CH629241A5 - Dye preparations for cellulose or cellulose-containing textile material - Google Patents

Description

The invention relates to aqueous dye preparations for dyeing and printing cellulose or cellulose-containing textile material which, in addition to other constituents such as one or more conventional dispersants, water retention agents and optionally a disinfectant, contain one or more dyes of the formula (I) free from sulfonic acid groups.

(I)

n included in the

A an optionally substituted anthraquinonyl residue or a substituted anthraquinonyl residue fused in the 1,9-position with a pyrimidine or pyridone ring,

X and Y are the same or different radicals of the formulas

/ T2

-Nf or-S-T3

N.'pl and n denote the number 1 or 2 and wherein in the formulas T2 for hydrogen, an aliphatic radical or phenoxy-Cr to 45 C4-alkyl or Cr to C6-alkylthio, T1 for hydrogen, an aliphatic, cycloaliphatic, araliphatic or aromatic residue or the group

T2

-N also for a saturated 5-, 6- or 7-membered he-

50

T1

terocyclic radical and T3 represent an aliphatic, alicyclic or aromatic radical.

Residues for A are:

mono- or divalent a-anthraquinonyl radicals which carry non-water-solubilizing substituents in the further a-positions or in the β-positions, anthrapyridone or anthra-pyrimidine radicals which optionally carry up to 3 substituents.

The usual non-water-solubilizing substituents in anthrachinoid dyes are e.g. considered:

a) for the remaining a positions: chlorine, bromine, Cr to C6-alkyl, Cp to C5-alkoxy, phenoxy optionally substituted by Cr to Q-alkyl, chlorine or bromine; Cp to C6-alkylthio, optionally substituted by Cp to C6-alkyl, chlorine or bromine, phenylthio; Hydroxy, amino, Cp to Q-alkylamino, where the alkyl can be substituted by hydroxy, Cp to C_r alkoxy, cyano or carbonyl-C2- to Cb-alkoxy; optionally by Cp to C5-alkyl, methoxy, ethoxy, chlorine,

629 241

Bromine or phenoxy substituted phenylamino and the residues of the formein

-NH-C-R 'and -NH-C-NH-

-NH- / v where R 'for Cp to

O Z

C5-alkyl or phenyl which is optionally substituted by Cr to Q-alkyl, bromine, chlorine, methoxy or ethoxy and Z is O or S. If there is more than one substituent, these may be the same or different.

b) for the 2-position: cyan, acetyl, propionyl, benzoyl optionally substituted by 1 to 3 methyl, methoxy or phenoxy; Cp to C6-alkylsulfonyl, phenylsulfonyl, N-Cp to C6-alkylisulfamoyl, N, N-bis (Cl- to C6-alkyl) -sulfamoyl, N-C3-to Cl2-alkoxyalkylsulfamoyl, N, N-bis (C3- bis C12-alkoxyalkyl) -sulfamoyl, Cp to C6-alkoxycarbonyl, cyclohexoxycarbonyl, N-Cp to C6-alkylaminocarbonyl, N, N-bis (Cr to C6-al-kyI) -amino-carbonyI, N-phenylaminocarbonyl, N- (Cp to C6 alkylphenyl) aminocarbonyl; Oxdiazolyl- (2) which in the 5-position is a phenyl which is optionally substituted by Cr to C6-alkyl, Ci to C4-alkoxy, chlorine or bromine; a optionally by chlorine, bromine, hydroxy, cyano, Cr to C4-alkoxy, di- (Cp to C4-alkyl) amino, carbamoyl, carbonyl-C2- to C9-alk-oxy, Ci- to C5-alkylthio, phenyi or phenoxy-substituted Cp to C10-alkyl (the phenyl radicals being substituted by chlorine, bromine, Cr to C4-alkyl, methoxy, ethoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl and / or N-alkylsulfamoyl with 1 to 4 carbon atoms per alkyl may) carry a Cp to C5 alkylthio, a C7 to C10 phenalkylthio or a phenylthio optionally substituted by chlorine, bromine, Cp to C4 alkyl, methoxy or ethoxy; Thiodiazolyl- (2), which in the 5-position as a substituent Cp to C3-alkyl, Cp to Cg-alkylthio, C3- to C8-alkoxyalkyl, Cp to C5-alkylamino, methoxy, ethoxy or optionally by Cr to C6-alkyli , Cp to C4-alkoxy, chlorine or bromine substituted phenyl, or isoxdiazoIyI- (5) which in the 3-position as a substituent is optionally substituted by saturated 5- or 6-membered heterocyclic rings containing N as ring member, Cp to C8 alkyl substituted by phenoxy, phenalkoxy, Cp to C5-alkylthio or Cp to C5-alkylsulfonyl; C3- to C8-alkoxy alkyl, phen-Cpbis Q-alkyl, phenyl or a 6-membered saturated or unsaturated heterocyclic ring, the phenyl nucleus or the heterocycles optionally by Cp to Cs-alkyl, chlorine, bromine, hydroxy or Cr to C4-alkoxy are substituted, and wherein a C atom in the 2-, 5- or S-position also carry a -N02 group and the number of substituents can be 0 to 6. _

The a-anthrapyridone or a-anthrapyrimidine residues are optionally substituted by Ci to Q-alkyl and optionally 1 hydrogen atom by hydroxy, Cp to C6-alkoxycarbonyl, phenyl, Cp to C6-alkylphenyl, Cp to C4-alkylcarbonyl, benzoyl or cyano. The number of substituents is 0 to 2, preferably 1.

In addition to hydrogen, the following substituents come into consideration for T2: linear or branched Cp to C8 alkyl; by hydroxy, cyan, chlorine, bromine, carbonylalkoxy with a total of 2 to 5 carbon atoms, N-alkylaminocarbonyl or N, N-dialkylaminocarbonyl with 1 to 8 carbon atoms per alkyl, by Cp to C4-alkylsulfonyl, Cp Cp to C4-alkyl substituted by C4-alkylthio or phenoxy; Alkoxyalkyl with a total of 3 to 6 carbon atoms or Cp to Cs-alkylthio.

As residues T2 are e.g. to be mentioned in detail: hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, 6-methylheptyl- (l), 2-hydroxyethyl, 2-chloroethyl, 2 -Bromethyl, 2- (methylthio) ethyl, 2-cyanoethyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 2- (butoxycarbonyl) ethyl, 2- (methylsulfonyl) ethyl or 2- (butylsulfonyl) ethyl.

T2 preferably represents hydrogen or Cp to C4-alkyl, of which hydrogen is particularly preferred.

For T1 come as aliphatic, cycloaliphatic, aliphatic or aromatic radicals e.g. into consideration: a) saturated, 5 linear or branched Cr to C18-alkyl, b) by cyan, chlorine, bromine, carbonylalkoxy with a total of 2 to 5 C atoms, N-alkylaminocarbonyl or N, N-dialkylaminocarbonyl with 1 to 8 C Atoms per alkyl, Cp to C4-alkylsulfonyl, amino, dialkylamino with 1 to 4 carbon atoms per alkyl or phenoxy w substituted C2- to C8-alkyl, the number of substituents being 2 or preferably 1; c) alkoxyalkyl with a total of 3 to 11 carbon atoms, d) hydroxyalkoxyalkyl and alkoxyalkoxyalkyl with a total of 4 to 10 carbon atoms, e) phenoxyalkoxyalkyl with a total of 10 to 12 atoms; f) saturated 5-, 6-, 7- or 15 8-membered cycloalkyl or polycycloalkyl, g) cycloalkyl optionally substituted by 1 to 3 Cp to C8-alkyl, cycloalkyl or hydroxyl, h) phenalkyl with a total of 7 to 10 C atoms , in which the alkyl radical is optionally substituted by hydroxyl and optionally the phenyl radical by Cp to C15-alkyl; i) phenyl, et- or ß-naphthyl, in which optionally 1 to 3, preferably 1 or 2, in particular 1 hydrogen by Cp to C18-alkyl, hydroxy, chlorine, bromine, trifluoromethyl, nitro, cyano, Cp to C5-alkoxy , Cr to C4-alkylthio, alkanoyl-amino with 2 to 5 carbon atoms, sulfamoyl, N-alkyl or N, N-25 dialkylsulfamoyl with 1 to 8 carbon atoms per alkyl, N-phenylsulfamoyl, carbamoyl, N -Alkylaminocarbonyl or N, N-dialkyl-aminocarbonyl with 1 to 8 carbon atoms per alkyl, N-phenylaminocarbonyl, where the phenyl radical can be substituted by methoxy, ethoxy or methyl, carbonylalkoxy with a total of 2 30 to 6 carbon atoms, Cp to C4-alkylsulfonyl, phenylsulfonyl, which is optionally substituted in the phenyl by alkyl, Cp to C4-alkylcarbonyl, phenalkoxy having 7 to 10 carbon atoms or phenoxy and where the substituents can be identical or different 35 and in the case of more than one Alkyl, alkoxy or alkyl and alkoxy the sum of the C atoms in this substituent is a maximum of 12.

In addition to those already mentioned, e.g. considered:

1) optionally substituted alkyl radicals: the alkyl radicals mentioned for T2 and n-pentyl, isoamyl, sec.-pentyl, neopentyl, n-hexyl, methylpentyl, dimethylbutyl, n-heptyl, methylhexyl, dimethyipentyl, trimethylbutyi, n-octyl, Isooctyl, me- + 5 thylheptyl, 2-ethylhexyl, dimethylhexyl, trimethylpentyl, tetramethylbutyl, n-nonyl, isononyl, dimethylheptyl, trimethylhexyl, decyl, undecyl, dodecyl, 2,2-dimethyldecyl, tetradecyl, hexadecyl, Octadecyl, 2-chloroethyl, 2-bromoethyl, 2-methylthioethyl, 2-butylthioethyl, 2-cyanoethyl, 2- (methoxycarbo-50 nyl) ethyl, 2- (ethoxycarbonyl) ethyl, 2- (butoxycarbonyl) ethyl , 2- (methylsulfonyl) ethyl, 2- (ethylsulfonyl) ethyl, 2- (butylsulfonyl) ethyl, 2- (N, N-diethyiamino) ethyl, 2- (N, M-dimethylamino) ethyl, 2- (N, N-dibutylamino) ethyl, 3- (N, N-di-ethylamino) propyl, 3- (N, M-dimethyiamino) propyl, 3- (N, N-55 dibutylamino ) -propyl, 3-aminopropyl, 2-aminoethyl,

2-phenoxyethyl, 3-phenoxypropyl, 4-phenoxybutyl; 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl,

3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-iso-propoxypropyl, 3-butoxypropyl, 3- (2'-ethylhexoxy -) - propyl,

60 3-isobutoxypropyl; 2- (2'-hydroxy-ethoxy) ethyl, 2- (3'-hydroxypropoxy) ethyl, 2- (4'-hydroxybutoxy) ethyl, 3- (2'-hydroxy oxyoxy) propyI, 3- (3'-Hydroxypropoxy) propyl, 3- (4'-Hydroxybutoxy) propyl, 3- (3'-Hydroxypropoxy) propyl, 3- (4'-Hydroxybutoxy) propyl; 2- (2'-methoxyethoxy) ethyl, 2- (2'-65 ethoxy ethoxy) ethyl, 2- (2'-butoxyethoxy) ethyl, 3- (2'-ethoxyethoxy) propyl, 3- (2-butoxyethoxy) propyl; 2- (2'-phenoxyethoxy) ethyl, 3- (2'-phenoxyethoxy) propyl, 2- (3'-phenoxy propoxy) ethyl, 3- (3 'phenoxy propoxy) propyl;

7

2) optionally substituted cycloalkyl or polycycloalkyl:

629 241

(ch) j-v

~ \ ïD »3 m» c (; ch3) 3j m = 1, 2, 3

Oh

- <H) -C8H17, - <H) - (K>, - <^ H), J ©, - <Ff,

■ Ì> 0H '

ch20h,

-Oh

3) optionally substituted phenylalkylene radicals: -CH; ~ Ct, H5, -CH2-CH; -C0H5. -CH ^ CH-QHj,

CH,

-CH, -CH, -CH, -C ,, H <.- CH, -CH.-CH-CfiH <,

CH3

-CH, -CH-C „H5, and -QH4-CH,

!

OH

instead of C6H5; -CH -> - C6H4-C12Hi5, -CH2 ~ C <, H4-C, H17, -CH2-C6H4-C9H19. -CH; -C6H4-CftH13;

4) optionally substituted phenyl or naphthyl radicals: phenyl, 2-, 3- and 4-methylphenyl, 2,4-, 2,5- and 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 2-, 3- and 4-ethylphenyl, 2,4-, 2,5- and 2,5-diethylphenyl, triethylphenyl, 2-, 3- and 4-propylphenyl, 3- and 4-isopropylphenyl, 2-, 3- and 4- Butylphenyl, 3- and 4-isobutylphenyl, 3- and 4-sec-butylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-octylphenyl, 4-isooctylphenyl, 4-dodecylphenyl, 4-octadecylphenyl; 3- and 4-hydroxyphenyl, 2-, 3- and 4-chlorophenyl, 2,4-dichlorophenyl, 3,5-dichlorophenyl, 5-chloro-4-methoxyphenyl, bromophenyl; 3-tri-fluorophenyl, nitrophenyl, nitro-methylphenyl; Cyanophenyl, methyl-cyanophenyl; Methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, propoxyphenyl, diisopropoxyphenyl, butoxyphenyl, pentoxyphenyl, (2'-methoxyethyl) phenyl, (2'-propoxyethyl) phenyl, (3'-methoxypropyl) phenyl, (3 ' -Propoxy-propyl) -phenyl; Methoxycarbonylphenyl, ethoxycarbonylphenyl, butoxycarbonylphenyl, pentoxycarbonylphenyl, methoxyethylcarbonylphenyl, ethoxyethylcarbonylphenyl, propoxyethyicarbonylphenyl; Methylsulfonylphenyl, ethylsulfonylphenyl, butylsulfonylphenyl; Phenyisulfonyiphenyl, 4'-methylphenylsuifonylphenyl; Acetylaminophenyl, propionylaminophenyl; N-methylamino-carbonylphenyl, NN-dimethylcarbonylamino-no-phenyl, N-ethyl and N, N-diethylaminocarbonylphenyl, N-butyl and N, N-dibutyaminocarbonylphenyl, N-hexylamino-nocarbonylphenyl, N-octylamino-carbonylphenyl, N- (2'-ethylhexylamino) carbonylphenyl; N-phenylamino-carbonyl-phenyl, N- (methoxyphenyl) amino-carbonyl-phenyl, N- (ethoxyphenyl) amino-carbonyl-phenyl, N- (methylphenyl) -

amino-carbonyl-phenyl; N'-Methyl- and N, N-DimethylsuIfamo-ylphenyl, N-Athyl- and N, N-DiethvlsulfamoylphenyI, N-Bu- "° tyl- and N, N-Dibutylsulfamoylphenyl, N-Pentylsuifamoylphe-nyl. N- (2nd '-Ethylhexyl) -sulfamoylphenyl, N- (2'-hydroxyethyl) -sulfamoylphenyl, N, N-bis- (2'-hydroxyethyl) -sulfamoylphenyl, N- (2'-cyanoethyl) -sulfameoylphenyl, N, N-bis- (2'-cyanoethyl) sulfamoylphenyl, N- (3-methoxypropyl) sulfamoylphenyl, "" M-cyclohexylsulfamoylphenyl, N-phenylsulfamoylphenyl, N- (methylphenyl) sulfamoylphenyl; Benzyloxyphenyl, (2'-phenylethoxy) phenyl, (3'-phenylpropoxy) phenyl, (4'-phenylbutoxy) phenyl; Phenoxyphenyl, 2-chlorobenzyloxyphenyl, 4-chlorobenzyloxyphenyl, 2-cyanbenzyloxyphenyl.

40

Of the radicals mentioned for T1, the following may be mentioned as preferred: Cr to Q-alkyl such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, methylbutyl, methylpentyl, Methylhexyl, methylheptyl, 1,1,3- «trimethylbutyl, octyl, 2-ethylhexyl; Alkoxyalkyl with a total of 3 to 11 carbon atoms, such as 2-methoxyethyl, 2-propoxypropyl, 2-ethoxyethyl, 2-butoxyethyl, 3-methoxypropyl, 3-ethoxy-propyl, 3-isopropoxypropyl, 3-propoxypropyl, 3-butoxypropyl, 2- (2'-ethylhexoxy) ethyl, 3- (2'-ethylhexoxy) propyl; Alkoxy-30 aikoxy-alkyl with a total of 5 to 11 carbon atoms such as 2- (2'-methoxyethoxy) ethyl, 2- (2'-ethoxyethoxy) ethyl, 3- (2'-methoxyethoxy) - propyl, 3- (2'-ethoxyethoxy) propyl; Phenalkyl with a total of 7 to 10 carbon atoms, such as benzyl, 2-phenylethyl, 2-phenylpropyl, 3-phenylpropyl, 3-phenylbutyl, 4-phenylbutyl, 55 2-hydroxy-2-phenylethyl; Phenoxyalkyl with 2 to 4 carbon atoms in alkyl and phenoxyalkoxyalkyl with a total of 4 to 6 carbon atoms in alkoxyalkyl (= a total of 10 to 12 carbon atoms) such as 2-phenoxyethyl, 3-phenoxypropyl, 2- (2'-phenoxyethoxy) - ethyl, 3- (2'-phenoxyethoxy) propyl, 3- (3'-phenoxypropoxy) -60 propyl; N, N-dialkylaminoalkyl with a total of 4 to 12 carbon atoms, such as N, N-dimethylaminoethyl, N, N'-diethylaminoethyl, N, N-dibutylaminoethyl, N, N-dimethylaminopropyl, N, N'-di-ethylaminopropyl , N, N-dibutylaminopropyl; Cyclohexyl; Phenyl or phenyl in which 1 to 3, in particular 1 or 2, hydrogen-65 by Cp to C4-alkyl, methoxy, ethoxy, chlorine or bromine and / or 1 hydrogen by alkoxycarbonyl with a total of 2 to 5 carbon atoms, N- Alkylaminocarbonyl with 1 to 4 carbon atoms in alkyl, N, N-dialkylsulfamoyl with 1 to 4 carbon atoms

629 241 8

each alkyl, phenoxy or benzyloxy are substituted, such as oxycarbonylphenyl, 4-N-methylaminocarbonylphenyl, 4-N-

4-tolyl, 4-ethylphenyl, 4-isopropylphenyl, 2,4-dimethylphe-ethylaminocarbonylphenyl, 4-N-ButylaminocarbonyIpher.y !.

nyl, 2,5-dimethylphenyl, 4-butylphenyl, 4-tert-butylphenyl, 4-N-octylaminocarbonylphenyl, 4-N- (2'-ethylhexyl) -am; -

p-chlorophenyl, p-bromopheny [, 2-methyl-4-chlorophenyl, nocarbonylphenyl, N, N-diethyisuIfamoylphenyl, N, M-Di — s-

4-methoxyphenyl, 4-aihoxyphenyl, 4-methoxy-5-chlorophenyl, 5 thylsulfamoylphenyl, N, M-dibutylsulfamoylphenyl, N'-Athy ', -

4-methoxycarbonylphenyl, 4'-ethoxycarbonylphenyl, 4-but-N-butylsulfamoylphenyl.

t2

For group 1, -NH - ^^ - OCH ^,

-NH - <^ ~~ ^> - 0C2H5, -NH - ^ * ~ ^ -C2H5J -NH- ^ ^ -01,

-NH - / ^> - 0CH5, '-NH-CHg- /, -NH-CH2-CH0- / ~~ \

ch2-ch (ch3) 2

Cl

-nh-ck2-ciï- (3, -nh- (ch2) 2-ch

CH-, CH-,

J? -3-

-NH-CH (CH3) 2J -N (C3H7 (n)) 2J -NH-C ^ Hg (n), -NH-C ^ (tert.),

-nh-ch2-ch (ch3) 2 / -nh-ch-c2h5, -nh- (ch2) 2-ch (ch5) 2,

ch3

-nh- (ch2) -5-ch (ch3) 2j -nh- (ch2) 3t0ch3, -nh- (ch2) 2-0-ch (ch3) 2

and -NH- (CH2) 3 ~ 0- (CH2) 2-0- ^ particularly preferred.

/ T2

5-, 6- or propyl, 3-propoxypropyl, 3-butoxypropyl; Phenoxymethyl,

T1 dichlorophenoxymethyl, p-methylphenoxymethyl;

7-membered saturated heterocyclic radicals, which are 2. phenalkyl with 7 to 10 carbon atoms:

may also contain -O—, -S— or another N atom- benzyl, 2-phenylethyl, 2-phenylpropyl, 3-phenylpropyl, 4-phenyl

nen. In particular, e.g. the residues of pyrrolidine, piperidine, nylbutyl;

Morpholins, Thiomorpholins, Hexamethylenimins, Piperazins 3. optionally substituted phenyl:

and to name the N'-methyl or N'-ethyl piperazine. Phenyl, 2-, 3- and 4-methylphenyl, 2,4-, 2,5- and 3,5-dime

In addition to hydrogen, T3 comes as aliphatic, alicycli- 55thylphenyl, 2,4,6-trimethylphenyl, 2-, 3- and 4-ethylphenyl,

see or aromatic residues e.g. considered: linear or mixed diethylphenyl, triethylphenyl, 2-, 3- and 4-propylphenyl, 3-

branched Cr to C8 alkyl; by Cp to C4-alkoxy or phen- and 4-isopropylphenyl, 2-, 3- and 4-butylphenyl, 3- and 4-iso-

oxy substituted C [to C8 alkyl; Phenalkyl with 7 to 10 butylphenyl, 3- and 4-sec.-butylphenyl, 4-tert.-butylphenyl,

Carbon atoms; Cyclohexyl; Phenyl which may be replaced by 1 to 4-octylphenyl, 4-isooctyiphenyl, 4- (2'-ethylhexyl) phenyl,

3, preferably by 1 or 2, in particular by 1 Cr to 4-decylphenyl, 4-dodecylphenyl, 4-octadecylphenyl, 2-, 3-

Cl8-alkyl, Cp to C4-alkoxy, Cp to C4-alkylthio, chlorine, and 4-methoxyphenyl, dimethoxyphenyl, 2-, 3- and 4-ethoxy-

Bromine is substituted and the substituents are identical or phenyl, diethoxyphenyl, 3- and 4-propoxyphenyl, diisoprop

can be different. oxyphenyl, 3- and 4-butoxyphenyl, 2-, 3- and 4-chlorophenyl,.

For T3, the residues include, in addition to the named 2,4- 3,4- and 3,5-dichlorophenyl, 3- and 4-bromophenyl, 2,4-

ten e.g. considered: 6S and 3,5-dibromophenyl.

1. alkyl: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, for T3 is methyl, ethyl, propyl, isopropyl, butyl, benzyl sec-butyl, hexyl, octyl, 2-ethylhexyl; 2-methoxyethyl, and p-methoxyphenyl, especially phenyl, preferred.

2-Ethoxyethyl, 2-butoxyethyl, 3-methoxypropyl, 3-ethoxy- For A are as mono- and divalent, optionally substituted

629 241

tuated a-anthraquinone residues, those with 0 to 6, preferably in formula I A is e.g. for a mono- or di-valent those with up to 4 substituents. Anthraquinonyl radical of the formulas in which Hai is chlorine or bromine and m 'is 1, 2 preferably 0 and, if appropriate, in the remaining a-positions (b, c and d) and in the 2-position (a) further non-water-solubilizing substituents customary in anthraquinone dyes, the substituents being the same or different.

For A, e.g. Remains of the following formulas are considered:

(Shark)

(IIa), (rl = l)

(Hàl)

(IIb), (n = 2)

î8 11:

(nd)

(n = l)

Shark and R are in the formulas! to R13 for the following substituents:

Shark: chlorine, bromine; m '= 1, 2 or preferably 0 (zero), R': hydrogen, chlorine, bromine, methyl, ethyl, Cp to C6-alkoxy, phenoxy, alkylphenoxy with 1 to 6 carbon atoms in the alkyl, chlorophenoxy, bromophenoxy, Cr to C6-alkylthio, phenylthio, alkylphenylthio with 1 to 6 carbon atoms in alkyl, acetyl, propionyl, benzoyl, mono-, di- and trimethylbenzoyl, methoxybenzoyl, phenoxybenzoyl, C- to Q-alkoxycarbonyl, cyclohexoxycarbonyl, N-alkyl or N , N-Dialkylaminocarbonyl with 1 to 6 C atoms per alkyl, phenylaminocarbonyl, Al-30 kylphenylaminocarbonyl with 1 to 6 C atoms in alkyl, cyano, nitro, C, - to C6-AlkyIsulfonyl, phenylsulfonyl, Cp to Q- Al-kylphenylsulfonyl, N-alkyl- or N, N-dialkylsulfamoyl with 1 to ó C-atoms per alkyl, N- (alkoxyalkyl) - or N, N-bis- (alkoxyalkyl) sulfamoyl with 3 to 12 C-atoms per alkoxyalkyl . 25 R2: hydrogen, hydroxy, Cr to C4-alkoxy, amino, Cp to Q-alkylamino; Cp to C8-alkylamino substituted by hydroxy, Cr to C4-alkoxy, cyano or carbonylalkoxy with a total of 2 to 6 C atoms; Phenylamino; Phenylamino substituted with Cp to C5 alkyl, methoxy, ethoxy, phenoxy, chlorine or bromine; Cp to C6 alkylthio; Phenylthio; phenylthio substituted by Cr to C5-alkyl; -NH-C-R12,

and o

in the R12 is a saturated, linear or branched Cp to 33 Cj-alkyl, phenyl, phenyl substituted by Cr to C4-alkyl, bromine, chlorine, methoxy or ethoxy or

-NH-C-NH— (f, where Z is O or S.

II W

40 t

R3 and R4: hydrogen, hydroxy, amino, Cp to C4-alkylamino, phenylamino, phenylamino substituted by Cp to Cr alkyl, methoxy, ethoxy, chlorine, bromine or phenoxy, Cp to C6-alkylthio, phenylthio, by Cp to C5 -Alkyl substituted 45 phenylthio, -NH-C-R12, wherein R12 is the above

Has meaning, or -NH — C-NH - {^ y1> where Z is for O

50 t

or S stands. The radicals R3 and R4 can be the same or different. One of the residues R3 or R4 can also stand for nitro.

R5: hydrogen, methoxy,

R6: nitro or the groups mentioned for R7, in which case R7 and R6 may be the same or different.

R7: hydrogen, hydroxy, saturated linear or branched Cr to Cj-alkylamino, where the alkyl can be substituted by Cr to C4-alkoxy, hydroxy or cyano.

R8: amino, Cp to C5-alkylamino, hydroxy,

R9: phenyl; phenyl substituted by Cp to C6 alkyl, Cr to C4 alkoxy, chlorine, bromine; Cp to C1 (r alkyl; Cp to C, u-alkyl, which by chlorine, bromine, hydroxy, cyano, Cp to C4-alkoxy, dialkylamino with 1 to 4 carbon atoms per alkyl, carbamoyl, carbonylalkoxy with a total of 2 to 9 C atoms, Cp to C5-alkylthio, phenyl or phenoxy is substituted, in the phenyl substituents optionally 1 or 2 hydrogen atoms by chlorine, bromine, Cp to Cj-alkyl, methoxy, ethoxy, alk-

55

65

629 241

oxycarbonyl, alkylthio, alkylsulfonyl and / or N-alkylsulfamoyl with 1 to 4 carbon atoms per alkyl are substituted; Cr to C5 alkylthio; C7 to C10 phenylalkylthio; Phenylthio; phenylthio substituted by chlorine, bromine, Cp to C4-alkyl, methoxy or ethoxy.

R10: Cr to C5 alkyl; Cp to Cg alkylthio, C3 to CB

10th

Alkoxyalkyl; Cp to C5 alkylamino; Methoxy, ethoxy; Phenyl, which is optionally substituted by Cp to C6-alkyl, Cr to C4-alkoxy, chlorine or bromine.

Rn: amino, Cp to C5-AlkyIamino.

In addition, for A e.g. Remains of the formulas (n = 1)

or to call. In the formulas, the residues R15 to R19 stand for:

R1S: hydrogen, Cp to C5-alkoxycarbonyl, Cp to C4-alkylcarbonyl, benzoyl, cyan.

R18: hydrogen, Cp to C5 alkyl, phenyl.

R16: hydrogen, Cp to Cs-alkyl, phenyl, Cx to C5-alkylphenyl or halophenyl.

R17 and R19: hydrogen, hydroxy, amino or -NH-C — R12, in which R12 has the meaning given above and II

O

the radicals R17 and R19 can be the same or different.

Preferred substituents are:

for R1: hydrogen, acetyl, benzoyl, cyano, methyl, dimethyl and trimethylbenzoyl, methoxy and ethoxybenzoyl, phenoxybenzoyl; Cp to C5 alkoxycarbonyl, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy or isobutoxycarbonyl; Cyclohexoxycarbonyl; Cp to C4-alkylninocarbonyl, such as N-ethylamino, N-propylamino, N-isopropylamino, N-butylamino or N-isobutylaminocarbonyl, phenylaminocarbonyl, phenylaminocarbonyl substituted by methyl, chlorine, bromine, methoxy, ethoxy, Cp to C6 Alkylthio, such as methylthio, ethylthio, butylthio, hexylthio, phenylthio, Cp to C4-alkylphenylthio, such as methylphenylthio, Cp to Cs-alkoxy such as methoxy, ethoxy, butoxy, hexoxy, 2-ethylhexoxy; Phenoxy, chlorophenoxy, bromophenoxy, methylphenoxy, Cp to C4-alkylsulfonyl such as methyl, ethyl, propyl or butylsulfonyl; Phenylsulfonyl and methylphenylsulfonyl;

for R2: hydrogen, hydroxy, amino, Cp to Q-alkylamino such as methylamino, ethylamino, isopropylamino, isobutylamino; Phenylamino, phenylamino substituted by Cp to C5-alkyl, methoxy, ethoxy, phenoxy, Q- to C4-C-acyloxy such as methylphenylamino, methoxyphenylamino, chlorophenylamino, 4-acetoxyphenylamino, phenoxyphenylamino, Cp to C4-alkoxy such as methoxy, ethoxy Butoxy; —NH-CO-R ', in which R' is Cp to C5-alkyl or phenyl or

-NH — C-NH, where Z is O or S.

for R3 and R4: hydrogen, hydroxy, amino, phenylamino, chlorophenylamino, methylphenylamino, methoxyphenylamino, phenoxyphenylamino, ethoxyphenylamino, thiophenyl, benzoylamino, acetylamino, where the substituents can be the same or different. One of the radicals R3 or R4 can also be nitro or -NH-C-NH-C6H5, where Z is O or S

means.

for R5, R6 and R7: hydrogen;

for R8: amino.

25 for R9: phenoxyalkyl having 1 to 6 carbon atoms in alkyl such as phenoxymethyl, 3-phenoxypropyl, 5-phenoxypentyl, 2- (di-chlorophenoxy) ethyl, 4-chloro-2-methylphenoxymethyl; Phenalkyl with 1 to 6 carbon atoms in alkyl such as 5 '- (diphenyl) pentyl, 3' - (4-methylphenyl) propyl, Cp to C5 alkyl such as methyl, 30 ethyl, propyl, butyl or phenyl.

for R10: Cp to C5-alkyl, Cp to C5-alkylthio, phenalkyl-thio with 2 to 4 carbon atoms in alkyl or phenyl.

for R11: Amino.

for R15: hydrogen.

35 for R16: hydrogen, phenyl, Cp to C3-alkylphenyl such as methylphenyl, halophenyl such as chlorophenyl.

for R17 and R19: hydrogen, hydroxy.

for R18: hydrogen, methyl.

The preparations according to the invention are advantageously prepared by grinding a suspension of 15 to 40, preferably 20 to 35 parts of dye (I), 4 to 10 parts of dispersant, 5 to 15 parts of water retention agent and approximately 0.5 to 1.5 parts of disinfectant approximately 75.5 to 33.5 parts of water are made in an agitator ball mill, a bead mill or 45 sand mill until the particle size is about 0.5 µm and below. This gives storage-stable dye dispersions.

Suitable dispersing agents are the anionic and nonionic substances normally used for the production of finely divided preparations of disperse dyes at 5 °. As anionic dispersants are e.g. To name: Ligninsulfon-te, salts of phenol-formaldehyde-sodium sulfite-condensation products (DE-OS 23 01 638), salts of 2-naphthalene-sulfonic acid-formaldehyde condensation products, salts of -s phenolsulfonic acid-urea-formaldehyde condensation products , Salts of condensation products from phenolsulfonic acid-urea-formaldehyde which have been post-condensed with phenol and formaldehyde.

Above all, ethylene-60-lenoxide and propylene oxide-ethylene oxide adducts come into consideration as nonionic dispersants. Such are e.g. in U.S. Patents 2,979,528 and 3,841,888.

The amount of dispersant depends on the dye and its concentration in the dispersion; the 65 amount of dispersant is generally between 4 and 10% by weight, based on the preparation.

Glycols, such as ethylene glycol, propylene glycol, diethylene glycol, are particularly preferred as water retention agents

11

629 241

Dipropylene glycol into consideration. The amount is generally between 5 and 15, preferably between 8 and 12% by weight, based on the preparation.

The dyes of the formula (I) can be prepared in a manner known per se by reacting the compounds of the formula

A- (NH2) n

(5)

with cyanuric chloride in a ratio of 1: n mol in inert solvents and subsequent replacement of the remaining 2 chlorine atoms in the triazinyl radical by the radicals -X and -Y (process a). A, X and Y have the meanings given above.

The procedure can also be such that compound (5) is mixed with n mol of the chlorotriazine of the formula

Cl

N "

Cl

(6a)

half-sided in an inert solvent, optionally in the presence of bases, and then the remaining chlorine atom is replaced by the rest -Y (method b).

In addition, the compound (5) with n mol of the chlorotriazine of the formula

(6b)

Apply Cl at elevated temperature until all chlorine is replaced. The reaction product is then isolated in the usual way.

The half-conversion according to process variant (b) 5 takes place at temperatures between 20 and 130 ° C, preferably between 45 and 90 ° C. The amount of (6b) depends on whether A has one or two reactive amino groups and, in the case of two reactive amino groups in A, on whether both or only one of these amino groups should be reacted. The half-reaction is generally complete in the polar, aprotic or protic solvents after 1 to 4 hours. Then the stoichiometric amount required is added to an excess of the nucleophile H-Y and the mixture is kept at 60 to 200 ° C, preferably at 70 to 130 ° C, 15 until all chlorine has been replaced. The reaction product is isolated in a manner known per se.

In process (c), the reaction is usually carried out at temperatures between 60 and 200 ° C. The reaction is complete after 2 to 10 hours. The reaction product is worked up as usual.

Dye preparations which contain dyes or dye mixtures of the formula (Ia) are of particular technical value.

30th

N

NH-

ZN \

T6

■ c «

7

W - = / T

N. T

XN

(Ia)

n are implemented (method c).

This reaction also advantageously takes place in inert solvents or diluents and, if appropriate, in the presence of bases.

Inert solvents or diluents are e.g. aromatic hydrocarbons and aromatic chlorinated hydrocarbons such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene, trichlorobenzene, nitrobenzene, N, N-dialkylcarboxylic acid amides such as N, N-dimethylformamide or N-methylpyrrolidone.

Suitable for processes (b) and (c) are preferably aprotic polar solvents such as N.N-dimethylformamide and N-methylpyrrolidone, and also phenols such as phenol, cresol, xylenol, pyrocatechol, resorcinol and hydroquinone.

In process (a), the reaction with cyanuric chloride generally takes place at temperatures between 0 and 100 ° C., preferably between 20 and 60 ° C. This gives a condensation product in which there are still two chlorine atoms on the triazine residue. The subsequent reactions with the nucleophiles H — X and H-Y with the exchange of the two chlorine atoms are expediently carried out at temperatures between 20 and 180 ° C., preferably between 60 and 130 ° C.

In general, it is not necessary to isolate the primary condensation products that still contain chlorine. Instead, the subsequent exchange reactions can be carried out in the same reaction vessel using the "one-pot process".

Advantageously, the less reactive nucleophile is generally used first and then the more reactive nucleophile is used as the last reaction component

40 included.

In formula Ia, T5 and T7 are Cr to Cs-alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl; Alkoxyalkyl with a total of 3 to 7 carbon atoms, hydroxyalkoxyalkyl with a total of 4 to 7 carbon atoms, such as 2-methoxyethyl, 2-ethoxyethyl, 45 propoxyethyl, 2-butoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-butoxypropyl, 3- (4'-hydroxybutoxy) propyl; Phenalkyl with a total of 7 to 10 carbon atoms, such as benzyl,

2-phenylethyl, 3- and 4-phenylbutyl, 3-phenylpropyl; Phenoxyalkyl with 2 to 4 carbon atoms in the alkyl such as 2-phenoxyethyl,

so 3-phenoxypropyl; Phenoxyalkoxyalkyl having 4 to 6 carbon atoms in alkoxyalkyl, such as 2- (2'-phenoxyethoxy) ethyl, 3- (2'-phenoxyethoxy) propyl; Cyclohexyl, phenyl or phenyl, in which 1 to 3 hydrogen by methyl, ethyl, methoxy, ethoxy, chlorine or bromine or a hydrogen by carbonalkoxy with a total of 2 to 5 carbon atoms, an alkylaminocarbonyl or a dialkylsulfamoyl with 1 up to 4 carbon atoms per alkyl, a phenoxy or a benzyloxy is substituted, such as methylphenyl, dimethyl- and trimethylphenyl, chlorophenyl, bromophenyl, methoxyphenyl,

3-chloro-4-methoxyphenyl, ethoxyphenyl, 3-methoxycarbonyl-6 »phenyl, 3-butoxycarbonylphenyl, 2-ethoxycarbonylphenyl,

3-N-methylaminocarbonylphenyl, 3-N-ethylaminocarbonylphenyl, 3-N-butylaminocarbonylphenyl, N, N-dimethylsulf-amoylphenyi, N, N-diethylsulfamoyIphenyI, N, N-dibutylamino-nosulfamoylphenyl, N-ethyl-sulfyloylphenyl;

65 ^ T5

and T6 and T4 are hydrogen or the group -N x for a piperidine or morpholine residue,

629 241

12th

T4, T5, T6 and T7 can also represent Cr to C4-, alkyl, preferably propyl.

In the formula (Ia) A 'preferably represents a radical of the formulas o d'

(7a)

(7b)

h «0

(7c)

n-ck.

(7d)

(7e),

in which the substituents D ', E', H ', F', G 'and K' represent the following radicals:

D 'for hydrogen, hydroxyl, amino, Q- to C4-alkylamino, phenylamino, in the 4-position substituted by methyl, methoxy, phenoxy, chlorine or bromine, phenylamino, alkylcarbonylamino with 1 to 3 carbon atoms in the alkyl or Benzoylamino.

E 'for acetyl, methoxycarbonyl, ethoxycarbonyl, n-prop-oxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, benzoyl, 4-methylbenzoyl, 2,4,6-trimethylbenzoyl, 4-methoxybenzoyl, 4-phenoxybenzoyl, N-propylaminocarbonyl, N-phenylamino-carbonyl , Methylsulfonyl, ethylsulfonyl, phenylsulfonyl, p-methylphenylsulfonyl, methoxy, phenoxy, 2-oxdiazolyl or 2-thiodiazolyl radicals which, in the 5-position, carry the substituents mentioned for R9 and R10, preferably phenyl.

F 'for hydroxy, amino, Cr to C5-alkylamino, phenylamino, phenylamino substituted in the 4-position by methyl, methoxy, phenoxy, chlorine or bromine.

G 'for hydroxy, amino, phenylamino, phenylamino, benzoylamino, alkylcarbonylamino with 1 to 3 C atoms in the alkyl substituted in the 4-position by methyl, methoxy, phenoxy, one of the substituents G' or H ', preferably H, can also be used for Nitro stand.

H 'is hydrogen, hydroxyl, amino, phenylamino, thiophenyl, where at least one of the substituents F', G 'or H', preferably F 'is OH.

Preferred dyes of the formula (10c) are those in which F 'is OH and G' and H 'are phenylamino which is optionally substituted by methyl, methoxy or phenoxy. For technical reasons, dyes of the formula (10c) are very particularly preferred, in which F 'is a phenylamino which is optionally substituted by methyl, methoxy, phenoxy, chlorine or bromine, G' is hydroxyl and H 'is nitro.

K 'for hydrogen, methyl, phenyl, 4-methylphenyl, 45 4-chlorophenyl.

Preparations of the dyes of the formulas (8) and IX are very particularly preferred because of their application properties and coloristic properties.

0 NH

■ y * '

60 N \ j £ ^ N

y '

65 where K ', X' and Y 'have the following meanings:

(8th) ,

K '

0

-c-nh-0

-c-0-ch (ch3) 2

13

-NH-

-NH- / V

■ C1

-NH

Y1

Cl

-NH- / ~ ^

629 241

0

ît

-c-o-

0

—N (n-C ^ Hy) g

-N "(n-C3H7) 2

-NH

J

0

1!

-C-CH-

-l / A-

OCH-

-nh-ch2-ch (ch3) 2

-NH - / "^

-NH - <^ ~ ^> -N (n — C ^ Hy) 2

-m-ch-c2h5 CH3

-nh-ch2-ch (ch3) 2

-nh-c (ch3)

D

_NH ~ V_y

-N (n-C ^ Jg

M 'O V

P 'O NH

TvT y t

YV

N \ ^ N Y '

(9),

where L ', M', P ', X' and Y 'have the following meanings:

629 241

l1 / -oh

14

m '

-nh,

p1

-Oh

-nh-

/ \

Oh oh

-nh- Ì ~ \ - 0 ~ f ~~ \

-nh- / ~~ ^!

• ci oh oh oh oh oh

-nh

-> ffî - </ ~ ^) - CH3 -N-CH2CH (CH3) 2

-NH- / ~ Vo- / ~>

-no,

no,

no,

-nh- (ch2) 3-0-ch (ch3).

-nh-ch2- / v>

-nh-ch (ch3) 2

-nh-ch2-çh - / ^ \

Ciî ^^

-nh-ch (ch3) 2 -nh- (ch2) 3-0- (ch2) 20- /

-nh-ch (ch ^) 2 -NH- ^

-nh-ch2-çh - <^ \

ch-

3rd

-nh- / ~ ^

15

629 241

l1

-nh- -ch

3rd

m '

Oh

P '

-no,

x '= y'

• nh-ch2-çh- / ~ \

ch,

3rd

Oh

-nh-

w

-NH

.r%. «Hii

-nh- / ~~ ^

-NH-

V

och-

such as

L '= OH

M '= P' = -NH-

/ V

OCH,

X '= -NH- (CH,) 3-OCH (CH3);

Y '= -NH-C4H9 (n)

and

L '= M' = P '= H X' = -NH- (CH2) 3-OCH3

Y '

och-

-NH- <;

-nh- (ch2) 2-

ch (ch3) 2

30th

The dyes of the formulas (I) and (la) can be referred to as disperse dyes in their constitution. They differ from vat dyes by their significantly better solubility in organic solvents.

In DE-PS 1 811 796, however, a method is described which enables the printing of water-insoluble dyes on cellulose or cellulose-containing textile material. The statements made in the patent with regard to the process conditions also apply analogously to the dye preparations according to the invention.

Furthermore, DE-OS 25 24 243 and 25 28 743 describe further processes by which the dye preparations according to the invention can be applied. Printing processes are preferred.

The dye formulations according to the invention give dyeings and prints with very good fastness properties, of which the wet fastness, the fastness to rubbing, the dry cleaning fastness and the light fastness are to be mentioned in particular. When printing, there is no bleeding of any white fund that may be present.

In the following examples, the parts and percentages are by weight unless otherwise noted. The room parts relate to the parts by weight like the liter to the kilogram.

The formulas belonging to the examples are shown on the drawing sheets. Example and formula numbers match.

example 1

a) A cotton fabric is printed in rotary film printing with a printing paste which consists of 10 parts of the dye of the formula see drawing sheet No. 1, example 1, in the form of a

40

30% preparation (see c), 100 parts of polyethylene oxide with a molecular weight of 300 and 790 parts of a 3% alginate thickening consists and dries the pressure at 100 ° C. Then treat with hot air for 1 minute at 200 ° C, rinse the pressure cold, soap it at the boil, rinse again cold and dry.

You get a light and washable purple print on a white background.

bl) The dye used is prepared as follows: To 34.6 parts of 1,4-diamino-2-phenyImercapto-anthraquinone in 250 room parts of N-methylpyrrolidone (NMP), a solution of 20.3 parts of cyanuric chloride in 200 room parts of NMP added dropwise at 20 ° C. The temperature rises to 30 ° C. The mixture is stirred at this temperature for 2 hours, after which it is stirred at 60 ° C. for a further 2 hours. After adding 37.2 parts of aniline, the mixture is heated to 80.degree. The mixture is stirred at this temperature for 2 hours, after which it is stirred at 100 ° C. for a further 2 hours. After cooling, the mixture is stirred into 1000 parts of water, the precipitate is filtered off with suction, washed first with methanol and then with water. After drying, 57 parts of the dye of the above formula are obtained in the form of a violet powder. The dye contains less than 0.5 percent chlorine.

b2) The dye used can also be prepared in the following way:

34.6 parts l, 4-diamino-2-phenylmercaptoanthraquinone and 32.6 parts 2,4 bis-phenylamino-6-chloro-l, 3,5-triazine are 50 den in 300 parts NMP 6 hours to 180 ° C heated. After cooling, the mixture is stirred into 600 parts of H20, the precipitate is filtered off with suction, washed first with methanol, then with water and dried.

c) The dye obtained according to bl) is converted into an aqueous, commercially available dye preparation in the following manner: 30 parts of the dye from bl), 6 parts of lignin sulfonate and 10 parts of dipropylene glycol are stirred in 50 parts of water and the suspension obtained is ground in a sand mill, until the particle size is 0.5 | xm and below. 60 parts of pentachlorophenol are then added and the dye content is adjusted to 30% by adding water. A storage-stable preparation is obtained.

If the above-mentioned dye is replaced by the same amount of a dye mentioned in the following table, then dyeings with equivalent fastness properties are obtained in the hues given in the table, see drawing sheets Nos. 2 to 9, Examples 2 to 49. Mixtures of the dyes indicated in the table can also be used

629 241

16

the. The dyes are prepared analogously to lbl) or lb2) and converted into dye preparations in the same way as lc).

At

At

At

game

Hue match

Hue match

hue

2nd

violet

17th

violet

33

violet

3rd

reddish

18th

do.

34

do.

blue

19th

do.

35

do.

4th

violet

20th

do.

36

do.

5

do.

21st

do.

37

purple

6

do.

22

do.

38

do.

7

do.

23

do.

39

do.

8th

do.

24th

do.

40

do.

9

do.

25th

reddish

41

do.

10th

reddish

blue

42

do.

blue

26

violet

43

do.

11

violet

27th

do.

44

do.

12th

do.

28

do.

45

do.

13

reddish

29

do.

46

do.

blue

30th

do.

47

do.

14

do.

31

do.

48

do.

15

violet

32

do.

49

do.

16

reddish

blue

Example 50

a) A mixed fabric of polyester / cotton (weight ratio 67:33) is printed with a paste consisting of 20 parts of the dye of the formula see drawing no. 10, example 50 in the form of the aqueous preparation prepared according to c), 120 parts of the reaction product consists of polyethylene oxide of molecular weight 300 with boric acid in a molar ratio of 3: 1 and 860 parts of a 10% alginate thickener. The pressure is dried at 105 ° C. and heated to 180 ° C. with hot steam for 6 minutes. First rinse with cold water, then soap the pressure at 80 ° C, rinse cold and dry.

You get a lightfast and washable blue print on a white background.

bl) The compound mentioned in 50 a) is prepared as follows: A solution of 10 parts of cyanuric chloride and 70 is at room temperature to a solution of 17.8 parts of 1,4-diamino-anthrachi-non-2-carboxylic acid anilide in 250 parts of nitrobenzene Parts of nitrobenzene were added dropwise. The mixture is then heated at 30 ° C. for 2 hours, at 60 ° C. for 2 hours and at 80 ° C. for 1 hour until a thin layer chromatogram shows that the reaction is complete. Then 15 parts of aniline and 15 parts of soda are added. This mixture is heated to 80 ° C for 2 hours and to 120 ° C for 4 hours. A thin layer chromatogram shows that the conversion was complete and selective. After cooling, the reaction mixture is diluted with methanol, the precipitate is filtered off with suction, washed with methanol and then with water and dried. 32 parts of the dye described above are obtained.

b2) The dye mentioned in 50 a) can also be prepared in the following way:

17.8 parts of 1,4-diamino-anthraquinone-2-carboxylic acid anilide are dissolved in 250 parts of molten phenol. 17 parts of 2,4-bis-phenylamino-6-chloro-l, 3,5-triazine are added to this mixture at 80.degree. The mixture is slowly heated to 180 ° C. within 2 hours and stirred at this temperature for 4 hours. The phenol is removed by steam distillation. The resulting dye is filtered off, washed with methanol and hot water and then dried.

c) The dye powder is, as indicated in Example lc), transferred to an aqueous preparation.

If the dye mentioned in the printing paste is replaced by the same amount of a dye listed in the table see drawing sheets Nos. 11 to 18, Examples 51 to 105, dyeings with similar fastness properties are obtained in the hues indicated in the table. The dyes mentioned in the table are prepared analogously to Examples 50 b1) or 50 b2) and converted into a liquid preparation analogously to Example 1 c).

At

hue

At

hue

At

Hue match

game

game

51

violet

70

blue

90

blue

52

do.

71

do.

91

do.

53

reddish

72

do.

92

do.

blue

73

do.

93

do.

54

do.

74

do.

93a do.

55

do.

75

do.

94

do.

56

do.

76

do.

95

do.

57

do.

77

do.

96

do.

58

do.

78

do.

97

do.

59

violet

79

do.

98

do.

60

violet

80

do.

99

do.

61

reddish

81

do.

100

do.

blue

82

do.

101

do.

62

do.

83

do.

102

do.

63

do.

84

do.

103

do.

64

blue

85

do.

104

do.

65

do.

S6

do.

105

do.

66

do.

S7

do.

67

do.

88

do.

68

do.

89

do.

69

do.

Example 106

a) A cotton fabric is printed in rouleaux printing with a printing paste which consists of 15 parts of the dye of the formula see drawing no. 19, example 106 in the form of a 30% strength aqueous preparation, 110 parts of polyethylene oxide with a molecular weight of 350.30 parts of oleic acid diethanolamide and 845 parts there is a 10% alginate thickening. The pressure is dried at 100 ° C. and then fixed by treatment with hot air at 195 ° C. Duration: 1 minute. You finish as described in Example 1 and get a real blue print on a white background.

b) The compound mentioned in 106a) is prepared as follows: A solution of 20.0 parts of cyanuric chloride in 300 parts of nitrobenzene is added to 34.4 parts of l-amino-4-p-anisidinoanthraquinone in 500 parts of nitrobenzene at room temperature. The mixture is then heated to 60 ° C. for 3 hours and stirred at 80 ° C. for 2 hours. After cooling, the mixture is stirred into 800 parts of methanol. The precipitate is filtered off, washed twice with 100 parts of methanol and dried in vacuo at 60 ° C. 41 parts of a violet powder containing 14.0% chlorine are obtained.

20 parts of this powder are dissolved in 100 parts of N-methyl-pyrrolidone at 80 ° C. 16.2 parts of di-n-propylamine are added to this solution and the mixture is stirred at 80 ° C. for 2 hours. The mixture is then stirred for a further 2 hours at 100 ° C., the reaction mixture is diluted with water, the precipitate is filtered off with suction, washed with water and dried. 21.9 parts of the dye indicated at 106 a) are obtained. It contains practically no chlorine.

c) The dye is, as indicated in Example lc), transferred to an aqueous preparation.

If the dye mentioned in Example 106 a) is replaced by the same amount of a dye mentioned in the table see drawing sheets Nos. 20 to 26, Examples 107 to 158, dyeings with similar fastness properties are obtained in the hues indicated in the table. The dyes

5

10th

15

2C

25th

30th

35

40

45

50

55

60

65

17th

629 241

are prepared analogously to Example 106 b) and converted into aqueous, stable preparations analogously to Example 1 c).

At

hue

At

hue

At

Hue match

game

game

107

blue

124

violet

141

orange

108

do.

125

do.

142

do.

109

do.

126

red

143

red

110

do.

127

do.

144

do.

111

do.

128

do.

145

do.

112

do.

129

blue

146

do.

113

do.

130

do.

147

do.

114

do.

131

do.

148

do.

115

do.

132

do.

149

do.

116

do.

133

do.

150

yellow

117

do.

134

red

151

do.

118

do.

135

do.

152

do.

119

do.

136

do.

153

do.

120

do.

137

do.

154

do.

121

violet

138

do.

155

do.

122

do.

139

orange

156

do.

123

do.

140

do.

157

do.

158

do.

Example 159

a) A cotton fabric is padded on a foulard with a hotte, the 20 parts of the dye of the formula see drawing no.27, example 159, in the form of a 30% aqueous, finely divided preparation, 300 parts of a 3% alginate thickener, 550 parts Contains water and 130 parts of polyethylene oxide with a molecular weight of 300. The liquor absorption is 80%, based on tissue. The fabric is dried at 100 ° C. To fix the dye, treat it with hot steam at 190 ° C for 5 minutes. Then rinsed cold, washed at 90 ° C in a bath containing 0.3% of an ethylene oxide adduct based on a Ci; - to C15-alcohol mixture. A blue color is obtained.

If a polyester / cotton blend (weight ratio 67:33) is used instead of a cotton fabric, a blue dyeing is obtained after fixation, in which both fibers are dyed the same shade. Instead of treatment with hot steam, fixation can also be done with hot air in 2 minutes at 195 ° C.

b) The dye used in Example 159 a) is prepared in the following way: 67.5 parts of 4,8-diamino-anthra-rufin in 500 parts by volume of N-methylpyrrolidone at 30 ° C., a solution of 48 parts of cyanuric chloride in 700 parts of the space N-Methylpyrrolidone added dropwise. The temperature rises to 35 ° C. The mixture is then stirred for 2 hours at this temperature. 60 parts of toluidine mixture are then added and the mixture is stirred at 100 ° C. for 3 hours. After cooling, the mixture is diluted with water, the precipitate is filtered off, washed with warm water and dried. 135 parts of a violet-blue color powder are obtained.

c) The dye is, as indicated in Example 1 c), converted into a stable aqueous preparation.

If a mixture of 4,8-diamino-an-thrarufin and 4,5-diamino-chrysazine is used in b), a dye with very similar properties is obtained.

If the dye mentioned in Example 159 a) is replaced by the same amount of the dyes mentioned in the table, see drawing sheets Nos. 28 to 39, Examples 160 to 249, dyeings with similar fastness properties are obtained. The color shades of the dyeings are given in the table. The dyes can be prepared analogously to Example 159 b) and converted into stable, aqueous, finely divided preparations according to Example 1 c).

example

160; 161

162

163

164

165 io 166

167

168

169

170 15 171

172

173

174

175 20 176

177

178

179

180 25 181

182

183

184

185 so 186

187

188

189

190 35 191

192

193

194

195

•"O

Example 250

a) You print a cotton fabric in rotary film printing with a color that consists of 10 parts of the dye of

For the 4s formula, see drawing no. 40, example 250, in the form of a 25 percent aqueous, finely divided preparation, 100 parts of polyethylene oxide with a molecular weight of 300 and 790 parts of a 3% thickening of alginate, and dries the pressure at 100 ° C. Then treat with hot air at 200 ° C for 1 minute, rinse the pressure cold, soap it at the boil, rinse again cold and dry. You get a light and washable purple print on a white background.

b) The dye mentioned in Example 250 a) is prepared as follows:

55 23.8 parts of 1,4-diamino-anthraquinone are dissolved in 300 parts of nitrobenzene. 38 parts of cyanuric chloride (finely powdered) and 38 parts of soda are added to this solution. This mixture is stirred at 70 ° C for 3.5 hours and then cooled to 60 ° C. 25 parts of aniline 60 are added at this temperature. The mixture is then stirred at 60 ° C for 4 hours. When a thin layer chromatogram shows that the reaction is complete, 30 parts of 5-methylhexylamine are added and the mixture is stirred for 3 hours at 100 ° C. and 1 hour at 130 ° C. The reaction mixture is stirred in methanol, the precipitated dye is filtered off with suction and washed first with methanol, then with warm water. After drying, the dye mentioned in Example 250 a) is obtained as a violet powder in good yield.

hue

At

hue

At

hue

game

game

blue

196

blue

226

green do.

196a do.

227

do.

do.

197

do.

228

do.

do.

198

do.

228a do.

do.

199

do.

228b do.

do.

200

do.

229

do.

do.

201

do.

230

do.

do.

202

do.

231

do.

do.

203

do.

232

do.

do.

204

do.

233

do.

do.

204a do.

234

do.

do.

205

do.

235

do.

do.

206

do.

236

orange do.

207

do.

237

do.

do.

208

green

238

do.

do.

209

do.

239

do.

do.

210

do.

240

do.

do.

211

do.

241

do.

do.

211a do.

242

do.

do.

211b do.

243

do.

do.

212

do.

244

violet do.

213

do.

245

do.

do.

214

do.

246

do.

do.

215

do.

247

do.

turquoise

216

do.

248

do.

do.

217

do.

249

do.

do.

218

do.

do.

219

do.

do.

219a do.

do.

219b do.

do.

220

do.

do.

221

do.

blue

222

do.

do.

223

do.

do.

224

do.

do.

225

do.

629 241

18th

c) The dye is, as indicated in Example 1 c), converted into a finely divided, stable aqueous preparation.

If, instead of the dye mentioned in Example 250 a), one of the dyes mentioned in the table see drawing no. 40, Examples 251 to 225 a is used, dyeings with similar fastness properties are obtained in the specified shades. The dyes are prepared analogously to Example 250 a) and converted into liquid, finely divided preparations analogously to Example 1 c).

At

hue

At

hue

At

Hue match

game

game

251

violet

253

violet

255

violet

252

do.

254

do.

255a do.

Example 256

a) A cotton fabric is padded on the foulard with a liquor of 150 parts of polyethylene oxide in 850 parts of water so that the liquor absorption is 80% and the padded fabric is dried at 100.degree. The fabric pretreated in this way is printed on a rotary film printing machine with a color consisting of 30 parts of the dye of the formula see drawing no. 41, example 256, in the form of a 30 percent aqueous, finely divided preparation and 970 parts of a 10% alginate thickener. After the pressure has dried at 105 ° C., it is heated with hot steam to 185 ° C. for 7 minutes and then, as described in Example 1 a), finished by rinsing and soaping. You get a real yellow print on a white background.

b) The dye described in Example 256 a) is prepared analogously to Example 50 b2) by reacting C-phenyl-4-amino- (1,9) -anthrapyrimidine with 2,4-bis-isopropylamino-6-chloro-1,3 , 5-tria-zin.

c) The dye is, as indicated in Example 1 c), converted into a finely divided, stable aqueous preparation.

If the dye mentioned in Example 256 a) is replaced by one of the dyes mentioned in the tables, see drawing sheets Nos. 42 and 43, Examples 257 to 268, then dyeings are obtained in the specified colors with similar fastness properties. The dyes are prepared analogously to the information in Example 50 b2) and converted into a stable liquid preparation in accordance with Example 1 c).

At

hue

At

hue

At

Hue match

game

game

257

yellow

259

yellow

261

yellow

258

do.

260

do.

262

do.

263 do.

Color hue color hue color hue

264 red 266 red 268 red

265 do. 267 do.

Example 269

a) A mixed fabric of polyester / cellulose (weight ratio 67:33) is printed on a film printing machine with a color consisting of 30 parts of the dye of the formula see drawing no. 43, example 269,100 parts of the reaction product of polyethylene oxide with a molecular weight of 300 and boric acid in Molar ratio 3: 1.30 parts of oleic acid diethanol amide and 840 parts of a 3 percent alginate thickening consists and dries the pressure at 110 ° C. It is then treated with hot steam at 185 ° C. for 5 minutes and finished as described in Example 1. You get a real purple print on a white background.

b) The dye used in Example 269 a) is prepared as follows:

25.2 parts of l-amino-4- (4,6-dichloro-l, 3,5-triazin-2-yl) ami-no-anthraquinone-2-carboxylic acid anilide are dissolved in 300 parts of N-methyl-pyrrolidone. Then 15 parts of thiophenol with 12 parts of soda are added and the mixture is stirred for 3 hours at 100 ° C and 2 hours at 130 ° C. The mixture is then diluted with methanol, the dye which has precipitated is filtered off with suction and washed with methanol. After drying, 26 parts of the dye mentioned in 269 a) are obtained.

c) The dye is converted into a stable, finely divided preparation analogously to Example 1 c).

If, instead of the dye mentioned in Example 269 a), the same amount of one of the dyes shown in the table see drawing sheets Nos. 44 to 46, Examples 270 to 291 is used, dyeings with similar fastness properties are obtained with the hues given in the table. The dyes are prepared analogously to paragraph b) of Example 269 and converted into liquid preparations in accordance with Example 1 c).

5

10th

IS

20th

25th

30th

35

40

45

50

c

46 sheets of drawings

Claims (6)

629 241 PATENT CLAIMS 1. Commercial dye preparations for dyeing and printing cellulose and cellulose-containing textile material, containing, among other components, dyes of the formula I free from sulfonic acid groups -nh- * -C y (I), n in the A an optionally substituted anthraquinonyl residue or a substituted anthraquinonyl residue fused in the 1,9-position with a pyrimidine or pyridone ring, X and Y are identical or different radicals of the formulas r / T2 -N C or —S — T3 and T1, n is the number 1 or 2 and where in the formulas T2 is hydrogen, an aliphatic radical or phenoxy-Cr to C4-alkyl or Cr to C6-alkylthio, T1 for hydrogen, an aliphatic, cycloaliphatic, araliphatic or aromatic radical or the group / T2 -N: \ T1 for a saturated 5-, 6- or 7-membered heterocyclic radical and T3 represents an aliphatic, alicyclic or aromatic radical. 2. dye preparations according to claim 1, comprising, in addition to dispersants, water retention agents and water, dyes of the formula I in which n is the number 1 or 2, A (1) is a mono- or divalent anthraquinonyl radical, which a) optionally in further a-positions as substituents chlorine, bromine, Cr to Q-alkyl, CL to C6 alkoxy; phenoxy optionally substituted by Cp to C6-alkyl, chlorine or bromine; Q to C6 alkylthio; phenylthio optionally substituted by Ct to C6 alkyl, chlorine or bromine; Hydroxy, amino, Cr to C8-alkylamino, where the alkyl can be substituted by hydroxy, Cr to C4-alkoxy, cyano or carbonyl-C2- to C6-alkoxy; phenylamino optionally substituted by Q- to C5-alkyl, methoxy, ethoxy, chlorine, bromine or phenoxy and -NH-C-R 'and -NH-C-NH- where R 'for Q- bis O Z Cs-alkyl or phenyl optionally substituted by Ct to C4-alkyl, bromine, chlorine, methoxy or ethoxy and Z represents O or S, where in the case of more than one substituent these may be the same or different and the b ) optionally in the 2-position as a substituent cyan, acetyl, propionyl, optionally substituted by 1 to 3 methyl, methoxy or phenoxy benzoyl; Cr to C6-alkylsulfonyl, phenylsulfonyl, N-Cr to C6-alkylsulfamoyI, N, N-bis (C! - to C6-alkyl) -sulfamoyl, N-C3- to C12-alkoxyalkylsulfamoyl, N, N-bis ( C3- to C12-alkoxyalkyl) -sulfamoyl, Cr to C6-alkoxycarbonyl, cyclohexoxycarbonyl, N-Cr to C6-alkyaminocarbonyl, N, N-bis (Cr to C6-alkyl) amino-carbonyl, N-phenylamino- carbonyl, N- (C [- to C6-alkylphenyl) aminocarbonyl; Oxdiazo-lyl- (2), which in the 5-position is a phenyl which is optionally substituted by Cr to C6-alkyl, C [- to C4-alkoxy, chlorine or bromine, an optionally by chlorine, bromine, hydroxy, cyano, 5 Cr to Ct-alkoxy, di- (Cr to C4-alkyl) amino, carbamoyl, carbonyl-C2- to Q-alkoxy, Cr to C5-alkylthio, phenyl or phenoxy-substituted Ci- to C10-alkyl, the phenyl radicals can be substituted by chlorine, bromine, Q- to C4-alkyl, methoxy, ethoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl and / or io N-alkylsulfamoyl with 1 to 4 C atoms per alkyl, a Cr to C5-alkylthio, a C7 - C10-Phenal-kylthio or a phenylthio optionally substituted by chlorine, bromine, Q- to C4-alkyl, methoxy or ethoxy as a substituent; ThiodiazoIyl- (2), which is in the 5-position as a substituent 15 to Cr to C5-alkyl, Cr to C8-alkylthio, C3 to C8-alkoxy-alkyl, Ct to Cs-alkylamino, methoxy, ethoxy or optionally phenyl substituted by Cr to C6-alkyl, Cr to C4-alkoxy, chlorine or bromine, or isoxdiazoIyl- (5), which in the 3-position as a substituent is optionally substituted by saturated 20 or 5-membered or 6-membered heterocyclic rings , which contain N as a ring member, substituted by phenoxy, phenalkoxy, Cr to C5-alkylthio or Cr to C5-alkylsulfonyl-substituted Cr to C8-alkyl; C3- to Cg-alkoxyalkyl, phen-Cr to C5-alkyl, phenyl or a 6-membered saturated or unsaturated heterocycli-25 see ring, the phenyl nucleus or the heterocycles optionally by Cr to C5-alkyl, chlorine, bromine, hydroxy or Q- to C4-alkoxy are substituted, and wherein a C atom in the 2-, 5- or 8-position can also carry a nitro group and the number of substituents can be 0 to 6, or 30 (2) an a Anthrapyrimidine or a-anthrapyridone radical, these radicals optionally by Q- to Cs-alkyl and optionally 1 hydrogen atom by hydroxyl, Q- to C6-alkoxycarbonyl, phenyl, Q- to C6-alkylphenyl, Cr to Q-alkyl- carbonyl, benzoyl or cyan are substituted and the number of 35 substituents can be 0 to 2, T1 a) saturated, linear or branched Cr to Cla alkyl, b) by cyan, chlorine, bromine, carbonylalkoxy with a total of 40 2 to 5 carbon atoms, N-alkylaminocarbonyl or N, N-dialkylaminocarbonyl with 1 to 8 carbon atoms per alkyl, Cr to C4-alkylsulfonyl, amino, dialkylamino CV to C8-alkyl substituted with 1 to 4 carbon atoms per alkyl or phenoxy, the number of substituents being 2 or preferably 1; 45 c) alkoxyalkyl with a total of 3 to 11 carbon atoms, d) hydroxyalkoxyalkyl and alkoxyalkoxyalkyl with a total of 4 to 10 carbon atoms, e) phenoxyalkoxyalkyl with a total of 10 to 12 carbon atoms, f) saturated 5-, 6-, 7- or 8-membered cycloalkyl or 5 ° polycycloalkyl, g) cycloalkyl optionally substituted by 1 to 3 Cr to C8-alkyl, cycloalkyl or hydroxyl, h) phenalkyl with a total of 7 to 10 carbon atoms, in which optionally the alkyl radical by hydroxyl and optionally 55 the phenyl radical is substituted by Q to C15 alkyl, i) phenyl, a- or β-naphthyl, in which 1 to 3 hydrogen through Cr to Cl8-alkyl, hydroxy, chlorine, bromine, trifluoromethyl, nitro, cyano, Cr to C5-alkoxy, C ^ to C4-alkylthio, if appropriate, Alkanoylamino with 2 to 5 carbon atoms, sulfamoyl, 60 N-alkyl- or N, N-dialkylsulfamoyl with 1 to 8 C atoms per alkyl, N-phenylsulfamoyl, carbamoyl, N-alkylaminocarbonyl or N, N-dialkylaminocarbonyl with 1 to 8 C atoms per alkyl, N-phenylamino carbonyl, where the phenyl radical can be substituted by methoxy, ethoxy or methyl, carbonylalkoxy with 65 in total 2 to 6 carbon atoms, Cr to C4-alkylsulfonyl, phenylsulfonyl, which is optionally substituted in the phenyl by alkyl, Cr to Q-alkylcarbonyi , Phenalkoxy are substituted with 7 to 10 carbon atoms or phenoxy and where the substituents can be the same or different and, in the case of more than one alkyl, alkoxy or alkyl and alkoxy, the sum of the C atoms in this substituent is at most 12, T2 hydrogen, linear or branched Cr to C8-alkyl; by hydroxy, cyan, chlorine, bromine, carbonylalkoxy with a total of 2 to 5 carbon atoms, N-alkylaminocarbonyl or N, N-dialkylaminocarbonyl with 1 to 8 carbon atoms per alkyl, by C [- to C4-alkyIsulfonyl, Cr C to C4 alkylthio or phenoxy substituted Cr to C4 alkyl; Total alkoxyalkyl 3,629,241 Thiomorpholins, hexamethyleneimines, piperazines, N'-methyl or N'-ethylpiperazines and T3 is a linear or branched C 1 -C 8 alkyl; Cj to Cs alkyl substituted by C (- to Q-alkoxy or phenoxy; 3 to 6 carbon atoms or Cp to C6-alkylthio or the group / T2 -N \ a residue of pyrrolidine, piperidine, morpholine, 4. dye preparations according to claims 1 and 3, vorin R1 is hydrogen, acetyl, benzoyl, cyano, methyl, dimethyl ind trimethylbenzoyl, methoxy and ethoxybenzoyl, phen-> xybenzoyI; Cr to Cs alkoxycarbonyl, cyclohexoxycarbonyl; Zr to C4-alkylaminocarbonyl, phenylaminocarbonyl, phenyl-iminocarbonyl substituted by methyl, chlorine, bromine, methoxy, ethoxy, Cr to C6-alkylthio, phenylthio, Cr to C4-vinylphenylthio, Cr to C8-alkoxy, phenoxy, chlorophenoxy, îromphenoxy, methylphen , Cr to C4 alkylsulfonyl, phenylsulfonyl and methylsulfonyl; 55 60 or stands in which D 'hydrogen, hydroxyl, amino, Cr to C4-alkylamino, phenylamino, phenylamino substituted in the 4-position by methyl, methoxy, phenoxy, 65 chlorine or bromine, alkylcarbonylamino with 1 to 3 C atoms in the alkyl or benzoylamino, E 'acetyl, methoxycarbonyl, ethoxycarbonyl, n-propoxy-carbonyl, isopropoxycarbonyl, butoxycarbonyl, benzoyl, 4-Me- 4th "Mkyl, phenyl, phenyl substituted by C 1 -C 4 alkyl, bromine, chlorine, methoxy or ethoxy or -NH-C — NH— v v), where Z is O or S, 20th R3 and R4 are hydrogen, hydroxy, amino, Cr to C4-alkylimino, phenylamino, phenylamino substituted by Cr to C4-alkyl, methoxy, ethoxy, chlorine, bromine or phenoxy, Cr to 1H C6-alkylthio, phenylthio, by Cp to C5 alkyl substituted phenylthio, —NH-C-R12, wherein R12 is the above Has meaning, or -NH-C — NH— $, where Z is O I! W / Z D is S, where the R3 and R4 radicals can be the same or different and one of the R3 or R4 radicals can also be nitro, R5 is hydrogen or methoxy, R6 nitro or the groups mentioned for R7, in which case R7 and R6 can be the same or different, R7 is hydrogen, hydroxy, saturated linear or branched Cr to C5-alkylamino, where the alkyl can be substituted by CL- to C4-alkoxy, hydroxy or cyano; R8 amino, Cr to C5-alkylamino or hydroxy, R9phenyl; by Cr to C6-alkyl, Cp to C4-alkoxy, Chlorine, bromine, substituted phenyl; Cp to C [C0 alkyl; Cp to C10 alkyl by chlorine, bromine. Hydroxy, cyano, Cp to C4- ^ lkoxy, dialkylamino with 1 to 4 C atoms per alkyl, carbimoyl, carbonylalkoxy with a total of 2 to 9 C atoms, C, - to C5-alkylthio, phenyl or phenoxy is substituted ( where in 1 phenyi substituents optionally 1 or 2 hydrogen atoms by chlorine, bromine, Cr to C4-alkyl, methoxy, ethoxy, 3 <alkoxycarbonyl, alkylthio, alkylsulfonyl and / or N-alkylsul- "amoyl with 1 to 4 carbon atoms each Alkyl are substituted); Cr to Cs-alkylthio; C7 to C10-phenylalkylthio; phenylthio or phenylthio substituted by chlorine, bromine, Cr to C4-alkyl, methoxy or ethoxy; R10 Cp to C5 alkyl; Cp to Cg alkylthio, C3 to Cs alk alkoxyalkyl; Cp to C5 alkylamino; Methoxy, ethoxy or Phe-iiyl, which is optionally substituted by Cp to C6-alkyl, Ct to C4-alk-Dxy, chlorine or bromine, and Ru amino or Cp to C5-alkylamino, R1S is hydrogen, Cp to C6-alkoxycarbonyl, Cr to C4-Al-icylcarbonyl, benzoyl or cyan; R18 is hydrogen, Cr to Q-alkyl or phenyl; R16 is hydrogen, Cr to C5 alkyl, phenyl, Cr to C5 alkyl phenyl or halophenyl; 50 R17 and R19 are hydrogen, hydroxy, -NH-C-R12, wherein R12 R2 hydrogen, hydroxy, amino, Cr to C4-alkylamino, phenylamino, phenylamino substituted by Cr to C5-alkyl, methoxy, ethoxy, phenoxy, C2- to C4-C-acyloxy, Cr to C4-alkoxy, -NH-CO- R ', in which R' for Cp to C5 alkyl or Phenyl, or -NH-C-NH- ^ ^, where Z is O or Z S stands; R3 and R4 are hydrogen, hydroxyl, amino, phenylamino, chlorophenylamino, methylphenylamino, methoxyphenylamino, phenoxyphenylamino, ethoxyphenylamino, thiophenyl, benzoylamino or acetylamino, where the substituents can be the same or different and one of the radicals R3 or R4 also for nitro or for - NH-C-NH-C6H5 may be where 30th Z represents O or S; Rs, R6 and R7 are hydrogen; R8 amino; R9 phenoxyalkyl with 1 to 6 C atoms in the alkyl, phenalkyl with 1 to 6 C atoms in the alkyl, Cr to C5 alkyl or phenyl; R10 Q to Cj-alkyl, Cr to C5-alkylthio, phenalkylthio with 2 to 4 carbon atoms in the alkyl, or phenyl; Rn amino; R15 is hydrogen; R16 is hydrogen, phenyl or Cr to C:, - alkylpheny [; R17 and R19 are hydrogen or hydroxyl and R! S are hydrogen or methyl. 5. Dye preparations according to claim 1, wherein in the formula IA for a radical of the formulas 40 45 iie has the meaning given above or amino, where R17 and R19 may be the same or different, and T1, T2 and T3 have the meaning given in claim 2. 5 629 241 thylbenzoyl, 2,4,6-trimethylbenzoyl, 4-methoxybenzoyl, 4-phenoxybenzoyl, N-propylaminocarbonyl, N-phenylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, p-methethylphenylsulfonyl, methoxy, pheniazol, 2-oxoxy or 2-oxoxy -Thiodiazolylreste, which in the 5-position carry the substituents mentioned in claim 4 for R9 and Rin, F 'hydroxyl, amino, Cp to Cj-alkylamino, phenylamino or phenylamino substituted in the 4-position by methyl, methoxy, phenoxy, chlorine or bromine, G 'hydroxy, amino, phenylamino, phenylamino, benzoyl-amino or alkylcarbonylamino with 1 to 3 C atoms in the alkyl substituted in the 4-position by methyl, methoxy, phenoxy, where one of the substituents G' or H 'can stand for nitro, H 'is hydrogen, hydroxy, amino, phenylamino, thiophene, where at least one of the substituents F', G 'or H' is hydroxy, K 'hydrogen, methyl, phenyl, 4-methylpheny! or 4-chlorophenyl, X is a radical of the formula —N v and n Y for a radical of the formula -N \ stenen. bliss T5 stands in what K 'phenylaminocarbonyl, 4-methoxyphenylaminocarbonyI. Mean isopropoxycarbonyl, cyclohexoxycarbonyl or acetyl, and X and Y are phenylamino, 4-chlorophenylamino, 2-butylamino, di-n-propylamino, 2-methylpropylamino or tert-butylamino, where X and Y can be the same or different. 7. Dye preparations according to claim 1, wherein in the formula IA represents a radical of the formula in which L 'hydroxy, 4-phenoxyphenylamino, 4-chlorophenylamino, 4-methylphenylamino or phenylamino, M 'hydroxy, amino, phenylamino or 4-methoxyphenyl-j amino and P 'is hydroxy, phenylamino, 4-methoxyphenylamino, 4-phenoxyphenylamino or nitro, where at least one of the substituents L', M 'or P' is hydroxy, and X and Y are phenylamino, 3-chloro-4-methoxyphenylamino, 10 N- (l-isobutyl) phenylamino, benzylamino, 2-phenylpropyl-3mino- (l), 2-propylamino, 3-methyl-butylamino- (l), 3-iso-propoxypropylamino- (l) or 3- (2'-phenoxyethoxy) propylamino (1). T1 and T6 are hydrogen or Ct to C alkyl, and T and T7 are Cp to Cp alkyl, alkoxyalkyl with a total of 3 to 7 C atoms, hydroxyalkoxyalkyl with a total of 4 to 7 C atoms, phenalkyl with a total of 7 to 10 C Atoms, phenoxy-C2 to Ci-alkyl, phenoxyalkoxyalkyl with 4 to 6 carbon atoms in alkoxyalkyl, cyclohexyl, phenyl or phenyl. in which i to 3 hydrogen by methyl, methoxy, ethoxy, chlorine and / or bromine or a hydrogen by carbonalkoxy with a total of 2 to 5 carbon atoms. an alkylaminocarbonyl or a diaikylsulfamoyl with 1 to 4 carbon atoms per alkyl, a phenoxy or a benzyloxy, or the radical -N -, T * is a piperidine or morpholine residue. 5 phenalkyl with 7 to 10 carbon atoms; Cyclohexyl or phenyl, which is optionally substituted by 1 to 3 Ct to C18 alkyl, Cr to C4 alkoxy, Cr to C4 alkylthio, chlorine or bromine and where the substituents can be the same or different. 10 3. dye preparations according to claim 1, wherein in the formula IA for O R or , 15th 0 stands in which Shark chlorine or bromine, m '0.1 or 2; R1 hydrogen, chlorine, bromine, methyl, ethyl, Cr to C6-alkoxy, phenoxy, alkylphenoxy with 1 to 6 carbon atoms in alkyl, chlorophenoxy, bromophenoxy, Cr to Q-alkylthio, phenylthio, alkylphenylthio with 1 to 6 carbon atoms in alkyl, acetyl, propionyl, benzoyl, mono-, di- and trimethylbenzoyl, methoxybenzoyl, phenoxybenzoyl, Ct- to C6-alkoxycarbonyl, cyclohexoxycarbonyl, N-alkyl or N, N-dialkylaminocarbonyl with 1 to 6 carbon atoms each alkyl, phenylaminocarbonyl, alkylphenylaminocarbonyl with 1 to 6 carbon atoms in alkyl, cyano, nitro, C [- to C6-alkylsulfonyl, phenylsulfonyl, Cr to C6-Al- kylphenylsulfonyl, N-alkyl or N, N-dialkylsulfamoyl with 1 to 6 carbon atoms per alkyl, N- (alkoxyalkyl) - or N, N-bis (A1-koxyalkyl) sulfamoyl with 3 to 12 carbon atoms per alkoxyalkyl ; R2 is hydrogen, hydroxy, Cr to C4 alkoxy, amino, Q-60 to C8 alkylamino; Cr to Cg-alkylamino substituted by hydroxy, Cr to C4-alkoxy, cyan or carbonylalkoxy with a total of 2 to 6 C atoms; Phenylamino; phenylamino substituted by Q to C5 alkyl, methoxy, ethoxy, phenoxy, chlorine or bromine; Cr to C6 alkylthio; Phenylthio; phenylthio substituted by 65 Cr to C5-alkyl; -NH-C-R12, in the II O R12 for a saturated, linear or branched Q to C3 529 241 6. dye preparations according to claim 1, wherein in the formula IA for a radical of the formula