DE1935482C - Azo compounds and their use for coloring and printing - Google Patents

Description

The objects of the friction are those which are soluble in water Azo compounds of the 2-cyano-4-alkyl or ihenyl - sulfonyl - 2 '- acylamino - 4' - dialkykimino-.l'-azohenzene series, which are excellent for dyeing, printing fibers or using laser material oll- or semi-synthetic, hydrophobic, high molecular Fabrics are suitable.

The new compounds correspond to the formula

CN

R ₁ -O ₁ S-

-N = N-

-N

A 0Π Il

R,

NH-R,

R, a hydrogen, chlorine or bromine atom,

R _{2 is} an alkyl group with 1 to 4 carbon atoms which can be unsubstituted or substituted by a chlorine atom, cyano, hydroxyl or phenyl groups, a phenyl radical which can be unsubstituted or substituted by a chlorine atom, or an amino group. which is unsubstituted or methyl, ethyl, hydroxyethyl, hydroxypropyl, cyanoethyl, cyanopropyl or methoxy groups. Bears phenyl, chlorophenyl or benzyl groups as substituents, or an N-pyrrolidine group.

R _{3 is} an alkyl group with 1 to 4 carbon atoms which is unsubstituted or a C'hloratom as a substituent. Carries hydroxyl, cyano, phenyl, methoxy or benzoyloxy groups.

R _{4 is} an alkyl group with 1 to 4 carbon atoms which is unsubstituted or a C'hloratom as a substituent. Hydroxyl, cyano. Methoxy-. Phenyl-. Pyridyl, formyloxy. Acetoxy, propionyloxy. Benzoyloxy, methoxybenzoyloxy. Aminocarbonyl, methoxycarbonyl, methoxycarhonyloxy. Acctylamino, phthalimino or sulfophthalimino groups.

R <is an alkylcarbonyl group with 1 to 1 carbon atoms in the alkyl radical. which is unsuhMituierl or a (chloroatom, cyano, methoxy, phenoxy or uenzyloxy group as a substituent, an alkoxycarbonyl group with 1 to 3 carbon atoms in the alkyl radical. which is unsiibstiiuicrl or carries a chlorine atom, a methoxy group or a phenyl group as a substituent, a l-ormyl, methylsulfonyl, benzoyl or chlorobinzoyl group and

Rf, a hydrogen atom or a methyl. Ethyl-, Methoxy or ethoxy group means

Particularly preferred compounds of the formula (I) are those in which R ₁ denotes an alkyl group having 1 to carbon atoms which is unsubstituted or a chlorine atom as a substituent. Hydroxyl, cyano, methoxy. Phenyl-. Pyridyl, benzoyloxy, methoxybenzoyloxy, aminocarbonyl, aectylamino, phthalimino or sulfophthalimino groups are deceptive.

The new connections are made '« by coupling a diazotized amine of formula (II)

CN

with a compound of the formula | lll)

Hill

N11 K., ⁴

The coupling generally takes place in an acidic, optionally buffered, medium under cooling instead of. Sodium acetate is particularly suitable as a buffer substance.

The compounds of the formula (I) can also be prepared by reacting a compound of the formula (IV)

Halogen R ₁ , i>

R, SO,

Ml

(-5 R ₁ -SO ₁ -

-N = N-

• N

I IV)

R.

NH-R,

K ₁

where halogen is a chlorine or bromine atom, with a metal cyanide in an organic solvent (in analogy to that of Friedman "in J. org. Chem., 26, [196I]. P. 2522 reactions described).

It is particularly advantageous to use the new To convert dyes into color preparations before they are used. Processing to dye preparations takes place in well known manner, e.g. B. by grinding in the presence of dispersants and / or fillers. With the preparations, optionally dried in a vacuum or by atomization, one can. after adding more or less water, dye in so-called long or short liquor, plop oiler to print.

The dyes draw from aqueous suspension excellently on lasers or threads and textile materials made from them made of fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic substances. They are particularly suitable for dyeing. Padding or printing of lextile material made of linear, aromatic polyesters, made of Ccllulosc-2 ¹ 2-acetate. Cellulose triacetate and synthetic polyamides. Also polyolefins. Acrylonitrile polymerization products and polyvinyl compounds can be colored with them.

One dyes or prints according to known ones. z. B. that in French patent specification I 445 371 described procedure.

The dyeings obtained have very good blemishes. in particular, they are excellent thermofixicr-. Sublime, pleated, ozone and leek gas resistant. The Nalkchtheilen are also very good. z. B. the water, sea water and wash fastness. I should be emphasized are also the dye fastness. el ic l ightness and the good migration characteristics. the The substances are externally resistant to the effects of the fin of the various permitting procedures. They can also be overcooked and reduced at temperatures of up to about 220 C and especially at 140 C. as well as acid and alkali resistant in a wide range.

These constants are not determined either by the correlation or by the presence of Fä'rtic.schlcun.be adversely affected.

Compared to known dyes from the German Auslcgeschriften I Oft ') 313 and I 108 355 and

Patent specifications I 226 501 and the next comparisons, remember

ile French
I "1S2 (, 54 own

dm. ^ mnal.ter. Dyes a better harm I hire hermolixierechlheii, better drawing power h / v », ene better friction fastness. The predominantly very clear advantages of the ingenious geni.il'.eii I arhslofle towards the well-known Farhsi, men were because of the structure and subsiiuieiiieii great resemblance of the dyes not to civ .inen.

I> he parts mentioned in the examples are Gev.khisieiL \ the temperatures are in degrees Celsius

B e i s ρ i e I 1

20 parts of concentrated sulfuric acid are ^{slowly s 7} O (■ with vigorous stirring

no

given sodium nitrite. Mimten is stirred at WV, then cooled to 10 and 19.6 parts of 4-amino-3-cyanoethylsulfonylbenzene are added to this temperature. After 3 hours, the ia / is completed otierung. The sulfuric acid / onium salt solution is poured into a mixture of 25.5 parts of I v-chloropropionylaminoO-NN-diethylaminobe-voi. 100 parts of glacial acetic acid, 750 parts of ice and K) parts of xminosulfonic acid. The coupling is pH-value 2.0 conducted in an acidic medium by blunting with sodium acetate, lithium up to 2.5 to the end. The E'arbsuJ forms immediately and falls out. It is filtered off, washed free and dried. The resulting F; i,; istoff dyes synthetic fibers: ί in ruby red .v> bn.i.inten shades with excellent fastness properties.

Example 2

ί ¹ 1.6 parts of the dye

(Ί

N N

H ₁ CO (MN

ΠΙ _: (ΊΙ _Λ

UiTilcn in M) l'rush dimethylformamide. One (5.2 parts of CiMCN) ₂ is added and the reaction mixture is stirred for 2 hours at \ M) . whereby the umpi-.et/te dye precipitates in crystalline form. One l.illt aiii cool room temperature, diluted with | (i (i parts of ethanol, then filtered the resulting I arbsl'iff from washed with water and dried. |.) Cr so enaltene dye fiirht synthetic nscrn I v> in ruby Ions with excellent fastness properties.

Dyeing instruction I

¹ l of the dye obtained according to Example I is Heulen nil 4 parts of dinaphthylmethandisulfonsaiirem ss sodium. 4 parts of sodium cetyl sulfate and 5 parts of sodium sulfate were ground to a fine powder in a ball mill for 48 hours. 2 parts of the dye prepanite obtained in this way are dispersed in .UXK) parts of water which contains 1 part of a weak solution of a highly sulfonated castor oil and 20 parts of an emulsion of a chlorinated HCl. For 20 to 2f < one brings in KK) parts of polyester fiber fabric. get the had in about .10 minutes at 95 to HX) and colors I hour at «5 to KX). The dyed material is removed from the fts Had, rinsed for 15 minutes at 70 'of 0.1 mil "" solution of a Alkylphenylpolvylykoläihcr ¹ "soaped, rinsed again and dried to give a ruby red coloration with excellent Yaniu Neten fastnesses.

T'ärvorschrill 2
.10 parts of the dye formula

CN

Cl

N-N-

H ₁ COCHN

CH ₂ CH ₁

CH ₁ CII,

are dinaphthylmelhandisulfonsau with 40 parts rem sodium, 50 parts of sodium cetyl sulfate and 50 parts Anhydrous sodium sulfate was ground to a fine powder in a ball mill for 4X hours.

To 4 parts of the dye preparation obtained ir KX) O parts of 40 to 50 'of warm water are added 100 parts of purified polyester fiber material and heated slowly. One stains in parts for about 60 minutes Pressure at 130 and after rinsing, gets soaps Rinsing and drying a purple dye with excellent fastness properties.

Dyeing instruction 3

An aqueous, finely dispersed suspension of 30 parts of the dye of the formula

CN

CH ₁ NHO ₂ S

N = ■ N </ - N

H ₁ COCHN

CIKCH,

CH ₂ CH ₁

70 parts of dinaphthylmethandisulfo.-yjurem sodium and 3 hours of sodium alginate is mixed with water aiii KKM) parts placed and mixed well. A polyester fabric is with the resulting padding at 20 padded. air dried from 60 to 100 and then air dried from 230 Treated for 60 seconds. The fabric is then rinsed, soaped, rinsed again and dried. You get a ruby red, level dyeing with good fastness properties.

I ärrrrschril'l 4

7 parts of the TaibsloH of the formula
CN

CH, O, S

N - N

11, CH ₁ COOCHN

CII, CII ₁

CH ₂ (TI ₁

are with 13 parts Sullil cellulose liquor powder and KX) parts of water ground in a ball mill. The paste obtained is dried by atomization I part of the I ärcpräparates obtained is made into a paste with a little water and passed through a sieve 4 parts of N - () leyl-N'-hytlroxy-iithyl-N '- <3'-sulfc »-2'-hy droxypiopyll-iithylenediamine in 4 (XX) parts of water containing I iiibebad added. Now add IfKI parts of polyamide fiber material (nylon) at 20 'in the had. heats this up within 30 minutes at KX) and stains for 1 hour at KX). The preserved ruby scroll The warning is rinsed and dried. She doesn't care and has good skills.

The following tables indicate further dyes of the formula (I) which can be prepared according to the invention; In the case of the dyes in Table I, _{R e always denotes a hydrogen atom.} Table 1

:> piell R, R, - CH, -C ₂ H, K * -2 ^M 5 3 H - NH ₂ - C ₃ H- -C ₃ H- 4th H - NHCH, - CH., -CH ₃ 5 H -CH ₂ -C _n K, - C ₂ H ₅ -C ₂ H ₅ 6th H j -CHXH, -C ₂ H ₅ -C ₂ H ₅ - H -NHCH ₂ CH, - C ₂ H ₅ CH ₂ C _n H ₅ 8th H - NHCH- - CH ₂ C _n H ₅ -CH ₃ H - No,), - C ₂ H ₅ -C ₂ H ₅ IO Cl -NlCH ₂ CH ₃ ), -C ₂ H ₅ -C ₂ H ₅ 11th Br ί -NH ₂ Ct H < -C ₂ H ₅ 12th Br ^: -CH ₃ -C ₂ H ₅ C u
* -2 "5 1? Cl -CH ₂ CH ₂ CH ₃ -C ₂ H ₅ - C ₂ H ₅ 14th H -CH ₂ CH ₂ CH ₅ -C ₂ H ₅ -C ₂ H ₅ 15th H -CH ₂ CH ₂ CH ₂ CH, -C ₂ H ₅ -CH ₅ 16 H - CH ₂ CH ₅ -C ₂ H ₅ - C ₂ H, 1" Cl -CHCH ₃ C · »H ^ -CH ₅ IS H -CH ₂ CI -C ₂ H ₅ - C ₂ H ₅ I «J H - CH ₂ CN -CH ₃ - CH ₃ 20th H ; -CHCH ₃ -CH ₃ -CH ₂ -C ₁₁ H ₅ 21 H , CN -CH ₂ CHXI - C ₂ H ₅ -C ₂ H ₅ H - CHCH, -C ₂ H ₅ - C ₂ H ₅ 23 H Cl -CH ₂ CH ₂ OH -C ₂ H ₅ -C ₂ H ₅ 24 η i -NIChM, -CH, --CH, H ί

Nuance on New Year's Eve

■ COCH ₂ CH ₃ j ruby red • COCH ₂ CH ₃ ] ruby red

COCH ₂ --C _n H ₅ ! Ruby red

COCH ₃ j ruby red

COOCH ₃ j ruby red

CHO J Rubinroi COOCH ₃ Ruby red

COCH ₂ CN violet

COOCH ₂ OCH ₃ purple

COOCH ₂ - C _n H ₅ j purple

■ COCH ₂ CH ₃ i violet COCH ₃ i ruby red COOCH _{3 ruby red}

■ COCH ₂ CH ₂ CH ₃ j Rubinroi COOCH (CH ₃ I ₂ ! Violet

-CO-CH ₂ OC _n H ₅ j ruby red

- COCH ₃ \ Rubinroi

- COCH ₂ CH ₃ j ruby red

- COOCH ₃ j ruby red

- COOCH ₂ CHXl ruby red

-CO-C _n H ₅ j ruby red

ί I

- COCH,! Ruby red

CO CJi

(Continuation)

K,

26 H 27; H

.M) H H , -t H 33 H H 35 H 3ft H 37 H 3 X H 19th H 40 H 41 H 42 H 43 H 44 Cl

NHCH., N CHjCHjCN -CjH, CH, -CU, CH, n ''! CH, -CjH. CH, CH, CH, - CjH, NIl - · '· ■■ Cl NHCHj - C _h H ₅ C * LJ NH - -C ₁ , H, NHCH, - CjH, NH- H- N (CH,), NHCHjCHXHjOCI 1., N (CH ₁ ), - C ₂ H, CH, N (CH.,) J N (CH ₁ ), CH, N (CH,), -ChU NHCH, - CjH, N (CH,), C ₂ H, -CjH, C ₂ H ₅ - CjH, CjH, C ₂ H, - C ₂ H, -CH,

C \

CjH,

C ₂ H,

CjH,

-CjH,

-CjH, -CjH ₅

-C ₂ H,

-C ₂ H ₅ -C ₂ H ₅ -C ₂ H, -C ₂ H ₅ -C ₂ H ₅ -C ₂ H ₅ -C ₂ H, -C ₂ H, -C ₂ H,

Nuanci: -α <O .iul PoKestur Oi SOXH, Red -fs COCH, Ruby red OO COCH ₂ CH, Ruby red to COCHjCH, Ruby red COCHXH, Ruby red COCHjCH, Ruby red COCHjCH, Ruby red 004 r NJ CO-CH, Ruby red CO - CHj - CH, Ruby red CO- -Cl Ruby Roi COCH, Ruby red COCH, Ruby red COCH, Ruby red COCH ₂ CH, Ruby red COOCHjCH, Ruby red COOCH, Ruby red COCHjCHjCI Ruby red COCHjCH ₂ CI Ruby red COCH, violet

(Continuation)

example

R ₁

Cl
Br
Cl
H
H

50 H 51 H 52 H 5 ;, H 54 H 55 H 56 H 57 H 58 H 59 H 60 H 61 H 62 H 63 Cl 64 Cl 65 Cl 66 Cl 1-1

N (CH,),

N (CH,),

N (CH,),

CH,

CH,

CH, Π .1 CH, : η CH, Ή 3 CH, "H NHC C _n H ₅ NHC - C _n H ₅ NHC C ₁₁ H ₅ NHC - C ,, H ₅ CH, - C ₁₁ H ₅ CH, - C ₁₁ H, CH, - C ₁₁ H ₅ CH, - C ₁₁ H ₅ CH, - CH, CH, CH, CH, πι.

C ₂ H ₅ QH ₅ C ₂ H ₅ C ₂ H, C ₂ H ₅

- C ₂ H ₅ • C ₂ H ₅

- C ₂ H ₅ -C ₂ H _5. C ₂ H ₅ -C ₂ H ₅ -C ₂ H ₅

C ₂ H ₅ -C ₂ H ₅ C ₂ H ₅ C ₂ H ₅ C ₂ H ₅ C ₂ H ₅ C, H <shade on polyester

C ₂ H ₅ C ₂ H ₅ C ₂ H ₅ C ₂ H ₅ C ₂ H ₅

C ₂ H ₅ C ₂ H ₅ C ₂ H ₅ -C ₂ H, C ₂ H, C ₂ H ₅

-C ₂ H ₅ -C ₂ H ₅ -C ₂ H ₅

C ₂ H ₅ -C ₂ H ₅ - C ₂ H ₅

C ₂ H ₅ -C ₂ H ₅

C ₂ H ₅

C ₂ H ₅

C ₂ H ₅ ■ CH, CH, CN

- COCH ₂ CH, ¹ purple <O - COCH, violet - COOCH, j purple cn - COOCH, Ruby red OD - COCHCH, Ruby red N) Ci - COCH, i ruby red - COOCH ₂ CH ₂ Cl ! Ruby red ■ - CC) OCH ₂ CH, I ruby red - SO ₂ CH, Ruby red - COCH ₂ CH ₂ Cl ! Ruby red - COCH - CH, Ruby red Cl - COCH ₂ CHCI ₂ Ruby red - C (JCH ₂ CN Ruby red - COCH ₂ CN ; Ruby red - COCH ₂ CH, ! Ruby red - COCH ₂ CH ₂ Cl Ruby red - COOCH, Ruby red - COOCH ₂ CH, Ruby red -COOCH ₂ CHj violet - COCH, 'Violet - COCH ₂ CH, violet -COCH ₂ CH ₂ CI violet - COCH, Ruby red

example

68 Cl 69 Cl 70 Cl 71 Cl 72 H 73 H 74 H 75 Cl 76 H 77 H 78 C. 79 Cl 80 H 81 C! 82 Cl

Cl

H
H

(Continuation)

R,

NHCH ₃

NHCH.,

NHCH ₁

NHCH ₁

CH ₂ -C ₁₁ H-,

CH ₂ -C _n H,

CH ₁
■ N (CH ₁ ),

CH ₃ -CH, -C _n H,

- N (CH ₃ ),

- NHCH,

- NHCH ₃

- NHCH ₃ CH ₃

- N (CH ₃ ),

CH ₂ -C ₀ H ₅

CH ₃
CH ₃

C ₂ II ₅

C ₂ H ₅ -C ₂ H ₅ -C ₂ H ₅ -C ₂ H ₅ -C ₂ H ₅ -C ₂ H ₅

C ₂ H ₅

- CH ₂ CH ₂ CN

- CH ₂ CH ₂ CN

- CH ₂ CH ₂ CN

- CH ₂ CH ₂ CN -CH ₂ CH ₂ CN -CH ₂ CH ₂ OH

- CH ₂ CH ₂ CI

- CH, CH, CN

- CH ₂ CH ₂ CN

- CH ₂ CH ₂ CN

- CH, CH, CN

CH ₂ CH ₂ Cl
CH ₂ CH ₂ CONH ₂ -CH ₂ CH ₂ COOCH ₃ CH ₂ CH ₂ CN

• CH ₂ CH ₂ CN CH ₂ CH ₂ OCOC ₀ H ₅ CH ₂ CH ₂ OCOC ₀ H ₅ CH ₂ CH ₂ OH CH ₂ CH ₂ OCOCH ₃

• CH ₂ CH ₂ OCOCH ₃

■ CH ₂ CH ₂ OCOOCH ₃ CH ₂ CH ₂ OCOCH ₃ CH ₂ CH ₂ OCOQH, CH ₂ CH ₂ OH CH, CH, CI

- CH ₂ CH, - N

CO

CO

SO,

- CH ₂ CH, - N

CO

- CH ₂ CH ₂ OCH ₃

- CH ₂ CH ₂ OCO- \ VOCH ₃

- COCH ₂ CH ₃

- COCH ₂ CH ₃

- COCH ₃

- COOCH ₃

- COCH ₂ CH ₃

- COCH ₃

- COCH ₃

- COCH ₂ CH ₃

- COCH ₃

- COCH ₂ CH ₃

- COCH ₃

- COCH ₁

- COCH ₃

- COCH ₂ CH ₃

- COCH ₂ CH ₃

- COCH ₃

- COCH ₃

- COCH ₃ -COCH ₃

nuance

on

violet CO violet O4 violet CJi violet OO Ruby red ND Ruby red Ruby red violet Ruby red Ruby red violet violet Ruby red violet violet

violet

Ruby red

Ruby red ruby red

R, R ₁ K (Continuation) R, R, nuance
on polyester example H - N (CH ₂ CHj) ₂ -CH ₂ CHCH, - CH ₂ CH ₂ OCOCH ₂ Ch ₃ - COCH, Ruby red 87 CN H -CH ₂ -C ₆ H, - CH ₂ CH ₁ OCH ₃ -CH ₂ CH ₂ OCHj - COCHj Ruby red -* 88 H -C ₆ H, - CHXH ₃ -CHXH ₂ NHCOCHj - COCHj Ruby red S 9 H -CH, -CH ₂ CH ₂ CN -CH ₂ CH ₂ - ^ j> - COCH ₃ Ruby red 90 H -CH, C ₂ H ₅ -C ₂ H, -COCH ₂ OCH ₂ -C ₆ H ₅ Ruby red 91 H -CH ₃ -CH ₂ CH ₂ OCOC ₆ H ₅ -CHXH ₂ OCOC ₆ H ₅ - COCH ₂ CH ₃ Ruby red 92 Cl - N (CHj) ₂ - CH ₂ CH ₂ CN -CH ₂ CH ₂ OCHO - COOCH, Purple __ 93 H CH ₂ C ₆ H, -CH ₂ CHXN -CHXH ₁ OCHO - COCH ₃ Ruby red <£) 94 Cl - CH, - C ₂ H ₅ -C ₂ H, - COCH ₃ Purple ^ 95 Cl - CH, -CH ₃ -C ₄ H ₀ - COCHj cn
Vidett 96 H - (V- ei -C ₂ H, -C ₂ H ₅ - COOC ₂ H, Ruby red OO 97 H - NHCH ₂ CH ₂ CN -C ₂ H ₅ -QH ₅ - COCH ₂ CH ₃ Ruby red 98 Cl - Ν - CHXH ₁ CN
ι -CH ₂ CH ₂ CN -CH ₂ CH ₂ OCOCH ₅ - COOCH, Ruby red 99 CH, H - N (CH ₂ CH ₂ CN) ₂ -C ₂ H ₅ - C ₂ H ₅ - COCH ₃ Ruby red 100 Cl -N (CH ₂ CHXN) ₂ -C ₂ H ₅ -C ₂ H ₅ - COOCH ₂ CH ₃ violet 101 Cl -N-CH ₂ CH ₂ OH - CH ₂ CH ₂ CN -CH ₂ CH ₂ OCOC ₆ H ₅ - COCH ₂ CH ₃ Ruby red *> · 102 CH, H - N (CH ₁ CH ₂ OH) ₂ - CHXHXN -CH ₂ CH ₂ OCOC ₆ H ₅ - COOCH ₂ CH ₃ Red 103: H -N (CH ₂ CHCH,), - CH ₂ CH ₂ CN -CH ₂ CH ₂ OCOC ₆ H, - COOCH ₂ CHj Red 104 '
j OH j Cl - NlCHXH - ■■ CH,), -CH ₂ CHXN -CH ₂ CH ₂ OCOCH, - COOCHXH, Red 105;

ki-
piL'l K, Hi-Fi H | II7 Π IHS Cl Kl ') Br lid Il 111 H 112 Br 113 Il 114 M.

R ₂

* CH,
■ - CH,

- NO,
-CH ₂ C _n H ₅

-CH ₂ CI

- NHCHj
-NH ₂

- N (CH ₃ ),

R ₃

CH ₃

C ₂ II ₅

C ₂ H ₅

C ₂ II ₅

CHj

CH ₃

CH ₂ CH ₂ CN

CH ₂ CH ₂ CN

table

CHj

C ₂ II,

C-H,

C ₂ H,

CH ₂ C _n II,

CH ₂ C _n II,

CH ₂ CH ₂ OClU)

CH ₂ CH ₂ (COOK,

COOCl I ₃

COCH ₂ CN

COCH ₂ OCH,

(οπι, αι.α

(OC ₂ II, SO ₂ CH, SO ₂ CH, (OCH ₃ COCH ₃

cn.,

OCH,

OCH,

OC ₂ II,

OC ₂ IU

(.11,

OCH,

OC ₂ II,

N 11.UKc

.Ulf I'oheiUT

violet
violet
Violas
Violas
violet
\ ioIl-II
Violas violas

OCH, I violas

Claims (1)

Patent claims:
Azo compounds of the formula R ₁ -O ₁ S wonr = N-C NH-R ₅ Λ ' (I) Kl Ri is a hydrogen, chlorine or bromine atom. R _{2 is} an alkyl group having 1 to 4 carbon atoms which can be unsubstituted or substituted by a chlorine atom, cyano, hydroxy or phenyl groups, a phenyl group which can be unsubstituted or substituted by a chlorine atom, or an amino group which is unsubstituted or Methyl-. Ethyl, hydroxyethyl, hydroxypropyl, cyanoethyl, cyanopropyl or methoxypropyl groups, phenyl, chlorophenyl or benzyl groups as substitutes, or an N-pyrrolidine group. R _{1 is} an alkyl group with 1 to 4 carbon atoms which is unsubstituted or, as a substitute, a chlorine atom, hydroxyl. Carries cyano, phenyl, methoxy or benzoyl groups. R _{4 is} an alkyl group with 1 to 4 carbon atoms which is unsubstituted or a chlorine atom as a substituent. Hydroxyl, cyano, methoxy, phenyl, pyridyl, formyloxy. Acetoxy-. Propionyloxy, benzoyloxy. Methoxybenzoyloxy-, aminocarbonyl-. Methoxycarbonyl-, melhoxycarbonyloxy-. Carries acetylamino, phthalimino or sulfophthalimino groups, R _{5 is} an unsubstituted or unsubstituted or unsubstituted or unsubstituted or substituted chlorine, methoxy, phenoxy or benzyloxy group alkyl carbonyl group with 1 to 3 carbon atoms in the unsubstituted alkyl group or a chlorine atom, carries a methoxy group or a phenyl group as a substituent, an methyl, methylsulfonyl, benzoyl or chlorobenzoyl group. and
R _{6 is} a hydrogen atom or a methyl, Al hy! -. Methoxy or ethoxy group.
2. A process for dyeing or printing fibers or threads or materials made therefrom made of fully or semi-synthetic, hydrophobic, high molecular weight organic substances, characterized in that the dyes according to claim I are used.