DE741470C - Process for the production of acidic wool dyes - Google Patents

Description

Process for the preparation of acidic wool dyes Addition to patent 687 607 Subject of 4es patent 687 607 is a process for the preparation of acidic wool dyes, which consists in using nitro compounds of the general formula (in which Y is halogen or an alkoxy group and X is an alkylsulphone, aryl, sulphone or cycloalkylsulphone group) with compounds of the general formula R, -NH-R2-NH2 (in which R, aryl or cycloalkyl, R2 is aryl and R1 or R2 or R1 and R2 contain a sulfonic acid group) condensed. It has now been found that one arrives at equally valuable sour wool, dyes, substances, if one uses nitro compounds of the general formula (wherein Y is halogen or an alkoxy group and Z is -SO2- or - 02S - aryl - S 02 -) condenses with the above-mentioned amino compounds of the diphenylamine series.

The acidic wool dyes obtained in this way are in particular .by a good fastness to washing, perspiration, seawater and ironing of the dyeings obtained therewith excellent.

Example i 28.6 kg of 4-aminodiphenylamine-2-sulfonic acid sodium become dissolved in about ten times the amount of water. 18.8 kg of 4 # 4'-dichloro-3 are then added . 3'-dinitrodiphenyl sulfone, 10 kg of sodium acetate and about 300 liters of alcohol are added and heated to boiling for several hours. The alcohol is then distilled off and after before filtering, salt out the filtrate with table salt. The dye thus obtained dyes wool from an acid bath in yellow-brown shades with excellent fastness properties.

Example 2 Condensed to 31.6 kg 4 '-methoxy-4-aminodiphenylamine-2-sulfonate in an analogous manner, i as in Example 1 with 8.8 kg 4 # 3 # 4'-dichloro-3'-dinitrodiphenylsulfone in the presence of 5 kg of magnesium oxide, a dye is obtained which dyes wool from an acid bath in brown shades of equally excellent fastness properties.

A completely analogous dye is obtained when 33 kg of 4'-ethoxy-4-aminodiphenylamine-2-sulfonic acid sodium are used instead of 31.6 kg of the corresponding 4'-methoxy compounds. In contrast, a significantly deeper brown is obtained when using the equivalent amount of 3'4'-dimethoxy-4-ainodiphenylamine-2-sulfonic acid sodium.

Example 3 28.6 kg of 4-aminodiphenylamine-2-sulfonic acid sodium are mixed with about twenty times the amount of 50% aqueous alcohol and 28.3 kg of naphthalene-1-5-di- (3'-nitro-4'-chlorophenyl) -sulfone with a melting point of 306 to 307 ° C in the presence of 10 kg of magnesium oxide in a stirred autoclave heated to about 14o to 15o ° C for a few hours. After conversion into the sodium salt by adding: the appropriate amount of soda, the alcohol is distilled off, impurities are filtered hot, and: the filtrate is evaporated to dryness or salted out with common salt. The dye obtained in this way dyes wool from an acid bath in brown shades which also have good fastness properties.

Analogous dyes are obtained if instead of 28.6 k. ' Sodium 4-aminodiplienylamine-2-sulfonic acid, its 4'-methoxy or 4'-ethoxy compound or similar derivatives are used.

Example 4 63.2 kg of q @ -methoxy-4-, aminodiphenylainin-2-sulfonic acid Sodium and 41 kg of 3 - 3'-Dinitro-4 - 4 '5'-trichlorodiphenyl sulfone are with the about twenty times the amount of 50% aqueous alcohol in the presence of 20 kg of sodium acetate heated under reflux or under pressure until the dye formation ceases is. The alcohol is then distilled off and minor impurities are filtered off and the filtrate either evaporated to dryness or the dye becomes by addition deposited by table salt. The same results in yellow-brown dyeings on wool from an acidic bath equally good fastness properties.

An analogous dye is obtained when. one in place of 41 kg 3 - 3'-dinitro-4. # 4 '5'-trichlorodiphenylsulfone the equivalent amount of 3 # 3'-dinitro-5-methyl-4 # 4' 5'-trichloro-diphenyl sulfone is used.

Example 5 28.6 kg of 4-aminodiphenyla: min-2-sulfonic acid sodium become with about twenty times the amount of 50 ° 1ogen aqueous alcohol and 25.9 kg of benzene i # 3-di- (3'-nitro-4'-chlorophenyl) sulfone in the presence of 10 kg of magnesium oxide! heated in a stirred autoclave for a few hours to 14o to 15o °. After by adding the conversion into the sodium salt caused by the corresponding amount of soda becomes the alcohol distilled off, filtered hot from impurities and from the brown solution of the Salt the dye out with table salt. The same dyes wool from an acid bath in yellow-brown Tones with good fastness properties.

Claims (1)

PATENT CLAIM: Modification of the process according to patent 687 607 for the production of acidic wool dyes, characterized in that. that one nitro compounds of the general formula (in which Y is halogen or an alkoxy group and Z is -SO2- or - 02 S-aryl-S 02 -) with compounds of the general formula R, - NH-R2-NH2 (in which R, aryl or cycloalkyl, R2 is aryl and R1 or R2 or R1 and R2 contain a sulfonic acid group) heated in a molar ratio r: 2 in solvents and in the presence of acid-binding agents. To distinguish the subject matter of the application from the state of the art, the following publications were considered in the granting procedure: German patent specification No. 263 655.28: 2.317 and. 447 0 z5.