(2-Chloro-4-cyanophenyl) (4-dialkylaminophenyl)-diazine dye useful for transfer printing

Dyes useful for transfer printing and having the formula ##STR1## in which X and Y are hydrogen or halogen, PA1 Z is hydrogen or methyl, PA1 R.sup.1 is hydrogen, lower alkyl or alkoxy, PA1 R.sup.2 is hydrogen, chlorine, lower alkyl, alkoxy, alkanoylamino or pyrrolidonyl, and PA1 R.sup.3 and R.sup.4 are alkyl optionally substituted by alkoxy, chlorine, alkanoyl or alkoxycarbonyl. The dyes are especially useful for the transfer printing of polyamides, giving prints having very good light and wet fastnesses.

The invention relates to the use of dyes of the formula (I): 
##STR2## 
in which X is hydrogen, chloro or bromo; 
Y is hydrogen or chloro; 
Z is hydrogen or methyl; 
R.sup.1 is hydrogen, C.sub.1 to C.sub.4 alkyl, methoxy or ethoxy; 
R.sup.2 is hydrogen, C.sub.1 to C.sub.4 alkyl, chloro, methoxy, ethoxy, 
C.sub.1 to C.sub.4 alkanoylamino which may bear chloro, methoxy or ethoxy 
as a substituent of 
##STR3## 
R.sup.3 is allyl, methallyl, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.8 
alkanoyloxy-C.sub.2 - to C.sub.4 -alkyl optionaly bearing chloro, methoxy 
or ethoxy as a subtituent in the alkanoyl or C.sub.2 to C.sub.4 alkyl 
bearing chloro or C.sub.1 to C.sub.8 alkoxycarbonyl as a substituent; and 
R.sup.4 is C.sub.1 to C.sub.4 alkyl, or C.sub.2 to C.sub.4 alkyl bearing 
C.sub.1 to C.sub.4 alkoxy or chloro as a substituent for transfer printing 
and also the new dyes. 
The alkyl radical R.sup.1 may be butyl, propyl or ethyl and particularly 
methyl. 
Suitable radicals R.sup.2, besides those already specified, are butyl, 
propyl, ethyl, formylamino, chloroacetylamino, methoxyacetylamino, 
ethoxyacetylamino and particularly methyl, acetylamino, propionylamino, 
n-butyrylamino or isobutyrylamino. 
Examples of radicals R.sup.3 are: methyl, butyl, hexoxyethyl, 
.beta.-ethylhexoxyethyl, hexoxypropyl, .beta.-ethylhexoxypropyl, 
methoxybutyl, ethoxybutyl, formyloxyethyl, formyloxypropyl, 
chloroacetoxyethyl, chloroacetoxypropyl, ethoxyacetoxyethyl, 
ethoxyacetoxypropyl, hexanoyloxyethyl, hexanoyloxypropyl, 
.beta.-ethylhexanoyloxyethyl, .beta.ethylhexanoyloxypropyl, 
methoxycarbonylpropyl, ethoxycarbonylpropyl, propoxycarbonylpropyl, 
butoxycarbonylproyl, hexoxycarbonylethyl, hexoxycarbonylpropyl, 
.beta.-ethylhexoxycarbonylethyl, .beta.-ethylhexoxycarbonylpropyl and 
particularly ethyl, propyl, chloroethyl, methoxyethyl, methoxypropyl, 
ethoxyethyl, ethoxypropyl, n-propoxyethyl, isopropoxyethyl, 
n-propoxypropyl, isopropoxypropyl, acetoxyethyl, acetoxypropyl 
methoxyacetoxyethyl, methoxyacetoxypropyl, propionyloxyethyl, 
propionyloxypropyl, n-butyryloxyethyl, isobutyryloxyethyl, 
methoxycarbonylethyl, n-propoxycarbonylethyl, isopropoxycarbonylethyl, 
n-butoxycarbonylethyl, isobutoxycarbonylethyl or t-butoxycarbonylethyl. 
Examples of radicals R.sup.4 are: methyl, butyl and chloroethyl and 
particularly ethyl, propyl, methoxyethyl, ethoxyethyl, n-propoxyethyl, 
isopropoxyethyl, n-butoxyethyl, isobutoxyethyl, methoxypropyl, 
ethoxypropyl, n-propoxyypropyl, isopropoxyethyl, n-butoxypropyl and 
isobutoxypropyl. 
Particular technical importance attaches to dyes of the formula (Ia): 
##STR4## 
in which R.sup.5 is hydrogen or methyl; 
R.sup.6 is hydrogen, methyl, ethyl or C.sub.2 to C.sub.4 alkanoylamino; 
R.sup.7 is C.sub.2 to C.sub.4 alkyl or C.sub.2 to C.sub.3 alkyl bearing 
C.sub.1 to C.sub.4 alkoxy, chloro, C.sub.2 to C.sub.4 alkanoylalkyl or 
C.sub.1 to C.sub.4 alkoxycarbonyl as a substituent; and 
R.sup.8 is C.sub.2 to C.sub.4 alkyl or C.sub.2 to C.sub.4 alkyl bearing 
C.sub.1 to C.sub.4 alkoxy as a substituent. 
One group of preferred dyes in that of formula (Ia) in which R.sup.5 is 
hydrogen and R.sup.6 is C.sub.1 - to C.sub.4 - alkyl. 
Methyl or ethyl is particularly preferred for R.sup.6. 
The dyes of formula (I) may be prepared by reacting a diazo compound of an 
amine of the formula (II): 
##STR5## 
with a coupling component of the formula (III): 
##STR6## 
Dyes of the formula (I), some of which are new, are outstandingly suitable 
for transfer printing on substrates such as acrylonitrile polymers and 
preferably polyesters and polyamides. 
For a long time there has been a demand for red dyes with which it is 
possible to obtain light-fast and wet-fast dyeings on polyamides by the 
transfer method. Light-fast red dyes transferable in particular onto 
polyamides have not hitherto been available. With the red compounds of the 
formula (I) it is possible to obtain on polyamides dyeings which are fast 
to both light and wet treatments and the wet fastness properties and the 
transferability can be preferentially influenced by the radicals R.sup.3 
and R.sup.4. Radicals R.sup.3 and R.sup.4 preferably contain an ether 
oxygen atom or are preferably alkyl radicals. 
Another group of preferred dyes in that of the formula (Ib) 
##STR7## 
in which R.sup.9 is C.sub.1 - to C.sub.4 -alkyl; R.sup.7 is C.sub.2 - to 
C.sub.4 -alkyl, C.sub.1 - to C.sub.4 -alkoxy-C.sub.2 - to C.sub.3 -alkyl 
or .beta.-chloroethyl; and R.sup.8 is C.sub.2 - to C.sub.4 -alkyl or 
C.sub.1 - to C.sub.4 -alkoxy-C.sub.2 - to C.sub.4 -alkyl. In formula (Ib), 
methyl is particularly preferred for R.sup.9. 
Generally preferred dyes are those of the formula 
##STR8## 
in which R.sup.1 is hydrogen, C.sub.1 - to C.sub.4 -alkyl, methoxy or 
ethoxy, 
R.sup.2 is hydrogen, chlorine or C.sub.1 - to C.sub.4 -alkyl, 
R.sup.3 is C.sub.1 - to C.sub.4 -alkyl or C.sub.2 - to C.sub.4 -alkyl 
substituted by C.sub.1 - to C.sub.6 -alkoxy, chloro, C.sub.1 - to C.sub.4 
-alkanoyl, chloroacetyl, chloropropionyl, methoxyacetyl, ethoxyacetyl or 
C.sub.1 - to C.sub.4 -alkoxycarbonyl, 
R.sup.4 is C.sub.1 - to C.sub.6 -alkyl or C.sub.2 - to C.sub.4 -alkyl 
substituted by C.sub.1 - to C.sub.4 -alkoxy or chloro and 
Z is hydrogen or methyl. Those dyes of the formula (Ic) are especially 
preferred in which 
R.sup.1 is hydrogen, R.sup.2 is C.sub.1 - to C.sub.4 -alkyl, and R.sup.3, 
R.sup.4 and Z have the same meanings as given under formula (Ic). 
Transfer printing processes are known for example from French Pat. No. 
1,223,330 and German Laid-Open Specification (DOS) No. 1,769,757 and 
auxiliary carriers and printing inks therefor are known from German 
Laid-Open Specifications (DOS) Nos. 1,771,812 and 1,771,813.