JP3861882B2 - コーティング用組成物 - Google Patents
コーティング用組成物 Download PDFInfo
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- JP3861882B2 JP3861882B2 JP2004022696A JP2004022696A JP3861882B2 JP 3861882 B2 JP3861882 B2 JP 3861882B2 JP 2004022696 A JP2004022696 A JP 2004022696A JP 2004022696 A JP2004022696 A JP 2004022696A JP 3861882 B2 JP3861882 B2 JP 3861882B2
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- Prior art keywords
- pigment
- coating composition
- dispersion
- organic
- group
- 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.)
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- 239000008199 coating composition Substances 0.000 title claims description 50
- 239000006185 dispersion Substances 0.000 claims description 59
- 239000011248 coating agent Substances 0.000 claims description 51
- 238000000576 coating method Methods 0.000 claims description 51
- 239000011521 glass Substances 0.000 claims description 45
- 239000012860 organic pigment Substances 0.000 claims description 32
- 125000000524 functional group Chemical group 0.000 claims description 30
- -1 silicon alkoxide compound Chemical class 0.000 claims description 26
- 239000000758 substrate Substances 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 150000003918 triazines Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 239000010703 silicon Substances 0.000 claims description 8
- 238000001179 sorption measurement Methods 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 239000000049 pigment Substances 0.000 description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- 239000000975 dye Substances 0.000 description 31
- 239000002245 particle Substances 0.000 description 26
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 24
- 239000010408 film Substances 0.000 description 24
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- 239000000203 mixture Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
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- 150000001875 compounds Chemical class 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 10
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- 239000000243 solution Substances 0.000 description 10
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- 239000011259 mixed solution Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 7
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- 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 7
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 6
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- 125000000962 organic group Chemical group 0.000 description 6
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- 125000004432 carbon atom Chemical group C* 0.000 description 5
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- 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 4
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
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- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 3
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- 238000003980 solgel method Methods 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical compound C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- 229910052759 nickel Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 2
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- 229910052726 zirconium Inorganic materials 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
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- XQGDNRFLRLSUFQ-UHFFFAOYSA-N 2H-pyranthren-1-one Chemical class C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 XQGDNRFLRLSUFQ-UHFFFAOYSA-N 0.000 description 1
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- ZEHOVWPIGREOPO-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-[2-(4,5,6,7-tetrachloro-1,3-dioxoinden-2-yl)quinolin-8-yl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C(=O)N1C(C1=N2)=CC=CC1=CC=C2C1C(=O)C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2C1=O ZEHOVWPIGREOPO-UHFFFAOYSA-N 0.000 description 1
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- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
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- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
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- ZLFVRXUOSPRRKQ-UHFFFAOYSA-N chembl2138372 Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 ZLFVRXUOSPRRKQ-UHFFFAOYSA-N 0.000 description 1
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- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
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- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical compound C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 description 1
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- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- ZZSIDSMUTXFKNS-UHFFFAOYSA-N perylene red Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N(C(=O)C=1C2=C3C4=C(OC=5C=CC=CC=5)C=1)C(=O)C2=CC(OC=1C=CC=CC=1)=C3C(C(OC=1C=CC=CC=1)=CC1=C2C(C(N(C=3C(=CC=CC=3C(C)C)C(C)C)C1=O)=O)=C1)=C2C4=C1OC1=CC=CC=C1 ZZSIDSMUTXFKNS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000001051 pigments by color Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 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
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- Paints Or Removers (AREA)
Description
また、本発明は、上記組成物が更にケイ素アルコキシド化合物もしくは金属アルコキシド化合物を含有することを特徴とするコーティング用組成物に関する。
更に、本発明は、上記吸着処理がメディア型分散機で行われることを特徴とする、コーティング用組成物に関する。
一般式(1)
Q1;有機色素残基、アントラキノン残基またはアミノ基を有するアリール基
X1;直接結合,−CONH−Y2 −,−SO2 NH−Y2- または−CH2 NHCOCH2 NH−Y2 −(Y2;置換基を有してもよいアルキレン基またはアリーレン基を表す。)
Y1 ;−NH−または−O−
Z;水酸基、アルコキシ基または下記一般式(2)で示される基で、nは1〜4の整数を表す。またn=1の場合 −NH−X−Q1であってもよい。
R1 ,R2 ;それぞれ独立に置換もしくは無置換のアルキル基。
m;1〜6の整数。
一般式(2)
Y3 ;−NH−または−O−
R3 ,R4 ;それぞれ独立に置換もしくは無置換のアルキル基またはR3 とR4 とが一体
となって形成されたヘテロ環。
m;1〜6の整数。
一般式(3)
Q2−(−X2−Y4)n
式中の記号は下記の意味を表す。
Q2;有機色素残基またはアントラキノン残基
X2;直接結合,−CONH−Y5−,−SO2 NH−Y5 −または−CH2 NHCOCH2NH−Y2 −(Y2は置換基を有してもよいアルキレン基またはアリーレン基を表す。)
Y4;下記一般式(4)で示される基
n;1〜4の整数。
一般式(4)
R5 , R6; それぞれ独立に置換もしくは無置換のアルキル基
m;1〜6の整数。
(R7)pSi(OR8)4−p (5)
R8(OSi(OR8)2)qOR8 (6)
M(OR9)r (7)
式中、
R7は、炭素数1から4のアルキル基および/または重合性有機基であり、
R8およびR9は炭素数1から4のアルキル基であり、
pは1から3の整数であり、
qは1から10の整数であり、
Mは3価または4価の金属イオンであり、
rはMの価数に応じて3または4の整数であり、
各化合物が複数のR7、R8、またはR9を含むとき、それらは同一であっても異なっていてもよい。
テトラエトキシシラン11.4部、エチルシリケート40(三菱化学社製)9.8部、水3.9部、硝酸3.3部、メタノール6.5部、エタノール58.6部、イソプロピルアルコール(IPA)6.5部を3時間撹拌した後、IPA:n−ブタノール=7:3(重量比)の混合液で、固形分濃度が1.0重量%になるように希釈し、オーバーコート用の塗布液(コート液1))を得た。
テトラエトキシシラン9.8部、エチルシリケート40(三菱化学社製)8.1部、ビニルトリメトキシシラン3.3部、水3.9部、硝酸3.3部、メタノール6.5部、エタノール58.6部、イソプロピルアルコール(IPA)6.5部を3時間撹拌混合し、バインダー液(バインダー液2))を得た。
Claims (5)
- 有機顔料と、塩基性官能基を有する有機色素誘導体または塩基性官能基を有するトリアジン誘導体とを、分子量が300以下の酸の存在下、誘電率が15以上の有機溶剤中で吸着処理した有機顔料分散体を含有することを特徴とするコーティング用組成物。
- プロトン性の有機溶剤を含有することを特徴とする請求項1記載のコーティング用組成物。
- 更に、ケイ素アルコキシド化合物もしくは金属アルコキシド化合物を含有してなることを特徴とする請求項1または2記載のコーティング用組成物。
- 吸着処理がメディア型分散機で行われる請求項1ないし3いずれか記載のコーティング用組成物。
- 用途がガラス基材の着色コーティングである請求項1ないし4いずれか記載のコーティング用組成物。
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JP3861882B2 true JP3861882B2 (ja) | 2006-12-27 |
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JP2007041552A (ja) * | 2005-06-17 | 2007-02-15 | Toyo Ink Mfg Co Ltd | 静電荷像現像用トナーおよびその製造方法 |
JP2008280518A (ja) * | 2007-04-11 | 2008-11-20 | Fujifilm Corp | 有機顔料水分散液及びその製造方法、並びにこれを用いた着色コーティング用組成物及び塗布物 |
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