Monoazo reactive dye which contains a dicyanoaminotriazinyl grou

Details Monoazo reactive dye which contains a dicyanoaminotriazinyl grou Monoazo reactive dye which contains a dicyanoaminotriazinyl grou

1993-01-21

1994-03-01

Lee, Mary C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

8549, C09B 6251, D06P 1384

Patent

active

052909239

DESCRIPTION:

BRIEF SUMMARY
The invention relates to the field of fiber-reactive dyes.
Fiber-reactive azo dyes having carboxamide groups as substituents on an aromatic radical are known for example from U.S. Pat. Nos. 4,448,583, 4,707,545 and 4,769,446 and European Patent Application Publication No. 0 210 492A. However, under alkaline dyeing conditions the amide bond may break, which leads to a marked shift in hue. By contrast, this effect is not shown by dyes having a chloro-s-triazinyl-containing amino group bonded to an aromatic radical, as known for example from U.S. Pat. No. 4,725,675 and European Patent Application Publication No. 0 066 819A. However, these dyes have the disadvantage that they are not dischargeable and therefore have only limited usefulness in ground dyeing.
The present invention provides water-soluble monoazo compounds which are improved in this respect and have the formula (1) , indicated and defined hereinafter, and which have very good fiber-reactive, dyeing properties. ##STR2##
In the formula (1): ##STR3## where Me has one of the abovementioned meanings and ##STR4## where Me has one of the abovementioned meanings, in particular methyl, which may be sulfo-, carboxyl- or sulfato-substituted, alkoxy of from 1 to 4 carbon atoms, such as ethoxy and in particular methoxy, which may be sulfo-, carboxyl or sulfato-substituted, chlorine, bromine, hydroxyl, cyano, carboxyl or sulfo, preferably hydrogen, methyl, methoxy or ethoxy, in particular methyl, or alkoxy of from 1 to 4 carbon atoms, such as ethoxy and in particular methoxy, preferably hydrogen or methoxy, which is eliminable by alkali to form a vinyl group, and
In the formula (3a) the group Y--SO.sub.2 -- is preferably bonded to the benzene ring meta or para to the free bond leading to the azo group, and in the formula (3c) this group is preferably bonded to the benzene ring meta or para to the aminocarbonyl group. In the formula (3b) the free bond which leads to the azo group is preferably in the 2-position of the naphthalene radical.
The individual variables can be identical or different relative to one another within their meanings.
Substituents which are in the .beta.-position of the ethyl group of the variable Y and which are alkali-enminable are for example alkanoyloxy groups of from 2 to 5 carbon atoms, such as acetyloxy groups, aroyloxy groups, such as benzoyloxy, sulfobenzoyloxy or carboxybenzoyloxy, alkyl and dialkyl-amino groups having alkyl moieties of from 1 to 4 carbon atoms, such as in particular dimethylamino and diethylamino, trialkylammonium groups having alkyl moieties of from 1 to 4 carbon atoms, such as trimethylammonium, the anion thereof being a customary colorless anion, such as chloride, hydrogensulfate or sulfate, alkylsulfonyloxy groups of from 1 to 4 carbon atoms, such as methylsulfonyloxy, fluorine or bromine and in particular a phosphato, thiosulfato or sulfato group. Preferably, the Y--SO.sub.2 -- group is vinylsulfonyl or .beta.-chloroethylsulfonyl, .beta.-thiosulfatoethylsulfonyl or .beta.-sulfatoethylsulfonyl, in particular .beta.-sulfatoethylsulfonyl.
Sulfo, carboxyl, sulfato, thiosulfato and phosphato groups are groups of the formula --SO.sub.3 Me, --COOMe, --OSO.sub.3 Me, --S--SO.sub.3 Me or --OPO.sub.3 Me.sub.2, in each of which Me has one of the abovementioned meanings.
The radical D is for example: 4-(.beta.-sulfatoethylsulfonyl)phenyl and
Preferably, the radical --K--NH-- is a radical of the formula (4a), (4b) or (4c) ##STR5## where Me has the abovementioned meaning and in the formula (4a) the --SO.sub.3 Me group is either meta or para to the amino group. Particularly preferably, the radical --NH--K-- is a radical of the formula (4a), where again the --SO.sub.3 Me group is preferably meta to the amino group.
The present invention further relates to a process for preparing the monoazo compounds of the formula (1), which comprises coupling a compound of the formula (5) ##STR6## where K and Me are each as defined above, with a diazonium compound of an aromatic amine of the formula D--NH.sub.2, where D is as defined above,

REFERENCES:
patent: 3758470 (1973-09-01), Ackermann et al.
patent: 4448583 (1984-05-01), Corso
patent: 4649193 (1987-03-01), Meininger et al.
patent: 4707545 (1987-11-01), Meininger et al.
patent: 4725675 (1988-02-01), Meininger et al.
patent: 4769446 (1988-09-01), Corso et al.
patent: 5225544 (1993-07-01), Dannheim et al.

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