DE2818101A1 - MONOAZODISPERSION DYES, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE FOR COLORING SYNTHETIC TEXTILE MATERIALS - Google Patents

Description

PATENT ADVOCATE. RICHARD KNBSSL Widanmryerstr. 4S

D-8000 MUNICH Tel. 089/295125

Folder 24443

ICI Case Dd 29494

IMPERIAL CHEMICAL INDUSTRIES LTD. London, UK

Monoazo disperse dyes. Process for their production and their use for dyeing synthetic Textilma materials

Priority: 4/25/1977 - Great Britain

809844/0944

DESCRIPTION:

The invention relates to monoazodispersed dyes, which are suitable for dyeing synthetic textile materials.

According to the invention there are monoazo disperse dyes proposed that are free of sulfonic acid groups and the formula:

OHC

-LJ-

= N-E

have, in which

X represents nitro, cyano, optionally substituted phenyl, -COOR, -CONHR ¹ , -COR ¹ or SO ₂ R ² ,

Y stands for hydrogen, optionally substituted alkyl or phenyl stands,

R represents hydrogen or optionally substituted alkyl, cycloalkyl or phenyl,

R represents hydrogen or optionally substituted alkyl or phenyl,

R for optionally substituted alkyl or phenyl or optionally substituted Amino stands and

E stands for the remainder of a coupling component.

Throughout this specification, the terms "lower alkyl" and "lower alkoxy" refer to alkyl and alkoxy radicals, respectively each having 1 to 4 carbon atoms.

1 2

Examples of substituted phenyl radicals R, R, R, X and Y are lower alkylphenyl radicals, such as tolyl and xylyl, Lower alkoxyphenyl radicals, such as anisyl, halogenophenyl radicals, such as chlorophenyl and bromophenyl, lower alkoxycarbonylphenyl radicals, such as methoxycarbonylphenyl and ethoxycarbonylphenyl, and nitrophenyl radicals. It is preferred

8098U / 09U

1 ?
admits that when R, R, R, X and Y are phenyl radicals, they are unsubstituted phenyl radicals.

1 2 Examples of optionally substituted alkyl radicals R, R, R and Y are alkyl radicals with 1 to 18 carbon atoms, which can be substituted, for example, by halogeno, cyano, hydroxy, carboxyl or lower alkoxy. It will, however

1 2

it is preferred that the alkyl radicals R, R, R and Y optionally substituted Are lower alkyl radicals. Examples of such unsubstituted radicals are methyl, ethyl, n-propyl, isopropyl, η-butyl, sec-butyl and isobutyl. Examples of substituted lower alkyl radicals R and R are hydroxy lower alkyl radicals, like ß-hydroxyethyl, Ct-methyl-ß-hydroxyethyl, ß- or / -methoxyethyl, ß-ethoxyethyl and a-methoxypropyl, Lower alkoxycarbonyl-lower alkyl radicals, such as ß-ethoxycarbonylethyl, carboxy-lower alkyl radicals such as ß-carboxymethyl, Cyano-lower alkyl radicals, such as ß-cyanoethyl, halogeno-lower alkyl radicals, such as ß-chloro and ß-bromoethyl, and phenyl lower alkyl radicals such as benzyl and ß-phenylethyl. unsubstituted lower alkyl radicals are particularly preferred. Examples of cycloalkyl radicals R are cyclopentyl and cyclohexyl.

1 2 Specific examples of the radicals -COR and -SC ^ R _r represented by X are acetyl, propionyl, benzoyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl and p-tolylsulfonyl. Examples of the -CONHR radicals represented by X are carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl and N-phenylcarbamoyl, and examples of the -COOR radicals represented by X are carboxy, methoxycarbonyl, ethoxycarbonyl, n -Butoxycarbonyl, ß-hydroxyethoxycarbonyl, ß-methoxyethoxycarbonyl, ß- (ß'-methoxyethoxy) ethoxycarbonyl, phenoxycarbonyl and cyclohexyloxycarbonyl. However, it is preferred that X be nitro, cyano, or lower alkoxycarbonyl.

809844/094 *

The remainder of the coupling component E can be the remainder of any be from the series of coupling components that couple with diazo compounds, such as the remainder of a coupling component the acylacetarylamide, pyrazolone, aminopyrazole, Phenol, naphthol, 2,6-diaminopyridine or 2,6-dihydroxypyridine series. In particular, E is the remainder of a coupling component of the aromatic series due to the presence of an optionally substituted amino group, such as the remainder of a coupling component of the 1-naphthylamine series, and especially the remainder of a coupling component of the aniline series, which is p-position to a optionally substituted amino group.

The remainder of the coupling component E preferably has the formula:

1 '2

wherein Z and Z each independently represent hydrogen or an optionally substituted hydrocarbon radical, in particular an optionally substituted lower alkyl radical, stand and the benzene ring B contain additional substituents or part of an optionally further substituted Can form naphthalene or quinoline rings.

In particular, E represents a radical of the formula:

809844/0944

where W is hydrogen, lower alkyl or lower alkoxy, V is hydrogen, lower alkyl, lower alkoxy, Chlorine, bromine or acylamino, especially an acylamino

2 3 2

group of the formula -NHCOT or -NHSO ₂ T (where T = hydrogen, alkyl, in particular lower alkyl, aryl, amino or aminoalkyl, T = optionally substituted lower alkyl or aryl), Z is hydrogen or optionally substituted alkyl, in particular lower alkyl, and Z represents hydrogen or optionally substituted alkyl, in particular lower alkyl, or optionally substituted aryl or cycloalkyl.

Examples of optionally substituted lower alkyl radicals Z and Z are hydroxy lower alkyl radicals, such as ß-hydroxyethyl, <X-methyl-ß-hydroxyethyl, ß- or g'-hydroxypropyl and S-hydroxybutyl, Lower alkoxy lower alkyl radicals, such as ß- (methoxy or ethoxy) ethyl and ^ -methoxypropyl, cyano lower alkyl radicals, such as ß-cyanoethyl, phenyl lower alkyl radicals such as benzyl and ß-phenylethyl, acyloxy lower alkyl radicals such as ß-acetoxyethyl and 1-acetoxy-2-propyl, carboxy-lower alkyl radicals, such as ß-carboxyethyl and 0-carboxybutyl, lower alkoxycarbonyl-lower alkyl radicals, such as ß-methoxycarbonylethyl, hydroxy-lower alkoxy-lower alkyl radicals, such as ß- (ß'-hydroxyethoxy) ethyl, Lower alkoxy-lower alkoxy-lower alkyl radicals, such as ß- (ß'-methoxyethoxy) ethyl, lower alkoxy-lower alkoxycarbonyl-lower alkyl radicals, like ß- (ß'-methoxyethoxycarbonyl) ethyl, Acyloxy lower alkyl radicals, especially lower alkylcarbonyloxy-lower alkyl radicals, such as ß-acetoxyethyl and 0-acetoxybutyl, chloro-lower alkyl radicals, such as g'-chloropropyl, and lower alkoxycarbonyloxy lower alkyl radicals, like ß-ethoxycarbonyloxyethyl.

According to the invention, a process for the preparation of the azo dyes defined above is also proposed, which is carried out by using an amine of the formula:

809844/09 * 4

- 9 Y X

OHC

ι ι

.NH,

diazotized and the diazo compound obtained with a Coupling component of the formula E-H, where E, X and Y have the meanings given above and that The amine and the coupling component are free of sulfonic acid groups.

The inventive method can expediently thereby be carried out that one sodium nitrate to a solution or dispersion of the amine in a strong inorganic acid or an aqueous solution thereof or that one the amine is stirred with nitroylsulfuric acid, whereupon the resulting solution or dispersion of the diazo component to a solution of the coupling component in water or in a mixture of water and a water-miscible one organic liquid is added, if necessary readjusts the pH of the mixture to facilitate the coupling reaction and finally isolating the resulting dye by conventional methods.

These amines can themselves be obtained by conventional methods, for example by Vilsmeier formylation of 2-acetylaminothiophene and subsequent nitration (the nitro group enters the 3-position) and hydrolysis, whereby 2-amino-3-nitrothiophene-5-aldehyde is obtained will. In some cases the Vilsmeier reaction conditions can be used to make other modifications as desired to make on the 2-aminothiophene-5-aldehyde structure. For example, if 2-acetylamino-3-aminocarbony1-thiophene is heated with phosphorus oxychloride in dimethylformamide, then the 5-aldehyde group is introduced, but in addition the aminocarbonyl group is also dehydrated, creating the cyano group and the acetylamino group in converted to the easily hydrolyzable dimethylformamidino group.

809344/0944

The amines mentioned can also be obtained from the corresponding 5-methyl, 5-chloromethyl or 5-hydroxymethyl compounds can be obtained by oxidation, the amino group being protected beforehand if necessary.

Specific examples of these amines are 2-amino-3-nitro-4-methylthiophene-5-aldehyde, 2-amino-3- (methoxycarbonyl-, -ethoxycarbonyl-, -acetyl-, -benzoyl-, -methylsulfonyl- or -N-methylcarbaiaoyl) thiophene-5-aldehyde and preferably 2-amino-3-nitrothiophene-5-aldehyde or 2-amino-3-cyanothiophene-5-aldehyde.

Examples of these coupling components are acylacetarylamides, such as acetoacetanilide and acetoacet-2,5-dimethoxyanilide; Aminopyrazoles such as 1-phenyl-3-methyl-5-aminopyrazole; Pyrazolones such as 1,3-dimethyl-5-pyrazolone and in particular 1-phenyl-3- (methyl-, -carbonamido- or -carbomethoxy) -5-pyrazolones, wherein the phenyl radical is optionally replaced by, for example, methyl, methoxy, ethoxy, chlorine, bromine, nitro, sulfonamido or acetylamino is substituted; 2,6-dihydroxypyridines such as 3-cyano-4-methyl-2,6-dihydroxypyridine and 1-ethyl-3-cyano-4-methyl-6-hydroxypyrid-2-one; 2,6-diaminopyridines, such as 3-cyano-4-methyl-2,6-di (N-2-methoxyethylamino) pyridine; Phenols such as o-cresol, resorcinol and 3-acetylaminophenol; Naphthols such as β-naphthol; and especially arylamines of the kaphthylamine series, such as 1-naphthylamine, and most particularly the aniline series, such as 2,5-dimethoxyaniline, Ν, Ν-diethylaniline, N, N-Di (ß-hydroxyethyl) -m-toluidine, N, N-Di (ß-cyanoethyl) aniline, N-ethyl-N- (ß-ethoxyethyl) aniline, N, N-di (ß-carbornethoxyethyl) -m-toluidine, 2-methoxy-5-methyl-N- (ß-acetoxy-methylethyl) aniline, N- / B- (ß'-methoxyethoxycarbonyl) äthyJaniiin, N, N-di- (ß-acetoxyethyl) -m-toluidine, N-ethyl-N- (ß-cyanoethyianiline, N-ethyl-N- (5-acetoxybutyl) aniline, N-ethyl-N-benzyl-m-toluene and N, N-diethyl-m-acetamidoaniline.

The azo dyes according to the invention are suitable for dyeing

809844/0944

of synthetic textile materials, especially those made from secondary cellulose acetate and cellulose triacetate, polyamide, such as polyhexamethylene adipamide, and especially aromatic polyesters such as polyethylene terephthalate. Such materials are in the form of threads, fibers, or woven or knitted materials.

The azo dyes mentioned can be applied to synthetic textile materials can be applied by methods commonly used for applying disperse dyes such textile materials are used. So the dyes can be in the form of aqueous dispersions by padding, Dyeing or printing processes are applied, the Conditions and other adjuncts common to the practice of such procedures may be used. Alternatively For example, the dyes can be applied to synthetic textile materials by solvent dyeing processes by applying a solution or dispersion of the dye in perchlorethylene, which may be a smaller one Contains amount of water on the textile material, preferably at an elevated temperature.

If the azo dyes according to the invention on synthetic Textile materials are applied, then they result in colorations, the color of which ranges from yellow to green and the one exhibit excellent fastness to light and wet and dry treatments. The dye obtained remains largely unaffected by the dyebath conditions, such as pH. The dyes mentioned also have on synthetic textile materials, especially those made from aromatic polyesters, excellent structural properties, so that deep color tones can be easily obtained. In this regard, these dyes are appropriate known dyes which have an acetyl group (instead of the aldehyde group) in the 5-position of the thiophene nucleus included, consider. Alternatively, the color

8098U / 0944

fabrics are used for the coloring of synthetic polymers in bulk, which are then converted into fibers or Threads are to be transferred. The dyes can also be transferred to synthetic textile materials by a transfer printing process be applied, which may be carried out under reduced pressure or under wet or damp conditions will.

The invention is illustrated in more detail by the following examples, in which the parts and percentages are expressed by weight are.

Example 1

1.72 parts of 2-amino-3-nitrothiophene-5-aldehyde are added to a solution of nitrosylsulfuric acid (obtained by dissolving 0.75 parts of sodium nitrite in 24.5 parts of sulfuric acid at 70 ° C., cooling and diluting with 30 parts of acetic acid and 5 Parts of propionic acid has been obtained) are added, the temperature being kept at -5 to ⁰ ° C. by external cooling. The temperature of the mixture is raised to 0 C and stirring is continued for 45 minutes. The resulting solution of the diazo compound is then added to a mixture of 3.5 parts of N, N-di (β-acetoxyethyl) -m-toluidine, 1 part of sulfamic acid, 20 parts of a 1% strength aqueous sulfuric acid and 500 parts of ice / water. and the pH of the mixture is then raised to 4 by the addition of sodium acetate. The mixture is stirred for an additional hour and the precipitated dye is filtered off, washed with water and dried.

When the dye is dispersed in an aqueous medium, it dyes aromatic polyester textile materials in bluish violet shades.

The 2-amino-3-nitrothiophene-5-aldehyde used in the above example was obtained itself as follows:

8098U / 09U

180 parts of a nitration mixture obtained by mixing 66.3 parts of nitric acid (see G. 1.50), 120 parts of 20% strength Oleum and 713 parts of sulfuric acid slowly became a solution of 33.8 parts of 2-acetylaminothiophene-5-aldehyde (prepared according to the procedure of Journal of American Chemical Society, 1953, Vol. 75, p. 989 was added) in 310 parts of sulfuric acid, the temperature of the mixture between -10 and -5 C. was held. The mixture was then stirred for an additional 5 minutes and poured into an ice / water mixture containing 5 parts of sulfamic acid contained, poured. The precipitated 2-acetylamino-3-nitrothiophene-5-aldehyde was then filtered off, washed with water and dried. The N-acetyl group was then removed by stirring the solid in a 4% strength aqueous solution of sodium hydroxide at 40-50 C and the resulting 2-amino-3-nitrothiophene-5-aldehyde was filtered off.

Examples 2 and 3

The following table relates to further dyes according to the invention, which are obtained in that the 3.5 parts of N, N-di (ß-acetoxyethyl) -m-toluidine of Example 1 by equivalent amounts of those in the second column of the following table the coupling components listed must be replaced. The shades obtained with these dyes are in the third Column of the table.

Example coupling component color

2 S-acetylamino-NfN-diethyl greenish blue aniline

3 3-methyl-N, N-diethylaniline blue

809844/094 *

- 14 Example 4

2-Acetylamino-3-aminocarbonylthiophene, mp 220-222 ° C., was prepared by treating 2-jtoino-3-aminocarbonylthiophene (prepared according to Bull. Soc-Chim. France, 19 74 _r p. 2869) with acetic anhydride. 36.8 parts of the acetylic compound was added to 280 parts of dimethylformamide, and 55.6 parts of phosphorus oxychloride were added dropwise to the mixture. The temperature

with _o

was / kept below 60 ° C. by external cooling. The mixture was then stirred for 75 min at 60 ° C., cooled and poured into an ice / water mixture.

2- (Ν, Ν-Dimethylformamidino) -3-cyano-5-formylthiophene crystallized slowly from the aqueous mixture and was collected and from a 20: 10: 1 propanol / methylcelloso1ve / Recrystallized water mixture, orange needles, melting point 192-193 ° C., being obtained.

20 parts of this compound were mixed with 100 parts of methyl cellosolve and 100 parts of cold 2η sodium hydroxide solution were mixed, and the mixture was heated to 60 ° C. for 5 minutes. The solution obtained was filtered and acidified with 120 parts of 2η hydrochloric acid. The precipitated 2-amino-3-cyano-5-formylthiophene was filtered off. The IR spectrum of the compound (Nujol muli) had peaks at 3390, 3295, 3150, 2210, 1695 and 1650.

15.2 parts of 2-amino-3-cyano-5-formylthiophene were added to a mixture of / 220, parts of acetic acid, 40 parts of propionic acid, /

\ £ i '* ir MvikiMärt * ¹ CJwA l £ H) \ Z.ivit-r Jt, lttftf & l.f <ii * rfl _: BfLa.Ht t / i * /

and T60 parts of JTCitrosylsulfuric acid (which contained 13 parts of Jrnitrosylsulfuric acid) were added at a temperature below ⁰ ° C. After stirring at ⁰ ° C. for 90 minutes, the above mixture was poured into a mixture of 2000 parts of ice and water, 100 parts of 2 η sulfuric acid, 20.6 parts of Ν, Ν-diethyl-m-aminoacetanilide and 50 parts of 1 m sulfamin-

809844/0944

acid poured. The pH was adjusted to 3-4 by the addition of sodium acetate, and the precipitated dye was filtered off after stirring the mixture for 30 minutes.

If the dye from an aqueous dispersion on a ' Textile material -from an aromatic polyester was applied, then reddish-blue shades with good Retain authenticity properties.

Example 5

3.6 parts of 2-acetylamino-3-cyano-4-methylthiophene were added a previously prepared mixture of 14 parts of dimethylformamide and 5.5 parts of phosphorus oxychloride at about 10.degree admitted. A slow exothermic reaction took place so that the temperature rose to approximately 35 ° C. After 2 st the mixture was poured into ice and water. Yellow crystals of 2- (Ν, Ν-dimethylformamidino) -3-cyano-4-methyl-5-formylthiophene slowly precipitated and were filtered off. This compound was made by that described in Example 4 Process hydrolyzed to give 2-amino-3-cyano-4-methyl-5-formylthiophene. The latter connection was made diazotized and coupled with Ν, Ν-diethyl-m-aminoacetaniiid according to the procedure of Example 4, with a dye which dyed aromatic polyester textile materials in bright blue-violet hues when he applied by conventional exhaustion dyeing techniques became.

Examples 6-18

The following table relates to further dyes according to the invention, where the column headings X, Y, V, W, Z and

2
Z refer to the following formula. The last column of the table shows the color shades that are

809844/0944

th when an aqueous dispersion of the respective dye on a textile material made of an aromatic Polyester is applied.

809844/0944

281810t

- (S3 - Is rö E E ro E. X! S. m -μ (Ö 4Y as -μ ϋ -μ • μ E. E. ro rH E. CN I— ( ffi = Ü ffi ■ μ H -μ rH • μ -H O + j .— * ö U -H CNl (D Λ ω X) CU η -μ U ω 8th ro O O ή d U ■ Η H CNl rH d ο rH U ffi -μ ro c m O ο O : rö U O ffi U : 3 rH -H • Η ro -H rH
A. •H S. Far t> U j.,, Q a in ffi O E E ro CJ ffi cn ro t - ι
I-I ffi in U O ro ffi CNl ffi in ffi O CNl ffi CN U E ffi ffi ffi U in CN] ffi U U ffi U U CN ffi ■ if O U O ffi m U O O CN O ffi U U ffi O O CN υ CN O O O O CN tH CNl O ffi U U in ffi U U O U CNl U OO E E O CN] ffi U ■ si ¹ U ffi ffi ffi ffi ro r> ffi CN! υ CN CN CN! in ffi O CN] U U U U ffi O ¹ T * U in CN ffi O CRF ro ffi ro O in X! O ffi ro ffi ffi in in CN] ffi m ffi r_) E S ffi U ffi ffi U U U ffi CNl 'S · Q U O CNl CN O O CN U rH H O O O U in U O O ffi in U - ι φ CNl ffi * O U ffi U U CN ffi ■ Η -Η U CN] O ■■ * CN] U CN! ffi (U CU U r> - co = ffi U ffi K U ffi (B ω ffi CNl CN CNl ffi CN] U ro U U ffi ffi O ffi ffi ffi ro U K ffi ro O ffi U ffi oo K ro ffi ro ffi ffi ffi ro O U * ri
W- * ffi ffi ro O U U U ro U ffi ffi U O O O ffi ffi O U ffi U U ffi U IS OO ffi ffi OO ro U ffi ffi ffi E. ffi H ffi E. E. U U O U E. m I.
ε ffi ffi E. E. ffi S. oo O E. E. ffi ffi ffi - E. r— α E. CNl E. E. O E. E. in E. S. ffi E. r- CN] CN ro - E. O j2 CN CTi E. U COO U CN VO ro in O CN! τ— τ »· OO CN! r— CN] KO x - cn O T— τ—

C.
O
+ J

ι α)

-H · Η
Q) Ci

CQ ω

χ: ϋ

-H

Cn

4J -U

+ J Q) O -H ί-)

+ J

O = U

• Η J-I

CM ΓΟ

rc u_

rc

CM

rc u

ΓΟ

rc u

O U O

CM U

(Tl

rc =

ΓΟ

rc

u ο

O O

CM U

ro

rc u

in m o

rc rc

CM CM

U U ^ r

rc

CM U

rc rc

ro

rc rc rc rc rc rc u u

ro

rc u

O U

rc

ro ro

ro

rc

U ro

rc rc rc o uuuuu

rc s

ro

rc u

rc rc ο u

rc rc rc rc rc rc

CM

rc ro CM ro ro CM vo rc rc rc in rc O U U U rc u s S. CM O O CM vo-u O U U O U S S. ω CM CM I. O O O Ui Ui

CN

in front of co σι ο

CM CM CM CM CM CO

809844/0944

Examples 32-38

The following table relates to further examples of the invention Dyes obtained when the diazonium compound obtained by diazotizing the in the second Amine indicated in the column of the table is obtained with the coupling component indicated in the third column of the table is coupled. The hue produced when the corresponding dye is applied from an aqueous Dispersion on a textile material made of an aromatic polyester is obtained in the fourth column the table.

at
game Amine Coupling component hue 32 2-amino-3-nitro-5-
formylthiophene N-phenylmorpholine violet 33 If 1-phenyl-3-methyl-S-
pyrazolone Red - 34 2-amino-3-cyano-4-
methyl-5-formyl-
thiophene Resorcinol It 35 Il 1 -Ethyl-S-cyanoM-me-
ethyl-6-hydroxypyrid-
2-on Il 36 Il N- (ß-hydroxyethyl) -1-
naphthylamine blue 37 2-amino-3-cyano-5-
formylthiophene ß-naphthol Red 38 If Acetoacetanilide orange

8098U / 0944

Claims (12)

PATENT CLAIMS: 1.J Monoazodxspersion dyes that are free from sulfonic acid are regroups and the formula: OHC = N-E own what X represents nitro, cyano, optionally substituted phenyl, -COOR, -CONHR ¹ , -COR ¹ or SO ₂ R ² , Y represents hydrogen, optionally substituted alkyl or Phe- - .nyl, R represents hydrogen or optionally substituted alkyl, cycloalkyl or phenyl, R represents hydrogen or optionally substituted alkyl or Phenyl stands,
2
R for optionally substituted alkyl or phenyl or optionally substituted amino and
E stands for the remainder of a coupling component. 2. Dyes according to claim 1, wherein the phenyl radicals 1 2
R, R, R, X and Y are unsubstituted phenyl radicals. 3. Dyes according to claim 1, wherein the substituted 1 2 or unsubstituted alkyl radicals R, R, R and Y substituted or unsubstituted lower alkyl radicals are. 1 2 4. Dyes according to claim 3, wherein R, R, R and Y are unsubstituted Are lower alkyl radicals. 5. Dyes according to claim 1, wherein X is nitro, cyano or lower alkoxycarbonyl. 8098U / 09U ORIGINAL one of the _{| (} ^
6. Dyes according to / claims 1 to 5, wherein the remainder of the Coupling component Ξ the formula: - (/ B Ni N \ 2 ix where Z ¹ and Z each independently represent hydrogen or an optionally substituted hydrocarbon radical and the benzene ring B may contain additional substituents or form part of an optionally further substituted naphthalene or quinoline ring. 7. "Dyestuffs according to claim 6, wherein the optionally substituted hydrocarbon radicals Z and Z are optionally substituted lower alkyl radicals. 8. Dyes according to any one of claims 1 to 5, wherein the The remainder of the coupling component E has the formula: has, wherein W is hydrogen, lower alkyl or lower alkoxy, V is hydrogen, lower alkyl, lower alkoxy, chlorine, bromine or acylamino, Z is hydrogen or optionally substituted alkyl and Z ^{4 is} hydrogen, optionally substituted alkyl or aryl or for Cycloalkyl. 9. Dyestuffs according to claim 8, wherein the acylamino group V has the formula -NHCOT ² or -NHSO ₂ T ³ , wherein T ² 8098U / Ö9U represents hydrogen, alkyl, aryl, amino or alkylamino and T
Aryl stands. 3
and T stands for. optionally substituted lower alkyl or 10. Dyes according to claim 9, wherein the alkyl radical 2 1 T and the optionally substituted alkyl radicals Z and Z are lower alkyl radicals or optionally substituted lower alkyl radicals. 11. Process for the preparation of the monoazodisperse dyes according to claim 1, characterized in that an amine of the formula: OHC diazotized and the resulting diazo compound with a coupling component of the formula E-H, where E, X and Y have the meanings given in claim 1 and the amine and the coupling component are free of sulfonic acid groups. 12. Use of the Monoazodispersionsfarbstoffe as an aqueous dispersion for coloring synthetic textile materials, in particular aromatic polyesters, by a dyeing _r padding or printing processes. 809844/0944