JP2015105298A - 塗料組成物及び塗装物品 - Google Patents
塗料組成物及び塗装物品 Download PDFInfo
- Publication number
- JP2015105298A JP2015105298A JP2013247069A JP2013247069A JP2015105298A JP 2015105298 A JP2015105298 A JP 2015105298A JP 2013247069 A JP2013247069 A JP 2013247069A JP 2013247069 A JP2013247069 A JP 2013247069A JP 2015105298 A JP2015105298 A JP 2015105298A
- Authority
- JP
- Japan
- Prior art keywords
- polyester resin
- hydroxyl group
- containing polyester
- acid
- resin
- 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.)
- Granted
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- 239000008199 coating composition Substances 0.000 title claims abstract description 27
- 229920001225 polyester resin Polymers 0.000 claims abstract description 65
- 239000004645 polyester resin Substances 0.000 claims abstract description 65
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 64
- 238000000576 coating method Methods 0.000 claims abstract description 55
- 239000011248 coating agent Substances 0.000 claims abstract description 54
- 239000012508 resin bead Substances 0.000 claims abstract description 27
- 239000007787 solid Substances 0.000 claims abstract description 27
- 230000009477 glass transition Effects 0.000 claims abstract description 22
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 20
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- 239000000758 substrate Substances 0.000 claims abstract description 10
- -1 cyclic polyol compound Chemical class 0.000 claims description 36
- 239000003973 paint Substances 0.000 claims description 9
- 150000007519 polyprotic acids Polymers 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- 239000000126 substance Substances 0.000 abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 15
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 14
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 12
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 239000002245 particle Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 239000008096 xylene Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 10
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229920003023 plastic Polymers 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000001361 adipic acid Substances 0.000 description 7
- 235000011037 adipic acid Nutrition 0.000 description 7
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000011324 bead Substances 0.000 description 6
- 230000035807 sensation Effects 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 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 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920001707 polybutylene terephthalate Polymers 0.000 description 4
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- VYGUBTIWNBFFMQ-UHFFFAOYSA-N [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O Chemical compound [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O VYGUBTIWNBFFMQ-UHFFFAOYSA-N 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 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 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 2
- 229920002877 acrylic styrene acrylonitrile Polymers 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 150000001298 alcohols Chemical class 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
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000004566 building material Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000011151 fibre-reinforced plastic Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 239000008269 hand cream Substances 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920013716 polyethylene resin Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 230000037072 sun protection Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 1
- ZQHJVIHCDHJVII-OWOJBTEDSA-N (e)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(\Cl)C(O)=O ZQHJVIHCDHJVII-OWOJBTEDSA-N 0.000 description 1
- JRIBKPOOFKYMRQ-UHFFFAOYSA-N 1,1,2,3-tetrachlorohex-1-ene Chemical compound CCCC(Cl)C(Cl)=C(Cl)Cl JRIBKPOOFKYMRQ-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-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
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- UJMZZAZBRIPOHZ-UHFFFAOYSA-N 2-ethylhexan-1-ol;titanium Chemical compound [Ti].CCCCC(CC)CO UJMZZAZBRIPOHZ-UHFFFAOYSA-N 0.000 description 1
- GNBPEYCZELNJMS-UHFFFAOYSA-N 2-methylbutane-1,3-diol Chemical compound CC(O)C(C)CO GNBPEYCZELNJMS-UHFFFAOYSA-N 0.000 description 1
- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 description 1
- HJJZIMFAIMUSBW-UHFFFAOYSA-N 3-methylbutane-1,2-diol Chemical compound CC(C)C(O)CO HJJZIMFAIMUSBW-UHFFFAOYSA-N 0.000 description 1
- OGLLAZUAZSIDFE-UHFFFAOYSA-N 3-methylpentane-1,2-diol Chemical compound CCC(C)C(O)CO OGLLAZUAZSIDFE-UHFFFAOYSA-N 0.000 description 1
- RLWWHEFTJSHFRN-UHFFFAOYSA-N 3-methylpentane-2,3-diol Chemical compound CCC(C)(O)C(C)O RLWWHEFTJSHFRN-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- YAAQEISEHDUIFO-UHFFFAOYSA-N C=CC#N.OC(=O)C=CC=CC1=CC=CC=C1 Chemical compound C=CC#N.OC(=O)C=CC=CC1=CC=CC=C1 YAAQEISEHDUIFO-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 206010016322 Feeling abnormal Diseases 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
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Landscapes
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Laminated Bodies (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
ここで、SF valueは、ソフトフィール値の略語であり、そしてMIU、MMD、Ra、q max及びHUは、それぞれ、摩擦係数、摩擦係数平均偏差、算術平均粗さ、表面示差熱、及びユニバーサル硬度を意味する。摩擦係数MIU及び摩擦係数平均偏差MMDは、摩擦感テスターKES−SE(商品名、カトーテック社製)を用いて測定した表面摩擦抵抗値から得られる値である。表面示差熱q maxは、精密迅速熱物性測定装置KES−F7(商品名、カトーテック社製)により測定した値である。算術平均粗さRaは、表面粗度計SURFCOM101(商品名、東京精密機器社製)により測定した値である。また、ユニバーサル硬度HUは、硬度計FISHCHER H100(商品名、フィッシャー・インストルメンツ社製)により測定した値である。
水酸基含有ポリエステル樹脂(A1)溶液の製造
製造例1
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸134.8部、1,6−ヘキサンジオール82.4部、ネオペンチルグリコール3.1部、およびイソシアヌル酸トリス(2−ヒドロキシエチル)71.3部を仕込み、窒素雰囲気下で140℃まで昇温した。
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸142.6部、1,6−ヘキサンジオール82.4部、ネオペンチルグリコール3.1部、およびイソシアヌル酸トリス(2−ヒドロキシエチル)71.3部を仕込み、窒素雰囲気下で140℃まで昇温した。
その後、1.5時間かけて200℃まで昇温し、キシレンを加えて水を留去しながら還流下反応させた。所望の酸価になったところで冷却後、次いで酢酸ブチルで希釈して固形分含有率50%のポリエステル樹脂(A1−2)溶液を得た。このポリエステル樹脂(A1−2)の数平均分子量は3,200であり、水酸基価106mgKOH/g、ガラス転移温度が−5℃であった。
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸134.9部、1,6−ヘキサンジオール82.4部、ネオペンチルグリコール3.1部、およびトリメチロールプロパン36.6部を仕込み、窒素雰囲気下で140℃まで昇温した。
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸142.6部、1,6−ヘキサンジオール82.4部、ネオペンチルグリコール3.1部、およびトリメチロールプロパン36.6部を仕込み、窒素雰囲気下で140℃まで昇温した。
その後、1.5時間かけて200℃まで昇温し、キシレンを加えて水を留去しながら還流下反応させた。所望の酸価になったところで冷却後、次いで酢酸ブチルで希釈して固形分含有率50%のポリエステル樹脂(A1−4)溶液を得た。このポリエステル樹脂(A1−4)の数平均分子量は3,200であり、水酸基価106mgKOH/g、ガラス転移温度が0℃であった。
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸134.9部、1,6−ヘキサンジオール100.9部、ネオペンチルグリコール3.1部、およびイソシアヌル酸トリス(2−ヒドロキシエチル)30.3部を仕込み、窒素雰囲気下で140℃まで昇温した。
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸134.9部、シクロヘキサンジメタノール81.9部、ネオペンチルグリコール1.9部、およびイソシアヌル酸トリス(2−ヒドロキシエチル)108.1部を仕込み、窒素雰囲気下で140℃まで昇温した。
水酸基含有ポリエステル樹脂(A2)溶液の製造
製造例7
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸69.3部、アジピン酸73.0部、1,6−ヘキサンジオール106.2部、およびトリメチロールプロパン13.4部を仕込み、窒素雰囲気下で140℃まで昇温した。
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸62.5部、アジピン酸65.7部、1,6−ヘキサンジオール106.4部、およびトリメチロールプロパン13.4部を仕込み、窒素雰囲気下で140℃まで昇温した。
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸70.8部、アジピン酸74.5部、1,6−ヘキサンジオール106.4部、およびトリメチロールプロパン13.4部を仕込み、窒素雰囲気下で140℃まで昇温した。
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸68.6部、アジピン酸72.2部、1,6−ヘキサンジオール94.8部、および
トリメチロールプロパン26.6部を仕込み、窒素雰囲気下で140℃まで昇温した。
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸69.9部、アジピン酸73.5部、1,6−ヘキサンジオール112.3部、およびトリメチロールプロパン6.7部を仕込み、窒素雰囲気下で140℃まで昇温した。
撹拌機、温度計、精留塔および水分離器を装備した反応容器に、ヘキサヒドロ無水フタル酸57.8部、アジピン酸60.9部、シクロヘキサンジメタノール132.1部、およびトリメチロールプロパン11.1部を仕込み、窒素雰囲気下で140℃まで昇温した。
塗料組成物の製造
実施例1〜18及び比較例1〜7
表1に記載の配合組成に従って、ポリエステル樹脂と分散剤で、公知の分散方法によってカーボンブラックを分散した後、残りの成分を容器に配合し、混合・攪拌して固形分約40%の各主剤を作成した。この主剤に表1に記載の配合組成に従ってポリイソシアネート硬化剤を加え、均一に混合して、各塗料組成物No.1〜25を作成し、希釈溶剤で粘度25秒/フォードカップ#4/20℃に粘調した。尚、表1は固形分表示であり、表1中における(注1)〜(注9)は下記の通りである。
(注2)ウレタン樹脂ビーズ(B−2):根上工業社製、「P−800T」、平均粒子径6μm
(注3)アクリル樹脂ビーズ(B−3):積水化成品工業社製、「AFX−8」、平均粒子径8μm
(注4)中空発泡樹脂粒子(B−4):EXPANCEL社製、「461−20」、平均粒子径8μm
(注5)架橋ゴム粒子(B−5):D.O.G社製、「Deogrip Micro S」、平均粒子径10μm
(注6)分散剤:ルブリゾール社製、「ソルスパーズ37500」
(注7)硬化触媒:日東化成社製、「ネオスタン U−100」
(注8)ポリイソシアネート(C−1):旭化成ケミカルズ社製、「デュラネート24A−90E」、ビュレット体
(注9)ポリイソシアネート(C−2):住友バイエルウレタン社製、「スミジュールN3300」、ヌレート体。
次いでABS板(脱脂処理済み)に、上記のとおり粘調した各塗料組成物No.1〜25を乾燥膜厚で約40μmになるようにエアスプレー塗装を行ない、80℃で30分間加熱し硬化させて各試験塗板を得た。
(*1)鉛筆硬度:JIS K 5600−5−4に準じて実施した。各試験塗板の塗膜面に対し約45°の角度に鉛筆の芯を当て、芯が折れない程度に強く塗膜面に押し付けながら、鉛筆を前方に均一な速さで約10mm動かす。当該操作を、場所を変えて5回繰り返し、塗膜に鉛筆芯の痕がつかない最も硬い鉛筆の硬度記号を鉛筆硬度とした。
(*2)付着性:各試験塗板の塗膜面に素地に達するようにカッターで切り込み線を入れ、大きさ2mm×2mmのマス目を100個作り、その表面に粘着セロハンテープを貼着し、20℃においてそれを急激に剥離した後のマス目の残存塗膜数を調べた。全く剥離なしを○、1マス以上剥がれたものを×とした。
(*3)しっとり感:各試験塗板の塗膜面の触感を評価するため、指で触れた際のしっとり感を、下記判断基準に従って評価した。
○:硬化塗膜を手で触れた際に、弾力がある
△:硬化塗膜を手で触れた際に、やや弾力がある
×:硬化塗膜を手で触れた際に、ほとんど弾力がない。
(*4)ソフトフィール値(SF値):各試験塗板の塗膜のソフトフィール値(SF値)を、前述の計算式に従って計測した。
(*5)耐薬品性:各試験塗板の塗膜面に薬品(コパトーンSPF50)を滴下し塗り広げて、50℃で3時間放置した後に、表面の薬品をふき取り塗膜外観、上記(*1)の鉛筆硬度及び(*2)の付着性を評価した。
○:異常なし
×:ちぢみ、変色、跡付きなど発生
Claims (3)
- 水酸基含有ポリエステル樹脂(A)及び樹脂ビーズ(B)を含有する主剤と、ポリイソシアネート硬化剤とからなる塗料組成物であって、
水酸基含有ポリエステル樹脂(A)が、水酸基価50〜200mgKOH/g、ガラス転移温度−30〜0℃の水酸基含有ポリエステル樹脂(A1)、及び水酸基価30〜100mgKOH/g、ガラス転移温度−30℃未満の水酸基含有ポリエステル樹脂(A2)を含むものであり、
該水酸基含有ポリエステル樹脂(A1)及び(A2)の固形分質量比が、(A1)/(A2)=80/20〜20/80であり、且つ
樹脂ビーズ(B)を主剤中の全固形分質量を基準として20〜80質量%含有することを特徴とする塗料組成物。 - 水酸基含有ポリエステル樹脂(A1)が、ヌレート構造を有する環状ポリオール化合物(a1)を含む多価アルコールと多塩基酸との反応によって得られる水酸基含有ポリエステル樹脂(A1−1)である請求項1記載の塗料組成物。
- 基材面に、請求項1または2に記載の塗料組成物を塗装して得られる塗装物品。
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JP2017031387A (ja) * | 2015-07-29 | 2017-02-09 | 東ソー株式会社 | 耐紫外線吸収剤性ポリウレタン組成物、該組成物を用いたコーティング材 |
JP2017128715A (ja) * | 2016-01-15 | 2017-07-27 | 荒川化学工業株式会社 | 塗料組成物、塗料皮膜及び成形物 |
JP2017149873A (ja) * | 2016-02-25 | 2017-08-31 | 東ソー株式会社 | 塗料用ウレタン樹脂組成物 |
JP2021050265A (ja) * | 2019-09-24 | 2021-04-01 | 大日本塗料株式会社 | 2液型ウレタン塗料組成物 |
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JP2017031387A (ja) * | 2015-07-29 | 2017-02-09 | 東ソー株式会社 | 耐紫外線吸収剤性ポリウレタン組成物、該組成物を用いたコーティング材 |
JP2017128715A (ja) * | 2016-01-15 | 2017-07-27 | 荒川化学工業株式会社 | 塗料組成物、塗料皮膜及び成形物 |
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JP2021050265A (ja) * | 2019-09-24 | 2021-04-01 | 大日本塗料株式会社 | 2液型ウレタン塗料組成物 |
JP7379043B2 (ja) | 2019-09-24 | 2023-11-14 | 大日本塗料株式会社 | 2液型ウレタン塗料組成物 |
CN114106606A (zh) * | 2021-12-16 | 2022-03-01 | 青岛大学 | 防轮胎变色保护液及其制备方法 |
CN114106606B (zh) * | 2021-12-16 | 2022-11-29 | 青岛大学 | 防轮胎变色保护液及其制备方法 |
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