* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
In a 1 L three-necked flask equipped with an electrically heated magnetic stirrer, a thermocouple and condenser (distillation unit) were installed. , In three84.5 g PPA (0.25 mol) of polyphosphoric acid was added to the flask, and after 3 hours at 100 ° C, 18.8 g of 2,5-dimethylAniline terephthalic acid (0.05mol), add the material, the reaction at 125 3h, stop the reaction. The crude product 2,9-dimethylquinacridone 16.93g, yield 99.59percent.
97%
at 20 - 130℃; for 2.25 h;
Example12; 2000 g of phosphoric acid 85.0percent are placed at 20-25° C in a 10000 ml"All In One Reactor M) of (Drais Mannheim Germany) followed by the. slow addition of 2000 g of P2O5 under stirring and letting the temperature to go up to 80° C. Thereafter 1500 parts of 2,5-di-(4- toluidino) terephthalic acid (Formula V wherein R2=R3-4-CH3) are added thereto under stirring and nitrogen flow. The mixture is now heated to 120° C within 30 minutes and maintained at 120° C for 30 minutes. Thereafter, the mixture is heated to 130° C in 15 minutes and kept at 130° C for one hour. The mixture is cooled to. 70° C followed by metering in of 3000 ml of isobutanol over a period of 2 hours with external cooling, and thereby allowing the temperature to reach the maximum reflux temperature of isobutanol. The mixture is stirred at reflux temperature for one hour, cooled to 70° C and emptied into a stainless steel container. The resulting product is colleted by filtration and reslurried in water containing sodium hydroxide to pH greater than 10. The slurry is heated at 90° to 95° C. for one hour. then again collected by filtration, washed until free of alkali, and dried to give 1316 g (97percent theory) of the compound. of the formula SXVII.
85%
at 20 - 130℃; for 2.25 h;
Example 7 ; 5000 g ofpolyphosphoricacid containing. 85. 0percent P. sub. 2 O. sub. 5. and 1250 parts of 2, 5-di- (4-toluidino) terephthalic acid (Formula V wherein R2=R3= 4-CH3) are placed at 20-25° C in a 10000 ml"All In One Reactor" of (Drais Mannheim Germany). Under stirring and nitrogen flow the mixture is heated to 120'C, within 3 0 minutes and maintained at i20. C for 30 minutes. Thereafter, the mixture is heated to 130 C in 15 minutes and kept at 130 C for one hour. The mixture is cooled to 70 C followed by metering in of 3000 g isobutanol over a period of 2 hours with external cooling, and thereby allowing the temperature to reach the maximum reflux temperature of isobutanol. The mixture is stirred at reflux temperature for one hour, cooled to 70 C and emptied into a Steel container. The resulting 2,9- dimethylquinacridone 1AVILI is colleted by filtration and reslurried in water containing sodium hydroxide (pH greater than 10). The slurry was heated at 90 to 95. degree. C. for one hour, then collected by filtration, washed until free of alkali, and dried to give an 85percent yield of quinacridone of the formula XXVII (95percent purity).
Reference：
[1] Patent: CN106831763, 2017, A, . Location in patent: Paragraph 0033
[2] Patent: WO2005/85364, 2005, A1, . Location in patent: Page/Page column 16
[3] Patent: WO2005/85364, 2005, A1, . Location in patent: Page/Page column 13-14
[4] Justus Liebigs Annalen der Chemie, 1935, vol. 518, p. 245,257
[5] Justus Liebigs Annalen der Chemie, 1935, vol. 518, p. 245,257
[6] Patent: EP1516896, 2005, A1, . Location in patent: Page/Page column 29
[7] Patent: US2009/20043, 2009, A1, . Location in patent: Page/Page column 5
[8] Patent: US2009/20043, 2009, A1, . Location in patent: Page/Page column 5-6
In a 1 L three-necked flask equipped with an electrically heated magnetic stirrer, a thermocouple and condenser (distillation unit) were installed. , In three84.5 g PPA (0.25 mol) of polyphosphoric acid was added to the flask, and after 3 hours at 100 C, 18.8 g of 2,5-dimethylAniline terephthalic acid (0.05mol), add the material, the reaction at 125 3h, stop the reaction. The crude product 2,9-dimethylquinacridone 16.93g, yield 99.59%.
97%
With phosphoric acid; phosphorus pentoxide; at 20 - 130℃; for 2.25h;Product distribution / selectivity;
Example12; 2000 g of phosphoric acid 85.0% are placed at 20-25 C in a 10000 ml"All In One Reactor M) of (Drais Mannheim Germany) followed by the. slow addition of 2000 g of P2O5 under stirring and letting the temperature to go up to 80 C. Thereafter 1500 parts of 2,5-di-(4- toluidino) terephthalic acid (Formula V wherein R2=R3-4-CH3) are added thereto under stirring and nitrogen flow. The mixture is now heated to 120 C within 30 minutes and maintained at 120 C for 30 minutes. Thereafter, the mixture is heated to 130 C in 15 minutes and kept at 130 C for one hour. The mixture is cooled to. 70 C followed by metering in of 3000 ml of isobutanol over a period of 2 hours with external cooling, and thereby allowing the temperature to reach the maximum reflux temperature of isobutanol. The mixture is stirred at reflux temperature for one hour, cooled to 70 C and emptied into a stainless steel container. The resulting product is colleted by filtration and reslurried in water containing sodium hydroxide to pH greater than 10. The slurry is heated at 90 to 95 C. for one hour. then again collected by filtration, washed until free of alkali, and dried to give 1316 g (97% theory) of the compound. of the formula SXVII.
85%
With PPA; at 20 - 130℃; for 2.25h;Product distribution / selectivity;
Example 7 ; 5000 g ofpolyphosphoricacid containing. 85. 0% P. sub. 2 O. sub. 5. and 1250 parts of 2, 5-di- (4-toluidino) terephthalic acid (Formula V wherein R2=R3= 4-CH3) are placed at 20-25 C in a 10000 ml"All In One Reactor" of (Drais Mannheim Germany). Under stirring and nitrogen flow the mixture is heated to 120'C, within 3 0 minutes and maintained at i20. C for 30 minutes. Thereafter, the mixture is heated to 130 C in 15 minutes and kept at 130 C for one hour. The mixture is cooled to 70 C followed by metering in of 3000 g isobutanol over a period of 2 hours with external cooling, and thereby allowing the temperature to reach the maximum reflux temperature of isobutanol. The mixture is stirred at reflux temperature for one hour, cooled to 70 C and emptied into a Steel container. The resulting 2,9- dimethylquinacridone 1AVILI is colleted by filtration and reslurried in water containing sodium hydroxide (pH greater than 10). The slurry was heated at 90 to 95. degree. C. for one hour, then collected by filtration, washed until free of alkali, and dried to give an 85% yield of quinacridone of the formula XXVII (95% purity).
With toluene-4-sulfonic acid; In ethylene glycol; N,N-dimethyl-formamide; at 150℃; for 0.5h;Product distribution / selectivity;
(Example 12) Synthesis of 2,9-dimethylquinacridone by dehydration condensation A solution was prepared by mixing 2.0 g of 2,5-di-(p-toluidino)-terephthalic acid, 0.1 g of p-toluenesulfonic acid, 15 mL of ethylene glycol, and 20 mL of dimethylformamide. A fused silica glass capillary (equivalent diameter, 0.20 mm; and length, 4.0 m) was provided as a reactor, and was fixed in such a manner that a portion of 2.5m length out of the whole capillary was immersed in an oil bath. The oil bath was heated to 150C, and this solution was fed into the reactor at a flow velocity of 1.1 mL/hr (retention time: 5 minutes) with a syringe pump. A pigment having a vivid magenta color was obtained from the discharge port of the capillary. (Comparative Example 7) A solution was prepared by mixing 2.0 g of 2,5-di-(p-toluidino)-terephthalic acid, 0.1 g of p-toluenesulfonic acid, 15 mL of ethylene glycol, and 20 mL of dimethylformamide. An oil bath was heated to 150C to heat the solution in a 50mL flask. The solution was stirred for 30 minutes. The thus-produced pigment was analyzed, and it was proved that the starting materials remained slightly.
With methanesulfonic acid; for 0.166667h;Heating / reflux;Product distribution / selectivity;
The present example was implemented by a synthesis route, such as shown by reaction scheme (1) below. In the present example, 2,5-di-(p-toluidino)-terephthalic acid was used as an N-arylanthranilic acid derivative. A total of 10 parts of 2,5-di(p-toluidino)-terephthalic acid was placed into an eggplant-shaped 100 mL flask, 30 parts of methanesulfonic acid was added thereto at normal temperature and a solution was prepared.The eggplant-shaped flask was immersed in an oil bath heated to a temperature of 160 C., and stirring under heating was performed for 10 minutes under an argon gas atmosphere. The solution changed color from yellow to deep blue-purple, the formation of 2,9-dimethylquinacridone, which is a quinoline derivative, by a condensation ring-closing reaction was confirmed, and the product was taken as a reaction liquid. The reaction liquid was cooled to normal temperature, 15 parts of sodium dodecylsulfate was added as a dispersant, and stirring was performed.A micro-sized flow channel 2a, such as shown in FIG. 1, was used to supply the fluids to a mixing field 1. The micro-sized flow channel 2a for supplying the reaction liquid 4a having the dispersant added thereto to the mixing field 1 was formed from a glass round pipe and the diameter of an opening 3a thereof was 900 mum. The reaction liquid 4a was supplied to the mixing field at a flow rate of 5 mL/min by using a syringe pump.Yet another micro-sized flow channel 2b was formed from a round pipe made from glass that had a diameter of an opening 3b of 500 mum. This micro-sized flow channel 2b served to supply a 0.14N aqueous solution of potassium hydroxide 4b. This solution was supplied to the mixing field at a flow rate of 10 mL/min by using a syringe pump.These two fluids merged in the mixing field 1 provided in air, particles of 2,9-dimethylquinacridone were instantaneously produced and dispersed, and a dispersion of magenta color was obtained at a high concentration. The particles of the obtained dispersion had a very uniform diameter, and the mean particle size was 70 nm. The content of 2,9-dimethylquinacridone particles contained in the dispersion was 6 wt. %.The dispersion liquid obtained was subjected to ultrafiltration, purification, and concentration. Because the original dispersion that was obtained had a high concentration, the processing could be completed within a short period of time.The obtained quinacridone was used as a coloration pigment (C. I. Pigment Red-122), the dispersion thereof was used as an ink-jet ink, the ink was loaded into an ink tank of a BJ Printer S530 (manufactured by Canon Inc.), and printing was performed on the typical paper. The printing produced beautiful text.
With sulfuric acid; sodium dodecyl-sulfate; for 0.166667h;Heating / reflux;Product distribution / selectivity;
A total of 10 parts of 2,5-di-(p-toluidino)terephthalic acid and 15 parts of sodium dodecylsulfate were introduced into an eggplant-shaped 100 mL flask, and 30 parts of concentrated sulfuric acid was added thereto at normal temperature to prepare a solution. The solution color changed to deep brown. The eggplant-shaped flask was immersed in an oil bath heated to 160 C., and stirring under heating was performed for 10 minutes under an argon gas atmosphere. The solution was colored black and dissolution of sodium dodecylsulfate was confirmed.
With sulfuric acid; In 1-methyl-pyrrolidin-2-one; at 40℃; for 1.5h;Purification / work up;
Example 3(Method of Making I) Preparation of Nanopigment Red 122 Without the Steric StabilizerCommercially available Pigment Red 122 (Dainichiseika ECR-186Y) (1.5 g, 0.0044 mol) was dissolved with stirring in 20 mL concentrated sulfuric acid. The violet-indigo solution was added via a dropping funnel with stirring into 100 mL of N-methyl-2-pyrrolidinone during a period of 60 minutes. The temperature of the reaction mixture was maintained below 40 C. (preferably at room temperature) during the addition. The suspension color changed from indigo to cherry red and finally raspberry red. At the end of the addition, the suspension was allowed to stir for another 30 minutes. Isopropanol (50 mL) was added dropwise to the final slurry. The resulted suspension was filtered using a glass frit. The solid was washed three times with dimethyl formamide and once with a mixture of 1:1 dimethyl formamide and deionized water. The resulting solid (1 g) was freeze dried over night; D50=89+/-1.2 nm, GSD=1.5+/-0.02. The particle morphology and range in size observed by Transmission Electron Microscopy showed particles having irregular rod-like and platelet shapes between about 30 and about 200 nm.
6
[ 67906-32-5 ]
[ 10109-95-2 ]
[ 10291-28-8 ]
[ 1047-16-1 ]
[ 980-26-7 ]
[ 10228-01-0 ]
Yield
Reaction Conditions
Operation in experiment
With PPA; at 90 - 125℃; for 3h;
250 parts of polyphosphoric acid containing P2O5 (85.0%) are metered into a stirred vessel. Then 45 parts of the product obtained according to Example 1 are added at 90 C. with stirring and the mixture is heated to 125 C. for 3 hours during which ring closure takes place. The mixture is cooled to 110 C. and 6 parts of water are gradually added over 10 minutes. Then, the mixture is poured into 750 parts of water at 50 C. and stirred at 60 C. for 1.5 hours. The solid is collected by filtration and washed with water until the washing water is neutral. 100 parts of the presscake obtained are reslurried in 170 parts of methanol and the slurry is heated in a pressure reactor at about 90 C. for 3 hours. The mixture is cooled and the pH is adjusted to 9-9.5 with sodium hydroxide solution (50%). The solid is collected by filtration and washed with water. The wet presscake is dried in an oven or used as it is. Upon drying in an oven at 80 C., about 19 parts of a solid solution are collected comprising the compounds of formulae [C00026] [00026] [0156] in a ratio of 69.7:28.1:2.2 as established by the relative peak areas according to HPLC.
With PPA; at 90 - 125℃; for 3h;
250 parts of polyphosphoric acid containing P2O5 (85.0%) are metered into a stirred vessel. Then 45 parts of the product obtained according to Example 2A are added at 90 C. with stirring and the mixture is heated to 125 C. for 3 hours during which ring closure takes place. The mixture is cooled to 110 C. and 6 parts of water are gradually added over 10 minutes. Then, the mixture is poured into 750 parts of water at 50 C. and stirred at 60 C. for 1.5 hours. The solid is collected by filtration and washed with water until the washing water is neutral. 100 parts of the presscake obtained are reslurried in 170 parts of methanol and the slurry is heated in a pressure reactor at about 90 C. for 3 hours. The mixture is cooled and the pH is adjusted to 9-9.5 with sodium hydroxide solution (50%). The solid is collected by filtration and washed with water. The wet presscake is dried in an oven or used as it is. Upon drying in an oven at 80 C., about 19 parts of a solid solution are collected comprising the compounds of formulae (115), (116) and (117) in a ratio of in a ratio of 70.3:25.2:4.5, as established by the relative peak areas according to HPLC
With PPA; at 90 - 125℃; for 3h;
250 parts of polyphosphoric acid containing P2O5 (85.0%) are metered into a stirred vessel. Then 45 parts of the product obtained according to Example 2B are added at 90 C. with stirring and the mixture is heated to 125 C. for 3 hours during which ring closure takes place. The mixture is cooled to 110 C. and 6 parts of water are gradually added over 10 minutes. Then, the mixture is poured into 750 parts of water at 50 C. and stirred at 60 C. for 1.5 hours. The solid is collected by filtration and washed with water until the washing water is neutral. 100 parts of the presscake obtained are reslurried in 170 parts of methanol and the slurry is heated in a pressure reactor at about 90 C. for 3 hours. The mixture is cooled and the pH is adjusted to 9-9.5 with sodium hydroxide solution (50%). The solid is collected by filtration and washed with water. The wet presscake is dried in an oven or used as it is. Upon drying in an oven at 80 C., about 19 parts of a solid solution are collected comprising the compounds of formulae (115), (116) and (117) in a ratio of in a ratio of 86.6:4.6:8.9 as established by the relative peak areas according to HPLC
With PPA; at 90 - 125℃; for 3h;
250 parts of polyphosphoric acid containing P2O5 (85.0%) are metered into a stirred vessel. Then 45 parts of the product obtained according to Example 1 are added at 90 C. with stirring and the mixture is heated to 125 C. for 3 hours during which ring closure takes place. The mixture is cooled to 110 C. and 6 parts of water are gradually added over 10 minutes. Then the mixture is poured into 750 parts of water at 50 C. and stirred at 60 C. for 1.5 hours. The solid is collected by filtration and washed with water until the washing water is neutral. 100 parts of the presscake obtained are reslurried in 150 parts of ethanol, 15 parts of sodium hydroxide solution (50%) and C-33 surfactant (cocoalkyl quaternary ammonium salt, 33% sol.) and the slurry is heated in a pressure reactor at about 120 C. for 5 hours. The mixture is cooled, the solid is collected by filtration and washed with water. The wet presscake is dried in an oven at 80 C. About 19 parts of a solid solution are collected comprising the compounds of formulae (115), (116) and (117) in a ratio of 69.7:28.1:2.2 as established by the relative peak areas according to HPLC.
With sodium t-butanolate; In tert-butyl alcohol; at 30 - 90℃; under 37.5038 - 600.06 Torr;
1700 g of the crude dimethyl quinacridone pigment <strong>[980-26-7]C. I. Pigment Red 122</strong>,3500g of tert-butyl alcohol and 960G of sodium TERT-BUTYLATE are placed in a 10000 ml"All In One REACTOR" of (Drais Mannheim Germany) at 30 C. Under stirring and nitrogen flow the mixture is heated to 80 C and maintained at 80 C for 3 hours. From 50 C ONWARDS the reaction mixture becomes considerably thicker and is finally converted into a paste. Thereafter, the mixture is slowly heated to approx. 90 C. After reaching an inside temperature of 85 C a vacuum of 800 mbar is applied at the outlet of the condenser which is then gradually further reduced to 50 mbar, thereby allowing the tert-butyl alcohol to distil off. The inside temperature first drops to 75 C and thereafter rises again to 85 C as soon as the alcohol is completely distilled off. The reaction mass becomes crumbly and finally largely disintegrates into an almost semi-powdery material. The mixture is stirred for another 30 minutes at 85 C under vacuum of 50 mbar. The reaction mixture is cooled to 60 C. The material is emptied into a steel drum affording 1890 g of the product of the formula XXX. Approximately 30 G of the product are still contained in the reactor to be used in the next batch. The distillate is also used for the next batch.
With dihydrogen peroxide; potassium hydroxide; at 90 - 110℃; for 4h;pH 10 - 11;
Oxidation process: Add 2,9-dimethyl-6,13-dihydroquinacridone obtained through condensation and ring closure reaction to the reaction vessel,Then add onion ketone-2-sulfonate sodium, adjust the pH to 10-11 with KOH solution, and heat to 90 C,Slowly add hydrogen peroxide solution to the reaction vessel to control the molar ratio of hydrogen peroxide, sodium onion-2-sulfonate and 2,9-dimethyl-6,13-dihydroquinacridone to be 1.8: 0.05: 1.Continue to heat up to 105-110 , maintain the temperature, the reaction 4h,End of reactionCool the reaction solution to 80 C, pour it into a beaker, add the same volume of cold water as the reaction solution,Stir and cool to room temperature, filter, filter cake was washed and beaten with methanol for 1h, Filter and top wash to get PR122 crude product;Purification process: Add N, N-dimethylformamide and crude PR122 to the four-necked bottle in sequence,After mechanical stirring for 15 minutes, the solution began to be heated; the temperature was first raised to 68 C and maintained for 30 minutes.Then continue to heat up until the solution has reflux, keep the temperature 2.5h, the reaction is over;Reduce the temperature to 50-55 C, add sodium hydroxide solution dropwise to adjust the pH of the material to 7-7.5, and continue to stir for 30 min,Check the pH of the solution again. If there is no change in the pH, the reaction ends; if the pH of the solution decreases, repeat the operation of adding sodium hydroxide solution dropwise until the pH of the solution is constant;The solution was filtered, and the filter cake was washed again with methanol and water, and dried in a blast dryer to obtain the final product pigment PR122.The yield of the product pigment red PR122 obtained was 91.13%.
With sodium hydroxide; dihydrogen peroxide; In water; polyethylene glycol 400; at 20 - 60℃; for 1h;Product distribution / selectivity;
(Example 11) Synthesis of 2,9-dimethylquinacridone by oxidization reaction To 2.0 g of 2,9-dimethyl-6,13-dihydroquinacridone, were added 10.0 mL of a 5 mol/L aqueous sodium hydroxide solution, and 18 g of polyethylene glycol 400, and the resultant mixture was stirred at room temperature. The resultant solution, the color of which was deep green, is referred to as Solution A. The Solution A was fed at a flow velocity of 3.0 mL/hr by use of a syringe pump. Separately, as Solution B, a 30% by mass aqueous hydrogen peroxide solution was fed at a flow velocity of 0.5 mL/hr, by use of a syringe pump. These Solutions A and B were fed to a micro-mixer (channel width, 45 mum; depth, 200 mum) manufactured by IMM Co., and then mixed in a micro-space therein. At the discharge port of the micro-mixer, the production of a dispersion having a vivid magenta color was observed. The dispersion was analyzed, and it was proved that 2,9-dimethylquinacridone having a purity of 96% or more was produced. (Comparative Example 6) To 2.0 g of 2,9-dimethyl-6,13-dihydroquinacridone, were added 10.0 mL of a 5N aqueous sodium hydroxide solution, and 18 g of polyethylene glycol 400, and the resultant mixture was stirred at room temperature. To the resultant solution, the color of which was deep green, was dropwise added 2.0 mL of a 30% by mass aqueous hydrogen peroxide solution, and then the resultant solution was stirred at 60C for 1 hour, and cooled to room temperature. The resultant was analyzed, and it was proved that the conversion ratio of the starting material was 80%, and that 2,9-dimethylquinacridone having a pigment purity of 94% or more was produced.
Example 11; 1140 g of dimethyl succinnoylsuccinate (formula II, in which R1 = CH3, 4-cyclohexanedione- 2 ; 5-di (carboxylic acid methyl ester), 1113 g of p-toluidine, 1000parts of isobutanol, and 25g of phosphoric acid of 85 % concentration are placed at 20-25 C in a 10000 ml"All In One Reactor "No. of (Drais Mannheim Germany). Under stirring and nitrogen flow the mixture is heated to 100 C within 60 minutes. From 80 C onwards the reaction mixture becomes considerably thicker and is finally converted into a paste.. The temperature is maintained at 99 to 100 C for three hours, thereby allowing the mixture of isobutanol and water formed to distil off. The reaction mass becomes crumbly and finally largely disintegrates into an almost semi-powdery material. The reaction mixture is heated to 120 C in 30 minutes and kept at 120 C for 30 minutes under vacuum of 50mbar. The mixture is cooled to 50 C. For the cyclisation 5000 g of a dimethylnaphthalene isomer mixture are now introduced into the reactor and under stirring and nitrogen flow the mixture is heated to 280 C within 60 minutes. The temperature is maintained at 280 for 30 minutes, thereby allowing the methanol formed to distil off. The reaction mass becomes thick and crumbly. The mixture is cooled to 60 C. Into the reactor are metered over the course of 2 hours 2000 parts of methanol. Then, 1350 g of sodium m-nitrobenzenesulfonate are added, and immediately thereafter, 2400 parts of a 50% NaOH aqueous solution ale added. Then. the mixture is refluxed for 4 hours ; acidified with sulphuric acid to PH 3 to give 3675 g (of a theoretical value) of the compound of the formula XXVII after emptying out, filtration and washing, water and drying.
With toluene-4-sulfonic acid; for 0.166667h;Heating / reflux;Product distribution / selectivity;
The present example was implemented by a synthesis route, such as shown by reaction scheme (3) below. In the present example, a methyl ester of 2,5-di-(p-toluidino)-terephthalic acid was used as an N-arylanthranilic acid derivative. A total of 10 parts of this compound was placed into an eggplant-shaped 100 mL flask, 10 parts of p-toluenesulfonic acid was added thereto at normal temperature, the components were heated to 110 C., and a solution was prepared. The eggplant-shaped flask was immersed in an oil bath heated to a temperature of 180 C., and stirring under heating was performed for 10 minutes under an argon gas atmosphere.The solution changed color from yellow to deep blue-purple, the formation of 2,9-dimethylquinacridone, which is a quinoline derivative, by a condensation ring-closing reaction was confirmed, and the product was taken as a reaction liquid. The reaction liquid was cooled to 110 C., 15 parts of sodium dodecylsulfate was added as a dispersant, and stirring was performed.A total of 10 parts of an aqueous solution of 0.14N sodium hydroxide was added to the eggplant-shaped flask immersed in ice water, stirring was performed with a magnetic stirrer, and the reaction liquid having a dispersant added thereto and maintained at a liquid temperature of 110 C. was dropwise added. As a result, particles of 2,9-dimethylquinacridone were instantaneously produced and dispersed, and a dispersion of a magenta color was obtained with a high concentration.The particles of the obtained dispersion had a very uniform diameter, and the mean particle size was 135 nm. The content of 2,9-dimethylquinacridone particles in the dispersion was 22 wt. %.
poly(formaldehyde-co-1-naphtalene sulfonic acid sodium salt-co-2-naphtalene sulfonic acid sodium salt); 2,9-dimethylquinacridone; mixture of[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
A one-liter flask equipped with a stirrer, thermometer, condenser and drying tube is charged with 200 ml concentrated (95-98%) sulfuric acid. 17 G 2, 9-DIMETHYLQUINACRIDONE pigment (CROMOPHTALS PINK PT, Ciba Specialty Chemicals Inc.) is added at a temperature below 45oC and the mixture is stirred for 10 minutes at 40-45oC to completely dissolve the pigment. 19.9 g of a wet naphthalene sulfonic acid sodium salt presscake with a solid content of 58%, a mixture containing 80% 1-naphthalene sulfonic acid sodium salt and 20% 2- naphthalene sulfonic acid sodium salt (Shanghai Shen Li Chemical Factory) are added at a temperature BELOW 45oC and the mixture is stirred for 30 minutes at 40-45oC followed by the rapid addition of 1.6 g para formaldehyde. The reaction mixture is stirred for one hour at 58-60oC then poured into 2.5 liter ice water. The bluish violet precipitate is stirred for 1 hour at 5-20oC, and then filtered. The violet press cake is washed with water to a pH of 2-2.5 and kept as presscake. About 0.5 g of the press cake are reslurried in 20 ML hot water yielding a magenta colored liquid which is filtered through paper to remove little aggregated material. The filtrate is magenta and appears like a dye solution. However, the electron micrograph shows the 2, 9-dimethyl quinacridone in nanosize particle form with an average particle size of from 10 to 30 nm.
2,9-dimethyl-3,10-di(4-chlorobutyryl)quinacridone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
90%
With zirconium chloride; In tetrachloromethane; at 10 - 60℃; for 48h;
(1) Take pigment red 122 35g (0.1mol, 98% purity, BASF), Zirconium chloride 51 g (0.22 mol) was added to a four-necked flask containing 500 ml of carbon tetrachloride, cooled to 10C, and a mixed solution of 35.5 g (0.25 mol) of chlorobutyl chloride and 100 ml of carbon tetrachloride was added dropwise thereto. After completion of the dropwise addition, the reaction was heated to 60 for 48 hours, and then mixed with a mixture of 1000 ml of ice water and 500 ml of hydrochloric acid (30%), and the mixture was allowed to stand for stratification, the organic layer was collected, washed with water until neutral, and dried over anhydrous sodium sulfate, filtered, carbon tetrachloride was recovered and by the time Intermediate (a-2), 2,9-dimethyl-3,10-di(4-chlorobutyryl)quinacridone 50 g was obtained in in a yield of 90%,
2,9-dimethyl-5,12-bis(6-bromohexyl)-5,12-dihydroquino[2,3-b]acridine-7,14-dione[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
With sodium hydride; In tetrahydrofuran; for 24h;Reflux;
<strong>[980-26-7]2,9-dimethyl-5,12-dihydroquino[2,3-b]acridine-7,14-dione</strong> (3.40 g, 10 mmol),1,6-dibromohexane (12.20 g, 50 mmol),Sodium hydride (1.20g, 50mmol) and 50mL of solvent tetrahydrofuran were mixed together in a 150mL pressure bottle, heated and stirred for reflux for 24h.The solid was removed by suction filtration using a suction filter, and the obtained filtrate was evaporated to remove the solvent to give a crude product which was applied to silica gel column chromatography.Dichloromethane: petroleum ether = 1:1 as a developing solvent to obtain a solid compound A-14.33 g, yield 65%.
To 100 parts of polyphosphoric acid, 1 part of the intermediate (B) prepared above and 9 parts of the intermediate (C-2) were added, and the mixture was heated at 120 to 130 C. for 2 hours.The reaction product was poured into ice water, and the precipitate was filtered.After washing the precipitate with water until the filtrate is neutral,After drying at 80 C., 9 parts of a quinacridone solid solution pigment represented by the following formulas (D) and (E-2) were obtained.
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