Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1991-10-22
1993-05-11
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544189, C09B 1467, C09B 6728
Patent
active
052101908
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to an improved process for preparing anthraquinone dyes of the general formula I ##STR4## where Ar is aryl and the A radicals are each anthraquinonyl radicals, by reacting an aryldihalotriazine of the general formula II ##STR5## where Hal is chlorine or bromine, with an aminoanthraquinone III
Anthraquinone dyes of the formula I belong to the important group of the vat dyes.
As is already known from DE patents 551,884, 637,937 and 1,026,456, the dyes I are obtainable by reacting the aryldichlorotriazines II with the amino-anthraquinones III in a high-boiling aromatic solvent such as nitrobenzene or di- or trichlorobenzene. However, the yields of from 85 to 90% obtainable with this process are unsatisfactory.
Attempts to improve the process by including bases and a copper(I)amine catalyst (DE patent 1,795,102) had only limited success and in the case of the particularly important dye Vat Blue 66 (Ar = phenyl, A =1-amino-2-acetylanthraquinon-4-yl) led even to a yield of only 53%.
It is an object of the present invention to make available the dyes I in better yields and in a more economical manner.
We have found that this object is achieved by a process for preparing an anthraquinone dye of the general formula I ##STR6## where Ar is aryl and the A radicals are each anthraquinonyl, by reacting an aryldihalotriazine of the general formula II ##STR7## where Hal is chlorine or bromine, with an aminoanthraquinone III N--C.sub.1 -C.sub.4 -alkylpyrrolid-2-one, N--C.sub.1 -C.sub.4 -alkylpiperid-2-one, N-di-C -C -alkylacetamide or N-di-C.sub.1 -C.sub.4 -alkylpropionamide or a urea derivative of the formula IV ##STR8## where the radicals R are identical or different alkyl groups of from 1 to 4 carbon atoms which can also be linked to one another to form a 5- or 6-membered ring containing the urea group.
Suitable solvents for the purposes of the present invention are N-isopropyl- or N-n-butyl-pyrrolidone, preferably N-methylpyrrolidone, N-isopropyl- or N-n-butylpiperidone, preferably N-methylpiperidone, -C.sub.4 -alkyl groups as radicals R such as tetra-n-propyl-, tetra-n-butyl- or dimethyldiethyl-urea, preferably tetramethyl- or tetraethyl-urea, or with radicals R which link together as ethyleneor propylene-ureas to form a 5- or 6-membered ring containing the urea group, such as 1,3-diethyl- or 1,3-dipropyl-imidazolidin-2-one or 1,3-diethyl- or 1,3-dipropyl-tetrahydro-2(lH)-pyrimidinone, preferably 1,3-dimethylimidazolidin-2-one or 1,3-dimethyl-tetrahydro-2(1H)-pyrimidinone, and di-n-propyl- or di-n-butyl-acetamide or dimethyl-, diethyl-, di-n-propyl- or di-n-butylpropionamide, preferably dimethylacetamide.
These solvents are very potent solvents for the starting materials of the process. Thus, the amount of solvent is in general only 2-6, preferably 2.5-4 kg per kg of III.
The reaction can also be carried out in the presence of acid-binding agents such as the alkali metal salts of weak acids, for example sodium acetate, sodium carbonate or potassium carbonate.
Furthermore, it is also possible to use a catalyst in the form of an addition compound of copper(I) iodide or bromide with a tertiary base such as triethylamine, pyridine or related compounds.
The starting compounds II an III are known or obtainable by known methods. The molar ratio of II to III is advantageously from 0.5:1 to 1:1, in particular from 0.6:1 to 0.8:1.
In general, the reaction is carried out at from 80 to 200.degree. C., preferably at from 100 to 160.degree. C. The reactants can be added alternatively before or after the reaction temperature has been reached. It is also possible to increase the temperature during the reaction in order to achieve complete conversion.
The reaction is in general carried out under atmospheric pressure but can also be carried out under reduced pressure.
The reaction times including the after-stirring times are in general from 5 to 12, preferably from 6 to 8, hours.
The reaction mixture is worked up for the products in a conventional manner, preferably by cooling the solution and separating o
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Epple Gerhard
Helwig Reinhard
Hoch Helmut
BASF - Aktiengesellschaft
Higel Floyd D.
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