JP6733831B2 - 含フッ素活性エネルギー線硬化性樹脂、撥液剤、これを含む樹脂組成物及び硬化膜 - Google Patents
含フッ素活性エネルギー線硬化性樹脂、撥液剤、これを含む樹脂組成物及び硬化膜 Download PDFInfo
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- JP6733831B2 JP6733831B2 JP2019557072A JP2019557072A JP6733831B2 JP 6733831 B2 JP6733831 B2 JP 6733831B2 JP 2019557072 A JP2019557072 A JP 2019557072A JP 2019557072 A JP2019557072 A JP 2019557072A JP 6733831 B2 JP6733831 B2 JP 6733831B2
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- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011146 organic particle Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- WCAOBJJSISYNMN-UHFFFAOYSA-N oxetane;terephthalic acid Chemical compound C1COC1.C1COC1.OC(=O)C1=CC=C(C(O)=O)C=C1 WCAOBJJSISYNMN-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- CDQJAQUVBFYJGR-UHFFFAOYSA-N phenyl 2-(2-phenoxycarbonylprop-2-enoxymethyl)prop-2-enoate Chemical compound C=1C=CC=CC=1OC(=O)C(=C)COCC(=C)C(=O)OC1=CC=CC=C1 CDQJAQUVBFYJGR-UHFFFAOYSA-N 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical compound O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 229940099800 pigment red 48 Drugs 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000001008 quinone-imine dye Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- STZCRXQWRGQSJD-UHFFFAOYSA-N sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-N 0.000 description 1
- ZKDDJTYSFCWVGS-UHFFFAOYSA-M sodium;diethoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].CCOP([S-])(=S)OCC ZKDDJTYSFCWVGS-UHFFFAOYSA-M 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- WNQPPENQFWLADQ-UHFFFAOYSA-J tetrasodium;4-hydroxy-5-[[4-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]carbamoylamino]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(N=NC3=C(C)C=C(C(=C3)OC)NC(=O)NC3=CC(C)=C(N=NC=4C5=C(O)C=C(C=C5C=C(C=4)S([O-])(=O)=O)S([O-])(=O)=O)C=C3OC)=CC(S([O-])(=O)=O)=CC2=C1 WNQPPENQFWLADQ-UHFFFAOYSA-J 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical class CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 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
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- VRVDFJOCCWSFLI-UHFFFAOYSA-K trisodium 3-[[4-[(6-anilino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(c3cccc(c3c2)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O VRVDFJOCCWSFLI-UHFFFAOYSA-K 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/142—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Materials For Photolithography (AREA)
- Polyethers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
Description
少なくとも一つの、前記(A)以外の2価のフェノール性水酸基含有化合物(B)の残基及び/又は2価のカルボン酸(C)の残基と、を有し、
それらが下記構造式(1)
で表される連結基で結合されてなる構造単位を有し、
且つ1分子中に含まれる前記構造式(1)で表される連結基のうち少なくとも一つは重合性基を有する1価の有機基(x1)であることを特徴とする含フッ素活性エネルギー線硬化性樹脂及び撥液剤、これを含む樹脂組成物及びその硬化膜を提供するものである。
両末端が水酸基であって水素原子の少なくとも1つがフッ素原子に置換されたアルキレン鎖(但し、前記アルキレン鎖はエーテル性の酸素原子を有するものを含む。)(A)とジカルボン酸無水物(E)との反応物の残基と
少なくとも一つの、前記(A)以外の2価の水酸基含有化合物(F)の残基と、を有し、
それらが下記構造式(1)
で表される連結基で結合されてなる構造単位を有し、
且つ1分子中に含まれる前記構造式(1)で表される連結基のうち少なくとも一つは重合性基を有する1価の有機基(x1)であることを特徴とする含フッ素活性エネルギー線硬化性樹脂、その製造方法及び撥液剤、これを含む樹脂組成物及びその硬化膜を提供するものである。
少なくとも一つの、前記(A)以外の2価のフェノール性水酸基含有化合物(B)の残基及び/又は2価のカルボン酸(C)の残基と、を有し、
それらが下記構造式(1)
で表される連結基で結合されてなる構造単位を有し、
且つ1分子中に含まれる前記構造式(1)で表される連結基のうち少なくとも一つは重合性基を有する1価の有機基(x1)であることを特徴とする。以下、これを含フッ素活性エネルギー線硬化性樹脂(I−1)と称する場合がある。
両末端が水酸基であって水素原子の少なくとも1つがフッ素原子に置換されたアルキレン鎖(但し、前記アルキレン鎖はエーテル性の酸素原子を有するものを含む。)(A)とジカルボン酸無水物(E)との反応物の残基と
少なくとも一つの、前記(A)以外の2価の水酸基含有化合物(F)の残基と、を有し、
それらが下記構造式(1)
で表される連結基で結合されてなる構造単位を有し、
且つ1分子中に含まれる前記構造式(1)で表される連結基のうち少なくとも一つは重合性基を有する1価の有機基(x1)であることを特徴とする。以下、これを含フッ素活性エネルギー線硬化性樹脂(I−2)と称する場合がある。
で表される連結基で結合されてなる構造単位を有し、
且つ1分子中に含まれる前記構造式(1)で表される連結基のうち少なくとも一つは重合性基を有する1価の有機基(x1)であることを特徴とする。
で表される構造を含む連結基であることが特に好ましい。
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテック製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
水素原子の少なくとも1つがフッ素原子に置換されたアルキレン鎖(但し、前記アルキレン鎖はエーテル性の酸素原子を有するものを含む。)とエポキシ基とを有する化合物(a1)における、アルキレン鎖は、前述と同意であり、すなわち、炭素原子数1〜6のパーフルオロアルキレン鎖、又は炭素原子数1〜6のパーフルオロアルキレン鎖が酸素原子で連結してなる繰り返し構造を有するパーフルオロアルキレンエーテル鎖であることが好ましい。
製法2では、水素原子の少なくとも1つがフッ素原子に置換されたアルキレン鎖(但し、前記アルキレン鎖はエーテル性の酸素原子を有するものを含む。)とカルボキシ基又は水酸基とを有する化合物(a5)と、2価のエポキシ化合物(a6)とを必須の原料として反応させて得られる反応物中の2級水酸基に、活性エネルギー線硬化性の官能基とイソシアネート基とを有する化合物(a4)を反応させて、活性エネルギー線硬化性の官能基を導入するものであるが、この時に用いる2価のエポキシ化合物、活性エネルギー線硬化性の官能基とイソシアネート基とを有する化合物(a4)は、製法1で用いるものと同様の化合物を挙げることができ、好ましいものも同様である。
・酸性基を有する(メタ)アクリル系重合性単量体を必須の成分として重合させて得られるアルカリ可溶性樹脂(1)。
・反応性基を持つ(メタ)アクリル系重合性単量体を必須の成分として重合させて得られる酸性基を有さない重合体と、該反応性基に対して反応性を有する反応性基と酸基とを有する化合物とを反応させて得られるアルカリ可溶性樹脂(2)
・エポキシ基含有(メタ)アクリレートと、他の重合性単量体との共重合体に対し、該共重合体が有するエポキシ基の少なくとも一部に不飽和モノカルボン酸を付加させ、さらに不飽和モノカルボン酸の付加反応により生じた水酸基の少なくとも一部にポリカルボン酸の酸無水物を付加反応させて得られるアルカリ可溶性樹脂(3)。
・カルボキシ基と重合性不飽和基を有するエポキシ(メタ)アクリレート樹脂(4)
・カルボキシ基と重合性不飽和基を有するカルド型樹脂(5)
以下に、上記(1)〜(5)について詳細に説明する。
撹拌装置、温度計、冷却管及び滴下装置を備えたガラスフラスコに、下記式で表される両末端に水酸基を有するパーフルオロポリエーテル化合物(以下、「化合物(1)と略記する。水酸基当量は、740g/eq。繰り返し数を示すaは5、bは7である。)50部、エピクロロヒドリン62.5部及びエタノール20部を仕込んだ。次いで、窒素気流下で攪拌を開始し、フラスコ内温度を50℃に保ちながら、49%水酸化ナトリウム水溶液8.3部を2時間かけて滴下した。滴下終了後、60℃まで昇温して3時間攪拌した後、室温に戻した。
撹拌装置、温度計、冷却管及び滴下装置を備えたガラスフラスコに、前記化合物(1)と同様の式で表され、aが5、bが7の水酸基当量754g/eqである化合物(3)50部、無水マレイン酸6.5部を仕込んだ。次いで、窒素気流下で攪拌を開始し、フラスコ内温度を160℃に上昇させ、1時間撹拌した。その後、エステル化触媒としてジブチルスズジラウレート0.01部を加えフラスコ内温度を170℃に昇温させ、5時間撹拌した。そして、室温に戻すことで、下記式(a5−1)で表されるポリ(パーフルオロアルキレンエーテル)鎖とその両末端にカルボキシ基を有する化合物(以下、「化合物(a5−1)」と略記する。)56.5部を得た。この化合物(a5−1)は透明液体で、酸価は64.0mgKOH/gであった。
撹拌装置、温度計、冷却管及び滴下装置を備えたガラスフラスコに、化合物(a1−1)49.0部とビスフェノールFジグリシジルエーテル16.3部とビスフェノールF14.6部と、テトラブチルホスホニウムヒドロキシド(TBPH)1000ppmを仕込み、150℃で40時間加熱し、Mw26,000の化合物(5)を得た。ついで、化合物(5)をプロピレングリコールモノメチルエーテルアセテート(PGMEA)で希釈したNV=50%の溶液160部にウレタン化触媒としてジブチルスズジラウレート0.03部、重合禁止剤としてp−メトキシフェノール0.1部を加え、空気気流下で攪拌を開始し、75℃に昇温したのち、2−アクリロイルオキシエチルイソシアネート20.1部を1時間かけて滴下し、75分で30分撹拌し、80℃に昇温して更に2時間攪拌することにより反応を行った結果、IRスペクトル測定でイソシアネート基由来の2360cm−1付近の吸収ピークの消失を確認した。次いでPGMEAを加え、含フッ素活性エネルギー線硬化性樹脂(1−ii)を10%含有するPGMEA溶液を得た。
撹拌装置、温度計、冷却管及び滴下装置を備えたガラスフラスコに、化合物(a1−1)51.4部と1,6−ナフタレンジグリシジルエーテル15.2部と1,6−ナフタレンジオール12.2部と、テトラブチルホスホニウムヒドロキシド(TBPH)1000ppmを仕込み、150℃で40時間加熱し、Mw27,000の化合物(6)を得た。ついで、化合物(6)をプロピレングリコールモノメチルエーテルアセテート(PGMEA)で希釈したNV=50%の溶液158部にウレタン化触媒としてジブチルスズジラウレート0.03部、重合禁止剤としてp−メトキシフェノール0.1部を加え、空気気流下で攪拌を開始し、75℃に昇温したのち、2−アクリロイルオキシエチルイソシアネート21.1部を1時間かけて滴下し、75分で30分撹拌し、80℃に昇温して更に2時間攪拌することにより反応を行った結果、IRスペクトル測定でイソシアネート基由来の2360cm−1付近の吸収ピークの消失を確認した。次いでPGMEAを加え、含フッ素活性エネルギー線硬化性樹脂(1−iii)を10%含有するPGMEA溶液を得た。
撹拌装置、温度計、冷却管及び滴下装置を備えたガラスフラスコに、化合物(a1−1)48.4部とビスフェノールAジグリシジルエーテル17.6部とビスフェノールA16.4部と、テトラブチルホスホニウムヒドロキシド(TBPH)1000ppmを仕込み、150℃で40時間加熱し、Mw28,000の化合物(7)を得た。ついで、化合物(7)をプロピレングリコールモノメチルエーテルアセテート(PGMEA)で希釈したNV=50%の溶液165部に、無水コハク酸5.7部とトリフェニルホスフィン3000ppmを仕込み、110℃へ昇温して4時間ホールドした。酸価により、反応終点を確認したのち、75℃へ冷却し、ウレタン化触媒としてジブチルスズジラウレート0.03部、重合禁止剤としてp−メトキシフェノール0.1部を加え、空気気流下で2−アクリロイルオキシエチルイソシアネート19.4部を1時間かけて滴下し、75分で30分撹拌し、80℃に昇温して更に2時間攪拌することにより反応を行った結果、IRスペクトル測定でイソシアネート基由来の2360cm−1付近の吸収ピークの消失を確認した。次いでPGMEAを加え、含フッ素活性エネルギー線硬化性樹脂(1−iv)を10%含有するPGMEA溶液を得た。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、前記化合物(a1−1−1)20部、溶媒としてジイソプロピルエーテル20部、重合禁止剤としてp−メトキシフェノール0.02部及び中和剤としてトリエチルアミン3.1質量部を仕込み、空気気流下にて攪拌を開始し、フラスコ内を10℃に保ちながらアクリル酸クロライド2.7質量部を1時間かけて滴下した。滴下終了後、10℃で1時間攪拌し、昇温して30℃で1時間攪拌した後、50℃に昇温して10時間攪拌することにより反応を行い、ガスクロマトグラフィー測定にてアクリル酸クロライドの消失が確認された。次いで、溶媒としてジイソプロピルエーテル40部を追加した後、イオン交換水80部を混合して攪拌してから静置し水層を分離させて取り除く方法による洗浄を3回繰り返した。次いで、重合禁止剤としてp−メトキシフェノール0.02部を添加し、脱水剤として硫酸マグネシウム8部を添加して1日間静置することで完全に脱水した後、脱水剤を濾別した。次いで、減圧下で溶媒を留去することによって、下記式で表されるパーフルオロポリエーテル鎖の両末端にアクリロイル基を有する化合物(8)21.5部を得た。
DIC株式会社製ユニディックRS20−160を3.0部、東亞合成化学株式会社製アロニックスM−402を1.2部、実施例及び比較製造例で得られた樹脂を固形分比で0.1%、0.5%、1.0%、2.0%添加し、PGMEAで希釈し、NV19.5%になるように溶液を調製した。調整溶液1mLを7cm×7cmのガラス基板の中央部分に滴下し、回転数1000rpm、回転時間10秒でスピンコ−ティングした後、80℃で3分間加熱乾燥させ溶剤を揮発させた。次に、乾燥した塗膜に紫外線硬化装置(空気雰囲気下、高圧水銀灯、紫外線照射量0.5kJ/m2)で紫外線(UV)を照射して硬化させた。更に230℃で20分間熱処理し、実施例6〜10及び比較例1として塗膜を作製した。フッ素系界面活性剤を用いない以外は、比較例1と同様にして、比較例2の塗膜を作製した。
塗膜表面について、接触角測定装置(協和界面科学株式会社製「MODEL CA−W701」)を用いて、PGMEAの接触角を測定した。結果を表1に示す。比較例2(ブランク)の接触角は15°であった。
Claims (19)
- 1分子中に、少なくとも一つの、両末端が水酸基であって水素原子の少なくとも1つがフッ素原子に置換されたアルキレン鎖(但し、前記アルキレン鎖はエーテル性の酸素原子を有するものを含む。)(A)の残基と、
少なくとも一つの、前記(A)以外の2価のフェノール性水酸基含有化合物(B)の残基及び/又は2価のカルボン酸(C)の残基と、を有し、
それらが下記構造式(1)
で表される連結基で結合されてなる構造単位を有し、
且つ1分子中に含まれる前記構造式(1)で表される連結基のうち少なくとも一つは下記構造式(2)
で表される連結基である、又はXが(メタ)アクリロイル基である前記構造式(1)で表される連結基であることを特徴とする含フッ素活性エネルギー線硬化性樹脂。 - 1分子中に、少なくとも一つの、両末端がカルボキシ基であって水素原子の少なくとも1つがフッ素原子に置換されたアルキレン鎖(但し、前記アルキレン鎖はエーテル性の酸素原子を有するものを含む。)(D)の残基、又は
両末端が水酸基であって水素原子の少なくとも1つがフッ素原子に置換されたアルキレン鎖(但し、前記アルキレン鎖はエーテル性の酸素原子を有するものを含む。)(A)とジカルボン酸無水物(E)との反応物の残基と
少なくとも一つの、前記(A)以外の2価の水酸基含有化合物(F)の残基と、を有し、
それらが下記構造式(1)
で表される連結基で結合されてなる構造単位を有し、
且つ1分子中に含まれる前記構造式(1)で表される連結基のうち少なくとも一つにおけるXが、ビニル基又は(メタ)アクリロイル基を有する1価の有機基であることを特徴とする含フッ素活性エネルギー線硬化性樹脂。 - 末端が、水素原子、カルボキシ基又はグリシジル基である請求項1又は2記載の含フッ素活性エネルギー線硬化性樹脂。
- 前記含フッ素活性エネルギー線硬化性樹脂のフッ素原子含有率が3〜40質量%の範囲である請求項1〜3の何れか1項記載の含フッ素活性エネルギー線硬化性樹脂。
- 前記含フッ素活性エネルギー線硬化性樹脂の重量平均分子量が5,000〜200,000の範囲である請求項1〜4の何れか1項記載の含フッ素活性エネルギー線硬化性樹脂。
- 前記含フッ素活性エネルギー線硬化性樹脂の活性エネルギー線硬化性の官能基濃度が0.5〜3.0mmol/gの範囲である請求項1〜5の何れか1項記載の含フッ素活性エネルギー線硬化性樹脂。
- 前記両末端が水酸基であって水素原子の少なくとも1つがフッ素原子に置換されたアルキレン鎖(但し、前記アルキレン鎖はエーテル性の酸素原子を有するものを含む。)(A)、前記両末端がカルボキシ基であって水素原子の少なくとも1つがフッ素原子に置換されたアルキレン鎖(但し、前記アルキレン鎖はエーテル性の酸素原子を有するものを含む。)(D)が、パーフルオロアルキレンエーテル鎖を有するものである請求項1〜6の何れか1項記載の含フッ素活性エネルギー線硬化性樹脂。
- 前記2価のフェノール性水酸基含有化合物(B)、前記2価の水酸基含有化合物(F)が、芳香環上に置換基を有していてもよい、ビフェノール、ビスフェノール、ビナフトール又はナフタレンジオールである請求項1〜7の何れか1項記載の含フッ素活性エネルギー線硬化性樹脂。
- 前記構造式(1)が、下記構造式(2)
で表される構造である請求項1〜8のいずれか1項記載の含フッ素活性エネルギー線硬化性樹脂。 - 水素原子の少なくとも1つがフッ素原子に置換されたアルキレン鎖(但し、前記アルキレン鎖はエーテル性の酸素原子を有するものを含む。)とエポキシ基とを有する化合物(a1)と、2価のフェノール性水酸基含有化合物(a2)及び/又は2価のカルボン酸(a3)とを必須の原料として反応させて得られる反応物中の2級水酸基に、活性エネルギー線硬化性の官能基である(メタ)アクリロイル基とイソシアネート基とを有する化合物(a4)を反応させることを特徴とする含フッ素活性エネルギー線硬化性樹脂の製造方法。
- 水素原子の少なくとも1つがフッ素原子に置換されたアルキレン鎖(但し、前記アルキレン鎖はエーテル性の酸素原子を有するものを含む。)とカルボキシ基又は水酸基とを有する化合物(a5)と、2価のエポキシ化合物(a6)とを必須の原料として反応させて得られる反応物中の2級水酸基に、活性エネルギー線硬化性の官能基である(メタ)アクリロイル基とイソシアネート基とを有する化合物(a4)を反応させることを特徴とする含フッ素活性エネルギー線硬化性樹脂の製造方法。
- さらに2級水酸基に対して酸無水物基含有化合物(a7)を反応させるものである請求項10又は11記載の含フッ素活性エネルギー線硬化性樹脂の製造方法。
- 請求項1〜9の何れか1項記載の含フッ素活性エネルギー線硬化性樹脂を含むことを特徴とする撥液剤。
- 請求項1〜9の何れか1項記載の含フッ素活性エネルギー線硬化性樹脂と、前記含フッ素活性エネルギー線硬化性樹脂以外の活性エネルギー線硬化性樹脂(II)又は活性エネルギー線硬化性単量体(III)を含む、活性エネルギー線硬化性樹脂組成物。
- 前記活性エネルギー線硬化性樹脂(II)、活性エネルギー線硬化性単量体(III)がアルカリ可溶性である請求項14記載の活性エネルギー線硬化性樹脂組成物。
- さらに重合開始剤を含む請求項14又は15記載の活性エネルギー線硬化性樹脂組成物。
- レジスト組成物である、請求項14〜16の何れか1項記載の活性エネルギー線硬化性樹脂組成物。
- 請求項14〜17の何れか1項記載の活性エネルギー線硬化性樹脂組成物から得られる硬化膜。
- 隔壁である請求項18記載の硬化膜。
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