DE260662C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

'- M 260662 CLASS 22 b. GROUP

Patent specification 230172 of class 12 ⁰ shows that when uj-w'-tetrabromo-m-xylene is heated with alkaline iodine in the presence of acetone, the corresponding ω-ω'-tetraiododimethyl derivative is formed (cf. . Ges. 43 [2], p. 1528).

In contrast, it was found that in the same treatment of the ou-dihalomethylanthraquinones and their derivatives containing one or more ω- dihalomethyl groups, e.g. B. of dianthraquinonyl, instead of the expected iodine derivatives, condensation products, which are vat dyes, are obtained by the halogen-free radicals coming together. Thus, cu-dibromo-2-methyl-anthraquinone gives bis-2-anthraquinonylethylene (diphtaloylstilbene) and 1-bromo- ω- dibromo-2-methylanthraquinone gives the corresponding bis-ibromo-2-anthraquinonylethylene. In a similar way, from u) -to'-tetrachloro- or tetrabromo-2 · 2 ¹ -dimethyl-i · i ^x -dianthraquinonyl of patent specification 240834 of class 12 ^0, diphtaloyl-3 · 4 · 5 · 6-phenanthrene is obtained .

Examples:

ι. ■. ι part u! ~ Dibromo-2-methylanthraquinone and 2 parts of sodium iodine are heated to 100 ° with 10 parts of acetone for about 12 to 14 hours. The deposited product is identical to the dye described in the patent specification 199756 of class 12 ^{0, the one there}

erroneously the constitution has the formula C ₃₀ H ₁₄ O ₄

and

.CO

is assigned and which arises from the fact that 2-methylanthraquinone or its in the Side chain halogenated derivatives with condensing agents such as caustic alkalis, alcoholic potash or caustic soda or alkaline earths.

2. Part cu-u) '- tetrabromo-2 · 2 ¹ -dimethyl-I · I ¹ -dianthraquinonyl is heated to 100 ° with 2 parts of sodium iodine and 10 parts of acetone for about 12 to 14 hours. After cooling, the deposited product is filtered off and boiled successively with acetone and with water. The diphtaloylphenanthrene obtained in this way forms an orange-brown powder which turns purple-tinged red from a red vat; in the air this color changes to a brown-orange. Treating it with a chlorinated lime solution will make it purer. The dye is soluble in a dirty brown color in concentrated sulfuric acid; in organic solvents it dissolves with yellow to brownish

yellow color, heavy in benzene, fairly light in nitrobenzene; he separates from the latter indistinctly crystalline. It is very sparingly soluble in ether, ligroin and alcohol.

That the reaction proceeds as indicated is directly from the behavior given above of i-bromo -ω-dibromo-2-methylanthraquinone, which can only be explained in that way, close. The dye obtained therefrom, which still contains the bromine in the i-position unchanged, is that of the example ι so similar that it must be assumed that both belong to the same class and are stilbene derivatives. This is consistent with the characteristics of the latter Dye, in particular with the oxidisability to anthraquinone-2-carboxylic acid and the Can be converted into a bromine addition product, from which the bromine is easily split off again leaves. The dianthraquinone derivatives can also be regarded as stilbene derivatives.

Claims (1)

Patent claim: Process for the preparation of condensation products of the anthraquinone series, characterized in that u; -dihalomethylanthraquinones or one or more co-dihalomethyl groups thereof containing derivatives, e.g. B. Dianthraquinonyl treated with iodine alkalis.