JP5047974B2 - 非水性液体コーティング組成物 - Google Patents
非水性液体コーティング組成物 Download PDFInfo
- Publication number
- JP5047974B2 JP5047974B2 JP2008532388A JP2008532388A JP5047974B2 JP 5047974 B2 JP5047974 B2 JP 5047974B2 JP 2008532388 A JP2008532388 A JP 2008532388A JP 2008532388 A JP2008532388 A JP 2008532388A JP 5047974 B2 JP5047974 B2 JP 5047974B2
- Authority
- JP
- Japan
- Prior art keywords
- diol
- coating composition
- component
- polyurethane resin
- diisocyanate
- 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.)
- Expired - Fee Related
Links
- 239000008199 coating composition Substances 0.000 title claims description 55
- 239000007788 liquid Substances 0.000 title claims description 16
- 229920005749 polyurethane resin Polymers 0.000 claims description 59
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 239000007787 solid Substances 0.000 claims description 32
- 239000002245 particle Substances 0.000 claims description 28
- 238000002844 melting Methods 0.000 claims description 26
- 230000008018 melting Effects 0.000 claims description 26
- 239000011247 coating layer Substances 0.000 claims description 13
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000004971 Cross linker Substances 0.000 claims description 6
- 238000013007 heat curing Methods 0.000 claims 1
- 150000002009 diols Chemical class 0.000 description 141
- 239000000203 mixture Substances 0.000 description 32
- 125000005442 diisocyanate group Chemical group 0.000 description 30
- 229920002635 polyurethane Polymers 0.000 description 30
- 239000004814 polyurethane Substances 0.000 description 30
- 239000011230 binding agent Substances 0.000 description 25
- 238000000576 coating method Methods 0.000 description 24
- 239000000049 pigment Substances 0.000 description 22
- 239000011248 coating agent Substances 0.000 description 20
- 239000010410 layer Substances 0.000 description 20
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 19
- 125000001931 aliphatic group Chemical group 0.000 description 17
- 239000003960 organic solvent Substances 0.000 description 16
- -1 aliphatic diols Chemical class 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 229920005862 polyol Polymers 0.000 description 14
- 150000003077 polyols Chemical class 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 10
- 239000003431 cross linking reagent Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 6
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 5
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- JTDWCIXOEPQECG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC(C)(C)C Chemical compound N=C=O.N=C=O.CCCCCC(C)(C)C JTDWCIXOEPQECG-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 3
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 239000012738 dissolution medium Substances 0.000 description 3
- 230000009977 dual effect Effects 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 238000011403 purification operation Methods 0.000 description 3
- 238000007665 sagging Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000001029 thermal curing Methods 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 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
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 2
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 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
- 230000001588 bifunctional effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- OQHAOYHGURHBDD-UHFFFAOYSA-N butane-1,1-diol propane Chemical compound CCC.CCCC(O)O OQHAOYHGURHBDD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000003010 ionic group Chemical group 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000010309 melting process Methods 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 2
- 230000003711 photoprotective effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000012798 spherical particle Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- OQQOAWVKVDAJOI-UHFFFAOYSA-N (2-dodecanoyloxy-3-hydroxypropyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCC OQQOAWVKVDAJOI-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- VXKUOGVOWWPRNM-UHFFFAOYSA-N 3-ethoxypropyl acetate Chemical compound CCOCCCOC(C)=O VXKUOGVOWWPRNM-UHFFFAOYSA-N 0.000 description 1
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 1
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000000026 Pentaerythritol tetranitrate Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000006115 industrial coating Substances 0.000 description 1
- 239000001034 iron oxide pigment Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 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
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000012708 photoinduced radical polymerization Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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Description
このような組成物は、「デュアル硬化」コーティング組成物とも呼ばれる。
下記の一般合成方法に従って、HDI(1,6−ヘキサンジイソシアネート)、またはHDIとDCMDI(ジシクロヘキシルメタンジイソシアネート)の混合物と、1つもしくは複数のジオールを反応させることによって、ポリウレタンジオールを生成した。
下記の一般合成方法に従って、HDI、または混合物HDIとDCMDIの混合物と、GLY(グリセロール)と1つもしくは複数のジオールの混合物を反応させることによって、ポリウレタンポリオールを生成した。
下記の成分を混合することによって、ベースを調製した。
61.6部:Solvesso(登録商標)100と酢酸ブチルの混合物(2:1)中、メタクリル酸系コポリマー(酸価:5mgのKOH/g、ヒドロキシル値:147mgのKOH/g)の65重量%溶液
6.7部:Solvesso(登録商標)100中、分枝状ポリエステル(酸価:41mgのKOH/g、ヒドロキシル値:198mgのKOH/g、数平均分子量:1000)の65重量%溶液
5.3部:エトキシプロピルアセテート
6.8部:Solvesso(登録商標)150
1.2部:Ciba製Tinuvin(登録商標)292(光保護剤)
1.2部:Ciba製Tinuvin(登録商標)384(紫外線吸収剤)
2.0部:酢酸ブチル
4.3部:ブチルジグリコールアセテート
4.4部:ブチルグリコールアセテート
6.5部:Solvesso(登録商標)100
実施例1a、d、e、f、h、k、lの固体ポリウレタンジオール、ならびに実施例2aおよび2dの固体ポリウレタンポリオールを、いずれの場合も、粉体コーティングの生成で一般的な粉砕および篩い分け方法によって粉砕し、すり砕き、篩い分けし、この方式で、平均粒径50μmの結合剤粉末(レーザー回折によって決定)に変換した。
下記の成分を混合することによって、クリアコートを調製した。
53.3部:Solvesso(登録商標)100とブタノールの混合物(4:1)中、メタクリル酸系コポリマー(酸価:20mgのKOH/g、ヒドロキシル値:119mgのKOH/g)の65重量%溶液
28.0部:BASF製Luwipal(登録商標)018(メラミン樹脂)
11.8部:Solvesso(登録商標)150
0.9部:Ciba製Tinuvin(登録商標)1130(紫外線吸収剤)
0.9部:Ciba製Tinuvin(登録商標)144(光保護剤)
0.9部:King製Nacure(登録商標)5225(触媒)
4.2部:Solvesso(登録商標)100
ヒドロキシル官能性メタクリル酸系コポリマーの一部分を、実施例4a〜4iで記載したように調製された粉末状のポリウレタンジオールまたはポリウレタンポリオールに置換して、実施例5を数回繰り返した。置換は、いずれの場合も10モル%の条件で、または第2のシリーズでは、いずれの場合も20モル%のOH置換の条件で、粉末状のポリウレタンジオールまたはポリオールを、メタクリル酸系コポリマーの溶液の一部分の代わりに使用することによって行った。必要に応じて、初期フロー時間を、実施例5の場合と同様の値に調整した。
次に、本発明の好ましい態様を示す。
1. 少なくとも1つのヒドロキシル官能性成分A、前記少なくとも1つの成分Aとは異なる少なくとも1つのヒドロキシル官能性ポリウレタン樹脂B、ならびにAおよびBのヒドロキシル基に対して反応性がある基を有する少なくとも1つの架橋剤Cを含有する非水性液体コーティング組成物であって、前記少なくとも1つの成分Aは、室温で固体でなく、および/または溶解された形で存在し、前記少なくとも1つのポリウレタン樹脂Bは、40〜180℃の融点を有する粒子として存在するコーティング組成物。
2. 固形分が40〜85重量%であり、有機溶媒含有量が15〜60重量%であり、前記固形分と前記有機溶媒含有量の重量%の合計が90〜100重量%であり、前記固形分は、樹脂固形分、ならびに任意の成分:顔料、充填剤、および非揮発性添加剤からなる上記1に記載のコーティング組成物。
3. 前記樹脂固形分が、50〜90重量%の成分AおよびBからなる結合剤固形分、10〜50重量%の1つまたは複数の架橋剤C、ならびに0〜30重量%の1つまたは複数の成分D(ただし、重量百分率は合計100重量%になる)からなる上記2に記載のコーティング組成物。
4. 前記結合剤固形分が、0重量%より多く95重量%までの少なくとも1つのヒドロキシル官能性成分A、および5重量%から100重量%未満の少なくとも1つのヒドロキシル官能性ポリウレタン樹脂B(ただし、重量百分率は合計100重量%になる)からなる上記3に記載のコーティング組成物。
5. 前記少なくとも1つのポリウレタン樹脂Bの融点が、30〜150℃の幅広い溶融範囲の上端である上記1〜4のいずれか一項に記載のコーティング組成物。
6. 前記少なくとも1つのポリウレタン樹脂Bの溶解性が、20℃において10g未満/酢酸ブチル1リットルである上記1〜5のいずれか一項に記載のコーティング組成物。
7. レーザー回折によって決定された前記ポリウレタン樹脂B粒子の平均粒径が1〜100μmである上記1〜6のいずれか一項に記載のコーティング組成物。
8. 前記ポリウレタン樹脂B粒子が、前記少なくとも1つの固体ポリウレタン樹脂Bの粉砕、または前記少なくとも1つのポリウレタン樹脂Bの溶解媒体での熱溶解、続いて冷却中および/または冷却後の粒子形成によって形成される上記1〜7のいずれか一項に記載のコーティング組成物。
9. 前記少なくとも1つのポリウレタン樹脂Bが、1,6−ヘキサンジイソシアネートとジオール成分を、x:(x+1)のモル比(式中、xは、2〜6の任意の所望の値を意味する)で反応させることによって調製することができるポリウレタンジオールであり、前記ジオール成分が、単一ジオールまたはジオールの組合せである上記1〜8のいずれか一項に記載のコーティング組成物。
10. 前記少なくとも1つのポリウレタン樹脂Bが、ジイソシアネート成分とジオール成分を、x:(x+1)のモル比(式中、xは、2〜6の任意の所望の値を意味する)で反応させることによって調製することができるポリウレタンジオールであり、前記ジイソシアネート成分の50〜80モル%は、1,6−ヘキサンジイソシアネートで生成され、20〜50モル%は、1つまたは2つのジイソシアネートで生成され、それぞれ、前記ジイソシアネート成分の少なくとも10モル%を構成し、トルイレンジイソシアネート、ジフェニルメタンジイソシアネート、ジシクロヘキシルメタンジイソシアネート、イソホロンジイソシアネート、トリメチルヘキサンジイソシアネート、シクロヘキサンジイソシアネート、シクロヘキサンジメチレンジイソシアネート、およびテトラメチレンキシリレンジイソシアネートからなる群から選択され、前記それぞれのジイソシアネートのモル%は合計100モル%になり、前記ジオール成分の20〜100モル%は、少なくとも1つの線状脂肪族α,ω−C2〜C12−ジオールで生成され、0〜80モル%は、線状脂肪族α,ω−C2〜C12−ジオールと異なる少なくとも1つのジオールで生成され、前記それぞれのジオールのモル%は合計100モル%になる上記1〜8のいずれか一項に記載のコーティング組成物。
11. 所定の比率の前記ジオール成分が、少なくとも1つのトリオールを含むトリオール成分で置換される上記9または10に記載のコーティング組成物。
12. コーティング層の調製方法であって、
下記の連続ステップ:
1)上記1〜11のいずれか一項に記載のコーティング組成物によるコーティング層を塗布するステップと、
2)場合によっては、前記塗布されたコーティング層をフラッシュオフして、溶媒を除去するステップと、
3)前記コーティング層を、前記少なくとも1つのポリウレタン樹脂Bの融点を超える物体温度で熱硬化するステップと
を含む方法。
13. 前記コーティング層が、単層コーティング、および多層コーティング内のコーティング層からなる群から選択される上記12に記載の方法。
14. 前記多層コーティング内のコーティング層が、自動車車体、および自動車車体部品からなる群から選択された基材上の自動車用多層コーティングである上記13に記載の方法。
15. 前記コーティング層が、プライマーサーフェーサー層、外側クリアトップコート層、および透明シーリング層からなる群から選択される上記14に記載の方法。
Claims (2)
- 少なくとも1つのヒドロキシル官能性成分A、前記少なくとも1つの成分Aとは異なる少なくとも1つのヒドロキシル官能性ポリウレタン樹脂B、ならびにAおよびBのヒドロキシル基に対して反応性がある基を有する少なくとも1つの架橋剤Cを含有する非水性液体コーティング組成物であって、前記少なくとも1つの成分Aは、室温で固体でなく、および/またはコーティング組成物に溶解された形で存在し、前記少なくとも1つのポリウレタン樹脂Bは、40〜180℃の融点を有する粒子として存在し、
融点は、DSC(示差走査熱分析)により10K/分の加熱速度で決定される、コーティング組成物。 - コーティング層の調製方法であって、
下記の連続ステップ:
1)請求項1に記載のコーティング組成物によるコーティング層を塗布するステップと、
2)前記コーティング層を、前記少なくとも1つのポリウレタン樹脂Bの融点を超える物体温度で熱硬化するステップと
を含み、
融点は、DSC(示差走査熱分析)により10K/分の加熱速度で決定される、方法。
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WO2007081846A2 (en) * | 2006-01-09 | 2007-07-19 | E. I. Du Pont De Nemours And Company | Non-aqueous, liquid coating compositions |
US20070185266A1 (en) * | 2006-02-07 | 2007-08-09 | Carmen Flosbach | Non-aqueous, liquid coating compositions curable by free-radical polymerization of olefinic double bonds |
WO2007133407A2 (en) * | 2006-05-03 | 2007-11-22 | E. I. Du Pont De Nemours And Company | Liquid coating compositions comprising polyurethane resin sag control agents |
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EP2514778B1 (en) * | 2009-09-28 | 2013-10-16 | Coatings Foreign IP Co. LLC | Liquid two-component coating compositions |
US8685497B2 (en) * | 2010-05-07 | 2014-04-01 | Axalta Coating Systems Ip Co., Llc | Liquid coating composition |
EP2566907B1 (en) | 2010-05-07 | 2014-12-10 | Coatings Foreign IP Co. LLC | Liquid coating composition |
US20140072815A1 (en) * | 2012-09-12 | 2014-03-13 | Ppg Industries Ohio, Inc. | Curable film-forming compositions demonstrating burnish resistance and low gloss |
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US8691006B2 (en) | 2005-09-21 | 2014-04-08 | Axalta Coating Systems Ip Co., Llc | Non-aqueous, liquid coating compositions |
EP1966262B1 (en) | 2005-12-09 | 2016-03-09 | Coatings Foreign IP Co. LLC | Non-aqueous, liquid coating compositions |
WO2007081846A2 (en) * | 2006-01-09 | 2007-07-19 | E. I. Du Pont De Nemours And Company | Non-aqueous, liquid coating compositions |
WO2007081844A2 (en) | 2006-01-09 | 2007-07-19 | E. I. Du Pont De Nemours And Company | Non-aqueous, liquid coating compositions |
-
2006
- 2006-09-21 US US11/990,069 patent/US8691006B2/en not_active Expired - Fee Related
- 2006-09-21 WO PCT/US2006/036843 patent/WO2007035876A1/en active Application Filing
- 2006-09-21 DE DE602006006709T patent/DE602006006709D1/de active Active
- 2006-09-21 EP EP06803996A patent/EP1937739B1/en not_active Expired - Fee Related
- 2006-09-21 JP JP2008532388A patent/JP5047974B2/ja not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8691006B2 (en) | 2005-09-21 | 2014-04-08 | Axalta Coating Systems Ip Co., Llc | Non-aqueous, liquid coating compositions |
Also Published As
Publication number | Publication date |
---|---|
DE602006006709D1 (de) | 2009-06-18 |
EP1937739A1 (en) | 2008-07-02 |
WO2007035876A1 (en) | 2007-03-29 |
US8691006B2 (en) | 2014-04-08 |
US20090035471A1 (en) | 2009-02-05 |
JP2009509028A (ja) | 2009-03-05 |
EP1937739B1 (en) | 2009-05-06 |
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