JP2006509083A - フタロシアニン顔料配合物 - Google Patents
フタロシアニン顔料配合物 Download PDFInfo
- Publication number
- JP2006509083A JP2006509083A JP2004557989A JP2004557989A JP2006509083A JP 2006509083 A JP2006509083 A JP 2006509083A JP 2004557989 A JP2004557989 A JP 2004557989A JP 2004557989 A JP2004557989 A JP 2004557989A JP 2006509083 A JP2006509083 A JP 2006509083A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- copper phthalocyanine
- pigment
- phthalocyanine pigment
- ethanol
- 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.)
- Pending
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 166
- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 238000009472 formulation Methods 0.000 title claims abstract description 45
- 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 title claims description 11
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims abstract description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 55
- 238000007639 printing Methods 0.000 claims abstract description 51
- 239000002270 dispersing agent Substances 0.000 claims abstract description 38
- 239000002966 varnish Substances 0.000 claims abstract description 23
- 239000006185 dispersion Substances 0.000 claims abstract description 19
- 239000000020 Nitrocellulose Substances 0.000 claims abstract description 18
- 229920001220 nitrocellulos Polymers 0.000 claims abstract description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 7
- -1 copper phthalocyanine sulfonates Chemical class 0.000 claims description 68
- 239000000976 ink Substances 0.000 claims description 61
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000003973 paint Substances 0.000 claims description 10
- 238000010298 pulverizing process Methods 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 7
- 238000004898 kneading Methods 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000011368 organic material Substances 0.000 claims description 4
- 238000004040 coloring Methods 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 32
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
- 235000002639 sodium chloride Nutrition 0.000 description 24
- 239000002904 solvent Substances 0.000 description 21
- 239000001257 hydrogen Substances 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 17
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 17
- 238000000227 grinding Methods 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- 238000000576 coating method Methods 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 13
- 150000004665 fatty acids Chemical class 0.000 description 13
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 239000003760 tallow Substances 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 229920000151 polyglycol Polymers 0.000 description 10
- 239000010695 polyglycol Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000002191 fatty alcohols Chemical class 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000001993 wax Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000003086 colorant Substances 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000009837 dry grinding Methods 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000000518 rheometry Methods 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 125000000542 sulfonic acid group Chemical group 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000010698 whale oil Substances 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
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- 150000002576 ketones Chemical class 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
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- 229910052717 sulfur Inorganic materials 0.000 description 4
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 3
- 125000001807 C7-C38 aralkyl group Chemical group 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 125000000524 functional group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 125000004193 piperazinyl group Chemical group 0.000 description 3
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- 150000003141 primary amines Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- 125000001272 (C1-C4)-alkylene-phenyl group Chemical group 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
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- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical class [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000011355 unsaturated synthetic resin Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/32—Cationic phthalocyanine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
- C09B67/0016—Influencing the physical properties by treatment with a liquid, e.g. solvents of phthalocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0032—Treatment of phthalocyanine pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0035—Mixtures of phthalocyanines
-
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/16—Writing inks
- C09D11/17—Writing inks characterised by colouring agents
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
- G03G9/0918—Phthalocyanine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Cosmetics (AREA)
Abstract
Description
a)動的粘度及びチキソトロピーを28重量%の銅フタロシアニン顔料配合物(乾燥)、9重量%のニトロセルロース(ISO 14446,規格27Aに従う)、62.3重量%のエタノール及び0.7重量%の酢酸エチルからなる顔料分散液中23℃の温度で回転粘度計を用いて測定するとして、動的粘度が180mPas以下、好ましくは165mPas以下、特に150mPas以下及び/またはチキソトロピーが800Pa/s以下、好ましくは600Pa/s以下、特に450Pa/s以下であること、及び
b)75〜85重量%のエタノール及び9〜11重量%のニトロセルロース(ISO 14446,規格27A及び30Aに従う)を2:7.5の比で含有するエタノール/ニトロセルロースグラビアワニス及び印刷インクの総重量に基づいて6.6重量%以下、好ましくは6.5重量%以下、特に6.4重量%以下の銅フタロシアニン顔料配合物(乾燥)からなる印刷インクが対応色相のDIN 53235に従う1/3標準色深みに達するような色の濃さであること
を特徴とする銅フタロシアニン顔料配合物を提供する。
に相当する。
を有する基である;または
Tは上記と同義であり、gは1〜6、好ましくは2〜4の数であり、A1は式(IIb):
を有する基である;または
Tは上記と同義であり、gは1〜4の数であり、A1は式(IId):
を有する基である;または
Tは上記と同義であり、所望により更に1〜3個のスルホン酸基で置換されていてもよく、gは1〜4、好ましくは1〜3の数であり、A1は式(IIe):
を有するフタルイミドメチレン基である;または
Tは上記と同義であり、gは1〜4の数であり、A1は式(IIf):
を有するo−スルホベンズイミドメチレン基である;または
Tは上記と同義であり、gは1〜4の数であり、A1は式(IIg):
を有する基である;または
Tは上記と同義であり、gは1〜4の数であり、A1は式(IIh):
−G−O−A4+ (IIh)
(式中、Gは上記と同義であり;A4+はホスホニウムイオン、または置換または未置換アンモニウムイオンである)
を有する基である]
を有する銅フタロシアニンを主成分とするものである。
N+R9R10R11R12
[式中、
置換基R9、R10、R11及びR12は同一でも異なっていてもよく、水素、フェニル、C1−4アルキレン−フェニル、C5−30シクロアルキル、C2−30アルケニル、または直鎖もしくは分枝鎖C1−30アルキルであり、前記したフェニル環、C1−4アルキレン−フェニル基、C5−30シクロアルキル基、C2−30アルケニル基及びC1−30アルキル基は1個以上(例えば、1〜4個)のCl、Br、CN、NH2、OH、C6H5、1〜3個のC1−20アルコキシ基で置換されたC6H5、カルバモイル、カルボキシル、C2−4アシル、C1−8アルキル、NR2R3(式中、R2及びR3は上記と同義である)及びC1−4アルコキシ(例えば、メトキシまたはエトキシ)からなる群から選択される置換基で置換され得、またはアルキル基及びアルケニル基は過フッ素化または部分的にフッ素化され得るか、または式(1b):
−[X−Y]h−R3 (1b)
(式中、hは0〜100、好ましくは0〜20、より好ましくは0〜5の数であり;XはC2−6アルキレン基、C5−7シクロアルキレン基またはその組合せであり、前記した基は1〜4個のC1−4アルキル基、ヒドロキシ基、C1−4アルコキシ基、C1−4ヒドロキシアルキル基及び/または1〜2個の別のC5−7シクロアルキル基であり、h>1のときには前記した定義の組合せであり得;Yは−O−、
を有する基であり;または
置換基R9及びR10はアンモニウムイオンの窒素原子と一緒になって、所望ならばO、N及びSから選択される追加ヘテロ原子またはカルボニル基を含み、所望ならば1又は2個の縮合飽和、不飽和または芳香族の炭素環式またはヘテロ環式環を有する、例えばピロリドン、イミダゾリジン、ヘキサメチレンイミン、ピペリジン、ピペラジンまたはモルホリンタイプの5〜7員飽和または不飽和環系を形成し得、前記環系及び適当な場合に縮合される環はOH、NH2、フェニル、CN、Cl、Br、C1−4アルキル、C1−4アルコキシ、C2−4アシル及びカルバモイルからなる群から選択される1〜3個の基で置換されていてもよく;または
置換基R9、R10及びR11はアンモニウムイオンの窒素原子と一緒になって、所望ならばO、N及びSから選択される追加ヘテロ原子またはカルボニル基を含み、所望ならば1〜2個の縮合飽和、不飽和または芳香族の炭素環式またはヘテロ環式環を有する、例えばピロール、イミダゾール、ピリジン、ピコリン、ピラジン、キノリンまたはイソキノリンタイプの5〜7員芳香族環系を形成し得、前記環系及び適当な場合に縮合される環はOH、NH2、フェニル、CN、Cl、Br、C1−4アルキル、C1−4アルコキシ、C2−4アシル及びカルバモイルからなる群から選択される1〜3個の基で置換されていてもよい]
を有するイオンである。
R15、R16、R17及びR18は相互に独立して水素または式(Id):
−[(CH(R80)−)jO]k−R81 (Id)
{式中、jは2または3の数であり;kは1〜100の数であり;基R80は水素、C1−4アルキル、またはk>1のときにはその組合せであり得;基R81は水素、C1−4アルキル、または基−(CH(R82)−)iNH2(ここで、iは2または3であり、基R82は水素、C1−4アルキルまたはその組合せである)である}
を有する(ポリ)アルキレンオキシ基であり、
qは1〜10、好ましくは1〜5の数であり、
pは1〜5の数であり、ただしp≦q+1であり、
A20は直鎖もしくは分枝鎖C2−6アルキレン基であるか、q>1のときには直鎖もしくは分枝鎖C2−6アルキレン基の組合せでもあり得る]
を有するアンモニウムイオンの1/p当量も適当である。
R40はC6−30アルキル(好ましくは、線状C8−20アルキル)またはC6−30アルケニル(好ましくは、線状)であり、
R41は自由原子価、水素、C1−30アルキル、C2−30アルケニル、C3−30シクロアルキル、C6−14アリールまたはC7−38アルアルキルであり、
R42、R43及びR45は同一でも異なっていてもよく、C1−6アルキル(好ましくは、メチル)、C3−30シクロアルキル、C6−14アリールまたはC7−38アルアルキルであり、
R44は、R41及びR44が同時に自由原子価のことはない条件で自由原子価、水素、C1−6アルキル(好ましくは、メチル)、C3−30シクロアルキル、C6−14アリールまたはC7−38アルアルキルであり、
rは2、またはR41またはR44が自由原子価のときには1の数であり、
A10はC1−12アルキレンまたはC2−14アルケニレンであり、好ましくは2〜4個、特に3個の炭素原子を含み、または
R41及びR43はこれらが結合している2個の窒素原子及びA10と一緒になって環、好ましくはピペラジニルを形成し、及び/または
R44及びR45はこれらが結合している窒素原子と一緒になって環、好ましくはピペリジニル、モルホリニル、ピペラジニルまたはN−(C1−6アルキル)ピペラジニルを形成する)
を有するジアミン誘導アンモニウムイオンの1/r当量である。
A+は、好ましくは例えばメチル化または塩化ベンジルとの反応により上記油脂から得られるアルコキシル化脂肪アミンまたはアミンから誘導される第4級アンモニウムイオンであり、例えばステアリルベンジル−またはココアルキル−ジメチル−ベンジルアンモニウムまたは−2,4−ジクロロベンジルアンモニウム、ヘキサデシル−,ステアリル−,ドデシル−またはセチルトリメチルアンモニウム、ジ水素化タローアルキル、ジココアルキル−またはジステアリルジメチルアンモニウム、オレイル−またはココジ(2−ヒドロキシエチル)メチルアンモニウム、水素化ポリオキシエチレン(15)タローメチルアンモニウム、N,N,N’,N’,N’−ペンタメチル−N−タロー1,3−プロパンジアンモニウム、過メチル化N−ステアリルジエチレントリアミン、過メチル化N−ステアリルトリエチレンテトラミン、N−(3−ドデシルオキシ−2−ヒドロキシプロピル)オクタデシルジメチルアンモニウム、メチルトリ(2−オクチル)アンモニウム、N,N−ジ(β−ステアロイルエチル)−N,N−ジメチルアンモニウム、ラウリルピリジニウム、2−ヒドロキシ−[5−クロロ−、5−イソオクチル、5−t−ブチル−またはn−ノニル−]−1,3−キシレン−ビスピリジニウム、2−メトキシ−5−イソオクチル−1,3−キシリレン−ビスピリジニアム、2−ヒドロキシ−5−イソオクチル−1,3−キシリレン−ビスキノリニウム、2−ヒドロキシ−5−イソオクチル−1,3−キシリレン−ビスイソキノリニウムまたはベヘニルトリメチルアンモニウムである;または
A+は、好ましくはヘキシデシルトリブチルホスホニウム、エチルトリオクチルホスホニウムまたはテトラブチルホスホニウムのようなホスホニウムイオンである;
前記した第4級アンモニウム化合物またはホスホニウム化合物の元のアニオンとして例えばハライド、スルフェート、アルコキシスルフェート、アルコキシホスフェートを使用し得る。
5 非常に流動性、
4 液体、
3 粘性、
2 僅かに硬化、
1 硬化。
a) 28%印刷インク濃厚物の調製
プッシュオン蓋を備えた250ml容量のPEプラスチック製ビーカー(φ55mm×125mm)に直径1.0〜1.25mmのジルコニウム混合酸化物ビーズ(69% ZrO2,31% 非晶質SiO2)(150g)を充填し、顔料配合物(28.00g)、25.0%のニトロセルロースA500(ISO 14 446,27Aに従う)及び75.0%の無水エタノールからなるグラビアワニス(1)(36.00g)及び98.0%の99.9% エタノール及び2.0%の99.9% 酢酸エチルからなる溶剤混合物(36.00g)を秤量して添加する。混合物をヘーメルに所在のLAU GmbH製DAS 200K分散装置において660rpmで楕円振とう運動により45分間分散させる(換気段階1、すなわち分散中の温度は40℃を超えない)。ジルコニウム混合酸化物ビーズを篩を用いて分離した。
分散液濃厚物を室温(21〜25℃)で24時間保存し、23℃で30分間状態調整した後測定する。分散液濃厚物の粘度及びチキソトロピーはカールスルーエに所在のHaake製RS75またはRS1回転粘度計を用いて測定する。測定計器はDIN 53019/ISO3219に従う同軸円筒システムである。測定中、計器中のサンプルは23±0.1℃に状態調整する。線形剪断率ランプは少なくとも50直線勾配させながら180秒で0から250sec−1、その直後更に少なくとも50直線勾配させながら180秒で250から0sec−1への直線的ランプを行う。粘度値は測定ポイントに内挿することにより200sec−1で上行ブランチで測定する。チキソトロピー値はランプの上行ブランチ及び下行ブランチにおける剪断率(sec−1)に対する剪断ストレス(Pa)の曲線の下の面積の差として測定し、Pa/secで表す。
28%印刷インク濃厚物(セクションa)参照)を無水エタノール(1部)及び30.0%のISO 14446,規格30Aに従うニトロセルロースA 400(65% エタノール含有)、4.0%のGenomoll 140(フタル酸ジブチル)、8.0%の1−メトキシ−2−プロパノール及び58.0%の無水エタノールからなるグラビアワニス(2)(1部)の混合物を用いて10%顔料濃度とする。この印刷インクを、彫刻深さ29μmの印刷板を用いてプリントを作成し、色の濃さを1/3標準色深みと比較して測定する。その後、印刷インク濃厚物に添加する(1部の無水エタノール及び1部のグラビアワニス(2)からなる)グラビアワニス(3)の量を1/3標準色深みに達するまで増加させる。それぞれ28%印刷インク濃厚物を出発分とする。
印刷基板:Algro Finesse 80g/m2、
印刷速度:125スケール区分、
印刷板:彫刻深さ29μmの板、
彫刻板の29μmフィールドの詳細:
X−対角線:178μm、
y−対角線:126μm、
深さ:29μm、
ハーフトーン:70%印刷面積、
角度:30°、
容量面積:11.8ml/m2。
粗なフタロシアニンブルー15顔料(550部)、硫酸ナトリウム(550部)及びジエチレングリコール(120部)を鉄棒を有する振動ミルを用いて90分間粉砕する。練り顔料を5% 水性硫酸(4000部)中90℃で2時間撹拌する。懸濁液を濾過し、塩がなくなるまで水で洗浄する。こうして、顔料の60.4%プレスケーキ(740.6部)を得る。
上記A)からの60.4%プレスケーキ(165.6部)をtert−アミルアルコール(620部)及び水(350.2部)中に懸濁させる。水酸化ナトリウケム(4.2部)及び銅フタロシアニン基1個あたり1.5スルホン酸基の平均置換度を有する銅フタロシアニンスルホン酸の水性32.4%プレスケーキ(15.4部)を添加し、懸濁液を150℃に加熱する。150℃で2時間撹拌した後アミルアルコールを留去させ、懸濁液を濾過し、プレスケーキを塩がなくなるまで洗浄する。こうして、フタロシアニン顔料配合物の40.4%プレスケーキ(239部)を得る。
B)からのプレスケーキ(59部)を80℃で乾燥する。こうして、フタロシアニン顔料配合物(23.8部)を得る。
B)からのプレスケーキ(79.7部)を水(250部)中でペースト化し、80℃に加熱する。銅フタロシアニン基1個あたり1.5スルホン酸基の平均置換度を有する銅フタロシアニンスルホン酸の水性32.4%プレスケーキ(7.7部)を添加し、懸濁液を80℃で1時間撹拌する。懸濁液を濾過し、プレスケーキを洗浄し、乾燥する。こうして、フタロシアニン顔料配合物(32.6部)を得る。
3つの標準の市販品並びに実施例1C及びDの結果を下表に示す。
Claims (10)
- 銅フタロシアニン顔料、及び銅フタロシアニンスルホン酸及び銅フタロシアニンスルホン酸塩からなる群から選択される少なくとも1つの顔料分散剤を含み、
a)動的粘度及びチキソトロピーを28重量%の銅フタロシアニン顔料配合物(乾燥)、9重量%のニトロセルロース(ISO 14446,規格27Aに従う)、62.3重量%のエタノール及び0.7重量%の酢酸エチルからなる顔料分散液中23℃の温度で回転粘度計を用いて測定するとして、動的粘度が180mPas以下及び/またはチキソトロピーが800Pa/s以下であること、及び
b)75〜85重量%のエタノール及び9〜11重量%のニトロセルロース(ISO 14446,規格27A及び30Aに従う)を2:7.5の比で含有するエタノール/ニトロセルロースグラビアワニス及び印刷インクの総重量に基づいて6.6重量%以下の銅フタロシアニン顔料配合物(乾燥)からなる印刷インクが対応色相のDIN 53235に従う1/3標準色深みに達するような色の濃さであること
を特徴とする銅フタロシアニン顔料配合物。 - 動的粘度が150mPas以下及び/またはチキソトロピーが600Pa/s以下である請求の範囲第1項に記載の銅フタロシアニン顔料配合物。
- 75〜85重量%のエタノール及び9〜11重量%のニトロセルロース(ISO 14 446,規格27A及び30Aに従う)を2:7.5の比で含有するエタノール/ニトロセルロースグラビアワニス及び印刷インクの総重量に基づいて6.5重量%以下の銅フタロシアニン顔料配合物(乾燥)からなる印刷インクが対応色相のDIN 53235に従う1/3標準色深みに達するような色の濃さである請求の範囲第1項または第2項に記載の銅フタロシアニン顔料配合物。
- a)動的粘度が150mPas以下及びチキソトロピーが450Pa/s以下である、及び
b)75〜85重量%のエタノール及び9〜11重量%のニトロセルロース(ISO 14446,規格27A及び30Aに従う)を2:7.5の比で含有するエタノール/ニトロセルロースグラビアワニス及び印刷インクの総重量に基づいて6.4重量%以下の銅フタロシアニン顔料配合物(乾燥)からなる印刷インクが対応色相のDIN 53235に従う1/3標準色深みに達するような色の濃さである
請求の範囲第1項に記載の銅フタロシアニン顔料配合物。 - 銅フタロシアニン顔料が0〜6重量%の塩素を含む請求の範囲第1項〜第5項のいずれか1項に記載の銅フタロシアニン顔料配合物。
- 銅フタロシアニン顔料に基づいて0.1〜25重量%、好ましくは0.5〜20重量%の銅フタロシアニンスルホン酸及びその塩からなる群から選択される顔料分散剤を含む請求の範囲第1項〜第6項のいずれか1項に記載の銅フタロシアニン顔料配合物。
- 粗な銅フタロシアニン顔料を乾式粉砕及び塩混練からなる群から選択される方法により微粉砕してプレ顔料を形成した後、このプレ顔料を水と有機溶剤の混合物中高温及びアルカリpHで銅フタロシアニンスルホン酸及び銅フタロシアニンスルホン酸塩からなる群から選択される少なくとも1つの顔料分散剤の存在下で仕上げ処理にかけることを含む請求の範囲第1項〜第7項のいずれか1項に記載の銅フタロシアニン顔料配合物の製造方法。
- プラスチック、樹脂、ワニス、ペイント、電子写真用途トナー及び現像剤、エレクトレット材料、カラーフィルター、印刷インクを含めたインク及びシードのような高分子量有機材料を着色するための請求の範囲第1項〜第7項のいずれか1項に記載の銅フタロシアニン顔料配合物の使用。
- 0.05〜30重量%の請求の範囲第1項〜第7項のいずれか1項に記載の銅フタロシアニン顔料配合物を含む高分子量有機材料。
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| DE10257498A DE10257498A1 (de) | 2002-12-10 | 2002-12-10 | Verfahren zur Herstellung von Phthalocyaninpigmentzubereitungen |
| PCT/EP2003/013690 WO2004052997A1 (de) | 2002-12-10 | 2003-12-04 | Phthalocyaninpigmentzubereitungen |
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2003
- 2003-11-27 CN CNB2003801014478A patent/CN1329455C/zh not_active Expired - Fee Related
- 2003-11-27 EP EP03782237A patent/EP1572809B2/de not_active Expired - Lifetime
- 2003-11-27 WO PCT/EP2003/013362 patent/WO2004052996A1/de not_active Ceased
- 2003-11-27 JP JP2004557941A patent/JP4738813B2/ja not_active Expired - Fee Related
- 2003-11-27 ES ES03782237T patent/ES2266888T5/es not_active Expired - Lifetime
- 2003-11-27 KR KR1020057010444A patent/KR101009900B1/ko not_active Expired - Fee Related
- 2003-11-27 DE DE50303749T patent/DE50303749D1/de not_active Expired - Lifetime
- 2003-11-27 US US10/539,033 patent/US7459016B2/en not_active Expired - Lifetime
- 2003-12-04 DE DE50310083T patent/DE50310083D1/de not_active Expired - Lifetime
- 2003-12-04 ES ES03785732T patent/ES2308009T3/es not_active Expired - Lifetime
- 2003-12-04 WO PCT/EP2003/013690 patent/WO2004052997A1/de not_active Ceased
- 2003-12-04 US US10/539,034 patent/US7255734B2/en not_active Expired - Fee Related
- 2003-12-04 KR KR1020057010449A patent/KR20050085476A/ko not_active Ceased
- 2003-12-04 EP EP03785732A patent/EP1572810B8/de not_active Expired - Lifetime
- 2003-12-04 CN CNB2003801014482A patent/CN1326951C/zh not_active Expired - Fee Related
- 2003-12-04 JP JP2004557989A patent/JP2006509083A/ja active Pending
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| JPS60188470A (ja) * | 1984-03-08 | 1985-09-25 | Sumitomo Chem Co Ltd | 銅フタロシアニン顔料の製造法 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006509081A (ja) * | 2002-12-10 | 2006-03-16 | クラリアント・ゲーエムベーハー | フタロシアニン顔料配合物の製造方法 |
| JP2006096922A (ja) * | 2004-09-30 | 2006-04-13 | Toyo Ink Mfg Co Ltd | 印刷インキ |
| JP2006160805A (ja) * | 2004-12-03 | 2006-06-22 | Toyo Ink Mfg Co Ltd | 着色組成物 |
| JP2016505866A (ja) * | 2012-11-14 | 2016-02-25 | セイジ・エレクトロクロミクス,インコーポレイテッド | バスバーのためのカラーマッチングさせたコーティング |
| JP2017082100A (ja) * | 2015-10-28 | 2017-05-18 | 旭化成株式会社 | ポリオキシメチレン樹脂組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1572810B1 (de) | 2008-07-02 |
| JP4738813B2 (ja) | 2011-08-03 |
| EP1572809B2 (de) | 2009-11-18 |
| KR20050084218A (ko) | 2005-08-26 |
| ES2308009T3 (es) | 2008-12-01 |
| US7459016B2 (en) | 2008-12-02 |
| WO2004052997A1 (de) | 2004-06-24 |
| EP1572810B8 (de) | 2008-08-13 |
| KR20050085476A (ko) | 2005-08-29 |
| DE10257498A1 (de) | 2004-07-01 |
| DE50310083D1 (de) | 2008-08-14 |
| EP1572810A1 (de) | 2005-09-14 |
| US7255734B2 (en) | 2007-08-14 |
| KR101009900B1 (ko) | 2011-01-20 |
| US20060137573A1 (en) | 2006-06-29 |
| DE50303749D1 (de) | 2006-07-20 |
| ES2266888T5 (es) | 2010-02-22 |
| EP1572809B1 (de) | 2006-06-07 |
| ES2266888T3 (es) | 2007-03-01 |
| CN1705718A (zh) | 2005-12-07 |
| CN1326951C (zh) | 2007-07-18 |
| CN1705719A (zh) | 2005-12-07 |
| WO2004052996A1 (de) | 2004-06-24 |
| CN1329455C (zh) | 2007-08-01 |
| EP1572809A1 (de) | 2005-09-14 |
| US20060112856A1 (en) | 2006-06-01 |
| JP2006509081A (ja) | 2006-03-16 |
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