DE1048374B - Process for the production of dyes - Google Patents

Description

GERMAN

Class 22e 7/02

INTERNAT. KL. C 09 b

PATENT OFFICE

EXPLAINING PAPER 1048 374

F 22873 IVb / 22 e

REGISTRATION DATE: APRIL 2, 1957

NOTICE
THE NOTICE
AND ISSUE OF THE
EXECUTIVE LETTER: 8th YES NU AR 1 959

In the French patent specification 1111 620 is a Process for dyeing synthetic fibers, including those made of polyesters, with condensation products of 1,8-naphthalenedicarboxylic acid or theirs Anhydride and unsubstituted or substituted aromatic o-diamines described. Contain the dyes listed in the examples of this patent specification as a substituent in the benzene nucleus of the o-diamine a chlorine, methyl or methoxy group.

The reworking of these examples showed that the dyes described have a good affinity for Have polyester fiber and the dyeings obtained have good wet and iron fastness properties, but that Fastness to hot air fixation (thermoset fastness) is very low. This deficiency makes the fibrous matter Unsuitable for a wider range of textiles, because most of the dyeing is done using hot air fixation is subjected.

It has now been found that dyes with excellent heat-setting properties can also be obtained which are otherwise very good Have general fastnesses, if one uses 1,8-naphthalenedicarboxylic acids or their anhydrides aromatic o-diamines condensed in such a way that the resulting dye has at least one free hydroxyl or contains carboxylic acid group. The introduction of the hydroxyl or carboxylic acid group into the dye molecule can be done in such a way that 1,8-naphthalenedicarboxylic acid with an aromatic o-diamine condenses that in the benzene nucleus a hydroxyl or carboxylic acid group or in a side chain a hydroxyl group contains. Furthermore, you can also 1,8-naphthalenedicarboxylic acid, which is in the naphthalene nucleus by a Hydroxyl or carboxylic acid group is substituted with a substituted or unsubstituted aromatic Condense o-diamine. It is essential that in the dye molecule at least one free hydroxyl or carboxylic acid group is present.

The dyes obtained have the following general formula

Process for the production of dyes

Applicant:

Farbwerke Hoechst Aktiengesellschaft

formerly Master Lucius & Brüning,

Frankfurt / M., Brüningstr. 45

Dr. Wilhelm Eckert, Frankfurt / M.-Unterliederbach,

Dr. Otto Fuchs, Frankfurt / M.-Zeilsheim, Dr. Friedrich Raizner, Frankfurt / M.,

and Dr. Heinz Rentel, Frankfurt / M.-Unterliederbach, have been named as the inventor

wherein the benzene nucleus by a halogen atom, an alkyl, alkoxy, hydroxyl or carboxylic acid group or ι by the group O - CH ₂ - CH ₂ - OH and the

Naphthalene nucleus can be substituted by a hydroxyl or carboxylic acid group and in which at least one of the two nuclei contains at least one free hydroxyl-1 or carboxylic acid group.

The production of the dyes can be done in boiling

organic solvents such as pyridine, glacial acetic acid, chlorobenzene or o-dichlorobenzene, or in water under Printing.

The new dyes dye fibers and films from aromatic polyesters, especially Polyäthylente-

rephthalaten, from an aqueous liquor at the addition of an wearer (carrier) such as o-phenylphenol or others, at temperatures near the boiling point, without addition of an advantageous transfer agent at temperatures practicing 100 ⁰ C under pressure in grünstichiggelben to goldorangeni

Shades that are characterized by very good fastness properties-i shafts, especially thanks to an excellent thermal i fastness to flex, distinguish. The dyes obtained are also good for printing polyester fabrics suitable.

example 1

NN
O- CC

A mixture of 19.8 parts by weight of 1,8-naphthalene dicarboxylic anhydride, 16.5 parts by weight of 3,4-diamino-benzene-1-carboxylic acid and 150 parts by weight of glacial acetic acid is heated to the boil for 3 hours. The dye which crystallizes out on cooling ¹ is filtered off with suction, washed with methanol and dried. It dyes polyester fibers ¹ from aqueous dispersion in grünstichiggelben tones of ^one excellent heat setting.

509 728760 I.

Claims (1)

Example 2 19.8 parts by weight of 1,8-naphthalenedicarboxylic anhydride are mixed with 19 parts by weight of 3,4-diaminophenyljö-oxäthyläther heated to boiling in 300 parts by weight of chlorobenzene for several hours. The one out of the solution The exuding dye is bright for both dyeing and printing polyester fabrics greenish yellow tones. It is distinguished from that of 1,8-naphthalenedicarboxylic anhydride and 3,4-diamino-l-ethoxybenzene available dye through its completely flawless thermosetting and ironing fastness Example 3 21.4 parts by weight of S-oxy-1.S-naphthalenedicarboxylic anhydride are with 16 parts by weight of 3,4-diaminobenzene-1-carboxylic acid in 200 parts by weight of glacial acetic acid Heated to the boil for 2 hours. When it cools down, beautifully developed, yellow leaflets separate from them allow a mixture of dimethylformamide and water to recrystallize. Polyester fibers are made from aqueous dispersion dyed in greenish yellow shades of very good fastness properties. Example 4 If, instead of the 3,4-diaminobenzene-1-carboxylic acid given in Example 3, 16 parts by weight of 3,4-diamino-1-chlorobenzene are used, in this way a dye is obtained, the polyester fibers in greenish yellow hues of dyes with excellent heat-setting fastness. The implementation of S-oxy-l.S-naphthalenedicarboxylic acid under the same conditions as specified in Example 3, with 3,4-diamino-1-bromobenzene also gives a greenish yellow dye with excellent fastness properties. Example 5 21.4 parts by weight of S-oxy-1.S-naphthalenedicarboxylic anhydride and 17 parts by weight of 3,4-diaminophenyl / 9-oxethyl ether are heated to boiling in 200 parts by weight of glacial acetic acid for 2 hours. The one after the work-up The resulting crystalline greenish yellow dye is due to its excellent fastness properties excellent for dyeing and printing polyester fabrics. Example 6 In Example 5, the 3,4-diaminophenyl / I-oxethyl ether is replaced by 3,4-diamino-l-ethoxybenzene, a greenish yellow dye is also obtained, which shows the same excellent fastness properties. Example 7 10 parts by weight of naphthalene-l ^ .S-tricarboxylic anhydride boil for a few hours with 5 parts by weight of o-phenylenediamine in 50 parts by weight of pyridine heated. After cooling, the resulting dye is removed from the brown solution with dilute hydrochloric acid failed. For cleaning, the dye can be dissolved in dilute sodium hydroxide solution and then with a mineral acid precipitate again after clarification of the solution. Polyester fibers are made from aqueous dispersion in greenish yellow Dyed shades of excellent fastness properties. Example 8
^r 30 parts by weight of naphthalene-lAS-tricarboxylic acid are with 23 parts by weight of 3,4-diamino-phenyl - ^ - oxäthyläther heated in 300 parts by weight of water in an autoclave for 5 hours at 150 to 160 ⁰ C. The dye, which is easy to isolate after cooling, produces yellow dyeings of excellent heat-setting fastness on polyethylene glycol terephthalate fibers. Is used in place of 3,4-diaminophenyl - /? - oxethyl ether 21 parts by weight of 3,4-diamino-1-ethoxybenzene, a beautiful golden yellow color is obtained from same authenticity. The use of 3,4-diamino-1-methoxybenzene also leads to golden yellow coloring agents. P Λ T E N T A N S P RU C II. Process for the production of dyes used for dyeing fibers or films made from aromatic polyesters, in particular polyethylene terephthalates, are suitable by condensation of 1,8-naphthalenedicarboxylic acids or their anhydrides with aromatic o-diamines, characterized in that the The reaction participants are selected in such a way that the resulting dye is at least contains a free hydroxyl or carboxylic acid group. Considered publications:
French patent specification No. 1 111 620. A coloring table was displayed when the application was announced. © 809 728/260 12.58