KR20190025813A - Organosilicon compound and surface treatment composition - Google Patents
Organosilicon compound and surface treatment composition Download PDFInfo
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- KR20190025813A KR20190025813A KR1020187027539A KR20187027539A KR20190025813A KR 20190025813 A KR20190025813 A KR 20190025813A KR 1020187027539 A KR1020187027539 A KR 1020187027539A KR 20187027539 A KR20187027539 A KR 20187027539A KR 20190025813 A KR20190025813 A KR 20190025813A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- water
- organosilicon compound
- formula
- carbon atoms
- Prior art date
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- 150000003961 organosilicon compounds Chemical class 0.000 title claims abstract description 86
- 239000000203 mixture Substances 0.000 title claims abstract description 58
- 238000004381 surface treatment Methods 0.000 title claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 238000000576 coating method Methods 0.000 claims abstract description 24
- 239000011248 coating agent Substances 0.000 claims abstract description 23
- 239000012756 surface treatment agent Substances 0.000 claims abstract description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000000732 arylene group Chemical group 0.000 claims abstract description 4
- 239000005871 repellent Substances 0.000 claims description 48
- 239000000758 substrate Substances 0.000 claims description 39
- 125000005647 linker group Chemical group 0.000 claims description 20
- 239000011521 glass Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 15
- 230000002940 repellent Effects 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000003377 silicon compounds Chemical class 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 239000007859 condensation product Substances 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000000919 ceramic Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
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- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 238000000280 densification Methods 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
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- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
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- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
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- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- RCNRJBWHLARWRP-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane;platinum Chemical compound [Pt].C=C[Si](C)(C)O[Si](C)(C)C=C RCNRJBWHLARWRP-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 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
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 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
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- XAKYZBMFCZISAU-UHFFFAOYSA-N platinum;triphenylphosphane Chemical compound [Pt].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 XAKYZBMFCZISAU-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- KSZAFPAEKQQXLJ-UHFFFAOYSA-N trichloro(2,2,2-trifluoroethyl)silane Chemical compound FC(F)(F)C[Si](Cl)(Cl)Cl KSZAFPAEKQQXLJ-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-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
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Combustion & Propulsion (AREA)
- Materials Engineering (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
- Surface Treatment Of Glass (AREA)
Abstract
일반식 (1)로 표시되는 유기 규소 화합물은 발수성, 활수성, 내구성이 우수한 피막을 제공하므로, 표면처리제 조성물에 적합하게 사용할 수 있다.
{식 (1) 중, R1은, 서로 독립하여, 탄소 원자수 1∼12의 알킬기 또는 식 (2)로 표시되는 기를 나타내고,
[식 (2) 중, R4는, 서로 독립하여, 탄소 원자수 1∼12의 알킬기 또는 식 (3)로 표시되는 기를 나타낸다. (식 (3) 중, R5는, 서로 독립하여, 탄소 원자수 1∼12의 알킬기를 나타낸다.)]
R2는 서로 독립하여 탄소 원자수 1∼12의 알킬기를, R3은 서로 독립하여 탄소 원자수 1∼4의 알킬기를, X는 서로 독립하여 하이드록시기 또는 가수분해성 기를, Y는 아릴렌기 또는 불화 알킬렌기를 함유하는 2가 연결기를, a는 1∼100의 수를, b는 0∼2의 수를 나타낸다.}The organosilicon compound represented by the general formula (1) provides a coating film excellent in water repellency, fluidity and durability, and thus can be suitably used in a surface treatment agent composition.
(In the formula (1), R 1 , independently of each other, represents an alkyl group having 1 to 12 carbon atoms or a group represented by the formula (2)
[In the formula (2), R 4 independently represents an alkyl group having 1 to 12 carbon atoms or a group represented by the formula (3). (In the formula (3), R 5 , independently of each other, represents an alkyl group having 1 to 12 carbon atoms.)]
R 2 is independently of each other an alkyl group of 1 to 12 carbon atoms, R 3 is independently of each other an alkyl group of 1 to 4 carbon atoms, X is independently of each other a hydroxyl group or a hydrolyzable group, Y is an arylene group or A represents a number of 1 to 100, and b represents a number of 0 to 2. "
Description
본 발명은 유기 규소 화합물 및 표면처리제 조성물에 관한 것으로, 더욱 상세하게 설명하면, 가열하지 않고 실온에서 경화하여, 발수성, 활수성(물방울의 낙하성), 및 내구성이 우수한 발수막을 공급하는 유기 규소 화합물 및 그것을 사용한 표면처리제 조성물, 및 당해 조성물에 의한 표면처리로 형성된 발수막 부착 기재, 및 당해 조성물을 사용한 발수막의 형성 방법에 관한 것이다.The present invention relates to an organosilicon compound and a surface treatment agent composition. More specifically, the present invention relates to an organosilicon compound and a surface treatment agent composition which cure at room temperature without heating to provide a water repellent film having excellent water repellency, And a surface treatment agent composition using the same, a water-repellent film-adhered base formed by surface treatment with the composition, and a method of forming a water-repellent film using the composition.
종래, 유리의 발수처리제로서 플루오로알킬실레인이나 아미노 변성 폴리실록세인을 배합한 발수제 조성물이 제안되었다(특허문헌 1∼6 참조).Conventionally, a water repellent composition comprising a fluoroalkylsilane or an amino-modified polysiloxane as a water-repellent agent for glass has been proposed (see Patent Documents 1 to 6).
이들 각 특허문헌에 개시된 발수제 조성물로부터 제작된 발수막은 발수성은 우수하지만, 막 표면에 있어서의 물방울의 활수성이 불충분하다.The water repellent film produced from the water repellent composition disclosed in each of these patent documents is excellent in water repellency, but the water repellency of the water droplet on the film surface is insufficient.
따라서, 당해 발수막을 자동차의 창유리에 적용하는 경우에는, 강우 시에 있어서의 양호한 시계를 확보하기 위해, 더한층의 활수성의 개선이 요구된다.Therefore, when the water repellent film is applied to a window pane of an automobile, it is required to further improve the wettability in order to secure a good watch at the time of rainfall.
이 점에서, 양호한 발수성과 활수성을 겸비한 발수 도포막을 주는 조성물로서, 특허문헌 7에는, 직쇄 편말단 작용성 폴리다이메틸실록세인 화합물과 실레인 커플링제를 포함하는 조성물이 제안되었다.From this point of view, as a composition for imparting a water-repellent coating film having good water repellency and water-activatability, Patent Document 7 proposes a composition comprising a straight-chain terminal functional polydimethylsiloxane compound and a silane coupling agent.
그러나, 특허문헌 7의 조성물로 형성된 발수막은 내구성이 충분하지 않다고 하는 문제가 있어, 내수성이나 내마모성을 충분히 발현시킬 수 없고, 또한 장기에 걸쳐 발수성을 유지하는 것이 곤란했다.However, the water-repellent film formed of the composition of Patent Document 7 has a problem that the durability is not sufficient, and thus the water resistance and abrasion resistance can not be sufficiently exhibited and it is difficult to maintain the water repellency over a long period of time.
본 발명은 상기 사정을 감안하여 이루어진 것으로, 발수성, 활수성 및 내구성이 우수한 피막을 형성할 수 있는 유기 규소 화합물 및 그것을 포함하는 표면처리제 조성물, 및 당해 조성물에 의한 표면처리로 형성된 발수막 부착 기재 및 당해 조성물을 사용한 발수막의 형성 방법을 제공하는 것을 목적으로 한다.The present invention has been made in view of the above circumstances, and it is an object of the present invention to provide an organosilicon compound capable of forming a coating film excellent in water repellency, fluidity and durability and a surface treatment agent composition containing the organosilicon compound and a water- And a method for forming a water repellent film using the composition.
본 발명자는 상기 과제를 해결하기 위해 예의 검토한 결과, 특정 연결기, 가수분해성 기, 및 실록시기를 갖는 유기 규소 화합물을 포함하는 조성물이 가열하지 않고 실온에서 경화하여, 발수성, 활수성 및 내구성이 우수한 피막을 공급하는 것을 발견하고, 본 발명을 완성하였다.As a result of intensive studies for solving the above problems, the present inventors have found that a composition comprising an organosilicon compound having a specific linking group, a hydrolyzable group and a siloxy group is cured at room temperature without heating to exhibit excellent water repellency, And the present invention has been completed.
즉, 본 발명은,That is,
1. 일반식 (1)로 표시되는 것을 특징으로 하는 유기 규소 화합물,1. An organosilicon compound represented by the general formula (1)
{식 중, R1은, 서로 독립하여, 탄소 원자수 1∼12의 알킬기 또는 식 (2)로 표시되는 기를 나타내고,(Wherein R 1 represents, independently of each other, an alkyl group having 1 to 12 carbon atoms or a group represented by formula (2)
[식 중, R4는, 서로 독립하여, 탄소 원자수 1∼12의 알킬기 또는 식 (3)으로 표시되는 기를 나타낸다.[Wherein R 4 independently represents an alkyl group having 1 to 12 carbon atoms or a group represented by formula (3).
(식 중, R5는, 서로 독립하여, 탄소 원자수 1∼12의 알킬기를 나타낸다.)](Wherein R 5 , independently of each other, represents an alkyl group having 1 to 12 carbon atoms)]]
R2는, 서로 독립하여, 탄소 원자수 1∼12의 알킬기를 나타내고, R3은, 서로 독립하여, 탄소 원자수 1∼4의 알킬기를 나타내고, X는, 서로 독립하여, 하이드록시기 또는 가수분해성 기를 나타내고, Y는 아릴렌기 또는 불화 알킬렌기를 함유하는 2가 연결기를 나타내고, a는 1∼100의 수를 나타내고, b는 0∼2의 수를 나타낸다.}R 2 represents, independently of each other, an alkyl group of 1 to 12 carbon atoms, R 3 represents, independently of each other, an alkyl group of 1 to 4 carbon atoms and X represents, independently of each other, A represents a number of from 1 to 100, and b represents a number of from 0 to 2. < RTI ID = 0.0 > A < / RTI >
2. 상기 Y가 식 (4)로 표시되는 2가 연결기인 1의 유기 규소 화합물,2. The organosilicon compound of claim 1, wherein Y is a divalent linking group represented by formula (4)
[식 중, Z는 식 (5)∼(7)로부터 선택되는 어느 1개의 2가 연결기를 나타내고, R6 및 R7은, 서로 독립하여, 단결합 또는 Z와 상이한 2가 연결기를 나타낸다.Wherein Z represents any one divalent linking group selected from the formulas (5) to (7), and R 6 and R 7 independently represent a single bond or a divalent linking group different from Z.
(식 (5) 중, c는 1∼10의 수를 나타내고, 식 (7) 중, R8은, 서로 독립하여, 탄소 원자수 1∼12의 알킬기를 나타낸다.)](In the formula (5), c represents a number of 1 to 10, and in the formula (7), R 8 independently represent an alkyl group having 1 to 12 carbon atoms.)]
3. 식 (8) 또는 식 (9)로 표시되는 2의 유기 규소 화합물,3. Organosilicon compounds of the formula (2) represented by the formula (8) or (9)
[식 중, Z는 식 (5)∼(7)로부터 선택되는 어느 1개의 2가 연결기를 나타내고, R3, R6, R7, X, a 및 b는 상기와 동일한 의미를 나타낸다.Wherein Z represents any one of divalent linking groups selected from the formulas (5) to (7), and R 3 , R 6 , R 7 , X, a and b have the same meanings as defined above.
(식 (5) 중, c는 상기와 동일한 의미를 나타내고, 식 (7) 중, R8은 메틸기를 나타낸다.)](In the formula (5), c has the same meaning as defined above, and in the formula (7), R 8 represents a methyl group.)]
4. 상기 R6 및 R7이 서로 독립하여 식 (10)으로 표시되는 2 또는 3의 유기 규소 화합물,4. The organic silicon compound of the above R 6 and R 7 are independently 2 or 3 is represented by the formula (10) with each other,
(식 중, d는 0∼10의 수를 나타낸다.)(Wherein d represents the number of 0 to 10).
5. 상기 X가 하이드록시기, 알콕시기, 할로젠 원자 또는 아이소사이아네이트기인 1∼4 중 어느 하나의 유기 규소 화합물,5. The organosilicon compound according to any one of 1 to 4, wherein X is a hydroxyl group, an alkoxy group, a halogen atom or an isocyanate group,
6. 1∼5 중 어느 하나의 유기 규소 화합물의 가수분해 축합물,6. A hydrolysis-condensation product of any one of organosilicon compounds 1 to 5,
7. 1∼5 중 어느 하나의 유기 규소 화합물, 그 가수분해 축합물, 또는 그것들의 혼합물과, 유기 용제를 포함하는 표면처리제 조성물,7. A surface treatment composition comprising any one of organosilicon compounds, hydrolysis-condensation products thereof, mixtures thereof, and an organic solvent,
8. 메테인설폰산, p-톨루엔설폰산 및 황산으로부터 선택되는 적어도 1종의 가수분해 촉매를 함유하는 7의 표면처리제 조성물,8. A surface treatment agent composition according to 7, which contains at least one hydrolysis catalyst selected from methanesulfonic acid, p-toluenesulfonic acid and sulfuric acid,
9. 1∼5 중 어느 하나의 유기 규소 화합물 이외의, 그 밖의 가수분해성 기를 갖는 유기 규소 화합물, 그 가수분해 축합물, 또는 그것들의 혼합물을 함유하는 7 또는 8의 표면처리제 조성물,9. A surface treatment composition of 7 or 8 containing an organosilicon compound having a hydrolyzable group other than any one of the organosilicon compounds 1 to 5, a hydrolysis-condensation product thereof, or a mixture thereof,
10. 수송기용 유리의 발수 처리용인 7∼9 중 어느 하나의 표면처리제 조성물,10. A surface treatment composition according to any one of 7 to 9 for water-repellent treatment of glass for transportation,
11. 수송기용 보디의 발수 처리용인 7∼9 중 어느 하나의 표면처리제 조성물,11. A surface treatment composition according to any one of 7 to 9 for water-repellent treatment of a body for a transporter,
12. 기재와, 이 기재 위에 설치된, 7∼9 중 어느 하나의 표면처리제 조성물을 사용하여 이루어지는 발수막을 갖는 발수막 부착 기재,12. A water-repellent film-adhered substrate having a water-repellent film formed by using a substrate and any one of the surface treating agent compositions of 7 to 9 provided on the substrate,
13. 상기 기재와 발수막 사이에 개재하는 하지층을 구비하고, 상기 하지층이 1∼5 중 어느 하나의 유기 규소 화합물 이외의, 그 밖의 가수분해성 기를 갖는 유기 규소 화합물의 가수분해 생성물로 이루어지는 11의 발수막 부착 기재,13. A process for producing a water-repellent film comprising a base layer interposed between the substrate and a water-repellent film, wherein the base layer comprises a hydrolysis product of an organic silicon compound other than any one of the organic silicon compounds 1 to 5 Water-repellent film-attached substrate,
14. 상기 기재가 유리, 금속, 세라믹 또는 수지인 12 또는 13의 발수막 부착 기재,14. A water-repellent film-adhered substrate of 12 or 13 wherein the substrate is glass, metal, ceramic or resin,
15. 기재 위에, 7∼9 중 어느 하나의 표면처리제 조성물을 도포하여 도포막을 형성하고, 이 도포막 표면을 물로 닦아 내어 처리한 후, 5∼35℃에서 경화 피막을 형성하는 발수막의 형성 방법15. A method for forming a water-repellent film, which comprises applying a surface treatment composition of any one of 7 to 9 on a substrate to form a coating film, wiping the surface of the coating film with water to form a cured film at 5 to 35 캜
을 제공한다..
본 발명에 의하면, 실온 경화가 가능하며, 발수성, 활수성 및 내구성이 우수한 피막을 형성할 수 있는 유기 규소 화합물 및 이것을 포함하는 표면처리제 조성물을 제공할 수 있다.According to the present invention, it is possible to provide an organosilicon compound capable of being cured at room temperature and capable of forming a coating film excellent in water repellency, lubricity and durability, and a surface treatment agent composition containing the organosilicon compound.
본 발명의 표면처리제 조성물을 사용함으로써, 발수성, 활수성 및 내구성이 우수한 발수막 부착 기재를 간편한 방법으로 제작할 수 있다.By using the surface treatment agent composition of the present invention, a water-repellent film-adhered base excellent in water repellency, flowability and durability can be produced by a simple method.
특히, 차량용, 선박용 및 항공기용의 창유리나 미러 등으로서 사용되는 투명 기재에 본 발명의 발수막을 적용함으로써, 우수한 발수성 및 활수성을 부여할 수 있는 결과, 강우 시에도 양호한 시계를 확보할 수 있게 된다.In particular, by applying the water repellent film of the present invention to a transparent substrate used as a window glass or a mirror for a vehicle, a ship, and an aircraft, excellent water repellency and lubricity can be imparted, and as a result, .
(발명을 실시하기 위한 형태)(Mode for carrying out the invention)
이하, 본 발명에 대해 구체적으로 설명한다.Hereinafter, the present invention will be described in detail.
본 발명에 따른 유기 규소 화합물은 식 (1)로 표시된다.The organosilicon compound according to the present invention is represented by the formula (1).
식 (1)에 있어서, R1은, 서로 독립하여, 탄소 원자수 1∼12의 알킬기 또는 식 (2)로 표시되는 기를 나타내고, R2는, 서로 독립하여, 탄소 원자수 1∼12의 알킬기를 나타내고, R3은, 서로 독립하여, 탄소 원자수 1∼4의 알킬기를 나타낸다.In formula (1), R 1 independently represents an alkyl group having 1 to 12 carbon atoms or a group represented by formula (2), R 2 is an alkyl group having 1 to 12 carbon atoms And R 3 independently represent an alkyl group having 1 to 4 carbon atoms.
또한, a는 1∼100의 수이지만, 경화 피막의 활수성 향상의 관점에서, a는 5∼50의 수가 바람직하다. 또한, a가 100을 초과하면, 얻어지는 경화 피막의 내구성이 저하된다.In addition, a is a number of 1 to 100, and a is preferably 5 to 50 from the viewpoint of improving the curability of the cured coating. When a exceeds 100, the durability of the resulting cured coating is deteriorated.
b는 0∼2의 수이지만, 0 또는 1이 바람직하고, 0이 보다 바람직하다. 또한, b가 2를 초과하면, 얻어지는 경화 피막의 내구성이 불충분하게 된다.b is a number of 0 to 2, but 0 or 1 is preferable, and 0 is more preferable. When b is more than 2, the durability of the resulting cured coating becomes insufficient.
(R4는, 서로 독립하여, 탄소 원자수 1∼12의 알킬기 또는 식 (3)으로 표시되는 기를 나타낸다.)(R 4 represents, independently of each other, an alkyl group having 1 to 12 carbon atoms or a group represented by formula (3)).
(R5는, 서로 독립하여, 탄소 원자수 1∼12의 알킬기를 나타낸다.)(R 5 is, independently from each other, represents an alkyl group of 1 to 12 carbon atoms.)
상기 R1, R2, R4 및 R5에 있어서의 탄소 원자수 1∼12의 알킬기로서는 직쇄상, 환상, 분지상의 어떤 것이어도 되고, 그 구체예로서는 메틸, 에틸, n-프로필, i-프로필, n-뷰틸, s-뷰틸, t-뷰틸, n-펜틸, n-헥실, n-헵틸, n-옥틸, n-노닐, n-데실, n-운데실, n-도데실, 사이클로프로필, 사이클로뷰틸, 사이클로펜틸, 사이클로헥실, 사이클로헵틸, 사이클로옥틸기 등을 들 수 있다.The alkyl group having 1 to 12 carbon atoms in R 1 , R 2 , R 4 and R 5 may be any of linear, cyclic, and branched, and specific examples thereof include methyl, ethyl, n- N-pentyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, , Cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl group and the like.
상기 R3에 있어서의 탄소 원자수 1∼4의 알킬기로서는 직쇄상, 환상, 분지상의 어떤 것이어도 되고, 그 구체예로서는 메틸, 에틸, n-프로필, i-프로필, n-뷰틸, s-뷰틸, t-뷰틸, 사이클로프로필, 사이클로뷰틸기 등을 들 수 있다.The alkyl group having 1 to 4 carbon atoms in R 3 may be any of linear, cyclic and branched, and specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n- , t-butyl, cyclopropyl, and cyclobutyl groups.
본 발명에 있어서, 상기 R1, R2, R4 및 R5로서는 발수성, 활수성 및 원료 입수의 용이성의 관점에서, 탄소 원자수가 8 이하의 알킬기가 바람직하고, 특히 메틸기가 바람직하다. 또한, 이들 탄소 원자수가 12를 초과하면, 발수성 및 활수성이 저하되는 경우가 있다.In the present invention, as the above-mentioned R 1 , R 2 , R 4 and R 5 , an alkyl group having 8 or less carbon atoms is preferable, and a methyl group is particularly preferable from the viewpoints of water repellency, fluidity and easiness of obtaining a raw material. When the number of carbon atoms exceeds 12, the water repellency and the water activity may be lowered.
또한, R3은 메틸, 에틸기가 바람직하고, 특히 메틸기가 바람직하다.R 3 is preferably a methyl group or an ethyl group, particularly preferably a methyl group.
X는, 서로 독립하여, 하이드록시기 또는 가수분해성 기를 나타내고, X가 가수분해성 기인 경우, 본 발명의 유기 규소 화합물은 분자 말단의 Si 원자에 결합한 가수분해성 기가 가수분해함으로써 형성되는 실란올기(≡Si-OH)에 의해, 내구성이 있는 피막을 형성한다.X is independently a hydroxyl group or a hydrolyzable group, and when X is a hydrolyzable group, the organosilicon compound of the present invention has a silanol group (≡Si) formed by hydrolysis of a hydrolyzable group bonded to a Si atom at the molecular end -OH) to form a durable film.
이러한 가수분해성 기의 구체예로서는 메톡시, 에톡시, n-프로폭시, n-뷰톡시기 등의 알콕시기, 염소 원자 등의 할로젠 원자, 아이소사이아네이트기 등을 들 수 있지만, 이것들 중에서도, 특히 메톡시기, 염소 원자가 바람직하다.Specific examples of such hydrolysable groups include alkoxy groups such as methoxy, ethoxy, n-propoxy and n-butoxy groups, halogen atoms such as chlorine atoms, and isocyanate groups. Of these, A methoxy group, and a chlorine atom are preferable.
Y는 얻어지는 도포막에 있어서의 분자의 배향성을 향상시켜, 경화 피막의 치밀화, 균일화를 촉진시키기 위한 기이며, 특히, π-π 스택이나 수소 결합 등에 의한 상호 작용성이 있는 작용기나, 강직 구조를 취하는 원자단을 함유하는 2가 연결기를 적합하게 사용할 수 있다. 이들 2가 연결기를 분자 내의 특정 위치에 도입함으로써, 경화 피막의 발수성 및 활수성을 양호하게 유지하면서, 내구성을 더욱 향상시킬 수 있다.Y is a group for promoting the densification and uniformization of the cured film by improving the orientation of the molecules in the resulting coating film. Particularly, a functional group having an interactivity by a π-π stack or hydrogen bonding or a rigid structure A divalent linking group containing an atomic group to be taken is suitably used. By introducing these divalent linking groups at specific positions in the molecule, the durability can be further improved while satisfactorily maintaining the water repellency and the fluidity of the cured coating.
본 발명에서는, 이러한 2가 연결기로서, 아릴렌기 또는 불화 알킬렌기를 함유하는 2가 연결기를 채용한다.In the present invention, as such a divalent linking group, a divalent linking group containing an arylene group or an alkylene fluoride group is employed.
아릴렌기의 구체예로서는 페닐렌, 바이페닐렌, 나프틸렌기 등을 들 수 있다.Specific examples of the arylene group include phenylene, biphenylene, naphthylene and the like.
불화 알킬렌기의 구체예로서는 -(CHF)c-, -(CF2)c-(c는 1∼100의 수를 나타낸다.) 등을 들 수 있다.Specific examples of the fluorinated alkylene group include - (CHF) c -, - (CF 2 ) c - (c represents a number of 1 to 100), and the like.
본 발명에서, 피막 중의 분자의 배향성을 보다 높이고, 경화 피막의 치밀화, 균일화를 더한층 촉진시키는 것을 고려하면, 상기 Y로서는, 특히, 식 (4)로 표시되는 2가 연결기가 적합하다.In the present invention, the divalent linking group represented by the formula (4) is particularly suitable as the Y, considering that the orientation of the molecules in the film is further enhanced and the densification and uniformization of the cured film are further promoted.
여기에서, Z는 식 (5)∼(7)로부터 선택되는 어느 1개의 2가 연결기를 나타내고, 기재 위에서의 분자의 배향성을 향상시켜, 경화 피막의 치밀화, 균일화를 촉진시키는 기이다. 이들 연결기를 분자 내의 특정 위치에 도입함으로써, 경화 피막의 발수성 및 활수성을 양호하게 유지하면서, 또한 내구성을 향상할 수 있다.Here, Z represents any one of divalent linking groups selected from the formulas (5) to (7), and improves the orientation of the molecules on the substrate to promote densification and uniformity of the cured coating. By introducing these linking groups at specific positions in the molecule, durability can be improved while satisfactorily maintaining the water repellency and the fluidity of the cured coating.
그중에서도, 식 (5)로 표시되는 퍼플루오로알킬렌기가 바람직하다. 식 (5)에 있어서, c는 1∼10의 수이지만, 1∼8이 바람직하고, 1∼6이 보다 바람직하다.Among them, a perfluoroalkylene group represented by the formula (5) is preferable. In the formula (5), c is a number of 1 to 10, preferably 1 to 8, and more preferably 1 to 6.
또한, 식 (7)에 있어서의, R8의 탄소 원자수 1∼12의 알킬기로서는 상기와 동일한 것을 들 수 있지만, 특히 메틸기가 바람직하다.The alkyl group having 1 to 12 carbon atoms represented by R < 8 > in the formula (7) may be the same as described above, but a methyl group is particularly preferable.
(식 (7) 중, R8은, 서로 독립하여, 탄소 원자수 1∼12의 알킬기를 나타내고, c는 1∼10의 수를 나타낸다.)(In the formula (7), R 8 , independently of each other, represents an alkyl group of 1 to 12 carbon atoms, and c represents a number of 1 to 10.)
R6 및 R7은, 서로 독립하여, 단결합 또는 Z와 상이한 2가 연결기를 나타내고, 이러한 2가 연결기로서는 상술한 Z와 다른 것이면 특별히 한정되는 것은 아니고, 그 구체예로서는 에터 결합(-O-), 싸이오에터 결합(-S-), 이미노기(-NH-) 등의 헤테로 원자를 개재해도 되는 알킬렌기 등을 들 수 있다.R 6 and R 7 independently represent a single bond or a divalent linking group different from Z, and the divalent linking group is not particularly limited as long as it is different from Z described above, and specific examples thereof include an ether linkage (-O-) , A thioether bond (-S-), an imino group (-NH-), and the like.
이것들 중에서도, R6 및 R7로서는 모두 식 (10)으로 표시되는 기가 적합하다.Among them, R 6 and R 7 are all groups represented by the formula (10).
식 (10)에 있어서, d는 0∼10의 수이지만, 0∼5가 바람직하고, 0∼3이 보다 바람직하고, 1∼3이 더한층 바람직하고, 상기 유기 규소 화합물의 제조의 용이성 및 입수의 염가성을 고려하면, 에틸렌, 트라이메틸렌기가 적합하다.In the formula (10), d is a number of 0 to 10, preferably 0 to 5, more preferably 0 to 3, further preferably 1 to 3, and the ease of production and availability of the organosilicon compound Considering the low cost, ethylene and trimethylene groups are suitable.
(식 중, d는 0∼10의 수를 나타낸다.)(Wherein d represents the number of 0 to 10).
따라서, 본 발명의 유기 규소 화합물은 일반식 (1')으로 표시되는 것이 바람직하고, 식 (8), (9) 및 (11)로 표시되는 것이 보다 바람직하다.Therefore, the organosilicon compound of the present invention is preferably represented by the general formula (1 '), more preferably represented by the formulas (8), (9) and (11).
(식 중, R1∼R3, R6, R7, X, Z, a 및 b는 상기와 동일한 의미를 나타낸다.)(Wherein R 1 to R 3 , R 6 , R 7 , X, Z, a and b have the same meanings as defined above)
식 중, Z는 식 (5)∼(7)로부터 선택되는 어느 1개의 2가 연결기를 나타내고, R3, R6, R7, X, a 및 b는 상기와 동일한 의미를 나타낸다.Z represents any one of divalent linking groups selected from the formulas (5) to (7), and R 3 , R 6 , R 7 , X, a and b have the same meanings as defined above.
(식 (5) 중, c는 상기와 동일한 의미를 나타내고, 식 (7) 중, R8은 메틸기를 나타낸다.)](In the formula (5), c has the same meaning as defined above, and in the formula (7), R 8 represents a methyl group.)]
적합한 유기 규소 화합물로서, 예를 들면, 이하와 같은 화합물을 들 수 있지만, 이것들에 한정되는 것은 아니다.Suitable organic silicon compounds include, for example, the following compounds, but are not limited thereto.
본 발명의 유기 규소 화합물은 공지의 방법으로 합성할 수 있다. 예를 들면, 상기 식 (1')으로 표시되는 유기 규소 화합물은 하기 반응식 (A), (B)에 나타내어지는 바와 같이, 공지의 하이드로실릴화 반응에 의해 합성할 수 있다.The organosilicon compound of the present invention can be synthesized by a known method. For example, the organosilicon compound represented by the formula (1 ') can be synthesized by a known hydrosilylation reaction as shown in the following reaction formulas (A) and (B).
상기 하이드로실릴화 반응에 사용되는 백금 화합물 함유 촉매로서는 특별히 한정되는 것은 아니고, 그 구체예로서는 염화백금산, 염화백금산의 알코올 용액, 백금-1,3-다이바이닐-1,1,3,3-테트라메틸다이실록세인 착체의 톨루엔 또는 자일렌 용액, 테트라키스트라이페닐포스핀백금, 다이클로로비스트라이페닐포스핀백금, 다이클로로비스아세토나이트릴백금, 다이클로로비스벤조나이트릴백금, 다이클로로사이클로옥타다이엔백금 등이나, 백금-탄소, 백금-알루미나, 백금-실리카 등의 담지 촉매 등을 들 수 있다.The platinum compound-containing catalyst used in the hydrosilylation reaction is not particularly limited, and specific examples thereof include chloroplatinic acid, an alcohol solution of chloroplatinic acid, platinum-1,3-divinyl-1,1,3,3-tetramethyl A toluene or xylene solution of a dicyloxane complex, tetrakis triphenylphosphine platinum, dichlorobistriphenylphosphine platinum, dichlorobisacetonitrile platinum, dichlorobisbenzonitrile platinum, dichlorocyclooctadiene Platinum and the like, supported catalysts such as platinum-carbon, platinum-alumina, and platinum-silica.
하이드로실릴화 시의 선택성의 면에서, 0가의 백금 착체가 바람직하고, 백금-1,3-다이바이닐-1,1,3,3-테트라메틸다이실록세인 착체의 톨루엔 또는 자일렌 용액이 보다 바람직하다.From the viewpoint of selectivity at the time of hydrosilylation, a zero-valent platinum complex is preferable, and a toluene or xylene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex is more preferable Do.
백금 화합물 함유 촉매의 사용량은 특별히 한정되는 것은 아니지만, 반응성이나, 생산성 등의 점에서, Si-H기를 갖는 유기 규소 화합물 1mol에 대하여, 함유되는 백금 원자가 1×10-7∼1×10-2mol이 되는 양이 바람직하고, 1×10-7∼1×10-3mol이 되는 양이 보다 바람직하다.The amount of the platinum compound-containing catalyst to be used is not particularly limited. However, from the viewpoints of reactivity and productivity, the amount of the platinum atom contained in 1 mol of the Si-H group-containing organosilicon compound ranges from 1 x 10 -7 to 1 x 10 -2 mol , And more preferably 1 x 10 < -7 > to 1 x 10 < -3 > mol.
또한, 상기 반응은 무용매로도 진행하지만, 용매를 사용할 수도 있다.In addition, the above reaction proceeds without solvent, but a solvent may also be used.
사용 가능한 용매의 구체예로서는 펜테인, 헥세인, 사이클로헥세인, 헵테인, 아이소옥테인, 벤젠, 톨루엔, 자일렌 등의 탄화수소계 용매; 다이에틸에터, 테트라하이드로퓨란, 다이옥세인 등의 에터계 용매; 아세트산 에틸, 아세트산 뷰틸 등의 에스터계 용매; N,N-다이메틸폼아마이드 등의 비프로톤성 극성 용매; 다이클로로메테인, 클로로폼 등의 염소화 탄화수소계 용매 등을 들 수 있고, 이들 용매는 1종을 단독으로 사용해도, 2종 이상을 혼합하여 사용해도 된다.Specific examples of usable solvents include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene and xylene; Ether solvents such as diethyl ether, tetrahydrofuran and dioxane; Ester solvents such as ethyl acetate and butyl acetate; Aprotic polar solvents such as N, N-dimethylformamide; And chlorinated hydrocarbon solvents such as dichloromethane and chloroform. These solvents may be used singly or in combination of two or more kinds.
상기 하이드로실릴화 반응에 있어서의 반응온도는 특별히 한정되는 것은 아니고, 0℃로부터 가열하에서 행할 수 있지만, 0∼200℃가 바람직하다.The reaction temperature in the hydrosilylation reaction is not particularly limited and can be carried out under heating from 0 占 폚, preferably 0 to 200 占 폚.
적당한 반응속도를 얻기 위해서는 가열하에서 반응시키는 것이 바람직하고, 이러한 관점에서, 반응온도는 40∼110℃가 보다 바람직하고, 60∼100℃가 더한층 바람직하다.In order to obtain an appropriate reaction rate, the reaction is preferably carried out under heating. From this viewpoint, the reaction temperature is more preferably 40 to 110 占 폚, and further preferably 60 to 100 占 폚.
또한, 반응시간도 특별히 한정되는 것은 아니고, 통상, 1∼60시간 정도이지만, 1∼30시간이 바람직하고, 1∼20시간이 보다 바람직하다.The reaction time is not particularly limited, but is usually about 1 to 60 hours, preferably 1 to 30 hours, more preferably 1 to 20 hours.
본 발명의 표면처리제 조성물은 상술한 유기 규소 화합물, 그 가수분해 축합물, 또는 그것들의 혼합물과, 유기 용제를 포함하여 구성된다.The surface treatment agent composition of the present invention comprises the aforementioned organic silicon compound, a hydrolyzed condensate thereof, or a mixture thereof and an organic solvent.
사용 가능한 유기 용제의 구체예로서는 아세트산 에틸, 아세트산 프로필, 아세트산 아이소프로필, 아세트산 뷰틸, 아세트산 아이소뷰틸 등의 에스터류; 헥세인, 사이클로헥세인, 헵테인, 옥테인, 데케인, 도데케인, 톨루엔, 자일렌 등의 탄화수소류; 다이클로로메테인, 1,1-다이클로로에테인, 1,2-다이클로로에테인 등의 할로젠화 탄화수소류; 메틸에틸케톤, 2-펜탄온, 메틸아이소뷰틸케톤 등의 케톤류; 다이에틸렌글라이콜모노메틸에터, 다이프로필렌글라이콜모노메틸에터 등의 에터류; 에탄올, 1-프로판올, 2-프로판올, 1-뷰탄올, 2-뷰탄올, 아이소뷰틸알코올 등의 알코올류 등을 들 수 있고, 이것들은 1종 단독으로 사용해도, 2종 이상을 조합하여 사용해도 된다.Specific examples of usable organic solvents include esters such as ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, and isobutyl acetate; Hydrocarbons such as hexane, cyclohexane, heptane, octane, decane, dodecane, toluene and xylene; Halogenated hydrocarbons such as dichloromethane, 1,1-dichloroethane and 1,2-dichloroethane; Ketones such as methyl ethyl ketone, 2-pentanone, and methyl isobutyl ketone; Ethers such as diethylene glycol monomethyl ether and dipropylene glycol monomethyl ether; And alcohols such as ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol and isobutyl alcohol. These may be used singly or in combination of two or more do.
표면처리제 조성물 중에 포함되는 본 발명의 유기 규소 화합물의 농도는 특별히 한정되는 것은 아니지만, 조성물 전체에 대하여, 0.1∼20질량%가 바람직하고, 0.5∼10질량%가 보다 바람직하고, 0.5∼5.0질량%가 더한층 바람직하고, 이 범위로 함으로써 도포막 자체에 균일하고 우수한 발수성, 활수성을 줄 수 있다.The concentration of the organosilicon compound of the present invention contained in the surface treatment agent composition is not particularly limited, but is preferably 0.1 to 20 mass%, more preferably 0.5 to 10 mass%, more preferably 0.5 to 5.0 mass% By weight, more preferably within this range, uniform and excellent water repellency and fluidity can be imparted to the coating film itself.
또한, 본 발명의 표면처리제 조성물에는, 유기 규소 화합물이 갖는 가수분해성 기와 물과의 반응을 촉진하고, 실란올기의 생성을 촉진할 목적으로 가수분해 촉매가 포함되어 있어도 된다.The surface treatment agent composition of the present invention may contain a hydrolysis catalyst for the purpose of accelerating the reaction between the hydrolyzable group of the organosilicon compound and water and promoting the production of silanol groups.
가수분해 촉매의 구체예로서는 아세트산, 폼산, 메테인설폰산, p-톨루엔설폰산 등의 유기산; 염산, 질산, 황산 등의 무기산을 들 수 있고, 이것들은 단독으로 사용해도, 2종 이상 조합하여 사용해도 된다.Specific examples of the hydrolysis catalyst include organic acids such as acetic acid, formic acid, methanesulfonic acid and p-toluenesulfonic acid; And inorganic acids such as hydrochloric acid, nitric acid, and sulfuric acid. These may be used alone or in combination of two or more.
이것들 중에서도, 메테인설폰산, p-톨루엔설폰산, 황산이 바람직하고, 특히 황산이 바람직하다.Of these, methanesulfonic acid, p-toluenesulfonic acid and sulfuric acid are preferable, and sulfuric acid is particularly preferable.
촉매의 농도는, 유기 규소 화합물에 대하여, 0.1∼15.0질량%가 바람직하고, 1.0∼10.0질량%가 보다 바람직하다.The concentration of the catalyst is preferably 0.1 to 15.0 mass%, more preferably 1.0 to 10.0 mass%, with respect to the organosilicon compound.
또한, 본 발명의 표면처리제 조성물은 경화 촉매를 포함하고 있어도 된다.Further, the surface treatment agent composition of the present invention may contain a curing catalyst.
경화 촉매의 구체예로서는 타이타늄테트라아이소프로폭사이드, 타이타늄테트라노말뷰톡사이드, 타이타늄테트라-2-에틸헥스옥사이드, 타이타늄테트라아세틸아세토네이트 등의 타이타늄 촉매; 다이뷰틸주석다이라우레이트, 다이뷰틸주석다이아세테이트, 다이옥틸주석다이아세테이트 등의 주석 촉매; 알루미늄세컨더리뷰톡사이드, 알루미늄트리스아세틸아세토네이트, 알루미늄비스에틸아세토아세테이트모노아세틸아세토네이트, 알루미늄트리스에틸아세토아세테이트 등의 알루미늄 촉매; 노말프로필지르코네이트, 노말뷰틸지르코네이트, 지르코늄테트라아세틸아세토네이트, 지르코늄테트라아세틸아세토네이트, 지르코늄모노아세틸아세토네이트, 지르코늄테트라아세틸아세토네이트 등의 지르코늄 촉매 등을 들 수 있다.Specific examples of the curing catalyst include titanium catalysts such as titanium tetraisopropoxide, titanium tetra-n-butoxide, titanium tetra-2-ethylhexoxide, and titanium tetraacetylacetonate; Tin catalysts such as dibutyltin dilaurate, dibutyltin diacetate, and dioctyltin diacetate; Aluminum catalysts such as aluminum secondary butoxide, aluminum tris acetylacetonate, aluminum bis ethylacetoacetate monoacetylacetonate and aluminum tris ethyl acetoacetate; And zirconium catalysts such as normal propyl zirconate, normal butyl zirconate, zirconium tetraacetylacetonate, zirconium tetraacetylacetonate, zirconium monoacetylacetonate, and zirconium tetraacetylacetonate.
촉매의 농도는, 유기 규소 화합물에 대하여, 0.1∼15.0질량%가 바람직하고, 1.0∼10.0질량%가 보다 바람직하다.The concentration of the catalyst is preferably 0.1 to 15.0 mass%, more preferably 1.0 to 10.0 mass%, with respect to the organosilicon compound.
본 발명의 표면처리제 조성물은, 상술한 본 발명의 유기 규소 화합물 이외의, Si 원자에 결합한 하이드록시기 또는 가수분해성 기를 갖는 그 밖의 유기 규소 화합물, 그 가수분해 축합물, 또는 그것들의 혼합물을 더 포함하고 있어도 된다.The surface treatment agent composition of the present invention further includes other organosilicon compounds having hydrolyzable groups or hydrolyzable groups bonded to Si atoms other than the above-described organosilicon compounds of the present invention, hydrolysis-condensation products thereof, or mixtures thereof .
가수분해성 기로서는 알콕시기, 할로젠 원자, 아실옥시기, 아이소사이아네이트기 등을 들 수 있다.Examples of the hydrolyzable group include an alkoxy group, a halogen atom, an acyloxy group, and an isocyanate group.
그 밖의 유기 규소 화합물의 구체예로서는 알콕시실릴기를 갖는 실레인 화합물로서 테트라메톡시실레인, 테트라에톡시실레인, 메틸트라이메톡시실레인, 메틸트라이에톡시실레인, 다이메틸다이메톡시실레인, 다이메틸다이에톡시실레인, 페닐트라이메톡시실레인, 페닐트라이에톡시실레인, n-프로필트라이메톡시실레인, n-프로필트라이에톡시실레인, 다이페닐다이메톡시실레인, 헥실트라이메톡시실레인, 헥실트라이에톡시실레인, 데실트라이메톡시실레인, 트라이플루오로프로필트라이메톡시실레인, 헥사메틸다이실라잔, 바이닐트라이메톡시실레인, 바이닐트라이에톡시실레인, 3-글라이시드옥시프로필트라이메톡시실레인, 3-메타크릴옥시프로필트라이메톡시실레인, 3-아크릴옥시프로필트라이메톡시실레인, 3-아미노프로필트라이메톡시실레인, 3-유레이도프로필트라이에톡시실레인, 3-머캡토프로필트라이메톡시실레인, 3-머캡토프로필메틸다이메톡시실레인, 비스(트라이에톡시실릴프로필)테트라설파이드, 3-아이소사이아네이트프로필트라이에톡시실레인 등을 들 수 있고, 할로젠화 실릴기를 갖는 실레인 화합물로서 메틸트라이클로로실레인, 에틸트라이클로로실레인, 다이메틸다이클로로실레인, 트라이메틸클로로실레인, 페닐트라이클로로실레인, 다이페닐다이클로로실레인, 트라이플루오로에틸트라이클로로실레인 등을 들 수 있다.Specific examples of other organosilicon compounds include silane compounds having an alkoxysilyl group such as tetramethoxysilane, tetraethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, dimethyldimethoxysilane, N-propyltrimethoxysilane, n-propyltriethoxysilane, diphenyldimethoxysilane, hexyltriethoxysilane, hexyltriethoxysilane, hexyltriethoxysilane, hexyltriethoxysilane, Hexyltrimethoxysilane, hexyltrimethoxysilane, hexyltrimethoxysilane, hexyltrimethoxysilane, hexyltrimethoxysilane, hexamethyldisilazane, vinyltrimethoxysilane, vinyltriethoxysilane, 3 -Glycidoxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3- 3-mercaptopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, bis (triethoxysilylpropyl) tetrasulfide, 3-isocyanate propyltrimethoxysilane, Triethoxysilane, and the like. As the silane compound having a halogenated silyl group, methyl trichlorosilane, ethyl trichlorosilane, dimethyl dichlorosilane, trimethyl chlorosilane, phenyl trichlorosilane Diphenyldichlorosilane, trifluoroethyl trichlorosilane, and the like.
그 밖의 유기 규소 화합물의 첨가량은 얻어지는 경화 피막의 발수성 및 활수성에 영향을 미치지 않는 양이면 특별히 제한은 없지만, 본 발명의 유기 규소 화합물에 대하여, 20질량% 이하가 바람직하다.The amount of other organosilicon compounds to be added is not particularly limited as long as the amount does not affect the water repellency and the fluidity of the resulting cured coating, but is preferably 20% by mass or less based on the organosilicon compound of the present invention.
또한, 본 발명의 표면처리제 조성물은, 이상에서 설명한 각 성분과 더불어, 각종 첨가제를 첨가할 수 있다.Further, in the surface treatment agent composition of the present invention, various additives may be added in addition to the components described above.
첨가제로서는 금속 산화물, 수지, 염료, 안료, 자외선흡수제, 산화방지제 등을 들 수 있고, 구체적으로는, 실리카졸, 티타니아졸, 알루미나졸 등을 들 수 있다.Examples of the additive include metal oxides, resins, dyes, pigments, ultraviolet absorbers and antioxidants. Specific examples thereof include silica sol, titania sol and alumina sol.
첨가제의 첨가량은 얻어지는 경화 피막의 발수성 및 활수성에 영향을 미치지 않는 양이면 특별히 제한은 없지만, 본 발명의 유기 규소 화합물에 대하여 30질량% 이하가 바람직하다.The amount of the additive to be added is not particularly limited as far as it does not affect the water repellency and the fluidity of the resulting cured film, but is preferably 30% by mass or less based on the organosilicon compound of the present invention.
이상에서 설명한 본 발명의 표면처리제 조성물을 기재에 도포하고, 건조시킴으로써 기재 위에 발수막을 형성할 수 있다.The water repellent film can be formed on the substrate by applying the surface treatment agent composition of the present invention described above to the substrate and drying the substrate.
기재로서는 유리, 금속, 세라믹, 수지 등을 적합하게 사용할 수 있다. 금속으로서는 철, 스테인리스 등을 들 수 있고, 세라믹으로서는 티타니아, 알루미나, 지르코니아 등을 들 수 있고, 수지로서는 폴리에틸렌, 폴리프로필렌, 폴리에틸렌테레프탈레이트, 폴리카보네이트, 염화바이닐, 폴리스타이렌, ABS 수지, 페놀 수지, 에폭시 수지, 아크릴 등을 들 수 있다.As the substrate, glass, metal, ceramic, resin, or the like can be suitably used. Examples of the ceramic include titanium, alumina and zirconia. Examples of the resin include polyethylene, polypropylene, polyethylene terephthalate, polycarbonate, vinyl chloride, polystyrene, ABS resin, phenol resin, epoxy Resin, acryl, and the like.
도포 방법으로서는 와이핑 도포, 스핀 코팅, 바 코팅, 침지 도포, 스키지 도포, 스프레이 도포 등의 종래 공지의 방법을 적당히 채용할 수 있다.As a coating method, conventionally known methods such as wiping coating, spin coating, bar coating, immersion coating, squeegee coating, spray coating and the like can be suitably employed.
도포 후의 건조는 자연 건조, 가열 건조의 어떤 것이어도 좋지만, 5∼150℃의 범위에서 행하는 것이 바람직하다. 5℃ 미만에서는 기재에의 본 발명의 유기 규소 화합물의 반응속도가 작아져, 반응에 시간을 요하여, 충분한 내구성이 얻어지지 않는 경우가 있다. 150℃를 초과하면 도포한 표면처리제 조성물의 변성이나 열 분해가 일어나기 쉬워, 충분한 발수성, 활수성이 얻어지지 않는 경우가 있다.Drying after application may be natural drying or heat drying, but it is preferably carried out in the range of 5 to 150 캜. If the temperature is less than 5 ° C, the reaction rate of the organosilicon compound of the present invention on the substrate becomes small, and the reaction may take time, resulting in insufficient durability. When the temperature is higher than 150 ° C, the applied surface treatment agent composition tends to undergo denaturation or thermal decomposition, resulting in poor water repellency and water fastness.
특히, 표면처리제 조성물을 기재 위에 도포한 후, 도포막 표면을 물로 닦아 내어 처리하는 것이 바람직하고, 경화 피막을 형성하는 온도는 실온 근방(5∼35℃)이 바람직하다.Particularly, it is preferable that the surface treatment composition is coated on the substrate, then the surface of the coated film is wiped off with water, and the temperature for forming the cured coating is preferably in the vicinity of room temperature (5 to 35 DEG C).
발수막의 막 두께는 특별히 한정되는 것은 아니지만, 투명성 및 막의 기계적 강도 등을 고려하면, 100nm 이하가 바람직하다.The thickness of the water-repellent film is not particularly limited, but it is preferably 100 nm or less in consideration of transparency and mechanical strength of the film.
또한, 상기 발수막은 2㎕ 물방울로 100° 이상의 수접촉각, 30° 이하의 전락 각을 갖는 것이 바람직하고, 헤이즈값(흐림값)이 바람직하게는 5 이하, 보다 바람직하게는 1 이하, 더한층 바람직하게는 0.5 이하의 투명성을 갖는 것이 바람직하다.The water-repellent film preferably has a water contact angle of 100 DEG or more and a tilting angle of 30 DEG or less with 2 mu l of water drops, and preferably has a haze value (fog value) of 5 or less, more preferably 1 or less, Has a transparency of 0.5 or less.
본 발명의 표면처리제 조성물은 기재 표면에 직접 도포하여 발수막(경화 피막)을 형성할 수도 있지만, 기재 표면과 발수막 사이에, 본 발명의 유기 규소 화합물 이외의, 가수분해성 기를 갖는 규소 화합물의 가수분해 생성물로 형성되는 하지층을 개재시키는 것이 바람직하다. 이러한 하지층을 설치함으로써, 발수막과 기재와의 결합이 보다 강고하게 되어, 본 발명의 발수막의 내구성이 향상된다.The surface treatment agent composition of the present invention may be applied directly to the surface of the substrate to form a water repellent film (cured film). However, it is preferable that a water-soluble film of a silicon compound having a hydrolyzable group other than the organic silicon compound of the present invention It is preferable to interpose a ground layer formed of decomposition products. By providing such a base layer, the bonding between the water-repellent film and the substrate becomes stronger, and the durability of the water-repellent film of the present invention is improved.
하지층 형성에 사용되는 유기 규소 화합물로서는 가수분해성이 높고, 실온 근방(5∼35℃)에서 기재 위에 박막을 형성한다고 하는 점을 고려하면, 하기 일반식 (12)로 표시되는 아이소사이아네이트실레인 화합물이 적합하다.Considering that a thin film is formed on a substrate in the vicinity of room temperature (5 to 35 캜), the organosilicon compound used for forming the base layer has a high hydrolyzability, and an isocyanate silane represented by the following general formula (12) Phosphorus compounds are suitable.
(식 중, k는 0 또는 1을 나타낸다.)(Wherein k represents 0 or 1).
이상에서 설명한 본 발명의 표면처리제 조성물로 이루어지는 막은 발수성, 활수성 및 투명성이 우수하기 때문에, 수송기용의 유리나 차체의 발수 처리에 적합하게 사용할 수 있다. 특히, 창유리나 미러에 적용한 경우, 우천시에 있어서의 물방울 부착에 의한 시인성 저하를 효율적으로 방지할 수 있다.The film made of the surface treatment agent composition of the present invention as described above is excellent in water repellency, fluidity and transparency, and thus can be suitably used for water-repellent treatment of glass for a transport machine or a car body. In particular, when applied to a window glass or a mirror, deterioration in visibility due to adhesion of water droplets during rain can be effectively prevented.
실시예Example
이하, 실시예 및 비교예를 들어 본 발명을 보다 구체적으로 설명하지만, 본 발명은 이들 실시예에 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited to these examples.
[1] 유기 규소 화합물의 합성[1] Synthesis of organosilicon compounds
[실시예 1-1] 유기 규소 화합물 (13)의 합성[Example 1-1] Synthesis of organosilicon compound (13)
교반기, 온도계, 에스터 어댑터 및 딤로스 냉각기 냉각관을 구비한 1리터의 3구 플라스크에, 톨루엔 23.8g, 화합물 (14) 5.05g(0.0225mol), 및 바이닐실록세인 배위 Pt의 톨루엔 용액(Pt 농도: 0.5질량%) 0.3g을 가하고, 80℃까지 승온하고, 다음에 80∼90℃로 유지하면서, 화합물 (15) 50.0g(0.0225mol)을 적하하고, 또한, 90℃에서 5시간 반응을 행했다. 알카리수 첨가에 의한 수소 가스 발생량 측정 및 IR 측정을 행하여, ≡Si-H기의 반응 완결을 확인했다.23.8 g of toluene, 5.05 g (0.0225 mol) of the compound (14), and a toluene solution of the vinylsiloxane coordination Pt (concentration of Pt (concentration of the Pt compound)) were added to a 1-liter three-necked flask equipped with a stirrer, a thermometer, : 0.5% by mass), and the temperature was raised to 80 占 폚. Then, 50.0 g (0.0225 mol) of the compound (15) was added dropwise while maintaining the temperature at 80 to 90 占 폚 and the reaction was further carried out at 90 占 폚 for 5 hours . Measurement of the amount of generated hydrogen gas by the addition of alkaline water and IR measurement were carried out to confirm the completion of the reaction of? Si-H group.
계속해서, 딤로스 냉각기 냉각관을 배기 가스관에 바꾸어 연결하고, 질소 가스 버블링하, 계 내 압력 10mmHg, 150℃에서 3시간 가열한 후, 25℃까지 냉각하고, 압력을 상압으로 복압한 후, 얻어진 액체를 여과 정제하여, 유기 규소 화합물 (13) 49.5g을 얻었다.Subsequently, the Dimrose cooler cooling tube was connected to an exhaust gas pipe and heated under a nitrogen gas bubbling pressure of 10 mmHg at 150 캜 for 3 hours, cooled to 25 캜, pressurized to normal pressure, The liquid was filtrated and purified to obtain 49.5 g of the organosilicon compound (13).
[실시예 1-2] 유기 규소 화합물 (16)의 합성[Example 1-2] Synthesis of organosilicon compound (16)
교반기, 온도계, 에스터 어댑터 및 딤로스 냉각기 냉각관을 구비한 1리터의 3구 플라스크에, 톨루엔 17.1g, 화합물 (18) 31.7g(0.0146mol), 및 바이닐실록세인 배위 Pt의 톨루엔 용액(Pt 농도: 0.5질량%) 0.3g을 가하고, 80℃까지 승온하고, 다음에 80∼90℃로 유지하면서, 화합물 (17) 5.0g(0.0146mol)을 적하하고, 또한 90℃에서 5시간 반응을 행했다. 여기에서, 합성예 1과 동일한 방법으로, Si-H기의 반응완결을 확인했다.17.1 g of toluene, 31.7 g (0.0146 mol) of the compound (18), and a toluene solution of the vinylsiloxane-coordinated Pt (concentration of Pt (concentration of the catalyst) were added to a 1-liter three-necked flask equipped with a stirrer, a thermometer, : 0.5% by mass), and the temperature was raised to 80 占 폚. Then, 5.0 g (0.0146 mol) of the compound (17) was added dropwise while maintaining the temperature at 80 to 90 占 폚 and the reaction was further carried out at 90 占 폚 for 5 hours. Here, the completion of the reaction of the Si-H group was confirmed in the same manner as in Synthesis Example 1.
딤로스 냉각기 냉각관을 배기 가스관에 바꾸어 연결하고, 질소 가스 버블링하, 계 내 압력 10mmHg, 150℃에서 3시간 가열한 후, 25℃까지 냉각하고, 압력을 상압으로 복압한 후, 얻어진 액체를 여과 정제하여, 유기 규소 화합물 (16) 33.0g을 얻었다.The dimox cooler cooling tube was connected to an exhaust gas pipe and heated under a nitrogen gas bubbling pressure of 10 mmHg at 150 캜 for 3 hours and then cooled to 25 캜 and pressurized to normal pressure, And purified to obtain 33.0 g of the organosilicon compound (16).
[실시예 1-3] 유기 규소 화합물 (19)의 합성[Example 1-3] Synthesis of organosilicon compound (19)
교반기, 온도계, 에스터 어댑터 및 딤로스 냉각기 냉각관을 구비한 1리터의 3구 플라스크에, 톨루엔 29.6g, 화합물 (20) 10.0g(0.0266mol), 및 바이닐실록세인 배위 Pt의 톨루엔 용액(Pt 농도: 0.5질량%) 0.3g을 가하고, 80℃까지 승온하고, 80∼90℃로 유지하면서, 화합물 (15) 59.1g(0.0266mol)을 적하하고, 또한 90℃에서 5시간 반응을 행했다. 여기에서, 합성예 1과 동일한 방법으로, Si-H기의 반응완결을 확인했다.A three-liter three-necked flask equipped with a stirrer, a thermometer, an ester adapter and a Dimroth condenser cooling tube was charged with 29.6 g of toluene, 10.0 g (0.0266 mol) of the compound (20), and a toluene solution of the vinylsiloxane- : 0.5% by mass), and the temperature was raised to 80 占 폚. 59.1 g (0.0266 mol) of the compound (15) was added dropwise while maintaining the temperature at 80 to 90 占 폚 and the reaction was further carried out at 90 占 폚 for 5 hours. Here, the completion of the reaction of the Si-H group was confirmed in the same manner as in Synthesis Example 1.
딤로스 냉각기 냉각관을 배기 가스관에 바꾸어 연결하고, 질소 가스 버블링하, 계 내 압력 10mmHg, 150℃에서 3시간 가열한 후, 25℃까지 냉각하고, 압력을 상압으로 복압한 후, 얻어진 액체를 여과 정제하여, 유기 규소 화합물 (29) 62.2g을 얻었다.The dimox cooler cooling tube was connected to an exhaust gas pipe and heated under a nitrogen gas bubbling pressure of 10 mmHg at 150 캜 for 3 hours and then cooled to 25 캜 and pressurized to normal pressure, And purified to obtain 62.2 g of the organosilicon compound (29).
[실시예 1-4] 유기 규소 화합물 (21)의 합성[Example 1-4] Synthesis of organosilicon compound (21)
교반기, 온도계, 에스터 어댑터 및 딤로스 냉각기 냉각관을 구비한 1리터의 3구 플라스크에, 톨루엔 22.4g, 화합물 (20) 8.57g(0.0228mol), 및 바이닐실록세인 배위 Pt의 톨루엔 용액(Pt 농도: 0.5질량%) 0.3g을 가하고, 80℃까지 승온하고, 80∼90℃로 유지하면서, 화합물 (22) 54.0g(0.0228mol)을 적하하고, 또한 90℃에서 5시간 반응했다. 여기에서, 합성예 1과 동일한 방법으로, Si-H기의 반응완결을 확인했다.22.4 g of toluene, 8.57 g (0.0228 mol) of the compound (20), and a toluene solution of the vinylsiloxane-coordinated Pt (concentration of Pt (concentration : 0.5% by mass), and the temperature was raised to 80 占 폚. 54.0 g (0.0228 mol) of the compound (22) was added dropwise while maintaining the temperature at 80 to 90 占 폚 and the mixture was reacted at 90 占 폚 for 5 hours. Here, the completion of the reaction of the Si-H group was confirmed in the same manner as in Synthesis Example 1.
딤로스 냉각기 냉각관을 배기 가스관에 바꾸어 연결하고, 질소 가스 버블링하, 계 내 압력 10mmHg, 150℃에서 3시간 가열한 후, 25℃까지 냉각하고, 압력을 상압으로 복압한 후, 얻어진 액체를 여과 정제하여, 유기 규소 화합물 (21) 56.7g을 얻었다.The dimox cooler cooling tube was connected to an exhaust gas pipe and heated under a nitrogen gas bubbling pressure of 10 mmHg at 150 캜 for 3 hours and then cooled to 25 캜 and pressurized to normal pressure, And purified to obtain 56.7 g of the organosilicon compound (21).
[실시예 1-5] 유기 규소 화합물 (23)의 합성[Example 1-5] Synthesis of organosilicon compound (23)
교반기, 온도계, 에스터 어댑터 및 딤로스 냉각기 냉각관을 구비한 1리터의 3구 플라스크에, 톨루엔 30.1g, 화합물 (20) 10.0g(0.0266mol), 및 바이닐실록세인 배위 Pt의 톨루엔 용액(Pt 농도: 0.5질량%) 0.3g을 가하고, 80℃까지 승온하고, 80∼90℃로 유지하면서, 화합물 (24) 60.2g(0.0266mol)을 적하하고, 또한 90℃에서 5시간 반응을 행했다. 여기에서, 합성예 1과 동일한 방법으로, Si-H기의 반응 완결을 확인했다.To a 1-liter three-necked flask equipped with a stirrer, a thermometer, an ester adapter and a Dimroth condenser cooling tube, 30.1 g of toluene, 10.0 g (0.0266 mol) of the compound (20), and a toluene solution of the vinylsiloxane- : 0.5% by mass), and the temperature was raised to 80 占 폚. 60.2 g (0.0266 mol) of the compound (24) was added dropwise while maintaining the temperature at 80 to 90 占 폚 and the reaction was further carried out at 90 占 폚 for 5 hours. Here, the completion of the reaction of the Si-H group was confirmed in the same manner as in Synthesis Example 1.
딤로스 냉각기 냉각관을 배기 가스관에 바꾸어 연결하고, 질소 가스 버블링하, 계 내 압력 10mmHg, 150℃에서 3시간 가열한 후, 25℃까지 냉각하고, 압력을 상압으로 복압한 후, 얻어진 액체를 여과 정제하여, 유기 규소 화합물 (23) 63.1g을 얻었다.The dimox cooler cooling tube was connected to an exhaust gas pipe and heated under a nitrogen gas bubbling pressure of 10 mmHg at 150 캜 for 3 hours and then cooled to 25 캜 and pressurized to normal pressure, And purified to obtain 63.1 g of the organosilicon compound (23).
[2] 표면처리제 조성물의 조제[2] Preparation of surface treatment agent composition
[실시예 2-1][Example 2-1]
아세트산 에틸 19.0g에, 실시예 1-1에서 얻어진 유기 규소 화합물 (13) 0.920g, 및 98% 황산 0.080g을 가하고 혼합하여, 표면처리제 조성물을 얻었다.To 19.0 g of ethyl acetate, 0.920 g of the organosilicon compound (13) obtained in Example 1-1 and 0.080 g of 98% sulfuric acid were added and mixed to obtain a surface treatment composition.
[실시예 2-2][Example 2-2]
유기 규소 화합물 (13)을 실시예 1-2에서 얻어진 유기 규소 화합물 (16)으로 변경한 이외는, 실시예 2-1과 동일하게 하여 표면처리제 조성물을 얻었다.A surface treating agent composition was obtained in the same manner as in Example 2-1 except that the organosilicon compound (13) was changed to the organosilicon compound (16) obtained in Example 1-2.
[실시예 2-3][Example 2-3]
유기 규소 화합물 (13)을 실시예 1-3에서 얻어진 유기 규소 화합물 (19)로 변경한 이외는 실시예 2-1과 동일하게 하여 표면처리제 조성물을 얻었다.A surface treating agent composition was obtained in the same manner as in Example 2-1 except that the organosilicon compound (13) was changed to the organosilicon compound (19) obtained in Example 1-3.
[실시예 2-4][Example 2-4]
유기 규소 화합물 (13)을 실시예 1-4에서 얻어진 유기 규소 화합물 (21)로 변경한 이외는, 실시예 2-1과 동일하게 하여 표면처리제 조성물을 얻었다.A surface treating agent composition was obtained in the same manner as in Example 2-1 except that the organosilicon compound (13) was changed to the organosilicon compound (21) obtained in Example 1-4.
[실시예 2-5][Example 2-5]
유기 규소 화합물 (13)을 실시예 1-5에서 얻어진 유기 규소 화합물 (23)으로 변경한 이외는, 실시예 2-1과 동일하게 하여 표면처리제 조성물을 얻었다.A surface treating agent composition was obtained in the same manner as in Example 2-1 except that the organosilicon compound (13) was changed to the organosilicon compound (23) obtained in Example 1-5.
[비교예 2-1][Comparative Example 2-1]
유기 규소 화합물 (13)을 하기 식으로 표시되는 유기 규소 화합물로 변경한 이외는, 실시예 2-1과 동일하게 하여 표면처리제 조성물을 얻었다.A surface treating agent composition was obtained in the same manner as in Example 2-1 except that the organosilicon compound (13) was changed to an organosilicon compound represented by the following formula.
[비교예 2-2][Comparative Example 2-2]
유기 규소 화합물 (13)을 하기 식으로 표시되는 유기 규소 화합물로 변경한 이외는, 실시예 2-1과 동일하게 하여 표면처리제 조성물을 얻었다.A surface treating agent composition was obtained in the same manner as in Example 2-1 except that the organosilicon compound (13) was changed to an organosilicon compound represented by the following formula.
상기 실시예 2-1∼2-5 및 비교예 2-1, 2-2에서 조제한 각 표면처리제 조성물을 티슈 페이퍼에 함침하고, 유리 기판에 와이핑 도공을 행했다. 1분간, 자연 건조한 후, 티슈 페이퍼에 물을 함침하고, 유리 기판의 도공면의 닦음 처리를 행했다. 25℃에서 1시간, 자연 건조를 행하여, 발수막 부착 유리 기판을 얻었다.Each of the surface treatment agent compositions prepared in Examples 2-1 to 2-5 and Comparative Examples 2-1 and 2-2 was impregnated with a tissue paper, and a wiping coating was performed on the glass substrate. After natural drying for 1 minute, the tissue paper was impregnated with water, and the coated surface of the glass substrate was wiped. Followed by natural drying at 25 DEG C for 1 hour to obtain a glass substrate with a water-repellent film.
얻어진 발수막 부착 유리 기판을 사용하여, 하기 (1)∼(4)의 평가 시험을 행했다. 결과를 표 1에 나타낸다.Using the obtained glass substrate with a water-repellent film, evaluation tests of the following (1) to (4) were carried out. The results are shown in Table 1.
또한, 수접촉각 및 물방울 활락 각도(전락각)는 활락 유닛을 구비한 접촉각계(쿄와카이멘카가쿠(주)제 Drop Master DM-701)에 의해 측정했다.The water contact angle and water drop angle (tilting angle) were measured by a contact angle meter (Drop Master DM-701 made by Kyowa Hakko Kiken Kagaku Co., Ltd.) equipped with an elastic unit.
(1) 발수성(1) Water repellency
발수막 부착 유리 기판의 피처리면 위에 2㎕의 물을 적하하고, 수접촉각을 측정했다.Water 2 占 퐇 of water was dropped onto the surface of the glass substrate with water repellent film, and the water contact angle was measured.
(2) 활수성(2)
발수막 부착 유리 기판의 피처리면 위에 체적 2㎕의 물방울을 적하하고, 전락 각을 측정했다.On the surface of the glass substrate with the water-repellent film, 2 mu l of water droplets were dropped, and the angle of inclination was measured.
(3) 내수성 시험(3) Water resistance test
발수막 부착 유리 기판을 1질량% 계면활성제(라이폰 F, 라이온하이진(주)제) 수용액 중에 침지하고, 초음파(100W, 42kHz)를 30분간 조사했다. 시험 전후의 발수막 부착 유리 기판에 관하여, 발수성, 활수성을 평가했다.The water-repellent film-adhered glass substrate was immersed in an aqueous solution of 1% by mass of a surfactant (manufactured by Lion F, Lion High-Jean Co.) and irradiated with ultrasonic waves (100 W, 42 kHz) for 30 minutes. With respect to the glass substrate with the water-repellent film before and after the test, the water repellency and the water-activatability were evaluated.
(4) 내마모성 시험(4) Abrasion resistance test
발수막 부착 유리 기판의 피처리면 위에, 2cm×2cm 플란넬천, 1.2kg 하중, 1,200회 왕복의 조건으로 마모 시험을 실시했다. 시험 전후의 발수막 부착 유리 기판에 관하여, 발수성, 활수성을 평가했다.The abrasion test was performed on the surface of the glass substrate with the water repellent film on a condition of a 2 cm x 2 cm flannel cloth, 1.2 kg load, and 1,200 reciprocations. With respect to the glass substrate with the water-repellent film before and after the test, the water repellency and the water-activatability were evaluated.
표 1에 나타내어지는 바와 같이, 실시예 2-1∼2-5에서 얻어진 발수막 부착 유리 기판은 초기, 내수성 시험 후 및 내마모성 시험 후에 있어서의 발수성, 활수성이 양호한 것을 알 수 있다.As shown in Table 1, the glass substrates with water repellent films obtained in Examples 2-1 to 2-5 were found to have good water repellency and water fastness after the initial water resistance test and the abrasion resistance test.
한편, 비교예 2-1, 2-2에서 얻어진 발수막 부착 유리 기판은 내수성 시험 후나 내마모성 시험 후에 있어서, 특히 활수성이 현저하게 저하된 것을 알 수 있다.On the other hand, the glass substrates with a water repellent film obtained in Comparative Examples 2-1 and 2-2 showed remarkably decreased water resistance after the water resistance test and the abrasion resistance test.
Claims (15)
{식 중, R1은, 서로 독립하여, 탄소 원자수 1∼12의 알킬기 또는 식 (2)로 표시되는 기를 나타내고,
[식 중, R4는, 서로 독립하여, 탄소 원자수 1∼12의 알킬기 또는 식 (3)으로 표시되는 기를 나타낸다.
(식 중, R5는, 서로 독립하여, 탄소 원자수 1∼12의 알킬기를 나타낸다.)]
R2는, 서로 독립하여, 탄소 원자수 1∼12의 알킬기를 나타내고,
R3은, 서로 독립하여, 탄소 원자수 1∼4의 알킬기를 나타내고,
X는, 서로 독립하여, 하이드록시기 또는 가수분해성 기를 나타내고,
Y는 아릴렌기 또는 불화 알킬렌기를 함유하는 2가 연결기를 나타내고,
a는 1∼100의 수를 나타내고, b는 0∼2의 수를 나타낸다.}An organosilicon compound represented by the general formula (1).
(Wherein R 1 represents, independently of each other, an alkyl group having 1 to 12 carbon atoms or a group represented by formula (2)
[Wherein R 4 independently represents an alkyl group having 1 to 12 carbon atoms or a group represented by formula (3).
(Wherein R 5 , independently of each other, represents an alkyl group having 1 to 12 carbon atoms)]]
R 2 independently represent an alkyl group having 1 to 12 carbon atoms,
R 3 independently represent an alkyl group having 1 to 4 carbon atoms,
X represents, independently of each other, a hydroxyl group or a hydrolyzable group,
Y represents a divalent linking group containing an arylene group or an alkylene fluoride group,
a represents a number of 1 to 100, and b represents a number of 0 to 2.}
[식 중, Z는 식 (5)∼(7)로부터 선택되는 어느 1개의 2가 연결기를 나타내고, R6 및 R7은, 서로 독립하여, 단결합 또는 Z와 상이한 2가 연결기를 나타낸다.
(식 (5) 중, c는 1∼10의 수를 나타내고, 식 (7) 중, R8은, 서로 독립하여, 탄소 원자수 1∼12의 알킬기를 나타낸다.)]The organosilicon compound according to claim 1, wherein Y is a divalent linking group represented by formula (4).
Wherein Z represents any one divalent linking group selected from the formulas (5) to (7), and R 6 and R 7 independently represent a single bond or a divalent linking group different from Z.
(In the formula (5), c represents a number of 1 to 10, and in the formula (7), R 8 independently represent an alkyl group having 1 to 12 carbon atoms.)]
[식 중, Z는 식 (5)∼(7)로부터 선택되는 어느 1개의 2가 연결기를 나타내고, R3, R6, R7, X, a 및 b는 상기와 동일한 의미를 나타낸다.
(식 (5) 중, c는 상기와 동일한 의미를 나타내고, 식 (7) 중, R8은 메틸기를 나타낸다.)]The organosilicon compound according to claim 2, which is represented by formula (8) or formula (9).
Wherein Z represents any one of divalent linking groups selected from the formulas (5) to (7), and R 3 , R 6 , R 7 , X, a and b have the same meanings as defined above.
(In the formula (5), c has the same meaning as defined above, and in the formula (7), R 8 represents a methyl group.)]
(식 중, d는 0∼10의 수를 나타낸다.)4. The organosilicon compound according to claim 2 or 3, wherein R < 6 > and R < 7 >
(Wherein d represents the number of 0 to 10).
A surface treatment composition as claimed in any one of claims 7 to 9 is applied to a substrate to form a coating film and the surface of the coating film is wiped with water and then a water repellent film / RTI >
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| JP5990909B2 (en) * | 2011-12-28 | 2016-09-14 | 信越化学工業株式会社 | One-end functional group-containing organopolysiloxane and method for producing the same |
| JP2016050276A (en) * | 2014-09-01 | 2016-04-11 | スリーボンドファインケミカル株式会社 | Surface treatment agent for coated steel panel |
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Also Published As
| Publication number | Publication date |
|---|---|
| CN108884227B (en) | 2021-08-10 |
| CN108884227A (en) | 2018-11-23 |
| JP6642309B2 (en) | 2020-02-05 |
| KR102463768B1 (en) | 2022-11-07 |
| JP2018002933A (en) | 2018-01-11 |
| WO2018008505A1 (en) | 2018-01-11 |
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