DE1086370B - Process for the preparation of water-insoluble disazo dyes - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN MfKiSS. PATENT OFFICE

class 22a 6

INTERNAT. KL. C 09 b

EXPLAINING PAPER 1086 370

F24043IVb / 22a

A N M E L D E TA G: SEPTEMBER 27, 1957

ß E NOTIFICATION
DEB REGISTRATION
AND ISSUE OF THE
EDITORIAL: AUGUST 4, 1960

From German patents 251 233, 260 998 and 262 694 it is known that by coupling the Tetrazo compound of 4,4'-diamino-3,3'-dimethyldiphenyl or 4,4'-diamino-3,3'-dimethoxydiphenyl with Arylamides of 2,3-oxynaphthoic acid to blue water-insoluble Disazo dyes that produce dyeings of good wash fastness on vegetable fibers, however, of moderate lightfastness.

From the German patent specification 651043 is also it has become known that by coupling the tetrazo compound of 4,4'-diamino-3,3'-dimethoxydiphenyl with 3-oxydiphenylene oxide on cellulose esters a brown one Color received.

It has now been found that new, valuable, water-insoluble disazo dyes are obtained, if one mole of a tetrazo compound of a 4,4'-diamino-3,3'-dialkyldiphenyl or a 4,4'-diamino-3,3'-dialkoxydiphenyl with 1 mol of an arylamide of 2,3-oxynaphthoic acid and with 1 mol of 3-oxydiphenylene oxide or one of its substitution products in substance, on the fiber or on another substrate couples and thereby chooses the components so that they are free of water-solubilizing groups.

N = N

OH

CO-NH-R

wherein X is an alkyl or alkoxy group, R is an aromatic radical and R _{1 is} hydrogen, a halogen atom, an alkyl or alkoxy group.

With these dyes on vegetable fibers, including those made from regenerated cellulose, using the known dyeing and printing processes, full brilliant black tones with very good wash and light fastness properties.

For example, cellulose fibers can be impregnated with a solution of the two azo components and the Then dyeings by treatment with a tetrazo compound according to the usual dyeing or printing methods to be developed. The processes in which the tetrazo compounds are particularly advantageous in stabilized form, for example as tetrazoamino compounds or as bis-antidiazotates, together be used with the two azo components according to the known printing methods.

The dyes can also be produced in bulk or on another substrate and used for dyeing Process for the preparation of water-insoluble disazo dyes

Applicant:

Farbwerke Hoechst Aktiengesellschaft formerly Master Lucius & Brüning,

Frankfurt / M., Brüningstr. 45

Dr. Reinhard Mohr, Offenbach / M., has been named as the inventor

According to the method according to the invention, one arrives at to disazo dyes presumably of the following composition:

N = N

HO-

high molecular weight plastic masses or for the preparation of colored lacquers.

The azo components used in the present process are the known aryl amides of 2,3-oxynaphthoic acid into consideration, e.g. B.

2,3-oxynaphthoylaminobenzene,
l- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene,

the same -2-methylbenzene, the same -3-nitrobenzene, the same -2-ethoxybenzene, the same ^ -methyM-methoxybenzene, the same ^^ - dimethoxy-S-chlorine- benzene, the same -2,5-dimethoxybenzene, the same -4-methoxybenzene or the same -4-ethoxybenzene, as well as that lenylene oxide and its in 5-, 6-, 7- or 009 569/361

8-position by a halogen atom, an alkyl or after squeezing the goods and an air

Alkoxy group-substituted derivatives, for example, about 40 seconds is briefly heated to 70 ° C

S-Oxy-S-cmordiphenylene oxide, ^Wa f ^e _n ^{r treated} , β * ρΒ &, nit Ig «dm» exposure

" _Λ , ,,,. ,,, Product of about 10 moles of ethylene oxide to 1 mole

3-oxy-o-chlorodiphenylene oxide, _{5 isododecylpheilol and 3 g of} sodium carbonate per liter

S-Oxy ^ -chlorodiphenylene oxide, ^{soaped in water at 9O 0} C, rinsed and dried.

S-Oxy-S-chlorodiphenylene oxide, a full black color of good ones is obtained

■ S-Oxy-S-methyldiphenylene oxide, fastness properties that look good white and colored

S-Oxy-o-methyldiphenylene oxide, can be ^etched

S-Oxy ^ -methyldiphenylene oxide, ¹⁰ Example 3

S-Oxy-S-methyldiphenylene oxide, 60 g of a mixture containing 17.6 g of 2,3-oxy-

3-oxy-6-ethyldiphenylene oxide, naphthoylanünobenzene, 12.4 g 3-oxydiphenylene oxide,

3-oxy-7-ethyldiphenylene oxide or 42 g bis-antidiazotate from 4,4'-diamino-3,3'-dimethoxy

3-oxy-7-methoxydiphenylene oxide. ¹ S % & ** & ( ⁴¹ ' ⁵ ° / ο ^) · ³ £ S Sodium Hydroxide and

Contains 24.2 g of sodium acetate, 20 g of denatured

Compared to the alcohol from German Patent 651043, 20 g of a wetting agent of the type

known, by coupling of tetrazotized 4,4'-di-oil sulfonate, 20 g sodium hydroxide solution of 38 ° Be and 150 g

amino-3,3'-dimethoxydiphenyl dissolved with 3-oxydiphenylene warm water. The solution thus obtained is

oxide available water-insoluble disazo dye and diluted 20 with water, in 500 g neutral starch tragacanth

the thickening known from German Patent 251 233, stirred in and, after adding 50 g of sodium

by coupling tetrazotized 4,4'-diamino-3,3'-di-chromate solution, 30% / ₀ ig, adjusted to 1 kg with water,

methoxydiphenyl with 2,3-oxynaphthoylaminobenzene. The printing paste obtained becomes cotton fabric

available water-insoluble disazo dye draw printed. It is then dried for 5 minutes

: the water-insoluble 25 available according to the process, acid-steamed, rinsed cold and warm, with 1 g of sodium

Disazo dyes are characterized by better lightfastness. earbonate and 1 g of a condensation product

an aminoalkylsulfonic acid and a higher molecular weight

Example 1 Fatty acid soaped, rinsed and boiled per liter of water

Cotton fabric is then dried on the foulard. A full black print is obtained

standing solution padded and dried: 3 ° of good fastness properties.

8.8 g of 2,3-oxynaphthoylaminobenzene and 6.2 g of 3-oxy- The development of the pressure can also be caused by new-

Diphenylene oxide is steamed with 50 ecm of a wetting agent or by a treatment in one

of the type of oil sulfonate made into a paste and after adding bath at 70 to 80 ° C take place in the liter of water

20 ecm sodium hydroxide solution of 38 ° Be with hot water to 50 ecm acetic acid, 50 ° / ^, and 30 g sodium chloride

1 1 set. 35 contains.

The dried fabric is printed using Example 4 below
paste printed and dried:

8.2 g of 4,4'-diamino-3,3'-dimethoxydiphenyl in the form of 75 g of a mixture (A) in 100 g of 17.6 g of 2,3-oxide of the tetrazonium chloride chlorzinc double salt in naphthoylaminobenzene, 12.4 g of 3-oxydiphenylene oxide, a mixture of 2 g of an action product of 4 ° 63.6 g of the tetrazoamino compound from 1 mole of tetrazo-ethylene oxide on a fatty alcohol, 10 g of acetic acid, tated 4,4'-diamino-3,3'-dimethoxydiphenyl and 2 mol 5O ⁰ Z ₀ Ig, and 300 g of water dissolved. The thus obtained methyl taurine (59, l ° / ₀ solution) and 5.6 g sodium sulfate in 500 g holds is entLösung neutral starch tragacanth comparison, are stirred thickening in a mixture of 20 g sodium hydroxide solution and adjusted with water to 1 kg . of 38 ° Be, 20 g of denatured alcohol, 20 g of urea,

Then in the usual way in soda 45 7 g of a wetting agent of the type of oil sulfonate and

rinsed in alkaline bath, soaped at boiling temperature, dissolved 40 g of hot water. The solution thus obtained

and dried. You get a full black one is diluted with a little warm water, in 500 g new-

Printing of good fastness properties. central starch-tragacanth-thickening stirred in and after

By simultaneous printing of other diazo- addition of 25 g of sodium chromate solution, 30 ° / ₀ ig, with

Primed primary aromatic amines can be adjusted to 1 kg in addition to 5 ° water.

The black printing also uses different colored prints. The printing paste obtained becomes cotton fabric

produce. printed. Then it is dried at 60 ° C,

The printing process can also be applied to other fibers - 5 minutes acid steamed, cold and warm rinsed, with types, for example viscose or rayon, 1 g of sodium carbonate and 1 g of a condensation are carried out. 55 product from an aminoalkylsulfonic acid and a Example 2 high molecular weight fatty acid in a liter of boiling water

soaped, rinsed and dried.

Cotton fabric is traced on the foulard. A full black print of good quality is obtained

standing solution padded and dried: fastness properties.

9.8 g of l- (2 ', 3'-Oxynäphthoylamino) -2-methoxybenzene 60 is used in the above example instead of the

and 6.2 g of 3-oxydiphenylene oxide are given with 50 ecm mixture (A) a mixture (B), which in 100 g

of a wetting agent of the oil sulfonate type pasted 17.6 g of 2,3-oxynaphthoylaminobenzene, 12.4 g of 3-oxy-

and after adding 20 ecm of sodium hydroxide solution of 38 ° Be diphenylene oxide, 44 g of the tetrazoamino compound from

set to 1 1 with hot water. 1 mole of tetrazotized 4,4'-diamino-3,3'-dimethyldiphe-

The dried fabric is on the padder with a 65 nyl and 2 mol of methyl taurine (78.5 ° / ₀ ig) and 25.2 g

Diazo solution developed, which contains sodium sulfate in one liter of water,

10.25 g of 4,4'-diamino-3,3'-dimethoxydiphenyl in the form or a mixture (C), which is in 100 g

of the tetrazonium chloride chlorzinc double salt, 2 g of an 18.5 g of l- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene,

The product of the action of ethylene oxide on a fatty 11.5 g of 3-oxydiphenylene oxide, 58.6 g of the tetrazoamino

contains alcohol and 20 ecm of acetic acid, 50%. 70 compound of 1 mol of tetrazotized 4,4'-diamino

Contains 3,3'-dimethoxydiphenyl and 2 moles of methyl taurine (59.1 ° / _o solution) and 10.2 g of sodium sulfate,

this also gives full black prints with good fastness properties.

The printing process can also be carried out on other types of fiber, for example viscose or rayon will.

Example 5

24.4 parts by weight 4,4'-diamino-3,3'-dimethoxydiphenyl are diazotized in the usual way. The Tetrazo

solution is blunted with sodium acetate and stirred into an acetic acid suspension of a mixture of 26.3 parts by weight of 2,3-oxynaphthoylaminobenzene and 18.4 parts by weight of 3-oxydiphenylene oxide. The after finished The dye obtained from coupling is filtered off, washed well and dried. He puts a black one Powder.

The following table also contains a number of further components which can be used according to the invention, ίο which also produce black dyes with good fastness properties:

Diazo component Azo component I. Azo component II 4,4'-diamino-3,3'-dimethoxy
diphenyl 3-oxydiphenylene oxide l- (2 ', 3'-oxynaphthoylamino) -
2-methylbenzene the same the same l- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene the same the same l- (2 ', 3'-oxynaphthoylamino) -
2-ethoxybenzene the same the same l- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-methoxybenzene the same the same l- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene the same the same l- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxybenzene the same the same l- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene the same 3-oxy-5-chlorodiphenylene oxide 2,3-oxynaphthoylaminobenzene the same 3-oxy-6-chlorodiphenylene oxide the same the same 3-oxy-7-chlorodiphenylene oxide the same the same 3-oxy-8-chlorodiphenylene oxide the same the same 3-oxy-5-methyldiphenylene oxide the same the same 3-oxy-6-methyldiphenylene oxide the same the same 3-oxy-7-methyldiphenylene oxide the same the same 3-oxy-8-methyldiphenylene oxide the same the same 3-oxy-6-ethyldiphenylene oxide the same the same 3-oxy-7-ethyldiphenylene oxide the same the same 3-oxy-7-methoxydiphenylene oxide the same 4,4'-diamino-3,3'-diethoxydiphenyl 3-oxydiphenylene oxide the same the same the same l- (2 ', 3'-oxynaphthoylamino) -
2-methoxybenzene 4,4'-diamino-3,3'-diethyldiphenyl the same the same the same the same 2,3-oxynaphthoylaminobenzene

Claims (1)

Claim: Process for the preparation of water-insoluble disazo dyes, characterized in that 1 mol of a tetrazo compound of a 4,4'-diamino-3,3'-dialkyldiphenyl or a 4,4'-diamino-3,3'-dialkoxydiphenyl is mixed with 1 mol of an arylamide the 2,3-oxynaphthoic acid and with 1 mole of 3-oxydiphenylene oxide or one of its substitution products in substance, on the fiber or on another substrate and the components are chosen so that they are free of water-solubilizing groups. Considered publications:
German patent specifications No. 251 233, 651 043. When the application was announced, a coloring table with an explanation was displayed. © 009 569061 7.60