DEP0049252DA - Process for the production of vat dyes - Google Patents

Description

^IE N GESELLSCHAFT, BASEL (SWITZERLAND) Di pi .-! Ng. E. Spianeman®

Hamburg 36 Hamburg 36 ι B Ju! I ¹ P49

Neuer Wall 10, 4th floor Neuer Wall 10, 4th floor

Call 34 7900

Oasis 2566 / E
Germany

Process for the production of vat dyes,

It is already known that valuable vat dyes can be obtained if one or more isophthalic acid. reacts their functional derivatives with connectable amines. However, some of these dyes are not entirely satisfactory Extent, in particular, there are some yellow dyes that have otherwise useful to good fastness properties have the disadvantage of damaging the fibers. The property of the dyeings is here under fiber damage to understand when exposing BEZW. to suffer a greater loss of strength during weathering than the corresponding uncolored one Fiber. As is well known, there are also dyes which have fiber-protecting properties such that the dyed fiber is more resistant is than the uncolored. In the area of yellow to red vat dyes, however, there is a certain or even significant fiber damage is common.

It has now been found that valuable vat dyes can be prepared using compounds of the general formula

where one X and one Y are hydrogen and the other X and the other Y are halogen or hydrogen, with a responsive. Acylated derivative of an aromatic monocarboxylic acid.

Those used as starting materials for the present process. Compounds of the above general formula can, for .3. be obtained by nitrating isophthalic acid, converting the 5 "Nitro ™ isophthalic acid thus produced into a functional derivative 3, in particular the acid chlorine, this with 2 moles of a l-aminoanthraquinone, which has a halogenation; in 6 or / f 7 "3 position, can bszw. Reacts with 2 moles of two different such 1-aminoanthraquinones; and finally I reduced the nitro group. It can thus in the above. Formula both X and both Y signify hydrogen o;! Er es Sram κ; , B. one. X stands for a B'alogenatoiiif aB a chlorine or bromine ε ·· to ·.; · Or scaliesalich can mean both an X and a y halogen.

Use j Π-Sbepondere dia acid chlorides, - ^eri.lde: ite AVC-natirac αε r Fi ο ro acids know swedcmässlg äs ^ s Säir ^s ehalof; as reactive Deriv.

As examples of aromatic monocarboron: acids that,

As stated, it is expedient to use their chlorides in the form of anthraquinone-carboxylic acids, in particular anthraquinones called p-carboxylic acid, which also have other substituents

oils can, but preferably aromatisclie monocarboxylic acids, ¹ ^ a maximum of two, optionally have fused aromatic rings each other, such as naphthalenecarboxylic acids, BEZW diphenyl, Dipnenylsulfoncarbonsäuren, and in particular benzene carboxylic acids.

The monocarboxylic acids mentioned can expediently also have other substituents, such as those in vat dyes usually occur. According to the present process, benzene carbonic acids are particularly advantageous. their responsive Derivatives are used which contain a sulfur atom as a core substituent which is bonded to a further carbon atom. As examples of such substituents, the alkylsulfone groups, in particular methylsulfone groups, are selenium., A:. 'Ylsulfone groups, in particular Phenylsulfongruppen, as well as alkyl ^ meroaptogruxjpen, for example =

wisely called the methyl mercapto group, also a dialkyl sulfaid

group comes into consideration as a core substituent

a high boiling solvent "uie Nit: £ robes; ol at temparatures, egg © ..legen to or substantially above 100 ⁰ ^ V ', a, .B, at the boiling point of the respective solvent by stirring v / arden. Depending on the circumstances, it may be advisable to add condensing or acidic agents. The solution is generally carried out with remarkable ease, which in view of the

massively large molecule of the compounds of the above general formula was not to be expected without further ado.

The dyes according to the present invention can be used as pigment dyes. They are suitable for Dyeing and printing of a wide variety of fibers, in particular cellulosic fibers such as cotton, rayon and rayon made of regenerated cellulose, using the usual processes for vat dyes.

The following examples explain the present invention without, however, restricting it in any way. Included Unless otherwise noted, the parts denote weight ■ -tsi ^ TeV, the percentages are percentages by weight, and the temperatures are given in degrees Celsius.

21.6 parts of 5-amino-isophthaloyl-di- (l'-anthraquinoyl) amide of the formula

0 NH-CO. CO-NH 0

I), Il

0 KH ₂ 0

and 8 * 8 parts of m-methylsulfonyl benzotrichloride of the formula

COCl

SO ₂ CH,

are heated to boiling sum in 1200 parts of nitrobenzene until the reaction is complete. One lets; cool down, suck off, first washes with nitrobenzene, then with benaol and dries. A yellow powder, cotton, is obtained in this way in good yield from a violet vat in yellow tones ^ on. good fastness dyes, which are particularly characterized by low fiber damage.

If you take in place of. nv-Kethylsulfonjlben.zcylchlorid the corresponding amount of benzoylchloride _; in this way a yellow dye is also obtained, which dyes cotton from a violet vat in yellow: tones.

The 5 ~ Am: lr-oisophthaloyl used in this example. ~ Di ~ {l ^? -anthrachinoyl) -amid is obtained from: the following balance; 125 parts of S-NitrolBophtha'Läur ^ ichloria (available

on the one hand by nitrating isophthalic acid in concentrated nitric acid and treating the 5-kitroisophthalic acid thus obtained with thionyl chloride) are heated to boiling for 1/2 hour together with 220 parts of 1-aminoanthrachlnone in 1800 parts of nitrobe: azole. After cooling, it is suctioned off and worked up as usual. The 5-nitroi3ophthaioyl-di- (l ^: -anthrachlnoyl) -amide obtained in this way is converted into the corresponding amine or levate by vatting with hydrosulfite and sodium hydroxide solution, a product which can be recrystallized from nitrobenzene. convicted.

If one uses halogensubstituiepte 1-aminoanthraquinones instead of l-aminoarrthraquinone and / or acid chlorides of other aromatic monocarboxylic acids as acylating agents, so vat dyes are also used, as can be seen from the following taballo.

Color of the dye acid chloride _{component j dye on} cotton

Anthracliinone component

1-Am inoanthrach ino η

1 -Am ino anthr.achino η

l-amlnoanthraquinone

1-Am ^ no -6 -chlor antifachinon

1-amino-6-chloro anthraquinone

1-aminoanthrachmone 1-amino-6 -chlor

1 -amino -6 -chlor anthraquinone η

l-Amj.non.nthrachinori

Claims (1)

Claims. 1.) Process for the preparation of vat dyes, characterized in that compounds of the general formula = 0 0 = -NH-CO- / ViO-NB he NH ₂ wherein one X and one Y is hydrogen and the other X and the other Y is a halogen atom or hydrogen, acylated with a reactive derivative of an aromatic monocarboxylic acid. ? ..) Process according to claim 1, characterized in that the at most two aromatic rings are acylated by means of acid chlorides of such aromatic monocarboxylic acids exhibit. ^{? ote} £ * ο-η CIBA AKTIENGESELLSCHAFT Patent application in Germany ~ P 49252 IYd / 22 bB- Oase 2566 / S, Explanation of the color β table Dyeing 1 g dye according to Example I ₅ 1 * paragraph dyeing 2 s 5 “dye in the table on page 7 dyeing 3 ι 6“ dye in the table on page 7 ■ · »1 $ S - 1 f * Dyes on cotton aas sodium hydroxide and natriuni- liydrosiilfit eritiialtendea bath at 40 to 50 'oxidized j acidified and soaped at the boil. Afterwards in the air CIBA AKTIENGESELLSCHAFT