DE1719073C - Process for the preparation of water-insoluble monoazo dyes. Eliminated from: 1276843 - Google Patents

Description

I 719073

IZs have been found to be valuable water-insoluble Azo dyes obtained when the diazo compound of 2,5-dichloro-4-cyano-aiiilin with a Amine of the general formula

R,

couples in the p-position to the amino group.

In the general formula, X is hydrogen. Alkyl. Alkoxy. Halogen; R ₁ represents cyanoalkyl. , .- Carboalkoxyäthyl or Tür the radical R ₁ ; R ₁ means a group

Il

-CH ₁ CH ₁ -OCOR ₃

20th

where R _{3 represents} a lower alkyl radical.

The starting component is coupled in the customary manner, preferably in an acidic solution or Suspension.

As coupling components in the process according to the invention, for. B. the amines with the following Formulas are used:

V-N

V-N

CM ₃

V-N

CII ₃

Prints of very good authenticity properties, inslv very good light. Washing and sublining unit.

The dyes are also suitable for dyeing and printing cellulose acetate and triacetyl cellul, ^ and from polyamide and polyacrylonitrile fiber material. The dyes are also distinguished by their good crystallization capacity and good drawability.

Compared to the dye described in US ^{Pat. No. 2 24 C} ) 74 ') (last six diazoc; mponenle of the table on page 5 in combination with the coupling component No. Is of the table on cable 4) is the dye of the formula obtainable according to the invention

Cl

NC -.

VN (C ₁ H ₄ OCtK) C ₁ H ₅ N

Cl

CH ₃

C ₁ H ₄ CN 30 g

C ₂ H ₄ OCOC ₂ H ₅

il

O

C ₂ H ₄ COOCH,

C ₂ H ₄ OCOCH ₃

C)

Il

C ₂ H ₄ CXOCH ₃

V ₂ H ₄ OCOCH, O O

Ij

C ₂ H ₄ OCOCH ₃

V ₂ H ₄ OCOCH ₃ O

The dyes obtainable according to the process are eminently suitable for dyeing and printing more hydrophobic Materials such as textiles or fibers made from aromatic polyesters. / .. H. von Polyälnlen-terephthalatcn or from Komlcnsationspnulii'klcn Terephthalic acid and 1,4- (bis-hydroxymethyl) -nen / ol. On these materials one obtains Färbimucii and the advantage of the better lightfastness of the dyeings on super polyamide fabrics.

example

7 parts by weight of 2,5-dichloro-4-cyano-aniline are dissolved in 400 parts by weight of concentrated sulfuric acid at 0 to 15 ° C. and diazotized with 170 parts by volume of nitrosylsulfuric acid (42 g of nitrite in 100 ml of H ₂ SO ₄ ) with thorough stirring and cooling, and afterwards Poured sth on about 3000 weight of ice for 5 hours. A small excess of nitride is removed with sulfamic acid and the solution is filtered. This solution is then mixed with a solution of 29.7 percentages of the amino compounds of the formula

C ₂ H ₄ OCOCH ₃

■ ^ C ₂ H ₄ OCOCH ₃

'

combined, partially neutralized with dilute sodium hydroxide solution and the coupling with sodium acetal was completed. The dye is filtered and soaked. When dry it forms an orange-red powder that dissolves in organic solvents, like acetone or alcohol, dissolves with an orange color. It dyes acetate silk and polyamide fabric. through Suitable additives brought into leash distribution, in clear orange-red tones of good washing and washing Lightfastness on.

In the same way, the following dye can be obtained from the corresponding starting component, the fabric made of aromatic polyesters, such as polyethylene terephthalate, has a yellowish red color:

CI

NC- '

egg

ν - /

CH ₃

Il

C ₂ H ₄ OCOCH ₃
V ₂ H ₄ OCOCH,

• I! · ο

Claims (1)

Claim: 1. Process for the production of water-insoluble FklonoazofarhstolTe, characterized in that the dia / over bond of 2,5-difhlor-4-cyano-aniline with an amine of the general formula R ₁ -N R, wherein X is hydrogen, alkyl, alkoxy or halogen and R _{1 is} a group -CH ₂ CH ₂ -OCOR, where R _{3 is} a lower alkyl _{resl and where R 2 is} cyanoalkyl. / i'-L'arbualkoxyäthyl or represents a radical R ₁ , couples in p-position to the amino group.