WO2022138333A1 - 表面処理剤 - Google Patents
表面処理剤 Download PDFInfo
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- WO2022138333A1 WO2022138333A1 PCT/JP2021/046080 JP2021046080W WO2022138333A1 WO 2022138333 A1 WO2022138333 A1 WO 2022138333A1 JP 2021046080 W JP2021046080 W JP 2021046080W WO 2022138333 A1 WO2022138333 A1 WO 2022138333A1
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- 239000012756 surface treatment agent Substances 0.000 title claims description 67
- 125000000962 organic group Chemical group 0.000 claims description 101
- -1 silane compound Chemical class 0.000 claims description 73
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 63
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 61
- 229910000077 silane Inorganic materials 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 40
- 125000001153 fluoro group Chemical group F* 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 30
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 27
- 125000002947 alkylene group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 229920002545 silicone oil Polymers 0.000 claims description 17
- 230000003287 optical effect Effects 0.000 claims description 16
- 229910052710 silicon Inorganic materials 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 14
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 8
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 8
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 8
- 125000006551 perfluoro alkylene group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052789 astatine Inorganic materials 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
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- 230000000052 comparative effect Effects 0.000 description 6
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- 125000006273 (C1-C3) 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- PGISRKZDCUNMRX-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-(trifluoromethoxy)butane Chemical compound FC(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)F PGISRKZDCUNMRX-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
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- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OHMPIQOZXCOSLG-UHFFFAOYSA-N N-prop-2-enylpentan-2-amine Chemical compound CCCC(C)NCC=C OHMPIQOZXCOSLG-UHFFFAOYSA-N 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
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- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
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- QIROQPWSJUXOJC-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(trifluoromethyl)cyclohexane Chemical class FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F QIROQPWSJUXOJC-UHFFFAOYSA-N 0.000 description 1
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- 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
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- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-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
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- 241000282575 Gorilla Species 0.000 description 1
- ICBJCVRQDSQPGI-UHFFFAOYSA-N Methyl hexyl ether Chemical compound CCCCCCOC ICBJCVRQDSQPGI-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- KWWOQRSLYPHAMK-UHFFFAOYSA-N ethyl 2-hydroxybutanoate Chemical compound CCOC(=O)C(O)CC KWWOQRSLYPHAMK-UHFFFAOYSA-N 0.000 description 1
- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960004624 perflexane Drugs 0.000 description 1
- LOQGSOTUHASIHI-UHFFFAOYSA-N perfluoro-1,3-dimethylcyclohexane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)C1(F)F LOQGSOTUHASIHI-UHFFFAOYSA-N 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
- C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/18—Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films
Definitions
- the present disclosure relates to a novel fluoropolyether group-containing silane compound and a surface treatment agent containing such a compound.
- fluoropolyether group-containing silane compounds can provide excellent water repellency, oil repellency, stain resistance, etc. when used for surface treatment of a substrate.
- Layers obtained from surface treatment agents containing fluoropolyether group-containing silane compounds are various as so-called functional thin films such as glass, plastics, fibers, sanitary products, and building materials. (Patent Document 1).
- the fluoropolyether group-containing silane compound described in Patent Document 1 can provide a surface-treated layer having excellent functions, but a surface-treated layer having higher durability is required.
- the disclosure includes the following aspects: [1] The following formula (1) or (2): [During the ceremony: RF1 is Rf 1 - RF-O q- ; RF2 is -Rf 2 p -RF -O q- ; Rf 1 is a C 1-16 alkyl group optionally substituted with one or more fluorine atoms; Rf 2 is a C 1-6 alkylene group optionally substituted with one or more fluorine atoms; RFs are independently divalent fluoropolyether groups; p is 0 or 1; q is 0 or 1 independently of each other; R 1 is independently each of -R 3- (OR 2 ) m -On-R 4 -R 5 ; R 2 is a C 1-6 alkylene group, independently of each appearance; m is an integer from 2 to 10; n is 0 or 1; R 3 is a single bond or C 1-6 alkylene group; R4 is a single bond or C 1-6 alkylene group; R 5 is
- R 53 is a phenyl group, a C 1-6 alkyl group or a C 1-6 alkoxy group independently at each appearance.
- R 54 is a hydrogen atom, a phenyl group or a C 1-6 alkyl group independently at each appearance.
- m5 is an integer from 1 to 100 independently for each appearance.
- n5 is an integer of 1 to 20 independently at each appearance.
- p5 is an integer from 1 to 10.
- X B can be independently single-bonded or the following formula: -(X 61 ) p6- (During the ceremony: X 61 is an independent -O-, -S-, o-, m- or p-phenylene group, -C (O) O-, -OC (O)-, -Si (R) at each appearance.
- R 63 is a phenyl group, a C 1-6 alkyl group or a C 1-6 alkoxy group independently at each appearance.
- R 64 is a hydrogen atom, a phenyl group or a C 1-6 alkyl group independently at each appearance.
- m6 is an integer from 1 to 100 independently for each appearance.
- n6 is an integer of 1 to 20 independently at each appearance.
- p6 is an integer from 1 to 10.
- It is a group represented by.
- RF is independent of each appearance, and the formula: -(OC 6 F 12 ) a- (OC 5 F 10 ) b- (OC 4 F 8 ) c- (OC 3 R Fa 6 ) d- (OC 2 F 4 ) e- (OCF 2 ) f- [In the formula, R Fa is a hydrogen atom, a fluorine atom or a chlorine atom independently at each appearance.
- a, b, c, d, e and f are independently integers of 0 to 200, and the sum of a, b, c, d, e and f is 1 or more, and a, b,
- the order of existence of each repeating unit in parentheses with c, d, e or f is arbitrary in the equation, provided that all R Fas are hydrogen or chlorine atoms, a, b, At least one of c, e and f is one or more.
- RF is independently represented by the following equations (f1), (f2), (f3), (f4) or (f5): -(OC 3 F 6 ) d- (OC 2 F 4 ) e- (f1) [In the formula, d is an integer from 1 to 200, and e is 0 or 1.
- c and d are independently integers from 0 to 30; e and f are independently integers from 1 to 200; The sum of c, d, e and f is an integer from 10 to 200; The order of existence of each repeating unit with the subscripts c, d, e or f and enclosed in parentheses is arbitrary in the formula.
- R 6 is OCF 2 or OC 2 F 4 ;
- R 7 is a group selected from OC 2 F 4 , OC 3 F 6 , OC 4 F 8 , OC 5 F 10 and OC 6 F 12 , or two or three selected from these groups. It is a combination of groups; g is an integer of 2 to 100.
- e is an integer of 1 or more and 200 or less, and a, b, c, d and f are independently integers of 0 or more and 200 or less, and a, b, c, d and e.
- the sum of and f is at least 1, and the order of existence of each repeating unit in parentheses with a, b, c, d, e or f is arbitrary in the equation.
- f is an integer of 1 or more and 200 or less, and a, b, c, d and e are independently integers of 0 or more and 200 or less, and a, b, c, d, e.
- the sum of and f is at least 1, and the order of existence of each repeating unit in parentheses with a, b, c, d, e or f is arbitrary in the equation.
- R 11 is a hydroxyl group or a hydrolyzable group independently at each appearance;
- R 12 is a hydrogen atom or a monovalent organic group, independently of each appearance;
- n1 is an integer of 0 to 3 independently for each unit (SiR 11 n1 R 12 3-n1 );
- X 11 is an independent, single-bonded or divalent organic group at each appearance;
- R 13 is an independent hydrogen atom or monovalent organic group at each appearance;
- t is an integer greater than or equal to 2 independently for each appearance;
- R 14 is a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1 R 12 3-n1 independently at each appearance;
- R15 is a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkyleneoxy group having 1 to 6 carbon atoms, independently of each other at each appearance;
- R a1 is -Z 1 -SiR 21 p1 R 22 q1
- R e1 l2 R f1 m2 ; Z 4 is an independent, single bond, oxygen atom or divalent organic group at each appearance; However, in the formulas (S1), (S2), (S3), (S4) and (S5), at least one Si atom to which a hydroxyl group or a hydrolyzable group is bonded is present.
- the fluoropolyether group-containing silane compound according to the above [8], wherein R Si bonded to X B is a group represented by the formula (S3) or (S4).
- R Si in R 1 is the fluoropolyether group-containing silane compound according to the above [8] or [9], which is a group represented by the formula (S2).
- X and A are independently single-bonded or the following formula: -(R 51' ) p5' -(X 51' ) q5' -(R 51' ) p5 " - (During the ceremony: R 51'is an independent C 1-6 alkylene group, respectively.
- X 51' is O, p5'is 0 or 1 and is "p5" is 0 or 1 and is q5'is 0 or 1 and is Here, at least one of p5'and p5'is 1.) It is a group represented by; X B can be independently single-bonded or the following formula: -(R 61' ) p6' -(X 61' ) q6' -(R 61' ) p6 " - (During the ceremony: R 61'is an independent C 1-6 alkylene group and is a C 1-6 alkylene group.
- the substrate and the surface of the substrate may be any of the fluoropolyether group-containing silane compound according to any one of the above [1] to [12] or any of the above [13] to [16].
- monovalent organic group means a carbon-containing monovalent group.
- the monovalent organic group is not particularly limited, but may be a hydrocarbon group or a derivative thereof.
- a hydrocarbon group derivative is a group having one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy, etc. at the end or molecular chain of the hydrocarbon group.
- organic group simply means a monovalent organic group.
- divalent organic group means a divalent group containing carbon.
- the divalent organic group is not particularly limited, and examples thereof include a divalent group obtained by desorbing one hydrogen atom from the organic group.
- hydrocarbon group means a group containing carbon and hydrogen, from which one hydrogen atom has been desorbed from the hydrocarbon.
- the hydrocarbon group is not particularly limited, but may be substituted with one or more substituents, such as a C 1-20 hydrocarbon group, for example, an aliphatic hydrocarbon group or an aromatic group. Hydrocarbon groups and the like can be mentioned.
- the above-mentioned "aliphatic hydrocarbon group” may be linear, branched or cyclic, and may be saturated or unsaturated. Further, the hydrocarbon group may contain one or more ring structures.
- the substituent of the "hydrocarbon group” is not particularly limited, but may be substituted with, for example, one or more halogen atoms, C 1-6 alkyl.
- hydrolyzable group means a group capable of undergoing a hydrolysis reaction, i.e., a group capable of being removed from the main skeleton of the compound by the hydrolysis reaction.
- the fluoropolyether group-containing silane compound of the present disclosure has the following formula (1) or (2): [During the ceremony: RF1 is Rf 1 - RF-O q- ; RF2 is -Rf 2 p -RF -O q- ; Rf 1 is a C 1-16 alkyl group optionally substituted with one or more fluorine atoms; Rf 2 is a C 1-6 alkylene group optionally substituted with one or more fluorine atoms; RFs are independently divalent fluoropolyether groups; p is 0 or 1; q is 0 or 1 independently for each appearance; R 1 is independently each of -R 3- (OR 2 ) m -On-R 4 -R 5 ; R 2 is a C 1-6 alkylene group, independently of each appearance; m is an integer from 2 to 10; n is 0 or 1; R 3 is a single bond or C 1-6 alky
- R 53 is a phenyl group, a C 1-6 alkyl group or a C 1-6 alkoxy group independently at each appearance.
- R 54 is a hydrogen atom, a phenyl group or a C 1-6 alkyl group independently at each appearance.
- m5 is an integer from 1 to 100 independently for each appearance.
- n5 is an integer of 1 to 20 independently at each appearance.
- p5 is an integer from 1 to 10.
- X B can be independently single-bonded or the following formula: -(X 61 ) p6- (During the ceremony: X 61 is an independent -O-, -S-, o-, m- or p-phenylene group, -C (O) O-, -OC (O)-, -Si (R) at each appearance.
- R 63 is a phenyl group, a C 1-6 alkyl group or a C 1-6 alkoxy group independently at each appearance.
- R 64 is a hydrogen atom, a phenyl group or a C 1-6 alkyl group independently at each appearance.
- m6 is an integer from 1 to 100 independently for each appearance.
- n6 is an integer of 1 to 20 independently at each appearance.
- p6 is an integer from 1 to 10.
- It is a group represented by. ] It is a fluoropolyether group-containing silane compound represented by.
- RF1 is Rf 1 ⁇ RF ⁇ O q ⁇ .
- RF2 is ⁇ Rf 2 p ⁇ RF ⁇ Oq ⁇ .
- Rf 1 is a C 1-16 alkyl group which may be substituted with one or more fluorine atoms.
- the "C 1-16 alkyl group" in the C 1-16 alkyl group which may be substituted with one or more fluorine atoms may be a straight chain or a branched chain, and is preferable. Is a linear or branched C 1-6 alkyl group, particularly a C 1-3 alkyl group, more preferably a linear C 1-6 alkyl group, particularly a C 1-3 alkyl group.
- the Rf 1 is preferably a C 1-16 alkyl group substituted with one or more fluorine atoms, more preferably a CF 2HC 1-15 perfluoroalkylene group, and even more preferably. Is a C 1-16 perfluoroalkyl group.
- the C 1-16 perfluoroalkyl group may be linear or branched, preferably a linear or branched C 1-6 perfluoroalkyl group, particularly C 1- .
- a 3 perfluoroalkyl group more preferably a linear C 1-6 perfluoroalkyl group, particularly a C 1-3 perfluoroalkyl group, specifically -CF 3 , -CF 2 CF 3 , or -CF. 2 CF 2 CF 3 .
- Rf 2 is a C 1-6 alkylene group which may be substituted with one or more fluorine atoms.
- the "C 1-6 alkylene group" in the C 1-6 alkylene group which may be substituted with one or more fluorine atoms may be a straight chain or a branched chain, and is preferable. Is a straight chain or branched C 1-3 alkylene group, more preferably a straight chain C 1-3 alkylene group.
- the Rf 2 is preferably a C 1-6 alkylene group substituted with one or more fluorine atoms, more preferably a C 1-6 perfluoroalkylene group, and even more preferably a C 1- . 3 Perfluoroalkylene group.
- the C 1-6 perfluoroalkylene group may be linear or branched, preferably a linear or branched C 1-3 perfluoroalkylene group, and more preferably. Is a linear C 1-3 perfluoroalkylene group, specifically ⁇ CF 2- , ⁇ CF 2 CF 2- , or ⁇ CF 2 CF 2 CF 2- .
- p is 0 or 1. In one embodiment, p is 0. In another embodiment p is 1.
- q is 0 or 1 independently of each other. In one embodiment, q is 0. In another embodiment q is 1.
- RF is a divalent fluoropolyether group independently at each appearance.
- RF is preferably the formula: -(OC 6 F 12 ) a- (OC 5 F 10 ) b- (OC 4 F 8 ) c- (OC 3 R Fa 6 ) d- (OC 2 F 4 ) e- (OCF 2 ) f- [During the ceremony: R Fa is a hydrogen atom, a fluorine atom or a chlorine atom independently at each appearance. a, b, c, d, e and f are each independently an integer of 0 to 200, and the sum of a, b, c, d, e and f is 1 or more.
- each repeating unit in parentheses with a, b, c, d, e or f is arbitrary in the formula. However, when all R Fas are hydrogen atoms or chlorine atoms, at least one of a, b, c, e and f is 1 or more. ] It is a group represented by.
- R Fa is preferably a hydrogen atom or a fluorine atom, and more preferably a fluorine atom. However, when all R Fas are hydrogen atoms or chlorine atoms, at least one of a, b, c, e and f is 1 or more.
- A, b, c, d, e and f are preferably independent integers of 0 to 100.
- the sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, and may be, for example, 15 or more or 20 or more.
- the sum of a, b, c, d, e and f is preferably 200 or less, more preferably 100 or less, still more preferably 60 or less, and may be, for example, 50 or less or 30 or less.
- repeating units may be linear or branched.
- -(OC 6 F 12 )- is-(OCF 2 CF 2 CF 2 CF 2 CF 2 CF 2 )-,-(OCF (CF 3 ) CF 2 CF 2 CF 2 )-,-(OCF) 2 CF (CF 3 ) CF 2 CF 2 CF 2 )-,-(OCF 2 CF 2 CF (CF 3 ) CF 2 CF 2 )-,-(OCF 2 CF 2 CF (CF 3 ) CF 2 CF 2 )-,-(OCF 2 CF 2 CF 2 CF (CF 3 ) CF 2 )- ,-(OCF 2 CF 2 CF 2 CF 2 CF (CF 3 ))-and the like.
- -(OC 3 F 6 )-(that is, R Fa is a fluorine atom in the above formula) is-(OCF 2 CF 2 CF 2 )-,-(OCF (CF 3 ) CF 2 )-and-( It may be either OCF 2 CF (CF 3 ))-.
- -(OC 2 F 4 )- may be any of-(OCF 2 CF 2 )-and-(OCF (CF 3 ))-.
- the repeating unit is linear. By making the repeating unit linear, the surface slipperiness, wear durability, etc. of the surface treatment layer can be improved.
- the repeating unit is branched and chain-shaped.
- the coefficient of dynamic friction of the surface treatment layer can be increased.
- RF is a group represented by any of the following formulas (f1) to ( f5 ) independently in each appearance.
- -(OC 3 F 6 ) d- (OC 2 F 4 ) e- (f1) [In the formula, d is an integer from 1 to 200, and e is 0 or 1. ];
- c and d are independently integers of 0 or more and 30 or less, and e and f are independently integers of 1 or more and 200 or less.
- f is an integer of 1 or more and 200 or less, and a, b, c, d and e are independently integers of 0 or more and 200 or less, and a, b, c, d.
- the order of existence of each repeating unit enclosed in parentheses with, e or f is arbitrary in the equation.
- d is preferably an integer of 5 to 200, more preferably 10 to 100, still more preferably 15 to 50, for example 25 to 35.
- e is 1.
- e is 0.
- OC 3 F 6 is preferably OCF 2 CF 2 CF 2 , OCF 2 CF (CF 3 ), or OCF (CF 3 ) CF 2 , and more preferably OC F 2 CF 2 CF 2 . be.
- e and f are independently integers of preferably 5 to 200, more preferably 10 to 200, respectively. Further, the sum of c, d, e and f is preferably 5 or more, more preferably 10 or more, and may be, for example, 15 or more or 20 or more.
- the above formula (f2) is preferably ⁇ (OCF 2 CF 2 CF 2 CF 2 ) c ⁇ (OCF 2 CF 2 CF 2 ) d ⁇ (OCF 2 CF 2 ) e ⁇ (OCF 2 ). It is a group represented by f ⁇ .
- the formula (f2) may be a group represented by ⁇ (OC 2 F 4 ) e ⁇ (OCF 2 ) f ⁇ .
- R 6 is preferably OC 2 F 4 .
- R 7 is preferably a group selected from OC 2 F 4 , OC 3 F 6 and OC 4 F 8 , or 2 or independently selected from these groups. It is a combination of three groups, more preferably a group selected from OC 3 F 6 and OC 4 F 8 .
- the combination of two or three groups independently selected from OC 2 F 4 , OC 3 F 6 and OC 4 F 8 is not particularly limited, but is, for example, -OC 2 F 4 OC 3 F 6- , -OC.
- g is preferably an integer of 3 or more, more preferably 5 or more.
- the above g is preferably an integer of 50 or less.
- OC 2 F 4 , OC 3 F 6 , OC 4 F 8 , OC 5 F 10 and OC 6 F 12 may be either linear or branched, preferably straight. It is a chain.
- the above formula (f3) is preferably ⁇ (OC 2 F 4 ⁇ OC 3 F 6 ) g ⁇ or ⁇ (OC 2 F 4 ⁇ OC 4 F 8 ) g ⁇ .
- e is preferably an integer of 1 or more and 100 or less, more preferably 5 or more and 100 or less.
- the sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, for example, 10 or more and 100 or less.
- f is preferably an integer of 1 or more and 100 or less, and more preferably 5 or more and 100 or less.
- the sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, for example, 10 or more and 100 or less.
- the RF is a group represented by the above formula ( f1 ).
- the RF is a group represented by the above formula ( f2 ).
- the RF is a group represented by the above formula ( f3 ).
- the RF is a group represented by the above formula ( f4 ).
- the RF is a group represented by the above formula ( f5 ).
- the ratio of e to f (hereinafter referred to as “e / f ratio”) is 0.1 to 10, preferably 0.2 to 5, and more preferably 0.2 to 2. Yes, more preferably 0.2 to 1.5, and even more preferably 0.2 to 0.85.
- e / f ratio the slipperiness, abrasion durability and chemical resistance (for example, durability against artificial sweat) of the surface treatment layer obtained from this compound are further improved.
- the smaller the e / f ratio the more the slipperiness and wear durability of the surface treatment layer are improved.
- the e / f ratio to 0.1 or more, the stability of the compound can be further enhanced. The larger the e / f ratio, the better the stability of the compound.
- the e / f ratio is preferably 0.2 to 0.95, more preferably 0.2 to 0.9.
- the e / f ratio is preferably 1.0 or more, and more preferably 1.0 to 2.0.
- the number average molecular weight of the RF1 and RF2 moieties is not particularly limited, but is, for example, 500 to 30,000, preferably 1,500 to 30,000, more preferably. Is 2,000 to 10,000. In the present specification, the number average molecular weight of RF1 and RF2 is a value measured by 19 F -NMR.
- the number average molecular weight of the RF1 and RF2 moieties is 500 to 30,000, preferably 1,000 to 20,000, more preferably 2,000 to 15,000, even more preferably 2,. It can be 000 to 10,000, for example 3,000 to 6,000.
- the number average molecular weight of the RF1 and RF2 moieties can be 4,000 to 30,000, preferably 5,000 to 10,000, more preferably 6,000 to 10,000.
- R 1 is independently each of -R 3- (OR 2 ) m -On-R 4 -R 5 .
- R 2 is a C 1-6 alkylene group independently at each appearance.
- the C 1-6 alkylene group may be a straight chain or a branched chain, and is preferably a straight chain.
- R 2 is preferably a C 1-4 alkylene group, more preferably a C 1-3 alkylene group, and particularly preferably -CH 2 CH 2- .
- m is an integer of 2 to 10, preferably an integer of 2 to 6, and more preferably an integer of 2 to 4.
- R 3 is a single bond or a C 1-6 alkylene group.
- the C 1-6 alkylene group may be a straight chain or a branched chain, and is preferably a straight chain.
- the R 3 is preferably a C 1-6 alkylene group, more preferably a C 1-3 alkylene group, and particularly preferably a methylene group.
- R 4 is a single bond or a C 1-6 alkylene group.
- the C 1-6 alkylene group may be a straight chain or a branched chain, and is preferably a straight chain.
- the R4 is preferably a C 1-6 alkylene group, more preferably a C 1-3 alkylene group, and particularly preferably a methylene group.
- n 0 or 1.
- n 0.
- n 1
- R 5 is a hydrogen atom or R Si .
- R Si may be the same as or different from R Si bound to XB.
- the R Si in R 1 is the same as the R Si bound to X B.
- the R Si in R 1 is different from the R Si bound to X B.
- the R5 is a hydrogen atom.
- the R5 is RSi .
- RSi is a monovalent group containing a Si atom to which a hydroxyl group or a hydrolyzable group is bonded independently at each appearance.
- RSi is the following formula (S1), (S2), (S3), (S4) or (S5) :. It is a group represented by.
- R 11 is a hydroxyl group or a hydrolyzable group independently at each appearance.
- R 11 is preferably an independently hydrolyzable group at each appearance.
- R j represents a substituted or unsubstituted C 1-4 alkyl group), more preferably —OR j (ie, an alkoxy group).
- Rj include an unsubstituted alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group and an isobutyl group; and a substituted alkyl group such as a chloromethyl group.
- an alkyl group particularly an unsubstituted alkyl group is preferable, and a methyl group or an ethyl group is more preferable.
- R j is a methyl group and in another embodiment, R j is an ethyl group.
- R 12 is a hydrogen atom or a monovalent organic group independently at each appearance.
- the monovalent organic group is a monovalent organic group excluding the hydrolyzable group.
- the monovalent organic group is preferably a C 1-20 alkyl group, more preferably a C 1-6 alkyl group, and even more preferably a methyl group.
- n1 is an integer of 0 to 3 independently for each unit (SiR 11 n1 R 12 3-n1 ).
- R Si is a group represented by the formula (S1) or (S2)
- the R Si portion at the end of the formula (1) and the formula (2) (hereinafter, simply the formula (1) and the formula (2)).
- terminal portion there is at least one unit in which n1 is 1 to 3 (SiR 11 n1 R 12 3-n1 ). That is, not all n1s are zero at the same time in such an end portion.
- at the terminal portions of the formulas (1) and (2) there is at least one Si atom to which a hydroxyl group or a hydrolyzable group is bonded.
- n1 is an integer of preferably 1 to 3, more preferably 2 to 3, and even more preferably 3 independently for each unit (SiR 11 n1 R 12 3-n1 ).
- X 11 is a single bond or a divalent organic group independently at each appearance.
- a divalent organic group is preferably -R 28 -O x -R 29- (in the formula, R 28 and R 29 are independently single-bonded or C 1-20 alkylene groups, respectively, at each appearance.
- X is 0 or 1.).
- the C 1-20 alkylene group may be a straight chain or a branched chain, but is preferably a straight chain.
- the C 1-20 alkylene group is preferably a C 1-10 alkylene group, more preferably a C 1-6 alkylene group, and even more preferably a C 1-3 alkylene group.
- X 11 is -C 1-6 alkylene-OC 1-6 alkylene- or -OC 1-6 alkylene-, independently of each appearance.
- X 11 is an independently single-bonded or linear C 1-6 alkylene group at each appearance, preferably a single-bonded or straight-chain C 1-3 alkylene group, more preferably a single. It is a bonded or straight C 1-2 alkylene group, more preferably a straight C 1-2 alkylene group.
- R 13 is a hydrogen atom or a monovalent organic group independently at each appearance.
- the monovalent organic group is preferably a C 1-20 alkyl group.
- the C 1-20 alkyl group may be linear or branched, but is preferably linear.
- R 13 is independently a hydrogen atom or a linear C 1-6 alkyl group at each appearance, preferably a hydrogen atom or a linear C 1-3 alkyl group, preferably a hydrogen atom. Or it is a methyl group.
- t is an integer of 2 or more independently at each appearance.
- t is an integer of 2 to 10, preferably an integer of 2 to 6, independently of each appearance.
- R 14 is a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1 R 12 3-n1 independently at each appearance.
- the halogen atom is preferably an iodine atom, a chlorine atom or a fluorine atom, and more preferably a fluorine atom.
- R 14 is a hydrogen atom.
- R15 is a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkyleneoxy group having 1 to 6 carbon atoms, independently of each other at each appearance.
- R15 is an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkyleneoxy group having 1 to 6 carbon atoms, independently of each other at each appearance.
- R15 is a single bond.
- the formula (S1) is the following formula (S1-a).
- R 11 , R 12 , R 13 , X 11 , and n1 have the same meaning as the description in the above formula (S1);
- t1 and t2 are independently one or more integers, preferably 1 to 10 integers, more preferably 2 to 10 integers, for example 1 to 5 integers or 2 to 5 integers, respectively;
- the order of existence of each repeating unit in parentheses with t1 and t2 is arbitrary in the equation.
- the formula (S1) is the following formula (S1-b). [In the formula, R 11 , R 12 , R 13 , X 11 , n1 and t have the same meaning as the description in the above formula (S1)].
- R a1 is ⁇ Z1 ⁇ SiR 21 p1 R 22 q1 R 23 r1 independently at each appearance.
- Z 1 is an oxygen atom or a divalent organic group independently at each appearance.
- the right side is coupled to (SiR 21 p1 R 22 q1 R 23 r1 ).
- Z 1 is a divalent organic group.
- Z 1 does not include those that form a siloxane bond with the Si atom to which Z 1 is attached.
- Si—Z1 - Si does not contain a siloxane bond.
- Z 1 is preferably a C 1-6 alkylene group,-(CH 2 ) z1 -O- (CH 2 ) z2- (in the formula, z1 is an integer of 0 to 6, for example, an integer of 1 to 6).
- z2 is an integer of 0 to 6, for example, an integer of 1 to 6) or-(CH 2 ) z3 -phenylene-(CH 2 ) z4- (in the formula, z3 is an integer of 0 to 6).
- z4 is an integer of 0 to 6, for example, an integer of 1 to 6).
- the C 1-6 alkylene group may be a straight chain or a branched chain, but is preferably a straight chain.
- These groups may be substituted with one or more substituents selected from, for example, a fluorine atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, and a C 2-6 alkynyl group. However, it is preferably unsubstituted.
- Z 1 is a C 1-6 alkylene group or-(CH 2 ) z3 -phenylene- (CH 2 ) z4- , preferably -phenylene- (CH 2 ) z4- .
- Z 1 is such a group, light resistance, especially UV resistance, can be higher.
- the Z 1 is a C 1-3 alkylene group. In one embodiment, Z 1 can be -CH 2 CH 2 CH 2- . In another embodiment, Z 1 can be -CH 2 CH 2- .
- R 21 is ⁇ Z 1 ′ -SiR 21 ′ p1 ′ R 22 ′ q1 ′ R 23 ′ r1 ′ independently in each appearance.
- the Z 1' is an oxygen atom or a divalent organic group independently at each appearance.
- the right side is coupled to (SiR 21'p1'R 22'q1'R 23'r1 ' ) .
- Z 1' is a divalent organic group.
- Z 1'does not include those forming a siloxane bond with the Si atom to which Z 1'is attached.
- Si—Z 1′ - Si does not contain a siloxane bond.
- Z 1' is preferably a C 1-6 alkylene group,-(CH 2 ) z1' -O- (CH 2 ) z2' -(in the formula, z1'is an integer of 0 to 6, for example, 1 to 1'. It is an integer of 6, and z2'is an integer of 0 to 6, for example, an integer of 1 to 6) or- (CH 2 ) z3'-phenylene- (CH 2 ) z4' -(in the formula, z3'. Is an integer of 0 to 6, for example, an integer of 1 to 6, and z4'is an integer of 0 to 6, for example, an integer of 1 to 6).
- the C 1-6 alkylene group may be a straight chain or a branched chain, but is preferably a straight chain. These groups may be substituted with one or more substituents selected from, for example, a fluorine atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, and a C 2-6 alkynyl group. However, it is preferably unsubstituted.
- Z 1' is a C 1-6 alkylene group or- (CH 2 ) z3' -phenylene- (CH 2 ) z4'- , preferably-phenylene- (CH 2 ) z4'- .
- Z 1' is a such group, light resistance, especially UV resistance, can be higher.
- the Z 1' is a C 1-3 alkylene group. In one embodiment, Z 1'can be -CH 2 CH 2 CH 2- . In another embodiment, Z 1'can be -CH 2 CH 2- .
- R 21' is independently ⁇ Z 1 ” -SiR 22” q1 ” R 23” r1 ” at each appearance.
- Z 1 " is an oxygen atom or a divalent organic group independently at each appearance.
- the right side is (SiR 22 “ q1" R 23 " r1”. ).
- Z 1 " is a divalent organic group.
- Z 1 " does not include those forming a siloxane bond with the Si atom to which Z 1" is attached.
- Z 1 does not include those forming a siloxane bond with the Si atom to which Z 1" is attached.
- (Si—Z1 ′′ -Si) does not contain a siloxane bond.
- Z 1 " is preferably a C 1-6 alkylene group,-(CH 2 ) z1" -O- (CH 2 ) z2 " -(in the formula, z1" is an integer of 0 to 6, for example, 1 to 1. It is an integer of 6, and z2 "is an integer of 0 to 6, for example, an integer of 1 to 6) or-(CH 2 ) z3" -phenylene- (CH 2 ) z4 " -(in the formula, z3". Is an integer of 0 to 6, for example an integer of 1 to 6, and z4 "is an integer of 0 to 6, for example, an integer of 1 to 6).
- Such a C 1-6 alkylene group is a straight chain.
- These groups are, for example, a fluorine atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, and a C 2- . It may be substituted with one or more substituents selected from the 6 alkynyl groups, but is preferably unsubstituted.
- the Z 1 " is a C 1-6 alkylene group or- (CH 2 ) z3" -phenylene- (CH 2 ) z4 " -, preferably-phenylene- (CH 2 ) z4" -.
- light resistance particularly UV resistance, can be higher.
- the Z 1 " is a C 1-3 alkylene group. In one embodiment, the Z 1" can be -CH 2 CH 2 CH 2- . In another embodiment, Z 1 " can be -CH 2 CH 2- .
- the R 22 " is an hydroxyl group or a hydrolyzable group independently at each appearance.
- the R 22 " is preferably an independently hydrolyzable group at each appearance.
- R j indicates a substituted or unsubstituted C 1-4 alkyl group), more preferably ⁇ OR j (that is, an alkoxy group), and R j is a methyl group, an ethyl group, and the like.
- Unsubstituted alkyl groups such as propyl group, isopropyl group, n-butyl group and isocyanate group; substituted alkyl groups such as chloromethyl group are mentioned.
- an alkyl group particularly an unsubstituted alkyl group is preferable, and a methyl group or a methyl group or Ethyl groups are more preferred.
- R j is a methyl group and in another embodiment, R j is an ethyl group.
- the R 23 " is independently a hydrogen atom or a monovalent organic group at each appearance.
- the monovalent organic group is a monovalent organic group excluding the hydrolyzable group.
- the monovalent organic group is preferably a C 1-20 alkyl group, or-(CH 2 ) y1 -O- (CH 2 ) y2- (in the formula, y1 is an integer of 0 to 6".
- y1 is an integer of 0 to 6
- y2 is an integer of 0 to 6, for example, an integer of 1 to 6
- a C 1-20 alkyl group is , Preferably a C 1-6 alkyl group, more preferably a methyl group.
- the q1 " is an integer of 0 to 3 independently at each appearance, and the r1" is an integer of 0 to 3 independently at each appearance.
- the total of q1 "and r1" is 3 in the unit of (SiR 22 " q1" R 23 " r1” ).
- q1 " is an integer of preferably 1 to 3, more preferably 2 to 3, and even more preferably 3 independently for each unit (SiR 22" q1 " R 23" r1 " ).
- the R 22' is a hydroxyl group or a hydrolyzable group independently at each appearance.
- R 22' is preferably a hydrolyzable group, independently of each appearance.
- R j indicates a substituted or unsubstituted C 1-4 alkyl group), and more preferably —OR j (that is, an alkoxy group).
- Rj examples include an unsubstituted alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group and an isobutyl group; and a substituted alkyl group such as a chloromethyl group.
- an alkyl group, particularly an unsubstituted alkyl group is preferable, and a methyl group or an ethyl group is more preferable.
- R j is a methyl group and in another embodiment, R j is an ethyl group.
- the R 23' is a hydrogen atom or a monovalent organic group independently at each appearance.
- the monovalent organic group is a monovalent organic group excluding the hydrolyzable group.
- the monovalent organic group is preferably a C 1-20 alkyl group, or-(CH 2 ) y3 -O- (CH 2 ) y4- (in the formula, y3 is an integer of 0 to 6).
- y4 is an integer of 0 to 6, for example, an integer of 1 to 6
- the C 1-20 alkyl group is preferably a C 1-6 alkyl group, more preferably a methyl group.
- p1' is 0.
- p1' is an integer of 1 to 3 or an integer of 2 to 3 or 3 independently for each unit (SiR 21'p1'R 22'q1'R 23'r1 ' ) . May be. In a preferred embodiment, p1'is 3.
- q1' is an integer of 1 to 3, preferably an integer of 2 to 3, independently of each unit (SiR 21'p1'R 22'q1'R 23'r1 ' ) . More preferably, it is 3.
- p1' is 0 and q1'is an integer of 1 to 3 independently for each unit (SiR 21'p1'R 22'q1'R 23'r1 ' ) , which is preferable. Is an integer of 2 to 3, more preferably 3.
- the R 22 is a hydroxyl group or a hydrolyzable group independently at each appearance.
- R 22 is preferably an independently hydrolyzable group at each appearance.
- R j represents a substituted or unsubstituted C 1-4 alkyl group), more preferably —OR j (ie, an alkoxy group).
- Rj include an unsubstituted alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group and an isobutyl group; and a substituted alkyl group such as a chloromethyl group.
- an alkyl group particularly an unsubstituted alkyl group is preferable, and a methyl group or an ethyl group is more preferable.
- R j is a methyl group and in another embodiment, R j is an ethyl group.
- the R 23 is a hydrogen atom or a monovalent organic group independently at each appearance.
- the monovalent organic group is a monovalent organic group excluding the hydrolyzable group.
- the monovalent organic group is preferably a C 1-20 alkyl group, or-(CH 2 ) y5 -O- (CH 2 ) y6- (in the formula, y5 is an integer of 0 to 6, for example. It is an integer of 1 to 6, where y6 is an integer of 0 to 6, for example an integer of 1 to 6), more preferably a C 1-20 alkyl group.
- the C 1-20 alkyl group is preferably a C 1-6 alkyl group, more preferably a methyl group.
- p1 is an integer of 0 to 3 independently at each appearance
- q1 is an integer of 0 to 3 independently at each appearance
- r1 is an integer of 0 to 3 independently at each appearance. It is an integer from 0 to 3.
- the total of p1, q1 and r1 is 3 in the unit of (SiR 21 p1 R 22 q1 R 23 r1 ).
- p1 is 0.
- p1 may be an integer of 1 to 3, an integer of 2 to 3, or 3 independently for each unit (SiR 21 p1 R 22 q1 R 23 r1 ). In a preferred embodiment, p1 is 3.
- q1 is an integer of 1 to 3 independently of each unit (SiR 21 p1 R 22 q1 R 23 r1 ), preferably an integer of 2 to 3, and more preferably 3.
- p1 is 0 and q1 is an integer of 1 to 3 independently of each unit (SiR 21 p1 R 22 q1 R 23 r1 ), preferably an integer of 2 to 3, and further. It is preferably 3.
- R b1 is a hydroxyl group or a hydrolyzable group independently at each appearance.
- the R b1 is preferably a hydrolyzable group independently at each appearance.
- R j indicates a substituted or unsubstituted C 1-4 alkyl group), and more preferably —OR j (that is, an alkoxy group).
- Rj examples include an unsubstituted alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group and an isobutyl group; and a substituted alkyl group such as a chloromethyl group.
- an alkyl group, particularly an unsubstituted alkyl group is preferable, and a methyl group or an ethyl group is more preferable.
- R j is a methyl group and in another embodiment, R j is an ethyl group.
- R c1 is a hydrogen atom or a monovalent organic group independently at each appearance.
- the monovalent organic group is a monovalent organic group excluding the hydrolyzable group.
- the monovalent organic group is preferably a C 1-20 alkyl group, or-(CH 2 ) y7- O- (CH 2 ) y8- (in the formula, y7 is an integer of 0 to 6).
- y7 is an integer of 0 to 6
- y8 is an integer of 0 to 6
- more preferably a C 1-20 alkyl group is preferably a C 1-6 alkyl group, more preferably a methyl group.
- k1 is an integer of 0 to 3 independently at each appearance
- l1 is an integer of 0 to 3 independently at each appearance
- m1 is an integer of 0 to 3 independently at each appearance. It is an integer from 0 to 3.
- the total of k1, l1 and m1 is 3 in the unit of (SiR a1 k1 R b1 l1 R c1 m1 ).
- k1 is an integer of 1 to 3 independently of each unit (SiR a1 k1 R b1 l1 R c1 m1 ), preferably 2 or 3, and more preferably 3. In a preferred embodiment, k1 is 3.
- R Si is a group represented by the formula (S3)
- a hydroxyl group or a hydrolyzable group is preferably used at the terminal portions of the formulas (1) and (2).
- the group represented by the formula (S3) is ⁇ Z1 - SiR 22 q1 R 23 r1 (in the formula, q1 is an integer of 1 to 3, preferably 2 or 3, more preferably 3).
- R1 is an integer of 0 to 2), -Z 1'- SiR 22'q1'R 23' r1 ' (in the formula, q1'is an integer of 1 to 3, preferably 2 Or 3, more preferably 3, r1'is an integer of 0 to 2), or -Z 1 " -SiR 22" q1 " R 23" r1 " (in the formula, q1" is 1 to It is an integer of 3, preferably 2 or 3, more preferably 3, and r1 "is an integer of 0 to 2).
- Z 1 , Z 1' , Z 1". , R 22 , R 23 , R 22' , R 23' , R 22 " , and R 23" have the same meaning as above.
- q1 is an integer of 1 to 3, preferably 2 or 3, in at least one, preferably all R 21 ' . It is preferably 3.
- R 21 is present in formula (S3)
- p1' is 0 and q1'is an integer of 1-3, preferably in at least one, preferably all R 21 ,. Is 2 or 3, more preferably 3.
- R a1 is present in formula (S3)
- p1 is 0 and q1 is an integer of 1 to 3, preferably 2 in at least one, preferably all Ra 1 . Or 3, more preferably 3.
- k1 is 2 or 3, preferably 3, p1 is 0, and q1 is 2 or 3, preferably 3.
- R d1 is -Z 2 -CR 31 p2 R 32 q2 R 33 r2 independently at each appearance.
- Z 2 is a single bond, oxygen atom or divalent organic group independently at each appearance.
- the right side is coupled to (CR 31 p2 R 32 q2 R 33 r2 ).
- Z 2 is a divalent organic group.
- Z 2 is preferably a C 1-6 alkylene group,-(CH 2 ) z5 -O- (CH 2 ) z6- (in the formula, z5 is an integer of 0 to 6, for example, an integer of 1 to 6).
- z6 is an integer of 0 to 6, for example, an integer of 1 to 6) or-(CH 2) z7-phenylene-(CH 2 ) z8- ( in the formula, z7 is an integer of 0 to 6).
- z8 is an integer of 0 to 6, for example, an integer of 1 to 6).
- the C 1-6 alkylene group may be a straight chain or a branched chain, but is preferably a straight chain.
- These groups may be substituted with one or more substituents selected from, for example, a fluorine atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, and a C 2-6 alkynyl group. However, it is preferably unsubstituted.
- Z 2 is a C 1-6 alkylene group or- (CH 2 ) z7-phenylene- (CH 2 ) z8- , preferably -phenylene- (CH 2 ) z8- .
- Z 2 is a such group, light resistance, especially UV resistance, can be higher.
- the Z 2 is a C 1-3 alkylene group. In one embodiment, Z 2 can be -CH 2 CH 2 CH 2- . In another embodiment, Z 2 can be -CH 2 CH 2- .
- R 31 is independently of -Z 2' - CR 32'q2'R 33'r2' at each appearance.
- Z 2' is a single bond, oxygen atom or divalent organic group independently at each appearance.
- the right side is coupled to (CR 32'q2'R 33'r2 ' ) .
- Z 2' is preferably a C 1-6 alkylene group,-(CH 2 ) z5' -O- (CH 2 ) z6' -(in the formula, z5' is an integer of 0 to 6, for example, 1 to 1. It is an integer of 6, and z6'is an integer of 0 to 6, for example, an integer of 1 to 6) or- (CH 2) z7'-phenylene- (CH 2 ) z8' -(in the formula, z7'. Is an integer of 0 to 6, for example, an integer of 1 to 6, and z8'is an integer of 0 to 6, for example, an integer of 1 to 6).
- the C 1-6 alkylene group may be a straight chain or a branched chain, but is preferably a straight chain. These groups may be substituted with one or more substituents selected from, for example, a fluorine atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, and a C 2-6 alkynyl group. However, it is preferably unsubstituted.
- Z 2' is a C 1-6 alkylene group or-(CH 2 ) z7' -phenylene- (CH 2 ) z8'- , preferably-phenylene- (CH 2 ) z8'- .
- Z 2' is a such group, light resistance, especially UV resistance, can be higher.
- the Z 2' is a C 1-3 alkylene group.
- Z 2'can be -CH 2 CH 2 CH 2- .
- Z 2'can be -CH 2 CH 2- .
- the R 32' is independently -Z 3 -SiR 34 n2 R 35 3-n2 at each appearance.
- Z 3 is a single bond, an oxygen atom or a divalent organic group independently at each appearance.
- the right side is coupled to (SiR 34 n2 R 35 3-n2 ).
- Z 3 is an oxygen atom.
- Z 3 is a divalent organic group.
- the above Z 3 is preferably a C 1-6 alkylene group,-(CH 2 ) z5 " -O- (CH 2 ) z6" -(in the formula, z5 "is an integer of 0 to 6, for example, 1 to 6.
- Z6 is an integer of 0 to 6, for example, an integer of 1 to 6) or- (CH 2) z7 "-phenylene- (CH 2 ) z8" -(in the formula, z7 "is , 0 to 6, for example, an integer of 1 to 6, and z8 "is an integer of 0 to 6, for example, an integer of 1 to 6).
- the C 1-6 alkylene group may be a straight chain or a branched chain, but is preferably a straight chain.
- These groups may be substituted with one or more substituents selected from, for example, a fluorine atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, and a C 2-6 alkynyl group. However, it is preferably unsubstituted.
- Z 3 is a C 1-6 alkylene group or- (CH 2) z7 "-phenylene- (CH 2 ) z8" -, preferably -phenylene- (CH 2 ) z8 " -.
- the light resistance, especially the UV resistance, can be higher if the group is such a group.
- the Z 3 is a C 1-3 alkylene group. In one embodiment, Z 3 can be -CH 2 CH 2 CH 2- . In another embodiment, Z 3 can be -CH 2 CH 2- .
- the R 34 is a hydroxyl group or a hydrolyzable group independently at each appearance.
- R 34 is preferably an independently hydrolyzable group at each appearance.
- R j represents a substituted or unsubstituted C 1-4 alkyl group), more preferably —OR j (ie, an alkoxy group).
- Rj include an unsubstituted alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group and an isobutyl group; and a substituted alkyl group such as a chloromethyl group.
- an alkyl group particularly an unsubstituted alkyl group is preferable, and a methyl group or an ethyl group is more preferable.
- R j is a methyl group and in another embodiment, R j is an ethyl group.
- the R 35 is a hydrogen atom or a monovalent organic group independently at each appearance.
- the monovalent organic group is a monovalent organic group excluding the hydrolyzable group.
- the monovalent organic group is preferably a C 1-20 alkyl group, or-(CH 2 ) y9 -O- (CH 2 ) y10- (in the formula, y9 is an integer of 0 to 6).
- y9 is an integer of 0 to 6
- y10 is an integer of 0 to 6
- more preferably a C 1-20 alkyl group is preferably a C 1-6 alkyl group, more preferably a methyl group.
- n2 is an integer of 0 to 3 independently for each unit (SiR 34 n2 R 35 3-n2 ).
- R Si is a group represented by the formula (S4)
- n2 is 1 to 3 in the terminal portions of the formulas (1) and (2) (SiR 34 n2 R 35 3-n2 ) units.
- there is at the terminal portions of the formulas (1) and (2) there is at least one Si atom to which a hydroxyl group or a hydrolyzable group is bonded.
- n2 is an integer of preferably 1 to 3, more preferably 2 to 3, and even more preferably 3 independently for each unit (SiR 34 n2 R 35 3-n2 ).
- the R 33' is a hydrogen atom, a hydroxyl group or a monovalent organic group independently at each appearance.
- the monovalent organic group is a monovalent organic group excluding the hydrolyzable group.
- the monovalent organic group is preferably a C 1-20 alkyl group or-(C s H 2s ) t 1- (OC s H 2s ) t 2 (in the formula, s is 1 to 6).
- R 33' is a hydroxyl group.
- R 33' is a monovalent organic group, preferably a C 1-20 alkyl group, more preferably a C 1-6 alkyl group.
- the q2' is an integer of 0 to 3 independently at each appearance, and the r2'is an integer of 0 to 3 independently at each appearance.
- q2' is an integer of preferably 1 to 3, more preferably 2 to 3, and even more preferably 3 independently for each unit (CR 32'q2'R 33'r2 ' ) .
- R 32 is -Z 3 -SiR 34 n2 R 35 3-n2 independently in each appearance.
- Such -Z 3 -SiR 34 n2 R 35 3-n2 has the same meaning as the description in the above R 32' .
- the R 33 is a hydrogen atom, a hydroxyl group or a monovalent organic group independently at each appearance.
- the monovalent organic group is a monovalent organic group excluding the hydrolyzable group.
- the monovalent organic group is preferably a C 1-20 alkyl group or-(C s H 2s ) t 1- (OC s H 2s ) t 2 (in the formula, s is 1 to 6). It is an integer, preferably an integer of 2 to 4, t1 is 1 or 0, preferably 0, and t2 is an integer of 1 to 20, preferably an integer of 2 to 10, and more preferably an integer of 2 to 6. ), More preferably a C 1-20 alkyl group, still more preferably a C 1-6 alkyl group, and particularly preferably a methyl group.
- R 33 is a hydroxyl group.
- R 33 is a monovalent organic group, preferably a C 1-20 alkyl group, more preferably a C 1-6 alkyl group.
- p2 is an integer of 0 to 3 independently at each appearance
- q2 is an integer of 0 to 3 independently at each appearance
- r2 is an integer of 0 to 3 independently at each appearance. It is an integer from 0 to 3.
- the total of p2, q2 and r2 is 3 in the unit of (CR 31 p2 R 32 q2 R 33 r2 ).
- p2 is 0.
- p2 may be an integer of 1 to 3, an integer of 2 to 3, or 3 independently for each unit (CR 31 p2 R 32 q2 R 33 r2 ). In a preferred embodiment, p2 is 3.
- q2 is an integer of 1 to 3 independently of each unit (CR 31 p2 R 32 q2 R 33 r2 ), preferably an integer of 2 to 3, and more preferably 3.
- p2 is 0 and q2 is an integer of 1 to 3 independently of each unit (CR 31 p2 R 32 q2 R 33 r2 ), preferably an integer of 2 to 3, and further. It is preferably 3.
- R e1 is -Z 3 -SiR 34 n2 R 35 3-n2 independently at each appearance.
- Such -Z 3 -SiR 34 n2 R 35 3-n2 has the same meaning as the description in the above R 32' .
- the R f1 is a hydrogen atom, a hydroxyl group or a monovalent organic group independently at each appearance.
- the monovalent organic group is a monovalent organic group excluding the hydrolyzable group.
- the monovalent organic group is preferably a C 1-20 alkyl group or-(C s H 2s ) t 1- (OC s H 2s ) t 2 (in the formula, s is 1 to 6). It is an integer, preferably an integer of 2 to 4, t1 is 1 or 0, preferably 0, and t2 is an integer of 1 to 20, preferably an integer of 2 to 10, and more preferably an integer of 2 to 6. ), More preferably a C 1-20 alkyl group, still more preferably a C 1-6 alkyl group, and particularly preferably a methyl group.
- R f1 is a hydroxyl group.
- R f1 is a monovalent organic group, preferably a C 1-20 alkyl group, more preferably a C 1-6 alkyl group.
- k2 is an integer of 0 to 3 independently at each appearance
- l2 is an integer of 0 to 3 independently at each appearance
- m2 is an integer of 0 to 3 independently at each appearance. It is an integer from 0 to 3.
- the total of k2, l2 and m2 is 3 in the unit of (CR d1 k2 R e1 l2 R f1 m2 ).
- n2 is 1 to 3, preferably 2 or 3, more preferably 3 (SiR 34 n2 R 35 3-n2 ) units.
- n2 is 1 to 3, preferably 2 or 3, more preferably 3 (SiR 34 n2 R 35 3-n2 ) units.
- two or more for example, 2 to 27 pieces, preferably 2 to 9 pieces, more preferably 2 to 6 pieces, still more preferably 2 to 3 pieces. Particularly preferably, there are three.
- n2 is an integer of 1 to 3, preferably 2 or 3, more preferably in at least one, preferably all R 32 ' . Is 3.
- n2 is an integer of 1 to 3, preferably 2 or 3, more preferably 3 in at least one, preferably all R 32 . Is.
- n2 is an integer of 1 to 3, preferably 2 or 3, more preferably 3 in at least one, preferably all Ra1 . Is.
- k2 is 0, l2 is 2 or 3, preferably 3, and n2 is 2 or 3, preferably 3.
- R g1 and R h1 are independently in each appearance, -Z 4 -SiR 11 n1 R 12 3-n1 , -Z 4 -SiR a1 k1 R b1 l1 R c1 m1 , -Z 4 -CR d1 k2 .
- R e1 l2 R f1 m2 R 11 , R 12 , R a1 , R b2 , R c1 , R d1 , R e1 , R f1 , n1, k1, l1, m1, k2, l2, and m2 have the same meanings as described above.
- R g1 and R h1 are independently ⁇ Z4 -SiR 11 n1 R 12 3-n1 .
- the Z 4 is a single bond, an oxygen atom or a divalent organic group independently at each appearance.
- the right side is coupled to (SiR 11 n1 R 12 3-n1 ).
- Z 4 is an oxygen atom.
- Z4 is a divalent organic group.
- the above Z 4 is preferably a C 1-6 alkylene group,-(CH 2 ) z5 " -O- (CH 2 ) z6" -(in the formula, z5 "is an integer of 0 to 6, for example, 1 to 6.
- Z6 is an integer of 0 to 6, for example, an integer of 1 to 6) or- (CH 2) z7 "-phenylene- (CH 2 ) z8" -(in the formula, z7 "is , 0 to 6, for example, an integer of 1 to 6, and z8 "is an integer of 0 to 6, for example, an integer of 1 to 6).
- the C 1-6 alkylene group may be a straight chain or a branched chain, but is preferably a straight chain.
- These groups may be substituted with one or more substituents selected from, for example, a fluorine atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, and a C 2-6 alkynyl group. However, it is preferably unsubstituted.
- Z 4 is a C 1-6 alkylene group or- (CH 2) z7 "-phenylene- (CH 2 ) z8" -, preferably -phenylene- (CH 2 ) z8 " -.
- the light resistance, especially the UV resistance, can be higher if the group is such a group.
- the Z 4 is a C 1-3 alkylene group. In one embodiment, Z 4 can be -CH 2 CH 2 CH 2- . In another embodiment, Z 4 can be -CH 2 CH 2- .
- RSi is a group represented by the formula (S2), (S3), (S4) or (S5). These compounds can form a surface-treated layer having high surface slipperiness.
- R Si is a group represented by the formula (S1), (S3), (S4) or (S5). Since these compounds have a plurality of hydrolyzable groups at one end, they can strongly adhere to the substrate and form a surface treatment layer having high wear durability.
- RSi is a group represented by the formula (S1), (S3) or (S4). Since these compounds have a plurality of hydrolyzable groups at one end, they can strongly adhere to the substrate and form a surface treatment layer having high wear durability.
- RSi is a group represented by the formula (S3) or (S4). Since these compounds may have a plurality of hydrolyzable groups branched from one Si atom or C atom at one end, a surface treatment layer having higher wear durability can be formed.
- R Si is a group represented by the formula (S1).
- RSi is a group represented by the formula (S2).
- RSi is a group represented by the formula (S3).
- RSi is a group represented by the formula (S4).
- RSi is a group represented by the formula (S5).
- RSi bound to XB is a group represented by the formula (S3) or (S4).
- RSi bound to XB is a group represented by the formula (S4).
- R Si in R 1 is a group represented by the formula (S2).
- the R Si bound to X B is a group represented by the formula (S3) or (S4), preferably a group represented by the formula (S4), and the R Si in R 1 is a group represented by the formula (S4). It is a group represented by S2).
- XA is independently single-bonded or the following formula: -(X 51 ) p5- [During the ceremony: X 51 is an independent -O-, -S-, o-, m- or p-phenylene group, -C (O) O-, -OC (O)-, -Si (R) at each appearance.
- R 53 is independently a phenyl group, a C 1-6 alkyl group or a C 1-6 alkoxy group at each appearance, preferably a phenyl group or a C 1-6 alkyl group, more preferably a methyl group.
- R 54 is a hydrogen atom, a phenyl group or a C 1-6 alkyl group (preferably a methyl group) independently at each appearance.
- m5 is an integer of 1 to 100, preferably an integer of 1 to 20, independently of each appearance.
- n5 is an integer of 1 to 20, preferably an integer of 1 to 6, and more preferably an integer of 1 to 3, independently of each appearance.
- p5 is an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably an integer of 1 to 3.
- It is a group represented by. In the description of XA , the left side of each group is bonded to RF1 or RF2 in the formula, and the right side is bonded to the carbon atom of CONR 1 .
- XA does not contain a siloxane bond (-Si - O-Si-).
- XA is a single bond.
- X A is-(X 51 ) p5- .
- the X 51 is independently at each appearance, -O-, -C (O) O-, -OC (O)-, -CONR 54-, -NR 54 CO- , -O-CONR. It is a group selected from the group consisting of 54-, -NR 54 CO-O-, -NR 54- and- (CH 2 ) n5- .
- X 51 is a group independently selected from the group consisting of -O-, -CONR 54-, -NR 54 CO-, and- (CH 2 ) n5- , respectively at each appearance. ..
- X 51 is a group selected independently from the group consisting of —O— and ⁇ (CH 2 ) n5 ⁇ at each appearance.
- XA is independently single-bonded or the following formula: -(R 51' ) p5' -(X 51' ) q5' -(R 51' ) p5 " - (During the ceremony: R 51'is an independent C 1-6 alkylene group, respectively.
- R 51' is O, p5'is 0 or 1 and is "p5" is 0 or 1 and is q5'is 0 or 1 and is Here, at least one of p5'and p5'is 1.) It is a group represented by.
- each XA is independently a C 1-6 alkylene group.
- X B is independently single-bonded or the following formula: -(X 61 ) p6- [During the ceremony: X 61 is an independent -O-, -S-, o-, m- or p-phenylene group, -C (O) O-, -OC (O)-, -Si (R) at each appearance.
- R 63 is independently a phenyl group, a C 1-6 alkyl group or a C 1-6 alkoxy group at each appearance, preferably a phenyl group or a C 1-6 alkyl group, more preferably a methyl group.
- R 64 is a hydrogen atom, a phenyl group or a C 1-6 alkyl group (preferably a methyl group) independently at each appearance.
- m6 is an integer of 1 to 100, preferably an integer of 1 to 20, independently of each appearance.
- n6 is an integer of 1 to 20, preferably an integer of 1 to 6, and more preferably an integer of 1 to 3, independently of each appearance.
- p6 is an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably an integer of 1 to 3.
- It is a group represented by. In the description of XB, the left side of each group is bonded to the nitrogen atom of CONR 1 in the formula, and the right side is bonded to RSi.
- XB does not contain a siloxane bond (-Si - O-Si-).
- XB is a single bond.
- XB is- (X 61 ) p6- .
- the X- 61 is independently at each appearance, -O-, -C (O) O-, -OC (O)-, -CONR 64- , -NR 64 CO-, -O-CONR. It is a group selected from the group consisting of 64- , -NR 64 CO-O-, -NR 64- and-(CH 2 ) n6- .
- the X 61 is a group independently selected from the group consisting of -O-, -CONR 64- , -NR 64 CO-, and- (CH 2 ) n6- , respectively, at each appearance. ..
- X 61 is a group selected independently from the group consisting of —O— and ⁇ (CH 2 ) n6 -in each appearance.
- the X Bs are independently single-bonded or the following formula: -(R 61' ) p6' -(X 61' ) q6' -(R 61' ) p6 " - (During the ceremony: R 61'is an independent C 1-6 alkylene group and is a C 1-6 alkylene group. X 61'is O, p6'is 0 or 1 and is "p6" is 0 or 1 and is q6'is 0 or 1 and is Here, at least one of p6'and p6'is 1.) It is a group represented by.
- each XB is independently a C 1-6 alkylene group.
- X A is a single bond and X B is an independent C 1-6 alkylene group.
- the fluoropolyether group-containing silane compound represented by the formula (1) or the formula (2) does not contain a siloxane bond (-Si-O-Si-).
- the fluoropolyether group-containing silane compound represented by the above formula (1) or the formula (2) is not particularly limited, but may have an average molecular weight of 5 ⁇ 10 2 to 1 ⁇ 10 5 . Within such a range, it is preferable to have an average molecular weight of 2,000 to 32,000, more preferably 2,500 to 12,000, from the viewpoint of wear durability.
- the "average molecular weight” refers to a number average molecular weight, and the "average molecular weight” is a value measured by 19 F-NMR.
- the fluoropolyether group-containing silane compound represented by the above formulas (1) and (2) can be produced, for example, by the following method.
- R26 is independently a hydrogen atom, a monovalent organic group, a hydroxyl group, a hydrolyzable group, or a halogen atom.
- R26 is independently a hydrogen atom, a monovalent organic group, a hydroxyl group, a hydrolyzable group, or a halogen atom.
- the surface treatment agent of the present disclosure contains at least one fluoropolyether group-containing silane compound represented by the formula (1) or (2).
- the fluoropolyether group-containing silane compound in the surface treatment agent of the present disclosure is a compound represented by the formula (1).
- the fluoropolyether group-containing silane compound in the surface treatment agent of the present disclosure is a compound represented by the formula (2).
- the fluoropolyether group-containing silane compound is a compound represented by the formula (1) and a compound represented by the formula (2).
- the compound represented by the formula (2) is preferably 0.1 with respect to the total of the compound represented by the formula (1) and the compound represented by the formula (2). It is 1 mol% or more and 35 mol% or less.
- the lower limit of the content of the compound represented by the formula (2) with respect to the total of the compound represented by the formula (1) and the compound represented by the formula (2) is preferably 0.1 mol%, more preferably 0.1 mol%. It can be 0.2 mol%, more preferably 0.5 mol%, even more preferably 1 mol%, particularly preferably 2 mol%, and particularly 5 mol%.
- the upper limit of the content of the compound represented by the formula (2) with respect to the total of the compound represented by the formula (1) and the compound represented by the formula (2) is preferably 35 mol%, more preferably 30 mol%. %, More preferably 20 mol%, even more preferably 15 mol% or 10 mol%.
- the compound represented by the formula (2) is preferably 0.1 mol% or more and 30 mol% or less, more preferably more preferably 0.1 mol% or more and 30 mol% or less, based on the total of the compound represented by the formula (1) and the compound represented by the formula (2).
- 0.1 mol% or more and 20 mol% or less more preferably 0.2 mol% or more and 10 mol% or less, still more preferably 0.5 mol% or more and 10 mol% or less, particularly preferably 1 mol% or more and 10 mol% or less.
- it is, for example, 2 mol% or more and 10 mol% or less, or 5 mol% or more and 10 mol% or less.
- the content of the compound represented by the above formula (1) or (2) is preferably 0.1 to 50.0% by mass, more preferably 1.0 to 30.0 with respect to the entire surface treatment agent. It may be% by mass, more preferably 5.0 to 25.0% by mass, and particularly preferably 10.0 to 20.0% by mass.
- the surface treatment agent of the present disclosure is a solvent, a (non-reactive) fluoropolyether compound that can be understood as a fluorine-containing oil, preferably a perfluoro (poly) ether compound (hereinafter collectively referred to as "fluorine-containing oil”).
- fluorine-containing oil preferably a perfluoro (poly) ether compound
- Silicone compounds (non-reactive) that can be understood as silicone oils (hereinafter referred to as "silicone oils”), alcohols, catalysts, surfactants, polymerization inhibitors, sensitizers and the like may be included.
- solvent examples include aliphatic hydrocarbons such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane and mineral spirit; 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 spirit
- aromatic hydrocarbons such as benzene, toluene, xylene, naphthalene and solvent naphtha.
- the fluorine-containing oil is not particularly limited, and examples thereof include a compound represented by the following general formula (3) (perfluoro (poly) ether compound).
- Rf 5 represents an alkyl group having 1 to 16 carbon atoms (preferably a perfluoroalkyl group having C 1-16 ) which may be substituted with one or more fluorine atoms
- Rf 6 is a perfluoroalkyl group.
- a', b', c'and d' represent the number of repeating units of four types of perfluoro (poly) ethers constituting the main skeleton of the polymer, and are integers of 0 or more and 300 or less independently of each other.
- A', b', c'and d' are at least 1, preferably 1 to 300, and more preferably 20 to 300.
- the order of existence of each repeating unit with the subscripts a', b', c'or d'and enclosed in parentheses is arbitrary in the equation.
- -(OC 4 F 8 )- is-(OCF 2 CF 2 CF 2 CF 2 )-,-(OCF (CF 3 ) CF 2 CF 2 )-,-(OCF 2 CF (CF) 3 ) CF 2 )-,-(OCF 2 CF 2 CF (CF 3 ))-,-(OCF 2 C (CF 3 ) 2 )-,-(OCF) (CF 3 ) CF (CF 3 ))-,-(OCF (C 2 F 5 ) CF 2 )-and (OCF 2 CF (C 2 F 5 ))-may be any of-, but preferably- (OCF 2 CF 2 CF 2 CF 2 )-.
- -(OC 3 F 6 )- may be any of-(OCF 2 CF 2 CF 2 )-,-(OCF (CF 3 ) CF 2 )-and (OCF 2 CF (CF 3 ))-.
- -(OC 2 F 4 )- may be any of-(OCF 2 CF 2 )-and (OCF (CF 3 ))-, but is preferably-(OCF 2 CF 2 )-.
- the perfluoro (poly) ether compound represented by the general formula (3) the compound represented by any of the following general formulas (3a) and (3b) (one or a mixture of two or more) is used. It may be).
- Rf 5 and Rf 6 are as described above; in equation (3a), b "is an integer of 1 or more and 100 or less; in equation (3b), a" and b “are independent of each other. Is an integer of 0 or more and 30 or less, and c "and d" are independently integers of 1 or more and 300 or less.
- the subscripts a ", b", c ", and d" are added and enclosed in parentheses. The order of existence of each repeating unit is arbitrary in the equation.
- the fluorine-containing oil may be a compound represented by the general formula Rf 3 -F (in the formula, Rf 3 is a C 5-16 perfluoroalkyl group). Further, it may be a chlorotrifluoroethylene oligomer.
- the fluorine-containing oil may have an average molecular weight of 500 to 10000.
- the molecular weight of the fluorinated oil can be measured using GPC.
- the fluorine-containing oil may be contained in, for example, 0 to 50% by mass, preferably 0 to 30% by mass, and more preferably 0 to 5% by mass with respect to the surface treatment agent of the present disclosure.
- the surface treatment agents of the present disclosure are substantially free of fluorinated oils.
- substantially free of fluorinated oil means that it may contain no fluorinated oil or may contain a very small amount of fluorinated oil.
- the average molecular weight of the fluorine-containing oil may be larger than the average molecular weight of the fluoropolyether group-containing silane compound.
- the average molecular weight of the fluorine-containing oil may be smaller than the average molecular weight of the fluoropolyether group-containing silane compound.
- the fluorine-containing oil contributes to improving the surface slipperiness of the layer formed by the surface treatment agent of the present disclosure.
- the silicone oil for example, a linear or cyclic silicone oil having a siloxane bond of 2,000 or less can be used.
- the linear silicone oil may be a so-called straight silicone oil or a modified silicone oil.
- the straight silicone oil include dimethyl silicone oil, methyl phenyl silicone oil, and methyl hydrogen silicone oil.
- the modified silicone oil include straight silicone oils modified with alkyl, aralkyl, polyether, higher fatty acid ester, fluoroalkyl, amino, epoxy, carboxyl, alcohol and the like.
- Examples of the cyclic silicone oil include cyclic dimethylsiloxane oil.
- such silicone oil is used, for example, with respect to a total of 100 parts by mass (in the case of two or more kinds, the total of these, the same applies hereinafter) of the above-mentioned fluoropolyether group-containing silane compound of the present disclosure. It may be contained in an amount of 0 to 300 parts by mass, preferably 50 to 200 parts by mass.
- Silicone oil contributes to improving the surface slipperiness of the surface treatment layer.
- the alcohols include alcohols having 1 to 6 carbon atoms which may be substituted with one or more fluorine atoms, for example, methanol, ethanol, iso-propanol, tert-butanol, CF 3 CH 2 OH, and the like. CF 3 CF 2 CH 2 OH, (CF 3 ) 2 CHOH can be mentioned.
- the alcohol is preferably 2,2,3,3,3-pentafluoro-1-propanol or 2,2,2-trifluoroethanol.
- the catalyst examples include acids (for example, acetic acid, trifluoroacetic acid, etc.), bases (for example, ammonia, triethylamine, diethylamine, etc.), transition metals (for example, Ti, Ni, Sn, etc.) and the like.
- acids for example, acetic acid, trifluoroacetic acid, etc.
- bases for example, ammonia, triethylamine, diethylamine, etc.
- transition metals for example, Ti, Ni, Sn, etc.
- the catalyst promotes hydrolysis and dehydration condensation of the fluoropolyether group-containing silane compound of the present disclosure, and promotes the formation of a layer formed by the surface treatment agent of the present disclosure.
- Examples of other components include tetraethoxysilane, methyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, methyltriacetoxysilane, and the like.
- the surface treatment agent of the present disclosure can be made into pellets by impregnating a porous substance such as a porous ceramic material, a metal fiber, for example, steel wool into a cotton-like solidified material.
- the pellet can be used, for example, for vacuum deposition.
- the surface treatment agent of the present disclosure contains, for example, a trace amount of impurities such as Pt, Rh, Ru, 1,3-divinyltetramethyldisiloxane, triphenylphosphine, NaCl, KCl, and a condensate of silane. obtain.
- the article of the present disclosure includes a base material and a layer (surface treatment layer) formed from the surface treatment agent of the present disclosure on the surface of the base material.
- the substrates that can be used in the present disclosure are, for example, glass, resin (natural or synthetic resin, for example, general plastic material may be used), metal, ceramics, semiconductor (silicon, germanium, etc.), fiber (woven fabric, non-woven fabric, etc.). Etc.), fur, leather, wood, ceramics, stones, etc., building materials, sanitary goods, and any suitable material.
- the material constituting the surface of the base material may be a material for the optical member, for example, glass or transparent plastic.
- some layer (or film), such as a hard coat layer or an antireflection layer may be formed on the surface (outermost layer) of the base material.
- the antireflection layer either a single-layer antireflection layer or a multi-layer antireflection layer may be used.
- the article to be manufactured is an optical glass component for a touch panel
- a thin film using a transparent electrode such as indium tin oxide (ITO) or zinc oxide is provided on a part of the surface of the base material (glass).
- the base material may be an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), an atomized film layer, a hard coating film layer, a polarizing film, a phase difference film, etc., depending on the specific specifications thereof.
- the base material may be an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), an atomized film layer, a hard coating film layer, a polarizing film, a phase difference film, etc., depending on the specific specifications thereof.
- I-CON decorative frame layer
- an atomized film layer atomized film layer
- a hard coating film layer a polarizing film
- a phase difference film etc.
- the shape of the base material is not particularly limited, and may be, for example, a plate, a film, or any other form. Further, the surface region of the base material on which the surface treatment layer should be formed may be at least a part of the surface of the base material, and may be appropriately determined according to the use and specific specifications of the article to be manufactured.
- the base material may be made of a material having a hydroxyl group originally at least on its surface.
- a material having a hydroxyl group include glass, and examples thereof include metals (particularly base metals) in which a natural oxide film or a thermal oxide film is formed on the surface, ceramics, semiconductors, and the like.
- the hydroxyl group is introduced on the surface of the base material by applying some pretreatment to the base material. Can be increased or increased. Examples of such pretreatment include plasma treatment (for example, corona discharge) and ion beam irradiation.
- Plasma treatment can introduce or increase hydroxyl groups on the surface of the base material, and can also be suitably used for cleaning the surface of the base material (removing foreign substances and the like).
- an interfacial adsorbent having a carbon-carbon unsaturated bond group is previously subjected to a monomolecular film on the surface of a substrate by an LB method (Langmuir-Blogget method), a chemisorption method, or the like. Examples thereof include a method of forming the morphology and then cleaving the unsaturated bond in an atmosphere containing oxygen, nitrogen and the like.
- the substrate may be such that at least its surface portion is made of a silicone compound having another reactive group, for example, one or more Si—H groups, or a material containing an alkoxysilane. ..
- the base material is glass.
- glass sapphire glass, soda lime glass, alkaline aluminum silicate glass, borosilicate glass, non-alkali glass, crystal glass and quartz glass are preferable, and chemically strengthened soda lime glass and chemically strengthened alkaline aluminum silicate glass are used. And chemically bonded borosilicate glass are particularly preferred.
- the article of the present disclosure forms a layer of the above-mentioned surface treatment agent of the present disclosure on the surface of the above-mentioned base material, and post-treats this layer as necessary, whereby a layer is formed from the above-mentioned surface treatment agent of the present disclosure. It can be manufactured by forming.
- the layer formation of the surface treatment agent of the present disclosure can be carried out by applying the surface treatment agent to the surface of the base material so as to cover the surface.
- the coating method is not particularly limited. For example, a wet coating method and a dry coating method can be used.
- wet coating methods include dip coating, spin coating, flow coating, spray coating, roll coating, gravure coating and similar methods.
- dry coating methods include vapor deposition (usually vacuum deposition), sputtering, CVD and similar methods.
- vapor deposition method usually a vacuum vapor deposition method
- CVD method include plasma-CVD, optical CVD, thermal CVD and similar methods.
- the surface treatment agents of the present disclosure may be diluted with a solvent before being applied to the surface of the substrate.
- a solvent for example, perfluoroaliphatic hydrocarbons having 5-12 carbon atoms (eg, perfluorohexanes, perfluoromethylcyclohexanes and).
- Perfluoro-1,3-dimethylcyclohexane Perfluoro-1,3-dimethylcyclohexane); polyfluoroaromatic hydrocarbons (eg, bis (trifluoromethyl) benzene); polyfluoroaliphatic hydrocarbons (eg, C6 F 13 CH 2 CH 3 ( eg, Asahi Glass) Asahiclean (registered trademark) AC-6000) manufactured by Asahiclean Co., Ltd., 1,1,2,2,3,3,4-heptafluorocyclopentane (for example, Zeorora (registered trademark) H manufactured by Nippon Zeon Co., Ltd.); Hydrofluoroether (HFE) (for example, perfluoropropylmethyl ether (C 3 F 7 OCH 3 )) (for example, Novec 7000 manufactured by Sumitomo 3M Co., Ltd.), perfluorobutyl methyl ether (C 4 F 9 OCH 3 ).
- HFE Hydrofluor
- Novec TM 7100 manufactured by Sumitomo 3M Co., Ltd. Perfluorobutyl ethyl ether ( C4 F 9 OC 2 H 5 ) (for example, Novec TM 7200 manufactured by Sumitomo 3M Co., Ltd.), Perfluoro Alkyl perfluoroalkyl ethers such as hexylmethyl ether (C 2 F 5 CF (OCH 3 ) C 3 F 7 ) (for example, Novec TM 7300 manufactured by Sumitomo 3M Co., Ltd.) (perfluoroalkyl group and alkyl group are direct).
- CF 3 CH 2 OCF 2 CHF 2 eg, Asahiclean® AE-3000 manufactured by Asahi Glass Co., Ltd.
- solvents can be used alone or It can be used as a mixture of two or more kinds.
- a hydrocarbon ether is preferable, and a perfluorobutylmethyl ether (C4 F 9 OCH 3 ) and / or a perfluorobutyl ethyl ether ( C 4 F 9 OC 2 H ) is preferable. 5 ) is particularly preferable.
- the surface treatment agent of the present disclosure may be subjected to the dry coating method as it is, or may be diluted with the above-mentioned solvent and then subjected to the dry coating method.
- the layer formation of the surface treatment agent is preferably carried out so that the surface treatment agent of the present disclosure is present in the layer together with a catalyst for hydrolysis and dehydration condensation.
- the catalyst may be added to the diluted solution of the surface treatment agent of the present disclosure immediately after diluting the surface treatment agent of the present disclosure with a solvent and immediately before applying to the surface of the substrate.
- the surface treatment agent of the present disclosure to which a catalyst is added is subjected to thin-film deposition (usually, vacuum-film deposition) as it is, or the surface treatment agent of the present disclosure to which a catalyst is added to a metal porous body such as iron or copper.
- a vapor deposition (usually vacuum vapor deposition) treatment may be performed using a pellet-like substance impregnated with.
- any suitable acid or base can be used as the catalyst.
- the acid catalyst for example, acetic acid, formic acid, trifluoroacetic acid and the like can be used.
- the base catalyst for example, ammonia, organic amines and the like can be used.
- the surface-treated layer contained in the article of the present disclosure has both high wear durability.
- the surface treatment layer has water repellency, oil repellency, and stain resistance (for example, prevents fingerprints and the like from adhering), depending on the composition of the surface treatment agent used. It may have waterproofness (preventing water from entering electronic parts, etc.), surface slipperiness (or lubricity, such as wiping off stains such as fingerprints, and excellent tactile sensation to fingers), chemical resistance, and the like. It can be suitably used as a functional thin film.
- the present disclosure further relates to an optical material having the surface-treated layer as the outermost layer.
- optical material examples include optical materials related to displays and the like as exemplified below, as well as a wide variety of optical materials: for example, a cathode line tube (CRT; for example, a personal computer monitor), a liquid crystal display, a plasma display, and an organic EL.
- CTR cathode line tube
- LCD liquid crystal display
- plasma display a plasma display
- organic EL organic EL.
- Display such as display, inorganic thin film EL dot matrix display, rear projection type display, fluorescent display tube (VFD), electric field emission display (FED; Field Mission Display) or a protective plate for those displays, or an antireflection film on their surface. Processed.
- the article of the present disclosure is not particularly limited, but may be an optical member.
- optical components include: lenses such as eyeglasses; front protective plates for displays such as DVDs and LCDs, antireflection plates, polarizing plates, anti-glare plates; for devices such as mobile phones and mobile information terminals. Touch panel sheet; Blu-ray (registered trademark) disc, DVD disc, CD-R, MO, etc. Optical disc surface; Optical fiber; Clock display surface, etc.
- the article of the present disclosure may be a medical device or a medical material. Further, the article having a layer obtained by the present disclosure may be an automobile interior / exterior member. Examples of exterior materials include: windows, light covers, external camera covers. Examples of interior materials include: instrument panel covers, navigation system touch panels, decorative interior materials.
- the thickness of the above layer is not particularly limited.
- the thickness of the layer is preferably in the range of 1 to 50 nm, 1 to 30 nm, preferably 1 to 15 nm from the viewpoint of optical performance, wear durability and antifouling property.
- the end point of the reaction was that the chemical shift of -CF 2- at the carbonyl group ⁇ position of CF 3- (OCF 2 CF 2 ) m- (OCF 2 ) n -COOH was shifted to a low magnetic field by 19 F-NMR, and 1 It was confirmed by 1 H-NMR that the methylene proton at the ⁇ -position of the amino group of diallylamine was shifted to a low magnetic field.
- the lower phase which was separated by adding 1N-hydrochloric acid to the reaction solution, was washed with water, dried over magnesium sulfate, and concentrated. The obtained concentrate was dissolved in perfluorohexane and washed with acetone three times to obtain 4.0 g of a mixture containing the polyether group-containing compound (A) and the polyether group-containing compound (A').
- Synthesis Example 2 4.0 g of the mixture obtained in Synthesis Example 1 was dissolved in 5 ml of 1,3-bis (trifluoromethyl) benzene, 0.01 g of triacetoxymethylsilane, and 1,3-divinyl-1,1,3. After adding 0.06 ml of a xylene solution containing 2% of the Pt complex of 3-tetramethyldisiloxane, 1.5 g of trichlorosilane was charged, heated to 60 ° C., and stirred for 4 hours.
- the operation was carried out to obtain 4.0 g of a mixture containing a polyether group-containing compound (F) and a polyether group-containing compound (F') (however, the content of the polyether group-containing compound (F') was 7 mol%). ..
- the operation was carried out to obtain 3.7 g of a mixture containing a polyether group-containing compound (H) and a polyether group-containing compound (H') (however, the content of the polyether group-containing compound (H') was 7 mol%). ..
- Example 1 The mixture containing the polyether group-containing compound (B) and the polyether group-containing compound (B') obtained in Synthesis Example 2 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (1) was prepared by dissolving it in Novec HFE-7200).
- Example 2 The mixture containing the polyether group-containing compound (C) and the polyether group-containing compound (C') obtained in Synthesis Example 3 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (2) was prepared by dissolving it in Novec HFE-7200).
- Example 3 The mixture containing the polyether group-containing compound (D) and the polyether group-containing compound (D') obtained in Synthesis Example 4 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (3) was prepared by dissolving it in Novec HFE-7200).
- Example 4 The mixture containing the polyether group-containing compound (E) and the polyether group-containing compound (E') obtained in Synthesis Example 5 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (4) was prepared by dissolving it in Novec HFE-7200).
- Example 5 The mixture containing the polyether group-containing compound (F) and the polyether group-containing compound (F') obtained in Synthesis Example 6 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (5) was prepared by dissolving it in Novec HFE-7200).
- Example 6 The mixture containing the polyether group-containing compound (G) and the polyether group-containing compound (G') obtained in Synthesis Example 7 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (6) was prepared by dissolving it in Novec HFE-7200).
- Example 7 The mixture containing the polyether group-containing compound (H) and the polyether group-containing compound (H') obtained in Synthesis Example 8 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (7) was prepared by dissolving it in Novec HFE-7200).
- Example 8 The mixture containing the polyether group-containing compound (I) and the polyether group-containing compound (I') obtained in Synthesis Example 9 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (8) was prepared by dissolving it in Novec HFE-7200).
- Example 9 The mixture containing the polyether group-containing compound (J) and the polyether group-containing compound (J') obtained in Synthesis Example 10 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (9) was prepared by dissolving it in Novec HFE-7200).
- Example 10 The mixture containing the polyether group-containing compound (K) and the polyether group-containing compound (K') obtained in Synthesis Example 11 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (10) was prepared by dissolving it in Novec HFE-7200).
- Example 11 The mixture containing the polyether group-containing compound (L) and the polyether group-containing compound (L') obtained in Synthetic Example 12 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (11) was prepared by dissolving it in Novec HFE-7200).
- Example 12 The mixture containing the polyether group-containing compound (M) and the polyether group-containing compound (M') obtained in Synthesis Example 13 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (12) was prepared by dissolving it in Novec HFE-7200).
- Example 13 The mixture containing the polyether group-containing compound (N) and the polyether group-containing compound (N') obtained in Synthesis Example 14 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (13) was prepared by dissolving it in Novec HFE-7200).
- Example 14 The mixture containing the polyether group-containing compound (O) and the polyether group-containing compound (O') obtained in Synthesis Example 15 is hydrofluoroether (manufactured by 3M) so as to have a concentration of 0.1% by mass.
- the surface treatment agent (14) was prepared by dissolving it in Novec HFE-7200).
- Example 2 The same procedure as in Example 2 was carried out except that the following control compounds (1) and (2) were used in place of the mixture containing the polyether group-containing compound (D) and the polyether group-containing compound (D'), respectively. Comparative surface treatment agents (1) and (2) were prepared.
- the static contact angle was measured by the following method using a fully automatic contact angle meter DropMaster 700 (manufactured by Kyowa Interface Science Co., Ltd.).
- the static contact angle was determined by dropping 2 ⁇ L of water from a microsyringe onto a horizontally placed substrate and taking a still image 1 second after the drop with a video microscope.
- Fingerprint adhesion and wiping property> (Fingerprint adhesion) A finger was pressed against a cured film formed by using a surface treatment agent or a comparative surface treatment agent, and the ease with which fingerprints were attached was visually determined. The evaluation was judged based on the following criteria. A: Fingerprints are difficult to attach, or even if they are attached, fingerprints are not noticeable. B: There was little fingerprint adhesion, but the fingerprint was sufficiently confirmed. C: Fingerprints were attached as clearly as the untreated glass substrate.
- the contact angle of the cured film formed by using the surface treatment agents (1) to (14) did not decrease even when wiped with ethanol.
- the contact angle of the cured film formed by using the comparative surface treatment agents (1) and (2) was reduced by wiping with ethanol. It is considered that this is because the cured film formed by the comparative surface treatment agent (1) or (2) has poor chemical resistance (that is, durability against a solvent).
- the fluoropolyether group-containing compound of the present disclosure can be suitably used for forming a surface treatment layer on the surface of various substrates, particularly optical members that are required to have friction durability.
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Abstract
Description
[1] 下記式(1)又は(2):
[式中:
RF1は、Rf1-RF-Oq-であり;
RF2は、-Rf2 p-RF-Oq-であり;
Rf1は、1個又はそれ以上のフッ素原子により置換されていてもよいC1-16アルキル基であり;
Rf2は、1個又はそれ以上のフッ素原子により置換されていてもよいC1-6アルキレン基であり;
RFは、それぞれ独立して、2価のフルオロポリエーテル基であり;
pは、0又は1であり;
qは、それぞれ独立して、0又は1であり;
R1は、それぞれ独立して、-R3-(OR2)m-On-R4-R5であり;
R2は、各出現においてそれぞれ独立して、C1-6アルキレン基であり;
mは、2~10の整数であり;
nは、0又は1であり;
R3は、単結合又はC1-6アルキレン基であり;
R4は、単結合又はC1-6アルキレン基であり;
R5は、水素原子又はRSiであり;
RSiは、それぞれ独立して、水酸基又は加水分解性基が結合したSi原子を含む1価の基であり;
XAは、それぞれ独立して、単結合又は下記式:
-(X51)p5-
(式中:
X51は、各出現においてそれぞれ独立して、-O-、-S-、o-、m-もしくはp-フェニレン基、-C(O)O-、-OC(O)-、-Si(R53)2-、-(Si(R53)2O)m5-Si(R53)2-、-CONR54-、-NR54CO-、-O-CONR54-、-NR54CO-O-、-NR54-及び-(CH2)n5-からなる群から選択される基であり、
R53は、各出現においてそれぞれ独立して、フェニル基、C1-6アルキル基又はC1-6アルコキシ基であり、
R54は、各出現においてそれぞれ独立して、水素原子、フェニル基又はC1-6アルキル基であり、
m5は、各出現においてそれぞれ独立して、1~100の整数であり、
n5は、各出現において、それぞれ独立して、1~20の整数であり、
p5は、1~10の整数である。)
で表される基であり;
XBは、それぞれ独立して、単結合又は下記式:
-(X61)p6-
(式中:
X61は、各出現においてそれぞれ独立して、-O-、-S-、o-、m-もしくはp-フェニレン基、-C(O)O-、-OC(O)-、-Si(R63)2-、-(Si(R63)2O)m6-Si(R63)2-、-CONR64-、-NR64CO-、-O-CONR64-、-NR64CO-O-、-NR64-及び-(CH2)n6-からなる群から選択される基であり、
R63は、各出現においてそれぞれ独立して、フェニル基、C1-6アルキル基又はC1-6アルコキシ基であり、
R64は、各出現においてそれぞれ独立して、水素原子、フェニル基又はC1-6アルキル基であり、
m6は、各出現においてそれぞれ独立して、1~100の整数であり、
n6は、各出現において、それぞれ独立して、1~20の整数であり、
p6は、1~10の整数である。)
で表される基である。]
で表されるフルオロポリエーテル基含有シラン化合物。
[2] Rf1は、各出現においてそれぞれ独立して、C1-16パーフルオロアルキル基であり、
Rf2は、各出現においてそれぞれ独立して、C1-6パーフルオロアルキレン基である、
上記[1]に記載のフルオロポリエーテル基含有シラン化合物。
[3] RFは、各出現においてそれぞれ独立して、式:
-(OC6F12)a-(OC5F10)b-(OC4F8)c-(OC3RFa 6)d-(OC2F4)e-(OCF2)f-
[式中、RFaは、各出現においてそれぞれ独立して、水素原子、フッ素原子又は塩素原子であり、
a、b、c、d、e及びfは、それぞれ独立して、0~200の整数であって、a、b、c、d、e及びfの和は1以上であり、a、b、c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意であり、ただし、すべてのRFaが水素原子又は塩素原子である場合、a、b、c、e及びfの少なくとも1つは、1以上である。]
で表される基である、上記[1]又は[2]に記載のフルオロポリエーテル基含有シラン化合物。
[4] RFaは、フッ素原子である、上記[3]に記載のフルオロポリエーテル基含有シラン化合物。
[5] RFは、各出現においてそれぞれ独立して、下記式(f1)、(f2)、(f3)、(f4)又は(f5):
-(OC3F6)d-(OC2F4)e- (f1)
[式中、dは1~200の整数であり、eは0又は1である。]、
-(OC4F8)c-(OC3F6)d-(OC2F4)e-(OCF2)f- (f2)
[式中、c及びdは、それぞれ独立して、0~30の整数であり;
e及びfは、それぞれ独立して、1~200の整数であり;
c、d、e及びfの和は、10~200の整数であり;
添字c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。]、
-(R6-R7)g- (f3)
[式中、R6は、OCF2又はOC2F4であり;
R7は、OC2F4、OC3F6、OC4F8、OC5F10及びOC6F12から選択される基であるか、あるいは、これらの基から選択される2又は3つの基の組み合わせであり;
gは、2~100の整数である。]、
-(OC6F12)a-(OC5F10)b-(OC4F8)c-(OC3F6)d-(OC2F4)e-(OCF2)f- (f4)
[式中、eは、1以上200以下の整数であり、a、b、c、d及びfは、それぞれ独立して0以上200以下の整数であって、a、b、c、d、e及びfの和は少なくとも1であり、また、a、b、c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。]
-(OC6F12)a-(OC5F10)b-(OC4F8)c-(OC3F6)d-(OC2F4)e-(OCF2)f- (f5)
[式中、fは、1以上200以下の整数であり、a、b、c、d及びeは、それぞれ独立して0以上200以下の整数であって、a、b、c、d、e及びfの和は少なくとも1であり、また、a、b、c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。]
で表される基である、上記[1]~[4]のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。
[6] R5は、水素原子である、上記[1]~[5]のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。
[7] R5は、RSiである、上記[1]~[4]のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。
[8] RSiは、それぞれ独立して、下記式(S1)、(S2)、(S3)、(S4)又は(S5):
R11は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
R12は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
n1は、(SiR11 n1R12 3-n1)単位毎にそれぞれ独立して、0~3の整数であり;
X11は、各出現においてそれぞれ独立して、単結合又は2価の有機基であり;
R13は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
tは、各出現においてそれぞれ独立して、2以上の整数であり;
R14は、各出現においてそれぞれ独立して、水素原子、ハロゲン原子又は-X11-SiR11 n1R12 3-n1であり;
R15は、各出現においてそれぞれ独立して、単結合、酸素原子、炭素数1~6のアルキレン基又は炭素数1~6のアルキレンオキシ基であり;
Ra1は、各出現においてそれぞれ独立して、-Z1-SiR21 p1R22 q1R23 r1であり;
Z1は、各出現においてそれぞれ独立して、酸素原子又は2価の有機基であり;
R21は、各出現においてそれぞれ独立して、-Z1’-SiR21’ p1’R22’ q1’R23’ r1’であり;
R22は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
R23は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
p1は、各出現においてそれぞれ独立して、0~3の整数であり;
q1は、各出現においてそれぞれ独立して、0~3の整数であり;
r1は、各出現においてそれぞれ独立して、0~3の整数であり;
p1、q1及びr1の合計は3であり;
Z1’は、各出現においてそれぞれ独立して、酸素原子又は2価の有機基であり;
R21’は、各出現においてそれぞれ独立して、-Z1”-SiR22” q1”R23” r1”であり;
R22’は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
R23’は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
p1’は、各出現においてそれぞれ独立して、0~3の整数であり;
q1’は、各出現においてそれぞれ独立して、0~3の整数であり;
r1’は、各出現においてそれぞれ独立して、0~3の整数であり;
p1’、q1’及びr1’の合計は3であり;
Z1”は、各出現においてそれぞれ独立して、酸素原子又は2価の有機基であり;
R22”は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
R23”は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
q1”は、各出現においてそれぞれ独立して、0~3の整数であり;
r1”は、各出現においてそれぞれ独立して、0~3の整数であり;
q1”及びr1”の合計は3であり;
Rb1は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
Rc1は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
k1は、各出現においてそれぞれ独立して、1~3の整数であり;
l1は、各出現においてそれぞれ独立して、0~3の整数であり;
m1は、各出現においてそれぞれ独立して、0~3の整数であり;
k1、l1及びm1の合計は3であり;
Rd1は、各出現においてそれぞれ独立して、-Z2-CR31 p2R32 q2R33 r2であり;
Z2は、各出現においてそれぞれ独立して、単結合、酸素原子又は2価の有機基であり;
R31は、各出現においてそれぞれ独立して、-Z2’-CR32’ q2’R33’ r2’であり;
R32は、各出現においてそれぞれ独立して、-Z3-SiR34 n2R35 3-n2であり;
R33は、各出現においてそれぞれ独立して、水素原子、水酸基又は1価の有機基であり;
p2は、各出現においてそれぞれ独立して、0~3の整数であり;
q2は、各出現においてそれぞれ独立して、0~3の整数であり;
r2は、各出現においてそれぞれ独立して、0~3の整数であり;
p2、q2及びr2の合計は3であり;
Z2’は、各出現においてそれぞれ独立して、単結合、酸素原子又は2価の有機基であり;
R32’は、各出現においてそれぞれ独立して、-Z3-SiR34 n2R35 3-n2であり;
R33’は、各出現においてそれぞれ独立して、水素原子、水酸基又は1価の有機基であり;
q2’は、各出現においてそれぞれ独立して、0~3の整数であり;
r2’は、各出現においてそれぞれ独立して、0~3の整数であり;
q2’及びr2’の合計は3であり;
Z3は、各出現においてそれぞれ独立して、単結合、酸素原子又は2価の有機基であり;
R34は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
R35は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
n2は、各出現においてそれぞれ独立して、0~3の整数であり;
Re1は、各出現においてそれぞれ独立して、-Z3-SiR34 n2R35 3-n2であり;
Rf1は、各出現においてそれぞれ独立して、水素原子、水酸基又は1価の有機基であり;
k2は、各出現においてそれぞれ独立して、0~3の整数であり;
l2は、各出現においてそれぞれ独立して、0~3の整数であり;
m2は、各出現においてそれぞれ独立して、0~3の整数であり;
k2、l2及びm2の合計は3であり;
Rg1及びRh1は、各出現においてそれぞれ独立して、-Z4-SiR11 n1R12 3-n1、-Z4-SiRa1 k1Rb1 l1Rc1 m1、又は-Z4-CRd1 k2Re1 l2Rf1 m2であり;
Z4は、各出現においてそれぞれ独立して、単結合、酸素原子又は2価の有機基であり;
ただし、式(S1)、(S2)、(S3)、(S4)及び(S5)中、水酸基又は加水分解性基が結合したSi原子が少なくとも1つ存在する。]
で表される基である、上記[1]~[7]のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。
[9] XBに結合するRSiは、式(S3)又は(S4)で表される基である、上記[8]に記載のフルオロポリエーテル基含有シラン化合物。
[10] R1におけるRSiは、式(S2)で表される基である、上記[8]又は[9]に記載のフルオロポリエーテル基含有シラン化合物。
[11] XAは、それぞれ独立して、単結合又は下記式:
-(R51’)p5’-(X51’)q5’-(R51’)p5”-
(式中:
R51’は、それぞれ独立して、C1-6アルキレン基であり、
X51’は、Oであり、
p5’は、0又は1であり、
p5”は、0又は1であり、
q5’は、0又は1であり、
ここに、p5’及びp5”の少なくとも一方は1である。)
で表される基であり;
XBは、それぞれ独立して、単結合又は下記式:
-(R61’)p6’-(X61’)q6’-(R61’)p6”-
(式中:
R61’は、それぞれ独立して、C1-6アルキレン基であり、
X61’は、Oであり、
p6’は、0又は1であり、
p6”は、0又は1であり、
q6’は、0又は1であり、
ここに、p6’及びp6”の少なくとも一方は1である。)
で表される基である、上記[1]~[10]のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。
[12] XAは、単結合であり、XBは、C1-6アルキレン基である、上記[1]~[11]のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。
[13] 上記[1]~[12]のいずれか1項に記載のフルオロ(ポリ)エーテル基含有シラン化合物を含有する、表面処理剤。
[14] 含フッ素オイル、シリコーンオイル、及び触媒から選択される1種又はそれ以上の他の成分をさらに含有する、上記[13]に記載の表面処理剤。
[15] さらに溶媒を含む、上記[13]又は[14]に記載の表面処理剤。
[16] 防汚性コーティング剤又は防水性コーティング剤として使用される、上記[13]~[15]のいずれか1項に記載の表面処理剤。
[17] 基材と、該基材の表面に、上記[1]~[12]のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物又は上記[13]~[16]のいずれかに記載の表面処理剤より形成された層とを含む物品。
[18] 光学部材である、上記[17]に記載の物品。
本開示のフルオロポリエーテル基含有シラン化合物は、下記式(1)又は(2):
[式中:
RF1は、Rf1-RF-Oq-であり;
RF2は、-Rf2 p-RF-Oq-であり;
Rf1は、1個又はそれ以上のフッ素原子により置換されていてもよいC1-16アルキル基であり;
Rf2は、1個又はそれ以上のフッ素原子により置換されていてもよいC1-6アルキレン基であり;
RFは、それぞれ独立して、2価のフルオロポリエーテル基であり;
pは、0又は1であり;
qは、各出現においてそれぞれ独立して、0又は1であり;
R1は、それぞれ独立して、-R3-(OR2)m-On-R4-R5であり;
R2は、各出現においてそれぞれ独立して、C1-6アルキレン基であり;
mは、2~10の整数であり;
nは、0又は1であり;
R3は、単結合又はC1-6アルキレン基であり;
R4は、単結合又はC1-6アルキレン基であり;
R5は、水素原子又はRSiであり;
RSiは、それぞれ独立して、水酸基又は加水分解性基が結合したSi原子を含む1価の基であり;
XAは、それぞれ独立して、単結合又は下記式:
-(X51)p5-
(式中:
X51は、各出現においてそれぞれ独立して、-O-、-S-、o-、m-もしくはp-フェニレン基、-C(O)O-、-OC(O)-、-Si(R53)2-、-(Si(R53)2O)m5-Si(R53)2-、-CONR54-、-NR54CO-、-O-CONR54-、-NR54CO-O-、-NR54-及び-(CH2)n5-からなる群から選択される基であり、
R53は、各出現においてそれぞれ独立して、フェニル基、C1-6アルキル基又はC1-6アルコキシ基であり、
R54は、各出現においてそれぞれ独立して、水素原子、フェニル基又はC1-6アルキル基であり、
m5は、各出現においてそれぞれ独立して、1~100の整数であり、
n5は、各出現において、それぞれ独立して、1~20の整数であり、
p5は、1~10の整数である。)
で表される基であり;
XBは、それぞれ独立して、単結合又は下記式:
-(X61)p6-
(式中:
X61は、各出現においてそれぞれ独立して、-O-、-S-、o-、m-もしくはp-フェニレン基、-C(O)O-、-OC(O)-、-Si(R63)2-、-(Si(R63)2O)m6-Si(R63)2-、-CONR64-、-NR64CO-、-O-CONR64-、-NR64CO-O-、-NR64-及び-(CH2)n6-からなる群から選択される基であり、
R63は、各出現においてそれぞれ独立して、フェニル基、C1-6アルキル基又はC1-6アルコキシ基であり、
R64は、各出現においてそれぞれ独立して、水素原子、フェニル基又はC1-6アルキル基であり、
m6は、各出現においてそれぞれ独立して、1~100の整数であり、
n6は、各出現において、それぞれ独立して、1~20の整数であり、
p6は、1~10の整数である。)
で表される基である。]
で表されるフルオロポリエーテル基含有シラン化合物である。
-(OC6F12)a-(OC5F10)b-(OC4F8)c-(OC3RFa 6)d-(OC2F4)e-(OCF2)f-
[式中:
RFaは、各出現においてそれぞれ独立して、水素原子、フッ素原子又は塩素原子であり、
a、b、c、d、e及びfは、それぞれ独立して、0~200の整数であって、a、b、c、d、e及びfの和は1以上である。a、b、c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。ただし、すべてのRFaが水素原子又は塩素原子である場合、a、b、c、e及びfの少なくとも1つは、1以上である。]
で表される基である。
-(OC3F6)d-(OC2F4)e- (f1)
[式中、dは、1~200の整数であり、eは0又は1である。];
-(OC4F8)c-(OC3F6)d-(OC2F4)e-(OCF2)f- (f2)
[式中、c及びdは、それぞれ独立して0以上30以下の整数であり、e及びfは、それぞれ独立して1以上200以下の整数であり、
c、d、e及びfの和は2以上であり、
添字c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。];
-(R6-R7)g- (f3)
[式中、R6は、OCF2又はOC2F4であり、
R7は、OC2F4、OC3F6、OC4F8、OC5F10及びOC6F12から選択される基であるか、あるいは、これらの基から独立して選択される2又は3つの基の組み合わせであり、
gは、2~100の整数である。];
-(OC6F12)a-(OC5F10)b-(OC4F8)c-(OC3F6)d-(OC2F4)e-(OCF2)f- (f4)
[式中、eは、1以上200以下の整数であり、a、b、c、d及びfは、それぞれ独立して0以上200以下の整数であって、また、a、b、c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。]
-(OC6F12)a-(OC5F10)b-(OC4F8)c-(OC3F6)d-(OC2F4)e-(OCF2)f- (f5)
[式中、fは、1以上200以下の整数であり、a、b、c、d及びeは、それぞれ独立して0以上200以下の整数であって、また、a、b、c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。]
R11、R12、R13、X11、及びn1は、上記式(S1)の記載と同意義であり;
t1及びt2は、各出現においてそれぞれ独立して、1以上の整数、好ましくは1~10の整数、より好ましくは2~10の整数、例えば1~5の整数又は2~5の整数であり;
t1及びt2を付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。]
-(X51)p5-
[式中:
X51は、各出現においてそれぞれ独立して、-O-、-S-、o-、m-もしくはp-フェニレン基、-C(O)O-、-OC(O)-、-Si(R53)2-、-(Si(R53)2O)m5-Si(R53)2-、-CONR54-、-NR54CO-、-O-CONR54-、-NR54CO-O-、-NR54-及び-(CH2)n5-からなる群から選択される基であり、
R53は、各出現においてそれぞれ独立して、フェニル基、C1-6アルキル基又はC1-6アルコキシ基であり、好ましくはフェニル基又はC1-6アルキル基であり、より好ましくはメチル基であり、
R54は、各出現においてそれぞれ独立して、水素原子、フェニル基又はC1-6アルキル基(好ましくはメチル基)であり、
m5は、各出現においてそれぞれ独立して、1~100の整数、好ましくは1~20の整数であり、
n5は、各出現においてそれぞれ独立して、1~20の整数、好ましくは1~6の整数、より好ましくは1~3の整数であり、
p5は、1~10の整数、好ましくは1~5の整数、より好ましくは1~3の整数である。]
で表される基である。なお、XAの説明において、各基の左側が式中のRF1又はRF2に結合し、右側がCONR1の炭素原子に結合する。
-(R51’)p5’-(X51’)q5’-(R51’)p5”-
(式中:
R51’は、それぞれ独立して、C1-6アルキレン基であり、
X51’は、Oであり、
p5’は、0又は1であり、
p5”は、0又は1であり、
q5’は、0又は1であり、
ここに、p5’及びp5”の少なくとも一方は1である。)
で表される基である。
-(X61)p6-
[式中:
X61は、各出現においてそれぞれ独立して、-O-、-S-、o-、m-もしくはp-フェニレン基、-C(O)O-、-OC(O)-、-Si(R63)2-、-(Si(R63)2O)m6-Si(R63)2-、-CONR64-、-NR64CO-、-O-CONR64-、-NR64CO-O-、-NR64-及び-(CH2)n6-からなる群から選択される基であり、
R63は、各出現においてそれぞれ独立して、フェニル基、C1-6アルキル基又はC1-6アルコキシ基であり、好ましくはフェニル基又はC1-6アルキル基であり、より好ましくはメチル基であり、
R64は、各出現においてそれぞれ独立して、水素原子、フェニル基又はC1-6アルキル基(好ましくはメチル基)であり、
m6は、各出現においてそれぞれ独立して、1~100の整数、好ましくは1~20の整数であり、
n6は、各出現においてそれぞれ独立して、1~20の整数、好ましくは1~6の整数、より好ましくは1~3の整数であり、
p6は、1~10の整数、好ましくは1~5の整数、より好ましくは1~3の整数である。]
で表される基である。なお、XBの説明において、各基の左側が式中のCONR1の窒素原子に結合し、右側がRSiに結合する。
-(R61’)p6’-(X61’)q6’-(R61’)p6”-
(式中:
R61’は、それぞれ独立して、C1-6アルキレン基であり、
X61’は、Oであり、
p6’は、0又は1であり、
p6”は、0又は1であり、
q6’は、0又は1であり、
ここに、p6’及びp6”の少なくとも一方は1である。)
で表される基である。
で表される化合物と、式(5):
R1は、式(1)及び(2)の記載と同意義であり;
R25は、C又はSiであり;
XB’は、単結合、又は2価の有機基である。]
で表される化合物を反応させて、式(1b)又は(2b):
で表されるパーフルオロポリエーテル基含有アリル化合物を得る。
HSiR26 3 (6)
[式中、R26は、それぞれ独立して、水素原子、1価の有機基、水酸基、加水分解性基、又はハロゲン原子である。]
で表される化合物と反応させ、適宜、Si原子に加水分解性基を導入することにより、式(1)又は(2)で表される化合物を得ることができる。
Rf5-(OC4F8)a’-(OC3F6)b’-(OC2F4)c’-(OCF2)d’-Rf6 ・・・(3)
式中、Rf5は、1個又はそれ以上のフッ素原子により置換されていてもよい炭素数1~16アルキル基(好ましくは、C1―16のパーフルオロアルキル基)を表し、Rf6は、1個又はそれ以上のフッ素原子により置換されていてもよい炭素数1~16アルキル基(好ましくは、C1-16パーフルオロアルキル基)、フッ素原子又は水素原子を表し、Rf5及びRf6は、より好ましくは、それぞれ独立して、C1-3パーフルオロアルキル基である。
a’、b’、c’及びd’は、ポリマーの主骨格を構成するパーフルオロ(ポリ)エーテルの4種の繰り返し単位数をそれぞれ表し、互いに独立して0以上300以下の整数であって、a’、b’、c’及びd’の和は少なくとも1、好ましくは1~300、より好ましくは20~300である。添字a’、b’、c’又はd’を付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。これら繰り返し単位のうち、-(OC4F8)-は、-(OCF2CF2CF2CF2)-、-(OCF(CF3)CF2CF2)-、-(OCF2CF(CF3)CF2)-、-(OCF2CF2CF(CF3))-、-(OC(CF3)2CF2)-、-(OCF2C(CF3)2)-、-(OCF(CF3)CF(CF3))-、-(OCF(C2F5)CF2)-及び(OCF2CF(C2F5))-のいずれであってもよいが、好ましくは-(OCF2CF2CF2CF2)-である。-(OC3F6)-は、-(OCF2CF2CF2)-、-(OCF(CF3)CF2)-及び(OCF2CF(CF3))-のいずれであってもよく、好ましくは-(OCF2CF2CF2)-である。-(OC2F4)-は、-(OCF2CF2)-及び(OCF(CF3))-のいずれであってもよいが、好ましくは-(OCF2CF2)-である。
Rf5-(OCF2CF2CF2)b”-Rf6 ・・・(3a)
Rf5-(OCF2CF2CF2CF2)a”-(OCF2CF2CF2)b”-(OCF2CF2)c”-(OCF2)d”-Rf6 ・・・(3b)
これら式中、Rf5及びRf6は上記の通りであり;式(3a)において、b”は1以上100以下の整数であり;式(3b)において、a”及びb”は、それぞれ独立して0以上30以下の整数であり、c”及びd”はそれぞれ独立して1以上300以下の整数である。添字a”、b”、c”、d”を付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。
CF3-(OCF2CF2)m-(OCF2)n-COOH(m≒21、n≒35)とHOCOCF2-(OCF2CF2)m-(OCF2)n-COOH(m≒21、n≒35)の混合物4.0g(ただし、HOCOCF2-(OCF2CF2)m-(OCF2)n-COOHの含有量は11mol%)を、1,3-ビス(トリフルオロメチル)ベンゼン6.0gに溶解し氷冷した。該溶液にチオニルクロライド3.0gを滴下した後、N,N-ジメチルホルムアミド0.3mgをさらに加え60℃で2時間撹拌した。この反応液からチオニルクロライドを留去した後、氷冷下、N-(3,6-ジオキサヘプチル)-2,2-ジ(2-プロペニル)-4-ペンチルアミン0.6g及びN,N-ジイソプロピルエチルアミン1.0gを加え室温で3時間撹拌した。反応の終点は19F-NMRによってCF3-(OCF2CF2)m-(OCF2)n-COOHのカルボニル基α位の-CF2-のケミカルシフトが低磁場にシフトしたこと、及び1H-NMRによって、ジアリルアミンのアミノ基α位のメチレンプロトンが低磁場にシフトしたことにより確認した。反応液に1N-塩酸を加え分液した下相を水洗し、硫酸マグネシウムを用いて乾燥、濃縮した。得られた濃縮物をパーフルオロヘキサンに溶解しアセトンで3回洗浄することによりポリエーテル基含有化合物(A)及びポリエーテル基含有化合物(A’)を含む混合物4.0gを得た。
ポリエーテル基含有化合物(A’):
(なお、パーフルオロポリエーテル基において、平均組成としては(OCF2CF2CF2CF2)単位及び(OCF2CF2CF2)単位が微量含まれていたが省略した。)
合成例1で得られた混合物4.0gを、1,3-ビス(トリフルオロメチル)ベンゼン5mlに溶解し、トリアセトキシメチルシラン0.01g、及び1,3-ジビニル-1,1,3,3-テトラメチルジシロキサンのPt錯体2%を含むキシレン溶液0.06mlを加えた後、トリクロロシラン1.5gを仕込み、60℃に加熱し、4時間撹拌した。その後、得られた溶液から減圧下で揮発分を留去した後、メタノール0.1g及びオルトギ酸トリメチル3.0gの混合溶液を加えた後、60℃に加熱し、3時間撹拌した。その後、精製を行うことにより、末端にトリメトキシシリル基を有する下記のポリエーテル基含有化合物(B)及びポリエーテル基含有化合物(B’)を含む混合物3.9g(ただし、ポリエーテル基含有化合物(B’)の含有量は11mol%)を得た。
ポリエーテル基含有化合物(B’):
(なお、パーフルオロポリエーテル基において、平均組成としては(OCF2CF2CF2CF2)単位及び(OCF2CF2CF2)単位が微量含まれていたが省略した。)
CF3-(OCF2CF2)m-(OCF2)n-COOH(m≒28、n≒26)及びHOCOCF2-(OCF2CF2)m-(OCF2)n-COOH(m≒28、n≒26)を含む混合物4.0g(ただし、HOCOCF2-(OCF2CF2)m-(OCF2)n-COOHの含有量は7mol%)を用いた以外は合成例1~2と同様の操作を行い、ポリエーテル基含有化合物(C)及びポリエーテル基含有化合物(C’)を含む混合物3.9g(ただし、ポリエーテル基含有化合物(C’)の含有量は7mol%)を得た。
ポリエーテル基含有化合物(C’):
(なお、パーフルオロポリエーテル基において、平均組成としては(OCF2CF2CF2CF2)単位及び(OCF2CF2CF2)単位が微量含まれていたが省略した。)
CF3CF2CF2-(OCF2CF2CF2)m―OCF2CF2COOH(m≒25)及びHOCOCF2CF2-(OCF2CF2CF2)m-OCF2CF2COOH(m≒25)を含む混合物4.2g(ただし、HOCOCF2CF2-(OCF2CF2CF2)m-OCF2CF2COOHの含有量は5mol%)を用いた以外は、合成例1~2と同様の操作を行い、ポリエーテル基含有化合物(D)及びポリエーテル基含有化合物(D’)を含む混合物4.2g(ただし、ポリエーテル基含有化合物(D’)の含有量は5mol%)を得た。
N-(3,6-ジオキサヘプチル)-2,2-ジ(2-プロペニル)-4-ペンチルアミンの代わりに、N-(3,6-ジオキサヘプチル)-2-(2-プロペニル)-4-ペンチルアミンを用いた以外は、合成例1~2と同様の操作を行い、ポリエーテル基含有化合物(E)及びポリエーテル基含有化合物(E’)を含む混合物3.8g(ただし、ポリエーテル基含有化合物(E’)の含有量は11mol%)を得た。
ポリエーテル基含有化合物(E’):
(なお、パーフルオロポリエーテル基において、平均組成としては(OCF2CF2CF2CF2)単位及び(OCF2CF2CF2)単位が微量含まれていたが省略した。)
CF3-(OCF2CF2)m-(OCF2)n-COOH(m≒28、n≒26)及びHOCOCF2-(OCF2CF2)m-(OCF2)n-COOH(m≒28、n≒26)を含む混合物4.0g(ただし、HOCOCF2-(OCF2CF2)m-(OCF2)n-COOHの含有量は7mol%)を用いた以外は合成例4と同様の操作を行い、ポリエーテル基含有化合物(F)、ポリエーテル基含有化合物(F’)を含む混合物4.0g(ただし、ポリエーテル基含有化合物(F’)の含有量は7mol%)を得た。
ポリエーテル基含有化合物(F’):
(なお、パーフルオロポリエーテル基において、平均組成としては(OCF2CF2CF2CF2)単位及び(OCF2CF2CF2)単位が微量含まれていたが省略した。)
N-(3,6-ジオキサヘプチル)-2,2-ジ(2-プロペニル)-4-ペンチルアミンの代わりに、N-(3,6,9-トリオキサデシル)-2,2-ジ(2-プロペニル)-4-ペンチルアミンを用いた以外は、合成例1~2と同様の操作を行い、ポリエーテル基含有化合物(G)及びポリエーテル基含有化合物(G’)を含む混合物3.9g(ただし、ポリエーテル基含有化合物(G’)の含有量は11mol%)を得た。
ポリエーテル基含有化合物(G’):
(なお、パーフルオロポリエーテル基において、平均組成としては(OCF2CF2CF2CF2)単位及び(OCF2CF2CF2)単位が微量含まれていたが省略した。)
CF3-(OCF2CF2)m-(OCF2)n-COOH(m≒28、n≒26)及びHOCOCF2-(OCF2CF2)m-(OCF2)n-COOH(m≒28、n≒26)を含む混合物4.0g(ただし、HOCOCF2-(OCF2CF2)m-(OCF2)n-COOHの含有量は7mol%)を用いた以外は合成例7と同様の操作を行い、ポリエーテル基含有化合物(H)、ポリエーテル基含有化合物(H’)を含む混合物3.7g(ただし、ポリエーテル基含有化合物(H’)の含有量は7mol%)を得た。
ポリエーテル基含有化合物(H’):
(なお、パーフルオロポリエーテル基において、平均組成としては(OCF2CF2CF2CF2)単位及び(OCF2CF2CF2)単位が微量含まれていたが省略した。)
CF3CF2CF2-(OCF2CF2CF2)m―OCF2CF2COOH(m≒25)及びHOCOCF2CF2-(OCF2CF2CF2)m-OCF2CF2COOH(m≒25)を含む混合物4.2g(ただし、HOCOCF2CF2-(OCF2CF2CF2)m-OCF2CF2COOHの含有量は5mol%)を用いた以外は、合成例8と同様の操作を行い、ポリエーテル基含有化合物(I)及びポリエーテル基含有化合物(I’)を含む混合物4.1g(ただし、ポリエーテル基含有化合物(I’)の含有量は5mol%)を得た。
N-(3,6-ジオキサヘプチル)-2,2-ジ(2-プロペニル)-4-ペンチルアミンの代わりに、N-(3,6,9,11-テトラオキサトリデシル)-2,2-ジ(2-プロペニル)-4-ペンチルアミンを用いた以外は合成例1~2と同様の操作を行い、ポリエーテル基含有化合物(J)及びポリエーテル基含有化合物(J’)を含む混合物3.6g(ただし、ポリエーテル基含有化合物(J’)の含有量は11mol%)を得た。
ポリエーテル基含有化合物(J’):
(なお、パーフルオロポリエーテル基において、平均組成としては(OCF2CF2CF2CF2)単位及び(OCF2CF2CF2)単位が微量含まれていたが省略した。)
CF3-(OCF2CF2)m-(OCF2)n-COOH(m≒28、n≒26)及びHOCOCF2-(OCF2CF2)m-(OCF2)n-COOH(m≒28、n≒26)を含む混合物4.0g(ただし、HOCOCF2-(OCF2CF2)m-(OCF2)n-COOHの含有量は7mol%)を用いた以外は、合成例10と同様の操作を行い、ポリエーテル基含有化合物(K)及びポリエーテル基含有化合物(K’)を含む混合物3.9g(ただし、ポリエーテル基含有化合物(K’)の含有量は7mol%)を得た。
ポリエーテル基含有化合物(K’):
(なお、パーフルオロポリエーテル基において、平均組成としては(OCF2CF2CF2CF2)単位及び(OCF2CF2CF2)単位が微量含まれていたが省略した。)
CF3CF2CF2-(OCF2CF2CF2)m―OCF2COOH(m≒25)及びHOCOCF2-(OCF2CF2CF2)m-OCF2COOH(m≒25)を含む混合物4.2g(ただし、HOCOCF2-(OCF2CF2CF2)m-OCF2COOHの含有量は5mol%)を用いた以外は、合成例11と同様の操作を行い、ポリエーテル基含有化合物(L)及びポリエーテル基含有化合物(L’)を含む混合物4.0g(ただし、ポリエーテル基含有化合物(L’)の含有量は5mol%)を得た。
N-(3,6-ジオキサヘプチル)-2,2-ジ(2-プロペニル)-4-ペンチルアミンの代わりに、N-(3-オキサヘキセ-5-イル)-2,2-ジ(2-プロペニル)-4-ペンチルアミンを用いた以外は、合成例1~2と同様の操作を行い、ポリエーテル基含有化合物(M)及びポリエーテル基含有化合物(M’)を含む混合物3.5g(ただし、ポリエーテル基含有化合物(M’)の含有量は11mol%)を得た。
ポリエーテル基含有化合物(M’):
(なお、パーフルオロポリエーテル基において、平均組成としては(OCF2CF2CF2CF2)単位及び(OCF2CF2CF2)単位が微量含まれていたが省略した。)
CF3-(OCF2CF2)m-(OCF2)n-COOH(m≒28、n≒26)及びHOCOCF2-(OCF2CF2)m-(OCF2)n-COOH(m≒28、n≒26)を含む混合物4.0g(ただし、HOCOCF2-(OCF2CF2)m-(OCF2)n-COOHの含有量は7mol%)を用いた以外は、合成例13と同様の操作を行い、ポリエーテル基含有化合物(N)及びポリエーテル基含有化合物(N’)を含む混合物3.8g(ただし、ポリエーテル基含有化合物(N’)の含有量は7mol%)を得た。
ポリエーテル基含有化合物(N’):
(なお、パーフルオロポリエーテル基において、平均組成としては(OCF2CF2CF2CF2)単位及び(OCF2CF2CF2)単位が微量含まれていたが省略した。)
CF3CF2CF2-(OCF2CF2CF2)m―OCF2COOH(m≒25)及びHOCOCF2-(OCF2CF2CF2)m-OCF2COOH(m≒25)を含む混合物4.2g(ただし、HOCOCF2-(OCF2CF2CF2)m-OCF2COOHの含有量は5mol%)を用いた以外は、合成例13と同様の操作を行い、ポリエーテル基含有化合物(O)及びポリエーテル基含有化合物(O’)を含む混合物4.2g(ただし、ポリエーテル基含有化合物(O’)の含有量は5mol%)を得た。
上記合成例2で得られたポリエーテル基含有化合物(B)及びポリエーテル基含有化合物(B’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(1)を調製した。
上記合成例3で得られたポリエーテル基含有化合物(C)及びポリエーテル基含有化合物(C’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(2)を調製した。
上記合成例4で得られたポリエーテル基含有化合物(D)及びポリエーテル基含有化合物(D’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(3)を調製した。
上記合成例5で得られたポリエーテル基含有化合物(E)及びポリエーテル基含有化合物(E’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(4)を調製した。
上記合成例6で得られたポリエーテル基含有化合物(F)及びポリエーテル基含有化合物(F’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(5)を調製した。
上記合成例7で得られたポリエーテル基含有化合物(G)及びポリエーテル基含有化合物(G’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(6)を調製した。
上記合成例8で得られたポリエーテル基含有化合物(H)及びポリエーテル基含有化合物(H’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(7)を調製した。
上記合成例9で得られたポリエーテル基含有化合物(I)及びポリエーテル基含有化合物(I’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(8)を調製した。
上記合成例10で得られたポリエーテル基含有化合物(J)及びポリエーテル基含有化合物(J’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(9)を調製した。
上記合成例11で得られたポリエーテル基含有化合物(K)及びポリエーテル基含有化合物(K’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(10)を調製した。
上記合成例12で得られたポリエーテル基含有化合物(L)及びポリエーテル基含有化合物(L’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(11)を調製した。
上記合成例13で得られたポリエーテル基含有化合物(M)及びポリエーテル基含有化合物(M’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(12)を調製した。
上記合成例14で得られたポリエーテル基含有化合物(N)及びポリエーテル基含有化合物(N’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(13)を調製した。
上記合成例15で得られたポリエーテル基含有化合物(O)及びポリエーテル基含有化合物(O’)を含む混合物を、濃度0.1質量%になるように、ハイドロフルオロエーテル(スリーエム社製、ノベックHFE-7200)に溶解させて、表面処理剤(14)を調製した。
ポリエーテル基含有化合物(D)及びポリエーテル基含有化合物(D’)を含む混合物の代わりに、それぞれ、下記対照化合物(1)及び(2)を用いた以外は実施例2と同様に行い、比較表面処理剤(1)及び(2)を調製した。
静的接触角は全自動接触角計DropMaster700(協和界面科学社製)を用いて次の方法で測定した。
静的接触角は、水平に置いた基板にマイクロシリンジから水を2μL滴下し、滴下1秒後の静止画をビデオマイクロスコープで撮影することにより求めた。
表面処理剤(1)~(14)及び比較表面処理剤(1)~(2)を、それぞれスピンコーターを用いて、化学強化ガラス(コーニング社製、「ゴリラ」ガラス、厚さ0.7mm)上に塗布した。スピンコートの条件は、300回転/分で3秒間、2000回転/分で30秒であった。塗布後のガラスを、大気下、恒温槽内で150℃30分間加熱し、硬化膜を形成した。
得られた硬化膜の特性を以下のように評価した。
(初期評価)
まず、初期評価として、硬化膜形成後、その表面に未だ何も触れていない状態で、水の静的接触角を測定した。
(エタノール拭き後の評価)
次に、上記硬化膜を、エタノールを十分に染み込ませたキムワイプ(商品名。十條キンバリー(株)製)を用いて5往復拭いた後、乾燥させた。乾燥後の硬化膜の水の静的接触角を測定した。
(指紋付着性)
表面処理剤又は比較表面処理剤を用いて形成された硬化膜に指を押し付け、指紋の付きやすさを目視で判定した。評価は、次の基準に基づいて判断した。
A:指紋が付きにくいか、付いても指紋が目立たなかった。
B:指紋の付着が少ないが、その指紋を充分に確認できた。
C:未処理のガラス基板と同程度に明確に指紋が付着した。
上記の指紋付着性試験後、付着した指紋をキムワイプ(商品名。十條キンバリー(株)製)で5往復拭き取り、付着した指紋の拭き取りやすさを目視で判定した。評価は次の基準に基づいて判断した。
A:指紋を完全に拭き取ることができた。
B:指紋の拭取り跡が残った。
C:指紋の拭取り跡が拡がり、除去することが困難であった。
得られた硬化膜の耐摩擦性を以下のように評価した。
ラビングテスター(新東科学社製)を用いて、下記条件で2500回擦る毎に耐水接触角を測定し、10000回もしくは100度未満となるまで試験を続けた。試験環境条件は25℃、湿度40%RHであった。
消しゴム:Raber Eraser(Minoan社製)
接地面積:6mmφ
移動距離(片道):30mm
移動速度:3,600mm/分
荷重:1kg/6mmφ
Claims (18)
- 下記式(1)又は(2):
[式中:
RF1は、Rf1-RF-Oq-であり;
RF2は、-Rf2 p-RF-Oq-であり;
Rf1は、1個又はそれ以上のフッ素原子により置換されていてもよいC1-16アルキル基であり;
Rf2は、1個又はそれ以上のフッ素原子により置換されていてもよいC1-6アルキレン基であり;
RFは、それぞれ独立して、2価のフルオロポリエーテル基であり;
pは、0又は1であり;
qは、それぞれ独立して、0又は1であり;
R1は、それぞれ独立して、-R3-(OR2)m-On-R4-R5であり;
R2は、各出現においてそれぞれ独立して、C1-6アルキレン基であり;
mは、2~10の整数であり;
nは、0又は1であり;
R3は、単結合又はC1-6アルキレン基であり;
R4は、単結合又はC1-6アルキレン基であり;
R5は、水素原子又はRSiであり;
RSiは、それぞれ独立して、水酸基又は加水分解性基が結合したSi原子を含む1価の基であり;
XAは、それぞれ独立して、単結合又は下記式:
-(X51)p5-
(式中:
X51は、各出現においてそれぞれ独立して、-O-、-S-、o-、m-もしくはp-フェニレン基、-C(O)O-、-OC(O)-、-Si(R53)2-、-(Si(R53)2O)m5-Si(R53)2-、-CONR54-、-NR54CO-、-O-CONR54-、-NR54CO-O-、-NR54-及び-(CH2)n5-からなる群から選択される基であり、
R53は、各出現においてそれぞれ独立して、フェニル基、C1-6アルキル基又はC1-6アルコキシ基であり、
R54は、各出現においてそれぞれ独立して、水素原子、フェニル基又はC1-6アルキル基であり、
m5は、各出現においてそれぞれ独立して、1~100の整数であり、
n5は、各出現において、それぞれ独立して、1~20の整数であり、
p5は、1~10の整数である。)
で表される基であり;
XBは、それぞれ独立して、単結合又は下記式:
-(X61)p6-
(式中:
X61は、各出現においてそれぞれ独立して、-O-、-S-、o-、m-もしくはp-フェニレン基、-C(O)O-、-OC(O)-、-Si(R63)2-、-(Si(R63)2O)m6-Si(R63)2-、-CONR64-、-NR64CO-、-O-CONR64-、-NR64CO-O-、-NR64-及び-(CH2)n6-からなる群から選択される基であり、
R63は、各出現においてそれぞれ独立して、フェニル基、C1-6アルキル基又はC1-6アルコキシ基であり、
R64は、各出現においてそれぞれ独立して、水素原子、フェニル基又はC1-6アルキル基であり、
m6は、各出現においてそれぞれ独立して、1~100の整数であり、
n6は、各出現において、それぞれ独立して、1~20の整数であり、
p6は、1~10の整数である。)
で表される基である。]
で表されるフルオロポリエーテル基含有シラン化合物。 - Rf1は、各出現においてそれぞれ独立して、C1-16パーフルオロアルキル基であり、
Rf2は、各出現においてそれぞれ独立して、C1-6パーフルオロアルキレン基である、
請求項1に記載のフルオロポリエーテル基含有シラン化合物。 - RFは、各出現においてそれぞれ独立して、式:
-(OC6F12)a-(OC5F10)b-(OC4F8)c-(OC3RFa 6)d-(OC2F4)e-(OCF2)f-
[式中、RFaは、各出現においてそれぞれ独立して、水素原子、フッ素原子又は塩素原子であり、
a、b、c、d、e及びfは、それぞれ独立して、0~200の整数であって、a、b、c、d、e及びfの和は1以上であり、a、b、c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意であり、ただし、すべてのRFaが水素原子又は塩素原子である場合、a、b、c、e及びfの少なくとも1つは、1以上である。]
で表される基である、請求項1又は2に記載のフルオロポリエーテル基含有シラン化合物。 - RFaは、フッ素原子である、請求項3に記載のフルオロポリエーテル基含有シラン化合物。
- RFは、各出現においてそれぞれ独立して、下記式(f1)、(f2)、(f3)、(f4)又は(f5):
-(OC3F6)d-(OC2F4)e- (f1)
[式中、dは1~200の整数であり、eは0又は1である。]、
-(OC4F8)c-(OC3F6)d-(OC2F4)e-(OCF2)f- (f2)
[式中、c及びdは、それぞれ独立して、0~30の整数であり;
e及びfは、それぞれ独立して、1~200の整数であり;
c、d、e及びfの和は、10~200の整数であり;
添字c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。]、
-(R6-R7)g- (f3)
[式中、R6は、OCF2又はOC2F4であり;
R7は、OC2F4、OC3F6、OC4F8、OC5F10及びOC6F12から選択される基であるか、あるいは、これらの基から選択される2又は3つの基の組み合わせであり;
gは、2~100の整数である。]、
-(OC6F12)a-(OC5F10)b-(OC4F8)c-(OC3F6)d-(OC2F4)e-(OCF2)f- (f4)
[式中、eは、1以上200以下の整数であり、a、b、c、d及びfは、それぞれ独立して0以上200以下の整数であって、a、b、c、d、e及びfの和は少なくとも1であり、また、a、b、c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。]
-(OC6F12)a-(OC5F10)b-(OC4F8)c-(OC3F6)d-(OC2F4)e-(OCF2)f- (f5)
[式中、fは、1以上200以下の整数であり、a、b、c、d及びeは、それぞれ独立して0以上200以下の整数であって、a、b、c、d、e及びfの和は少なくとも1であり、また、a、b、c、d、e又はfを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。]
で表される基である、請求項1~4のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。 - R5は、水素原子である、請求項1~5のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。
- R5は、RSiである、請求項1~5のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。
- RSiは、それぞれ独立して、下記式(S1)、(S2)、(S3)、(S4)又は(S5):
R11は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
R12は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
n1は、(SiR11 n1R12 3-n1)単位毎にそれぞれ独立して、0~3の整数であり;
X11は、各出現においてそれぞれ独立して、単結合又は2価の有機基であり;
R13は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
tは、各出現においてそれぞれ独立して、2以上の整数であり;
R14は、各出現においてそれぞれ独立して、水素原子、ハロゲン原子又は-X11-SiR11 n1R12 3-n1であり;
R15は、各出現においてそれぞれ独立して、単結合、酸素原子、炭素数1~6のアルキレン基又は炭素数1~6のアルキレンオキシ基であり;
Ra1は、各出現においてそれぞれ独立して、-Z1-SiR21 p1R22 q1R23 r1であり;
Z1は、各出現においてそれぞれ独立して、酸素原子又は2価の有機基であり;
R21は、各出現においてそれぞれ独立して、-Z1’-SiR21’ p1’R22’ q1’R23’ r1’であり;
R22は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
R23は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
p1は、各出現においてそれぞれ独立して、0~3の整数であり;
q1は、各出現においてそれぞれ独立して、0~3の整数であり;
r1は、各出現においてそれぞれ独立して、0~3の整数であり;
p1、q1及びr1の合計は3であり;
Z1’は、各出現においてそれぞれ独立して、酸素原子又は2価の有機基であり;
R21’は、各出現においてそれぞれ独立して、-Z1”-SiR22” q1”R23” r1”であり;
R22’は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
R23’は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
p1’は、各出現においてそれぞれ独立して、0~3の整数であり;
q1’は、各出現においてそれぞれ独立して、0~3の整数であり;
r1’は、各出現においてそれぞれ独立して、0~3の整数であり;
p1’、q1’及びr1’の合計は3であり;
Z1”は、各出現においてそれぞれ独立して、酸素原子又は2価の有機基であり;
R22”は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
R23”は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
q1”は、各出現においてそれぞれ独立して、0~3の整数であり;
r1”は、各出現においてそれぞれ独立して、0~3の整数であり;
q1”及びr1”の合計は3であり;
Rb1は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
Rc1は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
k1は、各出現においてそれぞれ独立して、1~3の整数であり;
l1は、各出現においてそれぞれ独立して、0~3の整数であり;
m1は、各出現においてそれぞれ独立して、0~3の整数であり;
k1、l1及びm1の合計は3であり;
Rd1は、各出現においてそれぞれ独立して、-Z2-CR31 p2R32 q2R33 r2であり;
Z2は、各出現においてそれぞれ独立して、単結合、酸素原子又は2価の有機基であり;
R31は、各出現においてそれぞれ独立して、-Z2’-CR32’ q2’R33’ r2’であり;
R32は、各出現においてそれぞれ独立して、-Z3-SiR34 n2R35 3-n2であり;
R33は、各出現においてそれぞれ独立して、水素原子、水酸基又は1価の有機基であり;
p2は、各出現においてそれぞれ独立して、0~3の整数であり;
q2は、各出現においてそれぞれ独立して、0~3の整数であり;
r2は、各出現においてそれぞれ独立して、0~3の整数であり;
p2、q2及びr2の合計は3であり;
Z2’は、各出現においてそれぞれ独立して、単結合、酸素原子又は2価の有機基であり;
R32’は、各出現においてそれぞれ独立して、-Z3-SiR34 n2R35 3-n2であり;
R33’は、各出現においてそれぞれ独立して、水素原子、水酸基又は1価の有機基であり;
q2’は、各出現においてそれぞれ独立して、0~3の整数であり;
r2’は、各出現においてそれぞれ独立して、0~3の整数であり;
q2’及びr2’の合計は3であり;
Z3は、各出現においてそれぞれ独立して、単結合、酸素原子又は2価の有機基であり;
R34は、各出現においてそれぞれ独立して、水酸基又は加水分解性基であり;
R35は、各出現においてそれぞれ独立して、水素原子又は1価の有機基であり;
n2は、各出現においてそれぞれ独立して、0~3の整数であり;
Re1は、各出現においてそれぞれ独立して、-Z3-SiR34 n2R35 3-n2であり;
Rf1は、各出現においてそれぞれ独立して、水素原子、水酸基又は1価の有機基であり;
k2は、各出現においてそれぞれ独立して、0~3の整数であり;
l2は、各出現においてそれぞれ独立して、0~3の整数であり;
m2は、各出現においてそれぞれ独立して、0~3の整数であり;
k2、l2及びm2の合計は3であり;
Rg1及びRh1は、各出現においてそれぞれ独立して、-Z4-SiR11 n1R12 3-n1、-Z4-SiRa1 k1Rb1 l1Rc1 m1、又は-Z4-CRd1 k2Re1 l2Rf1 m2であり;
Z4は、各出現においてそれぞれ独立して、単結合、酸素原子又は2価の有機基であり;
ただし、式(S1)、(S2)、(S3)、(S4)及び(S5)中、水酸基又は加水分解性基が結合したSi原子が少なくとも1つ存在する。]
で表される基である、請求項1~7のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。 - XBに結合するRSiは、式(S3)又は(S4)で表される基である、請求項8に記載のフルオロポリエーテル基含有シラン化合物。
- R1におけるRSiは、式(S2)で表される基である、請求項8又は9に記載のフルオロポリエーテル基含有シラン化合物。
- XAは、それぞれ独立して、単結合又は下記式:
-(R51’)p5’-(X51’)q5’-(R51’)p5”-
(式中:
R51’は、それぞれ独立して、C1-6アルキレン基であり、
X51’は、Oであり、
p5’は、0又は1であり、
p5”は、0又は1であり、
q5’は、0又は1であり、
ここに、p5’及びp5”の少なくとも一方は1である。)
で表される基であり;
XBは、それぞれ独立して、単結合又は下記式:
-(R61’)p6’-(X61’)q6’-(R61’)p6”-
(式中:
R61’は、それぞれ独立して、C1-6アルキレン基であり、
X61’は、Oであり、
p6’は、0又は1であり、
p6”は、0又は1であり、
q6’は、0又は1であり、
ここに、p6’及びp6”の少なくとも一方は1である。)
で表される基である、請求項1~10のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。 - XAは、単結合であり、XBは、C1-6アルキレン基である、請求項1~11のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物。
- 請求項1~12のいずれか1項に記載のフルオロ(ポリ)エーテル基含有シラン化合物を含有する、表面処理剤。
- 含フッ素オイル、シリコーンオイル、及び触媒から選択される1種又はそれ以上の他の成分をさらに含有する、請求項13に記載の表面処理剤。
- さらに溶媒を含む、請求項13又は14に記載の表面処理剤。
- 防汚性コーティング剤又は防水性コーティング剤として使用される、請求項13~15のいずれか1項に記載の表面処理剤。
- 基材と、該基材の表面に、請求項1~12のいずれか1項に記載のフルオロポリエーテル基含有シラン化合物又は請求項13~16のいずれかに記載の表面処理剤より形成された層とを含む物品。
- 光学部材である、請求項17に記載の物品。
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JP2014005353A (ja) * | 2012-06-22 | 2014-01-16 | Nicca Chemical Co Ltd | パーフルオロポリエーテル変性シラン化合物、防汚性被膜形成用組成物、防汚性被膜、およびこの被膜を有する物品 |
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