CN103781819B - (全)氟聚醚嵌段共聚物 - Google Patents
(全)氟聚醚嵌段共聚物 Download PDFInfo
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- CN103781819B CN103781819B CN201280040826.XA CN201280040826A CN103781819B CN 103781819 B CN103781819 B CN 103781819B CN 201280040826 A CN201280040826 A CN 201280040826A CN 103781819 B CN103781819 B CN 103781819B
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- 229920001400 block copolymer Polymers 0.000 title claims abstract description 50
- 125000005010 perfluoroalkyl group Chemical group 0.000 title abstract description 4
- 239000004721 Polyphenylene oxide Substances 0.000 title abstract 2
- 229920000570 polyether Polymers 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
- 239000001257 hydrogen Substances 0.000 claims abstract description 54
- -1 polyoxy Polymers 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 239000011737 fluorine Substances 0.000 claims abstract description 8
- 229920001577 copolymer Polymers 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 110
- 229910052705 radium Inorganic materials 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- OFWDLJKVZZRPOX-UHFFFAOYSA-N 2,2,3,3-tetrafluorooxetane Chemical compound FC1(F)COC1(F)F OFWDLJKVZZRPOX-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 150000001265 acyl fluorides Chemical class 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 239000000314 lubricant Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 230000002940 repellent Effects 0.000 claims description 4
- 239000005871 repellent Substances 0.000 claims description 4
- 238000007142 ring opening reaction Methods 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910003827 NRaRb Inorganic materials 0.000 claims description 2
- 229910005960 SO2 a Inorganic materials 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 125000004185 ester group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract 4
- 125000001118 alkylidene group Chemical group 0.000 abstract 3
- 230000003252 repetitive effect Effects 0.000 abstract 2
- 238000005461 lubrication Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 16
- 150000002430 hydrocarbons Chemical group 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 12
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 11
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- 238000012360 testing method Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
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- 150000003254 radicals Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000012544 monitoring process Methods 0.000 description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 239000001307 helium Substances 0.000 description 5
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- ZEYZKQUPVUMZKV-UHFFFAOYSA-N dichloro carbonate Chemical compound ClOC(=O)OCl ZEYZKQUPVUMZKV-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- 229910001506 inorganic fluoride Inorganic materials 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- ACEKLXZRZOWKRY-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,5-undecafluoropentane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ACEKLXZRZOWKRY-UHFFFAOYSA-N 0.000 description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- CJFUEPJVIFJOOU-UHFFFAOYSA-N 2-perfluorobutyltetrahydrofuran Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1CCCO1 CJFUEPJVIFJOOU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical class [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VNIBTHCKBVEHRM-UHFFFAOYSA-N FP(N=P(F)(F)F)(NP)(F)F Chemical compound FP(N=P(F)(F)F)(NP)(F)F VNIBTHCKBVEHRM-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007866 anti-wear additive Substances 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
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- 239000000460 chlorine Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
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- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
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- 125000006239 protecting group Chemical group 0.000 description 2
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- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- OKIYQFLILPKULA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane Chemical compound COC(F)(F)C(F)(F)C(F)(F)C(F)(F)F OKIYQFLILPKULA-UHFFFAOYSA-N 0.000 description 1
- TXJYONBSFGLSSF-UHFFFAOYSA-N 1-(diethylamino)propane-1,2-diol Chemical compound CCN(CC)C(O)C(C)O TXJYONBSFGLSSF-UHFFFAOYSA-N 0.000 description 1
- KEDSBJOHAWJRQU-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6-nonafluoro-6-(1,1,2,2,3,3,3-heptafluoropropyl)oxane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C(F)(F)C1(F)F KEDSBJOHAWJRQU-UHFFFAOYSA-N 0.000 description 1
- 241000854350 Enicospilus group Species 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
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical group CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- AJIPIJNNOJSSQC-NYLIRDPKSA-N estetrol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)[C@@H]4O)O)[C@@H]4[C@@H]3CCC2=C1 AJIPIJNNOJSSQC-NYLIRDPKSA-N 0.000 description 1
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- 238000013467 fragmentation Methods 0.000 description 1
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- 230000007274 generation of a signal involved in cell-cell signaling Effects 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
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- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- ZUQIVGCFGVFWNR-UHFFFAOYSA-N isocyanatoethane;2-methylprop-2-enoic acid Chemical compound CCN=C=O.CC(=C)C(O)=O ZUQIVGCFGVFWNR-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
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- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 238000005329 nanolithography Methods 0.000 description 1
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- 238000004806 packaging method and process Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/02—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from isocyanates with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/126—Saturated ethers containing halogen having more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/32—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11171363.2 | 2011-06-24 | ||
| EP11171363 | 2011-06-24 | ||
| PCT/EP2012/061782 WO2012175534A1 (en) | 2011-06-24 | 2012-06-20 | (per)fluoropolyether block copolymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103781819A CN103781819A (zh) | 2014-05-07 |
| CN103781819B true CN103781819B (zh) | 2016-11-16 |
Family
ID=44453874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280040826.XA Expired - Fee Related CN103781819B (zh) | 2011-06-24 | 2012-06-20 | (全)氟聚醚嵌段共聚物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9394243B2 (enExample) |
| EP (1) | EP2723798A1 (enExample) |
| JP (1) | JP6196970B2 (enExample) |
| CN (1) | CN103781819B (enExample) |
| WO (1) | WO2012175534A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5668887B1 (ja) * | 2013-08-23 | 2015-02-12 | ダイキン工業株式会社 | パーフルオロ（ポリ）エーテル基含有二官能化合物、パーフルオロ（ポリ）エーテル基含有二官能化合物を含む組成物およびこれらの製造方法 |
| US10351669B2 (en) * | 2014-11-19 | 2019-07-16 | Solvay Specialty Polymers Italy S.P.A. | Amino derivatives of perfluoropolyethers |
| CN107722256A (zh) * | 2017-11-05 | 2018-02-23 | 王玉兰 | 一种新型聚氢氟醚的制备方法 |
| JP2019108466A (ja) * | 2017-12-18 | 2019-07-04 | 住鉱潤滑剤株式会社 | 溶剤希釈型潤滑剤 |
| CN110452307B (zh) * | 2019-07-24 | 2021-05-11 | 衢州学院 | 一种改性纳米纤维素及其制备方法 |
| KR102710234B1 (ko) * | 2019-09-13 | 2024-09-27 | 다이킨 고교 가부시키가이샤 | 플루오로폴리에테르기 함유 화합물 및 그 제조 방법 |
| JP6888698B2 (ja) * | 2019-09-13 | 2021-06-16 | ダイキン工業株式会社 | フルオロポリエーテル基含有化合物およびその製造方法 |
| CN113583736B (zh) * | 2021-08-23 | 2022-09-13 | 中国石油化工股份有限公司 | 全氟聚醚型聚脲润滑脂的制法及全氟聚醚型聚脲润滑脂 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0293863A2 (en) * | 1987-06-02 | 1988-12-07 | Daikin Industries, Limited | Fluorine-containing polyether and process for preparing the same |
| US4845268A (en) * | 1983-12-26 | 1989-07-04 | Daikin Industries, Ltd. | Halogen-containing polyether |
| CN1044951A (zh) * | 1989-02-09 | 1990-08-29 | 奥西蒙特公司 | 具有防锈性、用作润滑油和润滑脂的组分或添加剂的全氟聚醚 |
| CN1052502A (zh) * | 1989-12-12 | 1991-06-26 | 奥西蒙特公司 | 具有抗磨损性质的全氟聚醚润滑剂 |
| CN1703442A (zh) * | 2002-10-18 | 2005-11-30 | 旭硝子株式会社 | 全氟聚醚衍生物 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3847978A (en) | 1968-07-01 | 1974-11-12 | Montedison Spa | Perfluorinated linear polyethers having reactive terminal groups at both ends of the chain and process for the preparation thereof |
| JPS60137928A (ja) * | 1983-12-26 | 1985-07-22 | Daikin Ind Ltd | 新規含フツ素ポリエ−テルおよびその製法 |
| CA1263405A (en) | 1984-05-23 | 1989-11-28 | Giantommaso Viola | Process for preparing neutral and functional perfluoropolyethers with controlled molecular weight |
| JPH0768338B2 (ja) * | 1987-06-02 | 1995-07-26 | ダイキン工業株式会社 | 含フッ素ポリエーテルおよびその製法 |
| JP3622204B2 (ja) | 1996-07-08 | 2005-02-23 | ダイキン工業株式会社 | フッ素系オイルを含有する化粧料 |
| ITMI20011424A1 (it) * | 2001-07-05 | 2003-01-05 | Ausimont Spa | Dispersioni di polimeri fluorurati |
| JP2003231719A (ja) | 2002-02-08 | 2003-08-19 | Daikin Ind Ltd | 架橋用含フッ素エラストマー組成物 |
| ITMI20021733A1 (it) | 2002-08-01 | 2004-02-02 | Ausimont S P A Ora Solvay Solexis Spa | Processo per la preparazione di perfluoropolieteri acil-fluoruro terminati per riduzione dei corrispondenti perfluoropolieteri perossidici. |
| ITMI20030971A1 (it) | 2003-05-15 | 2004-11-16 | Solvay Solexis Spa | Preparazione di perfluoropolieteri aventi almeno un terminale -ch2oh oppure -ch(cf3)oh. |
| US7589234B2 (en) | 2003-07-02 | 2009-09-15 | Daikin Industries, Ltd. | Fluoroalkyl carboxylic acid derivative, method for producing fluorine-containing polymer, and aqueous dispersion of fluorine-containing polymer |
| ATE554759T1 (de) | 2007-01-31 | 2012-05-15 | Guangzhou Zhongwei Biotechnology Ltd | Salzsaures gefriergetrocknetes piperphentonamin- pulver zur herstellung einer injektionslösung, herstellungsverfahren und verwendungen |
| US8318869B2 (en) * | 2007-05-16 | 2012-11-27 | Solvay Solexis S.P.A. | Fluorinated polyurethane composition |
| JP2009173644A (ja) | 2008-01-03 | 2009-08-06 | Daikin Ind Ltd | フルオロエーテルカルボン酸及びその製造方法、界面活性剤、それを利用した含フッ素ポリマーの製造方法並びに水性分散体 |
| JP2009215555A (ja) | 2008-03-06 | 2009-09-24 | Daikin Ind Ltd | 重合用界面活性剤、それを利用した含フッ素ポリマーの製造方法及び水性分散体 |
| EP2221664A1 (en) | 2009-02-19 | 2010-08-25 | Solvay Solexis S.p.A. | Nanolithography process |
| JP5705860B2 (ja) * | 2009-10-06 | 2015-04-22 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | 真空ポンプ用潤滑剤組成物 |
-
2012
- 2012-06-20 WO PCT/EP2012/061782 patent/WO2012175534A1/en not_active Ceased
- 2012-06-20 CN CN201280040826.XA patent/CN103781819B/zh not_active Expired - Fee Related
- 2012-06-20 US US14/128,020 patent/US9394243B2/en not_active Expired - Fee Related
- 2012-06-20 JP JP2014516319A patent/JP6196970B2/ja not_active Expired - Fee Related
- 2012-06-20 EP EP12729557.4A patent/EP2723798A1/en not_active Withdrawn
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4845268A (en) * | 1983-12-26 | 1989-07-04 | Daikin Industries, Ltd. | Halogen-containing polyether |
| EP0293863A2 (en) * | 1987-06-02 | 1988-12-07 | Daikin Industries, Limited | Fluorine-containing polyether and process for preparing the same |
| US4904417A (en) * | 1987-06-02 | 1990-02-27 | Daikin Industries Ltd. | Fluorine-containing polyether and process for preparing the same |
| CN1044951A (zh) * | 1989-02-09 | 1990-08-29 | 奥西蒙特公司 | 具有防锈性、用作润滑油和润滑脂的组分或添加剂的全氟聚醚 |
| CN1052502A (zh) * | 1989-12-12 | 1991-06-26 | 奥西蒙特公司 | 具有抗磨损性质的全氟聚醚润滑剂 |
| CN1703442A (zh) * | 2002-10-18 | 2005-11-30 | 旭硝子株式会社 | 全氟聚醚衍生物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2723798A1 (en) | 2014-04-30 |
| JP2014517131A (ja) | 2014-07-17 |
| JP6196970B2 (ja) | 2017-09-13 |
| US9394243B2 (en) | 2016-07-19 |
| WO2012175534A1 (en) | 2012-12-27 |
| US20140135244A1 (en) | 2014-05-15 |
| CN103781819A (zh) | 2014-05-07 |
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Granted publication date: 20161116 Termination date: 20200620 |