Methanol → 5,12-Dihydroquinolino[2,3-b]acridine-7,14-dione;2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione

HRID 896966Notes

Reaction equation

C=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9](O)(=O)C=C.[CH3:14][OH:15].[OH-:16].[K+].C1C(C=O)=CC=C(C=O)C=1.[CH:28]1[CH:33]=[C:32]2[C:34]([C:36]3[C:41]([NH:42][C:31]2=[CH:30][CH:29]=1)=[CH:40][C:39]1[C:43]([C:45]2[C:50]([NH:51][C:38]=1[CH:37]=3)=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:44])=[O:35]>CS(C)=O.CC1C=CC2NC3C(C(=O)C=2C=1)=CC1NC2C=CC(C)=CC=2C(=O)C=1C=3.O>[CH:47]1[CH:46]=[C:45]2[C:43]([C:39]3[C:38]([NH:51][C:50]2=[CH:49][CH:48]=1)=[CH:37][C:36]1[C:34]([C:32]2[C:31]([NH:42][C:41]=1[CH:40]=3)=[CH:30][CH:29]=[CH:28][CH:33]=2)=[O:35])=[O:44].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:51][C:38]3[C:39]([C:14](=[O:15])[C:5]=2[CH:4]=1)=[CH:40][C:41]1[NH:42][C:31]2[CH:30]=[CH:29][C:28]([CH3:9])=[CH:33][C:32]=2[C:34](=[O:16])[C:36]=1[CH:37]=3

Participants

Conditions

Temperature: 0 °C

Procedure

Five parts of a styrene/acrylic acid copolymer (acid value: 250; molecular weight: 5,000) as a dispersing agent and 4 parts of polyvinyl alcohol (low degree of saponification; degree of polymerization: 1,000) as a compound having a crosslinkable functional group were dissolved in 80 parts of dimethyl sulfoxide, and 10 parts of a quinacridone pigment (C.I. Pigment Red 122) were suspended in the resultant solution in a flask at 25° C. under an air atmosphere. A 30% methanol solution of potassium hydroxide was then added dropwise little by little to dissolve the quinacridone pigment. After the pigment solution was stirred for 3 hours, terephthaldialdehyde as a crosslinking agent was added to and dissolved in the pigment solution in a proportion of 1 part per 10 parts of the pigment, and the resultant solution was quickly poured into ion-exchanged water (400 parts of ion-exchanged water per 10 parts of the pigment; 0° C.) stirred by an impellor type agitating blade (800 rpm), purged with nitrogen and cooled and temperature-maintained by means of 2 system dispensers (manufactured by Musashi Engineering K.K.; needle internal diameter: 0.57 mm; delivery pressure: 4.0 kgf/cm2) to obtain an aqueous dispersion of quinacridone-pigment-containing particles having an average particle diameter of 38.9 nm. This aqueous dispersion was transferred to a reaction vessel equipped with a mantle heater, cooling tower, stirrer and thermometer, and this system was purged with nitrogen with stirring at 300 rpm and heated to an internal temperature of 80° C. While retaining the internal temperature of 80° C., 10% hydrochloric acid was added dropwise to adjust the pH of the reaction mixture to 4.0. After continuing the reaction for additional 5 hours, the reaction mixture was cooled back to room temperature. Thereafter, aggregates formed were filtered under reduced pressure through a membrane filter (holding particle diameter: 0.45 μm) and washed 3 times with 500 ml of ion-exchanged water to obtain a paste of an aqueous dispersion of the quinacridone-pigment-containing particles desalted and desolvated.

Workup

stirringagitating blade (800 rpm)
custompurged with nitrogen
temperaturecooled
temperaturetemperature-maintained by means of 2 system dispensers (manufactured by Musashi Engineering K.K.; needle internal diameter: 0.57 mm; delivery pressure: 4.0 kgf/cm2)

Sources & evidence

ORD record: ord-0c8a0ae0de99451680f112d093220a96
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921433B2

Reaction notes

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