Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1992-12-30
1994-03-01
Lee, Mary C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534637, 544197, 8549, C09B 62513, D06P 1384
Patent
active
052909220
DESCRIPTION:
BRIEF SUMMARY
The invention relates to the field of fiber-reactive dyes.
Fiber-reactive azo dyes which contain two radicals of azo chromophores which are each connected to a triazine radical via an amino group are known for example from U.S. Pat. Nos. 4,485,041 and 4,806,127, British Patent No. 2,007,698, German Offenlegungschrift 3,320,972 and Japanese Patent Publication Sho 62-132,968. However, increased expectations of the quality of dyeings and of the economics of the dyeing process have made it necessary to develop improved dyes. This is because especially the dyeing of cellulose fiber materials, such as cotton, by the cold pad-batch method requires dyes which are readily soluble and which are highly reactive at the low dyeing and fixing temperatures. They should have a high degree of fixation to be not only economically but also ecologically advantageous. Moreover, the dyeings obtained should be dischargeable, for example in order to be able to be used as a ground dyeing in discharge printing.
This object is achieved according to the present invention by the water-soluble disazo dyes of the formula (1), indicated and defined hereinafter, which have very good fiber-reactive dyeing properties. ##STR2##
In the formula (1):
Me is hydrogen or an alkali metal, such as sodium, potassium or lithium;
K.sup.1 is a radical of the formula (2a) ##STR3## where Me has one of the abovementioned meanings and
K.sup.2 is a radical of the formula (2b) ##STR4## where Me and n are each as defined above;
D.sup.1 and D.sup.2 are each independently of the other a group of the formula (3a), (3b) or (3c) ##STR5## 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 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 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-eliminable 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 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 is vinylsulfonyl or .beta.-chloroethylsulfonyl, .beta.-thiosulfatoethylsulfonyl or .beta.-sulfatoethylsulfonyl, in particular .beta.-sulfatoethyl.
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 radicals D.sup.1 and D.sup.2 are for example:
Preferably, the radicals D.sup.1 and D.sup.2 are groups of identical structure.
Preferably, the radical --K.sup.1 --NH-- is a radical of the formula (4a), (4b) or (4c) ##STR6## where Me has the abovementioned meaning, a
REFERENCES:
patent: 3758470 (1973-09-01), Ackermann et al.
patent: 4378312 (1983-03-01), Hoyer et al.
patent: 4485041 (1984-11-01), Hoyer et al.
patent: 4649193 (1987-03-01), Meininger et al.
patent: 4806127 (1989-02-01), Schlafer et al.
Gleibner Rolf
Springer Hartmut
Hoechst Aktiengesellschaft
Lee Mary C.
Powers Fiona T.
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