DE69629541T2 - Verfahren zur Herstellung transparenter Chincridon-Pigmente durch Säure-Schwellung vorgemahlener Chinacridon Sub-pigmente in Gegenwart einer organische Flüssigkeit - Google Patents
Verfahren zur Herstellung transparenter Chincridon-Pigmente durch Säure-Schwellung vorgemahlener Chinacridon Sub-pigmente in Gegenwart einer organische Flüssigkeit Download PDFInfo
- Publication number
- DE69629541T2 DE69629541T2 DE69629541T DE69629541T DE69629541T2 DE 69629541 T2 DE69629541 T2 DE 69629541T2 DE 69629541 T DE69629541 T DE 69629541T DE 69629541 T DE69629541 T DE 69629541T DE 69629541 T2 DE69629541 T2 DE 69629541T2
- Authority
- DE
- Germany
- Prior art keywords
- quinacridone
- pigment
- sulfuric acid
- weight
- pigments
- 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.)
- Expired - Fee Related
Links
- 239000000049 pigment Substances 0.000 title claims description 111
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 title claims description 44
- 238000000034 method Methods 0.000 title claims description 40
- 230000008569 process Effects 0.000 title claims description 17
- 239000007788 liquid Substances 0.000 title claims description 12
- 239000002253 acid Substances 0.000 title description 41
- 230000008961 swelling Effects 0.000 title description 12
- 238000004519 manufacturing process Methods 0.000 title description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 36
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 28
- 239000000843 powder Substances 0.000 claims description 21
- 239000002002 slurry Substances 0.000 claims description 17
- 239000006104 solid solution Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- -1 acridone compound Chemical class 0.000 claims description 10
- 239000003966 growth inhibitor Substances 0.000 claims description 9
- KSLLMGLKCVSKFF-UHFFFAOYSA-N 5,12-dihydroquinolino[2,3-b]acridine-6,7,13,14-tetrone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C(=O)C(C(=O)C1=CC=CC=C1N1)=C1C2=O KSLLMGLKCVSKFF-UHFFFAOYSA-N 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 7
- YEIYQKSCDPOVNO-UHFFFAOYSA-N 5,8,9,12-tetrahydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=CC=C2C(=O)C(C=C2N3)=C1C=C2C(=O)C1=C3C=CCC1 YEIYQKSCDPOVNO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- SJIQTGOBEGYKSI-UHFFFAOYSA-N 2-[(1,3-dioxoisoindol-2-yl)methyl]-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC=C(NC=2C(=CC3=C(C(C4=CC=CC=C4N3)=O)C=2)C2=O)C2=C1 SJIQTGOBEGYKSI-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 4
- XPZQBGDNVOHQIS-UHFFFAOYSA-N 2,9-dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(Cl)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)Cl)N1)C1=C2 XPZQBGDNVOHQIS-UHFFFAOYSA-N 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 2
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 claims description 2
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 claims description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 2
- 239000003760 tallow Substances 0.000 claims description 2
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 claims description 2
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002245 particle Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- 239000012071 phase Substances 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000003973 paint Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000227 grinding Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229940037003 alum Drugs 0.000 description 7
- 238000003801 milling Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000005070 ripening Effects 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007730 finishing process Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 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 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002987 primer (paints) Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 238000006424 Flood reaction Methods 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000010951 particle size reduction Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 230000003867 tiredness Effects 0.000 description 1
- 208000016255 tiredness Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
- 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
- C09B67/0022—Wet grinding of pigments
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/36—Pearl essence, e.g. coatings containing platelet-like pigments for pearl lustre
-
- 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
- C09B67/0017—Influencing the physical properties by treatment with an acid, H2SO4
-
- 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
- C09B67/0036—Mixtures of quinacridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Developing Agents For Electrophotography (AREA)
- Optical Filters (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US742695P | 1995-11-21 | 1995-11-21 | |
| US7426 | 1995-11-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69629541D1 DE69629541D1 (de) | 2003-09-25 |
| DE69629541T2 true DE69629541T2 (de) | 2004-04-08 |
Family
ID=21726088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69629541T Expired - Fee Related DE69629541T2 (de) | 1995-11-21 | 1996-11-12 | Verfahren zur Herstellung transparenter Chincridon-Pigmente durch Säure-Schwellung vorgemahlener Chinacridon Sub-pigmente in Gegenwart einer organische Flüssigkeit |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0775703B1 (enExample) |
| JP (1) | JPH09176507A (enExample) |
| KR (1) | KR100420908B1 (enExample) |
| CN (1) | CN1071364C (enExample) |
| CA (1) | CA2190719A1 (enExample) |
| DE (1) | DE69629541T2 (enExample) |
| MX (1) | MX9605696A (enExample) |
| TW (1) | TW353677B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100480336C (zh) * | 2000-07-07 | 2009-04-22 | 西巴特殊化学品控股有限公司 | 颜料酞菁铜固溶体以及包含它的透明分散体 |
| WO2009019180A2 (de) * | 2007-08-03 | 2009-02-12 | Basf Se | Verfahren zur formierung von organischen pigmenten |
| JP2009108199A (ja) * | 2007-10-30 | 2009-05-21 | Fujifilm Corp | 水分散体、それを用いた記録液、画像形成方法、及び画像形成装置、並びに水分散体の製造方法及びそれにより得られるインクジェット用インク |
| CN107446374A (zh) * | 2017-08-01 | 2017-12-08 | 南京工业大学 | 一类喹吖啶酮多季铵盐衍生物及其制备方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2402167A (en) | 1942-12-24 | 1946-06-18 | Du Pont | Physical form of organic pigment |
| US3051720A (en) | 1958-12-29 | 1962-08-28 | Du Pont | Production of phthalocyanine pigments |
| US3030370A (en) | 1959-08-24 | 1962-04-17 | Du Pont | Particle size reduction of quinacridone and phthalocyanine pigments |
| US3326918A (en) | 1965-10-21 | 1967-06-20 | Du Pont | Process for the preparation of beta phase quinacridone |
| US3607336A (en) | 1969-07-09 | 1971-09-21 | Du Pont | Process for making solid solutions |
| US3681100A (en) | 1970-10-08 | 1972-08-01 | Du Pont | Light stable orange pigment based on quinacridone solid solution |
| DE2342907A1 (de) * | 1973-08-24 | 1975-05-15 | Sun Chemical Corp | Verfahren zur aufbereitung von chinacridon durch saeurequellung |
| US4088506A (en) * | 1976-12-08 | 1978-05-09 | E. I. Du Pont De Nemours And Company | Process for preparing pigmentary quinacridone using low-salt milling |
| CA1144927A (en) * | 1978-12-10 | 1983-04-19 | Wilfried G. Holtje | Light stable quinacridonequinone yellow pigment |
| US4247695A (en) * | 1979-02-26 | 1981-01-27 | E. I. Du Pont De Nemours And Company | Process for preparation of quinacridone pigments using moderately concentrated acid |
| US4298398A (en) * | 1980-08-28 | 1981-11-03 | E. I. Du Pont De Nemours And Company | Process for converting premilled crude quinacridone to pigmentary form |
| US4455173A (en) * | 1981-07-07 | 1984-06-19 | E. I. Du Pont De Nemours And Company | Preparation of pigmentary form of quinacridone pigments |
| CA1199026A (en) * | 1982-06-21 | 1986-01-07 | Edward E. Jaffe | Preparation of pigmentary grade pigment from crude pigment |
| US4541872A (en) | 1982-06-21 | 1985-09-17 | Ciba-Ceigy Corporation | Preparation of pigmentary grade pigment from crude pigment |
| JPH0778179B2 (ja) | 1986-12-11 | 1995-08-23 | 住友化学工業株式会社 | ジオキサジンバイオレツト顔料の製造方法 |
| US4895949A (en) * | 1988-06-20 | 1990-01-23 | Ciba-Geigy Corporation | Process for preparation of quinacridone solid solutions |
| JPH041462A (ja) | 1990-04-13 | 1992-01-06 | Nissan Motor Co Ltd | 燃料噴射弁の弁体構造 |
| DE4403231A1 (de) * | 1994-02-03 | 1995-08-10 | Hoechst Ag | Verfahren zur Herstellung von Chinacridonpigmenten |
-
1996
- 1996-10-29 TW TW085113152A patent/TW353677B/zh active
- 1996-11-12 EP EP96810774A patent/EP0775703B1/en not_active Expired - Lifetime
- 1996-11-12 DE DE69629541T patent/DE69629541T2/de not_active Expired - Fee Related
- 1996-11-19 MX MX9605696A patent/MX9605696A/es unknown
- 1996-11-19 CA CA002190719A patent/CA2190719A1/en not_active Abandoned
- 1996-11-20 KR KR1019960055745A patent/KR100420908B1/ko not_active Expired - Fee Related
- 1996-11-20 CN CN96123347A patent/CN1071364C/zh not_active Expired - Fee Related
- 1996-11-21 JP JP8309828A patent/JPH09176507A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0775703A2 (en) | 1997-05-28 |
| CN1158874A (zh) | 1997-09-10 |
| JPH09176507A (ja) | 1997-07-08 |
| EP0775703A3 (en) | 1997-06-04 |
| EP0775703B1 (en) | 2003-08-20 |
| CN1071364C (zh) | 2001-09-19 |
| DE69629541D1 (de) | 2003-09-25 |
| CA2190719A1 (en) | 1997-05-22 |
| TW353677B (en) | 1999-03-01 |
| KR970027227A (ko) | 1997-06-24 |
| MX9605696A (es) | 1997-05-31 |
| KR100420908B1 (ko) | 2005-06-16 |
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