DE2742066A1 - Kupferphthalocyanin-pigmentzusammensetzungen und verfahren zu deren herstellung - Google Patents
Kupferphthalocyanin-pigmentzusammensetzungen und verfahren zu deren herstellungInfo
- Publication number
- DE2742066A1 DE2742066A1 DE19772742066 DE2742066A DE2742066A1 DE 2742066 A1 DE2742066 A1 DE 2742066A1 DE 19772742066 DE19772742066 DE 19772742066 DE 2742066 A DE2742066 A DE 2742066A DE 2742066 A1 DE2742066 A1 DE 2742066A1
- Authority
- DE
- Germany
- Prior art keywords
- copper
- phthalocyanine
- parts
- compound
- copper phthalocyanine
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims description 50
- 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 title claims description 49
- 238000000034 method Methods 0.000 title claims description 42
- 239000000049 pigment Substances 0.000 title claims description 40
- 230000008569 process Effects 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000012986 modification Methods 0.000 claims description 51
- 230000004048 modification Effects 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 27
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 22
- 239000013078 crystal Substances 0.000 claims description 19
- 238000002441 X-ray diffraction Methods 0.000 claims description 15
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group 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 14
- -1 phthalocyanine radical Chemical class 0.000 claims description 13
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000011368 organic material Substances 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 238000000227 grinding Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 230000000485 pigmenting effect Effects 0.000 claims description 4
- 239000005749 Copper compound Substances 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 3
- 150000001880 copper compounds Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000003607 modifier Substances 0.000 claims description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 239000011733 molybdenum Substances 0.000 claims 1
- 230000002485 urinary effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 14
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
- 239000004202 carbamide Substances 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 8
- 238000002083 X-ray spectrum Methods 0.000 description 8
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000976 ink Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 150000001879 copper Chemical class 0.000 description 4
- 229960003280 cupric chloride Drugs 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000001256 steam distillation Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 208000012641 Pigmentation disease Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 2
- 229920006391 phthalonitrile polymer Polymers 0.000 description 2
- 230000019612 pigmentation Effects 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical compound COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 description 1
- JRBAVVHMQRKGLN-UHFFFAOYSA-N 16,16-dimethylheptadecan-1-amine Chemical compound CC(C)(C)CCCCCCCCCCCCCCCN JRBAVVHMQRKGLN-UHFFFAOYSA-N 0.000 description 1
- DTNSDCJFTHMDAK-UHFFFAOYSA-N 2-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C#N DTNSDCJFTHMDAK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000974482 Aricia saepiolus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
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- 241001648288 Kineosporiaceae Species 0.000 description 1
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- 125000003368 amide group Chemical group 0.000 description 1
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- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
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- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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- DIRCCMJPRSFUPX-UHFFFAOYSA-N copper 2,11,20,29,38,40-hexaza-37,39-diazanidanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1(36),2,4(9),5,7,10(40),11,13,15,17,19,21(38),22(27),23,25,28,30,32,34-nonadecaene-6,25-disulfonic acid Chemical compound [Cu++].OS(=O)(=O)c1ccc2c3nc(nc4[n-]c(nc5nc(nc6[n-]c(n3)c3ccccc63)c3ccc(cc53)S(O)(=O)=O)c3ccccc43)c2c1 DIRCCMJPRSFUPX-UHFFFAOYSA-N 0.000 description 1
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- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
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- 150000002367 halogens Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 150000002605 large molecules Chemical class 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 229920003023 plastic Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
-
- 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
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0026—Crystal modifications; Special X-ray patterns 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3898376A GB1544695A (en) | 1976-09-21 | 1976-09-21 | Pigment composition |
| GB807977 | 1977-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2742066A1 true DE2742066A1 (de) | 1978-03-23 |
Family
ID=26241900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772742066 Ceased DE2742066A1 (de) | 1976-09-21 | 1977-09-19 | Kupferphthalocyanin-pigmentzusammensetzungen und verfahren zu deren herstellung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4135944A (enExample) |
| JP (1) | JPS5339325A (enExample) |
| BR (1) | BR7706279A (enExample) |
| CA (1) | CA1088703A (enExample) |
| CH (1) | CH629237A5 (enExample) |
| DE (1) | DE2742066A1 (enExample) |
| DK (1) | DK415877A (enExample) |
| FR (1) | FR2364954A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010072561A1 (en) * | 2008-12-23 | 2010-07-01 | Solvay Sa | An efficient process for preparation of copper phthalocyanine particles exhibiting epsilon crystallographic form |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1575562A (en) * | 1977-03-19 | 1980-09-24 | Ciba Geigy Ag | Pigment composition |
| DE3025790A1 (de) * | 1980-07-08 | 1982-02-04 | Hoechst Ag, 6000 Frankfurt | Wasserloesliche phthalocyaninverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| JPS57141453A (en) * | 1981-02-25 | 1982-09-01 | Dainippon Ink & Chem Inc | Production of epsilon-type copper phthalocyanine |
| JPS57149358A (en) * | 1981-03-13 | 1982-09-14 | Dainippon Ink & Chem Inc | Production of epsilon type copper phthalocyanine |
| JPS59129718A (ja) * | 1983-01-14 | 1984-07-26 | Sankyo Seiki Mfg Co Ltd | 連続プレス焼入れ移送装置 |
| US4785091A (en) * | 1986-10-31 | 1988-11-15 | Sumitomo Chemical Company, Limited | Process for producing copper phthalocyanine pigment |
| JPS63162476A (ja) * | 1986-12-24 | 1988-07-06 | アヲハタ株式会社 | 組み合わせ容器 |
| JP2536563B2 (ja) | 1987-12-10 | 1996-09-18 | 住友化学工業株式会社 | 新規結晶型銅フタロシアニン |
| DE19652241A1 (de) * | 1996-12-16 | 1998-06-18 | Basf Ag | Verfahren zur Herstellung von metallfreiem Phthalocyanin unter Steuerung der gebildeten Modifikation |
| DE60117627T8 (de) * | 2000-02-04 | 2006-12-07 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Pigmentzusammensetzungen, deren Herstellungsverfahren, Farbmittel sowie gefärbte Artikel |
| KR100822654B1 (ko) | 2000-07-07 | 2008-04-17 | 시바 스페셜티 케미칼스 홀딩 인크. | 안료성 구리 프탈로시아닌 고용체 및 이를 함유하는 투명한 분산물, 이들의 용도 및 당해 분산물의 제조방법 |
| US7211664B2 (en) * | 2004-03-26 | 2007-05-01 | Toyo Ink Mfg. Co., Ltd. | Process for the production of epsilon crystal form copper phthalocyanine |
| JP5205715B2 (ja) * | 2006-06-16 | 2013-06-05 | 東洋インキＳｃホールディングス株式会社 | ε型銅フタロシアニン顔料、その製造方法およびそれを用いた着色組成物 |
| DE102007001851A1 (de) | 2007-01-12 | 2008-07-17 | Clariant International Ltd. | Feinteilige Epsilon-Kupferphthalocyanin-Komposition (Pigment Blau 15:6) zur Verwendung als Pigment |
| CA2673741A1 (en) * | 2007-02-07 | 2008-08-14 | Ciba Holding Inc. | Blue phthalocyanine pigment composition and its preparation |
| DE102007033191A1 (de) | 2007-07-17 | 2009-01-22 | Clariant International Ltd. | Feinteilige epsilon-Kupferphthalocyanin-Pigmentzubereitung |
| TW200918610A (en) * | 2007-07-17 | 2009-05-01 | Clariant Int Ltd | Pigment preparations based on C. I. pigment blue 15:6 |
| JP6498470B2 (ja) * | 2015-02-20 | 2019-04-10 | デクセリアルズ株式会社 | 透明導電膜およびその製造方法 |
| WO2018085346A1 (en) | 2016-11-03 | 2018-05-11 | Sun Chemical Corporation | Pigment compositions containing chlorinated copper phthalocyanine pigments in the gamma crystal form |
| JP7135616B2 (ja) * | 2018-09-07 | 2022-09-13 | コニカミノルタ株式会社 | 静電荷像現像用トナー |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3051721A (en) * | 1959-01-13 | 1962-08-28 | American Cyanamid Co | Pigmentary copper phthalocyanine in the "r" form and its preparation |
| DE1181248B (de) * | 1960-08-09 | 1964-11-12 | Koege Kemisk Vaerk | Blauhaltige Druckfarben |
| DE2026057A1 (enExample) * | 1969-06-03 | 1970-12-17 | ||
| DE2424531A1 (de) * | 1973-05-22 | 1974-12-12 | Ugine Kuhlmann | Neue zubereitungen auf phthalocyaninbasis |
| GB1411880A (en) * | 1972-03-02 | 1975-10-29 | Basf Ag | Production pf phthalocyanine pigments of the epsilon-modification |
| DE2012505B2 (de) * | 1970-03-17 | 1977-09-15 | Bayer Ag, 5090 Leverkusen | Kupfer- und nickelphthalocyanin- mischkondensat-pigmente |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1263684A (en) | 1970-01-23 | 1972-02-16 | Ciba Geigy Uk Ltd | Treatment of pigments |
| GB1388048A (en) * | 1972-03-14 | 1975-03-19 | Ciba Geigy Ag | Phthalocyanine pigments |
| GB1501184A (en) * | 1975-09-09 | 1978-02-15 | Ciba Geigy Ag | Phthalocyanine pigment composition |
-
1977
- 1977-09-19 CH CH1140477A patent/CH629237A5/de not_active IP Right Cessation
- 1977-09-19 CA CA287,015A patent/CA1088703A/en not_active Expired
- 1977-09-19 DE DE19772742066 patent/DE2742066A1/de not_active Ceased
- 1977-09-20 DK DK415877A patent/DK415877A/da not_active Application Discontinuation
- 1977-09-20 BR BR7706279A patent/BR7706279A/pt unknown
- 1977-09-20 US US05/835,072 patent/US4135944A/en not_active Expired - Lifetime
- 1977-09-21 FR FR7728398A patent/FR2364954A1/fr active Granted
- 1977-09-21 JP JP11391077A patent/JPS5339325A/ja active Granted
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3051721A (en) * | 1959-01-13 | 1962-08-28 | American Cyanamid Co | Pigmentary copper phthalocyanine in the "r" form and its preparation |
| DE1181248B (de) * | 1960-08-09 | 1964-11-12 | Koege Kemisk Vaerk | Blauhaltige Druckfarben |
| DE2026057A1 (enExample) * | 1969-06-03 | 1970-12-17 | ||
| DE2012505B2 (de) * | 1970-03-17 | 1977-09-15 | Bayer Ag, 5090 Leverkusen | Kupfer- und nickelphthalocyanin- mischkondensat-pigmente |
| GB1411880A (en) * | 1972-03-02 | 1975-10-29 | Basf Ag | Production pf phthalocyanine pigments of the epsilon-modification |
| DE2424531A1 (de) * | 1973-05-22 | 1974-12-12 | Ugine Kuhlmann | Neue zubereitungen auf phthalocyaninbasis |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010072561A1 (en) * | 2008-12-23 | 2010-07-01 | Solvay Sa | An efficient process for preparation of copper phthalocyanine particles exhibiting epsilon crystallographic form |
| CN102264844A (zh) * | 2008-12-23 | 2011-11-30 | 索尔维公司 | 用于制备呈现ε晶形的酞菁铜颗粒的有效方法 |
| CN102264844B (zh) * | 2008-12-23 | 2014-11-05 | 索尔维公司 | 用于制备呈现ε晶形的酞菁铜颗粒的有效方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5746465B2 (enExample) | 1982-10-04 |
| CA1088703A (en) | 1980-11-04 |
| US4135944A (en) | 1979-01-23 |
| JPS5339325A (en) | 1978-04-11 |
| CH629237A5 (de) | 1982-04-15 |
| BR7706279A (pt) | 1978-05-30 |
| FR2364954B1 (enExample) | 1980-04-18 |
| DK415877A (da) | 1978-03-22 |
| FR2364954A1 (fr) | 1978-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: ASSMANN, E., DIPL.-CHEM. DR.RER.NAT. ZUMSTEIN, F., |
|
| 8131 | Rejection |