JP6652120B2 - Naphthalocyanine solid solution and coloring composition thereof - Google Patents
Naphthalocyanine solid solution and coloring composition thereof Download PDFInfo
- Publication number
- JP6652120B2 JP6652120B2 JP2017251878A JP2017251878A JP6652120B2 JP 6652120 B2 JP6652120 B2 JP 6652120B2 JP 2017251878 A JP2017251878 A JP 2017251878A JP 2017251878 A JP2017251878 A JP 2017251878A JP 6652120 B2 JP6652120 B2 JP 6652120B2
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- JP
- Japan
- Prior art keywords
- group
- solid solution
- naphthalocyanine
- pigment
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 80
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 title claims description 66
- 239000006104 solid solution Substances 0.000 title claims description 66
- 238000004040 coloring Methods 0.000 title claims description 45
- 239000000049 pigment Substances 0.000 claims description 68
- 229920005989 resin Polymers 0.000 claims description 32
- 239000011347 resin Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 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 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 229910052751 metal Chemical group 0.000 claims description 13
- 239000002184 metal Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000010949 copper Substances 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 239000011651 chromium Substances 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000011572 manganese Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium(II) oxide Chemical compound [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 3
- -1 isobutenyl group Chemical group 0.000 description 87
- 239000002904 solvent Substances 0.000 description 33
- 239000003963 antioxidant agent Substances 0.000 description 24
- 235000006708 antioxidants Nutrition 0.000 description 24
- 235000002639 sodium chloride Nutrition 0.000 description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- 235000014113 dietary fatty acids Nutrition 0.000 description 18
- 239000000194 fatty acid Substances 0.000 description 18
- 229930195729 fatty acid Natural products 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- 230000003078 antioxidant effect Effects 0.000 description 13
- 239000000975 dye Substances 0.000 description 11
- 239000001056 green pigment Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 238000002441 X-ray diffraction Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000003801 milling Methods 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.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 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000005011 phenolic resin Substances 0.000 description 6
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 5
- 239000003945 anionic surfactant Substances 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000000976 ink Substances 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000004062 sedimentation Methods 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- 229910017053 inorganic salt Inorganic materials 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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- 230000008859 change Effects 0.000 description 3
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- 239000011521 glass Substances 0.000 description 3
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- 238000010438 heat treatment Methods 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
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- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000003071 polychlorinated biphenyls Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003902 salicylic acid esters Chemical group 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- PMJMHCXAGMRGBZ-UHFFFAOYSA-N subphthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(=N3)N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C3=N1 PMJMHCXAGMRGBZ-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical class C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- KXEMQEGRZWUKJS-QIYNHLNTSA-N tetraphylline Chemical class COC1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-QIYNHLNTSA-N 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical class [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical class C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- BWPNIANVWARHPR-UHFFFAOYSA-N tridecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCCOP(O)O BWPNIANVWARHPR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QHCNTMCHBZHBDY-UHFFFAOYSA-N trihydroxy-(6-methylheptyl)-phenyl-lambda5-phosphane Chemical compound CC(C)CCCCCP(O)(O)(O)C1=CC=CC=C1 QHCNTMCHBZHBDY-UHFFFAOYSA-N 0.000 description 1
- SFESXIFARCRODZ-UHFFFAOYSA-N trihydroxy-(8-methylnonyl)-phenyl-$l^{5}-phosphane Chemical compound CC(C)CCCCCCCP(O)(O)(O)C1=CC=CC=C1 SFESXIFARCRODZ-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Description
本発明は安全性が高く、廃棄やリサイクルの際に有害物質が発生しない、ハロゲンフリーなナフタロシアニン顔料およびフタロシアニン顔料の固溶体による緑色顔料の製造法およびこれを用いる着色組成物についてである。 The present invention relates to a halogen-free naphthalocyanine pigment and a method for producing a green pigment using a solid solution of a phthalocyanine pigment, which is highly safe and does not generate harmful substances during disposal or recycling, and a coloring composition using the green pigment.
近年、化学物質による環境汚染の懸念が深まっており、廃棄や焼却の際の生成物に対する配慮への要求が高まっている。ハロゲン化物は焼却の際にPCBやダイオキシンなどの有害物質を生成する可能性があり、製品の素材としての使用を控える動きある。一方、現行の緑色顔料はフタロシアニングリーン(例えば、PG7およびPG36)で占められているが、フタロシアニングリーンはその化学構造に塩素や臭素を含んでいるため、燃焼時にダイオキシンなどの有毒物質が発生する事が欠点として挙げられる。しかし、現時点ではフタロシアンニングリーンに代わる安価、高耐性、高彩度な有機顔料候補が存在せず、緑色顔料として広く使われている。このような背景から、近年、ハロゲン原子を含有しないハロゲンフリー緑色顔料の探索・開発が行われており、ハロゲンフリーの青色顔料および黄色顔料の調色によりハロゲンフリーの緑色顔料を目指す試みが行われているが(例えば、特許文献1参照。)、構造の異なる顔料の混合によるため、明度や彩度の両立に限界があり、また、顔料成分の耐光性の違いによる光退色に伴う色調の変化が課題である。以上の背景から、耐性、明度、彩度を兼ね備えたハロゲンフリー緑色顔料候補は得られていない。 In recent years, there has been a growing concern about environmental pollution due to chemical substances, and there has been an increasing demand for consideration of products during disposal and incineration. Halides can produce harmful substances such as PCBs and dioxins during incineration, and are being refrained from being used as product materials. On the other hand, the current green pigment is occupied by phthalocyanine green (for example, PG7 and PG36), but since phthalocyanine green contains chlorine and bromine in its chemical structure, toxic substances such as dioxin are generated during combustion. Is a disadvantage. However, at present, there is no low-cost, high-resistance and high-coloring organic pigment candidate replacing phthalocyanine green, and it is widely used as a green pigment. Against this background, search and development of halogen-free green pigments containing no halogen atoms have been conducted in recent years, and attempts have been made to achieve halogen-free green pigments by toning halogen-free blue pigments and yellow pigments. However, because of the mixture of pigments having different structures, there is a limit in balancing lightness and chroma, and a change in color tone due to light fading due to the difference in light resistance of the pigment components. Is the challenge. From the above background, no halogen-free green pigment candidate having both resistance, lightness, and saturation has been obtained.
ナフタロシアニン顔料は従来から知られており、その分光特性や堅牢性から近赤外吸収顔料および染料などとして使われている。ナフタロシアニン顔料、たとえば無金属ナフタロシアニンや銅ナフタロシアニンは緑色を示す事は知られており、ハロゲンフリー緑色顔料としての用途が期待されるものの、いずれも彩度が低く、緑色顔料として実用に耐えないという欠点があった。 Naphthalocyanine pigments have hitherto been known and are used as near-infrared absorbing pigments and dyes because of their spectral characteristics and fastness. Naphthalocyanine pigments, such as metal-free naphthalocyanine and copper naphthalocyanine, are known to exhibit green color, and although they are expected to be used as halogen-free green pigments, all have low chroma and are practically usable as green pigments. There was a disadvantage that there was no.
高彩度、高耐光性、および環境衛生性を全て備えたハロゲンフリー緑色顔料、および着色組成物を提供することである。 An object of the present invention is to provide a halogen-free green pigment and a coloring composition having high chroma, high light fastness and environmental health.
本発明者らは、課題を解決すべくナフタロシアニン顔料、添加物、および顔料処理方法等の検討を行った結果、ナフタロシアニン顔料の固溶体を生成させる事で、高彩度、高耐光の緑色顔料が得られる事を見出し、本発明に至った。 The present inventors have studied naphthalocyanine pigments, additives, pigment treatment methods and the like in order to solve the problems, and as a result, by producing a solid solution of naphthalocyanine pigments, a high chroma, high lightfast green pigment was obtained. And found that the present invention was achieved.
すなわち本発明は、一般式(1)で表されるナフタロシアニン顔料(I)とフタロシアニン顔料(II)とからなる固溶体に関する。
That is, the present invention relates to a solid solution comprising the naphthalocyanine pigment (I) and the phthalocyanine pigment (II) represented by the general formula (1).
また、本発明は、一般式(1)において、X1が2つの水素原子である上記固溶体に関する。 The present invention also relates to the solid solution, wherein X 1 is two hydrogen atoms in the general formula (1).
また、本発明は、一般式(1)において、X2が2つの水素原子またはオキソチタン(TiO)である上記固溶体に関する。 The present invention also relates to the solid solution, wherein X 2 is two hydrogen atoms or oxo titanium (TiO) in the general formula (1).
また、本発明は、上記記載の固溶体と樹脂とを含有することを特徴とする着色組成物に関する。 The present invention also relates to a coloring composition containing the solid solution described above and a resin.
本発明により、ナフタロシアニン顔料の固溶体を用いた高彩度、高耐光性の全てを備えた緑色着色組成物を提供することができる。 According to the present invention, a green coloring composition using a solid solution of a naphthalocyanine pigment and having high chroma and high light resistance can be provided.
以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
一般的に、多成分顔料がその複数成分の物理的混合物のX線回折図とは異なるX線回折図を示す場合には、その顔料は固溶体と呼ばれる。固溶体には明瞭に区別される2つの型「ゲスト−ホスト型固溶体」と「固体化合物型固溶体」が存在する。「ゲスト−ホスト型固溶体」は、その固溶体のX線回折図が、固溶体成分のうちのホストと呼ばれる成分の1つのX線回折図と実質的に同じである固溶体である。ホスト成分は、他の成分すなわちゲストをその結晶格子の中に受容するといわれる。「固体化合物型固溶体」は、2つの成分が互いに連携して、それら2つの成分のいずれの成分または物理的混合物のX線回折図とは異なる1つのX線回折図をつくり出している固溶体である。 Generally, when a multi-component pigment exhibits an X-ray diffraction pattern that is different from the X-ray diffraction pattern of the physical mixture of the components, the pigment is called a solid solution. There are two distinct types of solid solutions, "guest-host type solid solutions" and "solid compound type solid solutions". A “guest-host type solid solution” is a solid solution in which the X-ray diffraction pattern of the solid solution is substantially the same as the X-ray diffraction pattern of one of the components of the solid solution called host. The host component is said to accept another component, the guest, in its crystal lattice. A “solid compound-type solid solution” is a solid solution in which two components work together to create an X-ray diffraction diagram that is different from the X-ray diffraction diagram of any of the two components or a physical mixture. .
本発明に用いるナフタロシアニン固溶体は、少なくとも下記一般式(1)で表される2種類の異なるナフタロシアニン顔料(I)とフタロシアニン顔料(II)から形成される。 The naphthalocyanine solid solution used in the present invention is formed from at least two different naphthalocyanine pigments (I) and (II) represented by the following general formula (1).
R1〜R45における炭素数1〜5のアルキル基としては、直鎖状でも分岐状でもよく、具体例としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、ペンチル基、sec−ペンチル基、tert−ペンチル基、ネオペンチル基等を挙げることができる。 The alkyl group having 1 to 5 carbon atoms in R 1 to R 45 may be linear or branched, and specific examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and sec. -Butyl group, tert-butyl group, pentyl group, sec-pentyl group, tert-pentyl group, neopentyl group and the like.
R1〜R45における炭素数1〜5のアルケニル基としては、直鎖状でも分岐状でもよく、具体例としては、ビニル基、1−プロペニル基、2−ブテニル基、3−ブテニル基、イソプロペニル基、イソブテニル基、1,3−ブタジエニル基、1−ペンテニル基、2−ペンテニル基、3−ペンテニル基、4−ペンテニル基、等を挙げることができるが、これらに限定されるものではない。 The alkenyl group having 1 to 5 carbon atoms in R 1 to R 45 may be linear or branched, and specific examples thereof include a vinyl group, a 1-propenyl group, a 2-butenyl group, a 3-butenyl group, Examples thereof include, but are not limited to, a propenyl group, an isobutenyl group, a 1,3-butadienyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, and a 4-pentenyl group.
R1〜R45における炭素数6〜10のアリール基としては、置換もしくは未置換の単環または縮合多環芳香族基であり、例えば、フェニル基、1−ナフチル基、2−ナフチル基、o−トリル基、m−トリル基、p−トリル基などを挙げることができるが、これらに限定されるものではない。 The aryl group having 6 to 10 carbon atoms in R 1 to R 45 is a substituted or unsubstituted monocyclic or condensed polycyclic aromatic group, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, o -Tolyl group, m-tolyl group, p-tolyl group, and the like, but are not limited thereto.
ナフタロシアニン顔料(I)とフタロシアニン顔料(II)の具体例としては、下記に示すナフタロシアニン顔料等があげられるが、本発明はこれらに限定されるものではない。R1〜R40のうち、下記において明示されていないものは水素原子(H)とする。 Specific examples of the naphthalocyanine pigment (I) and the phthalocyanine pigment (II) include the following naphthalocyanine pigments, but the present invention is not limited thereto. Among R 1 to R 40 , those not specified below are hydrogen atoms (H).
表1に、代表的な置換基パターンと固溶体の組み合わせを示す。
表1記載のMeはメチル基、Buはブチル基、Phはフェニル基、vinylはビニル基、p−tolylはp−メチルフェニル基を示す。
Table 1 shows combinations of typical substituent patterns and solid solutions.
In Table 1, Me represents a methyl group, Bu represents a butyl group, Ph represents a phenyl group, vinyl represents a vinyl group, and p-tolyl represents a p-methylphenyl group.
(ナフタロシアニン顔料の製造方法)
本発明に用いるナフタロシアニン顔料は、例えば特開2000−86919号公報に示されるように、対応する2,3−ジシアノナフタレン誘導体を有機溶媒中で反応させることにより製造できる。ナフロシアニン顔料の製造方法は、この方法に限定されるものではない。
(Production method of naphthalocyanine pigment)
The naphthalocyanine pigment used in the present invention can be produced, for example, by reacting a corresponding 2,3-dicyanonaphthalene derivative in an organic solvent as shown in JP-A-2000-86919. The method for producing a naphthocyanine pigment is not limited to this method.
(ナフタロシアニン顔料固溶体の製造方法)
本発明のナフタロシアニン顔料固溶体の製造方法としては、少なくとも2種類のナフタロシアニン顔料を溶媒に溶解した後、その他溶媒と混合して析出させる方法やソルトミリング処理を用いて両者を混合する方法が挙げられるが、ナフタロシアニン顔料固溶体の製造方法は、この方法に限定されるものではない。ナフタロシアニン顔料(I)とフタロシアニン顔料(II)の混合比率は、顔料(I)が顔料(II)に対するモル比で5〜99モル%であり、より好ましくは80〜99モル%である。ナフタロシアニン顔料は、固溶体が形成可能であれば、2種以上を混合して使用してもよい。
(Method for producing naphthalocyanine pigment solid solution)
Examples of the method for producing the naphthalocyanine pigment solid solution of the present invention include a method in which at least two types of naphthalocyanine pigments are dissolved in a solvent, and then mixed with another solvent to precipitate them, or a method in which both are mixed using a salt milling treatment. However, the method for producing the naphthalocyanine pigment solid solution is not limited to this method. The mixing ratio of the naphthalocyanine pigment (I) and the phthalocyanine pigment (II) is such that the molar ratio of the pigment (I) to the pigment (II) is 5 to 99 mol%, and more preferably 80 to 99 mol%. The naphthalocyanine pigment may be used as a mixture of two or more as long as a solid solution can be formed.
ナフタロシアニン顔料を溶解させる溶媒の例としては、硫酸、N,N−ジメチルホルムアミド、N−メチルホルムアミド、テトラメチル尿素、N,N−ジメチルアセトアミド、N−メチルピロリドン、ジメチルスルホキシド、スルホラン等が挙げられるが、これらに限定されるものではない。硫酸以外の溶媒は、2種以上混合してもよい。 Examples of the solvent for dissolving the naphthalocyanine pigment include sulfuric acid, N, N-dimethylformamide, N-methylformamide, tetramethylurea, N, N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, sulfolane and the like. However, the present invention is not limited to these. Two or more solvents other than sulfuric acid may be mixed.
ナフタロシアニン顔料を溶媒に溶解した後に析出させるのに用いる溶媒は、上記の極性溶剤と混合可能で、本発明のナフタロシアニン顔料固溶体が析出する溶媒であれば何でもよい。本発明のナフタロシアニン顔料固溶体を析出させるのにより好ましい溶媒は水である。 The solvent used to precipitate the naphthalocyanine pigment after dissolving it in the solvent may be any solvent as long as it can be mixed with the above-mentioned polar solvent and precipitates the naphthalocyanine pigment solid solution of the present invention. A more preferred solvent for precipitating the naphthalocyanine pigment solid solution of the present invention is water.
ナフタロシアニン顔料の溶解温度は、溶媒の沸点にもよるが10〜100℃であり、20〜60℃がより好ましい。溶解時間は30分間から24時間が好ましい。他の溶媒と混合して析出させる場合は、粒子を微細にしたい場合は、−10〜30℃の低温が好ましい。さらに粒子を大きくコントロールする場合は、析出溶媒を混合した後に40〜100℃で加熱してもよく、加熱時間は30分間から24時間が好ましい。 The dissolution temperature of the naphthalocyanine pigment depends on the boiling point of the solvent, but is from 10 to 100C, preferably from 20 to 60C. The dissolution time is preferably from 30 minutes to 24 hours. When mixing with another solvent and precipitating, if it is desired to make the particles fine, a low temperature of -10 to 30C is preferable. When particles are further controlled, the mixture may be heated at 40 to 100 ° C. after mixing the precipitation solvent, and the heating time is preferably 30 minutes to 24 hours.
ソルトミリング処理は、ナフタロシアニン顔料およびフタロシアニン顔料の共アシッドペースト処理品と、水溶性無機塩と、水溶性有機溶剤との混合物を、ニーダー、2本ロールミル、3本ロールミル、ボールミル、アトライター、サンドミル、プラネタリーミキサー、フーバーマーラー等の混練機を用いて、加熱しながら機械的に混練した後、水、メタノール、2−メチルピロリドン等での洗浄により無機塩と易溶性有機物を除去する処理である。ソルトミリング処理の混練温度は、20〜150℃が好ましく、混練時間は1〜24時間が好ましい。顔料の共アシッドペースト処理品と混合するアルカリ土類金属塩の量は、顔料の共アシッドペースト処理品に対して質量比で0.01〜70質量%であり、より好ましくは質量比で1.0〜50質量%である。 The salt milling treatment is a kneader, a two-roll mill, a three-roll mill, a ball mill, an attritor, and a sand mill. This is a process of mechanically kneading while heating using a kneading machine such as a planetary mixer, a Hoover Mahler or the like, and then removing inorganic salts and easily soluble organic substances by washing with water, methanol, 2-methylpyrrolidone, or the like. . The kneading temperature of the salt milling treatment is preferably from 20 to 150 ° C., and the kneading time is preferably from 1 to 24 hours. The amount of the alkaline earth metal salt mixed with the pigment co-acid paste-treated product is 0.01 to 70% by mass based on the pigment co-acid paste-treated product, and more preferably 1. 0 to 50% by mass.
水溶性無機塩としては、塩化ナトリウム、塩化カリウム、硫酸ナトリウム等を用いることができるが、価格の点から塩化ナトリウム(食塩)を用いるのが好ましい。水溶性無機塩は、処理効率と生産効率の両面から、顔料の全質量を基準(100質量%)として、50〜2000質量%用いることが好ましく、300〜1000質量%用いることが最も好ましい。 As the water-soluble inorganic salt, sodium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of cost. The water-soluble inorganic salt is preferably used in an amount of 50 to 2000% by mass, and most preferably 300 to 1000% by mass, based on the total mass of the pigment (100% by mass) in terms of both processing efficiency and production efficiency.
水溶性有機溶剤は、顔料及び水溶性無機塩を湿潤する働きをするものであり、水に溶解(混和)し、かつ用いる無機塩を実質的に溶解しないものであれば特に限定されない。ただし、ソルトミリング時に温度が上昇し、溶剤が蒸発し易い状態になるため、安全性の点から、沸点120℃以上の高沸点溶剤が好ましい。例えば、2−メトキシエタノール、2−ブトキシエタノール、2−(イソペンチルオキシ)エタノール、2−(ヘキシルオキシ)エタノール、ジエチレングリコール、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、トリエチレングリコール、トリエチレングリコールモノメチルエーテル、液状のポリエチレングリコール、1−メトキシ−2−プロパノール、1−エトキシ−2−プロパノール、ジプロピレングリコール、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、液状のポリプロピレングリコール等が用いられる。水溶性有機溶剤は、顔料の全質量を基準(100質量%)として、5〜1000質量%用いることが好ましく、50〜500質量%用いることが最も好ましい。 The water-soluble organic solvent functions to wet the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) with water and does not substantially dissolve the inorganic salt to be used. However, since the temperature rises during salt milling and the solvent is likely to evaporate, a high boiling solvent having a boiling point of 120 ° C. or higher is preferred from the viewpoint of safety. For example, 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, Liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, and the like are used. The water-soluble organic solvent is preferably used in an amount of 5 to 1000% by mass, and most preferably 50 to 500% by mass, based on the total mass of the pigment (100% by mass).
ソルトミリング処理する際には、必要に応じて樹脂を添加してもよい。用いられる樹脂の種類は特に限定されず、天然樹脂、変性天然樹脂、合成樹脂、天然樹脂で変性された合成樹脂等を用いることができる。用いられる樹脂は、室温で固体であり、水不溶性であることが好ましく、かつ上記有機溶剤に一部可溶であることがさらに好ましい。樹脂の使用量は、顔料の全質量を基準(100質量%)として、5〜200質量%の範囲であることが好ましい。 During the salt milling treatment, a resin may be added as necessary. The type of the resin used is not particularly limited, and a natural resin, a modified natural resin, a synthetic resin, a synthetic resin modified with a natural resin, or the like can be used. The resin used is preferably solid at room temperature, insoluble in water, and more preferably partially soluble in the organic solvent. The amount of the resin used is preferably in the range of 5 to 200% by mass based on the total mass of the pigment (100% by mass).
ソルトミリング処理する際には、必要に応じて色素誘導体を添加してもよい。色素誘導体は、色素にフタルイミドメチル基や、下記一般式(4)、(5)、(6)で示される置換基を導入した化合物である。
一般式(4)において、
Xは、直接結合、−CH2NHCOCH2−、−SO2NH−、−CONHOCH2NH−、または−(CH2)pNH−を表す。
R1、R2は、それぞれ独立に、置換基を有してもよい飽和もしくは不飽和のアルキル基、またはR1、R2が一体となって形成する、窒素、酸素もしくは硫黄原子を含む、置換基を有してもよい複素環を示す。
ただし、n、pは1〜10の整数を表す。
In the general formula (4),
X is a direct bond, -CH 2 NHCOCH 2 -, - SO 2 NH -, - CONHOCH 2 NH-, or - (CH 2) represents a p NH-.
R 1 and R 2 each independently include a saturated or unsaturated alkyl group which may have a substituent, or a nitrogen, oxygen or sulfur atom formed by R 1 and R 2 together; A heterocyclic ring which may have a substituent is shown.
Here, n and p represent an integer of 1 to 10.
一般式(4)中、R1、R2において、置換基を有してもよい飽和もしくは不飽和のアルキル基の「置換基」としては、シアノ基、ニトロ基、水酸基、カルバモイル基、N−置換カルバモイル基、スルファモイル基、N−置換スルファモイル基、カルボキシル基、スルホ基、カルボキシル基またはスルホ基から選ばれる酸性基の1価〜3価の金属塩(例えば、ナトリウム塩、カリウム塩、アルミニウム塩等)などが挙げられるが、これらに限定されるものではない。 In the general formula (4), in R 1 and R 2 , as the “substituent” of the optionally substituted saturated or unsaturated alkyl group, a cyano group, a nitro group, a hydroxyl group, a carbamoyl group, an N- A monovalent to trivalent metal salt of an acidic group selected from a substituted carbamoyl group, a sulfamoyl group, an N-substituted sulfamoyl group, a carboxyl group, a sulfo group, a carboxyl group or a sulfo group (eg, sodium salt, potassium salt, aluminum salt, etc.) )), But is not limited thereto.
また、R1、R2において、置換基を有してもよい複素環基の「置換基」としては、炭素数1〜4のアルキル基、炭素数1〜4のアルコキシル基、シアノ基、ニトロ基、水酸基、カルバモイル基、N−置換カルバモイル基、スルファモイル基、N−置換スルファモイル基、カルボキシル基、スルホ基、カルボキシル基またはスルホ基から選ばれる酸性基の1価〜3価の金属塩(例えば、ナトリウム塩、カリウム塩、アルミニウム塩等)などが挙げられるが、これらに限定されるものではない。また、「複素環」とは、環系を構成する原子の中に、炭素原子以外のヘテロ原子が1個以上含まれるものを意味し、飽和環であっても不飽和環であっても良く、更に単環であっても縮合環であっても良い。したがって、複素環としては、ピリジン環、ピラジン環、ピリミジン環、ピリダジン環、トリアジン環、ピロール環、フラン環、チオフェン環、イミダゾール環、ピラゾール環、オキサゾール環、チアゾール環、イソオキサゾール環、イソチアゾール環、トリアゾール環、チアジアゾール環、オキサジアゾール環、キノリン環、ベンゾフラン環、インドール環、モルホリン環、ピロリジン環、ピペリジン環、テトラヒドロフラン環などが挙げられる。ゆえに、複素環基とは、これら複素環から水素原子を除いて誘導される一価の遊離基を意味する。 In R 1 and R 2 , the “substituent” of the heterocyclic group which may have a substituent includes an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a cyano group, and a nitro group. A monovalent to trivalent metal salt of an acidic group selected from a group, a hydroxyl group, a carbamoyl group, an N-substituted carbamoyl group, a sulfamoyl group, an N-substituted sulfamoyl group, a carboxyl group, a sulfo group, a carboxyl group or a sulfo group (for example, Sodium salt, potassium salt, aluminum salt and the like), but are not limited thereto. The term “heterocycle” means a ring system containing one or more heteroatoms other than carbon atoms, and may be a saturated ring or an unsaturated ring. Or a single ring or a condensed ring. Therefore, as the heterocycle, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, an isoxazole ring, and an isothiazole ring , A triazole ring, a thiadiazole ring, an oxadiazole ring, a quinoline ring, a benzofuran ring, an indole ring, a morpholine ring, a pyrrolidine ring, a piperidine ring, and a tetrahydrofuran ring. Therefore, the heterocyclic group means a monovalent radical derived by removing a hydrogen atom from these heterocycles.
一般式(5)において、
Yは、直接結合、−SO2−、−CO−、−CH2NHCOCH2−、−(CH2)q−、−SO2NH−、−CONH−、−CH2NHCOCH2NH−、または−(CH2)qNH−を表す。ただし、qは1〜10の整数を表す。
R3、R4、R5、R6は、それぞれ独立に、水素原子、置換基を有してもよい飽和もしくは不飽和のアルキル基、またはアリール基を表す。
R7は、置換基を有してもよい飽和もしくは不飽和のアルキル基またはアリール基を表す。
In the general formula (5),
Y is a direct bond, -SO 2 -, - CO - , - CH 2 NHCOCH 2 -, - (CH 2) q -, - SO 2 NH -, - CONH -, - CH 2 NHCOCH 2 NH-, or - (CH 2) represents a q NH-. Here, q represents an integer of 1 to 10.
R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom, a saturated or unsaturated alkyl group which may have a substituent, or an aryl group.
R 7 represents a saturated or unsaturated alkyl group or aryl group which may have a substituent.
一般式(5)中、R3、R4、R5、R6、R7において、置換基を有してもよい飽和もしくは不飽和のアルキル基またはアリール基の「置換基」としては、シアノ基、ニトロ基、水酸基、カルバモイル基、N−置換カルバモイル基、スルファモイル基、N−置換スルファモイル基、カルボキシル基、スルホ基、カルボキシル基またはスルホ基から選ばれる酸性基の1価〜3価の金属塩(例えば、ナトリウム塩、カリウム塩、アルミニウム塩等)などが挙げられるが、これらに限定されるものではない。 In the general formula (5), in R 3 , R 4 , R 5 , R 6 , and R 7 , as the “substituent” of the optionally substituted saturated or unsaturated alkyl group or aryl group, cyano Monovalent to trivalent metal salt of an acidic group selected from a group, nitro group, hydroxyl group, carbamoyl group, N-substituted carbamoyl group, sulfamoyl group, N-substituted sulfamoyl group, carboxyl group, sulfo group, carboxyl group or sulfo group (Eg, sodium salt, potassium salt, aluminum salt, etc.), but are not limited thereto.
一般式(6)において、Pcは、フタロシアニンを表し、Zは、水素原子、1〜3価の金属原子、有機アミン、またはアンモニアの何れかである。
1〜3価の金属原子としては、リチウム、カリウム、ナトリウム、カルシウム、マグネシウム、ストロンチウム、アルミニウム等が、有機アミンとしては、エチルアミン、ブチルアミン等のモノアルキルアミン、ジメチルアミン、ジエチルアミン等のジアルキルアミン、トリメチルアミン、トリエチルアミン等のトリアルキルアミンモノエタノールアミン、ジエタノールアミン、トリエタノールアミン等のアルカノールアミン等が挙げられる。
In the general formula (6), Pc represents phthalocyanine, and Z is any one of a hydrogen atom, a monovalent metal atom, an organic amine, and ammonia.
Examples of the trivalent metal atom include lithium, potassium, sodium, calcium, magnesium, strontium, and aluminum. Examples of the organic amine include monoalkylamines such as ethylamine and butylamine, dialkylamines such as dimethylamine and diethylamine, and trimethylamine. Alkanolamines such as trialkylamine monoethanolamine, diethanolamine, and triethanolamine.
色素誘導体としては、無金属ナフタロシアニン顔料の色相を汚さない観点からフタロシアニン誘導体が好ましい。 The dye derivative is preferably a phthalocyanine derivative from the viewpoint of not polluting the hue of the metal-free naphthalocyanine pigment.
フタロシアニン誘導体としては、以下の化合物を用いることができるが、これらに限定されるものではない。 The following compounds can be used as the phthalocyanine derivative, but are not limited thereto.
ソルトミリング処理する際には、必要に応じて色素誘導体の他に樹脂、界面活性剤、高級脂肪酸を添加してもよい。
使用可能な樹脂としては特に制限はないが、ロジン、ロジン誘導体、ロジン変性マレイン酸樹脂、ロジン変性フェノール樹脂、ゴム誘導体、タンパク誘導体、ポリ酢酸ビニル、エポキシ樹脂、アクリル樹脂、マレイン酸樹脂、スチレン樹脂、スチレン−マレイン酸共重合樹脂、ブチラール樹脂、ポリエステル樹脂、メラミン樹脂、フェノール樹脂、ポリウレタン樹脂、ポリアマイド樹脂、ポリイミド樹脂、アルキッド樹脂、ゴム系樹脂、セルロース類、ベンゾグアナミン樹脂、尿素樹脂を挙げることができる。また、界面活性剤としても特に制限はなく、アニオン性、中性、カチオン性のいずれの界面活性剤を用いても良い。
At the time of the salt milling treatment, a resin, a surfactant, and a higher fatty acid may be added as necessary in addition to the dye derivative.
Although there are no particular restrictions on the resins that can be used, rosin, rosin derivatives, rosin-modified maleic resin, rosin-modified phenolic resins, rubber derivatives, protein derivatives, polyvinyl acetate, epoxy resins, acrylic resins, maleic resins, and styrene resins Styrene-maleic acid copolymer resin, butyral resin, polyester resin, melamine resin, phenol resin, polyurethane resin, polyamide resin, polyimide resin, alkyd resin, rubber resin, celluloses, benzoguanamine resin, and urea resin. . The surfactant is not particularly limited, and any of anionic, neutral, and cationic surfactants may be used.
高級脂肪酸としては、炭素数が多い酸でグリセリンとの反応で油脂を構成し、広く動物脂肪や植物油の成分として含まれる、親油性の強い水に難溶の酸であり、パルミチン酸、リノール酸、ステアリン酸、リノレン酸、オレイン酸等がある。高級脂肪酸としては、炭素数10以上の脂肪酸が好ましく、さらに20〜30℃で液体である不飽和高級脂肪酸が好ましい。これに対して、炭素数の少ない脂肪酸には酢酸、吉草酸、ラク酸があり、遊離酸の状態になり親水性である。顔料を湿潤させて摩砕効果を増大させ、微細化を促進する脂肪酸としては、親油性の強い高級脂肪酸が適している。また、湿式粉砕で使用する水溶性無機塩類および水溶性有機溶剤は、水で洗浄することにより微細顔料から分離するが、炭素数の少ない親水性の脂肪酸は水中に溶解してしまい、生物化学的酸素要求量(BOD)、化学的酸素要求量(COD)の増加の要因になるので好ましくない。高級脂肪酸は、必要に応じて2種類以上を混合して使用してもよい。 Higher fatty acids are acids with a large number of carbon atoms that form fats and oils by reaction with glycerin, and are sparingly soluble in lipophilic water, widely contained as components of animal fats and vegetable oils, such as palmitic acid and linoleic acid. , Stearic acid, linolenic acid, oleic acid and the like. As the higher fatty acid, a fatty acid having 10 or more carbon atoms is preferable, and an unsaturated higher fatty acid which is liquid at 20 to 30 ° C. is more preferable. On the other hand, fatty acids having a small number of carbon atoms include acetic acid, valeric acid and lactic acid, which are in a free acid state and hydrophilic. Higher lipophilic fatty acids are suitable as the fatty acids that moisten the pigment, increase the milling effect, and promote fineness. In addition, water-soluble inorganic salts and water-soluble organic solvents used in wet grinding are separated from fine pigments by washing with water, but hydrophilic fatty acids having a small number of carbon atoms are dissolved in water and biochemically. It is not preferable because it causes an increase in oxygen demand (BOD) and chemical oxygen demand (COD). The higher fatty acids may be used as a mixture of two or more as needed.
ナフタロシアニン顔料固溶体は、溶剤と混合し溶剤処理をすることで、粒径を制御してもよい。この時用いる溶剤としては、ナフタロシアニン顔料固溶体を溶解させない溶剤がよい。溶剤処理に使用される溶剤としては、例えば、トルエンやキシレン、メトキシベンゼン等の芳香族系溶剤、酢酸エチルや酢酸ブチル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート等の酢酸エステル系溶剤、エトキシエチルプロピオネート等のプロピオネート系溶剤、メタノール、エタノール等のアルコール系溶剤、ブチルセロソルブ、プロピレングリコールモノメチルエーテル、ジエチレングリコールエチルエーテル、ジエチレングリコールジメチルエーテル等のエーテル系溶剤、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン系溶剤、ヘキサン等の脂肪族炭化水素系溶剤等が挙げられる。 The naphthalocyanine pigment solid solution may be mixed with a solvent and subjected to a solvent treatment to control the particle size. As the solvent used at this time, a solvent that does not dissolve the naphthalocyanine pigment solid solution is preferable. Examples of the solvent used in the solvent treatment include, for example, aromatic solvents such as toluene, xylene, and methoxybenzene, ethyl acetate and butyl acetate, propylene glycol monomethyl ether acetate, and acetic acid ester solvents such as propylene glycol monoethyl ether acetate. Propionate solvents such as ethoxyethyl propionate, alcohol solvents such as methanol and ethanol, butyl cellosolve, ether solvents such as propylene glycol monomethyl ether, diethylene glycol ethyl ether, and diethylene glycol dimethyl ether; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone Examples of the solvent include aliphatic hydrocarbon solvents such as a solvent and hexane.
ナフタロシアニン顔料固溶体の溶剤処理温度は、溶媒の沸点にもよるが10〜1200℃であり、溶剤処理時間は、30分間から24時間が好ましい。ナフタロシアニン顔料固溶体の制御したい粒径に応じて、溶剤種、処理温度、時間を設定することが望ましい。 The solvent treatment temperature of the naphthalocyanine pigment solid solution depends on the boiling point of the solvent, but is preferably from 10 to 1200 ° C., and the solvent treatment time is preferably from 30 minutes to 24 hours. It is desirable to set the solvent type, processing temperature, and time according to the particle size of the naphthalocyanine pigment solid solution to be controlled.
本発明の着色組成物は、本発明のナフタロシアニン固溶体、樹脂、および水系もしくは非水系の媒体を分散装置により分散することで得られる。本発明のナフタロシアニン固溶体を分散する方法は特に制限は無い。 The colored composition of the present invention is obtained by dispersing the naphthalocyanine solid solution of the present invention, a resin, and an aqueous or non-aqueous medium using a dispersing device. The method for dispersing the naphthalocyanine solid solution of the present invention is not particularly limited.
本発明の着色組成物は、水系であっても非水系であっても良い。本発明の着色組成物において本発明の無金属フタロシアニン顔料を分散する媒体としては、水、有機溶剤、重合性モノマー等が使用できる。本発明の着色組成物が水性着色組成物の場合には、水を主成分とし、所望により親水性有機溶剤を添加した混合物を用いることができる。親水性有機溶剤としては、例えば、メタノール、エタノール、1−プロパノール、2−プロパノール、1−ブタノール、イソブチルアルコール、2−ブタノール、イソブタノール、tert−ブチルアルコール、ペンタノール、ヘキサノール、シクロヘキサノール、ベンジルアルコール、ジアセトンアルコール等のアルコール類、エチレングリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、プロピレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、ジプロピレングリコール、ポリプロピレングリコール、ブチレングリコール、ヘキサンジオール、1、5−ペンタンジオール、グリセリン、1,2,6−ヘキサントリオール、チオジグリコール等の多価アルコール類、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノブチルエーテル、トリエチレングリコールモノメチルエーテル、エチレングリコールジアセテート、エチレングリコールモノメチルエーテルアセテートトリエチレングリコールモノエチルエーテル、エチレングリコールモノフェニルエーテル、ジグリセリンのエチレンオキサイド付加物等のグリコール誘導体、エタノールアミン、ジエタノールアミン、トリエタノールアミン、N−メチルジエタノールアミン、N−エチルジエタノールアミン、モルホリン、N−エチルモルホリン、エチレンジアミン、ジエチレントリアミン、トリエチレンテトラミン、ポリエチレンイミン、テトラメチルプロピレンジアミン等のアミン類、その他、ホルムアミド、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、ジメチルスルホキシド、チオジエタノール、チオジグリセロール、スルホラン、2−ピロリドン、N−メチル−2−ピロリドン、N−ビニル−2−ピロリドン、2−オキサゾリドン、1,3−ジメチル−2−イミダゾリジノン、アセトニトリル、アセトン、メチルエチルケトン、エチレンカーボネート、プロピレンカーボネート等の水溶性溶媒が挙げられる。 The coloring composition of the present invention may be aqueous or non-aqueous. As a medium in which the metal-free phthalocyanine pigment of the present invention is dispersed in the coloring composition of the present invention, water, an organic solvent, a polymerizable monomer, or the like can be used. When the coloring composition of the present invention is an aqueous coloring composition, a mixture containing water as a main component and optionally adding a hydrophilic organic solvent can be used. Examples of the hydrophilic organic solvent include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, isobutyl alcohol, 2-butanol, isobutanol, tert-butyl alcohol, pentanol, hexanol, cyclohexanol, and benzyl alcohol. , Alcohols such as diacetone alcohol, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, 1,2-propanediol, 1,3-propanediol, dipropylene glycol, polypropylene glycol, butylene glycol, hexanediol Polyhydric alcohols such as 1,5-pentanediol, glycerin, 1,2,6-hexanetriol, and thiodiglycol; Coal monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monobutyl ether, Glycol derivatives such as triethylene glycol monomethyl ether, ethylene glycol diacetate, ethylene glycol monomethyl ether acetate triethylene glycol monoethyl ether, ethylene glycol monophenyl ether, and ethylene oxide adduct of diglycerin, ethanolamine Amines such as diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, morpholine, N-ethylmorpholine, ethylenediamine, diethylenetriamine, triethylenetetramine, polyethyleneimine, tetramethylpropylenediamine, etc., and other formamides, N, N -Dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, thiodiethanol, thiodiglycerol, sulfolane, 2-pyrrolidone, N-methyl-2-pyrrolidone, N-vinyl-2-pyrrolidone, 2-oxazolidone, 1,3 Water-soluble solvents such as -dimethyl-2-imidazolidinone, acetonitrile, acetone, methyl ethyl ketone, ethylene carbonate and propylene carbonate. .
さらに、本発明の水系着色組成物には水性樹脂を含んでいても良い。水性樹脂としては、水に溶解する水溶解性の樹脂、水に分散する水分散性の樹脂、コロイダルディスバーション樹脂、またはそれらの混合物が挙げられる。水性樹脂としては具体的には、アクリル系、スチレン−アクリル系、ポリエステル系、ポリアミド系、ポリウレタン系等の樹脂が挙げられる。 Further, the aqueous coloring composition of the present invention may contain an aqueous resin. Examples of the aqueous resin include a water-soluble resin that dissolves in water, a water-dispersible resin that disperses in water, a colloidal dispersion resin, and a mixture thereof. Specific examples of the aqueous resin include acrylic, styrene-acrylic, polyester, polyamide, and polyurethane resins.
さらに、本発明のナフタロシアニン固溶体の分散体および本発明の着色組成物には、界面活性剤および分散剤を用いてもよい。界面活性剤としては、アニオン性、ノニオン性、カチオン性、両イオン性の界面活性剤が挙げられ、いずれの界面活性剤を用いても良いが、アニオン性、またはノニオン性の界面活性剤を用いるのが好ましい。アニオン性界面活性剤としては、例えば、脂肪酸塩、アルキル硫酸エステル塩、アルキルベンゼンスルホン酸塩、アルキルナフタレンスルホン酸塩、ジアルキルスルホコハク酸塩、アルキルジアリールエーテルジスルホン酸塩、アルキルリン酸塩、ポリオキシエチレンアルキルエーテル硫酸塩、ポリオキシエチレンアルキルアリールエーテル硫酸塩、ナフタレンスルホン酸ホルマリン縮合物、ポリオキシエチレンアルキルリン酸エステル塩、グリセロールボレイト脂肪酸エステル、ポリオキシエチレングリセロール脂肪酸エステル等が挙げられる。 Furthermore, a surfactant and a dispersant may be used in the dispersion of the naphthalocyanine solid solution of the present invention and the coloring composition of the present invention. Examples of the surfactant include anionic, nonionic, cationic, and amphoteric surfactants. Any surfactant may be used, but an anionic or nonionic surfactant is used. Is preferred. Examples of the anionic surfactant include fatty acid salts, alkyl sulfate salts, alkyl benzene sulfonates, alkyl naphthalene sulfonates, dialkyl sulfosuccinates, alkyl diaryl ether disulfonates, alkyl phosphates, polyoxyethylene alkyls Examples include ether sulfates, polyoxyethylene alkyl aryl ether sulfates, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl phosphate esters, glycerol borate fatty acid esters, and polyoxyethylene glycerol fatty acid esters.
ノニオン性界面活性剤としては,例えば、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンオキシプロピレンブロックコポリマー、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレンソルビトール脂肪酸エステル、グリセリン脂肪酸エステル、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレンアルキルアミン、シリコン系等が挙げられる。 Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene oxypropylene block copolymer, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, and glycerin. Examples include fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene alkylamines, and silicon-based ones.
本発明の着色組成物が非水性着色組成物の場合は、本発明のナフタロシアニンおよびフタロシアニン顔料固溶体を媒体として非水系バインダーに分散してなるものである。非水系バインダーに使用される樹脂は、例えば、石油系樹脂、カゼイン、セラック、ロジン変性マレイン酸樹脂、ロジン変性フェノール樹脂、ニトロセルロース、セルロースアセテートブチレート、環化ゴム、酸化ゴム、フェノール樹脂、アルキド樹脂、ポリエステル樹脂、不飽和ポリエステル樹脂、アミノ樹脂、エポキシ樹脂、ビニル樹脂、アクリル樹脂、メタクリル樹脂、ポリウレタン樹脂、シリコン樹脂、乾性油、合成乾性油、スチレン/マレイン酸樹脂、スチレン/アクリル樹脂、ポリアミド樹脂、ポリイミド樹脂、ベンゾグアナミン樹脂、メラミン樹脂、ブチラール樹脂等が挙げられる。非水系バインダーとして、光硬化性樹脂を用いてもよい。 When the coloring composition of the present invention is a non-aqueous coloring composition, the coloring composition is obtained by dispersing the naphthalocyanine and the phthalocyanine pigment solid solution of the present invention as a medium in a non-aqueous binder. The resin used for the non-aqueous binder includes, for example, petroleum resin, casein, shellac, rosin-modified maleic resin, rosin-modified phenol resin, nitrocellulose, cellulose acetate butyrate, cyclized rubber, oxide rubber, phenolic resin, alkyd Resin, polyester resin, unsaturated polyester resin, amino resin, epoxy resin, vinyl resin, acrylic resin, methacrylic resin, polyurethane resin, silicone resin, drying oil, synthetic drying oil, styrene / maleic resin, styrene / acrylic resin, polyamide Resins, polyimide resins, benzoguanamine resins, melamine resins, butyral resins, and the like. A photocurable resin may be used as the non-aqueous binder.
また、非水系バインダーに使用される溶剤としては、例えば、トルエンやキシレン、メトキシベンゼン等の芳香族系溶剤、酢酸エチルや酢酸ブチル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート等の酢酸エステル系溶剤、エトキシエチルプロピオネート等のプロピオネート系溶剤、メタノール、エタノール等のアルコール系溶剤、ブチルセロソルブ、プロピレングリコールモノメチルエーテル、ジエチレングリコールエチルエーテル、ジエチレングリコールジメチルエーテル等のエーテル系溶剤、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン系溶剤、ヘキサン等の脂肪族炭化水素系溶剤、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、γ−ブチロラクタム、N−メチル−2−ピロリドン、アニリン、ピリジン等の窒素化合物系溶剤、γ−ブチロラクトン等のラクトン系溶剤、カルバミン酸メチルとカルバミン酸エチルの48:52の混合物のようなカルバミン酸エステル等が挙げられる。 Examples of the solvent used for the non-aqueous binder include, for example, aromatic solvents such as toluene, xylene, and methoxybenzene; ethyl acetate and butyl acetate; and acetic acid esters such as propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate. Solvents, propionate solvents such as ethoxyethyl propionate, alcohol solvents such as methanol and ethanol, butyl cellosolve, ether solvents such as propylene glycol monomethyl ether, diethylene glycol ethyl ether and diethylene glycol dimethyl ether, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc. Ketone solvents, aliphatic hydrocarbon solvents such as hexane, N, N-dimethylformamide, N, N-dimethylacetate Nitrogen compound solvents such as amide, γ-butyrolactam, N-methyl-2-pyrrolidone, aniline and pyridine; lactone solvents such as γ-butyrolactone; carbamines such as a 48:52 mixture of methyl carbamate and ethyl carbamate Acid esters and the like.
(光重合性単量体)
本発明の着色組成物には、必要に応じて光重合性単量体を添加してもよい。光重合性単量体には、紫外線や熱などにより硬化して透明樹脂を生成するモノマーもしくはオリゴマーが含まれる。
(Photopolymerizable monomer)
A photopolymerizable monomer may be added to the coloring composition of the present invention as needed. The photopolymerizable monomer includes a monomer or oligomer that is cured by ultraviolet light or heat to form a transparent resin.
紫外線や熱などにより硬化して透明樹脂を生成するモノマー、オリゴマーとしては、例えば、メチル(メタ)アクリレート、エチル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、β−カルボキシエチル(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、トリプロピレングリコールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、1,6−ヘキサンジオールジグリシジルエーテルジ(メタ)アクリレート、ビスフェノールAジグリシジルエーテルジ(メタ)アクリレート、ネオペンチルグリコールジグリシジルエーテルジ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、トリシクロデカニル(メタ)アクリレート、エステルアクリレート、メチロール化メラミンの(メタ)アクリル酸エステル、エポキシ(メタ)アクリレート、ウレタンアクリレート等の各種アクリル酸エステルおよびメタクリル酸エステル、(メタ)アクリル酸、スチレン、酢酸ビニル、ヒドロキシエチルビニルエーテル、エチレングリコールジビニルエーテル、ペンタエリスリトールトリビニルエーテル、(メタ)アクリルアミド、N−ヒドロキシメチル(メタ)アクリルアミド、N−ビニルホルムアミド、アクリロニトリル等が挙げられるが、必ずしもこれらに限定されるものではない。
これらの光重合性化合物は、1種を単独で、または必要に応じて任意の比率で2種以上混合して用いることができる。
Examples of monomers and oligomers which are cured by ultraviolet light or heat to produce a transparent resin include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate , Cyclohexyl (meth) acrylate, β-carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di ( (Meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1,6-hexanediol diglycine Di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, neopentyl glycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, tricyclodeca Nyl (meth) acrylate, ester acrylate, (meth) acrylate of methylolated melamine, epoxy (meth) acrylate, urethane acrylate and various acrylates and methacrylates, (meth) acrylic acid, styrene, vinyl acetate, Hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl Examples include, but are not necessarily limited to, tyl (meth) acrylamide, N-vinylformamide, acrylonitrile, and the like.
One of these photopolymerizable compounds may be used alone, or two or more of them may be used in an optional ratio as needed.
光重合性単量体の配合量は、着色剤100質量部に対し、5〜400質量部であることが好ましく、光硬化性および現像性の観点から10〜300質量部であることがより好ましい。 The blending amount of the photopolymerizable monomer is preferably from 5 to 400 parts by mass, more preferably from 10 to 300 parts by mass from the viewpoint of photocurability and developability, based on 100 parts by mass of the colorant. .
(光重合開始剤)
本発明の着色組成物は、必要に応じて、該組成物を紫外線照射により硬化させ、フォトリソグラフィー法によりフィルタセグメントを形成するために、光重合開始剤を加えて溶剤現像型あるいはアルカリ現像型感光性着色組成物の形態で調製することができる。
(Photopolymerization initiator)
The coloring composition of the present invention is, if necessary, cured by irradiating the composition with ultraviolet light, and added with a photopolymerization initiator to form a filter segment by a photolithography method. It can be prepared in the form of a sex coloring composition.
光重合開始剤としては、ジエトキシアセトフェノン、1−(4−イソプロピルフェニル)−2−ヒドロキシ−2−メチルプロパン−1−オン、1−ヒドロキシシクロヘキシルフェニルケトン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノプロパン−1−オン、2−(ジメチルアミノ)−2−[(4−メチルフェニル)メチル]−1−[4−(4−モルホリニル)フェニル]−1−ブタノン、または2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタン−1−オン等のアセトフェノン系化合物;ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、またはベンジルジメチルケタール等のベンゾイン系化合物;ベンゾフェノン、ベンゾイル安息香酸、ベンゾイル安息香酸メチル、4−フェニルベンゾフェノン、ヒドロキシベンゾフェノン、アクリル化ベンゾフェノン、4−ベンゾイル−4’−メチルジフェニルサルファイド、または3,3’,4,4’−テトラ(t−ブチルパーオキシカルボニル)ベンゾフェノン等のベンゾフェノン系化合物;チオキサントン、2−メチルチオキサントン、イソプロピルチオキサントン、2,4−ジイソプロピルチオキサントン、または2,4−ジエチルチオキサントン等のチオキサントン系化合物;1,2−オクタンジオン,1−〔4−(フェニルチオ)−,2−(O−ベンゾイルオキシム)〕、またはO−(アセチル)−N−(1−フェニル−2−オキソ−2−(4’−メトキシ−ナフチル)エチリデン)ヒドロキシルアミン等のオキシムエステル系化合物;ビス(2,4,6−トリメチルベンゾイル)フェニルホスフィンオキサイド、または2,4,6−トリメチルベンゾイルジフェニルホスフィンオキサイド等のホスフィン系化合物;9,10−フェナンスレンキノン、カンファーキノン、エチルアントラキノン等のキノン系化合物; ボレート系化合物; カルバゾール系化合物;イミダゾール系化合物;あるいは、チタノセン系化合物等が用いられる。
これらの光重合開始剤は、1種を単独で、または必要に応じて任意の比率で2種以上混合して用いることができる。
Examples of the photopolymerization initiator include diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, and 2-methyl-1- [4- ( Methylthio) phenyl] -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone Or an acetophenone compound such as 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or benzyl dimethyl ketal Benzoin compounds such as benzophenone and benzoylbenzoate , Methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenylsulfide, or 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone Benzophenone-based compounds such as thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, and 2,4-diethylthioxanthone; 1,2-octanedione, 1- [4- (phenylthioxanthone; )-, 2- (O-benzoyloxime)] or oxime ester compounds such as O- (acetyl) -N- (1-phenyl-2-oxo-2- (4'-methoxy-naphthyl) ethylidene) hydroxylamine Conversion Phosphine compounds such as bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide; 9,10-phenanthrenequinone, camphorquinone, ethylanthraquinone, etc. Quinone compounds; borate compounds; carbazole compounds; imidazole compounds; or titanocene compounds.
One of these photopolymerization initiators may be used alone, or two or more of them may be used in an optional ratio as needed.
光重合開始剤の含有量は、着色剤100質量部に対し、2〜200質量部であることが好ましく、光硬化性及び現像性の観点から3〜150質量部であることがより好ましい。 The content of the photopolymerization initiator is preferably from 2 to 200 parts by mass, more preferably from 3 to 150 parts by mass from the viewpoint of photocurability and developability, based on 100 parts by mass of the coloring agent.
(増感剤)
さらに、本発明の着色組成物には、必要に応じて増感剤を含有させることができる。
増感剤としては、カルコン誘導体、ジベンザルアセトン等に代表される不飽和ケトン類、ベンジルやカンファーキノン等に代表される1,2−ジケトン誘導体、ベンゾイン誘導体、フルオレン誘導体、ナフトキノン誘導体、アントラキノン誘導体、キサンテン誘導体、チオキサンテン誘導体、キサントン誘導体、チオキサントン誘導体、クマリン誘導体、ケトクマリン誘導体、シアニン誘導体、メロシアニン誘導体、オキソノ−ル誘導体等のポリメチン色素、アクリジン誘導体、アジン誘導体、チアジン誘導体、オキサジン誘導体、インドリン誘導体、アズレン誘導体、アズレニウム誘導体、スクアリリウム誘導体、ポルフィリン誘導体、テトラフェニルポルフィリン誘導体、トリアリールメタン誘導体、テトラベンゾポルフィリン誘導体、テトラピラジノポルフィラジン誘導体、フタロシアニン誘導体、テトラアザポルフィラジン誘導体、テトラキノキサリロポルフィラジン誘導体、ナフタロシアニン誘導体、サブフタロシアニン誘導体、ピリリウム誘導体、チオピリリウム誘導体、テトラフィリン誘導体、アヌレン誘導体、スピロピラン誘導体、スピロオキサジン誘導体、チオスピロピラン誘導体、金属アレーン錯体、有機ルテニウム錯体、又はミヒラーケトン誘導体、α−アシロキシエステル、アシルフォスフィンオキサイド、メチルフェニルグリオキシレート、ベンジル、9,10−フェナンスレンキノン、カンファーキノン、エチルアンスラキノン、4,4’−ジエチルイソフタロフェノン、3,3’,又は4,4’−テトラ(t−ブチルパーオキシカルボニル)ベンゾフェノン、4,4’−ジエチルアミノベンゾフェノン等が挙げられる。
これらの増感剤は、1種を単独で、または必要に応じて任意の比率で2種以上混合して用いることができる。
(Sensitizer)
Further, the coloring composition of the present invention may contain a sensitizer as needed.
Examples of the sensitizer include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, and anthraquinone derivatives. , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, polymethine dyes such as oxanol derivatives, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivative, azulhenium derivative, squarylium derivative, porphyrin derivative, tetraphenylporphyrin derivative, triarylmethane derivative, tetrabenzoporphyrin derivative, Trapyrazinoporphyrazine derivative, phthalocyanine derivative, tetraazaporphyrazine derivative, tetraquinoxaliloporphyrazine derivative, naphthalocyanine derivative, subphthalocyanine derivative, pyrylium derivative, thiopyrylium derivative, tetraphyllin derivative, annulene derivative, spiropyran derivative, spirooxazine Derivative, thiospiropyran derivative, metal arene complex, organic ruthenium complex, or Michler's ketone derivative, α-acyloxy ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethyl Anthraquinone, 4,4′-diethylisophthalophenone, 3,3 ′, or 4,4′-tetra (t-butylperoxycarbonyl) benzopheno And 4,4′-diethylaminobenzophenone.
One of these sensitizers can be used alone, or two or more of them can be used in an optional ratio as needed.
さらに具体的には、大河原信ら編、「色素ハンドブック」(1986年、講談社)、大河原信ら編、「機能性色素の化学」(1981年、シーエムシー)、池森忠三朗ら編、及び「特殊機能材料」(1986年、シーエムシー)に記載の増感剤が挙げられるがこれらに限定されるものではない。また、その他、紫外から近赤外域にかけての光に対して吸収を示す増感剤を含有させることもできる。 More specifically, edited by Shin Okawara et al., "Dye Handbook" (1986, Kodansha), edited by Shin Okawara et al., "Chemistry of Functional Dyes" (1981, CMC), edited by Chusaburo Ikemori, and others. Sensitizers described in "Specially Functional Materials" (1986, CMC), but are not limited thereto. In addition, a sensitizer that absorbs light in the ultraviolet to near infrared region can be contained.
増感剤の含有量は、着色組成物中に含まれる光重合開始剤100質量部に対し、3〜60質量部であることが好ましく、光硬化性、現像性の観点から5〜50質量部であることがより好ましい。 The content of the sensitizer is preferably 3 to 60 parts by mass with respect to 100 parts by mass of the photopolymerization initiator contained in the coloring composition, and from the viewpoint of photocurability and developability, 5 to 50 parts by mass. Is more preferable.
(酸化防止剤)
本発明の着色組成物は、必要に応じて酸化防止剤を含有することができる。酸化防止剤は、特にカラーフィルター用途に用いられる場合に含まれている光重合開始剤や熱硬化性化合物が、熱硬化やITO(酸化インジウムスズ)アニール時の熱工程によって酸化し黄変することを防ぐため、塗膜の透過率を高くすることができる。そのため、酸化防止剤を含むことで、加熱工程時の酸化による黄変を防止し、高い塗膜の透過率を得る事ができる。
(Antioxidant)
The coloring composition of the present invention can contain an antioxidant as needed. The antioxidant is that a photopolymerization initiator or a thermosetting compound contained especially when used for a color filter is oxidized and yellowed by a heat process at the time of thermosetting or annealing of ITO (indium tin oxide). In order to prevent this, the transmittance of the coating film can be increased. Therefore, by containing an antioxidant, yellowing due to oxidation during the heating step can be prevented, and high transmittance of the coating film can be obtained.
本発明における「酸化防止剤」とは、紫外線吸収機能、ラジカル補足機能、または、過酸化物分解機能を有する化合物であればよく、具体的には、酸化防止剤としてヒンダードフェノール系、ヒンダードアミン系、リン系、イオウ系、ベンゾトリアゾール系、ベンゾフェノン系、ヒドロキシルアミン系、サルチル酸エステル系、およびトリアジン系の化合物があげられ、公知の紫外線吸収剤、酸化防止剤等が使用できる。 The "antioxidant" in the present invention may be a compound having an ultraviolet absorbing function, a radical scavenging function, or a peroxide decomposing function. Specifically, hindered phenol-based and hindered amine-based antioxidants are used. And phosphorus-based, sulfur-based, benzotriazole-based, benzophenone-based, hydroxylamine-based, salicylate-based, and triazine-based compounds. Known UV absorbers and antioxidants can be used.
これらの酸化防止剤の中でも、塗膜の透過率と感度の両立の観点から、好ましいものとしては、ヒンダードフェノール系酸化防止剤、ヒンダードアミン系酸化防止剤、リン系酸化防止剤またはイオウ系酸化防止剤が挙げられる。また、より好ましくは、ヒンダードフェノール系酸化防止剤、ヒンダードアミン系酸化防止剤、またはリン系酸化防止剤である。 Among these antioxidants, preferred are hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants or sulfur-based antioxidants, from the viewpoint of achieving both the transmittance and the sensitivity of the coating film. Agents. Further, more preferred are a hindered phenol-based antioxidant, a hindered amine-based antioxidant, and a phosphorus-based antioxidant.
ヒンダードフェノール系酸化防止剤としては、2,4−ビス〔(ラウリルチオ)メチル〕−o−クレゾール、1,3,5−トリス(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)、1,3,5−トリス(4−t−ブチル−3−ヒドロキシ−2,6−ジメチルベンジル)、2,4−ビス−(n−オクチルチオ)−6−(4−ヒドロキシ−3,5−ジ−t−ブチルアニリノ)−1,3,5−トリアジン、ペンタエリスリトールテトラキス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート、2,6−ジ−t−ブチル−4−ノニルフェノール、2,2’−イソブチリデン−ビス−(4,6−ジメチル−フェノール)、4,4’−ブチリデン−ビス−(2−t−ブチル−5−メチルフェノール)、2,2’−チオ−ビス−(6−t−ブチル−4−メチルフェノール)、2,5−ジ−t−アミル−ヒドロキノン、2,2’チオジエチルビス−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)−プロピオネート、1,1,3−トリス−(2’−メチル−4’−ヒドロキシ−5’−t−ブチルフェニル)−ブタン、2,2’−メチレン−ビス−(6−(1−メチル−シクロヘキシル)−p−クレゾール)、2,4−ジメチル−6−(1−メチル−シクロヘキシル)−フェノール、N,N−ヘキサメチレンビス(3,5−ジ−t−ブチル−4−ヒドロキシ−ヒドロシンナムアミド)等が挙げられる。その他ヒンダードフェノール構造を有するオリゴマータイプ及びポリマータイプの化合物等も使用することが出来る。 Hindered phenolic antioxidants include 2,4-bis [(laurylthio) methyl] -o-cresol, 1,3,5-tris (3,5-di-t-butyl-4-hydroxybenzyl), 1,3,5-tris (4-t-butyl-3-hydroxy-2,6-dimethylbenzyl), 2,4-bis- (n-octylthio) -6- (4-hydroxy-3,5-di -T-butylanilino) -1,3,5-triazine, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, 2,6-di-t-butyl-4- Nonylphenol, 2,2′-isobutylidene-bis- (4,6-dimethyl-phenol), 4,4′-butylidene-bis- (2-t-butyl-5-methylphenol), 2,2′-thio -Bis- (6-tert-butyl-4-methylphenol), 2,5-di-tert-amyl-hydroquinone, 2,2'thiodiethylbis- (3,5-di-tert-butyl-4-hydroxy) Phenyl) -propionate, 1,1,3-tris- (2′-methyl-4′-hydroxy-5′-tert-butylphenyl) -butane, 2,2′-methylene-bis- (6- (1- Methyl-cyclohexyl) -p-cresol), 2,4-dimethyl-6- (1-methyl-cyclohexyl) -phenol, N, N-hexamethylenebis (3,5-di-t-butyl-4-hydroxy- Hydrocinnamamide) and the like. In addition, oligomer type and polymer type compounds having a hindered phenol structure can also be used.
ヒンダードアミン系酸化防止剤としては、ビス(2,2,6,6−テトラメチル−4−ピペリジル)セバケート、ビス(N−メチル−2,2,6,6−テトラメチル−4−ピペリジル)セバケート、N,N’−ビス(2,2,6,6−テトラメチル−4−ピペリジル)−1,6−ヘキサメチレンジアミン、2−メチル−2−(2,2,6,6−テトラメチル−4−ピペリジル)アミノ−N−(2,2,6,6−テトラメチル−4−ピペリジル)プロピオンアミド、テトラキス(2,2,6,6−テトラメチル−4−ピペリジル)(1,2,3,4−ブタンテトラカルボキシレート、ポリ〔{6−(1,1,3,3−テトラメチルブチル)イミノ−1,3,5−トリアジン−2,4−ジイル}{(2,2,6,6−テトラメチル−4−ピペリジル)イミノ}ヘキサメチル{(2,2,6,6−テトラメチル−4−ピペリジル)イミノ}〕、ポリ〔(6−モルホリノ−1,3,5−トリアジン−2,4−ジイル){(2,2,6,6−テトラメチル−4−ピペリジル)イミノ}ヘキサメチン{(2,2,6,6−テトラメチル−4−ピペリジル)イミノ}〕、コハク酸ジメチルと1−(2−ヒドロキシエチル)−4−ヒドロキシ−2,2,6,6−テトラメチルピペリジンとの重縮合物、N,N′−4,7−テトラキス〔4,6−ビス{N−ブチル−N−(1,2,2,6,6−ペンタメチル−4−ピペリジル)アミノ}−1,3,5−トリアジン−2−イル〕−4,7−ジアザデカン−1,10−ジアミン等が挙げられる。その他ヒンダードアミン構造を有するオリゴマータイプ及びポリマータイプの化合物等も使用することが出来る。 As the hindered amine antioxidant, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (N-methyl-2,2,6,6-tetramethyl-4-piperidyl) sebacate, N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) -1,6-hexamethylenediamine, 2-methyl-2- (2,2,6,6-tetramethyl-4 -Piperidyl) amino-N- (2,2,6,6-tetramethyl-4-piperidyl) propionamide, tetrakis (2,2,6,6-tetramethyl-4-piperidyl) (1,2,3 4-butanetetracarboxylate, poly [{6- (1,1,3,3-tetramethylbutyl) imino-1,3,5-triazine-2,4-diyl} (2,2,6,6 -Tetramethyl-4-piperidi ) Imino {hexamethyl} (2,2,6,6-tetramethyl-4-piperidyl) imino}], poly [(6-morpholino-1,3,5-triazine-2,4-diyl)} (2 2,6,6-tetramethyl-4-piperidyl) imino {hexamethine {(2,2,6,6-tetramethyl-4-piperidyl) imino}], dimethyl succinate and 1- (2-hydroxyethyl)- Polycondensation product with 4-hydroxy-2,2,6,6-tetramethylpiperidine, N, N'-4,7-tetrakis [4,6-bis {N-butyl-N- (1,2,2 , 6,6-pentamethyl-4-piperidyl) amino {-1,3,5-triazin-2-yl] -4,7-diazadecane-1,10-diamine, etc. Other oligomer types having a hindered amine structure as well as Rimmer type of compounds and the like can also be used.
リン系酸化防止剤としては、トリス(イソデシル)フォスファイト、トリス(トリデシル)フォスファイト、フェニルイソオクチルフォスファイト、フェニルイソデシルフォスファイト、フェニルジ(トリデシル)フォスファイト、ジフェニルイソオクチルフォスファイト、ジフェニルイソデシルフォスファイト、ジフェニルトリデシルフォスファイト、トリフェニルフォスファイト、トリス(ノニルフェニル)フォスファイト、4,4’イソプロピリデンジフェノールアルキルフォスファイト、トリスノニルフェニルフォスファイト、トリスジノニルフェニルフォスファイト、トリス(2,4−ジ−t−ブチルフェニル)フォスファイト、トリス(ビフェニル)フォスファイト、ジステアリルペンタエリスリトールジフォスファイト、ジ(2,4−ジ−t−ブチルフェニル)ペンタエリスリトールジフォスファイト、ジ(ノニルフェニル)ペンタエリスリトールジフォスファイト、フェニルビスフェノールAペンタエリスリトールジフォスファイト、テトラトリデシル4,4’−ブチリデンビス(3−メチル−6−t−ブチルフェノール)ジフォスファイト、ヘキサトリデシル1,1,3−トリス(2−メチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタントリフォスファイト、3,5−ジ−t−ブチル−4−ヒドロキシベンジルフォスファイトジエチルエステル、ソジウムビス(4−t−ブチルフェニル)フォスファイト、ソジウム−2,2−メチレン−ビス(4,6−ジ−t−ブチルフェニル)−フォスファイト、1,3−ビス(ジフェノキシフォスフォニロキシ)−ベンゼン、亜リン酸エチルビス(2,4−ジtert−ブチル−6−メチルフェニル)等が挙げられる。その他フォスファイト構造を有するオリゴマータイプ及びポリマータイプの化合物等も使用することが出来る。 Examples of the phosphorus antioxidants include tris (isodecyl) phosphite, tris (tridecyl) phosphite, phenylisooctylphosphite, phenylisodecylphosphite, phenyldi (tridecyl) phosphite, diphenylisooctylphosphite, and diphenylisodecyl. Phosphite, diphenyltridecylphosphite, triphenylphosphite, tris (nonylphenyl) phosphite, 4,4′isopropylidenediphenolalkylphosphite, trisnonylphenylphosphite, trisdinonylphenylphosphite, tris (2 , 4-di-t-butylphenyl) phosphite, tris (biphenyl) phosphite, distearylpentaerythritol diphosphite, di ( , 4-Di-t-butylphenyl) pentaerythritol diphosphite, di (nonylphenyl) pentaerythritol diphosphite, phenylbisphenol A pentaerythritol diphosphite, tetratridecyl 4,4'-butylidenebis (3-methyl- 6-t-butylphenol) diphosphite, hexatridecyl 1,1,3-tris (2-methyl-4-hydroxy-5-t-butylphenyl) butanetriphosphite, 3,5-di-t-butyl 4-hydroxybenzyl phosphite diethyl ester, sodium bis (4-t-butylphenyl) phosphite, sodium-2,2-methylene-bis (4,6-di-t-butylphenyl) -phosphite, 1,3 -Bis (diphenoxyphosphoniloxy)- Benzene, phosphorous acid ethyl bis (2,4-di-tert- butyl-6-methylphenyl), and the like. In addition, oligomer type and polymer type compounds having a phosphite structure can also be used.
イオウ系酸化防止剤としては、2,2−チオ−ジエチレンビス〔3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート〕、2,4−ビス〔(オクチルチオ)メチル〕−o−クレゾール、2,4−ビス〔(ラウリルチオ)メチル〕−o−クレゾール等が挙げられる。その他チオエーテル構造を有するオリゴマータイプ及びポリマータイプの化合物等も使用することが出来る。 Examples of the sulfur-based antioxidants include 2,2-thio-diethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] and 2,4-bis [(octylthio) methyl]- o-cresol, 2,4-bis [(laurylthio) methyl] -o-cresol and the like. In addition, oligomer type and polymer type compounds having a thioether structure can also be used.
ベンゾトリアゾール系酸化防止剤としては、ベンゾトリアゾール構造を有するオリゴマータイプ及びポリマータイプの化合物等を使用することが出来る。 As the benzotriazole-based antioxidant, oligomer type and polymer type compounds having a benzotriazole structure can be used.
ベンゾフェノン系酸化防止剤として具体的には、2−ヒドロキシ−4−メトキシベンゾフェノン、2,4−ジヒドロキシベンゾフェノン、2−ヒドロキシ−4−n−オクトキシベンゾフェノン、4−ドデシロキシ−2−ヒドロキシベンゾフェノン、2−ヒドロキシ−4−オクタデシロキシベンゾフェノン、2,2’ジヒドロキシ−4−メトキシベンゾフェノン、2,2’ジヒドロキシ−4,4’−ジメトキシベンゾフェノン、2,2’,4,4’−テトラヒドロキシベンゾフェノン、2−ヒドロキシ−4−メトキシ−5スルフォベンゾフェノン、2−ヒドロキシ−4−メトキシ−2’−カルボキシベンゾフェノン等が挙げられる。その他ベンゾフェノン構造を有するオリゴマータイプ及びポリマータイプの化合物等も使用することが出来る。 Specific examples of the benzophenone-based antioxidant include 2-hydroxy-4-methoxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, Hydroxy-4-octadecyloxybenzophenone, 2,2'dihydroxy-4-methoxybenzophenone, 2,2'dihydroxy-4,4'-dimethoxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone, 2- Hydroxy-4-methoxy-5sulfobenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone, and the like. In addition, oligomer type and polymer type compounds having a benzophenone structure can also be used.
トリアジン系酸化防止剤としては、2,4−ビス(アリル)−6−(2−ヒドロキシフェニル)1,3,5−トリアジン等が挙げられる。その他トリアジン構造を有するオリゴマータイプ及びポリマータイプの化合物等も使用することが出来る。 Examples of the triazine antioxidant include 2,4-bis (allyl) -6- (2-hydroxyphenyl) 1,3,5-triazine and the like. In addition, oligomer type and polymer type compounds having a triazine structure can also be used.
サルチル酸エステル系酸化防止剤としては、サリチル酸フェニル、サリチル酸p−オクチルフェニル、サリチル酸p−tertブチルフェニル等が挙げられる。その他サルチル酸エステル構造を有するオリゴマータイプ及びポリマータイプの化合物等も使用することが出来る。 Examples of the salicylate-based antioxidants include phenyl salicylate, p-octylphenyl salicylate, p-tertbutylphenyl salicylate and the like. In addition, oligomer type and polymer type compounds having a salicylate structure can also be used.
これらの酸化防止剤は、1種を単独で、または必要に応じて任意の比率で2種以上混合して用いることができる。 These antioxidants can be used singly or as a mixture of two or more at any ratio as needed.
また酸化防止剤の含有量は、着色組成物の固形分質量を基準として、0.5〜5.0質量%の場合、色相的により好ましい。 When the content of the antioxidant is 0.5 to 5.0% by mass based on the mass of the solid content of the coloring composition, it is more preferable in terms of hue.
(アミン系化合物)
また、本発明の着色組成物には、必要に応じて、溶存している酸素を還元する働きのあるアミン系化合物を含有させることができる。
(Amine compound)
Further, the coloring composition of the present invention can contain an amine compound having a function of reducing dissolved oxygen, if necessary.
このようなアミン系化合物としては、トリエタノールアミン、メチルジエタノールアミン、トリイソプロパノールアミン、4−ジメチルアミノ安息香酸メチル、4−ジメチルアミノ安息香酸エチル、4−ジメチルアミノ安息香酸イソアミル、安息香酸2−ジメチルアミノエチル、4−ジメチルアミノ安息香酸2−エチルヘキシル、およびN,N−ジメチルパラトルイジン等が挙げられる。 Examples of such an amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, and 2-dimethylamino benzoate. Examples include ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, and N, N-dimethylparatoluidine.
(レベリング剤)
本発明の着色組成物には、必要に応じて、ガラス、プラスチック基板、またはフィルム上での組成物のレベリング性をよくするため、レベリング剤を含有させることができる。レベリング剤としては、主鎖にポリエーテル構造またはポリエステル構造を有するジメチルシロキサンが好ましい。主鎖にポリエーテル構造を有するジメチルシロキサンの具体例としては、東レ・ダウコーニング社製FZ−2122、ビックケミー社製BYK−333などが挙げられる。主鎖にポリエステル構造を有するジメチルシロキサンの具体例としては、ビックケミー社製BYK−310、BYK−370などが挙げられる。主鎖にポリエーテル構造を有するジメチルシロキサンと、主鎖にポリエステル構造を有するジメチルシロキサンとは、併用することもできる。レベリング剤の含有量は通常、着色組成物の全質量を基準(100質量%)として、0.003〜0.5質量%用いることが好ましい。
(Leveling agent)
If necessary, the coloring composition of the present invention may contain a leveling agent to improve the leveling property of the composition on a glass, plastic substrate, or film. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable. Specific examples of dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Dow Corning Toray and BYK-333 manufactured by Big Chemie. Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK-Chemie. Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can be used in combination. Usually, the content of the leveling agent is preferably 0.003 to 0.5% by mass based on the total mass of the coloring composition (100% by mass).
レベリング剤として特に好ましいものとしては、分子内に疎水基と親水基を有するいわゆる界面活性剤の一種で、親水基を有しながらも水に対する溶解性が小さく、着色組成物に添加した場合、その表面張力低下能が低いという特徴を有し、さらに表面張力低下能が低いにも拘らずガラス板への濡れ性が良好なものが有用であり、泡立ちによる塗膜の欠陥が出現しない添加量において十分に帯電性を抑止できるものが好ましく使用できる。このような好ましい特性を有するレベリング剤として、ポリアルキレンオキサイド単位を有するジメチルポリシロキサンが好ましく使用できる。ポリアルキレンオキサイド単位としては、ポリエチレンオキサイド単位、ポリプロピレンオキサイド単位があり、ジメチルポリシロキサンは、ポリエチレンオキサイド単位とポリプロピレンオキサイド単位とを共に有していてもよい。 Particularly preferred as a leveling agent is a kind of a so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, which has a low solubility in water while having a hydrophilic group, and when added to a coloring composition, It has the feature that surface tension lowering ability is low, and even though the surface tension lowering ability is low, it is useful that the wettability to the glass plate is good, and at the amount of addition that does not cause defects in the coating film due to foaming Those which can sufficiently suppress the charging property can be preferably used. As a leveling agent having such preferable characteristics, dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. The polyalkylene oxide unit includes a polyethylene oxide unit and a polypropylene oxide unit, and the dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.
また、ポリアルキレンオキサイド単位のジメチルポリシロキサンとの結合形態は、ポリアルキレンオキサイド単位がジメチルポリシロキサンの繰り返し単位中に結合したペンダント型、ジメチルポリシロキサンの末端に結合した末端変性型、ジメチルポリシロキサンと交互に繰り返し結合した直鎖状のブロックコポリマー型のいずれであってもよい。ポリアルキレンオキサイド単位を有するジメチルポリシロキサンは、東レ・ダウコーニング株式会社から市販されており、例えば、FZ−2110、FZ−2122、FZ−2130、FZ−2166、FZ−2191、FZ−2203、FZ−2207が挙げられるが、これらに限定されるものではない。 The bonding form of the polyalkylene oxide unit with dimethylpolysiloxane is a pendant type in which the polyalkylene oxide unit is bonded in a repeating unit of dimethylpolysiloxane, a terminal-modified type in which the polyalkylene oxide unit is bonded to a terminal of dimethylpolysiloxane, and dimethylpolysiloxane. Any of a linear block copolymer type alternately and repeatedly bonded may be used. Dimethyl polysiloxane having a polyalkylene oxide unit is commercially available from Dow Corning Toray Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ -2207, but is not limited thereto.
レベリング剤には、アニオン性、カチオン性、ノニオン性、または両性の界面活性剤を補助的に加えることも可能である。界面活性剤は、2種以上混合して使用しても構わない。
レベリング剤に補助的に加えるアニオン性界面活性剤としては、ポリオキシエチレンアルキルエーテル硫酸塩、ドデシルベンゼンスルホン酸ナトリウム、スチレン−アクリル酸共重合体のアルカリ塩、アルキルナフタリンスルホン酸ナトリウム、アルキルジフェニルエーテルジスルホン酸ナトリウム、ラウリル硫酸モノエタノールアミン、ラウリル硫酸トリエタノールアミン、ラウリル硫酸アンモニウム、ステアリン酸モノエタノールアミン、ステアリン酸ナトリウム、ラウリル硫酸ナトリウム、スチレン−アクリル酸共重合体のモノエタノールアミン、ポリオキシエチレンアルキルエーテルリン酸エステルなどが挙げられる。
Anionic, cationic, nonionic, or amphoteric surfactants can also be added to the leveling agent. Two or more surfactants may be used as a mixture.
Anionic surfactants to be added to the leveling agent as auxiliary agents include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalene sulfonate, alkyl diphenyl ether disulfonic acid Sodium, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, styrene-acrylic acid copolymer monoethanolamine, polyoxyethylene alkyl ether phosphate Esters and the like.
レベリング剤に補助的に加えるカオチン性界面活性剤としては、アルキル4級アンモニウム塩やそれらのエチレンオキサイド付加物が挙げられる。レベリング剤に補助的に加えるノニオン性界面活性剤としては、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンノニルフェニルエーテル、ポリオキシエチレンアルキルエーテルリン酸エステル、ポリオキシエチレンソルビタンモノステアレート、ポリエチレングリコールモノラウレート等が挙げられる。また、アルキルジメチルアミノ酢酸ベタインなどのアルキルベタイン、アルキルイミダゾリンなどの両性界面活性剤、また、シリコーン系の界面活性剤が挙げられる。 Examples of the chaotic surfactant supplementally added to the leveling agent include an alkyl quaternary ammonium salt and an ethylene oxide adduct thereof. Nonionic surfactants to be added to the leveling agent supplementally include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonyl phenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate And polyethylene glycol monolaurate. Further, an alkyl betaine such as an alkyldimethylaminoacetic acid betaine, an amphoteric surfactant such as an alkylimidazoline, and a silicone-based surfactant may be used.
(硬化剤、硬化促進剤)
また本発明の着色組成物には、熱硬化性樹脂の硬化を補助するため、必要に応じて、硬化剤、硬化促進剤などを含有させることができる。硬化剤としては、フェノール系樹脂、アミン系化合物、酸無水物、活性エステル、カルボン酸系化合物、スルホン酸系化合物などが有効であるが、特にこれらに限定されるものではなく、熱硬化性樹脂と反応し得るものであれば、いずれの硬化剤を使用してもよい。また、これらの中でも、1分子内に2個以上のフェノール性水酸基を有する化合物、アミン系硬化剤が好ましく挙げられる。上記硬化促進剤としては、例えば、アミン化合物(例えば、ジシアンジアミド、ベンジルジメチルアミン、4−(ジメチルアミノ)−N,N−ジメチルベンジルアミン、4−メトキシ−N,N−ジメチルベンジルアミン、4−メチル−N,N−ジメチルベンジルアミン等)、4級アンモニウム塩化合物(例えば、トリエチルベンジルアンモニウムクロリド等)、ブロックイソシアネート化合物(例えば、ジメチルアミン等)、イミダゾール誘導体二環式アミジン化合物およびその塩(例えば、イミダゾール、2−メチルイミダゾール、2−エチルイミダゾール、2−エチル−4−メチルイミダゾール、2−フェニルイミダゾール、4−フェニルイミダゾール、1−シアノエチル−2−フェニルイミダゾール、1−(2−シアノエチル)−2−エチル−4−メチルイミダゾール等)、リン化合物(例えば、トリフェニルホスフィン等)、グアナミン化合物(例えば、メラミン、グアナミン、アセトグアナミン、ベンゾグアナミン等)、S−トリアジン誘導体(例えば、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン、2−ビニル−2,4−ジアミノ−S−トリアジン、2−ビニル−4,6−ジアミノ−S−トリアジン・イソシアヌル酸付加物、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン・イソシアヌル酸付加物等)などを用いることができる。これらは1種単独で使用してもよく、2種以上を併用してもよい。上記硬化促進剤の含有量としては、熱硬化性樹脂100質量部に対し、0.01〜15質量部が好ましい。
(Curing agent, curing accelerator)
In addition, the coloring composition of the present invention may contain a curing agent, a curing accelerator, and the like, if necessary, to assist the curing of the thermosetting resin. As a curing agent, a phenolic resin, an amine compound, an acid anhydride, an active ester, a carboxylic acid compound, a sulfonic acid compound, and the like are effective, but not particularly limited thereto, and a thermosetting resin Any curing agent may be used as long as it can react with the curing agent. Among these, a compound having two or more phenolic hydroxyl groups in one molecule and an amine-based curing agent are preferably exemplified. Examples of the curing accelerator include amine compounds (for example, dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, 4-methyl -N, N-dimethylbenzylamine, etc.), quaternary ammonium salt compounds (eg, triethylbenzylammonium chloride, etc.), blocked isocyanate compounds (eg, dimethylamine, etc.), imidazole derivative bicyclic amidine compounds and salts thereof (eg, Imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1- (2-cyanoethyl) -2- Tyl-4-methylimidazole, etc.), phosphorus compounds (eg, triphenylphosphine, etc.), guanamine compounds (eg, melamine, guanamine, acetoguanamine, benzoguanamine, etc.), S-triazine derivatives (eg, 2,4-diamino-6) -Methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine / isocyanuric acid adduct, 2,4-diamino-6 Methacryloyloxyethyl-S-triazine / isocyanuric acid adduct) and the like. These may be used alone or in combination of two or more. The content of the curing accelerator is preferably 0.01 to 15 parts by mass based on 100 parts by mass of the thermosetting resin.
(その他の添加剤成分)
本発明の着色組成物には、必要に応じて、経時粘度を安定化させるために貯蔵安定剤を含有させることができる。また、ガラス、プラスチック基板、またはフィルムとの密着性を高めるためにシランカップリング剤等の密着向上剤を含有させることもできる。
(Other additive components)
If necessary, the coloring composition of the present invention may contain a storage stabilizer to stabilize the viscosity over time. In addition, an adhesion improver such as a silane coupling agent may be contained in order to enhance the adhesion to a glass, a plastic substrate, or a film.
貯蔵安定剤としては、例えば、ベンジルトリメチルクロライド、ジエチルヒドロキシアミンなどの4級アンモニウムクロライド、乳酸、シュウ酸などの有機酸およびそのメチルエーテル、t−ブチルピロカテコール、テトラエチルホスフィン、テトラフェニルフォスフィンなどの有機ホスフィン、亜リン酸塩等が挙げられる。貯蔵安定剤は、着色剤100質量部に対し、0.1〜10質量部の量で用いることができる。 As the storage stabilizer, for example, benzyltrimethyl chloride, quaternary ammonium chloride such as diethylhydroxyamine, lactic acid, organic acids such as oxalic acid and its methyl ether, t-butyl pyrocatechol, tetraethylphosphine, tetraphenylphosphine and the like Organic phosphines, phosphites and the like can be mentioned. The storage stabilizer can be used in an amount of 0.1 to 10 parts by mass based on 100 parts by mass of the colorant.
密着向上剤としては、ビニルトリス(β−メトキシエトキシ)シラン、ビニルエトキシシラン、ビニルトリメトキシシラン等のビニルシラン類、γ−メタクリロキシプロピルトリメトキシシラン等の(メタ)アクリルシラン類、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、β−(3,4−エポキシシクロヘキシル)メチルトリメトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、β−(3,4−エポキシシクロヘキシル)メチルトリエトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン等のエポキシシラン類、N−β(アミノエチル)γ−アミノプロピルトリメトキシシラン、N−β(アミノエチル)γ−アミノプロピルトリエトキシシラン、N−β(アミノエチル)γ−アミノプロピルメチルジエトキシシシラン、γ−アミノプロピルトリエトキシシラン、γ−アミノプロピルトリメトキシシラン、N−フェニル−γ−アミノプロピルトリメトキシシラン、N−フェニル−γ−アミノプロピルトリエトキシシラン等のアミノシラン類、γ−メルカプトプロピルトリメトキシシラン、γ−メルカプトプロピルトリエトキシシラン等のチオシラン類等のシランカップリング剤が挙げられる。密着向上剤は、着色組成物中の着色剤100質量部に対して、0.01〜10質量部、好ましくは0.05〜5質量部の量で用いることができる。 Examples of the adhesion improver include vinylsilanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane and vinyltrimethoxysilane, (meth) acrylsilanes such as γ-methacryloxypropyltrimethoxysilane, β- (3 4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxycyclohexyl) Epoxysilanes such as methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (amino Ethyl) γ-aminopropyltrie Xysilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N-phenyl Silane coupling agents such as aminosilanes such as -γ-aminopropyltriethoxysilane and thiosilanes such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyltriethoxysilane. The adhesion improver can be used in an amount of 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, based on 100 parts by mass of the coloring agent in the coloring composition.
本発明のナフタロシアニン固溶体の分散には、アンカー翼等の一般に用いられている混合撹拌装置を用いることができ、特に制限は無い。混合撹拌装置の中では、ウルトラディスパー〔浅田鉄鋼株式会社、商品名〕、エバラマイルダー〔株式会社荏原製作所、商品名〕、TKホモミクサー、TKパイプラインミクサー、TKホモジェッター、TKホモミックラインフロー、フィルミックス〔以上、特殊機化工業株式会社、商品名〕、クリアミックス〔エム・テクニック株式会社、商品名〕、ケイディーミル〔キネティック・ディスパージョン社、商品名〕等の高速攪拌混合装置が好ましい。その他、ロールミル、ビーズミル、ニーダー、エクストルーダ等の混練機、高圧ホモゲナイザー〔株式会社イズミフードマシナリ、商品名〕、ミニラボ8.3H型〔Rannie社、商品名〕に代表されるホモバルブ式の高圧ホモジナイザー、マイクロフルイダイザー〔Microfluidics社、商品名〕、ナノマイザー〔ナノマイザー株式会社、商品名〕、アルティマイザー〔スギノマシン株式会社、商品名〕、ジーナスPY〔白水化学株式会社、商品名〕、DeBEE2000〔日本ビーイーイー株式会社、商品名〕等のチャンバー式の高圧ホモジナイザー等を用いて分散する方法が挙げられる。これらの中では、小粒子径化の観点から、ロールミル、ビーズミル、ニーダー及び高圧ホモジナイザーが好ましい。これらの装置は複数を組み合わせることもできる。 For dispersing the naphthalocyanine solid solution of the present invention, a commonly used mixing and stirring device such as an anchor blade can be used, and there is no particular limitation. Among the mixing and stirring devices, Ultra Disper (Asada Steel Corp., trade name), Ebara Milder (Ebara Corporation, trade name), TK homomixer, TK pipeline mixer, TK homojetter, TK homomic line flow, A high-speed stirring and mixing apparatus such as Fill Mix (above, Tokushu Kika Kogyo Co., Ltd., trade name), Clear Mix (M Technic Co., Ltd., trade name), K-Die Mill (Kinetic Dispersion Co., trade name) is preferred. In addition, kneading machines such as a roll mill, a bead mill, a kneader, and an extruder, a high-pressure homogenizer [Izumi Food Machinery Co., Ltd., trade name], a homo-valve high-pressure homogenizer represented by Minilab 8.3H [Rannie, trade name], micro Fluidizer [Microfluidics Co., trade name], Nanomizer [Nanomizer Co., trade name], Ultimizer [Sugino Machine Co., trade name], Genus PY [Shiromizu Chemical Co., trade name], DeBEE2000 [Nihon BEE Co., Ltd. Dispersion using a chamber-type high-pressure homogenizer such as a trade name]. Among them, a roll mill, a bead mill, a kneader and a high-pressure homogenizer are preferable from the viewpoint of reducing the particle diameter. These devices can be used in combination.
ナフタロシアニン固溶体を分散する際には、必要に応じて色素誘導体を添加してもよい。色素誘導体は、ソルトミリング処理する際に記述した化合物と同義である。 When dispersing the naphthalocyanine solid solution, a dye derivative may be added as necessary. The dye derivative is synonymous with the compound described when performing the salt milling treatment.
このような方法で着色組成物を得た後、沈殿物や粗大粒子を除去するために、更に遠心分離して、沈殿物を分離する工程を含んでも良い。遠心分離に使用する装置としては、一般に、無孔の回転ボウルを高速回転させることによって懸濁物質を遠心沈降させる遠心沈降機、及び側壁に細孔又はスリットを有する回転バスケットが用いられた遠心濾過・脱水機が知られている。本発明では、これらのうち、遠心沈降機を好適に用いることができる〔例えば、化学工学会編「化学装置便覧」、改訂二版第2刷、丸善株式会社、平成8年4月5日、798頁参照〕。遠心沈降機としては、例えば、遠心沈降管型、円筒型、分離板型、バスケット型、スクリデカンター型等の遠心沈降機が挙げられる。 After obtaining the coloring composition by such a method, the method may further include a step of separating the precipitate by centrifugation to remove the precipitate and coarse particles. As a device used for centrifugation, generally, a centrifugal sedimentation device that centrifugally sediments suspended substances by rotating a non-porous rotating bowl at high speed, and a centrifugal filtration using a rotating basket having pores or slits on side walls. -Dehydrators are known. In the present invention, among these, a centrifugal sedimentation machine can be preferably used [for example, “Chemical Equipment Handbook” edited by the Society of Chemical Engineers, 2nd revised edition, Maruzen Co., Ltd., April 5, 1996, 798]. Examples of the centrifugal sedimentation machine include a centrifugal sedimentation machine such as a centrifugal sedimentation tube type, a cylindrical type, a separation plate type, a basket type and a Scridecanter type.
本発明の着色組成物に含まれるナフタロシアニン固溶体の濃度は、1〜35質量%の範囲であることが好ましく、2〜25質量%の範囲であることがより好ましい。 The concentration of the naphthalocyanine solid solution contained in the coloring composition of the present invention is preferably in the range of 1 to 35% by mass, and more preferably in the range of 2 to 25% by mass.
本発明の着色組成物の用途としては、画像、特にカラー画像を形成するための画像記録材料が挙げられ、具体的には、オフセット、グラビア、フレキソ、スクリーン、インクジェットなどの各種印刷インキや塗料、LCD、PDP、有機エレクトロルミネッセンス、電子紙などのディスプレイやCCDなどの撮像素子で用いられるカラーフィルターに適用できる。 Examples of uses of the coloring composition of the present invention include an image, particularly an image recording material for forming a color image, and specifically, offset, gravure, flexo, screen, various printing inks and paints such as inkjet, The present invention can be applied to displays such as LCDs, PDPs, organic electroluminescence, electronic paper, and color filters used in imaging devices such as CCDs.
以下に、本発明を実施例に基づいて説明するが、本発明はこれによって限定されるものではない。なお、実施例中「部」とは、「質量部」を表す。 Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In the examples, “parts” means “parts by mass”.
[実施例1]
(無金属ナフタロシアニン・チタニルフタロシアニン固溶体(P−1)の製造)
反応容器に濃硫酸600部を加え、氷冷した。氷冷下、無金属ナフタロシアニン9.18部とチタニルフタロシアニン0.82部を攪拌しながらゆっくり加え、更に3時間攪拌した。この混合物を氷水20000部に注入し、2時間攪拌した。これをろ過し、ろ液が中性になるまで水10000部で洗浄し、N−メチルピロリドン5000部およびメタノール5000部で洗浄後、40℃で一晩乾燥させた。一連の手順により、9.1部の混合物を回収した。次いで、この混合物2部に塩化ナトリウム10部およびジエチレングリコール5部を加えた後に、150lb(=667N)の荷重を掛けたフーバーマーラーで回転速度100rpmにて5分間、4回混練した。処理後の混合物に対し2000部の水を加え、30分攪拌した。これをろ過し、水3000部で洗浄した後、40℃で一晩乾燥させた。一連の手順により、1.5部の無金属ナフタロシアニン・チタニルフタロシアニン固溶体(P−1)を回収した。
得られた粉体はCuKα線によるX線回折パターンが、回折角2θ = 6.0°、13.5°、16.6°、17.4°、24.8°、26.8°にピークを有していた。また、赤外吸収スペクトルでは 3976, 3955, 3939, 3911, 3891, 3880, 3864, 3847, 3830, 3807, 3774, 3765, 3744, 3739, 3718, 3696, 3683, 3663, 3641, 3624, 3603, 3575, 3560, 3533, 3509, 3473, 3410, 3343, 3216, 3051, 2709, 2529, 2352, 2331, 2159, 2024, 1976, 1767, 1706, 1696, 1652, 1626, 1550, 1511, 1464, 1444, 1389, 1349, 1336, 1324, 1260, 1211, 1199, 1162, 1143, 1129, 1088, 1024, 1000, 952, 942, 887, 833, 798, 780, 741, 718, 693, 666, 639, 612, 563, 535, 497, 465, 428, 414, 405 cm-1にピークを有していた。
[Example 1]
(Production of metal-free naphthalocyanine / titanyl phthalocyanine solid solution (P-1))
600 parts of concentrated sulfuric acid was added to the reaction vessel and cooled with ice. Under ice-cooling, 9.18 parts of metal-free naphthalocyanine and 0.82 parts of titanyl phthalocyanine were slowly added with stirring, and further stirred for 3 hours. This mixture was poured into 20,000 parts of ice water and stirred for 2 hours. This was filtered, washed with 10,000 parts of water until the filtrate became neutral, washed with 5000 parts of N-methylpyrrolidone and 5000 parts of methanol, and dried overnight at 40 ° C. A series of procedures recovered 9.1 parts of the mixture. Next, 10 parts of sodium chloride and 5 parts of diethylene glycol were added to 2 parts of the mixture, and the mixture was kneaded four times at a rotation speed of 100 rpm for 5 minutes by a Hoover Maller under a load of 150 lb (= 667 N). 2000 parts of water was added to the mixture after the treatment, and the mixture was stirred for 30 minutes. This was filtered, washed with 3000 parts of water, and dried at 40 ° C. overnight. Through a series of procedures, 1.5 parts of a metal-free naphthalocyanine / titanyl phthalocyanine solid solution (P-1) was recovered.
The X-ray diffraction pattern of the obtained powder by CuKα ray peaks at diffraction angles 2θ = 6.0 °, 13.5 °, 16.6 °, 17.4 °, 24.8 °, 26.8 °. Had. In the infrared absorption spectrum, 3976, 3955, 3939, 3911, 3891, 3880, 3864, 3847, 3830, 3807, 3774, 3765, 3744, 3739, 3718, 3696, 3683, 3663, 3641, 3624, 3603, 3575. , 3560, 3533, 3509, 3473, 3410, 3343, 3216, 3051, 2709, 2529, 2352, 2331, 2159, 2024, 1976, 1767, 1767, 1706, 1696, 1652, 1626, 1550, 1511, 1464, 1489. , 1349, 1336, 1324, 1260, 1211, 1199, 1162, 1143, 1129, 1088, 1024, 1000, 952 942, 887, 833, 798, 780, 741, 718, 693, 666, 639, 612, 563, 535, 497, 465, 428, 414, 405 cm -1 .
[実施例2]
(無金属ナフタロシアニン・無金属フタロシアニン固溶体(P−2)の製造)
実施例1の無金属ナフタロシアニン9.18部とチタニルフタロシアニン0.82部を、無金属ナフタロシアニン9.26部と無金属フタロシアニン0.74部に変え、実施例1と同様の方法で無金属ナフタロシアニン・無金属フタロシアニン固溶体P−2を得た。
得られた粉体はCuKα線によるX線回折パターンが、回折角2θ =6.0°、13.4°、17.7°、24.7°、26.7°にピークを有していた。また、赤外吸収スペクトルでは、3791, 3697, 3661, 3284, 3051, 2157, 1978, 1768, 1707, 1508, 1389, 1349, 1324, 1260, 1211, 1162, 1143, 1129, 1088, 1024, 1000, 942, 886, 833, 780, 740, 717, 694, 612, 565, 496, 465, 407 cm-1にピークを有していた。
[Example 2]
(Production of metal-free naphthalocyanine / metal-free phthalocyanine solid solution (P-2))
9.18 parts of metal-free naphthalocyanine and 0.82 parts of titanyl phthalocyanine of Example 1 were changed to 9.26 parts of metal-free naphthalocyanine and 0.74 parts of metal-free phthalocyanine, and a metal-free metal was obtained in the same manner as in Example 1. A naphthalocyanine / metal-free phthalocyanine solid solution P-2 was obtained.
The X-ray diffraction pattern of the obtained powder by CuKα radiation had peaks at diffraction angles 2θ = 6.0 °, 13.4 °, 17.7 °, 24.7 °, 26.7 °. . In the infrared absorption spectrum, 3791, 3697, 3661, 3284, 3051, 2157, 1978, 1768, 1707, 1508, 1389, 1349, 1324, 1260, 1211, 1162, 1143, 1129, 1088, 1024, 1000, It had peaks at 942, 886, 833, 780, 740, 717, 694, 612, 565, 496, 465, 407 cm -1 .
[実施例3](P−3)
(無金属ナフタロシアニン・チタニルフタロシアニン固溶体(P−3)の製造)
無金属ナフタロシアニン1.84部とチタニルフタロシアニン0.16部に塩化ナトリウム10部およびジエチレングリコール5部を加えた。この混合物を150lb(=667N)の荷重を掛けたフーバーマーラーで回転速度100rpmにて5分間、4回混練した。処理後の混合物に対し2000部の水を加え、30分間攪拌した。これをろ過し、水3000部で洗浄した後、40℃で一晩乾燥させた。一連の手順により、1.5部の無金属ナフタロシアニン・チタニルフタロシアニン固溶体(P−3)を回収した。
得られた粉体はCuKα線によるX線回折パターンが、回折角2θ = 6.0°、13.4°、16.6°、17.5°、18.5°、24.6°、26.9°にピークを有していた。また、赤外吸収スペクトルでは3891, 3845, 3789, 3695 3661, 3638, 3576, 3289, 3054 2532, 2158, 2022, 1975, 1767 1714, 1610, 1510, 1390, 1350 1325, 1261, 1212, 1163, 1144 1129, 1119, 1089, 1025, 1002 942, 887, 833, 747, 728, 718, 694, 612, 563, 496, 466, 428, 416, 409 cm-1にピークを有していた。
[Example 3] (P-3)
(Production of metal-free naphthalocyanine / titanyl phthalocyanine solid solution (P-3))
To 1.84 parts of metal-free naphthalocyanine and 0.16 parts of titanyl phthalocyanine, 10 parts of sodium chloride and 5 parts of diethylene glycol were added. This mixture was kneaded four times for 5 minutes at a rotation speed of 100 rpm with a Hoover Mahler under a load of 150 lb (= 667 N). 2000 parts of water was added to the mixture after the treatment, and the mixture was stirred for 30 minutes. This was filtered, washed with 3000 parts of water, and dried at 40 ° C. overnight. Through a series of procedures, 1.5 parts of a metal-free naphthalocyanine / titanyl phthalocyanine solid solution (P-3) was recovered.
The obtained powder has an X-ray diffraction pattern by CuKα ray, diffraction angles 2θ = 6.0 °, 13.4 °, 16.6 °, 17.5 °, 18.5 °, 24.6 °, 26 Had a peak at 0.9 °. In the infrared absorption spectrum, 3891, 3845, 3789, 3695 3661, 3638, 3576, 3289, 3054 2532, 2158, 2022, 1975, 1767 1714, 1610, 1510, 1390, 1350 1325, 1261, 1212, 1163, 1144. It had peaks at 1129, 1119, 1089, 1025, 1002 942, 887, 833, 747, 728, 718, 694, 612, 563, 496, 466, 428, 416, 409 cm -1 .
[実施例4](P−4)
(無金属ナフタロシアニン・無金属フタロシアニン固溶体(P−4)の製造)
無金属ナフタロシアニン1.85部と無金属フタロシアニン0.15部に塩化ナトリウム10部およびジエチレングリコール5部を加えた。この混合物を150lb(=667N)の荷重を掛けたフーバーマーラーで回転速度100rpmにて5分間、4回混練した。処理後の混合物に対し2000部の水を加え、30分間攪拌した。これをろ過し、水3000部で洗浄した後、40℃で一晩乾燥させた。一連の手順により、1.5部の無金属ナフタロシアニン・無金属フタロシアニン固溶体(P−4)を回収した。
得られた粉体はCuKα線によるX線回折パターンが、回折角2θ =5.9°、13.4°、16.5°、17.5°、18.5°、24.7°、26.8°にピークを有していた。また、赤外吸収スペクトルでは3817, 3746, 3672, 3647, 3054, 2536, 2158, 2031, 1973, 1763, 1713, 1509, 1390, 1350, 1325, 1261, 1211, 1162, 1129, 1089, 1025, 1001, 942, 887, 833, 742, 717, 694, 612, 496, 466, 435, 419 cm-1にピークを有していた。
[Example 4] (P-4)
(Production of metal-free naphthalocyanine / metal-free phthalocyanine solid solution (P-4))
To 1.85 parts of metal-free naphthalocyanine and 0.15 parts of metal-free phthalocyanine, 10 parts of sodium chloride and 5 parts of diethylene glycol were added. This mixture was kneaded four times for 5 minutes at a rotation speed of 100 rpm with a Hoover Mahler under a load of 150 lb (= 667 N). 2000 parts of water was added to the mixture after the treatment, and the mixture was stirred for 30 minutes. This was filtered, washed with 3000 parts of water, and dried at 40 ° C. overnight. Through a series of procedures, 1.5 parts of a metal-free naphthalocyanine / metal-free phthalocyanine solid solution (P-4) was recovered.
The obtained powder had an X-ray diffraction pattern by CuKα ray, diffraction angles 2θ = 5.9 °, 13.4 °, 16.5 °, 17.5 °, 18.5 °, 24.7 °, 26 Had a peak at 0.8 °. In the infrared absorption spectrum, 3817, 3746, 3672, 3647, 3054, 2536, 2158, 2031, 1973, 1763, 1713, 1509, 1390, 1350, 1325, 1261, 1211, 1162, 1129, 1089, 1025, 1001 , 942, 887, 833, 742, 717, 694, 612, 496, 466, 435, and 419 cm -1 .
[実施例5]
(着色組成物(T−1))
実施例1で得られた固溶体(P−1)5部、ワニス(タマノール361(荒川化学工業株式会社製:ロジン変性フェノール樹脂)25部を150lb(=667N)の荷重を掛けたフーバーマーラーで回転速度100rpmにて1分間、4回混練し、着色組成物T−1を得た。
[Example 5]
(Coloring composition (T-1))
5 parts of the solid solution (P-1) obtained in Example 1 and 25 parts of a varnish (Tamanol 361 (manufactured by Arakawa Chemical Industries, Ltd .: rosin-modified phenol resin)) were rotated by a Hoover Mahler with a load of 150 lb (= 667N). The mixture was kneaded four times at a speed of 100 rpm for 1 minute to obtain a coloring composition T-1.
[実施例6]
(着色組成物(T−2))
固溶体(P−1)を実施例2で得られた固溶体(P−2)に変更し、実施例5と同様の方法で着色組成物(T−2)を作製した。
[Example 6]
(Coloring composition (T-2))
The solid solution (P-1) was changed to the solid solution (P-2) obtained in Example 2, and a coloring composition (T-2) was produced in the same manner as in Example 5.
[実施例7]
(着色組成物(T−3))
固溶体(P−1)を実施例3で得られた固溶体(P−3)に変更し、実施例5と同様の方法で着色組成物(T−3)を作製した。
[Example 7]
(Coloring composition (T-3))
The solid solution (P-1) was changed to the solid solution (P-3) obtained in Example 3, and a coloring composition (T-3) was produced in the same manner as in Example 5.
[実施例8]
(着色組成物(T−4))
固溶体(P−1)を実施例4で得られた固溶体(P−4)に変更し、実施例5と同様の方法で着色組成物(T−4)を作製した。
[Example 8]
(Coloring composition (T-4))
The solid solution (P-1) was changed to the solid solution (P-4) obtained in Example 4, and a coloring composition (T-4) was produced in the same manner as in Example 5.
[比較例1]
固溶体(P−1)を無金属ナフタロシアニンに変更し、実施例5と同様の方法で着色組成物(T−5)を作製した。
[Comparative Example 1]
A colored composition (T-5) was produced in the same manner as in Example 5, except that the solid solution (P-1) was changed to a metal-free naphthalocyanine.
[比較例2]
固溶体(P−1)を銅ナフタロシアニンに変更し、実施例5と同様の方法で着色組成物(T−6)を作製した。
[Comparative Example 2]
A colored composition (T-6) was produced in the same manner as in Example 5, except that the solid solution (P-1) was changed to copper naphthalocyanine.
[比較例3]
固溶体(P−1)5部を無金属ナフタロシアニン4.59部、チタニルフタロシアニン0.41部に変更し、実施例5と同様の方法で着色組成物(T−7)を作製した。
[Comparative Example 3]
A colored composition (T-7) was produced in the same manner as in Example 5, except that 5 parts of the solid solution (P-1) was changed to 4.59 parts of metal-free naphthalocyanine and 0.41 part of titanyl phthalocyanine.
[比較例4]
固溶体(P−1)5部を無金属ナフタロシアニン4.63部、無金属フタロシアニン0.37部に変更し、実施例5と同様の方法で着色組成物(T−8)を作製した。
[Comparative Example 4]
A colored composition (T-8) was produced in the same manner as in Example 5, except that 5 parts of the solid solution (P-1) was changed to 4.63 parts of metal-free naphthalocyanine and 0.37 parts of metal-free phthalocyanine.
[比較例5]
特開2002−194242の実施例1に従い、粗製銅フタロシアニン顔料 140部をPB15:3 100部、粗製ベンズイミダゾロン顔料 60部をPY185 100部に置き換えて顔料組成物(P−5)を得た。顔料組成物(P−5)を無金属ナフタロシアニンに変更し、実施例5と同様の方法で着色組成物(T−9)を作製した。
[Comparative Example 5]
According to Example 1 of JP-A-2002-194242, a pigment composition (P-5) was obtained by replacing 140 parts of crude copper phthalocyanine pigment with 100 parts of PB15: 3 and replacing 60 parts of crude benzimidazolone pigment with 100 parts of PY185. A pigmented composition (T-9) was prepared in the same manner as in Example 5, except that the pigment composition (P-5) was changed to a metal-free naphthalocyanine.
[着色組成物の評価]
実施例5〜8、比較例1〜5で得られた着色組成物(T−1〜9)0.5gと白インキ(酸化チタン50部を上記オフセットインキ用ワニス50部に分散して作成した)5.0gを50lb(=222N)の荷重を掛けたフーバーマーラーで回転速度25rpmにて4回混練して混合することでインキを得た。このインキの色相評価を分光光度計(日本分光社製V560)を用いて行った。表2に色相結果(L*,a*,b*,C*)を示す。なお、L*、a*、b*、C*は、JIS Z 8781−4に基づく。
[Evaluation of coloring composition]
0.5 g of the coloring compositions (T-1 to 9) obtained in Examples 5 to 8 and Comparative Examples 1 to 5 and white ink (50 parts of titanium oxide were dispersed in 50 parts of the varnish for offset ink described above). ) 5.0 g was kneaded and mixed four times at a rotation speed of 25 rpm with a Hoover muller under a load of 50 lb (= 222 N) to obtain an ink. The hue of this ink was evaluated using a spectrophotometer (V560 manufactured by JASCO Corporation). Table 2 shows the hue results (L * , a * , b *, C * ). In addition, L * , a * , b * , and C * are based on JISZ8781-4.
彩度を表すC*は、彩度が高いほど値は大きい。例えば、実施例5〜8は、顔料固溶体であり、無金属ナフタロシアニンである比較例1や、銅ナフタロシアニンである比較例2と彩度(C*)を比べると彩度が高い。同様に、実施例5〜8は、同成分比で調色した比較例3〜4と比べて彩度が高く、PB15:3とPY185で作製した比較例5よりも明度も彩度も高い。以上より、ナフタロシアニン顔料とフタロシアニン顔料を固溶体とする事で、彩度に優れたナフタロシアニン顔料とそれを用いた着色組成物を得た。 The value of C * representing the saturation increases as the saturation increases. For example, in Examples 5 to 8, which are pigment solid solutions, the chroma (C * ) is higher than that of Comparative Example 1 which is a metal-free naphthalocyanine or Comparative Example 2 which is a copper naphthalocyanine. Similarly, Examples 5 to 8 have higher chroma than Comparative Examples 3 and 4 toned with the same component ratio, and have higher brightness and chroma than Comparative Example 5 made with PB15: 3 and PY185. As described above, a naphthalocyanine pigment and a phthalocyanine pigment were made into a solid solution to obtain a naphthalocyanine pigment having excellent chroma and a coloring composition using the same.
[耐光性の評価]
得られた着色組成物を上質紙(日本製紙製ニューNPi)に塗布し、緑色塗膜を作製した。作製した塗膜の色度を色度計(X−rite社製i1BasicPro)を用いて色度[L*(1)、a*(1)、b*(1)]を測定した後、太陽光同等の分光分布となるキセノンランプを用いて、470W/m2での促進暴露試験(東洋精機社製SUNTEST CPS+)を24および96時間行った。光照射後の色度[L*(2)、a*(2)、b*(2)]を測定し、下記式により色差ΔE*abを算出した。
ΔE*ab= √((L*(2)- L*(1))2+ (a*(2)- a*(1)) 2+( b*(2)- b*(1)) 2)
色差ΔE*abが小さい方が、光照射での変色が小さく、耐光性良好な着色組成物となる。表4に色差ΔEを示す。
[Evaluation of light resistance]
The obtained coloring composition was applied to a high quality paper (New NPi manufactured by Nippon Paper Industries) to produce a green coating film. After measuring the chromaticity [L * (1), a * (1), b * (1)] of the chromaticity of the prepared coating film using a chromaticity meter (i-BasicPro manufactured by X-rite), sunlight was measured. Using a xenon lamp having the same spectral distribution, an accelerated exposure test at 470 W / m 2 (SUNEST CPS + manufactured by Toyo Seiki Co., Ltd.) was performed for 24 and 96 hours. The chromaticity [L * (2), a * (2), b * (2)] after light irradiation was measured, and the color difference ΔE * ab was calculated by the following equation.
ΔE * ab = √ ((L * (2) - L * (1)) 2 + (a * (2) - a * (1)) 2 + (b * (2) - b * (1)) 2 )
The smaller the color difference ΔE * ab, the smaller the color change upon light irradiation and the better the light resistance of the colored composition. Table 4 shows the color difference ΔE.
表4に示すように、本発明のナフタロシアニン固溶体を用いて作製した着色組成物は、96時間の光照射後でも色度の変化ΔEが小さかった。T−1は、顔料成分を調色により調製したT−7よりも高い耐光性を示し、これは同様の関係であるT−2、T−8でも同じ傾向であった。この事から、固溶体形成は耐光性向上に有効である。また、一度濃硫酸にて各顔料を溶解させる工程を省いたT−3、T−4は対応するT−1、T−2よりもやや耐光性に劣り、濃硫酸にて各顔料を溶解させる工程を行う事は耐光性の向上に有効である。PB15:3とPY185の調色で作製したT−9は、T−1〜T−4に比べて耐光性が劣り、固溶体形成の有効性が示された。 As shown in Table 4, the colored composition produced using the naphthalocyanine solid solution of the present invention had a small change in chromaticity ΔE even after 96 hours of light irradiation. T-1 exhibited higher light fastness than T-7 in which the pigment component was prepared by toning, and this tendency was the same for T-2 and T-8, which have a similar relationship. For this reason, the formation of a solid solution is effective in improving light resistance. In addition, T-3 and T-4, in which the step of dissolving each pigment once with concentrated sulfuric acid, is slightly inferior to the corresponding T-1 and T-2 in light resistance, and each pigment is dissolved with concentrated sulfuric acid. Performing the process is effective in improving light resistance. T-9 produced by the toning of PB15: 3 and PY185 was inferior to T-1 to T-4 in light resistance, indicating the effectiveness of solid solution formation.
T−1〜4は、T−5〜8と比較すると、彩度および耐光性がどちらも優れている。T−9はT−1〜4に近い彩度を有するが耐光性が明らかに低い。本発明におけるナフタロシアニン固溶体は、彩度および耐光性を高水準で両立している。
T-1 to 4 are superior to T-5 to 8 in both saturation and light fastness. T-9 has a saturation close to T-1 to T-4, but light resistance is clearly low. The naphthalocyanine solid solution according to the present invention has both high saturation and light fastness.
Claims (4)
[一般式(1)中、R1 〜R 24 は水素原子を表し、R 25 〜R40は、それぞれ独立して、水素原子、シアノ基、ニトロ基、アミノ基、炭素数1〜5のアルキル基、炭素数1〜5のアルケニル基、炭素数6〜10のアリール基、−OR41、−COOR42、−CONHR43、−NHCOR44または−SO2NHR45を表す。R41〜R45は、それぞれ独立して、水素原子、炭素数1〜5のアルキル基、炭素数1〜5のアルケニル基、炭素数6〜10のアリール基を表す。X1〜X2は、2つの水素原子または配位子を有していてもよい金属原子を表し、金属原子としてはチタン(Ti)、バナジウム(V)、クロム(Cr)、マンガン(Mn)、鉄(Fe)、コバルト(Co)、ニッケル(Ni)、銅(Cu)、および亜鉛(Zn)からなる群より選ばれる一つである。] Ri Do from the general formula (1) naphthalocyanine pigments represented by Formula (I) and a phthalocyanine pigment (II), the mixing ratio of the naphthalocyanine pigment (I) and a phthalocyanine pigment (II), the pigment (I) a pigment ( A solid solution having a molar ratio of 80 to 99 mol% with respect to II) .
[In the general formula (1), R 1 to R 24 represent a hydrogen atom, and R 25 to R 40 each independently represent a hydrogen atom, a cyano group, a nitro group, an amino group, an alkyl group having 1 to 5 carbon atoms. A alkenyl group having 1 to 5 carbon atoms, an aryl group having 6 to 10 carbon atoms, —OR 41 , —COOR 42 , —CONHR 43 , —NHCOR 44, or —SO 2 NHR 45 . R 41 to R 45 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 10 carbon atoms. X 1 to X 2 represent two hydrogen atoms or a metal atom which may have a ligand, and include titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn) as the metal atom. , Iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and zinc (Zn). ]
A coloring composition comprising the solid solution according to claim 1 and a resin.
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