WO2022265084A1 - 含フッ素ピラーアレーン - Google Patents
含フッ素ピラーアレーン Download PDFInfo
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- WO2022265084A1 WO2022265084A1 PCT/JP2022/024222 JP2022024222W WO2022265084A1 WO 2022265084 A1 WO2022265084 A1 WO 2022265084A1 JP 2022024222 W JP2022024222 W JP 2022024222W WO 2022265084 A1 WO2022265084 A1 WO 2022265084A1
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- 229910052731 fluorine Inorganic materials 0.000 title claims description 44
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title description 4
- 239000011737 fluorine Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 145
- 125000000962 organic group Chemical group 0.000 claims description 238
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 139
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 125000004432 carbon atom Chemical group C* 0.000 claims description 74
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 70
- 125000001153 fluoro group Chemical group F* 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 45
- 125000002947 alkylene group Chemical group 0.000 claims description 40
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 39
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 150000002430 hydrocarbons Chemical class 0.000 claims description 25
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000005871 repellent Substances 0.000 claims description 15
- 235000019000 fluorine Nutrition 0.000 claims description 14
- 230000003068 static effect Effects 0.000 claims description 12
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- -1 pillararene Chemical class 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 238000000034 method Methods 0.000 description 8
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- 125000001424 substituent group Chemical group 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
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- 241001120493 Arene Species 0.000 description 5
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- 238000000465 moulding Methods 0.000 description 5
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 4
- GCDCOBYBHQJKDU-UHFFFAOYSA-N 4,4,4-trifluorobutyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCCC(F)(F)F)C=C1 GCDCOBYBHQJKDU-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000005011 alkyl ether group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 229960001701 chloroform Drugs 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 239000012756 surface treatment agent Substances 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- BDLIHQYAFPYPHL-UHFFFAOYSA-N 4,4,5,5,5-pentafluoropentyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCCC(F)(F)C(F)(F)F)C=C1 BDLIHQYAFPYPHL-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000000274 adsorptive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
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- 239000003779 heat-resistant material Substances 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
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- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
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- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 2
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- 239000000843 powder Substances 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- JXMGZLBGSDLPKN-UHFFFAOYSA-N 1,1-dichloro-1,2,2,3,3-pentafluoropropane Chemical compound FC(F)C(F)(F)C(F)(Cl)Cl JXMGZLBGSDLPKN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
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- AZRBANUVPNINHV-UHFFFAOYSA-N 1,4-dipentoxybenzene Chemical compound CCCCCOC1=CC=C(OCCCCC)C=C1 AZRBANUVPNINHV-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- PSQZJKGXDGNDFP-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)(F)F PSQZJKGXDGNDFP-UHFFFAOYSA-N 0.000 description 1
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- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 1
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 1
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
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- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
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- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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- 235000019792 magnesium silicate Nutrition 0.000 description 1
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- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
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- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 229920002866 paraformaldehyde Polymers 0.000 description 1
- XDEPVFFKOVDUNO-UHFFFAOYSA-N pentafluorobenzyl bromide Chemical compound FC1=C(F)C(F)=C(CBr)C(F)=C1F XDEPVFFKOVDUNO-UHFFFAOYSA-N 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
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- 238000010791 quenching Methods 0.000 description 1
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- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
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- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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Definitions
- the present disclosure relates to fluorine-containing pillar arenes.
- cyclic compounds compounds such as pillararene, crown ether, cyclodextrin, calixarene, and cucurbituril are known.
- pillar arenes having a symmetrical columnar structure have attracted attention because of their various properties such as the ability to function as host molecules capable of incorporating guest molecules (Patent Document 1).
- An object of the present disclosure is to provide a novel pillar arene having good water repellency, particularly a novel pillar arene containing a fluorine atom.
- each occurrence of R 1a is independently a hydrogen atom or an organic group; each occurrence of R 2a is independently a hydrogen atom or an organic group; each occurrence of R 3a is independently a hydrogen atom or an organic group; each occurrence of R 4a is independently a hydrogen atom or an organic group; provided that at least one of R 1a , R 2a , R 3a and R 4a is an organic group having 2 or more carbon atoms and having a fluoroalkyl group or a fluorophenyl group; n1 is an integer from 4 to 20; ]
- a compound represented by [2] R 1a and R 3a are each independently an organic group; provided that at least one of R 1a and R 3a is an organic group having 2 or more carbon atoms having a fluoroalkyl group or a fluorophenyl group, or R 2a and R 4a are each independently an organic group; , provided that at least one of R 1a and R 3a are an organic group having 2 or more carbon
- R 1a and R 3a are each independently an organic group having 2 or more carbon atoms having a fluoroalkyl group or a fluorophenyl group, or R 2a and R 4a are each independently a fluoroalkyl is an organic group having 2 or more carbon atoms having a group or a fluorophenyl group, The compound according to the above [1] or [2].
- R 2a and R 4a are hydrogen atoms, or R 1a and R 3a are hydrogen atoms, The compound according to any one of [1] to [3] above.
- [5] The compound according to any one of [1] to [4] above, wherein n1 is an integer of 4 to 6.
- the organic group having 2 or more carbon atoms and having a fluoroalkyl group is —(O p1 —R 11a q1 )—Rf a ;
- R 11a is independently at each occurrence a C 1-10 alkylene group or —CONH—;
- Rf a is a C 1-10 fluoroalkyl group,
- p1 is an integer from 0 to 2
- q1 is an integer from 0 to 3
- the order of existence of O and R 11a is not limited, The compound according to any one of [1] to [5] above.
- the organic group having 2 or more carbon atoms and having a fluoroalkyl group is —OR 11a —(OR 11a ) r1 —Rf a ; each R 11a is independently a C 1-10 alkylene group or —CONH—; Rf a is a C 1-10 fluoroalkyl group, r1 is 0 or 1;
- [8] The compound according to any one of [1] to [7] above, wherein the fluoroalkyl group is a perfluoroalkyl group.
- R 1a and R 3a are —OR 11a —(OR 11a ) r1 —Rf a
- R 2a and R 4a are hydrogen atoms
- R 2a and R 4a are —OR 11a —(OR 11a ) r1 —Rf a
- R 1a and R 3a are hydrogen atoms
- each R 11a is independently a C 1-10 alkylene group or —CONH—
- Rf a is a C 1-10 perfluoroalkyl group, r1 is 0 or 1
- n1 is an integer from 4 to 6
- the organic group having 2 or more carbon atoms and having a fluorophenyl group is represented by the following formula: -(O p3 -R 11p q3 )-Rf p [In the formula: R 11p is independently at each occurrence a C 1-10 alkylene group; Rf p is 1-5 phenyl groups, p3 is an integer from 0 to 2, q3 is an integer from 0 to 3, In (O p3 -R 11p q3 ), the order of existence of O and R 11p is not limited.
- the organic group having 2 or more carbon atoms and having a fluorophenyl group is represented by the following formula: -OR 11p -Rf p [In the formula: R 11p is independently at each occurrence a C 1-10 alkylene group; Rf p is a phenyl group substituted with 1-5 fluorines.
- R 1a and R 3a are —OR 11p —Rf p and R 2a and R 4a are hydrogen atoms, or R 2a and R 4a are —OR 11p —Rf p and R 1a and R 3a are hydrogen atoms, each R 11p is independently a C 1-6 alkylene group, Rf p is a phenyl group substituted with 1 to 5 fluorines; n1 is an integer from 4 to 6;
- R 11p is independently a C 1-6 alkylene group
- Rf p is a phenyl group substituted with 1 to 5 fluorines
- n1 is an integer from 4 to 6
- R 1b and R 3b are each independently an organic group having a fluorine atom with an SP value of 8.0 or less, or R 2b and R 4b are each independently an SP value of 8.0 or less is an organic group having a fluorine atom, The compound according to the above [14] or [15].
- R 2b and R 4b are hydrogen atoms, or R 1b and R 3b are hydrogen atoms, The compound according to any one of [14] to [16] above.
- [18] The compound according to any one of [14] to [17] above, wherein n2 is an integer of 4 to 6.
- R 1b and R 3b are —OR 11b —(OR 11b ) r2 —Rf b and R 2b and R 4b are hydrogen atoms, or R 2b and R 4b are —OR 11b —(OR 11b ) r2 —Rf b , wherein R 1b and R 3b are hydrogen atoms; each R 11b is independently a C 1-10 alkylene group; Rf b is a C 1-10 perfluoroalkyl group, r2 is 0 or 1; n2 is an integer from 4 to 6; The compound according to any one of [14] to [21] above.
- each occurrence of R 1c is independently a hydrogen atom or an organic group; each occurrence of R 2c is independently a hydrogen atom or an organic group; each occurrence of R 3c is independently a hydrogen atom or an organic group; each occurrence of R 4c is independently a hydrogen atom or an organic group; provided that at least one of R lc , R 2c , R 3c , and R 4c is an organic group having a long-chain alkyl group with 17 or more carbon atoms, n3 is an integer of 4-20.
- R 1c and R 3c are each independently an organic group; provided that at least one of R 1c and R 3c is an organic group having a long-chain alkyl group with 17 or more carbon atoms, or R 2c and R 4c are each independently an organic group; provided that at least one of R 2c and R 4c is an organic group having a long-chain alkyl group with 17 or more carbon atoms, The compound described in [24] above.
- R 1c and R 3c are each independently an organic group having a long-chain alkyl group with 17 or more carbon atoms; R 2c and R 4c are each independently an organic group having a long-chain alkyl group with 17 or more carbon atoms, The compound described in [24] or [25] above. [27] The compound according to any one of [24] to [26] above, wherein the long-chain alkyl group has 17 to 30 carbon atoms. [28] R 1c and R 3c are each independently —OR 12c , or R 2c and R 4c are each independently —OR 12c ; R 12c is a C 17-30 alkyl group, The compound according to any one of [24] to [27] above.
- R 2c and R 4c are hydrogen atoms, or R 1c and R 3c are hydrogen atoms, The compound according to any one of [24] to [28] above.
- n3 is an integer of 4 to 6.
- R 1c and R 3c are —OR 12c and R 2c and R 4c are hydrogen atoms, or R 2c and R 4c are —OR 12c and R 1c and R 3c is a hydrogen atom, R 12c is a C 17-30 alkyl group, n3 is an integer from 4 to 6; The compound according to any one of [24] to [30] above.
- each occurrence of R 1d is independently a hydrogen atom or an organic group
- each occurrence of R 2d is independently a hydrogen atom or an organic group
- each occurrence of R 3d is independently a hydrogen atom or an organic group
- each occurrence of R 4d is independently a hydrogen atom or an organic group
- at least one of R 1d , R 2d , R 3d and R 4d is an organic group having an alkyl group, and the alkyl group has an SP value of 8.2 or more
- n4 is an integer of 4-20.
- R 1d and R 3d are each independently an organic group; provided that at least one of R 1d and R 3d is an organic group having an alkyl group with an SP value of 8.2 or more, or R 2d and R 4d are each independently an organic group, provided that at least one of R 2d and R 4d is an organic group having an alkyl group with an SP value of 8.2 or more.
- R 1d and R 3d are each independently an organic group having an alkyl group with an SP value of 8.2 or more, or R 2d and R 4d are each independently an SP value of The compound according to the above [33] or [34], which is an organic group having an alkyl group of 8.2 or more.
- R 2d and R 4d are hydrogen atoms, or R 1d and R 3d are hydrogen atoms, The compound according to any one of [33] to [35] above.
- n4 is an integer of 4 to 6.
- R 1d and R 3d are —OR 12d and R 2d and R 4d are hydrogen atoms, or R 2d and R 4d are —OR 12d and R 1d and R 3d is a hydrogen atom, R 12d is a C 17-30 alkyl group, n4 is an integer from 4 to 6;
- [42] A molded product of the compound described in any one of [1] to [40] above.
- [43] A molded article formed from the composition described in [41] above. [44] The formed article according to [42] or [43] above, which is a film. [45] A material comprising a substrate treated with the compound according to any one of [1] to [40] above or the composition according to [41] above. [46] Formula (1E) below: [In the formula: R 1e , R 2e , R 3e and R 4e are each independently a hydrogen atom or an organic group; n5 is 5 or 6; ] A liquid-repellent composition comprising a pillar arene represented by and a hydrocarbon compound. [47] The liquid-repellent composition according to [46] above, wherein the organic group is an organic group having 1 to 30 carbon atoms. [48] The liquid-repellent composition of [46] or [47] above, further comprising a solvent.
- a fluorine-containing pillar arene can be provided.
- a "monovalent organic group” means a monovalent group containing carbon.
- the monovalent organic group is not particularly limited, it may be a hydrocarbon group or a derivative thereof.
- a derivative of a hydrocarbon group is a group having one or more of N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy, etc. at the end of the hydrocarbon group or in the molecular chain. means In addition, when it shows simply as an "organic group", it means a monovalent organic group.
- hydrocarbon group means a group containing carbon and hydrogen from which one hydrogen atom has been removed from a hydrocarbon.
- Such hydrocarbon groups include, but are not limited to, C 1-20 hydrocarbon groups optionally substituted by one or more substituents, such as aliphatic hydrocarbon groups, aromatic A hydrocarbon group etc. are mentioned.
- the above “aliphatic hydrocarbon group” may be linear, branched or cyclic, and may be saturated or unsaturated. Hydrocarbon groups may also contain one or more ring structures.
- the substituent of the "hydrocarbon group” is not particularly limited, but for example, a halogen atom, C 1-6 alkyl optionally substituted by one or more halogen atoms group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 3-10 cycloalkyl group, C 3-10 unsaturated cycloalkyl group, 5-10 membered heterocyclyl group, 5-10 membered unsaturated heterocyclyl groups, C 6-10 aryl groups and 5-10 membered heteroaryl groups.
- each occurrence of R 1a is independently a hydrogen atom or an organic group; each occurrence of R 2a is independently a hydrogen atom or an organic group; each occurrence of R 3a is independently a hydrogen atom or an organic group; each occurrence of R 4a is independently a hydrogen atom or an organic group; provided that at least one of R 1a , R 2a , R 3a and R 4a is an organic group having 2 or more carbon atoms and having a fluoroalkyl group; n1 is an integer from 4 to 20; ] to provide a compound represented by
- each occurrence of R 1a is independently a hydrogen atom or an organic group
- each occurrence of R 2a is independently a hydrogen atom or an organic group
- R 3a is independently at each occurrence a hydrogen atom or an organic group
- R 4a at each occurrence is independently a hydrogen atom or an organic group
- R 1a , R 2a , R 3a and at least one of R 4a is an organic group having 2 or more carbon atoms having a fluoroalkyl group or a fluorophenyl group.
- at least one of R 1a , R 2a , R 3a and R 4a is an organic group having 2 or more carbon atoms and having a fluoroalkyl group.
- the compound represented by formula (1A) can have high compatibility, heat resistance, and water/oil repellency by having an organic group having 2 or more carbon atoms having a fluoroalkyl group or a fluorophenyl group.
- organic groups examples include groups containing alkyl groups, alkyloxy groups, alkyl ether groups, tosyl groups, triflate groups, phenyl groups, etc., which may be substituted with substituents.
- substituents are not particularly limited, but for example, a halogen atom, a C 1-6 alkyl group optionally substituted with one or more halogen atoms, a C 2-6 alkenyl group, a C 2-6 alkynyl group, C 3-10 cycloalkyl group, C 3-10 unsaturated cycloalkyl group, 5-10 membered heterocyclyl group, 5-10 membered unsaturated heterocyclyl group, C 6-10 aryl group, and 5-10 membered heteroaryl groups, as well as one or more groups selected from reactive functional groups.
- Examples of the reactive functional group include, but are not particularly limited to, a hydroxyl group, an amino group, a carboxyl group, a thiol group, an isocyanate group, a vinyl group, an acetylene group, a nitrile group, and an epoxy group.
- Said alkyl groups are preferably C 1-30 alkyl groups. Such alkyl groups may be straight or branched.
- the C 1-30 alkyl group may be a C 1-20 alkyl group, preferably a C 1-10 alkyl group, more preferably a C 1-30 alkyl group.
- the C 1-30 alkyl group may be a C 17-30 alkyl group, preferably a C 18-30 alkyl group, more preferably a C 26-30 alkyl group.
- the alkyloxy group is typically a group represented by —OR 31 (wherein R 31 is an alkyl group).
- the alkyl group for R 31 may be substituted with any of the substituents described above, preferably with a fluorine atom.
- Such alkyl groups are preferably C 1-30 alkyl groups optionally substituted by fluorine atoms.
- Such alkyl groups may be straight or branched.
- the C 1-30 alkyl group may be a C 1-20 alkyl group, preferably a C 1-10 alkyl group, more preferably a C 1-30 alkyl group.
- R 31 is preferably —R 32 —R 33 (wherein R 32 is an unsubstituted C 1-30 alkylene group, preferably a C 1-20 alkylene group, more preferably a C 1-10 alkylene group , R 33 is a C 1-10 perfluoroalkyl group, preferably a C 1-6 perfluoroalkyl group.).
- the alkyl ether group is a compound having one or more etheric oxygen atoms in the molecular chain of the alkyl group.
- Such alkyl ether groups are typically groups represented by --R 36 --R 37 --(OR 38 ) m --R 39 .
- R36 is a single bond or an oxygen atom.
- R 37 is a single bond or a C 1-10 alkylene group.
- R 38 is a C 1-10 alkylene group.
- R 39 is a C 1-10 alkyl group optionally substituted by a fluorine atom.
- the organic group can be an alkyl group, an alkyloxy group, or an alkyl ether group whose terminal is substituted with a reactive functional group.
- such a group may be further substituted with another substituent.
- R 1a and R 3a are each independently an organic group, and at least one of R 1a and R 3a is a fluoroalkyl group or a fluorophenyl group, preferably a carbon number having a fluoroalkyl group two or more organic groups, or R 2a and R 4a are each independently an organic group, and at least one of R 2a and R 4a is a fluoroalkyl group or a fluorophenyl group, preferably a fluoro It is an organic group having 2 or more carbon atoms and having an alkyl group.
- At least two of R 1a , R 2a , R 3a , and R 4a are organic groups having 2 or more carbon atoms having a fluoroalkyl group or a fluorophenyl group. In one aspect, at least two of R 1a , R 2a , R 3a and R 4a are organic groups having 2 or more carbon atoms and having a fluoroalkyl group.
- two of R 1a , R 2a , R 3a , and R 4a are organic groups having 2 or more carbon atoms having a fluoroalkyl group or a fluorophenyl group. In one aspect, two of R 1a , R 2a , R 3a , and R 4a are organic groups having 2 or more carbon atoms and having a fluoroalkyl group.
- R 1a and R 3a are each independently an organic group having 2 or more carbon atoms having a fluoroalkyl group or a fluorophenyl group, preferably a fluoroalkyl group, or R 2a and R 4a each independently represents a fluoroalkyl group or a fluorophenyl group, preferably an organic group having 2 or more carbon atoms having a fluoroalkyl group.
- R 2a and R 4a are hydrogen atoms, or R 1a and R 3a are hydrogen atoms.
- R 1a and R 3a are each independently an organic group having 2 or more carbon atoms having a fluoroalkyl group or a fluorophenyl group, preferably a fluoroalkyl group, and R 2a and R 4a are hydrogen atoms.
- R 2a and R 4a are each independently an organic group having 2 or more carbon atoms having a fluoroalkyl group or a fluorophenyl group, preferably a fluoroalkyl group
- R 1a and R 3a are It is a hydrogen atom.
- R 1a and R 3a are a fluoroalkyl group or a fluorophenyl group, preferably an organic group having 2 or more carbon atoms having a fluoroalkyl group, and R 2a and R 4a are hydrogen atoms, Alternatively, R 2a and R 4a are a fluoroalkyl group or a fluorophenyl group, preferably an organic group having 2 or more carbon atoms having a fluoroalkyl group, and R 1a and R 3a are hydrogen atoms.
- the fluoroalkyl group is preferably a C 1-10 fluoroalkyl group, more preferably a C 1-6 fluoroalkyl group.
- Such fluoroalkyl groups may be straight or branched, preferably straight chain.
- Such fluoroalkyl groups are preferably perfluoroalkyl groups.
- the fluorophenyl group may be a phenyl group substituted with 1 to 5 fluorines, preferably a phenyl group substituted with 5 fluorines.
- the organic group having 2 or more carbon atoms having the fluoroalkyl group is represented by the following formula: -(O p1 -R 11a q1 )-Rf a
- R 11a is independently at each occurrence a C 1-10 alkylene group or —CONH—
- Rf a is a C 1-10 fluoroalkyl group
- p1 is an integer from 0 to 2
- q1 is an integer from 0 to 3
- O (O p1 -R 11a q1 ) is not limited.
- ] is a group represented by
- the C 1-10 alkylene group in R 11a is preferably a C 1-6 alkylene group, more preferably a C 2-6 alkylene group.
- Such alkylene groups may be straight chain or branched, preferably straight chain.
- R 11a is independently at each occurrence a C 1-10 alkylene group.
- R 11a is independently at each occurrence -CONH-.
- the C 1-10 fluoroalkyl group in Rf a is preferably a C 1-6 fluoroalkyl group.
- Such fluoroalkyl groups may be straight or branched, preferably straight chain.
- Such fluoroalkyl groups are preferably perfluoroalkyl groups.
- p1 is an integer of 0 to 2, preferably 1 or 2. In one aspect, p1 is one. In another aspect, p1 is two.
- q1 is an integer of 0-3, preferably an integer of 1-3, more preferably 1 or 2. In one aspect, q1 is one. In another aspect, q1 is two.
- the organic group having 2 or more carbon atoms and having a fluoroalkyl group is —OR 11a —(OR 11a ) r1 —Rf a
- each R 11a is independently a C 1-10 alkylene group or —CONH—
- Rf a is a C 1-10 fluoroalkyl group, r1 is 0 or 1
- ] is a group represented by
- the organic group having 2 or more carbon atoms and having a fluoroalkyl group is —OR 11a —(OR 11a ) r1 —Rf a
- each R 11a is independently a C 1-10 alkylene group or —CONH—
- Rf a is a C 1-10 perfluoroalkyl group, r1 is 0 or 1
- ] is a group represented by
- the organic group having 2 or more carbon atoms having the fluorophenyl group is represented by the following formula: -(O p3 -R 11p q3 )-Rf p
- R 11p is independently at each occurrence a C 1-10 alkylene group, preferably a C 1-6 alkylene group, more preferably a C 1-3 alkylene group
- Rf p is a phenyl group substituted by 1 to 5, preferably 5 fluorines
- p3 is an integer from 0 to 2
- q3 is an integer from 0 to 3
- O (O p3 -R 11p q3 ) the order of existence of O and R 11p is not limited.
- ] is a group represented by
- the C 1-10 alkylene group in R 11p is preferably a C 1-6 alkylene group, more preferably a C 1-6 alkylene group.
- Such alkylene groups may be straight chain or branched, preferably straight chain.
- p3 is an integer of 0 to 2, preferably 1 or 2. In one aspect, p1 is one. In another aspect, p1 is two.
- q3 is an integer of 0-3, preferably an integer of 1-3, more preferably 1 or 2. In one aspect, q1 is one. In another aspect, q1 is two.
- the organic group having 2 or more carbon atoms having a fluorophenyl group is represented by the following formula: -OR 11p -Rf p [In the formula: R 11p is independently at each occurrence a C 1-10 alkylene group, preferably a C 1-6 alkylene group, more preferably a C 1-3 alkylene group; Rf p is a phenyl group substituted with 1 to 5, preferably 5, fluorines. ] is a group represented by
- n1 is an integer of 4-20, preferably an integer of 4-6, more preferably 5 or 6.
- R 1a and R 3a are —OR 11a —(OR 11a ) r1 —Rf a and R 2a and R 4a are hydrogen atoms, or R 2a and R 4a are —O— R 11a -(OR 11a ) r1 -Rf a , wherein R 1a and R 3a are hydrogen atoms; each R 11a is independently a C 1-10 alkylene group, preferably a C 1-6 alkylene group, Rf a is a C 1-10 perfluoroalkyl group, preferably a C 1-6 perfluoroalkyl group, r1 is 0 or 1, n1 is an integer of 4-6, preferably 5 or 6.
- R 1a and R 3a are —OR 11p —Rf p and R 2a and R 4a are hydrogen atoms, or R 2a and R 4a are —OR 11p —Rf p ; R 1a and R 3a are hydrogen atoms, each R 11p is independently a C 1-6 alkylene group, preferably a C 1-3 alkylene group, Rf p is a phenyl group substituted by 1 to 5, preferably 5 fluorines, n1 is an integer of 4-6, preferably 5 or 6.
- the molecular weight of the compound represented by formula (1A) is preferably 500 to 10,000, more preferably 1,000 to 5,000.
- the resulting film has a static contact angle with water of 80° or more, preferably 90° or more.
- the compound represented by the above formula (1A) can be obtained by converting the substituent of the pillar[n]arene to an organic group having 2 or more carbon atoms and having a fluoroalkyl group.
- the compound represented by the above formula (1A) introduces a hydroxyl group at a predetermined position of the pillar [n]arene, and the hydroxyl group and an organic group having 2 or more carbon atoms having a fluoroalkyl group can be obtained by reacting with a tosylate, halide or the like of
- each occurrence of R 1b is independently a hydrogen atom or an organic group; each occurrence of R 2b is independently a hydrogen atom or an organic group; each occurrence of R 3b is independently a hydrogen atom or an organic group; each occurrence of R 4b is independently a hydrogen atom or an organic group; provided that at least one of R 1b , R 2b , R 3b and R 4b is an organic group having a fluorine atom, and the organic group having a fluorine atom has an SP value of 8.0 or less, n2 is an integer from 4 to 20; ] to provide a compound represented by
- the SP value is a solubility parameter and serves as a measure of solubility.
- the SP value is a value unique to a substance, and the larger the value, the higher the polarity, and the smaller the value, the lower the polarity.
- each occurrence of R 1b is independently a hydrogen atom or an organic group
- each occurrence of R 2b is independently a hydrogen atom or an organic group
- R 3b is independently at each occurrence a hydrogen atom or an organic group
- R 4b at each occurrence is independently a hydrogen atom or an organic group
- R 1b , R 2b , R 3b , and at least one of R 4b is an organic group having a fluorine atom
- the organic group having a fluorine atom has an SP value of 8.0 or less.
- the compound represented by formula (1B) can have high compatibility, heat resistance, and water and oil repellency by having an organic group having a fluorine atom with an SP value of 8.0 or less.
- the above organic group has the same meaning as the organic group in formula (1A) above.
- R 1b and R 3b are each independently an organic group, and at least one of R 1b and R 3b is an organic group having a fluorine atom with an SP value of 8.0 or less.
- R 2b and R 4b are each independently an organic group, and at least one of R 2b and R 4b is an organic group having a fluorine atom with an SP value of 8.0 or less be.
- At least two of R 1b , R 2b , R 3b and R 4b are organic groups having a fluorine atom with an SP value of 8.0 or less.
- two of R 1b , R 2b , R 3b and R 4b are organic groups having a fluorine atom with an SP value of 8.0 or less.
- R 1b and R 3b are each independently an organic group having a fluorine atom with an SP value of 8.0 or less, or R 2b and R 4b are each independently an SP value of 8.0. It is an organic group having 0 or less fluorine atoms.
- R 2b and R 4b are hydrogen atoms, or R 1b and R 3b are hydrogen atoms.
- R 1b and R 3b are each independently an organic group having a fluorine atom with an SP value of 8.0 or less, and R 2b and R 4b are hydrogen atoms, or R 2b and R4b are each independently an organic group having a fluorine atom with an SP value of 8.0 or less, and R2b and R4b are hydrogen atoms.
- R 1b and R 3b are organic groups having a fluorine atom with an SP value of 8.0 or less
- R 2b and R 4b are hydrogen atoms
- R 2b and R 4b is an organic group having a fluorine atom with an SP value of 8.0 or less
- R 1b and R 3b are hydrogen atoms.
- the SP value of the organic group having a fluorine atom is preferably 4.0 to 7.5, more preferably 6.0 to 7.5.
- the fluorine atom-containing organic group comprises a C 1-10 fluoroalkyl group.
- fluoroalkyl groups are preferably C 1-6 fluoroalkyl groups.
- fluoroalkyl groups may be straight or branched, preferably straight chain.
- fluoroalkyl groups are preferably perfluoroalkyl groups.
- the organic group having a fluorine atom has a fluorophenyl group.
- fluorophenyl groups are phenyl groups substituted by 1 to 5, preferably 5, fluorines.
- the fluorine atom-containing organic group has the following formula: -(O p2 -R 11b q2 )-Rf b [In the formula: R 11b is independently at each occurrence a C 1-10 alkylene group; Rf b is a C 1-10 fluoroalkyl group, p2 is an integer from 0 to 2, q2 is an integer from 0 to 3, In (O p2 -R 11b q2 ), the order of existence of O and R 11b is not limited. ] is a group represented by
- the organic group having 2 or more carbon atoms having the fluorophenyl group is represented by the following formula: -(O p1 -R 11a q1 )-Rf p
- R 11a is independently at each occurrence a C 1-10 alkylene group
- Rf p is a phenyl group substituted by 1 to 5, preferably 5 fluorines
- p1 is an integer from 0 to 2
- q1 is an integer from 0 to 3
- O (O p1 -R 11a q1 ) is not limited.
- ] is a group represented by
- the C 1-10 alkylene group in R 11b is preferably a C 1-6 alkylene group, more preferably a C 2-6 alkylene group.
- Such alkylene groups may be straight chain or branched, preferably straight chain.
- the C 1-10 fluoroalkyl group in Rf b is preferably a C 1-6 fluoroalkyl group.
- Such fluoroalkyl groups may be straight or branched, preferably straight chain.
- Such fluoroalkyl groups are preferably perfluoroalkyl groups.
- p2 is an integer from 0 to 2, preferably 1 or 2. In one aspect, p2 is one. In another aspect, p2 is two.
- q2 is an integer of 0-3, preferably an integer of 1-3, more preferably 1 or 2. In one aspect, q2 is one. In another aspect, q2 is two.
- the organic group having a fluorine atom is —OR 11b —(OR 11b ) r2 —Rf b
- each R 11b is independently a C 1-10 alkylene group
- Rf b is a C 1-10 fluoroalkyl group, r2 is 0 or 1
- ] is a group represented by
- the organic group having a fluorine atom is —OR 11b —(OR 11b ) r2 —Rf b
- each R 11b is independently a C 1-10 alkylene group
- Rf b is a C 1-10 perfluoroalkyl group, r2 is 0 or 1
- ] is a group represented by
- n2 is an integer of 4-20, preferably an integer of 4-6, more preferably 5 or 6.
- R 1b and R 3b are —OR 11b —(OR 11b ) r2 —Rf b
- R 2b and R 4b are hydrogen atoms
- R 2b and R 4b are —O— R 11b -(OR 11b ) r2 -Rf b
- R 1b and R 3b are hydrogen atoms
- each R 11b is independently a C 1-10 alkylene group, preferably a C 1-6 alkylene group
- Rf b is a C 1-10 perfluoroalkyl group, preferably a C 1-6 perfluoroalkyl group
- r2 is 0 or 1
- n2 is an integer of 4-6, preferably 5 or 6.
- the molecular weight of the compound represented by formula (1B) is preferably 500 to 10,000, more preferably 1,000 to 5,000.
- the static contact angle of the obtained film with respect to water is 80° or more, preferably 90° or more.
- the compound represented by formula (1B) above can be produced by the same method as for the compound represented by formula (1A) above.
- a hydroxyl group is introduced at a predetermined position of the pillar [n]arene, and the hydroxyl group is combined with a tosylate, a halide, or the like of an organic group having a fluorine atom. It can be obtained by reacting.
- each occurrence of R lc is independently a hydrogen atom or an organic group; each occurrence of R 2c is independently a hydrogen atom or an organic group; each occurrence of R 3c is independently a hydrogen atom or an organic group; each occurrence of R 4c is independently a hydrogen atom or an organic group; provided that at least one of R lc , R 2c , R 3c , and R 4c is an organic group having a long-chain alkyl group with 17 or more carbon atoms, n3 is an integer of 4-20.
- R lc is independently a hydrogen atom or an organic group
- each occurrence of R 3c is independently a hydrogen atom or an organic group
- each occurrence of R 4c is independently a hydrogen atom or an organic group
- each occurrence of R 1c is independently a hydrogen atom or an organic group
- each occurrence of R 2c is independently a hydrogen atom or an organic group
- R 3c is independently at each occurrence a hydrogen atom or an organic group
- R 4c at each occurrence is independently a hydrogen atom or an organic group
- R 1c , R 2c , R 3c , and at least one of R 4c is an organic group having a long-chain alkyl group with 17 or more carbon atoms.
- the compound represented by formula (1C) can have high compatibility, heat resistance and water repellency by having an organic group having a long-chain alkyl group with 17 or more carbon atoms.
- the above organic group has the same meaning as the organic group in formula (1A) above.
- the number of carbon atoms in the long-chain alkyl group is preferably 17-30, more preferably 18-30, and even more preferably 26-30.
- the organic group having a long-chain alkyl group is preferably —O—R 12c (wherein R 12c is a long-chain alkyl group having 17 or more carbon atoms, preferably a C 17-30 alkyl group, preferably a C 18 -30 alkyl group, C 26-30 alkyl group).
- the long-chain alkyl group may be linear or branched, preferably linear.
- R 1c and R 3c are each independently an organic group, and at least one of R 1c and R 3c is an organic group having a long-chain alkyl group with 17 or more carbon atoms
- R 2c and R 4c are each independently an organic group, and at least one of R 2c and R 4c is an organic group having a long-chain alkyl group with 17 or more carbon atoms.
- At least two of R 1c , R 2c , R 3c , and R 4c are organic groups having a long-chain alkyl group with 17 or more carbon atoms.
- two of R 1c , R 2c , R 3c , and R 4c are organic groups having a long-chain alkyl group with 17 or more carbon atoms.
- R 1c and R 3c are each independently an organic group having a long-chain alkyl group with 17 or more carbon atoms, preferably —O—R 12c , or R 2c and R 4c each independently represents an organic group having a long-chain alkyl group having 17 or more carbon atoms, preferably —OR 12c .
- R 2c and R 4c are hydrogen atoms, or R 1c and R 3c are hydrogen atoms.
- R 1c and R 3c are each independently an organic group having a long-chain alkyl group with 17 or more carbon atoms, and R 2c and R 4c are hydrogen atoms, or R 2c and R 4c are each independently an organic group having a long-chain alkyl group with 17 or more carbon atoms, and R 1c and R 3c are hydrogen atoms.
- R 1c and R 3c are organic groups having a long-chain alkyl group with 17 or more carbon atoms, and R 2c and R 4c are hydrogen atoms, or R 2c and R 4c are , an organic group having a long-chain alkyl group having 17 or more carbon atoms, and R 1c and R 3c are hydrogen atoms.
- n3 is an integer of 4-20, preferably an integer of 4-6, more preferably 5 or 6.
- R 1c and R 3c are —OR 12c and R 2c and R 4c are hydrogen atoms, or R 2c and R 4c are —OR 12c , R 1c and R 3c are hydrogen atoms, R 12c is a C 17-30 alkyl group, preferably a C 18-30 alkyl group, a C 26-30 alkyl group, n3 is an integer of 4-6, preferably 5 or 6.
- the molecular weight of the compound represented by formula (1C) is preferably 500 to 10,000, more preferably 1,000 to 5,000.
- the static contact angle of the obtained film to water is 80° or more, preferably 90° or more.
- the compound represented by formula (1C) above can be produced by the same method as for the compound represented by formula (1A) above.
- a hydroxyl group is introduced at a predetermined position of the pillar [n]arene, and the hydroxyl group and an organic group having a long-chain alkyl group having 17 or more carbon atoms are It can be obtained by reacting with a tosylate, a halide, or the like.
- each occurrence of R 1d is independently a hydrogen atom or an organic group
- each occurrence of R 2d is independently a hydrogen atom or an organic group
- R 3d is independently at each occurrence a hydrogen atom or an organic group
- R 4d at each occurrence is independently a hydrogen atom or an organic group
- R ld , R 2d , R 3d , and R 4d is an organic group having an alkyl group, and the alkyl group has an SP value of 8.2 or more.
- the compound represented by formula (1D) can have high compatibility, heat resistance and water repellency by having an organic group having an alkyl group with an SP value of 8.2 or more.
- the above organic group has the same meaning as the organic group in formula (1A) above.
- R 1d and R 3d are each independently an organic group, and at least one of R 1d and R 3d is an organic group having an alkyl group with an SP value of 8.2 or more.
- R 2d and R 4d are each independently an organic group, and at least one of R 2d and R 4d is an organic group having an alkyl group with an SP value of 8.2 or more be.
- At least two of R 1d , R 2d , R 3d and R 4d are organic groups having an alkyl group with an SP value of 8.2 or more.
- two of R 1d , R 2d , R 3d and R 4d are organic groups having an alkyl group with an SP value of 8.2 or more.
- R 1d and R 3d are each independently an organic group having an alkyl group with an SP value of 8.2 or more, or R 2d and R 4d are each independently It is an organic group having an alkyl group with an SP value of 8.2 or more.
- R 2d and R 4d are hydrogen atoms, or R 1d and R 3d are hydrogen atoms.
- R 1d and R 3d are each independently an organic group having an alkyl group with an SP value of 8.2 or more, and R 2d and R 4d are hydrogen atoms, or R 2d and R4d are each independently an organic group having an alkyl group with an SP value of 8.2 or more, and R1d and R3d are hydrogen atoms.
- R 1d and R 3d are organic groups having an alkyl group with an SP value of 8.2 or more
- R 2d and R 4d are hydrogen atoms
- R 2d and R 4d is an organic group having an alkyl group with an SP value of 8.2 or more
- R 1d and R 3d are hydrogen atoms.
- the SP value of the alkyl group is preferably 8.2 to 8.4.
- the organic group having an alkyl group is preferably —O—R 12d (wherein R 12d is a long-chain alkyl group with 17 or more carbon atoms, preferably a C 17-30 alkyl group, preferably a C 18-30 alkyl group, C 26-30 alkyl group).
- the long-chain alkyl group may be linear or branched, preferably linear.
- n4 is an integer of 4-20, preferably an integer of 4-6, more preferably 5 or 6.
- R 1d and R 3d are —OR 12d and R 2d and R 4d are hydrogen atoms, or R 2d and R 4d are —OR 12d and R 1d and R 3d are , is a hydrogen atom, and R 12d is a C 17-30 alkyl group, preferably a C 18-30 alkyl group, a C 26-30 alkyl group, n4 is an integer from 4 to 6, preferably 5 or 6; A compound according to any one of claims 30-35.
- the molecular weight of the compound represented by the formula (1D) is preferably 500 to 10,000, more preferably 1,000 to 5,000.
- the resulting film has a static contact angle with water of 80° or more, preferably 90° or more.
- the compound represented by formula (1D) above can be produced by the same method as for the compound represented by formula (1A) above.
- a hydroxyl group is introduced at a predetermined position of the pillar [n]arene, and the hydroxyl group is combined with a tosylate, a halide, or the like of an organic group having an alkyl group. It can be obtained by reacting.
- composition comprising a compound represented by formula (1A), (1B), (1C), or (1D) above.
- composition of the present disclosure may contain the compounds of the present disclosure singly or may contain two or more of them in combination.
- composition of the present disclosure may be liquid or solid.
- each component may be included in the pillar arene of the present disclosure as a so-called inclusion, or the pillar arene of the present disclosure may include other components.
- composition of the present disclosure may contain a solvent in addition to the compound of the present disclosure.
- the solvent examples include water; aliphatic hydrocarbons such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, and mineral spirits; aromatic hydrocarbons such as benzene, toluene, xylene, naphthalene, and solvent naphtha.
- aliphatic hydrocarbons such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, and mineral spirits
- aromatic hydrocarbons such as benzene, toluene, xylene, naphthalene, and solvent naphtha.
- Hydrogens methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol methyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl-2-hydroxy Esters such as butyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, ethyl 2-hydroxyisobutyrate; acetone, ketones such as methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methylaminoketone, 2-heptanone;
- the compound represented by formula (1A), (1B), (1C), or (1D) may be swollen by the solvent.
- the solvent may be gas. That is, the composition of the present disclosure may contain a gaseous mixture of the compound represented by formula (1A), (1B), (1C), or (1D) above and the solvent above.
- the solvent as a gas may preferably be a hydrocarbon, more preferably a C4-10 hydrocarbon such as butane, pentane, hexane, cyclohexane, heptane, octane, nonane, or decane, more preferably pentane or hexane.
- a solvent gas By including such a solvent gas, the contact angle of the film obtained using the composition of the present disclosure can be improved.
- composition of the present disclosure may contain thermoplastic resins such as non-fluororesins and fluororesins.
- non-fluororesin examples include polyethylene (e.g., linear low-density polyethylene, low-density polyethylene, high-density polyethylene, ultra-high molecular weight polyethylene, etc.), various structural isomers (syndiotactic, isotactic, atactic structure) including polypropylene, poly-(4-methylpentene-1), ethylene-propylene copolymer, ethylene-vinyl acetate copolymer (EVA), chlorinated polyethylene resin, polyolefin resin such as modified polyolefin, cyclo Polyvinyl chloride resins such as olefin resins, polyvinyl chloride, polyvinylidene chloride, polystyrene or polystyrene derivative resins containing various structural isomers, polyamides, polyimides, polyamideimides, polycarbonates, ionomers, polymethyl containing various structural isomers Acrylic resins such as methacrylate (PMMA), acrylic acid
- fluororesin examples include polytetrafluoroethylene (PTFE), tetrafluoroethylene (TFE)/perfluoroalkyl vinyl ether (PAVE) copolymer [PFA], TFE/hexafluoropropylene (HFP) copolymer [FEP ], ethylene [Et] / TFE copolymer [ETFE], Et / TFE / HFP copolymer, polychlorotrifluoroethylene [PCTFE], chlorotrifluoroethylene (CTFE) / TFE copolymer, Et / CTFE copolymer Polymers, polyvinylidene fluoride [PVDF], vinylidene fluoride (VDF)/TFE copolymers, polyvinyl fluoride [PVF] and the like.
- composition of the present disclosure may contain fillers.
- filler examples include, in addition to silica and carbon black, metal oxides such as calcium oxide, titanium oxide, aluminum oxide and magnesium oxide; metals such as magnesium hydroxide, aluminum hydroxide and calcium hydroxide. Hydroxides; carbonates such as magnesium carbonate, aluminum carbonate, calcium carbonate, and barium carbonate; silicates such as magnesium silicate, calcium silicate, sodium silicate, and aluminum silicate; aluminum sulfate, calcium sulfate, barium sulfate, etc.
- metal oxides such as calcium oxide, titanium oxide, aluminum oxide and magnesium oxide
- metals such as magnesium hydroxide, aluminum hydroxide and calcium hydroxide.
- Hydroxides carbonates such as magnesium carbonate, aluminum carbonate, calcium carbonate, and barium carbonate
- silicates such as magnesium silicate, calcium silicate, sodium silicate, and aluminum silicate
- hydrotalcite synthetic hydrotalcite
- metal sulfides such as molybdenum disulfide, iron sulfide, copper sulfide; diatomaceous earth, asbestos, lithopone (zinc sulfide/barium sulfide), graphite, carbon fluoride, calcium fluoride, coke , fine quartz powder, talc, mica powder, wollastonite, carbon fibers, aramid fibers, various whiskers, glass fibers, organic reinforcing agents, organic fillers, polytetrafluoroethylene, mica, celite, clay and the like. You may use these individually or in mixture of 2 or more types.
- the compounds and compositions of the present disclosure can be used in a wide range of applications, such as compatibilizers, adhesives, surface treatment agents (e.g., water repellents), highly heat-resistant materials, adsorptive separation materials, and molding materials. .
- the compounds and compositions of the present disclosure can be molded into molded bodies. Accordingly, the disclosure also provides shaped bodies formed from the compounds and compositions of the disclosure.
- the method of molding the compound and composition of the present disclosure is not particularly limited, and general molding methods such as extrusion molding, injection molding, press molding, vacuum molding, transfer molding, cast molding, etc. can be used.
- the shape of the obtained molded product is not particularly limited, and may be any desired shape, for example, block-like, sheet-like, film-like, rod-like, and various other shapes depending on the application.
- the pillar arene of the present disclosure can be dissolved in a good solvent, cast on a substrate, and heated to the boiling point of the solvent or higher to volatilize the solvent to form a film.
- a molded article of the compound or composition of the present disclosure has high heat resistance and water repellency.
- Films obtained by casting the compounds or compositions of the present disclosure are made of a hydrocarbon, preferably a C4-10 hydrocarbon such as butane, pentane, hexane, cyclohexane, heptane, octane, nonane, or decane, more preferably decane.
- a hydrocarbon preferably a C4-10 hydrocarbon such as butane, pentane, hexane, cyclohexane, heptane, octane, nonane, or decane, more preferably decane.
- pentane or hexane gas can be treated with pentane or hexane gas to improve the water resistance contact angle.
- the disclosure provides materials comprising substrates treated with compounds and or compositions of the disclosure.
- Substrates that can be treated with the compounds and compositions of the present disclosure include, for example, glass, resins (which may be natural or synthetic resins, such as common plastic materials), metals, ceramics, semiconductors (silicon, germanium, etc.), It can be composed of fibers (woven fabrics, non-woven fabrics, etc.), furs, leathers, woods, ceramics, stone materials, building members, sanitary products, adsorption separation materials, and any suitable materials.
- a substrate treated with the compound or composition of the present disclosure has high heat resistance and water repellency.
- R 1e , R 2e , R 3e and R 4e are each independently a hydrogen atom or an organic group; n5 is 5 or 6; ]
- a liquid-repellent composition comprising a pillar arene represented by and a hydrocarbon compound.
- the molded article of the liquid-repellent composition has high water repellency.
- the above organic group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms.
- the liquid-repellent composition may further contain a solvent.
- the solvent contained in the liquid repellent composition can be a C4-10 hydrocarbon such as butane, pentane, hexane, cyclohexane, heptane, octane, nonane, or decane, more preferably pentane or hexane.
- the hydrocarbon compound contained in the liquid repellent composition can preferably be a C4-10 hydrocarbon such as butane, pentane, hexane, cyclohexane, heptane, octane, nonane, or decane, more preferably pentane or hexane. .
- the hydrocarbon compound contained in the liquid-repellent composition may be the same as or different from the solvent.
- it may be a pillar arene with a hydrocarbon compound adhering thereto, that is, a so-called surface deposit.
- the pillar arene represented by formula (1E) may be swollen by the solvent.
- the above inclusions and surface deposits can be obtained by treating the pillar arene represented by formula (1E) with a hydrocarbon compound gas.
- Synthesis example 2 Except using 4,4,5,5,5-pentafluoropentyl-p-toluenesulfonate (14.3 g, 42.9 mmol) instead of 1-tosyloxy-4,4,4-trifluorobutane. In the same manner as in Synthesis Example 1, the following substituted pillar[5]arene (yield 13%) was obtained.
- Synthesis example 3 8-[(6-bromohexyl)oxy]-1,1,1,2,2,3,3,4,4,5,5 instead of 1-tosyloxy-4,4,4-trifluorobutane ,6,6-tridecafluoro-octane (22.6 g, 42.9 mmol) was used to prepare the following substituted pillar[5]arene (yield 5.3%) in the same manner as in Synthesis Example 1. Obtained.
- Synthesis example 4 Hydroquinone pillar[5]arene was replaced with hydroquinone pillar[6]arene (1.30 g, 1.77 mmol), and 1-tosyloxy-4,4,4-trifluorobutane was replaced with 4 ,4,5,5,5-pentafluoropentyl-p-toluenesulfonate (14.3 g, 42.9 mmol) was used in the same manner as in Synthesis Example 1 to obtain the following substituted pillar[6]arene (yield rate of 24%) was obtained.
- Synthesis example 7 The hydroquinone pillar[5]arene (0.305 g, 0.5 mmol) was dissolved in dimethylsulfoxide (5 mL). Then stearyl isocyanate (1.478 g, 5 mmol) was added and 1 drop of dibutyltin laurate as a catalyst was added dropwise. The mixture was heated to 40° C. and allowed to react for 6 hours. The reaction solution and precipitate were washed with hexane and water in that order to obtain the target compound.
- SP value The SP values of the side chains of the pillar arenes of Synthesis Examples 1 to 4 were calculated by the method of Fedors described above. The results are shown in the table below.
- the SP values of the side chain structures of Synthesis Examples 1-4 ranged from 6.9 to 7.4.
- the SP values of both are close to each other, so it is considered that the pillar arene compound and the fluororesin have good compatibility.
- SP value When the side chain structure is a long chain alkyloxy group: -OC 17 H 35 , -OC 20 H 41 , -OC 26 H 53 , -OC 30 H 61 (all linear)
- the SP value of was calculated by the method of Fedors described above. The results are shown in the table below.
- the air-dried sample was dissolved in heavy chloroform, and the inclusion of the solvent in the pillar arene was confirmed from the integrated value of the 1 H NMR peaks of the pillar arene and the alkane moiety.
- Synthesis Examples 1, 2, and 4 especially the pillar arenes of Synthesis Examples 1 and 2, had a high melting point and excellent heat resistance. Due to the high melting point of the compound, softening of the resin when used as an additive to the resin can be suppressed. Therefore, the pillar arene of the present disclosure can be used in a wide range of applications such as applications requiring heat resistance.
- the compounds of the present disclosure can be used in a wide range of applications, such as compatibilizers, adhesives, surface treatment agents, highly heat-resistant materials, adsorptive separation materials, and molding materials.
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Abstract
Description
[1] 下記式(1A):
R1aは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R2aは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R3aは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R4aは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
ただし、R1a、R2a、R3a、及びR4aの少なくとも1つは、フルオロアルキル基又はフルオロフェニル基を有する炭素数2以上の有機基であり、
n1は、4~20の整数である。]
で表される化合物。
[2] R1a及びR3aは、それぞれ独立して、有機基であり、
ただし、R1a及びR3aの少なくとも1つは、フルオロアルキル基又はフルオロフェニル基を有する炭素数2以上の有機基であるか、あるいは
R2a及びR4aは、それぞれ独立して、有機基であり、
ただし、R2a及びR4aの少なくとも1つは、フルオロアルキル基又はフルオロフェニル基を有する炭素数2以上の有機基である、
上記[1]に記載の化合物。
[3] R1a及びR3aは、それぞれ独立して、フルオロアルキル基又はフルオロフェニル基を有する炭素数2以上の有機基であるか、あるいは
R2a及びR4aは、それぞれ独立して、フルオロアルキル基又はフルオロフェニル基を有する炭素数2以上の有機基である、
上記[1]又は[2]に記載の化合物。
[4] R2a及びR4aは、水素原子であるか、あるいは
R1a及びR3aは、水素原子である、
上記[1]~[3]のいずれか1項に記載の化合物。
[5] n1は、4~6の整数である、上記[1]~[4]のいずれか1項に記載の化合物。
[6] 前記フルオロアルキル基を有する炭素数2以上の有機基は、-(Op1-R11a q1)-Rfaであり、
R11aは、各出現においてそれぞれ独立して、C1-10アルキレン基又は-CONH-であり、
Rfaは、C1-10フルオロアルキル基であり、
p1は、0~2の整数であり、
q1は、0~3の整数であり、
(Op1-R11a q1)中、O及びR11aの存在順序は限定されない、
上記[1]~[5]のいずれか1項に記載の化合物。
[7] 前記フルオロアルキル基を有する炭素数2以上の有機基は、-O-R11a-(O-R11a)r1-Rfaであり、
R11aは、それぞれ独立して、C1-10アルキレン基又は-CONH-であり、
Rfaは、C1-10フルオロアルキル基であり、
r1は、0又は1である、
上記[1]~[6]のいずれか1項に記載の化合物。
[8] 前記フルオロアルキル基は、パーフルオロアルキル基である、上記[1]~[7]のいずれか1項に記載の化合物。
[9] R1a及びR3aは、-O-R11a-(O-R11a)r1-Rfaであり、R2a及びR4aは、水素原子であるか、あるいは
R2a及びR4aは、-O-R11a-(O-R11a)r1-Rfaであり、R1a及びR3aは、水素原子であり、
R11aは、それぞれ独立して、C1-10アルキレン基又は-CONH-であり、
Rfaは、C1-10パーフルオロアルキル基であり、
r1は、0又は1であり、
n1は、4~6の整数である、
上記[1]~[8]のいずれか1項に記載の化合物。
[10] 前記フルオロフェニル基を有する炭素数2以上の有機基は、下記式:
-(Op3-R11p q3)-Rfp
[式中:
R11pは、各出現においてそれぞれ独立して、C1-10アルキレン基であり、
Rfpは、1~5個フェニル基であり、
p3は、0~2の整数であり、
q3は、0~3の整数であり、
(Op3-R11p q3)中、O及びR11pの存在順序は限定されない。]
で表される基である、上記[1]~[5]のいずれか1項に記載の化合物。
[11] 前記フルオロフェニル基を有する炭素数2以上の有機基は、下記式:
-O-R11p-Rfp
[式中:
R11pは、各出現においてそれぞれ独立して、C1-10アルキレン基であり、
Rfpは、1~5個のフッ素により置換されたフェニル基である。]
で表される基である、上記[1]~[5]のいずれか1項に記載の化合物。
[12] R1a及びR3aは、-O-R11p-Rfpであり、R2a及びR4aは、水素原子であるか、あるいは
R2a及びR4aは、-O-R11p-Rfpであり、R1a及びR3aは、水素原子であり、
R11pは、それぞれ独立して、C1-6アルキレン基であり、
Rfpは、1~5個のフッ素により置換されたフェニル基であり、
n1は、4~6の整数である、
上記[1]~[5]のいずれか1項に記載の化合物。
[13] 成膜した場合の膜の水に対する静的接触角は、80°以上である、上記[1]~[12]のいずれか1項に記載の化合物。
[14] 下記式(1B):
R1bは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R2bは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R3bは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R4bは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
ただし、R1b、R2b、R3b、及びR4bの少なくとも1つは、フッ素原子を有する有機基であって、該フッ素原子を有する有機基は、SP値が8.0以下であり、
n2は、4~20の整数である。]
で表される化合物。
[15] R1b及びR3bは、それぞれ独立して、有機基であり、
ただし、R1b及びR3bの少なくとも1つは、SP値が8.0以下であるフッ素原子を有する有機基であるか、あるいは
R2b及びR4bは、それぞれ独立して、有機基であり、
ただし、R2b及びR4bの少なくとも1つは、SP値が8.0以下であるフッ素原子を有する有機基である、
上記[14]に記載の化合物。
[16] R1b及びR3bは、それぞれ独立して、SP値が8.0以下であるフッ素原子を有する有機基であるか、あるいは
R2b及びR4bは、それぞれ独立して、SP値が8.0以下であるフッ素原子を有する有機基である、
上記[14]又は[15]に記載の化合物。
[17] R2b及びR4bは、水素原子であるか、あるいは
R1b及びR3bは、水素原子である、
上記[14]~[16]のいずれか1項に記載の化合物。
[18] n2は、4~6の整数である、上記[14]~[17]のいずれか1項に記載の化合物。
[19] 前記フッ素原子を有する有機基のSP値は、4.0~7.5である、上記[14]~[18]のいずれか1項に記載の化合物。
[20] 前記フッ素原子を有する有機基は、C1-10フルオロアルキル基を有する、上記[14]~[19]のいずれか1項に記載の化合物。
[21] 前記C1-10フルオロアルキル基は、C1-10パーフルオロアルキル基である、上記[30]に記載の化合物。
[22] R1b及びR3bは、-O-R11b-(O-R11b)r2-Rfbであり、R2b及びR4bは、水素原子であるか、あるいは
R2b及びR4bは、-O-R11b-(O-R11b)r2-Rfbであり、R1b及びR3bは、水素原子であり、
R11bは、それぞれ独立して、C1-10アルキレン基であり、
Rfbは、C1-10パーフルオロアルキル基であり、
r2は、0又は1であり、
n2は、4~6の整数である、
上記[14]~[21]のいずれか1項に記載の化合物。
[23] 成膜した場合の膜の水に対する静的接触角は、80°以上である、上記[14]~[22]のいずれか1項に記載の化合物。
[24] 下記式(1C):
R1cは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R2cは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R3cは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R4cは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
ただし、R1c、R2c、R3c、及びR4cの少なくとも1つは、炭素数が17以上の長鎖アルキル基を有する有機基であり、
n3は、4~20の整数である。]
で表される化合物。
[25] R1c及びR3cは、それぞれ独立して、有機基であり、
ただし、R1c及びR3cの少なくとも1つは、炭素数が17以上の長鎖アルキル基を有する有機基であるか、あるいは
R2c及びR4cは、それぞれ独立して、有機基であり、
ただし、R2c及びR4cの少なくとも1つは、炭素数が17以上の長鎖アルキル基を有する有機基である、
上記[24]に記載の化合物。
[26] R1c及びR3cは、それぞれ独立して、炭素数が17以上の長鎖アルキル基を有する有機基である、
R2c及びR4cは、それぞれ独立して、炭素数が17以上の長鎖アルキル基を有する有機基である、
上記[24]又は[25]に記載の化合物。
[27] 前記長鎖アルキル基の炭素数は、17~30である、上記[24]~[26]のいずれか1項に記載の化合物。
[28] R1c及びR3cは、それぞれ独立して、-O-R12cであるか、あるいは
R2c及びR4cは、それぞれ独立して、-O-R12cであり、
R12cは、C17-30アルキル基である、
上記[24]~[27]のいずれか1項に記載の化合物。
[29] R2c及びR4cは、水素原子であるか、あるいは
R1c及びR3cは、水素原子である、
上記[24]~[28]のいずれか1項に記載の化合物。
[30] n3は、4~6の整数である、上記[24]~[29]のいずれか1項に記載の化合物。
[31] R1c及びR3cは、-O-R12cであり、R2c及びR4cは、水素原子であるか、あるいは
R2c及びR4cは、-O-R12cであり、R1c及びR3cは、水素原子であり、
R12cは、C17-30アルキル基であり、
n3は、4~6の整数である、
上記[24]~[30]のいずれか1項に記載の化合物。
[32] 成膜した場合の膜の水に対する静的接触角は、80°以上である、上記[24]~[31]のいずれか1項に記載の化合物。
[33] 下記式(1D):
R1dは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R2dは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R3dは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R4dは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
ただし、R1d、R2d、R3d、及びR4dの少なくとも1つは、アルキル基を有する有機基であり、該アルキル基は、SP値が8.2以上であり、
n4は、4~20の整数である。]
で表される化合物。
[34] R1d及びR3dは、それぞれ独立して、有機基であり、
ただし、R1d及びR3dの少なくとも1つは、SP値が8.2以上であるアルキル基を有する有機基であるか、あるいは
R2d及びR4dは、それぞれ独立して、有機基であり、
ただし、R2d及びR4dの少なくとも1つは、SP値が8.2以上であるアルキル基を有する有機基である、
上記[33]に記載の化合物。
[35] R1d及びR3dは、それぞれ独立して、SP値が8.2以上であるアルキル基を有する有機基であるか、あるいは
R2d及びR4dは、それぞれ独立して、SP値が8.2以上であるアルキル基を有する有機基である、上記[33]又は[34]に記載の化合物。
[36] R2d及びR4dは、水素原子であるか、あるいは
R1d及びR3dは、水素原子である、
上記[33]~[35]のいずれか1項に記載の化合物。
[37] n4は、4~6の整数である、上記[33]~[36]のいずれか1項に記載の化合物。
[38] 前記アルキル基のSP値は、8.2~8.4である、上記[33]~[37]のいずれか1項に記載の化合物。
[39] R1d及びR3dは、-O-R12dであり、R2d及びR4dは、水素原子であるか、あるいは
R2d及びR4dは、-O-R12dであり、R1d及びR3dは、水素原子であり、
R12dは、C17-30アルキル基であり、
n4は、4~6の整数である、
上記[33]~[38]のいずれか1項に記載の化合物。
[40] 成膜した場合の膜の水に対する静的接触角は、80°以上である、上記[33]~[39]のいずれか1項に記載の化合物。
[41] 上記[1]~[40]のいずれか1項に記載の化合物の少なくとも1種を含む組成物。
[42] 上記[1]~[40]のいずれか1項に記載の化合物の成形体。
[43] 上記[41]に記載の組成物から形成される成形体。
[44] フィルムである、上記[42]又は[43]に記載の成形体。
[45] 上記[1]~[40]のいずれか1項に記載の化合物、又は上記[41]に記載の組成物で処理された基材を含む材料。
[46] 下記式(1E):
R1e、R2e、R3e、及びR4eは、それぞれ独立して、水素原子または有機基であり、
n5は、5又は6である。]
で表されるピラーアレーン及び炭化水素化合物を含む、撥液性組成物。
[47] 前記有機基は、炭素数1~30の有機基である、上記[46]に記載の撥液性組成物。
[48] さらに、溶媒を含む、上記[46]又は[47]に記載の撥液性組成物。
R1aは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R2aは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R3aは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R4aは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
ただし、R1a、R2a、R3a、及びR4aの少なくとも1つは、フルオロアルキル基を有する炭素数2以上の有機基であり、
n1は、4~20の整数である。]
で表される化合物を提供する。
-(Op1-R11a q1)-Rfa
[式中:
R11aは、各出現においてそれぞれ独立して、C1-10アルキレン基又は-CONH-であり、
Rfaは、C1-10フルオロアルキル基であり、
p1は、0~2の整数であり、
q1は、0~3の整数であり、
(Op1-R11a q1)中、O及びR11aの存在順序は限定されない。]
で表される基である。
-O-R11a-(O-R11a)r1-Rfa
[式中:
R11aは、それぞれ独立して、C1-10アルキレン基又は-CONH-であり、
Rfaは、C1-10フルオロアルキル基であり、
r1は、0又は1である。]
で表される基である。
-O-R11a-(O-R11a)r1-Rfa
[式中:
R11aは、それぞれ独立して、C1-10アルキレン基又は-CONH-であり、
Rfaは、C1-10パーフルオロアルキル基であり、
r1は、0又は1である。]
で表される基である。
-(Op3-R11p q3)-Rfp
[式中:
R11pは、各出現においてそれぞれ独立して、C1-10アルキレン基、好ましくはC1-6アルキレン基、より好ましくはC1-3アルキレン基であり、
Rfpは、1~5個、好ましくは5個のフッ素により置換されたフェニル基であり、
p3は、0~2の整数であり、
q3は、0~3の整数であり、
(Op3-R11p q3)中、O及びR11pの存在順序は限定されない。]
で表される基である。
-O-R11p-Rfp
[式中:
R11pは、各出現においてそれぞれ独立して、C1-10アルキレン基、好ましくはC1-6アルキレン基、より好ましくはC1-3アルキレン基であり、
Rfpは、1~5個、好ましくは5個のフッ素により置換されたフェニル基である。]
で表される基である。
R1a及びR3aは、-O-R11a-(O-R11a)r1-Rfaであり、R2a及びR4aは、水素原子であるか、あるいは
R2a及びR4aは、-O-R11a-(O-R11a)r1-Rfaであり、R1a及びR3aは、水素原子であり、
R11aは、それぞれ独立して、C1-10アルキレン基、好ましくはC1-6アルキレン基であり、
Rfaは、C1-10パーフルオロアルキル基、好ましくはC1-6パーフルオロアルキル基であり、
r1は、0又は1であり、
n1は、4~6の整数、好ましくは5又は6である。
R1a及びR3aは、-O-R11p-Rfpであり、R2a及びR4aは、水素原子であるか、あるいは
R2a及びR4aは、-O-R11p-Rfpであり、R1a及びR3aは、水素原子であり、
R11pは、それぞれ独立して、C1-6アルキレン基、好ましくはC1-3アルキレン基であり、
Rfpは、1~5個、好ましくは5個のフッ素により置換されたフェニル基であり、
n1は、4~6の整数、好ましくは5又は6である。
R1bは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R2bは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R3bは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R4bは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
ただし、R1b、R2b、R3b、及びR4bの少なくとも1つは、フッ素原子を有する有機基であって、該フッ素原子を有する有機基は、SP値が8.0以下であり、
n2は、4~20の整数である。]
で表される化合物を提供する。
δ=(ΣΔei/ΣΔvi)1/2
-(Op2-R11b q2)-Rfb
[式中:
R11bは、各出現においてそれぞれ独立して、C1-10アルキレン基であり、
Rfbは、C1-10フルオロアルキル基であり、
p2は、0~2の整数であり、
q2は、0~3の整数であり、
(Op2-R11b q2)中、O及びR11bの存在順序は限定されない。]
で表される基である。
-(Op1-R11a q1)-Rfp
[式中:
R11aは、各出現においてそれぞれ独立して、C1-10アルキレン基であり、
Rfpは、1~5個、好ましくは5個のフッ素により置換されたフェニル基であり、
p1は、0~2の整数であり、
q1は、0~3の整数であり、
(Op1-R11a q1)中、O及びR11aの存在順序は限定されない。]
で表される基である。
-O-R11b-(O-R11b)r2-Rfb
[式中:
R11bは、それぞれ独立して、C1-10アルキレン基であり、
Rfbは、C1-10フルオロアルキル基であり、
r2は、0又は1である。]
で表される基である。
-O-R11b-(O-R11b)r2-Rfb
[式中:
R11bは、それぞれ独立して、C1-10アルキレン基であり、
Rfbは、C1-10パーフルオロアルキル基であり、
r2は、0又は1である。]
で表される基である。
R1b及びR3bは、-O-R11b-(O-R11b)r2-Rfbであり、R2b及びR4bは、水素原子であるか、あるいは
R2b及びR4bは、-O-R11b-(O-R11b)r2-Rfbであり、R1b及びR3bは、水素原子であり、
R11bは、それぞれ独立して、C1-10アルキレン基、好ましくはC1-6アルキレン基であり、
Rfbは、C1-10パーフルオロアルキル基、好ましくはC1-6パーフルオロアルキル基であり、
r2は、0又は1であり、
n2は、4~6の整数、好ましくは5又は6である。
R1cは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R2cは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R3cは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R4cは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
ただし、R1c、R2c、R3c、及びR4cの少なくとも1つは、炭素数が17以上の長鎖アルキル基を有する有機基であり、
n3は、4~20の整数である。]
で表される化合物を提供する。
R1c及びR3cは、-O-R12cであり、R2c及びR4cは、水素原子であるか、あるいは、
R2c及びR4cは、-O-R12cであり、R1c及びR3cは、水素原子であり、
R12cは、C17-30アルキル基、好ましくはC18-30アルキル基、C26-30アルキル基であり、
n3は、4~6の整数、好ましくは5又は6である。
R1dは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R2dは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R3dは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
R4dは、各出現においてそれぞれ独立して、水素原子、又は有機基であり、
ただし、R1d、R2d、R3d、及びR4dの少なくとも1つは、アルキル基を有する有機基であり、該アルキル基は、SP値が8.2以上であり、
n4は、4~20の整数である。]
で表される化合物を提供する。
R1d及びR3dは、-O-R12dであり、R2d及びR4dは、水素原子であるか、あるいは
R2d及びR4dは、-O-R12dであり、R1d及びR3dは、水素原子であり、
R12dは、C17-30アルキル基、好ましくはC18-30アルキル基、C26-30アルキル基であり、
n4は、4~6の整数、好ましくは5又は6である、
請求項30~35のいずれか1項に記載の化合物。
R1e、R2e、R3e、及びR4eは、それぞれ独立して、水素原子または有機基であり、
n5は、5又は6である。]
で表されるピラーアレーン及び炭化水素化合物を含む、撥液性組成物を提供する。
ヒドロキノン体のピラー[5]アレーン(1.30g,2.13mmol)に、脱水ジメチルホルムアミド(30mL)、及び脱水テトラヒドロフラン(30mL)を加えた後に、NaH(1.33g,66.7mmol)を加えた。1-トシルオキシ-4,4,4-トリフルオロブタン(12.1g,42.9mmol)を加えた後に、60℃で72時間反応を行った。室温に戻した後に、メタノールを加えて反応をクエンチした。濃縮した後に、ジクロロメタンと飽和食塩水で分液を行い、クロロホルム層にNa2SO4を加えて脱水を行った。濾過によりNa2SO4を除き、濃縮を行った。シリカカラムクロマトグラフィー(ヘキサン:ジクロロメタン=2:1)で精製し、下記の置換ピラー[5]アレーン(収率15%)を得た。
1-トシルオキシ-4,4,4-トリフルオロブタンの代わりに、4,4,5,5,5-ペンタフルオロペンチル-p-トルエンスルホネート(14.3g,42.9mmol)を用いること以外は、合成例1と同様にして、下記の置換ピラー[5]アレーン(収率13%)を得た。
1-トシルオキシ-4,4,4-トリフルオロブタンの代わりに、8-[(6-ブロモヘキシル)オキシ]-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(22.6g,42.9mmol)を用いること以外は、合成例1と同様にして、下記の置換ピラー[5]アレーン(収率5.3%)を得た。
ヒドロキノン体のピラー[5]アレーンの代わりに、ヒドロキノン体のピラー[6]アレーン(1.30g,1.77mmol)を用い、1-トシルオキシ-4,4,4-トリフルオロブタンの代わりに、4,4,5,5,5-ペンタフルオロペンチル-p-トルエンスルホネート(14.3g,42.9mmol)を用いること以外は、合成例1と同様にして、下記の置換ピラー[6]アレーン(収率24%)を得た。
窒素雰囲気下で、1,2-ジクロロエタン(20mL)に1,4-ジペンチルオキシベンゼン(1.66g,10mmol)を溶かした溶液にパラホルムアルデヒド(0.31g,10mmol)を加えた。次に三フッ化ホウ素ジエチルエーテラート(1.25mL,10mmol)を加えて、30℃の温度で3時間攪拌した。溶液をメタノールに注ぎ、沈殿物をろ過により収集した。沈殿物をトリクロロメタンに溶解させ、溶けなかった部分はろ過により取り除いた。減圧下でトリクロロメタンを取り除き、目的化合物(0.413g,収率23.2%)をアセトンにより晶出させた。
13C NMR (CDCl3, 100 MHz, TMS) δ 149.8, 128.5, 115.1, 63.8, 29.8, 15.0
ヒドロキノン体のピラー[6]アレーン(0.582g,0.795mmol)を、アセトニトリル(60mL)に溶解させた。次いで、ペンタフルオロベンジルブロミド(5.00g,19.2mmol))を添加し、さらに、K2CO3(1.65g,11.9mmol)、KI(0.319g,1.92mmol)を添加した。混合液を、60℃に加熱し、72時間反応させた。シリカゲルクロマトグラフィー(ジクロロメタン:ヘキサン=20~25:80~75)により目的物を単離した。1H NMRおよびHPLCにより、目的化合物が得られたことを確認した。
ヒドロキノン体のピラー[5]アレーン(0.305g,0.5mmol)を、ジメチルスルホキシド(5mL)に溶解させた。その後、ステアリルイソシアネート(1.478g,5mmol)を添加し、触媒としてジブチルスズラウレートを1滴滴下した。混合物を、40℃に加熱し、6時間反応させた。反応溶液および析出物をヘキサン、水の順で洗浄し、目的化合物を得た。得られた化合物については、FT-IRにより3000~3500cm-1付近にブロードに出るヒドロキノン体ピラーアレーン由来のピークの消失、2266cm-1のステアリルイソシアネート由来のC=Oのピークの消失、1708cm-1付近のウレタン結合由来のC=Oのピーク生成から確認した。
(SP値)
合成例1~4のピラーアレーンの側鎖のSP値を、上記Fedorsの方法により算出した。結果を下記表に示す。
下記表に示す通り、合成例1~4の側鎖構造のSP値は6.9~7.4の範囲であった。これに対して、例えばSP値が5.9のフッ素樹脂を選択した場合に両者のSP値が近いため、ピラーアレーン化合物とフッ素樹脂との相溶性が良好であると考えられる。
側鎖構造が、長鎖アルキルオキシ基:-O-C17H35、-O-C20H41、-O-C26H53、-O-C30H61(すべて直鎖)である場合のSP値を、上記Fedorsの方法により算出した。結果を下記表に示す。
下記表に示す通り、参考例1~4の側鎖構造のSP値は8.4~8.5であった。これに対して、例えばSP値が8.1の非フッ素樹脂を選択した場合に両者のSP値が近いため、ピラーアレーン化合物とフッ素樹脂との相溶性が良好であると考えられる。
(キャストフィルムの形成)
上記合成例1、2、4、及び5で得られたピラーアレーンを、ジクロロメタンに溶解させた。得られた溶液を、ガラス基板上にキャストし、室温でジクロロメタンを揮発させた後、160度まで加熱し、溶融させた。次いで、室温で冷却して、ピラーアレーンのキャストフィルムを得た。
溶媒を入れたサンプル瓶及び上記で得られたキャストフィルムを加え、キャストフィルムを17時間溶媒の蒸気に曝し、その後、ドラフト内で2時間風乾させ、溶媒処理フィルムを得た。キャストフィルムと溶媒の組み合わせは下記の通りである。
合成例2のキャストフィルム:ペンタン、ヘキサン、ヘプタン、オクタン
合成例4のキャストフィルム:シクロヘキサン
合成例5のキャストフィルム:ペンタン、ヘキサン
合成例1、2、4、及び5の化合物から得られたキャストフィルム、及び上記で得られた溶媒処理フィルムの接触角を、上記暴露前後で測定した。接触角は、水を用い、全自動小型接触角測定計(メイワフォーシス、P200A-HSM)で測定した。結果を下記表に示す。
合成例1、2、4、及び5の化合物から得られたキャストフィルムの融点を、DSC7020(Hitachi High-Tech Science Co., Tokyo, Japan)で測定した。結果を下記表に示す。
Claims (48)
- R1a及びR3aは、それぞれ独立して、有機基であり、
ただし、R1a及びR3aの少なくとも1つは、フルオロアルキル基又はフルオロフェニル基を有する炭素数2以上の有機基であるか、あるいは
R2a及びR4aは、それぞれ独立して、有機基であり、
ただし、R2a及びR4aの少なくとも1つは、フルオロアルキル基又はフルオロフェニル基を有する炭素数2以上の有機基である、
請求項1に記載の化合物。 - R1a及びR3aは、それぞれ独立して、フルオロアルキル基又はフルオロフェニル基を有する炭素数2以上の有機基であるか、あるいは
R2a及びR4aは、それぞれ独立して、フルオロアルキル基又はフルオロフェニル基を有する炭素数2以上の有機基である、
請求項1又は2に記載の化合物。 - R2a及びR4aは、水素原子であるか、あるいは
R1a及びR3aは、水素原子である、
請求項1~3のいずれか1項に記載の化合物。 - n1は、4~6の整数である、請求項1~4のいずれか1項に記載の化合物。
- 前記フルオロアルキル基を有する炭素数2以上の有機基は、-(Op1-R11a q1)-Rfaであり、
R11aは、各出現においてそれぞれ独立して、C1-10アルキレン基又は-CONH-であり、
Rfaは、C1-10フルオロアルキル基であり、
p1は、0~2の整数であり、
q1は、0~3の整数であり、
(Op1-R11a q1)中、O及びR11aの存在順序は限定されない、
請求項1~5のいずれか1項に記載の化合物。 - 前記フルオロアルキル基を有する炭素数2以上の有機基は、-O-R11a-(O-R11a)r1-Rfaであり、
R11aは、それぞれ独立して、C1-10アルキレン基又は-CONH-であり、
Rfaは、C1-10フルオロアルキル基であり、
r1は、0又は1である、
請求項1~6のいずれか1項に記載の化合物。 - 前記フルオロアルキル基は、パーフルオロアルキル基である、請求項1~7のいずれか1項に記載の化合物。
- R1a及びR3aは、-O-R11a-(O-R11a)r1-Rfaであり、R2a及びR4aは、水素原子であるか、あるいは
R2a及びR4aは、-O-R11a-(O-R11a)r1-Rfaであり、R1a及びR3aは、水素原子であり、
R11aは、それぞれ独立して、C1-10アルキレン基又は-CONH-であり、
Rfaは、C1-10パーフルオロアルキル基であり、
r1は、0又は1であり、
n1は、4~6の整数である、
請求項1~8のいずれか1項に記載の化合物。 - 前記フルオロフェニル基を有する炭素数2以上の有機基は、下記式:
-(Op3-R11p q3)-Rfp
[式中:
R11pは、各出現においてそれぞれ独立して、C1-10アルキレン基であり、
Rfpは、1~5個フェニル基であり、
p3は、0~2の整数であり、
q3は、0~3の整数であり、
(Op3-R11p q3)中、O及びR11pの存在順序は限定されない。]
で表される基である、請求項1~5のいずれか1項に記載の化合物。 - 前記フルオロフェニル基を有する炭素数2以上の有機基は、下記式:
-O-R11p-Rfp
[式中:
R11pは、各出現においてそれぞれ独立して、C1-10アルキレン基であり、
Rfpは、1~5個のフッ素により置換されたフェニル基である。]
で表される基である、請求項1~5のいずれか1項に記載の化合物。 - R1a及びR3aは、-O-R11p-Rfpであり、R2a及びR4aは、水素原子であるか、あるいは
R2a及びR4aは、-O-R11p-Rfpであり、R1a及びR3aは、水素原子であり、
R11pは、それぞれ独立して、C1-6アルキレン基であり、
Rfpは、1~5個のフッ素により置換されたフェニル基であり、
n1は、4~6の整数である、
請求項1~5のいずれか1項に記載の化合物。 - 成膜した場合の膜の水に対する静的接触角は、80°以上である、請求項1~12のいずれか1項に記載の化合物。
- R1b及びR3bは、それぞれ独立して、有機基であり、
ただし、R1b及びR3bの少なくとも1つは、SP値が8.0以下であるフッ素原子を有する有機基であるか、あるいは
R2b及びR4bは、それぞれ独立して、有機基であり、
ただし、R2b及びR4bの少なくとも1つは、SP値が8.0以下であるフッ素原子を有する有機基である、
請求項14に記載の化合物。 - R1b及びR3bは、それぞれ独立して、SP値が8.0以下であるフッ素原子を有する有機基であるか、あるいは
R2b及びR4bは、それぞれ独立して、SP値が8.0以下であるフッ素原子を有する有機基である、
請求項14又は15に記載の化合物。 - R2b及びR4bは、水素原子であるか、あるいは
R1b及びR3bは、水素原子である、
請求項14~16のいずれか1項に記載の化合物。 - n2は、4~6の整数である、請求項14~17のいずれか1項に記載の化合物。
- 前記フッ素原子を有する有機基のSP値は、4.0~7.5である、請求項14~18のいずれか1項に記載の化合物。
- 前記フッ素原子を有する有機基は、C1-10フルオロアルキル基を有する、請求項14~19のいずれか1項に記載の化合物。
- 前記C1-10フルオロアルキル基は、C1-10パーフルオロアルキル基である、請求項20に記載の化合物。
- R1b及びR3bは、-O-R11b-(O-R11b)r2-Rfbであり、R2b及びR4bは、水素原子であるか、あるいは
R2b及びR4bは、-O-R11b-(O-R11b)r2-Rfbであり、R1b及びR3bは、水素原子であり、
R11bは、それぞれ独立して、C1-10アルキレン基であり、
Rfbは、C1-10パーフルオロアルキル基であり、
r2は、0又は1であり、
n2は、4~6の整数である、
請求項14~21のいずれか1項に記載の化合物。 - 成膜した場合の膜の水に対する静的接触角は、80°以上である、請求項14~22のいずれか1項に記載の化合物。
- R1c及びR3cは、それぞれ独立して、有機基であり、
ただし、R1c及びR3cの少なくとも1つは、炭素数が17以上の長鎖アルキル基を有する有機基であるか、あるいは
R2c及びR4cは、それぞれ独立して、有機基であり、
ただし、R2c及びR4cの少なくとも1つは、炭素数が17以上の長鎖アルキル基を有する有機基である、
請求項24に記載の化合物。 - R1c及びR3cは、それぞれ独立して、炭素数が17以上の長鎖アルキル基を有する有機基である、
R2c及びR4cは、それぞれ独立して、炭素数が17以上の長鎖アルキル基を有する有機基である、
請求項24又は25に記載の化合物。 - 前記長鎖アルキル基の炭素数は、17~30である、請求項24~26のいずれか1項に記載の化合物。
- R1c及びR3cは、それぞれ独立して、-O-R12cであるか、あるいは
R2c及びR4cは、それぞれ独立して、-O-R12cであり、
R12cは、C17-30アルキル基である、
請求項24~27のいずれか1項に記載の化合物。 - R2c及びR4cは、水素原子であるか、あるいは
R1c及びR3cは、水素原子である、
請求項24~28のいずれか1項に記載の化合物。 - n3は、4~6の整数である、請求項24~29のいずれか1項に記載の化合物。
- R1c及びR3cは、-O-R12cであり、R2c及びR4cは、水素原子であるか、あるいは
R2c及びR4cは、-O-R12cであり、R1c及びR3cは、水素原子であり、
R12cは、C17-30アルキル基であり、
n3は、4~6の整数である、
請求項24~30のいずれか1項に記載の化合物。 - 成膜した場合の膜の水に対する静的接触角は、80°以上である、請求項24~31のいずれか1項に記載の化合物。
- R1d及びR3dは、それぞれ独立して、有機基であり、
ただし、R1d及びR3dの少なくとも1つは、SP値が8.2以上であるアルキル基を有する有機基であるか、あるいは
R2d及びR4dは、それぞれ独立して、有機基であり、
ただし、R2d及びR4dの少なくとも1つは、SP値が8.2以上であるアルキル基を有する有機基である、
請求項33に記載の化合物。 - R1d及びR3dは、それぞれ独立して、SP値が8.2以上であるアルキル基を有する有機基であるか、あるいは
R2d及びR4dは、それぞれ独立して、SP値が8.2以上であるアルキル基を有する有機基である、請求項33又は34に記載の化合物。 - R2d及びR4dは、水素原子であるか、あるいは
R1d及びR3dは、水素原子である、
請求項33~35のいずれか1項に記載の化合物。 - n4は、4~6の整数である、請求項33~36のいずれか1項に記載の化合物。
- 前記アルキル基のSP値は、8.2~8.4である、請求項33~37のいずれか1項に記載の化合物。
- R1d及びR3dは、-O-R12dであり、R2d及びR4dは、水素原子であるか、あるいは
R2d及びR4dは、-O-R12dであり、R1d及びR3dは、水素原子であり、
R12dは、C17-30アルキル基であり、
n4は、4~6の整数である、
請求項33~38のいずれか1項に記載の化合物。 - 成膜した場合の膜の水に対する静的接触角は、80°以上である、請求項33~39のいずれか1項に記載の化合物。
- 請求項1~40のいずれか1項に記載の化合物の少なくとも1種を含む組成物。
- 請求項1~40のいずれか1項に記載の化合物の成形体。
- 請求項41に記載の組成物から形成される成形体。
- フィルムである、請求項42又は43に記載の成形体。
- 請求項1~40のいずれか1項に記載の化合物、又は請求項41に記載の組成物で処理された基材を含む材料。
- 前記有機基は、炭素数1~30の有機基である、請求項46に記載の撥液性組成物。
- さらに、溶媒を含む、請求項46又は47に記載の撥液性組成物。
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WO2024080369A1 (ja) * | 2022-10-14 | 2024-04-18 | ダイキン工業株式会社 | ピラーアレーン複合体 |
WO2024080376A1 (ja) * | 2022-10-14 | 2024-04-18 | ダイキン工業株式会社 | ピラーアレーン複合体 |
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- 2022-06-16 JP JP2022097536A patent/JP7292690B2/ja active Active
- 2022-06-16 CN CN202280042592.6A patent/CN117545732A/zh active Pending
- 2022-06-16 EP EP22825072.6A patent/EP4357330A1/en active Pending
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OGOSHI TOMOKI, MARUYAMA KEISUKE, SAKATSUME YUMA, KAKUTA TAKAHIRO, YAMAGISHI TADA-AKI, ICHIKAWA TAKAHIRO, MIZUNO MOTOHIRO: "Guest Vapor-Induced State Change of Structural Liquid Pillar[6]arene", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 141, no. 2, 16 January 2019 (2019-01-16), pages 785 - 789, XP093017112, ISSN: 0002-7863, DOI: 10.1021/jacs.8b12253 * |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2024080369A1 (ja) * | 2022-10-14 | 2024-04-18 | ダイキン工業株式会社 | ピラーアレーン複合体 |
WO2024080376A1 (ja) * | 2022-10-14 | 2024-04-18 | ダイキン工業株式会社 | ピラーアレーン複合体 |
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TW202336002A (zh) | 2023-09-16 |
EP4357330A1 (en) | 2024-04-24 |
US20240132432A1 (en) | 2024-04-25 |
JP2023001080A (ja) | 2023-01-04 |
JP7292690B2 (ja) | 2023-06-19 |
CN117545732A (zh) | 2024-02-09 |
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