * | 1979-03-14 | 1981-06-16 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
| US4292449A (en) * | 1979-03-14 | 1981-09-29 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
| 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 |
| ES8605551A1 (es) * | 1984-02-27 | 1986-03-16 | Minnesota Mining & Mfg | Un metodo para preparar un articulo conformado a partir de conposiciones fluoroelastomeras que contienen sulfonamidas fluoroalifaticas en calidad de agentes de curado. |
| US5086123A (en) * | 1984-02-27 | 1992-02-04 | Minnesota Mining And Manufacturing Company | Fluoroelastomer compositions containing fluoroaliphatic sulfonamides as curing agents |
| US4897457A (en) * | 1987-08-14 | 1990-01-30 | Asahi Glass Company Ltd. | Novel fluorine-containing cyclic polymer |
| US4912171A (en) * | 1988-04-01 | 1990-03-27 | Minnesota Mining And Manufacturing Company | Fluoroelastomer curing process with phosphonium compound |
| CA2043971A1 (en) * | 1990-07-13 | 1992-01-14 | Jeffrey D. Weigelt | Curing fluorocarbon elastomers |
| 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 |
| US5214106A (en) * | 1991-05-22 | 1993-05-25 | E. I. Du Pont De Nemours And Company | Cured fluoroelastomer compositions |
| US5274159A (en) * | 1993-02-18 | 1993-12-28 | Minnesota Mining And Manufacturing Company | Destructable fluorinated alkoxysilane surfactants and repellent coatings derived therefrom |
| US5488142A (en) * | 1993-10-04 | 1996-01-30 | Minnesota Mining And Manufacturing Company | Fluorination in tubular reactor system |
| 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 |
-
1997
- 1997-01-06 US US08/779,297 patent/US5891965A/en not_active Expired - Lifetime
-
1998
- 1998-01-06 CA CA002274775A patent/CA2274775C/en not_active Expired - Fee Related
- 1998-01-06 KR KR10-1999-7006063A patent/KR100516575B1/ko not_active Expired - Fee Related
- 1998-01-06 EP EP98903369A patent/EP0950078B1/en not_active Expired - Lifetime
- 1998-01-06 AU AU60162/98A patent/AU6016298A/en not_active Abandoned
- 1998-01-06 CN CNB031594441A patent/CN1215117C/zh not_active Expired - Fee Related
- 1998-01-06 CN CNB988016680A patent/CN100371383C/zh not_active Expired - Fee Related
- 1998-01-06 DE DE69801981T patent/DE69801981T2/de not_active Expired - Lifetime
- 1998-01-06 JP JP53100398A patent/JP4134283B2/ja not_active Expired - Fee Related
- 1998-01-06 WO PCT/US1998/000098 patent/WO1998030631A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US5891965A (en) | 1999-04-06 |
| CA2274775A1 (en) | 1998-07-16 |
| WO1998030631A1 (en) | 1998-07-16 |
| DE69801981D1 (de) | 2001-11-15 |
| CN1495228A (zh) | 2004-05-12 |
| CN100371383C (zh) | 2008-02-27 |
| CA2274775C (en) | 2007-08-14 |
| EP0950078A1 (en) | 1999-10-20 |
| JP2001508105A (ja) | 2001-06-19 |
| AU6016298A (en) | 1998-08-03 |
| DE69801981T2 (de) | 2002-05-29 |
| CN1243529A (zh) | 2000-02-02 |
| KR100516575B1 (ko) | 2005-09-22 |
| KR20000069872A (ko) | 2000-11-25 |
| EP0950078B1 (en) | 2001-10-10 |
| JP4134283B2 (ja) | 2008-08-20 |
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