JP2008115258A - 含フッ素ウレタン(メタ)アクリレート及び界面活性剤 - Google Patents
含フッ素ウレタン(メタ)アクリレート及び界面活性剤 Download PDFInfo
- Publication number
- JP2008115258A JP2008115258A JP2006298988A JP2006298988A JP2008115258A JP 2008115258 A JP2008115258 A JP 2008115258A JP 2006298988 A JP2006298988 A JP 2006298988A JP 2006298988 A JP2006298988 A JP 2006298988A JP 2008115258 A JP2008115258 A JP 2008115258A
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- carbon atoms
- fluorine
- meth
- acrylate
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 56
- 239000011737 fluorine Substances 0.000 title claims abstract description 56
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 47
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 239000000178 monomer Substances 0.000 claims description 46
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 22
- 125000005647 linker group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 15
- 229910052799 carbon Inorganic materials 0.000 abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 5
- 229920000728 polyester Polymers 0.000 description 37
- 238000000576 coating method Methods 0.000 description 24
- -1 acrylate compound Chemical class 0.000 description 23
- 239000011248 coating agent Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 20
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000003973 paint Substances 0.000 description 18
- 239000000463 material Substances 0.000 description 16
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- 229920001577 copolymer Polymers 0.000 description 14
- 239000008199 coating composition Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- YOSXAXYCARLZTR-UHFFFAOYSA-N prop-2-enoyl isocyanate Chemical compound C=CC(=O)N=C=O YOSXAXYCARLZTR-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 125000005702 oxyalkylene group Chemical group 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 239000012778 molding material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YAOJJEJGPZRYJF-UHFFFAOYSA-N 1-ethenoxyhexane Chemical compound CCCCCCOC=C YAOJJEJGPZRYJF-UHFFFAOYSA-N 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-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
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 230000003373 anti-fouling effect Effects 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
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- 238000013461 design Methods 0.000 description 2
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- 239000002612 dispersion medium Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
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- 238000009501 film coating Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- RDMHXWZYVFGYSF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese Chemical compound [Mn].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RDMHXWZYVFGYSF-LNTINUHCSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- KIHQZLPHVZKELA-UHFFFAOYSA-N 1,3-dibromopropan-2-ol Chemical compound BrCC(O)CBr KIHQZLPHVZKELA-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
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- HWCLMKDWXUGDKL-UHFFFAOYSA-N 1-ethenoxy-2-ethoxyethane Chemical compound CCOCCOC=C HWCLMKDWXUGDKL-UHFFFAOYSA-N 0.000 description 1
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- NSOAQRMLVFRWIT-UHFFFAOYSA-N 1-ethenoxydecane Chemical compound CCCCCCCCCCOC=C NSOAQRMLVFRWIT-UHFFFAOYSA-N 0.000 description 1
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- XXCVIFJHBFNFBO-UHFFFAOYSA-N 1-ethenoxyoctane Chemical compound CCCCCCCCOC=C XXCVIFJHBFNFBO-UHFFFAOYSA-N 0.000 description 1
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- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 1
- RWXMAAYKJDQVTF-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl prop-2-enoate Chemical compound OCCOCCOC(=O)C=C RWXMAAYKJDQVTF-UHFFFAOYSA-N 0.000 description 1
- DAVVKEZTUOGEAK-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound COCCOCCOC(=O)C(C)=C DAVVKEZTUOGEAK-UHFFFAOYSA-N 0.000 description 1
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- UIUSRIAANRCPGF-UHFFFAOYSA-N 2-(ethenoxymethyl)oxolane Chemical compound C=COCC1CCCO1 UIUSRIAANRCPGF-UHFFFAOYSA-N 0.000 description 1
- RCSBILYQLVXLJG-UHFFFAOYSA-N 2-Propenyl hexanoate Chemical compound CCCCCC(=O)OCC=C RCSBILYQLVXLJG-UHFFFAOYSA-N 0.000 description 1
- PZGMUSDNQDCNAG-UHFFFAOYSA-N 2-Propenyl octanoate Chemical compound CCCCCCCC(=O)OCC=C PZGMUSDNQDCNAG-UHFFFAOYSA-N 0.000 description 1
- TXHZNLCKXHJYNX-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOC(=O)C(C)=C TXHZNLCKXHJYNX-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
(I)下記一般式(I)の構造を有する含フッ素ウレタン(メタ)アクリレートモノマーは新規である。
(2)前記含フッ素ウレタン(メタ)アクリレートモノマーは、モノマー中のフッ素含量のコントロールが容易であり、また含フッ素基と炭化水素基を同時に導入することが容易である。
(3)前記含フッ素ウレタン(メタ)アクリレートモノマーは、後述する一般式(II)で表される含フッ素アルコールと下記一般式(III)で表されるイソシアネート(メタ)アクリレートとを反応させることで、効率よく製造できる。
(4)前記含フッ素ウレタン(メタ)アクリレートモノマーを重合性エチレン性不飽和モノマーの少なくとも1種類として用いて重合したフッ素含有ポリマーは、ポリマー型フッ素系界面活性剤として用いた場合、パーフルオロアルキル基の炭素数が少なくても、塗布性・レベリング性に優れる。
本発明は、このような知見に基づくものである。
下記一般式(II)
その他の単量体の具体的な例示は、Polymer Handbook 2nd ed., J. Brandrup, WileyInterscience (1975) Chapter 2, Page 1〜483に記載されている。
で表される単量体を挙げることができる。
〔化合物I−7の合成〕
メチルエチルケトン(MEK)200mlに化合物II−7(37.0g、0.06mol)、化合物III−1(8.47g、0.06mol、昭和電工株式会社製、カレンズAOI)、メトキノン0.05g及びジブチル錫ジラウ レート0.05gを加え、70℃で4時間反応した。減圧下MEKを留去し、目的物45.4g(0.06mol)を得た。
1H−NMR(CDCl3):δ2.37(4H、m)、3.50(2H、q)、3.63(4H、d)、3.76(4H、m)、4.25(2H、t)、4.99(1H、m)、5.11(1H、br)、5.86(1H、d)、6.12(1H、q)、6.43(1H、d)
〔化合物I−23の合成〕
化合物II−13(51.01g、0.05mol)、化合物III−4(7.76g、0.05mol、昭和電工株式会社製、カレンズMOI)、メトキノン0.05g及びジブチル錫ジラウレート0.05gを加え、85℃で6時間反応した。ガスクロマトグラフィーで原料の消失を確認し、目的物58.77g(0.05mol)を得た。その他の本発明に関わるウレタン(メタ)アクリレートは実施例1または2と同様に合成した。
含フッ素ウレタン(メタ)アクリレート(化合物I−8)30重量部とプロピレンオキシドを側鎖に持つモノアクリレート化合物(ブレンマーPP−1000、日本油脂株式会社製)70重量部を100重量部のMIBKに溶解し、7.5重量部の開始剤パーブチルO(日本油脂株式会社製)を加えた。その混合溶液を窒素雰囲気下で、100重量部のMIBK溶液に還流下2時間かけて滴下し、さらに17時間重合反応を行った。溶媒を減圧下留去し、共重合体を得た。この共重合体をゲルパーミエーショングラフ(以後GPCと略す)により分析した結果、重量平均分子量(Mw、東ソー(株)製標準ポリスチレン換算)=4700であった。この共重合体をフッ素系界面活性剤1とする。
分離カラム:東ソー(株)製TSKgelSuperH−RCを2本、東ソー(株)製TSKgelGMHHR−Nを4本使用。
カラム温度:40℃
移動層:和光純薬工業(株)製テトラヒドロフラン
流速:1.0ml/分
試料濃度:0.1重量%
試料注入量:100マイクロリットル
検出器:示差屈折計
以下のGPC分析も同様の条件で重量平均分子量(以下、Mwと記す。)の分析を行った。
実施例3で用いた含フッ素ウレタン(メタ)アクリレートを〔(C4F9CH2CH2OCH2)2CHOCOCH=CH2〕で示されるフッ素化アルキル基含有アクリレートに置き換えた以外は、実施例2と同様にしてフッ素系界面活性剤2を得た。GPCによるこの共重合体の重量平均分子量(ポリスチレン換算)はMw=4300であった。
実施例3で用いた含フッ素ウレタン(メタ)アクリレートを〔C8F17CH2CH2OCOCH=CH2〕で示されるフッ素化アルキル基含有アクリレートに置き換えた以外は、実施例2と同様にしてフッ素系界面活性剤3を得た。GPCによるこの共重合体の重量平均分子量(ポリスチレン換算)はMw=5100であった。
参考例1〔II−7の合成〕
2−(パーフルオロブチル)−エタノール58.1g(0.22mol)、エピクロロヒドリン9.3g(0.10mol)、トリエチルベンジルアンモニウムクロリド1.1g(0.005mol)及び水酸化ナトリウム6.0g(0.15mol)を65℃で6時間反応させた。反応終了後、ジイソピロピルエーテル100mlを加え不溶物をろ過した。ろ液を濃縮し、残分を減圧蒸留し無色油状の目的物37.0g(0.06mol)を得た。
1、3−ジブロモ−2−プロパノール50.0g(0.23mol)と2−(パーフルオロブチル)−エタンチオール128.5g(0.46mol)、及び炭酸カリウム31.7g(0.23mol)をMIBK460ml中で混合し、95℃で17時間反応させた。室温で4N塩酸70mlを滴下し、460mlの酢酸エチルを加え抽出した。有機層を減圧下濃縮し、残分を減圧蒸留しアルコール体122.0g(0.20mol)を得た(8mmHg、140℃)。
2−(2−ヘプタフルオロプロポキシ−1、1、2、3、3、3−ヘキサフルオロプロポキシ)−2、3、3、3−テトラフルオロプロパノール144.6g(0.30mol)とエピクロロヒドリン9.3g(0.10mol)、トリエチルベンジルアンモニウムクロリド1.1g(0.005mol)及び水酸化ナトリウム6.0g(0.15mol)を65℃で6時間反応させた。反応終了後、ジイソピロピルエーテル100mlを加え不溶物をろ過した。ろ液を濃縮し、残分を減圧蒸留し無色油状の目的物86.0g(0.084mol)を得た(7mmHg、143〜145℃)。
2−エチルヘキシルグリシジルエーテル18.6gと2−(パーフルオロオクチル)−エタンチオール38.2gを混合し、窒素雰囲気下110℃で3時間反応させて目的物を54.8g得た。
実施例3及び比較例1、2で得られたフッ素系界面活性剤1〜3を用いて、以下のような評価を実施した。その結果を表1に記載する。
フェノライトKA−105L(大日本インキ化学工業株式会社製)125重量部をプロピレングリコールモノエチルエーテルアセテート375重量部に溶解して樹脂溶液を調製し、これに合成例1〜3で得られたフッ素系界面活性剤を、該樹脂溶液中の固形分に対して0.4重量%の濃度になる様に添加し、0.1μmのPTFE製フィルターで精密濾過してレジスト組成物を調製した。このレジスト組成物を縦、横10×10cmのCr基板上に回転数500rpmでスピンコーティングした後、ホットプレート上にて90秒間加熱して溶媒を除去し、膜厚が1.5μmのレジスト膜を有する塗膜基板を得た。得られた塗膜の外観を目視にて評価した結果を表1に示す。
ストリエーション:ナトリウムランプを使用して、ストリエーションの発生状況を目視にて観察した。
○:ストリエーションの発生が認められないもの。
△:ストリエーションの発生がやや認められるもの。
×:ストリエーションの発生が顕著に認められるもの。
モヤムラ:ナトリウムランプを使用して、モヤムラの発生状況を目視にて観察した。
○:モヤムラの発生が認められないもの。
△:モヤムラの発生がやや認められるもの。
×:モヤムラの発生が顕著に認められるもの。
チャック跡:ナトリウムランプを使用して、チャック跡の発生状況を目視にて観察した。
○:チャック跡の発生が認められないもの。
△:チャック跡の発生がやや認められるもの。
×:チャック跡の発生が顕著に認められるもの。
Claims (7)
- 下記一般式(I)で表される含フッ素ウレタン(メタ)アクリレート。
(構造式(c)中のR4は、炭素原子数1〜6のアルキル基を表す。) - 前記連結基Aが−CH2−CH2−である請求項1記載の含フッ素ウレタン(メタ)アクリレート。
- 前記一般式(I)中のR2がR1と同一である請求項1又は2記載の含フッ素ウレタン(メタ)アクリレート。
- R1がCnF2n+1基(n=1〜6の整数)、CnF2n+1CH2CH2基(n=1〜6の整数)、またはC3F7O(CF(CF3)CF2O)mCF(CF3)CH2基(m=0〜5の整数)である請求項3記載の含フッ素ウレタン(メタ)アクリレート。
- R1がC4F9CH2CH2基、C6F13CH2CH2基、C3F7OCF(CF3)CF2OCF(CF3)CH2基、C3F7O(CF(CF3)CF2O)2CF(CF3)CH2基である請求項3記載の含フッ素ウレタン(メタ)アクリレート。
- 請求項1〜5の何れか1つに記載の含フッ素ウレタン(メタ)アクリレートを重合性エチレン性不飽和モノマー類の必須成分として重合して得られる含フッ素ポリマー界面活性剤。
- 下記一般式(II)
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