DE82074C - - Google Patents

Description

IMPERIAL

PATENTAM

., In the patent specifications No. 75084 and No. 80853 is shown to DAF Surfoniren by the acetyl-aj-naphthylamine-c ^ -rnonosulfosäure and following it, cleaving the acetyl group to the α, ß--Naphtylamin ₃ a ₄ - disulfonic acid enters and that this Disulfonic acid when fused with alkalis at temperatures between 160 and 250 ° C. _{yields a Ct 1} -amido-ci ₄ -naphthol-ß-monosulfonic acid, which is different from all the β-sulfonic acids of Ct ₁ α ₄ -amidonaphthol known to date. Since the constitution of the above-mentioned et, -naphthylamine-βj ci ₄ -disulfonic acid is proven by the conversion of the same into the naphthalene-cij β ₂ -disulfonic acid when the amido group is split off, there is no doubt that the amidonaphthol sulfonic acid derived from it is also the same Has sulfo group in ß _3. :

The aj-amido-c ^ -naphthol-βg-monosulphonic acid is ideally suited for the preparation of simple and mixed disazo dyes, which are characterized by their complete alkali fastness and the valuable property of being further diazotized on the fiber and with phenols, To have amines, as well as their sulfo- and carboxylic acids coupled to new, extremely whackfast dyeings. Because of this ability as well as the ability to color well without the use of caustic alkalis, the dyes of the present patent advantageously differ from the corresponding dyes from the benzoylated Ci ₁ a ₄ -amidonaphthol-Ct ₃ -sulfonic acid (Patent No. 54662) . They also have the advantage over the non-benzoylated dyes of the patent mentioned and the disazo dyes of Patent No. 68462 (from Ci _x a ₄ -amidonaphthol monosulfonic acid H) of producing far clearer and bluer shades.

The process for the preparation of the simple disazo dyes of S ₁ -amido-α ₄ -naphthol-β ₃ -monosulfonic acid consists essentially in that one mol. of the acid mentioned, while the mixed dyes are obtained in such a way that either 1 mole of this acid is combined with 1 mole of a tetrazo compound and then 1 mole of a phenol, amine, diamine, amidophenol, amidophenol ether or with the intermediate product obtained the sulfo respectively. Carboxylic acid one of these. It connects derivatives or first represents the intermediate product of 1 mole of tetrazo compound and 1 mole of one of the components mentioned and then _{allows 1 mole of the Ct 1} - amido - o _% - naphthol - β ₃ - monosulfonic acid to act on the same.

Of the diamines, the following are used with particular advantage:

Benzidine, diamidophenyltolyl, tolidine, Diamidoalkyloxydiphenyl, diamidodiphenol

ether, diamidodiphenylene oxide, diamidostilbene disulfonic acid, p-phenylenediamine; among those used to represent the mixed combinations serving components the following:

Salicylic acid, α, - naphtylamine -Ct ₂ - monosulfonic acid, Ci ₁ - naphtylamine -β ₄ - monosulfonic acid, cij-naphtylamine-cij a ₄ - disulfonic acid S, ß, - naphtylamine - ß ₄ - monosulfonic acid, Ct ₁ -naphthol -Ct ₂ - monosulfonic acid, Ct ₁ - naphtholß ₂ a ₄ -disulfonic acid (ε), ßj-naphthol-ß ^ monosulfonic acid, a _; Amido-ß, -naphthol ether-ß ₃ -monosulfonic acid, α, - amido - α ₄ - naphtholß ₂ ßg-disulfonic acid, ßj-amido-a ₄ -naphthol-ß ₈ -monosulfonic acid (γ) and α, ct ₄ -dioxynaphthalene -a-monosulfonic acid.

When representing the ρ - phenylenediamine dyes, it is advantageous to use the p-nitroaniline or ρ - amidoacetanilide to start with, their diazo compounds with the relevant To couple components, then to reduce or reduce the nitro group. the acetyl group to split off, to diazotize the amidoazo body again and then with the relevant To combine components (see Schultz, Chemie des Steinkohlentheers, 2nd edition, Vol. 2, p. 263).

The following examples may serve to explain the process for preparing the dyes from Ct ₁ a ₄ - amidonaphthol-βg-sulfonic acid:

Example I.
Dye from tolidine and 2 mol. Ci ₁ Ci ₄ -amidonaphtol-ß ₃ -monosulfonic acid.

A solution of tetrazoditolyl corresponding to 21.2 kg of tolidine is poured into a well-cooled, soda-alkaline solution of 50 kg (= 2 mol.) _{Of α, α 4} -amidonaphthol-β ₃ -monosulfonic acid.

The formation of the disazo dye begins immediately and is completed after about 24 hours.

Dye from:

I. Benzidine 2. Diamidophenyltolyl 3- Tolidine 4- Diamidoethoxydiphenyl 5 · Diamidodiphenol ether 6th Diamidodiphenylene oxide 7 · Diamidostilbene disulfonic acid

3. p-phenylenediamine

+ 2 moles.

The dye is isolated, pressed and dried in the usual way. He dyes unheated ones Cotton in blue tones.

Example II.

Mixed dye from benzidine, ι mol. Ci ₁ -naphtol - a ₂ - monosulfonic acid and ι mol. Ol ₁ a ₄ - amidonaphtol - ß ₃ -

monosulfonic acid.

18.4 kg of benzidine are diazotized and the resulting solution of tetrazodiphenyl is allowed to flow into a solution of 24.6 kg of the sodium salt of C ^ -naphthol-C ^ -monosulphonic acid (Nevile-Winther), to which 30 kg of sodium acetate have been added. When the formation of the intermediate product has ended, a well-cooled, soda-alkaline solution of 24 kg of oil ₁ a ₄ - amidonaphthol - ß ₃ - monosulfonic acid is added.

The formation of the mixed dye, which begins immediately, is expediently through Warming finished. The dye is then isolated in the usual way, praised and dries it.

The same produces violet nuances on unheated cotton.

If you replace in Examples I. and II. The tetrazo compounds of tolidine respectively. Benzidine by the equivalent amount of another of the tetrazo compounds listed above respectively (in Example II.) the c ^ -naphtol-c ^ -monosulfonic acid by another of the. components mentioned above, one arrives at the analogous products.

The coupling of the mixed dyes can also be carried out in the reverse order, ie first combine the tetrazo compounds mentioned with the Ct ₁ c ^ -amidonaphthol ₃ -monosulfonic acid and combine the intermediate products obtained with the mentioned components.

The dyes obtainable by the present process have the following nuances:

naphtol-ß ₃ -

monosulfonic acid

blue blue blue greenish blue green Blue blue blue blue gray

Dye from:

■ 9- Benzidine ΙΟ. Tolidine I I. Diamidodiphenol
ether 12th · 3 · H- 15- 16. ■ 7 · ΐ8. I ₉ . 20th

Salicylic acid Brown itj-naphtholamine-cij-monosulfonic acid red-brown c ^ -Naphtol-cts-monosulfonic acid violet «! -Amido - ^ - naphtol-ßa ß _s -disulfonic acid Gray a ₁ -naphtholamine-ß ₄ -monosulfonic acid Brown ß ₁ -naphthylamine-ß ₄ -monosulfonic acid red-brown ß ₁ -naphtol-ß ₄ -monosulfonic acid blue-violet Ci ₁ c ^ -Dioxynaphthalene-α-monosulfonic acid blue £ ti-naphthylamine-a ₂ a ₄ -disulfonic acid S. violet «! -Emido-ß ^ naphthol ether-ßg-monosulfonic acid violet gray a _I -naphtol-ß ₂ K ₄ -disulfonic acid (ε) blue ß ^ amido-c ^ -naphtol-ßs-monosulfonic acid (γ) greenish blue.

Claims (2)

Patent Claims: 1. Process for the preparation of simple and mixed disazo dyes from the tetrazo compounds of diamines suitable for the preparation of substantive azo dyes and the α-amido- _{α 4} -naphthol-β ₃ -monosulfonic acid. 2. Execution of the under i. protected process using the following diamines for the representation of the simple and mixed dyes: Benzidine, diamidophenyltolyl (according to Pat. 50983), tolidine, diamidoalkyloxydiphenyl (according to Pat. 46134), diamidodiphenol ether, diamidodiphenylene oxide (according to Pat. 51570), diamidostilbene disulfonic acid (according to Pat. 38735), p-phenylenediamine and the following components to represent the mixed dyes: Salicylic acid, O ₁ - naphthylamine - a. ₂ - monosulfonic acid, Ct ₁ - naphthylamine - ß ₄ -monosulfonic acid, aj-naphthylamine-a. ₂ a ₄ -disulfonic acid S, ß, - naphthylamine - ß ₄ -monosulfonic acid, ttj-naphthol-ag-monosulfonic acid, O ₁ - naphthol - ß ₂ a ₄ - disulfonic acid (ε), ß _t -naphthol-ß ₄ - monosulfonic acid, CL ₁ - amido - ßj - naphthol ether - ß ₃ -monosulfonic acid, aj-amido - ^ - naphtholß ₂ ß ₃ - disulfonic acid (according to Pat. 70201), ßj - amido - α ₄ - naphthol - ß ₃ - monosulfonic acid ( y) (according to Pat. 57857) and cl _} a ₄ -dioxynaphthalene-a-monosulfonic acid.