US1546328A - Azo dyestuff and process of making same - Google Patents

Description

Patented July 14, 1925.

KARL THIESS, OF SINDLINGEN, NEAR HOCHST-ON-THE-MAIN, GERMANY, ASSIGNOR TO FABBWERKE VORM. MEISTER LUCIUS 80 BR'O'NING, OF HO'OHST-O-N-THE-MAIN, GERMANY, A CORPORATION OF GERMANY.

AZO DYESTUFF AND PROCESS OF MAKING SAME.

No Drawing. Application filed January To all whom it may concern:

Be it known that I, KARL THmss, a citizen of Germany, residing at Sindlingen, near Hochst-on-the-Main, Germany, have invented certain new and useful Improvements in Azo Dyestuffs and Processes of Making Same, of which the following is a specification.

I have found that by combining arylamides of the 2-hydroxynaphthalene-3-carboxylic acid with the hitherto unknown benzaldehyde-azo-a-naphthylamineswhich as such are obtained by the combination of diazotized aminobenzaldehydes with a-naphthylamines capable of being coupled in 4 position-there can be obtained chiefly black dye-stuffs of excellent properties as to fastness notwithstanding the fact that the said dyestuffs contain a free aldehyde group. These dyestuifs may be produced as pigment dyes or on a substratum or on the fibre itself. The latter method is carried out in such a manner that the material impregnated with arylamides of the 2-hydroxynap-hthalene-3-carboxylic acid is treated with a diazo compound of the benzaldehydeazo-l-naphthylamines.

According to the kind of components used, there are obtained reddish-black, black to greenish-black dyeings. The fastness of these dyeings, particularly their fastness to light, may be still enhanced by a treatment with copper salts. As disazo components may be used all aminoazo compounds with a free aldehyde group, which are obtained by coupling diazotized aminobenzaldehydes, their homologues and substitution products with oz-naphthylamine and its derivatives which are capable of being coupled in 4: position.

The following examples illustrate my invention:

1. Some cotton yarn is impregnated with the following solution: I

12 grams of 2.3-hydroxynaphthoic acid- {fi-naphthylamide, 36 com. of caustic soda 34 B., 2 1 ccm. of sodium Turkey-red oil per cent, 500 ccm. of hot water made up with water to 1 litre. The impregnated yarn is 29, 1925. Serial No. 5,647.

wound oil and dyed with a diazo solution which has been prepared in the following manner:

5.5 ams of benzaldehydeazo-a-naphthylamme (produced by means of m-amino benzaldehyde) in the form of a thin-liquid paste, are slowly introduced, while stirring, together with 1.75 grams of sodium nitrite into ice-water and 5 com. of hydrochloric acid 22 B. After the diazotization is complete, the solution is made up with cold water to one litre and the whole is neutralized with sodium acetate.

The grounded yarn is left for some time in the dye-bath, then rinsed, soaped and finished. Thus a full black tint with a somewhat red hue is obtained. The dyestufi dissolves in substance in concentrated sulfuric acid to a violet solution.

2. Some cotton yarn is impregnated with the following solution:

12 grams of 2.3-hydroxynaphthoic acid-@- naphthylamide, 86 com. of caustic soda solution 34 B., 24 com, of sodium Turkey-red oil 50 per cent, 500 ccm. of hot water made upwith water to 1 litre. The impregnated yarn is wound 0E and dyed with a diazo solution which has been prepared in the following nianiier:

5.5 grams of benzaldehyde-azo-ocnaphthylamine (produced by means of p-aminobenzaldehyde) in the form of a thin-liquid paste, are slowly introduced, while stirring, together with 1.75 grams of sodium nitrite into ice-water and 5 ccm. of hydrochloric acid of 22 B. After the diazotization is complete, the solution is made up with cold Water to one litre and the whole is neutralized with sodium acetate.

The grounded yarn is left for some time in the dye-bath, then rinsed, soaped and finished.

Thus a neutral black tint is obtained. The dyestuff dissolves in substance in concentrated sulfuric acid to a violet solution.

3. The dyeing-process is carried out as Y s ecified in Example 1 with the exception t at in the resent case 2.3-hydroxynaphthoic acid-a-nap thylamide is used, the tint obtained being reddish black. The dyestufi dissolves in substance in concentrated sulfuric acid to a green solution.

As the dyestuffs contain a free aldehyde group, they can be converted into compounds soluble in cold Water or hot water by means of bisulfite.

I claim:

1. Process of producing azo dyestuffs, consisting in coupling diazotized benzaldehydeazo-oc-naphthylamines with arylamides of the 2-hydroxynaphthalene-3-carboxylic acid.

2. Process of producing azo dyestuffs, consisting in coupling diazotized l-benzaldehyde 3- lazo-1.-amino-naphthalene)' with arylides of the 2-hydroxynaphthalene-3-carboxylic acid.

3. Process of producing azo dyestufis, consisting in coupling diazotized l-benzaldehyde-3- iazo-1-amino-n'aphthalene) with the fi-naphthylamide of the 2-hydroxynaph- A thalene-3-carboxylic acid.

C 4. As new products, azo dyestufls, substant1ally identical with those obtainable by coupllng diazotized benzaldehyde-azwabeing a bluish-black powder, insoluble in water, soluble in concentrated sulfuric acid with a violet color, giving with bisulfite soluble compounds.

9. As new articles, textile material dyed naphthylamines with arylamides of the 2- hydroxynaphthalene-3-carboxylic acid, being reddish to bluish-black powders, insoluble in water, soluble in concentrated sulfuric acid with characteristic shades of color, giving with bisulfite soluble compounds.

5. As new products, textile material dyed with an azo dyestuff asclaimed in claim 4, the said dyestufl' being formed on the material.v

6. As new products, azo dyestuffs, substantially identical with those obtainable by coupling diazotized 1-benzaldehyde-3-(4- azo-1-aminonaphthalene) with arylamides of the 2-hydroxynaphthalene-3-carboxylic 4 acid, being reddish to bluish-black powders, insoluble in water,'soluble in concentrated sulfuric acid with characteristic shades of color.

. 7. As new products, textile material dyed with the azo dyestuffs claimed in claim 6, the said dyestufi being formed on the material.

8. As a new product, the azo dyestuff of the following formula:

With the azo dyestufi' as claimed in claim 8, the said dyestuff being formed on the material.

In testimony whereof, I aflix my signature.

KARL THIESS.