DE1263950B - Process for the preparation of water-insoluble monoazo dyes - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Int. Cl .:

Number:
File number:
Registration date:
Display day:

C09b

German class: 22a-l

1263 950
F31100IVc / 22a
April 28, 1960
March 21, 1968

It has been found that water-insoluble monoazo dyes of the general formula

(I)

■ ν;

- CH ₂ - SO ₂

in which Z a non-water-solubilizing negative substituent and Ri a hydrogen atom or denotes a low molecular weight alkyl group and the benzene nuclei A, B and C denote further ones which do not make them soluble in water May contain substituents, obtained by the diazonium compound of an amine of the benzene series, which is in the 4-position carries negative, non-water-solubilizing substituents, and the additional non-water-solubilizing May contain substituents in the benzene nucleus, with an amine of the general formula

, R ₁

(Π)

CH ₂ - SO,

in which Ri is a hydrogen atom or a low molecular weight Alkyl group and the benzene nuclei A and B denote water-insolubilizing substituents can contain, in 4-position couplings.

As amines on which the diazo components used and which are used in 4-position contain a negative, non-water-solubilizing substituent, such 1-aminobenzene derivatives are used in the 4-position, for example, a halogen atom, a Contain nitro, nitrile or trifluoromethyl group, and also on the benzene nucleus by further groups that do not make water solubility, such as halogen atoms, nitro and alkoxy groups, can be substituted.

The amines of the above-mentioned general that are used as azo components Formula (II) can on the benzene nucleus A by non-water-solubilizing groups, such as, for example Halogen atoms, alkyl, trifluoromethyl, alkoxy or acylamino groups, and on the Behzol nucleus B through non-water-solubilizing groups, such as halogen atoms, alkyl, trifluoromethyl or alkoxy groups.

Process for the preparation of water-insoluble monoazo dyes

Applicant:

Farbwerke Hoechst Aktiengesellschaft
formerly Master Lucius & Brüning,
6000 Frankfurt

Named as inventor:

Dipl.-Chem. Dr. Helmut Gies, 6238 Hofheim;

Dipl.-Chem. Dr. Wilhelm Happe,

6208 Schwalbach

The coupling takes place in an acid medium, optionally in the presence of acid-binding agents such as sodium acetate, magnesium oxide or pyridine. The new dyes obtainable in this way are expediently processed in the customary manner, by kneading with known dispersants, to give coloring preparations. Today's dyes produce on materials made of polyester fibers, in particular those made of polyethylene terephthalate fibers, valuable dyeings with excellent fastness properties, above all very good sublimation fastness properties. For dyeing polyester materials, the new dyes are suitably used in the form of said dye preparations, which pass in this case in aqueous suspension at temperatures above 100 C ¹ under pressure or at about 100 ⁰ C with the addition of customary carriers used.

With the new dyes you get on materials made of polyethylene terephthalate fibers, yellow, orange, red, brown and blue shades.

Compared to constitutional monoazo dyes, which are used as azo component 1- (N-methylsulfonylethyl-N-methylamino) -3-methylbenzene (cf. USA Patent 2,830,043, column 1, lines 55 to 68), the ones obtainable according to the process stand out Monoazo dyes are characterized by a better thermosetting fastness of the polyester dyes.

Example I ^:

19.6.5 g of 2,4,6-trichloro-1-aminobenzene are like customarily diazotized and the resulting diazo solution slowly to a solution of 303 g of l- (N-4'-methyl

809 519/577

■ phenyIsulfonyläthyl-N-methylamino) -3-methylbenzene in 1500 g ■ hydrochloric acid 36%. After one hour, the reaction mixture is diluted to 151 with water and, after 24 hours, the dyestuff which has separated out is filtered off and dried. It represents an orange crystalline powder, the stains in dispersed form a fabric ausPolyäthylenterephthalatfasern in the presence of o-phenylphenol as a carrier at 100 ⁰ C in deep golden yellow shades. The dyeings obtained are very fast to light and sublimation.

Instead of the above-mentioned o-phenylphenol, other carriers, such as, for example, can also be used Diphenyl, chlorobenzene and 2-oxytoluene-3-carboric acid methyl ester, come into use.

Example 2

207 g of 2,6-dichloro-4-nitro-1-aminobenzene are diazotized as usual. The diazo solution thus obtained slowly becomes a solution of 303 g of 1- (N-4'-methylphenylsulfonylethyl - N-methylamino) - 3 - methylbenzene given in 1500 g of 75% sulfuric acid. To

one hour, the reaction mixture is diluted to 151 with water and, after 24 hours, the dyestuff which has separated out is filtered off and dried. It represents a violet brown powder, which stains in dispersed form materials ausPolyäthylenterephthalatfasern at 120 ⁰ C in copper brown tone. The coloration obtained in this way is very fast to light and sublimation.

The following table contains other water-insoluble monoazo dyes, which according to the information of Examples 1 and 2 are available. They correspond to the composition

R-N = N

nc

—CH ₂ —SO ₂ -R ₂

and are identified in the table below by the radicals R, Ri, R ₂ , X and Y and by their color on materials made of polyethylene terephthalate fibers.

R. X Y H R. R ₂ Hue on Materials from example 2,6-dichloro-4-nitro- H Cl CH ₃ 4-methylphenyl Polyethylene tere phenyl CH ₃ phthalate fibers 3 the same H CH ₃ CH ₃ the same Brown the same OCH ₃ H H the same 4th 2,4,6-trichlorophenyl OCH ₃ Cl H the same Brown 5 the same H CH ₃ CH ₃ the same Brown 6th the same H CH ₃ the same orange 7th 2,4-dinitro-6-chloro H NHCOCH ₃ CH ₃ the same yellow 8th phenyl NHCOCH ₃ yellow 9 the same OCH ₃ H the same violet 2,4-dinitro-6-bromo OCH ₃ CH ₃ H the same 10 ° phenyl CH ₃ blue 11 • 2-chloro-4-nitrophenyl H CH ₃ the same blue 2,4-dinitro-6-meth- H H CH ₃ the same 12th oxyphenyl Scarlet fever 13th 4-nitro-2-methoxy H CH ₃ CH ₃ Phenyl Bordo phenyl 14th 2-nitro-4-trifluoro H CH ₃ CH ₃ 4-chlorophenyl Scarlet fever methylphenyl 15th 4-cyano-2,5-dimeth- H NHCOCH3 CH ₃ 4-methoxy orange oxyphenyl phenyl 16 2,4,6-trinitrophenyl OCH ₃ H 4-methylphenyl Golden yellow 17th turquoise

Claims (1)

Claim: 60 Process for the production of water-insoluble monoazo dyes ^ characterized in that that the diazo compound of an amine of the benzene series, which in the 4-position has a negative, non-water-solubilizing Bears substituents and that, in addition, on the benzene nucleus, further non-water-solubilizing May contain substituents with an amine of the general formula ^ CH ₂ -CH ₂ -SO ₂ in which Ri denotes a hydrogen atom or a low molecular weight alkyl group and the Benzene nuclei A and B do not make water soluble . May contain substituents, in acidic medium, optionally in the presence of acid-binding 5 6 the means, with the formation of dyes in which Z is a non-water-solubilizing agent general formula negative substituents and Ri is a hydrogen y \ y \ atom or a low molecular weight alkyl group Z - ( C V- N = N - C A Vi means, and the benzene nuclei A, B and C mean more 5 non-water-solubilizing substituents I can hold the clutch. Considered publications:
^ CH ₂ - CH ₂ - SO ₂ - <f B } German Auslegeschrift No. 1 061 284. When the application was announced, a coloring table with explanations was laid out. 109 519/577 3.6t θ Bundesdruckerei Berlin