JPS6315862A - Paint composition - Google Patents
Paint compositionInfo
- Publication number
- JPS6315862A JPS6315862A JP61157961A JP15796186A JPS6315862A JP S6315862 A JPS6315862 A JP S6315862A JP 61157961 A JP61157961 A JP 61157961A JP 15796186 A JP15796186 A JP 15796186A JP S6315862 A JPS6315862 A JP S6315862A
- Authority
- JP
- Japan
- Prior art keywords
- copolymer
- formula
- isobutylene
- ester
- styrene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003973 paint Substances 0.000 title claims abstract description 4
- 239000000203 mixture Substances 0.000 title claims description 4
- 229920001577 copolymer Polymers 0.000 claims abstract description 30
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 229920005862 polyol Polymers 0.000 claims abstract description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000178 monomer Substances 0.000 claims abstract description 3
- -1 polyol compound Chemical class 0.000 claims description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 abstract description 10
- 238000000576 coating method Methods 0.000 abstract description 10
- 239000002904 solvent Substances 0.000 abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 6
- 239000000049 pigment Substances 0.000 abstract description 6
- 239000002270 dispersing agent Substances 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract description 3
- 229920001451 polypropylene glycol Polymers 0.000 abstract description 3
- 239000004925 Acrylic resin Substances 0.000 abstract description 2
- 229920000178 Acrylic resin Polymers 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 150000003077 polyols Chemical class 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 239000008199 coating composition Substances 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000005028 tinplate Substances 0.000 description 2
- GUYIZQZWDFCUTA-UHFFFAOYSA-N (pentadecachlorophthalocyaninato(2-))-copper Chemical compound [Cu+2].N1=C([N-]2)C3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3C2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC2=C(C(Cl)=C(C(Cl)=C3)Cl)C3=C1[N-]2 GUYIZQZWDFCUTA-UHFFFAOYSA-N 0.000 description 1
- JIRKHEPVCOYRND-UHFFFAOYSA-N 1,4-dihydroxy-2-methyl-2-propan-2-ylpiperazine Chemical compound CC(C)C1(C)CN(O)CCN1O JIRKHEPVCOYRND-UHFFFAOYSA-N 0.000 description 1
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- IYHIFXGFKVJNBB-UHFFFAOYSA-N 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonic acid Chemical compound C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S(O)(=O)=O IYHIFXGFKVJNBB-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910000004 White lead Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- AUNAPVYQLLNFOI-UHFFFAOYSA-L [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O Chemical compound [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O AUNAPVYQLLNFOI-UHFFFAOYSA-L 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- PPKVREKQVQREQD-UHFFFAOYSA-N antimony pentasulfide Chemical compound S=[Sb](=S)S[Sb](=S)=S PPKVREKQVQREQD-UHFFFAOYSA-N 0.000 description 1
- 229960001283 antimony pentasulfide Drugs 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- JYWJULGYGOLCGW-UHFFFAOYSA-N chloromethyl chloroformate Chemical compound ClCOC(Cl)=O JYWJULGYGOLCGW-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は塗料組成物に関し、詳しくは可撓性に優れた塗
膜を形成し得る塗料組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a coating composition, and more particularly to a coating composition capable of forming a coating film with excellent flexibility.
これまでに、スチレン−無水マレイン酸共重合体または
アクリル酸〜無水マレイン酸共重合体とエポキシ樹脂と
からなる塗料組成物が知られている。Hitherto, coating compositions comprising a styrene-maleic anhydride copolymer or an acrylic acid-maleic anhydride copolymer and an epoxy resin are known.
この塗料組成物によって形成される塗膜は、硬質の良好
なものであるが、可撓性に劣り、屈曲や振動によって、
亀裂やｆｆ１ｌ離を生じるという欠点があった。The coating film formed by this coating composition has good hardness, but is poor in flexibility and can be easily damaged by bending or vibration.
There was a drawback that cracks and ff1l separation occurred.
本発明は、前記欠点を解消した可撓性に優れた塗膜を形
成し得る塗料組成物を提供することを目的とする。An object of the present invention is to provide a coating composition that eliminates the above-mentioned drawbacks and can form a coating film with excellent flexibility.
本発明の塗料組成物はイソブチレン、スチレン、アクリ
ル酸またはそのエステルおよびメタアクリル酸またはそ
のエステルから選ばれた少なくとも１種のモノマーと、
マレイン酸またはその無水物もしくはエステルとの共重
合体およびポリオール化合物を含有することを特徴とす
る。The coating composition of the present invention contains at least one monomer selected from isobutylene, styrene, acrylic acid or its ester, and methacrylic acid or its ester,
It is characterized by containing a copolymer with maleic acid or its anhydride or ester and a polyol compound.
これらの共重合体において、 イソブチレン単位は次の式で表すことができる。In these copolymers, The isobutylene unit can be represented by the following formula.
ＣＨ３ 一←ｃ−ｃＨｚ＋ ＣＨ３ スチレン単位は例えば次の式で表すことができる。CH3 1←c-cHz+ CH3 The styrene unit can be represented by the following formula, for example.
ここでスチレンそのものの代わりとしてα−メチルスチ
レン、ビニルトルエン、２．４−ジメチルスチレン、ク
ロロスチレンおよびその他の置換したスチレンを用いて
もよく、またこれらを含有するスチレンを用いてもよい
。Here, instead of styrene itself, α-methylstyrene, vinyltoluene, 2,4-dimethylstyrene, chlorostyrene, and other substituted styrenes may be used, or styrene containing these may be used.
アクリル酸、メタアクリル酸またはそれらのエステル単
位は次の一般式で表すことができる。Acrylic acid, methacrylic acid, or their ester units can be represented by the following general formula.
−Ｇ−ＣＩＩ ２− ＣＩＩ Ｒ−井
０ＯＲ２
（ただし、Ｒ１は水素またはメチル基、Ｒ２は水素また
は低級アルキル基であり、好ましいのはメチル基である
。）
マレイン酸またはマレイン酸エステル単位は次の式で表
すことができる。-G-CII 2- CII R-I0OR2 (However, R1 is hydrogen or a methyl group, and R2 is hydrogen or a lower alkyl group, preferably a methyl group.) The maleic acid or maleic acid ester unit is the following It can be expressed by the formula.
＋ Ｃ１１−ＣＨ−）−
ＣＯＯＲ３ＣＯＯＲ’
（ただし、Ｒ３、Ｒ４は水素または低級アルキル基であ
り、Ｒ′３、Ｒ６は同一でも異なっていてもよい。）無
水マレイン酸単位は次の式で表すことができる。+ C11-CH-)- COOR3COOR' (However, R3 and R4 are hydrogen or lower alkyl groups, and R'3 and R6 may be the same or different.) The maleic anhydride unit should be represented by the following formula. Can be done.
−（−ＣＨ−ＣＩＩ ＋ ｃｏ ｃ。-(-CH-CII + co c.
これらの共重合体は、例えば次のようにして製造される
。すなわち、まず、イソブチレンを用いる場合はイソブ
チレンを除く各共重合成分の所定量を反応容器中に仕込
み、冷却するとともに充分脱気する。次いで、所定量の
イソブチレンを加え攪拌しながら共重合反応を行わせる
。このとき、反応温度は特に制限されないが、通常３０
〜２００°Ｃ１好ましくは４５〜２００°Ｃ１反応時間
は特に制限されないが、通常０．５〜２０時間、好まし
くは１〜１０時間に設定する。この共重合反応において
は、必要に応じて、エチルベンゼン、クメン、ｎ−’７
’チルヘンゼン、アセトコ１−リル、ニトロメタン、ニ
トロエタン、メチルエチルケトン、アセトン、Ｎ、 Ｎ
−ジメチルホルムアミド、ジメチルスルホキシドなどの
溶媒を単独でまたは混合して使用することができる。ま
た、過酸化ベンゾイル、過酸化ラウロイル、クメンヒド
ロパーオキシド、第３級ブチルヒドロパーオキシド、ジ
クミルパーオキシド、アゾビスイソブチロニトリルなど
の触媒も使用することができる。These copolymers are produced, for example, as follows. That is, first, when isobutylene is used, predetermined amounts of each copolymer component except isobutylene are charged into a reaction vessel, cooled and sufficiently degassed. Next, a predetermined amount of isobutylene is added and a copolymerization reaction is carried out with stirring. At this time, the reaction temperature is not particularly limited, but is usually 30
-200°C1, preferably 45-200°C1 The reaction time is not particularly limited, but is usually set to 0.5 to 20 hours, preferably 1 to 10 hours. In this copolymerization reaction, ethylbenzene, cumene, n-'7
'Chirhenzen, acetocol-1-lyl, nitromethane, nitroethane, methyl ethyl ketone, acetone, N, N
- Solvents such as dimethylformamide and dimethyl sulfoxide can be used alone or in combination. Catalysts such as benzoyl peroxide, lauroyl peroxide, cumene hydroperoxide, tertiary butyl hydroperoxide, dicumyl peroxide, and azobisisobutyronitrile can also be used.
本発明における共重合体としては、具体的にはイソブチ
レン−無水マレイン酸共重合体（Ｉ Ｂ−ＭＡ） 、ス
チレン−無水マレイン酸共重合体（ＳＴ−ＭＡ共重合体
）、アクリル酸メチル−無水マレイン酸共重合体（ＡＭ
−ＭＡ共重合体）等の二元共重合体、イソブチレン−ス
チレン−無水マレイン酸共重合体（ＩＢ−３Ｔ−ＭＡ共
重合体）、イソブチレン−アクリル酸メチル−無水マレ
イン酸共重合体（ＩＢ−ＡＭ−ＭＡ共重合体）、スヂレ
ンーアクリル酸メチルー無水マレイン酸共重合体（ＳＴ
−ＡＭ−ＭＡ共重合体）等の三元共重合体、イソブチレ
ン−スチレン−アクリル酸メチル−無水マレイン酸共重
合体（ＩＢ−３Ｔ−ＡＭ−ＭＡ共重合体）等の四元共重
合体等が挙げられる。Specifically, the copolymers in the present invention include isobutylene-maleic anhydride copolymer (IB-MA), styrene-maleic anhydride copolymer (ST-MA copolymer), and methyl acrylate-anhydride. Maleic acid copolymer (AM
-MA copolymer), isobutylene-styrene-maleic anhydride copolymer (IB-3T-MA copolymer), isobutylene-methyl acrylate-maleic anhydride copolymer (IB- AM-MA copolymer), styrene-methyl acrylate-maleic anhydride copolymer (ST
-AM-MA copolymer), quaternary copolymers such as isobutylene-styrene-methyl acrylate-maleic anhydride copolymer (IB-3T-AM-MA copolymer), etc. can be mentioned.
また、本発明における共重合体は、通常、その粘度平均
分子量が５００〜４．００，０００であり、好ましい粘
度平均分子量はｉ、ｏｏｏ〜２００゜０００である。Further, the copolymer in the present invention usually has a viscosity average molecular weight of 500 to 4.00,000, and preferably has a viscosity average molecular weight of i,ooo to 200.000.
さらに本発明における前記共重合体は、その粘度平均分
子量が前記範囲内にあるとしても、無水マレイン酸単位
の含有割合が、５〜６０モル％、特に１０〜５５モル％
であるのが好ましい。Furthermore, even if the copolymer in the present invention has a viscosity average molecular weight within the above range, the content of maleic anhydride units is 5 to 60 mol%, particularly 10 to 55 mol%.
It is preferable that
このようにして得られた共重合体にポリオール化合物と
溶媒、さらに必要に応じ顔料、分散剤等を配合して塗料
組成物として使用する。The copolymer thus obtained is blended with a polyol compound, a solvent, and, if necessary, a pigment, a dispersant, etc., and used as a coating composition.
本発明で用いられるポリオール化合物としては、ポリオ
キシプロピレングリコール、ポリオキシテトラメチレン
グリコール、ポリオキシエチレングリコール、１．２−
プロピレングリコール、ジブロピレングリコール、１．
２−ブタンジオール、１，３ブタンジオール、２．３−
ブタンジオール、１．２−ベンタンジオール、２．３−
ベンタンジオール、２．５−ヘキサンジオール、２．４
−ヘキサンジオール、２−エチル−１，３−ヘキサンジ
オール、シクロヘキサンジオール、グリセリン、Ｎ、Ｎ
’−ビスヒドロキシイソプロピル−２−メチルピペラジ
ン、ビスフェノールＡのプロピレンオキザイド付加物、
エチレングリコール、１．３−プロピレングリコール、
１．４−ブタンジオール、１，５−ベンタンジオール、
１．６−ヘキサンジオールなどが挙げられる。Polyol compounds used in the present invention include polyoxypropylene glycol, polyoxytetramethylene glycol, polyoxyethylene glycol, 1.2-
Propylene glycol, dibropylene glycol, 1.
2-butanediol, 1,3-butanediol, 2.3-
Butanediol, 1.2-bentanediol, 2.3-
Bentanediol, 2.5-hexanediol, 2.4
-hexanediol, 2-ethyl-1,3-hexanediol, cyclohexanediol, glycerin, N, N
'-bishydroxyisopropyl-2-methylpiperazine, propylene oxide adduct of bisphenol A,
ethylene glycol, 1,3-propylene glycol,
1,4-butanediol, 1,5-bentanediol,
Examples include 1,6-hexanediol.
これらの中で、ポリオキシプロピレングリコール、ポリ
オキタテ１〜ラメチレングリコール、ポリオキシエチレ
ングリコールが好ましく用いられる。Among these, polyoxypropylene glycol, polyoxylamethylene glycol, and polyoxyethylene glycol are preferably used.
ポリオール化合物は、特に制限されないが、前記共重合
体１００重量部に対して、通常３０〜７００重量部、好
ましくは５０〜５００重量部配合される。Although the polyol compound is not particularly limited, it is usually blended in an amount of 30 to 700 parts by weight, preferably 50 to 500 parts by weight, based on 100 parts by weight of the copolymer.
本発明に用いられる溶媒としては、特に制限されないが
、溶解度係数が９以上の有機溶媒が好ましく用いられる
。ここで溶解度係数とは、液体間の混合性の尺度となる
液体の特性値で次式で表せるものである。The solvent used in the present invention is not particularly limited, but an organic solvent having a solubility coefficient of 9 or more is preferably used. Here, the solubility coefficient is a characteristic value of a liquid that is a measure of miscibility between liquids, and can be expressed by the following equation.
溶解度係数（δ）−（八Ｅ／Ｖ）””
Ｅ−液体の分子凝集エネルギー
■−分分子
口のような有機溶媒としては、例えば、酢酸エチル（溶
解度係数：９．１）、メチルシクロヘキザノン（９，３
＞、メチルエチルケトン（９，３）、フラン（９，４）
、酢酸メチル（９，６）、アセトン（９，９＞、シクロ
ペンタノン（９，９）、シクロペンタノン（１，０，４
）、エチレングリコールモノエチルエーテル（１０，５
）、ジメチルホルムアミド（１０，６）、ジメチルスル
ホキサイド（１２，０）、二１〜口エタン（１１，１）
、ニトロメタン（１２゜７）、アセトニトリル（１１，
９）、クロロアセトニＩ・リル（１２，６＞などが挙げ
られる。Solubility coefficient (δ) - (8E/V)"" E- Molecular cohesive energy of liquid (9,3
>, methyl ethyl ketone (9,3), furan (9,4)
, methyl acetate (9,6), acetone (9,9>, cyclopentanone (9,9), cyclopentanone (1,0,4
), ethylene glycol monoethyl ether (10,5
), dimethylformamide (10,6), dimethyl sulfoxide (12,0), ethane (11,1)
, nitromethane (12°7), acetonitrile (11,
9), chloroacetonyl lyl(12,6>, etc.).
水素結合力を３段階（弱い、中程度、強い）評価したと
き、弱い、中程度のものが好ましい。When hydrogen bond strength is evaluated in three levels (weak, medium, strong), weak and medium are preferable.
溶媒は、特に制限されないが、前記共重合体１００重量
部に対して、通常１００〜１０００重量部、好ましくは
２００〜７００重量部配合される。The solvent is not particularly limited, but is usually blended in an amount of 100 to 1000 parts by weight, preferably 200 to 700 parts by weight, per 100 parts by weight of the copolymer.
塗料組成物には必要に応じ、顔料、分散剤が配合される
。顔料は特に制限されないが、通常５０〜５００重量部
、好ましくは１００〜３００重量部、分散剤は特に制限
されないが、通常１〜５０重量部、好ましくは２〜３０
重量部配合される。Pigments and dispersants are added to the coating composition as necessary. The pigment is not particularly limited, but usually 50 to 500 parts by weight, preferably 100 to 300 parts by weight. The dispersant is not particularly limited, but usually 1 to 50 parts by weight, preferably 2 to 30 parts by weight.
Parts by weight are added.
顔料としては特に制限されないが、有機顔料としてハン
ザイエロー、ベンジディンイエロー、パーマネントイエ
ローＨＲ，Ｉ−ルイジンレソド、レーキレッドＣ、キナ
クリドンレッド、ウオッチングレッド、銅フタロシアニ
ンブルー、銅フタロシアニングリーン、グリーンゴール
ド、ジオキザディンバイオレソ］・等が、無機顔料とし
て酸化チタン、硫化亜鉛、鉛白、リトポン、亜鉛華、ベ
ンガラ、鉛丹、朱、カドミウム赤、モリブデン赤、亜酸
化銅、アンチモン赤、フェリシアン銅、群青等が、体質
顔料としてパライト、沈降性硫酸バリウム、白亜、沈降
性炭酸カルシウム、胡粉、クレー、砥の粉、タルク、ケ
イソウ土、シリカ白、アルミナ白、セソコウ、チタン白
、ヘントナイト、ケイ酸カルシウム等が用いられる。Pigments are not particularly limited, but organic pigments include Hansa Yellow, Benzidine Yellow, Permanent Yellow HR, I-Luidine Red, Lake Red C, Quinacridone Red, Watching Red, Copper Phthalocyanine Blue, Copper Phthalocyanine Green, Green Gold, and Dioxa. Inorganic pigments such as titanium oxide, zinc sulfide, white lead, lithopone, zinc white, red red iron, red lead, vermilion, cadmium red, molybdenum red, cuprous oxide, antimony red, ferrician copper, ultramarine Palite, precipitated barium sulfate, chalk, precipitated calcium carbonate, chalk, clay, abrasive powder, talc, diatomaceous earth, silica white, alumina white, sesoko, titanium white, hentonite, calcium silicate, etc. are used as extender pigments. It will be done.
分散剤としては特に制限されないが、アクリル樹脂、ア
ルキド樹脂、１−リボリリン酸ソーダ等が用いられる。The dispersant is not particularly limited, but acrylic resins, alkyd resins, sodium 1-ribolyphosphate, and the like can be used.
また、必要に応じて通常塗料に用いられる凍結防止剤、
防腐剤、消泡剤等を添加してもよい。In addition, if necessary, antifreeze agents commonly used in paints,
Preservatives, antifoaming agents, etc. may be added.
以下、本発明を実施例に基づいて詳細に説明するが、本
発明はこれに限定されるものではない。Hereinafter, the present invention will be explained in detail based on Examples, but the present invention is not limited thereto.
共重合精製通
内容積１１のオートクレーブに、イソブチレンを用いる
場合はイソブチレンを除く表示の成分を表示量仕込み、
−１０’ｃに冷却するとともに、容器内を充分に脱気し
た。ついで、イソブチレンを表示量および溶媒としてア
セト二１−リル４６０ｃＣ１触媒として過酸化ヘンジイ
ル０．６ｇを加え、４００ｒｐｍで攪拌しながら１１０
℃において２時間共重合反応を行わせ、しかるのち生成
物を水中に投入して共重合体を得た。得られた共重合体
の粘度平均分子量、イソブチレン量、スチレン量、アク
リル酸メチル量およびマレイン酸量をモル比で表に示し
た。Copolymerization purification In an autoclave with an internal volume of 11, if isobutylene is used, charge the indicated amount of the indicated components except isobutylene,
While cooling to -10'C, the inside of the container was sufficiently degassed. Next, the indicated amount of isobutylene and 460 c of acetonyl-lyl as a solvent were added, and 0.6 g of hendyl peroxide was added as a C1 catalyst, and the mixture was heated at 110 rpm while stirring at 400 rpm.
The copolymerization reaction was carried out at .degree. C. for 2 hours, and then the product was poured into water to obtain a copolymer. The viscosity average molecular weight, isobutylene content, styrene content, methyl acrylate content, and maleic acid content of the obtained copolymer are shown in the table in molar ratio.
塗料組成物の調製と塗膜の評価
表に示す共重合体、ポリオール化合物および溶剤を表示
量、２５℃で３０分間攪拌混合して塗料組成物を調製し
た。Preparation of Coating Composition and Evaluation of Coating Film A coating composition was prepared by stirring and mixing the indicated amounts of the copolymer, polyol compound, and solvent shown in the table at 25° C. for 30 minutes.
この組成物をブリキ板（１，５０ｘ ５０ ｘ ０．３
龍）に塗り、１５０℃で３０分間焼付けて２００μｍの
塗膜を形成させた。This composition was spread on a tin plate (1,50 x 50 x 0.3
A coating film of 200 μm was formed by baking at 150° C. for 30 minutes.
上記の塗膜形成ブリキ板を用い、ＪＩＳ Ｋ５４００
に準じて、耐屈曲試験を行った。心棒の直径はＬｏｗと
した。Using the above coating film forming tin plate, JIS K5400
A bending resistance test was conducted in accordance with . The diameter of the mandrel was set to Low.
〈判定〉
Ａ：上記ブリキ板３枚のうち、３枚共、われはがれが認
められなかった。<Judgment> A: No peeling was observed in any of the three tin plates mentioned above.
Ｂ：１〜２枚にわれ、はがれが認められた。B: One or two pieces were broken and peeling was observed.
Ｃ１枚共、われ、はがれが認められた。Both sheets of C were found to have cracked and peeled off.
結果を表に示す。The results are shown in the table.
表から分かるように本発明の塗料組成物を用いて得られ
た塗膜は耐屈曲性に優れている。As can be seen from the table, the coating film obtained using the coating composition of the present invention has excellent bending resistance.
以下余白
〔発明の効果〕
本発明の塗料組成物は可撓性に優れた塗膜を形成し得る
もので、側屈曲性に優れた塗膜が得られ、その工業的価
値は大である。Margins below [Effects of the Invention] The coating composition of the present invention is capable of forming a coating film with excellent flexibility, and a coating film with excellent lateral bending properties can be obtained, and its industrial value is great.
Claims (1)
ステルおよびメタアクリル酸またはそのエステルから選
ばれた少なくとも１種のモノマーと、マレイン酸または
その無水物もしくはエステルとの共重合体およびポリオ
ール化合物を含有してなる塗料組成物。1. Contains a copolymer of at least one monomer selected from isobutylene, styrene, acrylic acid or its ester, and methacrylic acid or its ester, maleic acid or its anhydride or ester, and a polyol compound. Paint composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61157961A JPS6315862A (en) | 1986-07-07 | 1986-07-07 | Paint composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61157961A JPS6315862A (en) | 1986-07-07 | 1986-07-07 | Paint composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6315862A true JPS6315862A (en) | 1988-01-22 |
Family
ID=15661234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61157961A Pending JPS6315862A (en) | 1986-07-07 | 1986-07-07 | Paint composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6315862A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57192651A (en) * | 1981-05-22 | 1982-11-26 | Teijin Ltd | Timing belt |
| JPS607442U (en) * | 1983-06-28 | 1985-01-19 | 三ツ星ベルト株式会社 | polyurethane toothed belt |
-
1986
- 1986-07-07 JP JP61157961A patent/JPS6315862A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57192651A (en) * | 1981-05-22 | 1982-11-26 | Teijin Ltd | Timing belt |
| JPS607442U (en) * | 1983-06-28 | 1985-01-19 | 三ツ星ベルト株式会社 | polyurethane toothed belt |
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