DE1153841B - Process for the preparation of water-insoluble monoazo dyes - Google Patents

Description

GERMAN

PATENT OFFICE

F 31572 IVc / 22 a

REGISTRATION DATE: JULY 2, 1960

NOTICE
THE REGISTRATION
AND ISSUE OF
EDITORIAL: SEPTEMBER 5, 1963

It has been found that valuable, water-insoluble monoazo dyes are obtained if the Diazonium compounds from amines of the general formula

Method of manufacture
of water-insoluble monoazo dyes

NH ₂

Y-NH ₂

wherein X denotes hydrogen, a halogen atom, an alkyl or alkoxy group and Y _{denotes a CO or SO 2} group, with azo components of the general formula

Applicant:

Farbwerke Hoechst Aktiengesellschaft

formerly Master Lucius & Brüning,

Frankfurt / M.

OH -HN 1 -NH- C ₆ H ₅ CO Ri -J- -CO-

Dr. Konrad Lohe and Dr. Joachim Ribka,

Offenbach / M.,
have been named as inventors

wherein Ri and R _{2 are} hydrogen, a halogen atom, an alkyl or alkoxy group, couples.

The diazo components used in the process according to the invention are preferably m and p-aminobenzenesulfonic acid amides or carboxylic acid amides into consideration, for example l-aminobenzene-3- or -4-carboxamides or sulfonic acid amides, 1-amino-l-halogenobenzene-S-carboxamides or sulfonic acid amides, 1-amino-1-alkylbenzene-S-carboxamides or sulfonic acid amides, l-amino-2-alkoxybenzene-5-carboxamides or sulfonic acid amides.

The 1- (2 ', 3'-oxynaphthoylamino) -4-benzoylaminobenzenes used as azo components in the process of the invention the formula given are easily accessible by known methods, for example by reacting 2,3-Oxynaphthoic acid with the corresponding l-amino-4-benzoylaminobenzenes in a suitable Solvent, for example chlorobenzene, toluene or pyridine, in the presence of a condensing agent, for example phosphorus trichloride.

The dyes are produced by methods known per se, for example by Coupling of the diazonium compounds with the azo components in an aqueous medium in the presence a wetting or dispersing agent.

The dyes obtainable by the process according to the invention are water-insoluble pigments which are characterized by good solvent fastness. They are suitable for manufacture of colored lacquers or lacquer formers as well as solutions of acetyl cellulose, nitrocellulose, natural resins or synthetic resins, such as polymerization or condensation resins, e.g. B. aminoplasts, phenoplasts, polystyrene, polyethylene, polyacrylic compounds, Polyvinyl chloride, rubber, casein or silicone resins. They are also suitable for the Pigment printing on a substrate, in particular on a textile fiber, as well as on other two-dimensional Forms, for example paper.

309 670/279

The dyes can also be used for other uses, e.g. B. in finely divided form for dyeing of rayon made of rayon or cellulose ethers and cellulose esters, polyamides or polyurethanes in the spinning pulp or for dyeing paper, use.

Compared to the water-insoluble monoazo dyes known from German patent specification 673 082 those obtainable by the present process are characterized by a similar composition Dyes are characterized by better solvent fastness.

example

17.1 parts by weight of l-amino ^ -chlorobenzene-S-carboxamide "are dissolved hot with 50 parts by volume of 5N hydrochloric acid and 175 parts by volume of water and diazotized N sodium nitrite solution, after addition of ice at 5 ⁰ C with 20 parts by volume. 5 The diazo

is clarified and at 50 ° C with an aqueous suspension of 40.6 parts by weight of l- (2 ', 3'-oxynaphthoylamino) - 2 - methyl - 4 - benzoylaminobenzene, obtained by dissolving this compound in dilute Sodium hydroxide solution and precipitation with glacial acetic acid in the presence of an action product of about 20 mol Ethylene oxide was produced on 1 mole of octadecyl alcohol, combined. The one after the coupling has ended deposited dye is filtered off, washed and dried. It represents an orange-red Powder.

The nitrocellulose lacquers made with the dye result in a yellow-tinged red finish with good overspray fastness. By incorporating the The dye in polyvinyl chloride is yellowish-tinged red and has very good resistance to bleeding. The table below also contains a number of further components which can be used according to the invention as well as the color tones of the

zo provided dyes.

Diazo component Azo component hue l-amino ^ -methylbenzene-S-carboxylic acid-
amide l- (2 ', 3 ^/ -oxynaphthoylamino) -2-methyl-
4-benzoylaminobenzene Red l-aminobenzene-3-carboxamide the same Orange red 1-aminobenzene-4-carboxamide the same Red l-aminobenzene-3-sulfonic acid amide the same Red orange l-Armno-2-chlorobenzene-5-sulfonic acid amide the same Red l-amino ^ -chlorobenzene-S-carboxylic acid-
amide 1 - (2 ', 3' -oxynaphthoylamino) -4-benzoylamino-
benzene Yellow Red l-aminobenzene-3-sulfonic acid amide the same Red orange l-amino ^ -methylbenzene-S-caroonic acid-
amide 1 - (2 ', 3' -oxynaphthoylamino) -2-methyl-
4-benzoylamino-5-methoxybenzene Red l-amino ^ -methoxybenzene-S-carboxylic acid-
amide l- (2 ', 3'-oxynaphthoylamino) -2-chloro-
4-benzoylamino-5-methylbenzene Red the same l- (2 ', 3'-oxynaphthoylamino) -2-methyl-
4-benzoylaminobenzene Red 1-aminobenzene-4-sulfonic acid amide the same Red l-amino ^ -methoxybenzene-S-carboxylic acid-
amide l- (2 ^/ , 3'-oxynaphthoylamino) -4-benzoylamino-
benzene Red the same l- (2 ', 3'-oxynaphthoylamino) -2-methoxy-
4-benzoylaminobenzene Red 1-aminobenzene-3-sulfonic acid amide 1 - (2 ', 3' -oxynaphthoylamino) -2-chloro-
4-benzoylamino-5-methoxybenzene Red orange l-Amino-2-chlorobenzene-5-carboxamide l- (2 ', 3'-oxynaphthoylamino) -2-chloro-
4-benzoylamino-5-methylbenzene yellowish
Red the same l- (2 ', 3'-oxynaphthoylamino) -2-chloro-
4-benzoylaminobenzene orange l-amino ^ -methoxybenzene-S-carboxylic acid-
amide 1 - (2 ', 3' -oxynaphthoylamino) -3'chlor-
4-benzoylaminobenzene bluish tint
Red

Diazo component Azo component hue l-amino-2-diethylbenzene-5-carboxylic acid
amide l- (2 ', 3'-oxynaphthoylamino) -3-chloro-
4 - benzoylaminobenzene Red l-amino ^ -methoxybenzene-S-carboxylic acid-
amide l- (2 ^/ , 3'-oxynaphthoylamino) -3-methoxy-
4-benzoylaminobenzene Red the same l- (2 ', 3'-oxynaphthoylamino) -3-methyl-
4-benzoylaminobenzene Red l-Amino - ^ - chlorobenzene-S-carboxamide the same Red orange l-amino - ^ - methylbenzene-S-carboxylic acid
amide the same Red 1-aminobenzene-3-sulfonic acid amide the same yellowish
Red 1-aminobenzene-4-sulfonic acid amide the same Bright red 1-aminobenzene-4-carboxamide the same Red l-amino ^ -methoxybenzene-S-carboxylic acid-
amide l- (2 ', 3'-oxynaphthoylamino) -2-methoxy-
4-benzoylamino-5-methylbenzene Red l-amino ^ -methylbenzene-S-carboxylic acid-
amide the same Red l-Amino - ^ - chlorobenzene-S-carboxamide l- (2 ', 3'-oxynaphthoylamino) -2-methyl-
4-benzoylamino-5-chlorobenzene Red l-amino ^ -methoxybenzene-S-carboxylic acid-
amide the same Red the same 1 - (2 ', 3' -oxynaphthoylamino) -2,5-dimethyl-
4-benzoylaminobenzene Red l-Amino ^ -chlorobenzene-S-carboxamide the same orange l-amino ^ -methoxybenzene-S-carboxylic acid-
amide l- (2 ', 3 ^/ -oxynaphthoylamino) -2,5-dichloro-
4-benzoylaminobenzene Red l-Amino ^ -chlorobenzene-S-carboxamide the same Red orange l-amino ^ -methoxybenzene-S-carboxylic acid-
amide l- (2 ^/ , 3'-oxynaphthoylamino) -2-chloro-
4-benzoylamino-5-methoxybenzene bluish tint
Red the same l- (2 ', 3'-oxynaphthoylamino) -2-methyl-
4-benzoylamino-5-methoxybenzene bluish tint
Red the same 1 - (2 ', 3' -oxynaphthoylamino) -2-chloro-
4-benzoylaminobenzene Red the same l- (2 ^/ , 3'-oxynaphthoylamino) -2-methoxy-
4-benzoylamino-5-chlorobenzene Red l-amino - ^ - methylbenzoM-carboxylic acid-
amide l- (2 ', 3'-oxynaphthoylamino) -2,5-dimethyl-
4-benzoylaminobenzene Red l-Amino ^ -chlorobenzoM-carboxamide 1 - (2 ', 3' -oxynaphthoylamino) -3-methyl-
4-benzoylaminobenzene Red l-amino ^ -methoxybenzene ^ -carboxylic acid-
amide l- (2 ^/ , 3 ^/ -oxynaphthoylamino) -2-methyl-
4-benzoy'aminobenzene Red l-amino - ^ - methoxybenzene-S-sulfonic acid-
amide 1 - (2 ', 3' -oxynaphthoylamino) -
4-benzoylaminobenzene Red the same l- (2 ', 3 ^/ -oxynaphthoylamino) -2-methyl-
4-benzoylaminobenzene bluish tint
Red the same l- (2 ', 3 ^/ -oxynaphthoylamino) -2-chloro-
4-benzoylaminobenzene Red l-amino ^ -methylbenzene-S-sulfonic acid-
amide l- (2 ', 3'-oxynaphthoylamino) -3-methyl-
4-benzoylaminobenzene Red the same l- (2 ', 3'-oxynaphthoylamino) -2-methoxy-
4-benzoylamino-5-chlorobenzene bluish tint
Red

Claims (1)

PATENT CLAIM: Process for the preparation of water-insoluble monoazo dyes, characterized in that the diazonium compounds are obtained from amines of the general formula NH ₂ Y-NH ₂ where X is hydrogen, a halogen atom, an alkyl or alkoxy group and Y is a CO- or SOo group means with azo components the general formula OH CO-HN
Ri NH-CO-C ₆ H ₅ R ₂ wherein Ri and R _{2 are} hydrogen, a halogen atom, an alkyl or alkoxy group, couples. Publications considered: German Patent No. 673 082. When the application was announced, two color tables with explanations were laid out.