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 896963Notes

Reaction equation

HRID 896963 reaction equation
C=CC1C=CC=CC=1.C(O)(=O)C=C.CO.[OH-].[K+].[CH3:18][C:19]1[CH:24]=[CH:23][C:22]2[NH:25][C:26]3[C:31]([C:32](=[O:33])[C:21]=2[CH:20]=1)=[CH:30][C:29]1[NH:34][C:35]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][C:36]=2[C:37](=[O:38])[C:28]=1[CH:27]=3>CS(C)=O.C1C=C2C(C3C(NC2=CC=1)=CC1C(C2C(NC=1C=3)=CC=CC=2)=O)=O.O>[CH:40]1[CH:39]=[C:36]2[C:37]([C:28]3[C:29]([NH:34][C:35]2=[CH:42][CH:41]=1)=[CH:30][C:31]1[C:32]([C:21]2[C:22]([NH:25][C:26]=1[CH:27]=3)=[CH:23][CH:24]=[CH:19][CH:20]=2)=[O:33])=[O:38].[CH3:18][C:19]1[CH:24]=[CH:23][C:22]2[NH:25][C:26]3[C:31]([C:32](=[O:33])[C:21]=2[CH:20]=1)=[CH:30][C:29]1[NH:34][C:35]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][C:36]=2[C:37](=[O:38])[C:28]=1[CH:27]=3

Participants

8

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 704235,12-Dihydro-2,9-dimethylquino(2,3-b)acridine-7,14-dione2×HCID 22481611Styrene acrylic acid copolymer

Product 1

HCID 1317250385,12-Dihydroquinolino[2,3-b]acridine-7,14-dione;2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 13976QuinacridoneSolvent2×

Conditions

Temperature
0 °C

Procedure

Ten parts of a styrene/acrylic acid copolymer (acid value: 250; molecular weight: 5,000) as a dispersing agent 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, it 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) and cooled and temperature-maintained by means of two 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 27.6 nm.

Workup

  1. stirringagitating blade (800 rpm)
  2. temperaturecooled
  3. temperaturetemperature-maintained by means of two 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-6bb857439982471db9ca27fb9a72b6cd
Source dataset
uspto-grants-2005_07
Patent number
US06921433B2

Reaction notes

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