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 896969Notes

Reaction equation

HRID 896969 reaction equation
C=CC1C=CC=CC=1.C(O)(=O)C=C.C(OCC1OC1)(=O)C(C)=C.CO.[OH-].[K+].[CH3:28][C:29]1[CH:34]=[CH:33][C:32]2[NH:35][C:36]3[C:41]([C:42](=[O:43])[C:31]=2[CH:30]=1)=[CH:40][C:39]1[NH:44][C:45]2[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][C:46]=2[C:47](=[O:48])[C:38]=1[CH:37]=3>CS(C)=O.C1C=C2C(C3C(NC2=CC=1)=CC1C(C2C(NC=1C=3)=CC=CC=2)=O)=O.O>[CH:50]1[CH:49]=[C:46]2[C:47]([C:38]3[C:39]([NH:44][C:45]2=[CH:52][CH:51]=1)=[CH:40][C:41]1[C:42]([C:31]2[C:32]([NH:35][C:36]=1[CH:37]=3)=[CH:33][CH:34]=[CH:29][CH:30]=2)=[O:43])=[O:48].[CH3:28][C:29]1[CH:34]=[CH:33][C:32]2[NH:35][C:36]3[C:41]([C:42](=[O:43])[C:31]=2[CH:30]=1)=[CH:40][C:39]1[NH:44][C:45]2[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][C:46]=2[C:47](=[O:48])[C:38]=1[CH:37]=3

Participants

8

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 704235,12-Dihydro-2,9-dimethylquino(2,3-b)acridine-7,14-dione2×HCID 131725041Styrene acrylic acid glycidyl methacrylate

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/glycidyl methacrylate (7/2/1; molar ratio) terpolymer (molecular weight: 5,000) as a self-crosslinkable compound 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 impeller 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 30.2 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 60° C. While retaining the internal temperature of 60° C., the stirring was continued for additional 5 hours, and the reaction mixture was then cooled back to room temperature. Thereafter, 10% hydrochloric acid was added dropwise to adjust the pH of the reaction mixture to 4.0. The resultant aggregates 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

  1. stirringagitating blade (800 rpm)
  2. custompurged with nitrogen
  3. temperaturecooled
  4. 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-464e8a91e0b04c9cae08840e2165167d
Source dataset
uspto-grants-2005_07
Patent number
US06921433B2

Reaction notes

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