CN114867794B - Water-repellent coating composition for wet coating comprising silsesquioxane oligomer - Google Patents
Water-repellent coating composition for wet coating comprising silsesquioxane oligomer Download PDFInfo
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- CN114867794B CN114867794B CN202080089394.6A CN202080089394A CN114867794B CN 114867794 B CN114867794 B CN 114867794B CN 202080089394 A CN202080089394 A CN 202080089394A CN 114867794 B CN114867794 B CN 114867794B
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- fluorine
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- 239000008199 coating composition Substances 0.000 title claims abstract description 60
- 239000005871 repellent Substances 0.000 title claims abstract description 45
- 238000000576 coating method Methods 0.000 title claims description 65
- 239000011248 coating agent Substances 0.000 title claims description 59
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 57
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000011737 fluorine Substances 0.000 claims abstract description 56
- 239000000758 substrate Substances 0.000 claims abstract description 46
- 239000002904 solvent Substances 0.000 claims abstract description 44
- 239000000126 substance Substances 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- -1 acryl group Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 239000011247 coating layer Substances 0.000 claims description 26
- 239000003999 initiator Substances 0.000 claims description 17
- 239000010410 layer Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000002222 fluorine compounds Chemical class 0.000 claims description 8
- 125000000962 organic group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
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- KSOCRXJMFBYSFA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,6,6,6-tridecafluoro-5-(1,1,1,2,3,3,4,4,5,5,6,6,6-tridecafluorohexan-2-yloxy)hexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)OC(F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F KSOCRXJMFBYSFA-UHFFFAOYSA-N 0.000 claims description 2
- DFUYAWQUODQGFF-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane Chemical compound CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)F DFUYAWQUODQGFF-UHFFFAOYSA-N 0.000 claims description 2
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- IRPDMKHBZJZAMO-UHFFFAOYSA-N 5-hydrazinylpentan-1-amine Chemical compound NCCCCCNN IRPDMKHBZJZAMO-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- ZXLYUNPVVODNRE-UHFFFAOYSA-N 6-ethenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=C)=N1 ZXLYUNPVVODNRE-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides 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
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical compound N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- AENNXXRRACDJAY-UHFFFAOYSA-N bis(2-dodecylphenyl)iodanium Chemical compound CCCCCCCCCCCCC1=CC=CC=C1[I+]C1=CC=CC=C1CCCCCCCCCCCC AENNXXRRACDJAY-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012952 cationic photoinitiator Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- OHLKTJUGGBHLLU-UHFFFAOYSA-N dimethoxy-bis(2,3,4,5,6-pentafluorophenyl)silane Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1[Si](OC)(OC)C1=C(F)C(F)=C(F)C(F)=C1F OHLKTJUGGBHLLU-UHFFFAOYSA-N 0.000 description 1
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 230000003670 easy-to-clean Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
- XCGSMHBLIRBUGZ-UHFFFAOYSA-K ethyl(triphenyl)phosphanium;phosphate Chemical compound [O-]P([O-])([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 XCGSMHBLIRBUGZ-UHFFFAOYSA-K 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000007542 hardness measurement Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine powder Natural products NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940017144 n-butyl lactate Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- UVBBCQLPTZEDHT-UHFFFAOYSA-N pent-4-en-1-amine Chemical group NCCCC=C UVBBCQLPTZEDHT-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940089951 perfluorooctyl triethoxysilane Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- PMQIWLWDLURJOE-UHFFFAOYSA-N triethoxy(1,1,2,2,3,3,4,4,5,5,6,6,7,7,10,10,10-heptadecafluorodecyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F PMQIWLWDLURJOE-UHFFFAOYSA-N 0.000 description 1
- ZLGWXNBXAXOQBG-UHFFFAOYSA-N triethoxy(3,3,3-trifluoropropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)F ZLGWXNBXAXOQBG-UHFFFAOYSA-N 0.000 description 1
- NYIKUOULKCEZDO-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,6-nonafluorohexyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F NYIKUOULKCEZDO-UHFFFAOYSA-N 0.000 description 1
- BOVWGKNFLVZRDU-UHFFFAOYSA-N triethoxy(trifluoromethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)F BOVWGKNFLVZRDU-UHFFFAOYSA-N 0.000 description 1
- QALDFNLNVLQDSP-UHFFFAOYSA-N triethoxy-(2,3,4,5,6-pentafluorophenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=C(F)C(F)=C(F)C(F)=C1F QALDFNLNVLQDSP-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ZZJNLOGMYQURDL-UHFFFAOYSA-M trifluoromethanesulfonate;tris(4-methylphenyl)sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(C)=CC=C1[S+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZZJNLOGMYQURDL-UHFFFAOYSA-M 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- IJROHELDTBDTPH-UHFFFAOYSA-N trimethoxy(3,3,4,4,5,5,6,6,6-nonafluorohexyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F IJROHELDTBDTPH-UHFFFAOYSA-N 0.000 description 1
- ORVBHOQTQDOUIW-UHFFFAOYSA-N trimethoxy(trifluoromethyl)silane Chemical compound CO[Si](OC)(OC)C(F)(F)F ORVBHOQTQDOUIW-UHFFFAOYSA-N 0.000 description 1
- XFFHTZIRHGKTBQ-UHFFFAOYSA-N trimethoxy-(2,3,4,5,6-pentafluorophenyl)silane Chemical compound CO[Si](OC)(OC)C1=C(F)C(F)=C(F)C(F)=C1F XFFHTZIRHGKTBQ-UHFFFAOYSA-N 0.000 description 1
- RXRIEAKKQPAUKB-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1.CO[Si](OC)(OC)CCCOCC1CO1 RXRIEAKKQPAUKB-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- 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
-
- 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
Abstract
A water-repellent coating composition comprising a silsesquioxane oligomer, which is applicable to general substrates or hard coats, and coated articles using the same are disclosed. The waterproof coating composition of the present invention comprises a silsesquioxane oligomer represented by the following chemical formula 1, a fluorine-based compound, and a solvent. Chemical formula 1The definition of the chemical formula 1 is as described in the specification.
Description
Technical Field
The present invention relates to a water-repellent coating composition for wet coating comprising a silsesquioxane oligomer, and more particularly to a water-repellent coating composition comprising a silsesquioxane oligomer which can be applied to a substrate or a hard coat layer.
Background
Recently, designs of display products are rapidly evolving toward being wearable, rollable, and foldable. Accordingly, the glass substrates that were originally used are also gradually changing into plastic substrates having flexibility. However, plastic substrates have the advantages of light weight, splash prevention, and flexibility as compared to glass substrates, but at the same time have the disadvantages of poor mechanical strength, durability, weather resistance, and optical properties.
In order to overcome the disadvantages of the plastic substrates as described above, research activities are actively being conducted to improve mechanical strength, durability, and optical characteristics by adding a hard coating layer, and to improve stain resistance, weather resistance, easy-to-clean (easy-clean), fingerprint (Anti-finger) resistance, and scratch resistance characteristics to various contaminant substances to glass substrate levels by applying a waterproof coating layer such as an Anti-fingerprint (AF) coating layer on top of the hard coating layer.
In particular, water-resistant coatings are one of the most common functional coating techniques that have been applied to existing glass substrates and used on the outermost layer. In order to apply A Fingerprint (AF) resistant coating on a glass substrate, it is necessary to perform dry coating by vacuum deposition after cutting because of the rigidity of the glass substrate.
For example, in Korean laid-open patent publication No. 2012-0079117, there is disclosed a method of depositing SiO as a primer layer on a substrate x Thereafter, a technique of coating a fluorine compound by a thermal deposition method, and a technique of depositing fingerprint resistant and anti-reflection functional coating of a fluorine compound at the outermost profile after alternately depositing a high refractive substance and a low refractive substance are disclosed in korean laid-open patent No. 2012-0139919. However, when dry coating using vacuum deposition as described above is employed, excellent fingerprint (AF) resistance can be exhibited due to high coating density, but at the same time there is also a problem that large-area coating cannot be achieved and continuous engineering is difficultThe productivity is lowered.
In order to overcome the problems involved in dry coating as described above, research activities on fingerprint (AF) resistant coating liquids that can achieve wet coating have been actively conducted recently. For example, korean laid-open patent No. 2016-0010697 discloses a technique of imparting water repellency, oil repellency, and stain resistance to the surface of a raw material by wet coating the surface with a coating composition comprising a nano silica sol surface-treated with fluorosilane. However, the waterproof coating layer formed by wet coating has a problem that durability such as scratch resistance is lowered as compared with dry coating.
Disclosure of Invention
Problems to be solved by the invention
Accordingly, an object of the present invention is to provide a water-repellent coating composition for wet coating comprising a silsesquioxane oligomer, which can be applied to a general substrate or hard coating layer and can realize large-area coating and continuous engineering by wet coating, and which has durability such as abrasion resistance and scratch resistance comparable to dry coating.
Another object of the present invention is to provide a water-repellent coating composition for wet coating comprising a silsesquioxane oligomer, which can be applied to general substrates or hard coatings and imparts excellent water repellency, oil repellency, fingerprint resistance, stain resistance, durability, scratch resistance, chemical resistance, optical properties, etc. equivalent to glass substrates, and which can be applied to, for example, wearable, crimpable or foldable display products, and can also be used as protective layers for electronic products, mobile phone protective films, automobile interiors and exteriors, home appliances, paints, and various industrial products, etc.
Means for solving the problems
In order to achieve the above object, the present invention provides a waterproof coating composition comprising a silsesquioxane oligomer of the following chemical formula 1, a fluorine-based compound, and a solvent.
Chemical formula 1
In the chemical formula 1, R 1 Each independently is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoro-containing organic group having 1 to 30 carbon atoms, an amino group, (meth) acryloyl group, vinyl group, epoxy group or thiol group, R 1 At least one of which is a fluorine-containing organic group having a carbon number of 1 to 30; r is R 2 Each independently is hydrogen, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; n and m are each independently integers of 1 to 100000.
The present invention provides a coated article comprising: a substrate; and a waterproof coating layer which is a cured product of a waterproof coating composition comprising the silsesquioxane oligomer of chemical formula 1, a fluorine compound, and a solvent, and is located on the upper portion of the substrate.
Effects of the invention
The water-repellent coating composition for wet coating comprising a silsesquioxane oligomer according to the present invention can ensure excellent durability such as abrasion resistance and scratch resistance by comprising a silsesquioxane oligomer, can realize large-area coating and continuous engineering by wet coating, and thereby can ensure excellent productivity, and can also exhibit excellent water-repellent coating characteristics comparable to dry water-repellent coating.
Drawings
Fig. 1 is a schematic view illustrating a state in which a waterproof coating layer to which the embodiment of the present invention is applied is formed on an upper portion of a hard coating layer.
Fig. 2 is a schematic view illustrating a state in which a waterproof coating layer to which another embodiment of the present invention is applied is formed on an upper portion of a hard coating layer.
Fig. 3 is a schematic view illustrating a state in which a waterproof coating layer to which still another embodiment of the present invention is applied is formed on an upper portion of a hard coating layer.
FIG. 4 is a schematic diagram illustrating the results of thermogravimetric analysis (TGA) test of silsesquioxane oligomer synthesized in accordance with example 1 of the present invention.
FIG. 5 is a schematic diagram showing the results of thermogravimetric analysis (TGA) test of the silsesquioxane oligomer synthesized in accordance with synthetic comparative example 2 of the present invention.
Detailed Description
Next, in order to facilitate easy implementation of the present invention by those skilled in the art, embodiments of the present invention will be described in detail. However, the present invention may be realized in many different forms and is not limited to the embodiment described herein.
In the present specification, unless explicitly defined otherwise, the term "substituted" means that a hydrogen atom in a compound is substituted with a substituent selected from halogen atoms (F, br, cl or I), hydroxy, alkoxy, nitro, cyano, amino, azido, amidino, hydrazino, hydrazono, carbonyl, carbamoyl, thiol, ester, carboxyl or salts thereof, sulfonic acid or salts thereof, phosphoric acid or salts thereof, vinyl, C1 to C20 alkyl, C2 to C20 alkenyl, C2 to C20 alkynyl, C6 to C30 aryl, C7 to C30 aralkyl, C6 to C30 allyl, C1 to C30 alkoxy, C1 to C20 heteroalkyl, C3 to C20 heteroarylalkyl, C3 to C30 cycloalkyl, C3 to C15 cycloalkenyl, C6 to C15 cycloalkynyl, C3 to C30 heterocycloalkyl, and combinations thereof.
Furthermore, in the present specification, unless explicitly defined otherwise, the term "hetero" means each independently containing 1 to 10 heteroatoms selected from N, O, S and P.
Next, a waterproof coating composition to which an embodiment is applied will be described.
The water repellent coating composition (including fingerprint resistant (AF) coating composition) to which the present invention is applied comprises a silsesquioxane oligomer, a fluorine-based compound, and a solvent.
The silsesquioxane oligomer has the structure of the following chemical formula 1.
Chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
R 1 each independently is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoro-containing organic group having 1 to 30 carbon atoms, an amino group, (meth) acryloyl group, vinyl group, epoxy group or thiol group, R 1 At least one of which is a fluorine-containing organic group having a carbon number of 1 to 30; specifically, R 1 At least one of which is a fluoroalkyl group having a carbon number of 1 to 30 or a perfluoropolyether group having a carbon number of 1 to 30.
R 2 Each independently is hydrogen, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and specifically, may be hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl or hexyl.
The n and m are each independently an integer of 1 to 100000, preferably an integer of 1 to 1000, and the ratio of n/m is 1:1 to 50:1, and the adhesion properties between the water-repellent coating composition and the substrate can be adjusted according to the ratio of n/m.
In the silsesquioxane oligomer of chemical formula 1, R is relative to the whole 1 The proportion of fluorine may be 1 mol% to 10 mol% based on the total mole (mol) of the catalyst. The ratio of fluorine is relative to the whole R 1 As a result of calculation of the number of moles (mol) of fluorine in the total number of moles (mol), when the proportion of fluorine is less than 1 mol%, problems of water repellency and scratch resistance may be caused, and when it exceeds 10 mol%, problems of solubility in a fluorine solvent may be caused.
In the silsesquioxane oligomer of chemical formula 1, the content of hydroxyl groups (-OH) relative to the entire weight of the silsesquioxane oligomer is 0.5wt% or less. The hydroxyl group content is a calculation result of the hydroxyl group content relative to the entire weight of the silsesquioxane oligomer, and in the case where the hydroxyl group content exceeds 0.5wt%, there may be caused a problem that the stability of the silsesquioxane oligomer is lowered and the solubility in fluorine-based solvents is lowered.
The silsesquioxane oligomer of chemical formula 1 may be prepared by synthesizing a silane compound and a fluorosilane compound, the kind of which is not particularly limited, specifically, as the solvent, for example, trimethoxy- (3, 3-trifluoropropyl) silane (Trimethoxy- (3, 3-trifluoropropyl) silane) Triethoxy- (3, 3-trifluoropropyl) silane (Triethoxy- (3, 3-trifluoropropyl) silane) Triethoxy- (3, 3-trifluoropropyl) silane? Triethoxy- (3, 3-trifluoropropyl) silane).
When the fluorine-based silane compound having 5 or less fluorine atoms (F) is used, the effect of excellent durability such as abrasion resistance and scratch resistance of the waterproof coating composition can be achieved, and when the fluorine-based silane having 6 or more fluorine atoms (F) is used, the effect of excellent slip (water repellency) can be achieved.
The silsesquioxane oligomer of chemical formula 1 is an organic-inorganic hybrid polymer having a structure of a random copolymer including two repeating units. The silsesquioxane oligomer may be prepared by introducing an oxygen-containing-OR 2 The groups promote bonding and adhesion between the substrate and the water-repellent coating composition. In particular, the-OR 2 The groups may form covalent bonds with Si-OH, si-O, etc. of the substrate or hard coating surface, thereby enhancing bonding and adhesion to the substrate or hard coating upon coating.
The silsesquioxane oligomer is contained in an amount of 0.10 to 10 wt%, specifically 0.25 to 5wt%, relative to the entire water-repellent coating composition, and if it is out of the range, problems of water repellency, abrasion resistance, and scratch resistance may be caused.
The fluorine-based compound may be a silane compound having 1 to 50 carbon atoms containing fluorine or perfluoro (poly) ether group, a derivative thereof or a polymer thereof, and specifically, the compound may be selected from a substituted or unsubstituted alkylsilane having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxysilane having 1 to 50 carbon atoms, a substituted or unsubstituted arylsilane having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkylsilane having 3 to 50 carbon atoms, a substituted or unsubstituted chlorosilane having 1 to 50 carbon atoms or a mixture thereof.
Among the silane compounds having 1 to 50 carbon atoms of the fluorine-containing or perfluoro (poly) ether group, specifically, the silane compound may be selected from the group consisting of trifluoromethyl trimethoxysilane, trifluoromethyl triethoxysilane, trifluoropropyl trimethoxysilane, trifluoropropyl triethoxysilane, nonafluorobutyl ethyl trimethoxysilane, nonafluorobutyl ethyl triethoxysilane, nonafluorohexyl trimethoxysilane, nonafluorohexyl triethoxysilane, heptadecafluoro trimethoxysilane, heptadecafluoro decyl triethoxysilane, heptadecafluoro decyl triisopropylsilane, 3-trimethoxysilyl propyl pentafluoctanoate, 3-triethoxysilylpropyl pentafluoctanoate, 3-trimethoxysilyl propyl pentafluoctamide, 3-triethoxysilylpropyl pentafluoctamide, 2-trimethoxysilyl ethyl pentadecyl sulfide, 2-triethoxysilylethyl pentadecyl sulfide, pentafluorophenyl trimethoxysilane, pentafluorophenyl triethoxysilane, 4- (perfluorotolyl) trimethoxysilane, 4- (perfluorotolyl) triethoxysilane, dimethoxybis (pentafluorophenyl) silane, diethoxy bis (4-trifluoromethoxy) silane, trimethoxy-bis (4-tolyl) silane, and trimethoxy silane.
The content of the fluorine-based compound is 0.5 to 10% by weight, specifically 1 to 5% by weight, relative to the entire water-repellent coating composition, and if it exceeds the range, problems of coating property, water repellency, and scratch resistance may be caused.
As the solvent, a solvent which can dissolve the silsesquioxane oligomer and is easily removed by heating or the like can be used without limitation, for example, not only fluorine-based ones can be used; alcohols such as methanol, ethanol, isopropanol, butanol, cellosolve, and the like; lactic acid; ketones such as acetone and methyl (isobutyl) ethyl ketone; glycols such as ethylene glycol; furans such as tetrahydrofuran; polar solvents such as dimethylformamide, dimethylacetamide and N-methyl-2-pyrrolidone, and various solvents such as hexane, cyclohexane, cyclohexanone, toluene, xylene, cresol, chloroform, dichlorobenzene, xylene, trimethylbenzene, pyridine, methylnaphthalene, nitromethane, acrylonitrile, methylene chloride, octadecylamine, aniline, dimethylsulfoxide and benzyl alcohol can be used, but are not limited thereto, and specifically, fluorine-based solvents can be used.
As the fluorine-based solvent, a fluorine-based solvent alone or a mixed solvent of two or more solvents including a fluorine-based solvent and a non-fluorine-based solvent may be used. The use of a fluorine-based solvent alone means the use of one fluorine-based solvent or a mixture of two or more fluorine-based solvents. As the fluorine-based solvent, a fluorine-based solvent capable of dispersing a fluorine-based compound and dissolving the silsesquioxane oligomer may be used without limitation, and specifically, ethyl nonafluoroisobutyl ether, ethyl nonafluorobutyl ether, perfluorobutyl ethyl ether, perfluorohexyl methyl ether, and the like may be used.
As the non-fluorine-based solvent that can be used together with the fluorine-based solvent, a non-fluorine-based solvent that can dissolve the silsesquioxane oligomer and has no problem in terms of miscibility with the fluorine-based solvent and does not reduce the stability of the water-repellent coating composition can be used without limitation. For example, alcohols such as methanol, ethanol, isopropanol, butanol, cellosolve, and the like can be used; lactic acids such as ethyl lactate and n-butyl lactate; ketones such as acetone and methyl (isobutyl) ethyl ketone; glycols such as ethylene glycol; furans such as tetrahydrofuran; polar solvents such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, and various solvents such as hexane, cyclohexane, cyclohexanone, toluene, xylene, cresol, chloroform, dichlorobenzene, xylene, trimethylbenzene, pyridine, methylnaphthalene, nitromethane, acrylonitrile, methylene chloride, octadecylamine, aniline, dimethylsulfoxide, and benzyl alcohol can be used.
The content of the solvent is 80 to 99% by weight, specifically 85 to 99% by weight, relative to the entire water-repellent coating composition, and in the case where the content of the solvent is less than 80%, there is a possibility that the problem of lowering the coating property due to lowering of the dispersibility of the water-repellent coating composition, and in the case where it exceeds 99% by weight, there is a possibility that the problem of lowering of the scratch resistance due to failure to coat the water-repellent coating composition at a desired thickness may occur.
The solvent may contain a fluorine-based solvent, for example, 80 to 100 wt% of the fluorine-based solvent may be contained with respect to 100 wt% of the entire solvent, specifically, 90 to 100 wt% may be contained, and in the case where the content of the fluorine-based solvent is less than 80 wt%, there may be a problem that the compatibility with the silsesquioxane oligomer and the fluorine-based compound is lowered.
In one embodiment, the water-repellent coating composition may further comprise an initiator.
The initiator included is for curing and subsequent reaction of the coating composition, and different types of initiators may be used depending on the substituents of the silsesquioxane oligomer.
For example, in the case of the substituents of the silsesquioxane oligomer (specifically, R 1 ) In the case where unsaturated hydrocarbon or the like is contained, a radical initiator may be used, and as the radical initiator, as the catalyst, for example, trichloroacetophenone (trichloroacetophenone), diethoxyacetophenone (diethoxyacetophenone), 1-phenyl-2-hydroxy-2-methylpropan-1-one (1-phenyl-2-hydroxy-2-methylpropan-1-one), 1-hydroxycyclohexylphenyl ketone, 2-methyl-1- (4-methylthiophene) -2-morpholinopropane-1-one (2-methyl-1- (4-methylpropenyl) -2-morpholinopropane-1-one) 2,4,6-trimethylbenzoyldiphenyl phosphine oxide (2, 4, 6-trimethylbenzodiphenylphosphine oxide), camphorquinone (camphorquinone), 2' -azobis (2-methylbutyronitrile), 2' -azobis (2-methylbutyrate) dimethyl ester (2-methyl-2, 2' -azobis), 3-dimethyl-4-methoxy-benzophenone, p-methoxybenzophenone, 2-diethoxyacetophenone and 2, 2-dimethoxy-1, 2-diphenylethylPhoto radical initiators such as an alkane-1-one; thermal radical initiators such as t-butyl peroxymaleate, t-butyl hydroperoxide, 2, 4-dichlorobenzoyl peroxide, 1-bis (t-butyl peroxy) -3, 5-trimethylcyclohexane, and n-butyl 4,4' -bis (t-butyl peroxy) valerate; or mixtures thereof, and the like.
In addition, in the case where an epoxy group or the like is contained in the substituent of the silsesquioxane oligomer, a cationic initiator or an amine curing agent may be used.
As the cationic photoinitiator in the cationic initiator, sulfonium species such as triphenylsulfonium and diphenyl-4- (phenylthio) phenylsulfonium can be used without limitation; iodonium compounds such as diphenyliodonium and bis (dodecylphenyl) iodonium; diazos such as phenyl diazonium; ammonium compounds such as 1-benzyl-2-cyanopyridine and 1- (naphthylmethyl) -2-cyanopyridine; and (4-methylphenyl) [4- (2-methylpropyl) phenyl ] -iodonium hexafluorophosphate, bis (4-t-butylphenyl) iodonium hexafluorophosphate, iodonium diphenylhexafluorophosphate, iodonium diphenyltriflate, triphenylsulfonium tetrafluoroborate, tri-p-tolylsulfonium hexafluorophosphate, tri-p-tolylsulfonium triflate, etc., and as a cationic thermal initiator, cationic species such as trifluoromethanesulfonate, boron trifluoride ether complex, boron trifluoride, etc., or protonic acid catalysts can be used without limitation; various onium salts such as ammonium salts, phosphonium salts, and sulfonium salts; methyl triphenyl phosphonium bromide, ethyl triphenyl phosphonium bromide, phenyl triphenyl phosphonium bromide, and the like. The cationic initiator may be added in various mixed forms and may be mixed with the radical initiator.
Further, as the amine curing agent, for example, ethylene diamine, triethylene tetramine, tetraethylene pentamine, 1, 3-diaminopropane, dipropylene triamine, 3- (2-aminoethyl) amino-propylamine, N' -bis (3-aminopropyl) -ethylene diamine, 4, 9-dioxadodecane-1, 12-diamine, 4,7, 10-trioxatridecane-1, 13-diamine, hexamethylenediamine, 2-methylpentamethylene diamine, 1, 3-diaminomethylcyclohexane, bis (4-aminocyclohexyl) methane, norbornene diamine, 1, 2-diaminocyclohexane, and the like can be used.
In addition to the initiator, a curing accelerator for accelerating curing may be contained, and triazine compounds such as acetoguanamine, benzoguanamine, and 2, 4-diamino-6-vinyl-s-triazine may be used; imidazole compounds such as imidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, vinylimidazole, and 1-methylimidazole; 1, 5-diazabicyclo [4.3.0] nonene-5,1,8-diazabicyclo [5.4.0] undecene-7, triphenylphosphine, diphenyl (p-tri-yl) phosphine, tri (alkylphenyl) phosphine, tri (alkoxyphenyl) phosphine, ethyltriphenyl phosphonium phosphate, tetra-n-butylphosphine hydroxide, tetra-n-butylammonium acetate, tetra-n-butylphosphine bifluoride, tetra-n-butylphosphine trifluoride, and the like.
In addition, acid anhydride curing agents such as phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 2, 4-diethylglutaric anhydride, and the like can also be widely used.
The initiator may be contained in an appropriate amount according to the type of initiator.
There is provided a coated article coated with the waterproof coating composition of the present invention. The coated article comprising: a substrate; and a waterproof coating layer which is a cured product of a waterproof coating composition comprising the silsesquioxane oligomer of chemical formula 1, a fluorine compound, and a solvent, and is located on the upper portion of the substrate.
As the substrate, a known substrate can be used without limitation, specifically, a glass substrate and a plastic substrate can be used, more specifically, glass, polycarbonate (PC), polymethyl methacrylate (PMMA), polyethylene terephthalate (PET, polyethylene terephthalate), polyimide (PI), and the like can be included, and the substrate can be used in the form of a single substrate or a composite substrate.
In addition, the coated article may further include a hard coating layer formed between the substrate and the waterproof coating layer. The hard coat layer may be formed by applying a known hard coat composition to the substrate, and may improve physical properties, reliability, etc. of the substrate, and particularly in the case of including a silicon-based hard coat layer, may improve bonding force with a waterproof coating layer formed by wet coating and thereby further improve durability of the waterproof coating layer.
The waterproof coating is formed by wet coating with the waterproof coating composition. For example, the waterproof coating composition may be applied by a coating method such as Spray (Spray) coating, flow (Flow) coating, dip (Dip) coating, slit die (Slot die) coating, roll-to-Roll (Roll) coating, or the like, to form a waterproof coating.
In the coating method, in the case of dry coating, excellent waterproof coating characteristics such As Fingerprint (AF) resistance and the like can be exhibited because of high coating density and coating uniformity, but at the same time, there is a problem in that productivity is deteriorated because large-area coating and continuous engineering cannot be achieved. In contrast, wet coating has a problem that it is high in productivity in terms of large-area coating and continuous engineering, but at the same time, durability and scratch resistance are lowered as compared with dry coating.
However, the water-repellent coating composition suitable for use in the present invention may be prepared by the silsesquioxane oligomer, in particular, by-OR of the silsesquioxane oligomer 2 The group forms a covalent bond with si—oh, si—o, or the like without subjecting the substrate to surface treatment, and therefore, bonding and adhesion with the substrate can be improved and a stronger bond can be formed at the time of coating, so that excellent durability and scratch resistance can be achieved by a simple wet coating method, and large-area coating and continuous engineering can be achieved by a wet coating method, and a waterproof coated substrate having durability comparable to that of dry coating can be provided.
Fig. 1 to 3 are schematic views illustrating a state in which a waterproof coating layer of an applicable embodiment is formed on top of a hard coating layer. As can be seen from fig. 1 to 3, a coating layer containing silsesquioxane oligomer 1 and fluorine compound 2 was formed on the top of the hard coating layer, and at this time, the fluorine compound and the hard coating layer surface formed covalent bonds.
Fig. 1 shows that silsesquioxane oligomer 1 contains short-chain substituents, and has excellent properties such as abrasion resistance and scratch resistance of a water-repellent coating when the number of fluorine (F) in the substituents is 5 or less.
Fig. 2 shows that the silsesquioxane oligomer 1 contains a long-chain substituent, and has the characteristic of excellent slip properties (water repellency) of a water-repellent coating when the number of fluorine (F) in the substituent is 6 or more.
Fig. 3 shows that the silsesquioxane oligomer 1 contains both short-chain substituents and long-chain substituents, and the substituents having different fluorine amounts and different lengths can be mixed or the ratio thereof can be adjusted and used according to the physical properties of the desired waterproof coating.
The present invention will be described in more detail with reference to examples, but the present invention is not limited by the following examples.
Synthesis example 1: synthesis of silsesquioxane oligomers
In a dry beaker equipped with a cooling tube and a stirrer, 25.6g of distilled water and 100g of methanol were mixed, followed by slow dropwise addition of 209.29g (0.8 mol) of propyl 3- (Trichlorosilyl) methacrylate (3- (trichlolyl) propyl methacrylate) over 10 minutes. At this time, a temperature of-4℃was maintained. Then, 500g of toluene was added dropwise after stirring for 20 minutes, and stirring was continued for 10 minutes after the temperature was raised to a normal temperature state. Next, 23.63g (0.1 mol) of (3-Glycidoxypropyl) trimethoxysilane (3-Glycidoxypropyl) and 21.83g (0.1 mol) of Trimethoxy (3, 3-trifluoropropyl) silane (Trimethoxy (3, 3-trifluoropropyl) silane) were simultaneously added dropwise, and stirring was performed for 10 minutes.
In 20g of Na to be prepared separately 2 CO 3 A 20 wt% aqueous solution was added to the reactor, followed by raising the temperature to 100 ℃ and performing polycondensation reaction for 1 day. In the reactant obtained by the polycondensation reaction, layer separation and purification of water and toluene are performed twice,and after confirming that the pH was neutral, a toluene layer was obtained and all toluene was removed by vacuum depressurization, thereby obtaining a silsesquioxane oligomer.
Thermogravimetric analysis (TGA) was performed on the obtained silsesquioxane oligomer, and the result values thereof are shown in fig. 4 below. In the silsesquioxane oligomer of Synthesis example 1, there was no weight loss (weight loss) up to 150℃indicating that the hydroxyl group (-OH) content of the silsesquioxane oligomer was 0.5% by weight or less. The thermogravimetric analysis (TGA) test is performed while increasing the temperature from 0 ℃ to 800 ℃ at a rate of 10 ℃ (c/min) per minute.
Synthesis example 2: synthesis of silsesquioxane oligomers
Except that 56.83g (0.1 mol) of 1H, 2H-perfluorooctyltriethoxysilane (1H, 2H-perfluoretactyltriethoxycilane) were used instead of 21.83g (0.1 mol) of Trimethoxy (3, 3-trifluoropropyl) silane (Trimethoxy (3, 3-trifluoropropyl) silane), the preparation was carried out in the same manner as in Synthesis example 1.
Synthesis example 3: synthesis of silsesquioxane oligomers
Except that 10.91g (0.05 mol) of Trimethoxy (3, 3-trifluoropropyl) silane (Trimethoxy (3, 3-trifluoropropyl) silane) and 28.42g (0.05 mol) of 1H, 2H-perfluorooctyl tri-silane were used ethoxysilane (1H, 2H-perfluoretrimetoxy) in place of 21.83g (0.1 mol) of Trimethoxy (3, 3-trifluoropropyl) silane (trisxy (3, 3-trifluoropropyl) silane), the preparation was carried out in the same manner as in Synthesis example 1.
Comparative synthesis example 1: synthesis of silsesquioxane oligomers containing no fluorine (F)
In a dry beaker equipped with a cooling tube and a stirrer, 28.8g of distilled water and 100g of methanol were mixed, followed by slow dropwise addition of 235.45g (0.9 mol) of propyl 3- (Trichlorosilyl) methacrylate (3- (trichlolyl) propylmate) over 10 minutes. At this time, a temperature of-4℃was maintained. Then, 500g of toluene was added dropwise after stirring for 20 minutes, and stirring was continued for 10 minutes after the temperature was raised to a normal temperature state. Next, 23.63g (0.1 mol) of 3-glycidoxypropyl trimethoxysilane (3-glycidoxypropyrimethoxysilane) was added dropwise and stirring was performed for 10 minutes.
In 10g of Na to be prepared separately 2 CO 3 A 20 wt% aqueous solution was added to the reactor, followed by raising the temperature to 100 ℃ and performing polycondensation reaction for 1 day. In the reactant obtained by the polycondensation reaction, layer separation and purification of water and toluene were performed twice, and after confirming that the pH was neutral, a toluene layer was obtained and all toluene was removed by vacuum depressurization, thereby obtaining a silsesquioxane oligomer.
Comparative synthesis example 2: synthesis of silsesquioxane oligomers having hydroxyl (-OH) content exceeding 0.5wt%
In a dry beaker equipped with a cooling tube and a stirrer, 25.6g of distilled water and 100g of methanol were mixed, followed by slow dropwise addition of 209.29g (0.8 mol) of propyl 3- (Trichlorosilyl) methacrylate (3- (trichlolyl) propylmate) over 10 minutes. At this time, a temperature of-4℃was maintained. Then, 500g of toluene was added dropwise after stirring for 20 minutes, and stirring was continued for 10 minutes after the temperature was raised to a normal temperature state. Next, 23.63g (0.1 mol) of 3-glycidoxypropyl trimethoxysilane (3-glycidoxypropyl trimethoxysilane) and 21.83g (0.1 mol) of Trimethoxy (3, 3-trifluoropropyl) silane (Trimethoxy (3, 3-trifluoropropyl) silane) were simultaneously added dropwise, and stirring was performed for 10 minutes. Next, the temperature was raised to 100℃and polycondensation reaction was carried out for 1 day. In the reactant obtained by the polycondensation reaction, layer separation and purification of water and toluene were performed twice, and after confirming that the pH was neutral, a toluene layer was obtained and all toluene was removed by vacuum depressurization, thereby obtaining a silsesquioxane oligomer.
Thermogravimetric analysis (TGA) was performed on the obtained silsesquioxane oligomer, and the result values thereof are shown in fig. 5 below. In the silsesquioxane oligomer of comparative Synthesis example 2, weight loss (weight loss) occurred at about 150℃and the weight loss amount indicated that the hydroxyl group (-OH) content of the silsesquioxane oligomer was more than 0.5% by weight.
Example 1: preparation of a Water-repellent coating composition
1.0g of the silsesquioxane oligomer obtained in synthesis example 1 was dissolved in a fluorine-based solvent (3M company, FC-3283), thereby preparing 100g of a composition comprising 1.0 wt% of the silsesquioxane oligomer. Next, 2.0g of a fluorosilane (DAIKIN Co., OPTOOL UD 509) and 0.1g of a radical thermal initiator (Wako Co., V65) were added to the prepared 100g of the composition and stirred for 10 minutes, thereby preparing a water-repellent coating composition.
Example 2 and example 3: preparation of a Water-repellent coating composition
A waterproof coating composition was prepared in the same manner as in example 1, except that the silsesquioxane oligomer obtained in synthesis example 2 and synthesis example 3 was used.
Comparative example 1 and comparative example 2: preparation of a Water-repellent coating composition
A water-repellent coating composition was prepared in the same manner as in example 1, except that the silsesquioxane oligomer obtained in comparative synthesis example 1 and comparative synthesis example 2 was used.
Comparative example 3: preparation of a Water-repellent coating composition
A water-repellent coating composition was prepared in the same manner as in example 1, except that MA0735 (Methacryl polyhedral oligomeric silsesquioxane cage mixture, chemical formula 2 below) of Hybrid plastics was used as the silsesquioxane oligomer.
Chemical formula 2
Comparative example 4: preparation of a Water-repellent coating composition
A water-repellent coating composition was prepared in the same manner as in example 1, except that FL0578 (Trifluoropropyl POSS Cage Mixture, chemical formula 3 below) of Hybrid plastics was used as the silsesquioxane oligomer.
Chemical formula 3
Comparative example 5: preparation of a Water-repellent coating composition
A waterproof coating composition was prepared in the same manner as in example 1, except that trifluoropropyl methyl siloxane (chemical formula 4 below) was used instead of the silsesquioxane oligomer.
Chemical formula 4
Test example: preparation of coated articles
The waterproof coating compositions of examples 1 to 3 and comparative examples 1 to 5 were coated on a hard coat/Polycarbonate (PC) (eastern metaken company, 680 μm) substrate and cured at a temperature of 85 ℃ for 10 minutes, thereby preparing a coated substrate including a waterproof coating. Physical properties were evaluated by the following evaluation methods, and the results are shown in table 1 below.
Comparative test example: preparation of uncoated articles
Physical properties of a hard coat layer/Polycarbonate (PC) (680 μm, east asia mekinone) substrate on which a waterproof coating layer was not formed were evaluated in the same manner as in the above test example, and the results are shown in table 1 below.
Evaluation method
Surface hardness measurement: the measurement was carried out in accordance with JIS 5600-5-4 under a load of 1kgf which is a severely selected condition. Pencils used Mitsubishi corporation products, each of which was tested 5 times for hardness and judged to be bad when more than two scratch marks occurred.
Light transmittance, yellowness Index (YI) and haze (haze) measurements: the measurement was carried out according to ISO 14782 using COH-400 (Nippon Denshoku Co.). Each sample was measured 5 times and the average value is reported.
Rubber wear resistance test: implemented according to KS B ISO 9211-4. At this time, the rubber used for the abrasion resistance test, and contact angle values of the surfaces of the base material before and after the test were measured after repeated execution of 1500 times with a load of 1 kgf.
Salt spray test: according to JIS K5400, the treatment was carried out at 35℃under 5% brine concentration conditions for 72 hours. In order to confirm the durability against brine, contact angle values of the surfaces of the substrates before and after the test were measured.
High temperature and high humidity test: according to JIS C7021, the reaction was carried out at a temperature of 85℃under a humidity environment of 85% for 120 hours. In order to confirm the durability to the high-temperature and high-humidity environment, contact angle values of the surfaces of the substrates before and after the test were measured.
Scratch resistance: according to JIS K5600-5-9, a Steel wool (Steel wool) of #0000 was used to carry a load of 1 kgf. In this case, 10000 times, which are severe conditions, were selected as the number of rounds, and the presence or absence of scratch was checked by an optical microscope.
Durability evaluation: according to JIS K5600-5-9, a Steel wool (Steel wool) of #0000 was used to carry a load of 1 kgf. In this case, 10000 times, which are harsh conditions, are selected as the number of rounds, and contact angle values of the surfaces of the substrates before and after the test are measured.
TABLE 1
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As shown in table 1 above, examples 1 to 3 were excellent in surface hardness, light transmittance, and the like, and less in contact angle change before and after abrasion resistance, brine spray, high temperature and high humidity, durability test, indicating that durability under severe conditions was more excellent than comparative examples 1 to 5. In contrast, since the silsesquioxane oligomers used in comparative example 2 and comparative example 3 were low in compatibility with the solvent and could not be mixed with each other, a waterproof coating could not be formed, and thus physical properties thereof could not be evaluated.
As can be confirmed by comparing example 1 and example 2, example 1 showed less variation in contact angle before and after the abrasion resistance and durability test, indicating that example 1 was more excellent in abrasion resistance and durability than example 2.
In contrast, since the initial contact angle of example 2 before the test was more than 123 °, it was shown that example 2 was more excellent in slipping property (water repellency) than example 1.
From this, it was confirmed that abrasion resistance, durability, and the like can be improved in the case of a silsesquioxane oligomer having a short substituent with fluorine (F) of 5 or less, and that slip (water repellency) can be improved in the case of a silsesquioxane oligomer having a long substituent with fluorine of 6 or more.
Claims (13)
1. A waterproof coating composition, characterized in that,
comprising the following steps:
a silsesquioxane oligomer represented by the following chemical formula 1,
fluorine-based compounds, and, in addition,
a solvent;
in the silsesquioxane oligomer, the content of hydroxyl groups is 0.5wt% or less relative to the weight of the entire silsesquioxane oligomer;
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
R 1 each independently is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, a fluorine-containing organic group having 1 to 30 carbon atoms, an amino group, (meth) acryl group, vinyl group, epoxy groupRadicals or thiol radicals, R 1 At least one of which is a fluorine-containing organic group having a carbon number of 1 to 30;
R 2 each independently is hydrogen, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;
n and m are each independently integers of 1 to 100000.
2. The water-repellent coating composition according to claim 1, wherein,
in the silsesquioxane oligomer, R is relative to the whole 1 The proportion of fluorine is 1 to 10 mol%.
3. The water-repellent coating composition according to claim 1, wherein,
the R is 1 At least one of which is a fluoroalkyl group having a carbon number of 1 to 30 or a perfluoropolyether group having a carbon number of 1 to 30.
4. The water-repellent coating composition according to claim 1, wherein,
the fluorine compound is at least one selected from silane compounds, derivatives or polymers containing fluorine or perfluoro (poly) ether groups and having a carbon number of 1 to 50.
5. The water-repellent coating composition according to claim 4, wherein,
the fluorine-based compound is selected from the group consisting of a substituted or unsubstituted alkylsilane having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxysilane having 1 to 50 carbon atoms, a substituted or unsubstituted arylsilane having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkylsilane having 3 to 50 carbon atoms, a substituted or unsubstituted chlorosilane having 1 to 50 carbon atoms, and a mixture thereof.
6. The water-repellent coating composition according to claim 1, wherein,
the solvent comprises a fluorine-based solvent.
7. The water-repellent coating composition according to claim 6, wherein,
the fluorine-based solvent is selected from the group consisting of ethyl nonafluoroisobutyl ether, ethyl nonafluorobutyl ether, perfluorobutyl ethyl ether, and perfluorohexyl methyl ether, and mixtures thereof.
8. The water-repellent coating composition according to claim 6, wherein,
the fluorine-containing solvent is contained in an amount of 80 to 100% by weight based on 100% by weight of the entire solvent.
9. The water-repellent coating composition according to claim 1, wherein,
the silsesquioxane oligomer is contained in an amount of 0.1 to 10 wt% relative to the entire water-repellent coating composition; the fluorine-based compound is contained in an amount of 0.5 to 10% by weight; the solvent is contained in an amount of 80 to 99% by weight.
10. The water-repellent coating composition according to claim 1, wherein,
the water-repellent coating composition further comprises an initiator.
11. The water-repellent coating composition according to claim 1, wherein,
the waterproof coating composition is a wet coating composition.
12. A coated article, characterized in that,
comprising the following steps:
a substrate, a substrate for a semiconductor device,
a waterproof coating layer which is a cured product of a waterproof coating composition comprising a silsesquioxane oligomer represented by the following chemical formula 1, a fluorine compound, and a solvent, and is located on the upper portion of the substrate;
in the silsesquioxane oligomer, the content of hydroxyl groups is 0.5wt% or less relative to the weight of the entire silsesquioxane oligomer;
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
R 1 each independently is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, a fluorine-containing organic group having 1 to 30 carbon atoms, an amino group, (meth) acryl group, vinyl group, epoxy group or thiol group, R 1 At least one of which is a fluorine-containing organic group having a carbon number of 1 to 30;
R 2 each independently is hydrogen, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;
n and m are each independently integers of 1 to 100000.
13. The coated article of claim 12, wherein the coating comprises a coating comprising a metal selected from the group consisting of,
a hard coat layer is also included between the substrate and the waterproof coating layer.
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| KR1020200175179A KR20210086489A (en) | 2019-12-31 | 2020-12-15 | Water repellent coating composition for wet coatings including silsesquioxane oligomer |
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|---|---|---|---|---|
| EP1251155A1 (en) * | 2001-03-29 | 2002-10-23 | Shipley Company LLC | Method of forming optical waveguides using a photodefinable silsesquioxane composition |
| JP2003138216A (en) * | 2001-10-31 | 2003-05-14 | Denso Corp | Coating agent for wiper blade rubber and wiper blade rubber |
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| WO2019098622A1 (en) * | 2017-11-16 | 2019-05-23 | 주식회사 동진쎄미켐 | Silsesquioxane polymer and coating composition comprising same |
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| JP4118973B2 (en) * | 1997-03-14 | 2008-07-16 | 新日鐵化学株式会社 | Silicone compound and method for producing the same |
| US6911518B2 (en) * | 1999-12-23 | 2005-06-28 | Hybrid Plastics, Llc | Polyhedral oligomeric -silsesquioxanes, -silicates and -siloxanes bearing ring-strained olefinic functionalities |
| KR102035831B1 (en) * | 2016-03-17 | 2019-11-18 | 주식회사 엘지화학 | Polyhedral oligomeric silsesquioxane and method for preparing the same |
| KR20180058912A (en) * | 2016-11-24 | 2018-06-04 | 삼성디스플레이 주식회사 | Hard coating composition and flexible display device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1251155A1 (en) * | 2001-03-29 | 2002-10-23 | Shipley Company LLC | Method of forming optical waveguides using a photodefinable silsesquioxane composition |
| JP2003138216A (en) * | 2001-10-31 | 2003-05-14 | Denso Corp | Coating agent for wiper blade rubber and wiper blade rubber |
| CN105524552A (en) * | 2016-01-18 | 2016-04-27 | 矽时代材料科技股份有限公司 | High performance organic silicon-fluorine nano-paint and use of same |
| WO2019098622A1 (en) * | 2017-11-16 | 2019-05-23 | 주식회사 동진쎄미켐 | Silsesquioxane polymer and coating composition comprising same |
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