US2175795A

US2175795A - Monoazo dyestuffs soluble in water

Info

Publication number: US2175795A
Application number: US196901A
Authority: US
Inventors: Fischer Erich; Gmelin Walter
Original assignee: General Aniline Works Inc
Current assignee: General Aniline Works Inc
Priority date: 1937-03-24
Filing date: 1938-03-19
Publication date: 1939-10-10
Anticipated expiration: 1956-10-10

Description

Patented Oct. 10, 1939 UNITED STATES PATENT OFFICE MONOAZO DYESTUFFS SOLUBLE IN WATER Erich Fischer and Walter Gmelin, Bad Soden in Taunus, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application March 19, 1938, Serial No. 196,901. In Germany March 24, 1937 5 Claims.

wherein R. stands for an aryl radical not containing any group lending solubility and X stands for hydrogen or alkyl.

We have found that valuable monoazo-dyestuffs soluble in water are obtainable by combining in an acid or alkaline medium with any diazo-compound of the benzene series not containing any group lending solubility, an aminohydroxynaphthalene of the general constitution:

wherein R stands for a naphthalene nucleus which may contain further substituents, but must not contain a sulfonic acid group, X stands for hydrogen or alkyl with the proviso that derivatives of 1-amino-7-hydroxynaphthalene are excluded.

The dyestuffs thus obtained are especially suitable for dyeing wool yellow-brown, brown-red to Bordeaux-red tints from an acid bath below boiling temperature, for instance, at 60 to 90 C.

The sulfoalkylamino-hydroxynaphthalenes used as coupling components may be obtained by condensing the corresponding amino-hydroxynaphthalenes with halogenalkylsulfonic acids.

The following examples serve to illustrate the invention, but they are not intended to limit it thereto, the parts being by weight, unless otherwise stated. The ratio between parts by weight and parts by volume is that which exists between the kilo and the liter:

1. Into a solution obtained from 253 parts of 2-sulfethylamino-7-hydroxynaphthalene, water and 212 parts of sodium carbonate there is run a diazo-solution prepared in the usual manner from 93 parts of aminobenzene. When the coupling is complete the dyestuff is salted out, fil tered with suction and dried. It dyes wool throughout in an acid bath below boiling temperature, for instance at 60 C. to 80 (3., redbrown even tints. The dyestuff corresponds with the following formula:

2. If in Example 1 the aminobenzene is exchanged for 107 parts of 1-amino-2-methylbenzene, a dyestuif of similar properties is obtained.

3. By combining a diazo-solution from 151 parts of 1-aminobenz ene- 3-carboxylic jacid methyl-ester with a solution of 253 parts of 2- sulfethylamino-Z-hydroxynaphthalene or 267 parts of 2-sulfop-ropylamino-'7-hydroxynaphthalene and 220 parts of sodium carbonate in water there are obtained after salting out dyestufis which dye wool throughout already at 70 C. from an acid bath full brown even tints.

4. If in Example 3 the l-aminobenzene-3-carboxylic acid methyl-ester is exchanged for 147 parts of 1-amino-5.6.7.8-tetrahydronaphthalene, a red-brown product is obtained which dyes wool throughout below boiling temperature from an acid bath Bordeaux even tints.

5. If in Example 1 the 2-sulfethylamino-7-hydroxynaphthalene is exchanged for 253 parts of 2-.sulfethylamino-fi-hydroxynaphthalene a dyestuff of similar properties is obtained.

6. A dyestuif dyeing wool below boiling temperature in an acid bath brown-red even tints is obtained if in Example 1 the 2-sulfethylamino-7- hydroxynaphthalene is exchanged for the same Weight of 2-sulfethylamino-8-hydroxynaphthalene.

7. 107 parts of l-amino-i-methoxybenzene are diazotised in the usual manner and the diazosolution is combined in the presence of sodium carbonate in excess with an aqueous solution of 239 parts of 2-sulfomethylamino-'I-hydroxynaphthalene, while cooling. The dyestuff obtained is salted out and dried. It dyes wool throughout at 60 to 80 C. in an acid bath brownred tints.

8. 127.5 parts of 1-amino-3-chl0robenzene are diazotised in the usual manner and the diazocompound is introduced into a well cooled solution of 267 parts of 2-sulfethylmethylamino-7- hydroxynaphthalene rendered alkaline by means of sodium carbonate. When the coupling is complete the product obtained is salted out, filtered with suction and dried. A dyestuff is obtained which dyes wool throughout below boiling temperature in an acid bath red even tints.

9. If in Example 8 the Z-sulfethylmethylamino-l-hydroxynaphthalene is exchanged for 281 parts of 2-sulfethyl-ethylamino-7-hydroxynaphthalene a dyestufi" of similar properties is obtained.

10. 123 parts of l-amino-i-methoxybenzene are diazotised in hydrochloric acid in excess with 69 parts of sodium nitrite. The diazo-solution obtained is run into an aqueous solution, cooled to C., of 253 parts of 2-sulfethylamino-7-hydroxynaphthalene and sodium. carbonate in excess. The dyestufi? obtained is separated by means of sodium chloride and dried. It is a brown powder which dissolves easily in water and has the property of dying W001 throughout in an acid bath, for instance, at 70 C. Bordeaux-brown even tints.

We claim:

1. The water-soluble monoazo-dyestufis of the following general formula:

wherein R means a radical of the benzene series not containing a group lending solubility, X stands for one of the group consisting of hydrogen methyl and ethyl, and Y for one of the group consisting of methyl, ethyl and propyl, being brown powders which dye wool from an acid bath below boiling temperature, at 60 C. to 90 C., yellow-brown, brown-red to Bordeaux-red even shades.

2. The water-soluble monoazo-dyestufis of the following general formula:

HO N wherein R means a radical of the benzene series not containing a group lending solubility, X stands for one of the group consisting of hydrobeing a brown powder which dyes wool throughout in an acid bath below boiling temperature, for instance at 60 C.-80 C., red-brown even shades.

4. The water-soluble monoazo-dyestufi of the following formula:

being a brown powder which dyes wool throughout in an acid bath below boiling temperature, for instance, at 70 C., full brown even shades.

5. The water-soluble monoazo-dyestuff of the following formula:

being a brown powder which dissolves easily in water and dyes wool throughout in an acid bath below boiling temperature, for instance, at 70 C., Bordeaux-brown even shades.

ERICH FISCHER. WALTER GMELJN.