CS303891A3 - Process for preparing bis-isoindolinone pigments - Google Patents

Description

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Process for producing bis-isoindolinone pigments

Technical field

The present invention relates to a process for the preparation of bis-isoindolinone pigments in a manner known per se, but using 1,2,3-trimethylbenzene as a solvent.

Background Art

Bis-isoindolinone pigments have been known for a long time to produce them by condensing certain isoindolones such as compounds of formula

with diamines is described in a large number of publications, of which US Patent Nos. 2,973,358.3971,805, 4,006,162, 4,043,999, 4,231,931, and 4,327,024 are exemplified. it is carried out in o-dichlorobenzene as a solvent, which is generally also carried out on a large scale. In the publications mentioned above, it is generally indicated and shown in the examples that other solvents are also suitable, including, for example, xylene (U.S. Pat. No. 2,973,385, Example 4).

SUMMARY OF THE INVENTION

It has now been found that when 1,2,3-trimethylbenzene is used as the solvent for the condensation reaction 2 mentioned above, the produced compounds are obtained, which are surprisingly characterized by better properties and particularly high purity compared to the compounds produced by the process. using other chlorinated solvents as well as o-dichlorobenzene.

Therefore, the invention of seisoindolinone pigments is general

relates to formula I of production

wherein A represents a group of formula

wherein B is -O-, -S-, -SO 2 -, N = N-, -CH 2 -, -CH = CH-, -O- (- CH 2 - ^ - O-, O- -CONH- , -NHCONH-, -NHCOCONH-tert-CONHNHCO-, n is 1 to 4, Q is O or S and R and R are each independently hydrogen, atomhalogen, C 1 -C 4 alkyl, alkoxy C 1 -C 4 or phenoxy, X is halogen and X 1 and X 2 are halogen or C 1 -C 4 alkoxy,

by reacting 2 moles of isoindolinone of formula II 4 (Π),

wherein X, X1 and X2 have the meanings given above and

Z 2 wherein Z 1 is imino or thio and Z 2 is chloro, bromo, alkoxy of 1 to 4 carbon atoms or secondary amino,

with one mole of a diamine of formula III h2n-a-nh2 (III) in which A is as defined above, characterized in that the reaction is carried out in the presence of 1,2,3-trimethylbenzene as a solvent.

If the optional substituent is a halogen atom, it is, for example, a fluorine atom, preferably a bromine atom, especially a chlorine atom.

When R or R is C1 -C4 alkyl, it is meant to be methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl. A preferred group is methyl. R 1, R 2, X 2, X 2 and Z 2 represent, as alkoxy groups, 1 to 4 carbon atoms, for example methoxy, ethoxy, n-propoxy, n-butoxy or butoxy. Preferred is methoxy.

As a group of formulas

represents A, for example, a non-substituted p- or non-phenylene group, or 2-chloro-1,4-phenylene, 2-methyl-1,4-phenylene, 2-ethyl-1,4-phenylene, 2-n-propyl-1 , 4-phenylene, 2-isopropyl-1,4-phenylene, 2-tert-butyl-1,4-phenylene, 2-methoxy-1,4-phenylene, 2-ethoxy-1 , 4-phenylene, 2-tert-butoxy - 1,4-phenylene, 2,5-dichloro-1,4-phenylene, 2,5-dimethyl-1,4-phenylene, 2,5- diethyl 1,4-phenylene, 2,5-dimethoxy-1,4-phenylene, 2,5-diethoxy-1,4-phenylene, 2-chloro-5-methyl-1,4-phenylene group , 2-chloro-5-methoxy-1,4-phenylene, 2-methyl-5-methoxy-1,4-phenylene, 2,6-dichloro-1,4-phenylene, 2,6-dimethyl 1,4-phenylene, 6 2-chloro-6-methoxy-1,4-phenylene, 2-chloro-1,3-phenylene, 2-methyl-1,3-phenylene, 2-methoxy-1 , 3-phenylene, 2,5-dichloro-1,3-phenylene, 2,5-dimethyl-1,3-phenylene or a 2-chloro-5-methyl-1,3-phenylene group, especially a 1,3-phenylene group or a 1,4-phenylene group substituted in the 2-position by chloro, methyl, methoxy or ethoxy or unsubstituted at the 2 and 5 are the same or different substituents selected from chlorine, methyl, methoxy or ethoxy. Preferably, it is a 2-methyl-1,3-phenylene group.

If A means a group of formulas

for example, unsubstituted 4,4-biphenylylene or 3,3-dichloro-4,4-biphenylylene, 3,3-methyl-4,4-biphenylylene, 3,3-ethyl-4,4-biphenylylene a 3,3-diisopropyl-4,4-biphenylylene group, a 3,3-di-n-butyl-4,4-biphenylylene group, a 3,3-di-tert-butyl-4,4-biphenylylene group , 3,3-dimethoxy-4,4-biphenylylene, 3,3-diethyl-4,4-biphenylylene-4,4-biphenylylene-4,4-biphenylylene-biphenylylene-4,4-biphenylylene-4,4 -biphenylylene-4,4-biphenylylene group, group, group, group, group, 3,3-di-tert-butoxy-3,3,5,5-tetrachloro-3,3,5,5-tetramethyl -4,4,3,3,5,5-tetramethoxy-3,3-dichloro-5,5-dimethyl-3,3-dichloro-5,5-dimethoxy-, 3,3-dimethyl-5,5 -dimethoxy-4,4-biphenylylene group, especially 7 is a 4,4-biphenylylene group, which is substituted at the 3a and 3 positions with two identical substituents selected from atomuchlor, methyl, methoxy, and the like. pins and ethoxy groups.

If A represents a group of formulas

for example, the following groups are optionally substituted as mentioned above with biphenylylene derivatives, but preferably with unsubstituted 4,4-diphenylylene ether, 4,4-diphenylylene sulfide, 4,4-diphenylylene sulfone, 4,4-diphenylylenazo, 2-chloro-4,4-diphenylylenazo, 3-chloro-4,4-diphenylylenazo, 2-methyl-4,4-diphenylylenazo, 3-methyl-4,4-di-phenylylenazo, 2-methoxy-4, 4-diphenylylenazo, 3-methoxy-4,4-diphenylylenazo, 4,4-diphenylylene-methane, 4,4-diphenylylenethene, 4,4-diphenylenedioxymethane, 4,4-diphenylenedioxybenzene, 4,4- diphenylenecarbamido, 4,4-diphenyleneurea or 4,4-diphenylene-dicarbamylhydrazino. Preferred is 2-methyl-4,4-diphenylenazo. Furthermore, for example, the following groups, which may be optionally substituted with the abovementioned biphenylylene derivatives, but with the preferred substituted 1,4-naphthylene, 1,5-naphthylene, 2,6-naphthylene, 1,5-anthraquinonediyl, 1,4 -antrachinondiyl, 2,6- pyridine diyl, 2,7-carbazolyl, 2,8-dibenzofurandiyl, 3,8-dibenzofurandiyl, 3,7-dibenzofurandiyl, 6,4- (2-phenyl) a benzothiazolyl group, a 2,6-benzthiazolyl group, a 4, 4 "- (2,5-bisphenyl) oxadiazolyl group, or a 4, 4 '- (2,5-bisphenyl) thiadiazole diyl group.

wherein R and R are as defined above and B is -N = N-, -CONH-, -NHCONH- or -CONHNHCO- and especially the formula

However, the preferred isoindolinones of formula (II) are those wherein X, X 1 and X 2 represents a chlorine atom, as well as compounds wherein V represents a group of formula

The isoindolinones of formula II and the diamines of formula III are known compounds. With respect to the use of 1,2,3-trimethylbenzene as a solvent, the condensation is carried out according to known and generally customary methods. It is expedient to operate at a temperature of from 40 to 100 ° C, preferably from 70 to 90 ° C, at a reaction time of from 2 to 5 hours, preferably from 2 to 4 hours. In order to achieve the desired purity, crystallinity and particle size of the pigment, the reaction mixture is finally heated, for example, to a temperature above 130 ° C, preferably to a temperature of 140 to 160 ° C. The obtained compounds for some purposes directly useful as a crude pigment, but can also be conditioned by methods known per se. It is advantageous to use three to ten times, preferably five to eight times, the amount of 1,2,3-trimethylbenzene based on the isoindolinone of general formula II. Examples of inventions

The invention is illustrated by the following examples. Example 1

500 ml of 1,2,3-trimethylbenzene are added to a flask equipped with a 1500 ml ground-glass joint and 116.2 10 g (0.374 mol) of 96.2% of 3,4,5,6-tetrachloro-2-cyanobenzoic acid methyl ester are introduced. Sodium methoxide (70.7 g, 30% in methanol) was added over 10 minutes. The reaction mixture was finally heated to 60-65 ° C and allowed to stir for one hour to give the desired isoindolinone.

At the same time, 20.8g (0.167 mol) of 98.1% 2,6-diaminotoluene was dissolved in 400 ml of 1,2,3-trimethylbenzene in a 500 ml Erlenmeyer flask at 85 ° C. Then 1g of activated carbon is added and the resulting suspension is filtered to give a clear solution. The light 2,6-diaminotoluene solution is then added to the isoindolinone solution. The reaction mixture was heated to 80 ° C and stirred for 3 hours.

After this time, the pressure was carefully reduced with a water pump at 73-77 ° C and methanol was distilled off. 68 ml of glacial acetic acid are dropped into the orange viscous suspension. The yellow pigment suspension is heated for 60 minutes at 150-155 ° C and stirred for 2 hours under this temperature. The suspension is then allowed to cool to 100 DEG C. and 500 ml of methanol are added. The reaction mixture was filtered and the collected cake was washed with 800 mL of methanol and 1000 mL of water. The pigment was dried to constant weight at 100 ° C. Yield 108 g (98.6% of theory). Example 2

Place 1026 ml 1,2,3-trimethylbenzene in a flask fitted with a 3000 ml flat ground glass, add 166.5 g (0.557 mol) 96.2% 3.4.5.6-tetrachloro-2-cyanobenzoic acid methyl ester and mix the reaction mixture. room temperature. Simultaneously, 58 g (0.257 mol) of 4,4-diamino-2-methylazobenzene are stirred in 250 ml of methanol 11 and then filtered. The cake collected on the flask is added to the above reaction mixture together with 440 ml of methanol.

Finally, 100 g of methoxide in the form of a 30% solution in methanol is added to the reaction mixture. The reaction mixture is heated to 60-65 ° C, after 3 hours methanol 400 ml is continuously g65 g

150 ° C distilled off and 1,2,3-trimethylbenzene was added at the same time. During distillation, the temperature is raised to 85 ° C. Then acetic acid was added dropwise, the reaction mixture was warmed to room temperature and stirred at this temperature for 2 hours. After cooling to 100 ° C, 700 ml of methanol are added to the reaction mixture. The solid is filtered off, washed with 1200 ml of methanol and 1500 ml of water. The pigment was dried to constant weight at 120 ° C. The yield was 181 g, corresponding to 92.6% of theory.

Claims (6)

12 ♦ PATENT REQUIREMENTS JITDr.ívan GAME. Steelworker attorney $ c’.S <P * Žitná 25115 04 Prague 1 A method for producing isoindolinone pigments of general formula I wherein A represents a group of formula N 13 wherein B is -O-, -S-, -SO 2 -, N = N-, -CH 2 -, -CH = CH-, -CHCH 2 -O-, , -CONH-, -NHCONH-, -NHCOCONH-or-CONHNHCO-, n is 1 to 4, Q is O or S and R and R are independently hydrogen, atomhalogen, alkyl of 1 to 4; 4 carbon atoms, C 1 -C 4 alkoxy or phenoxy, X is halogen and X 1 and x 2 are halogen or C 1 -C 4 alkoxy by reacting 2 moles of isoindolinone of formula II wherein X, X 1 and X 2 are as defined above and 14 V represents a group of formula or Wherein Z 1 is imino or thio and Z 2 is chloro, bromo, alkoxy of 1 to 4 carbon atoms or secondary amino, with one mole of diamine III of h 2n-a-nh 2 (III) wherein A is as defined above, characterized in that the reaction is carried out in the presence of 1,2,3-trimethylbenzene as a solvent. 2. A process according to claim 1, wherein X, X1 and X2 are chloro in the formulas I and II. 3. A process according to claim 1, wherein V represents a group of formula 15 in formula II OCH 3 4. A process according to claim 1, wherein in formula (I) and (III) A is a group of formula wherein R and R are as defined in claim 1 and B is -N = N-, -CONH-, -NHCONH- or -CONHNHCO-. 5. A process according to claim 4, wherein in formula (I) and (III) A is a group of formula 6. The process of claim 1 wherein the reaction is carried out at a temperature of from 40 to 100 [deg.] C. and the pigment obtained is finally conditioned at a temperature of 16 to 140 [deg.] C to 160 [deg.] C. ΠΤΟΓ tvan KOBE * eK ffiSapa «", Wa '