DE2031561A1 - Process for the production of basic dyes - Google Patents

Description

Process for the production of basic dyes

The invention relates to new basic dyes for dyeing of PAlT fibers.

According to the West German interpretative document 1 287-16 it is known dyes of the formula

Anion

to produce, where R is hydrogen, the methyl or ethyl group, X is hydrogen, chlorine or the methyl group and! substituted pyrazolone radicals or - optionally Substituted - arylamines represent, but occur. There are no diamines as substituents. The so produced However, dyes usually show insufficient solubility

109826/1750

- 2 - 4 * 04.20 / 1492-

i) ie the French patent specification 1 421 912 and the West German one Auslegeschrift 1 011 396 show no benaimidazole compounds as in the above-mentioned interpretation, "but have a dye component as a substituent Diamino compounds.

The aim and object of the invention was _{to create 9} dyes for dyeing PAN fibers which show better solubilities than those of Auslegeschrift 1 287 716 and which in addition have nuances with higher luminosity with good coloring properties.

It has now been found that new dyes can be used for dyeing of PAH fibers of the general formula

whereby

At

u.

Alkyl with 1 to 4 carbon atoms

which can be the same or different,

H, -CH-;

-CH ₃ '\ _c

10 Π 826/1750

and

BATH

. ■ · 3 - ^ 04.20 / 1492

At anlons according to the Trimhanden (?) - charges

represent, can produce if you 5-Amino.-2-methylbenzimidasol diazotized, with amines of the general formula

3 h

-N-CH ₂ OH ₂ X III

coupling, where R ₂ , S ^, R ^ and X have the meaning given above, and then alkyliei't «

It is recommended to use the 5-An & no-2 ~ methyrbenzimidazole to be prepared shortly before the diazotization by acid hydrolysis of the corresponding 5-acetamino compound. I.

The alkylation is carried out with alkylating agents such as Diethyl sulfate or alkyl halide carried out.

However, the procedure can also be modified to this extent. be changed than one of 1,3-diethyl-5-amino-2 ^ iethylbenzimidaaoliumsalz can go out, which is then diazotized and coupled with an Amiη of the general formula III then there is no need for subsequent alkylation

109826/1750 _BAD ORIGWAt?

- 4 - 4 04.20 / 14-92

In this case, too, one can expediently start from the corresponding 5-acetamino compound, which is converted into the 5-amino compound by acid hydrolysis before diazotization

The dyes according to the invention show compared to the closest comparable dyes of the West German interpretative document 1 287 716 a significantly higher solubility · When compared with dyes from the West German Auslegeschrift 1,011,396 and French patent 1,421,912 give the dyes which can be prepared according to the invention much more brilliant nuances «

The following examples are intended to further the invention explain, without this being limited to it.

example 1

9 | 4 parts by weight of 5-Acetafl & nö-2-ethylbenzimidazole in 100 ml of water, to which 30 ml of hydrochloric acid are added by refluxing into the 5-amino-2-methylbenaimldazole transferred "

This solution is then used immediately for the diazotization · The diazotization takes place as usual at -2 to

The solution of the diazo compounds obtainable in this way it is left in a solution of 16-4 parts by weight for coupling N ^ Ithyl-BHP ^ oyl-eminoethyl-trimethylaomoniin 100 al water offered Ö- - 2 ° run in · with

1 0 9 8 2 _6/1 7 5 Q BAD original

■ '■ - 5 -. 4.04. 20 / 14-92

Saturated sodium acetate solution is adjusted to pH 4-5 posed. The clutch is finished after a short time. The dye is precipitated with HaOl and dried. The dried dye is dissolved in 150 ml of chlorobenzene (anhydrous) suspended and after adding about 7 Parts by weight of MgO and 18.5 parts by weight of dimethyl sulfate methylated at boiling point. When the ethylation has ended, the dye is removed from chlorobenzene. separates and suspended in water. Insoluble constituents are filtered off, and the dye is removed from the Solution precipitated by adding table salt and ZnOl ^ solution.

This dye dyes PAN and mixed polymer fibers with a minimum proportion of 50 % PAN. acetic acid bath in scarlet tones with very good general fastness properties.

Example 2

9 | 4 parts by weight of 5-acetamino-2-methylbenzimidazole converted into the diazo compound as described in Example 1 and this with 10.3 parts by weight of N-diethylaminoethyl-m * toluidine coupled. The dye obtained in this way is methylated analogously to Example 1. PAN fibers are in red tones with very good fastness properties stained.

BATH

109826717BO

2031 SB

- 6 - 4.04.20 / 1492

Example 3

The diazo solution prepared from 9.4 parts by weight of 5-acetamido-2 ~ methyl- »~ benz imidazole to the solution of 10.3 parts by weight of Nn-Eropyl-N-dimethylamino» »ethylaniline at pH 4 - 5 × coupled After Methy" lation of the dye according to the described in Example 1 »

• In the same way a dye is obtained, the PAN-Pasern in scarlet tones with "very good general fastness properties

stains.

Example 4

28.7 parts ^ -Aniino-I ^ Hiimethyl-S-methylbenziiiiidazoliujiH · metasulfate are dissolved in 250 ml of water · This solution is in a known manner after adding 30 ml of hydrochloric acid conc · diazotized at 0-5 °.

For coupling, the diazo solution is left to form a hydrochloric acid solution Solution of 20.6 parts of N-diethylaminoethyl-m ~ tolaidin run in at 0-5 °.

The termination of the coupling is achieved by adding Hatriuinr acetate solution reached. The dye is isolated by adding sodium chloride. PAN fibers are produced with good general fastness properties stained red.

. = - ■ BAD ORIGINAL

109B26 / 1750

Claims (1)

4.04.20 / 1492 Patent to ρ back. e 1, dyes for dyeing PAN fibers of the general formula whereby and -llaN - ^^ - IWJHgCHgX To (II) Alkyl having 1 to 4 carbon atoms,, which may be the same or different can, H, -CH-, ' H* At represent· ^
C. CH- CH ₃ CH ₃ CH ₃ and Anions according to the φ present 109826/1750 BATH ORIGINAL .04 ·. 20/1492 Process for the preparation of new dyes for dyeing of PAN fibers, characterized in that 5 "~ amino-2-methylbenzimidazole diazotized, with amines of the general formula (III) is coupled and then with alkylating agents to compounds of the general formula -N = N- is alkylated, where and Η *, Alkyl with 1 to 4 carbon atoms, which can be the same or different, H, H, 10 982-6 / 1 7BO. XIH ₃ Anions corresponding to the .Q charges represent. 3. Modification of the method according to claim 2, characterized in that 113-diethyl-5-amino-2-methylbenziinlaa- * zol and diazotized with amines of the general formula (III) is coupled Rbg / E 10 9 8 2 ß / 1 7 50