JP2006176632A - 硬化性樹脂組成物、クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 - Google Patents
硬化性樹脂組成物、クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 Download PDFInfo
- Publication number
- JP2006176632A JP2006176632A JP2004370975A JP2004370975A JP2006176632A JP 2006176632 A JP2006176632 A JP 2006176632A JP 2004370975 A JP2004370975 A JP 2004370975A JP 2004370975 A JP2004370975 A JP 2004370975A JP 2006176632 A JP2006176632 A JP 2006176632A
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- JP
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- Prior art keywords
- coating film
- curable resin
- containing acrylic
- acrylic resin
- resin composition
- 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
Links
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- 239000011248 coating agent Substances 0.000 title claims description 87
- 239000008199 coating composition Substances 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 68
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 54
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 54
- -1 isocyanate compound Chemical class 0.000 claims abstract description 50
- 239000000178 monomer Substances 0.000 claims abstract description 47
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 37
- 239000012948 isocyanate Substances 0.000 claims abstract description 37
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 29
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- 239000007787 solid Substances 0.000 claims abstract description 20
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- 239000002253 acid Substances 0.000 abstract description 29
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- 238000001723 curing Methods 0.000 description 18
- 229920005989 resin Polymers 0.000 description 13
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- 238000002156 mixing Methods 0.000 description 11
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- 238000010438 heat treatment Methods 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
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- 229910052751 metal Inorganic materials 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
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- 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 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 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
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
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- 238000005299 abrasion Methods 0.000 description 2
- 229920006243 acrylic copolymer Polymers 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
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- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 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
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
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- 238000001816 cooling Methods 0.000 description 2
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- 239000006260 foam Substances 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
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- 150000007970 thio esters Chemical class 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
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- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- KQALJCGUCSYRMJ-UHFFFAOYSA-N 1,3,5-triethyl-2,4-bis(isocyanatomethyl)benzene Chemical compound CCC1=CC(CC)=C(CN=C=O)C(CC)=C1CN=C=O KQALJCGUCSYRMJ-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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 1
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- 239000004606 Fillers/Extenders Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
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- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-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
- 238000003916 acid precipitation Methods 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
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- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
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- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
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- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
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- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
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- 239000003999 initiator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000014759 maintenance of location Effects 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
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- 125000005641 methacryl group Chemical group 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 239000011259 mixed solution Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
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- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
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- 239000004645 polyester resin Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
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- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 239000004576 sand Substances 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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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- C08G18/40—High-molecular-weight compounds
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- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/36—Successively applying liquids or other fluent materials, e.g. without intermediate treatment
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
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- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
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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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
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- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
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Abstract
【解決手段】 水酸基含有アクリル樹脂と多官能イソシアネート化合物とを含有する硬化性樹脂組成物であって、
前記水酸基含有アクリル樹脂が、少なくとも一部のモノマーとして炭素数4〜9のヒドロキシアルキル基を有するヒドロキシアルキル(メタ)アクリレートを用いて得た水酸基含有アクリル樹脂であり、
前記硬化性樹脂組成物は、下記一般式(1):
−(CH2)n− (1)
(式中、nは4以上の整数を表す。)
で表されるソフトセグメント部を、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対して25〜50質量%有しており、かつ、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対するラクトン含有モノマー由来のソフトセグメント部の割合が8質量%以下となるように調製されていることを特徴とする硬化性樹脂組成物。
【選択図】 なし
Description
前記水酸基含有アクリル樹脂が、少なくとも一部のモノマーとして炭素数4〜9のヒドロキシアルキル基を有するヒドロキシアルキル(メタ)アクリレートを用いて得た水酸基含有アクリル樹脂であり、
前記硬化性樹脂組成物は、下記一般式(1):
−(CH2)n− (1)
(式中、nは4以上の整数を表す。)
で表されるソフトセグメント部を、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対して25〜50質量%有しており、かつ、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対するラクトン含有モノマー由来のソフトセグメント部の割合が8質量%以下となるように調製されていることを特徴とするものである。
−(CH2)n− (1)
(式中、nは4以上の整数を表す。)
で表されるソフトセグメント部を、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対して25〜50質量%有しており、かつ、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対するラクトン含有モノマー由来のソフトセグメント部の割合が8質量%以下となるように調製されていることを特徴とするものである。
E'=3nRT (n:架橋密度、R:気体定数、T:絶対温度)。
撹拌羽根、窒素導入管、冷却コンデンサー及び滴下ロートを備えた2Lのガラス容器に、プロピレングリコールモノメチルエーテルアセテート358.0g及びキシレン90.0gを加え、窒素雰囲気下130℃に加温した。その容器に、滴下ロートを用いてプロピレングリコールモノメチルエーテルアセテート100.0g、tert−ブチルパーオキシ−2−エチルヘキサノエート100.0g、スチレン68.9g、アクリル酸−n−ブチル312.0g、メタクリル酸−2−エチルヘキシル182.1g、アクリル酸−4−ヒドロキシブチル437.0gを3時間かけて等速滴下した。その後130℃で0.5時間保持し、50.0gのプロピレングリコールモノメチルエーテルアセテートに溶解したtert−ブチルパーオキシ−2−エチルヘキサノエート10.0gを30分で等速滴下した。更に、130℃で1.0時間加温を続けることによって、目的の水酸基含有アクリル樹脂aを得た。
表1に示すモノマー成分、溶媒及び重合開始剤を用い、それらの配合量を表1に示すようにした以外は合成例1と同様にして、水酸基含有アクリル樹脂b〜fをそれぞれ合成した。なお、プラクセルFM−2としては2−ヒドロキシエチルメタクリレートとε−カプロラクトンの1:2付加物(ダイセル工業社製)、プラクセルFM−5としては2−ヒドロキシエチルメタクリレートとε−カプロラクトンの1:5付加物(ダイセル工業社製)を用いた。
表2に示した配合に従い、各成分を混合し、ディスパーで攪拌することによって実施例1〜5及び比較例1のクリヤー塗料組成物を得た。上記クリヤー塗料組成物を、プロピレングリコールモノメチルエーテルアセテート/3−エトキシプロピオン酸エチル=1/2(質量比)からなるシンナーによってNo.4フォードカップで25秒/20℃となるようにそれぞれ希釈した。なお、ビュレット型イソシアネート硬化剤としては、住化バイエルウレタン(株)社製スミジュールN−75を用いた。
実施例1〜5及び比較例1のクリヤー塗料組成物を用いて得られた複層塗膜について、以下の評価方法によって40%硫酸水溶液による耐酸性の評価を行った。
○:スポット部に塗膜のハガレは認められないもの。
△:スポット部の塗膜の一部にハガレが認められたもの。
×:スポット部の塗膜が完全にハガレているもの。
実施例1〜5及び比較例1のクリヤー塗料組成物を用いて得られた複層塗膜について、以下の評価方法によって耐擦り傷性の評価を行った。
Claims (5)
- 水酸基含有アクリル樹脂と多官能イソシアネート化合物とを含有する硬化性樹脂組成物であって、
前記水酸基含有アクリル樹脂が、少なくとも一部のモノマーとして炭素数4〜9のヒドロキシアルキル基を有するヒドロキシアルキル(メタ)アクリレートを用いて得た水酸基含有アクリル樹脂であり、
前記硬化性樹脂組成物は、下記一般式(1):
−(CH2)n− (1)
(式中、nは4以上の整数を表す。)
で表されるソフトセグメント部を、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対して25〜50質量%有しており、かつ、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対するラクトン含有モノマー由来のソフトセグメント部の割合が8質量%以下となるように調製されていることを特徴とする硬化性樹脂組成物。 - 前記ヒドロキシアルキル(メタ)アクリレートが、4−ヒドロキシブチルアクリレートであることを特徴とする請求項1に記載の硬化性樹脂組成物。
- 請求項1又は2に記載の硬化性樹脂組成物をバインダーとして含有することを特徴とするクリヤー塗料組成物。
- 被塗装物に対してトップコートを有する複層塗膜を形成する方法であって、請求項3に記載のクリヤー塗料組成物を前記トップコートとして塗装することを特徴とする複層塗膜の形成方法。
- 前記被塗装物にベース塗料組成物を塗布してベース未硬化塗膜を得た後、前記ベース未硬化塗膜に前記クリヤー塗料組成物を塗布してクリヤー未硬化塗膜を得、前記ベース未硬化塗膜及びクリヤー未硬化塗膜を同時に加熱して硬化させることを特徴とする請求項4に記載の複層塗膜の形成方法。
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PCT/JP2005/023572 WO2006068209A1 (ja) | 2004-12-22 | 2005-12-22 | 硬化性樹脂組成物、クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2006176634A (ja) * | 2004-12-22 | 2006-07-06 | Nippon Paint Co Ltd | 自動車用クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 |
WO2009024351A1 (en) | 2007-08-22 | 2009-02-26 | Basf Coatings Japan Ltd. | Paint compositions, a method of finish-painting and painted objects |
JP2011167614A (ja) * | 2010-02-17 | 2011-09-01 | Mazda Motor Corp | 積層塗膜形成方法 |
JP2012530816A (ja) * | 2009-06-24 | 2012-12-06 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 被覆剤及びそれから製造され、高い引掻強度をエリクセン深さ試験で良好な結果及び良好な耐ストーンチップ性と同時に有する被覆物 |
WO2013031976A1 (ja) | 2011-09-01 | 2013-03-07 | 日本ペイント株式会社 | クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 |
WO2013031977A1 (ja) | 2011-09-01 | 2013-03-07 | 日本ペイント株式会社 | クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 |
JP2013060586A (ja) * | 2011-08-19 | 2013-04-04 | Fuji Xerox Co Ltd | 樹脂材料 |
DE102017121277A1 (de) | 2016-09-28 | 2018-03-29 | Asahi Kasei Kabushiki Kaisha | Beschichtungsmaterialzusammensetzung |
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JPH07196982A (ja) * | 1993-12-28 | 1995-08-01 | Mitsubishi Rayon Co Ltd | 熱硬化被覆組成物 |
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JP4184689B2 (ja) * | 2001-03-29 | 2008-11-19 | 関西ペイント株式会社 | 塗料組成物 |
JP2003253191A (ja) * | 2002-02-28 | 2003-09-10 | Nippon Paint Co Ltd | クリヤー塗料組成物及び複層塗膜形成方法 |
JP2003301028A (ja) * | 2002-04-11 | 2003-10-21 | Nippon Paint Co Ltd | 硬化性樹脂組成物、クリヤー塗料組成物及び複層塗膜形成方法 |
JP2006008936A (ja) * | 2004-06-29 | 2006-01-12 | Nippon Paint Co Ltd | 自動車用クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 |
-
2004
- 2004-12-22 JP JP2004370975A patent/JP4902115B2/ja not_active Expired - Fee Related
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- 2005-12-22 WO PCT/JP2005/023572 patent/WO2006068209A1/ja active Application Filing
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- 2007-06-21 GB GB0712047A patent/GB2435192A/en not_active Withdrawn
Patent Citations (2)
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JPH07196982A (ja) * | 1993-12-28 | 1995-08-01 | Mitsubishi Rayon Co Ltd | 熱硬化被覆組成物 |
JP2002167422A (ja) * | 2000-11-30 | 2002-06-11 | Daicel Chem Ind Ltd | 低ラクトン変性ヒドロキシアルキル(メタ)アクリル酸エステル組成物を用いたイソシアネート硬化系塗料組成物 |
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JP2006176634A (ja) * | 2004-12-22 | 2006-07-06 | Nippon Paint Co Ltd | 自動車用クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 |
WO2009024351A1 (en) | 2007-08-22 | 2009-02-26 | Basf Coatings Japan Ltd. | Paint compositions, a method of finish-painting and painted objects |
US8236895B2 (en) | 2007-08-22 | 2012-08-07 | Basf Coatings Japan Ltd. | Paint compositions, a method of finish-painting and painted objects |
JP2012530816A (ja) * | 2009-06-24 | 2012-12-06 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 被覆剤及びそれから製造され、高い引掻強度をエリクセン深さ試験で良好な結果及び良好な耐ストーンチップ性と同時に有する被覆物 |
KR101736513B1 (ko) | 2009-06-24 | 2017-05-16 | 바스프 코팅스 게엠베하 | 에릭슨 깊이 시험에서 양호한 결과를 나타내고 양호한 스톤칩핑 저항 성질을 가지면서 높은 내스크래치성을 갖는 코팅 제제 및 이로부터 형성된 코팅 |
JP2011167614A (ja) * | 2010-02-17 | 2011-09-01 | Mazda Motor Corp | 積層塗膜形成方法 |
JP2013060586A (ja) * | 2011-08-19 | 2013-04-04 | Fuji Xerox Co Ltd | 樹脂材料 |
US8785564B2 (en) | 2011-08-19 | 2014-07-22 | Fuji Xerox Co., Ltd. | Resin material |
WO2013031976A1 (ja) | 2011-09-01 | 2013-03-07 | 日本ペイント株式会社 | クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 |
WO2013031977A1 (ja) | 2011-09-01 | 2013-03-07 | 日本ペイント株式会社 | クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 |
DE102017121277A1 (de) | 2016-09-28 | 2018-03-29 | Asahi Kasei Kabushiki Kaisha | Beschichtungsmaterialzusammensetzung |
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JP4902115B2 (ja) | 2012-03-21 |
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WO2006068209A1 (ja) | 2006-06-29 |
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