Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1998-01-26
1998-11-10
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534797, 534827, 8437, 8924, 8681, C09B 3110, D06P 324, D06P 332
Patent
active
058346023
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP96/03439 filed Aug. 5,1996.
The present invention relates to novel disazo dyes of the formula I ##STR2## where the ring A may be benzofused, -C.sub.4 -alkoxy-carbonyl or hydroxysulfonyl, -C.sub.4 -alkoxy-carbonyl, or R.sup.1 and R.sup.2 together are a radical of the formula L--NZ--CO, where L is methylene or carbonyl and Z is C.sub.1 -C.sub.4 -alkyl with or without C.sub.1 -C.sub.4 -alkoxy substitution or unsubstituted or C.sub.1 -C.sub.4 -alkyl- or C.sub.1 -C.sub.4 -alkoxy-substituted phenyl, and -alkoxy, phenoxy, C.sub.1 -C.sub.4 -alkanoyloxy or benzoyloxy,
It is an object of the present invention to provide novel disazo-class acid dyes having advantageous application properties.
We have found that this object is achieved by the above-defined disazo dyes of the formula I.
Any alkyl appearing in the abovementioned formula I can be straight-chain or branched.
R.sup.1, R.sup.2, R.sup.3, X and Z are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
R.sup.1 and R.sup.2 may each also be for example fluorine, chlorine, bromine, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl or butoxycarbonyl.
Z may also be for example 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxybutyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybutyl, 2- or 4-butoxybutyl, phenyl, 2-, 3- or 4-methylphenyl, 2,4-dimethylphenyl, 2-, 3- or 4-methoxyphenyl or 2,4-dimethoxyphenyl.
R.sup.3 may also be for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, formyloxy, acetyloxy, propionyloxy, butyryloxy or isobutyryloxy.
Since the disazo dyes of the formula I contain a plurality of hydroxysulfonyl groups, their salts are also covered by the invention.
Suitable salts here are metal or ammonium salts. Metal salts are, in particular, the lithium, sodium or potassium salts. For the purposes of the present invention, ammonium salts are taken to mean salts which contain either unsubstituted or substituted ammonium cations. Examples of substituted ammonium cations are monoalkyl-, dialkyl-, trialkyl-, tetraalkyl- or benzyltrialkyl-ammonium cations or cations which are derived from five- or six-membered, saturated, nitrogen-containing heterocyclic rings, such as pyrrolidinium, piperidinium, morpholinium or piperazinium cations, or N-monoalkyl- or N,N-dialkyl-substituted products thereof. Alkyl here is generally taken to mean straight-chain or branched C.sub.1 -C.sub.20 -alkyl, which may be substituted by 1 or 2 hydroxyl groups and/or interrupted by 1 to 4 oxygen atoms in ether function.
Preference is given to disazo dyes of the formula Ia ##STR3## where the ring A, X, R.sup.1, R.sup.2 and R.sup.3 are each as defined above.
Preference is further given to disazo dyes of the formula Ib ##STR4## where the ring A, X, R.sup.1, R.sup.2 and R.sup.3 are each as defined above.
Preference is further given to disazo dyes of the formula I where R.sup.1 is hydrogen, methyl, carboxyl, C.sub.1 - or C.sub.2 -alkoxycarbonyl or hydroxysulfonyl.
Preference is further given to disazo dyes of the formula I where R.sup.2 is hydrogen, methyl, carboxyl or C.sub.1 - or C.sub.2 -alkoxycarbonyl.
Preference is further given to disazo dyes of the formula I where R.sup.3 is hydrogen or hydroxyl.
Preference is further given to disazo dyes of the formula I where the ring A is not benzofused.
Preference is further given to disazo dyes of the formula I where at least one of R.sup.1, R.sup.2 and R.sup.3 is not hydrogen.
Preference is further given to disazo dyes of the formula I where X is hydrogen.
Particular preference is given to disazo dyes of the formula I where R.sup.3 is hydroxyl.
Very particular preference is given to disazo dyes of the formula I where R.sup.1 and R.sup.2 are each hydrogen and R.sup.3 is hydroxyl.
Of particular technical interest are disazo dyes of the formula Ic ##STR5## and the dye of the formula Id ##STR6## may be si
REFERENCES:
patent: 4479906 (1984-10-01), Zeidler et al.
patent: 4784668 (1988-11-01), Breitschaft et al.
Lamm Gunther
Reichelt Helmut
BASF - Aktiengesellschaft
Powers Fiona T.
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