JPS5823858A - 顔料形態のキナクリドン顔料の製造方法 - Google Patents
顔料形態のキナクリドン顔料の製造方法Info
- Publication number
- JPS5823858A JPS5823858A JP11631282A JP11631282A JPS5823858A JP S5823858 A JPS5823858 A JP S5823858A JP 11631282 A JP11631282 A JP 11631282A JP 11631282 A JP11631282 A JP 11631282A JP S5823858 A JPS5823858 A JP S5823858A
- Authority
- JP
- Japan
- Prior art keywords
- quinacridone
- parts
- product
- pigment
- crude
- 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.)
- Granted
Links
- 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 78
- 239000000049 pigment Substances 0.000 title description 71
- 238000004519 manufacturing process Methods 0.000 title description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 74
- 239000002245 particle Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 46
- 239000007788 liquid Substances 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000006104 solid solution Substances 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 11
- TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical group N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 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 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 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 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 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 2
- BUGUFPOZAOTHBP-UHFFFAOYSA-N C=12C(=O)C3=CC=CC=C3NC2=CC=CC=1NC1=CC=CC=C1 Chemical compound C=12C(=O)C3=CC=CC=C3NC2=CC=CC=1NC1=CC=CC=C1 BUGUFPOZAOTHBP-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000000498 ball milling Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 81
- 229910000831 Steel Inorganic materials 0.000 description 23
- 239000000843 powder Substances 0.000 description 23
- 239000010959 steel Substances 0.000 description 23
- 239000002002 slurry Substances 0.000 description 22
- 238000003801 milling Methods 0.000 description 20
- 238000000227 grinding Methods 0.000 description 19
- 230000000694 effects Effects 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- 239000003973 paint Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 229920001187 thermosetting polymer Polymers 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003966 growth inhibitor Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000009837 dry grinding Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002966 varnish Substances 0.000 description 5
- 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 description 4
- 239000000654 additive Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- BFEJTCHFLJECJN-UHFFFAOYSA-N 4,11-Dichloro-5,12-dihydroquino[2,3-b]acridine-7,14-dione Chemical compound N1C2=C(Cl)C=CC=C2C(=O)C2=C1C=C(C(C=1C=CC=C(C=1N1)Cl)=O)C1=C2 BFEJTCHFLJECJN-UHFFFAOYSA-N 0.000 description 1
- RXXVCHIRRGNGCO-UHFFFAOYSA-N 5-methyl-12h-quinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3N(C)C1=C2 RXXVCHIRRGNGCO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- -1 aluminum quinacridone sulfonates Chemical class 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 210000003323 beak Anatomy 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 description 1
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28119481A | 1981-07-07 | 1981-07-07 | |
| US368321 | 1982-04-16 | ||
| US281194 | 2005-11-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5823858A true JPS5823858A (ja) | 1983-02-12 |
| JPH0358389B2 JPH0358389B2 (enrdf_load_stackoverflow) | 1991-09-05 |
Family
ID=23076338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11631282A Granted JPS5823858A (ja) | 1981-07-07 | 1982-07-06 | 顔料形態のキナクリドン顔料の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5823858A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02180884A (ja) * | 1988-12-29 | 1990-07-13 | Toyo Ink Mfg Co Ltd | 新規な化合物，およびそれを用いた顔料並びに電子写真感光体 |
| JPH09165528A (ja) * | 1995-10-12 | 1997-06-24 | Dainippon Ink & Chem Inc | インダンスロンブルー顔料又はカルバゾールジオキサジンバイオレット顔料の製造方法 |
| WO2019187058A1 (ja) * | 2018-03-30 | 2019-10-03 | 大日精化工業株式会社 | キナクリドン固溶体顔料の製造方法、顔料分散液及びインクジェット用インキ |
| US11535755B2 (en) | 2016-10-28 | 2022-12-27 | Dainichiseika Color & Chemicals Mfg. Co.. Ltd. | Method for producing quinacridone solid solution pigment, pigment dispersion, and inkjet ink |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857400A (en) * | 1955-09-19 | 1958-10-21 | Du Pont | Pigment production |
| GB900757A (en) * | 1959-07-13 | 1962-07-11 | Ciba Ltd | Process for the manufacture of quinacridone pigments in a finely divided form |
| US3264300A (en) * | 1963-04-30 | 1966-08-02 | American Cyanamid Co | 2, 9-dimethylquinacridone in a "yellow" crystalline form |
| US3598625A (en) * | 1967-11-14 | 1971-08-10 | Cities Service Co | Production of pigmentary grade colorants |
-
1982
- 1982-07-06 JP JP11631282A patent/JPS5823858A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857400A (en) * | 1955-09-19 | 1958-10-21 | Du Pont | Pigment production |
| GB900757A (en) * | 1959-07-13 | 1962-07-11 | Ciba Ltd | Process for the manufacture of quinacridone pigments in a finely divided form |
| US3264300A (en) * | 1963-04-30 | 1966-08-02 | American Cyanamid Co | 2, 9-dimethylquinacridone in a "yellow" crystalline form |
| US3598625A (en) * | 1967-11-14 | 1971-08-10 | Cities Service Co | Production of pigmentary grade colorants |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02180884A (ja) * | 1988-12-29 | 1990-07-13 | Toyo Ink Mfg Co Ltd | 新規な化合物，およびそれを用いた顔料並びに電子写真感光体 |
| JPH09165528A (ja) * | 1995-10-12 | 1997-06-24 | Dainippon Ink & Chem Inc | インダンスロンブルー顔料又はカルバゾールジオキサジンバイオレット顔料の製造方法 |
| US11535755B2 (en) | 2016-10-28 | 2022-12-27 | Dainichiseika Color & Chemicals Mfg. Co.. Ltd. | Method for producing quinacridone solid solution pigment, pigment dispersion, and inkjet ink |
| US11773267B2 (en) | 2016-10-28 | 2023-10-03 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Method for producing quinacridone solid solution pigment, pigment dispersion, and inkjet ink |
| WO2019187058A1 (ja) * | 2018-03-30 | 2019-10-03 | 大日精化工業株式会社 | キナクリドン固溶体顔料の製造方法、顔料分散液及びインクジェット用インキ |
| JPWO2019187058A1 (ja) * | 2018-03-30 | 2021-03-18 | 大日精化工業株式会社 | キナクリドン固溶体顔料の製造方法、顔料分散液及びインクジェット用インキ |
| US11926741B2 (en) | 2018-03-30 | 2024-03-12 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Method for producing quinacridone solid-solution pigment, pigment dispersion, and ink-jet ink |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0358389B2 (enrdf_load_stackoverflow) | 1991-09-05 |
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