JP2011213837A - 含フッ素ポリエーテル化合物、その製造方法およびそれを含有する硬化性組成物 - Google Patents
含フッ素ポリエーテル化合物、その製造方法およびそれを含有する硬化性組成物 Download PDFInfo
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- JP2011213837A JP2011213837A JP2010082492A JP2010082492A JP2011213837A JP 2011213837 A JP2011213837 A JP 2011213837A JP 2010082492 A JP2010082492 A JP 2010082492A JP 2010082492 A JP2010082492 A JP 2010082492A JP 2011213837 A JP2011213837 A JP 2011213837A
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- Prior art keywords
- fluorine
- group
- general formula
- polyether compound
- containing polyether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 46
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 38
- 239000011737 fluorine Substances 0.000 title claims abstract description 38
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 33
- 229920000570 polyether Polymers 0.000 title claims abstract description 33
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- -1 dicarboxylic acid fluoride compound Chemical class 0.000 claims abstract description 53
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 abstract description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- TTYOSASOEDLIKD-UHFFFAOYSA-N CNC1=CC=C(C=C1)OC(=C(F)F)F Chemical compound CNC1=CC=C(C=C1)OC(=C(F)F)F TTYOSASOEDLIKD-UHFFFAOYSA-N 0.000 description 8
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 5
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000005499 phosphonyl group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- KVBKAPANDHPRDG-UHFFFAOYSA-N dibromotetrafluoroethane Chemical compound FC(F)(Br)C(F)(F)Br KVBKAPANDHPRDG-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 2
- WVADTUYIKJRSMI-UHFFFAOYSA-N 4-(2-bromo-1,1,2,2-tetrafluoroethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)C(F)(F)Br)C=C1 WVADTUYIKJRSMI-UHFFFAOYSA-N 0.000 description 2
- RHPLIERJFWOUDC-UHFFFAOYSA-N 4-(2-bromo-1,1,2,2-tetrafluoroethoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OC(F)(F)C(F)(F)Br)C=C1 RHPLIERJFWOUDC-UHFFFAOYSA-N 0.000 description 2
- ONDZWLHUIGNUEB-UHFFFAOYSA-N 4-(2-bromo-1,1,2,2-tetrafluoroethoxy)benzoyl chloride Chemical compound FC(F)(Br)C(F)(F)OC1=CC=C(C(Cl)=O)C=C1 ONDZWLHUIGNUEB-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- MAHBKWFRZKHOSU-UHFFFAOYSA-N C1=CC(=CC=C1C(=O)N=[N+]=[N-])OC(C(F)(F)Br)(F)F Chemical compound C1=CC(=CC=C1C(=O)N=[N+]=[N-])OC(C(F)(F)Br)(F)F MAHBKWFRZKHOSU-UHFFFAOYSA-N 0.000 description 2
- VZIKYPIPWOOORM-UHFFFAOYSA-N C1=CC(=CC=C1N=C=O)OC(C(F)(F)Br)(F)F Chemical compound C1=CC(=CC=C1N=C=O)OC(C(F)(F)Br)(F)F VZIKYPIPWOOORM-UHFFFAOYSA-N 0.000 description 2
- HJJCHSSAGVQANV-UHFFFAOYSA-N C1=CC=C(C(=C1)[N+](=O)[O-])S(=O)(=O)NC2=CC=C(C=C2)OC(C(F)(F)Br)(F)F Chemical compound C1=CC=C(C(=C1)[N+](=O)[O-])S(=O)(=O)NC2=CC=C(C=C2)OC(C(F)(F)Br)(F)F HJJCHSSAGVQANV-UHFFFAOYSA-N 0.000 description 2
- ONYCCXUJJLNOST-UHFFFAOYSA-N CN(C1=CC=C(C=C1)OC(C(F)(F)Br)(F)F)S(=O)(=O)C2=CC=CC=C2[N+](=O)[O-] Chemical compound CN(C1=CC=C(C=C1)OC(C(F)(F)Br)(F)F)S(=O)(=O)C2=CC=CC=C2[N+](=O)[O-] ONYCCXUJJLNOST-UHFFFAOYSA-N 0.000 description 2
- QGHJXHLDIZZOJM-UHFFFAOYSA-N CNC1=CC=C(C=C1)OC(C(F)(F)Br)(F)F Chemical compound CNC1=CC=C(C=C1)OC(C(F)(F)Br)(F)F QGHJXHLDIZZOJM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 101100388055 Mus musculus Polm gene Proteins 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001351 alkyl iodides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000007867 post-reaction treatment Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XAUHHCMRFFGRMF-UHFFFAOYSA-N 1-[1,1-bis[4-(1,2,2-trifluoroethenoxy)phenyl]ethyl]-4-(1,2,2-trifluoroethenoxy)benzene Chemical compound C=1C=C(OC(F)=C(F)F)C=CC=1C(C=1C=CC(OC(F)=C(F)F)=CC=1)(C)C1=CC=C(OC(F)=C(F)F)C=C1 XAUHHCMRFFGRMF-UHFFFAOYSA-N 0.000 description 1
- DFUYAWQUODQGFF-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane Chemical compound CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)F DFUYAWQUODQGFF-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
- SSFSNKZUKDBPIT-UHFFFAOYSA-N 2,4-dinitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C([N+]([O-])=O)=C1 SSFSNKZUKDBPIT-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- JRZVCSIBWPUFAQ-UHFFFAOYSA-N 4-(1,2,2-trifluoroethenoxy)aniline Chemical compound NC1=CC=C(OC(F)=C(F)F)C=C1 JRZVCSIBWPUFAQ-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 150000001503 aryl iodides Chemical class 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- WXRCVCQHYKVQLS-UHFFFAOYSA-N n-(1,2,2-trifluoroethenoxy)aniline Chemical compound FC(F)=C(F)ONC1=CC=CC=C1 WXRCVCQHYKVQLS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- DKGFIVSGQRBSOG-UHFFFAOYSA-M potassium;4-hydroxybenzoate Chemical compound [K+].OC1=CC=C(C([O-])=O)C=C1 DKGFIVSGQRBSOG-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000007966 viscous suspension Substances 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010082492A JP2011213837A (ja) | 2010-03-31 | 2010-03-31 | 含フッ素ポリエーテル化合物、その製造方法およびそれを含有する硬化性組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010082492A JP2011213837A (ja) | 2010-03-31 | 2010-03-31 | 含フッ素ポリエーテル化合物、その製造方法およびそれを含有する硬化性組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011213837A true JP2011213837A (ja) | 2011-10-27 |
| JP2011213837A5 JP2011213837A5 (enExample) | 2012-09-06 |
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| JP2010082492A Pending JP2011213837A (ja) | 2010-03-31 | 2010-03-31 | 含フッ素ポリエーテル化合物、その製造方法およびそれを含有する硬化性組成物 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013032455A (ja) * | 2011-08-03 | 2013-02-14 | Unimatec Co Ltd | 含フッ素ポリエーテル化合物およびその製造方法 |
| WO2015019809A1 (ja) | 2013-08-09 | 2015-02-12 | ユニマテック株式会社 | ビス（パーフルオロエーテルカルボン酸アルキル）アミノエステルおよびその製造法 |
| US10000444B2 (en) | 2015-02-03 | 2018-06-19 | Unimatec Co., Ltd. | Fluorine-containing ether monocarboxylic acid aminoalkyl ester and a method for producing the same |
| JPWO2023112714A1 (enExample) * | 2021-12-14 | 2023-06-22 | ||
| JPWO2023112713A1 (enExample) * | 2021-12-14 | 2023-06-22 |
-
2010
- 2010-03-31 JP JP2010082492A patent/JP2011213837A/ja active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013032455A (ja) * | 2011-08-03 | 2013-02-14 | Unimatec Co Ltd | 含フッ素ポリエーテル化合物およびその製造方法 |
| WO2015019809A1 (ja) | 2013-08-09 | 2015-02-12 | ユニマテック株式会社 | ビス（パーフルオロエーテルカルボン酸アルキル）アミノエステルおよびその製造法 |
| US9758470B2 (en) | 2013-08-09 | 2017-09-12 | Unimatec Co., Ltd. | Bis(perfluoroether carboxylic acid alkyl)amino ester and method for producing the same |
| US10000444B2 (en) | 2015-02-03 | 2018-06-19 | Unimatec Co., Ltd. | Fluorine-containing ether monocarboxylic acid aminoalkyl ester and a method for producing the same |
| JPWO2023112714A1 (enExample) * | 2021-12-14 | 2023-06-22 | ||
| JPWO2023112713A1 (enExample) * | 2021-12-14 | 2023-06-22 | ||
| WO2023112714A1 (ja) * | 2021-12-14 | 2023-06-22 | 信越化学工業株式会社 | 含フッ素活性エネルギー線硬化性組成物、硬化物、並びに物品 |
| WO2023112713A1 (ja) * | 2021-12-14 | 2023-06-22 | 信越化学工業株式会社 | フルオロポリエーテル基含有アクリル化合物 |
| JP7772089B2 (ja) | 2021-12-14 | 2025-11-18 | 信越化学工業株式会社 | 含フッ素活性エネルギー線硬化性組成物、硬化物、並びに物品 |
| JP7861798B2 (ja) | 2021-12-14 | 2026-05-19 | 信越化学工業株式会社 | フルオロポリエーテル基含有アクリル化合物 |
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