JP5513023B2 - 落書き防止塗料組成物 - Google Patents
落書き防止塗料組成物 Download PDFInfo
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- JP5513023B2 JP5513023B2 JP2009154615A JP2009154615A JP5513023B2 JP 5513023 B2 JP5513023 B2 JP 5513023B2 JP 2009154615 A JP2009154615 A JP 2009154615A JP 2009154615 A JP2009154615 A JP 2009154615A JP 5513023 B2 JP5513023 B2 JP 5513023B2
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- organopolysiloxane
- graffiti
- component
- meth
- Prior art date
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- 239000003973 paint Substances 0.000 title claims description 53
- 239000000203 mixture Substances 0.000 title claims description 16
- 230000002265 prevention Effects 0.000 title claims description 16
- 229920001296 polysiloxane Polymers 0.000 claims description 72
- 238000000576 coating method Methods 0.000 claims description 56
- 239000011248 coating agent Substances 0.000 claims description 48
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 22
- 229910018540 Si C Inorganic materials 0.000 claims description 20
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000008199 coating composition Substances 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000004567 concrete Substances 0.000 claims description 12
- 239000011521 glass Substances 0.000 claims description 12
- 239000000049 pigment Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 9
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 239000004925 Acrylic resin Substances 0.000 claims description 6
- 229920000178 Acrylic resin Polymers 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- -1 polysiloxane Polymers 0.000 description 117
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- 238000012360 testing method Methods 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 239000007921 spray Substances 0.000 description 12
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- 230000000052 comparative effect Effects 0.000 description 7
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 6
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
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- 125000003118 aryl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
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- 125000003545 alkoxy group Chemical group 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 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 5
- 238000011156 evaluation Methods 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
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- 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 5
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- 125000001424 substituent group Chemical group 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 125000004103 aminoalkyl group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000005417 glycidoxyalkyl group Chemical group 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 4
- 125000004344 phenylpropyl group Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 235000011187 glycerol Nutrition 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000003960 organic solvent Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
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- 239000011787 zinc oxide Substances 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
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- AJPODVQGWMNSJT-UHFFFAOYSA-N hexan-2-olate zirconium(4+) Chemical compound [Zr+4].CCCCC(C)[O-].CCCCC(C)[O-].CCCCC(C)[O-].CCCCC(C)[O-] AJPODVQGWMNSJT-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- JFZUABNDWZQLIJ-UHFFFAOYSA-N methyl 2-[(2-chloroacetyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CCl JFZUABNDWZQLIJ-UHFFFAOYSA-N 0.000 description 1
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- FIWHJQPAGLNURC-UHFFFAOYSA-N oxiran-2-ylmethyl 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)OCC1CO1 FIWHJQPAGLNURC-UHFFFAOYSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- NLDFTWSUPLJCQD-UHFFFAOYSA-N prop-1-en-2-yl propanoate Chemical compound CCC(=O)OC(C)=C NLDFTWSUPLJCQD-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 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
- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- JOAZIIBFQMIXJM-UHFFFAOYSA-N tris(4-chlorophenyl) borate Chemical compound C1=CC(Cl)=CC=C1OB(OC=1C=CC(Cl)=CC=1)OC1=CC=C(Cl)C=C1 JOAZIIBFQMIXJM-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- DJXRIQMCROIRCZ-XOEOCAAJSA-N vibegron Chemical compound C1([C@H]([C@@H]2N[C@H](CC=3C=CC(NC(=O)[C@H]4N5C(=O)C=CN=C5CC4)=CC=3)CC2)O)=CC=CC=C1 DJXRIQMCROIRCZ-XOEOCAAJSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Description
Si−C結合及び加水分解性シリル基を含有するオルガノポリシロキサン(a)が、ベンゼン環構造を含有するオルガノポリシロキサン(a1)並びに3次元構造のオルガノポリシロキサン骨格及び直鎖状のオルガノポリシロキサン骨格を分子中に共に含有するオルガノポリシロキサン(a2)を含有するものであり、
成分(a)及び成分(b)の使用割合が両者の合計質量に基づいて成分(a)が50〜99.9質量%、成分(b)が0.1〜50質量%の範囲内であって、成分(c)の含有量が成分(a)及び成分(b)の合計100質量部に対して0.1〜30質量部の範囲内であることを特徴とする落書き防止塗料組成物、及び該塗料組成物を被塗面に塗布してなる塗装方法に関する。
n1:上記式(1)、(2)、(3)及び(4)のオルガノシラン化合物における置換基R1の合計モル数、n2:置換基R1におけるメチル基のモル数
また本発明においてSi−C結合及び加水分解性シリル基を含有するオルガノポリシロキサン(a)は、形成される塗膜の耐ワレ性を向上させるために、ベンゼン環構造を含有するオルガノポリシロキサン(a1)を含有することが望ましく、該オルガノポリシロキサン(a1)のベンゼン環濃度は20mol%以上、好ましくは20〜70mol%であることが望ましい。
n1:上記式(1)、(2)、(3)及び(4)のオルガノシラン化合物における置換基R1の合計モル数、n3:置換基R1におけるベンゼン環のモル数。
k3は1〜20、好ましくは2〜20の整数を表し、R4はメチル基又は水素原子を表す。R41は、水素、炭素数が1〜3の置換もしくは非置換のアルキル基を表し、特に水素、メチル基が好適である。
製造例1
3口フラスコにメチルトリメトキシシラン80部、ジメチルジメトキシシラン20部を加え、攪拌下0.05N塩酸水10部を滴下し、68℃で1時間加水分解縮合した。これを120℃まで加熱して副生メタノールを除去し、ろ過を行って加水分解性シリル基を含有するオルガノポリシロキサン(A−1)を得た。
3口フラスコにメチルトリメトキシシラン50部、ジメチルジメトキシシラン20部、フェニルトリメトキシシラン30部を加え、攪拌下0.05N塩酸水10部を滴下し、68℃で1時間加水分解縮合した。これを120℃まで加熱して副生メタノールを除去し、ろ過を行って加水分解性シリル基を含有するオルガノポリシロキサン(A−2)を得た。
3口フラスコにメチルトリメトキシシラン85部、ビニルメチルジメトキシシラン15部を加え、攪拌下0.05N塩酸水15部を滴下し、68℃で2時間加水分解縮合した。これを120℃まで加熱して副生メタノールを除去し、ろ過を行ってオルガノポリシロキサン(a)を得た。
製造例4
温度計、還流冷却器、攪拌機及び滴下装置を備えた4口フラスコに、酢酸n−ブチル81.8部を仕込み、攪拌下で加熱し、95℃に保った。次に、95℃の温度で、「サイラプレーンFM−0721」(注3)20部、γ−メタクリロイルオキシプロピルトリメトキシシラン30部、2−ヒドロキシエチルメタクリレート10部、i−ブチルメタクリレート40部及び重合開始剤である2,2´−アゾビス(2,4−ジメチルバレロニトリル)4.2部からなる混合物を3時間かけて滴下した。滴下後95℃で2時間熟成し、固形分濃度55%及び数平均分子量1万の加水分解性シリル基、水酸基及びポリシロキサン鎖を有するアクリル樹脂(B)を得た。
実施例1〜14及び比較例1〜2
表1に記載の配合組成で各成分を配合し、攪拌混合することで落書き防止塗料(R−1)〜(R−16)を製造した。尚、表1中の(注4)〜(注11)は下記の通りである。
(注5)「メタシャイン1020RS」:商品名、日本板硝子社製、酸化チタン被覆ガラスフレーク顔料
(注6)「エチルシリケート40」:商品名、コルコート社製、テトラエトキシシラン縮合物、平均縮合度6、SiO2として40質量%を含有する。
(注7)「デュラネートTPA−90EK」:商品名、旭化成社製、ヘキサメチレンジイソシアネートのイソシアヌレート体、不揮発分90%、イソシアネート基含有量21%
(注8)「TINUVIN 123」:商品名、チバ・スペシャルティケミカル社製、ヒンダードアミン系光安定剤
(注9)「TINUVIN 405」:商品名、チバ・スペシャルティケミカル社製、ヒドロキシフェニルトリアジン系紫外線吸収剤
(注10)「MT−100SAS」:商品名、テイカ社製、微粒子酸化チタン
(注11)「MZ−505S」:商品名、テイカ社製、微粒子酸化亜鉛。
実施例15〜28及び比較例3、4
150×70×0.8mmのクロメート処理アルミニウム板上に、2液型弱溶剤系フッ素樹脂系塗料(「セラテクトFマイルド」;商品名、関西ペイント社製)をアプリケーターを用いて乾燥膜厚約25μmとなるように塗装し、気温23℃、相対湿度60%の条件下で24時間乾燥させたものを被塗板とした。この上に表2に示すように実施例1〜14及び比較例1〜2で得た各落書き防止塗料(R−1)〜(R−16)をアプリケーターを用いて乾燥膜厚約15μmとなるように塗装し、さらに気温23℃、相対湿度60%の条件下で14日間乾燥させたものを試験体とし、後述の性能試験に供した。評価試験結果を表2に示す。
150×70×10mmのコンクリート板上に「エクセラ100」(関西ペイント社製、浸透性吸水防止剤)を刷毛を用いて100g/m2となるように塗装し、気温23℃、相対湿度60%の条件下で24時間乾燥させたものを被塗板とした。この上に表3に示すように実施例1〜14及び比較例1〜2で得た各落書き防止塗料(R−1)〜(R−16)をアプリケーターを用いて乾燥膜厚約15μmとなるように塗装し、さらに気温23℃、相対湿度60%の条件下で14日間乾燥させたものを試験体とし、後述の性能試験に供した。評価試験結果を表3に示す。
150×70×10mmのコンクリート板上に水性2液ウレタン塗料(「リベルマイスター:(商品名、関西ペイント株式会社製)を(アプリケーター)で乾燥膜厚が30μmとなるように塗装し、気温23℃、相対湿度60%の条件下で24時間乾燥させたものを被塗板とした。この上に表4に示すように実施例1〜14及び比較例1〜2で得た各落書き防止塗料(R−1)〜(R−16)をアプリケーターを用いて乾燥膜厚約15μmとなるように塗装し、さらに気温23℃、相対湿度60%の条件下で14日間乾燥させたものを試験体とし、後述の性能試験に供した。評価試験結果を表4に示す。
150×70×0.8mmのクロメート処理アルミニウム板上に、2液型弱溶剤系フッ素樹脂系塗料(「セラテクトFマイルド」:商品名、関西ペイント社製)をアプリケーターを用いて乾燥膜厚約25μmとなるように塗装し、気温23℃、相対湿度60%の条件下で24時間乾燥させ、更にこの上に水性2液ウレタン樹脂系塗料(「リベルマイスター」:商品名、関西ペイント株式会社製、水酸基含有樹脂/ポリイソシアネート硬化剤)、水性1液ウレタン樹脂系塗料(「アクアレタン」:商品名、関西ペイント株式会社製)、水性2液フッソ樹脂系塗料(フッソ樹脂エマルション(「ルミフロンエマルション」:商品名、旭硝子社製)とポリイソシアネート硬化剤(「Bayhydur」:商品名、バイエル社製)を使用直前に混合してなる塗料)、水性1液フッソ樹脂系塗料(「アクアフッソII」、商品名、関西ペイント株式会社製)をアプリケーターで乾燥膜厚が30μmとなるように塗装し、気温23℃、相対湿度60%の条件下で24時間乾燥させたものを被塗板とした。この上に表5に示すように実施例4、5で得た各落書き防止塗料(R−4)〜(R−5)をアプリケーターを用いて乾燥膜厚約15μmとなるように塗装し、さらに気温23℃、相対湿度60%の条件下で1日間乾燥させたものを試験体とし、後述の性能試験に供した。評価試験結果を表5に示す。
(*1)落書き防止性:各試験体の塗面上に黒色のラッカースプレー(「アクリルラッカースプレー」、カンペハピオ社製)で落書きし、ハジキの程度を目視により評価した。
◎:非常によくはじいて、何を書いたか識別できない、
○:はじくが、わずかに落書きが識別できる、
△:わずかにはじくが、落書きが鮮明に識別できる、
×:全くはじかず、落書きが鮮明に識別できる。
各試験体の塗面上に黒色のラッカースプレー(「アクリルラッカースプレー」、カンペハピオ社製)で落書きし、気温23℃、相対湿度60%の条件下で24時間乾燥させた後、溶剤(トルエン/酢酸エチル=1/1の混合溶剤)で拭き取った時の状態を目視により評価した。
◎:落書きの痕跡が全く残らない、
○:落書きの痕跡がわずかに残る、
△:落書きの痕跡が残る、
×:落書きが全く除去できない。
JIS K 5600−7−4(耐湿潤冷熱繰り返し性)に準じ、23℃の水に18時間浸水後、−20℃で3時間、さらに50℃で3時間試験に供した。この繰り返しを10サイクル行い、試験終了後の塗膜の状態を目視により評価した。
○:ワレが認められない、
△:塗膜の一部にワレが認められる、
×:塗膜に著しいワレが認められる。
JIS K 5600−7−7(キセノンランプ法)の促進耐候性試験に準じて、1000時間照射した後、上記(*1)落書き防止性の評価を行った。
◎:非常によくはじいて、何を書いたか識別できない、
○:はじくが、わずかに落書きが識別できる、
△:わずかにはじくが、落書きが鮮明に識別できる、
×:全くはじかず、落書きが鮮明に識別できる。
JIS K 5600−5−6(クロスカット法)に準じ、各試験体上に2mm×2mmの大きさの碁盤目を25マス(縦5分割×横5分割)作製した。これにセロハン粘着テープを貼り付けて、瞬間的に引き剥がし、塗膜の剥がれの面積を測定することで評価した。
◎:塗膜の剥がれの面積が全面積の5%未満、
○:塗膜の剥がれの面積が全面積の5%以上、15%未満、
△:塗膜の剥がれの面積が全面積の15%以上、35%未満、
×:塗膜の剥がれの面積が全面積の35%以上。
(*6)耐溶剤性
各試験体の塗膜上にスポイトを用いてラッカーシンナーを2ml滴下し、ラッカーシンナー乾燥後の各試験体の塗膜状態を評価した。
○:塗膜に異常がない、
△:塗膜にチヂミがわずかに認められる、
×:塗膜にチヂミが生じる(リフティング)。
Claims (11)
- Si−C結合及び加水分解性シリル基を含有するオルガノポリシロキサン(a)、加水分解性シリル基を含有しないオルガノポリシロキサン(b)、及びガラスフレーク顔料(c)を含有し、
Si−C結合及び加水分解性シリル基を含有するオルガノポリシロキサン(a)が、ベンゼン環構造を含有するオルガノポリシロキサン(a1)並びに3次元構造のオルガノポリシロキサン骨格及び直鎖状のオルガノポリシロキサン骨格を分子中に共に含有するオルガノポリシロキサン(a2)を含有するものであり、
成分(a)及び成分(b)の使用割合が両者の合計質量に基づいて成分(a)が50〜99.9質量%、成分(b)が0.1〜50質量%の範囲内であって、成分(c)の含有量が成分(a)及び成分(b)の合計100質量部に対して0.1〜30質量部の範囲内であることを特徴とする落書き防止塗料組成物。 - ガラスフレーク顔料(c)が、金属酸化物を被覆したガラスフレーク顔料、又は金属をメッキしたガラスフレーク顔料である請求項1に記載の落書き防止塗料組成物。
- オルガノシリケート化合物(d)をさらに含有する請求項1又は2に記載の落書き防止塗料組成物。
- シロキサンマクロモノマー(e1)、加水分解性シリル基含有重合性不飽和モノマー(e2)、水酸基含有重合性不飽和モノマー(e3)、及び必要によりこれらと共重合可能な他の重合性不飽和モノマー(e4)の共重合により得られるアクリル樹脂(e)をさらに含有する請求項1ないし3のいずれか1項に記載の落書き防止塗料組成物。
- シランカップリング剤をさらに含有する請求項1ないし4のいずれか1項に記載の落書き防止塗料組成物。
- 有機金属系硬化触媒をさらに含有する請求項1ないし5のいずれか1項に記載の落書き防止塗料組成物。
- 被塗面に、請求項1ないし6のいずれか1項に記載の落書き防止塗料組成物を塗布することを特徴とする塗装方法。
- コンクリート面に浸透性吸水防止剤を塗布した後、請求項1ないし6のいずれか1項に記載の落書き防止塗料組成物を塗布することを特徴とする塗装方法。
- 被塗面に、水性ウレタン樹脂系塗料又は水性フッソ樹脂系塗料を塗布した後、請求項1ないし6のいずれか1項に記載の落書き防止塗料組成物を塗布することを特徴とする塗装方法。
- 水性ウレタン樹脂系塗料及び水性フッソ樹脂系塗料が、それぞれ水性2液ウレタン樹脂系塗料及び水性2液フッソ樹脂系塗料である請求項9に記載の塗装方法。
- 被塗面が、基材に弱溶剤系塗料による塗膜が設けられた塗装面である請求項9又は10に記載の塗装方法。
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