JP2022159483A - Composition - Google Patents
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- Publication number
- JP2022159483A JP2022159483A JP2022130244A JP2022130244A JP2022159483A JP 2022159483 A JP2022159483 A JP 2022159483A JP 2022130244 A JP2022130244 A JP 2022130244A JP 2022130244 A JP2022130244 A JP 2022130244A JP 2022159483 A JP2022159483 A JP 2022159483A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- hfe
- pfpe
- molecular weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 239000010702 perfluoropolyether Substances 0.000 claims abstract description 101
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- VNXYDFNVQBICRO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-methoxypropane Chemical compound COC(C(F)(F)F)C(F)(F)F VNXYDFNVQBICRO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 claims description 18
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- 239000003063 flame retardant Substances 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- LDTMPQQAWUMPKS-UPHRSURJSA-N (z)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C/Cl LDTMPQQAWUMPKS-UPHRSURJSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000011403 purification operation Methods 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 74
- 239000000243 solution Substances 0.000 description 38
- 239000011248 coating agent Substances 0.000 description 21
- 238000000576 coating method Methods 0.000 description 21
- -1 aliphatic nitro compounds Chemical class 0.000 description 18
- 238000012360 testing method Methods 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000000314 lubricant Substances 0.000 description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- CWIFAKBLLXGZIC-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1-(2,2,2-trifluoroethoxy)ethane Chemical compound FC(F)C(F)(F)OCC(F)(F)F CWIFAKBLLXGZIC-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 239000012459 cleaning agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- UJIGKESMIPTWJH-UHFFFAOYSA-N 1,3-dichloro-1,1,2,2,3-pentafluoropropane Chemical compound FC(Cl)C(F)(F)C(F)(F)Cl UJIGKESMIPTWJH-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- COAUHYBSXMIJDK-UHFFFAOYSA-N 3,3-dichloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)C(Cl)Cl COAUHYBSXMIJDK-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- QZYHIOPPLUPUJF-UHFFFAOYSA-N 3-nitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1 QZYHIOPPLUPUJF-UHFFFAOYSA-N 0.000 description 2
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Chemical class 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 229920006926 PFC Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- MMSLOZQEMPDGPI-UHFFFAOYSA-N p-Mentha-1,3,5,8-tetraene Chemical compound CC(=C)C1=CC=C(C)C=C1 MMSLOZQEMPDGPI-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ZDCRNXMZSKCKRF-UHFFFAOYSA-N tert-butyl 4-(4-bromoanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=C(Br)C=C1 ZDCRNXMZSKCKRF-UHFFFAOYSA-N 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 1
- ZHJBJVPTRJNNIK-UPHRSURJSA-N (z)-1,2-dichloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(\Cl)=C\Cl ZHJBJVPTRJNNIK-UPHRSURJSA-N 0.000 description 1
- XJSRKJAHJGCPGC-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane Chemical compound FC(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F XJSRKJAHJGCPGC-UHFFFAOYSA-N 0.000 description 1
- SKRWRXWNQFQGRU-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane Chemical compound CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SKRWRXWNQFQGRU-UHFFFAOYSA-N 0.000 description 1
- RTGGFPLAKRCINA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluorohexane Chemical compound CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F RTGGFPLAKRCINA-UHFFFAOYSA-N 0.000 description 1
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 description 1
- IDBYQQQHBYGLEQ-UHFFFAOYSA-N 1,1,2,2,3,3,4-heptafluorocyclopentane Chemical compound FC1CC(F)(F)C(F)(F)C1(F)F IDBYQQQHBYGLEQ-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- WEQSMXWTBRYPDN-UHFFFAOYSA-N 1,2,5-trimethylimidazole Chemical compound CC1=CN=C(C)N1C WEQSMXWTBRYPDN-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 description 1
- BYFNZOKBMZKTSC-UHFFFAOYSA-N 1,3-dimethyl-5-nitrobenzene Chemical compound CC1=CC(C)=CC([N+]([O-])=O)=C1 BYFNZOKBMZKTSC-UHFFFAOYSA-N 0.000 description 1
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- RDTIFYBSPQERAS-UHFFFAOYSA-N 1,4,5-trimethylimidazole Chemical compound CC=1N=CN(C)C=1C RDTIFYBSPQERAS-UHFFFAOYSA-N 0.000 description 1
- BLHTXORQJNCSII-UHFFFAOYSA-N 1,4-dimethylimidazole Chemical compound CC1=CN(C)C=N1 BLHTXORQJNCSII-UHFFFAOYSA-N 0.000 description 1
- FYFDQJRXFWGIBS-UHFFFAOYSA-N 1,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C([N+]([O-])=O)C=C1 FYFDQJRXFWGIBS-UHFFFAOYSA-N 0.000 description 1
- HQNBJNDMPLEUDS-UHFFFAOYSA-N 1,5-dimethylimidazole Chemical compound CC1=CN=CN1C HQNBJNDMPLEUDS-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- SUGXZLKUDLDTKX-UHFFFAOYSA-N 1-(2-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1[N+]([O-])=O SUGXZLKUDLDTKX-UHFFFAOYSA-N 0.000 description 1
- ARKIFHPFTHVKDT-UHFFFAOYSA-N 1-(3-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=CC([N+]([O-])=O)=C1 ARKIFHPFTHVKDT-UHFFFAOYSA-N 0.000 description 1
- WHLZPGRDRYCVRQ-UHFFFAOYSA-N 1-butyl-2-methylimidazole Chemical compound CCCCN1C=CN=C1C WHLZPGRDRYCVRQ-UHFFFAOYSA-N 0.000 description 1
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 description 1
- NYYVCPHBKQYINK-UHFFFAOYSA-N 1-ethyl-2-methylimidazole Chemical compound CCN1C=CN=C1C NYYVCPHBKQYINK-UHFFFAOYSA-N 0.000 description 1
- RESTWAHJFMZUIZ-UHFFFAOYSA-N 1-ethyl-4-nitrobenzene Chemical compound CCC1=CC=C([N+]([O-])=O)C=C1 RESTWAHJFMZUIZ-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- GVKYQGAKFDIAIL-UHFFFAOYSA-N 1-methyl-2-(2-methylpropyl)imidazole Chemical compound CC(C)CC1=NC=CN1C GVKYQGAKFDIAIL-UHFFFAOYSA-N 0.000 description 1
- DECWYWSYTFTUAV-UHFFFAOYSA-N 1-methyl-2-propylimidazole Chemical compound CCCC1=NC=CN1C DECWYWSYTFTUAV-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 1
- YCUKMYFJDGKQFC-UHFFFAOYSA-N 2-(octan-3-yloxymethyl)oxirane Chemical compound CCCCCC(CC)OCC1CO1 YCUKMYFJDGKQFC-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- WGYFINWERLNPHR-UHFFFAOYSA-N 3-nitroanisole Chemical compound COC1=CC=CC([N+]([O-])=O)=C1 WGYFINWERLNPHR-UHFFFAOYSA-N 0.000 description 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- YQYGPGKTNQNXMH-UHFFFAOYSA-N 4-nitroacetophenone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1 YQYGPGKTNQNXMH-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本発明は、パーフルオロポリエーテル基（以下、「ＰＦＰＥ基」ともいう）を有する化合物を溶解するための溶剤組成物に関する。 TECHNICAL FIELD The present invention relates to a solvent composition for dissolving a compound having a perfluoropolyether group (hereinafter also referred to as "PFPE group").
ＰＦＰＥ基を有する化合物（以下、単に「ＰＦＰＥ」ともいう）は、一般的に熱的、化学的に安定であり、電気絶縁性に優れる等といった種々の特徴を有する。ＰＦＰＥ基を有する化合物は、例えば、磁気記録媒体用等のフッ素系潤滑剤として知られている。 A compound having a PFPE group (hereinafter also simply referred to as “PFPE”) generally has various characteristics such as being thermally and chemically stable and having excellent electrical insulation. A compound having a PFPE group is known as, for example, a fluorine-based lubricant for magnetic recording media.
ＰＦＰＥ基を有する化合物は一般的に含フッ素系溶剤以外には溶解し難い。ＰＦＰＥ基を有する化合物を含む潤滑剤溶液の調製に用いる溶剤や、ＰＦＰＥ基を有する化合物が付着した物品から該化合物を除去するための洗浄剤として、クロロフルオロカーボン類（以下、「ＣＦＣ類」ともいう）、ハイドロクロロフルオロカーボン類（以下、「ＨＣＦＣ類」ともいう）、パーフルオロカーボン類（以下、「ＰＦＣ類」ともいう）、ハイドロフルオロカーボン類（以下、「ＨＦＣ類」ともいう）等が使用されてきた。しかしながら、ＣＦＣ類、ＨＣＦＣ類等は、オゾン層への悪影響の懸念から、先進国においては、使用が制限されたり、禁止される方向にある。ＰＦＣ類やＨＦＣ類は、地球温暖化係数（ＧＷＰ）が大きいことから、京都議定書で規制対象物質となっている。このことから、地球環境に与える影響が小さい物質の開発が求められている。これらの代替品としてハイドロクロロフルオロオレフィン類やハイドロフルオロオレフィン類（以下、これらを総称して「ＨＦＯ類」ともいう）やハイドロフルオロエーテル類（以下、「ＨＦＥ類」ともいう）が着目されている。 Compounds having a PFPE group are generally difficult to dissolve in solvents other than fluorine-containing solvents. Chlorofluorocarbons (hereinafter also referred to as "CFCs") are used as a solvent for preparing a lubricant solution containing a compound having a PFPE group and as a cleaning agent for removing the compound from an article to which the compound having a PFPE group is attached. ), hydrochlorofluorocarbons (hereinafter also referred to as "HCFCs"), perfluorocarbons (hereinafter also referred to as "PFCs"), hydrofluorocarbons (hereinafter also referred to as "HFCs"), etc. have been used. . However, CFCs, HCFCs, and the like are being restricted or banned from use in developed countries due to concerns about adverse effects on the ozone layer. Since PFCs and HFCs have a large global warming potential (GWP), they are regulated substances under the Kyoto Protocol. For this reason, there is a demand for the development of substances that have less impact on the global environment. Hydrochlorofluoroolefins, hydrofluoroolefins (hereinafter collectively referred to as "HFOs") and hydrofluoroethers (hereinafter also referred to as "HFEs") are drawing attention as substitutes for these. .
ＨＦＥ類の一種として、１，１，１，３，３，３－ヘキサフルオロイソプロピルメチルエーテル（以下、「ＨＦＥ－３５６ｍｍｚ」ともいう）が知られている（特許文献１、２）。 As one of HFEs, 1,1,1,3,3,3-hexafluoroisopropyl methyl ether (hereinafter also referred to as “HFE-356mmz”) is known (Patent Documents 1 and 2).
また、ＨＦＥ類の別の例として、１，１，２，２－テトラフルオロエチル－２，２，２－トリフルオロエチルエーテル（以下、「ＨＦＥ－３４７ｐｃ－ｆ」ともいう）が知られている。特許文献３には、溶剤としてＨＦＥ－３４７ｐｃ－ｆを用いた潤滑剤塗布溶液について記載されている。 As another example of HFEs, 1,1,2,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether (hereinafter also referred to as "HFE-347pc-f") is known. . Patent Document 3 describes a lubricant coating solution using HFE-347pc-f as a solvent.
本発明は、地球環境への負荷が小さく、かつ、ＰＦＰＥ基を有する化合物を溶解したときに安定性に優れる溶液とすることのできる溶剤組成物を提供することを課題とする。 SUMMARY OF THE INVENTION An object of the present invention is to provide a solvent composition which has a low impact on the global environment and can form a highly stable solution when a compound having a PFPE group is dissolved.
本発明者らは前記課題を解決するために鋭意検討を行った。その結果、１，１，１，３，３，３－ヘキサフルオロイソプロピルメチルエーテル（ＨＦＥ－３５６ｍｍｚ）を含む組成物が、パーフルオロポリエーテル（ＰＦＰＥ）を十分に溶解し、洗浄剤、溶剤として優れていることを見出し、本発明を完成させた。
本発明は、以下の態様を含む。
［１］
１，１，１，３，３，３－ヘキサフルオロイソプロピルメチルエーテル（ＨＦＥ－３５６ｍｍｚ）と、パーフルオロポリエーテル基を有する化合物とを含む、組成物。
［２］
シス－１－クロロ－３，３，３－トリフルオロプロペン（１２３３ｚｄ（Ｚ））または１，１，１，３，３－ペンタフルオロブタン（ＣＦ３－ＣＨ２－ＣＦ２－ＣＨ３、ＨＦＣ－３６５ｍｆｃ）を含む、［１］に記載の組成物。
［３］
ハイドロクロロフルオロカーボン（ＨＣＦＣ）類、ハイドロフルオロカーボン（ＨＦＣ）類、ハイドロフルオロエーテル（ＨＦＥ）類、ハイドロフルオロオレフィン（ＨＦＯ）類から選ばれる、有機溶剤を含む、［１］または［２］に記載の組成物。
［４］
ハイドロフルオロエーテル（ＨＦＥ）類が、Ｃ４Ｆ９ＯＣＨ３、Ｃ３Ｆ７ＯＣＨ３、１，１，２，２－テトラフルオロエトキシ－１－（２，２，２－トリフルオロ）エタン（ＨＦＥ－３４７ｐｃ－ｆ）から選ばれる、［３］に記載の組成物。
［５］
ハイドロフルオロオレフィン（ＨＦＯ）類が、炭素数３のＨＦＯ類である、［３］に記載の組成物。
［６］
安定剤、難燃剤、界面活性剤、金属不動態化剤または防錆剤を含む、［１］～［５］のいずれかに記載の組成物。
［７］
パーフルオロポリエーテル基を有する化合物が、数平均分子量１３００～８０００で一般式（１）で表される化合物、数平均分子量３２００～２３０００で一般式（２）で表される化合物、数平均分子量２０００～１１０００で一般式（３）で表される化合物または数平均分子量１０００～２００００で一般式（４）で表される化合物である、［１］～［６］のいずれかに記載の組成物。
（式中、ｍおよびｎは１以上の整数であり、ｍ＋ｎ＝８～１２０を満たし、Ｒ１およびＲ２はそれぞれ独立に炭素数１～３のパーフルオロアルキル基であり、ｐおよびｑは１以上の整数であり、ｐ＋ｑ＝２５～３５０を満たし、Ｒ３およびＲ４はそれぞれ独立に炭素数１～３のパーフルオロアルキル基であり、ｒは１０～８０の整数であり、Ｒ５は炭素数１～３のパーフルオロアルキル基であり、ｓ、ｔ、ｕおよびｖは１以上の整数であり、ｔ／ｓ＝２～５、（ｕ＋ｖ）／（ｓ＋ｔ＋ｕ＋ｖ）＝０．０７～０．２、ｓ／（ｓ＋ｔ＋ｕ＋ｖ）＝０．１～０．３を満たし、Ｒ６およびＲ７はそれぞれ独立に炭素数１～３のパーフルオロアルキル基である。）
［８］
パーフルオロポリエーテル基を有する化合物が、パーフルオロポリエーテル基を有する化合物の分子量のうち、パーフルオロポリエーテル基が５０％以上を占める化合物である、［１］～［６］のいずれかに記載の組成物。
［９］
パーフルオロポリエーテル基を有する化合物が、アルキル基、カルボキシ基、ヒドロキシ基、アミド基、カルボニル基、アミノ基またはアルコキシ基からなる群から少なくとも一つ選択される基を有する化合物である、［１］～［６］のいずれかに記載の組成物。
［１０］
パーフルオロポリエーテル基を有する化合物を、１，１，１，３，３，３－ヘキサフルオロイソプロピルメチルエーテル（ＨＦＥ－３５６ｍｍｚ）に溶解させることを特徴とする、［１］～［９］のいずれかに記載の組成物の溶液状態での安定化方法。
［１１］
［１］～［９］のいずれかに記載の組成物に精製操作を施して、１，１，１，３，３，３－ヘキサフルオロイソプロピルメチルエーテル（ＨＦＥ－３５６ｍｍｚ）を回収する方法。
なお本発明は、以下の態様も含む。
The present inventors have made intensive studies to solve the above problems. As a result, a composition containing 1,1,1,3,3,3-hexafluoroisopropyl methyl ether (HFE-356mmz) sufficiently dissolves perfluoropolyether (PFPE) and is excellent as a cleaning agent and solvent. The present invention was completed by finding that
The present invention includes the following aspects.
[1]
A composition comprising 1,1,1,3,3,3-hexafluoroisopropyl methyl ether (HFE-356mmz) and a compound having a perfluoropolyether group.
[2]
cis-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) or 1,1,1,3,3-pentafluorobutane (CF 3 —CH 2 —CF 2 —CH 3 , HFC- 365mfc), the composition of [1].
[3]
The composition according to [1] or [2], containing an organic solvent selected from hydrochlorofluorocarbons (HCFCs), hydrofluorocarbons (HFCs), hydrofluoroethers (HFEs), and hydrofluoroolefins (HFOs) thing.
[4]
Hydrofluoroethers (HFE) are C 4 F 9 OCH 3 , C 3 F 7 OCH 3 , 1,1,2,2-tetrafluoroethoxy-1-(2,2,2-trifluoro)ethane (HFE -347pc-f).
[5]
The composition according to [3], wherein the hydrofluoroolefins (HFOs) are C3 HFOs.
[6]
The composition according to any one of [1] to [5], comprising a stabilizer, flame retardant, surfactant, metal passivator or rust preventive.
[7]
A compound having a perfluoropolyether group is a compound represented by general formula (1) with a number average molecular weight of 1,300 to 8,000, a compound represented by general formula (2) with a number average molecular weight of 3,200 to 23,000, and a number average molecular weight of 2,000. The composition according to any one of [1] to [6], which is a compound represented by general formula (3) with a number average molecular weight of up to 11,000 or a compound represented by general formula (4) with a number average molecular weight of 1,000 to 20,000.
(Wherein, m and n are integers of 1 or more, satisfies m+n=8 to 120, R 1 and R 2 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms, and p and q are 1 p + q = 25 to 350, R 3 and R 4 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms, r is an integer of 10 to 80, and R 5 is a carbon a perfluoroalkyl group of numbers 1 to 3, s, t, u and v are integers of 1 or more, t/s = 2 to 5, (u + v) / (s + t + u + v) = 0.07 to 0.2 , s/(s+t+u+v)=0.1 to 0.3, and R 6 and R 7 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms.)
[8]
Any one of [1] to [6], wherein the compound having a perfluoropolyether group is a compound in which the perfluoropolyether group accounts for 50% or more of the molecular weight of the compound having a perfluoropolyether group. composition.
[9]
The compound having a perfluoropolyether group is a compound having at least one group selected from the group consisting of an alkyl group, a carboxy group, a hydroxy group, an amide group, a carbonyl group, an amino group, or an alkoxy group [1] The composition according to any one of to [6].
[10]
Any of [1] to [9], characterized in that a compound having a perfluoropolyether group is dissolved in 1,1,1,3,3,3-hexafluoroisopropyl methyl ether (HFE-356mmz). A method for stabilizing a composition according to any one of claims 1 to 1 in a solution state.
[11]
A method for recovering 1,1,1,3,3,3-hexafluoroisopropyl methyl ether (HFE-356mmz) by subjecting the composition according to any one of [1] to [9] to a purification operation.
The present invention also includes the following aspects.
本発明の実施形態の一つは、パーフルオロポリエーテル基を有する化合物を溶解するための溶剤組成物であって、１，１，１，３，３，３－ヘキサフルオロイソプロピルメチルエーテルを含む溶剤組成物である。この溶剤組成物において、シス－１－クロロ－３，３，３－トリフルオロプロペン（１２３３ｚｄ（Ｚ））、１，１，１，３，３－ペンタフルオロブタン（ＨＦＣ－３６５ｍｆｃ）から選択される少なくとも一つの化合物を含んでもよい。また、この溶剤組成物において、ハイドロクロロフルオロカーボン類、ハイドロフルオロカーボン類、ハイドロフルオロエーテル類、ハイドロフルオロオレフィン類から選ばれる有機溶剤を含んでもよい。また、この溶剤組成物において、安定剤、難燃剤、界面活性剤、金属不動態化剤または防錆剤を含んでもよい。 One embodiment of the present invention is a solvent composition for dissolving a compound having a perfluoropolyether group, the solvent comprising 1,1,1,3,3,3-hexafluoroisopropyl methyl ether composition. The solvent composition is selected from cis-1-chloro-3,3,3-trifluoropropene (1233zd(Z)), 1,1,1,3,3-pentafluorobutane (HFC-365mfc) It may contain at least one chemical compound. Moreover, this solvent composition may contain an organic solvent selected from hydrochlorofluorocarbons, hydrofluorocarbons, hydrofluoroethers, and hydrofluoroolefins. The solvent composition may also contain stabilizers, flame retardants, surfactants, metal passivators or rust inhibitors.
本発明の実施形態の一つは、前記溶剤組成物と、パーフルオロポリエーテル基を有する化合物とを含む、溶液である。この溶液はパーフルオロポリエーテル基を有する化合物を物品に塗布して塗膜を形成するための溶液として用いることができる。 One embodiment of the present invention is a solution containing the solvent composition and a compound having a perfluoropolyether group. This solution can be used as a solution for applying a compound having a perfluoropolyether group to an article to form a coating film.
本発明の実施形態の一つは、前記溶液を物品の表面に塗布し、次いで物品から溶剤組成物を蒸発させて、物品の表面にパーフルオロポリエーテル基を有する化合物を含む塗膜を形成する方法である。 In one embodiment of the present invention, the solution is applied to the surface of an article, and then the solvent composition is evaporated from the article to form a coating film containing a compound having a perfluoropolyether group on the surface of the article. The method.
本発明の実施形態の一つは、パーフルオロポリエーテル基を有する化合物が付着した物品を、前記溶剤組成物を用いて洗浄する方法である。 One of the embodiments of the present invention is a method of washing an article to which a compound having a perfluoropolyether group is attached, using the solvent composition.
パーフルオロポリエーテル基を有する化合物は、数平均分子量１３００～８０００で一般式（１）で表される化合物、数平均分子量３２００～２３０００で一般式（２）で表される化合物、数平均分子量２０００～１１０００で、一般式（３）で表される化合物、または、数平均分子量１０００～２００００を有し、一般式（４）で表される化合物であってもよい。
一般式（１）中、ｍおよびｎは１以上の整数であり、ｍ＋ｎ＝８～１２０を満たし、Ｒ１およびＲ２はそれぞれ独立に炭素数１～３のパーフルオロアルキル基である。一般式（２）中、ｐおよびｑは１以上の整数であり、ｐ＋ｑ＝２５～３５０を満たし、Ｒ３およびＲ４はそれぞれ独立に炭素数１～３のパーフルオロアルキル基である。一般式（３）中、ｒは１０～８０の整数であり、Ｒ５は炭素数１～３のパーフルオロアルキル基である。一般式（４）中、ｓ、ｔ、ｕおよびｖは１以上の整数であり、ｔ／ｓ＝２～５、（ｕ＋ｖ）／（ｓ＋ｔ＋ｕ＋ｖ）＝０．０７～０．２、ｓ／（ｓ＋ｔ＋ｕ＋ｖ）＝０．１～０．３を満たし、Ｒ６およびＲ７はそれぞれ独立に炭素数１～３のパーフルオロアルキル基である。 In general formula (1), m and n are integers of 1 or more, satisfying m+n=8 to 120, and R 1 and R 2 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms. In general formula (2), p and q are integers of 1 or more, satisfying p+q=25 to 350, and R 3 and R 4 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms. In general formula (3), r is an integer of 10 to 80, and R 5 is a perfluoroalkyl group having 1 to 3 carbon atoms. In the general formula (4), s, t, u and v are integers of 1 or more, t / s = 2 to 5, (u + v) / (s + t + u + v) = 0.07 to 0.2, s / (s + t + u + v )=0.1 to 0.3, and R 6 and R 7 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms.
本発明によれば、地球環境への負荷が小さく、かつ、ＰＦＰＥ基を有する化合物を溶解したときに安定性に優れる溶液とすることのできる溶剤組成物を提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the solvent composition which has a small load to global environment and can be made into the solution which is excellent in stability, when the compound which has a PFPE group is melt|dissolved can be provided.
後述の実施例においても示されるように、ＨＦＥ類とフッ素系潤滑剤の組み合わせによっては、該フッ素系潤滑剤が該ＨＦＥ類に溶解しないこともあり、また、溶液とすることができたとしても、安定的に均一溶液を保持できるか否かは不明である。このように、潤滑剤溶液を調製するために、溶剤とＰＦＰＥ基を有する化合物の好適な組み合わせを見出すことは容易ではない。特許文献３には、ＨＦＥ－３５６ｍｍｚを含む混合溶剤を用いた洗浄方法について記載されているものの、被洗浄物表面に付着している汚れがＰＦＰＥ基を有する化合物である場合についての詳細は記載されておらず、ＰＦＰＥ基を有する化合物を溶液状態としたときの安定性についても不明であった。 As shown in the examples below, depending on the combination of the HFEs and the fluorine-based lubricant, the fluorine-based lubricant may not dissolve in the HFEs. , it is unclear whether a homogeneous solution can be stably maintained. Thus, it is not easy to find a suitable combination of a solvent and a compound having PFPE groups for preparing a lubricant solution. Although Patent Document 3 describes a cleaning method using a mixed solvent containing HFE-356mmz, it does not describe in detail the case where the dirt adhering to the surface of the object to be cleaned is a compound having a PFPE group. Moreover, the stability of a compound having a PFPE group in a solution state was also unknown.
以下、本発明の実施形態について説明する。ただし本発明は、その要旨を逸脱しない範囲において様々な態様で実施することができ、以下に例示する実施形態の記載内容に限定して解釈されるものではない。また、以下の実施形態の態様によりもたらされる作用効果とは異なる他の作用効果であっても、本明細書の記載から明らかなもの、または、当業者において容易に予測し得るものについては、当然に本発明によりもたらされたものと解される。 Embodiments of the present invention will be described below. However, the present invention can be implemented in various aspects without departing from the gist thereof, and should not be construed as being limited to the description of the embodiments illustrated below. In addition, even if there are other effects that are different from the effects brought about by the aspects of the following embodiments, those that are obvious from the description of this specification or those that can be easily predicted by those skilled in the art are of course It is understood that it is brought about by the present invention.
［１．ＨＦＥ－３５６ｍｍｚを含む溶剤組成物］
本実施形態では、ＰＦＰＥ基を有する化合物を溶解するための溶剤組成物であって、ＨＦＥ－３５６ｍｍｚを含む溶剤組成物（以下、単に「本溶剤組成物」ともいう）を説明する。
[1. Solvent composition containing HFE-356mmz]
In the present embodiment, a solvent composition for dissolving a compound having a PFPE group and containing HFE-356mmz (hereinafter also simply referred to as "this solvent composition") will be described.
（ＨＦＥ－３５６ｍｍｚ）
本溶剤組成物には、ＨＦＥ－３５６ｍｍｚが含まれ、例えば、３０質量％以上含まれ、好ましくは５０質量％以上、より好ましくは７０質量％以上、特に好ましくは９０質量％以上含まれる。また、実質的にＨＦＥ－３５６ｍｍｚのみが含まれてもよい。なお、ＨＦＥ－３５６ｍｍｚは公知の化合物であり、例えば、アルカリ存在下、１，１，１，３，３，３－ヘキサフルオロイソプロアルコールとジメチル硫酸との反応により得ることができる（米国特許３３４６４４８号）。
(HFE-356mmz)
The present solvent composition contains HFE-356mmz, for example, 30% by mass or more, preferably 50% by mass or more, more preferably 70% by mass or more, and particularly preferably 90% by mass or more. It may also contain substantially only HFE-356mmz. HFE-356mmz is a known compound and can be obtained, for example, by reacting 1,1,1,3,3,3-hexafluoroisoproalcohol with dimethyl sulfate in the presence of an alkali (US Pat. No. 3,346,448). ).
（１２３３ｚｄ（Ｚ）、ＨＦＣ－３６５ｍｆｃ）
本溶剤組成物には、シス－１－クロロ－３，３，３－トリフルオロプロペン（以下、「１２３３ｚｄ（Ｚ）」ともいう）、１，１，１，３，３－ペンタフルオロブタン（以下、「ＨＦＣ－３６５ｍｆｃ」ともいう）が含まれてもよく、例えば、本溶剤組成物において、１２３３ｚｄ（Ｚ）とＨＦＣ－３６５ｍｆｃとの合計の割合は、７０質量％以下、５０質量％以下、３０質量％以下、１０質量％以下であってもよい。なお、１２３３ｚｄ（Ｚ）（ＣＥＬＥＦＩＮ（登録商標）１２３３Ｚ（セントラル硝子社製））、ＨＦＣ－３６５ｍｆｃ（ソルカン（登録商標）３６５ｍｆｃ（ソルベイ社製））は公知の化合物であり、それぞれ市販されている。
(1233zd(Z), HFC-365mfc)
The solvent composition includes cis-1-chloro-3,3,3-trifluoropropene (hereinafter also referred to as "1233zd (Z)"), 1,1,1,3,3-pentafluorobutane (hereinafter , also referred to as “HFC-365mfc”), for example, in the present solvent composition, the total ratio of 1233zd(Z) and HFC-365mfc is 70 mass% or less, 50 mass% or less, 30 % by mass or less, or 10% by mass or less. 1233zd(Z) (CELEFIN (registered trademark) 1233Z (manufactured by Central Glass)) and HFC-365mfc (Solcan (registered trademark) 365mfc (manufactured by Solvay)) are known compounds and are commercially available.
（他の有機溶剤）
本溶剤組成物には、他の有機溶剤が含まれてもよい。例えば、本溶剤組成物において、他の有機溶剤は３０質量％以下、２０質量％以下、１０質量％以下含まれてもよい。他の有機溶剤としては、例えば、ハイドロクロロフルオロカーボン類（ＨＣＦＣ類）、ハイドロフルオロカーボン類（ＨＦＣ類）、ハイドロフルオロエーテル類（ＨＦＥ類）、ハイドロフルオロオレフィン類（ＨＦＯ類）が挙げられる。これらは単独で用いてもよく、２種以上を併用してもよい。
(other organic solvents)
The solvent composition may contain other organic solvents. For example, the present solvent composition may contain other organic solvents in an amount of 30% by mass or less, 20% by mass or less, or 10% by mass or less. Other organic solvents include, for example, hydrochlorofluorocarbons (HCFCs), hydrofluorocarbons (HFCs), hydrofluoroethers (HFEs), and hydrofluoroolefins (HFOs). These may be used alone or in combination of two or more.
ＨＣＦＣ類としては、例えば、炭素数３～８の鎖状または環状のＨＣＦＣ類が挙げられる。より具体的には、３，３－ジクロロ－１，１，１，２，２－ペンタフルオロプロパン（ＨＣＦＣ－２２５ｃａ）、１，３－ジクロロ－１，１，２，２，３－ペンタフルオロプロパン（ＨＣＦＣ－２２５ｃｂ）等が挙げられるが、これらに限られない。 HCFCs include, for example, chain or cyclic HCFCs having 3 to 8 carbon atoms. More specifically, 3,3-dichloro-1,1,1,2,2-pentafluoropropane (HCFC-225ca), 1,3-dichloro-1,1,2,2,3-pentafluoropropane (HCFC-225cb) and the like, but not limited to these.
ＨＦＣ類としては、例えば、炭素数４～８の鎖状または環状のＨＦＣ類が挙げられ、１分子中のフッ素原子数が水素原子数以上であるＨＦＣ類が好ましい。より具体的には、１，１，１，３，３－ペンタフルオロブタン、１，１，１，２，２，３，４，５，５，５－デカフルオロペンタン、１，１，２，２，３，３，４－ヘプタフルオロシクロペンタン、１，１，１，２，２，３，３，４，４－ノナフルオロヘキサン、１，１，１，２，２，３，３，４，４，５，５，６，６－トリデカフルオロヘキサン、１，１，１，２，２，３，３，４，４，５，５，６，６－トリデカフルオロオクタン等が挙げられるが、これらに限られない。 HFCs include, for example, chain or cyclic HFCs having 4 to 8 carbon atoms, and HFCs in which the number of fluorine atoms in one molecule is equal to or greater than the number of hydrogen atoms is preferred. More specifically, 1,1,1,3,3-pentafluorobutane, 1,1,1,2,2,3,4,5,5,5-decafluoropentane, 1,1,2, 2,3,3,4-heptafluorocyclopentane, 1,1,1,2,2,3,3,4,4-nonafluorohexane, 1,1,1,2,2,3,3,4 , 4,5,5,6,6-tridecafluorohexane, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane and the like. However, it is not limited to these.
ＨＦＥ類としては、例えば、炭素数４～８の鎖状または環状のＨＦＥ類が挙げられる。
より具体的には、Ｃ４Ｆ９ＯＣＨ３、Ｃ３Ｆ７ＯＣＨ３、１，１，２，２－テトラフルオロエトキシ－１－（２，２，２－トリフルオロ）エタン（ＨＦＥ－３４７ｐｃ－ｆ。例えば、市販品としてアサヒクリン（登録商標）ＡＥ－３０００（ＡＧＣ社製）がある）等が挙げられるが、これらに限られない。
HFEs include, for example, chain or cyclic HFEs having 4 to 8 carbon atoms.
More specifically, C 4 F 9 OCH 3 , C 3 F 7 OCH 3 , 1,1,2,2-tetrafluoroethoxy-1-(2,2,2-trifluoro)ethane (HFE-347pc- f.For example, commercially available products include Asahiklin (registered trademark) AE-3000 (manufactured by AGC), etc., but not limited thereto.
ＨＦＯ類としては、例えば、炭素数３～６のＨＦＯ類が挙げられる。より具体的には、１，３，３，３－テトラフルオロプロペン、２，３，３，３－テトラフルオロプロペン、１，２－ジクロロ－３，３，３－トリフルオロプロペン等が挙げられるが、これらに限られない。 HFOs include, for example, HFOs having 3 to 6 carbon atoms. More specific examples include 1,3,3,3-tetrafluoropropene, 2,3,3,3-tetrafluoropropene, 1,2-dichloro-3,3,3-trifluoropropene, and the like. , but not limited to these.
（安定剤）
本溶剤組成物には、安定剤が含まれてもよい。安定剤が含まれることで、例えば、熱安定性、耐酸化性等を向上させることができる。例えば、本溶剤組成物において、安定剤は１０質量％以下、３質量％以下、１質量％以下、０．１質量％以下含まれてもよい。この安定剤としては、例えば、ニトロ化合物、エポキシ化合物、フェノール類、イミダゾール類、アミン類、不飽和炭化水素類等が挙げられるが、これらに限定されない。また、これらは単独で用いてもよく、２種以上を併用してもよい。
(stabilizer)
The solvent composition may also contain stabilizers. By containing a stabilizer, for example, thermal stability, oxidation resistance, etc. can be improved. For example, the solvent composition may comprise 10 wt% or less, 3 wt% or less, 1 wt% or less, 0.1 wt% or less of the stabilizer. Examples of the stabilizer include, but are not limited to, nitro compounds, epoxy compounds, phenols, imidazoles, amines, unsaturated hydrocarbons, and the like. Moreover, these may be used independently and may use 2 or more types together.
ニトロ化合物としては、例えば、脂肪族及び／または芳香族誘導体が挙げられる。脂肪族系ニトロ化合物としては、例えば、ニトロメタン、ニトロエタン、１－ニトロプロパン、２－ニトロプロパン等が挙げられる。芳香族ニトロ化合物としては、例えば、ニトロベンゼン、ｏ－、ｍ－又はｐ－ジニトロベンゼン、トリニトロベンゼン、ｏ－、ｍ－又はｐ－ニトロトルエン、ｏ－、ｍ－又はｐ－エチルニトロベンゼン、２，３－、２，４－、２，５－、２，６－、３，４－又は３，５－ジメチルニトロベンゼン、ｏ－、ｍ－又はｐ－ニトロアセトフェノン、ｏ－、ｍ－又はｐ－ニトロフェノール、ｏ－、ｍ－又はｐ－ニトロアニソール等が挙げられる。 Nitro compounds include, for example, aliphatic and/or aromatic derivatives. Examples of aliphatic nitro compounds include nitromethane, nitroethane, 1-nitropropane, 2-nitropropane and the like. Examples of aromatic nitro compounds include nitrobenzene, o-, m- or p-dinitrobenzene, trinitrobenzene, o-, m- or p-nitrotoluene, o-, m- or p-ethylnitrobenzene, 2,3- , 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethylnitrobenzene, o-, m- or p-nitroacetophenone, o-, m- or p-nitrophenol, o-, m- or p-nitroanisole and the like.
エポキシ化合物としては、例えばエチレンオキサイド、１，２－ブチレンオキサイド、プロピレンオキサイド、スチレンオキサイド、シクロヘキセンオキサイド、グリシドール、エピクロルヒドリン、グリシジルメタアクリレート、フェニルグリシジルエーテル、アリルグリシジルエーテル、メチルグリシジルエーテル、ブチルグリシジルエーテル、２－エチルヘキシルグリシジルエーテル等のモノエポキシ系化合物、ジエポキシブタン、ビニルシクロヘキセンジオキサイド、ネオペンチルグリコールジグリシジルエーテル、エチレングリコールジグリシジルエーテル、グリセリンポリグリシジルエーテル、トリメチロールプロパントルグリシジルエーテル等のポリエポキシ系化合物等が挙げられる。 Examples of epoxy compounds include ethylene oxide, 1,2-butylene oxide, propylene oxide, styrene oxide, cyclohexene oxide, glycidol, epichlorohydrin, glycidyl methacrylate, phenyl glycidyl ether, allyl glycidyl ether, methyl glycidyl ether, butyl glycidyl ether, 2 - monoepoxy compounds such as ethylhexyl glycidyl ether, polyepoxy compounds such as diepoxybutane, vinylcyclohexene dioxide, neopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, glycerin polyglycidyl ether, trimethylolpropane triglycidyl ether etc.
フェノール類としては、例えば、フェノール性水酸基とともに、アルキル基、アルケニル基、アルコキシ基、カルボキシル基、カルボニル基、ハロゲン等各種の置換基を含み得る芳香族化合物が挙げられる。このような芳香族化合物としては、例えば、２，６－ジ－ｔ－ブチル－ｐ－クレゾール、ｏ－クレゾール、ｍ－クレゾール、ｐ－クレゾール、チモール、ｐ－ｔ－ブチルフェノール、ｏ－メトキシフェノール、ｍ－メトキシフェノール、ｐ－メトキシフェノール、オイゲノール、イソオイゲノール、ブチルヒドロキシアニソール、フェノール、キシレノール等の１価のフェノールあるいはｔ－ブチルカテコール、２，５－ジ－ｔ－アミノハイドロキノン、２，５－ジ－ｔ－ブチルハイドロキノン等の２価のフェノール等が挙げられる。 Phenols include, for example, aromatic compounds that may contain various substituents such as alkyl groups, alkenyl groups, alkoxy groups, carboxyl groups, carbonyl groups, and halogens in addition to phenolic hydroxyl groups. Examples of such aromatic compounds include 2,6-di-t-butyl-p-cresol, o-cresol, m-cresol, p-cresol, thymol, pt-butylphenol, o-methoxyphenol, Monohydric phenols such as m-methoxyphenol, p-methoxyphenol, eugenol, isoeugenol, butylhydroxyanisole, phenol, xylenol, t-butylcatechol, 2,5-di-t-aminohydroquinone, 2,5-di - dihydric phenols such as t-butylhydroquinone and the like.
イミダゾール類としては、炭素数１～１８のアルキル基、シクロアルキル基、またはアリール基をＮ位の置換基とする、１－メチルイミダゾール、１－ｎ－ブチルイミダゾール、１－フェニルイミダゾール、１－ベンジルイミダゾール、１－（β－オキシエチル）イミダゾール、１－メチル－２－プロピルイミダゾール、１－メチル－２－イソブチルイミダゾール、１－ｎ－ブチル－２－メチルイミダゾール、１，２－ジメチルイミダゾール、１，４－ジメチルイミダゾール、１，５－ジメチルイミダゾール、１，２，５－トリメチルイミダゾール、１，４，５－トリメチルイミダゾール、１－エチル－２－メチルイミダゾール等が挙げられる。 Examples of imidazoles include 1-methylimidazole, 1-n-butylimidazole, 1-phenylimidazole and 1-benzyl having an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group, or an aryl group as a substituent at the N-position. imidazole, 1-(β-oxyethyl)imidazole, 1-methyl-2-propylimidazole, 1-methyl-2-isobutylimidazole, 1-n-butyl-2-methylimidazole, 1,2-dimethylimidazole, 1,4 -dimethylimidazole, 1,5-dimethylimidazole, 1,2,5-trimethylimidazole, 1,4,5-trimethylimidazole, 1-ethyl-2-methylimidazole and the like.
アミン類としては、ペンチルアミン、ヘキシルアミン、ジイソプロピルアミン、ジイソブチルアミン、ジ－ｎ－プロピルアミン、ジアリルアミン、トリエチルアミン、Ｎ－メチルアニリン、ピリジン、モルホリン、Ｎ－メチルモルホリン、トリアリルアミン、アリルアミン、α―メチルベンジルアミン、メチルアミン、ジメチルアミン、トリメチルアミン、エチルアミン、ジエチルアミン、プロピルアミン、イソプロピルアミン、ジプロピルアミン、ブチルアミン、イソブチルアミン、ジブチルアミン、トリブチルアミン、ジペンチルアミン、トリペンチルアミン、２－エチルヘキシルアミン、アニリン、Ｎ，Ｎ－ジメチルアニリン、Ｎ，Ｎ－ジエチルアニリン、エチレンジアミン、プロピレンジアミン、ジエチレントリアミン、テトラエチレンペンタミン、ベンジルアミン、ジベンジルアミン、ジフェニルアミン、ジエチルヒドロキシルアミン等が挙げられる。 Amines include pentylamine, hexylamine, diisopropylamine, diisobutylamine, di-n-propylamine, diallylamine, triethylamine, N-methylaniline, pyridine, morpholine, N-methylmorpholine, triallylamine, allylamine, α-methyl benzylamine, methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, propylamine, isopropylamine, dipropylamine, butylamine, isobutylamine, dibutylamine, tributylamine, dipentylamine, tripentylamine, 2-ethylhexylamine, aniline, N,N-dimethylaniline, N,N-diethylaniline, ethylenediamine, propylenediamine, diethylenetriamine, tetraethylenepentamine, benzylamine, dibenzylamine, diphenylamine, diethylhydroxylamine and the like.
不飽和炭化水素類としては、α－メチルスチレン、ｐ－イソプロペニルトルエン、イソプレン類、プロパジエン類、テルペン類等が挙げられる。 Examples of unsaturated hydrocarbons include α-methylstyrene, p-isopropenyltoluene, isoprenes, propadienes, terpenes and the like.
（難燃剤）
本溶剤組成物には、難燃剤が含まれてもよい。難燃剤が含まれることで、難燃性を向上させることができる。例えば、本溶剤組成物において、難燃剤は３質量％以下、１質量％以下、０．１質量％以下含まれてもよい。このような難燃剤としては、ホスフェート類、ハロゲン化芳香族化合物、フッ素化ヨードカーボン、フッ素化ブロモカーボン等が挙げられるが、これらに限定されない。
(Flame retardants)
The solvent composition may also contain a flame retardant. Flame retardancy can be improved by containing a flame retardant. For example, in the present solvent composition, the flame retardant may be contained in an amount of 3% by mass or less, 1% by mass or less, or 0.1% by mass or less. Such flame retardants include, but are not limited to, phosphates, halogenated aromatic compounds, fluorinated iodocarbons, fluorinated bromocarbons, and the like.
（界面活性剤）
本溶剤組成物には、界面活性剤が含まれてもよい。界面活性剤が含まれることで、例えば、洗浄力、界面作用等を向上させることができる。例えば、本溶剤組成物において、界面活性剤は３質量％以下、１質量％以下、０．１質量％以下含まれてもよい。界面活性剤としては、ソルビタンモノオレエート、ソルビタントリオレエート等のソルビタン脂肪族エステル類；ポリオキシエチレンのソルビットテトラオレエート等のポリオキシエチレンソルビット脂肪酸エステル類；ポリオキシエチレンモノラウレート等のポリエチレングリコール脂肪酸エステル類；ポリオキシエチレンラウリルエーテル等のポリオキシエチレンアルキルエーテル類；ポリオキシエチレンノニルフェニルエーテル等のポリオキシエチレンアルキルフェニルエーテル類；ポリオキシエチレンオレイン酸アミド等のポリオキシエチレンアルキルアミン脂肪酸アミド類等のノニオン系界面活性剤が挙げられる。
(Surfactant)
A surfactant may be included in the solvent composition. By containing a surfactant, for example, detergency, interfacial action, etc. can be improved. For example, in the solvent composition, the surfactant may be contained in an amount of 3% by mass or less, 1% by mass or less, or 0.1% by mass or less. Surfactants include sorbitan aliphatic esters such as sorbitan monooleate and sorbitan trioleate; polyoxyethylene sorbitol fatty acid esters such as polyoxyethylene sorbitol tetraoleate; polyethylene glycols such as polyoxyethylene monolaurate. Fatty acid esters; polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether; polyoxyethylene alkylphenyl ethers such as polyoxyethylene nonylphenyl ether; polyoxyethylene alkylamine fatty acid amides such as polyoxyethylene oleic acid amide Nonionic surfactants such as
（金属不動態化剤）
本溶剤組成物には、金属不動態化剤が含まれてもよい。例えば、本溶剤組成物において、金属不動態化剤は３質量％以下、１質量％以下、０．１質量％以下含まれてもよい。
(metal passivator)
The solvent composition may also include a metal passivator. For example, in the present solvent composition, the metal passivator may be included in an amount of 3% by mass or less, 1% by mass or less, or 0.1% by mass or less.
（防錆剤）
本溶剤組成物には、防錆剤が含まれてもよい。例えば、本溶剤組成物において、防錆剤は３質量％以下、１質量％以下、０．１質量％以下含まれてもよい。
(anti-rust)
The solvent composition may contain a rust inhibitor. For example, in the present solvent composition, the rust inhibitor may be contained in an amount of 3% by mass or less, 1% by mass or less, or 0.1% by mass or less.
（溶剤組成物の例示）
本溶剤組成物は、例えば、以下の組成が挙げられるが、この限りではない。
本溶剤組成物１００質量％に対し、
３０質量％以上のＨＦＥ－３５６ｍｍｚと、６０質量％以下の１２３３ｚｄ（Ｚ）またはＨＦＣ－３６５ｍｆｃと、０質量％以上１０質量％以下のその他の成分とを含む組成物；４０質量％以上のＨＦＥ－３５６ｍｍｚと、５０質量％以下の１２３３ｚｄ（Ｚ）またはＨＦＣ－３６５ｍｆｃと、０質量％以上１０質量％以下のその他の成分とを含む組成物；５０質量％以上のＨＦＥ－３５６ｍｍｚと、４０質量％以下の１２３３ｚｄ（Ｚ）またはＨＦＣ－３６５ｍｆｃと、０質量％以上１０質量％以下のその他の成分とを含む組成物；６０質量％以上のＨＦＥ－３５６ｍｍｚと、３０質量％以下の１２３３ｚｄ（Ｚ）またはＨＦＣ－３６５ｍｆｃと、０質量％以上１０質量％以下のその他の成分とを含む組成物；７０質量％以上のＨＦＥ－３５６ｍｍｚと、２０質量％以下の１２３３ｚｄ（Ｚ）またはＨＦＣ－３６５ｍｆｃと、０質量％以上１０質量％以下のその他の成分とを含む組成物；８０質量％以上のＨＦＥ－３５６ｍｍｚと、１０質量％以下の１２３３ｚｄ（Ｚ）またはＨＦＣ－３６５ｍｆｃと、０質量％以上１０質量％以下のその他の成分とを含む組成物；８５質量％以上のＨＦＥ－３５６ｍｍｚと、５質量％以下の１２３３ｚｄ（Ｚ）またはＨＦＣ－３６５ｍｆｃと、０質量％以上１０質量％以下のその他の成分とを含む組成物；９０質量％以上のＨＦＥ－３５６ｍｍｚを含む組成物；９５質量％以上のＨＦＥ－３５６ｍｍｚを含む組成物。
(Example of solvent composition)
Examples of the solvent composition include, but are not limited to, the following compositions.
For 100% by mass of the solvent composition,
A composition containing 30% by mass or more of HFE-356mmz, 60% by mass or less of 1233zd (Z) or HFC-365mfc, and 0% by mass or more and 10% by mass or less of other components; 40% by mass or more of HFE- Composition containing 356mmz, 50% by mass or less of 1233zd(Z) or HFC-365mfc, and 0% by mass or more and 10% by mass or less of other components; 50% by mass or more of HFE-356mmz, and 40% by mass or less of 1233zd(Z) or HFC-365mfc and 0 to 10% by weight of other components; 60% by weight or more of HFE-356mmz and 30% by weight or less of 1233zd(Z) or HFC - A composition containing 365mfc and 0% to 10% by weight of other components; 80% by mass or more of HFE-356mmz, 10% by mass or less of 1233zd(Z) or HFC-365mfc, and 0% by mass or more and 10% by mass or less of other components A composition containing 85% by mass or more of HFE-356mmz, 5% by mass or less of 1233zd (Z) or HFC-365mfc, and 0% by mass or more and 10% by mass or less of other components a composition containing 90% by mass or more of HFE-356mmz; a composition containing 95% by mass or more of HFE-356mmz.
（ＰＦＰＥ基を有する化合物）
本明細書において、ＰＦＰＥ基を有する化合物とは、－ＣａＦ２ａＯ－（ａは１～６の整数である）で表される繰り返し単位（オキシパーフルオロアルキレン基）、好ましくは、－Ｃ４Ｆ８Ｏ－、－Ｃ３Ｆ６Ｏ－、－Ｃ２Ｆ４Ｏ－および－ＣＦ２Ｏ－からなる群より選択される少なくとも一種の繰り返し単位を有する化合物である。本溶剤組成物で溶解するＰＦＰＥ基を有する化合物としては、ＰＦＰＥ基を有する化合物であれば特に制限されないが、ＰＦＰＥ基が化合物全体の主要部分を占める、すなわち、ＰＦＰＥ基を有する化合物の分子量のうち、ＰＦＰＥ基が５０％以上、６０％以上、７０％以上、８０％以上もしくは９０％以上を占める化合物が好ましい。ＰＦＰＥ基を有する化合物は、アルキル基、カルボキシ基、ヒドロキシ基、アミド基、カルボニル基、アミノ基またはアルコキシ基を有していてもよい。ＰＦＰＥ基を有する化合物は、パーフルオロ化合物、すなわち、パーフルオロポリエーテルであることが好ましい。
(Compound having PFPE group)
As used herein, a compound having a PFPE group means a repeating unit (oxyperfluoroalkylene group) represented by —C a F 2a O— (a is an integer of 1 to 6), preferably —C It is a compound having at least one repeating unit selected from the group consisting of 4F 8 O-, -C 3 F 6 O-, -C 2 F 4 O- and -CF 2 O-. The compound having a PFPE group that dissolves in the present solvent composition is not particularly limited as long as it is a compound having a PFPE group. , PFPE groups account for 50% or more, 60% or more, 70% or more, 80% or more or 90% or more. A compound having a PFPE group may have an alkyl group, a carboxy group, a hydroxy group, an amide group, a carbonyl group, an amino group or an alkoxy group. The compound having a PFPE group is preferably a perfluoro compound, ie perfluoropolyether.
ＰＦＰＥ基を有する化合物としては、例えば、フッ素系潤滑剤として一般的に用いられるパーフルオロポリエーテルである以下の（ａ）～（ｄ）の化合物が挙げられるが、これらに限定されない。
（ａ）数平均分子量１３００～８０００を有し、一般式（１）で表される化合物、
（ｂ）数平均分子量３２００～２３０００を有し、一般式（２）で表される化合物、
（ｃ）数平均分子量２０００～１１０００を有し、一般式（３）で表される化合物
（ｄ）数平均分子量１０００～２００００を有し、一般式（４）で表される化合物。
(a) a compound having a number average molecular weight of 1300 to 8000 and represented by the general formula (1);
(b) a compound having a number average molecular weight of 3200 to 23000 and represented by the general formula (2);
(c) a compound having a number average molecular weight of 2,000 to 11,000 and represented by general formula (3); (d) a compound having a number average molecular weight of 1,000 to 20,000 and represented by general formula (4).
一般式（１）中、ｍおよびｎは１以上の整数であり、ｍ＋ｎ＝８～１２０を満たし、Ｒ１およびＲ２はそれぞれ独立に炭素数１～３のパーフルオロアルキル基である。一般式（２）中、ｐおよびｑは１以上の整数であり、ｐ＋ｑ＝２５～３５０を満たし、Ｒ３およびＲ４はそれぞれ独立に炭素数１～３のパーフルオロアルキル基である。一般式（３）中、ｒは１０～８０の整数であり、Ｒ５は炭素数１～３のパーフルオロアルキル基である。一般式（４）中、ｓ、ｔ、ｕおよびｖは１以上の整数であり、ｔ／ｓ＝２～５、（ｕ＋ｖ）／（ｓ＋ｔ＋ｕ＋ｖ）＝０．０７～０．２、ｓ／（ｓ＋ｔ＋ｕ＋ｖ）＝０．１～０．３を満たし、Ｒ６およびＲ７はそれぞれ独立に炭素数１～３のパーフルオロアルキル基である。 In general formula (1), m and n are integers of 1 or more, satisfying m+n=8 to 120, and R 1 and R 2 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms. In general formula (2), p and q are integers of 1 or more, satisfying p+q=25 to 350, and R 3 and R 4 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms. In general formula (3), r is an integer of 10 to 80, and R 5 is a perfluoroalkyl group having 1 to 3 carbon atoms. In the general formula (4), s, t, u and v are integers of 1 or more, t / s = 2 to 5, (u + v) / (s + t + u + v) = 0.07 to 0.2, s / (s + t + u + v )=0.1 to 0.3, and R 6 and R 7 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms.
ここで、数平均分子量とは、ゲルパーミエーションクロマトグラフィー（ＧＰＣ）におけるポリスチレン換算の数平均分子量を指す。 Here, the number average molecular weight refers to the polystyrene equivalent number average molecular weight in gel permeation chromatography (GPC).
この他にも、本溶剤組成物で溶解するＰＦＰＥ基を有する化合物としては、例えば、パーフルオロポリエーテル改質アルキルオキシシランポリマーが挙げられる。 In addition, compounds having PFPE groups that are soluble in the present solvent composition include, for example, perfluoropolyether-modified alkyloxysilane polymers.
また、本溶剤組成物で溶解するＰＦＰＥ基を有する化合物としては、例えば、以下の製品が挙げられるがこれらに限られない：
ソルベイ スペシャリティポリマー社製のＦｏｍｂｌｉｎ（登録商標）Ｙシリーズ、Ｆｏｍｂｌｉｎ（登録商標）Ｍシリーズ、Ｆｏｍｂｌｉｎ（登録商標）Ｗシリーズ、Ｆｏｍｂｌｉｎ（登録商標）Ｚシリーズ；ダイキン工業社製のＤＥＭＮＵＭ（登録商標）シリーズ；デュポン社製のＫｒｙｔｏｘ（登録商標）シリーズ。
Compounds having PFPE groups that are soluble in the present solvent composition include, but are not limited to, the following products:
Fomblin® Y series, Fomblin® M series, Fomblin® W series, Fomblin® Z series manufactured by Solvay Specialty Polymers; DEMNUM® series manufactured by Daikin Industries; Krytox (registered trademark) series manufactured by DuPont.
パーフルオロポリエーテルを含有するフッ素系潤滑剤は、パーフルオロポリエーテルとともに添加剤（例えば防錆剤等）が含まれたり、ポリテトラフルオロエチレン樹脂パウダー等のフッ素系固体潤滑剤と混合して使用されることもある。本溶剤組成物は、ＰＦＰＥ基を有する化合物を溶解するとともに、このような成分が存在する場合にも有用である。
したがって、本発明においては、ＰＦＰＥ基を有する化合物が、パーフルオロポリエーテルとともにこのような成分を含有する組成物であっても適用できる。
Fluorine-based lubricants containing perfluoropolyether contain additives (such as rust inhibitors) together with perfluoropolyether, or are used by mixing with fluorine-based solid lubricants such as polytetrafluoroethylene resin powder. Sometimes it is done. The solvent composition dissolves compounds having PFPE groups and is also useful when such components are present.
Therefore, in the present invention, a compound having a PFPE group can be applied to a composition containing such a component together with perfluoropolyether.
［２．本溶剤組成物と、ＰＦＰＥ基を有する化合物とを含む、溶液］
本溶剤組成物は、ＰＦＰＥ基を有する化合物を溶解させて、本溶剤組成物とＰＦＰＥ基を有する化合物とを含む溶液とすることができる。この溶液は、例えば、ＰＦＰＥ基を有する化合物の塗膜を形成するための溶液（以下、「塗布用溶液」ともいう）として用いることができる。この塗布用溶液を物品の表面に塗布し、次いで物品から本溶剤組成物を蒸発させることにより、物品の表面にＰＦＰＥ基を有する化合物を含む塗膜を形成した塗膜付物品を製造することができる。
[2. Solution containing the present solvent composition and a compound having a PFPE group]
The present solvent composition can be prepared by dissolving a compound having a PFPE group to obtain a solution containing the present solvent composition and a compound having a PFPE group. This solution can be used, for example, as a solution for forming a coating film of a compound having a PFPE group (hereinafter also referred to as "coating solution"). By applying this coating solution to the surface of an article and then evaporating the present solvent composition from the article, a coated article having a coating film containing a compound having a PFPE group formed on the surface of the article can be produced. can.
例えば、刷毛による塗布、スプレーによる塗布、物品を塗布用溶液に浸漬することによる塗布、塗布用溶液を吸い上げることによりチューブや注射針の内壁に塗布用溶液を接触させる等の方法により、物品に塗布用溶液を塗布し、次いで乾燥により本溶剤組成物を蒸発させて、物品表面に塗膜を形成することができる。 For example, coating with a brush, coating with a spray, coating by immersing an article in the coating solution, and drawing up the coating solution to bring the coating solution into contact with the inner wall of a tube or a syringe needle. A coating solution can be applied and then dried to evaporate the solvent composition to form a coating film on the surface of the article.
ＨＦＥ－３５６ｍｍｚを含む本溶剤組成物は、蒸発速度が大きく、塗布物品から速やかに蒸発させることができるため、塗膜付物品の製造に好適である。本溶剤組成物１００質量％に対し、ＨＦＥ－３５６ｍｍｚが５０質量％以上、７０質量％以上、８０質量％以上、９０質量％以上含まれる場合が特に好適である。 The present solvent composition containing HFE-356mmz has a high evaporation rate and can be rapidly evaporated from the coated article, making it suitable for manufacturing coated articles. It is particularly preferable that HFE-356mmz is contained in an amount of 50% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more based on 100% by mass of the present solvent composition.
ＨＦＯ類やＨＦＥ類は、ＣＦＣ類等の代替品として期待されるものの、例えば、ＨＦＯ類の一種である１２１４ｙａは、空気中での安定性が低いため、空気中での使用において分解して酸性化し得る。また、ＨＦＥ類の一種である１，１，２，２－テトラフルオロエチル－２，２，２－トリフルオロエチルエーテル（３４７ｐｃ－ｆ）は、後述の実施例においても示されるように、ＰＦＰＥとの溶液の安定性が必ずしも良好とはいえない。その一方で、本溶剤組成物とＰＦＰＥ基を有する化合物との溶液は優れた安定性を示す。 HFOs and HFEs are expected as substitutes for CFCs and the like. can become In addition, 1,1,2,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether (347pc-f), which is a kind of HFEs, is PFPE and solution stability is not necessarily good. On the other hand, solutions of the present solvent composition and compounds having PFPE groups exhibit excellent stability.
ＰＦＰＥ基を有する化合物を本溶剤組成物に溶解させた溶液は、溶解直後にとどまらず、長期（例えば３日以上、１０日以上）にわたって均一性を示し、溶液状態での安定性（溶解安定性）に優れる。このため、ＰＦＰＥ基を有する化合物を含む塗膜を物品表面に形成するための溶液（塗布用溶液）として安定的に供給することができる。また、本溶剤組成物を洗浄剤として用いる場合、物品からＰＦＰＥ基を有する化合物を除去する際に、ＰＦＰＥ基を有する化合物と本溶剤組成物との溶液（以下、「洗浄工程後の溶液」ともいう）が形成される。本溶剤組成物のリサイクルのために、この洗浄工程後の溶液は回収された後に蒸留等の精製操作が施され、本溶剤組成物が回収される。このリサイクルは、一般的な方法においては、洗浄工程とは別途に行われるため、回収から精製操作までに長時間要することもある。この間、本洗浄工程後の溶液においては、ＰＦＰＥ基を有する化合物と本溶剤組成物とが均一性を示すため、ＰＦＰＥ基を有する化合物が回収容器に粘着したり、精製の妨げになることが少なく、本溶剤組成物の効率的なリサイクルが可能となる。 A solution obtained by dissolving a compound having a PFPE group in the present solvent composition exhibits uniformity not only immediately after dissolution but also over a long period of time (for example, 3 days or more, 10 days or more), and exhibits stability in a solution state (dissolution stability ). Therefore, it can be stably supplied as a solution (coating solution) for forming a coating film containing a compound having a PFPE group on the surface of an article. Further, when the present solvent composition is used as a cleaning agent, when removing the compound having a PFPE group from the article, a solution of the compound having a PFPE group and the present solvent composition (hereinafter also referred to as "solution after the cleaning process") ) is formed. In order to recycle the present solvent composition, the solution after the washing step is recovered and then subjected to purification such as distillation to recover the present solvent composition. Since this recycling is performed separately from the washing process in a general method, it may take a long time from recovery to refining operation. During this time, in the solution after this washing step, the compound having a PFPE group and the solvent composition exhibit uniformity, so that the compound having a PFPE group hardly sticks to the collection container or interferes with purification. , enabling efficient recycling of the solvent composition.
［３．物品の洗浄方法］
本溶剤組成物を用いた物品の洗浄方法は、ＰＦＰＥ基を有する化合物が付着した物品に対して本溶剤組成物を用いること以外は特に限定されない。本溶剤組成物とＰＦＰＥ基を有する化合物が付着した物品とを接触させることで、当該物品からＰＦＰＥ基を有する化合物を除去することができる。この接触としては、例えば、手拭き洗浄、浸漬洗浄、スプレー洗浄、浸漬揺動洗浄、浸漬超音波洗浄、煮沸洗浄、蒸気洗浄、これらを組み合わせ等による方法が挙げられるが、この限りではない。
[3. Article cleaning method]
The method for washing articles using the present solvent composition is not particularly limited, except that the present solvent composition is used for articles to which a compound having a PFPE group is adhered. By bringing the present solvent composition into contact with an article to which a compound having a PFPE group is attached, the compound having a PFPE group can be removed from the article. Examples of this contact include, but are not limited to, hand-wiping cleaning, immersion cleaning, spray cleaning, immersion rocking cleaning, immersion ultrasonic cleaning, boiling cleaning, steam cleaning, and combinations thereof.
この物品としては、金属、樹脂、ゴム、繊維、ガラス、セラミックス、これらの複合材料からなる材質のものが挙げられる。複合材料としては、金属と樹脂の積層体等が挙げられる。この物品は、具体的には、精密機械部品、電子材料（プリント基板、液晶表示器、磁気記録部品、半導体材料等）、樹脂加工部品、光学レンズ、繊維製品、医療器具等が挙げられるが、これらに限定されない。後述の実施例においても示されるように、本溶剤組成物は、ＰＣ（ポリカーボネート）、アクリル樹脂、ＡＢＳ樹脂等の各種樹脂への悪影響が少ないため、このような樹脂を物品の材料として用いる実施形態において特に有効である。 Examples of such articles include those made of metal, resin, rubber, fiber, glass, ceramics, and composite materials thereof. Composite materials include laminates of metal and resin. Specific examples of such articles include precision machine parts, electronic materials (printed circuit boards, liquid crystal displays, magnetic recording parts, semiconductor materials, etc.), resin-processed parts, optical lenses, textile products, and medical instruments. It is not limited to these. As shown in the examples below, the present solvent composition has little adverse effect on various resins such as PC (polycarbonate), acrylic resin, and ABS resin. It is particularly effective in
以下、実施例により本発明に係る実施形態を詳細に説明するが、本発明の実施形態は実施例に限定されるものではない。 Hereinafter, embodiments according to the present invention will be described in detail with reference to examples, but the embodiments of the present invention are not limited to the examples.
本実施例において、ＰＦＰＥ基を有する化合物として、以下に示す市販のＰＦＰＥ＃１～ＰＦＰＥ ＃６のいずれかを使用した。
ＰＦＰＥ＃１（Ｆｏｍｂｌｉｎ（登録商標）Ｙ Ｈ ＶＡＣ２５／６（ソルベイ スペシャリティポリマー社製））： ＣＦ３－［（ＯＣＦ（ＣＦ３）ＣＦ２）ｍ－（ＯＣＦ２）ｎ］－ＯＣＦ３で表される構造式を有するポリマー（数平均分子量３３００）、
ＰＦＰＥ＃２（Ｆｏｍｂｌｉｎ（登録商標）Ｍ１５（ソルベイ スペシャリティポリマー社製））： ＣＦ３－［（ＯＣ２Ｆ４）ｐ－（ＯＣＦ２）ｑ］－ＯＣＦ３で表される構造式を有するポリマー（数平均分子量９７００）、
ＰＦＰＥ＃３（ＤＥＭＮＵＭ（登録商標）Ｓ－６５（ダイキン工業社製））： Ｆ－（Ｃ３Ｆ６Ｏ）ｍ－Ｃ２Ｆ５で表される構造式を有するポリマー（数平均分子量４５００）、
ＰＦＰＥ＃４（Ｆｏｍｂｌｉｎ（登録商標）Ｙ２５（ソルベイ スペシャリティポリマー社製））： ＣＦ３－［（ＯＣＦ（ＣＦ３）ＣＦ２）ｍ－（ＯＣＦ２）ｎ］－ＯＣＦ３で表される構造式を有するポリマー（数平均分子量３７００）、
ＰＦＰＥ＃５（Ｆｏｍｂｌｉｎ（登録商標）Ｙ Ｌ ＶＡＣ０６／６（ソルベイ スペシャリティポリマー社製））： ＣＦ３－［（ＯＣＦ（ＣＦ３）ＣＦ２）ｍ－（ＯＣＦ２）ｎ］－ＯＣＦ３で表される構造式を有するポリマー（数平均分子量１８００）、
ＰＦＰＥ＃６（Ｋｒｙｔｏｘ（登録商標）１４３ＡＤ（デュポン社製））： Ｆ－（Ｃ３Ｆ６Ｏ）ｍ－Ｃ２Ｆ５で表される構造式を有するポリマー（数平均分子量７４８０）。
In this example, one of commercially available PFPE #1 to PFPE #6 shown below was used as a compound having a PFPE group.
PFPE #1 (Fomblin (registered trademark) YH VAC25/6 (manufactured by Solvay Specialty Polymers)): CF3-[(OCF(CF3)CF2)m-(OCF2)n]-OCF3 polymer (number average molecular weight 3300),
PFPE #2 (Fomblin (registered trademark) M15 (manufactured by Solvay Specialty Polymers)): a polymer having a structural formula represented by CF3-[(OC2F4)p-(OCF2)q]-OCF3 (number average molecular weight 9700),
PFPE #3 (DEMNUM (registered trademark) S-65 (manufactured by Daikin Industries, Ltd.)): a polymer having a structural formula represented by F-(C3F6O)m-C2F5 (number average molecular weight 4500),
PFPE #4 (Fomblin (registered trademark) Y25 (manufactured by Solvay Specialty Polymers)): CF3-[(OCF(CF3)CF2)m-(OCF2)n]-OCF3 polymer having a structural formula (number average molecular weight 3700),
PFPE#5 (Fomblin (registered trademark) Y L VAC06/6 (manufactured by Solvay Specialty Polymers)): CF3-[(OCF(CF3)CF2)m-(OCF2)n]-OCF3 polymer (number average molecular weight 1800),
PFPE #6 (Krytox (registered trademark) 143AD (manufactured by DuPont)): A polymer having a structural formula represented by F-(C3F6O)m-C2F5 (number average molecular weight 7480).
＜１．ＰＦＰＥ溶液の溶解安定性試験＞
［実施例１～実施例１６、比較例１～比較例１５］
１１０ｍＬ硝子製スクリュー管瓶に溶剤３８ｇを入れた後に、ＰＦＰＥ２ｇを入れ、十分に混合し均一な溶液とした。これを密閉状態、室温（２０℃）、遮光下で保存し、０日後（ＰＦＰＥと溶剤を混合した直後）、３日後、１０日後の溶液の状態を目視で観察した。溶液が無色透明（濁りが無い）状態のものを「○」と評価し、わずかに濁りが生じた状態のものを「△」と評価し、明らかな着色、ゲル化の発生または二層分離が生じた状態のものを「×」と評価した。その結果を表１および表２に示す。
[Examples 1 to 16, Comparative Examples 1 to 15]
After putting 38 g of the solvent into a 110 mL glass screw vial, 2 g of PFPE was put into the bottle and thoroughly mixed to obtain a uniform solution. This was stored in a sealed state at room temperature (20° C.) under light shielding, and the state of the solution was visually observed after 0 days (immediately after mixing PFPE and solvent), 3 days, and 10 days. If the solution is colorless and transparent (no turbidity), it is evaluated as "○", and if it is slightly turbid, it is evaluated as "△". The resulting state was evaluated as "x". The results are shown in Tables 1 and 2.
実施例１～実施例１６に示されるように、ＨＦＥ－３５６ｍｍｚ、ＨＦＥ－３５６ｍｍｚ／１２３３ｚｄ（Ｚ）混合液、ＨＦＥ－３５６ｍｍｚ／ＨＦＣ－３６５ｍｆｃ混合液を溶剤として用いた場合には、３日後、１０日後の溶液の状態はいずれも無色透明であった。一方で、比較例１～比較例１５に示されるように、ＨＦＯ類の一種である１２３３ｚｄ（Ｚ）や、ＨＦＥ類の一種である３４７ｐｃ－ｆ、ＨＦＣ類の一種であるＨＦＣ－３６５ｍｆｃを溶剤として用いた場合には、ＰＦＰＥとの混合直後から二層分離した。 As shown in Examples 1 to 16, when HFE-356mmz, HFE-356mmz/1233zd(Z) mixture, and HFE-356mmz/HFC-365mfc mixture were used as solvents, after 3 days, 10 After several days, the solutions were colorless and transparent. On the other hand, as shown in Comparative Examples 1 to 15, 1233zd (Z), which is a kind of HFOs, 347pc-f, which is a kind of HFEs, and HFC-365mfc, which is a kind of HFCs, were used as solvents. When used, two layers were separated immediately after mixing with PFPE.
全ての含フッ素化合物がＰＦＰＥ基を有する化合物を溶解できるわけではない。一般的に、化合物中のフッ素原子の割合が高い溶剤は、ＰＦＰＥ基を有する化合物を溶解すると考えられている。しかしながら、上記の比較例が示すように、化合物中のフッ素原子の割合がより高いＨＦＥ－３４７ｐｃ－ｆを溶剤として用いた場合には、ＰＦＰＥ＃１～ＰＦＰＥ ＃６を溶解できなかったのに対し、上記の実施例が示すように、化合物中のフッ素原子の割合がより低いＨＦＥ－３５６ｍｍｚやＨＦＥ－３５６ｍｍｚを含む混合液を溶剤として用いた場合には、ＰＦＰＥ＃１～ＰＦＰＥ ＃６を溶解することができた。 Not all fluorine-containing compounds can dissolve compounds with PFPE groups. Generally, solvents with a high proportion of fluorine atoms in the compound are believed to dissolve compounds having PFPE groups. However, as shown in the above comparative example, when HFE-347pc-f, which has a higher proportion of fluorine atoms in the compound, was used as a solvent, PFPE #1 to PFPE #6 could not be dissolved. , As shown in the above examples, when HFE-356mmz having a lower fluorine atom ratio in the compound or a mixed solution containing HFE-356mmz is used as a solvent, PFPE #1 to PFPE #6 are dissolved. I was able to
＜２．塗布性、乾燥性評価試験＞
［実施例１７～実施例３３］
ＰＦＰＥと溶剤を混合して、０．５質量％ＰＦＰＥ溶液を調製した。このＰＦＰＥ溶液をＳＵＳ３１６製テストピース上に塗布し、溶剤を風乾することにより、ＳＵＳ３１６製テストピース表面に膜厚２ｎｍのＰＦＰＥ塗膜を形成した。得られた塗膜の状態を目視で確認した。塗膜にムラが見られなかったものを、塗布性が良好である（「〇」と表記）と評価した。また、塗膜の形成時にただちに溶剤が蒸発したものを、乾燥性が良好である（「〇」と表記）と評価した。その結果を表３に示す。
[Examples 17 to 33]
A 0.5 mass % PFPE solution was prepared by mixing PFPE and a solvent. This PFPE solution was applied onto a SUS316 test piece, and the solvent was air-dried to form a 2 nm thick PFPE coating film on the surface of the SUS316 test piece. The state of the obtained coating film was visually confirmed. A sample in which no unevenness was observed in the coating film was evaluated as having good coatability (denoted as “◯”). In addition, when the solvent was evaporated immediately during the formation of the coating film, it was evaluated as having good drying property (denoted as “◯”). Table 3 shows the results.
＜３．洗浄性試験＞
［実施例３４］
３００ｍＬ硝子製ビーカーにＰＦＰＥ＃１を２００ｇ入れた。次に、ＳＵＳ３１６製テストピース（３０ｍｍ×１５ｍｍ×２ｍｍ）１枚をＰＦＰＥ＃１中に完全に浸漬させた。このテストピースをＰＦＰＥ＃１中から取り出して目視で確認したところ、テストピース表面にはＰＦＰＥ＃１が付着していた。その後、５００ｍＬ硝子製ビーカーにＨＦＥ－３５６ｍｍｚを２００ｇ入れ、前記ＰＦＰＥ＃１が付着したＳＵＳテストピースを完全に浸漬するように入れ、２５℃２分間超音波洗浄（超音波発振器：Ａｌｅｘ Ｃｏｒｐｏｒａｔｉｏｎ社製 ネオソニック、出力１００Ｗ、周波数２８ｋＨｚ）した。その後、テストピースを取り出し、８０℃で５分間乾燥した後、テストピースの表面を目視観察したところ、テストピース表面に汚れは確認されなかった。
<3. Detergency Test>
[Example 34]
200 g of PFPE#1 was placed in a 300 mL glass beaker. Next, one SUS316 test piece (30 mm×15 mm×2 mm) was completely immersed in PFPE#1. When this test piece was taken out from PFPE#1 and visually confirmed, PFPE#1 was adhered to the surface of the test piece. After that, put 200 g of HFE-356 mmz in a 500 mL glass beaker, put the SUS test piece with the PFPE # 1 attached so that it is completely immersed, and ultrasonically clean at 25 ° C. for 2 minutes (ultrasonic oscillator: Neo manufactured by Alex Corporation) Sonic, output 100 W, frequency 28 kHz). After that, the test piece was taken out and dried at 80° C. for 5 minutes. When the surface of the test piece was visually observed, no contamination was found on the surface of the test piece.
［実施例３５］
ＨＦＥ－３５６ｍｍｚの替わりに、ＨＦＥ－３５６ｍｍｚ／ＨＦＣ－３６５ｍｆｃ（質量比：６０／４０）混合溶剤を用いた以外は実施例３４と同様の操作を行った。その結果、洗浄乾燥後のテストピース表面に汚れは確認されなかった。
[Example 35]
The same operation as in Example 34 was performed except that HFE-356mmz/HFC-365mfc (mass ratio: 60/40) mixed solvent was used instead of HFE-356mmz. As a result, no dirt was found on the surface of the test piece after washing and drying.
［実施例３６］
ＨＦＥ－３５６ｍｍｚの替わりに、ＨＦＥ－３５６ｍｍｚ／１２３３ｚｄ（Ｚ）（質量比：５０／５０）混合溶剤を用いた以外は実施例３４と同様の操作を行った。その結果、洗浄乾燥後のテストピース表面に汚れは確認されなかった。
[Example 36]
The same operation as in Example 34 was performed except that HFE-356mmz/1233zd(Z) (mass ratio: 50/50) mixed solvent was used instead of HFE-356mmz. As a result, no dirt was found on the surface of the test piece after washing and drying.
実施例３４～実施例３６により、ＨＦＥ－３５６ｍｍｚ、ＨＦＥ－３５６ｍｍｚを含む混合液の良好なＰＦＰＥ洗浄性が示された。
Examples 34-36 demonstrated good PFPE detergency of HFE-356mmz and mixtures containing HFE-356mmz.
Claims (11)
（式中、ｍおよびｎは１以上の整数であり、ｍ＋ｎ＝８～１２０を満たし、Ｒ１およびＲ２はそれぞれ独立に炭素数１～３のパーフルオロアルキル基であり、ｐおよびｑは１以上の整数であり、ｐ＋ｑ＝２５～３５０を満たし、Ｒ３およびＲ４はそれぞれ独立に炭素数１～３のパーフルオロアルキル基であり、ｒは１０～８０の整数であり、Ｒ５は炭素数１～３のパーフルオロアルキル基であり、ｓ、ｔ、ｕおよびｖは１以上の整数であり、ｔ／ｓ＝２～５、（ｕ＋ｖ）／（ｓ＋ｔ＋ｕ＋ｖ）＝０．０７～０．２、ｓ／（ｓ＋ｔ＋ｕ＋ｖ）＝０．１～０．３を満たし、Ｒ６およびＲ７はそれぞれ独立に炭素数１～３のパーフルオロアルキル基である。） A compound having a perfluoropolyether group is a compound represented by general formula (1) with a number average molecular weight of 1,300 to 8,000, a compound represented by general formula (2) with a number average molecular weight of 3,200 to 23,000, and a number average molecular weight of 2,000. The composition according to any one of claims 1 to 6, which is a compound represented by the general formula (3) with a number average molecular weight of up to 11,000 or a compound represented by the general formula (4) with a number average molecular weight of 1,000 to 20,000.
(Wherein, m and n are integers of 1 or more, satisfies m+n=8 to 120, R 1 and R 2 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms, and p and q are 1 p + q = 25 to 350, R 3 and R 4 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms, r is an integer of 10 to 80, and R 5 is a carbon a perfluoroalkyl group of numbers 1 to 3, s, t, u and v are integers of 1 or more, t/s = 2 to 5, (u + v) / (s + t + u + v) = 0.07 to 0.2 , s/(s+t+u+v)=0.1 to 0.3, and R 6 and R 7 are each independently a perfluoroalkyl group having 1 to 3 carbon atoms.)
A method for recovering 1,1,1,3,3,3-hexafluoroisopropyl methyl ether (HFE-356mmz) by subjecting the composition according to any one of claims 1 to 9 to a purification operation.
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